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id="toc-Addition_of_carboxylic_acids_and_their_derivatives" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Addition_of_carboxylic_acids_and_their_derivatives"> <div class="vector-toc-text"> 4.2 Addition of carboxylic acids and their derivatives </div> </a> <ul id="toc-Addition_of_carboxylic_acids_and_their_derivatives-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Adding_ammonia_and_amines" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Adding_ammonia_and_amines"> <div class="vector-toc-text"> 4.3 Adding ammonia and amines </div> </a> <ul id="toc-Adding_ammonia_and_amines-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Halide_addition" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Halide_addition"> <div class="vector-toc-text"> 4.4 Halide addition </div> </a> <ul id="toc-Halide_addition-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Metalorganic_addition" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Metalorganic_addition"> <div class="vector-toc-text"> 4.5 Metalorganic addition </div> </a> <ul id="toc-Metalorganic_addition-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other_addition_reactions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Other_addition_reactions"> <div class="vector-toc-text"> 4.6 Other addition reactions </div> </a> <ul id="toc-Other_addition_reactions-sublist" class="vector-toc-list"> <li id="toc-Addition_of_hydrogen_cyanide" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Addition_of_hydrogen_cyanide"> <div class="vector-toc-text"> 4.6.1 Addition of hydrogen cyanide </div> </a> <ul id="toc-Addition_of_hydrogen_cyanide-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Addition_of_hydrogen_sulfide_and_mercaptans" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Addition_of_hydrogen_sulfide_and_mercaptans"> <div class="vector-toc-text"> 4.6.2 Addition of hydrogen sulfide and mercaptans </div> </a> <ul id="toc-Addition_of_hydrogen_sulfide_and_mercaptans-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Addition_of_nitrous_and_nitric_acids" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Addition_of_nitrous_and_nitric_acids"> <div class="vector-toc-text"> 4.6.3 Addition of nitrous and nitric acids </div> </a> <ul id="toc-Addition_of_nitrous_and_nitric_acids-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Reaction_with_compounds_containing_active_methylene_groups" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Reaction_with_compounds_containing_active_methylene_groups"> <div class="vector-toc-text"> 4.6.4 Reaction with compounds containing active methylene groups </div> </a> <ul id="toc-Reaction_with_compounds_containing_active_methylene_groups-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Alkylation_of_aromatic_compounds" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Alkylation_of_aromatic_compounds"> <div class="vector-toc-text"> 4.6.5 Alkylation of aromatic compounds </div> </a> <ul id="toc-Alkylation_of_aromatic_compounds-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Synthesis_of_crown_ethers" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Synthesis_of_crown_ethers"> <div class="vector-toc-text"> 4.6.6 Synthesis of crown ethers </div> </a> <ul id="toc-Synthesis_of_crown_ethers-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Isomerization" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Isomerization"> <div class="vector-toc-text"> 4.7 Isomerization </div> </a> <ul id="toc-Isomerization-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Reduction_reaction" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Reduction_reaction"> <div class="vector-toc-text"> 4.8 Reduction reaction </div> </a> <ul id="toc-Reduction_reaction-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Oxidation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Oxidation"> <div class="vector-toc-text"> 4.9 Oxidation </div> </a> <ul id="toc-Oxidation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Dimerization" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Dimerization"> <div class="vector-toc-text"> 4.10 Dimerization </div> </a> <ul id="toc-Dimerization-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Polymerization" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Polymerization"> <div class="vector-toc-text"> 4.11 Polymerization </div> </a> <ul id="toc-Polymerization-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Thermal_decomposition" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Thermal_decomposition"> <div class="vector-toc-text"> 4.12 Thermal decomposition </div> </a> <ul id="toc-Thermal_decomposition-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other_reactions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Other_reactions"> <div class="vector-toc-text"> 4.13 Other reactions </div> </a> <ul id="toc-Other_reactions-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Laboratory_synthesis" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Laboratory_synthesis"> <div class="vector-toc-text"> 5 Laboratory synthesis </div> </a> <button aria-controls="toc-Laboratory_synthesis-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Laboratory synthesis subsection </button> <ul id="toc-Laboratory_synthesis-sublist" class="vector-toc-list"> <li id="toc-Dehydrochlorination_of_ethylene_and_its_derivatives" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Dehydrochlorination_of_ethylene_and_its_derivatives"> <div class="vector-toc-text"> 5.1 Dehydrochlorination of ethylene and its derivatives </div> </a> <ul id="toc-Dehydrochlorination_of_ethylene_and_its_derivatives-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Direct_oxidation_of_ethylene_by_peroxy_acids" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Direct_oxidation_of_ethylene_by_peroxy_acids"> <div class="vector-toc-text"> 5.2 Direct oxidation of ethylene by peroxy acids </div> </a> <ul id="toc-Direct_oxidation_of_ethylene_by_peroxy_acids-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other_preparative_methods" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Other_preparative_methods"> <div class="vector-toc-text"> 5.3 Other preparative methods </div> </a> <ul id="toc-Other_preparative_methods-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Industrial_synthesis" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Industrial_synthesis"> <div class="vector-toc-text"> 6 Industrial synthesis </div> </a> <button aria-controls="toc-Industrial_synthesis-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Industrial synthesis subsection </button> <ul id="toc-Industrial_synthesis-sublist" class="vector-toc-list"> <li id="toc-History_2" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#History_2"> <div class="vector-toc-text"> 6.1 History </div> </a> <ul id="toc-History_2-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Chlorohydrin_process_of_production_of_ethylene_oxide" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Chlorohydrin_process_of_production_of_ethylene_oxide"> <div class="vector-toc-text"> 6.2 Chlorohydrin process of production of ethylene oxide </div> </a> <ul id="toc-Chlorohydrin_process_of_production_of_ethylene_oxide-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Direct_oxidation_of_ethylene" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Direct_oxidation_of_ethylene"> <div class="vector-toc-text"> 6.3 Direct oxidation of ethylene </div> </a> <ul id="toc-Direct_oxidation_of_ethylene-sublist" class="vector-toc-list"> <li id="toc-Usage_in_global_industry" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Usage_in_global_industry"> <div class="vector-toc-text"> 6.3.1 Usage in global industry </div> </a> <ul id="toc-Usage_in_global_industry-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Chemistry_and_kinetics_of_the_direct_oxidation_process" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Chemistry_and_kinetics_of_the_direct_oxidation_process"> <div class="vector-toc-text"> 6.3.2 Chemistry and kinetics of the direct oxidation process </div> </a> <ul id="toc-Chemistry_and_kinetics_of_the_direct_oxidation_process-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Process_overview" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Process_overview"> <div class="vector-toc-text"> 6.4 Process overview </div> </a> <ul id="toc-Process_overview-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-World_production_of_ethylene_oxide" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#World_production_of_ethylene_oxide"> <div class="vector-toc-text"> 6.5 World production of ethylene oxide </div> </a> <ul id="toc-World_production_of_ethylene_oxide-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Applications" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Applications"> <div class="vector-toc-text"> 7 Applications </div> </a> <button aria-controls="toc-Applications-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Applications subsection </button> <ul id="toc-Applications-sublist" class="vector-toc-list"> <li id="toc-Production_of_ethylene_glycol" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Production_of_ethylene_glycol"> <div class="vector-toc-text"> 7.1 Production of ethylene glycol </div> </a> <ul id="toc-Production_of_ethylene_glycol-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Production_of_glycol_ethers" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Production_of_glycol_ethers"> <div class="vector-toc-text"> 7.2 Production of glycol ethers </div> </a> <ul id="toc-Production_of_glycol_ethers-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Production_of_ethanolamines" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Production_of_ethanolamines"> <div class="vector-toc-text"> 7.3 Production of ethanolamines </div> </a> <ul id="toc-Production_of_ethanolamines-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Production_of_ethoxylates" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Production_of_ethoxylates"> <div class="vector-toc-text"> 7.4 Production of ethoxylates </div> </a> <ul id="toc-Production_of_ethoxylates-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Production_of_acrylonitrile" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Production_of_acrylonitrile"> <div class="vector-toc-text"> 7.5 Production of acrylonitrile </div> </a> <ul id="toc-Production_of_acrylonitrile-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Non-industrial_uses" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Non-industrial_uses"> <div class="vector-toc-text"> 8 Non-industrial uses </div> </a> <button aria-controls="toc-Non-industrial_uses-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Non-industrial uses subsection </button> <ul id="toc-Non-industrial_uses-sublist" class="vector-toc-list"> <li id="toc-Healthcare_sterilant" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Healthcare_sterilant"> <div class="vector-toc-text"> 8.1 Healthcare sterilant </div> </a> <ul id="toc-Healthcare_sterilant-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Niche_uses" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Niche_uses"> <div class="vector-toc-text"> 8.2 Niche uses </div> </a> <ul id="toc-Niche_uses-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Identification_of_ethylene_oxide" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Identification_of_ethylene_oxide"> <div class="vector-toc-text"> 9 Identification of ethylene oxide </div> </a> <ul id="toc-Identification_of_ethylene_oxide-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Accidents" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Accidents"> <div class="vector-toc-text"> 10 Accidents </div> </a> <button aria-controls="toc-Accidents-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Accidents subsection </button> <ul id="toc-Accidents-sublist" class="vector-toc-list"> <li id="toc-La_Canonja,_Spain_accident" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#La_Canonja,_Spain_accident"> <div class="vector-toc-text"> 10.1 La Canonja, Spain accident </div> </a> <ul id="toc-La_Canonja,_Spain_accident-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-2020_sesame_seeds_contamination" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#2020_sesame_seeds_contamination"> <div class="vector-toc-text"> 10.2 2020 sesame seeds contamination </div> </a> <ul id="toc-2020_sesame_seeds_contamination-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Physiological_effects" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Physiological_effects"> <div class="vector-toc-text"> 11 Physiological effects </div> </a> <button aria-controls="toc-Physiological_effects-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Physiological effects subsection </button> <ul id="toc-Physiological_effects-sublist" class="vector-toc-list"> <li id="toc-Effect_on_microorganisms" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Effect_on_microorganisms"> <div class="vector-toc-text"> 11.1 Effect on microorganisms </div> </a> <ul id="toc-Effect_on_microorganisms-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Effects_on_humans_and_animals" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Effects_on_humans_and_animals"> <div class="vector-toc-text"> 11.2 Effects on humans and animals </div> </a> <ul id="toc-Effects_on_humans_and_animals-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Global_demand" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Global_demand"> <div class="vector-toc-text"> 12 Global demand </div> </a> <ul id="toc-Global_demand-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Health_and_safety_regulations" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Health_and_safety_regulations"> <div class="vector-toc-text"> 13 Health and safety regulations </div> </a> <ul id="toc-Health_and_safety_regulations-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> 14 References </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Cited_sources" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Cited_sources"> <div class="vector-toc-text"> 15 Cited sources </div> </a> <ul id="toc-Cited_sources-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> 16 External links </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" title="Table of Contents" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" > Toggle the table of contents </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading">Ethylene oxide</h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 46 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-46" aria-hidden="true" > 46 languages </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%A3%D9%83%D8%B3%D9%8A%D8%AF_%D8%A7%D9%84%D8%A5%D9%8A%D8%AB%D9%8A%D9%84%D9%8A%D9%86" title="أكسيد الإيثيلين – Arabic" lang="ar" hreflang="ar" data-title="أكسيد الإيثيلين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target">العربية</a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Etilenoksid" title="Etilenoksid – Azerbaijani" lang="az" hreflang="az" data-title="Etilenoksid" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target">Azərbaycanca</a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%A7%D8%AA%DB%8C%D9%84%D9%86_%D8%A7%D9%88%DA%A9%D8%B3%D8%A7%DB%8C%D8%AF" title="اتیلن اوکساید – South Azerbaijani" lang="azb" hreflang="azb" data-title="اتیلن اوکساید" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target">تۆرکجه</a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/%C3%92xid_d%27etil%C3%A8" title="Òxid d'etilè – Catalan" lang="ca" hreflang="ca" data-title="Òxid d'etilè" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target">Català</a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Ethylenoxid" title="Ethylenoxid – Czech" lang="cs" hreflang="cs" data-title="Ethylenoxid" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target">Čeština</a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Ethylenoxid" title="Ethylenoxid – Danish" lang="da" hreflang="da" data-title="Ethylenoxid" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target">Dansk</a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Ethylenoxid" title="Ethylenoxid – German" lang="de" hreflang="de" data-title="Ethylenoxid" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target">Deutsch</a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Et%C3%BCleenoksiid" title="Etüleenoksiid – Estonian" lang="et" hreflang="et" data-title="Etüleenoksiid" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target">Eesti</a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%9F%CE%BE%CE%B9%CF%81%CE%AC%CE%BD%CE%B9%CE%BF" title="Οξιράνιο – Greek" lang="el" hreflang="el" data-title="Οξιράνιο" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target">Ελληνικά</a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/%C3%93xido_de_etileno" title="Óxido de etileno – Spanish" lang="es" hreflang="es" data-title="Óxido de etileno" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target">Español</a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Etilen_oxido" title="Etilen oxido – Basque" lang="eu" hreflang="eu" data-title="Etilen oxido" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target">Euskara</a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A7%D8%AA%DB%8C%D9%84%D9%86_%D8%A7%DA%A9%D8%B3%D8%A7%DB%8C%D8%AF" title="اتیلن اکساید – Persian" lang="fa" hreflang="fa" data-title="اتیلن اکساید" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target">فارسی</a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Oxyde_d%27%C3%A9thyl%C3%A8ne" title="Oxyde d'éthylène – French" lang="fr" hreflang="fr" data-title="Oxyde d'éthylène" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target">Français</a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%82%B0%ED%99%94_%EC%97%90%ED%8B%B8%EB%A0%8C" title="산화 에틸렌 – Korean" lang="ko" hreflang="ko" data-title="산화 에틸렌" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target">한국어</a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D4%B7%D5%A9%D5%AB%D5%AC%D5%A5%D5%B6%D6%85%D6%84%D5%BD%D5%AB%D5%A4" title="Էթիլենօքսիդ – Armenian" lang="hy" hreflang="hy" data-title="Էթիլենօքսիդ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target">Հայերեն</a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%87%E0%A4%A5%E0%A4%BF%E0%A4%B2%E0%A5%80%E0%A4%A8_%E0%A4%91%E0%A4%95%E0%A5%8D%E0%A4%B8%E0%A4%BE%E0%A4%87%E0%A4%A1" title="इथिलीन ऑक्साइड – Hindi" lang="hi" hreflang="hi" data-title="इथिलीन ऑक्साइड" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target">हिन्दी</a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Etilen-oksid" title="Etilen-oksid – Croatian" lang="hr" hreflang="hr" data-title="Etilen-oksid" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target">Hrvatski</a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Etilena_oksida" title="Etilena oksida – Indonesian" lang="id" hreflang="id" data-title="Etilena oksida" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target">Bahasa Indonesia</a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Ossido_di_etilene" title="Ossido di etilene – Italian" lang="it" hreflang="it" data-title="Ossido di etilene" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target">Italiano</a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%90%D7%AA%D7%99%D7%9C%D7%9F_%D7%90%D7%95%D7%A7%D7%A1%D7%99%D7%93" title="אתילן אוקסיד – Hebrew" lang="he" hreflang="he" data-title="אתילן אוקסיד" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target">עברית</a></li><li class="interlanguage-link interwiki-kn mw-list-item"><a href="https://kn.wikipedia.org/wiki/%E0%B2%8E%E0%B2%A5%E0%B2%BF%E0%B2%B2%E0%B3%80%E0%B2%A8%E0%B3%8D_%E0%B2%86%E0%B2%95%E0%B3%8D%E0%B2%B8%E0%B3%88%E0%B2%A1%E0%B3%8D" title="ಎಥಿಲೀನ್ ಆಕ್ಸೈಡ್ – Kannada" lang="kn" hreflang="kn" data-title="ಎಥಿಲೀನ್ ಆಕ್ಸೈಡ್" data-language-autonym="ಕನ್ನಡ" data-language-local-name="Kannada" class="interlanguage-link-target">ಕನ್ನಡ</a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%AD%D1%82%D0%B8%D0%BB%D0%B5%D0%BD_%D1%82%D0%BE%D1%82%D1%8B%D2%93%D1%8B" title="Этилен тотығы – Kazakh" lang="kk" hreflang="kk" data-title="Этилен тотығы" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target">Қазақша</a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Etil%C4%93noks%C4%ABds" title="Etilēnoksīds – Latvian" lang="lv" hreflang="lv" data-title="Etilēnoksīds" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target">Latviešu</a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Etil%C3%A9n-oxid" title="Etilén-oxid – Hungarian" lang="hu" hreflang="hu" data-title="Etilén-oxid" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target">Magyar</a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Etilena_oksida" title="Etilena oksida – Malay" lang="ms" hreflang="ms" data-title="Etilena oksida" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target">Bahasa Melayu</a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Etheenoxide" title="Etheenoxide – Dutch" lang="nl" hreflang="nl" data-title="Etheenoxide" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target">Nederlands</a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%A8%E3%83%81%E3%83%AC%E3%83%B3%E3%82%AA%E3%82%AD%E3%82%B7%E3%83%89" title="エチレンオキシド – Japanese" lang="ja" hreflang="ja" data-title="エチレンオキシド" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target">日本語</a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Etylenoksid" title="Etylenoksid – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Etylenoksid" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target">Norsk bokmål</a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Etilenoksid" title="Etilenoksid – Uzbek" lang="uz" hreflang="uz" data-title="Etilenoksid" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target">Oʻzbekcha / ўзбекча</a></li><li class="interlanguage-link interwiki-pnb mw-list-item"><a href="https://pnb.wikipedia.org/wiki/%D8%A7%DB%8C%D8%AA%DA%BE%D8%A7%D8%A6%D9%84%DB%8C%D9%86_%D8%A2%DA%A9%D8%B3%D8%A7%D8%A6%DA%88" title="ایتھائلین آکسائڈ – Western Punjabi" lang="pnb" hreflang="pnb" data-title="ایتھائلین آکسائڈ" data-language-autonym="پنجابی" data-language-local-name="Western Punjabi" class="interlanguage-link-target">پنجابی</a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Tlenek_etylenu" title="Tlenek etylenu – Polish" lang="pl" hreflang="pl" data-title="Tlenek etylenu" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target">Polski</a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/%C3%93xido_de_etileno" title="Óxido de etileno – Portuguese" lang="pt" hreflang="pt" data-title="Óxido de etileno" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target">Português</a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Oxid_de_etilen%C4%83" title="Oxid de etilenă – Romanian" lang="ro" hreflang="ro" data-title="Oxid de etilenă" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target">Română</a></li><li class="interlanguage-link interwiki-ru badge-Q17437796 badge-featuredarticle mw-list-item" title="featured article badge"><a href="https://ru.wikipedia.org/wiki/%D0%9E%D0%BA%D0%B8%D1%81%D1%8C_%D1%8D%D1%82%D0%B8%D0%BB%D0%B5%D0%BD%D0%B0" title="Окись этилена – Russian" lang="ru" hreflang="ru" data-title="Окись этилена" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target">Русский</a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Ethylene_oxide" title="Ethylene oxide – Simple English" lang="en-simple" hreflang="en-simple" data-title="Ethylene oxide" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target">Simple English</a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Etyl%C3%A9noxid" title="Etylénoxid – Slovak" lang="sk" hreflang="sk" data-title="Etylénoxid" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target">Slovenčina</a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Etilenoksid" title="Etilenoksid – Slovenian" lang="sl" hreflang="sl" data-title="Etilenoksid" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target">Slovenščina</a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Etilen_oksid" title="Etilen oksid – Serbian" lang="sr" hreflang="sr" data-title="Etilen oksid" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target">Српски / srpski</a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Etilen_oksid" title="Etilen oksid – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Etilen oksid" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target">Srpskohrvatski / српскохрватски</a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Etyleenioksidi" title="Etyleenioksidi – Finnish" lang="fi" hreflang="fi" data-title="Etyleenioksidi" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target">Suomi</a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Etenoxid" title="Etenoxid – Swedish" lang="sv" hreflang="sv" data-title="Etenoxid" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target">Svenska</a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B9%80%E0%B8%AD%E0%B8%97%E0%B8%B4%E0%B8%A5%E0%B8%B5%E0%B8%99%E0%B8%AD%E0%B8%AD%E0%B8%81%E0%B9%84%E0%B8%8B%E0%B8%94%E0%B9%8C" title="เอทิลีนออกไซด์ – Thai" lang="th" hreflang="th" data-title="เอทิลีนออกไซด์" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target">ไทย</a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Etilen_oksit" title="Etilen oksit – Turkish" lang="tr" hreflang="tr" data-title="Etilen oksit" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target">Türkçe</a></li><li class="interlanguage-link interwiki-uk badge-Q17437798 badge-goodarticle mw-list-item" title="good article badge"><a href="https://uk.wikipedia.org/wiki/%D0%9E%D0%BA%D1%81%D0%B8%D1%80%D0%B0%D0%BD" title="Оксиран – Ukrainian" lang="uk" hreflang="uk" data-title="Оксиран" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target">Українська</a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Ethylen_oxide" title="Ethylen oxide – Vietnamese" lang="vi" hreflang="vi" data-title="Ethylen oxide" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target">Tiếng Việt</a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a 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.hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">"Oxirane" redirects here. For oxiranes as a class of molecules, see <a href="/wiki/Epoxide" title="Epoxide">epoxide</a>.</div><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951" /><div role="note" class="hatnote navigation-not-searchable">Not to be confused with <a href="/wiki/Ethylene_dione" title="Ethylene dione">Ethylene dione</a> or <a href="/wiki/Ethyl_oxide" class="mw-redirect" title="Ethyl oxide">Ethyl oxide</a>.</div> <style data-mw-deduplicate="TemplateStyles:r1268415487">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}</style> <table class="infobox ib-chembox"> <caption>Ethylene oxide </caption> <tbody><tr> <td colspan="2" class="borderless" style="text-align:center"> <table border="0" style="width:100%;display:inline-table;"> <tbody><tr> <td style="border-right:1px solid #aaa; width:50%;"><figure class="mw-halign-center skin-invert" typeof="mw:File"><a href="/wiki/File:Ethylene_oxide.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/14/Ethylene_oxide.svg/100px-Ethylene_oxide.svg.png" decoding="async" width="100" height="104" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/14/Ethylene_oxide.svg/150px-Ethylene_oxide.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/14/Ethylene_oxide.svg/200px-Ethylene_oxide.svg.png 2x" data-file-width="72" data-file-height="75" /></a><figcaption></figcaption></figure> </td> <td style="width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Ethylene-oxide-from-xtal-3D-balls.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2d/Ethylene-oxide-from-xtal-3D-balls.png/250px-Ethylene-oxide-from-xtal-3D-balls.png" decoding="async" width="150" height="121" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2d/Ethylene-oxide-from-xtal-3D-balls.png/330px-Ethylene-oxide-from-xtal-3D-balls.png 2x" data-file-width="1100" data-file-height="889" /></a><figcaption></figcaption></figure> </td></tr></tbody></table> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">Oxirane<a href="#cite_note-1">[1]</a></div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature#Systematic_name" title="Chemical nomenclature">Systematic IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">Epoxyethane Oxacyclopropane</div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">Ethylene oxide Dimethylene oxide 1,2-Epoxyethane [3]-crown-1 Epoxide</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=75-21-8">75-21-8</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=O1CC1">Interactive image</a></li></ul></div> </td></tr> <tr> <td>Abbreviations </td> <td>EO, EtO </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Beilstein_database" title="Beilstein database">Beilstein Reference</a></div> </td> <td>102378 </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=27561">CHEBI:27561</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL1743219">ChEMBL1743219</a></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.6114.html">6114</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard">ECHA InfoCard</a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.000.773">100.000.773</a> <a href="https://www.wikidata.org/wiki/Q407473#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a> </td></tr> <tr> <td><a href="/wiki/European_Community_number" title="European Community number">EC Number</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li>200-849-9</li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Gmelin_database" title="Gmelin database">Gmelin Reference</a></div> </td> <td>676 </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/D03474">D03474</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div> </td></tr> <tr> <td><a href="/wiki/Medical_Subject_Headings" title="Medical Subject Headings">MeSH</a> </td> <td><a rel="nofollow" class="external text" href="https://www.nlm.nih.gov/cgi/mesh/2014/MB_cgi?mode=&term=Ethylene+Oxide">Ethylene+Oxide</a> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/6354">6354</a></li></ul></div> </td></tr> <tr> <td><a href="/wiki/RTECS" class="mw-redirect" title="RTECS">RTECS number</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li>KX2450000</li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/JJH7GNN18P">JJH7GNN18P</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div> </td></tr> <tr> <td><a href="/wiki/UN_number" title="UN number">UN number</a> </td> <td>1040 </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> (<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID0020600">DTXSID0020600</a> <a href="https://www.wikidata.org/wiki/Q407473#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C2H4O/c1-2-3-1/h1-2H2 <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: IAYPIBMASNFSPL-UHFFFAOYSA-N <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1/C2H4O/c1-2-3-1/h1-2H2</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: IAYPIBMASNFSPL-UHFFFAOYAX</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">O1CC1</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style>C2H4O </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td>44.052 g·mol−1<a href="#cite_note-r3430-2">[2]</a> </td></tr> <tr> <td>Appearance </td> <td>Colorless gas </td></tr> <tr> <td><a href="/wiki/Odor" title="Odor">Odor</a> </td> <td>Like diethyl ether<a href="#cite_note-3">[3]</a> </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>0.8821 g·cm−3<a href="#cite_note-r3430-2">[2]</a> </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>−112.46 °C (−170.43 °F; 160.69 K)<a href="#cite_note-r3430-2">[2]</a> </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>10.4 °C (50.7 °F; 283.5 K)<a href="#cite_note-r3430-2">[2]</a> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></div> </td> <td>Miscible </td></tr> <tr> <td><a href="/wiki/Vapor_pressure" title="Vapor pressure">Vapor pressure</a> </td> <td>1.46 atm (20 °C)<a href="#cite_note-PGCH-4">[4]</a> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Magnetic_susceptibility" title="Magnetic susceptibility">Magnetic susceptibility</a> (χ)</div> </td> <td>−30.5·10−6 cm3/mol<a href="#cite_note-5">[5]</a> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Refractive_index" title="Refractive index">Refractive index</a> (nD)</div> </td> <td>1.3597 (589 nm)<a href="#cite_note-r3430-2">[2]</a> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Dipole#Molecular_dipoles" title="Dipole">Dipole moment</a></div> </td> <td>1.94 D<a href="#cite_note-r1520-6">[6]</a> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Thermochemistry </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Heat_capacity" title="Heat capacity">Heat capacity</a> (C)</div> </td> <td>47.9 J·mol−1·K−1<a href="#cite_note-r522-7">[7]</a> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Standard_molar_entropy" title="Standard molar entropy">Std molar entropy</a> (S⦵298)</div> </td> <td>242.5 J·mol−1·K−1<a href="#cite_note-r522-7">[7]</a> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Standard_enthalpy_change_of_formation" class="mw-redirect" title="Standard enthalpy change of formation">Std enthalpy of formation</a> (ΔfH⦵298)</div> </td> <td>−52.6 kJ·mol−1<a href="#cite_note-r522-7">[7]</a> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Gibbs_free_energy#Standard_energy_change_of_formation" title="Gibbs free energy">Gibbs free energy</a> (ΔfG⦵)</div> </td> <td>−13.0 kJ·mol−1<a href="#cite_note-r522-7">[7]</a> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Hazards </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><a href="/wiki/Occupational_safety_and_health" title="Occupational safety and health">Occupational safety and health</a> (OHS/OSH): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Main hazards</div> </td> <td><a href="/wiki/Carcinogen" title="Carcinogen">Carcinogen</a> Extremely flammable </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals" title="Globally Harmonized System of Classification and Labelling of Chemicals">GHS labelling</a>: </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_pictograms" title="GHS hazard pictograms">Pictograms</a></div> </td> <td><a href="/wiki/File:GHS-pictogram-flamme.svg" class="mw-file-description" title="GHS02: Flammable"><img alt="GHS02: Flammable" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/GHS-pictogram-flamme.svg/50px-GHS-pictogram-flamme.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/GHS-pictogram-flamme.svg/75px-GHS-pictogram-flamme.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6d/GHS-pictogram-flamme.svg/100px-GHS-pictogram-flamme.svg.png 2x" data-file-width="512" data-file-height="512" /></a><a href="/wiki/File:GHS-pictogram-skull.svg" class="mw-file-description" title="GHS06: Toxic"><img alt="GHS06: Toxic" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/GHS-pictogram-skull.svg/60px-GHS-pictogram-skull.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/GHS-pictogram-skull.svg/120px-GHS-pictogram-skull.svg.png 1.5x" data-file-width="724" data-file-height="724" /></a><a href="/wiki/File:GHS-pictogram-silhouette.svg" class="mw-file-description" title="GHS08: Health hazard"><img alt="GHS08: Health hazard" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/50px-GHS-pictogram-silhouette.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/75px-GHS-pictogram-silhouette.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/100px-GHS-pictogram-silhouette.svg.png 2x" data-file-width="724" data-file-height="724" /></a> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_statements" title="GHS hazard statements">Hazard statements</a></div> </td> <td><abbr class="abbr" title="H220: Extremely flammable gas">H220</abbr>, <abbr class="abbr" title="H230: May react explosively even in the absence of air">H230</abbr>, <abbr class="abbr" title="H301: Toxic if swallowed">H301</abbr>, <abbr class="abbr" title="H314: Causes severe skin burns and eye damage">H314</abbr>, <abbr class="abbr" title="H331: Toxic if inhaled">H331</abbr>, <abbr class="abbr" title="H335: May cause respiratory irritation">H335</abbr>, <abbr class="abbr" title="H336: May cause drowsiness or dizziness">H336</abbr>, <abbr class="abbr" title="H340: May cause genetic defects">H340</abbr>, <abbr class="abbr" title="H350: May cause cancer">H350</abbr>, <abbr class="abbr" title="H360FD: May damage fertility. May damage the unborn child.">H360FD</abbr>, <abbr class="abbr" title="H372: Causes damage to organs through prolonged or repeated exposure">H372</abbr> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_precautionary_statements" title="GHS precautionary statements">Precautionary statements</a></div> </td> <td><abbr class="abbr" title="P202: Do not handle until all safety precautions have been read and understood.">P202</abbr>, <abbr class="abbr" title="P210: Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking.">P210</abbr>, <abbr class="abbr" title="P260: Do not breathe dust/fume/gas/mist/vapours/spray.">P260</abbr>, <abbr class="abbr" title="P280: Wear protective gloves/protective clothing/eye protection/face protection.">P280</abbr>, <abbr class="abbr" title="P301+P310+P330: IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. Rinse mouth.">P301+P310+P330</abbr>, <abbr class="abbr" title="P303+P361+P353: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water [or shower].">P303+P361+P353</abbr>, <abbr class="abbr" title="P305+P351+P338+P310: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician.">P305+P351+P338+P310</abbr>, <abbr class="abbr" title="P410+P403: Protect from sunlight. Store in a well ventilated place.">P410+P403</abbr><a href="#cite_note-sigmaaldrich_2020-8">[8]</a> </td></tr> <tr> <td><a href="/wiki/NFPA_704" title="NFPA 704">NFPA 704</a> (fire diamond) </td> <td><style data-mw-deduplicate="TemplateStyles:r1170367383">.mw-parser-output .nfpa-704-diamond-ref{float:right;padding:1px;text-align:right}.mw-parser-output .nfpa-704-diamond-container{width:82px;font-family:sans-serif;margin:0 auto}.mw-parser-output .nfpa-704-diamond-container-ref{float:left;margin-left:1em}.mw-parser-output .nfpa-704-diamond-images{float:left;font-size:20px;text-align:center;position:relative;height:80px;width:80px;padding:1px}.mw-parser-output .nfpa-704-diamond-map{position:absolute;height:80px;width:80px}.mw-parser-output .nfpa-704-diamond .noresize{margin:0 auto}.mw-parser-output .nfpa-704-diamond-code{line-height:1em;text-align:center;position:absolute}.mw-parser-output .nfpa-704-diamond-code>a{color:black}.mw-parser-output .nfpa-704-diamond-blue{width:13px;top:31px;left:15px}.mw-parser-output .nfpa-704-diamond-red{width:12px;top:12px;left:35px}.mw-parser-output .nfpa-704-diamond-yellow{width:13px;top:31px;left:54px}.mw-parser-output .nfpa-704-diamond-white-image{position:relative;top:51px;left:0}.mw-parser-output .nfpa-704-diamond-white-text{vertical-align:middle;text-align:center;line-height:80%;position:absolute;top:52px}.mw-parser-output .nfpa-704-diamond-white-text a>span{position:absolute;color:black}.mw-parser-output .nfpa-704-diamond-white-wors{font-size:15px;width:23px;left:29px}.mw-parser-output .nfpa-704-diamond-white-wox{font-size:15px;font-stretch:condensed;width:21px;line-height:80%;top:-4px;left:29px}.mw-parser-output .nfpa-704-diamond-white-abcp{font-size:13.5px;font-stretch:condensed;width:28px;left:26px}.mw-parser-output .nfpa-704-diamond-white-ac{font-size:10px;width:30px;left:25px}.mw-parser-output .nfpa-704-diamond-white-strike{text-decoration:line-through}</style><div class="nfpa-704-diamond notheme"><div class="nfpa-704-diamond-container"><div class="nfpa-704-diamond-images nounderlines"> <div class="nfpa-704-diamond-map"><figure class="noresize" typeof="mw:File"><img alt="NFPA 704 four-colored diamond" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/80px-NFPA_704.svg.png" decoding="async" width="80" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/120px-NFPA_704.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/160px-NFPA_704.svg.png 2x" data-file-width="512" data-file-height="512" usemap="#ImageMap_4516129a0d527770" /><map name="ImageMap_4516129a0d527770"><area href="/wiki/NFPA_704#Blue" shape="poly" coords="23,23,47,47,23,70,0,47" alt="Health 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gas" title="Health 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gas" /><area href="/wiki/NFPA_704#Red" shape="poly" coords="47,0,70,23,47,47,23,23" alt="Flammability 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propane" title="Flammability 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propane" /><area href="/wiki/NFPA_704#Yellow" shape="poly" coords="70,23,94,47,70,70,47,47" alt="Instability 3: Capable of detonation or explosive decomposition but requires a strong initiating source, must be heated under confinement before initiation, reacts explosively with water, or will detonate if severely shocked. E.g. hydrogen peroxide" title="Instability 3: Capable of detonation or explosive decomposition but requires a strong initiating source, must be heated under confinement before initiation, reacts explosively with water, or will detonate if severely shocked. E.g. hydrogen peroxide" /><area href="/wiki/NFPA_704#White" shape="poly" coords="47,47,70,70,47,94,23,70" alt="Special hazards (white): no code" title="Special hazards (white): no code" /></map><figcaption></figcaption></figure></div><div class="nfpa-704-diamond-code nfpa-704-diamond-blue"> <a href="/wiki/NFPA_704#Blue" title="NFPA 704">3</a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-red"> <a href="/wiki/NFPA_704#Red" title="NFPA 704"><span title="Flammability 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propane" class="notheme mw-no-invert">4</a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-yellow"> <a href="/wiki/NFPA_704#Yellow" title="NFPA 704"><span title="Instability 3: Capable of detonation or explosive decomposition but requires a strong initiating source, must be heated under confinement before initiation, reacts explosively with water, or will detonate if severely shocked. E.g. hydrogen peroxide" class="notheme mw-no-invert">3</a></div></div></div></div> </td></tr> <tr> <td><a href="/wiki/Flash_point" title="Flash point">Flash point</a> </td> <td>−20 °C (−4 °F; 253 K)<a href="#cite_note-r1520-6">[6]</a> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Autoignition_temperature" title="Autoignition temperature">Autoignition temperature</a></div> </td> <td>429 °C (804 °F; 702 K)<a href="#cite_note-r1520-6">[6]</a> </td></tr> <tr> <td><a href="/wiki/Explosive_limit" class="mw-redirect" title="Explosive limit">Explosive limits</a> </td> <td>3 to 100% </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;">Lethal dose or concentration (LD, LC): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">LC50 (<a href="/wiki/Lethal_dose#LC50" title="Lethal dose">median concentration</a>)</div> </td> <td>836 ppm (mouse, 4 hr) 4000 ppm (rat, 4 hr) 800 ppm (rat, 4 hr) 819 ppm (guinea pig, 4 hr) 1460 ppm (rat, 4 hr) 835 ppm (mouse, 4 hr) 960 ppm (dog, 4 hr)<a href="#cite_note-9">[9]</a> </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health">NIOSH</a> (US health exposure limits): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Permissible_exposure_limit" title="Permissible exposure limit">PEL</a> (Permissible)</div> </td> <td>TWA 1 ppm 5 ppm [15-minute excursion]<a href="#cite_note-PGCH-4">[4]</a> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Recommended_exposure_limit" title="Recommended exposure limit">REL</a> (Recommended)</div> </td> <td>Ca TWA <0.1 ppm (0.18 mg/m3) C 5 ppm (9 mg/m3) [10-min/day]<a href="#cite_note-PGCH-4">[4]</a> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/IDLH" class="mw-redirect" title="IDLH">IDLH</a> (Immediate danger)</div> </td> <td>Ca [800 ppm]<a href="#cite_note-PGCH-4">[4]</a> </td></tr> <tr> <td><a href="/wiki/Safety_data_sheet" title="Safety data sheet">Safety data sheet</a> (SDS) </td> <td><a rel="nofollow" class="external text" href="https://www.inchem.org/documents/icsc/icsc/eics0155.htm">ICSC 0155</a> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Related compounds </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related heterocycles</div> </td> <td><a href="/wiki/Aziridine" title="Aziridine">Aziridine</a>, <a href="/wiki/Thiirane" title="Thiirane">Thiirane</a>, <a href="/wiki/Borirane" title="Borirane">Borirane</a> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; color:inherit; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/12px-Yes_check.svg.png" decoding="async" width="12" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/18px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/24px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y <a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=446701253&page2=Ethylene+oxide">verify</a> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y<img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" />N ?) </div></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> Ethylene oxide is an <a href="/wiki/Organic_compound" title="Organic compound">organic compound</a> with the <a href="/wiki/Chemical_formula" title="Chemical formula">formula</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" />C2H4O. It is a cyclic <a href="/wiki/Ether" title="Ether">ether</a> and the simplest <a href="/wiki/Epoxide" title="Epoxide">epoxide</a>: a three-membered <a href="/wiki/Ring_(chemistry)" title="Ring (chemistry)">ring</a> consisting of one <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> atom and two <a href="/wiki/Carbon" title="Carbon">carbon</a> atoms. Ethylene oxide is a colorless and <a href="/wiki/Flammable" class="mw-redirect" title="Flammable">flammable</a> gas with a faintly sweet odor. Because it is a <a href="/wiki/Strained_ring" class="mw-redirect" title="Strained ring">strained ring</a>, ethylene oxide easily participates in a number of <a href="/wiki/Addition_reaction" title="Addition reaction">addition reactions</a> that result in ring-opening. Ethylene oxide is <a href="/wiki/Isomer" title="Isomer">isomeric</a> with <a href="/wiki/Acetaldehyde" title="Acetaldehyde">acetaldehyde</a> and with <a href="/wiki/Vinyl_alcohol" title="Vinyl alcohol">vinyl alcohol</a>. Ethylene oxide is industrially produced by <a href="/wiki/Oxidation" class="mw-redirect" title="Oxidation">oxidation</a> of <a href="/wiki/Ethylene" title="Ethylene">ethylene</a> in the presence of a <a href="/wiki/Silver" title="Silver">silver</a> <a href="/wiki/Catalyst" class="mw-redirect" title="Catalyst">catalyst</a>. The reactivity that is responsible for many of ethylene oxide's hazards also makes it useful. Although too dangerous for direct household use and generally unfamiliar to consumers, ethylene oxide is used for making many consumer products as well as non-consumer chemicals and intermediates. These products include detergents, thickeners, solvents, plastics, and various organic chemicals such as <a href="/wiki/Ethylene_glycol" title="Ethylene glycol">ethylene glycol</a>, ethanolamines, simple and complex <a href="/wiki/Glycols" class="mw-redirect" title="Glycols">glycols</a>, <a href="/wiki/Polyglycol_ether" class="mw-redirect" title="Polyglycol ether">polyglycol ethers</a>, and other compounds. Although it is a vital raw material with diverse applications, including the manufacture of products like <a href="/wiki/Polysorbate_20" title="Polysorbate 20">polysorbate 20</a> and <a href="/wiki/Polyethylene_glycol" title="Polyethylene glycol">polyethylene glycol</a> (PEG) that are often more effective and less toxic than alternative materials, ethylene oxide itself is a very hazardous substance. At room temperature it is a very flammable, <a href="/wiki/Carcinogenic" class="mw-redirect" title="Carcinogenic">carcinogenic</a>, <a href="/wiki/Mutagenicity" class="mw-redirect" title="Mutagenicity">mutagenic</a>, irritating, and <a href="/wiki/Anaesthetic" class="mw-redirect" title="Anaesthetic">anaesthetic</a> gas.<a href="#cite_note-Ullmann-10">[10]</a> Ethylene oxide is a surface <a href="/wiki/Disinfectant" title="Disinfectant">disinfectant</a> that is widely used in hospitals and the medical equipment industry to <a href="/wiki/Sterilization_(microbiology)#Ethylene_oxide" title="Sterilization (microbiology)">replace steam in the sterilization</a> of heat-sensitive tools and equipment, such as disposable plastic syringes.<a href="#cite_note-11">[11]</a> It is so flammable and extremely explosive that it is used as a main component of <a href="/wiki/Thermobaric_weapon" title="Thermobaric weapon">thermobaric weapons</a>;<a href="#cite_note-e1-12">[12]</a><a href="#cite_note-e2-13">[13]</a> therefore, it is commonly handled and shipped as a refrigerated liquid to control its hazardous nature.<a href="#cite_note-Ullmann-10">[10]</a><a href="#cite_note-14">[14]</a> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="History">History</h2>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=1" title="Edit section: History">edit</a>]</div> Ethylene oxide was first reported in 1859 by the <a href="/wiki/France" title="France">French</a> chemist <a href="/wiki/Charles-Adolphe_Wurtz" class="mw-redirect" title="Charles-Adolphe Wurtz">Charles-Adolphe Wurtz</a>,<a href="#cite_note-15">[15]</a> who prepared it by treating <a href="/wiki/2-chloroethanol" class="mw-redirect" title="2-chloroethanol">2-chloroethanol</a> with <a href="/wiki/Potassium_hydroxide" title="Potassium hydroxide">potassium hydroxide</a>: <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" />Cl−CH2CH2−OH + KOH → (CH2CH2)O + KCl + H2O</dd></dl> Wurtz measured the <a href="/wiki/Boiling_point" title="Boiling point">boiling point</a> of ethylene oxide as 13.5 °C (56.3 °F), slightly higher than the present value, and discovered the ability of ethylene oxide to react with acids and salts of metals.<a href="#cite_note-oe1-16">[16]</a> Wurtz mistakenly assumed that ethylene oxide has the properties of an organic base. This misconception persisted until 1896, when <a href="/wiki/Georg_Bredig" title="Georg Bredig">Georg Bredig</a> found that ethylene oxide is not an <a href="/wiki/Electrolyte" title="Electrolyte">electrolyte</a>.<a href="#cite_note-oe1-16">[16]</a><a href="#cite_note-17">[17]</a> That it differed from other <a href="/wiki/Ether" title="Ether">ethers</a> — particularly by its propensity to engage in the addition reactions typical of <a href="/wiki/Saturated_and_unsaturated_compounds" title="Saturated and unsaturated compounds">unsaturated compounds</a> — had long been a matter of debate. The heterocyclic triangular structure of ethylene oxide was proposed by 1868 or earlier.<a href="#cite_note-18">[18]</a> Wurtz's 1859 synthesis long remained the only method of preparing ethylene oxide, despite numerous attempts, including by Wurtz himself, to produce ethylene oxide directly from <a href="/wiki/Ethylene" title="Ethylene">ethylene</a>.<a href="#cite_note-ect-19">[19]</a> Only in 1931 did French chemist Theodore Lefort develop a method of direct oxidation of ethylene in the presence of <a href="/wiki/Silver" title="Silver">silver</a> <a href="/wiki/Catalyst" class="mw-redirect" title="Catalyst">catalyst</a>.<a href="#cite_note-20">[20]</a> Since 1940, almost all industrial production of ethylene oxide has relied on this process.<a href="#cite_note-21">[21]</a> Sterilization by ethylene oxide for the preservation of <a href="/wiki/Spice" title="Spice">spices</a> was patented in 1938 by the <a href="/wiki/United_States" title="United States">American</a> chemist <a href="/wiki/Lloyd_Hall" title="Lloyd Hall">Lloyd Hall</a>. Ethylene oxide achieved industrial importance during <a href="/wiki/World_War_I" title="World War I">World War I</a> as a precursor to both the coolant <a href="/wiki/Ethylene_glycol" title="Ethylene glycol">ethylene glycol</a> and the <a href="/wiki/Chemical_weapon" title="Chemical weapon">chemical weapon</a> <a href="/wiki/Mustard_gas" title="Mustard gas">mustard gas</a>.[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a>] <div class="mw-heading mw-heading2"><h2 id="Molecular_structure_and_properties">Molecular structure and properties</h2>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=2" title="Edit section: Molecular structure and properties">edit</a>]</div> <figure class="mw-halign-right skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Ethylene-oxide.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a7/Ethylene-oxide.png/250px-Ethylene-oxide.png" decoding="async" width="250" height="135" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a7/Ethylene-oxide.png/500px-Ethylene-oxide.png 1.5x" data-file-width="760" data-file-height="409" /></a><figcaption></figcaption></figure> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Ethylene_oxide_refrigerated_liquid.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/61/Ethylene_oxide_refrigerated_liquid.jpg/250px-Ethylene_oxide_refrigerated_liquid.jpg" decoding="async" width="220" height="165" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/61/Ethylene_oxide_refrigerated_liquid.jpg/330px-Ethylene_oxide_refrigerated_liquid.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/61/Ethylene_oxide_refrigerated_liquid.jpg/500px-Ethylene_oxide_refrigerated_liquid.jpg 2x" data-file-width="3968" data-file-height="2976" /></a><figcaption>Condensed ethylene oxide</figcaption></figure> The epoxy cycle of ethylene oxide is an almost regular triangle with bond angles of about 60° and a significant angular <a href="/wiki/Strain_(chemistry)" title="Strain (chemistry)">strain</a> corresponding to the energy of 105 kJ/mol.<a href="#cite_note-22">[22]</a><a href="#cite_note-traven-23">[23]</a> For comparison, in <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohols</a> the C–O–H angle is about 110°; in <a href="/wiki/Ether" title="Ether">ethers</a>, the C–O–C angle is 120°. The <a href="/wiki/Moment_of_inertia" title="Moment of inertia">moment of inertia</a> about each of the principal axes are IA=32.921×10−40 g·cm2, IB=37.926×10−40 g·cm2 and IC=59.510×10−40 g·cm2.<a href="#cite_note-24">[24]</a> The relative instability of the carbon-oxygen bonds in the molecule is revealed by the comparison in the table of the energy required to break two C–O bonds in the ethylene oxide or one C–O bond in <a href="/wiki/Ethanol" title="Ethanol">ethanol</a> and <a href="/wiki/Dimethyl_ether" title="Dimethyl ether">dimethyl ether</a>:<a href="#cite_note-25">[25]</a> <table class="wikitable" style="text-align:center"> <tbody><tr> <th>Reaction </th> <th>ΔH°298, kJ/mol </th> <th>Method </th></tr> <tr> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" />(C2H4)O → C2H4 + O (cleavage of two bonds) </td> <td>354.38 </td> <td>Calculated, from atomic enthalpies </td></tr> <tr> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><a href="/wiki/Ethanol" title="Ethanol">C2H5OH</a> → C2H5 + OH (breaking one bond) </td> <td>405.85 </td> <td>Electron impact </td></tr> <tr> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><a href="/wiki/Dimethyl_ether" title="Dimethyl ether">CH3OCH3</a> → CH3O + CH3 (breaking one bond) </td> <td>334.72 </td> <td>Calculated using enthalpies of radicals formation </td></tr></tbody></table> This instability correlates with its high reactivity, explaining the ease of its <a href="/wiki/Ring-opening_reaction" class="mw-redirect" title="Ring-opening reaction">ring-opening reactions</a> (see <a href="#Chemical_properties">Chemical properties</a>). <div class="mw-heading mw-heading2"><h2 id="Physical_properties">Physical properties</h2>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=3" title="Edit section: Physical properties">edit</a>]</div> Ethylene oxide is a colorless gas at 25 °C (77 °F) and is a mobile liquid at 0 °C (32 °F) – viscosity of liquid ethylene oxide at 0 °C is about 5.5 times lower than that of water. The gas has a characteristic sweet odor of ether, noticeable when its concentration in air exceeds 500 ppm.<a href="#cite_note-atsdr-26">[26]</a> Ethylene oxide is readily soluble in water, <a href="/wiki/Ethanol" title="Ethanol">ethanol</a>, <a href="/wiki/Diethyl_ether" title="Diethyl ether">diethyl ether</a>, and many organic solvents.<a href="#cite_note-27">[27]</a> Main thermodynamical constants are:<a href="#cite_note-sch1-28">[28]</a> <ul><li>The <a href="/wiki/Surface_tension" title="Surface tension">surface tension</a> of liquid ethylene oxide, at the interface with its own vapor, is 35.8 mJ/m2 (0.00079 cal/sq ft) at −50.1 °C (−58.2 °F) and 27.6 mJ/m2 (0.00061 cal/sq ft) at −0.1 °C (31.8 °F).<a href="#cite_note-29">[29]</a></li> <li>The boiling point increases with the vapor pressure as follows:<a href="#cite_note-30">[30]</a> 57.7 °C (135.9 °F) (2 atm (200 kPa; 29 psi)), 83.6 °C (182.5 °F) (5 atm (510 kPa; 73 psi)), and 114.0 °C (237.2 °F) (10 atm (1,000 kPa; 150 psi)).</li> <li><a href="/wiki/Viscosity" title="Viscosity">Viscosity</a> decreases with temperature with the values of 0.577 kPa·s at −49.8 °C (−57.6 °F), 0.488 kPa·s at −38.2 °C (−36.8 °F), 0.394 kPa·s at −21.0 °C (−5.8 °F), and 0.320 kPa·s at 0 °C (32 °F).<a href="#cite_note-31">[31]</a></li></ul> Between −91 and 10.5 °C (−131.8 and 50.9 °F), vapor pressure p (in mmHg) varies with temperature (T in °C) as <dl><dd><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle \lg p=6.251-{\frac {1115.1}{244.14+T}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mi>lg</mi> <mo>⁡</mo> <mi>p</mi> <mo>=</mo> <mn>6.251</mn> <mo>−</mo> <mrow class="MJX-TeXAtom-ORD"> <mfrac> <mn>1115.1</mn> <mrow> <mn>244.14</mn> <mo>+</mo> <mi>T</mi> </mrow> </mfrac> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle \lg p=6.251-{\frac {1115.1}{244.14+T}}}</annotation> </semantics> </math><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/2046b010613c48db0ab6d6c7fe90828e02b3359b" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -2.005ex; width:26.373ex; height:5.343ex;" alt="{\displaystyle \lg p=6.251-{\frac {1115.1}{244.14+T}}}" />.<a href="#cite_note-32">[32]</a></dd></dl> <table class="wikitable" style="text-align:center"> <caption>Properties of liquid ethylene oxide<a href="#cite_note-ect-19">[19]</a> </caption> <tbody><tr> <th>Temperature, °C </th> <th>Vapor pressure, kPa </th> <th>Enthalpy of the liquid, J/g </th> <th>Enthalpy of vaporization, J/g </th> <th>Density, kg/L </th> <th><a href="/wiki/Heat_capacity" title="Heat capacity">Heat capacity</a>, J/(kg·K) </th> <th><a href="/wiki/Thermal_conductivity" class="mw-redirect" title="Thermal conductivity">Thermal conductivity</a>, W/(m·K) </th></tr> <tr> <td>−40 </td> <td>8.35 </td> <td>0 </td> <td>628.6 </td> <td>0.9488 </td> <td>1878 </td> <td>0.20 </td></tr> <tr> <td>−20 </td> <td>25.73 </td> <td>38.8 </td> <td>605.4 </td> <td>0.9232 </td> <td>1912 </td> <td>0.18 </td></tr> <tr> <td>0 </td> <td>65.82 </td> <td>77.3 </td> <td>581.7 </td> <td>0.8969 </td> <td>1954 </td> <td>0.16 </td></tr> <tr> <td>20 </td> <td>145.8 </td> <td>115.3 </td> <td>557.3 </td> <td>0.8697 </td> <td>2008 </td> <td>0.15 </td></tr> <tr> <td>40 </td> <td>288.4 </td> <td>153.2 </td> <td>532.1 </td> <td>0.8413 </td> <td>2092 </td> <td>0.14 </td></tr> <tr> <td>60 </td> <td>521.2 </td> <td>191.8 </td> <td>505.7 </td> <td>0.8108 </td> <td>2247 </td> <td>0.14 </td></tr> <tr> <td>80 </td> <td>875.4 </td> <td>232.6 </td> <td>477.4 </td> <td>0.7794 </td> <td>2426 </td> <td>0.14 </td></tr> <tr> <td>100 </td> <td>1385.4 </td> <td>277.8 </td> <td>445.5 </td> <td>0.7443 </td> <td>2782 </td> <td>0.13 </td></tr> <tr> <td>120 </td> <td>2088 </td> <td>330.4 </td> <td>407.5 </td> <td>0.7052 </td> <td>3293 </td> <td>N/A* </td></tr> <tr> <td>140 </td> <td>3020 </td> <td>393.5 </td> <td>359.4 </td> <td>0.6609 </td> <td>4225 </td> <td>N/A </td></tr> <tr> <td>160 </td> <td>4224 </td> <td>469.2 </td> <td>297.1 </td> <td>0.608 </td> <td>N/A </td> <td>N/A </td></tr> <tr> <td>180 </td> <td>5741 </td> <td>551.2 </td> <td>222.5 </td> <td>0.533 </td> <td>N/A </td> <td>N/A </td></tr> <tr> <td>195.8 </td> <td>7191 </td> <td>N/A </td> <td>N/A </td> <td>N/A </td> <td>N/A </td> <td>N/A </td></tr></tbody></table> *N/A – data not available. <table class="wikitable" style="text-align:center"> <caption>Properties of ethylene oxide vapor <a href="#cite_note-ect-19">[19]</a> </caption> <tbody><tr> <th>Temperature, K </th> <th>Entropy, J/(mol·K) </th> <th>Heat of formation, kJ/mol </th> <th>Free energy of formation, kJ/mol </th> <th>Viscosity, μPa·s </th> <th>Thermal conductivity, W/(m·K) </th> <th>Heat capacity, J/(mol·K) </th></tr> <tr> <td>298 </td> <td>242.4 </td> <td>−52.63 </td> <td>−13.10 </td> <td>N/A </td> <td>N/A </td> <td>48.28 </td></tr> <tr> <td>300 </td> <td>242.8 </td> <td>−52.72 </td> <td>−12.84 </td> <td>9.0 </td> <td>0.012 </td> <td>48.53 </td></tr> <tr> <td>400 </td> <td>258.7 </td> <td>−56.53 </td> <td>1.05 </td> <td>13.5 </td> <td>0.025 </td> <td>61.71 </td></tr> <tr> <td>500 </td> <td>274.0 </td> <td>−59.62 </td> <td>15.82 </td> <td>15.4 </td> <td>0.038 </td> <td>75.44 </td></tr> <tr> <td>600 </td> <td>288.8 </td> <td>−62.13 </td> <td>31.13 </td> <td>18.2 </td> <td>0.056 </td> <td>86.27 </td></tr> <tr> <td>700 </td> <td>302.8 </td> <td>−64.10 </td> <td>46.86 </td> <td>20.9 </td> <td>0.075 </td> <td>95.31 </td></tr> <tr> <td>800 </td> <td>316.0 </td> <td>−65.61 </td> <td>62.80 </td> <td>N/A </td> <td>0.090 </td> <td>102.9 </td></tr></tbody></table> *N/A – data not available. <div class="mw-heading mw-heading2"><h2 id="Chemical_properties">Chemical properties</h2>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=4" title="Edit section: Chemical properties">edit</a>]</div> Ethylene oxide readily reacts with diverse compounds with opening of the ring. Its typical reactions are with nucleophiles which proceed via the <a href="/wiki/Nucleophilic_substitution" title="Nucleophilic substitution">SN2</a> mechanism both in acidic (weak nucleophiles: water, alcohols) and alkaline media (strong nucleophiles: OH−, RO−, NH3, RNH2, RR'NH, etc.).<a href="#cite_note-traven-23">[23]</a> The general reaction scheme is <dl><dd><a href="/wiki/File:Ethylene_oxide_reactions.png" class="mw-file-description" title="Ethylene oxide reactions"><img alt="Ethylene oxide reactions" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7c/Ethylene_oxide_reactions.png/400px-Ethylene_oxide_reactions.png" decoding="async" width="400" height="170" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7c/Ethylene_oxide_reactions.png/600px-Ethylene_oxide_reactions.png 1.5x, //upload.wikimedia.org/wikipedia/commons/7/7c/Ethylene_oxide_reactions.png 2x" data-file-width="695" data-file-height="295" /></a></dd></dl> and more specific reactions are described below. <div class="mw-heading mw-heading3"><h3 id="Addition_of_water_and_alcohols">Addition of water and alcohols</h3>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=5" title="Edit section: Addition of water and alcohols">edit</a>]</div> Aqueous solutions of ethylene oxide are rather stable and can exist for a long time without any noticeable chemical reaction. However adding a small amount of acid, such as strongly diluted <a href="/wiki/Sulfuric_acid" title="Sulfuric acid">sulfuric acid</a>, immediately leads to the formation of <a href="/wiki/Ethylene_glycol" title="Ethylene glycol">ethylene glycol</a>, even at room temperature: <dl><dd>(CH2CH2)O + H2O → HO–CH2CH2–OH</dd></dl> The reaction also occurs in the gas phase, in the presence of a <a href="/wiki/Phosphoric_acid" title="Phosphoric acid">phosphoric acid</a> salt as a catalyst.<a href="#cite_note-oe3-33">[33]</a> The reaction is usually carried out at about 60 °C (140 °F) with a large excess of water, in order to prevent the reaction of the formed ethylene glycol with ethylene oxide that would form <a href="/wiki/Diethylene_glycol" title="Diethylene glycol">di-</a> and <a href="/wiki/Triethylene_glycol" title="Triethylene glycol">triethylene glycol</a>:<a href="#cite_note-34">[34]</a> <dl><dd>2 (CH2CH2)O + H2O → HO–CH2CH2–O–CH2CH2–OH</dd> <dd>3 (CH2CH2)O + H2O → HO–CH2CH2–O–CH2CH2–O–CH2CH2–OH</dd></dl> The use of alkaline catalysts may lead to the formation of <a href="/wiki/Polyethylene_glycol" title="Polyethylene glycol">polyethylene glycol</a>: <dl><dd>n (CH2CH2)O + H2O → HO–(–CH2CH2–O–)n–H</dd></dl> Reactions with <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohols</a> proceed similarly yielding ethylene glycol ethers: <dl><dd>(CH2CH2)O + C2H5OH → HO–CH2CH2–OC2H5</dd></dl> <dl><dd>2 (CH2CH2)O + C2H5OH → HO–CH2CH2–O–CH2CH2–OC2H5</dd></dl> Reactions with lower alcohols occur less actively than with water and require more severe conditions, such as heating to 160 °C (320 °F) and pressurizing to 3 MPa (440 psi) and adding an acid or alkali catalyst. Reactions of ethylene oxide with fatty alcohols proceed in the presence of <a href="/wiki/Sodium" title="Sodium">sodium</a> metal, <a href="/wiki/Sodium_hydroxide" title="Sodium hydroxide">sodium hydroxide</a>, or <a href="/wiki/Boron_trifluoride" title="Boron trifluoride">boron trifluoride</a> and are used for the synthesis of <a href="/wiki/Surfactants" class="mw-redirect" title="Surfactants">surfactants</a>.<a href="#cite_note-oe3-33">[33]</a> <div class="mw-heading mw-heading3"><h3 id="Addition_of_carboxylic_acids_and_their_derivatives">Addition of carboxylic acids and their derivatives</h3>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=6" title="Edit section: Addition of carboxylic acids and their derivatives">edit</a>]</div> Reactions of ethylene oxide with <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acids</a> in the presence of a catalyst results in glycol mono- and diesters: <dl><dd>(CH2CH2)O + CH3CO2H → HOCH2CH2–O2CCH3</dd> <dd>(CH2CH2)O + (CH3CO)2O → CH3CO2CH2CH2O2CCH3</dd></dl> The addition of acid <a href="/wiki/Amide" title="Amide">amides</a> proceeds similarly: <dl><dd>(CH2CH2)O + CH3CONH2 → HOCH2CH2NHC(O)CH3</dd></dl> Addition of ethylene oxide to higher carboxylic acids is carried out at elevated temperatures (typically 140–180 °C (284–356 °F)) and pressure (0.3–0.5 MPa (44–73 psi)) in an inert atmosphere, in presence of an alkaline catalyst (concentration 0.01–2%), such as hydroxide or carbonate of sodium or potassium.<a href="#cite_note-35">[35]</a> The carboxylate ion acts as <a href="/wiki/Nucleophile" title="Nucleophile">nucleophile</a> in the reaction: <dl><dd>(CH2CH2)O + RCO2− → RCO2CH2CH2O−</dd> <dd>RCO2CH2CH2O− + RCO2H → RCO2CH2CH2OH + RCO2−</dd></dl> <div class="mw-heading mw-heading3"><h3 id="Adding_ammonia_and_amines">Adding ammonia and amines</h3>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=7" title="Edit section: Adding ammonia and amines">edit</a>]</div> Ethylene oxide reacts with <a href="/wiki/Ammonia" title="Ammonia">ammonia</a> forming a mixture of mono-, di-, and tri- <a href="/wiki/Ethanolamine" title="Ethanolamine">ethanolamines</a>. The reaction is stimulated by adding a small amount of water. <dl><dd>(CH2CH2)O + NH3 → HO–CH2CH2–NH2</dd></dl> <dl><dd>2 (CH2CH2)O + NH3 → (HO–CH2CH2)2NH</dd></dl> <dl><dd>3 (CH2CH2)O + NH3 → (HO–CH2CH2)3N</dd></dl> Similarly proceed the reactions with primary and secondary amines: <dl><dd>(CH2CH2)O + RNH2 → HO–CH2CH2–NHR</dd></dl> Dialkylamino ethanols can further react with ethylene oxide, forming amino polyethylene glycols:<a href="#cite_note-ect-19">[19]</a> <dl><dd>n (CH2CH2)O + R2NCH2CH2OH → R2NCH2CH2O–(–CH2CH2O–)n–H</dd></dl> <a href="/wiki/Trimethylamine" title="Trimethylamine">Trimethylamine</a> reacts with ethylene oxide in the presence of water, forming <a href="/wiki/Choline" title="Choline">choline</a>:<a href="#cite_note-36">[36]</a> <dl><dd>(CH2CH2)O + (CH3)3N + H2O → [HOCH2CH2N (CH3)3]+OH−</dd></dl> Aromatic primary and secondary amines also react with ethylene oxide, forming the corresponding arylamino alcohols. <div class="mw-heading mw-heading3"><h3 id="Halide_addition">Halide addition</h3>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=8" title="Edit section: Halide addition">edit</a>]</div> Ethylene oxide readily reacts with aqueous solutions of <a href="/wiki/Hydrochloric_acid" title="Hydrochloric acid">hydrochloric</a>, <a href="/wiki/Hydrobromic_acid" title="Hydrobromic acid">hydrobromic</a>, and <a href="/wiki/Hydroiodic_acid" title="Hydroiodic acid">hydroiodic acids</a> to form <a href="/wiki/Halohydrin" title="Halohydrin">halohydrins</a>. The reaction occurs easier with the last two acids: <dl><dd>(CH2CH2)O + HCl → HO–CH2CH2–Cl</dd></dl> The reaction with these acids competes with the acid-catalyzed hydration of ethylene oxide; therefore, there is always a by-product of ethylene glycol with an admixture of <a href="/wiki/Diethylene_glycol" title="Diethylene glycol">diethylene glycol</a>. For a cleaner product, the reaction is conducted in the gas phase or in an organic solvent. Ethylene fluorohydrin is obtained differently, by boiling <a href="/wiki/Hydrogen_fluoride" title="Hydrogen fluoride">hydrogen fluoride</a> with a 5–6% solution of ethylene oxide in <a href="/wiki/Diethyl_ether" title="Diethyl ether">diethyl ether</a>. The ether normally has a water content of 1.5–2%; in absence of water, ethylene oxide polymerizes.<a href="#cite_note-37">[37]</a> Halohydrins can also be obtained by passing ethylene oxide through aqueous solutions of metal halides:<a href="#cite_note-oe3-33">[33]</a> <dl><dd>2 (CH2CH2)O + CuCl2 + 2 H2O → 2 HO–CH2CH2–Cl + Cu(OH)2↓</dd></dl> <div class="mw-heading mw-heading3"><h3 id="Metalorganic_addition">Metalorganic addition</h3>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=9" title="Edit section: Metalorganic addition">edit</a>]</div> Interaction of ethylene oxide with <a href="/wiki/Organomagnesium" class="mw-redirect" title="Organomagnesium">organomagnesium</a> compounds, which are <a href="/wiki/Grignard_reaction" title="Grignard reaction">Grignard reagents</a>, can be regarded as <a href="/wiki/Nucleophilic_substitution" title="Nucleophilic substitution">nucleophilic substitution</a> influenced by <a href="/wiki/Carbanion" title="Carbanion">carbanion</a> organometallic compounds. The final product of the reaction is a primary alcohol: <dl><dd><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {(CH2CH2)O{}+RMgBr->R-CH2CH2-OMgBr->[{\ce {H2O}}]{\overset {primary~alcohol}{R-CH2CH2-OH}}}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <mtext>O</mtext> <mrow class="MJX-TeXAtom-ORD"> </mrow> <mo>+</mo> <mtext>RMgBr</mtext> <mo stretchy="false">⟶</mo> <mtext>R</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>OMgBr</mtext> <mrow class="MJX-TeXAtom-REL"> <mover> <mo>→</mo> <mpadded width="+0.611em" lspace="0.278em" voffset=".15em"> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mtext>O</mtext> </mrow> </mpadded> </mover> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mover> <mrow> <mtext>R</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>OH</mtext> </mrow> <mrow> <mtext>primary</mtext> <mtext> </mtext> <mtext>alcohol</mtext> </mrow> </mover> </mrow> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {(CH2CH2)O{}+RMgBr->R-CH2CH2-OMgBr->[{\ce {H2O}}]{\overset {primary~alcohol}{R-CH2CH2-OH}}}}}</annotation> </semantics> </math><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/7c48438564bd8b7fde140b00ad4dfd092cd8f6ce" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:73.788ex; height:4.843ex;" alt="{\displaystyle {\ce {(CH2CH2)O{}+RMgBr->R-CH2CH2-OMgBr->[{\ce {H2O}}]{\overset {primary~alcohol}{R-CH2CH2-OH}}}}}" /></dd></dl> Similar mechanism is valid for other organometallic compounds, such as alkyl lithium: <dl><dd><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {(CH2CH2)O{}+{\overset {alkyl~lithium}{RLi}}->R-CH2CH2-OLi->[{\ce {H2O}}]R-CH2CH2-OH}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <mtext>O</mtext> <mrow class="MJX-TeXAtom-ORD"> </mrow> <mo>+</mo> <mrow class="MJX-TeXAtom-ORD"> <mover> <mtext>RLi</mtext> <mrow> <mtext>alkyl</mtext> <mtext> </mtext> <mtext>lithium</mtext> </mrow> </mover> </mrow> <mo stretchy="false">⟶</mo> <mtext>R</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>OLi</mtext> <mrow class="MJX-TeXAtom-REL"> <mover> <mo>→</mo> <mpadded width="+0.611em" lspace="0.278em" voffset=".15em"> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mtext>O</mtext> </mrow> </mpadded> </mover> </mrow> <mtext>R</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>OH</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {(CH2CH2)O{}+{\overset {alkyl~lithium}{RLi}}->R-CH2CH2-OLi->[{\ce {H2O}}]R-CH2CH2-OH}}}</annotation> </semantics> </math><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/7141d68bc0b387f64be9a5ec8ef6ac288cc78080" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; margin-top: -0.279ex; width:71.737ex; height:4.843ex;" alt="{\displaystyle {\ce {(CH2CH2)O{}+{\overset {alkyl~lithium}{RLi}}->R-CH2CH2-OLi->[{\ce {H2O}}]R-CH2CH2-OH}}}" /></dd></dl> <div class="mw-heading mw-heading3"><h3 id="Other_addition_reactions">Other addition reactions</h3>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=10" title="Edit section: Other addition reactions">edit</a>]</div> <div class="mw-heading mw-heading4"><h4 id="Addition_of_hydrogen_cyanide">Addition of hydrogen cyanide</h4>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=11" title="Edit section: Addition of hydrogen cyanide">edit</a>]</div> Ethylene oxide easily reacts with <a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">hydrogen cyanide</a> forming <a href="/w/index.php?title=Ethylene_cyanohydrin&action=edit&redlink=1" class="new" title="Ethylene cyanohydrin (page does not exist)">ethylene cyanohydrin</a>: <dl><dd>(CH2CH2)O + HCN → HO–CH2CH2–CN</dd></dl> A slightly chilled (10–20 °C) aqueous solution of <a href="/wiki/Calcium_cyanide" title="Calcium cyanide">calcium cyanide</a> can be used instead of HCN:<a href="#cite_note-38">[38]</a> <dl><dd>2 (CH2CH2)O + Ca(CN)2 + 2 H2O → 2 HO–CH2CH2–CN + Ca(OH)2</dd></dl> Ethylene cyanohydrin easily loses water, producing <a href="/wiki/Acrylonitrile" title="Acrylonitrile">acrylonitrile</a>: <dl><dd>HO–CH2CH2–CN → CH2=CH–CN + H2O</dd></dl> <div class="mw-heading mw-heading4"><h4 id="Addition_of_hydrogen_sulfide_and_mercaptans">Addition of hydrogen sulfide and mercaptans</h4>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=12" title="Edit section: Addition of hydrogen sulfide and mercaptans">edit</a>]</div> When reacting with the <a href="/wiki/Hydrogen_sulfide" title="Hydrogen sulfide">hydrogen sulfide</a>, ethylene oxide forms <a href="/wiki/2-Mercaptoethanol" title="2-Mercaptoethanol">2-mercaptoethanol</a> and <a href="/wiki/Thiodiglycol" title="Thiodiglycol">thiodiglycol</a>, and with alkylmercaptans it produces 2-alkyl mercaptoetanol: <dl><dd>(CH2CH2)O + H2S → HO–CH2CH2–HS</dd> <dd>2 (CH2CH2)O + H2S → (HO–CH2CH2)2S</dd> <dd>(CH2CH2)O + RHS → HO–CH2CH2–SR</dd></dl> The excess of ethylene oxide with an aqueous solution of hydrogen sulfide leads to the tris-(hydroxyethyl) sulfonyl hydroxide: <dl><dd>3 (CH2CH2)O + H2S → [(HO–CH2CH2)3S+]OH−</dd></dl> <div class="mw-heading mw-heading4"><h4 id="Addition_of_nitrous_and_nitric_acids">Addition of nitrous and nitric acids</h4>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=13" title="Edit section: Addition of nitrous and nitric acids">edit</a>]</div> Reaction of ethylene oxide with aqueous solutions of <a href="/wiki/Barium_nitrite" title="Barium nitrite">barium nitrite</a>, <a href="/wiki/Calcium_nitrite" title="Calcium nitrite">calcium nitrite</a>, <a href="/w/index.php?title=Magnesium_nitrite&action=edit&redlink=1" class="new" title="Magnesium nitrite (page does not exist)">magnesium nitrite</a>, <a href="/w/index.php?title=Zinc_nitrite&action=edit&redlink=1" class="new" title="Zinc nitrite (page does not exist)">zinc nitrite</a>, or <a href="/wiki/Sodium_nitrite" title="Sodium nitrite">sodium nitrite</a> leads to the formation of <a href="/w/index.php?title=2-nitroethanol&action=edit&redlink=1" class="new" title="2-nitroethanol (page does not exist)">2-nitroethanol</a>:<a href="#cite_note-39">[39]</a> <dl><dd>2 (CH2CH2)O + Ca(NO2)2 + 2 H2O → 2 HO–CH2CH2–NO2 + Ca(OH)2</dd></dl> With <a href="/wiki/Nitric_acid" title="Nitric acid">nitric acid</a>, ethylene oxide forms mono- and <a href="/wiki/Ethylene_glycol_dinitrate" title="Ethylene glycol dinitrate">dinitroglycols</a>:<a href="#cite_note-40">[40]</a> <dl><dd><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {(CH2CH2)O{}+{\overset {nitric \atop acid}{HNO3}}->HO-CH2CH2-ONO2->[{\ce {+HNO3}}][{\ce {-H2O}}]O2NO-CH2CH2-ONO_{2}}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <mtext>O</mtext> <mrow class="MJX-TeXAtom-ORD"> </mrow> <mo>+</mo> <mrow class="MJX-TeXAtom-ORD"> <mover> <msubsup> <mtext>HNO</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mfrac linethickness="0"> <mtext>nitric</mtext> <mtext>acid</mtext> </mfrac> </mover> </mrow> <mo stretchy="false">⟶</mo> <mtext>HO</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <msubsup> <mtext>ONO</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mrow class="MJX-TeXAtom-REL"> <munderover> <mo>→</mo> <mpadded width="+0.611em" lspace="0.278em" voffset="-.24em"> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mtext>O</mtext> </mrow> </mpadded> <mpadded width="+0.611em" lspace="0.278em" voffset=".15em"> <mrow class="MJX-TeXAtom-ORD"> <mo>+</mo> <msubsup> <mtext>HNO</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> </mrow> </mpadded> </munderover> </mrow> <msubsup> <mtext>O</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mtext>NO</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <msubsup> <mtext>ONO</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {(CH2CH2)O{}+{\overset {nitric \atop acid}{HNO3}}->HO-CH2CH2-ONO2->[{\ce {+HNO3}}][{\ce {-H2O}}]O2NO-CH2CH2-ONO_{2}}}}</annotation> </semantics> </math><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/2371038f32a4744baec84d923cabd0010e476b31" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -2.427ex; margin-bottom: -0.577ex; width:83.247ex; height:7.676ex;" alt="{\displaystyle {\ce {(CH2CH2)O{}+{\overset {nitric \atop acid}{HNO3}}->HO-CH2CH2-ONO2->[{\ce {+HNO3}}][{\ce {-H2O}}]O2NO-CH2CH2-ONO_{2}}}}" /></dd></dl> <div class="mw-heading mw-heading4"><h4 id="Reaction_with_compounds_containing_active_methylene_groups">Reaction with compounds containing active methylene groups</h4>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=14" title="Edit section: Reaction with compounds containing active methylene groups">edit</a>]</div> In the presence of <a href="/wiki/Alkoxide" title="Alkoxide">alkoxides</a>, reactions of ethylene oxide with compounds containing active methylene group leads to the formation of <a href="/wiki/Gamma-Butyrolactone" class="mw-redirect" title="Gamma-Butyrolactone">butyrolactones</a>:<a href="#cite_note-41">[41]</a> <dl><dd><a href="/wiki/File:2-ACETYLBUTYROLACTONE-SYNTHESIS.png" class="mw-file-description" title="Synthesis of 2-acetylbutyrolactone"><img alt="Synthesis of 2-acetylbutyrolactone" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/55/2-ACETYLBUTYROLACTONE-SYNTHESIS.png/550px-2-ACETYLBUTYROLACTONE-SYNTHESIS.png" decoding="async" width="550" height="114" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/55/2-ACETYLBUTYROLACTONE-SYNTHESIS.png/825px-2-ACETYLBUTYROLACTONE-SYNTHESIS.png 1.5x, //upload.wikimedia.org/wikipedia/commons/5/55/2-ACETYLBUTYROLACTONE-SYNTHESIS.png 2x" data-file-width="842" data-file-height="175" /></a></dd></dl> <div class="mw-heading mw-heading4"><h4 id="Alkylation_of_aromatic_compounds">Alkylation of aromatic compounds</h4>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=15" title="Edit section: Alkylation of aromatic compounds">edit</a>]</div> Ethylene oxide enters into the <a href="/wiki/Friedel%E2%80%93Crafts_reaction" title="Friedel–Crafts reaction">Friedel–Crafts reaction</a> with benzene to form <a href="/wiki/Phenethyl_alcohol" title="Phenethyl alcohol">phenethyl alcohol</a>: <dl><dd><a href="/wiki/File:Oxirane%2Bbenzene.png" class="mw-file-description" title="Friedel-Crafts reaction with ethylene oxide"><img alt="Friedel-Crafts reaction with ethylene oxide" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c1/Oxirane%2Bbenzene.png/400px-Oxirane%2Bbenzene.png" decoding="async" width="400" height="73" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c1/Oxirane%2Bbenzene.png/600px-Oxirane%2Bbenzene.png 1.5x, //upload.wikimedia.org/wikipedia/commons/c/c1/Oxirane%2Bbenzene.png 2x" data-file-width="714" data-file-height="131" /></a></dd></dl> <a href="/wiki/Styrene" title="Styrene">Styrene</a> can be obtained in one stage if this reaction is conducted at elevated temperatures (315–440 °C (599–824 °F)) and pressures (0.35–0.7 MPa (51–102 psi)), in presence of an aluminosilicate catalyst.<a href="#cite_note-42">[42]</a> <div class="mw-heading mw-heading4"><h4 id="Synthesis_of_crown_ethers">Synthesis of crown ethers</h4>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=16" title="Edit section: Synthesis of crown ethers">edit</a>]</div> A series of polynomial <a href="/wiki/Heterocyclic_compound" title="Heterocyclic compound">heterocyclic compounds</a>, known as <a href="/wiki/Crown_ether" title="Crown ether">crown ethers</a>, can be synthesized with ethylene oxide. One method is the cationic cyclopolymerization of ethylene oxide, limiting the size of the formed cycle:<a href="#cite_note-crown-43">[43]</a> <dl><dd>n (CH2CH2)O → (–CH2CH2–O–)n</dd></dl> To suppress the formation of other linear polymers the reaction is carried out in a highly dilute solution.<a href="#cite_note-crown-43">[43]</a> Reaction of ethylene oxide with <a href="/wiki/Sulfur_dioxide" title="Sulfur dioxide">sulfur dioxide</a> in the presence of caesium salts leads to the formation of an 11-membered heterocyclic compound which has the complexing properties of crown ethers:<a href="#cite_note-autogenerated1-44">[44]</a> <dl><dd><a href="/wiki/File:Tetraoxathia-2-cycloundecanone.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/99/Tetraoxathia-2-cycloundecanone.png/500px-Tetraoxathia-2-cycloundecanone.png" decoding="async" width="350" height="98" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/99/Tetraoxathia-2-cycloundecanone.png/525px-Tetraoxathia-2-cycloundecanone.png 1.5x, //upload.wikimedia.org/wikipedia/commons/9/99/Tetraoxathia-2-cycloundecanone.png 2x" data-file-width="634" data-file-height="178" /></a></dd></dl> <div class="mw-heading mw-heading3"><h3 id="Isomerization">Isomerization</h3>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=17" title="Edit section: Isomerization">edit</a>]</div> When heated to about 400 °C (750 °F), or to 150–300 °C (300–570 °F) in the presence of a catalyst (<a href="/wiki/Aluminium_oxide" title="Aluminium oxide">Al2O3</a>, <a href="/wiki/Phosphoric_acid" title="Phosphoric acid">H3PO4</a>, etc.), ethylene oxide <a href="/wiki/Isomerization" title="Isomerization">isomerizes</a> into <a href="/wiki/Acetaldehyde" title="Acetaldehyde">acetaldehyde</a>:<a href="#cite_note-petrov-45">[45]</a> <dl><dd><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {(CH2CH2)O->[{\ce {200^{\circ }C}}][{\ce {Al2O3}}]{\overset {acetaldehyde}{CH3CHO}}}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <mtext>O</mtext> <mrow class="MJX-TeXAtom-REL"> <munderover> <mo>→</mo> <mpadded width="+0.611em" lspace="0.278em" voffset="-.24em"> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mtext>Al</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>O</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> </mrow> </mpadded> <mpadded width="+0.611em" lspace="0.278em" voffset=".15em"> <mrow class="MJX-TeXAtom-ORD"> <mn>200</mn> <msup> <mspace width="thinmathspace"></mspace> <mrow class="MJX-TeXAtom-ORD"> <mo>∘</mo> </mrow> </msup> <mtext>C</mtext> </mrow> </mpadded> </munderover> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mover> <mrow> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mtext>CHO</mtext> </mrow> <mtext>acetaldehyde</mtext> </mover> </mrow> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {(CH2CH2)O->[{\ce {200^{\circ }C}}][{\ce {Al2O3}}]{\overset {acetaldehyde}{CH3CHO}}}}}</annotation> </semantics> </math><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/200d83d07cf99e53654b630ae258d28935f164ae" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -2.473ex; margin-bottom: -0.531ex; width:29.758ex; height:6.843ex;" alt="{\displaystyle {\ce {(CH2CH2)O->[{\ce {200^{\circ }C}}][{\ce {Al2O3}}]{\overset {acetaldehyde}{CH3CHO}}}}}" /></dd></dl> The radical mechanism was proposed to explain this reaction in the gas phase; it comprises the following stages:<a href="#cite_note-benson-46">[46]</a> <style data-mw-deduplicate="TemplateStyles:r1266403038">.mw-parser-output table.numblk{border-collapse:collapse;border:none;margin-top:0;margin-right:0;margin-bottom:0}.mw-parser-output table.numblk>tbody>tr>td{vertical-align:middle;padding:0}.mw-parser-output table.numblk>tbody>tr>td:nth-child(2){width:99%}.mw-parser-output table.numblk>tbody>tr>td:nth-child(2)>table{border-collapse:collapse;margin:0;border:none;width:100%}.mw-parser-output table.numblk>tbody>tr>td:nth-child(2)>table>tbody>tr:first-child>td:first-child,.mw-parser-output table.numblk>tbody>tr>td:nth-child(2)>table>tbody>tr:first-child>td:last-child{padding:0 0.4ex}.mw-parser-output table.numblk>tbody>tr>td:nth-child(2)>table>tbody>tr:first-child>td:nth-child(2){width:100%;padding:0}.mw-parser-output table.numblk>tbody>tr>td:nth-child(2)>table>tbody>tr:last-child>td{padding:0}.mw-parser-output table.numblk>tbody>tr>td:last-child{font-weight:bold}.mw-parser-output table.numblk.numblk-raw-n>tbody>tr>td:last-child{font-weight:unset}.mw-parser-output table.numblk>tbody>tr>td:last-child::before{content:"("}.mw-parser-output table.numblk>tbody>tr>td:last-child::after{content:")"}.mw-parser-output table.numblk.numblk-raw-n>tbody>tr>td:last-child::before,.mw-parser-output table.numblk.numblk-raw-n>tbody>tr>td:last-child::after{content:none}.mw-parser-output table.numblk>tbody>tr>td{border:none}.mw-parser-output table.numblk.numblk-border>tbody>tr>td{border:thin solid}.mw-parser-output table.numblk>tbody>tr>td:nth-child(2)>table>tbody>tr:first-child>td{border:none}.mw-parser-output table.numblk.numblk-border>tbody>tr>td:nth-child(2)>table>tbody>tr:first-child>td{border:thin solid}.mw-parser-output table.numblk>tbody>tr>td:nth-child(2)>table>tbody>tr:last-child>td{border-left:none;border-right:none;border-bottom:none}.mw-parser-output table.numblk.numblk-border>tbody>tr>td:nth-child(2)>table>tbody>tr:last-child>td{border-left:thin solid;border-right:thin solid;border-bottom:thin solid}.mw-parser-output table.numblk:target{color:var(--color-base,#202122);background-color:#cfe8fd}@media screen{html.skin-theme-clientpref-night .mw-parser-output table.numblk:target{color:var(--color-base,#eaecf0);background-color:#301702}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output table.numblk:target{color:var(--color-base,#eaecf0);background-color:#301702}}</style><table role="presentation" class="numblk" style="margin-left: 1.6em;"><tbody><tr><td class="nowrap">(CH2CH2)O ↔ •CH2CH2O• → CH3CHO*</td> <td></td> <td class="nowrap">1</td></tr></tbody></table> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1266403038" /><table role="presentation" class="numblk" style="margin-left: 1.6em;"><tbody><tr><td class="nowrap">CH3CHO* → CH3• + CHO•</td> <td></td> <td class="nowrap">2</td></tr></tbody></table> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1266403038" /><table role="presentation" class="numblk" style="margin-left: 1.6em;"><tbody><tr><td class="nowrap">CH3CHO* + M → CH3CHO + M*</td> <td></td> <td class="nowrap">3</td></tr></tbody></table> In reaction (<a href="#math_3">3</a>), M refers to the wall of the reaction vessel or to a heterogeneous catalyst. The moiety CH3CHO* represents a short-lived (lifetime of 10−8.5 seconds), activated molecule of acetaldehyde. Its excess energy is about 355.6 kJ/mol, which exceeds by 29.3 kJ/mol the <a href="/wiki/Binding_energy" title="Binding energy">binding energy</a> of the C-C bond in acetaldehyde.<a href="#cite_note-benson-46">[46]</a> In absence of a catalyst, the thermal isomerization of ethylene oxide is never selective and apart from acetaldehyde yields significant amount of by-products (see section <a href="#Thermal_decomposition">Thermal decomposition</a>).<a href="#cite_note-oe2-47">[47]</a> <div class="mw-heading mw-heading3"><h3 id="Reduction_reaction">Reduction reaction</h3>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=18" title="Edit section: Reduction reaction">edit</a>]</div> Ethylene oxide can be hydrogenated into ethanol in the presence of a catalyst, such as <a href="/wiki/Nickel" title="Nickel">nickel</a>, <a href="/wiki/Platinum" title="Platinum">platinum</a>, <a href="/wiki/Palladium" title="Palladium">palladium</a>,<a href="#cite_note-oe2-47">[47]</a> <a href="/wiki/Borane" title="Borane">boranes</a>, <a href="/wiki/Lithium_aluminium_hydride" title="Lithium aluminium hydride">lithium aluminium hydride</a>, and some other <a href="/wiki/Hydride" title="Hydride">hydrides</a>.<a href="#cite_note-reduction-48">[48]</a> <dl><dd><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {(CH2CH2)O{}+H2->[{} \atop {\ce {Ni,Pt,Pd,BH3,LiAlH4}}{\text{ or other hydrides}}][{\ce {80^{\circ }C}}]{\underset {ethanol}{C2H5OH}}}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <mtext>O</mtext> <mrow class="MJX-TeXAtom-ORD"> </mrow> <mo>+</mo> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mrow class="MJX-TeXAtom-REL"> <munderover> <mo>→</mo> <mpadded width="+0.611em" lspace="0.278em" voffset="-.24em"> <mrow class="MJX-TeXAtom-ORD"> <mn>80</mn> <msup> <mspace width="thinmathspace"></mspace> <mrow class="MJX-TeXAtom-ORD"> <mo>∘</mo> </mrow> </msup> <mtext>C</mtext> </mrow> </mpadded> <mpadded width="+0.611em" lspace="0.278em" voffset=".15em"> <mfrac linethickness="0"> <mrow class="MJX-TeXAtom-ORD"> </mrow> <mrow> <mrow class="MJX-TeXAtom-ORD"> <mtext>Ni</mtext> <mo>,</mo> <mtext>Pt</mtext> <mo>,</mo> <mtext>Pd</mtext> <mo>,</mo> <msubsup> <mtext>BH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mo>,</mo> <msubsup> <mtext>LiAlH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>4</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mtext> or other hydrides</mtext> </mrow> </mrow> </mfrac> </mpadded> </munderover> </mrow> <mrow class="MJX-TeXAtom-ORD"> <munder> <mrow> <msubsup> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>5</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mtext>OH</mtext> </mrow> <mtext>ethanol</mtext> </munder> </mrow> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {(CH2CH2)O{}+H2->[{} \atop {\ce {Ni,Pt,Pd,BH3,LiAlH4}}{\text{ or other hydrides}}][{\ce {80^{\circ }C}}]{\underset {ethanol}{C2H5OH}}}}}</annotation> </semantics> </math><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/a842a87705b878acc5bca8ced590191d4a4d4ba6" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -2.838ex; margin-top: -0.418ex; width:54.44ex; height:7.009ex;" alt="{\displaystyle {\ce {(CH2CH2)O{}+H2->[{} \atop {\ce {Ni,Pt,Pd,BH3,LiAlH4}}{\text{ or other hydrides}}][{\ce {80^{\circ }C}}]{\underset {ethanol}{C2H5OH}}}}}" /></dd></dl> Conversely, with some other catalysts, ethylene oxide may be reduced by hydrogen to ethylene with the yield up to 70%. The reduction catalysts include mixtures of zinc dust and <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a>, of lithium aluminium hydride with <a href="/wiki/Titanium_trichloride" class="mw-redirect" title="Titanium trichloride">titanium trichloride</a> (the reducing agent is actually <a href="/wiki/Titanium(II)_chloride" title="Titanium(II) chloride">titanium dichloride</a>, formed by the reaction between LiAlH4 and TiCl3) and of <a href="/wiki/Iron(III)_chloride" title="Iron(III) chloride">iron(III) chloride</a> with <a href="/wiki/Butyllithium" title="Butyllithium">butyllithium</a> in <a href="/wiki/Tetrahydrofuran" title="Tetrahydrofuran">tetrahydrofuran</a>.<a href="#cite_note-reduction-48">[48]</a> <dl><dd><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {(CH2CH2)O{}+H2->[{} \atop {\ce {{Zn}+CH3COOH}}]{\underset {ethylene}{CH2=CH2}}+H2O}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <mtext>O</mtext> <mrow class="MJX-TeXAtom-ORD"> </mrow> <mo>+</mo> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mrow class="MJX-TeXAtom-REL"> <mover> <mo>→</mo> <mpadded width="+0.611em" lspace="0.278em" voffset=".15em"> <mfrac linethickness="0"> <mrow class="MJX-TeXAtom-ORD"> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mtext>Zn</mtext> </mrow> <mo>+</mo> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mtext>COOH</mtext> </mrow> </mfrac> </mpadded> </mover> </mrow> <mrow class="MJX-TeXAtom-ORD"> <munder> <mrow> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo>=</mo> </mrow> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> </mrow> <mtext>ethylene</mtext> </munder> </mrow> <mo>+</mo> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mtext>O</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {(CH2CH2)O{}+H2->[{} \atop {\ce {{Zn}+CH3COOH}}]{\underset {ethylene}{CH2=CH2}}+H2O}}}</annotation> </semantics> </math><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/75380f885abd2d715c695d5fa331d4c79c140286" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -3.005ex; margin-top: -0.433ex; width:48.982ex; height:7.176ex;" alt="{\displaystyle {\ce {(CH2CH2)O{}+H2->[{} \atop {\ce {{Zn}+CH3COOH}}]{\underset {ethylene}{CH2=CH2}}+H2O}}}" /></dd></dl> <div class="mw-heading mw-heading3"><h3 id="Oxidation">Oxidation</h3>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=19" title="Edit section: Oxidation">edit</a>]</div> Ethylene oxide can further be oxidized, depending on the conditions, to <a href="/wiki/Glycolic_acid" title="Glycolic acid">glycolic acid</a> or <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a>: <dl><dd><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {(CH2CH2)O{}+O2->[{\ce {AgNO3}}]{\overset {glycolic\ acid}{HOCH2CO2H}}}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <mtext>O</mtext> <mrow class="MJX-TeXAtom-ORD"> </mrow> <mo>+</mo> <msubsup> <mtext>O</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mrow class="MJX-TeXAtom-REL"> <mover> <mo>→</mo> <mpadded width="+0.611em" lspace="0.278em" voffset=".15em"> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mtext>AgNO</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> </mrow> </mpadded> </mover> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mover> <mrow> <msubsup> <mtext>HOCH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CO</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mtext>H</mtext> </mrow> <mrow> <mtext>glycolic</mtext> <mtext> </mtext> <mtext>acid</mtext> </mrow> </mover> </mrow> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {(CH2CH2)O{}+O2->[{\ce {AgNO3}}]{\overset {glycolic\ acid}{HOCH2CO2H}}}}}</annotation> </semantics> </math><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/03dd0ccebb53c85777b3684cd096d167877bc1a9" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; margin-top: -0.225ex; width:40.592ex; height:4.843ex;" alt="{\displaystyle {\ce {(CH2CH2)O{}+O2->[{\ce {AgNO3}}]{\overset {glycolic\ acid}{HOCH2CO2H}}}}}" /></dd></dl> Deep gas-phase reactor oxidation of ethylene oxide at 800–1,000 K (527–727 °C; 980–1,340 °F) and a pressure of 0.1–1 MPa (15–145 psi) yields a complex mixture of products containing O2, H2, <a href="/wiki/Carbon_monoxide" title="Carbon monoxide">CO</a>, <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">CO2</a>, <a href="/wiki/Methane" title="Methane">CH4</a>, <a href="/wiki/Acetylene" title="Acetylene">C2H2</a>, <a href="/wiki/Ethylene" title="Ethylene">C2H4</a>, <a href="/wiki/Ethane" title="Ethane">C2H6</a>, <a href="/wiki/Propylene" title="Propylene">C3H6</a>, <a href="/wiki/Propane" title="Propane">C3H8</a>, and <a href="/wiki/Acetaldehyde" title="Acetaldehyde">CH3CHO</a>.<a href="#cite_note-49">[49]</a> <div class="mw-heading mw-heading3"><h3 id="Dimerization">Dimerization</h3>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=20" title="Edit section: Dimerization">edit</a>]</div> In the presence of acid catalysts, ethylene oxide dimerizes to afford <a href="/wiki/Dioxane" class="mw-redirect" title="Dioxane">dioxane</a>: <dl><dd><a href="/wiki/File:Dioxane-synthesis.png" class="mw-file-description" title="Synthesis of dioxane"><img alt="Synthesis of dioxane" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/05/Dioxane-synthesis.png/250px-Dioxane-synthesis.png" decoding="async" width="250" height="70" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/05/Dioxane-synthesis.png/500px-Dioxane-synthesis.png 1.5x" data-file-width="512" data-file-height="144" /></a></dd></dl> The reaction mechanism is as follows:<a href="#cite_note-oe2-47">[47]</a> <dl><dd><a href="/wiki/File:Dioxan-HerstellungCZ.png" class="mw-file-description" title="Mechanism of dimerization"><img alt="Mechanism of dimerization" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Dioxan-HerstellungCZ.png/960px-Dioxan-HerstellungCZ.png" decoding="async" width="650" height="266" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Dioxan-HerstellungCZ.png/975px-Dioxan-HerstellungCZ.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Dioxan-HerstellungCZ.png/1300px-Dioxan-HerstellungCZ.png 2x" data-file-width="5461" data-file-height="2238" /></a></dd></dl> The dimerization reaction is unselective. By-products include <a href="/wiki/Acetaldehyde" title="Acetaldehyde">acetaldehyde</a> (due to <a href="#Isomerization">isomerization</a>). The selectivity and speed of dimerization can be increased by adding a catalyst, such as platinum, platinum-palladium, or <a href="/wiki/Iodine" title="Iodine">iodine</a> with <a href="/wiki/Sulfolane" title="Sulfolane">sulfolane</a>. 2-methyl-1,3-<a href="/wiki/Dioxolane" title="Dioxolane">dioxolane</a> is formed as a side product in the last case.<a href="#cite_note-50">[50]</a> <div class="mw-heading mw-heading3"><h3 id="Polymerization">Polymerization</h3>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=21" title="Edit section: Polymerization">edit</a>]</div> Liquid ethylene oxide can form <a href="/wiki/Polyethylene_glycol" title="Polyethylene glycol">polyethylene glycols</a>. The polymerization can proceed via radical and ionic mechanisms, but only the latter has a wide practical application.<a href="#cite_note-glycol-51">[51]</a> <a href="/wiki/Cationic_polymerization" title="Cationic polymerization">Cationic polymerization</a> of ethylene oxide is assisted by <a href="/wiki/Protic" class="mw-redirect" title="Protic">protic</a> acids (<a href="/wiki/Perchloric_acid" title="Perchloric acid">HClO4</a>, <a href="/wiki/Hydrochloric_acid" title="Hydrochloric acid">HCl</a>), Lewis acids (<a href="/wiki/Tin(IV)_chloride" title="Tin(IV) chloride">SnCl4</a>, <a href="/wiki/Boron_trifluoride" title="Boron trifluoride">BF3</a>, etc.), <a href="/wiki/Organometallic_compound" class="mw-redirect" title="Organometallic compound">organometallic compounds</a>, or more complex reagents:<a href="#cite_note-glycol-51">[51]</a> <dl><dd><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle n{\ce {(CH2CH2)O ->[{\ce {SnCl4}}]}}\ \overbrace {{\ce {(CH2CH2-O-)}}_{n}} ^{{\ce {polyethyleneglycol}}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mi>n</mi> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <mtext>O</mtext> <mrow class="MJX-TeXAtom-REL"> <mover> <mo>→</mo> <mpadded width="+0.611em" lspace="0.278em" voffset=".15em"> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mtext>SnCl</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>4</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> </mrow> </mpadded> </mover> </mrow> </mrow> <mtext> </mtext> <mover> <mrow class="MJX-TeXAtom-OP MJX-fixedlimits"> <mover> <msub> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>O</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mo stretchy="false">)</mo> </mrow> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mi>n</mi> </mrow> </msub> <mo>⏞</mo> </mover> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mtext>polyethyleneglycol</mtext> </mrow> </mrow> </mover> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle n{\ce {(CH2CH2)O ->[{\ce {SnCl4}}]}}\ \overbrace {{\ce {(CH2CH2-O-)}}_{n}} ^{{\ce {polyethyleneglycol}}}}</annotation> </semantics> </math><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/c8bba2c593a453d067fd3451b740268bbdcfade3" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; margin-right: -0.028ex; width:38.247ex; height:6.509ex;" alt="{\displaystyle n{\ce {(CH2CH2)O ->[{\ce {SnCl4}}]}}\ \overbrace {{\ce {(CH2CH2-O-)}}_{n}} ^{{\ce {polyethyleneglycol}}}}" /></dd></dl> The reaction mechanism is as follows.<a href="#cite_note-poly-52">[52]</a> At the first stage, the catalyst (MXm) is initiated by alkyl-or acylhalogen or by compounds with active hydrogen atoms, usually water, alcohol, or glycol: <dl><dd>MXm + ROH → MXmRO−H+</dd></dl> The resulting active complex reacts with ethylene oxide via the SN2 mechanism: <dl><dd>(CH2CH2)O + MXmRO−H+ → (CH2CH2)O•••H+O−RMXm</dd> <dd>(CH2CH2)O•••H+ O−RMXm → HO–CH2CH2+ + MXmRO−2</dd></dl> <dl><dd>HO–CH2CH2+ + n (CH2CH2)O → HO–CH2CH2–(O–CH2CH2)n+</dd></dl> The chain breaks as <dl><dd>HO–CH2CH2–(O–CH2CH2)n+ + MXmRO− → HO–CH2CH2–(O–CH2CH2)n–OR + MXm</dd></dl> <dl><dd>H(O–CH2CH2)n–O–CH2–CH2+ + MXmRO− → H(O–CH2CH2)n–O–CH=CH2 + MXm + ROH</dd></dl> <a href="/wiki/Anionic_polymerization" class="mw-redirect" title="Anionic polymerization">Anionic polymerization</a> of ethylene oxide is assisted by bases, such as <a href="/wiki/Alkoxide" title="Alkoxide">alkoxides</a>, <a href="/wiki/Hydroxide" title="Hydroxide">hydroxides</a>, <a href="/wiki/Carbonate" title="Carbonate">carbonates</a>, or other compounds of alkali or <a href="/wiki/Alkaline_earth_metal" title="Alkaline earth metal">alkaline earth metals</a>.<a href="#cite_note-glycol-51">[51]</a> The reaction mechanism is as follows:<a href="#cite_note-poly-52">[52]</a> <dl><dd>(CH2CH2)O + RONa → RO–CH2CH2–O−Na+</dd></dl> <dl><dd>RO–CH2CH2–O−Na+ + n (CH2CH2)O → RO–(CH2CH2–O)n–CH2CH2–O−Na+</dd></dl> <dl><dd>RO–(CH2CH2–O)n–CH2CH2–O−Na+ → RO–(CH2CH2–O)n–CH=CH2 + NaOH</dd></dl> <dl><dd>RO–(CH2CH2–O)n–CH2CH2–O−Na+ + H2O → RO–(CH2CH2–O)(n+1)OH + NaOH</dd></dl> <div class="mw-heading mw-heading3"><h3 id="Thermal_decomposition">Thermal decomposition</h3>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=22" title="Edit section: Thermal decomposition">edit</a>]</div> Ethylene oxide is relatively stable to heating – in the absence of a catalyst, it does not dissociate up to 300 °C (572 °F), and only above 570 °C (1,058 °F) there is a major <a href="/wiki/Exothermic" class="mw-redirect" title="Exothermic">exothermic</a> decomposition, which proceeds through the radical mechanism.<a href="#cite_note-oe2-47">[47]</a> The first stage involves <a href="#Isomerization">isomerization</a>, however high temperature accelerates the radical processes. They result in a gas mixture containing acetaldehyde, ethane, ethyl, methane, hydrogen, carbon dioxide, <a href="/wiki/Ketene" title="Ketene">ketene</a>, and <a href="/wiki/Formaldehyde" title="Formaldehyde">formaldehyde</a>.<a href="#cite_note-53">[53]</a> High-temperature <a href="/wiki/Pyrolysis" title="Pyrolysis">pyrolysis</a> (830–1,200 K (557–927 °C; 1,034–1,700 °F)) at elevated pressure in an inert atmosphere leads to a more complex composition of the gas mixture, which also contains <a href="/wiki/Acetylene" title="Acetylene">acetylene</a> and <a href="/wiki/Propane" title="Propane">propane</a>.<a href="#cite_note-Lifshitz-54">[54]</a> Contrary to the isomerization, initiation of the chain occurs mainly as follows:<a href="#cite_note-Lifshitz-54">[54]</a> <dl><dd>(CH2CH2)O → •CH2CH2O• → CH2O + CH2:</dd></dl> When carrying the thermal decomposition of ethylene oxide in the presence of transition metal compounds as catalysts, it is possible not only to reduce its temperature, but also to have <a href="/wiki/Ethyl_group" title="Ethyl group">ethyl</a> as the main product, that is to reverse the ethylene oxide synthesis reaction. <div class="mw-heading mw-heading3"><h3 id="Other_reactions">Other reactions</h3>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=23" title="Edit section: Other reactions">edit</a>]</div> <a href="/wiki/Thiocyanate" title="Thiocyanate">Thiocyanate</a> ions or <a href="/wiki/Thiourea" title="Thiourea">thiourea</a> transform ethylene oxide into <a href="/wiki/Thiirane" title="Thiirane">thiirane</a> (ethylene sulfide):<a href="#cite_note-55">[55]</a> <dl><dd>(CH2CH2)O + (NH2)2C=S → (CH2CH2)S + (NH2)2C=O</dd> <dd><a href="/wiki/File:Thiirane-synthesis.png" class="mw-file-description" title="mechanism synthesis thiiranes of ethylene oxide under the influence of thiocyanate ion"><img alt="mechanism synthesis thiiranes of ethylene oxide under the influence of thiocyanate ion" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fe/Thiirane-synthesis.png/550px-Thiirane-synthesis.png" decoding="async" width="550" height="254" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/f/fe/Thiirane-synthesis.png 1.5x" data-file-width="815" data-file-height="377" /></a></dd></dl> Reaction of <a href="/wiki/Phosphorus_pentachloride" title="Phosphorus pentachloride">phosphorus pentachloride</a> with ethylene oxide produces <a href="/wiki/Ethylene_dichloride" class="mw-redirect" title="Ethylene dichloride">ethylene dichloride</a>:<a href="#cite_note-oe3-33">[33]</a> <dl><dd>(CH2CH2)O + PCl5 → Cl–CH2CH2–Cl + POCl3</dd></dl> Other dichloro derivatives of ethylene oxide can be obtained by combined action of <a href="/wiki/Sulfuryl_chloride" title="Sulfuryl chloride">sulfuryl chloride</a> (SOCl2) and <a href="/wiki/Pyridine" title="Pyridine">pyridine</a> and of <a href="/wiki/Triphenylphosphine" title="Triphenylphosphine">triphenylphosphine</a> and <a href="/wiki/Carbon_tetrachloride" title="Carbon tetrachloride">carbon tetrachloride</a>.<a href="#cite_note-march2-56">[56]</a> <a href="/wiki/Phosphorus_trichloride" title="Phosphorus trichloride">Phosphorus trichloride</a> reacts with ethylene oxide forming chloroethyl esters of phosphorous acid:<a href="#cite_note-oe3-33">[33]</a> <dl><dd>(CH2CH2)O + PCl3 → Cl–CH2CH2–OPCl2</dd></dl> <dl><dd>2 (CH2CH2)O + PCl3 → (Cl–CH2CH2–O)2PCl</dd></dl> <dl><dd>3 (CH2CH2)O + PCl3 → Cl–CH2CH2–O)3P</dd></dl> The reaction product of ethylene oxide with <a href="/wiki/Acyl_chloride" title="Acyl chloride">acyl chlorides</a> in the presence of <a href="/wiki/Sodium_iodide" title="Sodium iodide">sodium iodide</a> is a complex iodoethyl ester:<a href="#cite_note-march2-56">[56]</a> <dl><dd>(CH2CH2)O + RCOCl + NaI → RC(O)–OCH2CH2–I + NaCl</dd></dl> Heating ethylene oxide to 100 °C with <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a>, in a non-polar solvent in the presence of bis-(triphenylphosphine)-nickel(0) results in <a href="/wiki/Ethylene_carbonate" title="Ethylene carbonate">ethylene carbonate</a>:<a href="#cite_note-57">[57]</a> <dl><dd><a href="/wiki/File:Ethylene-carbonate-syn.png" class="mw-file-description" title="Synthesis of ethylene carbonate"><img alt="Synthesis of ethylene carbonate" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b2/Ethylene-carbonate-syn.png/380px-Ethylene-carbonate-syn.png" decoding="async" width="380" height="83" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b2/Ethylene-carbonate-syn.png/570px-Ethylene-carbonate-syn.png 1.5x, //upload.wikimedia.org/wikipedia/commons/b/b2/Ethylene-carbonate-syn.png 2x" data-file-width="709" data-file-height="154" /></a></dd></dl> In industry, a similar reaction is carried out at high pressure and temperature in the presence of quaternary ammonium or phosphonium salts as a catalyst.<a href="#cite_note-58">[58]</a> Reaction of ethylene oxide with <a href="/wiki/Formaldehyde" title="Formaldehyde">formaldehyde</a> at 80–150 °C in the presence of a catalyst leads to the formation of <a href="/wiki/Dioxolane" title="Dioxolane">1,3-dioxolane</a>:<a href="#cite_note-fiser-59">[59]</a> <dl><dd><a href="/wiki/File:Dioxolane.png" class="mw-file-description" title="Synthesis of 1,3-dioxolane"><img alt="Synthesis of 1,3-dioxolane" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c4/Dioxolane.png/330px-Dioxolane.png" decoding="async" width="330" height="85" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c4/Dioxolane.png/495px-Dioxolane.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c4/Dioxolane.png/660px-Dioxolane.png 2x" data-file-width="663" data-file-height="170" /></a></dd></dl> Substituting formaldehyde by other aldehydes or ketones results in a 2-substituted 1,3-dioxolane (yield: 70–85%, catalyst: tetraethylammonium bromide).<a href="#cite_note-fiser-59">[59]</a> Catalytic <a href="/wiki/Hydroformylation" title="Hydroformylation">hydroformylation</a> of ethylene oxide gives hydroxypropanal which can be hydrogenated to <a href="/wiki/Propane-1,3-diol" class="mw-redirect" title="Propane-1,3-diol">propane-1,3-diol</a>:<a href="#cite_note-60">[60]</a> <dl><dd><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {(CH2CH2)O + CO + H2 -> CHO-CH2CH2-OH ->[{\ce {+H2}}] HO-CH2CH2CH2-OH}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <mtext>O</mtext> <mo>+</mo> <mtext>CO</mtext> <mo>+</mo> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mo stretchy="false">⟶</mo> <mtext>CHO</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>OH</mtext> <mrow class="MJX-TeXAtom-REL"> <mover> <mo>→</mo> <mpadded width="+0.611em" lspace="0.278em" voffset=".15em"> <mrow class="MJX-TeXAtom-ORD"> <mo>+</mo> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> </mrow> </mpadded> </mover> </mrow> <mtext>HO</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>OH</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {(CH2CH2)O + CO + H2 -> CHO-CH2CH2-OH ->[{\ce {+H2}}] HO-CH2CH2CH2-OH}}}</annotation> </semantics> </math><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/05c6cde688a68ef90108f9182bc519513f78e6b5" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; margin-top: -0.415ex; width:81.078ex; height:4.843ex;" alt="{\displaystyle {\ce {(CH2CH2)O + CO + H2 -> CHO-CH2CH2-OH ->[{\ce {+H2}}] HO-CH2CH2CH2-OH}}}" /></dd></dl> <div class="mw-heading mw-heading2"><h2 id="Laboratory_synthesis">Laboratory synthesis</h2>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=24" title="Edit section: Laboratory synthesis">edit</a>]</div> <div class="mw-heading mw-heading3"><h3 id="Dehydrochlorination_of_ethylene_and_its_derivatives">Dehydrochlorination of ethylene and its derivatives</h3>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=25" title="Edit section: Dehydrochlorination of ethylene and its derivatives">edit</a>]</div> Dehydrochlorination of <a href="/wiki/2-chloroethanol" class="mw-redirect" title="2-chloroethanol">2-chloroethanol</a>, developed by Wurtz in 1859, remains a common laboratory route to ethylene oxide: <dl><dd><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {Cl-CH2CH2-OH + NaOH -> (CH2CH2)O + NaCl + H2O}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mtext>Cl</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>OH</mtext> <mo>+</mo> <mtext>NaOH</mtext> <mo stretchy="false">⟶</mo> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <mtext>O</mtext> <mo>+</mo> <mtext>NaCl</mtext> <mo>+</mo> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mtext>O</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {Cl-CH2CH2-OH + NaOH -> (CH2CH2)O + NaCl + H2O}}}</annotation> </semantics> </math><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/130651bfa2ece3d2514287f4f644c21461806a03" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:60.921ex; height:3.009ex;" alt="{\displaystyle {\ce {Cl-CH2CH2-OH + NaOH -> (CH2CH2)O + NaCl + H2O}}}" /></dd></dl> The reaction is carried out at elevated temperature, and beside <a href="/wiki/Sodium_hydroxide" title="Sodium hydroxide">sodium hydroxide</a> or <a href="/wiki/Potassium_hydroxide" title="Potassium hydroxide">potassium hydroxide</a>, <a href="/wiki/Calcium_hydroxide" title="Calcium hydroxide">calcium hydroxide</a>, <a href="/wiki/Barium_hydroxide" title="Barium hydroxide">barium hydroxide</a>, <a href="/wiki/Magnesium_hydroxide" title="Magnesium hydroxide">magnesium hydroxide</a>, or <a href="/wiki/Carbonate" title="Carbonate">carbonates</a> of alkali or alkaline earth metals can be used.<a href="#cite_note-oe5-61">[61]</a> With a high yield (90%) ethylene oxide can be produced by treating <a href="/wiki/Calcium_oxide" title="Calcium oxide">calcium oxide</a> with ethyl hypochlorite; substituting calcium by other alkaline earth metals reduces the reaction yield:<a href="#cite_note-oeII-62">[62]</a> <dl><dd><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {2 CH3CH2-OCl + CaO -> 2 (CH2CH2)O + CaCl2 + H2O}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> <mspace width="thinmathspace"></mspace> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>OCl</mtext> <mo>+</mo> <mtext>CaO</mtext> <mo stretchy="false">⟶</mo> <mn>2</mn> <mspace width="thinmathspace"></mspace> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <mtext>O</mtext> <mo>+</mo> <msubsup> <mtext>CaCl</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mo>+</mo> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mtext>O</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {2 CH3CH2-OCl + CaO -> 2 (CH2CH2)O + CaCl2 + H2O}}}</annotation> </semantics> </math><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/a0be175b17e9ab21ccb419a36c720cd2f70ae911" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:59.65ex; height:3.009ex;" alt="{\displaystyle {\ce {2 CH3CH2-OCl + CaO -> 2 (CH2CH2)O + CaCl2 + H2O}}}" /></dd></dl> <div class="mw-heading mw-heading3"><h3 id="Direct_oxidation_of_ethylene_by_peroxy_acids">Direct oxidation of ethylene by peroxy acids</h3>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=26" title="Edit section: Direct oxidation of ethylene by peroxy acids">edit</a>]</div> Ethylene can be directly oxidized into ethylene oxide using <a href="/wiki/Peroxy_acid" title="Peroxy acid">peroxy acids</a>, for example, <a href="/wiki/Peroxybenzoic_acid" title="Peroxybenzoic acid">peroxybenzoic</a> or meta-chloro-peroxybenzoic acid:<a href="#cite_note-63">[63]</a> <dl><dd><a href="/wiki/File:Epoxides-synthesis.png" class="mw-file-description" title="Oxidation of ethylene by peroxy acids"><img alt="Oxidation of ethylene by peroxy acids" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4d/Epoxides-synthesis.png/500px-Epoxides-synthesis.png" decoding="async" width="500" height="87" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4d/Epoxides-synthesis.png/750px-Epoxides-synthesis.png 1.5x, //upload.wikimedia.org/wikipedia/commons/4/4d/Epoxides-synthesis.png 2x" data-file-width="814" data-file-height="141" /></a></dd></dl> Oxidation by peroxy acids is efficient for higher alkenes, but not for ethylene. The above reaction is slow and has low yield, therefore it is not used in the industry.<a href="#cite_note-oeII-62">[62]</a> <div class="mw-heading mw-heading3"><h3 id="Other_preparative_methods">Other preparative methods</h3>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=27" title="Edit section: Other preparative methods">edit</a>]</div> Other synthesis methods include<a href="#cite_note-oeII-62">[62]</a> reaction of diiodo ethane with <a href="/wiki/Silver_oxide" title="Silver oxide">silver oxide</a>: <dl><dd><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {I-CH2CH2-I + Ag2O -> (CH2CH2)O + 2AgI}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mtext>I</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>I</mtext> <mo>+</mo> <msubsup> <mtext>Ag</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mtext>O</mtext> <mo stretchy="false">⟶</mo> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <mtext>O</mtext> <mo>+</mo> <mn>2</mn> <mspace width="thinmathspace"></mspace> <mtext>AgI</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {I-CH2CH2-I + Ag2O -> (CH2CH2)O + 2AgI}}}</annotation> </semantics> </math><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/47ed75eddf10afeddf586e6971d4b3d00de63a08" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:48.654ex; height:3.009ex;" alt="{\displaystyle {\ce {I-CH2CH2-I + Ag2O -> (CH2CH2)O + 2AgI}}}" /></dd></dl> and decomposition of <a href="/wiki/Ethylene_carbonate" title="Ethylene carbonate">ethylene carbonate</a> at 200–210 °C (392–410 °F) in the presence of <a href="/wiki/Hexachloroethane" title="Hexachloroethane">hexachloroethane</a>: <dl><dd><a href="/wiki/File:Ethylenecarbonate-decomposition.png" class="mw-file-description" title="Decomposition of ethylene carbonate"><img alt="Decomposition of ethylene carbonate" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f0/Ethylenecarbonate-decomposition.png/500px-Ethylenecarbonate-decomposition.png" decoding="async" width="350" height="92" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f0/Ethylenecarbonate-decomposition.png/525px-Ethylenecarbonate-decomposition.png 1.5x, //upload.wikimedia.org/wikipedia/commons/f/f0/Ethylenecarbonate-decomposition.png 2x" data-file-width="558" data-file-height="146" /></a></dd></dl> <div class="mw-heading mw-heading2"><h2 id="Industrial_synthesis">Industrial synthesis</h2>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=28" title="Edit section: Industrial synthesis">edit</a>]</div> <div class="mw-heading mw-heading3"><h3 id="History_2">History</h3>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=29" title="Edit section: History">edit</a>]</div> Commercial production of ethylene oxide dates back to 1914 when <a href="/wiki/BASF" title="BASF">BASF</a> built the first factory which used the chlorohydrin process (reaction of ethylene chlorohydrin with calcium hydroxide). The chlorohydrin process was unattractive for several reasons, including low efficiency and loss of valuable chlorine into <a href="/wiki/Calcium_chloride" title="Calcium chloride">calcium chloride</a>.<a href="#cite_note-64">[64]</a> More efficient direct oxidation of ethylene by air was invented by Lefort in 1931 and in 1937 <a href="/wiki/Union_Carbide" title="Union Carbide">Union Carbide</a> opened the first plant using this process. It was further improved in 1958 by Shell Oil Co. by replacing air with oxygen and using elevated temperature of 200–300 °C (390–570 °F) and pressure (1–3 MPa (150–440 psi)).<a href="#cite_note-industrial-65">[65]</a> This more efficient route accounted for about half of ethylene oxide production in the 1950s in the US, and after 1975 it completely replaced the previous methods.<a href="#cite_note-industrial-65">[65]</a> The production of ethylene oxide accounts for approximately 11% of worldwide ethylene demand.<a href="#cite_note-66">[66]</a> <div class="mw-heading mw-heading3"><h3 id="Chlorohydrin_process_of_production_of_ethylene_oxide">Chlorohydrin process of production of ethylene oxide</h3>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=30" title="Edit section: Chlorohydrin process of production of ethylene oxide">edit</a>]</div> Although the chlorohydrin process is almost entirely superseded in the industry by the direct oxidation of ethylene, the knowledge of this method is still important for educational reasons and because it is still used in the production of <a href="/wiki/Propylene_oxide" title="Propylene oxide">propylene oxide</a>.<a href="#cite_note-67">[67]</a> The process consists of three major steps: synthesis of ethylene chlorohydrin, dehydrochlorination of ethylene chlorohydrin to ethylene oxide and purification of ethylene oxide. Those steps are carried continuously. In the first column, hypochlorination of ethylene is carried out as follows:<a href="#cite_note-uk-68">[68]</a> <dl><dd>Cl2 + H2O → HOCl + HCl</dd></dl> <dl><dd>CH2=CH2 + HOCl → HO–CH2CH2–Cl</dd></dl> <dl><dd>CH2=CH2 + Cl2 → Cl–CH2CH2–Cl</dd></dl> To suppress the conversion of ethylene into the <a href="/wiki/Ethylene_dichloride" class="mw-redirect" title="Ethylene dichloride">ethylene dichloride</a> (the last reaction), the concentration of ethylene is maintained at about 4–6%, and the solution is heated by steam to the boiling point.<a href="#cite_note-uk-68">[68]</a> Next, aqueous solution of ethylene chlorohydrin enters the second column, where it reacts with a 30% solution of calcium hydroxide at 100 °C (212 °F):<a href="#cite_note-uk-68">[68]</a> <dl><dd>2 HO–CH2CH2–Cl + Ca(OH)2 → 2 (CH2CH2)O + CaCl2 + 2H2O</dd></dl> The produced ethylene oxide is purified by <a href="/wiki/Rectified_spirit" title="Rectified spirit">rectification</a>. The chlorohydrin process allows to reach 95% conversion of ethylene chlorohydrin. The yield of ethylene oxide is about 80% of the theoretical value; for 1 tonne (0.98 long tons; 1.1 short tons) of ethylene oxide, about 200 kg (440 lb) of ethylene dichloride is produced.<a href="#cite_note-uk-68">[68]</a> But, the major drawbacks of this process are high chlorine consumption and effluent load. This process is now obsolete. <div class="mw-heading mw-heading3"><h3 id="Direct_oxidation_of_ethylene">Direct oxidation of ethylene</h3>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=31" title="Edit section: Direct oxidation of ethylene">edit</a>]</div> <div class="mw-heading mw-heading4"><h4 id="Usage_in_global_industry">Usage in global industry</h4>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=32" title="Edit section: Usage in global industry">edit</a>]</div> Direct oxidation of ethylene was patented by Lefort in 1931. This method was repeatedly modified for industrial use, and at least four major variations are known. They all use oxidation by oxygen or air and a silver-based catalyst, but differ in the technological details and hardware implementations.<a href="#cite_note-eos-69">[69]</a> <a href="/wiki/Union_Carbide" title="Union Carbide">Union Carbide</a> (currently a division of <a href="/wiki/Dow_Chemical_Company" title="Dow Chemical Company">Dow Chemical Company</a>) was the first company to develop the direct oxidation process.<a href="#cite_note-cmpa-70">[70]</a> A similar production method was developed by Scientific Design Co., but it received wider use because of the licensing system – it accounts for 25% of the world's production and for 75% of world's licensed production of ethylene oxide.<a href="#cite_note-cmpa-70">[70]</a><a href="#cite_note-71">[71]</a> A proprietary variation of this method is used by Japan Catalytic Chemical Co., which adapted synthesis of both ethylene oxide and ethylene glycol in a single industrial complex. A different modification was developed Shell International Chemicals BV. Their method is rather flexible with regard to the specific requirements of specific industries; it is characterized by high selectivity with respect to the ethylene oxide product and long lifetime of the catalyst (3 years). It accounts for about 40% of global production.<a href="#cite_note-cmpa-70">[70]</a> Older factories typically use air for oxidation whereas newer plants and processes, such as METEOR and Japan Catalytic, favor oxygen.<a href="#cite_note-72">[72]</a> <div class="mw-heading mw-heading4"><h4 id="Chemistry_and_kinetics_of_the_direct_oxidation_process">Chemistry and kinetics of the direct oxidation process</h4>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=33" title="Edit section: Chemistry and kinetics of the direct oxidation process">edit</a>]</div> Formally, the direct oxidation process is expressed by the following equation: <dl><dd><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {2CH_2=CH2 + O2 ->[{\ce {Ag}}] 2(CH2CH2)O}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> <mspace width="thinmathspace"></mspace> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo>=</mo> </mrow> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mo>+</mo> <msubsup> <mtext>O</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mrow class="MJX-TeXAtom-REL"> <mover> <mo>→</mo> <mpadded width="+0.611em" lspace="0.278em" voffset=".15em"> <mrow class="MJX-TeXAtom-ORD"> <mtext>Ag</mtext> </mrow> </mpadded> </mover> </mrow> <mn>2</mn> <mspace width="thinmathspace"></mspace> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <mtext>O</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {2CH_2=CH2 + O2 ->[{\ce {Ag}}] 2(CH2CH2)O}}}</annotation> </semantics> </math><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/3fde14a6cc111cfdc46c6324e44a305aae14f8ce" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; margin-top: -0.308ex; width:36.798ex; height:4.509ex;" alt="{\displaystyle {\ce {2CH_2=CH2 + O2 ->[{\ce {Ag}}] 2(CH2CH2)O}}}" />, ΔH=−105 kJ/mol</dd></dl> However, significant yield of carbon dioxide and water is observed in practice, which can be explained by the complete oxidation of ethylene or ethylene oxide: <dl><dd>CH2=CH2 + 3 O2 → 2 CO2 + 2 H2O, ΔH=−1327 kJ/mol</dd> <dd>(CH2CH2)O + 2.5 O2 → 2 CO2 + 2 H2O, ΔH=−1223 kJ/mol</dd></dl> According to a kinetic analysis by Kilty and Sachtler, the following reactions describe the pathway leading to EO. In the first step, a <a href="/wiki/Superoxide" title="Superoxide">superoxide</a> (O2−) species is formed:<a href="#cite_note-kilty-73">[73]</a> <dl><dd>O2 + Ag → Ag+O2−</dd></dl> This species reacts with ethylene <dl><dd>Ag+O2− + H2C=CH2 → (CH2CH2)O + AgO</dd></dl> The resulting silver oxide then oxidizes ethylene or ethylene oxide to CO2 and water. This reaction replenishes the silver catalyst. Thus the overall reaction is expressed as <dl><dd>7 CH2=CH2 + 6 O2 → 6 (CH2CH2)O + 2 CO2 + 2 H2O</dd></dl> and the maximum degree of conversion of ethylene to ethylene oxide is theoretically predicted to be 6/7 or 85.7%,<a href="#cite_note-kilty-73">[73]</a> although higher yields are achieved in practice.<a href="#cite_note-74">[74]</a> The catalyst for the reaction is metallic silver deposited on various matrixes, including <a href="/wiki/Pumice" title="Pumice">pumice</a>, <a href="/wiki/Silica_gel" title="Silica gel">silica gel</a>, various <a href="/wiki/Silicate" title="Silicate">silicates</a> and <a href="/wiki/Aluminosilicate" title="Aluminosilicate">aluminosilicates</a>, <a href="/wiki/Alumina" class="mw-redirect" title="Alumina">alumina</a>, and <a href="/wiki/Silicon_carbide" title="Silicon carbide">silicon carbide</a>, and activated by certain additives (<a href="/wiki/Antimony" title="Antimony">antimony</a>, <a href="/wiki/Bismuth" title="Bismuth">bismuth</a>, <a href="/wiki/Barium_peroxide" title="Barium peroxide">barium peroxide</a>, etc.).<a href="#cite_note-lebedev-75">[75]</a> The process temperature was optimized as 220–280 °C (430–540 °F). Lower temperatures reduce the activity of the catalyst, and higher temperatures promote the complete oxidation of ethylene thereby reducing the yield of ethylene oxide. Elevated pressure of 1–3 MPa (150–440 psi) increases the productivity of the catalyst and facilitates absorption of ethylene oxide from the reacting gases.<a href="#cite_note-lebedev-75">[75]</a> Whereas oxidation by air is still being used, oxygen (> 95% purity) is preferred for several reasons, such as higher molar yield of ethylene oxide (75–82% for oxygen vs. 63–75% for air), higher reaction rate (no gas dilution) and no need of separating nitrogen in the reaction products.<a href="#cite_note-ect-19">[19]</a><a href="#cite_note-76">[76]</a> <div class="mw-heading mw-heading3"><h3 id="Process_overview">Process overview</h3>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=34" title="Edit section: Process overview">edit</a>]</div> The production of ethylene oxide on a commercial scale is attained with the unification of the following <a href="/wiki/Unit_operations" class="mw-redirect" title="Unit operations">unit processes</a>: <ul><li>Main reactor</li> <li>Ethylene oxide <a href="/wiki/Scrubber" title="Scrubber">scrubber</a></li> <li>Ethylene oxide de-sorber</li> <li><a href="/wiki/Stripping_(chemistry)" title="Stripping (chemistry)">Stripping</a> and <a href="/wiki/Distillation_column" class="mw-redirect" title="Distillation column">distillation column</a></li> <li>CO2 scrubber and CO2 de-scrubber</li></ul> Main Reactor: The main reactor consists of thousands of catalyst tubes in bundles. These tubes are generally 6 to 15 m (20 to 50 ft) long with an inner diameter of 20 to 50 mm (0.8 to 2.0 in). The catalyst packed in these tubes is in the form of spheres or rings of diameter 3 to 10 mm (0.12 to 0.39 in). The operating conditions of 200–300 °C (390–570 °F) with a pressure of 1–3 MPa (150–440 psi) prevail in the reactor. To maintain this temperature, the cooling system of the reactor plays a vital role. With the aging of the catalyst, its selectivity decreases and it produces more exothermic side products of CO2. Ethylene oxide scrubber: After the gaseous stream from the main reactor, containing ethylene oxide (1–2%) and CO2 (5%), is cooled, it is then passed to the ethylene oxide scrubber. Here, water is used as the scrubbing media which scrubs away majority of ethylene oxide along with some amounts of CO2, N2, CH2=CH2, CH4 and <a href="/wiki/Aldehydes" class="mw-redirect" title="Aldehydes">aldehydes</a> (introduced by the recycle stream). Also, a small proportion of the gas leaving the ethylene oxide scrubber (0.1–0.2%) is removed continuously (combusted) to prevent the buildup of inert compounds (N2, Ar, and C2H6), which are introduced as impurities with the reactants. Ethylene oxide de-sorber: The aqueous stream resulting from the above scrubbing process is then sent to the ethylene oxide de-sorber. Here, ethylene oxide is obtained as the overhead product, whereas the bottom product obtained is known as the glycol bleed. When ethylene oxide is scrubbed from the recycle gas with an aqueous solution, ethylene glycols (viz. mono-ethylene glycol, di-ethylene glycol and other poly-ethylene glycols) get unavoidably produced. Thus, in-order to prevent them from building up in the system, they are continuously bled off. Stripping and distillation column: Here, the ethylene oxide stream is stripped off its low boiling components and then distilled in-order to separate it into water and ethylene oxide. CO2 scrubber: The recycle stream obtained from the ethylene oxide scrubber is compressed and a side-stream is fed to the CO2 scrubber. Here, CO2 gets dissolved into the hot aqueous solution of potassium carbonate (i.e., the scrubbing media). The dissolution of CO2 is not only a physical phenomenon, but a chemical phenomenon as well, for, the CO2 reacts with potassium carbonate to produce potassium hydrogen carbonate. <dl><dd>K2CO3 + CO2 + H2O → 2 KHCO3</dd></dl> CO2 de-scrubber: The above potassium carbonate solution (enriched with CO2) is then sent to the CO2 de-scrubber where CO2 is de-scrubbed by stepwise (usually two steps) <a href="/wiki/Flash_evaporation" title="Flash evaporation">flashing</a>. The first step is done to remove the hydrocarbon gases, and the second step is employed to strip off CO2. <div class="mw-heading mw-heading3"><h3 id="World_production_of_ethylene_oxide">World production of ethylene oxide</h3>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=35" title="Edit section: World production of ethylene oxide">edit</a>]</div> The world production of ethylene oxide was 20 Mt (22 million short tons) in 2009,<a href="#cite_note-dutia-77">[77]</a> 19 Mt (21 million short tons) in 2008 and 18 Mt (20 million short tons) in 2007.<a href="#cite_note-sri-78">[78]</a> This places ethylene oxide 14th most produced organic chemical, whereas the most produced one was ethylene with 113 Mt (125 million short tons).<a href="#cite_note-79">[79]</a> SRI Consulting forecasted the growth of consumption of ethylene oxide of 4.4% per year during 2008–2013 and 3% from 2013 to 2018.<a href="#cite_note-sri-78">[78]</a> In 2004, the global production of ethylene oxide by region was as follows:<a href="#cite_note-iars-80">[80]</a> <table class="wikitable" style="width:95%;"> <tbody><tr> <th align="center" width="40%">Region </th> <th align="center" width="30%">Number of major producers </th> <th align="center" width="30%">Production, thousand tonnes </th></tr> <tr> <td>North America <a href="/wiki/United_States" title="United States">United States</a> <a href="/wiki/Canada" title="Canada">Canada</a> <a href="/wiki/Mexico" title="Mexico">Mexico</a> </td> <td style="text-align:center;"> 10 3 3 </td> <td style="text-align:center;"> 4009 1084 350 </td></tr> <tr> <td>South America <a href="/wiki/Brazil" title="Brazil">Brazil</a> <a href="/wiki/Venezuela" title="Venezuela">Venezuela</a> </td> <td style="text-align:center;"> 2 1 </td> <td style="text-align:center;"> 312 82 </td></tr> <tr> <td>Europe <a href="/wiki/Belgium" title="Belgium">Belgium</a> <a href="/wiki/France" title="France">France</a> <a href="/wiki/Germany" title="Germany">Germany</a> <a href="/wiki/Netherlands" title="Netherlands">Netherlands</a> <a href="/wiki/Spain" title="Spain">Spain</a> <a href="/wiki/Turkey" title="Turkey">Turkey</a> <a href="/wiki/United_Kingdom" title="United Kingdom">United Kingdom</a> <a href="/wiki/Eastern_Europe" title="Eastern Europe">Eastern Europe</a> </td> <td style="text-align:center;"> 2 1 4 2 1 1 1 No data </td> <td style="text-align:center;"> 770 215 995 460 100 115 300 950 </td></tr> <tr> <td>Middle East <a href="/wiki/Iran" title="Iran">Iran</a> <a href="/wiki/Kuwait" title="Kuwait">Kuwait</a> <a href="/wiki/Saudi_Arabia" title="Saudi Arabia">Saudi Arabia</a> </td> <td style="text-align:center;"> 2 1 2 </td> <td style="text-align:center;"> 201 350 1781 </td></tr> <tr> <td>Asia <a href="/wiki/China" title="China">China</a> <a href="/wiki/Taiwan" title="Taiwan">Taiwan</a> <a href="/wiki/India" title="India">India</a> <a href="/wiki/Indonesia" title="Indonesia">Indonesia</a> <a href="/wiki/Japan" title="Japan">Japan</a> <a href="/wiki/Malaysia" title="Malaysia">Malaysia</a> <a href="/wiki/South_Korea" title="South Korea">South Korea</a> <a href="/wiki/Singapore" title="Singapore">Singapore</a> </td> <td style="text-align:center;"> No data 4 2 1 4 1 3 1 </td> <td style="text-align:center;"> 1354 820 488 175 949 385 740 80 </td></tr></tbody></table> The world's largest producers of ethylene oxide are <a href="/wiki/Dow_Chemical_Company" title="Dow Chemical Company">Dow Chemical Company</a> (3–3.5 Mt (3.3–3.9 million short tons) in 2006<a href="#cite_note-aq-81">[81]</a>), <a href="/wiki/SABIC" title="SABIC">Saudi Basic Industries</a> (2,000–2,500 tonnes (2,200–2,800 short tons) in 2006<a href="#cite_note-aq-81">[81]</a>), <a href="/wiki/Royal_Dutch_Shell" class="mw-redirect" title="Royal Dutch Shell">Royal Dutch Shell</a> (1.328 Mt (1.464 million short tons) in 2008–2009<a href="#cite_note-82">[82]</a><a href="#cite_note-83">[83]</a><a href="#cite_note-84">[84]</a>), <a href="/wiki/BASF" title="BASF">BASF</a> (1.175 Mt (1.295 million short tons) in 2008–2009<a href="#cite_note-85">[85]</a>), <a href="/wiki/China_Petrochemical_Corporation" class="mw-redirect" title="China Petrochemical Corporation">China Petrochemical Corporation</a> (~1 Mt (1.1 million short tons) in 2006<a href="#cite_note-aq-81">[81]</a>), <a href="/wiki/Formosa_Plastics" class="mw-redirect" title="Formosa Plastics">Formosa Plastics</a> (~1 Mt (1.1 million short tons) in 2006<a href="#cite_note-aq-81">[81]</a>), and <a href="/wiki/Ineos" title="Ineos">Ineos</a> (0.92 Mt (1.01 million short tons) in 2008–2009).<a href="#cite_note-86">[86]</a> <div class="mw-heading mw-heading2"><h2 id="Applications">Applications</h2>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=36" title="Edit section: Applications">edit</a>]</div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Eo-usesEN.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d8/Eo-usesEN.png/500px-Eo-usesEN.png" decoding="async" width="350" height="156" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d8/Eo-usesEN.png/525px-Eo-usesEN.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d8/Eo-usesEN.png/700px-Eo-usesEN.png 2x" data-file-width="949" data-file-height="424" /></a><figcaption>Global industrial use of ethylene oxide in 2007<a href="#cite_note-iars-80">[80]</a></figcaption></figure> Ethylene oxide is one of the most important raw materials used in large-scale chemical production. Most ethylene oxide is used for synthesis of <a href="/wiki/Ethylene_glycol" title="Ethylene glycol">ethylene glycols</a>, including diethylene glycol and triethylene glycol, that accounts for up to 75% of global consumption. Other important products include ethylene glycol ethers, ethanolamines, and ethoxylates. Among glycols, ethylene glycol is used as <a href="/wiki/Antifreeze" title="Antifreeze">antifreeze</a>, in the production of <a href="/wiki/Polyester" title="Polyester">polyester</a> and <a href="/wiki/Polyethylene_terephthalate" title="Polyethylene terephthalate">polyethylene terephthalate</a> (PET – raw material for plastic bottles), liquid coolants, and solvents. <table class="wikitable"> <tbody><tr> <th>Sector</th> <th>Demand share (%) </th></tr> <tr> <td><a href="/wiki/Agrochemicals" class="mw-redirect" title="Agrochemicals">Agrochemicals</a></td> <td>7 </td></tr> <tr> <td><a href="/wiki/Oil_field" class="mw-redirect" title="Oil field">Oilfield</a> chemicals</td> <td>10 </td></tr> <tr> <td><a href="/wiki/Detergents" class="mw-redirect" title="Detergents">Detergents</a></td> <td>25 </td></tr> <tr> <td><a href="/wiki/Textile" title="Textile">Textile</a></td> <td>35 </td></tr> <tr> <td>Personal care</td> <td>10 </td></tr> <tr> <td><a href="/wiki/Pharmaceuticals" class="mw-redirect" title="Pharmaceuticals">Pharmaceuticals</a></td> <td>8 </td></tr> <tr> <td>Others</td> <td>5 </td></tr> <tr> <td>Total [2009]</td> <td>5.2 Mt </td></tr></tbody></table> Polyethyleneglycols are used in perfumes, cosmetics, pharmaceuticals, <a href="/wiki/Lubricant" title="Lubricant">lubricants</a>, <a href="/wiki/Paint_thinner" title="Paint thinner">paint thinners</a>, and <a href="/wiki/Plasticizer" title="Plasticizer">plasticizers</a>. Ethylene glycol ethers are part of brake fluids, detergents, solvents, lacquers, and paints. Ethanolamines are used in the manufacture of soap and detergents and for purification of natural gas. Ethoxylates are reaction products of ethylene oxide with higher alcohols, acids, or amines. They are used in the manufacture of detergents, surfactants, <a href="/wiki/Emulsifier" class="mw-redirect" title="Emulsifier">emulsifiers</a>, and <a href="/wiki/Dispersant" title="Dispersant">dispersants</a>.<a href="#cite_note-87">[87]</a> Whereas synthesis of ethylene glycols is the major application of ethylene oxide, its percentage varies greatly depending on the region: from 44% in the <a href="/wiki/Western_Europe" title="Western Europe">Western Europe</a>, 63% in <a href="/wiki/Japan" title="Japan">Japan</a>, and 73% in <a href="/wiki/North_America" title="North America">North America</a> to 90% in the rest of <a href="/wiki/Asia" title="Asia">Asia</a>, and 99% in <a href="/wiki/Africa" title="Africa">Africa</a>.<a href="#cite_note-88">[88]</a> <div class="mw-heading mw-heading3"><h3 id="Production_of_ethylene_glycol">Production of ethylene glycol</h3>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=37" title="Edit section: Production of ethylene glycol">edit</a>]</div> Ethylene glycol is industrially produced by non-catalytic hydration of ethylene oxide at a temperature of 200 °C (392 °F) and a pressure of 1.5–2 MPa (220–290 psi):<a href="#cite_note-MEG-89">[89]</a> <dl><dd><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {(CH2CH2)O + H2O -> HOCH2CH2OH}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <mtext>O</mtext> <mo>+</mo> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mtext>O</mtext> <mo stretchy="false">⟶</mo> <msubsup> <mtext>HOCH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mtext>OH</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {(CH2CH2)O + H2O -> HOCH2CH2OH}}}</annotation> </semantics> </math><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/d7d7e3d3df5e0dcfbd41e88d5a26b642c65f5511" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:41.163ex; height:3.009ex;" alt="{\displaystyle {\ce {(CH2CH2)O + H2O -> HOCH2CH2OH}}}" /></dd></dl> By-products of the reaction are diethylene glycol, triethylene glycol, and polyglycols with the total of about 10%, which are separated from the ethylene glycol by distillation at reduced pressure.<a href="#cite_note-90">[90]</a> Another synthesis method is the reaction of ethylene oxide and CO2 (temperature 80–120 °C (176–248 °F) and pressure of 5.2 MPa (750 psi)) yielding <a href="/wiki/Ethylene_carbonate" title="Ethylene carbonate">ethylene carbonate</a> and its subsequent hydrolysis with decarboxylation:<a href="#cite_note-MEG-89">[89]</a> <dl><dd><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {(CH2CH2)O{}+CO2->{\overset {ethylene\ carbonate}{(O-CH2CH_{2}-O)C=O}}->[{\ce {+H2O}}][{\ce {-CO2}}]HOCH2CH2OH}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <mtext>O</mtext> <mrow class="MJX-TeXAtom-ORD"> </mrow> <mo>+</mo> <msubsup> <mtext>CO</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mo stretchy="false">⟶</mo> <mrow class="MJX-TeXAtom-ORD"> <mover> <mrow> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <mtext>O</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>O</mtext> <mo stretchy="false">)</mo> </mrow> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>=</mo> </mrow> <mtext>O</mtext> </mrow> <mrow> <mtext>ethylene</mtext> <mtext> </mtext> <mtext>carbonate</mtext> </mrow> </mover> </mrow> <mrow class="MJX-TeXAtom-REL"> <munderover> <mo>→</mo> <mpadded width="+0.611em" lspace="0.278em" voffset="-.24em"> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <msubsup> <mtext>CO</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> </mrow> </mpadded> <mpadded width="+0.611em" lspace="0.278em" voffset=".15em"> <mrow class="MJX-TeXAtom-ORD"> <mo>+</mo> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mtext>O</mtext> </mrow> </mpadded> </munderover> </mrow> <msubsup> <mtext>HOCH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mtext>OH</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {(CH2CH2)O{}+CO2->{\overset {ethylene\ carbonate}{(O-CH2CH_{2}-O)C=O}}->[{\ce {+H2O}}][{\ce {-CO2}}]HOCH2CH2OH}}}</annotation> </semantics> </math><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/d3a0280675f689878768f65af0ceb86f75fa2e00" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -2.427ex; margin-bottom: -0.577ex; width:71.62ex; height:7.009ex;" alt="{\displaystyle {\ce {(CH2CH2)O{}+CO2->{\overset {ethylene\ carbonate}{(O-CH2CH_{2}-O)C=O}}->[{\ce {+H2O}}][{\ce {-CO2}}]HOCH2CH2OH}}}" /></dd></dl> Modern technologies of production of ethylene glycol include the following.<a href="#cite_note-91">[91]</a> Shell OMEGA technology (Only Mono-Ethylene Glycol Advantage) is a two-step synthesis of ethylene carbonate using a <a href="/wiki/Phosphonium" title="Phosphonium">phosphonium</a> halide as a catalyst. The glycol yield is 99–99.5%, with other glycols practically absent. The main advantage of the process is production of pure ethylene glycol without the need for further purification. The first commercial plant which uses this method was opened in 2008 in South Korea.<a href="#cite_note-92">[92]</a> Dow METEOR (Most Effective Technology for Ethylene Oxide Reactions) is an integrated technology for producing ethylene oxide and its subsequent hydrolysis into ethylene glycol. The glycol yield is 90–93%. The main advantage of the process is relative simplicity, using fewer stages and less equipment. Conversion to ethylene glycol is also the means by which waste ethylene oxide is scrubbed before venting to the environment. Typically the EtO is passed over a matrix containing either sulfuric acid or potassium permanganate.[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a>] <div class="mw-heading mw-heading3"><h3 id="Production_of_glycol_ethers">Production of glycol ethers</h3>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=38" title="Edit section: Production of glycol ethers">edit</a>]</div> The major industrial esters of mono-, di-, and triethylene glycols are methyl, ethyl, and normal butyl ethers, as well as their acetates and phthalates. The synthesis involves reaction of the appropriate <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohol</a> with ethylene oxide:<a href="#cite_note-93">[93]</a> <dl><dd><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {(CH2CH2)O + ROH -> HOCH2CH2OR}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <mtext>O</mtext> <mo>+</mo> <mtext>ROH</mtext> <mo stretchy="false">⟶</mo> <msubsup> <mtext>HOCH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mtext>OR</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {(CH2CH2)O + ROH -> HOCH2CH2OR}}}</annotation> </semantics> </math><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/281f1e2b7707da670312ca2713877b0a718989f5" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:41.787ex; height:3.009ex;" alt="{\displaystyle {\ce {(CH2CH2)O + ROH -> HOCH2CH2OR}}}" /></dd> <dd><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {(CH2CH2)O + HOCH2CH2OR -> HOCH2CH2OCH2CH2OR}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <mtext>O</mtext> <mo>+</mo> <msubsup> <mtext>HOCH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mtext>OR</mtext> <mo stretchy="false">⟶</mo> <msubsup> <mtext>HOCH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>OCH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mtext>OR</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {(CH2CH2)O + HOCH2CH2OR -> HOCH2CH2OCH2CH2OR}}}</annotation> </semantics> </math><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/b513a2e6e365a815820eaeb85bf6947c42971320" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:63.305ex; height:3.009ex;" alt="{\displaystyle {\ce {(CH2CH2)O + HOCH2CH2OR -> HOCH2CH2OCH2CH2OR}}}" /></dd> <dd><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {(CH2CH2)O + HOCH2CH2OCH2CH2OR -> HOCH2CH2OCH2CH2OCH2CH2OR}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <mtext>O</mtext> <mo>+</mo> <msubsup> <mtext>HOCH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>OCH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mtext>OR</mtext> <mo stretchy="false">⟶</mo> <msubsup> <mtext>HOCH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>OCH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>OCH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mtext>OR</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {(CH2CH2)O + HOCH2CH2OCH2CH2OR -> HOCH2CH2OCH2CH2OCH2CH2OR}}}</annotation> </semantics> </math><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/3e164192f2b1c4a6cc0899c4da855213245bb88f" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:84.823ex; height:3.009ex;" alt="{\displaystyle {\ce {(CH2CH2)O + HOCH2CH2OCH2CH2OR -> HOCH2CH2OCH2CH2OCH2CH2OR}}}" /></dd></dl> The reaction of monoesters with an acid or its anhydride leads to the formation of the esters: <dl><dd><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {CH3CO2H + HOCH2CH2OR -> ROCH2CH2OCOCH3 + H2O}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CO</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mtext>H</mtext> <mo>+</mo> <msubsup> <mtext>HOCH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mtext>OR</mtext> <mo stretchy="false">⟶</mo> <msubsup> <mtext>ROCH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>OCOCH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mo>+</mo> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mtext>O</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {CH3CO2H + HOCH2CH2OR -> ROCH2CH2OCOCH3 + H2O}}}</annotation> </semantics> </math><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/5a6d2778b26a20fd1f4ed8b9bf08362b6ff82151" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:64.401ex; height:2.843ex;" alt="{\displaystyle {\ce {CH3CO2H + HOCH2CH2OR -> ROCH2CH2OCOCH3 + H2O}}}" /></dd></dl> <div class="mw-heading mw-heading3"><h3 id="Production_of_ethanolamines">Production of ethanolamines</h3>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=39" title="Edit section: Production of ethanolamines">edit</a>]</div> In the industry, <a href="/wiki/Ethanolamine" title="Ethanolamine">ethanolamines</a> (mono-, di-, and triethanolamines) are produced by reacting <a href="/wiki/Ammonia" title="Ammonia">ammonia</a> and ethylene oxide in anhydrous medium at a temperature of 40–70 °C (100–160 °F) and pressure of 1.5–3.5 MPa (220–510 psi) MPa:<a href="#cite_note-94">[94]</a> <dl><dd><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {(CH2CH2)O + NH3 -> HOCH2CH2NH2}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <mtext>O</mtext> <mo>+</mo> <msubsup> <mtext>NH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mo stretchy="false">⟶</mo> <msubsup> <mtext>HOCH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>NH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {(CH2CH2)O + NH3 -> HOCH2CH2NH2}}}</annotation> </semantics> </math><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/9d2f426f42063ca5d763685238a68e2c59fe538f" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:42.088ex; height:3.009ex;" alt="{\displaystyle {\ce {(CH2CH2)O + NH3 -> HOCH2CH2NH2}}}" /></dd> <dd><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {2 (CH2CH2)O + NH3 -> (HOCH2CH2)2NH}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> <mspace width="thinmathspace"></mspace> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <mtext>O</mtext> <mo>+</mo> <msubsup> <mtext>NH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mo stretchy="false">⟶</mo> <msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>HOCH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mtext>NH</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {2 (CH2CH2)O + NH3 -> (HOCH2CH2)2NH}}}</annotation> </semantics> </math><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/c146ddf5b57ab361421db25ca88c7176b319ca0d" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:45.446ex; height:3.009ex;" alt="{\displaystyle {\ce {2 (CH2CH2)O + NH3 -> (HOCH2CH2)2NH}}}" /></dd> <dd><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {3 (CH2CH2)O + NH3 -> (HOCH2CH2)3N}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> <mspace width="thinmathspace"></mspace> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <mtext>O</mtext> <mo>+</mo> <msubsup> <mtext>NH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mo stretchy="false">⟶</mo> <msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>HOCH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mtext>N</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {3 (CH2CH2)O + NH3 -> (HOCH2CH2)3N}}}</annotation> </semantics> </math><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/cf918030a7c3f5dbd768fe0a8f98003e40f0931f" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:43.703ex; height:3.009ex;" alt="{\displaystyle {\ce {3 (CH2CH2)O + NH3 -> (HOCH2CH2)3N}}}" /></dd></dl> All three ethanolamines are produced in the process, while ammonia and part of methylamine are recycled. The final products are separated by vacuum <a href="/wiki/Distillation" title="Distillation">distillation</a>. Hydroxyalkylamines are produced in a similar process: <dl><dd><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {(CH2CH2)O + RNH2 -> HOCH2CH2NHR}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <mtext>O</mtext> <mo>+</mo> <msubsup> <mtext>RNH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mo stretchy="false">⟶</mo> <msubsup> <mtext>HOCH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mtext>NHR</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {(CH2CH2)O + RNH2 -> HOCH2CH2NHR}}}</annotation> </semantics> </math><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/f108eae9aa65587f4bf76ea048a68887f844f79b" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:44.454ex; height:3.009ex;" alt="{\displaystyle {\ce {(CH2CH2)O + RNH2 -> HOCH2CH2NHR}}}" /></dd> <dd><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {2 (CH2CH2)O + RNH2 -> (HOCH2CH2)2NR}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> <mspace width="thinmathspace"></mspace> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <mtext>O</mtext> <mo>+</mo> <msubsup> <mtext>RNH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mo stretchy="false">⟶</mo> <msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>HOCH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mtext>NR</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {2 (CH2CH2)O + RNH2 -> (HOCH2CH2)2NR}}}</annotation> </semantics> </math><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/91c3a7097174d58b041c20305c3c23d9ce8f2eb2" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:47.124ex; height:3.009ex;" alt="{\displaystyle {\ce {2 (CH2CH2)O + RNH2 -> (HOCH2CH2)2NR}}}" /></dd></dl> Monosubstituted products are formed by reacting a large excess of amine with ethylene oxide in presence of water and at a temperature below 100 °C (212 °F). Disubstituted products are obtained with a small excess of ethylene oxide, at a temperature of 120–140 °C (250–280 °F) and a pressure of 0.3–0.5 MPa (45–75 psi).<a href="#cite_note-95">[95]</a><a href="#cite_note-96">[96]</a> <div class="mw-heading mw-heading3"><h3 id="Production_of_ethoxylates">Production of ethoxylates</h3>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=40" title="Edit section: Production of ethoxylates">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951" /><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Ethoxylation" title="Ethoxylation">Ethoxylation</a></div> Industrial production of ethoxylates is realized by a direct reaction of higher alcohols, acids, or amines with ethylene oxide in the presence of an alkaline catalyst at a temperature of 120–180 °C (250–360 °F). Modern plants producing ethoxylates are usually based on the BUSS LOOP reactors technology,<a href="#cite_note-buss-97">[97]</a> which is based on a three-stage continuous process. In the first stage, the initiator or catalyst of the reaction and the feedstock are fed into the container, where they are mixed, heated, and vacuum dried. Then reaction is carried out in a special insulated reactor in an inert atmosphere (nitrogen) to prevent a possible explosion of ethylene oxide. Finally, the reaction mixture is neutralized, degassed, and purified.<a href="#cite_note-98">[98]</a> <div class="mw-heading mw-heading3"><h3 id="Production_of_acrylonitrile">Production of acrylonitrile</h3>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=41" title="Edit section: Production of acrylonitrile">edit</a>]</div> Currently, most <a href="/wiki/Acrylonitrile" title="Acrylonitrile">acrylonitrile</a> (90% in 2008) is produced by the SOHIO method, which is based on the catalytic oxidation of <a href="/wiki/Propylene" title="Propylene">propylene</a> in the presence of ammonia and bismuth phosphomolybdate. However, until 1960 a key production process was addition of <a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">hydrogen cyanide</a> to ethylene oxide, followed by dehydration of the resulting <a href="/wiki/Cyanohydrin" title="Cyanohydrin">cyanohydrin</a>:<a href="#cite_note-ACS_Landmarks-99">[99]</a> <a href="#cite_note-100">[100]</a> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" />(CH2CH2)O + HCN → HOCH2CH2CN →−<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" />H2O <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" />CH2=CH−CN</dd></dl> Addition of hydrocyanic acid to ethylene oxide is carried out in the presence of a catalyst (<a href="/wiki/Sodium_hydroxide" title="Sodium hydroxide">sodium hydroxide</a> and <a href="/wiki/Diethylamine" title="Diethylamine">diethylamine</a>), and dehydration of cyanohydrin occurs in the gas phase upon the catalytic action of <a href="/wiki/Aluminium_oxide" title="Aluminium oxide">aluminium oxide</a>.<a href="#cite_note-101">[101]</a> <div class="mw-heading mw-heading2"><h2 id="Non-industrial_uses">Non-industrial uses</h2>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=42" title="Edit section: Non-industrial uses">edit</a>]</div> The direct use of ethylene oxide accounts for only 0.05% (2004 data) of its global production.<a href="#cite_note-iars-80">[80]</a> Ethylene oxide is used as a sterilizing agent, disinfecting agent and <a href="/wiki/Fumigation" title="Fumigation">fumigant</a> as a mixture with carbon dioxide (8.5–80% of ethylene oxide), nitrogen, or <a href="/wiki/Dichlorodifluoromethane" title="Dichlorodifluoromethane">dichlorodifluoromethane</a> (12% ethylene oxide). It is applied for gas-phase sterilization of medical equipment and instruments, packaging materials, clothing, and surgical and scientific equipment;<a href="#cite_note-iars-80">[80]</a> for processing of storage facilities (tobacco, packages of grain, sacks of rice, etc.), clothing, furs, and valuable documents.<a href="#cite_note-ew-102">[102]</a> <div class="mw-heading mw-heading3"><h3 id="Healthcare_sterilant">Healthcare sterilant</h3>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=43" title="Edit section: Healthcare sterilant">edit</a>]</div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Ethylene_oxide_sterilisation_sticker_on_box_of_medical_supplies.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/Ethylene_oxide_sterilisation_sticker_on_box_of_medical_supplies.jpg/250px-Ethylene_oxide_sterilisation_sticker_on_box_of_medical_supplies.jpg" decoding="async" width="220" height="220" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/Ethylene_oxide_sterilisation_sticker_on_box_of_medical_supplies.jpg/330px-Ethylene_oxide_sterilisation_sticker_on_box_of_medical_supplies.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c3/Ethylene_oxide_sterilisation_sticker_on_box_of_medical_supplies.jpg/500px-Ethylene_oxide_sterilisation_sticker_on_box_of_medical_supplies.jpg 2x" data-file-width="1487" data-file-height="1487" /></a><figcaption>Ethylene oxide indicator sticker on a box of sterile medical supplies. The red sticker turns blue when it comes into contact with ethylene oxide</figcaption></figure> Ethylene oxide is one of the most commonly used sterilization methods in the healthcare industry because of its non-damaging effects for delicate instruments and devices that require sterilization, and for its wide range of material compatibility.<a href="#cite_note-103">[103]</a> It is used for instruments that cannot tolerate heat, moisture, or abrasive chemicals, such as electronics, optical equipment, paper, rubber, and plastics.<a href="#cite_note-104">[104]</a> It was developed in the 1940s as a sterilant by the US military, and its use as a medical sterilant dates to the late 1950s, when the McDonald process was patented for medical devices.<a href="#cite_note-105">[105]</a> The <a href="/wiki/Anprolene" title="Anprolene">Anprolene</a> system was patented in the 1960s<a href="#cite_note-106">[106]</a> by Andersen Products,<a href="#cite_note-107">[107]</a> and it remains the most commonly used system in several niche markets, notably the veterinary market and some international markets.<a href="#cite_note-108">[108]</a> It relies on the use of a flexible sterilization chamber and an EtO cartridge for small volume sterilization, and where environmental and/or portability considerations dictate the use of a low dose. It is therefore referred to as the "flexible chamber sterilization" method, or the "gas diffusion sterilization" method. In the United States, the operation of EtO sterilization is overseen by the <a href="/wiki/EPA" class="mw-redirect" title="EPA">EPA</a> through the <a href="/wiki/National_Emissions_Standards_for_Hazardous_Air_Pollutants" title="National Emissions Standards for Hazardous Air Pollutants">National Emissions Standards for Hazardous Air Pollutants</a> (NESHAP).<a href="#cite_note-109">[109]</a> <div class="mw-heading mw-heading3"><h3 id="Niche_uses">Niche uses</h3>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=44" title="Edit section: Niche uses">edit</a>]</div> Ethylene oxide is used as a <a href="/wiki/Fungicide" title="Fungicide">fungicide</a> and as an accelerator of maturation of tobacco leaves.<a href="#cite_note-ew-102">[102]</a> Ethylene oxide is also used as a main component of <a href="/wiki/Thermobaric_weapon" title="Thermobaric weapon">thermobaric weapons</a> (fuel-air explosives).<a href="#cite_note-e1-12">[12]</a><a href="#cite_note-e2-13">[13]</a><a href="#cite_note-110">[110]</a> <div class="mw-heading mw-heading2"><h2 id="Identification_of_ethylene_oxide">Identification of ethylene oxide</h2>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=45" title="Edit section: Identification of ethylene oxide">edit</a>]</div> <a href="/wiki/Gas_chromatography" title="Gas chromatography">Gas chromatography</a> is the principal method for analysis and detection of ethylene oxide.<a href="#cite_note-iars-80">[80]</a> An inexpensive test for ethylene oxide exploits its precipitation of solid hydroxides of metals when it is passed through aqueous solutions of their salts: <dl><dd><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {2 (CH2CH2)O + MnCl2 + 2 H2O -> 2 HO-CH2CH2-Cl + Mn(OH)2 v}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> <mspace width="thinmathspace"></mspace> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <mtext>O</mtext> <mo>+</mo> <msubsup> <mtext>MnCl</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mo>+</mo> <mn>2</mn> <mspace width="thinmathspace"></mspace> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mtext>O</mtext> <mo stretchy="false">⟶</mo> <mn>2</mn> <mspace width="thinmathspace"></mspace> <mtext>HO</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>Cl</mtext> <mo>+</mo> <mtext>Mn</mtext> <msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <mtext>OH</mtext> <mo stretchy="false">)</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">↓</mo> </mrow> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {2 (CH2CH2)O + MnCl2 + 2 H2O -> 2 HO-CH2CH2-Cl + Mn(OH)2 v}}}</annotation> </semantics> </math><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/cb80e6facf9c9890eafeef76a539bcf12c20baa9" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:71.686ex; height:3.009ex;" alt="{\displaystyle {\ce {2 (CH2CH2)O + MnCl2 + 2 H2O -> 2 HO-CH2CH2-Cl + Mn(OH)2 v}}}" /></dd></dl> Similarly, ethylene oxide is detected by the bright pink color of the indicator when passing air through aqueous solutions of some salts of sodium or potassium (chlorides, iodides, thiosulfates, etc.) with the addition of <a href="/wiki/Phenolphthalein" title="Phenolphthalein">phenolphthalein</a>:<a href="#cite_note-oe4-111">[111]</a> <dl><dd><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {(CH2CH2)O + NaCl + H2O -> HO-CH2CH2-Cl + NaOH}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mo stretchy="false">(</mo> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mo stretchy="false">)</mo> </mrow> <mtext>O</mtext> <mo>+</mo> <mtext>NaCl</mtext> <mo>+</mo> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mtext>O</mtext> <mo stretchy="false">⟶</mo> <mtext>HO</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>Cl</mtext> <mo>+</mo> <mtext>NaOH</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {(CH2CH2)O + NaCl + H2O -> HO-CH2CH2-Cl + NaOH}}}</annotation> </semantics> </math><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/baa302f8a70a5096ffba64164f6807ef2f59c480" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:60.921ex; height:3.009ex;" alt="{\displaystyle {\ce {(CH2CH2)O + NaCl + H2O -> HO-CH2CH2-Cl + NaOH}}}" /></dd></dl> Other methods of ethylene oxide detection are<a href="#cite_note-oe4-111">[111]</a> color reactions with <a href="/wiki/Pyridine" title="Pyridine">pyridine</a> derivatives and hydrolysis of ethylene glycol with <a href="/wiki/Periodic_acid" title="Periodic acid">periodic acid</a>. The produced <a href="/wiki/Iodic_acid" title="Iodic acid">iodic acid</a> is detected with <a href="/wiki/Silver_nitrate" title="Silver nitrate">silver nitrate</a>. <div class="mw-heading mw-heading2"><h2 id="Accidents">Accidents</h2>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=46" title="Edit section: Accidents">edit</a>]</div> Ethylene oxide is extremely flammable, and its mixtures with air are explosive. When heated it may rapidly expand, causing fire and explosion.<a href="#cite_note-112">[112]</a> Several industrial accidents have been attributed to ethylene oxide explosion.<a href="#cite_note-113">[113]</a><a href="#cite_note-114">[114]</a><a href="#cite_note-115">[115]</a> The <a href="/wiki/Autoignition_temperature" title="Autoignition temperature">autoignition temperature</a> is 429 °C (804 °F), <a href="/wiki/Thermal_decomposition" title="Thermal decomposition">decomposition temperature</a> of 571 °C (1,060 °F) at 101.3 kPa (14.69 psi), minimum inflammable content in the air is 2.7%,<a href="#cite_note-116">[116]</a> and maximum limit is 100%. The NFPA 704 rating is Health, 3; Flammability, 4; Instability 2.<a href="#cite_note-117">[117]</a> Ethylene oxide in presence of water can hydrolyze to ethylene glycol and form polyethylene oxide, which then eventually is oxidized by air and leads to <a href="/wiki/Hot_spot_effect_in_subatomic_physics" title="Hot spot effect in subatomic physics">hotspots</a> that can trigger explosive decomposition. Fires caused by ethylene oxide are extinguished with conventional media including <a href="/wiki/Fire_retardant_foam" class="mw-redirect" title="Fire retardant foam">foam</a>, carbon dioxide, or water. Suppression of this activity can be done by blanketing with an <a href="/wiki/Inert_gas" title="Inert gas">inert gas</a> until total pressure reaches the nonexplosive range. Extinguishing of burning ethylene oxide is complicated by its ability to continue burning in an inert atmosphere and in water solutions. Fire suppression is reached only upon dilution with water above 22:1.<a href="#cite_note-118">[118]</a> <div class="mw-heading mw-heading3"><h3 id="La_Canonja,_Spain_accident">La Canonja, Spain accident</h3>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=47" title="Edit section: La Canonja, Spain accident">edit</a>]</div> On 14 January 2020 in an industrial estate near <a href="/wiki/Tarragona" title="Tarragona">Tarragona</a>, an explosion of an ethoxylation reactor owned by the chemical company Industrias Quimicas de Oxido de Etileno (IQOXE, part of the CL Industrial Group) occurred.<a href="#cite_note-119">[119]</a><a href="#cite_note-120">[120]</a> The accident launched substantial debris over a radius of about two and a half kilometers, one piece penetrating a distant home and killing an occupant.<a href="#cite_note-121">[121]</a> It is reported that at least three people were killed and seven injured as a direct result of the explosion.<a href="#cite_note-122">[122]</a> The company was, until the time of the explosion the only producer of ethylene oxide in Spain with an installed capacity of 140,000 tons/year. Half of that production was used to manufacture ethylene glycol for PET production.<a href="#cite_note-123">[123]</a> The accident will be investigated under EU regulations within the context of the <a href="/wiki/European_Agency_for_Safety_and_Health_at_Work" title="European Agency for Safety and Health at Work">European Agency for Safety and Health at Work</a>. <div class="mw-heading mw-heading3"><h3 id="2020_sesame_seeds_contamination">2020 sesame seeds contamination</h3>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=48" title="Edit section: 2020 sesame seeds contamination">edit</a>]</div> In September 2020, high levels of <a href="/wiki/Pesticides" class="mw-redirect" title="Pesticides">pesticides</a> were found in 268 tonnes of <a href="/wiki/Sesame" title="Sesame">sesame</a> seeds from <a href="/wiki/India" title="India">India</a>. The contamination had a level of 1000 to 3500 times the limit of 0.05 milligrams per kilogram for ethylene oxide allowed in <a href="/wiki/Europe" title="Europe">Europe</a>. This pesticide is forbidden in Europe, where it is recognized to be <a href="/wiki/Carcinogenic" class="mw-redirect" title="Carcinogenic">carcinogenic</a> and <a href="/wiki/Mutagenic" class="mw-redirect" title="Mutagenic">mutagenic</a>. A <a href="/wiki/Product_recall" title="Product recall">product recall</a> was made, half of the products had an <a href="/wiki/Organic_certification" title="Organic certification">organic certification</a>.<a href="#cite_note-124">[124]</a><a href="#cite_note-125">[125]</a> In September, alert was raised by Belgium by RASFF, but the product has also been sold in other EU single market countries such as France<a href="#cite_note-126">[126]</a> and Ireland. <div class="mw-heading mw-heading2"><h2 id="Physiological_effects">Physiological effects</h2>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=49" title="Edit section: Physiological effects">edit</a>]</div> <div class="mw-heading mw-heading3"><h3 id="Effect_on_microorganisms">Effect on microorganisms</h3>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=50" title="Edit section: Effect on microorganisms">edit</a>]</div> Exposure to ethylene oxide gas causes <a href="/wiki/Alkylation" title="Alkylation">alkylation</a> to microorganisms at a nuclear level.<a href="#cite_note-127">[127]</a> The disinfectant effect of ethylene oxide is similar to that of sterilization by heat, but because of limited penetration, it affects only the surface. ETO sterilization can take up to 12 hours due to its slow action upon microorganisms, and lengthy processing and aeration time.<a href="#cite_note-128">[128]</a> <div class="mw-heading mw-heading3"><h3 id="Effects_on_humans_and_animals">Effects on humans and animals</h3>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=51" title="Edit section: Effects on humans and animals">edit</a>]</div> Ethylene oxide is an <a href="/wiki/Alkylation" title="Alkylation">alkylating agent</a>; it has irritating, sensitizing, and narcotic effects.<a href="#cite_note-ChemAnalitica11-129">[129]</a> Chronic exposure to ethylene oxide is also <a href="/wiki/Mutagen" title="Mutagen">mutagenic</a>. The <a href="/wiki/International_Agency_for_Research_on_Cancer" title="International Agency for Research on Cancer">International Agency for Research on Cancer</a> classifies ethylene oxide into group 1, meaning it is a proven <a href="/wiki/Carcinogen" title="Carcinogen">carcinogen</a>.<a href="#cite_note-basesafework-130">[130]</a><a href="#cite_note-131">[131]</a> Ethylene oxide is classified as a class 2 carcinogen by the German MAK commission and as a class A2 carcinogen by the ACGIH. A 2003 study of 7,576 women exposed while at work in commercial sterilization facilities in the US suggests ethylene oxide is associated with <a href="/wiki/Breast_cancer" title="Breast cancer">breast cancer</a> incidence.<a href="#cite_note-132">[132]</a> A 2004 follow up study analyzing 18,235 men and women workers exposed to ethylene oxide from 1987 to 1998 concluded "There was little evidence of any excess cancer mortality for the cohort as a whole, with the exception of <a href="/wiki/Bone_cancer" class="mw-redirect" title="Bone cancer">bone cancer</a> based on small numbers. Positive exposure-response trends for lymphoid tumors were found for males only. Reasons for the sex specificity of this effect are not known. There was also some evidence of a positive exposure-response for breast cancer mortality."<a href="#cite_note-133">[133]</a> An increased incidence of brain tumors and mononuclear cell leukemia was found in rats that had inhaled ethylene oxide at concentrations of 10, 33 or 100 mL/m3 (0.0100, 0.0329 or 0.0997 imp fl oz/cu ft) over a period of two years.<a href="#cite_note-msds2-134">[134]</a> An increased incidence of peritoneal mesotheliomas was also observed in the animals exposed to concentrations of 33 and 100 mL/m3 (0.0329 and 0.0997 imp fl oz/cu ft). Results of human epidemiological studies on workers exposed to ethylene oxide differ. There is evidence from both human and animal studies that inhalation exposure to ethylene oxide can result in a wide range of carcinogenic effects. Ethylene oxide is toxic by inhalation, with a US <a href="/wiki/Occupational_Safety_and_Health_Administration" title="Occupational Safety and Health Administration">OSHA</a> permissible exposure limit calculated as a TWA (time weighted average) over 8 hours of 1 ppm, and a short term exposure limit (excursion limit) calculated as a TWA over 15 minutes of 5 ppm.<a href="#cite_note-msds-135">[135]</a> At concentrations in the air about 200 parts per million, ethylene oxide irritates <a href="/wiki/Mucous_membrane" title="Mucous membrane">mucous membranes</a> of the nose and throat; higher contents cause damage to the trachea and bronchi, progressing into the partial collapse of the lungs. High concentrations can cause <a href="/wiki/Pulmonary_edema" title="Pulmonary edema">pulmonary edema</a> and damage the cardiovascular system; the damaging effect of ethylene oxide may occur only after 72 hours after exposure.<a href="#cite_note-atsdr-26">[26]</a> The maximum content of ethylene oxide in the air according to the US standards (<a href="/wiki/American_Conference_of_Governmental_Industrial_Hygienists" title="American Conference of Governmental Industrial Hygienists">ACGIH</a>) is 1.8 mg/m3 (0.00079 gr/cu ft).<a href="#cite_note-136">[136]</a> <a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health">NIOSH</a> has determined that the Immediately Dangerous to Life and Health level (IDLH) is 800 ppm.<a href="#cite_note-137">[137]</a> Because the odor threshold for ethylene oxide varies between 250 and 700 ppm, the gas is already at toxic concentrations when it can be smelled. Even then, the odor of ethylene oxide is sweet and aromatic and can easily be mistaken for the aroma of <a href="/wiki/Diethyl_ether" title="Diethyl ether">diethyl ether</a>, a common laboratory solvent of very low toxicity. In view of these insidious properties, continuous electrochemical monitoring is standard practice, and it is forbidden to use ethylene oxide to fumigate building interiors in the <a href="/wiki/European_Union" title="European Union">EU</a> and some other jurisdictions.<a href="#cite_note-bnpuk-138">[138]</a> Ethylene oxide causes acute poisoning, accompanied by a variety of symptoms.<a href="#cite_note-ChemAnalitica11-129">[129]</a> Central nervous system effects are frequently associated with human exposure to ethylene oxide in occupational settings. Headache, nausea, and vomiting have been reported.[<a href="/wiki/Wikipedia:Please_clarify" title="Wikipedia:Please clarify">clarification needed</a>] Peripheral neuropathy, impaired hand-eye coordination and memory loss have been reported in more recent case studies of chronically-exposed workers at estimated average exposure levels as low as 3 ppm (with possible short-term peaks as high as 700 ppm).<a href="#cite_note-msds2-134">[134]</a> The metabolism of ethylene oxide is not completely known. Data from animal studies indicate two possible pathways for the metabolism of ethylene oxide: hydrolysis to ethylene glycol and glutathione conjugation to form <a href="/wiki/Mercapturic_acid" title="Mercapturic acid">mercapturic acid</a> and meththio-metabolites. Ethylene oxide easily penetrates through ordinary clothing and footwear, causing skin irritation and dermatitis with the formation of blisters, fever, and <a href="/wiki/Leukocytosis" title="Leukocytosis">leukocytosis</a>.<a href="#cite_note-ChemAnalitica11-129">[129]</a> Toxicity data for ethylene oxide are as follows:<a href="#cite_note-msds-135">[135]</a> <ul><li>Eye exposure: 18 mg (0.28 gr)/6 hours (rabbit)</li> <li>Oral: 72 mg/kg (0.00115 oz/lb) (rat, <a href="/wiki/Median_lethal_dose" title="Median lethal dose">LD50</a>), 1,186 mg/kg (0.01898 oz/lb) (rat, <a href="/wiki/Lowest_published_toxic_dose" title="Lowest published toxic dose">TDLo</a>), 5,112 mg/kg (0.08179 oz/lb) (rat, <a href="/wiki/Toxic_dose" class="mw-redirect" title="Toxic dose">TD</a>)</li> <li>Inhalation: 12,500 ppm (human, <a href="/wiki/Median_lethal_dose#Other_measures_of_toxicity" title="Median lethal dose">TCLo</a>), 960 ppm/4 hours (dog, <a href="/wiki/Median_lethal_dose" title="Median lethal dose">LC50</a>) 33–50 ppm (rat or mouse, TC), 800 ppm/4 hours (rat or mouse, LC50)</li> <li><a href="/wiki/Subcutaneous_injection" class="mw-redirect" title="Subcutaneous injection">Subcutaneous injection</a>: 100 mg/kg (0.0016 oz/lb) (cat, LDLo), 292 mg/kg (0.00467 oz/lb) (mouse, TDLo) 900–2,600 mg/kg (0.014–0.042 oz/lb) (mouse, TD), 187 mg/kg (0.00299 oz/lb) (rat, LD50).</li> <li><a href="/wiki/Intraperitoneal_injection" title="Intraperitoneal injection">Intraperitoneal injection</a>: 750 mg/kg (0.0120 oz/lb) (mouse, TDLo), 175 mg/kg (0.00280 oz/lb) (mouse, LD50)</li> <li>Intravenous injection: 175 mg/kg (0.00280 oz/lb) (rabbit, LD50), 290 mg/kg (0.0046 oz/lb) (mouse, LD50)</li> <li>The US Environmental Protection Agency (USEPA) estimated in 2016<a href="#cite_note-139">[139]</a> that for low doses, the inhalation of ethylene oxide for a lifetime could increase an individual's lifetime cancer risk by as much as 3.0 × 10−3 per μg/m3 (without considering that early-life exposures are likely more potent). The USEPA estimated the slope of the dose-response declines at higher doses, and extra cancer risk estimates for several occupational exposure scenarios are calculated.</li></ul> <div class="mw-heading mw-heading2"><h2 id="Global_demand">Global demand</h2>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=52" title="Edit section: Global demand">edit</a>]</div> Global EO demand has expanded from 16.6 <a href="/wiki/Tonne" title="Tonne">Mt</a> (18.3 million short tons) in 2004 to 20 Mt (22 million short tons) in 2009, while demand for refined EO expanded from 4.64 Mt (5.11 million short tons) in 2004 to 5.6 Mt (6.2 million short tons) in 2008. In 2009, demand is estimated to have declined to about 5.2 Mt (5.7 million short tons). Total EO demand registered a growth rate of 5.6% per annum during the period 2005 to 2009 and is projected to grow at 5.7% per annum during 2009 to 2013.<a href="#cite_note-dutia-77">[77]</a> <div class="mw-heading mw-heading2"><h2 id="Health_and_safety_regulations">Health and safety regulations</h2>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=53" title="Edit section: Health and safety regulations">edit</a>]</div> According to Merck Life Science UK 2020 Safety Data Sheet provided to the <a href="/wiki/European_Chemicals_Agency" title="European Chemicals Agency">European Chemicals Agency</a>'s <a href="/wiki/Registration,_Evaluation,_Authorisation_and_Restriction_of_Chemicals" title="Registration, Evaluation, Authorisation and Restriction of Chemicals">Registration, Evaluation, Authorisation and Restriction of Chemicals</a> (REACH)—a 2006 <a href="/wiki/European_Union_regulation" class="mw-redirect" title="European Union regulation">European Union regulation</a>,<a href="#cite_note-140">[140]</a> ethylene oxide is "presumed to have carcinogenic potential for humans."<a href="#cite_note-sigmaaldrich_2020-8">[8]</a> The United States EPA published an <a href="/wiki/Notice_of_proposed_rulemaking" title="Notice of proposed rulemaking">advance notice of proposed rulemaking</a> (NPRM) in the 12 December 2019 Federal Register seeking to limit EtO emissions.<a href="#cite_note-141">[141]</a> Over the next couple of years, information was collected and a proposed air toxics rule published in the 13 April 2023 Federal Register.<a href="#cite_note-142">[142]</a> Following a 60 day comment period that could be extended, due to many comments requesting an extension, the EPA rules that could reduce EtO emissions, both direct and fugitive, by over 80% could be implemented within 18 months of publishing the final rule in the Federal Register.<a href="#cite_note-143">[143]</a> Laboratory EtO emitters would still be exempt from the stricter compliance. Additionally, while effectively curbing EtO emissions in the USA, many industrial emitters may simply shift their EtO production to nearby less strict countries: Canada, Mexico, etc. In 2024, U.S. probed claims that popular Indian curry brands <a href="/wiki/MDH_(spice_company)" title="MDH (spice company)">MDH</a> and <a href="/wiki/Everest_Spices" title="Everest Spices">Everest Spices</a> carried ethylene oxide after Hong Kong and Singapore found the contamination in the products and took enforcement actions against them.<a href="#cite_note-144">[144]</a> <div class="mw-heading mw-heading2"><h2 id="References">References</h2>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=54" title="Edit section: References">edit</a>]</div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-1"><a href="#cite_ref-1">^</a> <style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFInternational_Union_of_Pure_and_Applied_Chemistry2014" class="citation book cs1"><a href="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">International Union of Pure and Applied Chemistry</a> (2014). 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Retrieved 1 September 2020.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Sigma-Aldrich&rft.atitle=Ethylene+oxide+387614&rft_id=https%3A%2F%2Fwww.sigmaaldrich.com%2Fcatalog%2Fproduct%2Faldrich%2F387614%3Flang%3Den%26region%3DGB&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthylene+oxide" class="Z3988"> <a rel="nofollow" class="external text" href="https://archive.org/download/ethylene-oxide-msds/Ethylene%20oxide%20MSDS.pdf">Alt URL</a> </li> <li id="cite_note-9"><a href="#cite_ref-9">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.cdc.gov/niosh/idlh/75218.html">"Ethylene oxide"</a>. Immediately Dangerous to Life or Health Concentrations (IDLH). <a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health">National Institute for Occupational Safety and Health</a> (NIOSH).</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Immediately+Dangerous+to+Life+or+Health+Concentrations+%28IDLH%29&rft.atitle=Ethylene+oxide&rft_id=https%3A%2F%2Fwww.cdc.gov%2Fniosh%2Fidlh%2F75218.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthylene+oxide" class="Z3988"> </li> <li id="cite_note-Ullmann-10">^ <a href="#cite_ref-Ullmann_10-0">a</a> <a href="#cite_ref-Ullmann_10-1">b</a> Rebsdat, Siegfried and Mayer, Dieter (2005) "Ethylene Oxide" in Ullmann's Encyclopedia of Industrial Chemistry. 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Features of the reactivity of ethylene oxide and the structure of its molecules". Ethylene oxide. Khimiya. pp. 15–17.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Part+I.+Structure+and+properties+of+ethylene+oxide.+Features+of+the+reactivity+of+ethylene+oxide+and+the+structure+of+its+molecules&rft.btitle=Ethylene+oxide&rft.pages=%3Cspan+class%3D%22nowrap%22%3E15-%3C%2Fspan%3E17&rft.pub=Khimiya&rft.date=1967&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthylene+oxide" class="Z3988"> </li> <li id="cite_note-17"><a href="#cite_ref-17">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBredig,_G.Usoff,_A.1896" class="citation journal cs1">Bredig, G.; Usoff, A. (1896). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=0cPmAAAAMAAJ&pg=PA116">"Ist Acetylen ein Elektrolyt?"</a> [Is acetylene an electrolyte?]. 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Boca Raton, FL: <a href="/wiki/CRC_Press" title="CRC Press">CRC Press</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1439855119" title="Special:BookSources/978-1439855119"><bdi>978-1439855119</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=CRC+Handbook+of+Chemistry+and+Physics&rft.place=Boca+Raton%2C+FL&rft.edition=92nd&rft.pub=CRC+Press&rft.date=2011&rft.isbn=978-1439855119&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthylene+oxide" class="Z3988"></li></ul> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2>[<a href="/w/index.php?title=Ethylene_oxide&action=edit&section=56" title="Edit section: External links">edit</a>]</div> <style data-mw-deduplicate="TemplateStyles:r1235681985">.mw-parser-output .side-box{margin:4px 0;box-sizing:border-box;border:1px solid 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oxide</a>.</div></div> </div> <ul><li><a rel="nofollow" class="external text" href="https://www.eosa.org/">EOSA Promoting the safe use of Ethylene Oxide for Sterilization</a></li> <li><a rel="nofollow" class="external text" href="https://webbook.nist.gov/cgi/cbook.cgi?ID=C75218">WebBook page for C2H4O</a></li> <li><a rel="nofollow" class="external text" href="https://www.cdc.gov/niosh/topics/ethyleneoxide/">National Institute for Occupational Safety and Health – Ethylene Oxide Topic Page</a></li> <li><a rel="nofollow" class="external text" href="https://www.cdc.gov/niosh/npg/npgd0275.html">CDC – NIOSH Pocket Guide to Chemical Hazards</a></li> <li><a rel="nofollow" class="external text" href="http://www.anpro.com/articles/EOSA%20update%20article.htm">EOSA memo about Ethylene Oxide (EtO) facts</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20171015044858/http://www.anpro.com/articles/EOSA%20update%20article.htm">Archived</a> 15 October 2017 at the <a 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href="/wiki/List_of_interstellar_and_circumstellar_molecules" title="List of interstellar and circumstellar molecules">Molecules detected in outer space</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Molecule" title="Molecule">Molecules</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Diatomic_molecule" title="Diatomic molecule">Diatomic</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aluminium_monochloride" title="Aluminium monochloride">Aluminium monochloride</a></li> <li><a href="/wiki/Aluminium_monofluoride" title="Aluminium monofluoride">Aluminium monofluoride</a></li> <li><a href="/wiki/Aluminium(II)_oxide" title="Aluminium(II) oxide">Aluminium(II) oxide</a></li> <li><a href="/wiki/Argonium" title="Argonium">Argonium</a></li> <li><a href="/wiki/Carbon_cation" class="mw-redirect" title="Carbon cation">Carbon cation</a></li> <li><a href="/wiki/Carbon_monophosphide" title="Carbon monophosphide">Carbon monophosphide</a></li> <li><a href="/wiki/Carbon_monosulfide" title="Carbon monosulfide">Carbon monosulfide</a></li> <li><a href="/wiki/Carbon_monoxide" title="Carbon monoxide">Carbon monoxide</a></li> <li><a href="/wiki/Cyano_radical" title="Cyano radical">Cyano radical</a></li> <li><a href="/wiki/Diatomic_carbon" title="Diatomic carbon">Diatomic carbon</a></li> <li><a href="/w/index.php?title=Fluoromethylidynium&action=edit&redlink=1" class="new" title="Fluoromethylidynium (page does not exist)">Fluoromethylidynium</a></li> <li><a href="/wiki/Helium_hydride_ion" title="Helium hydride ion">Helium hydride ion</a></li> <li><a href="/wiki/Hydrogen_chloride" title="Hydrogen chloride">Hydrogen chloride</a></li> <li><a href="/wiki/Hydrogen_fluoride" title="Hydrogen fluoride">Hydrogen fluoride</a></li> <li><a href="/wiki/Hydrogen" title="Hydrogen">Hydrogen</a> (molecular)</li> <li><a href="/wiki/Hydroxyl_radical" title="Hydroxyl radical">Hydroxyl radical</a></li> <li><a href="/wiki/Imidogen" title="Imidogen">Imidogen</a></li> <li><a href="/wiki/Iron(II)_oxide" title="Iron(II) oxide">Iron(II) oxide</a></li> <li><a href="/wiki/Magnesium_monohydride" title="Magnesium monohydride">Magnesium monohydride</a></li> <li><a href="/wiki/Methylidyne_radical" title="Methylidyne radical">Methylidyne radical</a></li> <li><a href="/wiki/Nitric_oxide" title="Nitric oxide">Nitric oxide</a></li> <li><a href="/wiki/Nitrogen" title="Nitrogen">Nitrogen</a> (molecular)</li> <li><a href="/wiki/Oxygen" title="Oxygen">Oxygen</a> (molecular)</li> <li><a href="/wiki/Phosphorus_monoxide" title="Phosphorus monoxide">Phosphorus monoxide</a></li> <li><a href="/wiki/Phosphorus_mononitride" title="Phosphorus mononitride">Phosphorus mononitride</a></li> <li><a href="/wiki/Potassium_chloride" title="Potassium chloride">Potassium chloride</a></li> <li><a href="/wiki/Silicon_carbide" title="Silicon carbide">Silicon carbide</a></li> <li><a href="/wiki/Silicon_monoxide" title="Silicon monoxide">Silicon monoxide</a></li> <li><a href="/wiki/Silicon_monosulfide" title="Silicon monosulfide">Silicon monosulfide</a></li> <li><a href="/wiki/Sodium_chloride" title="Sodium chloride">Sodium chloride</a></li> <li><a href="/wiki/Sodium_iodide" title="Sodium iodide">Sodium iodide</a></li> <li><a href="/wiki/Sulfanyl" title="Sulfanyl">Sulfanyl</a></li> <li><a href="/wiki/Sulfur_mononitride" title="Sulfur mononitride">Sulfur mononitride</a></li> <li><a href="/wiki/Sulfur_monoxide" title="Sulfur monoxide">Sulfur monoxide</a></li> <li><a href="/wiki/Titanium(II)_oxide" title="Titanium(II) oxide">Titanium(II) oxide</a></li></ul> </div></td><td class="noviewer navbox-image" rowspan="9" style="width:1px;padding:0 0 0 2px"><div><a href="/wiki/Nitrous_oxide" title="Nitrous oxide"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/93/Nitrous-oxide-3D-balls.png/60px-Nitrous-oxide-3D-balls.png" decoding="async" width="60" height="24" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/93/Nitrous-oxide-3D-balls.png/90px-Nitrous-oxide-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/93/Nitrous-oxide-3D-balls.png/120px-Nitrous-oxide-3D-balls.png 2x" data-file-width="1100" data-file-height="441" /></a> <a href="/wiki/Ethanol" title="Ethanol"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Ethanol-3D-balls.png/60px-Ethanol-3D-balls.png" decoding="async" width="60" height="41" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Ethanol-3D-balls.png/90px-Ethanol-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b0/Ethanol-3D-balls.png/120px-Ethanol-3D-balls.png 2x" data-file-width="1100" data-file-height="754" /></a> <a href="/wiki/Buckminsterfullerene" title="Buckminsterfullerene"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Buckminsterfullerene-perspective-3D-balls.png/60px-Buckminsterfullerene-perspective-3D-balls.png" decoding="async" width="60" height="63" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Buckminsterfullerene-perspective-3D-balls.png/120px-Buckminsterfullerene-perspective-3D-balls.png 1.5x" data-file-width="1056" data-file-height="1100" /></a></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Triatomic_molecule" title="Triatomic molecule">Triatomic</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aluminium(I)_hydroxide" class="mw-redirect" title="Aluminium(I) hydroxide">Aluminium(I) hydroxide</a></li> <li><a href="/w/index.php?title=Aluminium_isocyanide&action=edit&redlink=1" class="new" title="Aluminium isocyanide (page does not exist)">Aluminium isocyanide</a></li> <li><a href="/wiki/Amino_radical" title="Amino radical">Amino radical</a></li> <li><a href="/wiki/Carbon_dioxide" title="Carbon dioxide">Carbon dioxide</a></li> <li><a href="/wiki/Carbonyl_sulfide" title="Carbonyl sulfide">Carbonyl sulfide</a></li> <li><a href="/w/index.php?title=CCP_radical&action=edit&redlink=1" class="new" title="CCP radical (page does not exist)">CCP radical</a></li> <li><a href="/wiki/Halonium_ion" title="Halonium ion">Chloronium</a></li> <li><a href="/wiki/Diazenylium" title="Diazenylium">Diazenylium</a></li> <li><a href="/wiki/Dicarbon_monoxide" title="Dicarbon monoxide">Dicarbon monoxide</a></li> <li><a href="/w/index.php?title=Disilicon_carbide&action=edit&redlink=1" class="new" title="Disilicon carbide (page does not exist)">Disilicon carbide</a></li> <li><a href="/wiki/Ethynyl_radical" title="Ethynyl radical">Ethynyl radical</a></li> <li><a href="/w/index.php?title=Formyl_radical&action=edit&redlink=1" class="new" title="Formyl radical (page does not exist)">Formyl radical</a></li> <li><a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">Hydrogen cyanide</a> (HCN)</li> <li><a href="/wiki/Hydrogen_isocyanide" title="Hydrogen isocyanide">Hydrogen isocyanide</a> (HNC)</li> <li><a href="/wiki/Hydrogen_sulfide" title="Hydrogen sulfide">Hydrogen sulfide</a></li> <li><a href="/wiki/Hydroperoxyl" title="Hydroperoxyl">Hydroperoxyl</a></li> <li><a href="/wiki/Iron(II)_cyanide" title="Iron(II) cyanide">Iron cyanide</a></li> <li><a href="/w/index.php?title=Isoformyl&action=edit&redlink=1" class="new" title="Isoformyl (page does not exist)">Isoformyl</a></li> <li><a href="/wiki/Magnesium_cyanide" title="Magnesium cyanide">Magnesium cyanide</a></li> <li><a href="/w/index.php?title=Magnesium_isocyanide&action=edit&redlink=1" class="new" title="Magnesium isocyanide (page does not exist)">Magnesium isocyanide</a></li> <li><a href="/wiki/Methylene_(compound)" title="Methylene (compound)">Methylene</a></li> <li><a href="/wiki/Methylidynephosphane" title="Methylidynephosphane">Methylidynephosphane</a></li> <li><a href="/wiki/Diazenylium" title="Diazenylium">N2H+</a></li> <li><a href="/wiki/Nitrous_oxide" title="Nitrous oxide">Nitrous oxide</a></li> <li><a href="/wiki/Nitroxyl" title="Nitroxyl">Nitroxyl</a></li> <li><a href="/wiki/Ozone" title="Ozone">Ozone</a></li> <li><a href="/wiki/Potassium_cyanide" title="Potassium cyanide">Potassium cyanide</a></li> <li><a href="/wiki/Sodium_cyanide" title="Sodium cyanide">Sodium cyanide</a></li> <li><a href="/wiki/Sodium_hydroxide" title="Sodium hydroxide">Sodium hydroxide</a></li> <li><a href="/w/index.php?title=Silicon_carbonitride&action=edit&redlink=1" class="new" title="Silicon carbonitride (page does not exist)">Silicon carbonitride</a></li> <li><a href="/w/index.php?title=C-Silicon_dicarbide&action=edit&redlink=1" class="new" title="C-Silicon dicarbide (page does not exist)">c-Silicon dicarbide</a></li> <li><a href="/w/index.php?title=SiNC&action=edit&redlink=1" class="new" title="SiNC (page does not exist)">SiNC</a></li> <li><a href="/wiki/Sulfur_dioxide" title="Sulfur dioxide">Sulfur dioxide</a></li> <li><a href="/w/index.php?title=Thioformyl&action=edit&redlink=1" class="new" title="Thioformyl (page does not exist)">Thioformyl</a></li> <li><a href="/wiki/Thioxoethenylidene" title="Thioxoethenylidene">Thioxoethenylidene</a></li> <li><a href="/wiki/Titanium_dioxide" title="Titanium dioxide">Titanium dioxide</a></li> <li><a href="/wiki/Tricarbon" title="Tricarbon">Tricarbon</a></li> <li><a href="/wiki/Trihydrogen_cation" title="Trihydrogen cation">Trihydrogen cation</a></li> <li><a href="/wiki/Water" title="Water">Water</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Four atoms</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetylene" title="Acetylene">Acetylene</a></li> <li><a href="/wiki/Ammonia" title="Ammonia">Ammonia</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Cyanoethynyl</a></li> <li><a href="/wiki/Interstellar_formaldehyde" title="Interstellar formaldehyde">Formaldehyde</a></li> <li><a href="/wiki/Fulminic_acid" title="Fulminic acid">Fulminic acid</a></li> <li><a href="/w/index.php?title=HCCN&action=edit&redlink=1" class="new" title="HCCN (page does not exist)">HCCN</a></li> <li><a href="/wiki/Hydrogen_peroxide" title="Hydrogen peroxide">Hydrogen peroxide</a></li> <li><a href="/w/index.php?title=Hydromagnesium_isocyanide&action=edit&redlink=1" class="new" title="Hydromagnesium isocyanide (page does not exist)">Hydromagnesium isocyanide</a></li> <li><a href="/wiki/Isocyanic_acid" title="Isocyanic acid">Isocyanic acid</a></li> <li><a href="/wiki/Thiocyanic_acid" title="Thiocyanic acid">Isothiocyanic acid</a></li> <li><a href="/w/index.php?title=Ketenyl&action=edit&redlink=1" class="new" title="Ketenyl (page does not exist)">Ketenyl</a></li> <li><a href="/wiki/Methyl_cation" class="mw-redirect" title="Methyl cation">Methyl cation</a></li> <li><a href="/wiki/Methyl_radical" title="Methyl radical">Methyl radical</a></li> <li><a href="/w/index.php?title=Methylene_amidogen&action=edit&redlink=1" class="new" title="Methylene amidogen (page does not exist)">Methylene amidogen</a></li> <li><a href="/wiki/Propynylidyne" title="Propynylidyne">Propynylidyne</a></li> <li><a href="/w/index.php?title=Protonated_carbon_dioxide&action=edit&redlink=1" class="new" title="Protonated carbon dioxide (page does not exist)">Protonated carbon dioxide</a></li> <li><a href="/wiki/Protonated_hydrogen_cyanide" title="Protonated hydrogen cyanide">Protonated hydrogen cyanide</a></li> <li><a href="/w/index.php?title=Silicon_tricarbide&action=edit&redlink=1" class="new" title="Silicon tricarbide (page does not exist)">Silicon tricarbide</a></li> <li><a href="/wiki/Thiocyanic_acid" title="Thiocyanic acid">Thiocyanic acid</a></li> <li><a href="/wiki/Thioformaldehyde" title="Thioformaldehyde">Thioformaldehyde</a></li> <li><a href="/wiki/Tricarbon_monosulfide" title="Tricarbon monosulfide">Tricarbon monosulfide</a></li> <li><a href="/wiki/Tricarbon_monoxide" title="Tricarbon monoxide">Tricarbon monoxide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Five atoms</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ammonium" title="Ammonium">Ammonium</a> ion</li> <li><a href="/wiki/Polyyne" title="Polyyne">Butadiynyl</a></li> <li><a href="/wiki/Carbodiimide" title="Carbodiimide">Carbodiimide</a></li> <li><a href="/wiki/Cyanamide" title="Cyanamide">Cyanamide</a></li> <li><a href="/wiki/Cyanoacetylene" title="Cyanoacetylene">Cyanoacetylene</a></li> <li><a href="/w/index.php?title=Cyanoformaldehyde&action=edit&redlink=1" class="new" title="Cyanoformaldehyde (page does not exist)">Cyanoformaldehyde</a></li> <li><a href="/wiki/Cyanomethyl" title="Cyanomethyl">Cyanomethyl</a></li> <li><a href="/wiki/Cyclopropenylidene" title="Cyclopropenylidene">Cyclopropenylidene</a></li> <li><a href="/wiki/Formic_acid" title="Formic acid">Formic acid</a></li> <li><a href="/w/index.php?title=Isocyanoacetylene&action=edit&redlink=1" class="new" title="Isocyanoacetylene (page does not exist)">Isocyanoacetylene</a></li> <li><a href="/wiki/Ketene" title="Ketene">Ketene</a></li> <li><a href="/wiki/Methane" title="Methane">Methane</a></li> <li><a href="/wiki/Methoxy" class="mw-redirect" title="Methoxy">Methoxy radical</a></li> <li><a href="/w/index.php?title=Methylenimine&action=edit&redlink=1" class="new" title="Methylenimine (page does not exist)">Methylenimine</a></li> <li><a href="/w/index.php?title=Propadienylidene&action=edit&redlink=1" class="new" title="Propadienylidene (page does not exist)">Propadienylidene</a></li> <li><a href="/w/index.php?title=Protonated_formaldehyde&action=edit&redlink=1" class="new" title="Protonated formaldehyde (page does not exist)">Protonated formaldehyde</a></li> <li><a href="/wiki/Silane" title="Silane">Silane</a></li> <li><a href="/w/index.php?title=Silicon-carbide_cluster&action=edit&redlink=1" class="new" title="Silicon-carbide cluster (page does not exist)">Silicon-carbide cluster</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Six atoms</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetonitrile" title="Acetonitrile">Acetonitrile</a></li> <li><a href="/w/index.php?title=Cyanobutadiynyl_radical&action=edit&redlink=1" class="new" title="Cyanobutadiynyl radical (page does not exist)">Cyanobutadiynyl radical</a></li> <li><a href="/wiki/Cyclopropenone" title="Cyclopropenone">Cyclopropenone</a></li> <li><a href="/wiki/Diacetylene" title="Diacetylene">Diacetylene</a></li> <li><a href="/w/index.php?title=E-Cyanomethanimine&action=edit&redlink=1" class="new" title="E-Cyanomethanimine (page does not exist)">E-Cyanomethanimine</a></li> <li><a href="/wiki/Ethylene" title="Ethylene">Ethylene</a></li> <li><a href="/wiki/Formamide" title="Formamide">Formamide</a></li> <li><a href="/w/index.php?title=HC4N&action=edit&redlink=1" class="new" title="HC4N (page does not exist)">HC4N</a></li> <li><a href="/wiki/Ketenimine" class="mw-redirect" title="Ketenimine">Ketenimine</a></li> <li><a href="/wiki/Methanethiol" title="Methanethiol">Methanethiol</a></li> <li><a href="/wiki/Methanol" title="Methanol">Methanol</a></li> <li><a href="/wiki/Methyl_isocyanide" title="Methyl isocyanide">Methyl isocyanide</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Pentynylidyne</a></li> <li><a href="/wiki/Propynal" class="mw-redirect" title="Propynal">Propynal</a></li> <li><a href="/w/index.php?title=Protonated_cyanoacetylene&action=edit&redlink=1" class="new" title="Protonated cyanoacetylene (page does not exist)">Protonated cyanoacetylene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Seven atoms</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetaldehyde" title="Acetaldehyde">Acetaldehyde</a></li> <li><a href="/wiki/Acrylonitrile" title="Acrylonitrile">Acrylonitrile</a> <ul><li><a href="/wiki/Vinyl_cyanide" class="mw-redirect" title="Vinyl cyanide">Vinyl cyanide</a></li></ul></li> <li><a href="/wiki/Cyanopolyyne" title="Cyanopolyyne">Cyanodiacetylene</a></li> <li><a class="mw-selflink selflink">Ethylene oxide</a></li> <li><a href="/wiki/Glycolonitrile" title="Glycolonitrile">Glycolonitrile</a></li> <li><a href="/wiki/Hexatriynyl_radical" title="Hexatriynyl radical">Hexatriynyl radical</a></li> <li><a href="/wiki/Methyl_isocyanate" title="Methyl isocyanate">Methyl isocyanate</a></li> <li><a href="/wiki/Methylamine" title="Methylamine">Methylamine</a></li> <li><a href="/wiki/Propyne" title="Propyne">Propyne</a></li> <li><a href="/wiki/Vinyl_alcohol" title="Vinyl alcohol">Vinyl alcohol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Eight atoms</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetic_acid" title="Acetic acid">Acetic acid</a></li> <li><a href="/wiki/Acrolein" title="Acrolein">Acrolein</a></li> <li><a href="/wiki/Aminoacetonitrile" title="Aminoacetonitrile">Aminoacetonitrile</a></li> <li><a href="/w/index.php?title=Cyanoallene&action=edit&redlink=1" class="new" title="Cyanoallene (page does not exist)">Cyanoallene</a></li> <li><a href="/wiki/Ethanimine" title="Ethanimine">Ethanimine</a></li> <li><a href="/wiki/Glycolaldehyde" title="Glycolaldehyde">Glycolaldehyde</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Hexapentaenylidene</a></li> <li><a href="/wiki/Methyl_formate" title="Methyl formate">Methyl formate</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Methylcyanoacetylene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Nine atoms</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetamide" title="Acetamide">Acetamide</a></li> <li><a href="/wiki/Cyanopolyyne" title="Cyanopolyyne">Cyanohexatriyne</a></li> <li><a href="/wiki/Dimethyl_ether" title="Dimethyl ether">Dimethyl ether</a></li> <li><a href="/wiki/Ethanethiol" title="Ethanethiol">Ethanethiol</a></li> <li><a href="/wiki/Ethanol" title="Ethanol">Ethanol</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Methyldiacetylene</a></li> <li><a href="/wiki/N-Methylformamide" title="N-Methylformamide">N-Methylformamide</a></li> <li><a href="/wiki/Octatetraynyl_radical" title="Octatetraynyl radical">Octatetraynyl radical</a></li> <li><a href="/wiki/Propene" class="mw-redirect" title="Propene">Propene</a></li> <li><a href="/wiki/Propionitrile" title="Propionitrile">Propionitrile</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Ten atoms or more</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetone" title="Acetone">Acetone</a></li> <li><a href="/wiki/Benzene" title="Benzene">Benzene</a></li> <li><a href="/wiki/Benzonitrile" title="Benzonitrile">Benzonitrile</a></li> <li><a href="/wiki/Buckminsterfullerene" title="Buckminsterfullerene">Buckminsterfullerene</a> (C60, C60+, fullerene, buckyball)</li> <li><a href="/wiki/Butyronitrile" title="Butyronitrile">Butyronitrile</a></li> <li><a href="/wiki/C70_fullerene" title="C70 fullerene">C70 fullerene</a></li> <li><a href="/wiki/Cyanopolyyne" title="Cyanopolyyne">Cyanodecapentayne</a></li> <li><a href="/wiki/Ethyl_formate" title="Ethyl formate">Ethyl formate</a></li> <li><a href="/wiki/Ethylene_glycol" title="Ethylene glycol">Ethylene glycol</a></li> <li><a href="/w/index.php?title=Heptatrienyl_radical&action=edit&redlink=1" class="new" title="Heptatrienyl radical (page does not exist)">Heptatrienyl radical</a></li> <li><a href="/wiki/Methyl_acetate" title="Methyl acetate">Methyl acetate</a></li> <li><a href="/wiki/Cyanopolyyne" title="Cyanopolyyne">Methyl-cyano-diacetylene</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Methyltriacetylene</a></li> <li><a href="/wiki/Propionaldehyde" title="Propionaldehyde">Propionaldehyde</a></li> <li><a href="/wiki/Pyrimidine" title="Pyrimidine">Pyrimidine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Deuterium" title="Deuterium">Deuterated</a> molecules</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ammonia" title="Ammonia">Ammonia</a></li> <li><a href="/wiki/Ammonium" title="Ammonium">Ammonium</a> ion</li> <li><a href="/wiki/Formaldehyde" title="Formaldehyde">Formaldehyde</a></li> <li><a href="/wiki/Interstellar_formaldehyde#Interstellar_reactions" title="Interstellar formaldehyde">Formyl radical</a></li> <li><a href="/wiki/Heavy_water" title="Heavy water">Heavy water</a></li> <li><a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">Hydrogen cyanide</a></li> <li><a href="/wiki/Hydrogen_deuteride" title="Hydrogen deuteride">Hydrogen deuteride</a></li> <li><a href="/wiki/Hydrogen_isocyanide" title="Hydrogen isocyanide">Hydrogen isocyanide</a></li> <li><a href="/wiki/Diazenylium" title="Diazenylium">N2D+</a></li> <li><a href="/wiki/Propyne" title="Propyne">Propyne</a></li> <li><a href="/wiki/Trihydrogen_cation" title="Trihydrogen cation">Trihydrogen cation</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#Molecules" title="List of interstellar and circumstellar molecules">Unconfirmed</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Anthracene" title="Anthracene">Anthracene</a></li> <li><a href="/wiki/Dihydroxyacetone" title="Dihydroxyacetone">Dihydroxyacetone</a></li> <li><a href="/wiki/Glycine" title="Glycine">Glycine</a></li> <li><a href="/wiki/Graphene" title="Graphene">Graphene</a></li> <li><a href="/w/index.php?title=H2NCO%2B&action=edit&redlink=1" class="new" title="H2NCO+ (page does not exist)">H2NCO+</a></li> <li><a href="/wiki/Hemolithin" title="Hemolithin">Hemolithin</a></li> <li><a href="/wiki/Carbon" title="Carbon">Linear C5</a></li> <li><a href="/wiki/Methoxyethane" title="Methoxyethane">Methoxyethane</a></li> <li><a href="/wiki/Naphthalene" title="Naphthalene">Naphthalene cation</a></li> <li><a href="/wiki/Phosphine" title="Phosphine">Phosphine</a></li> <li><a href="/wiki/Pyrene" title="Pyrene">Pyrene</a></li> <li><a href="/wiki/Silylidyne" title="Silylidyne">Silylidyne</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_interstellar_and_circumstellar_molecules#See_also" title="List of interstellar and circumstellar molecules">Related</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Abiogenesis" title="Abiogenesis">Abiogenesis</a></li> <li><a href="/wiki/Astrobiology" title="Astrobiology">Astrobiology</a></li> <li><a href="/wiki/Astrochemistry" title="Astrochemistry">Astrochemistry</a></li> <li><a href="/wiki/Atomic_and_molecular_astrophysics" title="Atomic and molecular astrophysics">Atomic and molecular astrophysics</a></li> <li><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></li> <li><a href="/wiki/Circumstellar_dust" title="Circumstellar dust">Circumstellar dust</a></li> <li><a href="/wiki/Circumstellar_envelope" title="Circumstellar envelope">Circumstellar envelope</a></li> <li><a href="/wiki/Cosmic_dust" title="Cosmic dust">Cosmic dust</a></li> <li><a href="/wiki/Cosmic_ray" title="Cosmic ray">Cosmic ray</a></li> <li><a href="/wiki/Cosmochemistry" title="Cosmochemistry">Cosmochemistry</a></li> <li><a href="/wiki/Diffuse_interstellar_band" class="mw-redirect" title="Diffuse interstellar band">Diffuse interstellar band</a></li> <li><a href="/wiki/Earliest_known_life_forms" title="Earliest known life forms">Earliest known life forms</a></li> <li><a href="/wiki/Extraterrestrial_life" title="Extraterrestrial life">Extraterrestrial life</a></li> <li><a href="/wiki/Extraterrestrial_liquid_water" title="Extraterrestrial liquid water">Extraterrestrial liquid water</a></li> <li><a href="/wiki/Forbidden_mechanism" title="Forbidden mechanism">Forbidden mechanism</a></li> <li><a href="/wiki/Homochirality" title="Homochirality">Homochirality</a></li> <li><a href="/wiki/Intergalactic_dust" title="Intergalactic dust">Intergalactic dust</a></li> <li><a href="/wiki/Interplanetary_medium" title="Interplanetary medium">Interplanetary medium</a></li> <li><a href="/wiki/Interstellar_medium" title="Interstellar medium">Interstellar medium</a></li> <li><a href="/wiki/Iron%E2%80%93sulfur_world_theory" class="mw-redirect" title="Iron–sulfur world theory">Iron–sulfur world theory</a></li> <li><a href="/wiki/Kerogen" title="Kerogen">Kerogen</a></li> <li><a href="/wiki/Molecules_in_stars" title="Molecules in stars">Molecules in stars</a></li> <li><a href="/wiki/Nexus_for_Exoplanet_System_Science" title="Nexus for Exoplanet System Science">Nexus for Exoplanet System Science</a></li> <li><a href="/wiki/Organic_compound" title="Organic compound">Organic compound</a></li> <li><a href="/wiki/Outer_space" title="Outer space">Outer space</a></li> <li><a href="/wiki/PAH_world_hypothesis" title="PAH world hypothesis">PAH world hypothesis</a></li> <li><a href="/wiki/Photodissociation_region" title="Photodissociation region">Photodissociation region</a></li> <li><a href="/wiki/Polycyclic_aromatic_hydrocarbon" title="Polycyclic aromatic hydrocarbon">Polycyclic aromatic hydrocarbon</a> (PAH)</li> <li><a href="/wiki/Pseudo-panspermia" title="Pseudo-panspermia">Pseudo-panspermia</a></li> <li><a href="/wiki/RNA_world_hypothesis" class="mw-redirect" title="RNA world hypothesis">RNA world hypothesis</a></li> <li><a href="/wiki/Spectroscopy" title="Spectroscopy">Spectroscopy</a></li> <li><a href="/wiki/Tholin" title="Tholin">Tholin</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="font-weight: bold;"><div> 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