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<span>Preparation</span> </div> </a> <button aria-controls="toc-Preparation-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Preparation subsection</span> </button> <ul id="toc-Preparation-sublist" class="vector-toc-list"> <li id="toc-Partial_combustion_of_hydrocarbons" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Partial_combustion_of_hydrocarbons"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>Partial combustion of hydrocarbons</span> </div> </a> <ul id="toc-Partial_combustion_of_hydrocarbons-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Dehydrogenation_of_alkanes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Dehydrogenation_of_alkanes"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.2</span> <span>Dehydrogenation of alkanes</span> </div> </a> <ul id="toc-Dehydrogenation_of_alkanes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Carbochemical_method" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Carbochemical_method"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.3</span> <span>Carbochemical method</span> </div> </a> <ul id="toc-Carbochemical_method-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Bonding" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Bonding"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Bonding</span> </div> </a> <ul id="toc-Bonding-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Physical_properties" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Physical_properties"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Physical properties</span> </div> </a> <button aria-controls="toc-Physical_properties-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Physical properties subsection</span> </button> <ul id="toc-Physical_properties-sublist" class="vector-toc-list"> <li id="toc-Changes_of_state" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Changes_of_state"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Changes of state</span> </div> </a> <ul id="toc-Changes_of_state-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Other"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>Other</span> </div> </a> <ul id="toc-Other-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Applications" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Applications"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Applications</span> </div> </a> <button aria-controls="toc-Applications-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Applications subsection</span> </button> <ul id="toc-Applications-sublist" class="vector-toc-list"> <li id="toc-Welding" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Welding"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Welding</span> </div> </a> <ul id="toc-Welding-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Chemicals" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Chemicals"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>Chemicals</span> </div> </a> <ul id="toc-Chemicals-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Historical_uses" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Historical_uses"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.3</span> <span>Historical uses</span> </div> </a> <ul id="toc-Historical_uses-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Niche_applications" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Niche_applications"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.4</span> <span>Niche applications</span> </div> </a> <ul id="toc-Niche_applications-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Natural_occurrence" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Natural_occurrence"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Natural occurrence</span> </div> </a> <ul id="toc-Natural_occurrence-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Reactions" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Reactions</span> </div> </a> <button aria-controls="toc-Reactions-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Reactions subsection</span> </button> <ul id="toc-Reactions-sublist" class="vector-toc-list"> <li id="toc-Vinylation_reactions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Vinylation_reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.1</span> <span>Vinylation reactions</span> </div> </a> <ul id="toc-Vinylation_reactions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Organometallic_chemistry" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Organometallic_chemistry"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.2</span> <span>Organometallic chemistry</span> </div> </a> <ul id="toc-Organometallic_chemistry-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Acid-base_reactions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Acid-base_reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.3</span> <span>Acid-base reactions</span> </div> </a> <ul id="toc-Acid-base_reactions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Hydrogenation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Hydrogenation"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.4</span> <span>Hydrogenation</span> </div> </a> <ul id="toc-Hydrogenation-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Safety_and_handling" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Safety_and_handling"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Safety and handling</span> </div> </a> <ul id="toc-Safety_and_handling-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</span> <span>External links</span> </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" > <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" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </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"><span class="mw-page-title-main">Acetylene</span></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 71 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-71" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">71 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-af mw-list-item"><a href="https://af.wikipedia.org/wiki/Etyn" title="Etyn – Afrikaans" lang="af" hreflang="af" data-title="Etyn" data-language-autonym="Afrikaans" data-language-local-name="Afrikaans" class="interlanguage-link-target"><span>Afrikaans</span></a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%A3%D8%B3%D9%8A%D8%AA%D9%8A%D9%84%D9%8A%D9%86" title="أسيتيلين – Arabic" lang="ar" hreflang="ar" data-title="أسيتيلين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Asetilen" title="Asetilen – Azerbaijani" lang="az" hreflang="az" data-title="Asetilen" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%A7%D8%B3%D8%AA%DB%8C%D9%84%D9%86" title="استیلن – South Azerbaijani" lang="azb" hreflang="azb" data-title="استیلن" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%87%E0%A6%A5%E0%A6%BE%E0%A6%87%E0%A6%A8" title="ইথাইন – Bangla" lang="bn" hreflang="bn" data-title="ইথাইন" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%90%D1%86%D1%8D%D1%82%D1%8B%D0%BB%D0%B5%D0%BD" title="Ацэтылен – Belarusian" lang="be" hreflang="be" data-title="Ацэтылен" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%90%D1%86%D0%B5%D1%82%D0%B8%D0%BB%D0%B5%D0%BD" title="Ацетилен – Bulgarian" lang="bg" hreflang="bg" data-title="Ацетилен" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Acetilen" title="Acetilen – Bosnian" lang="bs" hreflang="bs" data-title="Acetilen" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Acetil%C3%A8" title="Acetilè – Catalan" lang="ca" hreflang="ca" data-title="Acetilè" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Ethyn" title="Ethyn – Czech" lang="cs" hreflang="cs" data-title="Ethyn" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Acetylen" title="Acetylen – Danish" lang="da" hreflang="da" data-title="Acetylen" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Ethin" title="Ethin – German" lang="de" hreflang="de" data-title="Ethin" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Atset%C3%BCleen" title="Atsetüleen – Estonian" lang="et" hreflang="et" data-title="Atsetüleen" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%91%CE%B9%CE%B8%CE%AF%CE%BD%CE%B9%CE%BF" title="Αιθίνιο – Greek" lang="el" hreflang="el" data-title="Αιθίνιο" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Acetileno" title="Acetileno – Spanish" lang="es" hreflang="es" data-title="Acetileno" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Etino" title="Etino – Esperanto" lang="eo" hreflang="eo" data-title="Etino" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Azetileno" title="Azetileno – Basque" lang="eu" hreflang="eu" data-title="Azetileno" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A7%D8%B3%D8%AA%DB%8C%D9%84%D9%86" title="استیلن – Persian" lang="fa" hreflang="fa" data-title="استیلن" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Ac%C3%A9tyl%C3%A8ne" title="Acétylène – French" lang="fr" hreflang="fr" data-title="Acétylène" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Aic%C3%A9itil%C3%A9in" title="Aicéitiléin – Irish" lang="ga" hreflang="ga" data-title="Aicéitiléin" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Acetileno" title="Acetileno – Galician" lang="gl" hreflang="gl" data-title="Acetileno" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%95%84%EC%84%B8%ED%8B%B8%EB%A0%8C" title="아세틸렌 – Korean" lang="ko" hreflang="ko" data-title="아세틸렌" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D4%B1%D6%81%D5%A5%D5%BF%D5%AB%D5%AC%D5%A5%D5%B6" title="Ացետիլեն – Armenian" lang="hy" hreflang="hy" data-title="Ացետիլեն" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%8F%E0%A4%B8%E0%A4%BF%E0%A4%9F%E0%A4%BF%E0%A4%B2%E0%A5%80%E0%A4%A8" title="एसिटिलीन – Hindi" lang="hi" hreflang="hi" data-title="एसिटिलीन" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Etin" title="Etin – Croatian" lang="hr" hreflang="hr" data-title="Etin" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-io mw-list-item"><a href="https://io.wikipedia.org/wiki/Acetileno" title="Acetileno – Ido" lang="io" hreflang="io" data-title="Acetileno" data-language-autonym="Ido" data-language-local-name="Ido" class="interlanguage-link-target"><span>Ido</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Asetilena" title="Asetilena – Indonesian" lang="id" hreflang="id" data-title="Asetilena" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Acetilene" title="Acetilene – Italian" lang="it" hreflang="it" data-title="Acetilene" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%90%D7%A6%D7%98%D7%99%D7%9C%D7%9F" title="אצטילן – Hebrew" lang="he" hreflang="he" data-title="אצטילן" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-jv mw-list-item"><a href="https://jv.wikipedia.org/wiki/Asetilena" title="Asetilena – Javanese" lang="jv" hreflang="jv" data-title="Asetilena" data-language-autonym="Jawa" data-language-local-name="Javanese" class="interlanguage-link-target"><span>Jawa</span></a></li><li class="interlanguage-link interwiki-kn mw-list-item"><a href="https://kn.wikipedia.org/wiki/%E0%B2%85%E0%B2%B8%E0%B2%BF%E0%B2%9F%E0%B2%BF%E0%B2%B2%E0%B3%80%E0%B2%A8%E0%B3%8D" title="ಅಸಿಟಿಲೀನ್ – Kannada" lang="kn" hreflang="kn" data-title="ಅಸಿಟಿಲೀನ್" data-language-autonym="ಕನ್ನಡ" data-language-local-name="Kannada" class="interlanguage-link-target"><span>ಕನ್ನಡ</span></a></li><li class="interlanguage-link interwiki-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%90%E1%83%AA%E1%83%94%E1%83%A2%E1%83%98%E1%83%9A%E1%83%94%E1%83%9C%E1%83%98" title="აცეტილენი – Georgian" lang="ka" hreflang="ka" data-title="აცეტილენი" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target"><span>ქართული</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%90%D1%86%D0%B5%D1%82%D0%B8%D0%BB%D0%B5%D0%BD" title="Ацетилен – Kazakh" lang="kk" hreflang="kk" data-title="Ацетилен" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%90%D1%86%D0%B5%D1%82%D0%B8%D0%BB%D0%B5%D0%BD" title="Ацетилен – Kyrgyz" lang="ky" hreflang="ky" data-title="Ацетилен" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target"><span>Кыргызча</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Acetil%C4%93ns" title="Acetilēns – Latvian" lang="lv" hreflang="lv" data-title="Acetilēns" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Acetilenas" title="Acetilenas – Lithuanian" lang="lt" hreflang="lt" data-title="Acetilenas" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Acetil%C3%A9n" title="Acetilén – Hungarian" lang="hu" hreflang="hu" data-title="Acetilén" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%90%D1%86%D0%B5%D1%82%D0%B8%D0%BB%D0%B5%D0%BD" title="Ацетилен – Macedonian" lang="mk" hreflang="mk" data-title="Ацетилен" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%85%E0%B4%B8%E0%B4%B1%E0%B5%8D%E0%B4%B1%E0%B5%8D%E2%80%8C%E0%B4%B2%E0%B5%80%E0%B5%BB" title="അസറ്റ്‌ലീൻ – Malayalam" lang="ml" hreflang="ml" data-title="അസറ്റ്‌ലീൻ" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target"><span>മലയാളം</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Asetilena" title="Asetilena – Malay" lang="ms" hreflang="ms" data-title="Asetilena" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Ethyn" title="Ethyn – Dutch" lang="nl" hreflang="nl" data-title="Ethyn" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%A2%E3%82%BB%E3%83%81%E3%83%AC%E3%83%B3" title="アセチレン – Japanese" lang="ja" hreflang="ja" data-title="アセチレン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Acetylen" title="Acetylen – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Acetylen" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-nn mw-list-item"><a href="https://nn.wikipedia.org/wiki/Acetylen" title="Acetylen – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Acetylen" data-language-autonym="Norsk nynorsk" data-language-local-name="Norwegian Nynorsk" class="interlanguage-link-target"><span>Norsk nynorsk</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Atsetilen" title="Atsetilen – Uzbek" lang="uz" hreflang="uz" data-title="Atsetilen" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Etyn" title="Etyn – Polish" lang="pl" hreflang="pl" data-title="Etyn" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Acetileno" title="Acetileno – Portuguese" lang="pt" hreflang="pt" data-title="Acetileno" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Acetilen%C4%83" title="Acetilenă – Romanian" lang="ro" hreflang="ro" data-title="Acetilenă" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%90%D1%86%D0%B5%D1%82%D0%B8%D0%BB%D0%B5%D0%BD" title="Ацетилен – Russian" lang="ru" hreflang="ru" data-title="Ацетилен" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sq mw-list-item"><a href="https://sq.wikipedia.org/wiki/Acetileni" title="Acetileni – Albanian" lang="sq" hreflang="sq" data-title="Acetileni" data-language-autonym="Shqip" data-language-local-name="Albanian" class="interlanguage-link-target"><span>Shqip</span></a></li><li class="interlanguage-link interwiki-scn mw-list-item"><a href="https://scn.wikipedia.org/wiki/Acitalena" title="Acitalena – Sicilian" lang="scn" hreflang="scn" data-title="Acitalena" data-language-autonym="Sicilianu" data-language-local-name="Sicilian" class="interlanguage-link-target"><span>Sicilianu</span></a></li><li class="interlanguage-link interwiki-si mw-list-item"><a href="https://si.wikipedia.org/wiki/%E0%B6%87%E0%B7%83%E0%B7%92%E0%B6%A7%E0%B6%BD%E0%B7%93%E0%B6%B1%E0%B7%8A" title="ඇසිටලීන් – Sinhala" lang="si" hreflang="si" data-title="ඇසිටලීන්" data-language-autonym="සිංහල" data-language-local-name="Sinhala" class="interlanguage-link-target"><span>සිංහල</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Acetylene" title="Acetylene – Simple English" lang="en-simple" hreflang="en-simple" data-title="Acetylene" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Acetyl%C3%A9n" title="Acetylén – Slovak" lang="sk" hreflang="sk" data-title="Acetylén" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Acetilen" title="Acetilen – Slovenian" lang="sl" hreflang="sl" data-title="Acetilen" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%90%D1%86%D0%B5%D1%82%D0%B8%D0%BB%D0%B5%D0%BD" title="Ацетилен – Serbian" lang="sr" hreflang="sr" data-title="Ацетилен" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Acetilen" title="Acetilen – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Acetilen" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Etyyni" title="Etyyni – Finnish" lang="fi" hreflang="fi" data-title="Etyyni" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Etyn" title="Etyn – Swedish" lang="sv" hreflang="sv" data-title="Etyn" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%85%E0%AE%9A%E0%AE%BF%E0%AE%9F%E0%AF%8D%E0%AE%9F%E0%AE%BF%E0%AE%B2%E0%AF%80%E0%AE%A9%E0%AF%8D" title="அசிட்டிலீன் – Tamil" lang="ta" hreflang="ta" data-title="அசிட்டிலீன்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-tt mw-list-item"><a href="https://tt.wikipedia.org/wiki/Atsetilen" title="Atsetilen – Tatar" lang="tt" hreflang="tt" data-title="Atsetilen" data-language-autonym="Татарча / tatarça" data-language-local-name="Tatar" class="interlanguage-link-target"><span>Татарча / tatarça</span></a></li><li class="interlanguage-link interwiki-te mw-list-item"><a href="https://te.wikipedia.org/wiki/%E0%B0%85%E0%B0%B8%E0%B0%BF%E0%B0%9F%E0%B0%BF%E0%B0%B2%E0%B0%BF%E0%B0%A8%E0%B1%8D" title="అసిటిలిన్ – Telugu" lang="te" hreflang="te" data-title="అసిటిలిన్" data-language-autonym="తెలుగు" data-language-local-name="Telugu" class="interlanguage-link-target"><span>తెలుగు</span></a></li><li class="interlanguage-link interwiki-tg mw-list-item"><a href="https://tg.wikipedia.org/wiki/%D0%90%D1%81%D0%B5%D1%82%D0%B8%D0%BB%D0%B5%D0%BD" title="Асетилен – Tajik" lang="tg" hreflang="tg" data-title="Асетилен" data-language-autonym="Тоҷикӣ" data-language-local-name="Tajik" class="interlanguage-link-target"><span>Тоҷикӣ</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Asetilen" title="Asetilen – Turkish" lang="tr" hreflang="tr" data-title="Asetilen" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%90%D1%86%D0%B5%D1%82%D0%B8%D0%BB%D0%B5%D0%BD" title="Ацетилен – Ukrainian" lang="uk" hreflang="uk" data-title="Ацетилен" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-ur mw-list-item"><a href="https://ur.wikipedia.org/wiki/%D8%B3%D8%B1%DA%A9%DB%8C%D9%86" title="سرکین – Urdu" lang="ur" hreflang="ur" data-title="سرکین" data-language-autonym="اردو" data-language-local-name="Urdu" class="interlanguage-link-target"><span>اردو</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Acetylen" title="Acetylen – Vietnamese" lang="vi" hreflang="vi" data-title="Acetylen" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-zh-classical mw-list-item"><a href="https://zh-classical.wikipedia.org/wiki/%E4%B9%99%E7%82%94" title="乙炔 – Literary Chinese" lang="lzh" hreflang="lzh" data-title="乙炔" data-language-autonym="文言" data-language-local-name="Literary Chinese" class="interlanguage-link-target"><span>文言</span></a></li><li class="interlanguage-link interwiki-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E4%B9%99%E7%82%94" title="乙炔 – Wu" lang="wuu" hreflang="wuu" data-title="乙炔" data-language-autonym="吴语" data-language-local-name="Wu" class="interlanguage-link-target"><span>吴语</span></a></li><li class="interlanguage-link interwiki-zh-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E4%B9%99%E7%82%94" title="乙炔 – Cantonese" lang="yue" hreflang="yue" data-title="乙炔" data-language-autonym="粵語" data-language-local-name="Cantonese" class="interlanguage-link-target"><span>粵語</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E4%B9%99%E7%82%94" title="乙炔 – Chinese" lang="zh" hreflang="zh" data-title="乙炔" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q133145#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> <div id="left-navigation"> <nav aria-label="Namespaces"> <div 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data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .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">"HCCH" redirects here. For other uses, see <a href="/wiki/HCCH_(disambiguation)" class="mw-disambig" title="HCCH (disambiguation)">HCCH (disambiguation)</a>.</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">"Ethyne" redirects here. Not to be confused with <a href="/wiki/Ethane" title="Ethane">ethane</a> or <a href="/wiki/Ethene" class="mw-redirect" title="Ethene">ethene</a>.</div> <p> <style data-mw-deduplicate="TemplateStyles:r1084375498">.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%}</style> </p> <table class="infobox ib-chembox"> <caption>Acetylene </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Acetylene-CRC-IR-dimensions-2D.svg" class="mw-file-description" title="Acetylene"><img alt="Acetylene" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6a/Acetylene-CRC-IR-dimensions-2D.svg/150px-Acetylene-CRC-IR-dimensions-2D.svg.png" decoding="async" width="150" height="95" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6a/Acetylene-CRC-IR-dimensions-2D.svg/225px-Acetylene-CRC-IR-dimensions-2D.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6a/Acetylene-CRC-IR-dimensions-2D.svg/300px-Acetylene-CRC-IR-dimensions-2D.svg.png 2x" data-file-width="1100" data-file-height="700" /></a></span> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Acetylene-CRC-IR-3D-balls.png" class="mw-file-description" title="Acetylene"><img alt="Acetylene" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8b/Acetylene-CRC-IR-3D-balls.png/150px-Acetylene-CRC-IR-3D-balls.png" decoding="async" width="150" height="43" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8b/Acetylene-CRC-IR-3D-balls.png/225px-Acetylene-CRC-IR-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8b/Acetylene-CRC-IR-3D-balls.png/300px-Acetylene-CRC-IR-3D-balls.png 2x" data-file-width="1100" data-file-height="318" /></a></span> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Acetylene-3D-vdW.png" class="mw-file-description" title="Acetylene – space-filling model"><img alt="Acetylene – space-filling model" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Acetylene-3D-vdW.png/150px-Acetylene-3D-vdW.png" decoding="async" width="150" height="101" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Acetylene-3D-vdW.png/225px-Acetylene-3D-vdW.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Acetylene-3D-vdW.png/300px-Acetylene-3D-vdW.png 2x" data-file-width="1100" data-file-height="741" /></a></span> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Acetylene-xtal-3D-vdW-111.png" class="mw-file-description" title="space-filling model of solid acetylene"><img alt="space-filling model of solid acetylene" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ea/Acetylene-xtal-3D-vdW-111.png/200px-Acetylene-xtal-3D-vdW-111.png" decoding="async" width="200" height="195" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ea/Acetylene-xtal-3D-vdW-111.png/300px-Acetylene-xtal-3D-vdW-111.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ea/Acetylene-xtal-3D-vdW-111.png/400px-Acetylene-xtal-3D-vdW-111.png 2x" data-file-width="1100" data-file-height="1075" /></a></span> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; 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;">Acetylene<sup id="cite_ref-iupac2013_1-0" class="reference"><a href="#cite_note-iupac2013-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-P-14.3.4.2_2-0" class="reference"><a href="#cite_note-P-14.3.4.2-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></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;">Ethyne<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup></div></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; 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><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=74-86-2">74-86-2</a></span><sup> <span typeof="mw:File"><span><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" /></span></span><span style="display:none">Y</span></sup></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><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=C%23C">Interactive image</a></span></li></ul></div> </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>906677 </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><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=27518">CHEBI:27518</a></span><sup> <span typeof="mw:File"><span><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" /></span></span><span style="display:none">Y</span></sup></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><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL116336">ChEMBL116336</a></span><sup> <span typeof="mw:File"><span><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" /></span></span><span style="display:none">Y</span></sup></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><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.6086.html">6086</a></span><sup> <span typeof="mw:File"><span><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" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.000.743">100.000.743</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q133145#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></span> </td></tr> <tr> <td><a href="/wiki/European_Community_number" title="European Community number"><span title="European Community number (chemical identifier)">EC Number</span></a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>200-816-9</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>210 </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><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/C01548">C01548</a></span><sup> <span typeof="mw:File"><span><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" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </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><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/6326">6326</a></span></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>AO9600000</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><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/OC7TV75O83">OC7TV75O83</a></span><sup> <span typeof="mw:File"><span><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" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/UN_number" title="UN number">UN number</a> </td> <td><a href="/wiki/List_of_UN_Numbers_1001_to_1100" class="mw-redirect" title="List of UN Numbers 1001 to 1100">1001</a> (dissolved)<br /><a href="/wiki/List_of_UN_Numbers_3101_to_3200" class="mw-redirect" title="List of UN Numbers 3101 to 3200">3138</a> (in mixture with <a href="/wiki/Ethylene" title="Ethylene">ethylene</a> and <a href="/wiki/Propylene" title="Propylene">propylene</a>) </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> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID6026379">DTXSID6026379</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q133145#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></span></span></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; background:transparent;"><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/C2H2/c1-2/h1-2H<sup> <span typeof="mw:File"><span><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" /></span></span><span style="display:none">Y</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: HSFWRNGVRCDJHI-UHFFFAOYSA-N<sup> <span typeof="mw:File"><span><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" /></span></span><span style="display:none">Y</span></sup></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/C2H2/c1-2/h1-2H</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: HSFWRNGVRCDJHI-UHFFFAOYAY</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; background:transparent;"><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%;">C#C</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; 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><span title="Carbon">C</span><sub>2</sub><span title="Hydrogen">H</span><sub>2</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7001260380000000000♠"></span>26.038</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td>Appearance </td> <td>Colorless gas </td></tr> <tr> <td><a href="/wiki/Odor" title="Odor">Odor</a> </td> <td>Odorless </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>1.1772 g/L = 1.1772 kg/m<sup>3</sup> (0 °C, 101.3 kPa)<sup id="cite_ref-GESTIS_4-0" class="reference"><a href="#cite_note-GESTIS-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>−80.8 °C (−113.4 °F; 192.3 K) <a href="/wiki/Triple_point" title="Triple point">Triple point</a> at 1.27 atm </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Sublimation_(phase_transition)" title="Sublimation (phase transition)">Sublimation<br />conditions</a></div> </td> <td>−84 °C; −119 °F; 189 K (1 atm) </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>slightly soluble </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> </td> <td>slightly soluble in alcohol <br /> soluble in <a href="/wiki/Acetone" title="Acetone">acetone</a>, <a href="/wiki/Benzene" title="Benzene">benzene</a> </td></tr> <tr> <td><a href="/wiki/Vapor_pressure" title="Vapor pressure">Vapor pressure</a> </td> <td>44.2 atm (20 °C)<sup id="cite_ref-NIOSH_5-0" class="reference"><a href="#cite_note-NIOSH-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">Acidity</a> (p<i>K</i><sub>a</sub>) </td> <td>25<sup id="cite_ref-airliquide_6-0" class="reference"><a href="#cite_note-airliquide-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Conjugate_acid" class="mw-redirect" title="Conjugate acid">Conjugate acid</a> </td> <td>Ethynium </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>−20.8<span style="margin:0 .15em 0 .25em">×</span>10<sup>−6</sup> cm<sup>3</sup>/mol <sup id="cite_ref-CRC97_7-0" class="reference"><a href="#cite_note-CRC97-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Thermal_conductivity" class="mw-redirect" title="Thermal conductivity">Thermal conductivity</a> </td> <td>21.4 mW·m<sup>−1</sup>·K<sup>−1</sup> (300 K) <sup id="cite_ref-CRC97_7-1" class="reference"><a href="#cite_note-CRC97-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Structure </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Molecular_geometry" title="Molecular geometry">Molecular shape</a></div> </td> <td><a href="/wiki/Linear_(chemistry)" class="mw-redirect" title="Linear (chemistry)">Linear</a> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Thermochemistry<sup id="cite_ref-CRC97_7-2" class="reference"><a href="#cite_note-CRC97-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </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> <span style="font-size:112%;">(<i>C</i>)</span></div> </td> <td>44.036 J·mol<sup>−1</sup>·K<sup>−1</sup> </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<br />entropy</a> <span style="font-size:112%;">(<i>S</i><sup>⦵</sup><sub>298</sub>)</span></div> </td> <td>200.927 J·mol<sup>−1</sup>·K<sup>−1</sup> </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<br />formation</a> <span style="font-size:112%;">(Δ<sub>f</sub><i>H</i><sup>⦵</sup><sub>298</sub>)</span></div> </td> <td>227.400 kJ·mol<sup>−1</sup> </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> <span style="font-size:112%;">(Δ<sub>f</sub><i>G</i><sup>⦵</sup>)</span></div> </td> <td>209.879 kJ·mol<sup>−1</sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Standard_enthalpy_change_of_combustion" class="mw-redirect" title="Standard enthalpy change of combustion">Std enthalpy of<br />combustion</a> <span style="font-size:112%;">(Δ<sub>c</sub><i>H</i><sup>⦵</sup><sub>298</sub>)</span></div> </td> <td>1300 kJ·mol<sup>−1</sup> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Hazards </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals" title="Globally Harmonized System of Classification and Labelling of Chemicals"><b>GHS</b> 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><span typeof="mw:File"><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></span><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-exclam.svg" class="mw-file-description" title="GHS07: Exclamation mark"><img alt="GHS07: Exclamation mark" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/50px-GHS-pictogram-exclam.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/75px-GHS-pictogram-exclam.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/100px-GHS-pictogram-exclam.svg.png 2x" data-file-width="512" data-file-height="512" /></a></span> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals#Signal_word" title="Globally Harmonized System of Classification and Labelling of Chemicals">Signal word</a></div> </td> <td><b>Danger</b> </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="H336: May cause drowsiness or dizziness">H336</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="P233: Keep container tightly closed.">P233</abbr>, <abbr class="abbr" title="P261: Avoid breathing dust/fume/gas/mist/vapours/spray.">P261</abbr>, <abbr class="abbr" title="P271: Use only outdoors or in a well-ventilated area.">P271</abbr>, <abbr class="abbr" title="P304: IF INHALED:">P304</abbr>, <abbr class="abbr" title="P312: Call a POISON CENTER or doctor/physician if you feel unwell.">P312</abbr>, <abbr class="abbr" title="P340: Remove victim to fresh air and keep at rest in a position comfortable for breathing.">P340</abbr>, <abbr class="abbr" title="P377: Leaking gas fire – do not extinguish unless leak can be stopped safely.">P377</abbr>, <abbr class="abbr" title="P381: In case of leakage, eliminate all ignition sources.">P381</abbr>, <abbr class="abbr" title="P403: Store in a well ventilated place.">P403</abbr>, <abbr class="abbr" title="P405: Store locked up.">P405</abbr>, <abbr class="abbr" title="P501: Dispose of contents/container to ...">P501</abbr> </td></tr> <tr> <td><a href="/wiki/NFPA_704" title="NFPA 704"><b>NFPA 704</b></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"><span><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_bf68974705340276" /></span><map name="ImageMap_bf68974705340276"><area href="/wiki/NFPA_704#Blue" shape="poly" coords="23,23,47,47,23,70,0,47" alt="Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentine" title="Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentine" /><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"><span title="Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentine" class="notheme mw-no-invert">1</span></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</span></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</span></a></div></div></div></div> </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<br />temperature</a></div> </td> <td>300 °C (572 °F; 573 K) </td></tr> <tr> <td><a href="/wiki/Explosive_limit" class="mw-redirect" title="Explosive limit">Explosive limits</a> </td> <td>2.5–100% </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health"><b>NIOSH</b></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>none<sup id="cite_ref-NIOSH_5-1" class="reference"><a href="#cite_note-NIOSH-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </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>C 2500 ppm (2662 mg/m<sup>3</sup>)<sup id="cite_ref-NIOSH_5-2" class="reference"><a href="#cite_note-NIOSH-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </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>N.D.<sup id="cite_ref-NIOSH_5-3" class="reference"><a href="#cite_note-NIOSH-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; 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;"><span typeof="mw:File"><span><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" /></span></span><span style="display:none">Y</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=477240406&page2=Acetylene">verify</a></span> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <sup><span typeof="mw:File"><span><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" /></span></span><span style="display:none">Y</span><span typeof="mw:File"><span><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" /></span></span><span style="display:none">N</span></sup> ?) </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> <p><b>Acetylene</b> (<a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">systematic name</a>: <b>ethyne</b>) is the <a href="/wiki/Chemical_compound" title="Chemical compound">chemical compound</a> with the formula <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><span class="chemf nowrap">C<sub class="template-chem2-sub">2</sub>H<sub class="template-chem2-sub">2</sub></span> and structure <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H−C≡C−H</span>. It is a <a href="/wiki/Hydrocarbon" title="Hydrocarbon">hydrocarbon</a> and the simplest <a href="/wiki/Alkyne" title="Alkyne">alkyne</a>.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> This colorless gas is widely used as a fuel and a chemical building block. It is unstable in its pure form and thus is usually handled as a solution.<sup id="cite_ref-Ullmann_9-0" class="reference"><a href="#cite_note-Ullmann-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> Pure acetylene is odorless, but commercial grades usually have a marked odor due to impurities such as <a href="/wiki/Divinyl_sulfide" title="Divinyl sulfide">divinyl sulfide</a> and <a href="/wiki/Phosphine" title="Phosphine">phosphine</a>.<sup id="cite_ref-Ullmann_9-1" class="reference"><a href="#cite_note-Ullmann-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-msds_10-0" class="reference"><a href="#cite_note-msds-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p><p>As an alkyne, acetylene is <a href="/wiki/Saturated_and_unsaturated_compounds" title="Saturated and unsaturated compounds">unsaturated</a> because its two carbon atoms are <a href="/wiki/Chemical_bond" title="Chemical bond">bonded</a> together in a <a href="/wiki/Triple_bond" title="Triple bond">triple bond</a>. The carbon–carbon triple bond places all four atoms in the same straight line, with CCH bond angles of 180°.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Discovery">Discovery</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetylene&action=edit&section=1" title="Edit section: Discovery"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Acetylene was discovered in 1836 by <a href="/wiki/Edmund_Davy" title="Edmund Davy">Edmund Davy</a>, who identified it as a "new carburet of hydrogen".<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> It was an accidental discovery while attempting to isolate <a href="/wiki/Potassium" title="Potassium">potassium</a> metal. By heating <a href="/wiki/Potassium_carbonate" title="Potassium carbonate">potassium carbonate</a> with carbon at very high temperatures, he produced a residue of what is now known as <a href="/wiki/Potassium_carbide" class="mw-redirect" title="Potassium carbide">potassium carbide</a>, (K<sub>2</sub>C<sub>2</sub>), which reacted with water to release the new gas. It was rediscovered in 1860 by French chemist <a href="/wiki/Marcellin_Berthelot" title="Marcellin Berthelot">Marcellin Berthelot</a>, who coined the name <i>acétylène</i>.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> Berthelot's empirical formula for acetylene (C<sub>4</sub>H<sub>2</sub>), as well as the alternative name "<i>quadricarbure d'hydrogène</i>" (hydrogen quadricarbide), were incorrect because many chemists at that time used the wrong atomic mass for carbon (6 instead of 12).<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> Berthelot was able to prepare this gas by passing vapours of organic compounds (methanol, ethanol, etc.) through a red hot tube and collecting the <a href="/wiki/Effluent" title="Effluent">effluent</a>. He also found that acetylene was formed by sparking electricity through mixed <a href="/wiki/Cyanogen" title="Cyanogen">cyanogen</a> and <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a> gases. Berthelot later obtained acetylene directly by passing hydrogen between the poles of a <a href="/wiki/Arc_lamp" title="Arc lamp">carbon arc</a>.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Preparation">Preparation</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetylene&action=edit&section=2" title="Edit section: Preparation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Partial_combustion_of_hydrocarbons">Partial combustion of hydrocarbons</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetylene&action=edit&section=3" title="Edit section: Partial combustion of hydrocarbons"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Since the 1950s, acetylene has mainly been manufactured by the partial combustion of <a href="/wiki/Methane" title="Methane">methane</a> in the US, much of the EU, and many other countries:<sup id="cite_ref-Ullmann_9-2" class="reference"><a href="#cite_note-Ullmann-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">3 CH<sub class="template-chem2-sub">4</sub> + 3 O<sub class="template-chem2-sub">2</sub> → C<sub class="template-chem2-sub">2</sub>H<sub class="template-chem2-sub">2</sub> + CO + 5 H<sub class="template-chem2-sub">2</sub>O</span></dd></dl> <p>It is a recovered side product in production of <a href="/wiki/Ethylene" title="Ethylene">ethylene</a> by <a href="/wiki/Cracking_(chemistry)" title="Cracking (chemistry)">cracking</a> of <a href="/wiki/Hydrocarbon" title="Hydrocarbon">hydrocarbons</a>. Approximately 400,000 tonnes were produced by this method in 1983.<sup id="cite_ref-Ullmann_9-3" class="reference"><a href="#cite_note-Ullmann-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> Its presence in ethylene is usually undesirable because of its explosive character and its ability to poison <a href="/wiki/Ziegler%E2%80%93Natta_catalyst" title="Ziegler–Natta catalyst">Ziegler–Natta catalysts</a>. It is selectively hydrogenated into ethylene, usually using <a href="/wiki/Palladium" title="Palladium">Pd</a>–<a href="/wiki/Silver" title="Silver">Ag</a> catalysts.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Dehydrogenation_of_alkanes">Dehydrogenation of alkanes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetylene&action=edit&section=4" title="Edit section: Dehydrogenation of alkanes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The heaviest alkanes in petroleum and natural gas are cracked into lighter molecules which are dehydrogenated at high temperature: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">2</sub>H<sub class="template-chem2-sub">6</sub> → C<sub class="template-chem2-sub">2</sub>H<sub class="template-chem2-sub">2</sub> + 2 H<sub class="template-chem2-sub">2</sub></span></dd> <dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">2 CH<sub class="template-chem2-sub">4</sub> → C<sub class="template-chem2-sub">2</sub>H<sub class="template-chem2-sub">2</sub> + 3 H<sub class="template-chem2-sub">2</sub></span></dd></dl> <p>This last reaction is implemented in the process of anaerobic decomposition of methane by microwave plasma.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup><sup class="noprint Inline-Template noprint Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:No_original_research#Primary,_secondary_and_tertiary_sources" title="Wikipedia:No original research"><span title="So I take it they're not planning on using Nuclear Fusion if it appears tomorrow, since it'll eventually fuse things to carbon and carbon is the devil incarnate, amirite? How are they powering the massive inefficient microwave plasma generators NOW? Do their employees not exhale? Should they maybe keep their ridiculous claims of any process being carbon free or neutral off the encyclopedia and stop letting marketing edit articles? Oh woops huge amounts of it were burned, producing a bunch of CO and CO2 gas depending on how rich the oxygen mix was. (October 2024)">non-primary source needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading3"><h3 id="Carbochemical_method">Carbochemical method</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetylene&action=edit&section=5" title="Edit section: Carbochemical method"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The first acetylene produced was by Edmund Davy in 1836, via postassium carbide.<sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> Acetylene was historically produced by hydrolysis (reaction with water) of calcium carbide: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CaC<sub class="template-chem2-sub">2</sub> + 2 H<sub class="template-chem2-sub">2</sub>O → Ca(OH)<sub class="template-chem2-sub">2</sub> + C<sub class="template-chem2-sub">2</sub>H<sub class="template-chem2-sub">2</sub></span></dd></dl> <p>This reaction was discovered by <a href="/wiki/Friedrich_W%C3%B6hler" title="Friedrich Wöhler">Friedrich Wöhler</a> in 1862,<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> but a suitable commercial scale production method which allowed acetylene to be put into wider scale use was not found until 1892 by the Canadian inventor <a href="/wiki/Thomas_Willson" title="Thomas Willson">Thomas Willson</a> while searching for a viable commercial production method for aluminum.<sup id="cite_ref-Willson_24-0" class="reference"><a href="#cite_note-Willson-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p><p>As late as the early 21st century, China, Japan, and Eastern Europe produced acetylene primarily by this method.<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> </p><p>The use of this technology has since declined worldwide with the notable exception of China, with its emphasis on coal-based chemical industry, as of 2013. Otherwise <a href="/wiki/Petroleum" title="Petroleum">oil</a> has increasingly supplanted <a href="/wiki/Coal" title="Coal">coal</a> as the chief source of <a href="/wiki/Redox" title="Redox">reduced</a> carbon.<sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> </p><p>Calcium carbide production requires high temperatures, ~2000 °C, necessitating the use of an <a href="/wiki/Electric_arc_furnace" title="Electric arc furnace">electric arc furnace</a>. In the US, this process was an important part of the late-19th century revolution in chemistry enabled by the massive <a href="/wiki/Hydroelectricity" title="Hydroelectricity">hydroelectric power</a> project at <a href="/wiki/Niagara_Falls" title="Niagara Falls">Niagara Falls</a>.<sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Bonding">Bonding</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetylene&action=edit&section=6" title="Edit section: Bonding"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In terms of <a href="/wiki/Valence_bond_theory" title="Valence bond theory">valence bond theory</a>, in each carbon atom the 2s <a href="/wiki/Atomic_orbital" title="Atomic orbital">orbital</a> <a href="/wiki/Orbital_hybridisation" title="Orbital hybridisation">hybridizes</a> with one 2p orbital thus forming an sp hybrid. The other two 2p orbitals remain unhybridized. The two ends of the two sp hybrid <a href="/wiki/Orbital_overlap" title="Orbital overlap">orbital overlap</a> to form a strong <a href="/wiki/Sigma_bond" title="Sigma bond">σ valence bond</a> between the carbons, while on each of the other two ends hydrogen atoms attach also by σ bonds. The two unchanged 2p orbitals form a pair of weaker <a href="/wiki/Pi_bond" title="Pi bond">π bonds</a>.<sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> </p><p>Since acetylene is a linear <a href="/wiki/Molecular_symmetry" title="Molecular symmetry">symmetrical molecule</a>, it possesses the D<sub>∞h</sub> <a href="/wiki/Molecular_symmetry#Point_group" title="Molecular symmetry">point group</a>.<sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Physical_properties">Physical properties</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetylene&action=edit&section=7" title="Edit section: Physical properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Changes_of_state">Changes of state</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetylene&action=edit&section=8" title="Edit section: Changes of state"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>At atmospheric pressure, acetylene cannot exist as a liquid and does not have a melting point. The <a href="/wiki/Triple_point" title="Triple point">triple point</a> on the <a href="/wiki/Phase_diagram" title="Phase diagram">phase diagram</a> corresponds to the melting point (−80.8 °C) at the minimal pressure at which liquid acetylene can exist (1.27 atm). At temperatures below the triple point, solid acetylene can change directly to the <a href="/wiki/Vapour" class="mw-redirect" title="Vapour">vapour</a> (gas) by <a href="/wiki/Sublimation_(phase_transition)" title="Sublimation (phase transition)">sublimation</a>. The sublimation point at atmospheric pressure is −84.0 °C.<sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Other">Other</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetylene&action=edit&section=9" title="Edit section: Other"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>At room temperature, the solubility of acetylene in <a href="/wiki/Acetone" title="Acetone">acetone</a> is 27.9 g per kg. For the same amount of <a href="/wiki/Dimethylformamide" title="Dimethylformamide">dimethylformamide</a> (DMF), the solubility is 51 g. At 20.26 bar, the solubility increases to 689.0 and 628.0 g for acetone and DMF, respectively. These solvents are used in pressurized gas cylinders.<sup id="cite_ref-Ull_31-0" class="reference"><a href="#cite_note-Ull-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Applications">Applications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetylene&action=edit&section=10" title="Edit section: Applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Welding">Welding</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetylene&action=edit&section=11" title="Edit section: Welding"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Approximately 20% of acetylene is supplied by the <a href="/wiki/Industrial_gas" title="Industrial gas">industrial gases industry</a> for <a href="/wiki/Oxyacetylene" class="mw-redirect" title="Oxyacetylene">oxyacetylene</a> <a href="/wiki/Gas_welding" class="mw-redirect" title="Gas welding">gas welding</a> and <a href="/wiki/Oxy-fuel_welding_and_cutting" title="Oxy-fuel welding and cutting">cutting</a> due to the high temperature of the flame. Combustion of acetylene with oxygen produces a flame of over 3,600 K (3,330 °C; 6,020 °F), releasing 11.8 <a href="/wiki/Kilojoule" class="mw-redirect" title="Kilojoule">kJ</a>/g. Oxygen with acetylene is the hottest burning common gas mixture.<sup id="cite_ref-Linde2013_32-0" class="reference"><a href="#cite_note-Linde2013-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> Acetylene is the third-hottest natural chemical flame after <a href="/wiki/Dicyanoacetylene" title="Dicyanoacetylene">dicyanoacetylene</a>'s 5,260 K (4,990 °C; 9,010 °F) and <a href="/wiki/Cyanogen" title="Cyanogen">cyanogen</a> at 4,798 K (4,525 °C; 8,177 °F). <a href="/wiki/Oxy-fuel_welding_and_cutting" title="Oxy-fuel welding and cutting">Oxy-acetylene welding</a> was a popular welding process in previous decades. The development and advantages of <a href="/wiki/Arc_welding" title="Arc welding">arc-based welding processes</a> have made oxy-fuel welding nearly extinct for many applications. Acetylene usage for welding has dropped significantly. On the other hand, oxy-acetylene welding <i>equipment</i> is quite versatile – not only because the torch is preferred for some sorts of iron or steel welding (as in certain artistic applications), but also because it lends itself easily to brazing, braze-welding, metal heating (for annealing or tempering, bending or forming), the loosening of corroded nuts and bolts, and other applications. <a href="/wiki/Bell_Canada" title="Bell Canada">Bell Canada</a> cable-repair technicians still use portable acetylene-fuelled torch kits as a <a href="/wiki/Soldering" title="Soldering">soldering</a> tool for sealing lead sleeve splices in <a href="/wiki/Manhole" title="Manhole">manholes</a> and in some aerial locations. Oxyacetylene welding may also be used in areas where electricity is not readily accessible. Oxyacetylene cutting is used in many metal fabrication shops. For use in welding and cutting, the working pressures must be controlled by a regulator, since above 15 psi (100 kPa), if subjected to a shockwave (caused, for example, by a <a href="/wiki/Flashback_(welding)" class="mw-redirect" title="Flashback (welding)">flashback</a>), acetylene <a href="/wiki/Decompose" class="mw-redirect" title="Decompose">decomposes</a> explosively into <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a> and <a href="/wiki/Carbon" title="Carbon">carbon</a>.<sup id="cite_ref-33" class="reference"><a href="#cite_note-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> </p> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Laskarbit.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/83/Laskarbit.jpg/200px-Laskarbit.jpg" decoding="async" width="200" height="301" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/83/Laskarbit.jpg/300px-Laskarbit.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/83/Laskarbit.jpg/400px-Laskarbit.jpg 2x" data-file-width="1288" data-file-height="1936" /></a><figcaption>Acetylene fuel container/burner as used in the island of <a href="/wiki/Bali" title="Bali">Bali</a></figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Chemicals">Chemicals</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetylene&action=edit&section=12" title="Edit section: Chemicals"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Acetylene is useful for many processes, but few are conducted on a commercial scale.<sup id="cite_ref-trot_34-0" class="reference"><a href="#cite_note-trot-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> </p><p>One of the major chemical applications is <a href="/wiki/Ethynylation" title="Ethynylation">ethynylation</a> of formaldehyde.<sup id="cite_ref-Ullmann_9-4" class="reference"><a href="#cite_note-Ullmann-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> Acetylene adds to <a href="/wiki/Aldehyde" title="Aldehyde">aldehydes</a> and <a href="/wiki/Ketone" title="Ketone">ketones</a> to form α-ethynyl alcohols: </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:Reppe-chemistry-endiol-V1.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/14/Reppe-chemistry-endiol-V1.svg/300px-Reppe-chemistry-endiol-V1.svg.png" decoding="async" width="300" height="106" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/14/Reppe-chemistry-endiol-V1.svg/450px-Reppe-chemistry-endiol-V1.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/14/Reppe-chemistry-endiol-V1.svg/600px-Reppe-chemistry-endiol-V1.svg.png 2x" data-file-width="810" data-file-height="287" /></a></span></dd></dl> <p>The reaction gives <a href="/wiki/1,4-Butynediol" title="1,4-Butynediol">butynediol</a>, with <a href="/wiki/Propargyl_alcohol" title="Propargyl alcohol">propargyl alcohol</a> as the by-product. <a href="/wiki/Copper(I)_acetylide" title="Copper(I) acetylide">Copper acetylide</a> is used as the catalyst.<sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-36" class="reference"><a href="#cite_note-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> </p><p>In addition to ethynylation, acetylene reacts with <a href="/wiki/Carbon_monoxide" title="Carbon monoxide">carbon monoxide</a>, acetylene reacts to give <a href="/wiki/Acrylic_acid" title="Acrylic acid">acrylic acid</a>, or acrylic esters. Metal catalysts are required. These derivatives form products such as <a href="/wiki/Acrylic_fiber" title="Acrylic fiber">acrylic fibers</a>, <a href="/wiki/Acrylic_glass" class="mw-redirect" title="Acrylic glass">glasses</a>, <a href="/wiki/Acrylic_paint" title="Acrylic paint">paints</a>, <a href="/wiki/Acrylic_resin" title="Acrylic resin">resins</a>, and <a href="/wiki/Acrylate_polymer" title="Acrylate polymer">polymers</a>. Except in China, use of acetylene as a chemical feedstock has declined by 70% from 1965 to 2007 owing to cost and environmental considerations.<sup id="cite_ref-37" class="reference"><a href="#cite_note-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> In China, acetylene is a major precursor to <a href="/wiki/Vinyl_chloride" title="Vinyl chloride">vinyl chloride</a>.<sup id="cite_ref-trot_34-1" class="reference"><a href="#cite_note-trot-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Historical_uses">Historical uses</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetylene&action=edit&section=13" title="Edit section: Historical uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Prior to the widespread use of petrochemicals, coal-derived acetylene was a building block for several industrial chemicals. Thus acetylene can be hydrated to give <a href="/wiki/Acetaldehyde" title="Acetaldehyde">acetaldehyde</a>, which in turn can be oxidized to acetic acid. Processes leading to acrylates were also commercialized. Almost all of these processes became obsolete with the availability of petroleum-derived ethylene and propylene.<sup id="cite_ref-38" class="reference"><a href="#cite_note-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Niche_applications">Niche applications</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetylene&action=edit&section=14" title="Edit section: Niche applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In 1881, the Russian chemist Mikhail Kucherov<sup id="cite_ref-39" class="reference"><a href="#cite_note-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> described the <a href="/wiki/Hydration_reaction" title="Hydration reaction">hydration</a> of acetylene to <a href="/wiki/Acetaldehyde" title="Acetaldehyde">acetaldehyde</a> using catalysts such as <a href="/wiki/Mercury(II)_bromide" title="Mercury(II) bromide">mercury(II) bromide</a>. Before the advent of the <a href="/wiki/Wacker_process" title="Wacker process">Wacker process</a>, this reaction was conducted on an industrial scale.<sup id="cite_ref-40" class="reference"><a href="#cite_note-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> </p><p>The <a href="/wiki/Polymerization" title="Polymerization">polymerization</a> of acetylene with <a href="/wiki/Ziegler%E2%80%93Natta_catalyst" title="Ziegler–Natta catalyst">Ziegler–Natta catalysts</a> produces <a href="/wiki/Polyacetylene" title="Polyacetylene">polyacetylene</a> films. Polyacetylene, a chain of CH centres with alternating single and double bonds, was one of the first discovered <a href="/wiki/Organic_semiconductor" title="Organic semiconductor">organic semiconductors</a>. Its reaction with <a href="/wiki/Iodine" title="Iodine">iodine</a> produces a highly electrically conducting material. Although such materials are not useful, these discoveries led to the developments of <a href="/wiki/Organic_semiconductor" title="Organic semiconductor">organic semiconductors</a>, as recognized by the <a href="/wiki/Nobel_Prize_in_Chemistry" title="Nobel Prize in Chemistry">Nobel Prize in Chemistry</a> in 2000 to <a href="/wiki/Alan_J._Heeger" title="Alan J. Heeger">Alan J. Heeger</a>, <a href="/wiki/Alan_G_MacDiarmid" class="mw-redirect" title="Alan G MacDiarmid">Alan G MacDiarmid</a>, and <a href="/wiki/Hideki_Shirakawa" title="Hideki Shirakawa">Hideki Shirakawa</a>.<sup id="cite_ref-Ullmann_9-5" class="reference"><a href="#cite_note-Ullmann-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>In the 1920s, pure acetylene was experimentally used as an <a href="/wiki/Inhalation_anesthetic" class="mw-redirect" title="Inhalation anesthetic">inhalation anesthetic</a>.<sup id="cite_ref-41" class="reference"><a href="#cite_note-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> </p><p>Acetylene is sometimes used for <a href="/wiki/Carburization" class="mw-redirect" title="Carburization">carburization</a> (that is, hardening) of steel when the object is too large to fit into a furnace.<sup id="cite_ref-BOC2006_42-0" class="reference"><a href="#cite_note-BOC2006-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> </p><p>Acetylene is used to volatilize carbon in <a href="/wiki/Radiocarbon_dating" title="Radiocarbon dating">radiocarbon dating</a>. The carbonaceous material in an archeological sample is treated with <a href="/wiki/Lithium" title="Lithium">lithium</a> metal in a small specialized research furnace to form <a href="/wiki/Lithium_carbide" title="Lithium carbide">lithium carbide</a> (also known as lithium acetylide). The carbide can then be reacted with water, as usual, to form acetylene gas to feed into a <a href="/wiki/Mass_spectrometer" class="mw-redirect" title="Mass spectrometer">mass spectrometer</a> to measure the isotopic ratio of carbon-14 to carbon-12.<sup id="cite_ref-43" class="reference"><a href="#cite_note-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> </p><p>Acetylene combustion produces a strong, bright light and the ubiquity of <a href="/wiki/Carbide_lamp" title="Carbide lamp">carbide lamps</a> drove much acetylene commercialization in the early 20th century. Common applications included coastal <a href="/wiki/Lighthouse" title="Lighthouse">lighthouses</a>,<sup id="cite_ref-44" class="reference"><a href="#cite_note-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Street_light" title="Street light">street lights</a>,<sup id="cite_ref-45" class="reference"><a href="#cite_note-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/Headlamp" title="Headlamp">automobile</a><sup id="cite_ref-46" class="reference"><a href="#cite_note-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/Miner%27s_helmet" class="mw-redirect" title="Miner's helmet">mining</a> <a href="/wiki/Headlamp_(outdoor)" title="Headlamp (outdoor)">headlamps</a>.<sup id="cite_ref-Thorpe-2005_47-0" class="reference"><a href="#cite_note-Thorpe-2005-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> In most of these applications, direct combustion is a <a href="/wiki/Fire_hazard" class="mw-redirect" title="Fire hazard">fire hazard</a>, and so acetylene has been replaced, first by <a href="/wiki/Incandescent_light_bulb" title="Incandescent light bulb">incandescent lighting</a> and many years later by low-power/high-lumen LEDs. Nevertheless, acetylene lamps remain in limited use in remote or otherwise inaccessible areas and in countries with a weak or unreliable central <a href="/wiki/Electrical_grid" title="Electrical grid">electric grid</a>.<sup id="cite_ref-Thorpe-2005_47-1" class="reference"><a href="#cite_note-Thorpe-2005-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Natural_occurrence">Natural occurrence</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetylene&action=edit&section=15" title="Edit section: Natural occurrence"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The energy richness of the C≡C triple bond and the rather high solubility of acetylene in water make it a suitable substrate for bacteria, provided an adequate source is available.<sup id="cite_ref-48" class="reference"><a href="#cite_note-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup> A number of bacteria living on acetylene have been identified. The <a href="/wiki/Enzyme" title="Enzyme">enzyme</a> <a href="/wiki/Acetylene_hydratase" title="Acetylene hydratase">acetylene hydratase</a> catalyzes the hydration of acetylene to give <a href="/wiki/Acetaldehyde" title="Acetaldehyde">acetaldehyde</a>:<sup id="cite_ref-49" class="reference"><a href="#cite_note-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">2</sub>H<sub class="template-chem2-sub">2</sub> + H<sub class="template-chem2-sub">2</sub>O → CH<sub class="template-chem2-sub">3</sub>CHO</span></dd></dl> <p>Acetylene is a moderately common chemical in the universe, often associated with the atmospheres of <a href="/wiki/Gas_giant" title="Gas giant">gas giants</a>.<sup id="cite_ref-50" class="reference"><a href="#cite_note-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup> One curious discovery of acetylene is on <a href="/wiki/Enceladus" title="Enceladus">Enceladus</a>, a moon of <a href="/wiki/Saturn" title="Saturn">Saturn</a>. Natural acetylene is believed to form from <a href="/wiki/Catalysis" title="Catalysis">catalytic</a> decomposition of long-chain hydrocarbons at temperatures of 1,700 K (1,430 °C; 2,600 °F) and above. Since such temperatures are highly unlikely on such a small distant body, this discovery is potentially suggestive of catalytic reactions within that moon, making it a promising site to search for prebiotic chemistry.<sup id="cite_ref-51" class="reference"><a href="#cite_note-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-52" class="reference"><a href="#cite_note-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Reactions">Reactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetylene&action=edit&section=16" title="Edit section: Reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Vinylation_reactions">Vinylation reactions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetylene&action=edit&section=17" title="Edit section: Vinylation reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In <a href="/wiki/Vinylation" title="Vinylation">vinylation</a> reactions, H−X compounds add across the triple bond. <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">Alcohols</a> and <a href="/wiki/Phenols" title="Phenols">phenols</a> add to acetylene to give <a href="/wiki/Enol_ether" title="Enol ether">vinyl ethers</a>. <a href="/wiki/Thiol" title="Thiol">Thiols</a> give vinyl thioethers. Similarly, <a href="/wiki/Vinylpyrrolidone" class="mw-redirect" title="Vinylpyrrolidone">vinylpyrrolidone</a> and <a href="/wiki/Vinylcarbazole" class="mw-redirect" title="Vinylcarbazole">vinylcarbazole</a> are produced industrially by vinylation of <a href="/wiki/2-Pyrrolidone" title="2-Pyrrolidone">2-pyrrolidone</a> and <a href="/wiki/Carbazole" title="Carbazole">carbazole</a>.<sup id="cite_ref-Ull_31-1" class="reference"><a href="#cite_note-Ull-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Ullmann_9-6" class="reference"><a href="#cite_note-Ullmann-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:Reppe-chemnistry-vinylization.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/85/Reppe-chemnistry-vinylization.png/300px-Reppe-chemnistry-vinylization.png" decoding="async" width="300" height="203" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/85/Reppe-chemnistry-vinylization.png/450px-Reppe-chemnistry-vinylization.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/85/Reppe-chemnistry-vinylization.png/600px-Reppe-chemnistry-vinylization.png 2x" data-file-width="876" data-file-height="593" /></a></span></dd></dl> <p>The hydration of acetylene is a vinylation reaction, but the resulting vinyl alcohol isomerizes to <a href="/wiki/Acetaldehyde" title="Acetaldehyde">acetaldehyde</a>. The reaction is catalyzed by mercury salts. This reaction once was the dominant technology for acetaldehyde production, but it has been displaced by the <a href="/wiki/Wacker_process" title="Wacker process">Wacker process</a>, which affords acetaldehyde by oxidation of <a href="/wiki/Ethylene" title="Ethylene">ethylene</a>, a cheaper feedstock. A similar situation applies to the conversion of acetylene to the valuable <a href="/wiki/Vinyl_chloride" title="Vinyl chloride">vinyl chloride</a> by <a href="/wiki/Hydrochlorination" class="mw-redirect" title="Hydrochlorination">hydrochlorination</a> vs the <a href="/wiki/Oxychlorination" title="Oxychlorination">oxychlorination</a> of ethylene. </p><p><a href="/wiki/Vinyl_acetate" title="Vinyl acetate">Vinyl acetate</a> is used instead of acetylene for some vinylations, which are more accurately described as <a href="/wiki/Transvinylation" class="mw-redirect" title="Transvinylation">transvinylations</a>.<sup id="cite_ref-53" class="reference"><a href="#cite_note-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> Higher esters of vinyl acetate have been used in the synthesis of <a href="/wiki/Vinyl_formate" title="Vinyl formate">vinyl formate</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Organometallic_chemistry">Organometallic chemistry</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetylene&action=edit&section=18" title="Edit section: Organometallic chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Acetylene and its derivatives (2-butyne, diphenylacetylene, etc.) form <a href="/wiki/Transition_metal_alkyne_complex" title="Transition metal alkyne complex">complexes with transition metals</a>. Its bonding to the metal is somewhat similar to that of ethylene complexes. These complexes are intermediates in many catalytic reactions such as <a href="/wiki/Alkyne_trimerisation" title="Alkyne trimerisation">alkyne trimerisation</a> to benzene, tetramerization to <a href="/wiki/Cyclooctatetraene" title="Cyclooctatetraene">cyclooctatetraene</a>,<sup id="cite_ref-Ullmann_9-7" class="reference"><a href="#cite_note-Ullmann-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> and carbonylation to <a href="/wiki/Hydroquinone" title="Hydroquinone">hydroquinone</a>:<sup id="cite_ref-Cyclization_54-0" class="reference"><a href="#cite_note-Cyclization-54"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:Reppe-chemistry-benzene.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/76/Reppe-chemistry-benzene.png/240px-Reppe-chemistry-benzene.png" decoding="async" width="240" height="84" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/76/Reppe-chemistry-benzene.png/360px-Reppe-chemistry-benzene.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/76/Reppe-chemistry-benzene.png/480px-Reppe-chemistry-benzene.png 2x" data-file-width="665" data-file-height="232" /></a></span></dd> <dd><span typeof="mw:File"><a href="/wiki/File:Reppe-chemistry-cyclooctatetraene.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a0/Reppe-chemistry-cyclooctatetraene.png/240px-Reppe-chemistry-cyclooctatetraene.png" decoding="async" width="240" height="93" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a0/Reppe-chemistry-cyclooctatetraene.png/360px-Reppe-chemistry-cyclooctatetraene.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a0/Reppe-chemistry-cyclooctatetraene.png/480px-Reppe-chemistry-cyclooctatetraene.png 2x" data-file-width="683" data-file-height="264" /></a></span></dd> <dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Fe(CO)<sub class="template-chem2-sub">5</sub> + 4 C<sub class="template-chem2-sub">2</sub>H<sub class="template-chem2-sub">2</sub> + 2 H<sub class="template-chem2-sub">2</sub>O → 2 C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">4</sub>(OH)<sub class="template-chem2-sub">2</sub> + FeCO<sub class="template-chem2-sub">3</sub></span> at basic conditions (50–<span class="nowrap"><span data-sort-value="7002353150000000000♠"></span>80 °C</span>, 20–<span class="nowrap"><span data-sort-value="7006253312500000000♠"></span>25 atm</span>).</dd></dl> <p>Metal <a href="/wiki/Acetylide" title="Acetylide">acetylides</a>, species of the formula <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">L<sub class="template-chem2-sub"><i>n</i></sub>M−C<sub class="template-chem2-sub">2</sub>R</span>, are also common. <a href="/wiki/Copper(I)_acetylide" title="Copper(I) acetylide">Copper(I) acetylide</a> and <a href="/wiki/Silver_acetylide" title="Silver acetylide">silver acetylide</a> can be formed in <a href="/wiki/Aqueous" class="mw-redirect" title="Aqueous">aqueous</a> solutions with ease due to a favorable <a href="/wiki/Solubility_equilibrium" title="Solubility equilibrium">solubility equilibrium</a>.<sup id="cite_ref-Viehe_55-0" class="reference"><a href="#cite_note-Viehe-55"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Acid-base_reactions">Acid-base reactions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetylene&action=edit&section=19" title="Edit section: Acid-base reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></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/Acetylide#Preparation" title="Acetylide">Acetylide § Preparation</a></div> <p>Acetylene has a <a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">p<i>K</i><sub>a</sub></a> of 25, acetylene can be <a href="/wiki/Deprotonation" title="Deprotonation">deprotonated</a> by a <a href="/wiki/Superbase" title="Superbase">superbase</a> to form an <a href="/wiki/Acetylide" title="Acetylide">acetylide</a>:<sup id="cite_ref-Viehe_55-1" class="reference"><a href="#cite_note-Viehe-55"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {HC#CH + RM -> RH + HC#CM}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mtext>HC</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>≡</mo> </mrow> <mtext>CH</mtext> <mo>+</mo> <mtext>RM</mtext> <mo stretchy="false">⟶</mo> <mtext>RH</mtext> <mo>+</mo> <mtext>HC</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>≡</mo> </mrow> <mtext>CM</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {HC#CH + RM -> RH + HC#CM}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/f579f973acd0d4d62e3da5fe185d867ae4fb5fbf" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -0.505ex; width:35.761ex; height:2.343ex;" alt="{\displaystyle {\ce {HC#CH + RM -> RH + HC#CM}}}"></span></dd></dl> <p>Various <a href="/wiki/Organometallic" class="mw-redirect" title="Organometallic">organometallic</a><sup id="cite_ref-Midland1990_56-0" class="reference"><a href="#cite_note-Midland1990-56"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/Inorganic_compound" title="Inorganic compound">inorganic</a><sup id="cite_ref-Coffman_57-0" class="reference"><a href="#cite_note-Coffman-57"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup> reagents are effective. </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:BASF_Nsw.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e4/BASF_Nsw.jpg/220px-BASF_Nsw.jpg" decoding="async" width="220" height="98" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e4/BASF_Nsw.jpg/330px-BASF_Nsw.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e4/BASF_Nsw.jpg/440px-BASF_Nsw.jpg 2x" data-file-width="2688" data-file-height="1200" /></a><figcaption>The <i>New acetylene plant</i> of <a href="/wiki/BASF" title="BASF">BASF</a>, commissioned in 2020</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Hydrogenation">Hydrogenation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetylene&action=edit&section=20" title="Edit section: Hydrogenation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Acetylene can be <a href="/wiki/Semihydrogenation" class="mw-redirect" title="Semihydrogenation">semihydrogenated</a> to <a href="/wiki/Ethylene" title="Ethylene">ethylene</a>, providing a feedstock for a variety of <a href="/wiki/Polyethylene" title="Polyethylene">polyethylene</a> plastics. Halogens add to the triple bond. </p> <div class="mw-heading mw-heading2"><h2 id="Safety_and_handling">Safety and handling</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetylene&action=edit&section=21" title="Edit section: Safety and handling"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Acetylene is not especially toxic, but when generated from <a href="/wiki/Calcium_carbide" title="Calcium carbide">calcium carbide</a>, it can contain toxic impurities such as traces of <a href="/wiki/Phosphine" title="Phosphine">phosphine</a> and <a href="/wiki/Arsine" title="Arsine">arsine</a>, which gives it a distinct <a href="/wiki/Garlic" title="Garlic">garlic</a>-like smell. It is also highly flammable, as are most light hydrocarbons, hence its use in welding. Its most singular hazard is associated with its intrinsic instability, especially when it is pressurized: under certain conditions acetylene can react in an <a href="/wiki/Exothermic" class="mw-redirect" title="Exothermic">exothermic</a> addition-type reaction to form a number of products, typically <a href="/wiki/Benzene" title="Benzene">benzene</a> and/or <a href="/wiki/Vinylacetylene" title="Vinylacetylene">vinylacetylene</a>, possibly in addition to <a href="/wiki/Carbon" title="Carbon">carbon</a> and <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a>.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (December 2016)">citation needed</span></a></i>]</sup> Consequently, acetylene, if initiated by intense heat or a shockwave, can decompose explosively if the absolute pressure of the gas exceeds about 200 kilopascals (29 psi). Most regulators and pressure gauges on equipment report <a href="/wiki/Gauge_pressure" class="mw-redirect" title="Gauge pressure">gauge pressure</a>, and the safe limit for acetylene therefore is 101 kPa<sub>gage</sub>, or 15 psig.<sup id="cite_ref-58" class="reference"><a href="#cite_note-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-law_59-0" class="reference"><a href="#cite_note-law-59"><span class="cite-bracket">[</span>59<span class="cite-bracket">]</span></a></sup> It is therefore supplied and stored dissolved in <a href="/wiki/Acetone" title="Acetone">acetone</a> or <a href="/wiki/Dimethylformamide" title="Dimethylformamide">dimethylformamide</a> (DMF),<sup id="cite_ref-law_59-1" class="reference"><a href="#cite_note-law-59"><span class="cite-bracket">[</span>59<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Industrial_Gases_60-0" class="reference"><a href="#cite_note-Industrial_Gases-60"><span class="cite-bracket">[</span>60<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-61" class="reference"><a href="#cite_note-61"><span class="cite-bracket">[</span>61<span class="cite-bracket">]</span></a></sup> contained in a <a href="/wiki/Gas_cylinder" title="Gas cylinder">gas cylinder</a> with a <a href="/wiki/Agamassan" title="Agamassan">porous filling</a>, which renders it safe to transport and use, given proper handling. Acetylene cylinders should be used in the upright position to avoid withdrawing acetone during use.<sup id="cite_ref-EIGA_62-0" class="reference"><a href="#cite_note-EIGA-62"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup> </p><p>Information on safe storage of acetylene in upright cylinders is provided by the OSHA,<sup id="cite_ref-63" class="reference"><a href="#cite_note-63"><span class="cite-bracket">[</span>63<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-OSHA_64-0" class="reference"><a href="#cite_note-OSHA-64"><span class="cite-bracket">[</span>64<span class="cite-bracket">]</span></a></sup> Compressed Gas Association,<sup id="cite_ref-law_59-2" class="reference"><a href="#cite_note-law-59"><span class="cite-bracket">[</span>59<span class="cite-bracket">]</span></a></sup> United States Mine Safety and Health Administration (MSHA),<sup id="cite_ref-65" class="reference"><a href="#cite_note-65"><span class="cite-bracket">[</span>65<span class="cite-bracket">]</span></a></sup> EIGA,<sup id="cite_ref-EIGA_62-1" class="reference"><a href="#cite_note-EIGA-62"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup> and other agencies. </p><p><a href="/wiki/Copper" title="Copper">Copper</a> catalyses the decomposition of acetylene, and as a result acetylene should not be transported in copper pipes.<sup id="cite_ref-brown_66-0" class="reference"><a href="#cite_note-brown-66"><span class="cite-bracket">[</span>66<span class="cite-bracket">]</span></a></sup> </p><p>Cylinders should be stored in an area segregated from oxidizers to avoid exacerbated reaction in case of fire/leakage.<sup id="cite_ref-law_59-3" class="reference"><a href="#cite_note-law-59"><span class="cite-bracket">[</span>59<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-OSHA_64-1" class="reference"><a href="#cite_note-OSHA-64"><span class="cite-bracket">[</span>64<span class="cite-bracket">]</span></a></sup> Acetylene cylinders should not be stored in confined spaces, enclosed vehicles, garages, and buildings, to avoid unintended leakage leading to explosive atmosphere.<sup id="cite_ref-law_59-4" class="reference"><a href="#cite_note-law-59"><span class="cite-bracket">[</span>59<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-OSHA_64-2" class="reference"><a href="#cite_note-OSHA-64"><span class="cite-bracket">[</span>64<span class="cite-bracket">]</span></a></sup> In the US, National Electric Code (NEC) requires consideration for hazardous areas including those where acetylene may be released during accidents or leaks.<sup id="cite_ref-NFPA_67-0" class="reference"><a href="#cite_note-NFPA-67"><span class="cite-bracket">[</span>67<span class="cite-bracket">]</span></a></sup> Consideration may include electrical classification and use of listed Group A electrical components in US.<sup id="cite_ref-NFPA_67-1" class="reference"><a href="#cite_note-NFPA-67"><span class="cite-bracket">[</span>67<span class="cite-bracket">]</span></a></sup> Further information on determining the areas requiring special consideration is in NFPA 497.<sup id="cite_ref-68" class="reference"><a href="#cite_note-68"><span class="cite-bracket">[</span>68<span class="cite-bracket">]</span></a></sup> In Europe, ATEX also requires consideration for hazardous areas where flammable gases may be released during accidents or leaks.<sup id="cite_ref-EIGA_62-2" class="reference"><a href="#cite_note-EIGA-62"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetylene&action=edit&section=22" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></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-iupac2013-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-iupac2013_1-0">^</a></b></span> <span class="reference-text"><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="CITEREFFavrePowell2014" class="citation book cs1">Favre, Henri A.; Powell, Warren H. (2014). <i>Nomenclature of Organic Chemistry. IUPAC Recommendations and Preferred Names 2013 (Blue Book)</i>. Cambridge: <a href="/wiki/Royal_Society_of_Chemistry" title="Royal Society of Chemistry">The Royal Society of Chemistry</a>. p. 375. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2F9781849733069">10.1039/9781849733069</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-85404-182-4" title="Special:BookSources/978-0-85404-182-4"><bdi>978-0-85404-182-4</bdi></a>. <q>The name acetylene is retained for the compound HC≡CH. It is the preferred IUPAC name, but substitution of any kind is not allowed; however, in general nomenclature, substitution is allowed, for example fluoroacetylene [fluoroethyne (PIN)], but not by alkyl groups or any other group that extends the carbon chain, nor by characteristic groups expressed by suffixes.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Nomenclature+of+Organic+Chemistry.+IUPAC+Recommendations+and+Preferred+Names+2013+%28Blue+Book%29&rft.place=Cambridge&rft.pages=375&rft.pub=The+Royal+Society+of+Chemistry&rft.date=2014&rft_id=info%3Adoi%2F10.1039%2F9781849733069&rft.isbn=978-0-85404-182-4&rft.aulast=Favre&rft.aufirst=Henri+A.&rft.au=Powell%2C+Warren+H.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetylene" class="Z3988"></span></span> </li> <li id="cite_note-P-14.3.4.2-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-P-14.3.4.2_2-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMoss,_G.P._(web_version)" class="citation web cs1">Moss, G.P. (web version). <a rel="nofollow" class="external text" href="https://iupac.qmul.ac.uk/BlueBook/P1.html#1403">"P-14.3 Locants"</a>. <i>Nomenclature of Organic Chemistry. IUPAC Recommendations and Preferred Names 2013</i>. London: Queen Mary University. Section P-14.3.4.2 (d)<span class="reference-accessdate">. Retrieved <span class="nowrap">24 August</span> 2024</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Nomenclature+of+Organic+Chemistry.+IUPAC+Recommendations+and+Preferred+Names+2013&rft.atitle=P-14.3+Locants&rft.pages=Section+P-14.3.4.2-%28d%29&rft.au=Moss%2C+G.P.+%28web+version%29&rft_id=https%3A%2F%2Fiupac.qmul.ac.uk%2FBlueBook%2FP1.html%231403&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetylene" class="Z3988"></span></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external text" href="http://www.acdlabs.com/iupac/nomenclature/79/r79_53.htm">Acyclic Hydrocarbons. Rule A-3. Unsaturated Compounds and Univalent Radicals</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20001010202833/http://www.acdlabs.com/iupac/nomenclature/79/r79_53.htm">Archived</a> 10 October 2000 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a>, IUPAC Nomenclature of Organic Chemistry</span> </li> <li id="cite_note-GESTIS-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-GESTIS_4-0">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external text" href="https://gestis.dguv.de/data?name=013570&lang=en">Record of <i>Acetylene</i></a> in the <a href="/wiki/GESTIS_Substance_Database" title="GESTIS Substance Database">GESTIS Substance Database</a> of the <a href="/wiki/Institute_for_Occupational_Safety_and_Health_of_the_German_Social_Accident_Insurance" title="Institute for Occupational Safety and Health of the German Social Accident Insurance">Institute for Occupational Safety and Health</a> </span> </li> <li id="cite_note-NIOSH-5"><span class="mw-cite-backlink">^ <a href="#cite_ref-NIOSH_5-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-NIOSH_5-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-NIOSH_5-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-NIOSH_5-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFNIOSH_Pocket_Guide_to_Chemical_Hazards" class="citation web cs1">NIOSH Pocket Guide to Chemical Hazards. <a rel="nofollow" class="external text" href="https://www.cdc.gov/niosh/npg/npgd0008.html">"#0008"</a>. <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%3Abook&rft.genre=unknown&rft.btitle=%230008&rft.pub=National+Institute+for+Occupational+Safety+and+Health+%28NIOSH%29&rft.au=NIOSH+Pocket+Guide+to+Chemical+Hazards&rft_id=https%3A%2F%2Fwww.cdc.gov%2Fniosh%2Fnpg%2Fnpgd0008.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetylene" class="Z3988"></span></span> </li> <li id="cite_note-airliquide-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-airliquide_6-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://encyclopedia.airliquide.com/Encyclopedia.asp?GasID=1#MajorApplications">"Acetylene – Gas Encyclopedia Air Liquide"</a>. <i>Air Liquide</i>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20220504220655/https://encyclopedia.airliquide.com/Encyclopedia.asp?GasID=1#MajorApplications">Archived</a> from the original on 4 May 2022<span class="reference-accessdate">. Retrieved <span class="nowrap">27 September</span> 2018</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Air+Liquide&rft.atitle=Acetylene+%E2%80%93+Gas+Encyclopedia+Air+Liquide&rft_id=http%3A%2F%2Fencyclopedia.airliquide.com%2FEncyclopedia.asp%3FGasID%3D1%23MajorApplications&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetylene" class="Z3988"></span></span> </li> <li id="cite_note-CRC97-7"><span class="mw-cite-backlink">^ <a href="#cite_ref-CRC97_7-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-CRC97_7-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-CRC97_7-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWilliam_M._HaynesDavid_R._LideThomas_J._Bruno2016" class="citation book cs1">William M. Haynes; David R. Lide; Thomas J. Bruno (2016). <a rel="nofollow" class="external text" href="https://www.worldcat.org/oclc/930681942"><i>CRC handbook of chemistry and physics : a ready-reference book of chemical and physical data</i></a> (2016-2017, 97th ed.). Boca Raton, Florida: CRC Press. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4987-5428-6" title="Special:BookSources/978-1-4987-5428-6"><bdi>978-1-4987-5428-6</bdi></a>. <a href="/wiki/OCLC_(identifier)" class="mw-redirect" title="OCLC (identifier)">OCLC</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/oclc/930681942">930681942</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20220504220656/https://www.worldcat.org/title/crc-handbook-of-chemistry-and-physics-a-ready-reference-book-of-chemical-and-physical-data/oclc/930681942">Archived</a> from the original on 4 May 2022<span class="reference-accessdate">. Retrieved <span class="nowrap">4 May</span> 2022</span>.</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+%3A+a+ready-reference+book+of+chemical+and+physical+data.&rft.place=Boca+Raton%2C+Florida&rft.edition=2016-2017%2C+97th&rft.pub=CRC+Press&rft.date=2016&rft_id=info%3Aoclcnum%2F930681942&rft.isbn=978-1-4987-5428-6&rft.au=William+M.+Haynes&rft.au=David+R.+Lide&rft.au=Thomas+J.+Bruno&rft_id=https%3A%2F%2Fwww.worldcat.org%2Foclc%2F930681942&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetylene" class="Z3988"></span></span> </li> <li id="cite_note-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-8">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFR._H._PetrucciW._S._HarwoodF._G._Herring2002" class="citation book cs1">R. H. Petrucci; W. S. Harwood; F. G. Herring (2002). <i>General Chemistry</i> (8th ed.). 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Retrieved <span class="nowrap">29 December</span> 2021</span>. <q>Atomic weights of 6 and 12 were both in use for carbon.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Chemical+Education&rft.atitle=The+Karlsruhe+Congress%3A+A+centennial+retrospective&rft.volume=38&rft.issue=2&rft.pages=83&rft.date=1961&rft_id=info%3Adoi%2F10.1021%2Fed038p83&rft_id=info%3Abibcode%2F1961JChEd..38...83I&rft.aulast=Ihde&rft.aufirst=Aaron+J.&rft_id=https%3A%2F%2Fpubs.acs.org%2Fdoi%2Fabs%2F10.1021%2Fed038p83&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetylene" class="Z3988"></span></span> </li> <li id="cite_note-16"><span class="mw-cite-backlink"><b><a href="#cite_ref-16">^</a></b></span> <span class="reference-text">Berthelot (1862) <a rel="nofollow" class="external text" href="http://gallica.bnf.fr/ark:/12148/bpt6k30115/f640.image.langEN">"<i>Synthèse de l'acétylène par la combinaison directe du carbone avec l'hydrogène</i>"</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20200814023647/https://gallica.bnf.fr/ark:/12148/bpt6k30115/f640.image.langEN">Archived</a> 14 August 2020 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a> (Synthesis of acetylene by the direct combination of carbon with hydrogen), <i>Comptes rendus</i>, series 3, <b>54</b>: 640–644.</span> </li> <li id="cite_note-17"><span class="mw-cite-backlink"><b><a href="#cite_ref-17">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external text" href="http://chestofbooks.com/crafts/metal/Welding-Cutting/Acetylene.html">Acetylene</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20120128110843/http://chestofbooks.com/crafts/metal/Welding-Cutting/Acetylene.html">Archived</a> 28 January 2012 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a>.</span> </li> <li id="cite_note-18"><span class="mw-cite-backlink"><b><a href="#cite_ref-18">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHabilSachsse1954" class="citation journal cs1">Habil, Phil; Sachsse, Hans (1954). 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Retrieved <span class="nowrap">10 October</span> 2024</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=American+Chemical+Society&rft.atitle=A+National+Historic+Chemical+Landmark+-+Discovery+of+the+Commercial+Processes+For+Making+Calcium+Carbide+and+Acetylene+-+Commemorative+Booklet&rft.date=1998&rft_id=https%3A%2F%2Fwww.acs.org%2Fcontent%2Fdam%2Facsorg%2Feducation%2Fwhatischemistry%2Flandmarks%2Fcalciumcarbideacetylene%2Fcommericialization-of-calcium-carbide-and-acetylene-commemorative-booklet.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetylene" class="Z3988"></span></span> </li> <li id="cite_note-25"><span class="mw-cite-backlink"><b><a href="#cite_ref-25">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGannon2000" class="citation book cs1">Gannon, Richard E. (2000). "Acetylene from Hydrocarbons". <i>Kirk-Othmer Encyclopedia of Chemical Technology</i>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F0471238961.0103052007011414.a01">10.1002/0471238961.0103052007011414.a01</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780471484943" title="Special:BookSources/9780471484943"><bdi>9780471484943</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Acetylene+from+Hydrocarbons&rft.btitle=Kirk-Othmer+Encyclopedia+of+Chemical+Technology&rft.date=2000&rft_id=info%3Adoi%2F10.1002%2F0471238961.0103052007011414.a01&rft.isbn=9780471484943&rft.aulast=Gannon&rft.aufirst=Richard+E.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetylene" class="Z3988"></span><sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Verifiability" title="Wikipedia:Verifiability"><span title="Quotation needed from source to verify. (October 2024)">need quotation to verify</span></a></i>]</sup></span> </li> <li id="cite_note-26"><span class="mw-cite-backlink"><b><a href="#cite_ref-26">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHolzrichterKnottMertschenkSalzinger2013" class="citation book cs1">Holzrichter, Klaus; Knott, Alfons; Mertschenk, Bernd; Salzinger, Josef (2013). "Calcium Carbide". <i>Ullmann's Encyclopedia of Industrial Chemistry</i>. pp. 1–14. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F14356007.a04_533.pub2">10.1002/14356007.a04_533.pub2</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-527-30673-2" title="Special:BookSources/978-3-527-30673-2"><bdi>978-3-527-30673-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Calcium+Carbide&rft.btitle=Ullmann%27s+Encyclopedia+of+Industrial+Chemistry&rft.pages=1-14&rft.date=2013&rft_id=info%3Adoi%2F10.1002%2F14356007.a04_533.pub2&rft.isbn=978-3-527-30673-2&rft.aulast=Holzrichter&rft.aufirst=Klaus&rft.au=Knott%2C+Alfons&rft.au=Mertschenk%2C+Bernd&rft.au=Salzinger%2C+Josef&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetylene" class="Z3988"></span></span> </li> <li id="cite_note-27"><span class="mw-cite-backlink"><b><a href="#cite_ref-27">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFreeman1919" class="citation journal cs1">Freeman, Horace (1919). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=5SAzAQAAMAAJ&q=calcium+carbide&pg=PA232">"Manufacture of Cyanamide"</a>. <i>The Chemical News and the Journal of Physical Science</i>. <b>117</b>: 232. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20210415083126/https://books.google.com/books?id=5SAzAQAAMAAJ&q=calcium+carbide&pg=PA232">Archived</a> from the original on 15 April 2021<span class="reference-accessdate">. Retrieved <span class="nowrap">23 December</span> 2013</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Chemical+News+and+the+Journal+of+Physical+Science&rft.atitle=Manufacture+of+Cyanamide&rft.volume=117&rft.pages=232&rft.date=1919&rft.aulast=Freeman&rft.aufirst=Horace&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D5SAzAQAAMAAJ%26q%3Dcalcium%2Bcarbide%26pg%3DPA232&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetylene" class="Z3988"></span></span> </li> <li id="cite_note-28"><span class="mw-cite-backlink"><b><a href="#cite_ref-28">^</a></b></span> <span class="reference-text">Organic Chemistry 7th ed. by J. McMurry, Thomson 2008</span> </li> <li id="cite_note-29"><span class="mw-cite-backlink"><b><a href="#cite_ref-29">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHousecroftSharpe2008" class="citation book cs1">Housecroft, C. E.; Sharpe, A. G. (2008). <i>Inorganic Chemistry</i> (3rd ed.). 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C-303 in Table <i>Physical Constants of Organic Compounds</i> (listed as <i>ethyne</i>).</span> </li> <li id="cite_note-Ull-31"><span class="mw-cite-backlink">^ <a href="#cite_ref-Ull_31-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Ull_31-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHarreusBackesEichlerFeuerhake2011" class="citation encyclopaedia cs1">Harreus, Albrecht Ludwig; Backes, R.; Eichler, J.-O.; Feuerhake, R.; Jäkel, C.; Mahn, U.; Pinkos, R.; Vogelsang, R. (2011). "2-Pyrrolidone". <i><a href="/wiki/Ullmann%27s_Encyclopedia_of_Industrial_Chemistry" title="Ullmann's Encyclopedia of Industrial Chemistry">Ullmann's Encyclopedia of Industrial Chemistry</a></i>. Weinheim: Wiley-VCH. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F14356007.a22_457.pub2">10.1002/14356007.a22_457.pub2</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3527306732" title="Special:BookSources/978-3527306732"><bdi>978-3527306732</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=2-Pyrrolidone&rft.btitle=Ullmann%27s+Encyclopedia+of+Industrial+Chemistry&rft.place=Weinheim&rft.pub=Wiley-VCH&rft.date=2011&rft_id=info%3Adoi%2F10.1002%2F14356007.a22_457.pub2&rft.isbn=978-3527306732&rft.aulast=Harreus&rft.aufirst=Albrecht+Ludwig&rft.au=Backes%2C+R.&rft.au=Eichler%2C+J.-O.&rft.au=Feuerhake%2C+R.&rft.au=J%C3%A4kel%2C+C.&rft.au=Mahn%2C+U.&rft.au=Pinkos%2C+R.&rft.au=Vogelsang%2C+R.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetylene" class="Z3988"></span></span> </li> <li id="cite_note-Linde2013-32"><span class="mw-cite-backlink"><b><a href="#cite_ref-Linde2013_32-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.linde-gas.com/en/products_and_supply/gases_fuel/acetylene.html">"Acetylene"</a>. <i>Products and Supply > Fuel Gases</i>. Linde. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20180112184128/http://www.linde-gas.com/en/products_and_supply/gases_fuel/acetylene.html">Archived</a> from the original on 12 January 2018<span class="reference-accessdate">. Retrieved <span class="nowrap">30 November</span> 2013</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Products+and+Supply+%3E+Fuel+Gases&rft.atitle=Acetylene&rft_id=http%3A%2F%2Fwww.linde-gas.com%2Fen%2Fproducts_and_supply%2Fgases_fuel%2Facetylene.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetylene" class="Z3988"></span></span> </li> <li id="cite_note-33"><span class="mw-cite-backlink"><b><a href="#cite_ref-33">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external text" href="http://www.esabna.com/euweb/oxy_handbook/589oxy3_3.htm">ESAB Oxy-acetylene welding handbook – Acetylene properties</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20200510192947/https://www.esabna.com/euweb/oxy_handbook/589oxy3_3.htm">Archived</a> 10 May 2020 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a>.</span> </li> <li id="cite_note-trot-34"><span class="mw-cite-backlink">^ <a href="#cite_ref-trot_34-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-trot_34-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFTrotuşZimmermannSchüth2014" class="citation journal cs1">Trotuş, Ioan-Teodor; Zimmermann, Tobias; Schüth, Ferdi (2014). <a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fcr400357r">"Catalytic Reactions of Acetylene: A Feedstock for the Chemical Industry Revisited"</a>. <i>Chemical Reviews</i>. <b>114</b> (3): 1761–1782. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fcr400357r">10.1021/cr400357r</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/24228942">24228942</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemical+Reviews&rft.atitle=Catalytic+Reactions+of+Acetylene%3A+A+Feedstock+for+the+Chemical+Industry+Revisited&rft.volume=114&rft.issue=3&rft.pages=1761-1782&rft.date=2014&rft_id=info%3Adoi%2F10.1021%2Fcr400357r&rft_id=info%3Apmid%2F24228942&rft.aulast=Trotu%C5%9F&rft.aufirst=Ioan-Teodor&rft.au=Zimmermann%2C+Tobias&rft.au=Sch%C3%BCth%2C+Ferdi&rft_id=https%3A%2F%2Fdoi.org%2F10.1021%252Fcr400357r&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetylene" class="Z3988"></span></span> </li> <li id="cite_note-35"><span class="mw-cite-backlink"><b><a href="#cite_ref-35">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGräfjeKörnigWeitzReiß2000" class="citation cs2">Gräfje, Heinz; Körnig, Wolfgang; Weitz, Hans-Martin; Reiß, Wolfgang; Steffan, Guido; Diehl, Herbert; Bosche, Horst; Schneider, Kurt; Kieczka, Heinz (15 June 2000), <a rel="nofollow" class="external text" href="https://onlinelibrary.wiley.com/doi/10.1002/14356007.a04_455">"Butanediols, Butenediol, and Butynediol"</a>, in Wiley-VCH Verlag GmbH & Co. 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Retrieved <span class="nowrap">30 November</span> 2016</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=law.resource.org+CGA+g-1+2009+%28incorporated+by+reference%29&rft_id=https%3A%2F%2Flaw.resource.org%2Fpub%2Fus%2Fcfr%2Fibr%2F003%2Fcga.g-1.2009.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetylene" class="Z3988"></span></span> </li> <li id="cite_note-Industrial_Gases-60"><span class="mw-cite-backlink"><b><a href="#cite_ref-Industrial_Gases_60-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDownie1997" class="citation book cs1">Downie, N. A. (1997). <i>Industrial Gases</i>. London; New York: Blackie Academic & Professional. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-7514-0352-7" title="Special:BookSources/978-0-7514-0352-7"><bdi>978-0-7514-0352-7</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Industrial+Gases&rft.place=London%3B+New+York&rft.pub=Blackie+Academic+%26+Professional&rft.date=1997&rft.isbn=978-0-7514-0352-7&rft.aulast=Downie&rft.aufirst=N.+A.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetylene" class="Z3988"></span></span> </li> <li id="cite_note-61"><span class="mw-cite-backlink"><b><a href="#cite_ref-61">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKorzun1986" class="citation book cs1">Korzun, Mikołaj (1986). <i>1000 słów o materiałach wybuchowych i wybuchu</i>. Warszawa: Wydawnictwo Ministerstwa Obrony Narodowej. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/83-11-07044-X" title="Special:BookSources/83-11-07044-X"><bdi>83-11-07044-X</bdi></a>. <a href="/wiki/OCLC_(identifier)" class="mw-redirect" title="OCLC (identifier)">OCLC</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/oclc/69535236">69535236</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=1000+s%C5%82%C3%B3w+o+materia%C5%82ach+wybuchowych+i+wybuchu&rft.place=Warszawa&rft.pub=Wydawnictwo+Ministerstwa+Obrony+Narodowej&rft.date=1986&rft_id=info%3Aoclcnum%2F69535236&rft.isbn=83-11-07044-X&rft.aulast=Korzun&rft.aufirst=Miko%C5%82aj&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetylene" class="Z3988"></span></span> </li> <li id="cite_note-EIGA-62"><span class="mw-cite-backlink">^ <a href="#cite_ref-EIGA_62-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-EIGA_62-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-EIGA_62-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20161201014426/http://eiga.web1.apollo-com.be/fileadmin/docs_pubs/Doc_123_13_Code_of_Practice_Acetylene.pdf">"EIGA Code of Practice: Acetylene"</a> <span class="cs1-format">(PDF)</span>. Archived from <a rel="nofollow" class="external text" href="http://eiga.web1.apollo-com.be/fileadmin/docs_pubs/Doc_123_13_Code_of_Practice_Acetylene.pdf">the original</a> <span class="cs1-format">(PDF)</span> on 1 December 2016<span class="reference-accessdate">. Retrieved <span class="nowrap">30 November</span> 2016</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=EIGA+Code+of+Practice%3A+Acetylene&rft_id=http%3A%2F%2Feiga.web1.apollo-com.be%2Ffileadmin%2Fdocs_pubs%2FDoc_123_13_Code_of_Practice_Acetylene.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetylene" class="Z3988"></span></span> </li> <li id="cite_note-63"><span class="mw-cite-backlink"><b><a href="#cite_ref-63">^</a></b></span> <span class="reference-text"><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.osha.gov/pls/oshaweb/owadisp.show_document?p_table=STANDARDS&p_id=9748">"OSHA 29 CFR 1910.102 Acetylene"</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20161201080130/https://www.osha.gov/pls/oshaweb/owadisp.show_document?p_table=STANDARDS&p_id=9748">Archived</a> from the original on 1 December 2016<span class="reference-accessdate">. Retrieved <span class="nowrap">30 November</span> 2016</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=OSHA+29+CFR+1910.102+Acetylene&rft_id=https%3A%2F%2Fwww.osha.gov%2Fpls%2Foshaweb%2Fowadisp.show_document%3Fp_table%3DSTANDARDS%26p_id%3D9748&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetylene" class="Z3988"></span></span> </li> <li id="cite_note-OSHA-64"><span class="mw-cite-backlink">^ <a href="#cite_ref-OSHA_64-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-OSHA_64-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-OSHA_64-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><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.osha.gov/pls/oshaweb/owadisp.show_document?p_table=STANDARDS&p_id=10696">"OSHA 29 CFR 1926.350 Gas Welding and cutting"</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20161201012751/https://www.osha.gov/pls/oshaweb/owadisp.show_document?p_table=STANDARDS&p_id=10696">Archived</a> from the original on 1 December 2016<span class="reference-accessdate">. Retrieved <span class="nowrap">30 November</span> 2016</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=OSHA+29+CFR+1926.350+Gas+Welding+and+cutting.&rft_id=https%3A%2F%2Fwww.osha.gov%2Fpls%2Foshaweb%2Fowadisp.show_document%3Fp_table%3DSTANDARDS%26p_id%3D10696&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetylene" class="Z3988"></span></span> </li> <li id="cite_note-65"><span class="mw-cite-backlink"><b><a href="#cite_ref-65">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external text" href="https://arlweb.msha.gov/alerts/hazardsofacetylene.htm">Special Hazards of Acetylene</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20160324115350/http://arlweb.msha.gov/alerts/hazardsofacetylene.htm">Archived</a> 24 March 2016 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a> UNITED STATES DEPARTMENT OF LABOR Mine Safety and Health Administration – MSHA.</span> </li> <li id="cite_note-brown-66"><span class="mw-cite-backlink"><b><a href="#cite_ref-brown_66-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDaniel_Sarachick2003" class="citation web cs1">Daniel_Sarachick (16 October 2003). <a rel="nofollow" class="external text" href="http://www.brown.edu/Administration/EHS/lab/assets/SA-2.2003.pdf">"ACETYLENE SAFETY ALERT"</a> <span class="cs1-format">(PDF)</span>. Office of Environmental Health & Safety (EHS). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20180713033908/http://www.brown.edu/Administration/EHS/lab/assets/SA-2.2003.pdf">Archived</a> <span class="cs1-format">(PDF)</span> from the original on 13 July 2018<span class="reference-accessdate">. Retrieved <span class="nowrap">27 September</span> 2018</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=ACETYLENE+SAFETY+ALERT&rft.pub=Office+of+Environmental+Health+%26+Safety+%28EHS%29&rft.date=2003-10-16&rft.au=Daniel_Sarachick&rft_id=http%3A%2F%2Fwww.brown.edu%2FAdministration%2FEHS%2Flab%2Fassets%2FSA-2.2003.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetylene" class="Z3988"></span></span> </li> <li id="cite_note-NFPA-67"><span class="mw-cite-backlink">^ <a href="#cite_ref-NFPA_67-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-NFPA_67-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.nfpa.org/codes-and-standards/all-codes-and-standards/list-of-codes-and-standards?mode=code&code=70&tab=editions">"NFPA free access to 2017 edition of NFPA 70 (NEC)"</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20161201075712/http://www.nfpa.org/codes-and-standards/all-codes-and-standards/list-of-codes-and-standards?mode=code&code=70&tab=editions">Archived</a> from the original on 1 December 2016<span class="reference-accessdate">. Retrieved <span class="nowrap">30 November</span> 2016</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=NFPA+free+access+to+2017+edition+of+NFPA+70+%28NEC%29&rft_id=http%3A%2F%2Fwww.nfpa.org%2Fcodes-and-standards%2Fall-codes-and-standards%2Flist-of-codes-and-standards%3Fmode%3Dcode%26code%3D70%26tab%3Deditions&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetylene" class="Z3988"></span></span> </li> <li id="cite_note-68"><span class="mw-cite-backlink"><b><a href="#cite_ref-68">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.nfpa.org/codes-and-standards/all-codes-and-standards/list-of-codes-and-standards?mode=code&code=497&tab=editions">"NFPA Free Access to NFPA 497 – Recommended Practice for the Classification of Flammable Liquids, Gases, or Vapors and of Hazardous (Classified) Locations for Electrical Installations in Chemical Process Areas"</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20161201015905/http://www.nfpa.org/codes-and-standards/all-codes-and-standards/list-of-codes-and-standards?mode=code&code=497&tab=editions">Archived</a> from the original on 1 December 2016<span class="reference-accessdate">. Retrieved <span class="nowrap">30 November</span> 2016</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=NFPA+Free+Access+to+NFPA+497+%E2%80%93+Recommended+Practice+for+the+Classification+of+Flammable+Liquids%2C+Gases%2C+or+Vapors+and+of+Hazardous+%28Classified%29+Locations+for+Electrical+Installations+in+Chemical+Process+Areas&rft_id=http%3A%2F%2Fwww.nfpa.org%2Fcodes-and-standards%2Fall-codes-and-standards%2Flist-of-codes-and-standards%3Fmode%3Dcode%26code%3D497%26tab%3Deditions&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcetylene" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acetylene&action=edit&section=23" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style 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Alive!</a></li> <li class="mw-empty-elt"></li> <li><style data-mw-deduplicate="TemplateStyles:r1041539562">.mw-parser-output .citation{word-wrap:break-word}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}</style><span class="citation gutenberg"> <i><a rel="nofollow" class="external text" href="https://gutenberg.org/ebooks/8144">Acetylene, the Principles of Its Generation and Use</a></i> at <a href="/wiki/Project_Gutenberg" title="Project Gutenberg">Project Gutenberg</a></span></li> <li><a rel="nofollow" class="external text" href="https://www.youtube.com/watch?v=KXh7__ri1VQ">Movie explaining acetylene formation from calcium carbide and the explosive limits forming fire hazards</a></li> <li><a rel="nofollow" class="external text" href="http://www.periodicvideos.com/videos/mv_calcium_carbide.htm">Calcium Carbide & Acetylene</a> at <i><a href="/wiki/The_Periodic_Table_of_Videos" class="mw-redirect" title="The Periodic Table of Videos">The Periodic Table of Videos</a></i> (University of Nottingham)</li> <li><a rel="nofollow" class="external text" href="https://www.cdc.gov/niosh/npg/npgd0008.html">CDC – NIOSH Pocket Guide to Chemical Hazards – Acetylene</a></li></ul> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl ol,.mw-parser-output .hlist dl ul,.mw-parser-output .hlist ol dl,.mw-parser-output .hlist ol ol,.mw-parser-output .hlist ol ul,.mw-parser-output .hlist ul dl,.mw-parser-output .hlist ul ol,.mw-parser-output .hlist ul ul{display:inline}.mw-parser-output .hlist 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href="mw-data:TemplateStyles:r1123817410"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"></div><div role="navigation" class="navbox" aria-labelledby="Alkynes" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><style 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abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Alkynes" title="Template:Alkynes"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Alkynes" title="Template talk:Alkynes"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Alkynes" title="Special:EditPage/Template:Alkynes"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Alkynes" style="font-size:114%;margin:0 4em"><a href="/wiki/Alkyne" title="Alkyne">Alkynes</a></div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a class="mw-selflink selflink">Ethyne</a> (<span class="chemf nowrap">C<sub class="template-chem2-sub">2</sub>H<sub class="template-chem2-sub">2</sub></span>)</li> <li><a href="/wiki/Propyne" title="Propyne">Propyne</a> (<span class="chemf nowrap">C<sub class="template-chem2-sub">3</sub>H<sub class="template-chem2-sub">4</sub></span>)</li> <li><a href="/wiki/Butyne" title="Butyne">Butyne</a> (<span class="chemf nowrap">C<sub class="template-chem2-sub">4</sub>H<sub class="template-chem2-sub">6</sub></span>) <ul><li><a href="/wiki/1-Butyne" title="1-Butyne">1</a></li> <li><a href="/wiki/2-Butyne" title="2-Butyne">2</a></li></ul></li> <li><a href="/wiki/Pentyne" title="Pentyne">Pentyne</a> (<span class="chemf nowrap">C<sub class="template-chem2-sub">5</sub>H<sub class="template-chem2-sub">8</sub></span>) <ul><li><a href="/wiki/1-Pentyne" title="1-Pentyne">1</a></li> <li><a href="/wiki/2-Pentyne" title="2-Pentyne">2</a></li></ul></li> <li><a href="/wiki/Hexyne" title="Hexyne">Hexyne</a> (<span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">10</sub></span>) <ul><li><a href="/wiki/1-Hexyne" title="1-Hexyne">1</a></li> <li><a href="/wiki/2-Hexyne" title="2-Hexyne">2</a></li> <li><a href="/wiki/3-Hexyne" title="3-Hexyne">3</a></li></ul></li> <li><a href="/wiki/Heptyne" title="Heptyne">Heptyne</a> (<span class="chemf nowrap">C<sub class="template-chem2-sub">7</sub>H<sub class="template-chem2-sub">12</sub></span>)</li> <li><a href="/wiki/Octyne" title="Octyne">Octyne</a> (<span class="chemf nowrap">C<sub class="template-chem2-sub">8</sub>H<sub class="template-chem2-sub">14</sub></span>) <ul><li><a href="/wiki/2-Octyne" title="2-Octyne">2</a></li> <li><a href="/wiki/4-Octyne" title="4-Octyne">4</a></li></ul></li> <li><a href="/wiki/Nonyne" title="Nonyne">Nonyne</a> (<span class="chemf nowrap">C<sub class="template-chem2-sub">9</sub>H<sub class="template-chem2-sub">16</sub></span>)</li> <li><a href="/wiki/Decyne" title="Decyne">Decyne</a> (<span class="chemf nowrap">C<sub class="template-chem2-sub">10</sub>H<sub class="template-chem2-sub">18</sub></span>) <ul><li><a href="/wiki/1-Decyne" title="1-Decyne">1</a></li> <li><a href="/wiki/5-Decyne" title="5-Decyne">5</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Preparations</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cracking_(chemistry)" title="Cracking (chemistry)">Cracking</a></li> <li><a href="/wiki/Dehydrogenation" title="Dehydrogenation">Dehydrogenation</a> of <a href="/wiki/Alkane" title="Alkane">alkane</a>, <a href="/wiki/Alkene" title="Alkene">alkene</a></li> <li><a href="/wiki/Alkylation" title="Alkylation">Alkylation</a> of <a href="/wiki/Acetylide" title="Acetylide">alkynyl anion</a></li> <li><a href="/wiki/Dehydrohalogenation" title="Dehydrohalogenation">Dehydrohalogenation</a> of <a href="/wiki/Dihaloalkane" class="mw-redirect" title="Dihaloalkane">dihaloalkane</a></li> <li><a href="/wiki/Fritsch%E2%80%93Buttenberg%E2%80%93Wiechell_rearrangement" title="Fritsch–Buttenberg–Wiechell rearrangement">Fritsch–Buttenberg–Wiechell rearrangement</a></li> <li><a href="/wiki/Corey%E2%80%93Fuchs_reaction" title="Corey–Fuchs reaction">Corey–Fuchs reaction</a></li> <li><a href="/wiki/Seyferth%E2%80%93Gilbert_homologation" title="Seyferth–Gilbert homologation">Seyferth–Gilbert homologation</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Reactions</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetylide" title="Acetylide">Deprotonation</a></li> <li><a href="/wiki/Hydrogenation" title="Hydrogenation">Hydrogenation</a></li> <li><a href="/wiki/Halogenation" title="Halogenation">Halogenation</a></li> <li><a href="/wiki/Hydration_reaction" title="Hydration reaction">Hydration</a></li> <li><a href="/wiki/Hydroboration" title="Hydroboration">Hydroboration</a></li> <li><a href="/wiki/Hydrohalogenation" title="Hydrohalogenation">Hydrohalogenation</a></li> <li><a href="/wiki/Alkynylation" title="Alkynylation">Alkynylation</a></li> <li><a href="/wiki/Thiol-yne_reaction" title="Thiol-yne reaction">Thiol-yne reaction</a></li> <li><a href="/wiki/Alkyne_trimerisation" title="Alkyne trimerisation">Alkyne trimerisation</a></li> <li><a href="/wiki/Diels%E2%80%93Alder_reaction" title="Diels–Alder reaction">Diels–Alder reaction</a></li> <li><a href="/wiki/Pauson%E2%80%93Khand_reaction" title="Pauson–Khand reaction">Pauson–Khand reaction</a></li> <li><a href="/wiki/Azide-alkyne_Huisgen_cycloaddition" title="Azide-alkyne Huisgen cycloaddition">Azide-alkyne Huisgen cycloaddition</a></li> <li><a href="/wiki/Sonogashira_coupling" title="Sonogashira coupling">Sonogashira coupling</a></li> <li><a href="/wiki/Cadiot%E2%80%93Chodkiewicz_coupling" title="Cadiot–Chodkiewicz coupling">Cadiot–Chodkiewicz coupling</a></li> <li><a href="/wiki/Glaser_coupling" title="Glaser coupling">Glaser coupling</a></li> <li><a href="/wiki/Favorskii_reaction" title="Favorskii reaction">Favorskii reaction</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Molecules_detected_in_outer_space" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Molecules_detected_in_outer_space" title="Template:Molecules detected in outer space"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Molecules_detected_in_outer_space" title="Template talk:Molecules detected in outer space"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Molecules_detected_in_outer_space" title="Special:EditPage/Template:Molecules detected in outer space"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Molecules_detected_in_outer_space" style="font-size:114%;margin:0 4em"><a 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/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/Imidogen" title="Imidogen">Imidogen</a></li> <li><a href="/wiki/Sulfur_mononitride" title="Sulfur mononitride">Sulfur mononitride</a></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_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><span typeof="mw:File"><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></span> <br /><br /><br /><br /> <span typeof="mw:File"><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></span> <br /><br /><br /><br /> <span typeof="mw:File"><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/90px-Buckminsterfullerene-perspective-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Buckminsterfullerene-perspective-3D-balls.png/120px-Buckminsterfullerene-perspective-3D-balls.png 2x" data-file-width="1056" data-file-height="1100" /></a></span></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="/w/index.php?title=Iron_cyanide&action=edit&redlink=1" class="new" title="Iron cyanide (page does not exist)">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/Diazenylium" title="Diazenylium">N<sub>2</sub>H<sup>+</sup></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/Methylidynephosphane" title="Methylidynephosphane">Methylidynephosphane</a></li> <li><a href="/wiki/Potassium_cyanide" title="Potassium cyanide">Potassium cyanide</a></li> <li><a href="/wiki/Trihydrogen_cation" title="Trihydrogen cation">Trihydrogen cation</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/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<br />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 class="mw-selflink selflink">Acetylene</a></li> <li><a href="/wiki/Ammonia" title="Ammonia">Ammonia</a></li> <li><a href="/wiki/Isocyanic_acid" title="Isocyanic acid">Isocyanic acid</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="/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/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="/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/Thioformaldehyde" title="Thioformaldehyde">Thioformaldehyde</a></li> <li><a href="/wiki/Tricarbon_monoxide" title="Tricarbon monoxide">Tricarbon monoxide</a></li> <li><a href="/wiki/Tricarbon_monosulfide" title="Tricarbon monosulfide">Tricarbon monosulfide</a></li> <li><a href="/wiki/Thiocyanic_acid" title="Thiocyanic acid">Thiocyanic acid</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<br />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<br />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="/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/Cyclopropenone" title="Cyclopropenone">Cyclopropenone</a></li> <li><a href="/wiki/Diacetylene" title="Diacetylene">Diacetylene</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)">HC<sub>4</sub>N</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<br />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 href="/wiki/Ethylene_oxide" title="Ethylene oxide">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/Propyne" title="Propyne">Propyne</a></li> <li><a href="/wiki/Methylamine" title="Methylamine">Methylamine</a></li> <li><a href="/wiki/Methyl_isocyanate" title="Methyl isocyanate">Methyl isocyanate</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<br />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/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/Polyyne" title="Polyyne">Methylcyanoacetylene</a></li> <li><a href="/wiki/Methyl_formate" title="Methyl formate">Methyl formate</a></li> <li><a href="/wiki/Acrolein" title="Acrolein">Acrolein</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<br />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/Ethanol" title="Ethanol">Ethanol</a></li> <li><a href="/wiki/Polyyne" title="Polyyne">Methyldiacetylene</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/Ethanethiol" title="Ethanethiol">Ethanethiol</a></li> <li><a href="/wiki/Propionitrile" title="Propionitrile">Propionitrile</a></li> <li><a href="/wiki/N-Methylformamide" title="N-Methylformamide">N-Methylformamide</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<br />atoms<br />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> (C<sub>60</sub>, C<sub>60</sub><sup>+</sup>, fullerene, buckyball)</li> <li><a href="/wiki/C70_fullerene" title="C70 fullerene">C<sub>70</sub> fullerene</a></li> <li><a href="/wiki/Cyanopolyyne" title="Cyanopolyyne">Cyanodecapentayne</a></li> <li><a href="/wiki/Ethylene_glycol" title="Ethylene glycol">Ethylene glycol</a></li> <li><a href="/wiki/Ethyl_formate" title="Ethyl formate">Ethyl formate</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/Butyronitrile" title="Butyronitrile">Butyronitrile</a></li> <li><a href="/wiki/Pyrimidine" title="Pyrimidine">Pyrimidine</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></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><br />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/Propyne" title="Propyne">Propyne</a></li> <li><a href="/wiki/Diazenylium" title="Diazenylium">N<sub>2</sub>D<sup>+</sup></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/Methoxyethane" title="Methoxyethane">Methoxyethane</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="/wiki/Hemolithin" title="Hemolithin">Hemolithin</a></li> <li><a href="/w/index.php?title=H2NCO%2B&action=edit&redlink=1" class="new" title="H2NCO+ (page does not exist)">H<sub>2</sub>NCO<sup>+</sup></a></li> <li><a href="/wiki/Carbon" title="Carbon">Linear C<sub>5</sub></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/Photodissociation_region" title="Photodissociation region">Photodissociation region</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/Pseudo-panspermia" title="Pseudo-panspermia">Pseudo-panspermia</a></li> <li><a href="/wiki/Polycyclic_aromatic_hydrocarbon" title="Polycyclic aromatic hydrocarbon">Polycyclic aromatic hydrocarbon</a> (PAH)</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> <ul><li><b><span class="noviewer" typeof="mw:File"><span title="Category"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/16px-Symbol_category_class.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/23px-Symbol_category_class.svg.png 1.5x, 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src="//upload.wikimedia.org/wikipedia/commons/thumb/0/00/Crab_Nebula.jpg/16px-Crab_Nebula.jpg" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/00/Crab_Nebula.jpg/24px-Crab_Nebula.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/00/Crab_Nebula.jpg/32px-Crab_Nebula.jpg 2x" data-file-width="3864" data-file-height="3864" /></span></span> </span><a href="/wiki/Portal:Astronomy" title="Portal:Astronomy">Astronomy portal</a></li> <li><span class="nowrap"><span class="noviewer" typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Papapishu-Lab-icon-6.svg/16px-Papapishu-Lab-icon-6.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Papapishu-Lab-icon-6.svg/24px-Papapishu-Lab-icon-6.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Papapishu-Lab-icon-6.svg/32px-Papapishu-Lab-icon-6.svg.png 2x" data-file-width="512" data-file-height="512" /></span></span> </span><a href="/wiki/Portal:Chemistry" title="Portal:Chemistry">Chemistry portal</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Binary_compounds_of_hydrogen" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Hydrides_by_group" title="Template:Hydrides by group"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Hydrides_by_group" title="Template talk:Hydrides by group"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Hydrides_by_group" title="Special:EditPage/Template:Hydrides by group"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Binary_compounds_of_hydrogen" style="font-size:114%;margin:0 4em"><a href="/wiki/Binary_compounds_of_hydrogen" title="Binary compounds of hydrogen">Binary compounds of hydrogen</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hydride#Ionic_hydrides" title="Hydride">Alkali metal <br />(Group 1) hydrides</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Lithium_hydride" title="Lithium hydride">LiH</a></li> <li><a href="/wiki/Sodium_hydride" title="Sodium hydride">NaH</a></li> <li><a href="/wiki/Potassium_hydride" title="Potassium hydride">KH</a></li> <li><a href="/wiki/Rubidium_hydride" title="Rubidium hydride">RbH</a></li> <li><a href="/wiki/Caesium_hydride" title="Caesium hydride">CsH</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hydride#Ionic_hydrides" title="Hydride">Alkaline <br />(Group 2) <br />earth hydrides</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Monohydrides" scope="row" class="navbox-group" style="width:1%">Monohydrides</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/Beryllium_monohydride" title="Beryllium monohydride">BeH</a></li> <li><a href="/wiki/Magnesium_monohydride" title="Magnesium monohydride">MgH</a></li> <li><a href="/wiki/Calcium_monohydride" title="Calcium monohydride">CaH</a></li> <li><a href="/w/index.php?title=Strontium_monohydride&action=edit&redlink=1" class="new" title="Strontium monohydride (page does not exist)">SrH</a></li> <li><a href="/w/index.php?title=Barium_monohydride&action=edit&redlink=1" class="new" title="Barium monohydride (page does not exist)">BaH</a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Dihydrides" scope="row" class="navbox-group" style="width:1%">Dihydrides</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/Beryllium_hydride" title="Beryllium hydride">BeH<sub>2</sub></a></li> <li><a href="/wiki/Magnesium_hydride" title="Magnesium hydride">MgH<sub>2</sub></a></li> <li><a href="/wiki/Calcium_hydride" title="Calcium hydride">CaH<sub>2</sub></a></li> <li><a href="/wiki/Strontium_hydride" title="Strontium hydride">SrH<sub>2</sub></a></li> <li><a href="/wiki/Barium_hydride" title="Barium hydride">BaH<sub>2</sub></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/Group_13_hydride" title="Group 13 hydride">Group 13 <br />hydrides</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Boranes" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Boranes" title="Boranes">Boranes</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/Borane" title="Borane">BH<sub>3</sub></a></li> <li><a href="/wiki/Boron_monohydride" title="Boron monohydride">BH</a></li> <li><a href="/wiki/Diborane" title="Diborane">B<sub>2</sub>H<sub>6</sub></a></li> <li><a href="/wiki/Diborane(2)" title="Diborane(2)">B<sub>2</sub>H<sub>2</sub></a></li> <li><a href="/wiki/Diborane(4)" title="Diborane(4)">B<sub>2</sub>H<sub>4</sub></a></li> <li><a href="/wiki/Tetraborane" title="Tetraborane">B<sub>4</sub>H<sub>10</sub></a></li> <li><a href="/wiki/Pentaborane(9)" title="Pentaborane(9)">B<sub>5</sub>H<sub>9</sub></a></li> <li><a href="/wiki/Pentaborane(11)" title="Pentaborane(11)">B<sub>5</sub>H<sub>11</sub></a></li> <li><a href="/wiki/Hexaborane(10)" title="Hexaborane(10)">B<sub>6</sub>H<sub>10</sub></a></li> <li><a href="/wiki/Hexaborane(12)" title="Hexaborane(12)">B<sub>6</sub>H<sub>12</sub></a></li> <li><a href="/wiki/Decaborane" title="Decaborane">B<sub>10</sub>H<sub>14</sub></a></li> <li><a href="/wiki/Octadecaborane" title="Octadecaborane">B<sub>18</sub>H<sub>22</sub></a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Alanes" scope="row" class="navbox-group" style="width:1%">Alanes</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_hydride" title="Aluminium hydride">AlH<sub>3</sub></a></li> <li><a href="/wiki/Dialane" title="Dialane">Al<sub>2</sub>H<sub>6</sub></a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Gallanes" scope="row" class="navbox-group" style="width:1%">Gallanes</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/Gallane" title="Gallane">GaH<sub>3</sub></a></li> <li><a href="/wiki/Digallane" title="Digallane">Ga<sub>2</sub>H<sub>6</sub></a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Indiganes" scope="row" class="navbox-group" style="width:1%">Indiganes</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/Indium_trihydride" title="Indium trihydride">InH<sub>3</sub></a></li> <li><a href="/w/index.php?title=Diindigane&action=edit&redlink=1" class="new" title="Diindigane (page does not exist)">In<sub>2</sub>H<sub>6</sub></a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Thallanes" scope="row" class="navbox-group" style="width:1%">Thallanes</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/Thallane" title="Thallane">TlH<sub>3</sub></a></li> <li><a href="/w/index.php?title=Dithallane&action=edit&redlink=1" class="new" title="Dithallane (page does not exist)">Tl<sub>2</sub>H<sub>6</sub></a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Nihonanes_(predicted)" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nihonium" title="Nihonium">Nihonanes</a> (<i>predicted</i>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>NhH</i></li> <li><i>NhH<sub>3</sub></i></li> <li><i>Nh<sub>2</sub>H<sub>6</sub></i></li> <li><i>NhH<sub>5</sub></i></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Group_14_hydride" title="Group 14 hydride">Group 14 hydrides</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Hydrocarbons" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hydrocarbon" title="Hydrocarbon">Hydrocarbons</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/Alkane" title="Alkane">alkanes</a></li> <li><a href="/wiki/Alkene" title="Alkene">alkenes</a></li> <li><a href="/wiki/Alkyne" title="Alkyne">alkynes</a></li> <li><a href="/wiki/Cycloalkane" title="Cycloalkane">Cycloalkanes</a></li> <li><a href="/wiki/Cycloalkene" title="Cycloalkene">Cycloalkenes</a></li> <li><a href="/wiki/Cycloalkyne" title="Cycloalkyne">Cycloalkynes</a></li> <li><a href="/wiki/Annulenes" class="mw-redirect" title="Annulenes">Annulenes</a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Methylidyne_radical" title="Methylidyne radical">CH</a></li> <li><a href="/wiki/Methylene_(compound)" title="Methylene (compound)">CH<sub>2</sub></a></li> <li><a href="/wiki/Methyl_radical" title="Methyl radical">CH<sub>3</sub></a></li> <li><a href="/wiki/Ethynyl_radical" title="Ethynyl radical">C<sub>2</sub>H</a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Silanes" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Silanes" title="Silanes">Silanes</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/Silane" title="Silane">SiH<sub>4</sub></a></li> <li><a href="/wiki/Disilane" title="Disilane">Si<sub>2</sub>H<sub>6</sub></a></li> <li><a href="/wiki/Trisilane" title="Trisilane">Si<sub>3</sub>H<sub>8</sub></a></li> <li><a href="/wiki/Tetrasilane" title="Tetrasilane">Si<sub>4</sub>H<sub>10</sub></a></li> <li><a href="/wiki/Pentasilane" class="mw-redirect" title="Pentasilane">Si<sub>5</sub>H<sub>12</sub></a></li> <li><a href="/wiki/Hexasilane" class="mw-redirect" title="Hexasilane">Si<sub>6</sub>H<sub>14</sub></a></li> <li><a href="/w/index.php?title=Heptasilane&action=edit&redlink=1" class="new" title="Heptasilane (page does not exist)">Si<sub>7</sub>H<sub>16</sub></a></li> <li><a href="/w/index.php?title=Octasilane&action=edit&redlink=1" class="new" title="Octasilane (page does not exist)">Si<sub>8</sub>H<sub>18</sub></a></li> <li><a href="/w/index.php?title=Nonasilane&action=edit&redlink=1" class="new" title="Nonasilane (page does not exist)">Si<sub>9</sub>H<sub>20</sub></a></li> <li><a href="/w/index.php?title=Decasilane&action=edit&redlink=1" class="new" title="Decasilane (page does not exist)">Si<sub>10</sub>H<sub>22</sub></a></li> <li><a href="/wiki/Silanes" title="Silanes">more...</a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Silenes" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Silenes" title="Silenes">Silenes</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/Disilene" title="Disilene">Si<sub>2</sub>H<sub>4</sub></a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Silynes" scope="row" class="navbox-group" style="width:1%"><a href="/w/index.php?title=Silynes&action=edit&redlink=1" class="new" title="Silynes (page does not exist)">Silynes</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/Disilyne" title="Disilyne">Si<sub>2</sub>H<sub>2</sub></a></li> <li><a href="/wiki/Silicon_monohydride" class="mw-redirect" title="Silicon monohydride">SiH</a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Germanes" scope="row" class="navbox-group" style="width:1%"><a href="/w/index.php?title=Germanes&action=edit&redlink=1" class="new" title="Germanes (page does not exist)">Germanes</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/Germane" title="Germane">GeH<sub>4</sub></a></li> <li><a href="/wiki/Digermane" title="Digermane">Ge<sub>2</sub>H<sub>6</sub></a></li> <li><a href="/w/index.php?title=Trigermane&action=edit&redlink=1" class="new" title="Trigermane (page does not exist)">Ge<sub>3</sub>H<sub>8</sub></a></li> <li><a href="/w/index.php?title=Tetragermane&action=edit&redlink=1" class="new" title="Tetragermane (page does not exist)">Ge<sub>4</sub>H<sub>10</sub></a></li> <li><a href="/w/index.php?title=Pentagermane&action=edit&redlink=1" class="new" title="Pentagermane (page does not exist)">Ge<sub>5</sub>H<sub>12</sub></a></li></ul> </div></td></tr></tbody></table><div></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Stannanes" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Stannanes" class="mw-redirect" title="Stannanes">Stannanes</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/Stannane" title="Stannane">SnH<sub>4</sub></a></li> <li><a href="/w/index.php?title=Distannane&action=edit&redlink=1" class="new" title="Distannane (page does not exist)">Sn<sub>2</sub>H<sub>6</sub></a></li></ul> </div></td></tr></tbody></table><div></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Plumbanes" scope="row" class="navbox-group" style="width:1%">Plumbanes</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/Plumbane" title="Plumbane">PbH<sub>4</sub></a></li></ul> </div></td></tr></tbody></table><div></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Flerovanes_(predicted)" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Flerovium" title="Flerovium">Flerovanes</a> (<i>predicted</i>)</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>FlH</i></li> <li><i>FlH<sub>2</sub></i></li> <li><i>FlH<sub>4</sub></i></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Pnictogen_hydride" title="Pnictogen hydride">Pnictogen <br />(Group 15) hydrides</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Azanes" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Azane" title="Azane">Azanes</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/Ammonia" title="Ammonia">NH<sub>3</sub></a></li> <li><a href="/wiki/Hydrazine" title="Hydrazine">N<sub>2</sub>H<sub>4</sub></a></li> <li><a href="/wiki/Triazane" title="Triazane">N<sub>3</sub>H<sub>5</sub></a></li> <li><a href="/w/index.php?title=Tetrazane&action=edit&redlink=1" class="new" title="Tetrazane (page does not exist)">N<sub>4</sub>H<sub>6</sub></a></li> <li><a href="/w/index.php?title=Pentazane&action=edit&redlink=1" class="new" title="Pentazane (page does not exist)">N<sub>5</sub>H<sub>7</sub></a></li> <li><a href="/w/index.php?title=Hexazane&action=edit&redlink=1" class="new" title="Hexazane (page does not exist)">N<sub>6</sub>H<sub>8</sub></a></li> <li><a href="/w/index.php?title=Heptazane&action=edit&redlink=1" class="new" title="Heptazane (page does not exist)">N<sub>7</sub>H<sub>9</sub></a></li> <li><a href="/w/index.php?title=Octazane&action=edit&redlink=1" class="new" title="Octazane (page does not exist)">N<sub>8</sub>H<sub>10</sub></a></li> <li><a href="/w/index.php?title=Nonazane&action=edit&redlink=1" class="new" title="Nonazane (page does not exist)">N<sub>9</sub>H<sub>11</sub></a></li> <li><a href="/w/index.php?title=Decazane&action=edit&redlink=1" class="new" title="Decazane (page does not exist)">N<sub>10</sub>H<sub>12</sub></a></li> <li><a href="/wiki/Azane" title="Azane">more...</a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Azenes" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Azo_compound" title="Azo compound">Azenes</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/Diazene" class="mw-redirect" title="Diazene">N<sub>2</sub>H<sub>2</sub></a></li> <li><a href="/wiki/Triazene" title="Triazene">N<sub>3</sub>H<sub>3</sub></a></li> <li><a href="/wiki/Tetrazene" title="Tetrazene">N<sub>4</sub>H<sub>4</sub></a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Phosphanes" scope="row" class="navbox-group" style="width:1%"><a href="/w/index.php?title=Phosphanes&action=edit&redlink=1" class="new" title="Phosphanes (page does not exist)">Phosphanes</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/Phosphine" title="Phosphine">PH<sub>3</sub></a></li> <li><a href="/wiki/Diphosphane" title="Diphosphane">P<sub>2</sub>H<sub>4</sub></a></li> <li><a href="/wiki/Triphosphane" title="Triphosphane">P<sub>3</sub>H<sub>5</sub></a></li> <li><a href="/w/index.php?title=Tetraphosphane&action=edit&redlink=1" class="new" title="Tetraphosphane (page does not exist)">P<sub>4</sub>H<sub>6</sub></a></li> <li><a href="/w/index.php?title=Pentaphosphane&action=edit&redlink=1" class="new" title="Pentaphosphane (page does not exist)">P<sub>5</sub>H<sub>7</sub></a></li> <li><a href="/w/index.php?title=Hexaphosphane&action=edit&redlink=1" class="new" title="Hexaphosphane (page does not exist)">P<sub>6</sub>H<sub>8</sub></a></li> <li><a href="/w/index.php?title=Heptaphosphane&action=edit&redlink=1" class="new" title="Heptaphosphane (page does not exist)">P<sub>7</sub>H<sub>9</sub></a></li> <li><a href="/w/index.php?title=Octaphosphane&action=edit&redlink=1" class="new" title="Octaphosphane (page does not exist)">P<sub>8</sub>H<sub>10</sub></a></li> <li><a href="/w/index.php?title=Nonaphosphane&action=edit&redlink=1" class="new" title="Nonaphosphane (page does not exist)">P<sub>9</sub>H<sub>11</sub></a></li> <li><a href="/w/index.php?title=Decaphosphane&action=edit&redlink=1" class="new" title="Decaphosphane (page does not exist)">P<sub>10</sub>H<sub>12</sub></a></li> <li><a href="/w/index.php?title=Phosphanes&action=edit&redlink=1" class="new" title="Phosphanes (page does not exist)">more...</a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Phosphenes" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Diphosphenes" title="Diphosphenes">Phosphenes</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/Diphosphene" title="Diphosphene">P<sub>2</sub>H<sub>2</sub></a></li> <li><a href="/w/index.php?title=Triphosphene&action=edit&redlink=1" class="new" title="Triphosphene (page does not exist)">P<sub>3</sub>H<sub>3</sub></a></li> <li><a href="/w/index.php?title=Tetraphosphene&action=edit&redlink=1" class="new" title="Tetraphosphene (page does not exist)">P<sub>4</sub>H<sub>4</sub></a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Arsanes" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Arsane" class="mw-redirect" title="Arsane">Arsanes</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/Arsine" title="Arsine">AsH<sub>3</sub></a></li> <li><a href="/wiki/Diarsine" class="mw-redirect" title="Diarsine">As<sub>2</sub>H<sub>4</sub></a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Stibanes" scope="row" class="navbox-group" style="width:1%">Stibanes</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/Stibine" title="Stibine">SbH<sub>3</sub></a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Bismuthanes" scope="row" class="navbox-group" style="width:1%">Bismuthanes</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/Bismuthine" title="Bismuthine">BiH<sub>3</sub></a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Moscovanes" scope="row" class="navbox-group" style="width:1%">Moscovanes</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Moscovium" title="Moscovium">McH<sub>3</sub></a></i> (<i>predicted</i>)</li></ul> </div></td></tr></tbody></table><div> <ul><li><a href="/wiki/Hydrazoic_acid" title="Hydrazoic acid">HN<sub>3</sub></a></li> <li><a href="/wiki/Imidogen" title="Imidogen">NH</a></li> <li><a href="/wiki/Pentazole" title="Pentazole">HN<sub>5</sub></a></li> <li><a href="/wiki/Nitrogen_pentahydride" title="Nitrogen pentahydride">NH<sub>5</sub></a> <i>(hypothetical)</i></li></ul></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hydrogen_chalcogenide" title="Hydrogen chalcogenide">Hydrogen <br />chalcogenides <br />(Group 16 hydrides)</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Polyoxidanes" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hydrogen_polyoxide" title="Hydrogen polyoxide">Polyoxidanes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <li><a href="/wiki/Properties_of_water" title="Properties of water">H<sub>2</sub>O</a></li> <li><a href="/wiki/Hydrogen_peroxide" title="Hydrogen peroxide">H<sub>2</sub>O<sub>2</sub></a></li> <li><a href="/wiki/Trioxidane" title="Trioxidane">H<sub>2</sub>O<sub>3</sub></a></li> <li><a href="/wiki/Tetraoxidane" title="Tetraoxidane">H<sub>2</sub>O<sub>4</sub></a></li> <li><a href="/wiki/Pentaoxidane" title="Pentaoxidane">H<sub>2</sub>O<sub>5</sub></a></li> <li><a href="/wiki/Hydrogen_polyoxide" title="Hydrogen polyoxide">more...</a></li> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Polysulfanes" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Polysulfane" title="Polysulfane">Polysulfanes</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/Hydrogen_sulfide" title="Hydrogen sulfide">H<sub>2</sub>S</a></li> <li><a href="/wiki/Hydrogen_disulfide" title="Hydrogen disulfide">H<sub>2</sub>S<sub>2</sub></a></li> <li><a href="/wiki/Trisulfane" title="Trisulfane">H<sub>2</sub>S<sub>3</sub></a></li> <li><a href="/w/index.php?title=Hydrogen_tetrasulfide&action=edit&redlink=1" class="new" title="Hydrogen tetrasulfide (page does not exist)">H<sub>2</sub>S<sub>4</sub></a></li> <li><a href="/w/index.php?title=Hydrogen_pentasulfide&action=edit&redlink=1" class="new" title="Hydrogen pentasulfide (page does not exist)">H<sub>2</sub>S<sub>5</sub></a></li> <li><a href="/w/index.php?title=Hydrogen_hexasulfide&action=edit&redlink=1" class="new" title="Hydrogen hexasulfide (page does not exist)">H<sub>2</sub>S<sub>6</sub></a></li> <li><a href="/w/index.php?title=Hydrogen_heptasulfide&action=edit&redlink=1" class="new" title="Hydrogen heptasulfide (page does not exist)">H<sub>2</sub>S<sub>7</sub></a></li> <li><a href="/w/index.php?title=Hydrogen_octasulfide&action=edit&redlink=1" class="new" title="Hydrogen octasulfide (page does not exist)">H<sub>2</sub>S<sub>8</sub></a></li> <li><a href="/w/index.php?title=Hydrogen_nonasulfide&action=edit&redlink=1" class="new" title="Hydrogen nonasulfide (page does not exist)">H<sub>2</sub>S<sub>9</sub></a></li> <li><a href="/w/index.php?title=Hydrogen_decasulfide&action=edit&redlink=1" class="new" title="Hydrogen decasulfide (page does not exist)">H<sub>2</sub>S<sub>10</sub></a></li> <li><a href="/wiki/Polysulfane" title="Polysulfane">more...</a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Selanes" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Selanes" class="mw-redirect" title="Selanes">Selanes</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/Hydrogen_selenide" title="Hydrogen selenide">H<sub>2</sub>Se</a></li> <li><a href="/wiki/Hydrogen_diselenide" title="Hydrogen diselenide">H<sub>2</sub>Se<sub>2</sub></a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Tellanes" scope="row" class="navbox-group" style="width:1%">Tellanes</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/Hydrogen_telluride" title="Hydrogen telluride">H<sub>2</sub>Te</a></li> <li><a href="/wiki/Hydrogen_ditelluride" title="Hydrogen ditelluride">H<sub>2</sub>Te<sub>2</sub></a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Polanes" scope="row" class="navbox-group" style="width:1%">Polanes</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/Polonium_hydride" title="Polonium hydride">PoH<sub>2</sub></a></li></ul> </div></td></tr></tbody></table><div> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Livermoranes" scope="row" class="navbox-group" style="width:1%">Livermoranes</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Livermorium" title="Livermorium">LvH<sub>2</sub></a></i> (<i>predicted</i>)</li></ul> </div></td></tr></tbody></table><div> <ul><li><a href="/wiki/Hydroxyl_radical" title="Hydroxyl radical">HO</a></li> <li><a href="/wiki/Hydroperoxyl" title="Hydroperoxyl">HO<sub>2</sub></a></li> <li><a href="/wiki/Hydrogen_ozonide" title="Hydrogen ozonide">HO<sub>3</sub></a></li> <li><a href="/w/index.php?title=Oxywater&action=edit&redlink=1" class="new" title="Oxywater (page does not exist)">H<sub>2</sub>O<sup>+</sup>–O<sup>–</sup></a> <i>(hypothetical)</i></li> <li><a href="/wiki/Sulfanyl" title="Sulfanyl">HS</a></li> <li><a href="/wiki/Semiheavy_water" title="Semiheavy water">HDO</a></li> <li><a href="/wiki/Heavy_water" title="Heavy water">D<sub>2</sub>O</a></li> <li><a href="/wiki/Tritiated_water" title="Tritiated water">T<sub>2</sub>O</a></li></ul></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hydrogen_halide" title="Hydrogen halide">Hydrogen halides <br />(Group 17 hydrides)</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <li><a href="/wiki/Hydrogen_fluoride" title="Hydrogen fluoride">HF</a></li> <li><a href="/wiki/Hydrogen_chloride" title="Hydrogen chloride">HCl</a></li> <li><a href="/wiki/Hydrogen_bromide" title="Hydrogen bromide">HBr</a></li> <li><a href="/wiki/Hydrogen_iodide" title="Hydrogen iodide">HI</a></li> <li><a href="/wiki/Hydrogen_astatide" title="Hydrogen astatide">HAt</a></li> <li><i><a href="/wiki/Tennessine" title="Tennessine">HTs</a></i> (<i>predicted</i>)</li> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Transition_metal_hydrides" class="mw-redirect" title="Transition metal hydrides">Transition metal hydrides</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Scandium_hydride" title="Scandium hydride">ScH<sub>2</sub></a></li> <li><a href="/wiki/Yttrium_hydride" title="Yttrium hydride">YH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Yttrium_trihydride&action=edit&redlink=1" class="new" title="Yttrium trihydride (page does not exist)">YH<sub>3</sub></a></li> <li><a href="/w/index.php?title=Yttrium_hexahydride&action=edit&redlink=1" class="new" title="Yttrium hexahydride (page does not exist)">YH<sub>6</sub></a></li> <li><a href="/w/index.php?title=Yttrium_nonahydride&action=edit&redlink=1" class="new" title="Yttrium nonahydride (page does not exist)">YH<sub>9</sub></a></li> <li><a href="/w/index.php?title=Lutetium_dihydride&action=edit&redlink=1" class="new" title="Lutetium dihydride (page does not exist)">LuH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Lutetium_trihydride&action=edit&redlink=1" class="new" title="Lutetium trihydride (page does not exist)">LuH<sub>3</sub></a></li> <li><a href="/wiki/Titanium_hydride" title="Titanium hydride">TiH<sub>2</sub></a></li> <li><a href="/wiki/Titanium(IV)_hydride" title="Titanium(IV) hydride">TiH<sub>4</sub></a></li> <li><a href="/wiki/Zirconium(II)_hydride" title="Zirconium(II) hydride">ZrH<sub>2</sub></a></li> <li><a href="/wiki/Zirconium_hydride" title="Zirconium hydride">ZrH<sub>4</sub></a></li> <li><a href="/w/index.php?title=Hafnium(II)_hydride&action=edit&redlink=1" class="new" title="Hafnium(II) hydride (page does not exist)">HfH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Hafnium_hydride&action=edit&redlink=1" class="new" title="Hafnium hydride (page does not exist)">HfH<sub>4</sub></a></li> <li><a href="/w/index.php?title=Vanadium(I)_hydride&action=edit&redlink=1" class="new" title="Vanadium(I) hydride (page does not exist)">VH</a></li> <li><a href="/w/index.php?title=Vanadium(II)_hydride&action=edit&redlink=1" class="new" title="Vanadium(II) hydride (page does not exist)">VH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Niobium_monohydride&action=edit&redlink=1" class="new" title="Niobium monohydride (page does not exist)">NbH</a></li> <li><a href="/w/index.php?title=Niobium_dihydride&action=edit&redlink=1" class="new" title="Niobium dihydride (page does not exist)">NbH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Tantalum_monohydride&action=edit&redlink=1" class="new" title="Tantalum monohydride (page does not exist)">TaH</a></li> <li><a href="/w/index.php?title=Tantalum_dihydride&action=edit&redlink=1" class="new" title="Tantalum dihydride (page does not exist)">TaH<sub>2</sub></a></li> <li><a href="/wiki/Chromium(I)_hydride" title="Chromium(I) hydride">CrH</a></li> <li><a href="/wiki/Chromium(II)_hydride" title="Chromium(II) hydride">CrH<sub>2</sub></a></li> <li><a href="/wiki/Chromium_hydride" title="Chromium hydride">CrH<sub>x</sub></a></li> <li><a href="/wiki/Iron(I)_hydride" title="Iron(I) hydride">FeH</a></li> <li><a href="/wiki/Iron(II)_hydride" title="Iron(II) hydride">FeH<sub>2</sub></a></li> <li><a href="/wiki/Iron_pentahydride" title="Iron pentahydride">FeH<sub>5</sub></a></li> <li><a href="/wiki/Cobalt(II)_hydride" title="Cobalt(II) hydride">CoH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Rhodium_hydride&action=edit&redlink=1" class="new" title="Rhodium hydride (page does not exist)">RhH<sub>2</sub></a></li> <li><a href="/wiki/Iridium_trihydride" title="Iridium trihydride">IrH<sub>3</sub></a></li> <li><a href="/wiki/Nickel_hydride" title="Nickel hydride">NiH</a></li> <li><a href="/wiki/Palladium_hydride" title="Palladium hydride">PdH<sub><i>x</i></sub> (<i>x</i> < 1)</a></li> <li><a href="/w/index.php?title=Platinum_hydride&action=edit&redlink=1" class="new" title="Platinum hydride (page does not exist)">PtH<sub><i>x</i></sub> (<i>x</i>< 1) </a></li> <li><i><a href="/wiki/Darmstadtium" title="Darmstadtium">DsH<sub>2</sub></a></i> (<i>predicted</i>)</li> <li><a href="/wiki/Copper_hydride" title="Copper hydride">CuH</a></li> <li><i><a href="/wiki/Roentgenium" title="Roentgenium">RgH</a></i> (<i>predicted</i>)</li> <li><a href="/wiki/Zinc_hydride" title="Zinc hydride">ZnH<sub>2</sub></a></li> <li><a href="/wiki/Cadmium_hydride" title="Cadmium hydride">CdH<sub>2</sub></a></li> <li><a href="/wiki/Mercury(I)_hydride" title="Mercury(I) hydride">HgH</a></li> <li><a href="/wiki/Mercury(I)_hydride" title="Mercury(I) hydride">Hg<sub>2</sub>H<sub>2</sub></a></li> <li><a href="/wiki/Mercury(II)_hydride" title="Mercury(II) hydride">HgH<sub>2</sub></a></li> <li><i><a href="/wiki/Copernicium" title="Copernicium">CnH<sub>2</sub></a></i> (<i>predicted</i>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/w/index.php?title=Lanthanide_hydrides&action=edit&redlink=1" class="new" title="Lanthanide hydrides (page does not exist)">Lanthanide hydrides</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Lanthanum_dihydride&action=edit&redlink=1" class="new" title="Lanthanum dihydride (page does not exist)">LaH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Lanthanum_trihydride&action=edit&redlink=1" class="new" title="Lanthanum trihydride (page does not exist)">LaH<sub>3</sub></a></li> <li><a href="/wiki/Lanthanum_decahydride" title="Lanthanum decahydride">LaH<sub>10</sub></a></li> <li><a href="/w/index.php?title=Cerium_dihydride&action=edit&redlink=1" class="new" title="Cerium dihydride (page does not exist)">CeH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Cerium_trihydride&action=edit&redlink=1" class="new" title="Cerium trihydride (page does not exist)">CeH<sub>3</sub></a></li> <li><a href="/w/index.php?title=Praseodymium_dihydride&action=edit&redlink=1" class="new" title="Praseodymium dihydride (page does not exist)">PrH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Praseodymium_hydride&action=edit&redlink=1" class="new" title="Praseodymium hydride (page does not exist)">PrH<sub>3</sub></a></li> <li><a href="/wiki/Neodymium(II)_hydride" title="Neodymium(II) hydride">NdH<sub>2</sub></a></li> <li><a href="/wiki/Neodymium(III)_hydride" title="Neodymium(III) hydride">NdH<sub>3</sub></a></li> <li><a href="/w/index.php?title=Samarium_dihydride&action=edit&redlink=1" class="new" title="Samarium dihydride (page does not exist)">SmH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Samarium_trihydride&action=edit&redlink=1" class="new" title="Samarium trihydride (page does not exist)">SmH<sub>3</sub></a></li> <li><a href="/wiki/Europium_hydride" title="Europium hydride">EuH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Gadolinium_dihydride&action=edit&redlink=1" class="new" title="Gadolinium dihydride (page does not exist)">GdH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Gadolinium_trihydride&action=edit&redlink=1" class="new" title="Gadolinium trihydride (page does not exist)">GdH<sub>3</sub></a></li> <li><a href="/w/index.php?title=Terbium_dihydride&action=edit&redlink=1" class="new" title="Terbium dihydride (page does not exist)">TbH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Terbium_trihydride&action=edit&redlink=1" class="new" title="Terbium trihydride (page does not exist)">TbH<sub>3</sub></a></li> <li><a href="/w/index.php?title=Dysprosium_dihydride&action=edit&redlink=1" class="new" title="Dysprosium dihydride (page does not exist)">DyH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Dysprosium_trihydride&action=edit&redlink=1" class="new" title="Dysprosium trihydride (page does not exist)">DyH<sub>3</sub></a></li> <li><a href="/w/index.php?title=Holmium_dihydride&action=edit&redlink=1" class="new" title="Holmium dihydride (page does not exist)">HoH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Holmium_trihydride&action=edit&redlink=1" class="new" title="Holmium trihydride (page does not exist)">HoH<sub>3</sub></a></li> <li><a href="/w/index.php?title=Erbium_dihydride&action=edit&redlink=1" class="new" title="Erbium dihydride (page does not exist)">ErH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Erbium_trihydride&action=edit&redlink=1" class="new" title="Erbium trihydride (page does not exist)">ErH<sub>3</sub></a></li> <li><a href="/w/index.php?title=Thulium_dihydride&action=edit&redlink=1" class="new" title="Thulium dihydride (page does not exist)">TmH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Thulium_trihydride&action=edit&redlink=1" class="new" title="Thulium trihydride (page does not exist)">TmH<sub>3</sub></a></li> <li><a href="/wiki/Ytterbium(II)_hydride" title="Ytterbium(II) hydride">YbH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Lutetium_dihydride&action=edit&redlink=1" class="new" title="Lutetium dihydride (page does not exist)">LuH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Lutetium_trihydride&action=edit&redlink=1" class="new" title="Lutetium trihydride (page does not exist)">LuH<sub>3</sub></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/w/index.php?title=Actinide_hydrides&action=edit&redlink=1" class="new" title="Actinide hydrides (page does not exist)">Actinide hydrides</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Actinium_dihydride&action=edit&redlink=1" class="new" title="Actinium dihydride (page does not exist)">AcH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Thorium_hydride&action=edit&redlink=1" class="new" title="Thorium hydride (page does not exist)">ThH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Thorium(IV)_hydride&action=edit&redlink=1" class="new" title="Thorium(IV) hydride (page does not exist)">ThH<sub>4</sub></a></li> <li>Th<sub>4</sub>H<sub>15</sub></li> <li><a href="/wiki/Protactinium_trihydride" title="Protactinium trihydride">PaH<sub>3</sub></a></li> <li><a href="/wiki/Uranium(III)_hydride" title="Uranium(III) hydride">UH<sub>3</sub></a></li> <li><a href="/wiki/Uranium(IV)_hydride" title="Uranium(IV) hydride">UH<sub>4</sub></a></li> <li><a href="/w/index.php?title=Neptunium_dihydride&action=edit&redlink=1" class="new" title="Neptunium dihydride (page does not exist)">NpH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Neptunium_trihydride&action=edit&redlink=1" class="new" title="Neptunium trihydride (page does not exist)">NpH<sub>3</sub></a></li> <li><a href="/wiki/Plutonium_hydride" title="Plutonium hydride">PuH<sub>2</sub></a></li> <li><a href="/wiki/Plutonium_hydride" title="Plutonium hydride">PuH<sub>3</sub></a></li> <li><a href="/w/index.php?title=Americium_dihydride&action=edit&redlink=1" class="new" title="Americium dihydride (page does not exist)">AmH<sub>2</sub></a></li> <li><a href="/wiki/Americium_trihydride" title="Americium trihydride">AmH<sub>3</sub></a></li> <li><a href="/w/index.php?title=Curium_hydride&action=edit&redlink=1" class="new" title="Curium hydride (page does not exist)">CmH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Berkelium_dihydride&action=edit&redlink=1" class="new" title="Berkelium dihydride (page does not exist)">BkH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Berkelium_trihydride&action=edit&redlink=1" class="new" title="Berkelium trihydride (page does not exist)">BkH<sub>3</sub></a></li> <li><a href="/w/index.php?title=Californium_dihydride&action=edit&redlink=1" class="new" title="Californium dihydride (page does not exist)">CfH<sub>2</sub></a></li> <li><a href="/w/index.php?title=Californium_trihydride&action=edit&redlink=1" class="new" title="Californium trihydride (page does not exist)">CfH<sub>3</sub></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Exotic_atoms" class="mw-redirect" title="Exotic atoms">Exotic matter hydrides</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Positronium_hydride" title="Positronium hydride">PsH</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"><style data-mw-deduplicate="TemplateStyles:r1038841319">.mw-parser-output .tooltip-dotted{border-bottom:1px dotted;cursor:help}</style><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"></div><div role="navigation" class="navbox authority-control" aria-label="Navbox" style="padding:3px"><table class="nowraplinks hlist navbox-inner" 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class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"><ul><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="Acetylin"><a rel="nofollow" class="external text" href="https://d-nb.info/gnd/4000345-0">Germany</a></span></span></li><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="Acetylene"><a rel="nofollow" class="external text" href="https://id.loc.gov/authorities/sh85000470">United States</a></span></span></li><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="Acétylène"><a rel="nofollow" class="external text" href="https://catalogue.bnf.fr/ark:/12148/cb11982014p">France</a></span></span></li><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="Acétylène"><a rel="nofollow" class="external text" href="https://data.bnf.fr/ark:/12148/cb11982014p">BnF data</a></span></span></li><li><span class="uid"><a 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