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</button> <ul id="toc-Industrial_uses-sublist" class="vector-toc-list"> <li id="toc-In_polymer_chemistry" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#In_polymer_chemistry"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>In polymer chemistry</span> </div> </a> <ul id="toc-In_polymer_chemistry-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Bleaching_and_disinfecting_agents" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Bleaching_and_disinfecting_agents"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>Bleaching and disinfecting agents</span> </div> </a> <ul id="toc-Bleaching_and_disinfecting_agents-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Preparation" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Preparation"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <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-From_hydrogen_peroxide" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#From_hydrogen_peroxide"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>From hydrogen peroxide</span> </div> </a> <ul id="toc-From_hydrogen_peroxide-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-From_O2" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#From_O2"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>From O<sub>2</sub></span> </div> </a> <ul id="toc-From_O2-sublist" class="vector-toc-list"> </ul> </li> </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">6</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-Homolysis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Homolysis"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.1</span> <span>Homolysis</span> </div> </a> <ul id="toc-Homolysis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Self-oxidation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Self-oxidation"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2</span> <span>Self-oxidation</span> </div> </a> <ul id="toc-Self-oxidation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Cumene_process" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Cumene_process"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.3</span> <span>Cumene process</span> </div> </a> <ul id="toc-Cumene_process-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Anthraquinone_process" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Anthraquinone_process"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.4</span> <span>Anthraquinone process</span> </div> </a> <ul id="toc-Anthraquinone_process-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Reduction" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Reduction"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.5</span> <span>Reduction</span> </div> </a> <ul id="toc-Reduction-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Organic_synthesis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Organic_synthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.6</span> <span>Organic synthesis</span> </div> </a> <ul id="toc-Organic_synthesis-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Analysis_of_peroxides" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Analysis_of_peroxides"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Analysis of peroxides</span> </div> </a> <button aria-controls="toc-Analysis_of_peroxides-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 Analysis of peroxides subsection</span> </button> <ul id="toc-Analysis_of_peroxides-sublist" class="vector-toc-list"> <li id="toc-Active_oxygen_in_peroxides" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Active_oxygen_in_peroxides"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.1</span> <span>Active oxygen in peroxides</span> </div> </a> <ul id="toc-Active_oxygen_in_peroxides-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Safety" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Safety"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Safety</span> </div> </a> <ul id="toc-Safety-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>See also</span> </div> </a> <ul id="toc-See_also-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> <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">11</span> <span>References</span> </div> </a> <ul id="toc-References-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" 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class="firstHeading mw-first-heading"><span class="mw-page-title-main">Organic peroxides</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 25 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-25" 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">25 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%A8%D9%8A%D8%B1%D9%88%D9%83%D8%B3%D9%8A%D8%AF_%D8%B9%D8%B6%D9%88%D9%8A" title="بيروكسيد عضوي – Arabic" lang="ar" hreflang="ar" data-title="بيروكسيد عضوي" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%9C%E0%A7%88%E0%A6%AC_%E0%A6%AA%E0%A6%BE%E0%A6%B0%E0%A6%85%E0%A6%95%E0%A7%8D%E0%A6%B8%E0%A6%BE%E0%A6%87%E0%A6%A1" title="জৈব পারঅক্সাইড – Bangla" lang="bn" hreflang="bn" data-title="জৈব পারঅক্সাইড" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Per%C3%B2xid_org%C3%A0nic" title="Peròxid orgànic – Catalan" lang="ca" hreflang="ca" data-title="Peròxid orgànic" 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/Organick%C3%BD_peroxid" title="Organický peroxid – Czech" lang="cs" hreflang="cs" data-title="Organický peroxid" 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/Organisk_peroxid" title="Organisk peroxid – Danish" lang="da" hreflang="da" data-title="Organisk peroxid" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de badge-Q70894304 mw-list-item" title=""><a href="https://de.wikipedia.org/wiki/Organische_Peroxide" title="Organische Peroxide – German" lang="de" hreflang="de" data-title="Organische Peroxide" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%9F%CF%81%CE%B3%CE%B1%CE%BD%CE%B9%CE%BA%CE%AC_%CF%85%CF%80%CE%B5%CF%81%CE%BF%CE%BE%CE%B5%CE%AF%CE%B4%CE%B9%CE%B1" title="Οργανικά υπεροξείδια – Greek" lang="el" hreflang="el" data-title="Οργανικά υπεροξείδια" 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/Per%C3%B3xido_org%C3%A1nico" title="Peróxido orgánico – Spanish" lang="es" hreflang="es" data-title="Peróxido orgánico" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Peroxido_organiko" title="Peroxido organiko – Basque" lang="eu" hreflang="eu" data-title="Peroxido organiko" 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/%D9%BE%D8%B1%D8%A7%DA%A9%D8%B3%DB%8C%D8%AF_%D8%A2%D9%84%DB%8C" title="پراکسید آلی – Persian" lang="fa" hreflang="fa" data-title="پراکسید آلی" 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/Peroxyde_organique" title="Peroxyde organique – French" lang="fr" hreflang="fr" data-title="Peroxyde organique" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Per%C3%B3xido_org%C3%A1nico" title="Peróxido orgánico – Galician" lang="gl" hreflang="gl" data-title="Peróxido orgánico" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Perossidi_organici" title="Perossidi organici – Italian" lang="it" hreflang="it" data-title="Perossidi organici" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Szerves_peroxidok" title="Szerves peroxidok – Hungarian" lang="hu" hreflang="hu" data-title="Szerves peroxidok" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%9A%E3%83%AB%E3%82%AA%E3%82%AD%E3%82%B7%E3%83%89" title="ペルオキシド – Japanese" lang="ja" hreflang="ja" data-title="ペルオキシド" 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-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Per%C3%B3xido_org%C3%A2nico" title="Peróxido orgânico – Portuguese" lang="pt" hreflang="pt" data-title="Peróxido orgânico" 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/Peroxid_organic" title="Peroxid organic – Romanian" lang="ro" hreflang="ro" data-title="Peroxid organic" 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%9E%D1%80%D0%B3%D0%B0%D0%BD%D0%B8%D1%87%D0%B5%D1%81%D0%BA%D0%B8%D0%B5_%D0%BF%D0%B5%D1%80%D0%BE%D0%BA%D1%81%D0%B8%D0%B4%D1%8B" title="Органические пероксиды – Russian" lang="ru" hreflang="ru" data-title="Органические пероксиды" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Organick%C3%BD_peroxid" title="Organický peroxid – Slovak" lang="sk" hreflang="sk" data-title="Organický peroxid" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Organski_peroksid" title="Organski peroksid – Serbian" lang="sr" hreflang="sr" data-title="Organski peroksid" 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/Organski_peroksid" title="Organski peroksid – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Organski peroksid" 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/Orgaaniset_peroksidit" title="Orgaaniset peroksidit – Finnish" lang="fi" hreflang="fi" data-title="Orgaaniset peroksidit" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%95%E0%AE%B0%E0%AE%BF%E0%AE%AE_%E0%AE%AA%E0%AF%86%E0%AE%B0%E0%AE%BE%E0%AE%95%E0%AF%8D%E0%AE%9A%E0%AF%88%E0%AE%9F%E0%AF%81" title="கரிம பெராக்சைடு – Tamil" lang="ta" hreflang="ta" data-title="கரிம பெராக்சைடு" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-uk badge-Q70893996 mw-list-item" title=""><a href="https://uk.wikipedia.org/wiki/%D0%9E%D1%80%D0%B3%D0%B0%D0%BD%D1%96%D1%87%D0%BD%D1%96_%D0%BF%D0%B5%D1%80%D0%BE%D0%BA%D1%81%D0%B8%D0%B4%D0%B8" title="Органічні пероксиди – Ukrainian" lang="uk" hreflang="uk" data-title="Органічні пероксиди" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E6%9C%89%E6%9C%BA%E8%BF%87%E6%B0%A7%E5%8C%96%E7%89%A9" title="有机过氧化物 – Chinese" lang="zh" hreflang="zh" data-title="有机过氧化物" 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 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<div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Organic compounds of the form R–O–O–R’</div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Peroxy_general.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9c/Peroxy_general.svg/150px-Peroxy_general.svg.png" decoding="async" width="150" height="127" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9c/Peroxy_general.svg/225px-Peroxy_general.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9c/Peroxy_general.svg/300px-Peroxy_general.svg.png 2x" data-file-width="512" data-file-height="432" /></a><figcaption>The general structure of an organic peroxide</figcaption></figure> <p>In <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a>, <b>organic peroxides</b> are <a href="/wiki/Organic_compound" title="Organic compound">organic compounds</a> containing the <a href="/wiki/Peroxide" title="Peroxide">peroxide</a> <a href="/wiki/Functional_group" title="Functional group">functional group</a> (<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">R−O−O−R′</span>). If the R′ is <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a>, the compounds are called <a href="/wiki/Hydroperoxide" title="Hydroperoxide">hydroperoxides</a>, which are discussed in that article. The O−O bond of peroxides easily breaks, producing <a href="/wiki/Free_radical" class="mw-redirect" title="Free radical">free radicals</a> of the form <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">RO<sup class="template-chem2-sup">•</sup></span> (the dot represents an <a href="/wiki/Unpaired_electron" title="Unpaired electron">unpaired electron</a>). Thus, organic peroxides are useful as <a href="/wiki/Radical_initiator" title="Radical initiator">initiators</a> for some types of <a href="/wiki/Polymerization" title="Polymerization">polymerization</a>, such as the <a href="/wiki/Acrylic_resin" title="Acrylic resin">acrylic</a>, unsaturated polyester, and <a href="/wiki/Vinyl_ester" title="Vinyl ester">vinyl ester</a> <a href="/wiki/Resin" title="Resin">resins</a> used in <a href="/wiki/Glass-reinforced_plastic" class="mw-redirect" title="Glass-reinforced plastic">glass-reinforced plastics</a>. <a href="/wiki/Methyl_ethyl_ketone_peroxide" title="Methyl ethyl ketone peroxide">MEKP</a> and <a href="/wiki/Benzoyl_peroxide" title="Benzoyl peroxide">benzoyl peroxide</a> are commonly used for this purpose. However, the same property also means that organic peroxides can explosively combust. Organic peroxides, like their inorganic counterparts, are often powerful <a href="/wiki/Bleaching" class="mw-redirect" title="Bleaching">bleaching</a> agents.<sup id="cite_ref-Ullmann_1-0" class="reference"><a href="#cite_note-Ullmann-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Types_of_organic_peroxides">Types of organic peroxides</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organic_peroxides&action=edit&section=1" title="Edit section: Types of organic peroxides"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Organic peroxides are classified (i) by the presence or absence of a hydroxyl (-OH) terminus and (ii) by the presence of alkyl vs acyl substituents.<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <ul class="gallery mw-gallery-traditional"> <li class="gallerycaption">Examples of organic peroxides</li> <li class="gallerybox" style="width: 205px"> <div class="thumb" style="width: 200px; height: 143px;"><span typeof="mw:File"><a href="/wiki/File:Tert-Butyl_hydroperoxide_Structural_Formula_V2.svg" class="mw-file-description" title="tert-Butyl hydroperoxide, a hydroperoxide (formula: ROOH), which is used to epoxide alkenes."><img alt="tert-Butyl hydroperoxide, a hydroperoxide (formula: ROOH), which is used to epoxide alkenes." src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9c/Tert-Butyl_hydroperoxide_Structural_Formula_V2.svg/170px-Tert-Butyl_hydroperoxide_Structural_Formula_V2.svg.png" decoding="async" width="170" height="102" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9c/Tert-Butyl_hydroperoxide_Structural_Formula_V2.svg/255px-Tert-Butyl_hydroperoxide_Structural_Formula_V2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9c/Tert-Butyl_hydroperoxide_Structural_Formula_V2.svg/340px-Tert-Butyl_hydroperoxide_Structural_Formula_V2.svg.png 2x" data-file-width="659" data-file-height="396" /></a></span></div> <div class="gallerytext"><a href="/wiki/Tert-Butyl_hydroperoxide" title="Tert-Butyl hydroperoxide"><i>tert</i>-Butyl hydroperoxide</a>, a <a href="/wiki/Hydroperoxide" title="Hydroperoxide">hydroperoxide</a> (formula: ROOH), which is used to epoxide alkenes.</div> </li> <li class="gallerybox" style="width: 205px"> <div class="thumb" style="width: 200px; height: 143px;"><span typeof="mw:File"><a href="/wiki/File:Dicumyl_peroxide.svg" class="mw-file-description" title="Dicumyl peroxide, a dialkyl peroxide (formula: ROOR), which is used to initiate polymerizations."><img alt="Dicumyl peroxide, a dialkyl peroxide (formula: ROOR), which is used to initiate polymerizations." src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ee/Dicumyl_peroxide.svg/170px-Dicumyl_peroxide.svg.png" decoding="async" width="170" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ee/Dicumyl_peroxide.svg/255px-Dicumyl_peroxide.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ee/Dicumyl_peroxide.svg/340px-Dicumyl_peroxide.svg.png 2x" data-file-width="950" data-file-height="448" /></a></span></div> <div class="gallerytext"><a href="/wiki/Dicumyl_peroxide" title="Dicumyl peroxide">Dicumyl peroxide</a>, a dialkyl peroxide (formula: ROOR), which is used to initiate polymerizations.</div> </li> <li class="gallerybox" style="width: 205px"> <div class="thumb" style="width: 200px; height: 143px;"><span typeof="mw:File"><a href="/wiki/File:Tert-Butylperoxybenzoat_Strukturformel.svg" class="mw-file-description" title="tert-butylperoxybenzoate, a peroxy ester (formula: RCO3R') that used as a radical initiator."><img alt="tert-butylperoxybenzoate, a peroxy ester (formula: RCO3R') that used as a radical initiator." src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b3/Tert-Butylperoxybenzoat_Strukturformel.svg/170px-Tert-Butylperoxybenzoat_Strukturformel.svg.png" decoding="async" width="170" height="82" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b3/Tert-Butylperoxybenzoat_Strukturformel.svg/255px-Tert-Butylperoxybenzoat_Strukturformel.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b3/Tert-Butylperoxybenzoat_Strukturformel.svg/340px-Tert-Butylperoxybenzoat_Strukturformel.svg.png 2x" data-file-width="173" data-file-height="83" /></a></span></div> <div class="gallerytext"><a href="/wiki/Tert-Butyl_peroxybenzoate" title="Tert-Butyl peroxybenzoate"><i>tert</i>-butylperoxybenzoate</a>, a peroxy ester (formula: <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">RCO<sub class="template-chem2-sub">3</sub>R'</span>) that used as a radical initiator.</div> </li> <li class="gallerybox" style="width: 205px"> <div class="thumb" style="width: 200px; height: 143px;"><span typeof="mw:File"><a href="/wiki/File:Benzoyl-peroxide.svg" class="mw-file-description" title="dibenzoyl peroxide, a diacyl peroxide (formula: (RCO2)2)) is also used as an initiator for polymerizations."><img alt="dibenzoyl peroxide, a diacyl peroxide (formula: (RCO2)2)) is also used as an initiator for polymerizations." src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b8/Benzoyl-peroxide.svg/170px-Benzoyl-peroxide.svg.png" decoding="async" width="170" height="85" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b8/Benzoyl-peroxide.svg/255px-Benzoyl-peroxide.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b8/Benzoyl-peroxide.svg/340px-Benzoyl-peroxide.svg.png 2x" data-file-width="426" data-file-height="213" /></a></span></div> <div class="gallerytext"><a href="/wiki/Dibenzoyl_peroxide" class="mw-redirect" title="Dibenzoyl peroxide">dibenzoyl peroxide</a>, a diacyl peroxide (formula: <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(RCO<sub class="template-chem2-sub">2</sub>)<sub class="template-chem2-sub">2</sub>)</span>) is also used as an initiator for polymerizations.</div> </li> <li class="gallerybox" style="width: 205px"> <div class="thumb" style="width: 200px; height: 143px;"><span typeof="mw:File"><a href="/wiki/File:Ethaneperoxoic_acid_200.svg" class="mw-file-description" title="Peroxyacetic acid, a peroxycarboxylic acid (formula: (RCO3H), is a reagent in organic synthesis."><img alt="Peroxyacetic acid, a peroxycarboxylic acid (formula: (RCO3H), is a reagent in organic synthesis." src="//upload.wikimedia.org/wikipedia/commons/thumb/c/ce/Ethaneperoxoic_acid_200.svg/170px-Ethaneperoxoic_acid_200.svg.png" decoding="async" width="170" height="89" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/ce/Ethaneperoxoic_acid_200.svg/255px-Ethaneperoxoic_acid_200.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/ce/Ethaneperoxoic_acid_200.svg/340px-Ethaneperoxoic_acid_200.svg.png 2x" data-file-width="128" data-file-height="67" /></a></span></div> <div class="gallerytext"><a href="/wiki/Peroxyacetic_acid" class="mw-redirect" title="Peroxyacetic acid">Peroxyacetic acid</a>, a <a href="/wiki/Peroxycarboxylic_acid" class="mw-redirect" title="Peroxycarboxylic acid">peroxycarboxylic acid</a> (formula: <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(RCO<sub class="template-chem2-sub">3</sub>H</span>), is a reagent in <a href="/wiki/Organic_synthesis" title="Organic synthesis">organic synthesis</a>.</div> </li> <li class="gallerybox" style="width: 205px"> <div class="thumb" style="width: 200px; height: 143px;"><span typeof="mw:File"><a href="/wiki/File:Prostaglandin_G2.svg" class="mw-file-description" title="Prostaglandin G2, an endo peroxide, the precursor to other prostaglandins"><img alt="Prostaglandin G2, an endo peroxide, the precursor to other prostaglandins" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f7/Prostaglandin_G2.svg/154px-Prostaglandin_G2.svg.png" decoding="async" width="154" height="113" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f7/Prostaglandin_G2.svg/232px-Prostaglandin_G2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f7/Prostaglandin_G2.svg/308px-Prostaglandin_G2.svg.png 2x" data-file-width="675" data-file-height="495" /></a></span></div> <div class="gallerytext"><a href="/wiki/Prostaglandin_G2" title="Prostaglandin G2">Prostaglandin G2</a>, an endo peroxide, the precursor to other prostaglandins</div> </li> </ul> <p>One gap in the classes of organic peroxides is diphenyl peroxide. Quantum chemical calculations predict that it undergoes a nearly barrierless reaction akin to the <a href="/wiki/Benzidine_rearrangement" class="mw-redirect" title="Benzidine rearrangement">benzidine rearrangement</a>.<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> </p> <div class="mw-heading mw-heading2"><h2 id="Properties">Properties</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organic_peroxides&action=edit&section=2" title="Edit section: Properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The O−O <a href="/wiki/Bond_length" title="Bond length">bond length</a> in peroxides is about 1.45 <a href="/wiki/%C3%85ngstr%C3%B6m" class="mw-redirect" title="Ångström">Å</a>, and the R−O−O angles (R = H, C) are about 110° (water-like). Characteristically, the C−O−O−R (R = H, C) dihedral angles are about 120°. The O−O bond is relatively weak, with a <a href="/wiki/Bond_dissociation_energy" class="mw-redirect" title="Bond dissociation energy">bond dissociation energy</a> of 45–50 <a href="/wiki/Kilocalorie_per_mole" title="Kilocalorie per mole">kcal/mol</a> (190–210 <a href="/wiki/Joule_per_mole" title="Joule per mole">kJ/mol</a>), less than half the strengths of C−C, C−H, and C−O bonds.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Biology">Biology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organic_peroxides&action=edit&section=3" title="Edit section: Biology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Ascaridol2.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/cc/Ascaridol2.png/220px-Ascaridol2.png" decoding="async" width="220" height="86" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/cc/Ascaridol2.png/330px-Ascaridol2.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/cc/Ascaridol2.png/440px-Ascaridol2.png 2x" data-file-width="500" data-file-height="195" /></a><figcaption>The peroxide <a href="/wiki/Ascaridole" title="Ascaridole">ascaridole</a>, derived from <a href="/wiki/Terpinene" title="Terpinene">terpinene</a>.</figcaption></figure> <p>Peroxides play important roles in biology. Hundreds of peroxides and hydroperoxides are known, being derived from fatty acids, steroids, and terpenes.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/Prostaglandin" title="Prostaglandin">prostaglandins</a> are biosynthesized by initial formation of a bicyclic peroxide ("endoperoxide") derived from <a href="/wiki/Arachidonic_acid" title="Arachidonic acid">arachidonic acid</a>.<sup id="cite_ref-Marnett_7-0" class="reference"><a href="#cite_note-Marnett-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p><p>Many aspects of biodegradation or aging are attributed to the formation and decay of peroxides formed from oxygen in air. Countering these effects, an array of biological and artificial <a href="/wiki/Antioxidant" title="Antioxidant">antioxidants</a> destroy peroxides. </p><p>In <a href="/wiki/Firefly" title="Firefly">fireflies</a>, oxidation of <a href="/wiki/Firefly_luciferin" title="Firefly luciferin">luciferins</a>, which is catalyzed by <a href="/wiki/Luciferase" title="Luciferase">luciferases</a>, yields a peroxy compound <a href="/wiki/1,2-dioxetane" class="mw-redirect" title="1,2-dioxetane">1,2-dioxetane</a>. The dioxetane is unstable and decays spontaneously to <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a> and excited <a href="/wiki/Ketone" title="Ketone">ketones</a>, which release excess energy by emitting light (<a href="/wiki/Bioluminescence" title="Bioluminescence">bioluminescence</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> </p> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Luciferin_principle.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a4/Luciferin_principle.png/450px-Luciferin_principle.png" decoding="async" width="450" height="74" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a4/Luciferin_principle.png/675px-Luciferin_principle.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a4/Luciferin_principle.png/900px-Luciferin_principle.png 2x" data-file-width="2763" data-file-height="455" /></a><figcaption>Loss of CO<sub>2</sub> of a dioxetane, giving rise to an excited ketone, which relaxes by emitting light.</figcaption></figure> <div style="clear:both;" class=""></div> <div class="mw-heading mw-heading2"><h2 id="Industrial_uses">Industrial uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organic_peroxides&action=edit&section=4" title="Edit section: Industrial uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="In_polymer_chemistry">In polymer chemistry</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organic_peroxides&action=edit&section=5" title="Edit section: In polymer chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Many peroxides are used as a <a href="/wiki/Radical_initiator" title="Radical initiator">radical initiators</a>, e.g., to enable <a href="/wiki/Polymerization" title="Polymerization">polymerization</a> of acrylates. Industrial resins based on acrylic and/or <a href="/wiki/Methacrylic_acid" title="Methacrylic acid">methacrylic acid</a> esters are invariably produced by radical polymerization with organic peroxides at elevated temperatures.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> The polymerization rate is adjusted by suitable choice of temperature and type of peroxide.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Methyl_ethyl_ketone_peroxide" title="Methyl ethyl ketone peroxide">Methyl ethyl ketone peroxide</a>, <a href="/wiki/Benzoyl_peroxide" title="Benzoyl peroxide">benzoyl peroxide</a> and to a smaller degree <a href="/wiki/Acetone_peroxide" title="Acetone peroxide">acetone peroxide</a> are used as initiators for <a href="/wiki/Radical_polymerization" title="Radical polymerization">radical polymerization</a> of some <a href="/wiki/Thermoset" class="mw-redirect" title="Thermoset">thermosets</a>, e.g. <a href="/wiki/Unsaturated_polyester" class="mw-redirect" title="Unsaturated polyester">unsaturated polyester</a> and <a href="/wiki/Vinyl_ester" title="Vinyl ester">vinyl ester</a> resins, often encountered when making fiberglass or <a href="/wiki/Carbon-fiber-reinforced_polymers" class="mw-redirect" title="Carbon-fiber-reinforced polymers">carbon fiber composites</a> (CFRP), with examples including boats, RV units, bath tubs, pools, sporting equipment, wind turbine blades, and a variety of industrial applications. </p><p><a href="/wiki/Benzoyl_peroxide" title="Benzoyl peroxide">Benzoyl peroxide</a>, <a href="/w/index.php?title=Peroxyester&action=edit&redlink=1" class="new" title="Peroxyester (page does not exist)">peroxyesters</a>/<a href="/w/index.php?title=Peroxyketal&action=edit&redlink=1" class="new" title="Peroxyketal (page does not exist)">peroxyketals</a>, and <a href="/w/index.php?title=Alkylperoxy_monocarbonates&action=edit&redlink=1" class="new" title="Alkylperoxy monocarbonates (page does not exist)">alkylperoxy monocarbonates</a> are used in production of <a href="/wiki/Polystyrene" title="Polystyrene">polystyrene</a>, <a href="/wiki/Expanded_polystyrene" class="mw-redirect" title="Expanded polystyrene">expanded polystyrene</a>, and <a href="/wiki/High_Impact_Polystyrene" class="mw-redirect" title="High Impact Polystyrene">High Impact Polystyrene</a>, and benzoyl peroxide is utilized for many acrylate based adhesive applications. </p><p>Thermoplastic production techniques for many industrial polymerization applications include processes which are carried out in bulk, solution, or suspension type batches. Relevant polymers include: <a href="/wiki/Polyvinyl_chloride" title="Polyvinyl chloride">polyvinyl chloride</a> (PVC), <a href="/wiki/Low-density_polyethylene" title="Low-density polyethylene">low-density polyethylene</a> (LDPE), <a href="/wiki/High-density_polyethylene" title="High-density polyethylene">high-density polyethylene</a> (HDPE), <a href="/wiki/Poly(methyl_methacrylate)" title="Poly(methyl methacrylate)">polymethyl methacrylate</a> (PMMA), <a href="/wiki/Polystyrene" title="Polystyrene">Polystyrene</a>, and <a href="/wiki/Polycarbonates" class="mw-redirect" title="Polycarbonates">Polycarbonates</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Bleaching_and_disinfecting_agents">Bleaching and disinfecting agents</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organic_peroxides&action=edit&section=6" title="Edit section: Bleaching and disinfecting agents"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Benzoyl_peroxide" title="Benzoyl peroxide">Benzoyl peroxide</a> and <a href="/wiki/Hydrogen_peroxide" title="Hydrogen peroxide">hydrogen peroxide</a> are used as <a href="/wiki/Flour_bleaching_agent" title="Flour bleaching agent">bleaching and "maturing" agents</a> for treating <a href="/wiki/Flour" title="Flour">flour</a> to make its grain release <a href="/wiki/Gluten" title="Gluten">gluten</a> more easily; the alternative is letting the flour slowly oxidize by air, which is too slow for the industrialized era. <a href="/wiki/Benzoyl_peroxide" title="Benzoyl peroxide">Benzoyl peroxide</a> is an effective topical medication for treating most forms of <a href="/wiki/Acne_vulgaris" class="mw-redirect" title="Acne vulgaris">acne</a>. </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=Organic_peroxides&action=edit&section=7" title="Edit section: Preparation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="From_hydrogen_peroxide">From hydrogen peroxide</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organic_peroxides&action=edit&section=8" title="Edit section: From hydrogen peroxide"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Dialkyl peroxides, e.g., <a href="/wiki/Dicumyl_peroxide" title="Dicumyl peroxide">dicumyl peroxide</a>, are synthesized by addition of hydrogen peroxide to alkenes or by O-alkylation of hydroperoxides. </p><p>Diacyl peroxides are typically prepared by treating hydrogen peroxide with acid chlorides or acid anhydrides in the presence of base:<sup id="cite_ref-Ullmann_1-1" class="reference"><a href="#cite_note-Ullmann-1"><span class="cite-bracket">[</span>1<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">H<sub class="template-chem2-sub">2</sub>O<sub class="template-chem2-sub">2</sub> + 2 RCOCl → (RCO<sub class="template-chem2-sub">2</sub>)<sub class="template-chem2-sub">2</sub> + 2 HCl</span></dd> <dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>O<sub class="template-chem2-sub">2</sub> + (RCO)<sub class="template-chem2-sub">2</sub>O → (RCO<sub class="template-chem2-sub">2</sub>)<sub class="template-chem2-sub">2</sub> + H<sub class="template-chem2-sub">2</sub>O</span></dd></dl> <p>The reaction competes with hydrolysis of the acylating agent but the hydroperoxide anion is a superior nucleophile relative to hydroxide. Unsymmetrical diacyl peroxides can be produced by treating acyl chlorides with the peroxy acid. </p><p><a href="/wiki/Perester" class="mw-redirect" title="Perester">Peresters</a>, an example being <a href="/wiki/Tert-Butyl_peroxybenzoate" title="Tert-Butyl peroxybenzoate"><i>tert</i>-Butyl peroxybenzoate</a>, are produced by treating acid anhydrides or acid chlorides with hydroperoxides. </p> <div class="mw-heading mw-heading3"><h3 id="From_O2">From O<sub>2</sub></h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organic_peroxides&action=edit&section=9" title="Edit section: From O2"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style 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">Main article: <a href="/wiki/Autoxidation" title="Autoxidation">Autoxidation</a></div> <p>Cyclic peroxides can be obtained by <a href="/wiki/Cycloaddition" title="Cycloaddition">cycloaddition</a> of <a href="/wiki/Singlet_oxygen" title="Singlet oxygen">singlet oxygen</a> (generated by UV radiation) to dienes. An important example is <a href="/wiki/Rubrene" title="Rubrene">rubrene</a>. Six-membered cyclic peroxides are called endo peroxides.<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> The four-membered <a href="/wiki/1,2-dioxetane" class="mw-redirect" title="1,2-dioxetane">dioxetanes</a> can be obtained by 2+2 <a href="/wiki/Cycloaddition" title="Cycloaddition">cycloaddition</a> of oxygen to <a href="/wiki/Alkene" title="Alkene">alkenes</a>.<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> </p><p>The hazards associated with storage of ethers in air is attributed to the formation of hydroperoxides via the direct albeit slow reaction of triplet oxygen with <a href="/wiki/C-H_bond" class="mw-redirect" title="C-H bond">C-H bonds</a>. </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=Organic_peroxides&action=edit&section=10" title="Edit section: Reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Homolysis">Homolysis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organic_peroxides&action=edit&section=11" title="Edit section: Homolysis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Organic peroxides are widely used to initiate <a href="/wiki/Polymerization" title="Polymerization">polymerization</a> of <a href="/wiki/Olefin" class="mw-redirect" title="Olefin">olefins</a>, e.g. the formation of <a href="/wiki/Polyethylene" title="Polyethylene">polyethylene</a>. A key step is <a href="/wiki/Homolysis_(chemistry)" title="Homolysis (chemistry)">homolysis</a>: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">ROOR ⇌ 2 RO</span><sup>.</sup></dd></dl> <p>The tendency to homolyze is also exploited to modify polymers by <a href="/wiki/Graft_polymer" title="Graft polymer">grafting</a> or <a href="/wiki/Visbreaker" title="Visbreaker">visbreaking</a>, or <a href="/wiki/Cross-link" title="Cross-link">cross-link</a> polymers to create a <a href="/wiki/Thermoset" class="mw-redirect" title="Thermoset">thermoset</a>. When used for these purposes, the peroxide is highly diluted, so the heat generated by the <a href="/wiki/Exothermic" class="mw-redirect" title="Exothermic">exothermic</a> decomposition is safely absorbed by the surrounding medium (e.g. polymer compound or <a href="/wiki/Emulsion" title="Emulsion">emulsion</a>). </p> <div class="mw-heading mw-heading3"><h3 id="Self-oxidation">Self-oxidation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organic_peroxides&action=edit&section=12" title="Edit section: Self-oxidation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Especially when in concentrated form, organic peroxides can decompose by self-oxidation, since organic peroxides contain both an oxidizer (the O-O bond) and fuel (C-H and C-C bonds). A "self-accelerating decomposition" occurs when the <a href="/wiki/Reaction_rate" title="Reaction rate">rate</a> of peroxide decomposition generates heat at a faster rate than it can be dissipated to the environment. Temperature is the main factor in the rate of decomposition. The lowest temperature at which a packaged organic peroxide will undergo a self-accelerating decomposition within a week is defined as the <i><a href="/wiki/Self_accelerating_decomposition_temperature" title="Self accelerating decomposition temperature">self-accelerating decomposition temperature</a></i> (SADT). A large fire at the Arkema Chemical Plant in Crosby, Texas (USA) in 2017 was caused by the decomposition of various organic peroxides following power failure and subsequent loss of cooling systems.<sup id="cite_ref-USCSB_14-0" class="reference"><a href="#cite_note-USCSB-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> This occurred due to extreme flooding from <a href="/wiki/Hurricane_Harvey" title="Hurricane Harvey">Hurricane Harvey</a>, which destroyed main and back-up power generators at the site.<sup id="cite_ref-USCSB_14-1" class="reference"><a href="#cite_note-USCSB-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Cumene_process">Cumene process</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organic_peroxides&action=edit&section=13" title="Edit section: Cumene process"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Hydroperoxides are intermediates or reagents in major commercial processes. In the <a href="/wiki/Cumene_process" title="Cumene process">cumene process</a>, acetone and phenol are produced by decomposition of <a href="/wiki/Cumene_hydroperoxide" title="Cumene hydroperoxide">cumene hydroperoxide</a> (Me = methyl): </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>CMe<sub class="template-chem2-sub">2</sub>(O<sub class="template-chem2-sub">2</sub>H) → C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>OH + O=CMe<sub class="template-chem2-sub">2</sub></span></dd></dl> <div class="mw-heading mw-heading3"><h3 id="Anthraquinone_process"><a href="/wiki/Anthraquinone_process" title="Anthraquinone process">Anthraquinone process</a></h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organic_peroxides&action=edit&section=14" title="Edit section: Anthraquinone process"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Anthrahydroquinone reacts spontaneously with oxygen to form anthraquinone and hydrogen peroxide, possibly through some organic peroxide intermediate. After extraktion of the hydrogen peroxide the anthraquinone is catalytically reduced to anthrahydroquinone and reused in the process. There are other <a href="/wiki/Hydroquinone" title="Hydroquinone">hydroquinones</a> reacting in a similar fashion. </p> <div class="mw-heading mw-heading3"><h3 id="Reduction">Reduction</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organic_peroxides&action=edit&section=15" title="Edit section: Reduction"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Organoperoxides can be reduced to <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohols</a> with <a href="/wiki/Lithium_aluminium_hydride" title="Lithium aluminium hydride">lithium aluminium hydride</a>, as described in this idealized equation: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">4 ROOH + LiAlH<sub class="template-chem2-sub">4</sub> → LiAlO<sub class="template-chem2-sub">2</sub> + 2 H<sub class="template-chem2-sub">2</sub>O + 4 ROH</span></dd></dl> <p>The <a href="/wiki/Phosphite_ester" title="Phosphite ester">phosphite esters</a> and tertiary phosphines also effect reduction: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">ROOH + PR<sub class="template-chem2-sub">3</sub> → P(OR)<sub class="template-chem2-sub">3</sub> + ROH</span></dd></dl> <p>Cleavage to ketones and alcohols occurs in the base-catalyzed <a href="/wiki/Kornblum%E2%80%93DeLaMare_rearrangement" title="Kornblum–DeLaMare rearrangement">Kornblum–DeLaMare rearrangement</a>, which involves the breaking of bonds within peroxides to form these products. </p><p>Some peroxides are <a href="/wiki/Drug" title="Drug">drugs</a>, whose action is based on the formation of radicals at desired locations in the organism. For example, <a href="/wiki/Artemisinin" title="Artemisinin">artemisinin</a> and its derivatives, such as <a href="/wiki/Artesunate" title="Artesunate">artesunate</a>, possess the most rapid action of all current drugs against <a href="/wiki/Plasmodium_falciparum" title="Plasmodium falciparum">falciparum</a> <a href="/wiki/Malaria" title="Malaria">malaria</a>.<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> Artesunate is also efficient in reducing egg production in <i><a href="/wiki/Schistosoma_haematobium" title="Schistosoma haematobium">Schistosoma haematobium</a></i> infection.<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> </p> <div class="mw-heading mw-heading3"><h3 id="Organic_synthesis">Organic synthesis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organic_peroxides&action=edit&section=16" title="Edit section: Organic synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>tert-Butyl hydroperoxide is used for epoxidation and hydroxylation reagents in conjunction with metal catalysts.<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="Analysis_of_peroxides">Analysis of peroxides</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organic_peroxides&action=edit&section=17" title="Edit section: Analysis of peroxides"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Jodprobe.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e7/Jodprobe.jpg/220px-Jodprobe.jpg" decoding="async" width="220" height="153" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e7/Jodprobe.jpg/330px-Jodprobe.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e7/Jodprobe.jpg/440px-Jodprobe.jpg 2x" data-file-width="2118" data-file-height="1476" /></a><figcaption><a href="/wiki/Iodine_test" class="mw-redirect" title="Iodine test">Iodine-starch test</a>. Note the blackening (left) of initially yellowish (right) starch.</figcaption></figure> <p>Several analytical methods are used for qualitative and quantitative determination of peroxides.<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> A simple qualitative detection of peroxides is carried out with the <a href="/wiki/Iodine_test" class="mw-redirect" title="Iodine test">iodine-starch reaction</a>.<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> Here peroxides, hydroperoxides or peracids oxidize the added <a href="/wiki/Potassium_iodide" title="Potassium iodide">potassium iodide</a> into <a href="/wiki/Iodine" title="Iodine">iodine</a>, which reacts with <a href="/wiki/Starch" title="Starch">starch</a> producing a deep-blue color. Commercial paper indicators using this reaction are available. This method is also suitable for quantitative evaluation, but it can not distinguish between different types of peroxide compounds. Discoloration of various <a href="/wiki/Indigo_dye" title="Indigo dye">indigo dyes</a> in presence of peroxides is used instead for this purpose.<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> For example, the loss of blue color in leuco-<a href="/wiki/Methylene_blue" title="Methylene blue">methylene blue</a> is selective for hydrogen peroxide.<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> </p><p>Quantitative analysis of hydroperoxides can be performed using potentiometric <a href="/wiki/Titration" title="Titration">titration</a> with <a href="/wiki/Lithium_aluminium_hydride" title="Lithium aluminium hydride">lithium aluminium hydride</a>.<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> Another way to evaluate the content of peracids and peroxides is the volumetric titration with <a href="/wiki/Alkoxide" title="Alkoxide">alkoxides</a> such as <a href="/wiki/Sodium_ethoxide" title="Sodium ethoxide">sodium ethoxide</a>.<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> </p> <div class="mw-heading mw-heading3"><h3 id="Active_oxygen_in_peroxides">Active oxygen in peroxides</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organic_peroxides&action=edit&section=18" title="Edit section: Active oxygen in peroxides"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Each peroxy group is considered to contain one active oxygen atom. The concept of active oxygen content is useful for comparing the relative <a href="/wiki/Concentration_(chemistry)" class="mw-redirect" title="Concentration (chemistry)">concentration</a> of peroxy groups in formulations, which is related to the energy content. In general, energy content increases with active oxygen content, and thus the higher the <a href="/wiki/Molecular_weight" class="mw-redirect" title="Molecular weight">molecular weight</a> of the organic groups, the lower the energy content and, usually, the lower the hazard. </p><p>The term <b>active oxygen</b> is used to specify the amount of peroxide present in any organic peroxide formulation. One of the oxygen atoms in each peroxide group is considered "active". The theoretical amount of active oxygen can be described by the following equation:<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<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 A[\mathrm {O} ]_{\text{theoretical}}(\%)=16{\frac {p}{m}}\times 100,}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mi>A</mi> <mo stretchy="false">[</mo> <mrow class="MJX-TeXAtom-ORD"> <mi mathvariant="normal">O</mi> </mrow> <msub> <mo stretchy="false">]</mo> <mrow class="MJX-TeXAtom-ORD"> <mtext>theoretical</mtext> </mrow> </msub> <mo stretchy="false">(</mo> <mi mathvariant="normal">%</mi> <mo stretchy="false">)</mo> <mo>=</mo> <mn>16</mn> <mrow class="MJX-TeXAtom-ORD"> <mfrac> <mi>p</mi> <mi>m</mi> </mfrac> </mrow> <mo>×</mo> <mn>100</mn> <mo>,</mo> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle A[\mathrm {O} ]_{\text{theoretical}}(\%)=16{\frac {p}{m}}\times 100,}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/176ebe20ba1c311442630b59225f66d03b08fe5f" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.838ex; width:31.684ex; height:4.843ex;" alt="{\displaystyle A[\mathrm {O} ]_{\text{theoretical}}(\%)=16{\frac {p}{m}}\times 100,}"></span></dd></dl> <p>where <span class="texhtml mvar" style="font-style:italic;">p</span> is the number of peroxide groups in the molecule, and <span class="texhtml mvar" style="font-style:italic;">m</span> is the <a href="/wiki/Molecular_mass" title="Molecular mass">molecular mass</a> of the pure peroxide. </p><p>Organic peroxides are often sold as formulations that include one or more <a href="/wiki/Phlegmatized" class="mw-redirect" title="Phlegmatized">phlegmatizing agents</a>. That is, for safety sake or performance benefits the properties of an organic peroxide formulation are commonly modified by the use of additives to phlegmatize (desensitize), stabilize, or otherwise enhance the organic peroxide for commercial use. Commercial formulations occasionally consist of mixtures of organic peroxides, which may or may not be phlegmatized. </p> <div class="mw-heading mw-heading2"><h2 id="Safety">Safety</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organic_peroxides&action=edit&section=19" title="Edit section: Safety"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:UN_transport_pictogram_-_5.2_(white).svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/46/UN_transport_pictogram_-_5.2_%28white%29.svg/220px-UN_transport_pictogram_-_5.2_%28white%29.svg.png" decoding="async" width="220" height="220" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/46/UN_transport_pictogram_-_5.2_%28white%29.svg/330px-UN_transport_pictogram_-_5.2_%28white%29.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/46/UN_transport_pictogram_-_5.2_%28white%29.svg/440px-UN_transport_pictogram_-_5.2_%28white%29.svg.png 2x" data-file-width="1002" data-file-height="1002" /></a><figcaption>The GHS transport pictogram for organic peroxides.</figcaption></figure> <p>Peroxides are also strong oxidizers and easily react with skin, cotton and wood pulp.<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> For safety reasons, peroxidic compounds are stored in a cool, opaque container, as heating and illumination accelerate their <a href="/wiki/Chemical_reaction" title="Chemical reaction">chemical reactions</a>. Small amounts of peroxides, which emerge from storage or reaction vessels are neutralized using reducing agents such as <a href="/wiki/Iron(II)_sulfate" title="Iron(II) sulfate">iron(II) sulfate</a>. Safety measures in industrial plants producing large amounts of peroxides include the following: </p><p>1) The equipment is located within reinforced concrete structures with foil windows, which would relieve pressure and not shatter in case of explosion. </p><p>2) The products are bottled in small containers and are moved to a cold place promptly after the synthesis. </p><p>3) The containers are made of non-reactive materials such as stainless steel, some aluminium alloys or dark glass.<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>For safe handling of concentrated organic peroxides, an important parameter is temperature of the sample, which should be maintained below the <a href="/wiki/Self_accelerating_decomposition_temperature" title="Self accelerating decomposition temperature">self accelerating decomposition temperature</a> of the compound.<sup id="cite_ref-American_Chemistry_Council_2021_27-0" class="reference"><a href="#cite_note-American_Chemistry_Council_2021-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </p><p>The shipping of organic peroxides is restricted. The <a href="/wiki/US_Department_of_Transportation" class="mw-redirect" title="US Department of Transportation">US Department of Transportation</a> lists organic peroxide shipping restrictions and forbidden materials in 49 CFR 172.101 Hazardous Materials Table based on the concentration and physical state of the material: </p> <table class="wikitable sortable"> <tbody><tr> <th>Chemical name </th> <th><a href="/wiki/CAS_Number" class="mw-redirect" title="CAS Number">CAS Number</a> </th> <th>Prohibitions </th></tr> <tr> <td><a href="/w/index.php?title=Acetyl_acetone_peroxide&action=edit&redlink=1" class="new" title="Acetyl acetone peroxide (page does not exist)">Acetyl acetone peroxide</a> </td> <td>37187-22-7 </td> <td>> 9% by mass <a href="/wiki/Active_oxygen" class="mw-redirect" title="Active oxygen">active oxygen</a> </td></tr> <tr> <td><a href="/wiki/Acetyl_benzoyl_peroxide" class="mw-redirect" title="Acetyl benzoyl peroxide">Acetyl benzoyl peroxide</a> </td> <td>644-31-5 </td> <td>solid, or > 40% in solution </td></tr> <tr> <td><a href="/wiki/Ascaridole" title="Ascaridole">Ascaridole</a> </td> <td>512-85-6 </td> <td>(organic peroxide) </td></tr> <tr> <td><a href="/wiki/Tert-Butyl_hydroperoxide" title="Tert-Butyl hydroperoxide"><i>tert</i>-Butyl hydroperoxide</a> </td> <td>75-91-2 </td> <td>> 90% in solution (aqueous) </td></tr> <tr> <td><a href="/w/index.php?title=Di-(1-naphthoyl)peroxide&action=edit&redlink=1" class="new" title="Di-(1-naphthoyl)peroxide (page does not exist)">Di-(1-naphthoyl)peroxide</a> </td> <td>29903-04-6 </td> <td> </td></tr> <tr> <td><a href="/wiki/Diacetyl_peroxide" title="Diacetyl peroxide">Diacetyl peroxide</a> </td> <td>110-22-5 </td> <td>solid, or > 25% in solution </td></tr> <tr> <td><a href="/wiki/Ethyl_hydroperoxide" title="Ethyl hydroperoxide">Ethyl hydroperoxide</a> </td> <td>3031-74-1 </td> <td> </td></tr> <tr> <td><a href="/wiki/Methyl_ethyl_ketone_peroxide" title="Methyl ethyl ketone peroxide">Methyl ethyl ketone peroxide</a> </td> <td>1338-23-4 </td> <td>> 9% by mass active oxygen in solution </td></tr> <tr> <td><a href="/w/index.php?title=Methyl_isobutyl_ketone_peroxide&action=edit&redlink=1" class="new" title="Methyl isobutyl ketone peroxide (page does not exist)">Methyl isobutyl ketone peroxide</a> </td> <td>37206-20-5 </td> <td>> 9% by mass active oxygen in solution </td></tr> </tbody></table> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Organic_peroxides&action=edit&section=20" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Alkenyl_peroxides" title="Alkenyl peroxides">Alkenyl peroxides</a></li> <li><a href="/wiki/Peroxyacyl_nitrates" title="Peroxyacyl nitrates">Peroxyacyl nitrates</a></li> <li><a href="/wiki/Ozonide" title="Ozonide">Ozonide</a></li></ul> <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=Organic_peroxides&action=edit&section=21" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a rel="nofollow" class="external text" href="https://www.americanchemistry.com/industry-groups/organic-peroxide-producers-safety-division-oppsd">Organic Peroxide Producers Safety Division</a></li> <li><a rel="nofollow" class="external text" href="http://www.ccohs.ca/oshanswers/chemicals/organic/organic_peroxide.html">OSH Answers – organic peroxides</a></li> <li><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 class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20071218063252/http://www.carolina.com/chemistry/resources/peroxides.asp">"The Perils of Peroxides"</a>. <i>carolina.com</i>. Burlington, NC: Carolina Biological Supply Company. Archived from <a rel="nofollow" class="external text" href="http://www.carolina.com/chemistry/resources/peroxides.asp">the original</a> on 2007-12-18.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=carolina.com&rft.atitle=The+Perils+of+Peroxides&rft_id=http%3A%2F%2Fwww.carolina.com%2Fchemistry%2Fresources%2Fperoxides.asp&rfr_id=info%3Asid%2Fen.wikipedia.org%3AOrganic+peroxides" class="Z3988"></span></li> <li><a rel="nofollow" class="external text" href="https://www.eopsg.org">European Organic Peroxide Safety Group</a></li></ul> <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=Organic_peroxides&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-Ullmann-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-Ullmann_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Ullmann_1-1"><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="CITEREFKlenkGötzSiegmeierMayr" class="citation encyclopaedia cs1">Klenk, Herbert; Götz, Peter H.; Siegmeier, Rainer; Mayr, Wilfried. "Peroxy Compounds, Organic". <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.a19_199.pub2">10.1002/14356007.a19_199.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=Peroxy+Compounds%2C+Organic&rft.btitle=Ullmann%27s+Encyclopedia+of+Industrial+Chemistry&rft.place=Weinheim&rft.pub=Wiley-VCH&rft_id=info%3Adoi%2F10.1002%2F14356007.a19_199.pub2&rft.isbn=978-3-527-30673-2&rft.aulast=Klenk&rft.aufirst=Herbert&rft.au=G%C3%B6tz%2C+Peter+H.&rft.au=Siegmeier%2C+Rainer&rft.au=Mayr%2C+Wilfried&rfr_id=info%3Asid%2Fen.wikipedia.org%3AOrganic+peroxides" class="Z3988"></span></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSaul_Patai1983" class="citation book cs1">Saul Patai, ed. (1983). <i>PATAI'S Chemistry of Functional Groups: Peroxides</i>. Wiley. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780470771730" title="Special:BookSources/9780470771730"><bdi>9780470771730</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=PATAI%27S+Chemistry+of+Functional+Groups%3A+Peroxides&rft.pub=Wiley&rft.date=1983&rft.isbn=9780470771730&rfr_id=info%3Asid%2Fen.wikipedia.org%3AOrganic+peroxides" 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"><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.ch.imperial.ac.uk/rzepa/blog/?p=10252">"Henry Rzepa's Blog: Why diphenyl peroxide does not exist"</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Henry+Rzepa%27s+Blog%3A+Why+diphenyl+peroxide+does+not+exist.&rft_id=https%3A%2F%2Fwww.ch.imperial.ac.uk%2Frzepa%2Fblog%2F%3Fp%3D10252&rfr_id=info%3Asid%2Fen.wikipedia.org%3AOrganic+peroxides" class="Z3988"></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBachAyalaSchlegel1996" class="citation journal cs1">Bach, Robert D.; Ayala, Philippe Y.; Schlegel, H. B. (1996). "A Reassessment of the Bond Dissociation Energies of Peroxides. An <i>ab Initio</i> Study". <i><a href="/wiki/J._Am._Chem._Soc." class="mw-redirect" title="J. Am. Chem. Soc.">J. Am. Chem. 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(1931). <a rel="nofollow" class="external text" href="https://doi.org/10.1098%2Frspb.1931.0030">"The Effect of Light on the Oxidation of Fats"</a>. <i>Proceedings of the Royal Society B: Biological Sciences</i>. <b>108</b> (756): <span class="nowrap">175–</span>189. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1931RSPSB.108..175L">1931RSPSB.108..175L</a>. <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/10.1098%2Frspb.1931.0030">10.1098/rspb.1931.0030</a></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Proceedings+of+the+Royal+Society+B%3A+Biological+Sciences&rft.atitle=The+Effect+of+Light+on+the+Oxidation+of+Fats&rft.volume=108&rft.issue=756&rft.pages=%3Cspan+class%3D%22nowrap%22%3E175-%3C%2Fspan%3E189&rft.date=1931&rft_id=info%3Adoi%2F10.1098%2Frspb.1931.0030&rft_id=info%3Abibcode%2F1931RSPSB.108..175L&rft.aulast=Lea&rft.aufirst=C.+H.&rft_id=https%3A%2F%2Fdoi.org%2F10.1098%252Frspb.1931.0030&rfr_id=info%3Asid%2Fen.wikipedia.org%3AOrganic+peroxides" class="Z3988"></span></span> </li> <li id="cite_note-20"><span class="mw-cite-backlink"><b><a href="#cite_ref-20">^</a></b></span> <span class="reference-text">Veibel, S. <i>Analytik organischer Verbindungen</i>, Akademie-Verlag, Berlin, 1960, p. 262</span> </li> <li id="cite_note-21"><span class="mw-cite-backlink"><b><a href="#cite_ref-21">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFEissGiesecke1959" class="citation journal cs1">Eiss, M. I.; Giesecke, Paul (1959). "Colorimetric Determination of Organic Peroxides". <i>Analytical Chemistry</i>. <b>31</b> (9): 1558. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fac60153a038">10.1021/ac60153a038</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Analytical+Chemistry&rft.atitle=Colorimetric+Determination+of+Organic+Peroxides&rft.volume=31&rft.issue=9&rft.pages=1558&rft.date=1959&rft_id=info%3Adoi%2F10.1021%2Fac60153a038&rft.aulast=Eiss&rft.aufirst=M.+I.&rft.au=Giesecke%2C+Paul&rfr_id=info%3Asid%2Fen.wikipedia.org%3AOrganic+peroxides" class="Z3988"></span></span> </li> <li id="cite_note-22"><span class="mw-cite-backlink"><b><a href="#cite_ref-22">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHiguchiZuck1951" class="citation journal cs1">Higuchi, T.; Zuck, Donald Anton (1951). "Behaviors of Several Compounds as Indicators in Lithium Aluminum Hydride Titration of Functional Groups". <i>Journal of the American Chemical Society</i>. <b>73</b> (6): 2676. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fja01150a073">10.1021/ja01150a073</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+the+American+Chemical+Society&rft.atitle=Behaviors+of+Several+Compounds+as+Indicators+in+Lithium+Aluminum+Hydride+Titration+of+Functional+Groups&rft.volume=73&rft.issue=6&rft.pages=2676&rft.date=1951&rft_id=info%3Adoi%2F10.1021%2Fja01150a073&rft.aulast=Higuchi&rft.aufirst=T.&rft.au=Zuck%2C+Donald+Anton&rfr_id=info%3Asid%2Fen.wikipedia.org%3AOrganic+peroxides" class="Z3988"></span></span> </li> <li id="cite_note-23"><span class="mw-cite-backlink"><b><a href="#cite_ref-23">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMartin1957" class="citation journal cs1">Martin, A. J. (1957). "Potentiometric titration of hydroperoxide and peracid in Anhydrous Ethylenediamine". <i>Analytical Chemistry</i>. <b>29</b>: <span class="nowrap">79–</span>81. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fac60121a022">10.1021/ac60121a022</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Analytical+Chemistry&rft.atitle=Potentiometric+titration+of+hydroperoxide+and+peracid+in+Anhydrous+Ethylenediamine&rft.volume=29&rft.pages=%3Cspan+class%3D%22nowrap%22%3E79-%3C%2Fspan%3E81&rft.date=1957&rft_id=info%3Adoi%2F10.1021%2Fac60121a022&rft.aulast=Martin&rft.aufirst=A.+J.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AOrganic+peroxides" class="Z3988"></span></span> </li> <li id="cite_note-24"><span class="mw-cite-backlink"><b><a href="#cite_ref-24">^</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.astm.org/Standards/E298.htm">"ASTM E298, Standard Test Methods for Assay of Organic Peroxides"</a>. ASTM. 2010.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=ASTM+E298%2C+Standard+Test+Methods+for+Assay+of+Organic+Peroxides&rft.pub=ASTM&rft.date=2010&rft_id=http%3A%2F%2Fwww.astm.org%2FStandards%2FE298.htm&rfr_id=info%3Asid%2Fen.wikipedia.org%3AOrganic+peroxides" 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">Heinz G. O. Becker <i>Organikum</i>, Wiley-VCH, 2001, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/3-527-29985-8" title="Special:BookSources/3-527-29985-8">3-527-29985-8</a> pp. 741–762</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"><a rel="nofollow" class="external text" href="http://www.ozoneservices.com/articles/004.htm">Ozonelab Peroxide compatibility</a></span> </li> <li id="cite_note-American_Chemistry_Council_2021-27"><span class="mw-cite-backlink"><b><a href="#cite_ref-American_Chemistry_Council_2021_27-0">^</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="https://www.americanchemistry.com/industry-groups/organic-peroxide-producers-safety-division-oppsd/product-stewardship">"Product Stewardship"</a>. <i>American Chemistry Council</i>. 2021-01-17<span class="reference-accessdate">. Retrieved <span class="nowrap">2022-01-03</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=American+Chemistry+Council&rft.atitle=Product+Stewardship&rft.date=2021-01-17&rft_id=https%3A%2F%2Fwww.americanchemistry.com%2Findustry-groups%2Forganic-peroxide-producers-safety-division-oppsd%2Fproduct-stewardship&rfr_id=info%3Asid%2Fen.wikipedia.org%3AOrganic+peroxides" class="Z3988"></span></span> </li> </ol></div></div> <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 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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:Functional_groups" title="Template:Functional groups"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Functional_groups" title="Template talk:Functional groups"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Functional_groups" title="Special:EditPage/Template:Functional groups"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Functional_groups729" style="font-size:114%;margin:0 4em"><a href="/wiki/Functional_group" title="Functional group">Functional groups</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hydrocarbon" title="Hydrocarbon">Hydrocarbons</a> <br /><span class="nobold">(only C and H)</span></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/Alkyl" class="mw-redirect" title="Alkyl">Alkyl</a> <ul><li><a href="/wiki/Methyl_group" title="Methyl group">Methyl</a></li> <li><a href="/wiki/Ethyl_group" title="Ethyl group">Ethyl</a></li> <li><a href="/wiki/Propyl_group" title="Propyl group">Propyl</a></li> <li><a href="/wiki/Cyclopropyl" class="mw-redirect" title="Cyclopropyl">Cyclopropyl</a></li> <li><a href="/wiki/Butyl_group" title="Butyl group">Butyl</a></li> <li><a href="/wiki/Pentyl_group" title="Pentyl group">Pentyl</a></li></ul></li> <li><a href="/wiki/Methylene_group" title="Methylene group">Methylene</a> <ul><li><a href="/wiki/Methylene_bridge" title="Methylene bridge">Bridge</a></li> <li><a href="/wiki/Methine_group" title="Methine group">Methine</a></li></ul></li> <li><a href="/wiki/Alkene" title="Alkene">Alkene</a> <ul><li><a href="/wiki/Vinyl_group" title="Vinyl group">Vinyl</a></li> <li><a href="/wiki/Allyl_group" title="Allyl group">Allyl</a></li> <li><a href="/wiki/Propenyl" title="Propenyl">1-Propenyl</a></li> <li><a href="/wiki/Crotyl_group" title="Crotyl group">Crotyl</a></li> <li><a href="/wiki/Allenes" title="Allenes">Allene</a></li> <li><a href="/wiki/Cumulene" title="Cumulene">Cumulene</a></li></ul></li> <li><a href="/wiki/Aryl" class="mw-redirect" title="Aryl">Aryl</a> <ul><li><a href="/wiki/Phenyl_group" title="Phenyl group">Phenyl</a></li> <li><a href="/wiki/Benzyl_group" title="Benzyl group">Benzyl</a></li></ul></li> <li><a href="/wiki/Alkyne" title="Alkyne">Alkyne</a></li> <li><a href="/wiki/Carbene" title="Carbene">Carbene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Only <a href="/wiki/Carbon" title="Carbon">carbon</a>, <br /><a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a>, <br />and <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> <br /><span class="nobold">(only C, H and O)</span></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%">R-O-R</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/Acetal" title="Acetal">Acetal</a></li> <li><a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">Alcohol</a></li> <li><a href="/wiki/Alkoxy_group" title="Alkoxy group">Alkoxy</a> <ul><li><a href="/wiki/Methoxy_group" title="Methoxy group">Methoxy</a></li></ul></li> <li><a href="/wiki/Ether" title="Ether">Ether</a> <ul><li><a href="/wiki/Enol_ether" title="Enol ether">Enol ether</a></li> <li><a href="/wiki/Epoxide" title="Epoxide">Epoxide</a></li></ul></li> <li><a class="mw-selflink selflink">Peroxy</a> <ul><li><a href="/wiki/Hydroperoxide" title="Hydroperoxide">Hydroperoxy</a></li> <li><a href="/wiki/Dioxirane" title="Dioxirane">Dioxiranes</a></li></ul></li> <li><a href="/wiki/Ethylenedioxy" title="Ethylenedioxy">Ethylenedioxy</a></li> <li><a href="/wiki/Methylenedioxy" title="Methylenedioxy">Methylenedioxy</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Carbonyl_group" title="Carbonyl group">carbonyl</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/Acyl_group" title="Acyl group">Acyl</a> <ul><li><a href="/wiki/Acetyl_group" title="Acetyl group">Acetyl</a></li> <li><a href="/wiki/Acryloyl_group" class="mw-redirect" title="Acryloyl group">Acryloyl</a></li> <li><a href="/wiki/Benzoyl_group" title="Benzoyl group">Benzoyl</a></li></ul></li> <li><a href="/wiki/Aldehyde" title="Aldehyde">Aldehyde</a> <ul><li><a href="/wiki/Ketene" title="Ketene">Ketene</a></li></ul></li> <li><a href="/wiki/Ketone" title="Ketone">Ketone</a></li> <li><a href="/wiki/Ynone" title="Ynone">Ynone</a></li> <li><a href="/wiki/Reductone" title="Reductone">Reductone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">carboxy</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/Carboxylic_acid" title="Carboxylic acid">Carboxyl</a> <ul><li><a href="/wiki/Acetoxy_group" title="Acetoxy group">Acetoxy</a></li> <li><a href="/wiki/Carboxylic_anhydride" class="mw-redirect" title="Carboxylic anhydride">Anhydride</a></li></ul></li> <li><a href="/wiki/Ester" title="Ester">Ester</a> <ul><li><a href="/wiki/Orthoester" class="mw-redirect" title="Orthoester">Orthoester</a></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Only one <br />element, <br />not being <br />carbon, <br />hydrogen, <br />or oxygen <br /><span class="nobold">(one element, <br />not C, H or O)</span></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/Nitrogen" title="Nitrogen">Nitrogen</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/Amine" title="Amine">Amine</a> <ul><li><a href="/wiki/Enamine" title="Enamine">Enamine</a></li> <li><a href="/wiki/Quaternary_ammonium_cation" title="Quaternary ammonium cation">Ammonium</a></li></ul></li> <li><a href="/wiki/Hydrazines" title="Hydrazines">Hydrazo</a></li> <li><a href="/wiki/Nitrene" title="Nitrene">Nitrene</a></li> <li><a href="/wiki/Imine" title="Imine">Imine</a></li> <li><a href="/wiki/Oxime" title="Oxime">Oxime</a></li> <li><a href="/wiki/Hydrazone" title="Hydrazone">Hydrazone</a></li> <li><a href="/wiki/Azo_compound" title="Azo compound">Azo</a></li> <li><a href="/wiki/Amide_(functional_group)" title="Amide (functional group)">Amide</a></li> <li><a href="/wiki/Imidate" class="mw-redirect" title="Imidate">Imidate</a></li> <li><a href="/wiki/Amidine" title="Amidine">Amidine</a></li> <li><a href="/wiki/Carbamate" title="Carbamate">Carbamate</a></li> <li><a href="/wiki/Imide" title="Imide">Imide</a></li> <li><a href="/wiki/Nitrile" title="Nitrile">Nitrile</a></li> <li><a href="/wiki/Isocyanide" title="Isocyanide">Isonitrile</a></li> <li><a href="/wiki/Cyanate_ester" title="Cyanate ester">Cyanate</a></li> <li><a href="/wiki/Isocyanate" title="Isocyanate">Isocyanate</a></li> <li><a href="/wiki/Nitrate_ester" title="Nitrate ester">Nitrate</a></li> <li><a href="/wiki/Nitrite_ester" class="mw-redirect" title="Nitrite ester">Nitrite</a></li> <li><a href="/wiki/Nitro_compound" title="Nitro compound">Nitro</a></li> <li><a href="/wiki/Nitroso" title="Nitroso">Nitroso</a></li> <li><a href="/wiki/NONOate" title="NONOate">NONOate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Silicon" title="Silicon">Silicon</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">Silane</a> <ul><li><a href="/wiki/Hydrosilane" class="mw-redirect" title="Hydrosilane">Hydrosilane</a></li> <li><a href="/wiki/Chlorosilane" title="Chlorosilane">Chlorosilane</a></li></ul></li> <li><a href="/wiki/Organosilicon_chemistry#Silenes" title="Organosilicon chemistry">Silene</a></li> <li><a href="/wiki/Silanol" title="Silanol">Silanol</a></li> <li><a href="/wiki/Siloxide" title="Siloxide">Siloxide</a></li> <li><a href="/wiki/Siloxane" title="Siloxane">Siloxane</a></li> <li><a href="/wiki/Silanone" title="Silanone">Silanone</a></li> <li><a href="/wiki/Silyl_ether" title="Silyl ether">Silether</a></li> <li><a href="/wiki/Metalloles" class="mw-redirect" title="Metalloles">Silole</a></li> <li><a href="/wiki/Silatrane" class="mw-redirect" title="Silatrane">Silatrane</a></li> <li><a href="/wiki/Silicate" title="Silicate">Silicate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phosphorus" title="Phosphorus">Phosphorus</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/Organophosphate" title="Organophosphate">Phosphate</a> <ul><li><a href="/wiki/Phosphodiester" class="mw-redirect" title="Phosphodiester">Phosphodiester</a></li></ul></li> <li><a href="/wiki/Phosphonate" title="Phosphonate">Phosphonate</a> <ul><li><a href="/wiki/Phosphite_ester" title="Phosphite ester">Phosphite</a></li></ul></li> <li><a href="/wiki/Phosphonite" title="Phosphonite">Phosphonous</a></li> <li><a href="/wiki/Phosphinate" title="Phosphinate">Phosphinate</a></li> <li><a href="/wiki/Phosphine_oxide" title="Phosphine oxide">Phosphine oxide</a></li> <li><a href="/wiki/Organophosphine" title="Organophosphine">Phosphine</a> <ul><li><a href="/wiki/Phosphonium" title="Phosphonium">Phosphonium</a></li></ul></li> <li><a href="/wiki/Phosphaalkene" title="Phosphaalkene">Phosphaalkene</a></li> <li><a href="/wiki/Phosphaalkyne" title="Phosphaalkyne">Phosphaalkyne</a></li> <li><a href="/wiki/1-Phosphaallenes" title="1-Phosphaallenes">Phosphaallene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sulfur" title="Sulfur">Sulfur</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/Thiol" title="Thiol">Thiol</a></li> <li><a href="/wiki/Thioether" class="mw-redirect" title="Thioether">Thioether</a> <ul><li><a href="/wiki/Sulfonium" title="Sulfonium">Sulfonium</a></li></ul></li> <li><a href="/wiki/Persulfide" title="Persulfide">Persulfide</a></li> <li><a href="/wiki/Disulfide" title="Disulfide">Disulfide</a></li> <li><a href="/wiki/Sulfenic_acid" title="Sulfenic acid">Sulfenic acid</a></li> <li><a href="/wiki/Thiosulfinate" title="Thiosulfinate">Thiosulfinate</a></li> <li><a href="/wiki/Sulfoxide" title="Sulfoxide">Sulfoxide</a></li> <li><a href="/wiki/Thiosulfonate" title="Thiosulfonate">Thiosulfonate</a></li> <li><a href="/wiki/Sulfinic_acid" title="Sulfinic acid">Sulfinic acid</a></li> <li><a href="/wiki/Sulfone" title="Sulfone">Sulfone</a></li> <li><a href="/wiki/Sulfonic_acid" title="Sulfonic acid">Sulfonic acid</a></li> <li><a href="/wiki/Thioketone" title="Thioketone">Thioketone</a></li> <li><a href="/wiki/Thial" title="Thial">Thial</a></li> <li><a href="/wiki/Thioester" title="Thioester">Thioester</a></li> <li><a href="/wiki/Thionoester" class="mw-redirect" title="Thionoester">Thionoester</a></li> <li><a href="/wiki/Thioxanthate" title="Thioxanthate">Thioxanthate</a></li> <li><a href="/wiki/Xanthate" title="Xanthate">Xanthate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Boron" title="Boron">Boron</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/Boronic_acid" title="Boronic acid">Boronic acid</a></li> <li><a href="/wiki/Borinic_acid" title="Borinic acid">Borinic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Selenium" title="Selenium">Selenium</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/Selenol" title="Selenol">Selenol</a></li> <li><a href="/wiki/Selenonic_acid" title="Selenonic acid">Selenonic acid</a></li> <li><a href="/wiki/Seleninic_acid" title="Seleninic acid">Seleninic acid</a></li> <li><a href="/wiki/Selenenic_acid" title="Selenenic acid">Selenenic acid</a></li> <li><a href="/wiki/Selone" title="Selone">Selone</a></li> <li><a href="/wiki/Selenide#Inorganic_selenides" title="Selenide">Selenoether</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tellurium" title="Tellurium">Tellurium</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/Tellurol" title="Tellurol">Tellurol</a></li> <li><a href="/wiki/Telluroketone" title="Telluroketone">Telluroketone</a></li> <li><a href="/wiki/Telluride_(chemistry)#Organic_tellurides" title="Telluride (chemistry)">telluroether</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Polonium" title="Polonium">Polonium</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/Polonium_hydride#Properties" title="Polonium hydride">Polonol</a></li> <li><a href="/wiki/Organopolonium_chemistry" title="Organopolonium chemistry">Polonoether</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i><a href="/wiki/Halocarbon" title="Halocarbon">Halo</a></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><a href="/wiki/Haloalkane" title="Haloalkane">Haloalkane</a> <ul><li><a href="/wiki/Fluoroethyl" title="Fluoroethyl">Fluoroethyl</a></li> <li><a href="/wiki/Trifluoromethyl" class="mw-redirect" title="Trifluoromethyl">Trifluoromethyl</a></li> <li><a href="/wiki/Trichloromethyl_group" title="Trichloromethyl group">Trichloromethyl</a></li> <li><a href="/wiki/Trifluoromethoxy_group" title="Trifluoromethoxy group">Trifluoromethoxy</a></li> <li><a href="/wiki/Iodane" class="mw-redirect" title="Iodane">Hypervalent iodine</a></li></ul></li> <li><a href="/wiki/Vinyl_halide" title="Vinyl halide">Vinyl halide</a> <ul><li><a href="/wiki/Vinyl_iodide_functional_group" title="Vinyl iodide functional group">Iodide</a></li></ul></li> <li><a href="/wiki/Acyl_halide" title="Acyl halide">Acyl halide</a> <ul><li><a href="/wiki/Acyl_chloride" title="Acyl chloride">Chloride</a></li></ul></li> <li><a href="/wiki/Perchlorate_ester" class="mw-redirect" title="Perchlorate ester">Perchlorate</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</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/Isothiocyanate" title="Isothiocyanate">Isothiocyanate</a></li> <li><a href="/wiki/Phosphoramides" title="Phosphoramides">Phosphoramides</a></li> <li><a href="/wiki/Sulfenyl_chloride" title="Sulfenyl chloride">Sulfenyl chloride</a></li> <li><a href="/wiki/Sulfonamide" title="Sulfonamide">Sulfonamide</a></li> <li><a href="/wiki/Organic_thiocyanates" title="Organic thiocyanates">Thiocyanate</a></li> <li><a href="/wiki/Sulfinylamine" title="Sulfinylamine">Sulfinylamines</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt><span class="nobold">See also</span></dt> <dd><i><a href="/wiki/Chemical_classification" class="mw-redirect" title="Chemical classification">chemical classification</a></i></dd> <dd><i><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">chemical nomenclature</a></i> <dl><dd><a href="/wiki/IUPAC_nomenclature_of_inorganic_chemistry" title="IUPAC nomenclature of inorganic chemistry">inorganic</a></dd> <dd><a href="/wiki/IUPAC_nomenclature_of_organic_chemistry" title="IUPAC nomenclature of organic chemistry">organic</a></dd></dl></dd></dl> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link 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