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href="#Applications"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Applications</span> </div> </a> <button aria-controls="toc-Applications-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Applications subsection</span> </button> <ul id="toc-Applications-sublist" class="vector-toc-list"> <li id="toc-Terephthalic_acid_and_related_derivatives" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Terephthalic_acid_and_related_derivatives"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Terephthalic acid and related derivatives</span> </div> </a> <ul id="toc-Terephthalic_acid_and_related_derivatives-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Solvent_applications_and_industrial_purposes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Solvent_applications_and_industrial_purposes"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>Solvent applications and industrial purposes</span> </div> </a> <ul id="toc-Solvent_applications_and_industrial_purposes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Laboratory_use" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Laboratory_use"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.3</span> <span>Laboratory use</span> </div> </a> <ul id="toc-Laboratory_use-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Precursor_to_other_compounds" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Precursor_to_other_compounds"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.4</span> <span>Precursor to other compounds</span> </div> </a> <ul id="toc-Precursor_to_other_compounds-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Chemical_properties" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Chemical_properties"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Chemical properties</span> </div> </a> <ul id="toc-Chemical_properties-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Health_and_safety" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Health_and_safety"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Health and safety</span> </div> </a> <ul id="toc-Health_and_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">8</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" title="Table of Contents" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Xylene</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 47 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-47" 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">47 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-af mw-list-item"><a href="https://af.wikipedia.org/wiki/Xileen" title="Xileen – Afrikaans" lang="af" hreflang="af" data-title="Xileen" data-language-autonym="Afrikaans" data-language-local-name="Afrikaans" class="interlanguage-link-target"><span>Afrikaans</span></a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%B2%D9%8A%D9%84%D9%8A%D9%86" title="زيلين – Arabic" lang="ar" hreflang="ar" data-title="زيلين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Ksilollar" title="Ksilollar – Azerbaijani" lang="az" hreflang="az" data-title="Ksilollar" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%9C%E0%A6%BE%E0%A6%87%E0%A6%B2%E0%A6%BF%E0%A6%A8" title="জাইলিন – Bangla" lang="bn" hreflang="bn" data-title="জাইলিন" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Ksilol" title="Ksilol – Bosnian" lang="bs" hreflang="bs" data-title="Ksilol" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Xil%C3%A8" title="Xilè – Catalan" lang="ca" hreflang="ca" data-title="Xilè" 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/Xylen" title="Xylen – Czech" lang="cs" hreflang="cs" data-title="Xylen" 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/Xylen" title="Xylen – Danish" lang="da" hreflang="da" data-title="Xylen" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Xylole" title="Xylole – German" lang="de" hreflang="de" data-title="Xylole" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-el badge-Q17559452 badge-recommendedarticle mw-list-item" title="recommended article"><a href="https://el.wikipedia.org/wiki/%CE%9E%CF%85%CE%BB%CF%8C%CE%BB%CE%B9%CE%BF" title="Ξυλόλιο – Greek" lang="el" hreflang="el" data-title="Ξυλόλιο" 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/Xileno" title="Xileno – Spanish" lang="es" hreflang="es" data-title="Xileno" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Dumetilbenzeno" title="Dumetilbenzeno – Esperanto" lang="eo" hreflang="eo" data-title="Dumetilbenzeno" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Xileno" title="Xileno – Basque" lang="eu" hreflang="eu" data-title="Xileno" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%B2%D8%A7%DB%8C%D9%84%DB%8C%D9%86" title="زایلین – Persian" lang="fa" hreflang="fa" data-title="زایلین" 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/Xyl%C3%A8ne" title="Xylène – French" lang="fr" hreflang="fr" data-title="Xylène" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Xil%C3%A9in" title="Xiléin – Irish" lang="ga" hreflang="ga" data-title="Xiléin" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%9E%90%EC%9D%BC%EB%A0%8C" title="자일렌 – Korean" lang="ko" hreflang="ko" data-title="자일렌" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D5%94%D5%BD%D5%AB%D5%AC%D5%B8%D5%AC" title="Քսիլոլ – Armenian" lang="hy" hreflang="hy" data-title="Քսիլոլ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%9C%E0%A4%BE%E0%A4%87%E0%A4%B2%E0%A5%80%E0%A4%A8" title="जाइलीन – Hindi" lang="hi" hreflang="hi" data-title="जाइलीन" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Ksilen" title="Ksilen – Croatian" lang="hr" hreflang="hr" data-title="Ksilen" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Xilena" title="Xilena – Indonesian" lang="id" hreflang="id" data-title="Xilena" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Xilene" title="Xilene – Italian" lang="it" hreflang="it" data-title="Xilene" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%A7%D7%A1%D7%99%D7%9C%D7%9F" title="קסילן – Hebrew" lang="he" hreflang="he" data-title="קסילן" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%A5%E1%83%A1%E1%83%98%E1%83%9A%E1%83%94%E1%83%9C%E1%83%98" title="ქსილენი – Georgian" lang="ka" hreflang="ka" data-title="ქსილენი" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target"><span>ქართული</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Ksilols" title="Ksilols – Latvian" lang="lv" hreflang="lv" data-title="Ksilols" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Ksilenas" title="Ksilenas – Lithuanian" lang="lt" hreflang="lt" data-title="Ksilenas" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Xilol" title="Xilol – Hungarian" lang="hu" hreflang="hu" data-title="Xilol" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Xilena" title="Xilena – Malay" lang="ms" hreflang="ms" data-title="Xilena" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Xyleen" title="Xyleen – Dutch" lang="nl" hreflang="nl" data-title="Xyleen" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%AD%E3%82%B7%E3%83%AC%E3%83%B3" title="キシレン – Japanese" lang="ja" hreflang="ja" data-title="キシレン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Xylen" title="Xylen – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Xylen" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-nn mw-list-item"><a href="https://nn.wikipedia.org/wiki/Xylen" title="Xylen – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Xylen" data-language-autonym="Norsk nynorsk" data-language-local-name="Norwegian Nynorsk" class="interlanguage-link-target"><span>Norsk nynorsk</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Ksilollar" title="Ksilollar – Uzbek" lang="uz" hreflang="uz" data-title="Ksilollar" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Ksyleny" title="Ksyleny – Polish" lang="pl" hreflang="pl" data-title="Ksyleny" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Xileno" title="Xileno – Portuguese" lang="pt" hreflang="pt" data-title="Xileno" 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/Xilen" title="Xilen – Romanian" lang="ro" hreflang="ro" data-title="Xilen" 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%9A%D1%81%D0%B8%D0%BB%D0%BE%D0%BB%D1%8B" title="Ксилолы – Russian" lang="ru" hreflang="ru" data-title="Ксилолы" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Ksilen" title="Ksilen – Slovenian" lang="sl" hreflang="sl" data-title="Ksilen" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%9A%D1%81%D0%B8%D0%BB%D0%B5%D0%BD" title="Ксилен – Serbian" lang="sr" hreflang="sr" data-title="Ксилен" 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/Ksilen" title="Ksilen – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Ksilen" 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/Ksyleeni" title="Ksyleeni – Finnish" lang="fi" hreflang="fi" data-title="Ksyleeni" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Xylen" title="Xylen – Swedish" lang="sv" hreflang="sv" data-title="Xylen" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%9A%E0%AF%88%E0%AE%B2%E0%AF%80%E0%AE%A9%E0%AF%8D" title="சைலீன் – Tamil" lang="ta" hreflang="ta" data-title="சைலீன்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Ksilen" title="Ksilen – Turkish" lang="tr" hreflang="tr" data-title="Ksilen" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%9A%D1%81%D0%B8%D0%BB%D0%B5%D0%BD%D0%B8" title="Ксилени – Ukrainian" lang="uk" hreflang="uk" data-title="Ксилени" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Xylen" title="Xylen – Vietnamese" lang="vi" hreflang="vi" data-title="Xylen" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E4%BA%8C%E7%94%B2%E8%8B%AF" title="二甲苯 – Chinese" lang="zh" hreflang="zh" data-title="二甲苯" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit 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src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b3/IUPAC-cyclic.svg/400px-IUPAC-cyclic.svg.png" decoding="async" width="400" height="165" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b3/IUPAC-cyclic.svg/600px-IUPAC-cyclic.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b3/IUPAC-cyclic.svg/800px-IUPAC-cyclic.svg.png 2x" data-file-width="446" data-file-height="184" /></a><figcaption>The three xylene isomers: <a href="/wiki/O-Xylene" title="O-Xylene"><i>o</i>-xylene</a>, <a href="/wiki/M-Xylene" title="M-Xylene"><i>m</i>-xylene</a>, and <a href="/wiki/P-Xylene" title="P-Xylene"><i>p</i>-xylene</a></figcaption></figure> <p>In <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a>, <b>xylene</b> or <b>xylol</b> (from <a href="/wiki/Greek_language" title="Greek language">Greek</a> <i> </i>ξύλον<i> (xylon)</i> <span class="gloss-quot">'</span><span class="gloss-text">wood</span><span class="gloss-quot">'</span>;<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><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> <a href="/wiki/IUPAC_name" class="mw-redirect" title="IUPAC name">IUPAC name</a>: <b>dimethylbenzene</b>) are any of three <a href="/wiki/Organic_compound" title="Organic compound">organic compounds</a> with the formula <style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">(CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub>C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">4</sub></span>. They are derived from the substitution of two <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a> atoms with <a href="/wiki/Methyl_group" title="Methyl group">methyl groups</a> in a <a href="/wiki/Benzene" title="Benzene">benzene</a> ring; which hydrogens are substituted determines which of three <a href="/wiki/Structural_isomers" class="mw-redirect" title="Structural isomers">structural isomers</a> results. It is a colorless, flammable, slightly greasy liquid of great industrial value.<sup id="cite_ref-Ullmann_3-0" class="reference"><a href="#cite_note-Ullmann-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>The mixture is referred to as both xylene and, more precisely, xylenes. <b>Mixed xylenes</b> refers to a mixture of the xylenes plus <a href="/wiki/Ethylbenzene" title="Ethylbenzene">ethylbenzene</a>. The four compounds have identical <a href="/wiki/Molecular_formulas" class="mw-redirect" title="Molecular formulas">molecular formulas</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">C<sub class="template-chem2-sub">8</sub>H<sub class="template-chem2-sub">10</sub></span>. Typically the four compounds are produced together by various <a href="/wiki/Catalytic_reforming" title="Catalytic reforming">catalytic reforming</a> and <a href="/wiki/Pyrolysis" title="Pyrolysis">pyrolysis</a> methods.<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> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Occurrence_and_production">Occurrence and production</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Xylene&action=edit&section=1" title="Edit section: Occurrence and production"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Xylenes are an important <a href="/wiki/Petrochemical" title="Petrochemical">petrochemical</a> produced by <a href="/wiki/Catalytic_reforming" title="Catalytic reforming">catalytic reforming</a> and also by <a href="/wiki/Carbonization" title="Carbonization">coal carbonisation</a> in the manufacture of <a href="/wiki/Coke_(fuel)" title="Coke (fuel)">coke fuel</a>. They also occur in crude oil in concentrations of about 0.5–1%, depending on the source. Small quantities occur in <a href="/wiki/Gasoline" title="Gasoline">gasoline</a> and <a href="/wiki/Jet_fuel" title="Jet fuel">aircraft fuels</a>. </p><p>Xylenes are produced mainly as part of the <a href="/wiki/BTX_(chemistry)" title="BTX (chemistry)">BTX</a> aromatics (<a href="/wiki/Benzene" title="Benzene">benzene</a>, <a href="/wiki/Toluene" title="Toluene">toluene</a>, and xylenes) extracted from the product of <a href="/wiki/Catalytic_reforming" title="Catalytic reforming">catalytic reforming</a> known as <a href="/wiki/Reformate" class="mw-redirect" title="Reformate">reformate</a>. </p><p>Several million tons are produced annually.<sup id="cite_ref-Ullmann_3-1" class="reference"><a href="#cite_note-Ullmann-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> In 2011, a global consortium began construction of one of the world's largest xylene plants in <a href="/wiki/Singapore" title="Singapore">Singapore</a>.<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="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Xylene&action=edit&section=2" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Xylene was first isolated and named in 1850 by the French chemist <a href="/wiki/Auguste_Andr%C3%A9_Thomas_Cahours" title="Auguste André Thomas Cahours">Auguste Cahours</a> (1813–1891), having been discovered as a constituent of <a href="/wiki/Wood_tar" class="mw-redirect" title="Wood tar">wood tar</a>.<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> </p> <div class="mw-heading mw-heading2"><h2 id="Industrial_production">Industrial production</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Xylene&action=edit&section=3" title="Edit section: Industrial production"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Xylenes are produced by the <a href="/wiki/Methylation" title="Methylation">methylation</a> of <a href="/wiki/Toluene" title="Toluene">toluene</a> and <a href="/wiki/Benzene" title="Benzene">benzene</a>.<sup id="cite_ref-Ullmann_3-2" class="reference"><a href="#cite_note-Ullmann-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> Commercial or <a href="/wiki/Chemical_purity" title="Chemical purity">laboratory-grade</a> xylene produced usually contains about 40–65% of <a href="/wiki/M-Xylene" title="M-Xylene"><i>m</i>-xylene</a> and up to 20% each of <a href="/wiki/O-Xylene" title="O-Xylene"><i>o</i>-xylene</a>, <a href="/wiki/P-Xylene" title="P-Xylene"><i>p</i>-xylene</a> and <a href="/wiki/Ethylbenzene" title="Ethylbenzene">ethylbenzene</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><sup id="cite_ref-Kandyala_9-0" class="reference"><a href="#cite_note-Kandyala-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Sweden_10-0" class="reference"><a href="#cite_note-Sweden-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> The ratio of isomers can be shifted to favor the highly valued <i>p</i>-xylene via the patented UOP-<i>Isomar</i> process<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> or by <a href="/wiki/Transalkylation" title="Transalkylation">transalkylation</a> of xylene with itself or trimethylbenzene. These conversions are catalyzed by <a href="/wiki/Zeolite" title="Zeolite">zeolites</a>.<sup id="cite_ref-Ullmann_3-3" class="reference"><a href="#cite_note-Ullmann-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/ZSM-5" title="ZSM-5">ZSM-5</a> is used to facilitate some isomerization reactions leading to mass production of modern plastics. </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=Xylene&action=edit&section=4" title="Edit section: Properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The physical properties of the isomers of xylene differ slightly. The melting point ranges from −47.87 °C (−54.17 °F) (<i>m</i>-xylene) to 13.26 °C (55.87 °F) (<i>p</i>-xylene)—as usual, the para isomer's melting point is much higher because it packs more readily in the crystal structure. The boiling point for each isomer is around 140 °C (284 °F). The density of each isomer is around 0.87 g/mL (7.3 lb/US gal; 8.7 lb/imp gal) and thus is less dense than <a href="/wiki/Properties_of_water" title="Properties of water">water</a>. The odor of xylene is detectable at concentrations as low as 0.08 to 3.7 ppm (parts of xylene per million parts of air) and can be tasted in water at 0.53 to 1.8 ppm.<sup id="cite_ref-Kandyala_9-1" class="reference"><a href="#cite_note-Kandyala-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <table align="center" class="wikitable" style="background:white; border-color:#C0C090; text-align:center;"> <tbody><tr> <th style="background: #F8EABA; text-align: center;" colspan="5">Xylene isomers </th></tr> <tr> <th style="background: #F8EABA; text-align: center;" colspan="5">General </th></tr> <tr style="font-weight:bold;"> <td>Common name </td> <td>Xylenes<br />(mixture) </td> <td><a href="/wiki/O-Xylene" title="O-Xylene"><i>o</i>-Xylene</a> </td> <td><a href="/wiki/M-Xylene" title="M-Xylene"><i>m</i>-Xylene</a> </td> <td><a href="/wiki/P-Xylene" title="P-Xylene"><i>p</i>-Xylene</a> </td></tr> <tr> <td><a href="/wiki/IUPAC_nomenclature" class="mw-redirect" title="IUPAC nomenclature">Systematic name</a> </td> <td>Dimethylbenzene </td> <td>1,2-Dimethylbenzene </td> <td>1,3-Dimethylbenzene </td> <td>1,4-Dimethylbenzene </td></tr> <tr> <td>Other names </td> <td>Xylol </td> <td><i>o</i>-Xylol;<br />Orthoxylene </td> <td><i>m</i>-Xylol;<br />Metaxylene </td> <td><i>p</i>-Xylol;<br />Paraxylene </td></tr> <tr> <td><a href="/wiki/Chemical_formula" title="Chemical formula">Molecular formula</a> </td> <td colspan="4">C<sub>8</sub>H<sub>10</sub> </td></tr> <tr> <td><a href="/wiki/Simplified_molecular_input_line_entry_specification" class="mw-redirect" title="Simplified molecular input line entry specification">SMILES</a> </td> <td> </td> <td>Cc1c(C)cccc1 </td> <td>Cc1cc(C)ccc1 </td> <td>Cc1ccc(C)cc1 </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td colspan="4">106.16 g/mol </td></tr> <tr> <td>Appearance </td> <td colspan="4">Clear, colorless liquid </td></tr> <tr> <td><a href="/wiki/CAS_registry_number" class="mw-redirect" title="CAS registry number">CAS number</a> </td> <td>[1330-20-7] </td> <td>[95-47-6] </td> <td>[108-38-3] </td> <td>[106-42-3] </td></tr> <tr> <th style="background: #F8EABA; text-align: center;" colspan="5">Properties </th></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> and <a href="/wiki/Phase_(matter)" title="Phase (matter)">phase</a> </td> <td>0.864 g/mL, liquid </td> <td>0.88 g/mL, liquid </td> <td>0.86 g/mL, liquid </td> <td>0.86 g/mL, liquid </td></tr> <tr> <td><a href="/wiki/Soluble" class="mw-redirect" title="Soluble">Solubility</a> in water </td> <td colspan="4">Practically insoluble </td></tr> <tr> <td colspan="5">Soluble in non-polar solvents such as <a href="/wiki/Aromatic_hydrocarbon" class="mw-redirect" title="Aromatic hydrocarbon">aromatic hydrocarbons</a> </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>−47.4 °C (−53.3 °F; 226 K) </td> <td>−25 °C (−13 °F; 248 K) </td> <td>−48 °C (−54 °F; 225 K) </td> <td>13 °C (55 °F; 286 K) </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>138.5 °C (281.3 °F; 412 K) </td> <td>144 °C (291 °F; 417 K) </td> <td>139 °C (282 °F; 412 K) </td> <td>138 °C (280 °F; 411 K) </td></tr> <tr> <td><a href="/wiki/Viscosity" title="Viscosity">Viscosity</a> </td> <td> </td> <td>0.812 c<a href="/wiki/Poise_(unit)" title="Poise (unit)">P</a> at 20 °C (68 °F) </td> <td>0.62 c<a href="/wiki/Poise_(unit)" title="Poise (unit)">P</a> at 20 °C (68 °F) </td> <td>0.34 c<a href="/wiki/Poise_(unit)" title="Poise (unit)">P</a> at 30 °C (86 °F) </td></tr> <tr> <th style="background: #F8EABA; text-align: center;" colspan="5">Hazards </th></tr> <tr> <td><a href="/wiki/Safety_data_sheet" title="Safety data sheet">SDS</a> </td> <td><a rel="nofollow" class="external text" href="https://www.fishersci.com/store/msds?partNumber=X5FB50&productDescription=XYLENES+ACS+FB+50L&vendorId=VN00033897&countryCode=US&language=en">Xylenes</a> </td> <td><a rel="nofollow" class="external text" href="https://fscimage.fishersci.com/msds/17180.htm"><i>o</i>-Xylene</a> </td> <td><a rel="nofollow" class="external text" href="https://fscimage.fishersci.com/msds/95260.htm"><i>m</i>-Xylene</a> </td> <td><a rel="nofollow" class="external text" href="https://fscimage.fishersci.com/msds/95257.htm"><i>p</i>-Xylene</a> </td></tr> <tr> <td><a href="/wiki/GHS_hazard_pictograms" title="GHS hazard pictograms">EU pictograms</a> </td> <td colspan="4"><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-flamme.svg" class="mw-file-description" title="GHS02: Flammable"><img alt="GHS02: Flammable" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/GHS-pictogram-flamme.svg/50px-GHS-pictogram-flamme.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/GHS-pictogram-flamme.svg/75px-GHS-pictogram-flamme.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6d/GHS-pictogram-flamme.svg/100px-GHS-pictogram-flamme.svg.png 2x" data-file-width="512" data-file-height="512" /></a></span><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-exclam.svg" class="mw-file-description" title="GHS07: Exclamation mark"><img alt="GHS07: Exclamation mark" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/50px-GHS-pictogram-exclam.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/75px-GHS-pictogram-exclam.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/100px-GHS-pictogram-exclam.svg.png 2x" data-file-width="512" data-file-height="512" /></a></span><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-silhouette.svg" class="mw-file-description" title="GHS08: Health hazard"><img alt="GHS08: Health hazard" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/50px-GHS-pictogram-silhouette.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/75px-GHS-pictogram-silhouette.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/100px-GHS-pictogram-silhouette.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span> <p><br /> </p> </td></tr> <tr> <td><a href="/wiki/NFPA_704" title="NFPA 704">NFPA 704</a> </td> <td colspan="4"><style data-mw-deduplicate="TemplateStyles:r1170367383">.mw-parser-output .nfpa-704-diamond-ref{float:right;padding:1px;text-align:right}.mw-parser-output .nfpa-704-diamond-container{width:82px;font-family:sans-serif;margin:0 auto}.mw-parser-output .nfpa-704-diamond-container-ref{float:left;margin-left:1em}.mw-parser-output .nfpa-704-diamond-images{float:left;font-size:20px;text-align:center;position:relative;height:80px;width:80px;padding:1px}.mw-parser-output .nfpa-704-diamond-map{position:absolute;height:80px;width:80px}.mw-parser-output .nfpa-704-diamond .noresize{margin:0 auto}.mw-parser-output .nfpa-704-diamond-code{line-height:1em;text-align:center;position:absolute}.mw-parser-output .nfpa-704-diamond-code>a{color:black}.mw-parser-output .nfpa-704-diamond-blue{width:13px;top:31px;left:15px}.mw-parser-output .nfpa-704-diamond-red{width:12px;top:12px;left:35px}.mw-parser-output .nfpa-704-diamond-yellow{width:13px;top:31px;left:54px}.mw-parser-output .nfpa-704-diamond-white-image{position:relative;top:51px;left:0}.mw-parser-output .nfpa-704-diamond-white-text{vertical-align:middle;text-align:center;line-height:80%;position:absolute;top:52px}.mw-parser-output .nfpa-704-diamond-white-text a>span{position:absolute;color:black}.mw-parser-output .nfpa-704-diamond-white-wors{font-size:15px;width:23px;left:29px}.mw-parser-output .nfpa-704-diamond-white-wox{font-size:15px;font-stretch:condensed;width:21px;line-height:80%;top:-4px;left:29px}.mw-parser-output .nfpa-704-diamond-white-abcp{font-size:13.5px;font-stretch:condensed;width:28px;left:26px}.mw-parser-output .nfpa-704-diamond-white-ac{font-size:10px;width:30px;left:25px}.mw-parser-output .nfpa-704-diamond-white-strike{text-decoration:line-through}</style><div class="nfpa-704-diamond notheme"><div class="nfpa-704-diamond-container"><div class="nfpa-704-diamond-images nounderlines"> <div class="nfpa-704-diamond-map"><figure class="noresize" typeof="mw:File"><span><img alt="NFPA 704 four-colored diamond" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/80px-NFPA_704.svg.png" decoding="async" width="80" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/120px-NFPA_704.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/160px-NFPA_704.svg.png 2x" data-file-width="512" data-file-height="512" usemap="#ImageMap_9a02d12247c3a88a" /></span><map name="ImageMap_9a02d12247c3a88a"><area href="/wiki/NFPA_704#Blue" shape="poly" coords="23,23,47,47,23,70,0,47" alt="Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform" title="Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform" /><area href="/wiki/NFPA_704#Red" shape="poly" coords="47,0,70,23,47,47,23,23" alt="Flammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasoline" title="Flammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasoline" /><area href="/wiki/NFPA_704#Yellow" shape="poly" coords="70,23,94,47,70,70,47,47" alt="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" /><area href="/wiki/NFPA_704#White" shape="poly" coords="47,47,70,70,47,94,23,70" alt="Special hazards (white): no code" title="Special hazards (white): no code" /></map><figcaption></figcaption></figure></div><div class="nfpa-704-diamond-code nfpa-704-diamond-blue"> <a href="/wiki/NFPA_704#Blue" title="NFPA 704"><span title="Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform" class="notheme mw-no-invert">2</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-red"> <a href="/wiki/NFPA_704#Red" title="NFPA 704"><span title="Flammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasoline" class="notheme mw-no-invert">3</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-yellow"> <a href="/wiki/NFPA_704#Yellow" title="NFPA 704"><span title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" class="notheme mw-no-invert">0</span></a></div></div></div></div> </td></tr> <tr> <td><a href="/wiki/Flash_point" title="Flash point">Flash point</a> </td> <td>30 °C (86 °F) </td> <td>17 °C (63 °F) </td> <td>25 °C (77 °F) </td> <td>25 °C (77 °F) </td></tr> <tr> <td><a href="/wiki/GHS_hazard_statements" title="GHS hazard statements">H</a> & <a href="/wiki/GHS_precautionary_statements" title="GHS precautionary statements">P phrases</a> </td> <td colspan="4"><abbr class="abbr" title="H225: Highly flammable liquid and vapour">H225</abbr>, <abbr class="abbr" title="H226: Flammable liquid and vapour">H226</abbr>, <abbr class="abbr" title="H304: May be fatal if swallowed and enters airways">H304</abbr>, <abbr class="abbr" title="H312: Harmful in contact with skin">H312</abbr>, <abbr class="abbr" title="H315: Causes skin irritation">H315</abbr>, <abbr class="abbr" title="H319: Causes serious eye irritation">H319</abbr>, <abbr class="abbr" title="H332: Harmful if inhaled">H332</abbr>, <abbr class="abbr" title="H335: May cause respiratory irritation">H335</abbr>, <abbr class="abbr" title="H412: Harmful to aquatic life with long lasting effects">H412</abbr><br /> <p><abbr class="abbr" title="P210: Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking.">P210</abbr>, <abbr class="abbr" title="P233: Keep container tightly closed.">P233</abbr>, <abbr class="abbr" title="P240: Ground and bond container and receiving equipment.">P240</abbr>, <abbr class="abbr" title="P241: Use explosion-proof electrical/ventilating/light/.../equipment.">P241</abbr>, <abbr class="abbr" title="P242: Use only non-sparking tools.">P242</abbr>, <abbr class="abbr" title="P243: Take precautionary measures to prevent static discharges.">P243</abbr>, <abbr class="abbr" title="P261: Avoid breathing dust/fume/gas/mist/vapours/spray.">P261</abbr>, <abbr class="abbr" title="P264: Wash ... thoroughly after handling.">P264</abbr>, <abbr class="abbr" title="P271: Use only outdoors or in a well-ventilated area.">P271</abbr>, <abbr class="abbr" title="P273: Avoid release to the environment.">P273</abbr>, <abbr class="abbr" title="P280: Wear protective gloves/protective clothing/eye protection/face protection.">P280</abbr>, <abbr class="abbr" title="P301+P310: IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.">P301+P310</abbr>, <abbr class="abbr" title="P302+P352: IF ON SKIN: Wash with soap and water.">P302+P352</abbr>, <abbr class="abbr" title="P303+P361+P353: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water [or shower].">P303+P361+P353</abbr>, <abbr class="abbr" title="P304+P312: IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.">P304+P312</abbr>, <abbr class="abbr" title="P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing.">P304+P340</abbr>, <abbr class="abbr" title="P305+P351+P338: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing.">P305+P351+P338</abbr>, <abbr class="abbr" title="P312: Call a POISON CENTER or doctor/physician if you feel unwell.">P312</abbr>, <abbr class="abbr" title="P321: Specific treatment (see ... on this label).">P321</abbr>, <abbr class="abbr" title="P322: Specific measures (see ... on this label).">P322</abbr>, <abbr class="abbr" title="P331: Do NOT induce vomiting.">P331</abbr>, <abbr class="abbr" title="P332+P313: If skin irritation occurs: Get medical advice/attention.">P332+P313</abbr>, <abbr class="abbr" title="P337+P313: If eye irritation persists: Get medical advice/attention.">P337+P313</abbr>, <abbr class="abbr" title="P362: Take off contaminated clothing.">P362</abbr>, <abbr class="abbr" title="P363: Wash contaminated clothing before reuse.">P363</abbr>, <abbr class="abbr" title="P370+P378: In case of fire: Use ... to extinguish.">P370+P378</abbr>, <abbr class="abbr" title="P403+P233: Store in a well ventilated place. Keep container tightly closed.">P403+P233</abbr>, <abbr class="abbr" title="P403+P235: Store in a well ventilated place. Keep cool.">P403+P235</abbr>, <abbr class="abbr" title="P405: Store locked up.">P405</abbr>, <abbr class="abbr" title="P501: Dispose of contents/container to ...">P501</abbr> </p> </td></tr> <tr> <td><a href="/wiki/RTECS" class="mw-redirect" title="RTECS">RTECS</a> number </td> <td> </td> <td>ZE2450000 </td> <td>ZE2275000 </td> <td>ZE2625000 </td></tr> <tr> <th style="background: #F8EABA; text-align: center;" colspan="5">Related compounds </th></tr> <tr> <td>Related aromatic<br />hydrocarbons </td> <td colspan="4"><a href="/wiki/Toluene" title="Toluene">Toluene</a>, <a href="/wiki/Mesitylene" title="Mesitylene">mesitylene</a>, <a href="/wiki/Benzene" title="Benzene">benzene</a>, <a href="/wiki/Ethylbenzene" title="Ethylbenzene">ethylbenzene</a> </td></tr> <tr> <td>Related compounds </td> <td colspan="4">Xylenols – types of <a href="/wiki/Phenols" title="Phenols">phenols</a> </td></tr> <tr> <td style="background: #F8EABA; text-align: center;" colspan="5"><small>Except where noted otherwise, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state (at 25<span class="nowrap"> </span>°C, 100<span class="nowrap"> </span>kPa)</a><br /><a href="/wiki/Wikipedia:Chemical_infobox" title="Wikipedia:Chemical infobox">Infobox disclaimer and references</a></small> </td></tr></tbody></table> <p>Xylenes form <a href="/wiki/Azeotrope" title="Azeotrope">azeotropes</a> with water and a variety of alcohols. The azeotrope with water consists of 60% xylenes and boils at 94.5 °C.<sup id="cite_ref-Ullmann_3-4" class="reference"><a href="#cite_note-Ullmann-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> As with many <a href="/wiki/Alkylbenzene" title="Alkylbenzene">alkylbenzene</a> compounds, xylenes form complexes with various <a href="/wiki/Halocarbon" title="Halocarbon">halocarbons</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> The complexes of different isomers often have dramatically different properties from each other.<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> <div class="mw-heading mw-heading2"><h2 id="Applications">Applications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Xylene&action=edit&section=5" title="Edit section: Applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Terephthalic_acid_and_related_derivatives">Terephthalic acid and related derivatives</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Xylene&action=edit&section=6" title="Edit section: Terephthalic acid and related derivatives"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><i>p</i>-Xylene is the principal precursor to <a href="/wiki/Terephthalic_acid" title="Terephthalic acid">terephthalic acid</a> and <a href="/wiki/Dimethyl_terephthalate" title="Dimethyl terephthalate">dimethyl terephthalate</a>, both <a href="/wiki/Monomer" title="Monomer">monomers</a> used in the production of <a href="/wiki/Polyethylene_terephthalate" title="Polyethylene terephthalate">polyethylene terephthalate</a> (PET) <a href="/wiki/Plastic_bottle" title="Plastic bottle">plastic bottles</a> and <a href="/wiki/Polyester" title="Polyester">polyester</a> clothing. 98% of <i>p</i>-xylene production, and half of all xylenes produced is consumed in this manner.<sup id="cite_ref-Sweden_10-1" class="reference"><a href="#cite_note-Sweden-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> <i>o</i>-Xylene is an important precursor to <a href="/wiki/Phthalic_anhydride" title="Phthalic anhydride">phthalic anhydride</a>. The demand for <a href="/wiki/Isophthalic_acid" title="Isophthalic acid">isophthalic acid</a> is relatively modest, so <i>m</i>-xylene is rarely sought (and hence the utility of its conversion to the <i>o</i>- and <i>p</i>-isomers). </p> <div class="mw-heading mw-heading3"><h3 id="Solvent_applications_and_industrial_purposes">Solvent applications and industrial purposes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Xylene&action=edit&section=7" title="Edit section: Solvent applications and industrial purposes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Xylenes are used as a solvent in <a href="/wiki/Printing" title="Printing">printing</a>, <a href="/wiki/Rubber" class="mw-redirect" title="Rubber">rubber</a>, and <a href="/wiki/Leather" title="Leather">leather</a> industries. It is a common component of ink, <a href="/wiki/Rubber" class="mw-redirect" title="Rubber">rubber</a>, and <a href="/wiki/Adhesive" title="Adhesive">adhesives</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> In thinning <a href="/wiki/Paint" title="Paint">paints</a> and <a href="/wiki/Varnish" title="Varnish">varnishes</a>, it can be substituted for <a href="/wiki/Toluene" title="Toluene">toluene</a> where slower drying is desired, and thus is used by <a href="/wiki/Conservator-restorer" title="Conservator-restorer">conservators</a> of art objects in solubility testing.<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> Similarly it is a <a href="/wiki/Cleaning_agent" title="Cleaning agent">cleaning agent</a>, e.g., for <a href="/wiki/Steel" title="Steel">steel</a>, <a href="/wiki/Silicon_wafer" class="mw-redirect" title="Silicon wafer">silicon wafers</a>, and <a href="/wiki/Integrated_circuit" title="Integrated circuit">integrated circuits</a>. In dentistry, xylene can be used to dissolve <a href="/wiki/Gutta_percha" class="mw-redirect" title="Gutta percha">gutta percha</a>, a material used for endodontics (root-canal treatments). In the petroleum industry, xylene is also a frequent component of paraffin solvents, used when the tubing becomes clogged with paraffin wax. </p> <div class="mw-heading mw-heading3"><h3 id="Laboratory_use">Laboratory use</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Xylene&action=edit&section=8" title="Edit section: Laboratory use"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Xylene is used in the laboratory to make baths with dry ice to cool reaction vessels,<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> and as a <a href="/wiki/Solvent" title="Solvent">solvent</a> to remove synthetic <a href="/wiki/Immersion_oil" class="mw-redirect" title="Immersion oil">immersion oil</a> from the microscope <a href="/wiki/Objective_(optics)" title="Objective (optics)">objective</a> in <a href="/wiki/Optical_microscope" title="Optical microscope">light microscopy</a>.<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> In <a href="/wiki/Histology" title="Histology">histology</a>, xylene is the most widely used clearing agent.<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> Xylene is used to remove paraffin from dried microscope slides prior to staining. After staining, microscope slides are put in xylene prior to mounting with a coverslip. </p> <div class="mw-heading mw-heading3"><h3 id="Precursor_to_other_compounds">Precursor to other compounds</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Xylene&action=edit&section=9" title="Edit section: Precursor to other compounds"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In one large-scale application, para-xylene is converted to <a href="/wiki/Terephthalic_acid" title="Terephthalic acid">terephthalic acid</a>. The major application of ortho-xylene is as a precursor to <a href="/wiki/Phthalate_ester" class="mw-redirect" title="Phthalate ester">phthalate esters</a>, used as <a href="/wiki/Plasticizer" title="Plasticizer">plasticizer</a>. Meta-xylene is converted to <a href="/wiki/Isophthalic_acid" title="Isophthalic acid">isophthalic acid</a> derivatives, which are components of <a href="/wiki/Alkyd_resin" class="mw-redirect" title="Alkyd resin">alkyd resins</a>.<sup id="cite_ref-Ullmann_3-5" class="reference"><a href="#cite_note-Ullmann-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Chemical_properties">Chemical properties</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Xylene&action=edit&section=10" title="Edit section: Chemical properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Generally, two kinds of reactions occur with xylenes: those involving the methyl groups and those involving the ring C–H bonds. Being benzylic and hence weakened, the C–H bonds of the methyl groups are susceptible to free-radical reactions, including halogenation to the corresponding <a href="/wiki/Xylene_dichloride" class="mw-redirect" title="Xylene dichloride">xylene dichlorides</a> (bis(chloromethyl)benzenes), while <a href="/wiki/Free-radical_halogenation" title="Free-radical halogenation">mono-bromination</a> yields <a href="/wiki/Xylyl_bromide" title="Xylyl bromide">xylyl bromide</a>, a <a href="/wiki/Tear_gas" title="Tear gas">tear gas</a> agent. Oxidation and <a href="/wiki/Ammoxidation" title="Ammoxidation">ammoxidation</a> also target the methyl groups, affording dicarboxylic acids and the dinitriles. Electrophiles attack the aromatic ring, leading to chloro- and nitroxylenes.<sup id="cite_ref-Ullmann_3-6" class="reference"><a href="#cite_note-Ullmann-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Health_and_safety">Health and safety</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Xylene&action=edit&section=11" title="Edit section: Health and safety"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Xylene is flammable but of modest acute toxicity, with <a href="/wiki/Median_lethal_dose" title="Median lethal dose">LD<sub style="font-size:-1">50</sub></a> ranges from 200 to 5000 mg/kg for animals. Oral <a href="/wiki/Median_lethal_dose" title="Median lethal dose">LD<sub style="font-size:-1">50</sub></a> for rats is 4300 mg/kg. The principal mechanism of detoxification is oxidation to <a href="/wiki/Toluic_acid" title="Toluic acid">methylbenzoic acid</a> and hydroxylation to hydroxylene.<sup id="cite_ref-Ullmann_3-7" class="reference"><a href="#cite_note-Ullmann-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>The main effect of inhaling xylene vapor is <a href="/wiki/CNS_depression" class="mw-redirect" title="CNS depression">depression of the central nervous system</a> (CNS), with symptoms such as headache, dizziness, nausea and vomiting. At an exposure of 100 ppm, one may experience nausea or a headache. At an exposure between 200 and 500 ppm, symptoms can include feeling "high", dizziness, weakness, irritability, vomiting, and slowed reaction time.<sup id="cite_ref-:0_20-0" class="reference"><a href="#cite_note-:0-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup><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>The side effects of exposure to low concentrations of xylene (<span class="nowrap">< 200 ppm</span>) are reversible and do not cause permanent damage. Long-term exposure may lead to headaches, irritability, depression, insomnia, agitation, extreme tiredness, tremors, hearing loss, impaired concentration and short-term memory loss.<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><sup class="noprint Inline-Template" style="margin-left:0.1em; white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Please_clarify" title="Wikipedia:Please clarify"><span title="short-term memory loss? (June 2016)">clarification needed</span></a></i>]</sup> A condition called <a href="/wiki/Chronic_solvent-induced_encephalopathy" title="Chronic solvent-induced encephalopathy">chronic solvent-induced encephalopathy</a>, commonly known as "organic-solvent syndrome" has been associated with xylene exposure. There is very little information available that isolates xylene from other solvent exposures in the examination of these effects.<sup id="cite_ref-:0_20-1" class="reference"><a href="#cite_note-:0-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p><p>Hearing disorders have been also linked to xylene exposure, both from studies with experimental animals,<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><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> as well as clinical studies.<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><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><sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </p><p>Xylene is also a skin irritant and strips the skin of its oils, making it more permeable to other chemicals. The use of impervious gloves and masks, along with respirators where appropriate, is recommended to avoid occupational health issues from xylene exposure.<sup id="cite_ref-:0_20-2" class="reference"><a href="#cite_note-:0-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p><p>Xylenes are metabolized to <a href="/wiki/Methylhippuric_acid" title="Methylhippuric acid">methylhippuric acids</a>.<sup id="cite_ref-NIOSH_28-0" class="reference"><a href="#cite_note-NIOSH-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Inoue_29-0" class="reference"><a href="#cite_note-Inoue-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> The presence of methylhippuric acid can be used as a <a href="/wiki/Biomarker" title="Biomarker">biomarker</a> to determine exposure to xylene.<sup id="cite_ref-Inoue_29-1" class="reference"><a href="#cite_note-Inoue-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Xylene&action=edit&section=12" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Alkylbenzene" title="Alkylbenzene">Alkylbenzene</a></li> <li><a href="/wiki/C2-Benzenes" title="C2-Benzenes">C2-Benzenes</a></li> <li><a href="/wiki/Hydrodealkylation" title="Hydrodealkylation">Hydrodealkylation</a></li> <li><a href="/wiki/Transalkylation" title="Transalkylation">Transalkylation</a></li> <li><a href="/wiki/Xylene_cyanol" title="Xylene cyanol">Xylene cyanol</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=Xylene&action=edit&section=13" 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 reflist-columns references-column-width" style="column-width: 30em;"> <ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external text" href="https://www.perseus.tufts.edu/hopper/text?doc=Perseus:text:1999.04.0057:entry=cu/lon1"><span title="Ancient Greek (to 1453)-language text"><span lang="grc">ξύλον</span></span></a>. <a href="/wiki/Henry_Liddell" title="Henry Liddell">Liddell, Henry George</a>; <a href="/wiki/Robert_Scott_(philologist)" title="Robert Scott (philologist)">Scott, Robert</a>; <i><a href="/wiki/A_Greek%E2%80%93English_Lexicon" title="A Greek–English Lexicon">A Greek–English Lexicon</a></i> at the <a href="/wiki/Perseus_Project" class="mw-redirect" title="Perseus Project">Perseus Project</a>.</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"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFHarper" class="citation web cs1">Harper, Douglas. <a rel="nofollow" class="external text" href="https://www.etymonline.com/?term=xylene">"xylene"</a>. <i><a href="/wiki/Online_Etymology_Dictionary" class="mw-redirect" title="Online Etymology Dictionary">Online Etymology Dictionary</a></i>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Online+Etymology+Dictionary&rft.atitle=xylene&rft.aulast=Harper&rft.aufirst=Douglas&rft_id=https%3A%2F%2Fwww.etymonline.com%2F%3Fterm%3Dxylene&rfr_id=info%3Asid%2Fen.wikipedia.org%3AXylene" class="Z3988"></span></span> </li> <li id="cite_note-Ullmann-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-Ullmann_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Ullmann_3-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Ullmann_3-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Ullmann_3-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-Ullmann_3-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-Ullmann_3-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-Ullmann_3-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-Ullmann_3-7"><sup><i><b>h</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFFabriGraeserSimo2000" class="citation book cs1">Fabri, Jörg; Graeser, Ulrich; Simo, Thomas A. (2000). "Xylenes". <i>Ullmann's Encyclopedia of Industrial Chemistry</i>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F14356007.a28_433">10.1002/14356007.a28_433</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3527306732" title="Special:BookSources/978-3527306732"><bdi>978-3527306732</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Xylenes&rft.btitle=Ullmann%27s+Encyclopedia+of+Industrial+Chemistry&rft.date=2000&rft_id=info%3Adoi%2F10.1002%2F14356007.a28_433&rft.isbn=978-3527306732&rft.aulast=Fabri&rft.aufirst=J%C3%B6rg&rft.au=Graeser%2C+Ulrich&rft.au=Simo%2C+Thomas+A.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AXylene" 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="CITEREFCannella2000" class="citation book cs1">Cannella, William J. (2000). "Xylenes and Ethylbenzene". <i>Kirk-Othmer Encyclopedia of Chemical Technology</i>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F0471238961.2425120503011414.a01">10.1002/0471238961.2425120503011414.a01</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0471238961" title="Special:BookSources/0471238961"><bdi>0471238961</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Xylenes+and+Ethylbenzene&rft.btitle=Kirk-Othmer+Encyclopedia+of+Chemical+Technology&rft.date=2000&rft_id=info%3Adoi%2F10.1002%2F0471238961.2425120503011414.a01&rft.isbn=0471238961&rft.aulast=Cannella&rft.aufirst=William+J.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AXylene" class="Z3988"></span></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFTremblay2011" class="citation journal cs1">Tremblay, Jean-François (2011). "Making Aromatics in Singapore". <i>Chemical & Engineering News Archive</i>. <b>89</b> (38): <span class="nowrap">18–</span>19. <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%2Fcen-v089n038.p018">10.1021/cen-v089n038.p018</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemical+%26+Engineering+News+Archive&rft.atitle=Making+Aromatics+in+Singapore&rft.volume=89&rft.issue=38&rft.pages=%3Cspan+class%3D%22nowrap%22%3E18-%3C%2Fspan%3E19&rft.date=2011&rft_id=info%3Adoi%2F10.1021%2Fcen-v089n038.p018&rft.aulast=Tremblay&rft.aufirst=Jean-Fran%C3%A7ois&rfr_id=info%3Asid%2Fen.wikipedia.org%3AXylene" class="Z3988"></span></span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text">Cahours, Auguste (1850) <a rel="nofollow" class="external text" href="http://gallica.bnf.fr/ark:/12148/bpt6k2987x/f319.image.langEN">"Recherches sur les huiles légéres obtenues dans la distillation du bois"</a> (Investigations of light oils obtained by the distillation of wood), <i>Compte rendus</i>, <b>30</b> : 319-323; see especially p. 321. From p. 321: <i>"Je le désignerai sous le nomme </i>xylène<i>."</i> (I will designate it by the name of <i>xylene</i>.) Note: Cahours' empirical formula for xylene is incorrect because chemists at that time used the wrong atomic mass for carbon (6 instead of 12).</span> </li> <li id="cite_note-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text">Martindale, David C. and Kuchar, Paul J., <a rel="nofollow" class="external text" href="https://web.archive.org/web/20180717100321/http://patft.uspto.gov/netacgi/nph-Parser?Sect1=PTO2&Sect2=HITOFF&p=1&u=/netahtml/PTO/search-bool.html&r=1&f=G&l=50&co1=AND&d=PTXT&s1=5043502.PN.&OS=PN/5043502&RS=PN/5043502">Production of xylenes from light aliphatic hydrocarbons via dehydrocyclodimerization and methylation</a>, United States Patent No. 5,043,502, 1991-8-27. Accessed 2012-4-28.</span> </li> <li id="cite_note-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-8">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.epa.gov/airtoxics/hlthef/xylenes.html">"Xylene (Mixed Isomers), Air Toxic Hazard Summary"</a>. United States Environmental Protection Agency<span class="reference-accessdate">. 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(1977). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1008281">"Measurement by gas chromatography of urinary hippuric acid and methylhippuric acid as indices of toluene and xylene exposure"</a>. <i>Occupational and Environmental Medicine</i>. <b>34</b> (<span class="nowrap">305–</span>309): <span class="nowrap">305–</span>309. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1136%2Foem.34.4.305">10.1136/oem.34.4.305</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1008281">1008281</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/588486">588486</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Occupational+and+Environmental+Medicine&rft.atitle=Measurement+by+gas+chromatography+of+urinary+hippuric+acid+and+methylhippuric+acid+as+indices+of+toluene+and+xylene+exposure&rft.volume=34&rft.issue=%3Cspan+class%3D%22nowrap%22%3E305%E2%80%93%3C%2Fspan%3E309&rft.pages=%3Cspan+class%3D%22nowrap%22%3E305-%3C%2Fspan%3E309&rft.date=1977&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1008281%23id-name%3DPMC&rft_id=info%3Apmid%2F588486&rft_id=info%3Adoi%2F10.1136%2Foem.34.4.305&rft.au=Kira+S.&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1008281&rfr_id=info%3Asid%2Fen.wikipedia.org%3AXylene" class="Z3988"></span></span> </li> </ol></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Xylene&action=edit&section=14" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1235681985">.mw-parser-output .side-box{margin:4px 0;box-sizing:border-box;border:1px solid #aaa;font-size:88%;line-height:1.25em;background-color:var(--background-color-interactive-subtle,#f8f9fa);display:flow-root}.mw-parser-output .side-box-abovebelow,.mw-parser-output .side-box-text{padding:0.25em 0.9em}.mw-parser-output .side-box-image{padding:2px 0 2px 0.9em;text-align:center}.mw-parser-output .side-box-imageright{padding:2px 0.9em 2px 0;text-align:center}@media(min-width:500px){.mw-parser-output .side-box-flex{display:flex;align-items:center}.mw-parser-output .side-box-text{flex:1;min-width:0}}@media(min-width:720px){.mw-parser-output .side-box{width:238px}.mw-parser-output .side-box-right{clear:right;float:right;margin-left:1em}.mw-parser-output .side-box-left{margin-right:1em}}</style><style data-mw-deduplicate="TemplateStyles:r1237033735">@media print{body.ns-0 .mw-parser-output .sistersitebox{display:none!important}}@media screen{html.skin-theme-clientpref-night .mw-parser-output .sistersitebox img[src*="Wiktionary-logo-en-v2.svg"]{background-color:white}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .sistersitebox img[src*="Wiktionary-logo-en-v2.svg"]{background-color:white}}</style><div class="side-box side-box-right plainlinks sistersitebox"><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style> <div class="side-box-flex"> <div class="side-box-image"><span class="noviewer" typeof="mw:File"><a href="/wiki/File:Commons-logo.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/30px-Commons-logo.svg.png" decoding="async" width="30" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/45px-Commons-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/59px-Commons-logo.svg.png 2x" data-file-width="1024" data-file-height="1376" /></a></span></div> <div class="side-box-text plainlist">Wikimedia Commons has media related to <span style="font-weight: bold; font-style: italic;"><a href="https://commons.wikimedia.org/wiki/Category:Xylenes" class="extiw" title="commons:Category:Xylenes">Xylenes</a></span>.</div></div> </div> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFChisholm1911" class="citation encyclopaedia cs1"><a href="/wiki/Hugh_Chisholm" title="Hugh Chisholm">Chisholm, Hugh</a>, ed. (1911). <span class="cs1-ws-icon" title="s:1911 Encyclopædia Britannica/Xylene"><a class="external text" href="https://en.wikisource.org/wiki/1911_Encyclop%C3%A6dia_Britannica/Xylene">"Xylene" </a></span>. <i><a href="/wiki/Encyclop%C3%A6dia_Britannica_Eleventh_Edition" title="Encyclopædia Britannica Eleventh Edition">Encyclopædia Britannica</a></i> (11th ed.). Cambridge University Press.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Xylene&rft.btitle=Encyclop%C3%A6dia+Britannica&rft.edition=11th&rft.pub=Cambridge+University+Press&rft.date=1911&rfr_id=info%3Asid%2Fen.wikipedia.org%3AXylene" class="Z3988"></span></li> <li><a rel="nofollow" class="external text" href="https://www.cdc.gov/niosh/npg/npgd0668.html">NIOSH Pocket Guide to Chemical Hazards</a> (<i>o</i>-Xylene)</li> <li><a rel="nofollow" class="external text" href="https://www.cdc.gov/niosh/npg/npgd0669.html">NIOSH Pocket Guide to Chemical Hazards</a> (<i>m</i>-Xylene)</li> <li><a rel="nofollow" class="external text" href="https://www.cdc.gov/niosh/npg/npgd0670.html">NIOSH Pocket Guide to Chemical Hazards</a> (<i>p</i>-Xylene)</li> <li><a rel="nofollow" class="external text" href="https://www.epa.gov/haps/health-effects-notebook-hazardous-air-pollutants">Xylene, Hazard Summary (EPA)</a> (Mixed Isomers)</li> <li><a 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aria-labelledby="Hydrocarbons181" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2" style="background:azzurro;"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><style data-mw-deduplicate="TemplateStyles:r1239400231">.mw-parser-output .navbar{display:inline;font-size:88%;font-weight:normal}.mw-parser-output .navbar-collapse{float:left;text-align:left}.mw-parser-output .navbar-boxtext{word-spacing:0}.mw-parser-output .navbar ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output 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class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Methane" title="Methane">Methane</a></li> <li><a href="/wiki/Ethane" title="Ethane">Ethane</a></li> <li><a href="/wiki/Propane" title="Propane">Propane</a></li> <li><a href="/wiki/Butane" title="Butane">Butane</a></li> <li><a href="/wiki/Pentane" title="Pentane">Pentane</a></li> <li><a href="/wiki/Hexane" title="Hexane">Hexane</a></li> <li><a href="/wiki/Heptane" title="Heptane">Heptane</a></li> <li><a href="/wiki/Octane" title="Octane">Octane</a></li> <li><a href="/wiki/Nonane" title="Nonane">Nonane</a></li> <li><a href="/wiki/Decane" title="Decane">Decane</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Branched alkanes</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Isobutane" title="Isobutane">Isobutane</a></li> <li><a href="/wiki/Isopentane" title="Isopentane">Isopentane</a></li> <li><a href="/wiki/3-Methylpentane" title="3-Methylpentane">3-Methylpentane</a></li> <li><a href="/wiki/Neopentane" title="Neopentane">Neopentane</a></li> <li><a href="/wiki/2-Methylpentane" title="2-Methylpentane">Isohexane</a></li> <li><a href="/wiki/2-Methylhexane" title="2-Methylhexane">Isoheptane</a></li> <li><a href="/wiki/2,2,4-Trimethylpentane" title="2,2,4-Trimethylpentane">Isooctane</a></li> <li><a href="/wiki/2-Methyloctane" title="2-Methyloctane">Isononane</a></li> <li><a href="/w/index.php?title=Isodecane&action=edit&redlink=1" class="new" title="Isodecane (page does not exist)">Isodecane</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Cycloalkane" title="Cycloalkane">Cycloalkanes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cyclopropane" title="Cyclopropane">Cyclopropane</a></li> <li><a href="/wiki/Cyclobutane" title="Cyclobutane">Cyclobutane</a></li> <li><a href="/wiki/Cyclopentane" title="Cyclopentane">Cyclopentane</a></li> <li><a href="/wiki/Cyclohexane" title="Cyclohexane">Cyclohexane</a></li> <li><a href="/wiki/Cycloheptane" title="Cycloheptane">Cycloheptane</a></li> <li><a href="/wiki/Cyclooctane" title="Cyclooctane">Cyclooctane</a></li> <li><a href="/wiki/Cyclononane" title="Cyclononane">Cyclononane</a></li> <li><a href="/wiki/Cyclodecane" title="Cyclodecane">Cyclodecane</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/w/index.php?title=Alkylcycloalkane&action=edit&redlink=1" class="new" title="Alkylcycloalkane (page does not exist)">Alkylcycloalkanes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Methylcyclopropane" title="Methylcyclopropane">Methylcyclopropane</a></li> <li><a href="/w/index.php?title=Methylcyclobutane&action=edit&redlink=1" class="new" title="Methylcyclobutane (page does not exist)">Methylcyclobutane</a></li> <li><a href="/wiki/Methylcyclopentane" title="Methylcyclopentane">Methylcyclopentane</a></li> <li><a href="/wiki/Methylcyclohexane" title="Methylcyclohexane">Methylcyclohexane</a></li> <li><a href="/w/index.php?title=Isopropylcyclohexane&action=edit&redlink=1" class="new" title="Isopropylcyclohexane (page does not exist)">Isopropylcyclohexane</a></li> <li class="mw-empty-elt"></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/w/index.php?title=Bicycloalkane&action=edit&redlink=1" class="new" title="Bicycloalkane (page does not exist)">Bicycloalkanes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Housane" title="Housane">Housane</a> (bicyclo[2.1.0]pentane)</li> <li><a href="/wiki/Norbornane" title="Norbornane">Norbornane</a> (bicyclo[2.2.1]heptane)</li> <li><a href="/wiki/Decalin" title="Decalin">Decalin</a> (bicyclo[4.4.0]decane)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/w/index.php?title=Polycycloalkane&action=edit&redlink=1" class="new" title="Polycycloalkane (page does not exist)">Polycycloalkanes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Adamantane" title="Adamantane">Adamantane</a></li> <li><a href="/wiki/Diamondoid" title="Diamondoid">Diamondoid</a></li> <li><a href="/w/index.php?title=Perhydrophenanthrene&action=edit&redlink=1" class="new" title="Perhydrophenanthrene (page does not exist)">Perhydrophenanthrene</a></li> <li><a href="/wiki/Sterane" title="Sterane">Sterane</a></li> <li><a href="/wiki/Cubane" title="Cubane">Cubane</a></li> <li><a href="/wiki/Prismane" title="Prismane">Prismane</a></li> <li><a href="/wiki/Dodecahedrane" title="Dodecahedrane">Dodecahedrane</a></li> <li><a href="/wiki/Basketane" title="Basketane">Basketane</a></li> <li><a href="/wiki/Churchane" title="Churchane">Churchane</a></li> <li><a href="/wiki/Pagodane" title="Pagodane">Pagodane</a></li> <li><a href="/wiki/Twistane" title="Twistane">Twistane</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Spiroalkane&action=edit&redlink=1" class="new" title="Spiroalkane (page does not exist)">Spiroalkanes</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:azzurro;"><a href="/wiki/Unsaturated_hydrocarbon" class="mw-redirect" title="Unsaturated hydrocarbon">Unsaturated</a><br />aliphatic<br />hydrocarbons</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Alkene" title="Alkene">Alkenes</a><br />C<sub><i>n</i></sub>H<sub>2<i>n</i></sub></th><td class="navbox-list-with-group navbox-list navbox-odd" style="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:8.5em">Linear alkenes</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ethylene" title="Ethylene">Ethene</a></li> <li><a href="/wiki/Propene" class="mw-redirect" title="Propene">Propene</a></li> <li><a href="/wiki/Butene" title="Butene">Butene</a></li> <li><a href="/wiki/Pentene" title="Pentene">Pentene</a></li> <li><a href="/wiki/Hexene" title="Hexene">Hexene</a></li> <li><a href="/wiki/Heptene" title="Heptene">Heptene</a></li> <li><a href="/wiki/Octene" title="Octene">Octene</a></li> <li><a href="/wiki/Nonene" title="Nonene">Nonene</a></li> <li><a href="/wiki/Decene" title="Decene">Decene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Branched alkenes</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Isobutylene" title="Isobutylene">Isobutene</a></li> <li><a href="/wiki/Isopentene" class="mw-redirect" title="Isopentene">Isopentene</a></li> <li><a href="/w/index.php?title=Isohexene&action=edit&redlink=1" class="new" title="Isohexene (page does not exist)">Isohexene</a></li> <li><a href="/w/index.php?title=Isoheptene&action=edit&redlink=1" class="new" title="Isoheptene (page does not exist)">Isoheptene</a></li> <li><a href="/w/index.php?title=Isooctene&action=edit&redlink=1" class="new" title="Isooctene (page does not exist)">Isooctene</a></li> <li><a href="/w/index.php?title=Isononene&action=edit&redlink=1" class="new" title="Isononene (page does not exist)">Isononene</a></li> <li><a href="/w/index.php?title=Isodecene&action=edit&redlink=1" class="new" title="Isodecene (page does not exist)">Isodecene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Alkyne" title="Alkyne">Alkynes</a><br />C<sub><i>n</i></sub>H<sub>2<i>n</i> − 2</sub></th><td class="navbox-list-with-group navbox-list navbox-odd" style="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:8.5em">Linear alkynes</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetylene" title="Acetylene">Ethyne</a></li> <li><a href="/wiki/Propyne" title="Propyne">Propyne</a></li> <li><a href="/wiki/Butyne" title="Butyne">Butyne</a></li> <li><a href="/wiki/Pentyne" title="Pentyne">Pentyne</a></li> <li><a href="/wiki/3-Hexyne" title="3-Hexyne">Hexyne</a></li> <li><a href="/wiki/Heptyne" title="Heptyne">Heptyne</a></li> <li><a href="/wiki/Octyne" title="Octyne">Octyne</a></li> <li><a href="/wiki/Nonyne" title="Nonyne">Nonyne</a></li> <li><a href="/wiki/1-Decyne" title="1-Decyne">Decyne</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Branched alkynes</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Isopentyne&action=edit&redlink=1" class="new" title="Isopentyne (page does not exist)">Isopentyne</a></li> <li><a href="/w/index.php?title=Isohexyne&action=edit&redlink=1" class="new" title="Isohexyne (page does not exist)">Isohexyne</a></li> <li><a href="/w/index.php?title=Isoheptyne&action=edit&redlink=1" class="new" title="Isoheptyne (page does not exist)">Isoheptyne</a></li> <li><a href="/w/index.php?title=Isooctyne&action=edit&redlink=1" class="new" title="Isooctyne (page does not exist)">Isooctyne</a></li> <li><a href="/w/index.php?title=Isononyne&action=edit&redlink=1" class="new" title="Isononyne (page does not exist)">Isononyne</a></li> <li><a href="/w/index.php?title=Isodecyne&action=edit&redlink=1" class="new" title="Isodecyne (page does not exist)">Isodecyne</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Cycloalkene" title="Cycloalkene">Cycloalkenes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cyclopropene" title="Cyclopropene">Cyclopropene</a></li> <li><a href="/wiki/Cyclobutene" title="Cyclobutene">Cyclobutene</a></li> <li><a href="/wiki/Cyclopentene" title="Cyclopentene">Cyclopentene</a></li> <li><a href="/wiki/Cyclohexene" title="Cyclohexene">Cyclohexene</a></li> <li><a href="/wiki/Cycloheptene" title="Cycloheptene">Cycloheptene</a></li> <li><a href="/wiki/Cyclooctene" title="Cyclooctene">Cyclooctene</a></li> <li><a href="/wiki/Cyclononene" title="Cyclononene">Cyclononene</a></li> <li><a href="/wiki/Cyclodecene" title="Cyclodecene">Cyclodecene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/w/index.php?title=Alkylcycloalkene&action=edit&redlink=1" class="new" title="Alkylcycloalkene (page does not exist)">Alkylcycloalkenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/1-Methylcyclopropene" title="1-Methylcyclopropene">Methylcyclopropene</a></li> <li><a href="/w/index.php?title=Methylcyclobutene&action=edit&redlink=1" class="new" title="Methylcyclobutene (page does not exist)">Methylcyclobutene</a></li> <li><a href="/w/index.php?title=Methylcyclopentene&action=edit&redlink=1" class="new" title="Methylcyclopentene (page does not exist)">Methylcyclopentene</a></li> <li><a href="/wiki/Methylcyclohexene" title="Methylcyclohexene">Methylcyclohexene</a></li> <li><a href="/w/index.php?title=Isopropylcyclohexene&action=edit&redlink=1" class="new" title="Isopropylcyclohexene (page does not exist)">Isopropylcyclohexene</a></li> <li class="mw-empty-elt"></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/w/index.php?title=Bicycloalkene&action=edit&redlink=1" class="new" title="Bicycloalkene (page does not exist)">Bicycloalkenes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Norbornene" title="Norbornene">Norbornene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Cycloalkyne" title="Cycloalkyne">Cycloalkynes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cyclopropyne" class="mw-redirect" title="Cyclopropyne">Cyclopropyne</a></li> <li><a href="/wiki/Cyclobutyne" title="Cyclobutyne">Cyclobutyne</a></li> <li><a href="/wiki/Cyclopentyne" title="Cyclopentyne">Cyclopentyne</a></li> <li><a href="/w/index.php?title=Cyclohexyne&action=edit&redlink=1" class="new" title="Cyclohexyne (page does not exist)">Cyclohexyne</a></li> <li><a href="/w/index.php?title=Cycloheptyne&action=edit&redlink=1" class="new" title="Cycloheptyne (page does not exist)">Cycloheptyne</a></li> <li><a href="/wiki/Cyclooctyne" title="Cyclooctyne">Cyclooctyne</a></li> <li><a href="/w/index.php?title=Cyclononyne&action=edit&redlink=1" class="new" title="Cyclononyne (page does not exist)">Cyclononyne</a></li> <li><a href="/w/index.php?title=Cyclodecyne&action=edit&redlink=1" class="new" title="Cyclodecyne (page does not exist)">Cyclodecyne</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Diene" title="Diene">Dienes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Propadiene" title="Propadiene">Propadiene</a></li> <li><a href="/wiki/Butadiene" title="Butadiene">Butadiene</a></li> <li><a href="/wiki/Piperylene" title="Piperylene">Pentadiene</a></li> <li><a href="/wiki/1,5-Hexadiene" title="1,5-Hexadiene">Hexadiene</a></li> <li><a href="/w/index.php?title=Heptadiene&action=edit&redlink=1" class="new" title="Heptadiene (page does not exist)">Heptadiene</a></li> <li><a href="/wiki/1,7-Octadiene" title="1,7-Octadiene">Octadiene</a></li> <li><a href="/w/index.php?title=Nonadiene&action=edit&redlink=1" class="new" title="Nonadiene (page does not exist)">Nonadiene</a></li> <li><a href="/w/index.php?title=Decadiene&action=edit&redlink=1" class="new" title="Decadiene (page does not exist)">Decadiene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Alkatriene&action=edit&redlink=1" class="new" title="Alkatriene (page does not exist)">Alkatriene</a></li> <li><a href="/w/index.php?title=Alkadiyne&action=edit&redlink=1" class="new" title="Alkadiyne (page does not exist)">Alkadiyne</a></li> <li><a href="/wiki/Cumulene" title="Cumulene">Cumulene</a></li> <li><a href="/wiki/Cyclooctatetraene" title="Cyclooctatetraene">Cyclooctatetraene</a></li> <li><a href="/wiki/Cyclododecatriene" title="Cyclododecatriene">Cyclododecatriene</a></li> <li><a href="/wiki/Enyne" title="Enyne">Enyne</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:azzurro;"><a href="/wiki/Aromatic_hydrocarbon" class="mw-redirect" title="Aromatic hydrocarbon">Aromatic<br />hydrocarbons</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Polycyclic_aromatic_hydrocarbon" title="Polycyclic aromatic hydrocarbon">PAHs</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="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:8.5em"><a href="/wiki/Acene" title="Acene">Acenes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Naphthalene" title="Naphthalene">Naphthalene</a></li> <li><a href="/wiki/Anthracene" title="Anthracene">Anthracene</a></li> <li><a href="/wiki/Tetracene" title="Tetracene">Tetracene</a></li> <li><a href="/wiki/Pentacene" title="Pentacene">Pentacene</a></li> <li><a href="/wiki/Hexacene" title="Hexacene">Hexacene</a></li> <li><a href="/wiki/Heptacene" title="Heptacene">Heptacene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Azulene" title="Azulene">Azulene</a></li> <li><a href="/wiki/Fluorene" title="Fluorene">Fluorene</a></li> <li><a href="/wiki/Helicene" title="Helicene">Helicenes</a></li> <li><a href="/wiki/Circulene" title="Circulene">Circulenes</a></li> <li><a href="/wiki/Butalene" title="Butalene">Butalene</a></li> <li><a href="/wiki/Phenanthrene" title="Phenanthrene">Phenanthrene</a></li> <li><a href="/wiki/Chrysene" title="Chrysene">Chrysene</a></li> <li><a href="/wiki/Pyrene" title="Pyrene">Pyrene</a></li> <li><a href="/wiki/Corannulene" title="Corannulene">Corannulene</a></li> <li><a href="/wiki/Kekulene" title="Kekulene">Kekulene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Alkylbenzenes" class="mw-redirect" title="Alkylbenzenes">Alkylbenzenes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Toluene" title="Toluene">Toluene</a></li></ul> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/C2-Benzenes" title="C2-Benzenes">C2-Benzenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="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:8.5em"><a class="mw-selflink selflink">Xylenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/O-Xylene" title="O-Xylene"><i>o</i>-Xylene</a></li> <li><a href="/wiki/M-Xylene" title="M-Xylene"><i>m</i>-Xylene</a></li> <li><a href="/wiki/P-Xylene" title="P-Xylene"><i>p</i>-Xylene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ethylbenzene" title="Ethylbenzene">Ethylbenzene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/C3-Benzenes" title="C3-Benzenes">C3-Benzenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="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:8.5em"><a href="/wiki/Trimethylbenzenes" class="mw-redirect" title="Trimethylbenzenes">Trimethylbenzenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Mesitylene" title="Mesitylene">Mesitylene</a></li> <li><a href="/wiki/Pseudocumene" class="mw-redirect" title="Pseudocumene">Pseudocumene</a></li> <li><a href="/wiki/Hemellitene" class="mw-redirect" title="Hemellitene">Hemellitene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cumene" title="Cumene">Cumene</a></li> <li><a href="/wiki/N-Propylbenzene" title="N-Propylbenzene"><i>n</i>-Propylbenzene</a></li> <li><a href="/wiki/4-Ethyltoluene" title="4-Ethyltoluene">4-Ethyltoluene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/C4-Benzenes" title="C4-Benzenes">C4-Benzenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="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:8.5em"><a href="/wiki/Cymenes" class="mw-redirect" title="Cymenes">Cymenes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/O-Cymene" title="O-Cymene"><i>o</i>-Cymene</a></li> <li><a href="/wiki/M-Cymene" title="M-Cymene"><i>m</i>-Cymene</a></li> <li><a href="/wiki/P-Cymene" title="P-Cymene"><i>p</i>-Cymene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Tetramethylbenzenes" class="mw-redirect" title="Tetramethylbenzenes">Tetramethylbenzenes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Durene" title="Durene">Durene</a></li> <li><a href="/wiki/Prehnitene" title="Prehnitene">Prehnitene</a></li> <li><a href="/wiki/Isodurene" title="Isodurene">Isodurene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/N-Butylbenzene" title="N-Butylbenzene"><i>n</i>-Butylbenzene</a></li> <li><a href="/wiki/Sec-Butylbenzene" title="Sec-Butylbenzene"><i>sec</i>-Butylbenzene</a></li> <li><a href="/wiki/Tert-Butylbenzene" title="Tert-Butylbenzene"><i>tert</i>-Butylbenzene</a></li> <li><a href="/wiki/Isobutylbenzene" title="Isobutylbenzene">Isobutylbenzene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Hexamethylbenzene" title="Hexamethylbenzene">Hexamethylbenzene</a></li> <li><a href="/wiki/2-Phenylhexane" title="2-Phenylhexane">2-Phenylhexane</a></li> <li><a href="/wiki/1,3,5-Triethylbenzene" title="1,3,5-Triethylbenzene">1,3,5-Triethylbenzene</a></li> <li><a href="/wiki/1,3,5-Triheptylbenzene" title="1,3,5-Triheptylbenzene">1,3,5-Triheptylbenzene</a></li></ul> </div></td></tr></tbody></table><div> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Vinylbenzenes</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Styrene" title="Styrene">Styrene</a></li> <li><a href="/wiki/Divinylbenzene" title="Divinylbenzene">Divinylbenzene</a></li> <li><a href="/wiki/4-Vinyltoluene" title="4-Vinyltoluene">4-Vinyltoluene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:8.5em">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Benzene" title="Benzene">Benzene</a></li> <li><a href="/wiki/Cyclopropenylidene" title="Cyclopropenylidene">Cyclopropenylidene</a></li> <li><a href="/wiki/Phenylacetylene" title="Phenylacetylene">Phenylacetylene</a></li> <li><a href="/wiki/Trans-Propenylbenzene" title="Trans-Propenylbenzene"><i>trans</i>-Propenylbenzene</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:azzurro;">Other</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Annulene" title="Annulene">Annulenes</a></li> <li><a href="/wiki/Annulyne" title="Annulyne">Annulynes</a></li> <li><a href="/wiki/Alicyclic_compound" title="Alicyclic compound">Alicyclic compounds</a></li> <li><a href="/wiki/Petroleum_jelly" title="Petroleum jelly">Petroleum jelly</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /><style data-mw-deduplicate="TemplateStyles:r1038841319">.mw-parser-output .tooltip-dotted{border-bottom:1px dotted;cursor:help}</style></div><div role="navigation" class="navbox authority-control" aria-label="Navbox946" style="padding:3px"><table class="nowraplinks hlist navbox-inner" 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