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class="vector-toc-link" href="#Alkylation_by_carbon_electrophiles"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Alkylation by carbon electrophiles</span> </div> </a> <button aria-controls="toc-Alkylation_by_carbon_electrophiles-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 Alkylation by carbon electrophiles subsection</span> </button> <ul id="toc-Alkylation_by_carbon_electrophiles-sublist" class="vector-toc-list"> <li id="toc-C-alkylation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#C-alkylation"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>C-alkylation</span> </div> </a> <ul id="toc-C-alkylation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-N-,P-,_S-_alkylation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#N-,P-,_S-_alkylation"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.2</span> <span>N-,P-, S- alkylation</span> </div> </a> <ul id="toc-N-,P-,_S-_alkylation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-O-alkylation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#O-alkylation"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.3</span> <span>O-alkylation</span> </div> </a> <ul id="toc-O-alkylation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Oxidative_addition_to_metals" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Oxidative_addition_to_metals"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.4</span> <span>Oxidative addition to metals</span> </div> </a> <ul id="toc-Oxidative_addition_to_metals-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Electrophilic_alkylating_agents" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Electrophilic_alkylating_agents"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.5</span> <span>Electrophilic alkylating agents</span> </div> </a> <ul id="toc-Electrophilic_alkylating_agents-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Methylation_with_diazomethane" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Methylation_with_diazomethane"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.6</span> <span>Methylation with diazomethane</span> </div> </a> <ul id="toc-Methylation_with_diazomethane-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Hazards" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Hazards"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.7</span> <span>Hazards</span> </div> </a> <ul id="toc-Hazards-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Catalysts" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Catalysts"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.8</span> <span>Catalysts</span> </div> </a> <ul id="toc-Catalysts-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-In_biology" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#In_biology"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>In biology</span> </div> </a> <ul id="toc-In_biology-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Commodity_chemicals" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Commodity_chemicals"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Commodity chemicals</span> </div> </a> <ul id="toc-Commodity_chemicals-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Gasoline_production" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Gasoline_production"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Gasoline production</span> </div> </a> <ul id="toc-Gasoline_production-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Dealkylation" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Dealkylation"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Dealkylation</span> </div> </a> <ul id="toc-Dealkylation-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">7</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">8</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">9</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" 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Available in 39 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-39" 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">39 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%A3%D9%84%D9%83%D9%84%D8%A9" title="ألكلة – Arabic" lang="ar" hreflang="ar" data-title="ألكلة" 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/Alkill%C9%99%C5%9Fm%C9%99_prosesl%C9%99ri" title="Alkilləşmə prosesləri – Azerbaijani" lang="az" hreflang="az" data-title="Alkilləşmə prosesləri" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%90%D0%BB%D0%BA%D1%96%D0%BB%D1%96%D1%80%D0%B0%D0%B2%D0%B0%D0%BD%D0%BD%D0%B5" title="Алкіліраванне – Belarusian" lang="be" hreflang="be" data-title="Алкіліраванне" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%90%D0%BB%D0%BA%D0%B8%D0%BB%D0%B8%D1%80%D0%B0%D0%BD%D0%B5" title="Алкилиране – Bulgarian" lang="bg" hreflang="bg" data-title="Алкилиране" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Alkilacija" title="Alkilacija – Bosnian" lang="bs" hreflang="bs" data-title="Alkilacija" 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/Alquilaci%C3%B3" title="Alquilació – Catalan" lang="ca" hreflang="ca" data-title="Alquilació" 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/Alkylace" title="Alkylace – Czech" lang="cs" hreflang="cs" data-title="Alkylace" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Alkylierung" title="Alkylierung – German" lang="de" hreflang="de" data-title="Alkylierung" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Alk%C3%BC%C3%BClimine" title="Alküülimine – Estonian" lang="et" hreflang="et" data-title="Alküülimine" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%91%CE%BB%CE%BA%CF%85%CE%BB%CE%AF%CF%89%CF%83%CE%B7" title="Αλκυλίωση – Greek" lang="el" hreflang="el" data-title="Αλκυλίωση" 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/Alquilaci%C3%B3n" title="Alquilación – Spanish" lang="es" hreflang="es" data-title="Alquilación" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A2%D9%84%DA%A9%DB%8C%D9%84%E2%80%8C%D8%AF%D8%A7%D8%B1_%DA%A9%D8%B1%D8%AF%D9%86" title="آلکیل‌دار کردن – Persian" lang="fa" hreflang="fa" data-title="آلکیل‌دار کردن" 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/Alkylation" title="Alkylation – French" lang="fr" hreflang="fr" data-title="Alkylation" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Alquilaci%C3%B3n" title="Alquilación – Galician" lang="gl" hreflang="gl" data-title="Alquilación" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%95%8C%ED%82%AC%ED%99%94" title="알킬화 – Korean" lang="ko" hreflang="ko" data-title="알킬화" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D4%B1%D5%AC%D5%AF%D5%AB%D5%AC%D5%A1%D6%81%D5%B8%D6%82%D5%B4" title="Ալկիլացում – Armenian" lang="hy" hreflang="hy" data-title="Ալկիլացում" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Alkilasi" title="Alkilasi – Indonesian" lang="id" hreflang="id" data-title="Alkilasi" 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/Alchilazione" title="Alchilazione – Italian" lang="it" hreflang="it" data-title="Alchilazione" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%90%D7%9C%D7%A7%D7%99%D7%9C%D7%A6%D7%99%D7%94" title="אלקילציה – Hebrew" lang="he" hreflang="he" data-title="אלקילציה" 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%90%E1%83%9A%E1%83%99%E1%83%98%E1%83%9A%E1%83%98%E1%83%A0%E1%83%94%E1%83%91%E1%83%90" title="ალკილირება – Georgian" lang="ka" hreflang="ka" data-title="ალკილირება" 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/Alkil%C4%93%C5%A1ana" title="Alkilēšana – Latvian" lang="lv" hreflang="lv" data-title="Alkilēšana" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Pengalkilan" title="Pengalkilan – Malay" lang="ms" hreflang="ms" data-title="Pengalkilan" 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/Alkylering" title="Alkylering – Dutch" lang="nl" hreflang="nl" data-title="Alkylering" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%A2%E3%83%AB%E3%82%AD%E3%83%AB%E5%8C%96" title="アルキル化 – Japanese" lang="ja" hreflang="ja" data-title="アルキル化" 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-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Alkillash" title="Alkillash – Uzbek" lang="uz" hreflang="uz" data-title="Alkillash" 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/Alkilowanie" title="Alkilowanie – Polish" lang="pl" hreflang="pl" data-title="Alkilowanie" 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/Alquila%C3%A7%C3%A3o" title="Alquilação – Portuguese" lang="pt" hreflang="pt" data-title="Alquilação" 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/Alchilare" title="Alchilare – Romanian" lang="ro" hreflang="ro" data-title="Alchilare" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%90%D0%BB%D0%BA%D0%B8%D0%BB%D0%B8%D1%80%D0%BE%D0%B2%D0%B0%D0%BD%D0%B8%D0%B5" title="Алкилирование – Russian" lang="ru" hreflang="ru" data-title="Алкилирование" 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/Alkilacija" title="Alkilacija – Slovenian" lang="sl" hreflang="sl" data-title="Alkilacija" 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/Alkilacija" title="Alkilacija – Serbian" lang="sr" hreflang="sr" data-title="Alkilacija" 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/Alkilacija" title="Alkilacija – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Alkilacija" 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/Alkylointi" title="Alkylointi – Finnish" lang="fi" hreflang="fi" data-title="Alkylointi" 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/Alkylering" title="Alkylering – Swedish" lang="sv" hreflang="sv" data-title="Alkylering" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%85%E0%AE%B2%E0%AF%8D%E0%AE%95%E0%AF%88%E0%AE%B2%E0%AF%87%E0%AE%B1%E0%AF%8D%E0%AE%B1%E0%AE%AE%E0%AF%8D" title="அல்கைலேற்றம் – Tamil" lang="ta" hreflang="ta" data-title="அல்கைலேற்றம்" 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/Alkilasyon" title="Alkilasyon – Turkish" lang="tr" hreflang="tr" data-title="Alkilasyon" 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 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class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Transfer of an alkyl group from one molecule to another</div><figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:EthylbenzenePost2000route.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/09/EthylbenzenePost2000route.svg/330px-EthylbenzenePost2000route.svg.png" decoding="async" width="330" height="123" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/09/EthylbenzenePost2000route.svg/500px-EthylbenzenePost2000route.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/09/EthylbenzenePost2000route.svg/960px-EthylbenzenePost2000route.svg.png 2x" data-file-width="1543" data-file-height="574" /></a><figcaption>Typical route for alkylation of benzene with ethylene and <a href="/wiki/ZSM-5" title="ZSM-5">ZSM-5</a> as a heterogeneous catalyst</figcaption></figure><p><b>Alkylation</b> is a <a href="/wiki/Chemical_reaction" title="Chemical reaction">chemical reaction</a> that entails transfer of an <a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">alkyl</a> group. The alkyl group may be transferred as an alkyl <a href="/wiki/Carbocation" title="Carbocation">carbocation</a>, a <a href="/wiki/Free_radical" class="mw-redirect" title="Free radical">free radical</a>, a <a href="/wiki/Carbanion" title="Carbanion">carbanion</a>, or a <a href="/wiki/Carbene" title="Carbene">carbene</a> (or their equivalents). <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> <b>Alkylating agents</b> are <a href="/wiki/Reagent" title="Reagent">reagents</a> for effecting alkylation. Alkyl groups can also be removed in a process known as <b>dealkylation</b>. Alkylating agents are often classified according to their <a href="/wiki/Nucleophilic" class="mw-redirect" title="Nucleophilic">nucleophilic</a> or <a href="/wiki/Electrophilic" class="mw-redirect" title="Electrophilic">electrophilic</a> character. In oil refining contexts, <b>alkylation</b> refers to a particular alkylation of <a href="/wiki/Isobutane" title="Isobutane">isobutane</a> with <a href="/wiki/Alkene" title="Alkene">olefins</a>. For upgrading of <a href="/wiki/Petroleum" title="Petroleum">petroleum</a>, alkylation produces a premium blending stock for gasoline.<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> In medicine, alkylation of <a href="/wiki/DNA" title="DNA">DNA</a> is used in <a href="/wiki/Chemotherapy" title="Chemotherapy">chemotherapy</a> to damage the DNA of cancer cells. Alkylation is accomplished with the class of drugs called <a href="/wiki/Alkylating_antineoplastic_agent" title="Alkylating antineoplastic agent">alkylating antineoplastic agents</a>. </p><meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Nucleophilic_alkylating_agents">Nucleophilic alkylating agents</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkylation&action=edit&section=1" title="Edit section: Nucleophilic alkylating agents"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><b>Nucleophilic alkylating agents</b> deliver the equivalent of an <a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">alkyl</a> <a href="/wiki/Anion" class="mw-redirect" title="Anion">anion</a> (<a href="/wiki/Carbanion" title="Carbanion">carbanion</a>). The formal "alkyl anion" attacks an <a href="/wiki/Electrophile" title="Electrophile">electrophile</a>, forming a new <a href="/wiki/Covalent_bond" title="Covalent bond">covalent bond</a> between the alkyl group and the electrophile. The counterion, which is a cation such as lithium, can be removed and washed away in the <a href="/wiki/Work-up_(chemistry)" class="mw-redirect" title="Work-up (chemistry)">work-up</a>. Examples include the use of <a href="/wiki/Organometallic_compound" class="mw-redirect" title="Organometallic compound">organometallic compounds</a> such as <a href="/wiki/Grignard_reagent" title="Grignard reagent">Grignard (organomagnesium)</a>, <a href="/wiki/Organolithium" class="mw-redirect" title="Organolithium">organolithium</a>, <a href="/wiki/Organocopper" class="mw-redirect" title="Organocopper">organocopper</a>, and <a href="/wiki/Organosodium" class="mw-redirect" title="Organosodium">organosodium</a> reagents. These compounds typically can add to an electron-deficient carbon atom such as at a <a href="/wiki/Carbonyl_group" title="Carbonyl group">carbonyl group</a>. Nucleophilic alkylating agents can displace <a href="/wiki/Halide" title="Halide">halide</a> substituents on a carbon atom through the <a href="/wiki/SN2" class="mw-redirect" title="SN2">SN2</a> mechanism. With a <a href="/wiki/Catalysis" title="Catalysis">catalyst</a>, they also alkylate alkyl and <a href="/wiki/Aryl_group" title="Aryl group">aryl</a> halides, as exemplified by <a href="/wiki/Suzuki_coupling" class="mw-redirect" title="Suzuki coupling">Suzuki couplings</a>. </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Katalysezyklus-Kumada-Kupplung.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/55/Katalysezyklus-Kumada-Kupplung.png/500px-Katalysezyklus-Kumada-Kupplung.png" decoding="async" width="440" height="241" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/55/Katalysezyklus-Kumada-Kupplung.png/960px-Katalysezyklus-Kumada-Kupplung.png 1.5x" data-file-width="1275" data-file-height="699" /></a><figcaption>The <a href="/wiki/Kumada_coupling" title="Kumada coupling">Kumada coupling</a> employs both a nucleophilic alkylation step subsequent to the oxidative addition of the aryl halide (L = <a href="/wiki/Ligand" title="Ligand">Ligand</a>, Ar = <a href="/wiki/Aryl" class="mw-redirect" title="Aryl">Aryl</a>).</figcaption></figure><p> The SN2 mechanism is not available for aryl substituents, where the trajectory to attack the carbon atom would be inside the ring. Thus, only reactions catalyzed by organometallic catalysts are possible.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (January 2025)">citation needed</span></a></i>]</sup> </p><div class="mw-heading mw-heading2"><h2 id="Alkylation_by_carbon_electrophiles">Alkylation by carbon electrophiles</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkylation&action=edit&section=2" title="Edit section: Alkylation by carbon electrophiles"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="C-alkylation">C-alkylation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkylation&action=edit&section=3" title="Edit section: C-alkylation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>C-alkylation is a process for the formation of carbon-carbon bonds. The largest example of this takes place in the <a href="/wiki/Alkylation_unit" title="Alkylation unit">alkylation units</a> of petrochemical plants, which convert low-molecular-weight <a href="/wiki/Alkenes" class="mw-redirect" title="Alkenes">alkenes</a> into high octane <a href="/wiki/Gasoline" title="Gasoline">gasoline</a> components. Electron-rich species such as <a href="/wiki/Phenol" title="Phenol">phenols</a> are also commonly alkylated to produce a variety of products; examples include <a href="/wiki/Linear_alkylbenzene" title="Linear alkylbenzene">linear alkylbenzenes</a> used in the production of <a href="/wiki/Surfactants" class="mw-redirect" title="Surfactants">surfactants</a> like <a href="/wiki/Alkylbenzene_sulfonates" class="mw-redirect" title="Alkylbenzene sulfonates">LAS</a>, or butylated phenols like <a href="/wiki/Butylated_hydroxytoluene" title="Butylated hydroxytoluene">BHT</a>, which are used as <a href="/wiki/Antioxidant" title="Antioxidant">antioxidants</a>. This can be achieved using either acid catalysts like <a href="/wiki/Amberlyst" class="mw-redirect" title="Amberlyst">Amberlyst</a>, or <a href="/wiki/Lewis_acid" class="mw-redirect" title="Lewis acid">Lewis acids</a> like aluminium.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> On a laboratory scale the <a href="/wiki/Friedel%E2%80%93Crafts_reaction" title="Friedel–Crafts reaction">Friedel–Crafts reaction</a> uses <a href="/wiki/Alkyl_halide" class="mw-redirect" title="Alkyl halide">alkyl halides</a>, as these are often easier to handle than their corresponding alkenes, which tend to be gasses. The reaction is catalysed by <a href="/wiki/Aluminium_trichloride" class="mw-redirect" title="Aluminium trichloride">aluminium trichloride</a>. This approach is rarely used industrially as alkyl halides are more expensive than alkenes.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (January 2025)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading3"><h3 id="N-,P-,_S-_alkylation"><span id="N-.2CP-.2C_S-_alkylation"></span>N-,P-, S- alkylation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkylation&action=edit&section=4" title="Edit section: N-,P-, S- alkylation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>N-, P-, and S-alkylation are important processes for the formation of carbon-nitrogen, carbon-phosphorus, and carbon-sulfur bonds,<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (January 2025)">citation needed</span></a></i>]</sup> </p><p>Amines are readily alkylated. The rate of alkylation follows the order tertiary amine < secondary amine < primary amine. Typical alkylating agents are alkyl halides. Industry often relies on <a href="/wiki/Green_chemistry" title="Green chemistry">green chemistry</a> methods involving alkylation of amines with alcohols, the byproduct being water. <a href="/wiki/Hydroamination" title="Hydroamination">Hydroamination</a> is another green method for N-alkylation.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (January 2025)">citation needed</span></a></i>]</sup> </p><p>In the <a href="/wiki/Menshutkin_reaction" title="Menshutkin reaction">Menshutkin reaction</a>, a <a href="/wiki/Tertiary_amine" class="mw-redirect" title="Tertiary amine">tertiary amine</a> is converted into a <a href="/wiki/Quaternary_ammonium_salt" class="mw-redirect" title="Quaternary ammonium salt">quaternary ammonium salt</a> by reaction with an <a href="/wiki/Alkyl_halide" class="mw-redirect" title="Alkyl halide">alkyl halide</a>. Similar reactions occur when tertiary phosphines are treated with alkyl halides, the products being phosphonium salts. </p> <figure class="mw-default-size mw-halign-center" typeof="mw:File"><a href="/wiki/File:Menschutkin.svg" class="mw-file-description" title="Menshutkin-reaction"><img alt="Menshutkin-reaction" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/93/Menschutkin.svg/669px-Menschutkin.svg.png" decoding="async" width="669" height="134" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/93/Menschutkin.svg/1004px-Menschutkin.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/93/Menschutkin.svg/1338px-Menschutkin.svg.png 2x" data-file-width="669" data-file-height="134" /></a><figcaption>Menshutkin-reaction</figcaption></figure> <p><a href="/wiki/Thiol" title="Thiol">Thiols</a> are readily alkylated to give <a href="/wiki/Thioether" class="mw-redirect" title="Thioether">thioethers</a> via the <a href="/wiki/Thiol-ene_reaction" title="Thiol-ene reaction">thiol-ene reaction</a>.<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> The reaction is typically conducted in the presence of a base or using the conjugate base of the thiol. Thioethers undergo alkylation to give <a href="/wiki/Sulfonium_ion" class="mw-redirect" title="Sulfonium ion">sulfonium ions</a>. </p> <div class="mw-heading mw-heading3"><h3 id="O-alkylation">O-alkylation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkylation&action=edit&section=5" title="Edit section: O-alkylation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">Alcohols</a> alkylate to give <a href="/wiki/Ether" title="Ether">ethers</a>: </p> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {R-OH + R'-X -> R-O-R'}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mtext>R</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>OH</mtext> <mo>+</mo> <msup> <mtext>R</mtext> <mo>′</mo> </msup> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>X</mtext> <mo stretchy="false">⟶</mo> <mtext>R</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>O</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <msup> <mtext>R</mtext> <mo>′</mo> </msup> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {R-OH + R'-X -> R-O-R'}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/0ee8e9fa40ecf3b61455689b90a2ca6a7d3dfb4b" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -0.505ex; width:30.483ex; height:2.676ex;" alt="{\displaystyle {\ce {R-OH + R'-X -> R-O-R'}}}" /></span></dd></dl> <p>When the alkylating agent is an alkyl halide, the conversion is called the <a href="/wiki/Williamson_ether_synthesis" title="Williamson ether synthesis">Williamson ether synthesis</a>. Alcohols are also good alkylating agents in the presence of suitable acid catalysts. For example, most methyl amines are prepared by alkylation of ammonia with methanol. The alkylation of phenols is particularly straightforward since it is subject to fewer competing reactions.<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> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {Ph-O- + Me2-SO4 -> Ph-O-Me + Me-SO4-}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mtext>Ph</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <msup> <mtext>O</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> </msup> <mo>+</mo> <msubsup> <mtext>Me</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <msubsup> <mtext>SO</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>4</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mo stretchy="false">⟶</mo> <mtext>Ph</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>O</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>Me</mtext> <mo>+</mo> <mtext>Me</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <msubsup> <mtext>SO</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>4</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> </msubsup> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {Ph-O- + Me2-SO4 -> Ph-O-Me + Me-SO4-}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/df08f418ca83f8dfa4dbc3b39bb17177b130f994" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:50.006ex; height:3.176ex;" alt="{\displaystyle {\ce {Ph-O- + Me2-SO4 -> Ph-O-Me + Me-SO4-}}}" /></span></dd> <dd>(with <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">Na<sup class="template-chem2-sup">+</sup></span> as a <a href="/wiki/Spectator_ion" title="Spectator ion">spectator ion</a>)</dd></dl> <p>More complex alkylation of a alcohols and phenols involve <a href="/wiki/Ethoxylation" title="Ethoxylation">ethoxylation</a>. <a href="/wiki/Ethylene_oxide" title="Ethylene oxide">Ethylene oxide</a> is the alkylating group in this reaction. </p> <div class="mw-heading mw-heading3"><h3 id="Oxidative_addition_to_metals">Oxidative addition to metals</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkylation&action=edit&section=6" title="Edit section: Oxidative addition to metals"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In the process called <a href="/wiki/Oxidative_addition" title="Oxidative addition">oxidative addition</a>, low-valent metals often react with alkylating agents to give metal alkyls. This reaction is one step in the <a href="/wiki/Cativa_process" title="Cativa process">Cativa process</a> for the synthesis of <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a> from <a href="/wiki/Methyl_iodide" class="mw-redirect" title="Methyl iodide">methyl iodide</a>. Many <a href="/wiki/Cross_coupling_reaction" class="mw-redirect" title="Cross coupling reaction">cross coupling reactions</a> proceed via oxidative addition as well.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (January 2025)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading3"><h3 id="Electrophilic_alkylating_agents">Electrophilic alkylating agents</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkylation&action=edit&section=7" title="Edit section: Electrophilic alkylating agents"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Triethyloxonium_tetrafluoroborate.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4e/Triethyloxonium_tetrafluoroborate.png/250px-Triethyloxonium_tetrafluoroborate.png" decoding="async" width="220" height="82" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4e/Triethyloxonium_tetrafluoroborate.png/330px-Triethyloxonium_tetrafluoroborate.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4e/Triethyloxonium_tetrafluoroborate.png/500px-Triethyloxonium_tetrafluoroborate.png 2x" data-file-width="1276" data-file-height="474" /></a><figcaption><a href="/wiki/Triethyloxonium_tetrafluoroborate" title="Triethyloxonium tetrafluoroborate">Triethyloxonium tetrafluoroborate</a> is one of the most electrophilic alkylating agents.<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></figcaption></figure> <p>Electrophilic alkylating agents deliver the equivalent of an alkyl <a href="/wiki/Cation" class="mw-redirect" title="Cation">cation</a>. Alkyl halides are typical alkylating agents. <a href="/wiki/Trimethyloxonium_tetrafluoroborate" title="Trimethyloxonium tetrafluoroborate">Trimethyloxonium tetrafluoroborate</a> and <a href="/wiki/Triethyloxonium_tetrafluoroborate" title="Triethyloxonium tetrafluoroborate">triethyloxonium tetrafluoroborate</a> are particularly strong electrophiles due to their overt positive charge and an inert leaving group (dimethyl or diethyl ether). <a href="/wiki/Dimethyl_sulfate" title="Dimethyl sulfate">Dimethyl sulfate</a> is intermediate in electrophilicity.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (January 2025)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading3"><h3 id="Methylation_with_diazomethane">Methylation with diazomethane</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkylation&action=edit&section=8" title="Edit section: Methylation with diazomethane"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Diazomethane" title="Diazomethane">Diazomethane</a> is a popular <a href="/wiki/Methylating_agent" class="mw-redirect" title="Methylating agent">methylating agent</a> in the laboratory, but it is too hazardous (explosive gas with a high acute toxicity) to be employed on an industrial scale without special precautions.<sup id="cite_ref-proctor_7-0" class="reference"><a href="#cite_note-proctor-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> Use of diazomethane has been significantly reduced by the introduction of the safer and equivalent reagent <a href="/wiki/Trimethylsilyldiazomethane" title="Trimethylsilyldiazomethane">trimethylsilyldiazomethane</a>.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Hazards">Hazards</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkylation&action=edit&section=9" title="Edit section: Hazards"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Electrophilic, soluble alkylating agents are often toxic and carcinogenic, due to their tendency to alkylate DNA. This mechanism of toxicity is relevant to the function of anti-cancer drugs in the form of <a href="/wiki/Alkylating_antineoplastic_agents" class="mw-redirect" title="Alkylating antineoplastic agents">alkylating antineoplastic agents</a>. Some <a href="/wiki/Chemical_weapons" class="mw-redirect" title="Chemical weapons">chemical weapons</a> such as <a href="/wiki/Mustard_gas" title="Mustard gas">mustard gas</a> (sulfide of dichloroethyl) function as alkylating agents. Alkylated DNA either does not coil or uncoil properly, or cannot be processed by information-decoding enzymes.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (January 2025)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading3"><h3 id="Catalysts">Catalysts</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkylation&action=edit&section=10" title="Edit section: Catalysts"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Benzene_Friedel-Crafts_alkylation-diagram.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f4/Benzene_Friedel-Crafts_alkylation-diagram.svg/400px-Benzene_Friedel-Crafts_alkylation-diagram.svg.png" decoding="async" width="400" height="94" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f4/Benzene_Friedel-Crafts_alkylation-diagram.svg/600px-Benzene_Friedel-Crafts_alkylation-diagram.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f4/Benzene_Friedel-Crafts_alkylation-diagram.svg/800px-Benzene_Friedel-Crafts_alkylation-diagram.svg.png 2x" data-file-width="778" data-file-height="182" /></a><figcaption><a href="/wiki/Friedel-Crafts_reaction" class="mw-redirect" title="Friedel-Crafts reaction">Friedel-Crafts alkylation</a> of benzene is often catalyzed by aluminium trichloride.</figcaption></figure> <p>Electrophilic alkylation uses <a href="/wiki/Lewis_acid" class="mw-redirect" title="Lewis acid">Lewis acids</a> and <a href="/wiki/Br%C3%B8nsted_acid" class="mw-redirect" title="Brønsted acid">Brønsted acids</a>, sometimes both. Classically, Lewis acids, e.g., <a href="/wiki/Aluminium_trichloride" class="mw-redirect" title="Aluminium trichloride">aluminium trichloride</a>, are employed when the alkyl halide are used. Brønsted acids are used when alkylating with olefins. Typical catalysts are zeolites, i.e. solid acid catalysts, and sulfuric acid. <a href="/wiki/Silicotungstic_acid" title="Silicotungstic acid">Silicotungstic acid</a> is used to manufacture <a href="/wiki/Ethyl_acetate" title="Ethyl acetate">ethyl acetate</a> by the alkylation of <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a> by <a href="/wiki/Ethylene" title="Ethylene">ethylene</a>:<sup id="cite_ref-Misono_9-0" class="reference"><a href="#cite_note-Misono-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {C2H4 + CH3CO2H -> CH3CO2C2H5}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>4</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mo>+</mo> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CO</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <mtext>H</mtext> <mo stretchy="false">⟶</mo> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>CO</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>5</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em"></mspace> </mrow> </msubsup> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {C2H4 + CH3CO2H -> CH3CO2C2H5}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/fe64691954948912061e8821762180ecf56c60f3" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:38.77ex; height:2.843ex;" alt="{\displaystyle {\ce {C2H4 + CH3CO2H -> CH3CO2C2H5}}}" /></span></dd></dl> <div class="mw-heading mw-heading2"><h2 id="In_biology">In biology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkylation&action=edit&section=11" title="Edit section: In biology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Methylation" title="Methylation">methylation</a></div> <p>Alkylation in biology causes <a href="/wiki/DNA_damage" class="mw-redirect" title="DNA damage">DNA damage</a>. It is the transfer of alkyl groups to the <a href="/wiki/Nitrogenous_bases" class="mw-redirect" title="Nitrogenous bases">nitrogenous bases</a>. It is caused by alkylating agents such as EMS (Ethyl Methyl Sulphonate). Bifunctional alkyl groups which have two alkyl groups in them cause cross linking in DNA. Alkylation damaged ring nitrogen bases are repaired via the <a href="/wiki/Base_excision_repair" title="Base excision repair">Base Excision Repair</a> (BER) pathway.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:SN2_Mechanism_of_Methyltransferases.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/ab/SN2_Mechanism_of_Methyltransferases.png/500px-SN2_Mechanism_of_Methyltransferases.png" decoding="async" width="400" height="246" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/ab/SN2_Mechanism_of_Methyltransferases.png/960px-SN2_Mechanism_of_Methyltransferases.png 1.5x" data-file-width="5187" data-file-height="3185" /></a><figcaption>The S<sub>N</sub>2-like methyl transfer reaction in <a href="/wiki/DNA_methylation" title="DNA methylation">DNA methylation</a>. Only the <a href="/wiki/SAM_cofactor" class="mw-redirect" title="SAM cofactor">SAM cofactor</a> and cytosine base are shown for simplicity.</figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="Commodity_chemicals">Commodity chemicals</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkylation&action=edit&section=12" title="Edit section: Commodity chemicals"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Several commodity chemicals are produced by alkylation. Included are several fundamental benzene-based feedstocks such as <a href="/wiki/Ethylbenzene" title="Ethylbenzene">ethylbenzene</a> (precursor to <a href="/wiki/Styrene" title="Styrene">styrene</a>), <a href="/wiki/Cumene" title="Cumene">cumene</a> (precursor to <a href="/wiki/Phenol" title="Phenol">phenol</a> and <a href="/wiki/Acetone" title="Acetone">acetone</a>), <a href="/wiki/Linear_alkylbenzene_sulfonate" class="mw-redirect" title="Linear alkylbenzene sulfonate">linear alkylbenzene sulfonates</a> (for detergents).<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-default-size mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Sodium_dodecylbenzenesulfonate_skeletal.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/de/Sodium_dodecylbenzenesulfonate_skeletal.svg/220px-Sodium_dodecylbenzenesulfonate_skeletal.svg.png" decoding="async" width="220" height="139" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/de/Sodium_dodecylbenzenesulfonate_skeletal.svg/330px-Sodium_dodecylbenzenesulfonate_skeletal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/de/Sodium_dodecylbenzenesulfonate_skeletal.svg/440px-Sodium_dodecylbenzenesulfonate_skeletal.svg.png 2x" data-file-width="1435" data-file-height="905" /></a><figcaption>Sodium dodecylbenzene, obtained by alkylation of benzene with dodecene, is a precursor to <a href="/wiki/Linear_alkylbenzene_sulfonate" class="mw-redirect" title="Linear alkylbenzene sulfonate">linear alkylbenzene sulfonate</a> detergents.</figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="Gasoline_production">Gasoline production</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkylation&action=edit&section=13" title="Edit section: Gasoline production"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951" /><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Alkylation_unit" title="Alkylation unit">alkylation unit</a></div> <figure class="mw-default-size mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:2,4-Me2pentaneRoute.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fb/2%2C4-Me2pentaneRoute.png/330px-2%2C4-Me2pentaneRoute.png" decoding="async" width="290" height="52" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fb/2%2C4-Me2pentaneRoute.png/500px-2%2C4-Me2pentaneRoute.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fb/2%2C4-Me2pentaneRoute.png/960px-2%2C4-Me2pentaneRoute.png 2x" data-file-width="1249" data-file-height="224" /></a><figcaption>Typical acid-catalyzed route to <a href="/wiki/2,4-Dimethylpentane" title="2,4-Dimethylpentane">2,4-dimethylpentane</a>.</figcaption></figure> <p>In a conventional <a href="/wiki/Oil_refinery" title="Oil refinery">oil refinery</a>, <a href="/wiki/Isobutane" title="Isobutane">isobutane</a> is alkylated with low-molecular-weight <a href="/wiki/Alkene" title="Alkene">alkenes</a> (primarily a mixture of <a href="/wiki/Propene" class="mw-redirect" title="Propene">propene</a> and <a href="/wiki/Butene" title="Butene">butene</a>) in the presence of a Brønsted acid catalyst, which can include <a href="/wiki/Solid_acid" title="Solid acid">solid acids</a> (zeolites). The catalyst protonates the alkenes (propene, butene) to produce <a href="/wiki/Carbocation" title="Carbocation">carbocations</a>, which alkylate isobutane. The product, called "alkylate", is composed of a mixture of high-<a href="/wiki/Octane" title="Octane">octane</a>, branched-chain <a href="/wiki/Alkane" title="Alkane">paraffinic</a> <a href="/wiki/Hydrocarbon" title="Hydrocarbon">hydrocarbons</a> (mostly <a href="/wiki/Isoheptane" class="mw-redirect" title="Isoheptane">isoheptane</a> and <a href="/wiki/Isooctane" class="mw-redirect" title="Isooctane">isooctane</a>). Alkylate is a premium <a href="/wiki/Gasoline" title="Gasoline">gasoline</a> blending stock because it has exceptional antiknock properties and is clean burning. Alkylate is also a key component of <a href="/wiki/Avgas" title="Avgas">avgas</a>. By combining <a href="/wiki/Fluid_catalytic_cracking" title="Fluid catalytic cracking">fluid catalytic cracking</a>, polymerization, and alkylation, refineries can obtain a gasoline yield of 70 percent. The widespread use of <a href="/wiki/Sulfuric_acid" title="Sulfuric acid">sulfuric acid</a> and <a href="/wiki/Hydrofluoric_acid" title="Hydrofluoric acid">hydrofluoric acid</a> in refineries poses significant environmental risks.<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> <a href="/wiki/Ionic_liquid" title="Ionic liquid">Ionic liquids</a> are used in place of the older generation of strong Bronsted acids.<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><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> </p> <div class="mw-heading mw-heading2"><h2 id="Dealkylation">Dealkylation</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkylation&action=edit&section=14" title="Edit section: Dealkylation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Complementing alkylation reactions are the reverse, dealkylations. Prevalent are <a href="/wiki/Demethylation" title="Demethylation">demethylations</a>, which are prevalent in biology, organic synthesis, and other areas, especially for <a href="/wiki/Methyl_ether" title="Methyl ether">methyl ethers</a> and <a href="/wiki/Methyl_amine" class="mw-redirect" title="Methyl amine">methyl amines</a>.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (January 2025)">citation needed</span></a></i>]</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=Alkylation&action=edit&section=15" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Hydrodealkylation" title="Hydrodealkylation">Hydrodealkylation</a></li> <li><a href="/wiki/Transalkylation" title="Transalkylation">Transalkylation</a></li> <li><a href="/wiki/Alkynylation" title="Alkynylation">Alkynylation</a></li> <li><a href="/wiki/Friedel%E2%80%93Crafts_reaction" title="Friedel–Crafts reaction">Friedel–Crafts reaction</a></li> <li><a href="/wiki/Category:Alkylating_agents" title="Category:Alkylating agents">Category:Alkylating agents</a> <ul><li><a href="/wiki/Category:Ethylating_agents" title="Category:Ethylating agents">Category:Ethylating agents</a></li> <li><a href="/wiki/Category:Methylating_agents" title="Category:Methylating agents">Category:Methylating agents</a></li></ul></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=Alkylation&action=edit&section=16" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text">March Jerry; (1985). Advanced Organic Chemistry reactions, mechanisms and structure (3rd ed.). New York: John Wiley & Sons, inc. <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><a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-471-85472-7" title="Special:BookSources/0-471-85472-7">0-471-85472-7</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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFStefanidakis,_G.Gwyn,_J.E.1993" class="citation book cs1">Stefanidakis, G.; Gwyn, J.E. 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title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Industrial+%26+Engineering+Chemistry+Research&rft.atitle=Review+of+Isobutane+Alkylation+Technology+Using+Ionic+Liquid-Based+Catalysts%E2%80%94Where+Do+We+Stand%3F&rft.volume=59&rft.issue=36&rft.pages=%3Cspan+class%3D%22nowrap%22%3E15811-%3C%2Fspan%3E15838&rft.date=2020&rft_id=info%3Adoi%2F10.1021%2Facs.iecr.0c03418&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A225512999%23id-name%3DS2CID&rft.aulast=Kore&rft.aufirst=Rajkumar&rft.au=Scurto%2C+Aaron+M.&rft.au=Shiflett%2C+Mark+B.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlkylation" class="Z3988"></span></span> </li> <li id="cite_note-14"><span class="mw-cite-backlink"><b><a href="#cite_ref-14">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.oilandgaseng.com/articles/ionic-liquid-alkylation-technology-receives-award/">"Oil & Gas Engineering | Ionic liquid alkylation technology receives award"</a>. 2 January 2018.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Oil+%26+Gas+Engineering+%26%23124%3B+Ionic+liquid+alkylation+technology+receives+award&rft.date=2018-01-02&rft_id=https%3A%2F%2Fwww.oilandgaseng.com%2Farticles%2Fionic-liquid-alkylation-technology-receives-award%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAlkylation" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Alkylation&action=edit&section=17" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a rel="nofollow" class="external text" href="http://www.pslc.ws/mactest/pcsyn.htm">Macrogalleria page on polycarbonate production</a></li> <li><a rel="nofollow" class="external text" href="https://meshb.nlm.nih.gov/record/ui?name=Alkylating+agents">Alkylating+agents</a> at the U.S. National Library of Medicine <a href="/wiki/Medical_Subject_Headings" title="Medical Subject Headings">Medical Subject Headings</a> (MeSH)</li></ul> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl ol,.mw-parser-output .hlist dl ul,.mw-parser-output .hlist ol dl,.mw-parser-output .hlist ol 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