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</a> <ul id="toc-Usage-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Reactions" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Reactions</span> </div> </a> <button aria-controls="toc-Reactions-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Reactions subsection</span> </button> <ul id="toc-Reactions-sublist" class="vector-toc-list"> <li id="toc-Saturated_hydrocarbons" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Saturated_hydrocarbons"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Saturated hydrocarbons</span> </div> </a> <ul id="toc-Saturated_hydrocarbons-sublist" class="vector-toc-list"> <li id="toc-Cracking" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Cracking"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1.1</span> <span>Cracking</span> </div> </a> <ul id="toc-Cracking-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Oxidation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Oxidation"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Oxidation</span> </div> </a> <ul id="toc-Oxidation-sublist" class="vector-toc-list"> <li id="toc-Combustion" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Combustion"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2.1</span> <span>Combustion</span> </div> </a> <ul id="toc-Combustion-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Halogenation" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Halogenation"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2.2</span> <span>Halogenation</span> </div> </a> <ul id="toc-Halogenation-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Unsaturated_hydrocarbons" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Unsaturated_hydrocarbons"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3</span> <span>Unsaturated hydrocarbons</span> </div> </a> <ul id="toc-Unsaturated_hydrocarbons-sublist" class="vector-toc-list"> <li id="toc-Substitution" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Substitution"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3.1</span> <span>Substitution</span> </div> </a> <ul id="toc-Substitution-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Addition" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Addition"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3.2</span> <span>Addition</span> </div> </a> <ul id="toc-Addition-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Metathesis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Metathesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.4</span> <span>Metathesis</span> </div> </a> <ul id="toc-Metathesis-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Origin" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Origin"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Origin</span> </div> </a> <ul id="toc-Origin-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Environmental_impact" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Environmental_impact"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Environmental impact</span> </div> </a> <button aria-controls="toc-Environmental_impact-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 Environmental impact subsection</span> </button> <ul id="toc-Environmental_impact-sublist" class="vector-toc-list"> <li id="toc-Bioremediation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Bioremediation"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Bioremediation</span> </div> </a> <ul id="toc-Bioremediation-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Safety" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Safety"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Safety</span> </div> </a> <ul id="toc-Safety-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">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> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Hydrocarbon</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 103 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-103" 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">103 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/Koolwaterstof" title="Koolwaterstof – Afrikaans" lang="af" hreflang="af" data-title="Koolwaterstof" data-language-autonym="Afrikaans" data-language-local-name="Afrikaans" class="interlanguage-link-target"><span>Afrikaans</span></a></li><li class="interlanguage-link interwiki-am mw-list-item"><a href="https://am.wikipedia.org/wiki/%E1%88%80%E1%8B%AD%E1%8B%B5%E1%88%AE%E1%8A%AB%E1%88%AD%E1%89%A6%E1%8A%95" title="ሀይድሮካርቦን – Amharic" lang="am" hreflang="am" data-title="ሀይድሮካርቦን" data-language-autonym="አማርኛ" data-language-local-name="Amharic" class="interlanguage-link-target"><span>አማርኛ</span></a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%87%D9%8A%D8%AF%D8%B1%D9%88%D9%83%D8%B1%D8%A8%D9%88%D9%86" title="هيدروكربون – Arabic" lang="ar" hreflang="ar" data-title="هيدروكربون" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-ast mw-list-item"><a href="https://ast.wikipedia.org/wiki/Hidrocarburu" title="Hidrocarburu – Asturian" lang="ast" hreflang="ast" data-title="Hidrocarburu" data-language-autonym="Asturianu" data-language-local-name="Asturian" class="interlanguage-link-target"><span>Asturianu</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Karbohidrogenl%C9%99r" title="Karbohidrogenlər – Azerbaijani" lang="az" hreflang="az" data-title="Karbohidrogenlər" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D9%87%DB%8C%D8%AF%D8%B1%D9%88%DA%A9%D8%B1%D8%A8%D9%88%D9%86" title="هیدروکربون – South Azerbaijani" lang="azb" hreflang="azb" data-title="هیدروکربون" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%B9%E0%A6%BE%E0%A6%87%E0%A6%A1%E0%A7%8D%E0%A6%B0%E0%A7%8B%E0%A6%95%E0%A6%BE%E0%A6%B0%E0%A7%8D%E0%A6%AC%E0%A6%A8" title="হাইড্রোকার্বন – Bangla" lang="bn" hreflang="bn" data-title="হাইড্রোকার্বন" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-zh-min-nan mw-list-item"><a href="https://zh-min-nan.wikipedia.org/wiki/Th%C3%B2a%E2%81%BF-h%C3%B2a_ch%C3%BAi-s%C3%B2%CD%98" title="Thòaⁿ-hòa chúi-sò͘ – Minnan" lang="nan" hreflang="nan" data-title="Thòaⁿ-hòa chúi-sò͘" data-language-autonym="閩南語 / Bân-lâm-gú" data-language-local-name="Minnan" class="interlanguage-link-target"><span>閩南語 / Bân-lâm-gú</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%92%D1%83%D0%B3%D0%BB%D0%B5%D0%B2%D0%B0%D0%B4%D0%B0%D1%80%D0%BE%D0%B4%D1%8B" title="Вуглевадароды – Belarusian" lang="be" hreflang="be" data-title="Вуглевадароды" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-be-x-old mw-list-item"><a href="https://be-tarask.wikipedia.org/wiki/%D0%92%D1%83%D0%B3%D0%BB%D0%B5%D0%B2%D0%B0%D0%B4%D0%B0%D1%80%D0%BE%D0%B4%D1%8B" title="Вуглевадароды – Belarusian (Taraškievica orthography)" lang="be-tarask" hreflang="be-tarask" data-title="Вуглевадароды" data-language-autonym="Беларуская (тарашкевіца)" data-language-local-name="Belarusian (Taraškievica orthography)" class="interlanguage-link-target"><span>Беларуская (тарашкевіца)</span></a></li><li class="interlanguage-link interwiki-bcl mw-list-item"><a href="https://bcl.wikipedia.org/wiki/Hidrokarburo" title="Hidrokarburo – Central Bikol" lang="bcl" hreflang="bcl" data-title="Hidrokarburo" data-language-autonym="Bikol Central" data-language-local-name="Central Bikol" class="interlanguage-link-target"><span>Bikol Central</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%92%D1%8A%D0%B3%D0%BB%D0%B5%D0%B2%D0%BE%D0%B4%D0%BE%D1%80%D0%BE%D0%B4" title="Въглеводород – Bulgarian" lang="bg" hreflang="bg" data-title="Въглеводород" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bar mw-list-item"><a href="https://bar.wikipedia.org/wiki/Kuinwossastoffe" title="Kuinwossastoffe – Bavarian" lang="bar" hreflang="bar" data-title="Kuinwossastoffe" data-language-autonym="Boarisch" data-language-local-name="Bavarian" class="interlanguage-link-target"><span>Boarisch</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Ugljikovodik" title="Ugljikovodik – Bosnian" lang="bs" hreflang="bs" data-title="Ugljikovodik" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-br mw-list-item"><a href="https://br.wikipedia.org/wiki/Hidrokarbon" title="Hidrokarbon – Breton" lang="br" hreflang="br" data-title="Hidrokarbon" data-language-autonym="Brezhoneg" data-language-local-name="Breton" class="interlanguage-link-target"><span>Brezhoneg</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Hidrocarbur" title="Hidrocarbur – Catalan" lang="ca" hreflang="ca" data-title="Hidrocarbur" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cv mw-list-item"><a href="https://cv.wikipedia.org/wiki/%D0%93%D0%B8%D0%B4%D1%80o%D0%BA%D0%B0%D1%80%D0%B1%D0%BE%D0%BD" title="Гидрoкарбон – Chuvash" lang="cv" hreflang="cv" data-title="Гидрoкарбон" data-language-autonym="Чӑвашла" data-language-local-name="Chuvash" class="interlanguage-link-target"><span>Чӑвашла</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Uhlovod%C3%ADky" title="Uhlovodíky – Czech" lang="cs" hreflang="cs" data-title="Uhlovodíky" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Hydrocarbon" title="Hydrocarbon – Welsh" lang="cy" hreflang="cy" data-title="Hydrocarbon" data-language-autonym="Cymraeg" data-language-local-name="Welsh" class="interlanguage-link-target"><span>Cymraeg</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Kulbrinte" title="Kulbrinte – Danish" lang="da" hreflang="da" data-title="Kulbrinte" 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/Kohlenwasserstoffe" title="Kohlenwasserstoffe – German" lang="de" hreflang="de" data-title="Kohlenwasserstoffe" 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/S%C3%BCsivesinikud" title="Süsivesinikud – Estonian" lang="et" hreflang="et" data-title="Süsivesinikud" 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%A5%CE%B4%CF%81%CE%BF%CE%B3%CE%BF%CE%BD%CE%AC%CE%BD%CE%B8%CF%81%CE%B1%CE%BA%CE%B5%CF%82" title="Υδρογονάνθρακες – Greek" lang="el" hreflang="el" data-title="Υδρογονάνθρακες" 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/Hidrocarburo" title="Hidrocarburo – Spanish" lang="es" hreflang="es" data-title="Hidrocarburo" 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/Hidrokarbonido" title="Hidrokarbonido – Esperanto" lang="eo" hreflang="eo" data-title="Hidrokarbonido" 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/Hidrokarburo" title="Hidrokarburo – Basque" lang="eu" hreflang="eu" data-title="Hidrokarburo" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%87%DB%8C%D8%AF%D8%B1%D9%88%DA%A9%D8%B1%D8%A8%D9%86" title="هیدروکربن – Persian" lang="fa" hreflang="fa" data-title="هیدروکربن" 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/Hydrocarbure" title="Hydrocarbure – French" lang="fr" hreflang="fr" data-title="Hydrocarbure" 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/Hidreacarb%C3%B3n" title="Hidreacarbón – Irish" lang="ga" hreflang="ga" data-title="Hidreacarbón" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Hidrocarburo" title="Hidrocarburo – Galician" lang="gl" hreflang="gl" data-title="Hidrocarburo" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-gu mw-list-item"><a href="https://gu.wikipedia.org/wiki/%E0%AA%B9%E0%AA%BE%E0%AA%87%E0%AA%A1%E0%AB%8D%E0%AA%B0%E0%AB%8B%E0%AA%95%E0%AA%BE%E0%AA%B0%E0%AB%8D%E0%AA%AC%E0%AA%A8" title="હાઇડ્રોકાર્બન – Gujarati" lang="gu" hreflang="gu" data-title="હાઇડ્રોકાર્બન" data-language-autonym="ગુજરાતી" data-language-local-name="Gujarati" class="interlanguage-link-target"><span>ગુજરાતી</span></a></li><li class="interlanguage-link interwiki-hak mw-list-item"><a href="https://hak.wikipedia.org/wiki/Th%C3%A0n-kh%C3%AEn_Fa-ha%CC%8Dp-vu%CC%8Dt" title="Thàn-khîn Fa-ha̍p-vu̍t – Hakka Chinese" lang="hak" hreflang="hak" data-title="Thàn-khîn Fa-ha̍p-vu̍t" data-language-autonym="客家語 / Hak-kâ-ngî" data-language-local-name="Hakka Chinese" class="interlanguage-link-target"><span>客家語 / Hak-kâ-ngî</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%ED%83%84%ED%99%94%EC%88%98%EC%86%8C" title="탄화수소 – Korean" lang="ko" hreflang="ko" data-title="탄화수소" 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%AE%D5%AD%D5%A1%D5%BB%D6%80%D5%A1%D5%AE%D5%AB%D5%B6%D5%B6%D5%A5%D6%80" title="Ածխաջրածիններ – Armenian" lang="hy" hreflang="hy" data-title="Ածխաջրածիններ" 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%B9%E0%A4%BE%E0%A4%87%E0%A4%A1%E0%A5%8D%E0%A4%B0%E0%A5%8B%E0%A4%95%E0%A4%BE%E0%A4%B0%E0%A5%8D%E0%A4%AC%E0%A4%A8" title="हाइड्रोकार्बन – Hindi" lang="hi" hreflang="hi" data-title="हाइड्रोकार्बन" 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/Ugljikovodici" title="Ugljikovodici – Croatian" lang="hr" hreflang="hr" data-title="Ugljikovodici" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-io mw-list-item"><a href="https://io.wikipedia.org/wiki/Hidrokarbido" title="Hidrokarbido – Ido" lang="io" hreflang="io" data-title="Hidrokarbido" data-language-autonym="Ido" data-language-local-name="Ido" class="interlanguage-link-target"><span>Ido</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Hidrokarbon" title="Hidrokarbon – Indonesian" lang="id" hreflang="id" data-title="Hidrokarbon" 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-os mw-list-item"><a href="https://os.wikipedia.org/wiki/%C3%86%D0%B2%D0%B7%D0%B0%D0%BB%D1%8B%D0%B4%D0%BE%D0%BD%D0%B3%D1%83%D1%8B%D1%80%D1%82%C3%A6" title="Æвзалыдонгуыртæ – Ossetic" lang="os" hreflang="os" data-title="Æвзалыдонгуыртæ" data-language-autonym="Ирон" data-language-local-name="Ossetic" class="interlanguage-link-target"><span>Ирон</span></a></li><li class="interlanguage-link interwiki-is mw-list-item"><a href="https://is.wikipedia.org/wiki/Kolvetni_(l%C3%ADfr%C3%A6n_efnafr%C3%A6%C3%B0i)" title="Kolvetni (lífræn efnafræði) – Icelandic" lang="is" hreflang="is" data-title="Kolvetni (lífræn efnafræði)" data-language-autonym="Íslenska" data-language-local-name="Icelandic" class="interlanguage-link-target"><span>Íslenska</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Idrocarburi" title="Idrocarburi – Italian" lang="it" hreflang="it" data-title="Idrocarburi" 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%A4%D7%97%D7%9E%D7%99%D7%9E%D7%9F" title="פחמימן – Hebrew" lang="he" hreflang="he" data-title="פחמימן" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-jv mw-list-item"><a href="https://jv.wikipedia.org/wiki/Hidrokarbon" title="Hidrokarbon – Javanese" lang="jv" hreflang="jv" data-title="Hidrokarbon" data-language-autonym="Jawa" data-language-local-name="Javanese" class="interlanguage-link-target"><span>Jawa</span></a></li><li class="interlanguage-link interwiki-kn mw-list-item"><a href="https://kn.wikipedia.org/wiki/%E0%B2%B9%E0%B3%88%E0%B2%A1%E0%B3%8D%E0%B2%B0%E0%B3%8A%E0%B2%95%E0%B2%BE%E0%B2%B0%E0%B3%8D%E0%B2%AC%E0%B2%A8%E0%B3%8D%E0%B2%A8%E0%B3%81%E0%B2%97%E0%B2%B3%E0%B3%81" title="ಹೈಡ್ರೊಕಾರ್ಬನ್ನುಗಳು – Kannada" lang="kn" hreflang="kn" data-title="ಹೈಡ್ರೊಕಾರ್ಬನ್ನುಗಳು" data-language-autonym="ಕನ್ನಡ" data-language-local-name="Kannada" class="interlanguage-link-target"><span>ಕನ್ನಡ</span></a></li><li class="interlanguage-link interwiki-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%9C%E1%83%90%E1%83%AE%E1%83%A8%E1%83%98%E1%83%A0%E1%83%AC%E1%83%A7%E1%83%90%E1%83%9A%E1%83%91%E1%83%90%E1%83%93%E1%83%98" title="ნახშირწყალბადი – Georgian" lang="ka" hreflang="ka" data-title="ნახშირწყალბადი" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target"><span>ქართული</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%9A%D3%A9%D0%BC%D1%96%D1%80%D1%81%D1%83%D1%82%D0%B5%D0%BA" title="Көмірсутек – Kazakh" lang="kk" hreflang="kk" data-title="Көмірсутек" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-sw mw-list-item"><a href="https://sw.wikipedia.org/wiki/Hidrokaboni" title="Hidrokaboni – Swahili" lang="sw" hreflang="sw" data-title="Hidrokaboni" data-language-autonym="Kiswahili" data-language-local-name="Swahili" class="interlanguage-link-target"><span>Kiswahili</span></a></li><li class="interlanguage-link interwiki-ht mw-list-item"><a href="https://ht.wikipedia.org/wiki/Idwokabi" title="Idwokabi – Haitian Creole" lang="ht" hreflang="ht" data-title="Idwokabi" data-language-autonym="Kreyòl ayisyen" data-language-local-name="Haitian Creole" class="interlanguage-link-target"><span>Kreyòl ayisyen</span></a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Hydrocarboneum" title="Hydrocarboneum – Latin" lang="la" hreflang="la" data-title="Hydrocarboneum" data-language-autonym="Latina" data-language-local-name="Latin" class="interlanguage-link-target"><span>Latina</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Og%C4%BC%C5%ABde%C5%86ra%C5%BEi" title="Ogļūdeņraži – Latvian" lang="lv" hreflang="lv" data-title="Ogļūdeņraži" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-lb mw-list-item"><a href="https://lb.wikipedia.org/wiki/Kuelewaasserstoffer" title="Kuelewaasserstoffer – Luxembourgish" lang="lb" hreflang="lb" data-title="Kuelewaasserstoffer" data-language-autonym="Lëtzebuergesch" data-language-local-name="Luxembourgish" class="interlanguage-link-target"><span>Lëtzebuergesch</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Angliavandenilis" title="Angliavandenilis – Lithuanian" lang="lt" hreflang="lt" data-title="Angliavandenilis" 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/Sz%C3%A9nhidrog%C3%A9nek" title="Szénhidrogének – Hungarian" lang="hu" hreflang="hu" data-title="Szénhidrogének" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%88%D0%B0%D0%B3%D0%BB%D0%B5%D0%B2%D0%BE%D0%B4%D0%BE%D1%80%D0%BE%D0%B4" title="Јаглеводород – Macedonian" lang="mk" hreflang="mk" data-title="Јаглеводород" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-mg mw-list-item"><a href="https://mg.wikipedia.org/wiki/Akoranafo" title="Akoranafo – Malagasy" lang="mg" hreflang="mg" data-title="Akoranafo" data-language-autonym="Malagasy" data-language-local-name="Malagasy" class="interlanguage-link-target"><span>Malagasy</span></a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%B9%E0%B5%88%E0%B4%A1%E0%B5%8D%E0%B4%B0%E0%B5%8B%E0%B4%95%E0%B4%BE%E0%B5%BC%E0%B4%AC%E0%B4%A3%E0%B5%81%E0%B4%95%E0%B5%BE" title="ഹൈഡ്രോകാർബണുകൾ – Malayalam" lang="ml" hreflang="ml" data-title="ഹൈഡ്രോകാർബണുകൾ" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target"><span>മലയാളം</span></a></li><li class="interlanguage-link interwiki-mr mw-list-item"><a href="https://mr.wikipedia.org/wiki/%E0%A4%95%E0%A4%B0%E0%A5%8D%E0%A4%AC%E0%A5%8B%E0%A4%A6%E0%A4%95" title="कर्बोदक – Marathi" lang="mr" hreflang="mr" data-title="कर्बोदक" data-language-autonym="मराठी" data-language-local-name="Marathi" class="interlanguage-link-target"><span>मराठी</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Hidrokarbon" title="Hidrokarbon – Malay" lang="ms" hreflang="ms" data-title="Hidrokarbon" 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-mn mw-list-item"><a href="https://mn.wikipedia.org/wiki/%D0%9D%D2%AF%D2%AF%D1%80%D1%81%D1%83%D1%81%D1%82%D3%A9%D1%80%D3%A9%D0%B3%D1%87" title="Нүүрсустөрөгч – Mongolian" lang="mn" hreflang="mn" data-title="Нүүрсустөрөгч" data-language-autonym="Монгол" data-language-local-name="Mongolian" class="interlanguage-link-target"><span>Монгол</span></a></li><li class="interlanguage-link interwiki-my mw-list-item"><a href="https://my.wikipedia.org/wiki/%E1%80%9F%E1%80%AD%E1%80%AF%E1%80%80%E1%80%BA%E1%80%92%E1%80%9B%E1%80%AD%E1%80%AF%E1%80%80%E1%80%AC%E1%80%98%E1%80%BD%E1%80%94%E1%80%BA" title="ဟိုက်ဒရိုကာဘွန် – Burmese" lang="my" hreflang="my" data-title="ဟိုက်ဒရိုကာဘွန်" data-language-autonym="မြန်မာဘာသာ" data-language-local-name="Burmese" class="interlanguage-link-target"><span>မြန်မာဘာသာ</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Koolwaterstof" title="Koolwaterstof – Dutch" lang="nl" hreflang="nl" data-title="Koolwaterstof" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ne mw-list-item"><a href="https://ne.wikipedia.org/wiki/%E0%A4%B9%E0%A4%BE%E0%A4%87%E0%A4%A1%E0%A5%8D%E0%A4%B0%E0%A5%8B%E0%A4%95%E0%A4%BE%E0%A4%B0%E0%A5%8D%E0%A4%AC%E0%A4%A8" title="हाइड्रोकार्बन – Nepali" lang="ne" hreflang="ne" data-title="हाइड्रोकार्बन" data-language-autonym="नेपाली" data-language-local-name="Nepali" class="interlanguage-link-target"><span>नेपाली</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E7%82%AD%E5%8C%96%E6%B0%B4%E7%B4%A0" title="炭化水素 – Japanese" lang="ja" hreflang="ja" data-title="炭化水素" 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-frr mw-list-item"><a href="https://frr.wikipedia.org/wiki/K%C3%B6%C3%B6lweederstoof" title="Köölweederstoof – Northern Frisian" lang="frr" hreflang="frr" data-title="Köölweederstoof" data-language-autonym="Nordfriisk" data-language-local-name="Northern Frisian" class="interlanguage-link-target"><span>Nordfriisk</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Hydrokarbon" title="Hydrokarbon – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Hydrokarbon" 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/Hydrokarbon" title="Hydrokarbon – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Hydrokarbon" 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-oc mw-list-item"><a href="https://oc.wikipedia.org/wiki/Idrocarbur" title="Idrocarbur – Occitan" lang="oc" hreflang="oc" data-title="Idrocarbur" data-language-autonym="Occitan" data-language-local-name="Occitan" class="interlanguage-link-target"><span>Occitan</span></a></li><li class="interlanguage-link interwiki-om mw-list-item"><a href="https://om.wikipedia.org/wiki/Haayidirookaarboonii" title="Haayidirookaarboonii – Oromo" lang="om" hreflang="om" data-title="Haayidirookaarboonii" data-language-autonym="Oromoo" data-language-local-name="Oromo" class="interlanguage-link-target"><span>Oromoo</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Uglevodorodlar" title="Uglevodorodlar – Uzbek" lang="uz" hreflang="uz" data-title="Uglevodorodlar" 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-pa mw-list-item"><a href="https://pa.wikipedia.org/wiki/%E0%A8%B9%E0%A8%BE%E0%A8%88%E0%A8%A1%E0%A8%B0%E0%A9%8B%E0%A8%95%E0%A8%BE%E0%A8%B0%E0%A8%AC%E0%A8%A8" title="ਹਾਈਡਰੋਕਾਰਬਨ – Punjabi" lang="pa" hreflang="pa" data-title="ਹਾਈਡਰੋਕਾਰਬਨ" data-language-autonym="ਪੰਜਾਬੀ" data-language-local-name="Punjabi" class="interlanguage-link-target"><span>ਪੰਜਾਬੀ</span></a></li><li class="interlanguage-link interwiki-pnb mw-list-item"><a href="https://pnb.wikipedia.org/wiki/%DB%81%D8%A7%D8%A6%DB%8C%DA%88%D8%B1%D9%88%DA%A9%D8%A7%D8%B1%D8%A8%D9%86" title="ہائیڈروکاربن – Western Punjabi" lang="pnb" hreflang="pnb" data-title="ہائیڈروکاربن" data-language-autonym="پنجابی" data-language-local-name="Western Punjabi" class="interlanguage-link-target"><span>پنجابی</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/W%C4%99glowodory" title="Węglowodory – Polish" lang="pl" hreflang="pl" data-title="Węglowodory" 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/Hidrocarboneto" title="Hidrocarboneto – Portuguese" lang="pt" hreflang="pt" data-title="Hidrocarboneto" 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/Hidrocarbur%C4%83" title="Hidrocarbură – Romanian" lang="ro" hreflang="ro" data-title="Hidrocarbură" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-rue mw-list-item"><a href="https://rue.wikipedia.org/wiki/%D0%93%D0%B8%D0%B4%D1%80%D0%BE%D0%BA%D0%B0%D1%80%D0%B1%D0%BE%D0%BD%D1%8B" title="Гидрокарбоны – Rusyn" lang="rue" hreflang="rue" data-title="Гидрокарбоны" data-language-autonym="Русиньскый" data-language-local-name="Rusyn" class="interlanguage-link-target"><span>Русиньскый</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%A3%D0%B3%D0%BB%D0%B5%D0%B2%D0%BE%D0%B4%D0%BE%D1%80%D0%BE%D0%B4%D1%8B" title="Углеводороды – Russian" lang="ru" hreflang="ru" data-title="Углеводороды" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sco mw-list-item"><a href="https://sco.wikipedia.org/wiki/Hydrocaurbon" title="Hydrocaurbon – Scots" lang="sco" hreflang="sco" data-title="Hydrocaurbon" data-language-autonym="Scots" data-language-local-name="Scots" class="interlanguage-link-target"><span>Scots</span></a></li><li class="interlanguage-link interwiki-sq mw-list-item"><a href="https://sq.wikipedia.org/wiki/Hidrokarburet" title="Hidrokarburet – Albanian" lang="sq" hreflang="sq" data-title="Hidrokarburet" data-language-autonym="Shqip" data-language-local-name="Albanian" class="interlanguage-link-target"><span>Shqip</span></a></li><li class="interlanguage-link interwiki-scn mw-list-item"><a href="https://scn.wikipedia.org/wiki/Idrucarburu" title="Idrucarburu – Sicilian" lang="scn" hreflang="scn" data-title="Idrucarburu" data-language-autonym="Sicilianu" data-language-local-name="Sicilian" class="interlanguage-link-target"><span>Sicilianu</span></a></li><li class="interlanguage-link interwiki-si mw-list-item"><a href="https://si.wikipedia.org/wiki/%E0%B7%84%E0%B6%BA%E0%B7%92%E0%B6%A9%E0%B7%8A%E2%80%8D%E0%B6%BB%E0%B7%9C%E0%B6%9A%E0%B7%8F%E0%B6%B6%E0%B6%B1" title="හයිඩ්‍රොකාබන – Sinhala" lang="si" hreflang="si" data-title="හයිඩ්‍රොකාබන" data-language-autonym="සිංහල" data-language-local-name="Sinhala" class="interlanguage-link-target"><span>සිංහල</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Hydrocarbon" title="Hydrocarbon – Simple English" lang="en-simple" hreflang="en-simple" data-title="Hydrocarbon" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Uh%C4%BEovod%C3%ADk" title="Uhľovodík – Slovak" lang="sk" hreflang="sk" data-title="Uhľovodík" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Ogljikovodik" title="Ogljikovodik – Slovenian" lang="sl" hreflang="sl" data-title="Ogljikovodik" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-so mw-list-item"><a href="https://so.wikipedia.org/wiki/Haaydarokaarboon" title="Haaydarokaarboon – Somali" lang="so" hreflang="so" data-title="Haaydarokaarboon" data-language-autonym="Soomaaliga" data-language-local-name="Somali" class="interlanguage-link-target"><span>Soomaaliga</span></a></li><li class="interlanguage-link interwiki-ckb mw-list-item"><a href="https://ckb.wikipedia.org/wiki/%DA%BE%D8%A7%DB%8C%D8%AF%D8%B1%DB%86%DA%A9%D8%A7%D8%B1%D8%A8%DB%86%D9%86" title="ھایدرۆکاربۆن – Central Kurdish" lang="ckb" hreflang="ckb" data-title="ھایدرۆکاربۆن" data-language-autonym="کوردی" data-language-local-name="Central Kurdish" class="interlanguage-link-target"><span>کوردی</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%A3%D0%B3%D1%99%D0%BE%D0%B2%D0%BE%D0%B4%D0%BE%D0%BD%D0%B8%D0%BA" title="Угљоводоник – Serbian" lang="sr" hreflang="sr" data-title="Угљоводоник" 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/Ugljikovodici" title="Ugljikovodici – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Ugljikovodici" 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-su mw-list-item"><a href="https://su.wikipedia.org/wiki/Hidrokarbon" title="Hidrokarbon – Sundanese" lang="su" hreflang="su" data-title="Hidrokarbon" data-language-autonym="Sunda" data-language-local-name="Sundanese" class="interlanguage-link-target"><span>Sunda</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Hiilivedyt" title="Hiilivedyt – Finnish" lang="fi" hreflang="fi" data-title="Hiilivedyt" 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/Kolv%C3%A4te" title="Kolväte – Swedish" lang="sv" hreflang="sv" data-title="Kolväte" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-tl mw-list-item"><a href="https://tl.wikipedia.org/wiki/Hidrokarburo" title="Hidrokarburo – Tagalog" lang="tl" hreflang="tl" data-title="Hidrokarburo" data-language-autonym="Tagalog" data-language-local-name="Tagalog" class="interlanguage-link-target"><span>Tagalog</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%A8%E0%AF%80%E0%AE%B0%E0%AE%95%E0%AE%95%E0%AF%8D%E0%AE%95%E0%AE%B0%E0%AE%BF%E0%AE%AE%E0%AE%AE%E0%AF%8D" title="நீரகக்கரிமம் – Tamil" lang="ta" hreflang="ta" data-title="நீரகக்கரிமம்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-tt mw-list-item"><a href="https://tt.wikipedia.org/wiki/%D0%A3%D0%B3%D0%BB%D0%B5%D0%B2%D0%BE%D0%B4%D0%BE%D1%80%D0%BE%D0%B4%D0%BB%D0%B0%D1%80" title="Углеводородлар – Tatar" lang="tt" hreflang="tt" data-title="Углеводородлар" data-language-autonym="Татарча / tatarça" data-language-local-name="Tatar" class="interlanguage-link-target"><span>Татарча / tatarça</span></a></li><li class="interlanguage-link interwiki-te mw-list-item"><a href="https://te.wikipedia.org/wiki/%E0%B0%B9%E0%B1%88%E0%B0%A1%E0%B1%8D%E0%B0%B0%E0%B1%8B%E0%B0%95%E0%B0%BE%E0%B0%B0%E0%B1%8D%E0%B0%AC%E0%B0%A8%E0%B1%8D" title="హైడ్రోకార్బన్ – Telugu" lang="te" hreflang="te" data-title="హైడ్రోకార్బన్" data-language-autonym="తెలుగు" data-language-local-name="Telugu" class="interlanguage-link-target"><span>తెలుగు</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B9%84%E0%B8%AE%E0%B9%82%E0%B8%94%E0%B8%A3%E0%B8%84%E0%B8%B2%E0%B8%A3%E0%B9%8C%E0%B8%9A%E0%B8%AD%E0%B8%99" title="ไฮโดรคาร์บอน – Thai" lang="th" hreflang="th" data-title="ไฮโดรคาร์บอน" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Hidrokarbon" title="Hidrokarbon – Turkish" lang="tr" hreflang="tr" data-title="Hidrokarbon" data-language-autonym="Türkçe" 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src="//upload.wikimedia.org/wikipedia/en/thumb/1/1b/Semi-protection-shackle.svg/20px-Semi-protection-shackle.svg.png" decoding="async" width="20" height="20" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/1/1b/Semi-protection-shackle.svg/30px-Semi-protection-shackle.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/1/1b/Semi-protection-shackle.svg/40px-Semi-protection-shackle.svg.png 2x" data-file-width="512" data-file-height="512" /></a></span></div></div> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Organic compound consisting entirely of hydrogen and carbon</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">Not to be confused with <a href="/wiki/Carbohydrate" title="Carbohydrate">Carbohydrate</a>.</div> <p class="mw-empty-elt"> </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Methane-3D-balls.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/Methane-3D-balls.png/170px-Methane-3D-balls.png" decoding="async" width="170" height="171" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/Methane-3D-balls.png/255px-Methane-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/58/Methane-3D-balls.png/340px-Methane-3D-balls.png 2x" data-file-width="1091" data-file-height="1100" /></a><figcaption><a href="/wiki/Ball-and-stick_model" title="Ball-and-stick model">Ball-and-stick model</a> of the <a href="/wiki/Methane" title="Methane">methane</a> molecule, CH<sub>4</sub>. Methane is part of a <a href="/wiki/Homologous_series" title="Homologous series">homologous series</a> known as the <a href="/wiki/Alkane" title="Alkane">alkanes</a>, which contain single <a href="/wiki/Chemical_bond" title="Chemical bond">bonds</a> only.</figcaption></figure> <p>In <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a>, a <b>hydrocarbon</b> is an <a href="/wiki/Organic_compound" title="Organic compound">organic compound</a> consisting entirely of <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a> and <a href="/wiki/Carbon" title="Carbon">carbon</a>.<sup id="cite_ref-Silberberg_1-0" class="reference"><a href="#cite_note-Silberberg-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 620">: 620 </span></sup> Hydrocarbons are examples of <a href="/wiki/Group_14_hydride" title="Group 14 hydride">group 14 hydrides</a>. Hydrocarbons are generally colourless and <a href="/wiki/Hydrophobe" title="Hydrophobe">hydrophobic</a>; their odor is usually faint, and may be similar to that of <a href="/wiki/Gasoline" title="Gasoline">gasoline</a> or <a href="/wiki/Naphtha" title="Naphtha">lighter fluid</a>. They occur in a diverse range of molecular structures and phases: they can be <a href="/wiki/Gas" title="Gas">gases</a> (such as <a href="/wiki/Methane" title="Methane">methane</a> and <a href="/wiki/Propane" title="Propane">propane</a>), <a href="/wiki/Liquid" title="Liquid">liquids</a> (such as <a href="/wiki/Hexane" title="Hexane">hexane</a> and <a href="/wiki/Benzene" title="Benzene">benzene</a>), low melting <a href="/wiki/Solid" title="Solid">solids</a> (such as <a href="/wiki/Paraffin_wax" title="Paraffin wax">paraffin wax</a> and <a href="/wiki/Naphthalene" title="Naphthalene">naphthalene</a>) or <a href="/wiki/Polymer" title="Polymer">polymers</a> (such as <a href="/wiki/Polyethylene" title="Polyethylene">polyethylene</a> and <a href="/wiki/Polystyrene" title="Polystyrene">polystyrene</a>). </p><p>In the <a href="/wiki/Fossil_fuel" title="Fossil fuel">fossil fuel</a> industries, <i>hydrocarbon</i> refers to naturally occurring <a href="/wiki/Petroleum" title="Petroleum">petroleum</a>, <a href="/wiki/Natural_gas" title="Natural gas">natural gas</a> and <a href="/wiki/Coal" title="Coal">coal</a>, or their hydrocarbon derivatives and purified forms. Combustion of hydrocarbons is the main source of the world's energy. Petroleum is the dominant raw-material source for organic <a href="/wiki/Commodity_chemicals" title="Commodity chemicals">commodity chemicals</a> such as solvents and polymers. Most anthropogenic (human-generated) emissions of <a href="/wiki/Greenhouse_gas" title="Greenhouse gas">greenhouse gases</a> are either <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a> released by the burning of <a href="/wiki/Fossil_fuels" class="mw-redirect" title="Fossil fuels">fossil fuels</a>, or methane released from the handling of natural gas or from agriculture. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Types">Types</h2></div> <p>As defined by the <a href="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">International Union of Pure and Applied Chemistry</a>'s <a href="/wiki/IUPAC_nomenclature_of_organic_chemistry" title="IUPAC nomenclature of organic chemistry">nomenclature of organic chemistry</a>, hydrocarbons are classified as follows:<sup id="cite_ref-Ullmann_2-0" class="reference"><a href="#cite_note-Ullmann-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <ol><li><a href="/wiki/Saturated_and_unsaturated_compounds" title="Saturated and unsaturated compounds">Saturated</a> hydrocarbons, which are the simplest of the hydrocarbon types. They are composed entirely of <a href="/wiki/Single_bond" title="Single bond">single bonds</a> and are saturated with hydrogen. The formula for <a href="/wiki/Open-chain_compound" title="Open-chain compound">acyclic</a> saturated hydrocarbons (i.e., <a href="/wiki/Alkanes" class="mw-redirect" title="Alkanes">alkanes</a>) is C<sub><i>n</i></sub>H<sub>2<i>n</i>+2</sub>.<sup id="cite_ref-Silberberg_1-1" class="reference"><a href="#cite_note-Silberberg-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 623">: 623 </span></sup> The most general form of saturated hydrocarbons, (whether linear or branched species, and whether with or without one or more rings) is C<sub><i>n</i></sub>H<sub>2<i>n</i>+2(1-<i>r</i>)</sub>, where <i>r</i> is the number of rings. Those with exactly one ring are the <a href="/wiki/Cycloalkanes" class="mw-redirect" title="Cycloalkanes">cycloalkanes</a>. Saturated hydrocarbons are the basis of <a href="/wiki/Petroleum_fuels" class="mw-redirect" title="Petroleum fuels">petroleum fuels</a> and may be either linear or branched species. One or more of the hydrogen atoms can be replaced with other atoms, for example chlorine or another halogen: this is called a substitution reaction. An example is the conversion of methane to <a href="/wiki/Chloroform" title="Chloroform">chloroform</a> using a <a href="/wiki/Chlorination_reaction" class="mw-redirect" title="Chlorination reaction">chlorination reaction</a>. Halogenating a hydrocarbon produces something that is not a hydrocarbon. It is a very common and useful process. Hydrocarbons with the same <a href="/wiki/Molecular_formula" class="mw-redirect" title="Molecular formula">molecular formula</a> but different <a href="/wiki/Structural_formula" title="Structural formula">structural formulae</a> are called <a href="/wiki/Structural_isomer" title="Structural isomer">structural isomers</a>.<sup id="cite_ref-Silberberg_1-2" class="reference"><a href="#cite_note-Silberberg-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 625">: 625 </span></sup> As given in the example of <a href="/wiki/3-methylhexane" class="mw-redirect" title="3-methylhexane">3-methylhexane</a> and its higher <a href="/wiki/Homologous_series" title="Homologous series">homologues</a>, branched hydrocarbons can be <a href="/wiki/Chirality_(chemistry)" title="Chirality (chemistry)">chiral</a>.<sup id="cite_ref-Silberberg_1-3" class="reference"><a href="#cite_note-Silberberg-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 627">: 627 </span></sup> Chiral saturated hydrocarbons constitute the side chains of <a href="/wiki/Biomolecule" title="Biomolecule">biomolecules</a> such as <a href="/wiki/Chlorophyll" title="Chlorophyll">chlorophyll</a> and <a href="/wiki/Tocopherol" title="Tocopherol">tocopherol</a>.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Unsaturated_hydrocarbon" class="mw-redirect" title="Unsaturated hydrocarbon">Unsaturated hydrocarbons</a>, which have one or more double or triple bonds between carbon atoms. Those with one or more double bonds are called <a href="/wiki/Alkene" title="Alkene">alkenes</a>. Those with one <a href="/wiki/Double_bond" title="Double bond">double bond</a> have the formula C<sub><i>n</i></sub>H<sub>2<i>n</i></sub> (assuming non-cyclic structures).<sup id="cite_ref-Silberberg_1-4" class="reference"><a href="#cite_note-Silberberg-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 628">: 628 </span></sup> Those containing <a href="/wiki/Triple_bond" title="Triple bond">triple bonds</a> are called <a href="/wiki/Alkyne" title="Alkyne">alkyne</a>. Those with one triple bond have the formula C<sub><i>n</i></sub>H<sub>2<i>n</i>−2</sub>.<sup id="cite_ref-Silberberg_1-5" class="reference"><a href="#cite_note-Silberberg-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 631">: 631 </span></sup></li> <li><a href="/wiki/Aromatic_hydrocarbon" class="mw-redirect" title="Aromatic hydrocarbon">Aromatic hydrocarbons</a>, also known as <a href="/wiki/Arene" class="mw-redirect" title="Arene">arenes</a>, which are hydrocarbons that have at least one <a href="/wiki/Aromatic_ring" class="mw-redirect" title="Aromatic ring">aromatic ring</a>. 10% of total nonmethane organic carbon emission are aromatic hydrocarbons from the exhaust of gasoline-powered vehicles.<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></li></ol> <p>The term 'aliphatic' refers to non-aromatic hydrocarbons. Saturated aliphatic hydrocarbons are sometimes referred to as 'paraffins'. Aliphatic hydrocarbons containing a double bond between carbon atoms are sometimes referred to as 'olefins'. </p> <table class="wikitable" style="text-align:center"> <caption>Variations on hydrocarbons based on the number of carbon atoms </caption> <tbody><tr> <th scope="col">Number of<br />carbon atoms </th> <th scope="col"><a href="/wiki/Alkane" title="Alkane">Alkane</a> (single bond) </th> <th scope="col"><a href="/wiki/Alkene" title="Alkene">Alkene</a> (double bond) </th> <th scope="col"><a href="/wiki/Alkyne" title="Alkyne">Alkyne</a> (triple bond) </th> <th scope="col"><a href="/wiki/Cycloalkane" title="Cycloalkane">Cycloalkane</a> </th> <th scope="col"><a href="/wiki/Alkadiene" class="mw-redirect" title="Alkadiene">Alkadiene</a> </th></tr> <tr> <th scope="row">1 </th> <td><a href="/wiki/Methane" title="Methane">Methane</a></td> <td>—</td> <td>—</td> <td>—</td> <td>— </td></tr> <tr> <th scope="row">2 </th> <td><a href="/wiki/Ethane" title="Ethane">Ethane</a></td> <td><a href="/wiki/Ethene" class="mw-redirect" title="Ethene">Ethene</a> (ethylene)</td> <td><a href="/wiki/Acetylene" title="Acetylene">Ethyne</a> (acetylene)</td> <td>—</td> <td>— </td></tr> <tr> <th scope="row">3 </th> <td><a href="/wiki/Propane" title="Propane">Propane</a></td> <td><a href="/wiki/Propene" class="mw-redirect" title="Propene">Propene</a> (propylene)</td> <td><a href="/wiki/Methylacetylene" class="mw-redirect" title="Methylacetylene">Propyne</a> (methylacetylene)</td> <td><a href="/wiki/Cyclopropane" title="Cyclopropane">Cyclopropane</a></td> <td><a href="/wiki/Propadiene" title="Propadiene">Propadiene</a> (allene) </td></tr> <tr> <th scope="row">4 </th> <td><a href="/wiki/Butane" title="Butane">Butane</a></td> <td><a href="/wiki/Butene" title="Butene">Butene</a> (butylene)</td> <td><a href="/wiki/Butyne" title="Butyne">Butyne</a></td> <td><a href="/wiki/Cyclobutane" title="Cyclobutane">Cyclobutane</a></td> <td><a href="/wiki/1,3-Butadiene" class="mw-redirect" title="1,3-Butadiene">Butadiene</a> </td></tr> <tr> <th scope="row">5 </th> <td><a href="/wiki/Pentane" title="Pentane">Pentane</a></td> <td><a href="/wiki/Pentene" title="Pentene">Pentene</a></td> <td><a href="/wiki/Pentyne" title="Pentyne">Pentyne</a></td> <td><a href="/wiki/Cyclopentane" title="Cyclopentane">Cyclopentane</a></td> <td><a href="/wiki/Piperylene" title="Piperylene">Pentadiene</a> (piperylene) </td></tr> <tr> <th scope="row">6 </th> <td><a href="/wiki/Hexane" title="Hexane">Hexane</a></td> <td><a href="/wiki/Hexene" title="Hexene">Hexene</a></td> <td><a href="/wiki/Hexyne" title="Hexyne">Hexyne</a></td> <td><a href="/wiki/Cyclohexane" title="Cyclohexane">Cyclohexane</a></td> <td><a href="/wiki/Hexadiene" class="mw-redirect" title="Hexadiene">Hexadiene</a> </td></tr> <tr> <th scope="row">7 </th> <td><a href="/wiki/Heptane" title="Heptane">Heptane</a></td> <td><a href="/wiki/Heptene" title="Heptene">Heptene</a></td> <td><a href="/wiki/Heptyne" title="Heptyne">Heptyne</a></td> <td><a href="/wiki/Cycloheptane" title="Cycloheptane">Cycloheptane</a></td> <td><a href="/w/index.php?title=Heptadiene&action=edit&redlink=1" class="new" title="Heptadiene (page does not exist)">Heptadiene</a> </td></tr> <tr> <th scope="row">8 </th> <td><a href="/wiki/Octane" title="Octane">Octane</a></td> <td><a href="/wiki/Octene" title="Octene">Octene</a></td> <td><a href="/wiki/Octyne" title="Octyne">Octyne</a></td> <td><a href="/wiki/Cyclooctane" title="Cyclooctane">Cyclooctane</a></td> <td><a href="/wiki/Octadiene" class="mw-redirect" title="Octadiene">Octadiene</a> </td></tr> <tr> <th scope="row">9 </th> <td><a href="/wiki/Nonane" title="Nonane">Nonane</a></td> <td><a href="/wiki/Nonene" title="Nonene">Nonene</a></td> <td><a href="/wiki/Nonyne" title="Nonyne">Nonyne</a></td> <td><a href="/wiki/Cyclononane" title="Cyclononane">Cyclononane</a></td> <td><a href="/w/index.php?title=Nonadiene&action=edit&redlink=1" class="new" title="Nonadiene (page does not exist)">Nonadiene</a> </td></tr> <tr> <th scope="row">10 </th> <td><a href="/wiki/Decane" title="Decane">Decane</a></td> <td><a href="/wiki/Decene" title="Decene">Decene</a></td> <td><a href="/wiki/Decyne" title="Decyne">Decyne</a></td> <td><a href="/wiki/Cyclodecane" title="Cyclodecane">Cyclodecane</a></td> <td><a href="/w/index.php?title=Decadiene&action=edit&redlink=1" class="new" title="Decadiene (page does not exist)">Decadiene</a> </td></tr> <tr> <th scope="row">11 </th> <td><a href="/wiki/Undecane" title="Undecane">Undecane</a></td> <td><a href="/w/index.php?title=Undecene&action=edit&redlink=1" class="new" title="Undecene (page does not exist)">Undecene</a></td> <td><a href="/w/index.php?title=Undecyne&action=edit&redlink=1" class="new" title="Undecyne (page does not exist)">Undecyne</a></td> <td><a href="/wiki/Cycloundecane" title="Cycloundecane">Cycloundecane</a></td> <td><a href="/w/index.php?title=Undecadiene&action=edit&redlink=1" class="new" title="Undecadiene (page does not exist)">Undecadiene</a> </td></tr> <tr> <th scope="row">12 </th> <td><a href="/wiki/Dodecane" title="Dodecane">Dodecane</a></td> <td><a href="/wiki/Dodecene" class="mw-redirect" title="Dodecene">Dodecene</a></td> <td><a href="/w/index.php?title=Dodecyne&action=edit&redlink=1" class="new" title="Dodecyne (page does not exist)">Dodecyne</a></td> <td><a href="/wiki/Cyclododecane" title="Cyclododecane">Cyclododecane</a></td> <td><a href="/w/index.php?title=Dodecadiene&action=edit&redlink=1" class="new" title="Dodecadiene (page does not exist)">Dodecadiene</a> </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="Usage">Usage</h2></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:ShellMartinez-refi.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9c/ShellMartinez-refi.jpg/280px-ShellMartinez-refi.jpg" decoding="async" width="280" height="168" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9c/ShellMartinez-refi.jpg/420px-ShellMartinez-refi.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9c/ShellMartinez-refi.jpg/560px-ShellMartinez-refi.jpg 2x" data-file-width="800" data-file-height="480" /></a><figcaption><a href="/wiki/Oil_refineries" class="mw-redirect" title="Oil refineries">Oil refineries</a> are one way hydrocarbons are processed for use. <a href="/wiki/Crude_oil" class="mw-redirect" title="Crude oil">Crude oil</a> is processed in several stages to form desired hydrocarbons, used as fuel and in other products.</figcaption></figure> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:2018-05-04_(303)_Tank_wagon_33_80_7920_362-0_with_hydrocarbon_gas_at_Bahnhof_Enns.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6c/2018-05-04_%28303%29_Tank_wagon_33_80_7920_362-0_with_hydrocarbon_gas_at_Bahnhof_Enns.jpg/220px-2018-05-04_%28303%29_Tank_wagon_33_80_7920_362-0_with_hydrocarbon_gas_at_Bahnhof_Enns.jpg" decoding="async" width="220" height="165" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6c/2018-05-04_%28303%29_Tank_wagon_33_80_7920_362-0_with_hydrocarbon_gas_at_Bahnhof_Enns.jpg/330px-2018-05-04_%28303%29_Tank_wagon_33_80_7920_362-0_with_hydrocarbon_gas_at_Bahnhof_Enns.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6c/2018-05-04_%28303%29_Tank_wagon_33_80_7920_362-0_with_hydrocarbon_gas_at_Bahnhof_Enns.jpg/440px-2018-05-04_%28303%29_Tank_wagon_33_80_7920_362-0_with_hydrocarbon_gas_at_Bahnhof_Enns.jpg 2x" data-file-width="4000" data-file-height="3000" /></a><figcaption>Tank wagon 33 80 7920 362–0 with hydrocarbon gas at Bahnhof Enns (2018)</figcaption></figure> <p>The predominant use of hydrocarbons is as a combustible <a href="/wiki/Fuel" title="Fuel">fuel</a> source. Methane is the predominant component of natural gas. C<sup>6</sup> through C<sup>10</sup> alkanes, alkenes, cycloalkanes, and aromatic hydrocarbons are the main components of <a href="/wiki/Gasoline" title="Gasoline">gasoline</a>, <a href="/wiki/Petroleum_naphtha" title="Petroleum naphtha">naphtha</a>, <a href="/wiki/Jet_fuel" title="Jet fuel">jet fuel</a>, and specialized industrial solvent mixtures. With the progressive addition of carbon units, the simple non-ring structured hydrocarbons have higher <a href="/wiki/Viscosities" class="mw-redirect" title="Viscosities">viscosities</a>, lubricating indices, boiling points, and <a href="/wiki/Solidification" class="mw-redirect" title="Solidification">solidification</a> temperatures. At the opposite extreme from methane lie the heavy <a href="/wiki/Tar" title="Tar">tars</a> that remain as the <i>lowest fraction</i> in a crude oil <a href="/wiki/Refining_industry" class="mw-redirect" title="Refining industry">refining</a> retort. They are collected and widely utilized as roofing compounds, pavement material (<a href="/wiki/Bitumen" title="Bitumen">bitumen</a>), wood preservatives (the <a href="/wiki/Creosote" title="Creosote">creosote</a> series) and as extremely high viscosity shear-resisting liquids. </p><p>Some large-scale non-fuel applications of hydrocarbons begin with ethane and propane, which are obtained from petroleum and natural gas. These two gases are converted either to <a href="/wiki/Syngas" title="Syngas">syngas</a> or to <a href="/wiki/Ethylene" title="Ethylene">ethylene</a> and <a href="/wiki/Propylene" title="Propylene">propylene</a> respectively. Global consumption of benzene in 2021 is estimated at more than 58 million metric tons, which will increase to 60 million tons in 2022.<sup id="cite_ref-Chem-Systems-2010_5-0" class="reference"><a href="#cite_note-Chem-Systems-2010-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>Hydrocarbons are also prevalent in nature. Some eusocial arthropods, such as the Brazilian stingless bee, <i><a href="/wiki/Schwarziana_quadripunctata" title="Schwarziana quadripunctata">Schwarziana quadripunctata</a></i>, use unique <a href="/wiki/Cuticular_hydrocarbon" class="mw-redirect" title="Cuticular hydrocarbon">cuticular hydrocarbon</a> "scents" in order to determine kin from non-kin. This hydrocarbon composition varies between age, sex, nest location, and hierarchal position.<sup id="cite_ref-nunes09_6-0" class="reference"><a href="#cite_note-nunes09-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>There is also potential to harvest hydrocarbons from plants like <i><a href="/wiki/Euphorbia_lathyris" title="Euphorbia lathyris">Euphorbia lathyris</a></i> and <i><a href="/wiki/Euphorbia_tirucalli" title="Euphorbia tirucalli">E. tirucalli</a></i> as an alternative and renewable energy source for vehicles that use diesel.<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> Furthermore, <a href="/wiki/Endophytic" class="mw-redirect" title="Endophytic">endophytic</a> bacteria from plants that naturally produce hydrocarbons have been used in hydrocarbon degradation in attempts to deplete hydrocarbon concentration in polluted soils.<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-heading2"><h2 id="Reactions">Reactions</h2></div> <p>Saturated hydrocarbons are notable for their inertness. Unsaturated hydrocarbons (alkanes, alkenes and aromatic compounds) react more readily, by means of substitution, addition, polymerization. At higher temperatures they undergo dehydrogenation, oxidation and combustion.<sup id="cite_ref-Ullmann_2-1" class="reference"><a href="#cite_note-Ullmann-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Saturated_hydrocarbons">Saturated hydrocarbons</h3></div> <div class="mw-heading mw-heading4"><h4 id="Cracking">Cracking</h4></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/Cracking_(chemistry)" title="Cracking (chemistry)">Cracking (chemistry)</a></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Further information: <a href="/wiki/Steam_reforming" title="Steam reforming">Steam reforming</a></div> <p>The cracking of saturated hydrocarbons is the main industrial route to <a href="/wiki/Alkene" title="Alkene">alkenes</a> and <a href="/wiki/Alkyne" title="Alkyne">alkyne</a>. These reactions require <a href="/wiki/Heterogeneous_catalyst" class="mw-redirect" title="Heterogeneous catalyst">heterogeneous catalysts</a> and temperatures >500 °C. </p> <div class="mw-heading mw-heading3"><h3 id="Oxidation">Oxidation</h3></div> <p>Widely practice conversions of hydrocarbons involves their reaction with oxygen. In the presence of excess oxygen, hydrocarbons combust. With, however, careful conditions, which have been optimized for many years, partial oxidation results. Useful compounds can obtained in this way: <a href="/wiki/Maleic_acid" title="Maleic acid">maleic acid</a> from <a href="/wiki/Butane" title="Butane">butane</a>, <a href="/wiki/Terephthalic_acid" title="Terephthalic acid">terephthalic acid</a> from <a href="/wiki/Xylene" title="Xylene">xylenes</a>, <a href="/wiki/Acetone" title="Acetone">acetone</a> together with <a href="/wiki/Phenol" title="Phenol">phenol</a> from <a href="/wiki/Cumene" title="Cumene">cumene</a> (isopropylbenzene), and <a href="/wiki/Cyclohexanone" title="Cyclohexanone">cyclohexanone</a> from cyclohexane]]. The process, which is called <a href="/wiki/Autoxidation" title="Autoxidation">autoxidation</a>, begins with the formation of <a href="/wiki/Hydroperoxide" title="Hydroperoxide">hydroperoxides</a> (ROOH).<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Combustion">Combustion</h4></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/Combustion" title="Combustion">Combustion</a></div> <p>Combustion of hydrocarbons is currently the main source of the world's energy for <a href="/wiki/Electric_power" title="Electric power">electric power generation</a>, heating (such as home heating), and transportation.<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><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> Often this energy is used directly as heat such as in home heaters, which use either <a href="/wiki/Petroleum" title="Petroleum">petroleum</a> or <a href="/wiki/Natural_gas" title="Natural gas">natural gas</a>. The hydrocarbon is burnt and the heat is used to heat water, which is then circulated. A similar principle is used to create <a href="/wiki/Electrical_energy" title="Electrical energy">electrical energy</a> in <a href="/wiki/Power_Plants" class="mw-redirect" title="Power Plants">power plants</a>. Both saturated and unsaturated hydrocarbons undergo this process. </p><p>Common properties of hydrocarbons are the facts that they produce steam, <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a> and heat during <a href="/wiki/Combustion" title="Combustion">combustion</a> and that <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> is required for combustion to take place. The simplest hydrocarbon, <a href="/wiki/Methane" title="Methane">methane</a>, burns as follows: </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 {{\underset {methane}{CH4}}+ 2O2 -> CO2 + 2H2O}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <munder> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>4</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>methane</mtext> </munder> </mrow> <mo>+</mo> <mn>2</mn> <mspace width="thinmathspace" /> <msubsup> <mtext>O</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo stretchy="false">⟶</mo> <msubsup> <mtext>CO</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo>+</mo> <mn>2</mn> <mspace width="thinmathspace" /> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>O</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {{\underset {methane}{CH4}}+ 2O2 -> CO2 + 2H2O}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/8a72f60068ff686d0be397b219c224f7e0668254" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -2.838ex; width:32.003ex; height:4.676ex;" alt="{\displaystyle {\ce {{\underset {methane}{CH4}}+ 2O2 -> CO2 + 2H2O}}}"></span></dd></dl> <p>In inadequate supply of air, <a href="/wiki/Carbon_black" title="Carbon black">carbon black</a> and <a href="/wiki/Water_vapor" title="Water vapor">water vapour</a> are formed: </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 {{\underset {methane}{CH4}}+ O2 -> C + 2H2O}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <munder> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>4</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>methane</mtext> </munder> </mrow> <mo>+</mo> <msubsup> <mtext>O</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo stretchy="false">⟶</mo> <mtext>C</mtext> <mo>+</mo> <mn>2</mn> <mspace width="thinmathspace" /> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>O</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {{\underset {methane}{CH4}}+ O2 -> C + 2H2O}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/c27fa979f3dd2f59e1771a8029752c4839f4383e" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -2.838ex; width:27.591ex; height:4.676ex;" alt="{\displaystyle {\ce {{\underset {methane}{CH4}}+ O2 -> C + 2H2O}}}"></span></dd></dl> <p>And finally, for any <a href="/wiki/Linear_alkane" class="mw-redirect" title="Linear alkane">linear alkane</a> of n carbon atoms, </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 {C}}_{n}{\ce {H}}_{2n+2}+\left({{3n+1} \over 2}\right){\ce {O2->}}n{\ce {CO2}}+(n+1){\ce {H2O}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <msub> <mrow class="MJX-TeXAtom-ORD"> <mtext>C</mtext> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mi>n</mi> </mrow> </msub> <msub> <mrow class="MJX-TeXAtom-ORD"> <mtext>H</mtext> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> <mi>n</mi> <mo>+</mo> <mn>2</mn> </mrow> </msub> <mo>+</mo> <mrow> <mo>(</mo> <mrow class="MJX-TeXAtom-ORD"> <mfrac> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> <mi>n</mi> <mo>+</mo> <mn>1</mn> </mrow> <mn>2</mn> </mfrac> </mrow> <mo>)</mo> </mrow> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mtext>O</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo stretchy="false">⟶</mo> </mrow> <mi>n</mi> <mrow class="MJX-TeXAtom-ORD"> <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" /> </mrow> </msubsup> </mrow> <mo>+</mo> <mo stretchy="false">(</mo> <mi>n</mi> <mo>+</mo> <mn>1</mn> <mo stretchy="false">)</mo> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>O</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {C}}_{n}{\ce {H}}_{2n+2}+\left({{3n+1} \over 2}\right){\ce {O2->}}n{\ce {CO2}}+(n+1){\ce {H2O}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/c740b1a9a6a3627f98b9f405188b8f5ec94ffa5b" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -2.505ex; width:50.726ex; height:6.176ex;" alt="{\displaystyle {\ce {C}}_{n}{\ce {H}}_{2n+2}+\left({{3n+1} \over 2}\right){\ce {O2->}}n{\ce {CO2}}+(n+1){\ce {H2O}}}"></span></dd></dl> <p>Partial oxidation characterizes the reactions of alkenes and oxygen. This process is the basis of <a href="/wiki/Rancidification" title="Rancidification">rancidification</a> and <a href="/wiki/Drying_oil" title="Drying oil">paint drying</a>. </p><p><a href="/wiki/Benzene" title="Benzene">Benzene</a> burns with <a href="/wiki/Soot" title="Soot">sooty</a> flame when heated in air: </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 {{\underset {benzene}{C6H6}}+{15 \over 2}O2->6CO2{+}3H2O}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <munder> <mrow> <msubsup> <mtext>C</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>6</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>6</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> </mrow> <mtext>benzene</mtext> </munder> </mrow> <mo>+</mo> <mrow class="MJX-TeXAtom-ORD"> <mfrac> <mrow> <mn>15</mn> <mspace width="thinmathspace" /> </mrow> <mrow> <mn>2</mn> <mspace width="thinmathspace" /> </mrow> </mfrac> </mrow> <msubsup> <mtext>O</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo stretchy="false">⟶</mo> <mn>6</mn> <mspace width="thinmathspace" /> <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" /> </mrow> </msubsup> <mrow class="MJX-TeXAtom-ORD"> <mo>+</mo> </mrow> <mn>3</mn> <mspace width="thinmathspace" /> <msubsup> <mtext>H</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>O</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {{\underset {benzene}{C6H6}}+{15 \over 2}O2->6CO2{+}3H2O}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/0cd785f5ae505bd3b350f6674755292345f40ad0" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -2.838ex; width:34.062ex; height:6.176ex;" alt="{\displaystyle {\ce {{\underset {benzene}{C6H6}}+{15 \over 2}O2->6CO2{+}3H2O}}}"></span></dd></dl> <div class="mw-heading mw-heading4"><h4 id="Halogenation">Halogenation</h4></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/Free-radical_halogenation" title="Free-radical halogenation">Free-radical halogenation</a></div> <p>Saturated hydrocarbons react with <a href="/wiki/Chlorine" title="Chlorine">chlorine</a> and <a href="/wiki/Fluorine" title="Fluorine">fluorine</a>. In the case of chlorination, one of the chlorine atoms replaces a hydrogen atom. The reactions proceed via <a href="/wiki/Free-radical_pathway" class="mw-redirect" title="Free-radical pathway">free-radical pathways</a>, in which the halogen first dissociates into a two neutral radical atoms (<a href="/wiki/Homolysis_(chemistry)" title="Homolysis (chemistry)">homolytic fission</a>). </p> <dl><dd>CH<sub>4</sub> + Cl<sub>2</sub> → CH<sub>3</sub>Cl + HCl</dd> <dd>CH<sub>3</sub>Cl + Cl<sub>2</sub> → CH<sub>2</sub>Cl<sub>2</sub> + HCl</dd></dl> <p>all the way to CCl<sub>4</sub> (<a href="/wiki/Carbon_tetrachloride" title="Carbon tetrachloride">carbon tetrachloride</a>) </p> <dl><dd>C<sub>2</sub>H<sub>6</sub> + Cl<sub>2</sub> → C<sub>2</sub>H<sub>5</sub>Cl + HCl</dd> <dd>C<sub>2</sub>H<sub>4</sub>Cl<sub>2</sub> + Cl<sub>2</sub> → C<sub>2</sub>H<sub>3</sub>Cl<sub>3</sub> + HCl</dd></dl> <p>all the way to C<sub>2</sub>Cl<sub>6</sub> (<a href="/wiki/Hexachloroethane" title="Hexachloroethane">hexachloroethane</a>) </p> <div class="mw-heading mw-heading3"><h3 id="Unsaturated_hydrocarbons">Unsaturated hydrocarbons</h3></div> <div class="mw-heading mw-heading4"><h4 id="Substitution">Substitution</h4></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/Substitution_reaction" title="Substitution reaction">Substitution reaction</a></div> <p>Aromatic compounds, almost uniquely for hydrocarbons, undergo substitution reactions. The chemical process practiced on the largest scale is the reaction of benzene and <a href="/wiki/Ethene" class="mw-redirect" title="Ethene">ethene</a> to give <a href="/wiki/Ethylbenzene" title="Ethylbenzene">ethylbenzene</a>: </p> <dl><dd><style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">6</sub> + C<sub class="template-chem2-sub">2</sub>H<sub class="template-chem2-sub">4</sub> → C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>CH<sub class="template-chem2-sub">2</sub>CH<sub class="template-chem2-sub">3</sub></span></dd></dl> <p>The resulting ethylbenzene is dehydrogenated to <a href="/wiki/Styrene" title="Styrene">styrene</a> and then polymerized to manufacture <a href="/wiki/Polystyrene" title="Polystyrene">polystyrene</a>, a common <a href="/wiki/Thermoplastic" title="Thermoplastic">thermoplastic</a> material. </p> <div class="mw-heading mw-heading4"><h4 id="Addition">Addition</h4></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/Addition_reaction" title="Addition reaction">Addition reaction</a></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Hydrogenation" title="Hydrogenation">Hydrogenation</a></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Polyolefin" title="Polyolefin">Polyolefin</a></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Further information: <a href="/wiki/Addition_polymer" title="Addition polymer">Addition polymer</a></div> <p>Addition reactions apply to alkenes and alkynes. It is because they add reagents that they are called unsaturated. In this reaction a variety of reagents add "across" the pi-bond(s). Chlorine, hydrogen chloride, <a href="/wiki/Water" title="Water">water</a>, and <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a> are illustrative reagents. </p><p>Polymerization is a form of addition. <a href="/wiki/Alkenes" class="mw-redirect" title="Alkenes">Alkenes</a> and some alkynes also undergo <a href="/wiki/Polymerization" title="Polymerization">polymerization</a> by opening of the multiple bonds to produce <a href="/wiki/Polyethylene" title="Polyethylene">polyethylene</a>, <a href="/wiki/Polybutylene" title="Polybutylene">polybutylene</a>, and <a href="/wiki/Polystyrene" title="Polystyrene">polystyrene</a>. The alkyne <a href="/wiki/Acetylene" title="Acetylene">acetylene</a> polymerizes to produce <a href="/wiki/Polyacetylene" title="Polyacetylene">polyacetylene</a>. Oligomers (chains of a few monomers) may be produced, for example in the <a href="/wiki/Shell_higher_olefin_process" title="Shell higher olefin process">Shell higher olefin process</a>, where <a href="/wiki/Alpha-olefin" class="mw-redirect" title="Alpha-olefin">α-olefins</a> are extended to make longer α-olefins by adding ethylene repeatedly. </p> <div class="mw-heading mw-heading3"><h3 id="Metathesis">Metathesis</h3></div> <p>Some hydrocarbons undergo <i>metathesis</i>, in which substituents attached by C–C bonds are exchanged between molecules. For a single C–C bond it is <a href="/wiki/Alkane_metathesis" title="Alkane metathesis">alkane metathesis</a>, for a double C–C bond it is <a href="/wiki/Olefin_metathesis" title="Olefin metathesis">alkene metathesis</a> (olefin metathesis), and for a triple C–C bond it is <a href="/wiki/Alkyne_metathesis" title="Alkyne metathesis">alkyne metathesis</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Origin">Origin</h2></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Korna_natural_oil_seep_1.JPG" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a3/Korna_natural_oil_seep_1.JPG/260px-Korna_natural_oil_seep_1.JPG" decoding="async" width="260" height="195" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a3/Korna_natural_oil_seep_1.JPG/390px-Korna_natural_oil_seep_1.JPG 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a3/Korna_natural_oil_seep_1.JPG/520px-Korna_natural_oil_seep_1.JPG 2x" data-file-width="2272" data-file-height="1704" /></a><figcaption>Natural oil spring in <a href="/wiki/Kor%C5%88a" title="Korňa">Korňa</a>, <a href="/wiki/Slovakia" title="Slovakia">Slovakia</a></figcaption></figure> <p>The vast majority of hydrocarbons found on <a href="/wiki/Earth" title="Earth">Earth</a> occur in <a href="/wiki/Crude_oil" class="mw-redirect" title="Crude oil">crude oil</a>, petroleum, <a href="/wiki/Coal" title="Coal">coal</a>, and natural gas. Since thousands of years they have been exploited and used for a vast range of purposes.<sup id="cite_ref-van_Dijk_2022,_n_12-0" class="reference"><a href="#cite_note-van_Dijk_2022,_n-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> Petroleum (<abbr style="font-size:85%" title="literal translation">lit.</abbr><span style="white-space: nowrap;"> </span><span class="gloss-quot">'</span><span class="gloss-text">rock oil</span><span class="gloss-quot">'</span>) and coal are generally thought to be products of decomposition of organic matter. Coal, in contrast to petroleum, is richer in carbon and poorer in hydrogen. Natural gas is the product of <a href="/wiki/Methanogenesis" title="Methanogenesis">methanogenesis</a>.<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><p>A seemingly limitless variety of compounds comprise petroleum, hence the necessity of refineries. These hydrocarbons consist of saturated hydrocarbons, aromatic hydrocarbons, or combinations of the two. Missing in petroleum are alkenes and alkynes. Their production requires refineries. Petroleum-derived hydrocarbons are mainly consumed for fuel, but they are also the source of virtually all synthetic organic compounds, including plastics and pharmaceuticals. Natural gas is consumed almost exclusively as fuel. Coal is used as a fuel and as a reducing agent in <a href="/wiki/Steelmaking" title="Steelmaking">metallurgy</a>. </p><p>A small fraction of hydrocarbon found on earth, and all currently known hydrocarbon found on other planets and moons, is thought to be <a href="/wiki/Abiogenic_petroleum_origin" title="Abiogenic petroleum origin">abiological</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> </p><p>Hydrocarbons such as ethylene, isoprene, and monoterpenes are emitted by living vegetation.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p><p>Some hydrocarbons also are widespread and abundant in the <a href="/wiki/Solar_System" title="Solar System">Solar System</a>. Lakes of liquid methane and ethane have been found on <a href="/wiki/Titan_(moon)" title="Titan (moon)">Titan</a>, <a href="/wiki/Saturn" title="Saturn">Saturn</a>'s largest moon, as confirmed by the <i><a href="/wiki/Cassini%E2%80%93Huygens" title="Cassini–Huygens">Cassini–Huygens</a></i> space probe.<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> Hydrocarbons are also abundant in nebulae forming <a href="/wiki/Polycyclic_aromatic_hydrocarbon" title="Polycyclic aromatic hydrocarbon">polycyclic aromatic hydrocarbon</a> compounds.<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> </p> <div class="mw-heading mw-heading2"><h2 id="Environmental_impact">Environmental impact</h2></div> <p>Burning hydrocarbons as fuel, which produces <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a> and <a href="/wiki/Water" title="Water">water</a>, is a major contributor to anthropogenic <a href="/wiki/Global_warming" class="mw-redirect" title="Global warming">global warming</a>. Hydrocarbons are introduced into the environment through their extensive use as fuels and chemicals as well as through leaks or accidental spills during exploration, production, refining, or transport of fossil fuels. Anthropogenic hydrocarbon contamination of soil is a serious global issue due to contaminant persistence and the negative impact on human health.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Mechanisms_involved_in_phytoremediation.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Mechanisms_involved_in_phytoremediation.png/400px-Mechanisms_involved_in_phytoremediation.png" decoding="async" width="400" height="281" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Mechanisms_involved_in_phytoremediation.png/600px-Mechanisms_involved_in_phytoremediation.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Mechanisms_involved_in_phytoremediation.png/800px-Mechanisms_involved_in_phytoremediation.png 2x" data-file-width="3670" data-file-height="2579" /></a><figcaption>Mechanisms involved in hydrocarbon <a href="/wiki/Phytoremediation" title="Phytoremediation">phytoremediation</a><sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup></figcaption></figure> <p>When soil is contaminated by hydrocarbons, it can have a significant impact on its microbiological, chemical, and physical properties. This can serve to prevent, slow down or even accelerate the growth of vegetation depending on the exact changes that occur. Crude oil and natural gas are the two largest sources of hydrocarbon contamination of soil.<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> <div class="mw-heading mw-heading3"><h3 id="Bioremediation">Bioremediation</h3></div> <p>Bioremediation of hydrocarbon from soil or water contaminated is a formidable challenge because of the chemical inertness that characterize hydrocarbons (hence they survived millions of years in the source rock). Nonetheless, many strategies have been devised, bioremediation being prominent. The basic problem with bioremediation is the paucity of enzymes that act on them. Nonetheless, the area has received regular attention.<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> Bacteria in the <a href="/wiki/Gabbro" title="Gabbro">gabbroic layer</a> of the ocean's crust can degrade hydrocarbons; but the extreme environment makes research difficult.<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> Other bacteria such as <i><a href="/w/index.php?title=Lutibacterium_anuloederans&action=edit&redlink=1" class="new" title="Lutibacterium anuloederans (page does not exist)">Lutibacterium anuloederans</a></i> can also degrade hydrocarbons.<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> <a href="/wiki/Mycoremediation" title="Mycoremediation">Mycoremediation</a> or breaking down of hydrocarbon by <a href="/wiki/Mycelium" title="Mycelium">mycelium</a> and <a href="/wiki/Mushroom" title="Mushroom">mushrooms</a> is possible.<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> </p> <div class="mw-heading mw-heading2"><h2 id="Safety">Safety</h2></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/Hydrocarbon_poisoning" title="Hydrocarbon poisoning">Hydrocarbon poisoning</a></div> <p>Hydrocarbons are generally of low toxicity, hence the widespread use of gasoline and related volatile products. Aromatic compounds such as benzene and <a href="/wiki/Toluene" title="Toluene">toluene</a> are narcotic and chronic toxins, and benzene in particular is known to be <a href="/wiki/Carcinogen" title="Carcinogen">carcinogenic</a>. Certain rare polycyclic aromatic compounds are carcinogenic. Hydrocarbons are highly <a href="/wiki/Flammable" class="mw-redirect" title="Flammable">flammable</a>. </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2></div> <style data-mw-deduplicate="TemplateStyles:r1184024115">.mw-parser-output .div-col{margin-top:0.3em;column-width:30em}.mw-parser-output .div-col-small{font-size:90%}.mw-parser-output .div-col-rules{column-rule:1px solid #aaa}.mw-parser-output .div-col dl,.mw-parser-output .div-col ol,.mw-parser-output .div-col ul{margin-top:0}.mw-parser-output .div-col li,.mw-parser-output .div-col dd{page-break-inside:avoid;break-inside:avoid-column}</style><div class="div-col"> <ul><li><a href="/wiki/Abiogenic_petroleum_origin" title="Abiogenic petroleum origin">Abiogenic petroleum origin</a></li> <li><a href="/wiki/Biomass_to_liquid" title="Biomass to liquid">Biomass to liquid</a></li> <li><a href="/wiki/Carbohydrate" title="Carbohydrate">Carbohydrate</a></li> <li><a href="/wiki/Energy_storage" title="Energy storage">Energy storage</a></li> <li><a href="/wiki/Fractional_distillation" title="Fractional distillation">Fractional distillation</a></li> <li><a href="/wiki/Functional_group" title="Functional group">Functional group</a></li> <li><a href="/wiki/Hydrocarbon_mixtures" title="Hydrocarbon mixtures">Hydrocarbon mixtures</a></li> <li><a href="/wiki/Organic_nuclear_reactor" title="Organic nuclear reactor">Organic nuclear reactor</a></li></ul> </div> <div style="clear:both;" class=""></div> <div class="mw-heading mw-heading2"><h2 id="References">References</h2></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-Silberberg-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-Silberberg_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Silberberg_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Silberberg_1-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Silberberg_1-3"><sup><i><b>d</b></i></sup></a> <a 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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="CITEREFSilberberg,_Martin2004" class="citation book cs1">Silberberg, Martin (2004). <i>Chemistry: The Molecular Nature Of Matter and Change</i>. 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System</a></li><li class="portal-bar-item"><span class="nowrap"><span typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Papapishu-Lab-icon-6.svg/19px-Papapishu-Lab-icon-6.svg.png" decoding="async" width="19" height="19" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Papapishu-Lab-icon-6.svg/29px-Papapishu-Lab-icon-6.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Papapishu-Lab-icon-6.svg/38px-Papapishu-Lab-icon-6.svg.png 2x" data-file-width="512" data-file-height="512" /></span></span> </span><a href="/wiki/Portal:Chemistry" title="Portal:Chemistry">Chemistry</a></li><li class="portal-bar-item"><span class="nowrap"><span typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5c/Earth-moon.jpg/21px-Earth-moon.jpg" decoding="async" width="21" height="17" class="mw-file-element" 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</span><a href="/wiki/Portal:Engineering" title="Portal:Engineering">Engineering</a></li><li class="portal-bar-item"><span class="nowrap"><span typeof="mw:File"><a href="/wiki/File:Change_in_Average_Temperature.svg" class="mw-file-description"><img alt="icon" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/88/Change_in_Average_Temperature.svg/21px-Change_in_Average_Temperature.svg.png" decoding="async" width="21" height="18" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/88/Change_in_Average_Temperature.svg/32px-Change_in_Average_Temperature.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/88/Change_in_Average_Temperature.svg/42px-Change_in_Average_Temperature.svg.png 2x" data-file-width="960" data-file-height="816" /></a></span> </span><a href="/wiki/Portal:Global_warming" class="mw-redirect" title="Portal:Global warming">Global warming</a></li></ul></div><style data-mw-deduplicate="TemplateStyles:r1236088147">.mw-parser-output .sister-bar{display:flex;justify-content:center;align-items:baseline;font-size:88%;background-color:#fdfdfd;border:1px solid #a2a9b1;clear:both;margin:1em 0 0;padding:0 2em}.mw-parser-output .sister-bar-header{margin:0 1em 0 0.5em;padding:0.2em 0;flex:0 0 auto;min-height:24px;line-height:22px}.mw-parser-output .sister-bar-content{display:flex;flex-flow:row wrap;flex:0 1 auto;align-items:baseline;padding:0.2em 0;column-gap:1em;margin:0;list-style:none}.mw-parser-output .sister-bar-item{display:flex;align-items:baseline;margin:0.15em 0;min-height:24px;text-align:left}.mw-parser-output .sister-bar-logo{width:22px;line-height:22px;margin:0 0.2em;text-align:right}.mw-parser-output .sister-bar-link{margin:0 0.2em;text-align:left}@media screen and (max-width:960px){.mw-parser-output .sister-bar{flex-flow:column wrap;margin:1em auto 0}.mw-parser-output .sister-bar-header{flex:0 1}.mw-parser-output .sister-bar-content{flex:1;border-top:1px solid #a2a9b1;margin:0;list-style:none}.mw-parser-output .sister-bar-item{flex:0 0 20em;min-width:20em}}.mw-parser-output .navbox+link+.sister-bar,.mw-parser-output .navbox+style+.sister-bar,.mw-parser-output .portal-bar+link+.sister-bar,.mw-parser-output .portal-bar+style+.sister-bar,.mw-parser-output .sister-bar+.navbox-styles+.navbox,.mw-parser-output .sister-bar+.navbox-styles+.portal-bar{margin-top:-1px}@media print{body.ns-0 .mw-parser-output .sister-bar{display:none!important}}</style><div class="noprint metadata sister-bar" role="navigation" aria-label="sister-projects"><div class="sister-bar-header"><b>Hydrocarbon</b> at Wikipedia's <a href="/wiki/Wikipedia:Wikimedia_sister_projects" title="Wikipedia:Wikimedia sister projects"><span id="sister-projects" style="white-space:nowrap;">sister projects</span></a>:</div><ul class="sister-bar-content"><li class="sister-bar-item"><span class="sister-bar-logo"><span typeof="mw:File"><span><img alt="" 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href="https://en.wikibooks.org/wiki/A-level_Chemistry/OCR_(Salters)/Hydrocarbons" class="extiw" title="b:A-level Chemistry/OCR (Salters)/Hydrocarbons">Textbooks</a></b> from Wikibooks</span></li><li class="sister-bar-item"><span class="sister-bar-logo"><span typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/ff/Wikidata-logo.svg/21px-Wikidata-logo.svg.png" decoding="async" width="21" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/ff/Wikidata-logo.svg/32px-Wikidata-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/ff/Wikidata-logo.svg/42px-Wikidata-logo.svg.png 2x" data-file-width="1050" data-file-height="590" /></span></span></span><span class="sister-bar-link"><b><a href="https://www.wikidata.org/wiki/Q43648" class="extiw" title="d:Q43648">Data</a></b> from Wikidata</span></li></ul></div> <div class="navbox-styles"><style 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abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Orgchemsuffixes" title="Template:Orgchemsuffixes"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Orgchemsuffixes" title="Template talk:Orgchemsuffixes"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Orgchemsuffixes" title="Special:EditPage/Template:Orgchemsuffixes"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Organic_chemistry_affixes" style="font-size:114%;margin:0 4em"><a href="/wiki/IUPAC_nomenclature_of_organic_chemistry" title="IUPAC nomenclature of organic chemistry">Organic chemistry affixes</a><div style="clear:both;" class=""></div></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Carbon" title="Carbon">Carbon</a>-based</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/-ane" title="-ane">-ane</a> (<a href="/wiki/Alkane" title="Alkane">alkane</a>)</li> <li><a href="/wiki/-ene" title="-ene">-ene</a> (<a href="/wiki/Alkene" title="Alkene">alkene</a>)</li> <li><a href="/wiki/-ine" title="-ine">-ine</a> (unsaturated <a class="mw-selflink selflink">hydrocarbon</a>)</li> <li><a href="/wiki/-yne" title="-yne">-yne</a> (<a href="/wiki/Alkyne" title="Alkyne">alkyne</a>)</li> <li><a href="/wiki/Alk-" title="Alk-">alk-</a> (nonaromatic <a class="mw-selflink selflink">hydrocarbon</a>)</li> <li><a href="https://en.wiktionary.org/wiki/ar-" class="extiw" title="wiktionary:ar-">ar-</a> (<a href="/wiki/Aromatic" class="mw-redirect" title="Aromatic">aromatic</a>)</li> <li><a href="/wiki/Cyclo-" class="mw-redirect" title="Cyclo-">cyclo-</a> (<a href="/wiki/Alicyclic_compound" title="Alicyclic compound">cyclic</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Oxygen" title="Oxygen">Oxygen</a>-based</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/-al" title="-al">-al</a> (<a href="/wiki/Aldehyde" title="Aldehyde">aldehyde</a>)</li> <li><a href="/wiki/-oate" title="-oate">-oate</a> (<a href="/wiki/Ester" title="Ester">ester</a>)</li> <li><a href="/wiki/-oic_acid" class="mw-redirect" title="-oic acid">-oic acid</a> (<a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acid</a>)</li> <li><a href="/wiki/-ol" title="-ol">-ol</a> (<a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohol</a>)</li> <li><a href="/wiki/-one" title="-one">-one</a> (<a href="/wiki/Ketone" title="Ketone">ketone</a>)</li> <li><a href="/wiki/-ose" title="-ose">-ose</a> (<a href="/wiki/Sugar" title="Sugar">sugar</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nitrogen" title="Nitrogen">Nitrogen</a>-based</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/-ine" title="-ine">-ine</a> (<a href="/wiki/Alkaloid" title="Alkaloid">alkaloid</a>)</li> <li><a href="/wiki/Aza-" title="Aza-">aza-</a> (<a href="/wiki/Nitrogen" title="Nitrogen">N</a> replaces <a href="/wiki/Carbon" title="Carbon">C</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sulfur" title="Sulfur">Sulfur</a>-based</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Thio-" title="Thio-">thio-</a> (<a href="/wiki/Sulfur" title="Sulfur">S</a> replaces <a href="/wiki/Oxygen" title="Oxygen">O</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Counting axial atoms</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/Meth-" class="mw-redirect" title="Meth-">meth-</a> (1)</li> <li><a href="/wiki/Eth-" class="mw-redirect" title="Eth-">eth-</a> (2)</li> <li><a href="/wiki/Prop-" class="mw-redirect" title="Prop-">prop-</a> (3)</li> <li><a href="/wiki/But-" class="mw-redirect" title="But-">but-</a> (4)</li> <li>(and the rest are <a href="/wiki/Numeral_prefix#Greek_series" title="Numeral prefix">ordinary Greek/Latin prefixes</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/-ase" title="-ase">-ase</a> (<a href="/wiki/Enzyme" title="Enzyme">enzyme</a>)</li> <li><a href="/wiki/Substituent#Nomenclature" title="Substituent">-yl</a> (<a href="/wiki/Radical_(chemistry)" title="Radical (chemistry)">radical</a>)</li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Hydrocarbons" style="padding:3px"><table class="nowraplinks mw-collapsible expanded 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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Hydrocarbons" title="Template:Hydrocarbons"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Hydrocarbons" title="Template talk:Hydrocarbons"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Hydrocarbons" title="Special:EditPage/Template:Hydrocarbons"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Hydrocarbons" style="font-size:114%;margin:0 4em"><a class="mw-selflink selflink">Hydrocarbons</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:azzurro;">Saturated<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 id="AlkanesCnH2n_+_2" scope="row" class="navbox-group" style="width:8.5em"><a href="/wiki/Alkane" title="Alkane">Alkanes</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 alkanes</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/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 href="/wiki/Xylene" title="Xylene">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"></div><div role="navigation" class="navbox" aria-labelledby="Transport_of_hydrocarbon_fuels" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Fuel_Transport" title="Template:Fuel Transport"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Fuel_Transport" title="Template talk:Fuel Transport"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Fuel_Transport" title="Special:EditPage/Template:Fuel Transport"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Transport_of_hydrocarbon_fuels" style="font-size:114%;margin:0 4em">Transport of <a class="mw-selflink selflink">hydrocarbon</a> fuels</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Oil" title="Oil">Oil</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Oil_tanker" title="Oil tanker">Oil tanker</a></li> <li><a href="/wiki/Oil_terminal" title="Oil terminal">Oil terminal</a></li> <li><a href="/wiki/Tank_car" title="Tank car">Tank car</a></li> <li><a href="/wiki/Tank_truck" title="Tank truck">Tank truck</a></li> <li><a href="/wiki/List_of_oil_pipelines" title="List of oil pipelines">List of oil pipelines</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Liquefied_natural_gas" title="Liquefied natural gas">LNG</a> and <a href="/wiki/Liquefied_petroleum_gas" title="Liquefied petroleum gas">LPG</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/LNG_carrier" title="LNG carrier">LNG carrier</a> <ul><li><small><a href="/wiki/Regasification" title="Regasification">Regasification</a></small></li> <li><small><a href="/wiki/Liquefaction_of_gases" title="Liquefaction of gases">Liquefaction</a></small></li> <li><small><a href="/wiki/Gas_separation" title="Gas separation">Gas separation</a></small></li></ul></li> <li><a href="/wiki/Natural_gas_storage" title="Natural gas storage">Natural gas storage</a></li> <li><a href="/wiki/Black_powder_in_gas_pipelines" title="Black powder in gas pipelines">Black powder in gas pipelines</a></li> <li><a href="/wiki/List_of_natural_gas_pipelines" title="List of natural gas pipelines">List of natural gas pipelines</a></li> <li><a href="/wiki/List_of_LNG_terminals" title="List of LNG terminals">List of LNG terminals</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Coal" title="Coal">Coal</a>/misc.</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/Industrial_railway" title="Industrial railway">Industrial railway</a></li> <li><a href="/wiki/Intermodal_freight_transport" title="Intermodal freight transport">Intermodal freight transport</a></li> <li><a href="/wiki/Syngas" title="Syngas">Syngas</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 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href="/wiki/Help:Authority_control" title="Help:Authority control">Authority control databases</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q43648#identifiers" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">International</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"><ul><li><span class="uid"><a rel="nofollow" class="external text" href="http://id.worldcat.org/fast/964828/">FAST</a></span></li></ul></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">National</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"><ul><li><span class="uid"><a rel="nofollow" class="external text" href="https://d-nb.info/gnd/4125165-9">Germany</a></span></li><li><span class="uid"><a rel="nofollow" class="external text" href="https://id.loc.gov/authorities/sh85063372">United States</a></span></li><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="Hydrocarbures"><a rel="nofollow" class="external text" href="https://catalogue.bnf.fr/ark:/12148/cb119369263">France</a></span></span></li><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="Hydrocarbures"><a 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