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class="vector-toc-list"> <li id="toc-Aliphatic_acyl_halides" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Aliphatic_acyl_halides"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1</span> <span>Aliphatic acyl halides</span> </div> </a> <ul id="toc-Aliphatic_acyl_halides-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Aromatic_acyl_chlorides" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Aromatic_acyl_chlorides"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.2</span> <span>Aromatic acyl chlorides</span> </div> </a> <ul id="toc-Aromatic_acyl_chlorides-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Acyl_fluorides" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Acyl_fluorides"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.3</span> <span>Acyl fluorides</span> </div> </a> <ul id="toc-Acyl_fluorides-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Acyl_bromides_and_iodides" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Acyl_bromides_and_iodides"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.4</span> <span>Acyl bromides and iodides</span> </div> </a> <ul id="toc-Acyl_bromides_and_iodides-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Reactions" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Reactions</span> </div> </a> <ul id="toc-Reactions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Multiple_functional_groups" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Multiple_functional_groups"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Multiple functional groups</span> </div> </a> <ul id="toc-Multiple_functional_groups-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-General_hazards" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#General_hazards"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>General hazards</span> </div> </a> <ul id="toc-General_hazards-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">5</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span 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mw-list-item"><a href="https://da.wikipedia.org/wiki/Acylhalid" title="Acylhalid – Danish" lang="da" hreflang="da" data-title="Acylhalid" 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/S%C3%A4urehalogenide" title="Säurehalogenide – German" lang="de" hreflang="de" data-title="Säurehalogenide" 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/Hapete_haliidid" title="Hapete haliidid – Estonian" lang="et" hreflang="et" data-title="Hapete haliidid" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Haluro_de_%C3%A1cido" title="Haluro de ácido – Spanish" lang="es" hreflang="es" data-title="Haluro de ácido" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Azilo-haluro" title="Azilo-haluro – Basque" lang="eu" hreflang="eu" data-title="Azilo-haluro" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A2%D8%B3%DB%8C%D9%84_%D9%87%D8%A7%D9%84%DB%8C%D8%AF" title="آسیل هالید – Persian" lang="fa" hreflang="fa" data-title="آسیل هالید" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%95%84%EC%8B%A4_%ED%95%A0%EB%9D%BC%EC%9D%B4%EB%93%9C" title="아실 할라이드 – Korean" lang="ko" hreflang="ko" data-title="아실 할라이드" 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%B9%D5%A9%D5%B8%D6%82%D5%B6%D5%A5%D6%80%D5%AB_%D5%B0%D5%A1%D5%AC%D5%B8%D5%A3%D5%A5%D5%B6%D5%A1%D5%B0%D5%AB%D5%A4%D6%80%D5%AB%D5%BF%D5%B6%D5%A5%D6%80" title="Թթուների հալոգենահիդրիտներ – Armenian" lang="hy" hreflang="hy" data-title="Թթուների հալոգենահիդրիտներ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Asil_halida" title="Asil halida – Indonesian" lang="id" hreflang="id" data-title="Asil halida" 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-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Savhalogenidek" title="Savhalogenidek – Hungarian" lang="hu" hreflang="hu" data-title="Savhalogenidek" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%90%D1%86%D0%B8%D0%BB_%D1%85%D0%B0%D0%BB%D0%B8%D0%B4" title="Ацил халид – Macedonian" lang="mk" hreflang="mk" data-title="Ацил халид" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%85%E0%B4%B8%E0%B5%88%E0%B5%BD_%E0%B4%B9%E0%B4%BE%E0%B4%B2%E0%B5%88%E0%B4%A1%E0%B5%8D" title="അസൈൽ ഹാലൈഡ് – Malayalam" lang="ml" hreflang="ml" data-title="അസൈൽ ഹാലൈഡ്" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target"><span>മലയാളം</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Zuurhalogenide" title="Zuurhalogenide – Dutch" lang="nl" hreflang="nl" data-title="Zuurhalogenide" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E9%85%B8%E3%83%8F%E3%83%AD%E3%82%B2%E3%83%B3%E5%8C%96%E7%89%A9" title="酸ハロゲン化物 – Japanese" lang="ja" hreflang="ja" data-title="酸ハロゲン化物" 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-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Halogenur%C4%83_de_acil" title="Halogenură de acil – Romanian" lang="ro" hreflang="ro" data-title="Halogenură de acil" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Acylhalogenid" title="Acylhalogenid – Slovak" lang="sk" hreflang="sk" data-title="Acylhalogenid" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%85%E0%AE%AE%E0%AE%BF%E0%AE%B2_%E0%AE%86%E0%AE%B2%E0%AF%88%E0%AE%9F%E0%AF%81" title="அமில ஆலைடு – Tamil" lang="ta" hreflang="ta" data-title="அமில ஆலைடு" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%93%D0%B0%D0%BB%D0%BE%D0%B3%D0%B5%D0%BD%D0%B0%D0%BD%D0%B3%D1%96%D0%B4%D1%80%D0%B8%D0%B4%D0%B8" title="Галогенангідриди – Ukrainian" lang="uk" hreflang="uk" data-title="Галогенангідриди" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E9%85%B0%E5%8D%A4" title="酰卤 – Chinese" lang="zh" hreflang="zh" data-title="酰卤" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a 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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">Oxoacid compound with an –OH group replaced by a halogen</div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Acyl-halide.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3c/Acyl-halide.svg/144px-Acyl-halide.svg.png" decoding="async" width="144" height="134" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3c/Acyl-halide.svg/216px-Acyl-halide.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3c/Acyl-halide.svg/288px-Acyl-halide.svg.png 2x" data-file-width="512" data-file-height="476" /></a><figcaption>Acyl Halide</figcaption></figure> <p>In <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a>, an <b>acyl halide</b> (also known as an <b>acid halide</b>) is a <a href="/wiki/Chemical_compound" title="Chemical compound">chemical compound</a> derived from an <a href="/wiki/Oxoacid" class="mw-redirect" title="Oxoacid">oxoacid</a><sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> by replacing a <a href="/wiki/Hydroxyl" class="mw-redirect" title="Hydroxyl">hydroxyl</a> group (<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">−OH</span>) with a <a href="/wiki/Halide" title="Halide">halide</a> group (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−X</span>, where X is a <a href="/wiki/Halogen" title="Halogen">halogen</a>).<sup id="cite_ref-IUPAC_2-0" class="reference"><a href="#cite_note-IUPAC-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p>If the acid is a <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acid</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−C(=O)OH</span>), the compound contains a <b><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−C(=O)X</span></b> <a href="/wiki/Functional_group" title="Functional group">functional group</a>, which consists of a <a href="/wiki/Carbonyl" class="mw-redirect" title="Carbonyl">carbonyl</a> group (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C=O</span>) singly bonded to a halogen atom.<sup id="cite_ref-Patai_3-0" class="reference"><a href="#cite_note-Patai-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> The general formula for such an acyl halide can be written <b>RCOX</b>, where R may be, for example, an <a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">alkyl</a> group, CO is the carbonyl group, and X represents the halide, such as <a href="/wiki/Chloride" title="Chloride">chloride</a>. <a href="/wiki/Acyl_chloride" title="Acyl chloride">Acyl chlorides</a> are the most commonly encountered acyl halides, but <a href="/wiki/Acetyl_iodide" title="Acetyl iodide">acetyl iodide</a> is the one produced (transiently) on the largest scale. Billions of kilograms are generated annually in the production of <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a>.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Preparation">Preparation</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acyl_halide&action=edit&section=1" title="Edit section: Preparation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Aliphatic_acyl_halides">Aliphatic acyl halides</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acyl_halide&action=edit&section=2" title="Edit section: Aliphatic acyl halides"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>On an industrial scale, the reaction of <a href="/wiki/Acetic_anhydride" title="Acetic anhydride">acetic anhydride</a> with <a href="/wiki/Hydrogen_chloride" title="Hydrogen chloride">hydrogen chloride</a> produces a mixture of acetyl chloride and acetic acid:<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(CH<sub class="template-chem2-sub">3</sub>CO)<sub class="template-chem2-sub">2</sub>O + HCl → CH<sub class="template-chem2-sub">3</sub>COCl + CH<sub class="template-chem2-sub">3</sub>CO<sub class="template-chem2-sub">2</sub>H</span></dd></dl> <p>Common syntheses of acyl chlorides also entail the reaction of <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acids</a> with <a href="/wiki/Phosgene" title="Phosgene">phosgene</a>, <a href="/wiki/Thionyl_chloride" title="Thionyl chloride">thionyl chloride</a>,<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/Phosphorus_trichloride" title="Phosphorus trichloride">phosphorus trichloride</a><sup id="cite_ref-Friedel_7-0" class="reference"><a href="#cite_note-Friedel-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Phosphorus_pentabromide" title="Phosphorus pentabromide">Phosphorus pentabromide</a> is used for acyl bromides, which are rarely of value. </p> <div class="mw-heading mw-heading3"><h3 id="Aromatic_acyl_chlorides">Aromatic acyl chlorides</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acyl_halide&action=edit&section=3" title="Edit section: Aromatic acyl chlorides"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Benzoyl chloride is produced from <a href="/wiki/Benzotrichloride" title="Benzotrichloride">benzotrichloride</a> using either water or <a href="/wiki/Benzoic_acid" title="Benzoic acid">benzoic acid</a>:<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>CCl<sub class="template-chem2-sub">3</sub> + H<sub class="template-chem2-sub">2</sub>O → C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>COCl + 2 HCl</span></dd> <dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>CCl<sub class="template-chem2-sub">3</sub> + C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>CO<sub class="template-chem2-sub">2</sub>H → 2 C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>COCl + HCl</span></dd></dl> <p>As with other <a href="/wiki/Acyl_chloride" title="Acyl chloride">acyl chlorides</a>, it can be generated from the parent acid and other chlorinating agents <a href="/wiki/Phosphorus_pentachloride" title="Phosphorus pentachloride">phosphorus pentachloride</a> or <a href="/wiki/Thionyl_chloride" title="Thionyl chloride">thionyl chloride</a>. </p><p>Representative laboratory routes to <a href="/wiki/Aromatic_compound" title="Aromatic compound">aromatic</a> acyl halides are comparable to those for aliphatic acyl halides.<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> For example, <a href="/w/index.php?title=Chloroformylation&action=edit&redlink=1" class="new" title="Chloroformylation (page does not exist)">chloroformylation</a>, a specific type of <a href="/wiki/Friedel-Crafts_acylation" class="mw-redirect" title="Friedel-Crafts acylation">Friedel-Crafts acylation</a> which uses <a href="/wiki/Formaldehyde" title="Formaldehyde">formaldehyde</a> as a reagent<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="The Friedel-Crafts article link doesn't discuss this reaction variation. Blanc chloromethylation matches this description but doesn't produce this product. (February 2016)">citation needed</span></a></i>]</sup>, or by the <a href="/wiki/Halogenation#Chlorination" title="Halogenation">direct chlorination</a> of <a href="/wiki/Benzaldehyde" title="Benzaldehyde">benzaldehyde</a> <a href="/wiki/Derivative_(chemistry)" title="Derivative (chemistry)">derivatives</a>.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Acyl_fluorides">Acyl fluorides</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acyl_halide&action=edit&section=4" title="Edit section: Acyl fluorides"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Of commercial interest, <a href="/wiki/Acyl_chlorides" class="mw-redirect" title="Acyl chlorides">acyl chlorides</a> react with HF to give <a href="/wiki/Acyl" class="mw-redirect" title="Acyl">acyl</a> fluorides.<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> Aromatic (as well as aliphatic) acyl fluorides are conveniently prepared directly from carboxylic acids, using stable, inexpensive commodity chemicals: <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">PPh<sub class="template-chem2-sub">3</sub></span>, NBS and <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Et<sub class="template-chem2-sub">3</sub>N-<sub class="template-chem2-sub">3</sub>HF</span> in a bench-top protocol.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Cyanuric_fluoride" title="Cyanuric fluoride">Cyanuric fluoride</a> converts carboxylic acids to acyl fluorides.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p><p>Carboxylic acids react with <a href="/wiki/Sulfur_tetrafluoride" title="Sulfur tetrafluoride">sulfur tetrafluoride</a> to give the acyl fluoride:<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> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">SF<sub class="template-chem2-sub">4</sub> + RCO<sub class="template-chem2-sub">2</sub>H → SOF<sub class="template-chem2-sub">2</sub> + RC(O)F + HF</span></dd></dl> <div class="mw-heading mw-heading3"><h3 id="Acyl_bromides_and_iodides">Acyl bromides and iodides</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acyl_halide&action=edit&section=5" title="Edit section: Acyl bromides and iodides"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Acyl bromides and iodides are synthesized accordingly but are less common.<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> <div class="mw-heading mw-heading2"><h2 id="Reactions">Reactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acyl_halide&action=edit&section=6" title="Edit section: Reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Acyl halides are rather reactive compounds often synthesized to be used as intermediates in the synthesis of other organic compounds. For example, an acyl halide can <a href="/wiki/Chemical_reaction" title="Chemical reaction">react</a> with: </p> <ul><li><a href="/wiki/Water_(molecule)" class="mw-redirect" title="Water (molecule)">water</a>, to form a <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acid</a>. This hydrolysis is the most heavily exploited reaction for acyl halides as it occurs in the industrial synthesis of <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a>.</li></ul> <dl><dd><span typeof="mw:File"><a href="/wiki/File:Hydration_of_Acyl_Halide.PNG" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ee/Hydration_of_Acyl_Halide.PNG/450px-Hydration_of_Acyl_Halide.PNG" decoding="async" width="450" height="102" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ee/Hydration_of_Acyl_Halide.PNG/675px-Hydration_of_Acyl_Halide.PNG 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ee/Hydration_of_Acyl_Halide.PNG/900px-Hydration_of_Acyl_Halide.PNG 2x" data-file-width="938" data-file-height="212" /></a></span></dd></dl> <ul><li>an <a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohol</a> to form an <a href="/wiki/Ester" title="Ester">ester</a></li></ul> <dl><dd><span typeof="mw:File"><a href="/wiki/File:Acyl_Halide_plus_Alcohol.PNG" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6c/Acyl_Halide_plus_Alcohol.PNG/450px-Acyl_Halide_plus_Alcohol.PNG" decoding="async" width="450" height="99" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6c/Acyl_Halide_plus_Alcohol.PNG/675px-Acyl_Halide_plus_Alcohol.PNG 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6c/Acyl_Halide_plus_Alcohol.PNG/900px-Acyl_Halide_plus_Alcohol.PNG 2x" data-file-width="963" data-file-height="212" /></a></span></dd></dl> <ul><li>an <a href="/wiki/Amine" title="Amine">amine</a> to form an <a href="/wiki/Amide" title="Amide">amide</a></li></ul> <dl><dd><span typeof="mw:File"><a href="/wiki/File:Acyl_Halide_plus_Amine.PNG" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e0/Acyl_Halide_plus_Amine.PNG/450px-Acyl_Halide_plus_Amine.PNG" decoding="async" width="450" height="147" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e0/Acyl_Halide_plus_Amine.PNG/675px-Acyl_Halide_plus_Amine.PNG 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e0/Acyl_Halide_plus_Amine.PNG/900px-Acyl_Halide_plus_Amine.PNG 2x" data-file-width="973" data-file-height="318" /></a></span></dd></dl> <ul><li>an <a href="/wiki/Aromatic_compound" title="Aromatic compound">aromatic compound</a>, using a <a href="/wiki/Lewis_acid" class="mw-redirect" title="Lewis acid">Lewis acid</a> catalyst such as AlCl<sub>3</sub>, to form an aromatic <a href="/wiki/Ketone" title="Ketone">ketone</a>.<sup id="cite_ref-Friedel_7-1" class="reference"><a href="#cite_note-Friedel-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> <i>See</i> <a href="/wiki/Friedel-Crafts_acylation" class="mw-redirect" title="Friedel-Crafts acylation">Friedel-Crafts acylation</a>.</li> <li>carboxylic acids to form an <a href="/wiki/Organic_acid_anhydride" title="Organic acid anhydride">organic acid anhydrides</a>.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup></li></ul> <p>In the above reactions, HX (<a href="/wiki/Hydrogen_halide" title="Hydrogen halide">hydrogen halide</a> or hydrohalic acid) is also formed. For example, if the acyl halide is an acyl chloride, HCl (<a href="/wiki/Hydrogen_chloride" title="Hydrogen chloride">hydrogen chloride</a> or <a href="/wiki/Hydrochloric_acid" title="Hydrochloric acid">hydrochloric acid</a>) is also formed. </p> <div class="mw-heading mw-heading2"><h2 id="Multiple_functional_groups">Multiple functional groups</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acyl_halide&action=edit&section=7" title="Edit section: Multiple functional groups"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Adipoyl_chloride.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4e/Adipoyl_chloride.png/220px-Adipoyl_chloride.png" decoding="async" width="220" height="96" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4e/Adipoyl_chloride.png/330px-Adipoyl_chloride.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4e/Adipoyl_chloride.png/440px-Adipoyl_chloride.png 2x" data-file-width="508" data-file-height="222" /></a><figcaption>Adipoyl chloride</figcaption></figure> <p>A molecule can have more than one acyl halide functional group. For example, "adipoyl dichloride", usually simply called <a href="/wiki/Adipoyl_chloride" title="Adipoyl chloride">adipoyl chloride</a>, has two acyl chloride <a href="/wiki/Functional_group" title="Functional group">functional groups</a>; see the structure at right. It is the dichloride (i.e., double chloride) of the 6-carbon dicarboxylic acid <a href="/wiki/Adipic_acid" title="Adipic acid">adipic acid</a>. An important use of adipoyl chloride is <a href="/wiki/Polymerization" title="Polymerization">polymerization</a> with an organic di-amino compound to form a polyamide called <a href="/wiki/Nylon" title="Nylon">nylon</a> or polymerization with certain other organic compounds to form <a href="/wiki/Polyester" title="Polyester">polyesters</a>. </p><p><a href="/wiki/Phosgene" title="Phosgene">Phosgene</a> (carbonyl dichloride, Cl–CO–Cl) is a very toxic gas that is the dichloride of <a href="/wiki/Carbonic_acid" title="Carbonic acid">carbonic acid</a> (HO–CO–OH). Both chlorine atoms in phosgene can undergo reactions analogous to the preceding reactions of acyl halides. Phosgene is used a reactant in the production of <a href="/wiki/Polycarbonate" title="Polycarbonate">polycarbonate</a> polymers, among other industrial applications. </p> <div class="mw-heading mw-heading2"><h2 id="General_hazards">General hazards</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acyl_halide&action=edit&section=8" title="Edit section: General hazards"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Volatile acyl halides are <a href="/wiki/Tears" title="Tears">lachrymatory</a> because they can react with water at the surface of the eye producing hydrohalic and organic acids irritating to the eye. Similar problems can result if one inhales acyl halide vapors. In general, acyl halides (even non-volatile compounds such as <a href="/wiki/Tosyl_chloride" class="mw-redirect" title="Tosyl chloride">tosyl chloride</a>) are <a href="/wiki/Irritation" title="Irritation">irritants</a> to the eyes, skin and <a href="/wiki/Mucous_membrane" title="Mucous membrane">mucous membranes</a>. </p> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Acyl_halide&action=edit&section=9" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><a href="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">IUPAC</a>, <i><a href="/wiki/IUPAC_books#Gold_Book" class="mw-redirect" title="IUPAC books">Compendium of Chemical Terminology</a></i>, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "<a rel="nofollow" class="external text" href="https://goldbook.iupac.org/terms/view/A00123.html">acyl groups</a>". <style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1351%2Fgoldbook.A00123">10.1351/goldbook.A00123</a></span> </li> <li id="cite_note-IUPAC-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-IUPAC_2-0">^</a></b></span> <span class="reference-text"><a href="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">IUPAC</a>, <i><a href="/wiki/IUPAC_books#Gold_Book" class="mw-redirect" title="IUPAC books">Compendium of Chemical Terminology</a></i>, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "<a rel="nofollow" class="external text" href="https://goldbook.iupac.org/terms/view/A00124.html">acyl halides</a>". <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1351%2Fgoldbook.A00124">10.1351/goldbook.A00124</a></span> </li> <li id="cite_note-Patai-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-Patai_3-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSaul_Patai1972" class="citation book cs1">Saul Patai, ed. (1972). <i>Acyl Halides</i>. PATAI'S Chemistry of Functional Groups. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F9780470771273">10.1002/9780470771273</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780470771273" title="Special:BookSources/9780470771273"><bdi>9780470771273</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Acyl+Halides&rft.series=PATAI%27S+Chemistry+of+Functional+Groups&rft.date=1972&rft_id=info%3Adoi%2F10.1002%2F9780470771273&rft.isbn=9780470771273&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcyl+halide" class="Z3988"></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text">Hosea Cheung, Robin S. Tanke, G. Paul Torrence "Acetic Acid" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F14356007.a01_045">10.1002/14356007.a01_045</a></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCheungTankeTorrence2000" class="citation encyclopaedia cs1">Cheung, Hosea; Tanke, Robin S.; Torrence, G. Paul (2000). "Acetic Acid". <i><a href="/wiki/Ullmann%27s_Encyclopedia_of_Industrial_Chemistry" title="Ullmann's Encyclopedia of Industrial Chemistry">Ullmann's Encyclopedia of Industrial Chemistry</a></i>. 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"Benzoic Acid and Derivatives". <i><a href="/wiki/Ullmann%27s_Encyclopedia_of_Industrial_Chemistry" title="Ullmann's Encyclopedia of Industrial Chemistry">Ullmann's Encyclopedia of Industrial Chemistry</a></i>. 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Direct synthesis of acyl iodides from carboxylic acids, esters, lactones, acyl chlorides and anhydrides"</a>. <i>The Journal of Organic Chemistry</i>. <b>55</b> (12): 3922–3926. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fjo00299a042">10.1021/jo00299a042</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0022-3263">0022-3263</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Organic+Chemistry&rft.atitle=Diiodosilane.+3.+Direct+synthesis+of+acyl+iodides+from+carboxylic+acids%2C+esters%2C+lactones%2C+acyl+chlorides+and+anhydrides&rft.volume=55&rft.issue=12&rft.pages=3922-3926&rft.date=1990-06&rft_id=info%3Adoi%2F10.1021%2Fjo00299a042&rft.issn=0022-3263&rft.aulast=Keinan&rft.aufirst=Ehud&rft.au=Sahai%2C+M.&rft_id=https%3A%2F%2Fpubs.acs.org%2Fdoi%2Fabs%2F10.1021%2Fjo00299a042&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAcyl+halide" class="Z3988"></span></span> </li> <li id="cite_note-16"><span class="mw-cite-backlink"><b><a href="#cite_ref-16">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAllenKiblerMcLachlinWilson1946" class="citation journal cs1">Allen, C. 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