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<div class="vector-menu-heading"> 用於已登出編輯者的頁面 <a href="/wiki/Help:%E6%96%B0%E6%89%8B%E5%85%A5%E9%96%80" aria-label="了解更多有關編輯"><span>了解更多</span></a> </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="pt-anoncontribs" class="mw-list-item"><a href="/wiki/Special:%E6%88%91%E7%9A%84%E8%B4%A1%E7%8C%AE" title="由此 IP 位址編輯的清單[y]" accesskey="y"><span>貢獻</span></a></li><li id="pt-anontalk" class="mw-list-item"><a href="/wiki/Special:%E6%88%91%E7%9A%84%E8%AE%A8%E8%AE%BA%E9%A1%B5" title="對於來自此IP地址編輯的討論[n]" accesskey="n"><span>討論</span></a></li> </ul> </div> </div> </div> </div> </nav> </div> </header> </div> <div class="mw-page-container"> <div class="mw-page-container-inner"> <div class="vector-sitenotice-container"> <div id="siteNotice"></div> </div> <div class="vector-column-start"> <div class="vector-main-menu-container"> <div id="mw-navigation"> <nav id="mw-panel" class="vector-main-menu-landmark" aria-label="站台"> <div id="vector-main-menu-pinned-container" class="vector-pinned-container"> </div> </nav> </div> </div> <div class="vector-sticky-pinned-container"> <nav id="mw-panel-toc" aria-label="目次" data-event-name="ui.sidebar-toc" class="mw-table-of-contents-container vector-toc-landmark"> <div id="vector-toc-pinned-container" class="vector-pinned-container"> <div id="vector-toc" class="vector-toc vector-pinnable-element"> <div class="vector-pinnable-header vector-toc-pinnable-header vector-pinnable-header-pinned" data-feature-name="toc-pinned" data-pinnable-element-id="vector-toc" > <h2 class="vector-pinnable-header-label">目次</h2> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-toc.pin">移至側邊欄</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-toc.unpin">隱藏</button> </div> <ul class="vector-toc-contents" id="mw-panel-toc-list"> <li id="toc-mw-content-text" class="vector-toc-list-item vector-toc-level-1"> <a href="#" class="vector-toc-link"> <div class="vector-toc-text">序言</div> </a> </li> <li id="toc-有機化合物的鹵化:_各種類的反應" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#有機化合物的鹵化:_各種類的反應"> <div class="vector-toc-text"> <span class="vector-toc-numb">1</span> <span>有機化合物的鹵化: 各種類的反應</span> </div> </a> <button aria-controls="toc-有機化合物的鹵化:_各種類的反應-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>切換有機化合物的鹵化: 各種類的反應子章節</span> </button> <ul id="toc-有機化合物的鹵化:_各種類的反應-sublist" class="vector-toc-list"> <li id="toc-自由基鹵化" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#自由基鹵化"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1</span> <span>自由基鹵化</span> </div> </a> <ul id="toc-自由基鹵化-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-烯、炔的加成鹵化" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#烯、炔的加成鹵化"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.2</span> <span>烯、炔的加成鹵化</span> </div> </a> <ul id="toc-烯、炔的加成鹵化-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-芳香化合物的鹵化" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#芳香化合物的鹵化"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.3</span> <span>芳香化合物的鹵化</span> </div> </a> <ul id="toc-芳香化合物的鹵化-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-其他鹵化方法" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#其他鹵化方法"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.4</span> <span>其他鹵化方法</span> </div> </a> <ul id="toc-其他鹵化方法-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-有機化合物的鹵化：依鹵族元素歸類" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#有機化合物的鹵化：依鹵族元素歸類"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>有機化合物的鹵化：依鹵族元素歸類</span> </div> </a> <button aria-controls="toc-有機化合物的鹵化：依鹵族元素歸類-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>切換有機化合物的鹵化：依鹵族元素歸類子章節</span> </button> <ul id="toc-有機化合物的鹵化：依鹵族元素歸類-sublist" class="vector-toc-list"> <li id="toc-氟化" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#氟化"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>氟化</span> </div> </a> <ul id="toc-氟化-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-氯化" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#氯化"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.2</span> <span>氯化</span> </div> </a> <ul id="toc-氯化-sublist" class="vector-toc-list"> <li id="toc-氧氯化" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#氧氯化"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.2.1</span> <span>氧氯化</span> </div> </a> <ul id="toc-氧氯化-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-溴化" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#溴化"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.3</span> <span>溴化</span> </div> </a> <ul id="toc-溴化-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-碘化" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#碘化"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.4</span> <span>碘化</span> </div> </a> <ul id="toc-碘化-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-無機化學" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#無機化學"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>無機化學</span> </div> </a> <ul id="toc-無機化學-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-另見" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#另見"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>另見</span> </div> </a> <ul id="toc-另見-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-參考文獻" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#參考文獻"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>參考文獻</span> </div> </a> <ul id="toc-參考文獻-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="目次" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" lang="zh-Hant-TW" dir="ltr"> <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="切換目次" > <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">切換目次</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" lang="zh-Hant-TW" dir="ltr"><span class="mw-page-title-main">鹵化</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" lang="zh-Hant-TW" dir="ltr"> <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="前往別種語言的條目。有 38 種語言可用" > <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-38" 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">38 種語言</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%87%D9%84%D8%AC%D9%86%D8%A9" title="هلجنة – 阿拉伯文" lang="ar" hreflang="ar" data-title="هلجنة" data-language-autonym="العربية" data-language-local-name="阿拉伯文" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%B9%E0%A7%8D%E0%A6%AF%E0%A6%BE%E0%A6%B2%E0%A7%8B%E0%A6%9C%E0%A7%87%E0%A6%A8_%E0%A6%B8%E0%A6%82%E0%A6%AF%E0%A7%8B%E0%A6%97_%E0%A6%AC%E0%A6%BF%E0%A6%95%E0%A7%8D%E0%A6%B0%E0%A6%BF%E0%A6%AF%E0%A6%BC%E0%A6%BE" title="হ্যালোজেন সংযোগ বিক্রিয়া – 孟加拉文" lang="bn" hreflang="bn" data-title="হ্যালোজেন সংযোগ বিক্রিয়া" data-language-autonym="বাংলা" data-language-local-name="孟加拉文" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Halogenaci%C3%B3" title="Halogenació – 加泰蘭文" lang="ca" hreflang="ca" data-title="Halogenació" data-language-autonym="Català" data-language-local-name="加泰蘭文" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Halogenace" title="Halogenace – 捷克文" lang="cs" hreflang="cs" data-title="Halogenace" data-language-autonym="Čeština" data-language-local-name="捷克文" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Halogenierung" title="Halogenierung – 德文" lang="de" hreflang="de" data-title="Halogenierung" data-language-autonym="Deutsch" data-language-local-name="德文" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-en mw-list-item"><a href="https://en.wikipedia.org/wiki/Halogenation" title="Halogenation – 英文" lang="en" hreflang="en" data-title="Halogenation" data-language-autonym="English" data-language-local-name="英文" class="interlanguage-link-target"><span>English</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Halogenaci%C3%B3n" title="Halogenación – 西班牙文" lang="es" hreflang="es" data-title="Halogenación" data-language-autonym="Español" data-language-local-name="西班牙文" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Halogeenimine" title="Halogeenimine – 愛沙尼亞文" lang="et" hreflang="et" data-title="Halogeenimine" data-language-autonym="Eesti" data-language-local-name="愛沙尼亞文" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Halogenazio" title="Halogenazio – 巴斯克文" lang="eu" hreflang="eu" data-title="Halogenazio" data-language-autonym="Euskara" data-language-local-name="巴斯克文" 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%D8%A7%D9%84%D9%88%DA%98%D9%86%E2%80%8C%D8%AF%D8%A7%D8%B1_%DA%A9%D8%B1%D8%AF%D9%86" title="هالوژن‌دار کردن – 波斯文" lang="fa" hreflang="fa" data-title="هالوژن‌دار کردن" data-language-autonym="فارسی" data-language-local-name="波斯文" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Halogenointi" title="Halogenointi – 芬蘭文" lang="fi" hreflang="fi" data-title="Halogenointi" data-language-autonym="Suomi" data-language-local-name="芬蘭文" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Halog%C3%A9nation" title="Halogénation – 法文" lang="fr" hreflang="fr" data-title="Halogénation" data-language-autonym="Français" data-language-local-name="法文" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%94%D7%9C%D7%95%D7%92%D7%A0%D7%A6%D7%99%D7%94" title="הלוגנציה – 希伯來文" lang="he" hreflang="he" data-title="הלוגנציה" data-language-autonym="עברית" data-language-local-name="希伯來文" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%B9%E0%A5%88%E0%A4%B2%E0%A5%8B%E0%A4%9C%E0%A4%A8%E0%A4%A8" title="हैलोजनन – 印地文" lang="hi" hreflang="hi" data-title="हैलोजनन" data-language-autonym="हिन्दी" data-language-local-name="印地文" 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/Halogeniranje" title="Halogeniranje – 克羅埃西亞文" lang="hr" hreflang="hr" data-title="Halogeniranje" data-language-autonym="Hrvatski" data-language-local-name="克羅埃西亞文" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Halog%C3%A9nez%C3%A9s" title="Halogénezés – 匈牙利文" lang="hu" hreflang="hu" data-title="Halogénezés" data-language-autonym="Magyar" data-language-local-name="匈牙利文" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Halogenasi" title="Halogenasi – 印尼文" lang="id" hreflang="id" data-title="Halogenasi" data-language-autonym="Bahasa Indonesia" data-language-local-name="印尼文" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Alogenazione" title="Alogenazione – 義大利文" lang="it" hreflang="it" data-title="Alogenazione" data-language-autonym="Italiano" data-language-local-name="義大利文" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%8F%E3%83%AD%E3%82%B2%E3%83%B3%E5%8C%96" title="ハロゲン化 – 日文" lang="ja" hreflang="ja" data-title="ハロゲン化" data-language-autonym="日本語" data-language-local-name="日文" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%93%D0%B0%D0%BB%D0%BE%D0%B3%D0%B5%D0%BD%D0%B4%D0%B5%D1%83" title="Галогендеу – 哈薩克文" lang="kk" hreflang="kk" data-title="Галогендеу" data-language-autonym="Қазақша" data-language-local-name="哈薩克文" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-lb mw-list-item"><a href="https://lb.wikipedia.org/wiki/Halogenatioun" title="Halogenatioun – 盧森堡文" lang="lb" hreflang="lb" data-title="Halogenatioun" data-language-autonym="Lëtzebuergesch" data-language-local-name="盧森堡文" class="interlanguage-link-target"><span>Lëtzebuergesch</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Halogen%C4%93%C5%A1ana" title="Halogenēšana – 拉脫維亞文" lang="lv" hreflang="lv" data-title="Halogenēšana" data-language-autonym="Latviešu" data-language-local-name="拉脫維亞文" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Penghalogenan" title="Penghalogenan – 馬來文" lang="ms" hreflang="ms" data-title="Penghalogenan" data-language-autonym="Bahasa Melayu" data-language-local-name="馬來文" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Halogenering" title="Halogenering – 荷蘭文" lang="nl" hreflang="nl" data-title="Halogenering" data-language-autonym="Nederlands" data-language-local-name="荷蘭文" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Halogenering" title="Halogenering – 巴克摩挪威文" lang="nb" hreflang="nb" data-title="Halogenering" data-language-autonym="Norsk bokmål" data-language-local-name="巴克摩挪威文" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Halogenowanie" title="Halogenowanie – 波蘭文" lang="pl" hreflang="pl" data-title="Halogenowanie" data-language-autonym="Polski" data-language-local-name="波蘭文" 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/Halogena%C3%A7%C3%A3o" title="Halogenação – 葡萄牙文" lang="pt" hreflang="pt" data-title="Halogenação" data-language-autonym="Português" data-language-local-name="葡萄牙文" 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/Halogenare" title="Halogenare – 羅馬尼亞文" lang="ro" hreflang="ro" data-title="Halogenare" data-language-autonym="Română" data-language-local-name="羅馬尼亞文" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%93%D0%B0%D0%BB%D0%BE%D0%B3%D0%B5%D0%BD%D0%B8%D1%80%D0%BE%D0%B2%D0%B0%D0%BD%D0%B8%D0%B5" title="Галогенирование – 俄文" lang="ru" hreflang="ru" data-title="Галогенирование" data-language-autonym="Русский" data-language-local-name="俄文" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Halogenacija" title="Halogenacija – 塞爾維亞克羅埃西亞文" lang="sh" hreflang="sh" data-title="Halogenacija" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="塞爾維亞克羅埃西亞文" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Halogen%C3%A1cia" title="Halogenácia – 斯洛伐克文" lang="sk" hreflang="sk" data-title="Halogenácia" data-language-autonym="Slovenčina" data-language-local-name="斯洛伐克文" 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/Kloriranje" title="Kloriranje – 斯洛維尼亞文" lang="sl" hreflang="sl" data-title="Kloriranje" data-language-autonym="Slovenščina" data-language-local-name="斯洛維尼亞文" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%A5%D0%B0%D0%BB%D0%BE%D0%B3%D0%B5%D0%BD%D0%B0%D1%86%D0%B8%D1%98%D0%B0" title="Халогенација – 塞爾維亞文" lang="sr" hreflang="sr" data-title="Халогенација" data-language-autonym="Српски / srpski" data-language-local-name="塞爾維亞文" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Halogenering" title="Halogenering – 瑞典文" lang="sv" hreflang="sv" data-title="Halogenering" data-language-autonym="Svenska" data-language-local-name="瑞典文" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%86%E0%AE%B2%E0%AE%9A%E0%AE%A9%E0%AF%87%E0%AE%B1%E0%AF%8D%E0%AE%B1%E0%AE%AE%E0%AF%8D" title="ஆலசனேற்றம் – 坦米爾文" lang="ta" hreflang="ta" data-title="ஆலசனேற்றம்" data-language-autonym="தமிழ்" data-language-local-name="坦米爾文" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-tg mw-list-item"><a href="https://tg.wikipedia.org/wiki/%D2%B2%D0%BE%D0%BB%D1%83%D0%B6%D0%B5%D0%BD%D0%B4%D0%BE%D1%80_%D0%BA%D0%B0%D1%80%D0%B4%D0%B0%D0%BD" title="Ҳолужендор кардан – 塔吉克文" lang="tg" hreflang="tg" data-title="Ҳолужендор кардан" data-language-autonym="Тоҷикӣ" data-language-local-name="塔吉克文" class="interlanguage-link-target"><span>Тоҷикӣ</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Halojenleme" title="Halojenleme – 土耳其文" lang="tr" hreflang="tr" data-title="Halojenleme" data-language-autonym="Türkçe" data-language-local-name="土耳其文" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%93%D0%B0%D0%BB%D0%BE%D0%B3%D0%B5%D0%BD%D1%83%D0%B2%D0%B0%D0%BD%D0%BD%D1%8F" title="Галогенування – 烏克蘭文" lang="uk" hreflang="uk" data-title="Галогенування" data-language-autonym="Українська" data-language-local-name="烏克蘭文" class="interlanguage-link-target"><span>Українська</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q888529#sitelinks-wikipedia" title="編輯跨語言連結" class="wbc-editpage">編輯連結</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> <div id="left-navigation"> <nav aria-label="命名空間"> <div id="p-associated-pages" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-associated-pages" lang="zh-Hant-TW" dir="ltr"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="ca-nstab-main" class="selected vector-tab-noicon mw-list-item"><a href="/wiki/%E9%B9%B5%E5%8C%96" title="瀏覽條目正文[c]" accesskey="c"><span>條目</span></a></li><li id="ca-talk" class="vector-tab-noicon mw-list-item"><a href="/wiki/Talk:%E9%B9%B5%E5%8C%96" rel="discussion" title="關於此頁面的討論[t]" 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</div> </nav> </div> </div> <div id="bodyContent" class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> <div id="mw-indicator-noteTA-f683ec12" class="mw-indicator"><div class="mw-parser-output"><span class="skin-invert" typeof="mw:File"><span title="本頁使用了標題或全文手工轉換"><img alt="本頁使用了標題或全文手工轉換" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/cd/Zh_conversion_icon_m.svg/35px-Zh_conversion_icon_m.svg.png" decoding="async" width="35" height="22" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/cd/Zh_conversion_icon_m.svg/53px-Zh_conversion_icon_m.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/cd/Zh_conversion_icon_m.svg/70px-Zh_conversion_icon_m.svg.png 2x" data-file-width="32" data-file-height="20" /></span></span></div></div> </div> <div id="siteSub" class="noprint">維基百科，自由的百科全書</div> </div> <div id="contentSub" lang="zh-Hant-TW" dir="ltr"><div id="mw-content-subtitle" lang="zh-Hant-TW" dir="ltr"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="zh-Hant-TW" dir="ltr"><div id="noteTA-f683ec12" class="noteTA"><div class="noteTA-group"><div data-noteta-group-source="module" data-noteta-group="Chemistry"></div></div></div> <p><b>鹵化</b>（Halogenation）是一種<a href="/wiki/%E5%8C%96%E5%B7%A5%E5%8D%95%E5%85%83%E8%BF%87%E7%A8%8B" class="mw-redirect" title="化工單元過程">化工單元過程</a>，指的是將有機化合物<a href="/wiki/%E5%88%86%E5%AD%90" title="分子">分子</a>中引入鹵素<a href="/wiki/%E5%8E%9F%E5%AD%90" title="原子">原子</a>，最常用的是向<a href="/wiki/%E7%83%83" title="烴">烴</a>分子中引入鹵素原子，形成「鹵烴」，由於鹵烴相當活潑，很容易被其他原子或「基」置換，因此常用於有機合成製造中間體的過程。<b>鹵化</b>也可以指無機化合物（例如金屬）引入鹵素<a href="/wiki/%E5%8E%9F%E5%AD%90" title="原子">原子</a>的過程。 </p><p>鹵化的途徑和化學劑量和其化學結構的特性、有機化合物的<a href="/wiki/%E5%AE%98%E8%83%BD%E5%9F%BA" class="mw-redirect" title="官能基">官能基</a>或鹵化的鹵族元素都有關係。鹵素是<a href="/wiki/%E6%B0%9F" title="氟">氟</a>、<a href="/wiki/%E6%B0%AF" title="氯">氯</a>、<a href="/wiki/%E6%BA%B4" title="溴">溴</a>、<a href="/wiki/%E7%A2%98" title="碘">碘</a>、<a href="/wiki/%E7%A0%88" class="mw-redirect" title="砈">砈</a>五種<a href="/wiki/%E5%85%83%E7%B4%A0" class="mw-redirect" title="元素">元素</a>的總稱，因此鹵化也分為氟化、氯化、溴化和碘化。碘比氯和溴要貴上很多，因而化工生產中最常用的是氯化法和溴化法。常用的氯化劑是<a href="/wiki/%E6%B0%AF%E6%B0%94" title="氯氣">氯氣</a>或<a href="/wiki/%E6%B0%AF%E5%8C%96%E6%B0%A2" title="氯化氫">氯化氫</a>。因為氟氣氧化性太強，通常會將反應物直接氧化分解，因而氟化一般用相應的<a href="/wiki/%E6%B0%9F%E5%8C%96%E5%89%82" class="mw-redirect" title="氟化劑">氟化劑</a>。 </p><p>鹵化的例子有<a href="/wiki/%E4%B9%99%E7%82%94" title="乙炔">乙炔</a>被<a href="/wiki/%E6%B0%AF%E5%8C%96%E6%B0%A2" title="氯化氫">氯化氫</a>氯化，可以生成<a href="/wiki/%E6%B0%AF%E4%B9%99%E7%83%AF" title="氯乙烯">氯乙烯</a>，成為製造<a href="/wiki/%E5%A1%91%E6%96%99" title="塑膠">塑膠</a><a href="/wiki/%E8%81%9A%E6%B0%AF%E4%B9%99%E7%83%AF" title="聚氯乙烯">聚氯乙烯</a>的原料；<a href="/wiki/%E8%8B%AF" title="苯">苯</a>被氯化生成<a href="/wiki/%E5%85%AD%E6%B0%AF%E8%8B%AF" title="六氯苯">六氯苯</a>等。 </p><p>脫鹵反應（Dehalogenation）是鹵化的逆反應，就是從分子中移除鹵族元素，最常見的是<a href="/wiki/%E8%84%B1%E5%8D%A4%E5%8F%8D%E5%BA%94" title="脫鹵反應">脫鹵化氫反應</a><sup id="cite_ref-Patai_1-0" class="reference"><a href="#cite_note-Patai-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>。 </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="有機化合物的鹵化:_各種類的反應"><span id=".E6.9C.89.E6.A9.9F.E5.8C.96.E5.90.88.E7.89.A9.E7.9A.84.E9.B9.B5.E5.8C.96:_.E5.90.84.E7.A8.AE.E9.A1.9E.E7.9A.84.E5.8F.8D.E6.87.89"></span>有機化合物的鹵化: 各種類的反應</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E9%B9%B5%E5%8C%96&action=edit&section=1" title="編輯章節：有機化合物的鹵化: 各種類的反應"><span>編輯</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>有機化合物鹵化有很多反應途徑，包括<a href="/w/index.php?title=%E8%87%AA%E7%94%B1%E5%9F%BA%E9%B9%B5%E5%8C%96&action=edit&redlink=1" class="new" title="自由基鹵化（頁面不存在）">自由基鹵化</a>、<a href="/w/index.php?title=%E9%85%AE%E5%9F%BA%E9%B9%B5%E5%8C%96&action=edit&redlink=1" class="new" title="酮基鹵化（頁面不存在）">酮基鹵化</a>、<a href="/w/index.php?title=%E8%A6%AA%E9%9B%BB%E5%AD%90%E9%B9%B5%E5%8C%96&action=edit&redlink=1" class="new" title="親電子鹵化（頁面不存在）">親電子鹵化</a>和<a href="/w/index.php?title=%E9%B9%B5%E5%8C%96%E5%8A%A0%E6%88%90%E5%8F%8D%E6%87%89&action=edit&redlink=1" class="new" title="鹵化加成反應（頁面不存在）">鹵化加成反應</a>。 </p> <div class="mw-heading mw-heading3"><h3 id="自由基鹵化"><span id=".E8.87.AA.E7.94.B1.E5.9F.BA.E9.B9.B5.E5.8C.96"></span>自由基鹵化</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E9%B9%B5%E5%8C%96&action=edit&section=2" title="編輯章節：自由基鹵化"><span>編輯</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>典型的<a href="/wiki/%E9%A3%BD%E5%92%8C%E7%83%B4" class="mw-redirect" title="飽和烴">飽和碳氫化合物</a>（<a href="/wiki/%E7%83%B7%E7%83%83" title="烷烴">烷</a>、<a href="/wiki/%E7%8E%AF%E7%83%B7%E7%83%83" title="環烷烴">環烷</a>）透過<a href="/wiki/%E8%87%AA%E7%94%B1%E5%9F%BA" title="自由基">自由基</a>鹵化，藉由鹵族元素<a href="/wiki/%E5%8F%96%E4%BB%A3%E5%8F%8D%E5%BA%94" title="取代反應">取代</a>氫原子。鹵化烷類在區域化學上常常被決定於相對可使用較弱的C-H鍵結。這反應傾向二級和三級碳的位置，因愈穩定的結構愈會導致自由基和躍遷能階產生反應。自由基鹵化被使用在工業製造<a href="/wiki/%E7%94%B2%E7%83%B7" title="甲烷">甲烷</a>氯化物。<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> <dl><dd>CH<sub>4</sub> + Cl<sub>2</sub> → CH<sub>3</sub>Cl + HCl</dd></dl> <div class="mw-heading mw-heading3"><h3 id="烯、炔的加成鹵化"><span id=".E7.83.AF.E3.80.81.E7.82.94.E7.9A.84.E5.8A.A0.E6.88.90.E9.B9.B5.E5.8C.96"></span><a href="/wiki/%E7%83%AF%E7%83%83" title="烯烴">烯</a>、<a href="/wiki/%E7%82%94%E7%83%83" title="炔烴">炔</a>的<a href="/wiki/%E5%8A%A0%E6%88%90%E5%8F%8D%E5%BA%94" title="加成反應">加成</a>鹵化</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E9%B9%B5%E5%8C%96&action=edit&section=3" title="編輯章節：烯、炔的加成鹵化"><span>編輯</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/%E4%B8%8D%E9%A5%B1%E5%92%8C%E5%8C%96%E5%90%88%E7%89%A9" title="不飽和化合物">不飽和化合物</a>，特別是<a href="/wiki/%E7%83%AF" class="mw-redirect" title="烯">烯</a>和<a href="/wiki/%E7%82%94" class="mw-redirect" title="炔">炔</a>，行<b><a href="/wiki/%E5%8A%A0%E6%88%90%E5%8F%8D%E5%BA%94" title="加成反應">加成</a></b>鹵化： </p> <dl><dd><a href="/wiki/%E7%83%AF%E7%83%83" title="烯烴">RCH=CHR'</a>（<a href="/wiki/%E7%83%AF%E7%83%83" title="烯烴">烯</a>）+ <a href="/wiki/%E5%8D%A4%E7%B4%A0" title="鹵素">X<sub>2</sub></a>（鹵素）→ <a href="/wiki/%E5%8D%A4%E4%BB%A3%E7%83%B7%E7%83%83" title="鹵烷">RCHX-CHXR'</a></dd> <dd><a href="/wiki/%E7%82%94%E7%83%83" title="炔烴">RC≡CR</a>（<a href="/wiki/%E7%82%94%E7%83%83" title="炔烴">炔</a>）+ 2<a href="/wiki/%E5%8D%A4%E7%B4%A0" title="鹵素">X<sub>2</sub></a>（鹵素） → <a href="/wiki/%E5%8D%A4%E4%BB%A3%E7%83%B7%E7%83%83" title="鹵烷">RCHX-CHXR'</a></dd></dl> <p><a href="/wiki/%E7%83%AF%E7%83%83" title="烯烴">烯</a>類的<a href="/wiki/%E5%8A%A0%E6%88%90%E5%8F%8D%E5%BA%94" title="加成反應">加成</a>鹵化會產生中間產物<a href="/wiki/%E5%8D%A4%E7%B4%A0" title="鹵素">鹵</a><a href="/wiki/%E7%A6%BB%E5%AD%90" title="離子">離子</a>。特別地，這個<a href="/wiki/%E5%8F%8D%E5%BA%94%E4%B8%AD%E9%97%B4%E4%BD%93" title="反應中間體">中間產物</a>可以把它分離出來。 <sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><figure typeof="mw:File/Thumb"><a href="/wiki/File:Biadamantylidene-bromonium-ion-from-xtal-1994-2D-skeletal.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/64/Biadamantylidene-bromonium-ion-from-xtal-1994-2D-skeletal.png/170px-Biadamantylidene-bromonium-ion-from-xtal-1994-2D-skeletal.png" decoding="async" width="170" height="110" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/64/Biadamantylidene-bromonium-ion-from-xtal-1994-2D-skeletal.png/255px-Biadamantylidene-bromonium-ion-from-xtal-1994-2D-skeletal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/64/Biadamantylidene-bromonium-ion-from-xtal-1994-2D-skeletal.png/340px-Biadamantylidene-bromonium-ion-from-xtal-1994-2D-skeletal.png 2x" data-file-width="1100" data-file-height="712" /></a><figcaption>一個<a href="/wiki/%E6%BA%B4" title="溴">溴</a><a href="/wiki/%E9%8E%93%E5%8C%96%E5%90%88%E7%89%A9" title="鎓化合物">鎓離子</a>的結構</figcaption></figure></dd></dl> <div class="mw-heading mw-heading3"><h3 id="芳香化合物的鹵化"><span id=".E8.8A.B3.E9.A6.99.E5.8C.96.E5.90.88.E7.89.A9.E7.9A.84.E9.B9.B5.E5.8C.96"></span>芳香化合物的鹵化</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E9%B9%B5%E5%8C%96&action=edit&section=4" title="編輯章節：芳香化合物的鹵化"><span>編輯</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>芳香化合物的鹵化是親電子的鹵化反應：<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> <dl><dd>RC<sub>6</sub>H<sub>5</sub> + X<sub>2</sub> → HX + RC<sub>6</sub>H<sub>4</sub>X</dd></dl> <p>此鹵化機制受鹵族元素的影響，<a href="/wiki/%E6%B0%9F" title="氟">氟</a>和<a href="/wiki/%E6%B0%AF" title="氯">氯</a>比較有<a href="/wiki/%E4%BA%B2%E7%94%B5" class="mw-redirect" title="親電">親電</a>的特性以及為比較強的鹵化劑，<a href="/wiki/%E6%BA%B4" title="溴">溴</a>跟<a href="/wiki/%E6%B0%9F" title="氟">氟</a>和<a href="/wiki/%E6%B0%AF" title="氯">氯</a>比起來是比較弱的鹵化劑，但<a href="/wiki/%E7%A2%98" title="碘">碘</a>是它們當中反應最弱的。此脫氫鹵化的機制遵循反轉趨勢:碘是最容易從有機物中移除而有機氟化物則有最高穩定度。 </p> <div class="mw-heading mw-heading3"><h3 id="其他鹵化方法"><span id=".E5.85.B6.E4.BB.96.E9.B9.B5.E5.8C.96.E6.96.B9.E6.B3.95"></span>其他鹵化方法</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E9%B9%B5%E5%8C%96&action=edit&section=5" title="編輯章節：其他鹵化方法"><span>編輯</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/%E6%B1%89%E6%96%AF%E7%8B%84%E5%85%8B%E5%8F%8D%E5%BA%94" title="漢斯狄克反應">漢斯狄克反應</a>：從羧酸中提出短鍊鹵化物，其第一個會產生銀鹽，其之後會和鹵族元素氧化：</li></ul> <dl><dd><dl><dd>RCO<sub>2</sub>Ag + Br<sub>2</sub> → RBr + CO<sub>2</sub> + AgBr</dd></dl></dd></dl> <ul><li><a href="/wiki/%E6%A1%91%E5%BE%B7%E8%BF%88%E5%B0%94%E5%8F%8D%E5%BA%94" title="桑德邁爾反應">桑德邁爾反應</a>：從芳香鹵化物<a href="/wiki/%E9%87%8D%E6%B0%AE%E9%B9%BD" class="mw-redirect" title="重氮鹽">重氮鹽</a>中得到，此化合物是從<a href="/wiki/%E8%8B%AF%E8%83%BA" title="苯胺">苯胺</a>中得到。</li> <li><a href="/wiki/%E8%B5%AB%E5%B0%94%EF%BC%8D%E4%B9%8C%E5%B0%94%E5%93%88%EF%BC%8D%E6%B3%BD%E6%9E%97%E6%96%AF%E5%9F%BA%E5%8F%8D%E5%BA%94" class="mw-redirect" title="赫爾－烏爾哈－澤林斯基反應">赫爾－烏爾哈－澤林斯基反應</a>：羧酸中的α上碳進行鹵化。</li></ul> <div class="mw-heading mw-heading2"><h2 id="有機化合物的鹵化：依鹵族元素歸類"><span id=".E6.9C.89.E6.A9.9F.E5.8C.96.E5.90.88.E7.89.A9.E7.9A.84.E9.B9.B5.E5.8C.96.EF.BC.9A.E4.BE.9D.E9.B9.B5.E6.97.8F.E5.85.83.E7.B4.A0.E6.AD.B8.E9.A1.9E"></span>有機化合物的鹵化：依鹵族元素歸類</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E9%B9%B5%E5%8C%96&action=edit&section=6" title="編輯章節：有機化合物的鹵化：依鹵族元素歸類"><span>編輯</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="氟化"><span id=".E6.B0.9F.E5.8C.96"></span>氟化</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E9%B9%B5%E5%8C%96&action=edit&section=7" title="編輯章節：氟化"><span>編輯</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>氟和飽和或不飽和的有機化合物反應，反應快速，容易爆炸。此反應需要在專業環境下進行。實際應用中，有機化合物常用電化學進行鹵化。最近發現可用<a href="/wiki/%E6%B0%9F%E5%8C%96%E6%B0%A2%E6%A0%B9" title="氟化氫根">氟化氫</a>在陰極當作氟的來源，這方法叫作<a href="/w/index.php?title=%E9%9B%BB%E5%8C%96%E5%AD%B8%E6%B0%9F%E5%8C%96&action=edit&redlink=1" class="new" title="電化學氟化（頁面不存在）">電化學氟化</a>（ECF）。除了用電化學產生氟，還有各種氟化<a href="/wiki/%E5%8C%96%E5%AD%A6%E8%AF%95%E5%89%82" title="化學試劑">試劑</a>的應用像是<a href="/wiki/%E4%BA%8C%E6%B0%9F%E5%8C%96%E6%B0%99" title="二氟化氙">二氟化氙</a>和<a href="/wiki/%E6%B0%9F%E5%8C%96%E9%92%B4" title="氟化鈷">氟化鈷</a>。 </p> <div class="mw-heading mw-heading3"><h3 id="氯化"><span id=".E6.B0.AF.E5.8C.96"></span>氯化</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E9%B9%B5%E5%8C%96&action=edit&section=8" title="編輯章節：氯化"><span>編輯</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>氯化會產生<a href="/wiki/%E6%94%BE%E7%83%AD%E5%8F%8D%E5%BA%94" title="放熱反應">放熱</a>反應。所有的飽和或不飽和化合物會和氯直接產生反應。此組成常需要紫外光幫忙裂解氯原子。氯化在工業上常用來製造<a href="/wiki/1,2-%E4%BA%8C%E6%B0%AF%E4%B9%99%E7%83%B7" title="1,2-二氯乙烷">1,2 - 二氯乙烷</a>（PVC）還有當作溶劑的乙烷。另一種是用<a href="/wiki/%E6%B0%AF%E5%8C%96%E6%B0%A2" title="氯化氫">氯化氫</a>和<a href="/wiki/%E6%B0%A7" title="氧">氧</a>結合進行<a href="/w/index.php?title=%E6%B0%A7%E6%B0%AF%E5%8C%96&action=edit&redlink=1" class="new" title="氧氯化（頁面不存在）">氧氯化</a>，此效果必直接氯化（利用Cl<sub>2</sub>）來的好。 <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-heading4"><h4 id="氧氯化"><span id=".E6.B0.A7.E6.B0.AF.E5.8C.96"></span>氧氯化</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E9%B9%B5%E5%8C%96&action=edit&section=9" title="編輯章節：氧氯化"><span>編輯</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>氧氯化是混合<a href="/wiki/%E6%B0%AF%E5%8C%96%E6%B0%A2" title="氯化氫">氯化氫</a>和<a href="/wiki/%E6%B0%A7" title="氧">氧</a>（O<sub>2</sub>）讓碳氫化合物氯化，這個方法工業上很愛用因為氯化氫比氯便宜。<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>烯是最常用的反應物： </p> <dl><dd>CH<sub>2</sub>=CH<sub>2</sub> + 2 HCl + ½ O<sub>2</sub> → ClCH<sub>2</sub>CH<sub>2</sub>Cl + H<sub>2</sub>O</dd></dl> <p>此反應一開始由<a href="/wiki/%E6%B0%AF%E5%8C%96%E9%93%9C" title="氯化銅">氯化銅</a>（CuCl<sub>2</sub> ，一種從<a href="/wiki/1,2-%E4%BA%8C%E6%B0%AF%E4%B9%99%E7%83%B7" title="1,2-二氯乙烷">1,2-二氯乙烷</a>產生的催化劑），有時候氯化銅會在二氧化矽中做為助催化劑幫助產生<a href="/wiki/%E6%B0%AF%E5%8C%96%E9%92%BE" title="氯化鉀">氯化鉀</a>、<a href="/wiki/%E6%B0%AF%E5%8C%96%E9%95%A7" title="氯化鑭">氯化鑭</a>或<a href="/wiki/%E6%B0%AF%E5%8C%96%E9%93%9D" title="氯化鋁">氯化鋁</a>。除了二氧化矽，也可以用<a href="/wiki/%E7%9F%BE%E5%9C%9F" class="mw-redirect" title="礬土">礬土</a>、<a href="/wiki/%E7%9F%BD%E8%97%BB%E5%9C%9F" title="矽藻土">矽藻土</a>或<a href="/wiki/%E6%B5%AE%E7%9F%B3" class="mw-redirect" title="浮石">浮石</a>作為輔助反應。因為這些反應會放出高能量（238 kJ/mol），催化溫度上得受到控制以免熱裂解。催化對於碳氫化合物的雙鍵氯化扮演很重要的角色，因為氯化銅是其中提供氯原子雙鍵的化合物之一。反應式如下： </p> <dl><dd>CH<sub>2</sub>=CH<sub>2</sub> + 2 CuCl<sub>2</sub> → 2 CuCl + ClH<sub>2</sub>C-CH<sub>2</sub>Cl</dd></dl> <p>氯化銅依序會由氯化亞銅和氧反應再來和<a href="/wiki/%E6%B0%AF%E5%8C%96%E6%B0%A2" title="氯化氫">氯化氫</a>反應而產生： </p> <dl><dd><dl><dd>½ O<sub>2</sub> + 2 CuCl → CuOCuCl<sub>2</sub></dd></dl></dd> <dd>2 HCl + CuOCuCl<sub>2</sub> → 2 CuCl<sub>2</sub> + H<sub>2</sub>O</dd></dl> <p>氧氯化在製造1,2 - 二氯乙烷方面是很重要的，之後可以做出<a href="/wiki/%E6%B0%AF%E4%B9%99%E7%83%AF" title="氯乙烯">氯乙烯</a>，其反應式如下： </p> <dl><dd>ClCH<sub>2</sub>CH<sub>2</sub>Cl → CH<sub>2</sub>=CHCl + HCl</dd> <dd>2 HCl + CH<sub>2</sub>=CH<sub>2</sub> + ½ O<sub>2</sub> → ClCH<sub>2</sub>CH<sub>2</sub>Cl + H<sub>2</sub>O</dd></dl> <p>氯化氫由以上步驟循環反應進行氧氯化，反應物會自己產生也是工業上愛用氧氯化而不是氯化的原因。<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="溴化"><span id=".E6.BA.B4.E5.8C.96"></span>溴化</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E9%B9%B5%E5%8C%96&action=edit&section=10" title="編輯章節：溴化"><span>編輯</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>溴化比氯化還具有選擇性因為反應放出的能量比較少，一般的溴化是加成Br<sub>2</sub>到烯類上面，自然界中比較常有飽和碳氫化合物和芳香化合物的溴化，形成<a href="/w/index.php?title=%E6%9C%89%E6%A9%9F%E6%BA%B4%E5%8C%96%E5%8C%96%E5%90%88%E7%89%A9&action=edit&redlink=1" class="new" title="有機溴化化合物（頁面不存在）">有機溴化化合物</a>。常用的催化劑是<a href="/w/index.php?title=%E6%BA%B4%E9%81%8E%E6%B0%A7%E5%8C%96%E7%89%A9%E9%85%B6&action=edit&redlink=1" class="new" title="溴過氧化物酶（頁面不存在）">溴過氧化物酶</a>，其是利用溴和氧的結合形成氧化劑。 </p><p>在三氯乙烯中進行<a href="/wiki/%E6%9C%89%E6%9C%BA%E5%90%88%E6%88%90" title="有機合成">有機合成</a>製造麻醉劑<a href="/wiki/%E6%B0%9F%E7%83%B7" title="氟烷">氟烷</a>即為溴化的一個例子： <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> </p> <dl><dd><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Halothane_synthesis.png" class="mw-file-description" title="Halothane synthesis"><img alt="Halothane synthesis" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/43/Halothane_synthesis.png/600px-Halothane_synthesis.png" decoding="async" width="600" height="71" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/4/43/Halothane_synthesis.png 1.5x" data-file-width="761" data-file-height="90" /></a><figcaption>Halothane synthesis</figcaption></figure></dd></dl> <p>有機溴化合物是自然界中最常見的鹵化化合物，它的形成是透過<a href="/w/index.php?title=%E6%BA%B4%E9%81%8E%E6%B0%A7%E5%8C%96%E7%89%A9%E9%85%B6&action=edit&redlink=1" class="new" title="溴過氧化物酶（頁面不存在）">溴過氧化物酶</a>進行催化。海洋被估計每年會釋放1-2百萬噸的溴仿和56,000噸的溴甲烷。<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="碘化"><span id=".E7.A2.98.E5.8C.96"></span>碘化</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E9%B9%B5%E5%8C%96&action=edit&section=11" title="編輯章節：碘化"><span>編輯</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>碘是反應最弱的鹵化物，最難和大部分的有機化合物反應。碘與烯類加成是用一種分析的方法叫作<a href="/w/index.php?title=%E7%A2%98%E8%B3%AA&action=edit&redlink=1" class="new" title="碘質（頁面不存在）">碘質</a>，它是用來測量<a href="/wiki/%E8%84%82%E8%82%AA" title="脂肪">脂肪</a>的不飽和程度的一種方法。<a href="/wiki/%E7%A2%98%E4%BB%BF%E5%8F%8D%E5%BA%94" class="mw-redirect" title="碘仿反應">碘仿反應</a>包刮會降解甲基酮。 </p> <div class="mw-heading mw-heading2"><h2 id="無機化學"><span id=".E7.84.A1.E6.A9.9F.E5.8C.96.E5.AD.B8"></span>無機化學</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E9%B9%B5%E5%8C%96&action=edit&section=12" title="編輯章節：無機化學"><span>編輯</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>除了氬、氖、氦以外的元素都會直接和<a href="/wiki/%E6%B0%9F" title="氟">氟</a>反應形成氟化物。氯的選擇性較強，但仍可以和大部分的金屬元素和較重的非金屬元素反應。按照趨勢，溴的活性較弱，而碘的活性最弱。可能的反應像金的氯化產生<a href="/wiki/%E6%B0%AF%E5%8C%96%E9%87%91" title="氯化金">氯化金</a>。在工業上金屬直接氯化較不重要，因為比較容易金屬氧化物和鹵化氫反應來進行鹵化。像<a href="/wiki/%E4%B8%89%E6%B0%AF%E5%8C%96%E7%A3%B7" title="三氯化磷">三氯化磷</a>和<a href="/wiki/%E4%B8%80%E6%B0%AF%E5%8C%96%E7%A1%AB" class="mw-redirect" title="一氯化硫">一氯化硫</a>的生產，是較大規模直接進行無機化合物鹵化的例子<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-heading2"><h2 id="另見"><span id=".E5.8F.A6.E8.A6.8B"></span>另見</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E9%B9%B5%E5%8C%96&action=edit&section=13" title="編輯章節：另見"><span>編輯</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/%E5%8D%A4%E4%BB%A3%E7%83%B7%E7%83%83" title="鹵烷">鹵烷</a></li> <li><span class="ilh-all" data-orig-title="芳香鹵化物" data-lang-code="en" data-lang-name="英語" data-foreign-title="Aryl halide"><span class="ilh-page"><a href="/w/index.php?title=%E8%8A%B3%E9%A6%99%E9%B9%B5%E5%8C%96%E7%89%A9&action=edit&redlink=1" class="new" title="芳香鹵化物（頁面不存在）">芳香鹵化物</a></span><span class="noprint ilh-comment">（<span class="ilh-lang">英語</span><span class="ilh-colon">：</span><span class="ilh-link"><a href="https://en.wikipedia.org/wiki/Aryl_halide" class="extiw" title="en:Aryl halide"><span lang="en" dir="auto">Aryl halide</span></a></span>）</span></span></li> <li><span class="ilh-all" data-orig-title="自由基鹵化" data-lang-code="en" data-lang-name="英語" data-foreign-title="Free-radical halogenation"><span class="ilh-page"><a href="/w/index.php?title=%E8%87%AA%E7%94%B1%E5%9F%BA%E9%B9%B5%E5%8C%96&action=edit&redlink=1" class="new" title="自由基鹵化（頁面不存在）">自由基鹵化</a></span><span class="noprint ilh-comment">（<span class="ilh-lang">英語</span><span class="ilh-colon">：</span><span class="ilh-link"><a href="https://en.wikipedia.org/wiki/Free-radical_halogenation" class="extiw" title="en:Free-radical halogenation"><span lang="en" dir="auto">Free-radical halogenation</span></a></span>）</span></span></li> <li><a href="/wiki/%E5%8D%A4%E4%BB%A3%E9%85%AE" title="鹵代酮">鹵代酮</a></li> <li><a href="/wiki/%E8%A6%AA%E9%9B%BB%E5%8F%96%E4%BB%A3%E5%8F%8D%E6%87%89" class="mw-redirect" title="親電取代反應">親電取代反應</a></li> <li><a href="/wiki/%E6%9C%89%E6%A9%9F%E9%B9%B5%E5%8C%96%E7%89%A9" title="有機鹵化物">有機鹵化物</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="參考文獻"><span id=".E5.8F.83.E8.80.83.E6.96.87.E7.8D.BB"></span>參考文獻</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E9%B9%B5%E5%8C%96&action=edit&section=14" title="編輯章節：參考文獻"><span>編輯</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="reflist" style="list-style-type: decimal;"> <ol class="references"> <li id="cite_note-Patai-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-Patai_1-0">^</a></b></span> <span class="reference-text">Yoel Sasson "Formation of Carbon–Halogen Bonds (Cl, Br, I)" in Patai's Chemistry of Functional Groups, 2009, Wiley-VCH, Weinheim. <a href="/wiki/DOI" title="DOI">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F9780470682531.pat0011">10.1002/9780470682531.pat0011</a></span> </li> <li id="cite_note-Ullmann-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-Ullmann_2-0"><sup><b>2.0</b></sup></a> <a href="#cite_ref-Ullmann_2-1"><sup><b>2.1</b></sup></a></span> <span class="reference-text">M. Rossberg et al. 「Chlorinated Hydrocarbons」 in Ullmann’s Encyclopedia of Industrial Chemistry 2006, Wiley-VCH, Weinheim. <a href="/wiki/DOI" title="DOI">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F14356007.a06_233.pub2">10.1002/14356007.a06_233.pub2</a></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><cite class="citation journal">T. Mori, R. Rathore. X-Ray structure of bridged 2,2'-bi(adamant-2-ylidene) chloronium cation and comparison of its reactivity with a singly bonded chloroarenium cation. <a href="/w/index.php?title=Chem._Commun.&action=edit&redlink=1" class="new" title="Chem. Commun.（頁面不存在）">Chem. Commun.</a> 1998, (8): 927–928. <a rel="nofollow" class="external text" href="https://doi.org/10.1039%2Fa709063c"><span title="數位物件識別號">doi:10.1039/a709063c</span></a>.</cite><span title="ctx_ver=Z39.88-2004&rfr_id=info%3Asid%2Fzh.wikipedia.org%3A%E9%B9%B5%E5%8C%96&rft.atitle=X-Ray+structure+of+bridged+2%2C2%27-bi%28adamant-2-ylidene%29+chloronium+cation+and+comparison+of+its+reactivity+with+a+singly+bonded+chloroarenium+cation&rft.au=T.+Mori%2C+R.+Rathore&rft.date=1998&rft.genre=article&rft.issue=8&rft.jtitle=Chem.+Commun.&rft.pages=927-928&rft_id=info%3Adoi%2F10.1039%2Fa709063c&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal" class="Z3988"><span style="display:none;"> </span></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">Illustrative procedure for chlorination of an aromatic compound: <cite style="font-style:normal">Edward R. Atkinson, Donald M. Murphy, and James E. Lufkin (1951). "<a rel="nofollow" class="external text" href="http://www.orgsyn.org/demo.aspx?prep=CV4P0872">dl-4,4',6,6'-Tetrachlorodiphenic Acid</a>". <i><a href="/wiki/%E6%9C%89%E6%9C%BA%E5%90%88%E6%88%90_(%E6%9C%9F%E5%88%8A)" title="有機合成 (期刊)">Org. Synth.</a></i>; <i>Coll. Vol.</i> <b>4</b>: 872.</cite><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=dl-4%2C4%27%2C6%2C6%27-Tetrachlorodiphenic+Acid &rft.date=1951&rft.au=Edward+R.+Atkinson%2C+Donald+M.+Murphy%2C+and+James+E.+Lufkin"> </span></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text">Marshall, K. A. 2003. Chlorocarbons and Chlorohydrocarbons, Survey. Kirk-Othmer Encyclopedia of Chemical Technology</span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text">"Oxy | Oxychlorination." Oxy | Oxychlorination. N.p., n.d. Web. 10 Oct. 2012. <a rel="nofollow" class="external autonumber" href="http://www.oxy.com/OurBusinesses/Chemicals/TechnologyLicensing/Pages/OxyChlorination.aspx">[1]</a> （<a rel="nofollow" class="external text" href="//web.archive.org/web/20130104055309/http://www.oxy.com/OurBusinesses/Chemicals/TechnologyLicensing/Pages/OxyChlorination.aspx">頁面存檔備份</a>，存於<a href="/wiki/%E4%BA%92%E8%81%94%E7%BD%91%E6%A1%A3%E6%A1%88%E9%A6%86" title="網際網路檔案館">網際網路檔案館</a>）</span> </li> <li id="cite_note-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text"><i>Synthesis of essential drugs</i>, Ruben Vardanyan, Victor Hruby; Elsevier 2005 <a href="/wiki/Special:%E7%BD%91%E7%BB%9C%E4%B9%A6%E6%BA%90/0444521666" class="internal mw-magiclink-isbn">ISBN 0-444-52166-6</a></span> </li> <li id="cite_note-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-8">^</a></b></span> <span class="reference-text">Gordon W. Gribble 「The diversity of naturally occurring organobromine compounds」 Chemical Society Reviews, 1999, volume 28, pages 335 – 346.<a href="/wiki/DOI" title="DOI">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2Fa900201d">10.1039/a900201d</a></span> </li> <li id="cite_note-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-9">^</a></b></span> <span class="reference-text"><cite class="citation book">Greenwood, Norman Neill; Earnshaw, Alan. <a rel="nofollow" class="external text" href="https://www.worldcat.org/title/chemistry-of-the-elements/oclc/1040112384">Chemistry of the elements</a>. 2016. <a href="/wiki/Special:%E7%BD%91%E7%BB%9C%E4%B9%A6%E6%BA%90/978-0-7506-3365-9" title="Special:網絡書源/978-0-7506-3365-9"><span title="國際標準書號">ISBN</span> 978-0-7506-3365-9</a>. <a rel="nofollow" class="external text" href="//www.worldcat.org/oclc/1040112384"><span title="OCLC">OCLC 1040112384</span></a> <span style="font-family: sans-serif; cursor: default; 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