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<span class="vector-toc-numb">2</span> <span>Stereochemistry of poly-1-alkenes</span> </div> </a> <ul id="toc-Stereochemistry_of_poly-1-alkenes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Classes" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Classes"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Classes</span> </div> </a> <button aria-controls="toc-Classes-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 Classes subsection</span> </button> <ul id="toc-Classes-sublist" class="vector-toc-list"> <li id="toc-Heterogeneous_catalysts" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Heterogeneous_catalysts"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Heterogeneous catalysts</span> </div> </a> <ul id="toc-Heterogeneous_catalysts-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Homogeneous_catalysts" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Homogeneous_catalysts"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Homogeneous catalysts</span> </div> </a> <ul id="toc-Homogeneous_catalysts-sublist" class="vector-toc-list"> <li id="toc-Metallocene_catalysts" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Metallocene_catalysts"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2.1</span> <span>Metallocene catalysts</span> </div> </a> <ul id="toc-Metallocene_catalysts-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Non-metallocene_catalysts" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Non-metallocene_catalysts"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2.2</span> <span>Non-metallocene catalysts</span> </div> </a> <ul id="toc-Non-metallocene_catalysts-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> <li id="toc-Mechanism_of_Ziegler–Natta_polymerization" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Mechanism_of_Ziegler–Natta_polymerization"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Mechanism of Ziegler–Natta polymerization</span> </div> </a> <button aria-controls="toc-Mechanism_of_Ziegler–Natta_polymerization-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 Mechanism of Ziegler–Natta polymerization subsection</span> </button> <ul id="toc-Mechanism_of_Ziegler–Natta_polymerization-sublist" class="vector-toc-list"> <li id="toc-Termination_processes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Termination_processes"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Termination processes</span> </div> </a> <ul id="toc-Termination_processes-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Commercial_polymers_prepared_with_Ziegler–Natta_catalysts" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Commercial_polymers_prepared_with_Ziegler–Natta_catalysts"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Commercial polymers prepared with Ziegler–Natta catalysts</span> </div> </a> <ul id="toc-Commercial_polymers_prepared_with_Ziegler–Natta_catalysts-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">6</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Further_reading" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Further_reading"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Further reading</span> </div> </a> <ul id="toc-Further_reading-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 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Available in 21 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-21" 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">21 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%AD%D9%81%D8%A7%D8%B2_%D8%AA%D8%B3%D9%8A%D8%BA%D9%84%D8%B1-%D9%86%D8%A7%D8%AA%D8%A7" title="حفاز تسيغلر-ناتا – Arabic" lang="ar" hreflang="ar" data-title="حفاز تسيغلر-ناتا" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Tsiqler-Natta_katalizatorlar%C4%B1" title="Tsiqler-Natta katalizatorları – Azerbaijani" lang="az" hreflang="az" data-title="Tsiqler-Natta katalizatorları" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Catalitzador_de_Ziegler%E2%80%93Natta" title="Catalitzador de Ziegler–Natta – Catalan" lang="ca" hreflang="ca" data-title="Catalitzador de Ziegler–Natta" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Zieglerovy%E2%80%93Nattovy_katalyz%C3%A1tory" title="Zieglerovy–Nattovy katalyzátory – Czech" lang="cs" hreflang="cs" data-title="Zieglerovy–Nattovy katalyzátory" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Ziegler-Natta-Verfahren" title="Ziegler-Natta-Verfahren – German" lang="de" hreflang="de" data-title="Ziegler-Natta-Verfahren" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Catalizador_Ziegler-Natta" title="Catalizador Ziegler-Natta – Spanish" lang="es" hreflang="es" data-title="Catalizador Ziegler-Natta" 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/Ziegler-Natta_katalizatzaile" title="Ziegler-Natta katalizatzaile – Basque" lang="eu" hreflang="eu" data-title="Ziegler-Natta katalizatzaile" 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/%DA%A9%D8%A7%D8%AA%D8%A7%D9%84%DB%8C%D8%B2%DA%AF%D8%B1_%D8%B2%DB%8C%DA%AF%D9%84%D8%B1-%D9%86%D8%A7%D8%AA%D8%A7" title="کاتالیزگر زیگلر-ناتا – Persian" lang="fa" hreflang="fa" data-title="کاتالیزگر زیگلر-ناتا" 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/Catalyse_de_Ziegler-Natta" title="Catalyse de Ziegler-Natta – French" lang="fr" hreflang="fr" data-title="Catalyse de Ziegler-Natta" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%B9%98%EA%B8%80%EB%9F%AC-%EB%82%98%ED%83%80_%EC%B4%89%EB%A7%A4" title="치글러-나타 촉매 – Korean" lang="ko" hreflang="ko" data-title="치글러-나타 촉매" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%9C%E0%A4%BF%E0%A4%97%E0%A4%B2%E0%A4%B0-%E0%A4%A8%E0%A4%BE%E0%A4%9F%E0%A4%BE_%E0%A4%89%E0%A4%A4%E0%A5%8D%E0%A4%AA%E0%A5%8D%E0%A4%B0%E0%A5%87%E0%A4%B0%E0%A4%95" title="जिगलर-नाटा उत्प्रेरक – Hindi" lang="hi" hreflang="hi" data-title="जिगलर-नाटा उत्प्रेरक" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Katalis_Ziegler%E2%80%93Natta" title="Katalis Ziegler–Natta – Indonesian" lang="id" hreflang="id" data-title="Katalis Ziegler–Natta" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Catalizzatori_di_Ziegler-Natta" title="Catalizzatori di Ziegler-Natta – Italian" lang="it" hreflang="it" data-title="Catalizzatori di Ziegler-Natta" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Ziegler-Natta-katalysator" title="Ziegler-Natta-katalysator – Dutch" lang="nl" hreflang="nl" data-title="Ziegler-Natta-katalysator" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%81%E3%83%BC%E3%82%B0%E3%83%A9%E3%83%BC%E3%83%BB%E3%83%8A%E3%83%83%E3%82%BF%E8%A7%A6%E5%AA%92" title="チーグラー・ナッタ触媒 – Japanese" lang="ja" hreflang="ja" data-title="チーグラー・ナッタ触媒" 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-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Katalizatory_Zieglera-Natty" title="Katalizatory Zieglera-Natty – Polish" lang="pl" hreflang="pl" data-title="Katalizatory Zieglera-Natty" 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/Catalisador_Ziegler-Natta" title="Catalisador Ziegler-Natta – Portuguese" lang="pt" hreflang="pt" data-title="Catalisador Ziegler-Natta" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%9A%D0%B0%D1%82%D0%B0%D0%BB%D0%B8%D0%B7%D0%B0%D1%82%D0%BE%D1%80%D1%8B_%D0%A6%D0%B8%D0%B3%D0%BB%D0%B5%D1%80%D0%B0_%E2%80%94_%D0%9D%D0%B0%D1%82%D1%82%D0%B0" title="Катализаторы Циглера — Натта – Russian" lang="ru" hreflang="ru" data-title="Катализаторы Циглера — Натта" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Ziegler%E2%80%93Natta-katalyytti" title="Ziegler–Natta-katalyytti – Finnish" lang="fi" hreflang="fi" data-title="Ziegler–Natta-katalyytti" data-language-autonym="Suomi" data-language-local-name="Finnish" 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<div class="vector-body-before-content"> <div class="mw-indicators"> </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">Catalyst for synthesis of polymers of 1-alkenes</div> <p>A <b>Ziegler–Natta catalyst</b>, named after <a href="/wiki/Karl_Ziegler" title="Karl Ziegler">Karl Ziegler</a> and <a href="/wiki/Giulio_Natta" title="Giulio Natta">Giulio Natta</a>, is a <a href="/wiki/Catalyst" class="mw-redirect" title="Catalyst">catalyst</a> used in the synthesis of <a href="/wiki/Polymers" class="mw-redirect" title="Polymers">polymers</a> of 1-alkenes (<a href="/wiki/Alpha-olefin" class="mw-redirect" title="Alpha-olefin">alpha-olefins</a>). Two broad classes of Ziegler–Natta catalysts are employed, distinguished by their solubility: </p> <ul><li>Heterogeneous <a href="/wiki/Catalyst_support" title="Catalyst support">supported catalysts</a> based on titanium compounds are used in polymerization reactions in combination with cocatalysts, <a href="/wiki/Organoaluminum" class="mw-redirect" title="Organoaluminum">organoaluminum</a> compounds such as <a href="/wiki/Triethylaluminium" title="Triethylaluminium">triethylaluminium</a>, Al(C<sub>2</sub>H<sub>5</sub>)<sub>3</sub>. This class of catalyst dominates the industry.<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></li> <li>Homogeneous catalysts usually based on complexes of the <a href="/wiki/Group_4_elements" class="mw-redirect" title="Group 4 elements">group 4 metals</a> <a href="/wiki/Titanium" title="Titanium">titanium</a>, <a href="/wiki/Zirconium" title="Zirconium">zirconium</a> or <a href="/wiki/Hafnium" title="Hafnium">hafnium</a>. They are usually used in combination with a different organoaluminum cocatalyst, <a href="/wiki/Methylaluminoxane" title="Methylaluminoxane">methylaluminoxane</a> (or methylalumoxane, MAO). These catalysts traditionally contain <a href="/wiki/Metallocene" title="Metallocene">metallocenes</a> but also feature <a href="/wiki/Multidentate" class="mw-redirect" title="Multidentate">multidentate</a> oxygen- and nitrogen-based <a href="/wiki/Ligands" class="mw-redirect" title="Ligands">ligands</a>.<sup id="cite_ref-Handbook_2-0" class="reference"><a href="#cite_note-Handbook-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></li></ul> <p>Ziegler–Natta catalysts are used to polymerize terminal <a href="/wiki/Alkene" title="Alkene">alkenes</a> (ethylene and alkenes with the <a href="/wiki/Vinyl_group" title="Vinyl group">vinyl</a> double bond): </p> <dl><dd><i>n</i> CH<sub>2</sub>=CHR → −[CH<sub>2</sub>−CHR]<sub><i>n</i></sub>−;</dd></dl> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ziegler%E2%80%93Natta_catalyst&action=edit&section=1" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The 1963 <a href="/wiki/Nobel_Prize_in_Chemistry" title="Nobel Prize in Chemistry">Nobel Prize in Chemistry</a> was awarded to German <a href="/wiki/Karl_Ziegler" title="Karl Ziegler">Karl Ziegler</a>, for his discovery of first titanium-based catalysts, and Italian <a href="/wiki/Giulio_Natta" title="Giulio Natta">Giulio Natta</a>, for using them to prepare stereoregular polymers from <a href="/wiki/Propylene" title="Propylene">propylene</a>. Ziegler–Natta catalysts have been used in the commercial manufacture of various polyolefins since 1956. As of 2010, the total volume of plastics, elastomers, and rubbers produced from alkenes with these and related (especially Phillips) catalysts worldwide exceeds 100 million tonnes. Together, these polymers represent the largest-volume commodity plastics as well as the largest-volume commodity chemicals in the world. </p><p>In the early 1950s workers at <a href="/wiki/Phillips_Petroleum" class="mw-redirect" title="Phillips Petroleum">Phillips Petroleum</a> discovered that chromium catalysts are highly effective for the low-temperature polymerization of ethylene, which launched major industrial technologies culminating in the <a href="/wiki/Phillips_catalyst" title="Phillips catalyst">Phillips catalyst</a>. A few years later, Ziegler discovered that a combination of <a href="/wiki/Titanium_tetrachloride" title="Titanium tetrachloride">titanium tetrachloride</a> (TiCl<sub>4</sub>) and <a href="/wiki/Diethylaluminium_chloride" title="Diethylaluminium chloride">diethylaluminium chloride</a> (Al(C<sub>2</sub>H<sub>5</sub>)<sub>2</sub>Cl) gave comparable activities for the production of polyethylene. Natta used crystalline <a href="/wiki/Titanium_trichloride" class="mw-redirect" title="Titanium trichloride">α-TiCl<sub>3</sub></a> in combination with <a href="/wiki/Triethylaluminium" title="Triethylaluminium">Al(C<sub>2</sub>H<sub>5</sub>)<sub>3</sub></a> to produce first <a href="/wiki/Isotactic" class="mw-redirect" title="Isotactic">isotactic</a> <a href="/wiki/Polypropylene" title="Polypropylene">polypropylene</a>.<sup id="cite_ref-nattadanusso_3-0" class="reference"><a href="#cite_note-nattadanusso-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Usually Ziegler catalysts refer to <a href="/wiki/Titanium" title="Titanium">titanium</a>-based systems for conversions of <a href="/wiki/Ethylene" title="Ethylene">ethylene</a> and Ziegler–Natta catalysts refer to systems for conversions of <a href="/wiki/Propylene" title="Propylene">propylene</a>. </p><p>Also, in the 1960s, <a href="/wiki/BASF" title="BASF">BASF</a> developed a gas-phase, mechanically-stirred <a href="/wiki/Polymerization" title="Polymerization">polymerization</a> process for making <a href="/wiki/Polypropylene" title="Polypropylene">polypropylene</a>. In that process, the particle bed in the reactor was either not fluidized or not fully fluidized. In 1968, the first gas-phase fluidized-bed polymerization process, the Unipol process, was commercialized by <a href="/wiki/Union_Carbide" title="Union Carbide">Union Carbide</a> to produce polyethylene. In the mid-1980s, the Unipol process was further extended to produce <a href="/wiki/Polypropylene" title="Polypropylene">polypropylene</a>. </p><p>In the 1970s, <a href="/wiki/Magnesium_chloride" title="Magnesium chloride">magnesium chloride</a> (MgCl<sub>2</sub>) was discovered to greatly enhance the activity of the titanium-based catalysts. These catalysts were so active that the removal of unwanted amorphous polymer and residual titanium from the product (so-called deashing) was no longer necessary, enabling the commercialization of <a href="/wiki/Linear_low-density_polyethylene" title="Linear low-density polyethylene">linear low-density polyethylene</a> (LLDPE) resins and allowed the development of fully amorphous copolymers.<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><p>The fluidized-bed process remains one of the two most widely used processes for producing <a href="/wiki/Polypropylene" title="Polypropylene">polypropylene</a>.<sup id="cite_ref-Technology_Economics_Program_5-0" class="reference"><a href="#cite_note-Technology_Economics_Program-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Stereochemistry_of_poly-1-alkenes">Stereochemistry of poly-1-alkenes</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ziegler%E2%80%93Natta_catalyst&action=edit&section=2" title="Edit section: Stereochemistry of poly-1-alkenes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Natta first used polymerization catalysts based on titanium chlorides to polymerize <a href="/wiki/Propylene" title="Propylene">propylene</a> and other 1-alkenes. He discovered that these polymers are crystalline materials and ascribed their crystallinity to a special feature of the polymer structure called <a href="/wiki/Stereoregularity" class="mw-redirect" title="Stereoregularity">stereoregularity</a>. </p> <figure class="mw-default-size mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Polypropylene_tacticity.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8a/Polypropylene_tacticity.svg/400px-Polypropylene_tacticity.svg.png" decoding="async" width="400" height="113" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8a/Polypropylene_tacticity.svg/600px-Polypropylene_tacticity.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8a/Polypropylene_tacticity.svg/800px-Polypropylene_tacticity.svg.png 2x" data-file-width="821" data-file-height="231" /></a><figcaption>Short segments of polypropylene, showing examples of isotactic (above) and syndiotactic (below) <a href="/wiki/Tacticity" title="Tacticity">tacticity</a>.</figcaption></figure> <p>The concept of stereoregularity in polymer chains is illustrated in the picture on the left with polypropylene. Stereoregular poly(1-alkene) can be <a href="/wiki/Isotactic" class="mw-redirect" title="Isotactic">isotactic</a> or <a href="/wiki/Syndiotactic" class="mw-redirect" title="Syndiotactic">syndiotactic</a> depending on the relative orientation of the <a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">alkyl</a> groups in polymer chains consisting of units −[CH<sub>2</sub>−CHR]−, like the CH<sub>3</sub> groups in the figure. In the isotactic polymers, all stereogenic centers CHR share the same configuration. The stereogenic centers in syndiotactic polymers alternate their relative configuration. A polymer that lacks any regular arrangement in the position of its alkyl substituents (R) is called atactic. Both isotactic and syndiotactic polypropylene are crystalline, whereas atactic polypropylene, which can also be prepared with special Ziegler–Natta catalysts, is amorphous. The stereoregularity of the polymer is determined by the catalyst used to prepare it. </p> <div class="mw-heading mw-heading2"><h2 id="Classes">Classes</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ziegler%E2%80%93Natta_catalyst&action=edit&section=3" title="Edit section: Classes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Heterogeneous_catalysts">Heterogeneous catalysts</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ziegler%E2%80%93Natta_catalyst&action=edit&section=4" title="Edit section: Heterogeneous catalysts"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Heterogeneous_catalysis" title="Heterogeneous catalysis">Heterogeneous catalysis</a></div> <p>The first and dominant class of titanium-based catalysts (and some <a href="/wiki/Vanadium" title="Vanadium">vanadium</a>-based catalysts) for alkene polymerization can be roughly subdivided into two subclasses: </p> <ul><li>catalysts suitable for homopolymerization of ethylene and for ethylene/1-alkene <a href="/wiki/Copolymer" title="Copolymer">copolymerization</a> reactions leading to copolymers with a low 1-alkene content, 2–4 mol% (<a href="/wiki/LLDPE" class="mw-redirect" title="LLDPE">LLDPE</a> resins), and</li> <li>catalysts suitable for the synthesis of isotactic 1-alkenes.</li></ul> <p>The overlap between these two subclasses is relatively small because the requirements to the respective catalysts differ widely. </p><p>Commercial catalysts are supported by being bound to a solid with a high surface area. Both <a href="/wiki/Titanium_tetrachloride" title="Titanium tetrachloride">TiCl<sub>4</sub></a> and <a href="/wiki/Titanium_trichloride" class="mw-redirect" title="Titanium trichloride">TiCl<sub>3</sub></a> give active catalysts.<sup id="cite_ref-ref1_6-0" class="reference"><a href="#cite_note-ref1-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ref2_7-0" class="reference"><a href="#cite_note-ref2-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> The support in the majority of the catalysts is <a href="/wiki/Magnesium_chloride" title="Magnesium chloride">MgCl<sub>2</sub></a>. A third component of most catalysts is a carrier, a material that determines the size and the shape of catalyst particles. The preferred carrier is <a href="/wiki/Microporous" class="mw-redirect" title="Microporous">microporous</a> spheres of <a href="/wiki/Amorphous_silica" class="mw-redirect" title="Amorphous silica">amorphous silica</a> with a diameter of 30–40 mm. During the catalyst synthesis, both the titanium compounds and MgCl<sub>2</sub> are packed into the silica pores. All these catalysts are activated with organoaluminum compounds such as <a href="/wiki/Triethylaluminium" title="Triethylaluminium">Al(C<sub>2</sub>H<sub>5</sub>)<sub>3</sub></a>.<sup id="cite_ref-ref2_7-1" class="reference"><a href="#cite_note-ref2-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p><p>All modern supported Ziegler–Natta catalysts designed for polymerization of propylene and higher 1-alkenes are prepared with <a href="/wiki/Titanium_tetrachloride" title="Titanium tetrachloride">TiCl<sub>4</sub></a> as the active ingredient and <a href="/wiki/Magnesium_chloride" title="Magnesium chloride">MgCl<sub>2</sub></a> as a support. Another component of all such catalysts is an organic modifier, usually an <a href="/wiki/Ester" title="Ester">ester</a> of an <a href="/wiki/Aromatic_acid" title="Aromatic acid">aromatic diacid</a> or a <a href="/wiki/Ether" title="Ether">diether</a>. The modifiers react both with inorganic ingredients of the solid catalysts as well as with organoaluminum cocatalysts.<sup id="cite_ref-ref2_7-2" class="reference"><a href="#cite_note-ref2-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> These catalysts polymerize propylene and other 1-alkenes to highly crystalline isotactic polymers.<sup id="cite_ref-ref1_6-1" class="reference"><a href="#cite_note-ref1-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ref2_7-3" class="reference"><a href="#cite_note-ref2-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Homogeneous_catalysts">Homogeneous catalysts</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ziegler%E2%80%93Natta_catalyst&action=edit&section=5" title="Edit section: Homogeneous catalysts"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A second class of Ziegler–Natta catalysts are soluble in the reaction medium. Traditionally such homogeneous catalysts were derived from <a href="/wiki/Metallocene" title="Metallocene">metallocenes</a>, but the structures of active catalysts have been significantly broadened to include nitrogen-based ligands. </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:VersifyCats.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c9/VersifyCats.png/220px-VersifyCats.png" decoding="async" width="220" height="135" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c9/VersifyCats.png/330px-VersifyCats.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c9/VersifyCats.png/440px-VersifyCats.png 2x" data-file-width="1767" data-file-height="1085" /></a><figcaption>A post-metallocene catalyst developed at <a href="/wiki/Dow_Chemical" class="mw-redirect" title="Dow Chemical">Dow Chemical</a>.<sup id="cite_ref-Klosin_8-0" class="reference"><a href="#cite_note-Klosin-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup></figcaption></figure> <div class="mw-heading mw-heading4"><h4 id="Metallocene_catalysts">Metallocene catalysts</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ziegler%E2%80%93Natta_catalyst&action=edit&section=6" title="Edit section: Metallocene catalysts"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Kaminsky_catalyst" title="Kaminsky catalyst">Kaminsky catalyst</a></div> <p>These catalysts are metallocenes together with a cocatalyst, typically MAO, −[O−Al(CH<sub>3</sub>)]<sub><i>n</i></sub>−. The idealized metallocene catalysts have the composition <a href="/wiki/Cyclopentadienyl" title="Cyclopentadienyl">Cp</a><sub>2</sub>MCl<sub>2</sub> (M = Ti, <a href="/wiki/Zirconium" title="Zirconium">Zr</a>, <a href="/wiki/Hafnium" title="Hafnium">Hf</a>) such as <a href="/wiki/Titanocene_dichloride" title="Titanocene dichloride">titanocene dichloride</a>. Typically, the organic ligands are derivatives of <a href="/wiki/Cyclopentadienyl" title="Cyclopentadienyl">cyclopentadienyl</a>. In some complexes, the two <a href="/wiki/Cyclopentadiene" title="Cyclopentadiene">cyclopentadiene</a> (Cp) rings are linked with bridges, like −CH<sub>2</sub>−CH<sub>2</sub>− or >SiPh<sub>2</sub>. Depending on the type of their cyclopentadienyl ligands, for example by using an <a href="/wiki/Ansa-metallocene" title="Ansa-metallocene"><i>ansa</i>-bridge</a>, metallocene catalysts can produce either isotactic or syndiotactic polymers of propylene and other 1-alkenes.<sup id="cite_ref-ref1_6-2" class="reference"><a href="#cite_note-ref1-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ref2_7-4" class="reference"><a href="#cite_note-ref2-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><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><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-heading4"><h4 id="Non-metallocene_catalysts">Non-metallocene catalysts</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ziegler%E2%80%93Natta_catalyst&action=edit&section=7" title="Edit section: Non-metallocene catalysts"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Post-metallocene_catalyst" title="Post-metallocene catalyst">Post-metallocene catalyst</a></div> <p>Ziegler–Natta catalysts of the third class, non-metallocene catalysts, use a variety of complexes of various metals, ranging from scandium to lanthanoid and actinoid metals, and a large variety of ligands containing <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> (O<sub>2</sub>), <a href="/wiki/Nitrogen" title="Nitrogen">nitrogen</a> (N<sub>2</sub>), <a href="/wiki/Phosphorus" title="Phosphorus">phosphorus</a> (P), and <a href="/wiki/Sulfur" title="Sulfur">sulfur</a> (S). The complexes are activated using MAO, as is done for metallocene catalysts. </p><p>Most Ziegler–Natta catalysts and all the alkylaluminium cocatalysts are unstable in air, and the alkylaluminium compounds are <a href="/wiki/Pyrophoric" class="mw-redirect" title="Pyrophoric">pyrophoric</a>. The catalysts, therefore, are always prepared and handled under an inert atmosphere. </p> <div class="mw-heading mw-heading2"><h2 id="Mechanism_of_Ziegler–Natta_polymerization"><span id="Mechanism_of_Ziegler.E2.80.93Natta_polymerization"></span>Mechanism of Ziegler–Natta polymerization</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ziegler%E2%80%93Natta_catalyst&action=edit&section=8" title="Edit section: Mechanism of Ziegler–Natta polymerization"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The structure of active centers in Ziegler–Natta catalysts is well established only for metallocene catalysts. An idealized and simplified metallocene complex Cp<sub>2</sub>ZrCl<sub>2</sub> represents a typical precatalyst. It is unreactive toward alkenes. The dihalide reacts with MAO and is transformed into a metallocenium ion Cp<sub>2</sub><span class="sfrac nowrap;"><span style="display:none; display:inline-block; text-align:center;"><span style="display:block; line-height:0.8em; font-size:70%;">+</span><span style="display:block; line-height:1em;">Zr</span></span></span>CH<sub>3</sub>, which is ion-paired to some derivative(s) of MAO. A polymer molecule grows by numerous insertion reactions of C=C bonds of 1-alkene molecules into the Zr–C bond in the ion: </p> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:ZNonSingleSite.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ee/ZNonSingleSite.png/480px-ZNonSingleSite.png" decoding="async" width="480" height="68" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ee/ZNonSingleSite.png/720px-ZNonSingleSite.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ee/ZNonSingleSite.png/960px-ZNonSingleSite.png 2x" data-file-width="2957" data-file-height="418" /></a><figcaption>Simplified mechanism for Zr-catalyzed ethylene polymerization.</figcaption></figure> <p>Many thousands of alkene insertion reactions occur at each active center resulting in the formation of long polymer chains attached to the center. The <a href="/wiki/Cossee%E2%80%93Arlman_mechanism" title="Cossee–Arlman mechanism">Cossee–Arlman mechanism</a> describes the growth of stereospecific polymers.<sup id="cite_ref-nattadanusso_3-1" class="reference"><a href="#cite_note-nattadanusso-3"><span class="cite-bracket">[</span>3<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> This mechanism states that the polymer grows through alkene coordination at a vacant site at the titanium atom, which is followed by insertion of the C=C bond into the Ti−C bond at the active center. </p> <div class="mw-heading mw-heading3"><h3 id="Termination_processes">Termination processes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ziegler%E2%80%93Natta_catalyst&action=edit&section=9" title="Edit section: Termination processes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>On occasion, the polymer chain is disengaged from the active centers in the chain termination reaction. Several pathways exist for termination: </p> <dl><dd>Cp<sub>2</sub><span class="sfrac nowrap;"><span style="display:none; display:inline-block; text-align:center;"><span style="display:block; line-height:0.8em; font-size:70%;">+</span><span style="display:block; line-height:1em;">Zr</span></span></span>−(CH<sub>2</sub>−CHR)<sub><i>n</i></sub>−CH<sub>3</sub> + CH<sub>2</sub>=CHR → Cp<sub>2</sub><span class="sfrac nowrap;"><span style="display:none; display:inline-block; text-align:center;"><span style="display:block; line-height:0.8em; font-size:70%;">+</span><span style="display:block; line-height:1em;">Zr</span></span></span>−CH<sub>2</sub>−CH<sub>2</sub>R + CH<sub>2</sub>=CR–polymer</dd></dl> <p>Another type of chain termination reaction called a β-hydride elimination reaction also occurs periodically: </p> <dl><dd>Cp<sub>2</sub><span class="sfrac nowrap;"><span style="display:none; display:inline-block; text-align:center;"><span style="display:block; line-height:0.8em; font-size:70%;">+</span><span style="display:block; line-height:1em;">Zr</span></span></span>−(CH<sub>2</sub>−CHR)<sub>n</sub>−CH<sub>3</sub> → Cp<sub>2</sub><span class="sfrac nowrap;"><span style="display:none; display:inline-block; text-align:center;"><span style="display:block; line-height:0.8em; font-size:70%;">+</span><span style="display:block; line-height:1em;">Zr</span></span></span>−H + CH<sub>2</sub>=CR–polymer</dd></dl> <p>Polymerization reactions of alkenes with solid titanium-based catalysts occur at special titanium centers located on the exterior of the catalyst crystallites. Some titanium atoms in these crystallites react with organoaluminum cocatalysts with the formation of Ti–C bonds. The polymerization reaction of alkenes occurs similarly to the reactions in metallocene catalysts: </p> <dl><dd>L<sub><i>n</i></sub>Ti–CH<sub>2</sub>−CHR–polymer + CH<sub>2</sub>=CHR → L<sub><i>n</i></sub>Ti–CH<sub>2</sub>-CHR–CH<sub>2</sub>−CHR–polymer</dd></dl> <p>The two chain termination reactions occur quite rarely in Ziegler–Natta catalysis and the formed polymers have a too high molecular weight to be of commercial use. To reduce the molecular weight, hydrogen is added to the polymerization reaction: </p> <dl><dd>L<sub><i>n</i></sub>Ti–CH<sub>2</sub>−CHR–polymer + H<sub>2</sub> → L<sub><i>n</i></sub>Ti−H + CH<sub>3</sub>−CHR–polymer</dd></dl> <p>Another termination process involves the action of protic (acidic) reagents, which can be intentionally added or adventitious. </p> <div class="mw-heading mw-heading2"><h2 id="Commercial_polymers_prepared_with_Ziegler–Natta_catalysts"><span id="Commercial_polymers_prepared_with_Ziegler.E2.80.93Natta_catalysts"></span>Commercial polymers prepared with Ziegler–Natta catalysts</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ziegler%E2%80%93Natta_catalyst&action=edit&section=10" title="Edit section: Commercial polymers prepared with Ziegler–Natta catalysts"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Polyethylene" title="Polyethylene">Polyethylene</a></li> <li><a href="/wiki/Polypropylene" title="Polypropylene">Polypropylene</a></li> <li>Copolymers of ethylene and 1-alkenes</li> <li><a href="/wiki/Polybutene-1" class="mw-redirect" title="Polybutene-1">Polybutene-1</a></li> <li><a href="/wiki/Polymethylpentene" title="Polymethylpentene">Polymethylpentene</a></li> <li>Polycycloolefins</li> <li><a href="/wiki/Polybutadiene" title="Polybutadiene">Polybutadiene</a></li> <li><a href="/wiki/Polyisoprene" title="Polyisoprene">Polyisoprene</a></li> <li>Amorphous poly-alpha-olefins (<a href="/wiki/APAO" class="mw-redirect" title="APAO">APAO</a>)</li> <li><a href="/wiki/Polyacetylene" title="Polyacetylene">Polyacetylene</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ziegler%E2%80%93Natta_catalyst&action=edit&section=11" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist reflist-columns references-column-width" style="column-width: 30em;"> <ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFGiuliano_CecchinGiampiero_MoriniFabrizio_Piemontesi2003" class="citation encyclopaedia cs1">Giuliano Cecchin; Giampiero Morini; Fabrizio Piemontesi (2003). "Ziegler–Natta Catalysts". <i>Kirk-Othmer Encyclopedia of Chemical Technology</i>. Wiley-VCH. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F0471238961.2609050703050303.a01">10.1002/0471238961.2609050703050303.a01</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0471238961" title="Special:BookSources/0471238961"><bdi>0471238961</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Ziegler%E2%80%93Natta+Catalysts&rft.btitle=Kirk-Othmer+Encyclopedia+of+Chemical+Technology&rft.pub=Wiley-VCH&rft.date=2003&rft_id=info%3Adoi%2F10.1002%2F0471238961.2609050703050303.a01&rft.isbn=0471238961&rft.au=Giuliano+Cecchin&rft.au=Giampiero+Morini&rft.au=Fabrizio+Piemontesi&rfr_id=info%3Asid%2Fen.wikipedia.org%3AZiegler%E2%80%93Natta+catalyst" class="Z3988"></span></span> </li> <li id="cite_note-Handbook-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-Handbook_2-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHoffMathers2010" class="citation book cs1">Hoff, Ray; Mathers, Robert T., eds. (2010). <i>Handbook of Transition Metal Polymerization Catalysts</i> (Online ed.). John Wiley & Sons. <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%2F9780470504437">10.1002/9780470504437</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780470504437" title="Special:BookSources/9780470504437"><bdi>9780470504437</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Handbook+of+Transition+Metal+Polymerization+Catalysts&rft.edition=Online&rft.pub=John+Wiley+%26+Sons&rft.date=2010&rft_id=info%3Adoi%2F10.1002%2F9780470504437&rft.isbn=9780470504437&rfr_id=info%3Asid%2Fen.wikipedia.org%3AZiegler%E2%80%93Natta+catalyst" class="Z3988"></span></span> </li> <li id="cite_note-nattadanusso-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-nattadanusso_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-nattadanusso_3-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFNattaDanusso1967" class="citation book cs1">Natta, G.; Danusso, F., eds. (1967). <i>Stereoregular Polymers and Stereospecific Polymerizations</i>. Pergamon Press.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Stereoregular+Polymers+and+Stereospecific+Polymerizations&rft.pub=Pergamon+Press&rft.date=1967&rfr_id=info%3Asid%2Fen.wikipedia.org%3AZiegler%E2%80%93Natta+catalyst" class="Z3988"></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFNowlinMinkKissin2010" class="citation encyclopaedia cs1">Nowlin, T. E.; Mink, R. I.; Kissin, Y. V. (2010). "Supported Magnesium/Titanium-Based Ziegler Catalysts for Production of Polyethylene". In Hoff, Ray; Mathers, Robert T. (eds.). <i>Handbook of Transition Metal Polymerization Catalysts</i> (Online ed.). John Wiley & Sons. pp. 131–155. <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%2F9780470504437.ch6">10.1002/9780470504437.ch6</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780470504437" title="Special:BookSources/9780470504437"><bdi>9780470504437</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Supported+Magnesium%2FTitanium-Based+Ziegler+Catalysts+for+Production+of+Polyethylene&rft.btitle=Handbook+of+Transition+Metal+Polymerization+Catalysts&rft.pages=131-155&rft.edition=Online&rft.pub=John+Wiley+%26+Sons&rft.date=2010&rft_id=info%3Adoi%2F10.1002%2F9780470504437.ch6&rft.isbn=9780470504437&rft.aulast=Nowlin&rft.aufirst=T.+E.&rft.au=Mink%2C+R.+I.&rft.au=Kissin%2C+Y.+V.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AZiegler%E2%80%93Natta+catalyst" class="Z3988"></span></span> </li> <li id="cite_note-Technology_Economics_Program-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-Technology_Economics_Program_5-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation book cs1"><a rel="nofollow" class="external text" href="http://www.magcloud.com/browse/issue/411008"><i>Polypropylene Production via Gas Phase Process, Technology Economics Program</i></a>. 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New York: Wiley-InterScience. pp. 136–139.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Organotransition+Metal+Chemistry&rft.place=New+York&rft.pages=136-139&rft.pub=Wiley-InterScience&rft.date=2002&rft.aulast=Hill&rft.aufirst=A.+F.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AZiegler%E2%80%93Natta+catalyst" class="Z3988"></span></span> </li> <li id="cite_note-ref2-7"><span class="mw-cite-backlink">^ <a href="#cite_ref-ref2_7-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-ref2_7-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-ref2_7-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-ref2_7-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-ref2_7-4"><sup><i><b>e</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKissin2008" class="citation book cs1">Kissin, Y. V. (2008). "Chapter 4". <i>Alkene Polymerization Reactions with Transition Metal Catalysts</i>. Amsterdam: Elsevier.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Chapter+4&rft.btitle=Alkene+Polymerization+Reactions+with+Transition+Metal+Catalysts&rft.place=Amsterdam&rft.pub=Elsevier&rft.date=2008&rft.aulast=Kissin&rft.aufirst=Y.+V.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AZiegler%E2%80%93Natta+catalyst" class="Z3988"></span></span> </li> <li id="cite_note-Klosin-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-Klosin_8-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKlosin,_J.Fontaine,_P._P.Figueroa,_R.2015" class="citation journal cs1">Klosin, J.; Fontaine, P. P.; Figueroa, R. (2015). <a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Facs.accounts.5b00065">"Development of Group Iv Molecular Catalysts for High Temperature Ethylene-Α-Olefin Copolymerization Reactions"</a>. <i>Accounts of Chemical Research</i>. <b>48</b> (7): 2004–2016. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Facs.accounts.5b00065">10.1021/acs.accounts.5b00065</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/26151395">26151395</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Accounts+of+Chemical+Research&rft.atitle=Development+of+Group+Iv+Molecular+Catalysts+for+High+Temperature+Ethylene-%CE%91-Olefin+Copolymerization+Reactions&rft.volume=48&rft.issue=7&rft.pages=2004-2016&rft.date=2015&rft_id=info%3Adoi%2F10.1021%2Facs.accounts.5b00065&rft_id=info%3Apmid%2F26151395&rft.au=Klosin%2C+J.&rft.au=Fontaine%2C+P.+P.&rft.au=Figueroa%2C+R.&rft_id=https%3A%2F%2Fdoi.org%2F10.1021%252Facs.accounts.5b00065&rfr_id=info%3Asid%2Fen.wikipedia.org%3AZiegler%E2%80%93Natta+catalyst" class="Z3988"></span></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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBochmann1994" class="citation book cs1">Bochmann, M. (1994). <i>Organometallics 1, Complexes with Transition Metal-Carbon σ-Bonds</i>. New York: Oxford University Press. pp. 69–71. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780198558132" title="Special:BookSources/9780198558132"><bdi>9780198558132</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Organometallics+1%2C+Complexes+with+Transition+Metal-Carbon+%CF%83-Bonds&rft.place=New+York&rft.pages=69-71&rft.pub=Oxford+University+Press&rft.date=1994&rft.isbn=9780198558132&rft.aulast=Bochmann&rft.aufirst=M.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AZiegler%E2%80%93Natta+catalyst" class="Z3988"></span></span> </li> <li id="cite_note-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-10">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAltKoppl2000" class="citation journal cs1">Alt, H. G.; Koppl, A. (2000). "Effect of the Nature of Metallocene Complexes of Group IV Metals on Their Performance in Catalytic Ethylene and Propylene Polymerization". <i><a href="/wiki/Chem._Rev." class="mw-redirect" title="Chem. Rev.">Chem. Rev.</a></i> <b>100</b> (4): 1205–1222. <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%2Fcr9804700">10.1021/cr9804700</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/11749264">11749264</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chem.+Rev.&rft.atitle=Effect+of+the+Nature+of+Metallocene+Complexes+of+Group+IV+Metals+on+Their+Performance+in+Catalytic+Ethylene+and+Propylene+Polymerization&rft.volume=100&rft.issue=4&rft.pages=1205-1222&rft.date=2000&rft_id=info%3Adoi%2F10.1021%2Fcr9804700&rft_id=info%3Apmid%2F11749264&rft.aulast=Alt&rft.aufirst=H.+G.&rft.au=Koppl%2C+A.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AZiegler%E2%80%93Natta+catalyst" class="Z3988"></span></span> </li> <li id="cite_note-11"><span class="mw-cite-backlink"><b><a href="#cite_ref-11">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFElschenbroichSalzer1992" class="citation book cs1">Elschenbroich, C.; Salzer, A. (1992). <i>Organometallics: a Concise Introduction</i>. New York: VCH Verlag. pp. 423–425.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Organometallics%3A+a+Concise+Introduction&rft.place=New+York&rft.pages=423-425&rft.pub=VCH+Verlag&rft.date=1992&rft.aulast=Elschenbroich&rft.aufirst=C.&rft.au=Salzer%2C+A.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AZiegler%E2%80%93Natta+catalyst" class="Z3988"></span></span> </li> </ol></div> <div class="mw-heading mw-heading2"><h2 id="Further_reading">Further reading</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ziegler%E2%80%93Natta_catalyst&action=edit&section=12" title="Edit section: Further reading"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKissin2008" class="citation book cs1">Kissin, Y. V. (2008). <i>Alkene Polymerization Reactions with Transition Metal Catalysts</i>. Amsterdam: Elsevier.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Alkene+Polymerization+Reactions+with+Transition+Metal+Catalysts&rft.place=Amsterdam&rft.pub=Elsevier&rft.date=2008&rft.aulast=Kissin&rft.aufirst=Y.+V.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AZiegler%E2%80%93Natta+catalyst" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCorradiniGuerraCavallo2004" class="citation journal cs1">Corradini, P.; Guerra, G.; Cavallo, L. (2004). "Do New Century Catalysts Unravel the Mechanism of Stereocontrol of Old Ziegler–Natta Catalysts?". <i><a href="/wiki/Acc._Chem._Res." class="mw-redirect" title="Acc. Chem. Res.">Acc. Chem. Res.</a></i> <b>37</b> (4): 231–241. <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%2Far030165n">10.1021/ar030165n</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/15096060">15096060</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Acc.+Chem.+Res.&rft.atitle=Do+New+Century+Catalysts+Unravel+the+Mechanism+of+Stereocontrol+of+Old+Ziegler%E2%80%93Natta+Catalysts%3F&rft.volume=37&rft.issue=4&rft.pages=231-241&rft.date=2004&rft_id=info%3Adoi%2F10.1021%2Far030165n&rft_id=info%3Apmid%2F15096060&rft.aulast=Corradini&rft.aufirst=P.&rft.au=Guerra%2C+G.&rft.au=Cavallo%2C+L.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AZiegler%E2%80%93Natta+catalyst" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFTakahashi2001" class="citation encyclopaedia cs1">Takahashi, T. (2001). "Titanium(IV) Chloride-Triethylaluminum". <i>Encyclopedia of Reagents for Organic Synthesis</i>. John Wiley & Sons.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Titanium%28IV%29+Chloride-Triethylaluminum&rft.btitle=Encyclopedia+of+Reagents+for+Organic+Synthesis&rft.pub=John+Wiley+%26+Sons&rft.date=2001&rft.aulast=Takahashi&rft.aufirst=T.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AZiegler%E2%80%93Natta+catalyst" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBritovsekGibsonWass1999" class="citation journal cs1">Britovsek, G. J. P.; Gibson, V. C.; Wass, D. F. (1999). "The Search for New-Generation Olefin Polymerization Catalysts: Life beyond Metallocenes". <i><a href="/wiki/Angewandte_Chemie" title="Angewandte Chemie">Angew. Chem. Int. Ed.</a></i> <b>38</b> (4): 428–447. <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%2F%28SICI%291521-3773%2819990215%2938%3A4%3C428%3A%3AAID-ANIE428%3E3.0.CO%3B2-3">10.1002/(SICI)1521-3773(19990215)38:4<428::AID-ANIE428>3.0.CO;2-3</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/29711786">29711786</a>.</cite><span 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title="Ligand field theory">Ligand field theory</a></li> <li><a href="/wiki/18-electron_rule" title="18-electron rule">18-electron rule</a></li> <li><a href="/wiki/D_electron_count" title="D electron count">d electron count</a></li> <li><a href="/wiki/Polyhedral_skeletal_electron_pair_theory" title="Polyhedral skeletal electron pair theory">Polyhedral skeletal electron pair theory</a></li> <li><a href="/wiki/Isolobal_principle" title="Isolobal principle">Isolobal principle</a></li> <li><a href="/wiki/Pi_backbonding" title="Pi backbonding">π backbonding</a></li> <li><a href="/wiki/Dewar%E2%80%93Chatt%E2%80%93Duncanson_model" title="Dewar–Chatt–Duncanson model">Dewar–Chatt–Duncanson model</a></li> <li><a href="/wiki/Hapticity" title="Hapticity">Hapticity</a></li> <li><a href="/wiki/Spin_states_(d_electrons)" title="Spin states (d electrons)">spin states</a></li> <li><a href="/wiki/Agostic_interaction" title="Agostic interaction">Agostic interaction</a></li> <li><a href="/wiki/Metal%E2%80%93ligand_multiple_bond" title="Metal–ligand multiple bond">Metal–ligand multiple bond</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Reactions</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Oxidative_addition" title="Oxidative addition">Oxidative addition</a> / <a href="/wiki/Reductive_elimination" title="Reductive elimination">reductive elimination</a></li> <li><a href="/wiki/Migratory_insertion" title="Migratory insertion">Migratory insertion</a></li> <li><a href="/wiki/Beta-Hydride_elimination" class="mw-redirect" title="Beta-Hydride elimination">β-hydride elimination</a></li> <li><a href="/wiki/Transmetalation" title="Transmetalation">Transmetalation</a></li> <li><a href="/wiki/Carbometalation" title="Carbometalation">Carbometalation</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Types of compounds</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Gilman_reagent" title="Gilman reagent">Gilman reagents</a></li> <li><a href="/wiki/Grignard_reagent" title="Grignard reagent">Grignard reagents</a></li> <li><a href="/wiki/Cyclopentadienyl_complex" title="Cyclopentadienyl complex">Cyclopentadienyl complexes</a></li> <li><a href="/wiki/Transition_metal_indenyl_complex" title="Transition metal indenyl complex">Transition metal indenyl complexes</a></li> <li><a href="/wiki/Transition_metal_fullerene_complex" title="Transition metal fullerene complex">Transition metal fullerene complexes</a></li> <li><a href="/wiki/Metallocene" title="Metallocene">Metallocenes</a></li> <li><a href="/wiki/Metal_tetranorbornyl" title="Metal tetranorbornyl">Metal tetranorbornyls</a></li> <li><a href="/wiki/Sandwich_compound" title="Sandwich compound">Sandwich compounds</a></li> <li><a href="/wiki/Half_sandwich_compound" title="Half sandwich compound">Half sandwich compounds</a></li> <li><a href="/wiki/Transition_metal_acyl_complexes" title="Transition metal acyl complexes">Transition metal acyl complexes</a></li> <li><a href="/wiki/Transition_metal_carbene_complex" title="Transition metal carbene complex">Transition metal carbene complexes</a></li> <li><a href="/wiki/Transition_metal_carbyne_complex" title="Transition metal carbyne complex">Transition metal carbyne complexes</a></li> <li><a href="/wiki/Transition_metal_alkene_complex" title="Transition metal alkene complex">Transition metal alkene complexes</a></li> <li><a href="/wiki/Transition_metal_alkyne_complex" title="Transition metal alkyne complex">Transition metal alkyne complexes</a></li> <li><a href="/wiki/Transition-metal_allyl_complex" title="Transition-metal allyl complex">Transition-metal allyl complexes</a></li> <li><a href="/wiki/Metal_carbido_complex" title="Metal carbido complex">Transition metal carbides</a></li> <li><a href="/wiki/Arene_complexes_of_univalent_gallium,_indium,_and_thallium" title="Arene complexes of univalent gallium, indium, and thallium">Arene complexes of univalent gallium, indium, and thallium</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Applications</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Carbonylation" title="Carbonylation">Carbonylation</a></li> <li><a href="/wiki/Cativa_process" title="Cativa process">Cativa process</a></li> <li><a href="/wiki/Grignard_reaction" title="Grignard reaction">Grignard reaction</a></li> <li><a href="/wiki/Monsanto_process" title="Monsanto process">Monsanto process</a></li> <li><a href="/wiki/Olefin_metathesis" title="Olefin metathesis">Olefin metathesis</a></li> <li><a href="/wiki/Shell_higher_olefin_process" title="Shell higher olefin process">Shell higher olefin process</a></li> <li><a class="mw-selflink selflink">Ziegler–Natta process</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Related branches of <a href="/wiki/Chemistry" title="Chemistry">chemistry</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Organic_chemistry" title="Organic chemistry">Organic chemistry</a></li> <li><a href="/wiki/Inorganic_chemistry" title="Inorganic chemistry">Inorganic chemistry</a></li> <li><a href="/wiki/Bioinorganic_chemistry" title="Bioinorganic chemistry">Bioinorganic chemistry</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <ul><li><span class="noviewer" typeof="mw:File"><span title="Category"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/16px-Symbol_category_class.svg.png" decoding="async" width="16" height="16" class="mw-file-element" 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