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<title>Homogeneous catalysis</title>

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<span id="openzim-page-title" class="mw-page-title-main"><span class="mw-page-title-main">Homogeneous catalysis</span></span>

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<p>In chemistry, <b>homogeneous catalysis</b> is <a href="Catalysis" title="Catalysis">catalysis</a> where the catalyst is in same phase as reactants, principally by a soluble catalyst in a solution. In contrast, <a href="Heterogeneous_catalysis" title="Heterogeneous catalysis">heterogeneous catalysis</a> describes processes where the catalysts and substrate are in distinct phases, typically solid and gas, respectively.<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> The term is used almost exclusively to describe solutions and implies catalysis by <a href="Organometallic_compound" class="mw-redirect" title="Organometallic compound">organometallic compounds</a>. Homogeneous catalysis is an established technology that continues to evolve. An illustrative major application is the production of <a href="Acetic_acid" title="Acetic acid">acetic acid</a>. Enzymes are examples of homogeneous catalysts.<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>

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<div class="mw-heading mw-heading2"><h2 id="Examples">Examples</h2></div>

<div class="mw-heading mw-heading3"><h3 id="Acid_catalyst">Acid catalyst</h3></div>

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</style><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="Acid_catalysis" title="Acid catalysis">acid catalysis</a></div>

<p>The <a href="Proton" title="Proton">proton</a> is a pervasive homogeneous catalyst<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> because water is the most common solvent. Water forms protons by the process of <a href="Self-ionization_of_water" title="Self-ionization of water">self-ionization of water</a>. In an illustrative case, acids accelerate (catalyze) the <a href="Hydrolysis" title="Hydrolysis">hydrolysis</a> of <a href="Ester" title="Ester">esters</a>:

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<p>At neutral pH, aqueous solutions of most esters do not hydrolyze at practical rates.

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<div class="mw-heading mw-heading3"><h3 id="Transition_metal-catalysis">Transition metal-catalysis</h3></div>

<div class="mw-heading mw-heading4"><h4 id="Hydrogenation_and_related_reactions">Hydrogenation and related reactions</h4></div>

<p>A prominent class of reductive transformations are <a href="Hydrogenation" title="Hydrogenation">hydrogenations</a>. In this process, H<sub>2</sub> added to unsaturated substrates. A related methodology, <a href="Transfer_hydrogenation" title="Transfer hydrogenation">transfer hydrogenation</a>, involves by transfer of hydrogen from one substrate (the hydrogen donor) to another (the hydrogen acceptor). Related reactions entail "HX additions" where X = silyl (<a href="Hydrosilylation" title="Hydrosilylation">hydrosilylation</a>) and CN (<a href="Hydrocyanation" title="Hydrocyanation">hydrocyanation</a>). Most large-scale industrial hydrogenations – margarine, ammonia, benzene-to-cyclohexane – are conducted with heterogeneous catalysts. Fine chemical syntheses, however, often rely on homogeneous catalysts.

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<div class="mw-heading mw-heading4"><h4 id="Carbonylations">Carbonylations</h4></div>

<p><a href="Hydroformylation" title="Hydroformylation">Hydroformylation</a>, a prominent form of <a href="Carbonylation" title="Carbonylation">carbonylation</a>, involves the addition of H and "C(O)H" across a double bond. This process is almost exclusively conducted with soluble <a href="Rhodium" title="Rhodium">rhodium</a>- and <a href="Cobalt" title="Cobalt">cobalt</a>-containing complexes.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup>

</p><p>A related carbonylation is the conversion of alcohols to carboxylic acids. <a href="Methanol" title="Methanol">MeOH</a> and <a href="Carbon_monoxide" title="Carbon monoxide">CO</a> react in the presence of homogeneous catalysts to give <a href="Acetic_acid" title="Acetic acid">acetic acid</a>, as practiced in the <a href="Monsanto_process" title="Monsanto process">Monsanto process</a> and <a href="Cativa_process" title="Cativa process">Cativa processes</a>. Related reactions include <a href="Hydrocarboxylation" class="mw-redirect" title="Hydrocarboxylation">hydrocarboxylation</a> and <a href="Hydroesterification" class="mw-redirect" title="Hydroesterification">hydroesterifications</a>.

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<div class="mw-heading mw-heading4"><h4 id="Polymerization_and_metathesis_of_alkenes">Polymerization and metathesis of alkenes</h4></div>

<p>A number of polyolefins, e.g. polyethylene and polypropylene, are produced from ethylene and propylene by <a href="Ziegler-Natta_catalysis" class="mw-redirect" title="Ziegler-Natta catalysis">Ziegler-Natta catalysis</a>. Heterogeneous catalysts dominate, but many soluble catalysts are employed especially for stereospecific polymers.<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> <a href="Olefin_metathesis" title="Olefin metathesis">Olefin metathesis</a> is usually catalyzed heterogeneously in industry, but homogeneous variants are valuable in fine chemical synthesis.<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>

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<div class="mw-heading mw-heading4"><h4 id="Oxidations">Oxidations</h4></div>

<p>Homogeneous catalysts are also used in a variety of oxidations. In the <a href="Wacker_process" title="Wacker process">Wacker process</a>, acetaldehyde is produced from <a href="Ethene" class="mw-redirect" title="Ethene">ethene</a> and <a href="Oxygen" title="Oxygen">oxygen</a>. Many non-organometallic complexes are also widely used in catalysis, e.g. for the production of <a href="Terephthalic_acid" title="Terephthalic acid">terephthalic acid</a> from <a href="Xylene" title="Xylene">xylene</a>. Alkenes are epoxidized and dihydroxylated by metal complexes, as illustrated by the <a href="Halcon_process" title="Halcon process">Halcon process</a> and the <a href="Sharpless_dihydroxylation" class="mw-redirect" title="Sharpless dihydroxylation">Sharpless dihydroxylation</a>.

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<div class="mw-heading mw-heading3"><h3 id="Enzymes_(including_metalloenzymes)">Enzymes (including metalloenzymes)</h3></div>

<p><a href="Enzyme" title="Enzyme">Enzymes</a> are homogeneous catalysts that are essential for life but are also harnessed for industrial processes. A well-studied example is <a href="Carbonic_anhydrase" title="Carbonic anhydrase">carbonic anhydrase</a>, which catalyzes the release of CO<sub>2</sub> into the lungs from the bloodstream. Enzymes possess properties of both homogeneous and heterogeneous catalysts. As such, they are usually regarded as a third, separate category of catalyst. Water is a common reagent in enzymatic catalysis. Esters and amides are slow to hydrolyze in neutral water, but the rates are sharply affected by <a href="Metalloenzyme" class="mw-redirect" title="Metalloenzyme">metalloenzymes</a>, which can be viewed as large coordination complexes. Acrylamide is prepared by the enzyme-catalyzed hydrolysis of <a href="Acrylonitrile" title="Acrylonitrile">acrylonitrile</a>.<sup id="cite_ref-Ullmann_8-0" class="reference"><a href="#cite_note-Ullmann-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> US demand for <a href="Acrylamide" title="Acrylamide">acrylamide</a> was 253,000,000 pounds (115,000,000 kg) as of 2007.

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<div class="mw-heading mw-heading2"><h2 id="Advantages_and_disadvantages">Advantages and disadvantages</h2></div>

<div class="mw-heading mw-heading3"><h3 id="Advantages">Advantages</h3></div>

<ul><li>Homogeneous catalysts are often more selective than heterogeneous catalysts.</li>

<li>For exothermic processes, homogeneous catalysts dump heat into the solvent.</li>

<li>Homogeneous catalysts are easier to characterize, making their reaction mechanisms amenable to rational manipulation.<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></li></ul>

<div class="mw-heading mw-heading3"><h3 id="Disadvantages">Disadvantages</h3></div>

<ul><li>The separation of homogeneous catalysts from products can be challenging. In some cases involving high activity catalysts, the catalyst is not removed from the product. In other cases, distillation can extract volatile organic products.</li>

<li>Homogeneous catalysts have limited thermal stability compared to heterogeneous catalysts. Many organometallic complexes degrade below 100 °C. Some <a href="Pincer_complex" class="mw-redirect" title="Pincer complex">pincer-based catalysts</a>, however, operate near 200 °C.<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></li></ul>

<ul><li><a href="Concurrent_tandem_catalysis" title="Concurrent tandem catalysis">Concurrent tandem catalysis</a></li></ul>

<div class="mw-heading mw-heading2"><h2 id="References">References</h2></div>

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<li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><a href="International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">IUPAC</a>, <i><a href="IUPAC_books" class="mw-redirect" title="IUPAC books">Compendium of Chemical Terminology</a></i>, 5th ed. (the "Gold Book") (2025). Online version: (2006–) "<a rel="nofollow" class="external text" href="https://goldbook.iupac.org/terms/view/C00876.html">catalyst</a>". <style data-mw-deduplicate="TemplateStyles:r1238218222">

/* start https://en.wikipedia.org/ */

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</style><a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1351%2Fgoldbook.C00876">10.1351/goldbook.C00876</a></span>

</li>

<li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><cite id="CITEREFvan_LeeuwenChadwick2011" class="citation book cs1">van Leeuwen, P. W. N. M.; Chadwick, J. C. (2011). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=bvKkcQAACAAJ"><i>Homogeneous Catalysts: Activity - Stability - Deactivation</i></a>. Wiley-VCH, Weinheim. <a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>9783527635993</bdi>. <a href="OCLC_(identifier)" class="mw-redirect" title="OCLC (identifier)">OCLC</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/oclc/739118524">739118524</a>.</cite>.</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 id="CITEREFKlosinFontaineFigueroa2015" class="citation journal cs1">Klosin, Jerzy; Fontaine, Philip P.; Figueroa, Ruth (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): <span class="nowrap">2004–</span>2016. <a href="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="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>

</li>

<li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><cite id="CITEREFBell2013" class="citation book cs1">Bell, R. P. (11 November 2013). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=oefcBwAAQBAJ"><i>The Proton in Chemistry</i></a>. New York, NY: Springer Science & Business Media. <a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>978-1-4757-1592-7</bdi>. <a href="OCLC_(identifier)" class="mw-redirect" title="OCLC (identifier)">OCLC</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/oclc/1066192105">1066192105</a>.</cite></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"><cite id="CITEREFCornilsBörnerFrankeZhang2017" class="citation book cs1">Cornils, Boy; Börner, Armin; Franke, Robert; Zhang, Baoxin; Wiebus, Ernst; Schmid, Klaus (2017). "Hydroformylation". <i>Applied Homogeneous Catalysis with Organometallic Compounds</i>. pp. <span class="nowrap">23–</span>90. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F9783527651733.ch2">10.1002/9783527651733.ch2</a>. <a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>9783527328970</bdi>.</cite></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">Elschenbroich, C. ”Organometallics” (2006) Wiley-VCH: Weinheim. <a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>978-3-527-29390-2</bdi></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"><cite id="CITEREFBeckerleOkudaKaminskyLuinstra2017" class="citation book cs1">Beckerle, Klaus; Okuda, Jun; Kaminsky, Walter; Luinstra, Gerrit A.; Baier, Moritz C.; Mecking, Stefan; Ricci, Giovanni; Leone, Giuseppe; Mleczko, Leslaw; Wolf, Aurel; Grosse Böwing, Alexandra (2017). "Polymerization and Copolymerization". <i>Applied Homogeneous Catalysis with Organometallic Compounds</i>. pp. <span class="nowrap">191–</span>306. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F9783527651733.ch4">10.1002/9783527651733.ch4</a>. <a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>9783527328970</bdi>.</cite></span>

</li>

<li id="cite_note-Ullmann-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-Ullmann_8-0">^</a></b></span> <span class="reference-text"><cite id="CITEREFOharaSatoShimizuPrescher2003" class="citation encyclopaedia cs1">Ohara, Takashi; Sato, Takahisa; Shimizu, Noboru; Prescher, Günter; Schwind, Helmut; Weiberg, Otto; Marten, Klaus; Greim, Helmut (2003). "Acrylic Acid and Derivatives". <i><a href="Ullmann's_Encyclopedia_of_Industrial_Chemistry" title="Ullmann's Encyclopedia of Industrial Chemistry">Ullmann's Encyclopedia of Industrial Chemistry</a></i>. Weinheim: Wiley-VCH. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F14356007.a01_161.pub2">10.1002/14356007.a01_161.pub2</a>. <a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>3527306730</bdi>.</cite></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">G. O. Spessard and G. L. Miessler "Organometallic Chemistry", Prentice Hall, Upper Saddle River, NJ, 1997, pp. 249-251.</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"><cite id="CITEREFHaibachKunduBrookhartGoldman2012" class="citation journal cs1">Haibach, Michael C.; Kundu, Sabuj; Brookhart, Maurice; Goldman, Alan S. (2012). "Alkane Metathesis by Tandem Alkane-Dehydrogenation–Olefin-Metathesis Catalysis and Related Chemistry". <i>Accounts of Chemical Research</i>. <b>45</b> (6): <span class="nowrap">947–</span>958. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Far3000713">10.1021/ar3000713</a>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/22584036">22584036</a>.</cite></span>

</li>

</ol></div></div>

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</style></div><div role="navigation" class="navbox authority-control" aria-labelledby="Authority_control_databases_frameless&#124;text-top&#124;10px&#124;alt=Edit_this_at_Wikidata&#124;link=https&#58;//www.wikidata.org/wiki/Q1411716#identifiers&#124;class=noprint&#124;Edit_this_at_Wikidata1271" style="padding:3px"><table class="nowraplinks hlist mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><div id="Authority_control_databases_frameless&#124;text-top&#124;10px&#124;alt=Edit_this_at_Wikidata&#124;link=https&#58;//www.wikidata.org/wiki/Q1411716#identifiers&#124;class=noprint&#124;Edit_this_at_Wikidata1271" style="font-size:114%;margin:0 4em">Authority control databases </div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">National</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"><ul><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="Homogeneous catalysis"><a rel="nofollow" class="external text" href="https://id.loc.gov/authorities/sh2014001146">United States</a></span></span></li><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="Catalyse homogène"><a rel="nofollow" class="external text" href="https://catalogue.bnf.fr/ark:/12148/cb11991895p">France</a></span></span></li><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="Catalyse homogène"><a rel="nofollow" class="external text" href="https://data.bnf.fr/ark:/12148/cb11991895p">BnF data</a></span></span></li><li><span class="uid"><a rel="nofollow" class="external text" href="https://www.nli.org.il/en/authorities/987007583836805171">Israel</a></span></li></ul></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"><ul><li><span class="uid"><a rel="nofollow" class="external text" href="https://lux.collections.yale.edu/view/concept/47914cae-3c3d-4bd1-aae9-f8819dca8895">Yale LUX</a></span></li></ul></div></td></tr></tbody></table></div></div><div><div class="zim-footer">

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