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</ul> </li> <li id="toc-Solid-Liquid_and_Liquid-Liquid_Catalyzed_Reactions" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Solid-Liquid_and_Liquid-Liquid_Catalyzed_Reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Solid-Liquid and Liquid-Liquid Catalyzed Reactions</span> </div> </a> <ul id="toc-Solid-Liquid_and_Liquid-Liquid_Catalyzed_Reactions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span 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class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Cat%C3%A0lisi_heterog%C3%A8nia" title="Catàlisi heterogènia – Catalan" lang="ca" hreflang="ca" data-title="Catàlisi heterogènia" 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/Heterogenn%C3%AD_katal%C3%BDza" title="Heterogenní katalýza – Czech" lang="cs" hreflang="cs" data-title="Heterogenní katalýza" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Heterogen_katalyse" title="Heterogen katalyse – Danish" lang="da" hreflang="da" data-title="Heterogen katalyse" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de badge-Q17437798 badge-goodarticle mw-list-item" title="good article badge"><a href="https://de.wikipedia.org/wiki/Heterogene_Katalyse" title="Heterogene Katalyse – German" lang="de" hreflang="de" data-title="Heterogene Katalyse" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Heterogeenne_katal%C3%BC%C3%BCs" title="Heterogeenne katalüüs – Estonian" lang="et" hreflang="et" data-title="Heterogeenne katalüüs" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Cat%C3%A1lisis_heterog%C3%A9nea" title="Catálisis heterogénea – Spanish" lang="es" hreflang="es" data-title="Catálisis heterogénea" 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/Katalisi_heterogeneo" title="Katalisi heterogeneo – Basque" lang="eu" hreflang="eu" data-title="Katalisi heterogeneo" 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_%D9%86%D8%A7%D9%87%D9%85%DA%AF%D9%86" title="کاتالیز ناهمگن – Persian" lang="fa" hreflang="fa" data-title="کاتالیز ناهمگن" 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_h%C3%A9t%C3%A9rog%C3%A8ne" title="Catalyse hétérogène – French" lang="fr" hreflang="fr" data-title="Catalyse hétérogène" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Catalisi_eterogenea" title="Catalisi eterogenea – Italian" lang="it" hreflang="it" data-title="Catalisi eterogenea" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Heterog%C3%A9n_katal%C3%ADzis" title="Heterogén katalízis – Hungarian" lang="hu" hreflang="hu" data-title="Heterogén katalízis" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Kataliza_heterogeniczna" title="Kataliza heterogeniczna – Polish" lang="pl" hreflang="pl" data-title="Kataliza heterogeniczna" 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/Cat%C3%A1lise_heterog%C3%AAnea" title="Catálise heterogênea – Portuguese" lang="pt" hreflang="pt" data-title="Catálise heterogênea" 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%93%D0%B5%D1%82%D0%B5%D1%80%D0%BE%D0%B3%D0%B5%D0%BD%D0%BD%D1%8B%D0%B9_%D0%BA%D0%B0%D1%82%D0%B0%D0%BB%D0%B8%D0%B7" title="Гетерогенный катализ – Russian" lang="ru" hreflang="ru" data-title="Гетерогенный катализ" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%A5%D0%B5%D1%82%D0%B5%D1%80%D0%BE%D0%B3%D0%B5%D0%BD%D0%B0_%D0%BA%D0%B0%D1%82%D0%B0%D0%BB%D0%B8%D0%B7%D0%B0" title="Хетерогена катализа – Serbian" lang="sr" hreflang="sr" data-title="Хетерогена катализа" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Heterogeeninen_katalyysi" title="Heterogeeninen katalyysi – Finnish" lang="fi" hreflang="fi" data-title="Heterogeeninen katalyysi" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%AA%E0%AE%B2%E0%AE%AA%E0%AE%9F%E0%AE%BF%E0%AE%A4%E0%AF%8D%E0%AE%A4%E0%AE%BE%E0%AE%A9_%E0%AE%B5%E0%AE%BF%E0%AE%A9%E0%AF%88%E0%AE%B5%E0%AF%87%E0%AE%95_%E0%AE%AE%E0%AE%BE%E0%AE%B1%E0%AF%8D%E0%AE%B1%E0%AE%AE%E0%AF%8D" title="பலபடித்தான வினைவேக மாற்றம் – Tamil" lang="ta" hreflang="ta" data-title="பலபடித்தான வினைவேக மாற்றம்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%93%D0%B5%D1%82%D0%B5%D1%80%D0%BE%D0%B3%D0%B5%D0%BD%D0%BD%D0%B8%D0%B9_%D0%BA%D0%B0%D1%82%D0%B0%D0%BB%D1%96%D0%B7" title="Гетерогенний каталіз – Ukrainian" lang="uk" hreflang="uk" data-title="Гетерогенний каталіз" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link 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class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-appearance.unpin">hide</button> </div> </div> </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> <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">Type of catalysis involving reactants & catalysts in different phases of matter</div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Hydrogenation_on_catalyst.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/ac/Hydrogenation_on_catalyst.svg/220px-Hydrogenation_on_catalyst.svg.png" decoding="async" width="220" height="503" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/ac/Hydrogenation_on_catalyst.svg/330px-Hydrogenation_on_catalyst.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/ac/Hydrogenation_on_catalyst.svg/440px-Hydrogenation_on_catalyst.svg.png 2x" data-file-width="211" data-file-height="482" /></a><figcaption><a href="/wiki/Hydrogenation" title="Hydrogenation">Hydrogenation</a> of <a href="/wiki/Ethene" class="mw-redirect" title="Ethene">ethene</a> on a catalytic solid surface (1) Adsorption (2) Reaction (3) Desorption</figcaption></figure> <p><b>Heterogeneous catalysis</b> is <a href="/wiki/Catalysis" title="Catalysis">catalysis</a> where the <a href="/wiki/Phase_(matter)" title="Phase (matter)">phase</a> of catalysts differs from that of the <a href="/wiki/Reagents" class="mw-redirect" title="Reagents">reagents</a> or <a href="/wiki/Product_(chemistry)" title="Product (chemistry)">products</a>.<sup id="cite_ref-:1_1-0" class="reference"><a href="#cite_note-:1-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> The process contrasts with <a href="/wiki/Homogeneous_catalysis" title="Homogeneous catalysis">homogeneous catalysis</a> where the reagents, products and catalyst exist in the same phase. Phase distinguishes between not only <a href="/wiki/Solid" title="Solid">solid</a>, <a href="/wiki/Liquid" title="Liquid">liquid</a>, and <a href="/wiki/Gas" title="Gas">gas</a> components, but also <a href="/wiki/Immiscible" class="mw-redirect" title="Immiscible">immiscible</a> mixtures (e.g., <a href="/wiki/Oil" title="Oil">oil</a> and <a href="/wiki/Water" title="Water">water</a>), or anywhere an interface is present. </p><p>Heterogeneous catalysis typically involves solid phase catalysts and gas phase reactants.<sup id="cite_ref-:02_2-0" class="reference"><a href="#cite_note-:02-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> In this case, there is a cycle of molecular adsorption, reaction, and desorption occurring at the catalyst surface. Thermodynamics, mass transfer, and heat transfer influence the <a href="/wiki/Reaction_rate" title="Reaction rate">rate (kinetics) of reaction</a>. </p><p>Heterogeneous catalysis is very important because it enables faster, large-scale production and the selective product formation.<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> Approximately 35% of the world's GDP is influenced by catalysis.<sup id="cite_ref-:6_4-0" class="reference"><a href="#cite_note-:6-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> The production of 90% of chemicals (by volume) is assisted by solid catalysts.<sup id="cite_ref-:02_2-1" class="reference"><a href="#cite_note-:02-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> The chemical and energy industries rely heavily on heterogeneous catalysis. For example, the <a href="/wiki/Haber%E2%80%93Bosch_process" class="mw-redirect" title="Haber–Bosch process">Haber–Bosch process</a> uses metal-based catalysts in the synthesis of <a href="/wiki/Ammonia" title="Ammonia">ammonia</a>, an important component in fertilizer; 144 million tons of ammonia were produced in 2016.<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> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Adsorption">Adsorption</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Heterogeneous_catalysis&action=edit&section=1" title="Edit section: Adsorption"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Adsorption" title="Adsorption">Adsorption</a> is an essential step in heterogeneous catalysis. Adsorption is the process by which a gas (or solution) phase molecule (the adsorbate) binds to solid (or liquid) surface atoms (the adsorbent). The reverse of adsorption is <a href="/wiki/Desorption" title="Desorption">desorption</a>, the adsorbate splitting from adsorbent. In a reaction facilitated by heterogeneous catalysis, the catalyst is the adsorbent and the reactants are the adsorbate. </p> <div class="mw-heading mw-heading3"><h3 id="Types_of_adsorption">Types of adsorption</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Heterogeneous_catalysis&action=edit&section=2" title="Edit section: Types of adsorption"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Two types of adsorption are recognized: <a href="/wiki/Physisorption" title="Physisorption">physisorption</a>, weakly bound adsorption, and <a href="/wiki/Chemisorption" title="Chemisorption">chemisorption</a>, strongly bound adsorption. Many processes in heterogeneous catalysis lie between the two extremes. The <a href="/wiki/Lennard-Jones_potential" title="Lennard-Jones potential">Lennard-Jones model</a> provides a basic framework for predicting molecular interactions as a function of atomic separation.<sup id="cite_ref-:2_6-0" class="reference"><a href="#cite_note-:2-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Physisorption">Physisorption</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Heterogeneous_catalysis&action=edit&section=3" title="Edit section: Physisorption"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In physisorption, a molecule becomes attracted to the surface atoms via <a href="/wiki/Van_der_Waals_force" title="Van der Waals force">van der Waals forces</a>. These include dipole-dipole interactions, induced dipole interactions, and London dispersion forces. Note that no chemical bonds are formed between adsorbate and adsorbent, and their electronic states remain relatively unperturbed. Typical energies for physisorption are from 3 to 10 kcal/mol.<sup id="cite_ref-:02_2-2" class="reference"><a href="#cite_note-:02-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> In heterogeneous catalysis, when a reactant molecule physisorbs to a catalyst, it is commonly said to be in a precursor state, an intermediate energy state before chemisorption, a more strongly bound adsorption.<sup id="cite_ref-:2_6-1" class="reference"><a href="#cite_note-:2-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> From the precursor state, a molecule can either undergo chemisorption, desorption, or migration across the surface.<sup id="cite_ref-:3_7-0" class="reference"><a href="#cite_note-:3-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> The nature of the precursor state can influence the reaction kinetics.<sup id="cite_ref-:3_7-1" class="reference"><a href="#cite_note-:3-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Chemisorption">Chemisorption</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Heterogeneous_catalysis&action=edit&section=4" title="Edit section: Chemisorption"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>When a molecule approaches close enough to surface atoms such that their <a href="/wiki/Atomic_orbital" title="Atomic orbital">electron clouds</a> overlap, chemisorption can occur. In chemisorption, the adsorbate and adsorbent share electrons signifying the formation of <a href="/wiki/Chemical_bond" title="Chemical bond">chemical bonds</a>. Typical energies for chemisorption range from 20 to 100 kcal/mol.<sup id="cite_ref-:02_2-3" class="reference"><a href="#cite_note-:02-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Two cases of chemisorption are: </p> <ul><li>Molecular adsorption: the adsorbate remains intact. An example is alkene binding by platinum.</li> <li>Dissociation adsorption: one or more bonds break concomitantly with adsorption. In this case, the barrier to <a href="/wiki/Dissociation_(chemistry)" title="Dissociation (chemistry)">dissociation</a> affects the rate of adsorption. An example of this is the binding of H<sub>2</sub> to a metal catalyst, where the H-H bond is broken upon adsorption.</li></ul> <div class="mw-heading mw-heading2"><h2 id="Surface_reactions">Surface reactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Heterogeneous_catalysis&action=edit&section=5" title="Edit section: Surface reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Catalytic_reaction_coordinate.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1e/Catalytic_reaction_coordinate.jpg/300px-Catalytic_reaction_coordinate.jpg" decoding="async" width="300" height="225" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1e/Catalytic_reaction_coordinate.jpg/450px-Catalytic_reaction_coordinate.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1e/Catalytic_reaction_coordinate.jpg/600px-Catalytic_reaction_coordinate.jpg 2x" data-file-width="640" data-file-height="480" /></a><figcaption>Reaction Coordinate. (A) Uncatalyzed (B) Catalyzed (C) Catalyzed with discrete intermediates (transition states)</figcaption></figure> <p>Most metal surface reactions occur by <a href="/wiki/Chain_propagation" title="Chain propagation">chain propagation</a> in which catalytic intermediates are cyclically produced and consumed.<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> Two main mechanisms for surface reactions can be described for A + B → C.<sup id="cite_ref-:02_2-4" class="reference"><a href="#cite_note-:02-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <ul><li><a href="/wiki/Reactions_on_surfaces#Langmuir–Hinshelwood_mechanism" title="Reactions on surfaces">Langmuir–Hinshelwood mechanism</a>: The reactant molecules, A and B, both adsorb to the catalytic surface. While adsorbed to the surface, they combine to form product C, which then desorbs.</li> <li><a href="/wiki/Reactions_on_surfaces#Eley–Rideal_mechanism" title="Reactions on surfaces">Eley–Rideal mechanism</a>: One reactant molecule, A, adsorbs to the catalytic surface. Without adsorbing, B reacts with absorbed A to form C, that then desorbs from the surface.</li></ul> <p>Most heterogeneously catalyzed reactions are described by the Langmuir–Hinshelwood model.<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><p>In heterogeneous catalysis, reactants <a href="/wiki/Surface_diffusion" title="Surface diffusion">diffuse</a> from the bulk fluid phase to <a href="/wiki/Adsorb" class="mw-redirect" title="Adsorb">adsorb</a> to the catalyst surface. The adsorption site is not always an active catalyst site, so reactant molecules must migrate across the surface to an active site. At the active site, reactant molecules will react to form product molecule(s) by following a more energetically facile path through catalytic intermediates (see figure to the right). The product molecules then desorb from the surface and diffuse away. The catalyst itself remains intact and free to mediate further reactions. Transport phenomena such as heat and mass transfer, also play a role in the observed reaction rate. </p> <div class="mw-heading mw-heading2"><h2 id="Catalyst_design">Catalyst design</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Heterogeneous_catalysis&action=edit&section=6" title="Edit section: Catalyst design"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Zeolite-ZSM-5-3D-vdW.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/Zeolite-ZSM-5-3D-vdW.png/220px-Zeolite-ZSM-5-3D-vdW.png" decoding="async" width="220" height="244" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/Zeolite-ZSM-5-3D-vdW.png/330px-Zeolite-ZSM-5-3D-vdW.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/58/Zeolite-ZSM-5-3D-vdW.png/440px-Zeolite-ZSM-5-3D-vdW.png 2x" data-file-width="1100" data-file-height="1221" /></a><figcaption>Zeolite structure. A common catalyst support material in hydrocracking. Also acts as a catalyst in hydrocarbon alkylation and isomerization.</figcaption></figure> <p>Catalysts are not active towards reactants across their entire surface; only specific locations possess catalytic activity, called <a href="/wiki/Active_site" title="Active site"><b>active sites</b></a>. The surface area of a solid catalyst has a strong influence on the number of available active sites. In industrial practice, solid catalysts are often porous to maximize surface area, commonly achieving 50–400 m<sup>2</sup>/g.<sup id="cite_ref-:02_2-5" class="reference"><a href="#cite_note-:02-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Some <a href="/wiki/Mesoporous_silicates" class="mw-redirect" title="Mesoporous silicates">mesoporous silicates</a>, such as the MCM-41, have surface areas greater than 1000 m<sup>2</sup>/g.<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> Porous materials are cost effective due to their high surface area-to-mass ratio and enhanced catalytic activity. </p><p>In many cases, a solid catalyst is <a href="/wiki/Dispersion_(chemistry)" title="Dispersion (chemistry)">dispersed</a> on a supporting material to increase surface area (spread the number of active sites) and provide stability.<sup id="cite_ref-:02_2-6" class="reference"><a href="#cite_note-:02-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Usually <a href="/wiki/Catalyst_support" title="Catalyst support">catalyst supports</a> are inert, high melting point materials, but they can also be catalytic themselves. Most catalyst supports are porous (frequently carbon, silica, zeolite, or alumina-based)<sup id="cite_ref-:6_4-1" class="reference"><a href="#cite_note-:6-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> and chosen for their high surface area-to-mass ratio. For a given reaction, porous supports must be selected such that reactants and products can enter and exit the material. </p><p>Often, substances are intentionally added to the reaction feed or on the catalyst to influence catalytic activity, selectivity, and/or stability. These compounds are called promoters. For example, alumina (Al<sub>2</sub>O<sub>3</sub>) is added during ammonia synthesis to providing greater stability by slowing sintering processes on the Fe-catalyst.<sup id="cite_ref-:02_2-7" class="reference"><a href="#cite_note-:02-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Sabatier_principle" title="Sabatier principle">Sabatier principle</a> can be considered one of the cornerstones of modern theory of catalysis.<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> Sabatier principle states that the surface-adsorbates interaction has to be an optimal amount: not too weak to be inert toward the reactants and not too strong to poison the surface and avoid desorption of the products.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> The statement that the surface-adsorbate interaction has to be an optimum, is a qualitative one. Usually the number of adsorbates and <a href="/wiki/Transition_state" title="Transition state">transition states</a> associated with a chemical reaction is a large number, thus the <a href="/wiki/Optimum" class="mw-redirect" title="Optimum">optimum</a> has to be found in a many-dimensional space. Catalyst design in such a many-dimensional space is not a computationally viable task. Additionally, such optimization process would be far from intuitive. Scaling relations are used to decrease the dimensionality of the space of catalyst design.<sup id="cite_ref-:0_13-0" class="reference"><a href="#cite_note-:0-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> Such relations are correlations among adsorbates binding energies (or among adsorbate binding energies and transition states also known as <a href="/wiki/Bell%E2%80%93Evans%E2%80%93Polanyi_principle" title="Bell–Evans–Polanyi principle">BEP relations</a>)<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> that are "similar enough" e.g., OH versus OOH scaling.<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> Applying scaling relations to the catalyst design problems greatly reduces the space dimensionality (sometimes to as small as 1 or 2).<sup id="cite_ref-:7_16-0" class="reference"><a href="#cite_note-:7-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> One can also use micro-kinetic modeling based on such scaling relations to take into account the kinetics associated with adsorption, reaction and desorption of molecules under specific pressure or temperature conditions.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> Such modeling then leads to well-known volcano-plots at which the optimum qualitatively described by the Sabatier principle is referred to as the "top of the volcano". Scaling relations can be used not only to connect the energetics of <a href="/wiki/Radical_(chemistry)" title="Radical (chemistry)">radical</a> surface-adsorbed groups (e.g., O*,OH*),<sup id="cite_ref-:0_13-1" class="reference"><a href="#cite_note-:0-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> but also to connect the energetics of <a href="/wiki/Closed_shell" class="mw-redirect" title="Closed shell">closed-shell</a> molecules among each other or to the counterpart radical adsorbates.<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> A recent challenge for researchers in catalytic sciences is to "break" the scaling relations.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> The correlations which are manifested in the scaling relations confine the catalyst design space, preventing one from reaching the "top of the volcano". Breaking scaling relations can refer to either designing surfaces or motifs that do not follow a scaling relation, or ones that follow a different scaling relation (than the usual relation for the associated adsorbates) in the right direction: one that can get us closer to the top of the reactivity volcano.<sup id="cite_ref-:7_16-1" class="reference"><a href="#cite_note-:7-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> In addition to studying catalytic reactivity, scaling relations can be used to study and screen materials for selectivity toward a special product.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> There are special combination of binding energies that favor specific products over the others. Sometimes a set of binding energies that can change the selectivity toward a specific product "scale" with each other, thus to improve the selectivity one has to break some scaling relations; an example of this is the scaling between methane and methanol oxidative activation energies that leads to the lack of selectivity in direct conversion of methane to methanol.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Catalyst_deactivation">Catalyst deactivation</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Heterogeneous_catalysis&action=edit&section=7" title="Edit section: Catalyst deactivation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Catalyst deactivation is defined as a loss in catalytic activity and/or selectivity over time. </p><p>Substances that decrease reaction rate are called <b>poisons</b>. Poisons chemisorb to catalyst surface and reduce the number of available active sites for reactant molecules to bind to.<sup id="cite_ref-:4_22-0" class="reference"><a href="#cite_note-:4-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> Common poisons include Group V, VI, and VII elements (e.g. S, O, P, Cl), some toxic metals (e.g. As, Pb), and adsorbing species with multiple bonds (e.g. CO, unsaturated hydrocarbons).<sup id="cite_ref-:2_6-2" class="reference"><a href="#cite_note-:2-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:4_22-1" class="reference"><a href="#cite_note-:4-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> For example, sulfur disrupts the production of methanol by poisoning the Cu/ZnO catalyst.<sup id="cite_ref-:5_23-0" class="reference"><a href="#cite_note-:5-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> Substances that increase reaction rate are called <b>promoters</b>. For example, the presence of alkali metals in ammonia synthesis increases the rate of N<sub>2</sub> dissociation.<sup id="cite_ref-:5_23-1" class="reference"><a href="#cite_note-:5-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p><p>The presence of poisons and promoters can alter the <a href="/wiki/Activation_energy" title="Activation energy">activation energy</a> of the rate-limiting step and affect a catalyst's selectivity for the formation of certain products. Depending on the amount, a substance can be favorable or unfavorable for a chemical process. For example, in the production of ethylene, a small amount of chemisorbed chlorine will act as a promoter by improving Ag-catalyst selectivity towards ethylene over CO<sub>2</sub>, while too much chlorine will act as a poison.<sup id="cite_ref-:2_6-3" class="reference"><a href="#cite_note-:2-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>Other mechanisms for catalyst deactivation include: </p> <ul><li><a href="/wiki/Sintering" title="Sintering">Sintering</a>: when heated, dispersed catalytic metal particles can migrate across the support surface and form crystals. This results in a reduction of catalyst surface area.</li> <li><a href="/wiki/Fouling" title="Fouling">Fouling</a>: the deposition of materials from the fluid phase onto the solid phase catalyst and/or support surfaces. This results in active site and/or pore blockage.</li> <li><a href="/wiki/Coking" title="Coking">Coking</a>: the deposition of heavy, carbon-rich solids onto surfaces due to the decomposition of hydrocarbons<sup id="cite_ref-:4_22-2" class="reference"><a href="#cite_note-:4-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup></li> <li>Vapor-solid reactions: formation of an inactive surface layer and/or formation of a volatile compound that exits the reactor.<sup id="cite_ref-:4_22-3" class="reference"><a href="#cite_note-:4-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> This results in a loss of surface area and/or catalyst material.</li> <li><a href="/wiki/Phase_transition" title="Phase transition">Solid-state transformation</a>: solid-state diffusion of catalyst support atoms to the surface followed by a reaction that forms an inactive phase. This results in a loss of catalyst surface area.</li> <li>Erosion: continual attrition of catalyst material common in fluidized-bed reactors.<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> This results in a loss of catalyst material.</li></ul> <p>In industry, catalyst deactivation costs billions every year due to process shutdown and catalyst replacement.<sup id="cite_ref-:4_22-4" class="reference"><a href="#cite_note-:4-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Industrial_examples">Industrial examples</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Heterogeneous_catalysis&action=edit&section=8" title="Edit section: Industrial examples"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In industry, many design variables must be considered including reactor and catalyst design across multiple scales ranging from the subnanometer to tens of meters. The conventional heterogeneous catalysis reactors include <a href="/wiki/Batch_reactor" title="Batch reactor">batch</a>, <a href="/wiki/Continuous_reactor" title="Continuous reactor">continuous</a>, and <a href="/wiki/Fluidized_bed_reactor" title="Fluidized bed reactor">fluidized-bed reactors</a>, while more recent setups include fixed-bed, microchannel, and multi-functional <a href="/wiki/Heterogeneous_catalytic_reactor" title="Heterogeneous catalytic reactor">reactors</a>.<sup id="cite_ref-:2_6-4" class="reference"><a href="#cite_note-:2-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Other variables to consider are reactor dimensions, surface area, catalyst type, catalyst support, as well as reactor operating conditions such as temperature, pressure, and reactant concentrations. </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Heterrogenous_catalysis_across_scales.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5a/Heterrogenous_catalysis_across_scales.png/220px-Heterrogenous_catalysis_across_scales.png" decoding="async" width="220" height="136" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5a/Heterrogenous_catalysis_across_scales.png/330px-Heterrogenous_catalysis_across_scales.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5a/Heterrogenous_catalysis_across_scales.png/440px-Heterrogenous_catalysis_across_scales.png 2x" data-file-width="3069" data-file-height="1899" /></a><figcaption>Schematic representation of a heterogeneous catalytic system from the subnanometer to industrial scale.</figcaption></figure> <p>Some large-scale industrial processes incorporating heterogeneous catalysts are listed below.<sup id="cite_ref-:6_4-2" class="reference"><a href="#cite_note-:6-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <table class="wikitable" style="text-align:center"> <tbody><tr> <th>Process </th> <th>Reactants, Product/s (not balanced) </th> <th>Catalyst </th> <th>Comment </th></tr> <tr> <td>Sulfuric acid synthesis (<a href="/wiki/Contact_process" title="Contact process">Contact process</a>) </td> <td>SO<sub>2</sub> + O<sub>2</sub>, SO<sub>3</sub> </td> <td>vanadium oxides </td> <td>Hydration of SO<sub>3</sub> gives H<sub>2</sub>SO<sub>4</sub> </td></tr> <tr> <td>Ammonia synthesis (<a href="/wiki/Haber%E2%80%93Bosch_process" class="mw-redirect" title="Haber–Bosch process">Haber–Bosch process</a>) </td> <td>N<sub>2</sub> + H<sub>2</sub>, NH<sub>3</sub> </td> <td>iron oxides on <a href="/wiki/Alumina" class="mw-redirect" title="Alumina">alumina</a>(Al<sub>2</sub>O<sub>3</sub>) </td> <td>Consumes 1% of world's industrial energy budget<sup id="cite_ref-:02_2-8" class="reference"><a href="#cite_note-:02-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td>Nitric acid synthesis (<a href="/wiki/Ostwald_process" title="Ostwald process">Ostwald process</a>) </td> <td>NH<sub>3</sub> + O<sub>2</sub>, HNO<sub>3</sub> </td> <td>unsupported Pt-Rh gauze </td> <td>Direct routes from N<sub>2</sub> are uneconomical </td></tr> <tr> <td>Hydrogen production by <a href="/wiki/Steam_reforming" title="Steam reforming">Steam reforming</a> </td> <td>CH<sub>4</sub> + H<sub>2</sub>O, H<sub>2</sub> + CO<sub>2</sub> </td> <td>Nickel or K<sub>2</sub>O </td> <td>Greener routes to H<sub>2</sub> by <a href="/wiki/Water_splitting" title="Water splitting">water splitting</a> actively sought </td></tr> <tr> <td><a href="/wiki/Ethylene_oxide" title="Ethylene oxide">Ethylene oxide</a> synthesis </td> <td>C<sub>2</sub>H<sub>4</sub> + O<sub>2</sub>, C<sub>2</sub>H<sub>4</sub>O </td> <td><a href="/wiki/Silver" title="Silver">silver</a> on <a href="/wiki/Alumina" class="mw-redirect" title="Alumina">alumina</a>, with many promoters </td> <td>Poorly applicable to other alkenes </td></tr> <tr> <td>Hydrogen cyanide synthesis (<a href="/wiki/Andrussov_oxidation" class="mw-redirect" title="Andrussov oxidation">Andrussov oxidation</a>) </td> <td>NH<sub>3</sub> + O<sub>2</sub> + CH<sub>4</sub>, HCN </td> <td>Pt-Rh </td> <td>Related <a href="/wiki/Ammoxidation" title="Ammoxidation">ammoxidation</a> process converts hydrocarbons to <a href="/wiki/Nitrile" title="Nitrile">nitriles</a> </td></tr> <tr> <td>Olefin polymerization <a href="/wiki/Ziegler%E2%80%93Natta_polymerization" class="mw-redirect" title="Ziegler–Natta polymerization">Ziegler–Natta polymerization</a> </td> <td><a href="/wiki/Propylene" title="Propylene">propylene</a>, <a href="/wiki/Polypropylene" title="Polypropylene">polypropylene</a> </td> <td><a href="/wiki/Titanium_trichloride" class="mw-redirect" title="Titanium trichloride">TiCl<sub>3</sub></a> on <a href="/wiki/Magnesium_chloride" title="Magnesium chloride">MgCl<sub>2</sub></a> </td> <td>Many variations exist, including some <a href="/wiki/Homogeneous_catalysis" title="Homogeneous catalysis">homogeneous examples</a> </td></tr> <tr> <td>Desulfurization of petroleum (<a href="/wiki/Hydrodesulfurization" title="Hydrodesulfurization">hydrodesulfurization</a>) </td> <td>H<sub>2</sub> + R<sub>2</sub>S (idealized organosulfur impurity), RH + H<sub>2</sub>S </td> <td><a href="/wiki/Molybdenum" title="Molybdenum">Mo</a>-<a href="/wiki/Cobalt" title="Cobalt">Co</a> on alumina </td> <td>Produces low-sulfur hydrocarbons, sulfur recovered via the <a href="/wiki/Claus_process" title="Claus process">Claus process</a> </td></tr></tbody></table> <figure class="mw-default-size mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Haber-Bosch-En.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/db/Haber-Bosch-En.svg/610px-Haber-Bosch-En.svg.png" decoding="async" width="610" height="183" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/db/Haber-Bosch-En.svg/915px-Haber-Bosch-En.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/db/Haber-Bosch-En.svg/1220px-Haber-Bosch-En.svg.png 2x" data-file-width="512" data-file-height="154" /></a><figcaption>Process flow diagram illustrating the use of catalysis in the synthesis of <a href="/wiki/Ammonia" title="Ammonia">ammonia</a> (NH<sub>3</sub>)</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Other_examples">Other examples</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Heterogeneous_catalysis&action=edit&section=9" title="Edit section: Other examples"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li>Reduction of <a href="/wiki/Nitrile" title="Nitrile">nitriles</a> in the synthesis of <a href="/wiki/Phenethylamine" title="Phenethylamine">phenethylamine</a> with <a href="/wiki/Raney_nickel" title="Raney nickel">Raney nickel</a> catalyst and hydrogen in <a href="/wiki/Ammonia" title="Ammonia">ammonia</a>:<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:NitrileHydrogenation.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3c/NitrileHydrogenation.svg/330px-NitrileHydrogenation.svg.png" decoding="async" width="330" height="93" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3c/NitrileHydrogenation.svg/495px-NitrileHydrogenation.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3c/NitrileHydrogenation.svg/660px-NitrileHydrogenation.svg.png 2x" data-file-width="393" data-file-height="111" /></a><figcaption>Nitrile hydrogenation</figcaption></figure></li> <li>The cracking, <a href="/wiki/Isomerisation" class="mw-redirect" title="Isomerisation">isomerisation</a>, and reformation of <a href="/wiki/Hydrocarbons" class="mw-redirect" title="Hydrocarbons">hydrocarbons</a> to form appropriate and useful blends of petrol.</li> <li>In automobiles, <a href="/wiki/Catalytic_converter" title="Catalytic converter">catalytic converters</a> are used to catalyze three main reactions: <ul><li>The <a href="/wiki/Oxidation" class="mw-redirect" title="Oxidation">oxidation</a> of <a href="/wiki/Carbon_monoxide" title="Carbon monoxide">carbon monoxide</a> to <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a>: <dl><dd>2CO(g) + O<sub>2</sub>(g) → 2CO<sub>2</sub>(g)</dd></dl></li> <li>The <a href="/wiki/Redox" title="Redox">reduction</a> of <a href="/wiki/Nitrogen_monoxide" class="mw-redirect" title="Nitrogen monoxide">nitrogen monoxide</a> back to <a href="/wiki/Nitrogen" title="Nitrogen">nitrogen</a>: <dl><dd>2NO(g) + 2CO(g) → N<sub>2</sub>(g) + 2CO<sub>2</sub>(g)</dd></dl></li> <li>The <a href="/wiki/Oxidation" class="mw-redirect" title="Oxidation">oxidation</a> of <a href="/wiki/Hydrocarbons" class="mw-redirect" title="Hydrocarbons">hydrocarbons</a> to water and <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a>: <dl><dd>2 C<sub>6</sub>H<sub>6</sub> + 15 O<sub>2</sub> → 12 CO<sub>2</sub> + 6 H<sub>2</sub>O</dd></dl></li></ul></li> <li>This process can occur with any of <a href="/wiki/Hydrocarbons" class="mw-redirect" title="Hydrocarbons">hydrocarbon</a>, but most commonly is performed with <a href="/wiki/Petrol" class="mw-redirect" title="Petrol">petrol</a> or <a href="/wiki/Diesel_fuel" title="Diesel fuel">diesel</a>.</li> <li>Asymmetric heterogeneous catalysis facilitates the production of pure enantiomer compounds using chiral heterogeneous catalysts.<sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup></li> <li>The majority of heterogeneous catalysts are based on <a href="/wiki/Metal" title="Metal">metals</a><sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> or <a href="/wiki/Oxide" title="Oxide">metal oxides</a>;<sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> however, some chemical reactions can be <a href="/wiki/Carbocatalysis" title="Carbocatalysis">catalyzed by carbon</a>-based materials, e.g., oxidative <a href="/wiki/Dehydrogenation" title="Dehydrogenation">dehydrogenations</a><sup id="cite_ref-zhang_29-0" class="reference"><a href="#cite_note-zhang-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> or selective <a href="/wiki/Oxidation" class="mw-redirect" title="Oxidation">oxidations</a>.<sup id="cite_ref-frank_30-0" class="reference"><a href="#cite_note-frank-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> <ul><li><a href="/wiki/Ethylbenzene" title="Ethylbenzene">Ethylbenzene</a> + 1/2 O<sub>2</sub> → <a href="/wiki/Styrene" title="Styrene">Styrene</a> + H<sub>2</sub>O</li> <li><a href="/wiki/Acrolein" title="Acrolein">Acrolein</a> + 1/2 O<sub>2</sub> → <a href="/wiki/Acrylic_acid" title="Acrylic acid">Acrylic acid</a></li></ul></li></ul> <div class="mw-heading mw-heading2"><h2 id="Solid-Liquid_and_Liquid-Liquid_Catalyzed_Reactions">Solid-Liquid and Liquid-Liquid Catalyzed Reactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Heterogeneous_catalysis&action=edit&section=10" title="Edit section: Solid-Liquid and Liquid-Liquid Catalyzed Reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Although the majority of heterogeneous catalysts are solids, there are a few variations which are of practical value. For two immiscible solutions (liquids), one carries the catalyst while the other carries the reactant. This set up is the basis of biphasic catalysis as implemented in the industrial production of butyraldehyde by the hydroformylation of propylene.<sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> </p> <table class="wikitable" style="text-align:center"> <tbody><tr> <th>Reacting phases </th> <th>Examples given </th> <th>Comment </th></tr> <tr> <td>solid + solution </td> <td>hydrogenation of fatty acids with nickel </td> <td>used for the production of <a href="/wiki/Margarine" title="Margarine">margarine</a> </td></tr> <tr> <td>immiscible liquid phases </td> <td><a href="/wiki/Hydroformylation" title="Hydroformylation">hydroformylation</a> of <a href="/wiki/Propene" class="mw-redirect" title="Propene">propene</a> </td> <td>aqueous phase catalyst; reactants and products mainly in non-aqueous phase </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Heterogeneous_catalysis&action=edit&section=11" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Heterogeneous_gold_catalysis" title="Heterogeneous gold catalysis">Heterogeneous gold catalysis</a></li> <li><a href="/wiki/Nanomaterial-based_catalyst" title="Nanomaterial-based catalyst">Nanomaterial-based catalysts</a></li> <li><a href="/wiki/Platinum_nanoparticles" class="mw-redirect" title="Platinum nanoparticles">Platinum nanoparticles</a></li> <li><a href="/wiki/Temperature-programmed_reduction" title="Temperature-programmed reduction">Temperature-programmed reduction</a></li> <li><a href="/wiki/Thermal_desorption_spectroscopy" title="Thermal desorption spectroscopy">Thermal desorption spectroscopy</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=Heterogeneous_catalysis&action=edit&section=12" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-:1-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-:1_1-0">^</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="CITEREFSchlögl2015" class="citation journal cs1">Schlögl, Robert (9 March 2015). 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Ed</i>. <b>50</b> (43): 10226–10230. <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/10.1002%2Fanie.201103340">10.1002/anie.201103340</a></span>. <a href="/wiki/Hdl_(identifier)" class="mw-redirect" title="Hdl (identifier)">hdl</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://hdl.handle.net/11858%2F00-001M-0000-0012-0B9A-8">11858/00-001M-0000-0012-0B9A-8</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/22021211">22021211</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Angew.+Chem.+Int.+Ed.&rft.atitle=Oxygen+Insertion+Catalysis+by+sp%3Csup%3E2%3C%2Fsup%3E+Carbon&rft.volume=50&rft.issue=43&rft.pages=10226-10230&rft.date=2011&rft_id=info%3Ahdl%2F11858%2F00-001M-0000-0012-0B9A-8&rft_id=info%3Apmid%2F22021211&rft_id=info%3Adoi%2F10.1002%2Fanie.201103340&rft.aulast=Frank&rft.aufirst=B.&rft.au=Blume%2C+R.&rft.au=Rinaldi%2C+A.&rft.au=Trunschke%2C+A.&rft.au=Schl%C3%B6gl%2C+R.&rft_id=https%3A%2F%2Fdoi.org%2F10.1002%252Fanie.201103340&rfr_id=info%3Asid%2Fen.wikipedia.org%3AHeterogeneous+catalysis" class="Z3988"></span></span> </li> <li id="cite_note-31"><span class="mw-cite-backlink"><b><a href="#cite_ref-31">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBoy_CornilsWolfgang_A._Herrmann2004" class="citation book cs1">Boy Cornils; <a href="/wiki/Wolfgang_A._Herrmann" title="Wolfgang A. 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