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<title>Thioxanthate</title>

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

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<div id="mw-content-text" class="mw-body-content mw-content-ltr" lang="en" dir="ltr"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><p>In <a href="Chemistry" title="Chemistry">chemistry</a>, a <b>thioxanthate</b> is an <a href="Organosulfur_compound" class="mw-redirect" title="Organosulfur compound">organosulfur compound</a> with the formula RSCS<sub>2</sub>X. When X is an alkali metal, the thioxanthate is a salt. When X is a transition metal, the thioxanthate is a <a href="Ligand" title="Ligand">ligand</a>, and when X is an organic group, the compounds are called thioxanthate esters. They are usually yellow colored compounds that often dissolve in organic solvents. They are used as precursors to some catalysts, <a href="Froth_flotation" title="Froth flotation">froth flotation</a> agents, and additives for lubricants.

</p>

<div class="mw-heading mw-heading2"><h2 id="Preparation_and_reactions">Preparation and reactions</h2></div>

<p>The alkali metal thioxanthates are produced by treating a thiol with a base in the presence of <a href="Carbon_disulfide" title="Carbon disulfide">carbon disulfide</a>, as illustrated by the preparation of sodium ethyl thioxanthate:.<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>

</p>

<dl><dd>EtSH + NaOH + CS<sub>2</sub> → EtSCS<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">−</sup><br><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span>Na<sup>+</sup> + H<sub>2</sub>O</dd></dl>

<p>Sodium ethyl thioxanthate is similar structurally to <a href="Sodium_ethyl_xanthate" title="Sodium ethyl xanthate">sodium ethyl xanthate</a>.

</p><p><a href="Alkylation" title="Alkylation">Alkylation</a> of thioxanthate anions gives thioxanthate esters.<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>

The preparation of ethyl methyl thioxanthate is a simple illustration:

</p>

<dl><dd>EtSCS<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">−</sup><br><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span>Na<sup>+</sup> + MeI → EtSCS<sub>2</sub>Me + NaI</dd></dl>

<p>Thioxanthate esters are also called esters of <a href="Trithiocarbonate" class="mw-redirect" title="Trithiocarbonate">trithiocarbonate</a>.

</p>

<ul><li><a href="Thiocarbonic_acid" title="Thiocarbonic acid">Thiocarbonic acid</a></li>

<li><a href="Thiocarbonate" title="Thiocarbonate">Thiocarbonate</a></li></ul>

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

<li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text">Haiduc, I. "1,1-Dithiolato Ligands" in Comprehensive Coordination Chemistry II Edited by McCleverty, J. A.; Meyer, T. J 2004, volume 1, pp. 349-376.</span>

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</style><cite id="CITEREFJan_Larsen,_Christine_Lenoir1995" class="citation journal cs1">Jan Larsen, Christine Lenoir (1995). "2,2'-Bi-5,6-Dihydro-1,3-Dithiolo[4,5-b][1,4]Dithiinylidene (BEDT-TTF)". <i>Organic Syntheses</i>. <b>72</b>: 265. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.15227%2Forgsyn.072.0265">10.15227/orgsyn.072.0265</a>.</cite></span>

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</style><div id="Functional_groups729" style="font-size:114%;margin:0 4em"><a href="Functional_group" title="Functional group">Functional groups</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Hydrocarbon" title="Hydrocarbon">Hydrocarbons</a> <br><span class="nobold">(only C and H)</span></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="Alkyl" class="mw-redirect" title="Alkyl">Alkyl</a>

<ul><li><a href="Methyl_group" title="Methyl group">Methyl</a></li>

<li><a href="Ethyl_group" title="Ethyl group">Ethyl</a></li>

<li><a href="Propyl_group" title="Propyl group">Propyl</a></li>

<li><a href="Cyclopropyl" class="mw-redirect" title="Cyclopropyl">Cyclopropyl</a></li>

<li><a href="Butyl_group" title="Butyl group">Butyl</a></li>

<li><a href="Pentyl_group" title="Pentyl group">Pentyl</a></li></ul></li>

<li><a href="Methylene_group" title="Methylene group">Methylene</a>

<ul><li><a href="Methylene_bridge" title="Methylene bridge">Bridge</a></li>

<li><a href="Methine_group" title="Methine group">Methine</a></li></ul></li>

<li><a href="Alkene" title="Alkene">Alkene</a>

<ul><li><a href="Vinyl_group" title="Vinyl group">Vinyl</a></li>

<li><a href="Allyl_group" title="Allyl group">Allyl</a></li>

<li><a href="Propenyl" title="Propenyl">1-Propenyl</a></li>

<li><a href="Crotyl_group" title="Crotyl group">Crotyl</a></li>

<li><a href="Allenes" title="Allenes">Allene</a></li>

<li><a href="Cumulene" title="Cumulene">Cumulene</a></li></ul></li>

<ul><li><a href="Phenyl_group" title="Phenyl group">Phenyl</a></li>

<li><a href="Benzyl_group" title="Benzyl group">Benzyl</a></li></ul></li>

<li><a href="Alkyne" title="Alkyne">Alkyne</a></li>

<li><a href="Carbene" title="Carbene">Carbene</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Only <a href="Carbon" title="Carbon">carbon</a>, <br><a href="Hydrogen" title="Hydrogen">hydrogen</a>, <br>and <a href="Oxygen" title="Oxygen">oxygen</a> <br><span class="nobold">(only C, H and O)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">R-O-R</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="Acetal" title="Acetal">Acetal</a></li>

<li><a href="Alcohol_(chemistry)" title="Alcohol (chemistry)">Alcohol</a></li>

<li><a href="Alkoxy_group" title="Alkoxy group">Alkoxy</a>

<ul><li><a href="Methoxy_group" title="Methoxy group">Methoxy</a></li></ul></li>

<li><a href="Ether" title="Ether">Ether</a>

<ul><li><a href="Enol_ether" title="Enol ether">Enol ether</a></li>

<li><a href="Epoxide" title="Epoxide">Epoxide</a></li></ul></li>

<li><a href="Organic_peroxides" title="Organic peroxides">Peroxy</a>

<ul><li><a href="Hydroperoxide" title="Hydroperoxide">Hydroperoxy</a></li>

<li><a href="Dioxirane" title="Dioxirane">Dioxiranes</a></li></ul></li>

<li><a href="Ethylenedioxy" title="Ethylenedioxy">Ethylenedioxy</a></li>

<li><a href="Methylenedioxy" title="Methylenedioxy">Methylenedioxy</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Carbonyl_group" title="Carbonyl group">carbonyl</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="Acetyl_group" title="Acetyl group">Acetyl</a></li>

<li><a href="Acryloyl_group" class="mw-redirect" title="Acryloyl group">Acryloyl</a></li>

<li><a href="Benzoyl_group" title="Benzoyl group">Benzoyl</a></li></ul></li>

<li><a href="Aldehyde" title="Aldehyde">Aldehyde</a>

<ul><li><a href="Ketene" title="Ketene">Ketene</a></li></ul></li>

<li><a href="Ketone" title="Ketone">Ketone</a></li>

<li><a href="Ynone" title="Ynone">Ynone</a></li>

<li><a href="Reductone" title="Reductone">Reductone</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">carboxy</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="Carboxylic_acid" title="Carboxylic acid">Carboxyl</a>

<ul><li><a href="Acetoxy_group" title="Acetoxy group">Acetoxy</a></li>

<li><a href="Carboxylic_anhydride" class="mw-redirect" title="Carboxylic anhydride">Anhydride</a></li></ul></li>

<li><a href="Ester" title="Ester">Ester</a>

<ul><li><a href="Orthoester" class="mw-redirect" title="Orthoester">Orthoester</a></li></ul></li></ul>

</div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Only one <br>element, <br>not being <br>carbon, <br>hydrogen, <br>or oxygen <br><span class="nobold">(one element, <br>not C, H or O)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Nitrogen" title="Nitrogen">Nitrogen</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="Amine" title="Amine">Amine</a>

<ul><li><a href="Enamine" title="Enamine">Enamine</a></li>

<li><a href="Quaternary_ammonium_cation" title="Quaternary ammonium cation">Ammonium</a></li></ul></li>

<li><a href="Hydrazines" title="Hydrazines">Hydrazo</a></li>

<li><a href="Nitrene" title="Nitrene">Nitrene</a></li>

<li><a href="Imine" title="Imine">Imine</a></li>

<li><a href="Oxime" title="Oxime">Oxime</a></li>

<li><a href="Hydrazone" title="Hydrazone">Hydrazone</a></li>

<li><a href="Amide_(functional_group)" title="Amide (functional group)">Amide</a></li>

<li><a href="Imidate" class="mw-redirect" title="Imidate">Imidate</a></li>

<li><a href="Amidine" title="Amidine">Amidine</a></li>

<li><a href="Carbamate" title="Carbamate">Carbamate</a></li>

<li><a href="Imide" title="Imide">Imide</a></li>

<li><a href="Nitrile" title="Nitrile">Nitrile</a></li>

<li><a href="Isocyanide" title="Isocyanide">Isonitrile</a></li>

<li><a href="Cyanate_ester" title="Cyanate ester">Cyanate</a></li>

<li><a href="Isocyanate" title="Isocyanate">Isocyanate</a></li>

<li><a href="Nitrate_ester" title="Nitrate ester">Nitrate</a></li>

<li><a href="Nitrite_ester" class="mw-redirect" title="Nitrite ester">Nitrite</a></li>

<li><a href="Nitro_compound" title="Nitro compound">Nitro</a></li>

<li><a href="Nitroso" title="Nitroso">Nitroso</a></li>

<li><a href="NONOate" title="NONOate">NONOate</a></li>

<li><a href="Triazole" title="Triazole">Triazole</a></li>

<li><a href="Tetrazole" title="Tetrazole">Tetrazole</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Silicon" title="Silicon">Silicon</a></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="Silane" title="Silane">Silane</a>

<ul><li><a href="Hydrosilane" class="mw-redirect" title="Hydrosilane">Hydrosilane</a></li>

<li><a href="Chlorosilane" title="Chlorosilane">Chlorosilane</a></li></ul></li>

<li><a href="Organosilicon_chemistry#Silenes" title="Organosilicon chemistry">Silene</a></li>

<li><a href="Silanol" title="Silanol">Silanol</a></li>

<li><a href="Siloxide" title="Siloxide">Siloxide</a></li>

<li><a href="Siloxane" title="Siloxane">Siloxane</a></li>

<li><a href="Silanone" title="Silanone">Silanone</a></li>

<li><a href="Silyl_ether" title="Silyl ether">Silether</a></li>

<li><a href="Metalloles" class="mw-redirect" title="Metalloles">Silole</a></li>

<li><a href="Silatrane" class="mw-redirect" title="Silatrane">Silatrane</a></li>

<li><a href="Silicate" title="Silicate">Silicate</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Phosphorus" title="Phosphorus">Phosphorus</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="Organophosphate" title="Organophosphate">Phosphate</a>

<ul><li><a href="Phosphodiester" class="mw-redirect" title="Phosphodiester">Phosphodiester</a></li></ul></li>

<li><a href="Phosphonate" title="Phosphonate">Phosphonate</a>

<ul><li><a href="Phosphite_ester" title="Phosphite ester">Phosphite</a></li></ul></li>

<li><a href="Phosphonite" title="Phosphonite">Phosphonous</a></li>

<li><a href="Phosphinate" title="Phosphinate">Phosphinate</a></li>

<li><a href="Phosphine_oxide" title="Phosphine oxide">Phosphine oxide</a></li>

<li><a href="Organophosphine" title="Organophosphine">Phosphine</a>

<ul><li><a href="Phosphonium" title="Phosphonium">Phosphonium</a></li></ul></li>

<li><a href="Phosphaalkene" title="Phosphaalkene">Phosphaalkene</a></li>

<li><a href="Phosphaalkyne" title="Phosphaalkyne">Phosphaalkyne</a></li>

<li><a href="1-Phosphaallenes" title="1-Phosphaallenes">Phosphaallene</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Sulfur" title="Sulfur">Sulfur</a></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="Thiol" title="Thiol">Thiol</a></li>

<li><a href="Thioether" class="mw-redirect" title="Thioether">Thioether</a>

<ul><li><a href="Sulfonium" title="Sulfonium">Sulfonium</a></li>

<li><a href="Thia-crown_ether" title="Thia-crown ether">Thia-crown ether</a></li></ul></li>

<li><a href="Persulfide" title="Persulfide">Persulfide</a></li>

<li><a href="Disulfide" title="Disulfide">Disulfide</a></li>

<li><a href="Sulfenic_acid" title="Sulfenic acid">Sulfenic acid</a></li>

<li><a href="Thiosulfinate" title="Thiosulfinate">Thiosulfinate</a></li>

<li><a href="Sulfoxide" title="Sulfoxide">Sulfoxide</a></li>

<li><a href="Thiosulfonate" title="Thiosulfonate">Thiosulfonate</a></li>

<li><a href="Sulfinic_acid" title="Sulfinic acid">Sulfinic acid</a></li>

<li><a href="Sulfone" title="Sulfone">Sulfone</a></li>

<li><a href="Sulfonic_acid" title="Sulfonic acid">Sulfonic acid</a></li>

<li><a href="Thioketone" title="Thioketone">Thioketone</a></li>

<li><a href="Thial" title="Thial">Thial</a></li>

<li><a href="Thioester" title="Thioester">Thioester</a></li>

<li><a href="Thionoester" class="mw-redirect" title="Thionoester">Thionoester</a></li>

<li><a href="Xanthate" title="Xanthate">Xanthate</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Boron" title="Boron">Boron</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="Boronic_acid" title="Boronic acid">Boronic acid</a></li>

<li><a href="Borinic_acid" title="Borinic acid">Borinic acid</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Selenium" title="Selenium">Selenium</a></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="Selenol" title="Selenol">Selenol</a></li>

<li><a href="Selenonic_acid" title="Selenonic acid">Selenonic acid</a></li>

<li><a href="Seleninic_acid" title="Seleninic acid">Seleninic acid</a></li>

<li><a href="Selenenic_acid" title="Selenenic acid">Selenenic acid</a></li>

<li><a href="Selone" title="Selone">Selone</a></li>

<li><a href="Selenide#Inorganic_selenides" title="Selenide">Selenoether</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Tellurium" title="Tellurium">Tellurium</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="Tellurol" title="Tellurol">Tellurol</a></li>

<li><a href="Telluroketone" title="Telluroketone">Telluroketone</a></li>

<li><a href="Telluride_(chemistry)#Organic_tellurides" title="Telluride (chemistry)">telluroether</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Polonium" title="Polonium">Polonium</a></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="Polonium_hydride#Properties" title="Polonium hydride">Polonol</a></li>

<li><a href="Organopolonium_chemistry" title="Organopolonium chemistry">Polonoether</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i><a href="Halocarbon" title="Halocarbon">Halo</a></i></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="Haloalkane" title="Haloalkane">Haloalkane</a>

<ul><li><a href="Fluoroethyl" title="Fluoroethyl">Fluoroethyl</a></li>

<li><a href="Trifluoromethyl" class="mw-redirect" title="Trifluoromethyl">Trifluoromethyl</a></li>

<li><a href="Trichloromethyl_group" title="Trichloromethyl group">Trichloromethyl</a></li>

<li><a href="Trifluoromethoxy_group" title="Trifluoromethoxy group">Trifluoromethoxy</a></li>

<li><a href="Iodane" class="mw-redirect" title="Iodane">Hypervalent iodine</a></li></ul></li>

<li><a href="Vinyl_halide" title="Vinyl halide">Vinyl halide</a>

<ul><li><a href="Vinyl_iodide_functional_group" title="Vinyl iodide functional group">Iodide</a></li></ul></li>

<li><a href="Acyl_halide" title="Acyl halide">Acyl halide</a>

<ul><li><a href="Acyl_chloride" title="Acyl chloride">Chloride</a></li></ul></li>

<li><a href="Perchlorate_ester" class="mw-redirect" title="Perchlorate ester">Perchlorate</a></li></ul>

</div></td></tr></tbody></table><div></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><a href="Isothiocyanate" title="Isothiocyanate">Isothiocyanate</a></li>

<li><a href="Phosphoramides" title="Phosphoramides">Phosphoramides</a></li>

<li><a href="Sulfenyl_chloride" title="Sulfenyl chloride">Sulfenyl chloride</a></li>

<li><a href="Sulfonamide" title="Sulfonamide">Sulfonamide</a></li>

<li><a href="Organic_thiocyanates" title="Organic thiocyanates">Thiocyanate</a></li>

<li><a href="Sulfinylamine" title="Sulfinylamine">Sulfinylamines</a></li></ul>

</div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div>

<dd><i><a href="Chemical_classification" class="mw-redirect" title="Chemical classification">chemical classification</a></i></dd>

<dd><i><a href="Chemical_nomenclature" title="Chemical nomenclature">chemical nomenclature</a></i>

<dl><dd><a href="IUPAC_nomenclature_of_inorganic_chemistry" title="IUPAC nomenclature of inorganic chemistry">inorganic</a></dd>

<dd><a href="IUPAC_nomenclature_of_organic_chemistry" title="IUPAC nomenclature of organic chemistry">organic</a></dd></dl></dd></dl>

</div></td></tr></tbody></table></div></div><div><div class="zim-footer">

This article is issued from <a class="external text" title="Last edited on 2025-07-20" href="https://en.wikipedia.org/wiki/?title=Thioxanthate&oldid=1301620570">Wikipedia</a>. The text is available under <a class="external text" href="https://creativecommons.org/licenses/by-sa/4.0/deed.en">Creative Commons Attribution-Share Alike 4.0</a> unless otherwise noted. Additional terms may apply for the media files.

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