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<title>Xanthate</title>

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

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<p>A <b>xanthate</b> is a <a href="Salt_(chemistry)" title="Salt (chemistry)">salt</a> or <a href="Ester" title="Ester">ester</a> of a xanthic acid. The formula of the salt of xanthic acid is <style data-mw-deduplicate="TemplateStyles:r1123817410">

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</style><span class="chemf nowrap">[R−O−CS<sub class="template-chem2-sub">2</sub>]<sup class="template-chem2-sup">−</sup>M<sup class="template-chem2-sup">+</sup></span> (where R is <a href="Organyl" class="mw-redirect" title="Organyl">organyl</a> group and M is usually <a href="Sodium" title="Sodium">Na</a> or <a href="Potassium" title="Potassium">K</a>).<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> Xanthate also refers to the <a href="Anion" class="mw-redirect" title="Anion">anion</a> <span class="chemf nowrap">[R−O−CS<sub class="template-chem2-sub">2</sub>]<sup class="template-chem2-sup">−</sup></span>. The formula of a <b>xanthic acid</b> is <span class="chemf nowrap">R−O−C(=S)−S−H</span>, such as <a href="Ethyl_xanthic_acid" title="Ethyl xanthic acid">ethyl xanthic acid</a>, while the formula of a <b>xanthate ester</b> is <span class="chemf nowrap">R−O−C(=S)−S−R'</span>, where R and R' are organyl groups. The salts of xanthates are sometimes called <i>O</i>-organyl dithioates. The esters of xanthic acid are sometimes called <i>O</i>,<i>S</i>-diorganyl esters of <a href="Dithiocarbonate" class="mw-redirect" title="Dithiocarbonate">dithiocarbonic acid</a>. The name <i>xanthate</i> is derived from <a href="Ancient_Greek" title="Ancient Greek">Ancient Greek</a> <span title="Ancient Greek (to 1453)-language text"><span lang="grc">ξανθός</span></span> (<i>xanthos</i>) meaning 'yellowish' or 'golden', and indeed most xanthate salts are yellow. They were discovered and named in 1823 by Danish chemist <a href="William_Christopher_Zeise" title="William Christopher Zeise">William Christopher Zeise</a>. These <a href="Organosulfur_compound" class="mw-redirect" title="Organosulfur compound">organosulfur compounds</a> are important in two areas: the production of <a href="Cellophane" title="Cellophane">cellophane</a> and related polymers from <a href="Cellulose" title="Cellulose">cellulose</a> and (in mining) for extraction of certain sulphide bearing ores.<sup id="cite_ref-Ullmann_2-0" class="reference"><a href="#cite_note-Ullmann-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> They are also versatile intermediates in <a href="Organic_synthesis" title="Organic synthesis">organic synthesis</a>.

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<div class="mw-heading mw-heading2"><h2 id="Formation_and_structure">Formation and structure</h2></div>

<p>Xanthate salts of <a href="Alkali_metals" class="mw-redirect" title="Alkali metals">alkali metals</a> are produced by the treatment of an <a href="Alcohol_(chemistry)" title="Alcohol (chemistry)">alcohol</a>, <a href="Alkali" title="Alkali">alkali</a>, and <a href="Carbon_disulfide" title="Carbon disulfide">carbon disulfide</a>. The process is called <b>xanthation</b>.<sup id="cite_ref-Ullmann_2-1" class="reference"><a href="#cite_note-Ullmann-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> In chemical terminology, the alkali reacts with the alcohol to produce an <a href="Alkoxide" title="Alkoxide">alkoxide</a>, which is the <a href="Nucleophile" title="Nucleophile">nucleophile</a> that adds to the <a href="Electrophilic" class="mw-redirect" title="Electrophilic">electrophilic</a> carbon atom in CS<sub>2</sub>.<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> Often the alkoxide is generated <a href="In_situ" title="In situ">in situ</a> by treating the alcohol with <a href="Sodium_hydroxide" title="Sodium hydroxide">sodium hydroxide</a> or <a href="Potassium_hydroxide" title="Potassium hydroxide">potassium hydroxide</a>:

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<p>For example, <a href="Sodium_ethoxide" title="Sodium ethoxide">sodium ethoxide</a> gives <a href="Sodium_ethyl_xanthate" title="Sodium ethyl xanthate">sodium ethyl xanthate</a>. Many alcohols can be used in this reaction. Technical grade xanthate salts are usually of 90–95% purity. Impurities include <a href="Alkali_metal" title="Alkali metal">alkali metal</a> <a href="Sulfide" title="Sulfide">sulfides</a>, <a href="Sulfates" class="mw-redirect" title="Sulfates">sulfates</a>, <a href="Trithiocarbonate" class="mw-redirect" title="Trithiocarbonate">trithiocarbonates</a>, <a href="Thiosulfate" title="Thiosulfate">thiosulfates</a>, <a href="Sulfites" class="mw-redirect" title="Sulfites">sulfites</a>, or <a href="Carbonates" class="mw-redirect" title="Carbonates">carbonates</a> as well as residual raw material such as alcohol and <a href="Alkali_hydroxide" title="Alkali hydroxide">alkali hydroxide</a>. These salts are available commercially as powder, granules, flakes, sticks, and solutions are available.

</p><p>Some commercially or otherwise useful xanthate salts include:

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<ul><li><a href="Sodium_ethyl_xanthate" title="Sodium ethyl xanthate">sodium ethyl xanthate</a> CH<sub>3</sub>CH<sub>2</sub>OCS<sub>2</sub>Na</li>

<li><a href="Potassium_ethyl_xanthate" title="Potassium ethyl xanthate">potassium ethyl xanthate</a>, CH<sub>3</sub>CH<sub>2</sub>OCS<sub>2</sub>K</li>

<li>potassium isopropyl xanthate, (CH<sub>3</sub>)<sub>2</sub>CHOCS<sub>2</sub>K<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></li>

<li>sodium isobutyl xanthate, (CH<sub>3</sub>)<sub>2</sub>CHCH<sub>2</sub>OCS<sub>2</sub>Na</li>

<li><a href="Potassium_amyl_xanthate" title="Potassium amyl xanthate">potassium amyl xanthate</a>, CH<sub>3</sub>(CH<sub>2</sub>)<sub>4</sub>OCS<sub>2</sub>K</li></ul>

<p>The OCS<sub>2</sub> core of xanthate salts and esters, like that of the <a href="Carbonate" title="Carbonate">carbonates</a> and the <a href="Ester" title="Ester">esters</a> has <a href="Trigonal_planar_molecular_geometry" title="Trigonal planar molecular geometry">trigonal planar molecular geometry</a>. The central <a href="Carbon" title="Carbon">carbon</a> atom is <a href="Orbital_hybridisation#sp2" title="Orbital hybridisation">sp<sup>2</sup>-hybridized</a>. The potassium salt of the amyl xanthate (<span class="chemf nowrap">KS<sub class="template-chem2-sub">2</sub>COC<sub class="template-chem2-sub">5</sub>H<sub class="template-chem2-sub">11</sub></span>) has been characterized by <a href="X-ray_crystallography" title="X-ray crystallography">X-ray crystallography</a>. The COCS<sub>2</sub> portion of the anion is planar. The C-S bond lengths are both 1.65 Å, and the C-O distance is 1.38 Å.<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>

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

<div class="mw-heading mw-heading3"><h3 id="Acid-base_properties">Acid-base properties</h3></div>

<p><b>Xanthic acids</b>, with the formula ROC(S)SH, can be prepared by treating alkali metal xanthates, e.g. <a href="Potassium_ethyl_xanthate" title="Potassium ethyl xanthate">potassium ethyl xanthate</a>, with <a href="Hydrochloric_acid" title="Hydrochloric acid">hydrochloric acid</a> at low temperatures. The methyl and ethyl xanthic acids are oils that are soluble in organic solvents. Benzyl xanthic acid is a solid. They have <a href="PKa" class="mw-redirect" title="PKa">pKas</a> near 2.<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> These compounds thermally decompose in the presence of base to the alcohol and carbon disulfide.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup>

</p><p>Xanthic acids characteristically decompose:

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<p>This reaction is the reverse of the method for the preparation of the xanthate salts. The intermediate in the decomposition is the xanthic acid, ROC(S)SH, which can be isolated in certain cases.

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<div class="mw-heading mw-heading3"><h3 id="Cleavage_of_C-O_bonds">Cleavage of C-O bonds</h3></div>

<p>The C-O bond in xanthate esters can be cleaved in various ways, providing a means for deoxygenation of alcohols. In <a href="Barton%E2%80%93McCombie_deoxygenation" title="Barton–McCombie deoxygenation">Barton–McCombie deoxygenation</a>, tributyltin hydride is the source of H atom. Several variations of this deoxygenation are known, for example using <a href="Azobisisobutyronitrile" title="Azobisisobutyronitrile">AIBN</a> and hydrosilanes.<sup id="cite_ref-March_8-0" class="reference"><a href="#cite_note-March-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup>

</p><p>Xanthates are intermediates in the <a href="Chugaev_elimination" title="Chugaev elimination">Chugaev elimination</a> process. They can be used to control <a href="Living_polymerization" title="Living polymerization">radical polymerisation</a> under the <a href="RAFT_(chemistry)" class="mw-redirect" title="RAFT (chemistry)">RAFT</a> process, also termed MADIX (macromolecular design via interchange of xanthates).

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<div class="mw-heading mw-heading3"><h3 id="Reactions_with_electrophiles">Reactions with electrophiles</h3></div>

<p>Xanthate anions undergo <a href="Alkylation" title="Alkylation">alkylation</a> to give xanthate esters, which are generally stable:<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>

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<p>They can be oxidized to <a href="Dixanthogen_disulfide" title="Dixanthogen disulfide">dixanthogen disulfides</a>:

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<p>Acylation of xanthates gives alkyl xanthogen esters (ROC(S)SC(O)R') and related anhydrides.<sup id="cite_ref-Ullmann_2-2" class="reference"><a href="#cite_note-Ullmann-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>

</p><p>Xanthates bind to transition metal cations as bidentate <a href="Ligand" title="Ligand">ligands</a>. The charge-neutral complexes are soluble in organic solvents.<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>

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<div class="mw-heading mw-heading2"><h2 id="Industrial_applications">Industrial applications</h2></div>

<p>Cellulose reacts with <a href="Carbon_disulfide" title="Carbon disulfide">carbon disulfide</a> (CS<sub>2</sub>) in presence of <a href="Sodium_hydroxide" title="Sodium hydroxide">sodium hydroxide</a> (NaOH) to produces sodium cellulose xanthate, which upon neutralization with <a href="Sulfuric_acid" title="Sulfuric acid">sulfuric acid</a> (H<sub>2</sub>SO<sub>4</sub>) gives <a href="Viscose" class="mw-redirect" title="Viscose">viscose</a> rayon or <a href="Cellophane" title="Cellophane">cellophane</a> paper (<a href="Sellotape" title="Sellotape">Sellotape</a> or <a href="Scotch_Tape" class="mw-redirect" title="Scotch Tape">Scotch Tape</a>).

</p><p>Xanthate salts (e.g. sodium alkyl xanthates, <a href="Dixanthogen" class="mw-redirect" title="Dixanthogen">dixanthogen</a>) are widely used as <a href="Flotation_process" class="mw-redirect" title="Flotation process">flotation</a> agents in mineral processing.

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<div class="mw-heading mw-heading2"><h2 id="Related_compounds">Related compounds</h2></div>

<p>Rarely encountered, <a href="Thioxanthate" title="Thioxanthate">thioxanthates</a> arise by the reaction of CS<sub>2</sub> with thiolate salts. For example, sodium ethylthioxanthate has the formula C<sub>2</sub>H<sub>5</sub>SCS<sub>2</sub>Na. <a href="Dithiocarbamate" title="Dithiocarbamate">Dithiocarbamates</a> are also related compounds. They arise from the reaction of a secondary amine with CS<sub>2</sub>. For example, <a href="Sodium_diethyldithiocarbamate" title="Sodium diethyldithiocarbamate">sodium diethyldithiocarbamate</a> has the formula (C<sub>2</sub>H<sub>5</sub>)<sub>2</sub>NCS<sub>2</sub>Na.

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<div class="mw-heading mw-heading2"><h2 id="Environmental_impacts">Environmental impacts</h2></div>

<p>While biodegradable, this class of chemicals may be toxic to life in water at concentrations of less than 1 mg/L.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> Water downstream of mining operations is often contaminated with xanthates.<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>

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<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="IUPAC" class="mw-redirect" title="IUPAC">IUPAC</a> does not recommend the use of the term xanthate, although it is in current use in the scientific literature: <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/X06696.html">Xanthate</a>". <style data-mw-deduplicate="TemplateStyles:r1238218222">

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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.X06696">10.1351/goldbook.X06696</a></span>

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<li id="cite_note-Ullmann-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-Ullmann_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Ullmann_2-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Ullmann_2-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><cite id="CITEREFRoy" class="citation encyclopaedia cs1">Roy, Kathrin-Maria. "Xanthates". <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.a28_423">10.1002/14356007.a28_423</a>. <a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>978-3-527-30673-2</bdi>.</cite></span>

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<li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text">This report gives a detailed procedure for the <a href="Potassium_ethyl_xanthate" title="Potassium ethyl xanthate">potassium ethyl xanthate</a>: <cite id="CITEREFPriceStacy1948" class="citation journal cs1">Price, Charles C.; Stacy, Gardner W. (1948). "<i>p</i>-Nitrophenyl sulfide". <i>Organic Syntheses</i>. <b>28</b>: 82. <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.028.0082">10.15227/orgsyn.028.0082</a>.</cite></span>

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<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="CITEREFPerumalreddy_Chandrasekaran,_James_P._Donahue2009" class="citation journal cs1">Perumalreddy Chandrasekaran, James P. Donahue (2009). <a rel="nofollow" class="external text" href="https://doi.org/10.15227%2Forgsyn.086.0333">"Synthesis of 4,5-Dimethyl-1,3-Dithiol-2-One"</a>. <i>Organic Syntheses</i>. <b>86</b>: 333. <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/10.15227%2Forgsyn.086.0333">10.15227/orgsyn.086.0333</a></span>.</cite></span>

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<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="CITEREFN._A._Frolova,_T._I._Malinovskii,_V._Kh._Kravtsov,_Yu._M._Chumakov,_S._B._Leonov1991" class="citation journal cs1">N. A. Frolova, T. I. Malinovskii, V. Kh. Kravtsov, Yu. M. Chumakov, S. B. Leonov (1991). "Кристаппическая и молекчлярная стрчктчра амипксантогената калия" [Crystal and Molecular Structure of Potassium Amylxanthate]. <i>Dokl.Akad.Nauk SSSR (Proc.Nat.Acad.Sci.USSR)</i>. <b>316</b>: 371.</cite><span class="cs1-maint citation-comment"><code class="cs1-code">{{cite journal}}</code>: CS1 maint: multiple names: authors list (link)</span></span>

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<li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text"><cite id="CITEREFMillicanSauers1979" class="citation journal cs1">Millican, Robert J.; Sauers, Carol K. (1979). "General acid-catalyzed decomposition of alkyl xanthates". <i>The Journal of Organic Chemistry</i>. <b>44</b> (10): <span class="nowrap">1664–</span>1669. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fjo01324a018">10.1021/jo01324a018</a>.</cite></span>

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<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="CITEREFGattowBehrendt1977" class="citation book cs1">Gattow, Gerhard; Behrendt, Werner (1977). <i>Carbon Sulfides and their Inorganic and Complex Chemistry</i>. Stuttgart: Georg Thieme. <a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>3135262014</bdi>.</cite></span>

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<li id="cite_note-March-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-March_8-0">^</a></b></span> <span class="reference-text"><cite id="CITEREFSmithMarch2007" class="citation cs2">Smith, Michael B.; <a href="Jerry_March" title="Jerry March">March, Jerry</a> (2007), <a rel="nofollow" class="external text" href="https://books.google.com/books?id=JDR-nZpojeEC&printsec=frontcover"><i>Advanced Organic Chemistry: Reactions, Mechanisms, and Structure</i></a> (6th ed.), New York: Wiley-Interscience, p. 1833, <a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>978-0-471-72091-1</bdi></cite> </span>

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<li id="cite_note-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-9">^</a></b></span> <span class="reference-text"><cite id="CITEREFGagoszZard2007" class="citation journal cs1">Gagosz, Fabien; Zard, Samir Z. (2007). <a rel="nofollow" class="external text" href="http://www.orgsyn.org/demo.aspx?prep=V84P0032">"A Xanthate-Transfer Approach to α-Trifluoromethylamines"</a>. <i><a href="Organic_Syntheses" title="Organic Syntheses">Organic Syntheses</a></i>. <b>84</b>: 32</cite>; <cite class="citation cs2"><i>Collected Volumes</i>, vol. 11, p. 212</cite>.</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="CITEREFHaiduc2004" class="citation encyclopaedia cs1">Haiduc, I. (2004). "1,1-Dithiolato ligands". In McClevert, J. A.; Meyer, T. J. (eds.). <i>Comprehensive Coordination Chemistry II</i>. Vol. 1. pp. <span class="nowrap">349–</span>376.</cite></span>

</li>

<li id="cite_note-11"><span class="mw-cite-backlink"><b><a href="#cite_ref-11">^</a></b></span> <span class="reference-text"><cite id="CITEREFGalsbølSchäffer1967" class="citation book cs1">Galsbøl, F.; Schäffer, C. E. (1967). "Tris (O-Ethyldithiocarbonato) Complexes of Tripositive Chromium, Indium, and Cobalt". <i>Inorganic Syntheses</i>. <a href="Inorganic_Syntheses" title="Inorganic Syntheses">Inorganic Syntheses</a>. Vol. 10. pp. <span class="nowrap">42–</span>49. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F9780470132418.ch6">10.1002/9780470132418.ch6</a>. <a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>9780470132418</bdi>.</cite></span>

</li>

<li id="cite_note-Hauptmann-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-Hauptmann_12-0">^</a></b></span> <span class="reference-text">Siegfried Hauptmann: <i>Organische Chemie</i>, 2. durchgesehene Auflage, VEB Deutscher Verlag für Grundstoffindustrie, Leipzig, 1985, S. 652, <a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>3-342-00280-8</bdi>.</span>

</li>

<li id="cite_note-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-13">^</a></b></span> <span class="reference-text"><cite id="CITEREFBesserBrumbaughAllertPoulton2009" class="citation journal cs1">Besser, J.; Brumbaugh, W.; Allert, A.; Poulton, B.; Schmitt, C.; Ingersoll, C. (2009). <span class="id-lock-subscription" title="Paid subscription required"><a rel="nofollow" class="external text" href="http://digitalcommons.unl.edu/cgi/viewcontent.cgi?article=1882&context=usgsstaffpub">"Ecological impacts of lead mining on Ozark streams: toxicity of sediment and pore water"</a></span>. <i>Ecotoxicology and Environmental Safety</i>. <b>72</b> (2): <span class="nowrap">516–</span>526. <a href="Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2009EcoES..72..516B">2009EcoES..72..516B</a>. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.ecoenv.2008.05.013">10.1016/j.ecoenv.2008.05.013</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/18603298">18603298</a>.</cite></span>

</li>

<li id="cite_note-14"><span class="mw-cite-backlink"><b><a href="#cite_ref-14">^</a></b></span> <span class="reference-text"><cite id="CITEREFXuLayKorte1988" class="citation journal cs1">Xu, Y.; Lay, J. P.; Korte, F. (1988). "Fate and effects of xanthates in laboratory freshwater systems". <i>Bulletin of Environmental Contamination and Toxicology</i>. <b>41</b> (5): <span class="nowrap">683–</span>689. <a href="Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1988BuECT..41..683X">1988BuECT..41..683X</a>. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2FBF02021019">10.1007/BF02021019</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/3233367">3233367</a>. <a href="S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:2696850">2696850</a>.</cite></span>

</li>

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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="Thioxanthate" title="Thioxanthate">Thioxanthate</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 2025-05-25" href="https://en.wikipedia.org/wiki/?title=Xanthate&oldid=1292136764">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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