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m-Cresol
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<h2 id="production">Production</h2> <p>Together with many other compounds, <i>m</i>-cresol is traditionally extracted from <a href="/facts/Coal_tar/6lLDL4Ic">coal tar</a>, the volatile materials obtained in the production of <a href="/facts/Coke_(fuel)/vD8xjd0m">coke</a> from <a href="/facts/Bituminous_coal/ETUBa9ee">(bituminous) coal</a>. This residue contains a few percent by weight of <a href="/facts/Phenol/ACJs5NIU">phenol</a> and isomeric <a href="/facts/Cresol/dQ1s1qMC">cresols</a>. In the cymene–cresol process, <a href="/facts/Toluene/Pzdt8dwD">toluene</a> is alkylated with <a href="/facts/Propylene/5eLDmPvm">propylene</a> to give isomers of <a href="/facts/Cymene/6Rxk74DE">cymene</a>, which can be oxidatively dealkylated analogous to the <a href="/facts/Cumene_process/qG6AIc9j">cumene process</a>. Another method, involves <a href="/facts/Carbonylation/Jq8jghNR">carbonylation</a> of a mixture of <a href="/facts/Methallyl_chloride/LKvbJCyx">methallyl chloride</a> and <a href="/facts/Acetylene/yaDh6cmJ">acetylene</a> in the presence of <a href="/facts/Nickel_carbonyl/8Py5Dre1">nickel carbonyl</a>.<a class="footnote-ref" id="fnref:2" href="#fn:2"><sup>2</sup></a> </p> <h2 id="applications">Applications</h2> <p><i>m</i>-Cresol is a precursor to numerous compounds. Important applications include: </p> <ul><li>pesticides such as <a href="/facts/Fenitrothion/93frIpIz">fenitrothion</a> and <a href="/facts/Fenthion/72Nsh3bq">fenthion</a></li> <li>synthetic <a href="/facts/Vitamin_E/UcL1ghae">vitamin E</a> by <a href="/facts/Methylation/EvDMWVW5">methylation</a> to give 2,3,6-trimethylphenol<a class="footnote-ref" id="fnref:3" href="#fn:3"><sup>3</sup></a></li> <li><a href="/facts/Antiseptic/ua05WK9M">antiseptics</a>, such as <a href="/facts/Amylmetacresol/Hv1h4mwb">amylmetacresol</a></li> <li>a <a href="/facts/Solvent/LoMPMz8S">solvent</a> for <a href="/facts/Polymer/eF32E50K">polymers</a>. For example, <a href="/facts/Polyaniline/AoJ3IaWM">polyaniline</a> is cast from a solution of <i>m</i>-cresol to form a polyaniline film with a superior conductivity than polyaniline alone. This phenomenon is known as secondary doping.<a class="footnote-ref" id="fnref:4" href="#fn:4"><sup>4</sup></a></li> <li>preservatives in some <a href="/facts/Insulin/oXG0myt1">insulin</a> preparations</li> <li>the starting point in the <a href="/facts/Total_synthesis/3GGoqhBm">total synthesis</a> of <a href="/facts/Thymol/S6u6qWcL">thymol</a>,<a class="footnote-ref" id="fnref:5" href="#fn:5"><sup>5</sup></a> an important synthetic chemical for regions lacking natural sources of the flavor compound:<a class="footnote-ref" id="fnref:6" href="#fn:6"><sup>6</sup></a></li></ul> C7H8O + <a href="/facts/Propene/5eLDmPvm">C3H6</a> ⇌ <a href="/facts/Thymol/S6u6qWcL">C10H14O</a> <ul><li>synthesis of dicresulene and <a href="/facts/Policresulen/K97VtY79">policresulen</a></li> <li>synthesis of <a href="/facts/Toliprolol/zqWdE8pC">toliprolol</a>, <a href="/facts/Tolamolol/SP3gnv0t">tolamolol</a> & cresatin</li></ul> <h2 id="natural-occurrences">Natural occurrences</h2> <p><i>m</i>-Cresol is a component found in temporal glands secretions during <a href="/facts/Musth/Tpmcz2pt">musth</a> in male <a href="/facts/African_elephant/vMA6IWh1">African elephants</a> (<i>Loxodonta africana</i>).<a class="footnote-ref" id="fnref:7" href="#fn:7"><sup>7</sup></a> </p><p><i>m</i>-Cresol is a constituent of <a href="/facts/Tobacco_smoke/E3HVAVxL">tobacco smoke</a>.<a class="footnote-ref" id="fnref:8" href="#fn:8"><sup>8</sup></a> </p><p><i>m</i>-Cresol is a component found in secretions from the ant <i><a href="/facts/Colobopsis_saundersi/e4zvzLJG">Colobopsis saundersi</a></i> during <a href="/facts/Autothysis/VkALvUmx">Autothysis</a>.<a class="footnote-ref" id="fnref:9" href="#fn:9"><sup>9</sup></a> <a class="footnote-ref" id="fnref:10" href="#fn:10"><sup>10</sup></a> </p> <h2 id="see-also">See also</h2> <ul><li><a href="/facts/Cresol/dQ1s1qMC">Cresol</a></li></ul> <h2 id="external-links">External links</h2> <ul><li><a href="https://www.cdc.gov/niosh/npg/npgd0155.html">NIOSH Pocket Guide to Chemical Hazards</a> cdc.gov</li> <li><a href="http://www.chemicalbook.com/ChemicalProductProperty_EN_CB7852747.htm">Chemical and physical properties</a> chemicalbook.com</li></ul> <h2 id="references">References</h2> <ol> <li id="fn:1"><p>Helmut Fiege (2007). "Cresols and Xylenols". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a08_025. ISBN 978-3527306732. <a href="978-3527306732" target="_blank">978-3527306732</a> <a href="#fnref:1" class="footnote-back-ref">↩</a></p></li> <li id="fn:2"><p>Helmut Fiege (2007). "Cresols and Xylenols". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a08_025. ISBN 978-3527306732. <a href="978-3527306732" target="_blank">978-3527306732</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></p></li> <li id="fn:3"><p>Helmut Fiege (2007). "Cresols and Xylenols". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a08_025. ISBN 978-3527306732. <a href="978-3527306732" target="_blank">978-3527306732</a> <a href="#fnref:3" class="footnote-back-ref">↩</a></p></li> <li id="fn:4"><p>Alan G. MacDiarmid and Arthur J. Epstein. 1995. "Secondary Doping in Polyaniline" Synthetic Metals 69 (85-92). <a href="#fnref:4" class="footnote-back-ref">↩</a></p></li> <li id="fn:5"><p>Stroh, R.; Sydel, R.; Hahn, W. (1963). Foerst, Wilhelm (ed.). Newer Methods of Preparative Organic Chemistry, Volume 2 (1st ed.). New York: Academic Press. p. 344. ISBN 9780323150422. <a href="9780323150422" target="_blank">9780323150422</a> <a href="#fnref:5" class="footnote-back-ref">↩</a></p></li> <li id="fn:6"><p>Asim Kumar Mukhopadhyay (2004). Industrial Chemical Cresols and Downstream Derivatives. New York: CRC Press. pp. 99–100. ISBN 9780203997413. <a href="9780203997413" target="_blank">9780203997413</a> <a href="#fnref:6" class="footnote-back-ref">↩</a></p></li> <li id="fn:7"><p>Some chemical constituents of the secretion from the temporal gland of the African elephant (Loxodonta africana). Jack Adams, Alexander Garcia and Christopher S. Foote, Journal of Chemical Ecology, 1978, Volume 4, Number 1, 17-25, doi:10.1007/BF00988256 <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:7" class="footnote-back-ref">↩</a></p></li> <li id="fn:8"><p>Talhout, Reinskje; Schulz, Thomas; Florek, Ewa; Van Benthem, Jan; Wester, Piet; Opperhuizen, Antoon (2011). "Hazardous Compounds in Tobacco Smoke". International Journal of Environmental Research and Public Health. 8 (12): 613–628. doi:10.3390/ijerph8020613. ISSN 1660-4601. PMC 3084482. PMID 21556207. <a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3084482" target="_blank">https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3084482</a> <a href="#fnref:8" class="footnote-back-ref">↩</a></p></li> <li id="fn:9"><p>Jones, T. H.; Clark, D. A.; Edwards, A. A.; Davidson, D. W.; Spande, T. F.; Snelling, Roy R. (2004). "The chemistry of exploding ants, Camponotus spp. (cylindricus complex)". Journal of Chemical Ecology. 30 (8): 1479–1492. doi:10.1023/B:JOEC.0000042063.01424.28. PMID 15537154. S2CID 23756265. <a href="/wiki/Roy_Snelling" target="_blank">/wiki/Roy_Snelling</a> <a href="#fnref:9" class="footnote-back-ref">↩</a></p></li> <li id="fn:10"><p>Betz, Oliver (2010). "Adhesive Exocrine Glands in Insects: Morphology, Ultrastructure, and Adhesive Secretion". In von Byern, Janek; Grunwald, Ingo (eds.). Biological Adhesive Systems. pp. 111–152. doi:10.1007/978-3-7091-0286-2_8. ISBN 978-3-7091-0141-4. <a href="978-3-7091-0141-4" target="_blank">978-3-7091-0141-4</a> <a href="#fnref:10" class="footnote-back-ref">↩</a></p></li> </ol>