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Tetrakis(hydroxymethyl)phosphonium chloride
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<h2 id="synthesis-structure-and-reactions">Synthesis, structure and reactions</h2> <p>THPC can be synthesized with high yield by treating <a href="/facts/Phosphine/aYysn5TS">phosphine</a> with <a href="/facts/Formaldehyde/Ck8RLfqk">formaldehyde</a> in the presence of <a href="/facts/Hydrochloric_acid/HqItJlUT">hydrochloric acid</a>.<a class="footnote-ref" id="fnref:2" href="#fn:2"><sup>2</sup></a> </p> PH3 + 4 H2C=O + HCl → [P(CH2OH)4]Cl <p>The cation P(CH2OH)4+ features four-coordinate phosphorus, as is typical for <a href="/facts/Phosphonium_salt/uS2PCt7X">phosphonium salts</a>. </p><p>THPC converts to tris(hydroxymethyl)phosphine upon treatment with aqueous <a href="/facts/Sodium_hydroxide/xjtdYtq7">sodium hydroxide</a>:<a class="footnote-ref" id="fnref:3" href="#fn:3"><sup>3</sup></a> </p> [P(CH2OH)4]Cl + NaOH → P(CH2OH)3 + H2O + H2C=O + NaCl <h2 id="application-in-textiles">Application in textiles</h2> <p>THPC has industrial importance in the production of crease-resistant and <a href="/facts/Flame-retardant/0dpdUCYh">flame-retardant</a> <a href="/facts/Textile_finishing/Mn7PMJFW">finishes</a> on cotton textiles and other cellulosic fabrics.<a class="footnote-ref" id="fnref:4" href="#fn:4"><sup>4</sup></a> <a class="footnote-ref" id="fnref:5" href="#fn:5"><sup>5</sup></a> A flame-retardant finish can be prepared from THPC by the Proban Process,<a class="footnote-ref" id="fnref:6" href="#fn:6"><sup>6</sup></a> in which THPC is treated with urea. The <a href="/facts/Urea/6j84AoCG">urea</a> condenses with the hydroxymethyl groups on THPC. The phosphonium structure is converted to <a href="/facts/Phosphine_oxide/Tq9TMtn4">phosphine oxide</a> as the result of this reaction.<a class="footnote-ref" id="fnref:7" href="#fn:7"><sup>7</sup></a> </p> [P(CH2OH)4]Cl + NH2CONH2 → (HOCH2)2P(O)CH2NHC(O)NH2 + HCl + HCHO + H2 + H2O <p>This reaction proceeds rapidly, forming insoluble high molecular weight polymers. The resulting product is applied to the fabrics in a "pad-dry process". This treated material is then treated with ammonia and ammonia hydroxide to produce fibers that are flame-retardant. </p><p>THPC can condense with many other types of monomers in addition to urea. These monomers include amines, phenols and polybasic acids and anhydrides. </p> <h2 id="references">References</h2> <ol> <li id="fn:1"><p>Svara, Jürgen; Weferling, Norbert; Hofmann, Thomas (2006). "Phosphorus Compounds, Organic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_545.pub2. ISBN 3527306730. <a href="3527306730" target="_blank">3527306730</a> <a href="#fnref:1" class="footnote-back-ref">↩</a></p></li> <li id="fn:2"><p>Svara, Jürgen; Weferling, Norbert; Hofmann, Thomas (2006). "Phosphorus Compounds, Organic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_545.pub2. ISBN 3527306730. <a href="3527306730" target="_blank">3527306730</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></p></li> <li id="fn:3"><p>M. Caporali, L. Gonsalvi, F. Zanobini, M. Peruzzini "Synthesis of the Water-Soluble Bidentate (P,N) Ligand PTN(Me)" Inorg. Syntheses, 2011, Vol. 35, p. 92–108. doi:10.1002/9780470651568.ch5 <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:3" class="footnote-back-ref">↩</a></p></li> <li id="fn:4"><p>Fischer, Klaus; Marquardt, Kurt; Schlüter, Kaspar; Gebert, Karlheinz; Borschel, Eva-Marie; Heimann, Sigismund; Kromm, Erich; Giesen, Volker; Schneider, Reinhard; Lee Wayland, Rosser (2000). "Textile Auxiliaries". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a26_227. ISBN 3-527-30673-0. <a href="3-527-30673-0" target="_blank">3-527-30673-0</a> <a href="#fnref:4" class="footnote-back-ref">↩</a></p></li> <li id="fn:5"><p>Weil, Edward D.; Levchik, Sergei V. (2008). "Flame Retardants in Commercial Use or Development for Textiles". J. Fire Sci. 26 (3): 243–281. doi:10.1177/0734904108089485. S2CID 98355305. <a href="/wiki/J._Fire_Sci." target="_blank">/wiki/J._Fire_Sci.</a> <a href="#fnref:5" class="footnote-back-ref">↩</a></p></li> <li id="fn:6"><p>"Frequently asked questions: What is the PROBAN® process?". Rhodia Proban. Archived from the original on December 7, 2012. Retrieved February 25, 2013. <a href="https://web.archive.org/web/20121207081548/http://www.rhodia-proban.com/uk/faq.asp" target="_blank">https://web.archive.org/web/20121207081548/http://www.rhodia-proban.com/uk/faq.asp</a> <a href="#fnref:6" class="footnote-back-ref">↩</a></p></li> <li id="fn:7"><p>Reeves, Wilson A.; Guthrie, John D. (1956). "Intermediate for Flame-Resistant Polymers-Reactions of Tetrakis(hydroxymethyl)phosphonium Chloride". Industrial and Engineering Chemistry. 48 (1): 64–67. doi:10.1021/ie50553a021. <a href="/wiki/Industrial_and_Engineering_Chemistry" target="_blank">/wiki/Industrial_and_Engineering_Chemistry</a> <a href="#fnref:7" class="footnote-back-ref">↩</a></p></li> </ol>