Menu
Home Explore People Places Arts History Plants & Animals Science Life & Culture Technology
On this page
Tetrakis(hydroxymethyl)phosphonium chloride
Chemical compound

Tetrakis(hydroxymethyl)phosphonium chloride (THPC) is an organophosphorus compound with the chemical formula [P(CH2OH)4]Cl. It is a white water-soluble salt with applications as a precursor to fire-retardant materials and as a microbiocide in commercial and industrial water systems.

Related Image Collections Add Image
Profiles
1 Image
We don't have any YouTube videos related to Tetrakis(hydroxymethyl)phosphonium chloride yet.
We don't have any PDF documents related to Tetrakis(hydroxymethyl)phosphonium chloride yet.
We don't have any Books related to Tetrakis(hydroxymethyl)phosphonium chloride yet.
We don't have any archived web articles related to Tetrakis(hydroxymethyl)phosphonium chloride yet.

Synthesis, structure and reactions

THPC can be synthesized with high yield by treating phosphine with formaldehyde in the presence of hydrochloric acid.2

PH3 + 4 H2C=O + HCl → [P(CH2OH)4]Cl

The cation P(CH2OH)4+ features four-coordinate phosphorus, as is typical for phosphonium salts.

THPC converts to tris(hydroxymethyl)phosphine upon treatment with aqueous sodium hydroxide:3

[P(CH2OH)4]Cl + NaOH → P(CH2OH)3 + H2O + H2C=O + NaCl

Application in textiles

THPC has industrial importance in the production of crease-resistant and flame-retardant finishes on cotton textiles and other cellulosic fabrics.4 5 A flame-retardant finish can be prepared from THPC by the Proban Process,6 in which THPC is treated with urea. The urea condenses with the hydroxymethyl groups on THPC. The phosphonium structure is converted to phosphine oxide as the result of this reaction.7

[P(CH2OH)4]Cl + NH2CONH2 → (HOCH2)2P(O)CH2NHC(O)NH2 + HCl + HCHO + H2 + H2O

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.

THPC can condense with many other types of monomers in addition to urea. These monomers include amines, phenols and polybasic acids and anhydrides.

References

  1. 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. 3527306730 ↩

  2. 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. 3527306730 ↩

  3. 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 /wiki/Doi_(identifier) ↩

  4. 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. 3-527-30673-0 ↩

  5. 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. /wiki/J._Fire_Sci. ↩

  6. "Frequently asked questions: What is the PROBAN® process?". Rhodia Proban. Archived from the original on December 7, 2012. Retrieved February 25, 2013. https://web.archive.org/web/20121207081548/http://www.rhodia-proban.com/uk/faq.asp ↩

  7. 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. /wiki/Industrial_and_Engineering_Chemistry ↩