Process for preparing trihydrocarbyl (2,5-dihydroxyphenyl) phosp

Details Process for preparing trihydrocarbyl (2,5-dihydroxyphenyl) phosp Process for preparing trihydrocarbyl (2,5-dihydroxyphenyl) phosp

1976-04-23

1978-06-06

Sneed, Helen M. S.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260526N, 2606065F, 2606065N, C07C 5308

Patent

active

040936503

ABSTRACT:
The title compounds are prepared by reacting (a) a trihydrocarbylphosphine, (b) p-benzoquinone, and (c) a protic acid in a liquid reaction medium comprising a lower alkanol of from 1 to 4 carbon atoms, a 1,2-alkylene glycol, dialkylene glycol or trialkylene glycol or a lower alkyl mono-ether of said glycols. The glycols are either ethylene glycol, propylene glycol, or the indicated oligomers thereof. Methanol is the solvent of choice. As an example, tri-n-butyl (2,5-dihydroxyphenyl)phosphonium chloroacetate was prepared in excellent yields by slowly adding tri-n-butylphosphine, precooled to about 0.degree. C, to a vigorously stirred suspension of p-benzoquinone in a methanol solution of chloroacetic acid at a temperature of approximately -10.degree. C. A precatalyzed epoxy resin was obtained by merely adding the methanol solution of the phosphonium chloroacetate to a liquid epoxy resin (e.g., the diglycidyl ether of bisphenol-A).

REFERENCES:
patent: 2862970 (1958-12-01), Thielen
Arshad et al., Pakistan J. Sci. Ind. Res. 12, 334-336 (1970) (Corresponding C.A. Article of record).
Ramirez et al., J.A.C.S. 78, 5614-5622 (1956).
Kosolapoff, Organic Phosphorus Compounds, Wiley-Interscience N.Y. vol. 2, pp. 197-198 (1972).
Grapon et al., Topics in Phosphorus Chemistry, Interscience Publ. N.Y., vol. 3, pp. 23-27 (1966).
Arshad et al., Tetrahedron Letters, vol. 22, pp. 2203-2211 (1966), Chemical Abstracts, U73, 65576u (1970).

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