Process for the preparation of bisphenols

Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing

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568717, 568723, 568726, C07C 3718, C07C 3912

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active

051361108

ABSTRACT:
The invention is a process for the preparation of triaromatic bisphenols reacting a phenolic compound, e.g. phenol, with a suitable halo-compound, for instance 1,1-dichloroethylbenzene, 1-chlorostyrene, or mixtures thereof. The reaction may be conducted in the presence or absence of a solvent; an excess of the phenolic compound can serve as the solvent. The product is conveniently recovered by removing the by-product HCl, excess phenolic compound, excess solvent and cooling. Yields of bis-1,1-(4-hydroxyphenyl)-1-phenylethane which are greater than 90% of theoretical have been obtained by the reaction of phenol and 1,1-dichloroethylbenzene and a large portion of the yield is para isomer. Suitable halo-compounds include aromatic dihalo-compounds having at least one aliphatic substituent having two alpha-halogen atoms and at least one beta halogen atom, halo-styrenes having structures corresponding to such aromatic dihalo-compounds except that an alpha-halogen atom and a beta hydrogen atom are removed and there is a double bond between the alpha and beta carbon atoms, trihalotoluenes, and dihalocyanotoluenes.

REFERENCES:
patent: 2634297 (1953-04-01), Moyle
patent: 2858342 (1958-10-01), Bender et al.
patent: 3001972 (1961-09-01), Christenson et al.
patent: 3378518 (1968-04-01), Doyle
patent: 4467122 (1984-08-01), Szabolcs
Justus Liebig's Annalen der chemie 363: pp. 275-276 (1908).
Chemical Abstract 29:855(7) (1935).
Chemical Abstract 65:3795c (1966).
J. Amer. Chem. Soc. 37, pp. 2575-2591 (1915).
Chemical Abstract 85:192405k (Japan Kokai 76 86,434).
J. Amer. Chem. Soc. 61, pp. 345-348 (1939).
J. Amer. Chem. Soc. 76, pp. 4547-4550 (1954).

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