GB810069A - Improvements in the production of hydroxyethylated phenols - Google Patents

Abstract

Reaction products of a phenol of meltingpoint about 100 DEG C with ethylene oxide, one mol. of ethylene oxide having been absorbed for each hydroxyl group, may be used in the preparation of epoxy resins. Hydroxyethylation products specified are p,p1-bis-(beta-hydroxyethoxy) - diphenyl dimethylmethane, p,p1 - bis-(beta - hydroxyethoxy) - diphenylsulphone, p-bis - (beta - hydroxyethoxy) - benzene; 1,2,-bis-(beta-hydroxyethoxy)-anthraquinone.ALSO:The invention comprises a process for the production of hydroxyethylation products which have absorbed one mol. of ethylene oxide for each hydroxyl group, by reaction of a phenol of melting point above 100 DEG C. with ethylene oxide, below 100 DEG C. and an ethylene oxide pressure below the saturation pressure of the ethylene oxide, in the presence of an alkaline hydroxyethylation catalyst. The invention also comprises compounds of the formula <FORM:0810069/IV (b)/1> and <FORM:0810069/IV (b)/2> Suitable catalysts are, for example, sodium or potassium hydroxide, carbonate, bicarbonate, or cyanide, alkaline earth hydroxides and basic salts of an alkaline earth metal and quaternary ammonium salts, for example trimethylbenzyl-ammonium methoxide and ethoxide. The catalysts are directly introduced into the reaction vessel preferably in amounts of about 0.2 to 1 per cent by weight of the phenolic component in the liquid or solid state, preferably finely divided. The catalysts may also be converted into the phenolate before the reaction, or alcoholate, or added in aqueous solution. Suitable phenols which melt above 100 DEG C. are pyrocatechol, resorcinol, hydroquinone, pyrogallol, phloroglucinol, hydroxyhydroquinone, dihydroxyacetophenones, 4,41 dihydroxydiphenyl methane, p,p1-dihydroxydiphenyldimethylmethane, p-p1-dihydroxydiphenylsulphone, p-p1-dihydroxybenzophenone, hydroxynaphthalenes, hydroxyphenanthrenes, and hydroxyanthraquinones. The starting material may be in a solid finely powdered form or a fused state. The ethylene oxide may be supplied either continuously or batchwise, in small portions, preferably in liquid form, and the reaction vessel is previously rinsed out with an inert gas, e.g. nitrogen. The reaction is preferably carried out at 1-10 atmospheres between 70 DEG and 95 DEG C. Examples are given of the preparation of p-p1 - bis - (a - hydroxyethoxy) diphenyl dimethylmethane; p,p1 - bis - (b - hydroxyethoxy) diphenylsulphone; p - bis - (b - hydroxyethoxy) benzene; 1,2-bis-(b -hydroxyethoxy) anthraquinone.