GB821977A - Process for the production of monohydroxy polyethers of polyhydric alcohols - Google Patents

Abstract

Monohydroxy polyethers derived from polyhydric alcohols having at least 3 methylol, alkylmethylol or arylmethylol groups on one carbon atom are prepared by reacting 1 mol. of such a polyhydric alcohol, having 2, 3 or 4 free hydroxyl groups and 2, 1 or 0 etherified hydroxyl groups, with at leasst 1, 2 or 3 mols., respectively, of an organic monohalide, the halide atom of which is aliphatically bound and reactive, and of an alkali metal hydroxide, at 15 DEG to 200 DEG C. and in the absence of water or a volatile solvent. The invention also includes the diethers derived from trihydric alcohols having 3 methylol, alkylmethylol or arylmethylol groups attached to the same carbon atom. The reaction is preferably carried out at 50 DEG to 150 DEG C. in the absence of any solvent or in the presence of the monohydroxy polyether to be obtained or a similar monohydroxy polyether as diluent. Mixed ethers may be obtained by using a reactant containing etherified hydroxyl groups and etherifying all but one of the free hydroxyl groups according to the process above. The alcohol to be etherified may be of the type obtained by condensing formaldehyde with an aldehyde or ketone, for example, pentaerythritol, trimethylolethane, trimethylolethane, trimethylolpropane, trimethylo.butane, trimethylolphenylmethane, 3,3,3 - trimethylolpropan - 2 - ol, 3,3 - dimethylolbutan -2- ol, 2,2,2-trimethylol-1-phenylethanol or 2,2 - dimethylol - 1 - phenylpropanol. The organic monohalide may be a bromide, iodide or preferably chloride such as ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, hexyl, allyl, methallyl, crotyl, pentenyl, hexenyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, benzyl, phenyl ethyl, diphenylmethyl halides or haloethyl naphthalenes. The examples describe the preparation of trimethylolpropane diallyl ether, trimethylolpropane dibenzyl ether, trimethylolpropane dibutyl ether in the presence of the dibenzyl ether, trimethylolethane diallyl ether in the presence of the diallyl ether as diluent, trimethylolpropane dia -methallyl ether in the presence of the dibenzyl ether, trimethylolpropane monobenzyl monoallyl ether, pentaerythritol triallyl ether, pentaerythritol diallyl monobenzyl ether in the presence of trimethylolpropane diallyl ether and 3,3-dimethylolbutan-2-ol 3,3-diallyl ether in the presence of pentaerythritol trially ether. The diluents, where different from the products, are recovered by distilling off before or after the product ether.