GB557513A - - Google Patents

Abstract

557,513. Aryl ethers of trihydric alcohols. SHELL DEVELOPMENT CO. Feb. 4, 1942, No. 1471. Convention date, Jan. 21, 1941. [Class 2 (iii)] Aryl ethers of trihydric alcohols are produced by the process of reacting a metal phenolate with a trihydric alcohol in which at least one hydroxy group has been replaced by a halogen atom, characterized in that the reaction is effected in an organic solvent having at least a partial solvency for water, which solvent is selected from the group consisting of the propyl alcohols, the butyl alcohols, the amyl alcohols, the dioxanes, and mixtures of an alcohol and a lower aliphatic hydrocarbon ; the amount of solvent present in the reaction mixture being sufficient for the metal halide formed. The preferred solvents mentioned include an alcohol such as propyl. butyl or amyl alcohol, a dioxane or a mixture of an alcohol and a lower aromatic hydrocarbon. As the salt of the phenolate, the alkali metal salt is preferred, as the trihydric alcohol component there may be used a glycerin halohydrin, an alkyl ether of a glycerin halohydrin, or a glycerin epihalohydrin. Compounds mentioned include glycerol mono-, and di-chlorhydrin, monobromhydrin of alpha phenyl glycerol, monochlorhydrin of pentaglycerol, dichlorhydrin of alpha ethyl-gamma cyclopentyl glycerol, epichlorhydrin, epibromhydrin of beta methyl glycerol, epi-iodo-hydrin of alpha ethyl glycerol, epichlorhydrin of phenyl glycerol, epichlorhydrin of pentaglycerol, gamma-, and beta-methyl ether of glycerol alpha monochlorhydrin, alpha methyl ether of glycerol beta bromhydrin, gamma ethyl ether of glycerol mono iodo-hydrin, gamma methyl ether of alpha methyl glycerol alpha monochlorhydrin, beta isopropyl ether of beta ethyl glycerol chlorhydrin, amyl ether of pentaglycerol chlorhydrin. Phenols which may be used include both monohydric and polyhydric phenols. Compounds mentioned include phenol, o-, m-, and p-cresols, the xylenols, ethyl phenol, tertiary butyl phenol, tertiary amyl phenol, diphenylol, higher alkylated phenols, polynuclear phenols such as alpha and beta naphthol. In examples (1) sodium cresylate is reacted in the presence of dioxane with the gamma isopropyl ether of glycerol alpha monochlorhydrin; (2) sodium phenate is reacted in dioxane solution with the gamma isopropyl ether of glycerol alpha monochlorhydrin to give the corresponding glyceryl alpha isopropyl gamma phenyl di-ether; (3) sodium phenate is reacted in dioxane solution with glycerol alpha monochlorhydrin; (4) sodium phenate is reacted in dioxane solution with epichlorhydrin to give glyceryl alpha gamma diphenyl ether. The dicresyl ether may be similarly obtained ; (5) sodium phenate is reacted in dioxane solution with the alpha methyl ether of glycerol chlorhydrin ; (6) as in example (5) using a different method of isolation of the product.