Production of bis(alpha-alkylbenzyl)ethers

Claim 2

Process for the production of bis(alpha-alkylbenzyl) ethers corresponding to the formula: ##STR3## wherein, R is a member selected from the group consisting of lower alkyl, lower haloalkyl, chloro, bromo, sulfo and nitro radicals; m is an integer not greater that 3 and n is an integer of from 1 to 7, inclusive, comprising: (a) heating, while removing water of dehydration as formed, an alpha alkylbenzyl alcohol of the formula: ##STR4## wherein, R, m and n are as defined above, with agitation, at a temperature below about 200° C. in the presence of an acidic clay present in catalytic amount and having a surface area of at least about 200 square meters per gram, and an acidity of at least 1 milligram potassium hydroxide per gram of clay for a time sufficient to effect conversion of at least about 75% of at said alcohol to the desired ether and thereby forming a reaction product mixture; (b) introducing a basic compound to the reaction product mixture of Step (a), above, in an amount sufficient to deactivate the catalyst; and (c) recovering the desired bis(alpha-alkylbenzyl) ether from the reaction product mixture.

Claim 3

The process of claim 1 wherein said clay is present in an amount of between 0.05% and 5%, by weight, of said alcohol.

Claim 4

The process of claim 1 wherein said heating is carried out at a temperature of between about 125° C. and 150° C.

Claim 5

The process of claim 1 wherein heating of the alpha-alkylbenzyl alcohol is effected in an inert solvent.

Claim 6

The process of claim 2 wherein m is 0 and n is 1 in each of said formulas.

Claim 7

The process of claim 5 wherein said clay has a surface area of at least about 250 square meters per gram and an acidity of at least about 5 milligrams potassium hydroxide per gram of clay.

Claim 8

The process of claim 2 wherein the alpha methyl benzyl alcohol starting material is present, in major proportion, as a component of an aromatic rich distilland product mixture derived from the ethyl benzene hydroperoxide epoxidation of an olefinically unsaturated compound.

Claim 9

The process of claim 6 wherein the ether is recovered by subjecting the reaction product mixture to distillation in the presence of the clay.

Claim 10

In the process for the production of bis(alpha-methylbenzyl) ether by heating an alpha methylbenzyl alcohol reactant in the presence of an acid catalyst at an elevated temperature, followed by deactivation of the acidic catalyst by contact with a basic compound, and recovery of the desired ether, the improvement which comprises: (a) employing, as reactant, an aromatic-rich distilland product mixture containing alpha-methylbenzyl alcohol in major proportion and, obtained from the ethyl benzene hydroperoxide epoxidation of an olefinically unsaturated compound, (b) employing as said catalyst, an acidic clay having a surface area of at least about 200 square meters per gram, and an acidity of at least 1 milligram potassium hydroxide per gram of clay (c) heating of the mixture containing alpha-methylbenzyl alcohol is effected at a temperature of between about 125° C. and 175° C. for a time sufficient to effect conversion of at least about 75% of the alpha methylbenzyl alcohol contained in said mixture to the desired bis(alpha-methylbenzyl) ether, (d) recovering said bis(alpha-methylbenzyl) ether by distillation following removal of unreacted methyl benzyl alcohol and lower boiling impurities.

Claim 11

In the process for the production of bis(alpha-methylbenzyl) ether by heating an alpha methylbenzyl alcohol reactant in the presence of an acid catalyst at an elevated temperature, followed by deactivation of the acidic catalyst by contact with a basic compound, and recovery of the desired ether, the improvement which comprises: (a) employing, as reactant, an aromatic-rich distilland product mixture containing alpha-methylbenzyl alcohol in major proportion and, obtained from the ethyl benzene hydroperoxide epoxidation of an olefinically unsaturated compound, (b) employing as said catalyst, an acidic clay having a surface area of at least about 200 square meters per gram, and an acidity of at least 1 milligram potassium hydroxide per gram of clay (c) heating of the mixture containing alpha-methylbenzyl alcohol is effected at a temperature of between about 125° C. and 175° C. for a time sufficient to effect conversion of at least about 75% of the alpha methylbenzyl alcohol contained in said mixture to the desired bis(alpha-methylbenzyl) ether, (d) recovering said bis(alpha-methylbenzyl) ether by distillation following removal of unreacted methyl benzyl alcohol and lower boiling impurities.

Claim 12

The process of claim 9 wherein said clay has a surface area of at least about 250 square meters per gram and an acidity of at least about 5 milligrams potassium hydroxide per gram of clay.

Claim 13

The process of claim 9 wherein the distillation of step (d) is effected in the presence of the quenched clay catalyst.