Preparation of symmetrical ethers
AssigneeThe Dow Chemical Company
InventorsRobert A. Dubois, Harold H. Freedman
Life of this patent
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Abstract
Symmetrical ethers are prepared in high yield by reacting an alkyl halide, sulfate, or sulfonate with base in the presence of a catalytic amount of both an onium salt and a carboxylate salt. For example, dibenzyl ether is produced in yields exceeding 95 percent by contacting benzylchloride with a 50 percent sodium hydroxide solution in the presence of a catalytic amount of both tetra-n-butylammonium bisulfate and sodium acetate.
Claims12
A process for preparing symmetrical ethers comprising reacting by contacting a primary or secondary alkyl or inertly-substituted alkyl halide, sulfate, or sulfonate, with an alkali metal hydroxide or alkaline earth metal hydroxide in the presence of both a catalytic amount of a quaternary ammonium salt or a quaternary phosphonium salt of the formula
- R.sub.1 R.sub.2 R.sub.3 R.sub.4 Q.sup.+ A.sup.-
- wherein Q is a quaternized atom of nitrogen or phosphorus, A is a neutralizing anion, and R.sub.1 -R.sub.4 are hydrocarbyl groups of from 1 to about 16 carbon atoms each with a combined minimum total of at least about 10 carbon atoms and a catalytic amount of a carboxylate salt or thiocarboxylate salt comprised of an alkyl, aryl, arylalkyl, cycloalkyl or inertly-substituted derivatives thereof, carboxylate or thiocarboxylate anion and an alkali metal or alkaline earth metal cation.
Dependencies are inferred from the claim text.