Preparation of ethers

Claim 2

A process for the preparation of saturated mono-ethers by reacting a mono-olefin and a monohydric alcohol which comprises contacting in the absence of water and oxygen (a) a mono-olefinic compound with (b) a monohydric alcohol, in the presence of (c) a catalyst system comprising a palladium component, a copper component, and an alkali metal or alkaline earth metal halide component under reaction conditions of temperature and pressure sufficient to form a saturated mono-ether product.

Claim 3

A process in accordance with claim 1 wherein said contacting also takes place in the presence of a surfactant.

Claim 4

A process in accordance with claim 2 wherein said surfactant is selected from the group of: (1) quaternary ammonium salts of the general formula (R'") 4 N + X - , (2) alkali metal alkyl sulfates of the general formula R' v OSO 3 M, (3) alkali metal salts of alkanoic acids of the general formula R' v CO 2 M, (4) alkali metal salts of alkaryl sulfonic acids of the general formula ##STR5## (5) 1-alkyl pyridinium salts of the general formula ##STR6## wherein R'" is an alkyl radical of from 1 to 20 carbon atoms and wherein the total number of carbon atoms in said quaternary ammonium salt is from about 8 to about 30 carbon atoms; X - is selected from the group consisting of Br - , Cl - , I - , F - , R'"CO 2 - , QSO 3 - , BF 4 - , HSO 4 - wherein Q is an aryl or alkaryl radical of 6 to 10 carbon atoms; R' v is an alkyl radical of from 10 to about 20 carbon atoms; M is an alkali metal; R v is an alkyl radical of 1 to 4 carbon atoms and wherein n is 0 or an integer of from 1 to 4.

Claim 5

A process in accordance with claim 1 wherein said mono-olefin is selected from the group consisting of: (a) acyclic mono-olefinic compounds containing from 2-20 carbon atoms per molecule, and (b) cyclic mono-olefinic compounds containing 5-20 carbon atoms per molecule; and said monohydric alcohol has the general formula R 4 OH wherein R 4 is selected from the group consisting of: (1) alkyl radicals containing from 1 to about 20 carbon atoms per radical, (2) cycloalkyl radicals containing 5 to about 10 carbon atoms per radical, and (3) aralkyl radicals containing 7 to 20 carbon atoms per radical.

Claim 6

A process in accordance with claim 4 wherein said olefin is an acyclic mono-olefinic compound containing from 2 to 8 carbon atoms per molecule and said alcohol is an alkyl monohydric alcohol containing 1 to about 8 carbon atoms per molecule.

Claim 7

A process in accordance with claim 1 wherein said contacting takes place at a temperature of about 20° C. to about 200° C. under autogenous pressure.

Claim 8

A process in accordance with claim 1 wherein the molar ratio of the alcohol group to the olefinic group is in the range of about 20:1 to about 1:20, the molar ratio of the olefinic reactant to palladium of the catalyst system is in the range of about 5:1 to about 1,000:1, and the molar ratio of copper to palladium in the catalyst system is from about 1:1 to about 200:1.

Claim 9

A process in accordance with claim 7 wherein the molar ratio of the alcohol group to the olefinic group is in the range of about 0.5:1 to 10:1, the molar ratio of the olefinic reactant to palladium of the catalyst system is 10:1 to about 250:1, and the molar ratio of the copper to palladium in the catalyst system is from about 2:1 to about 50:1.

Claim 10

A process in accordance with claim 1 wherein the molar ratio of halide ion derived from the alkali metal or alkaline earth metal halide to palladium in the catalyst system is from about 5:1 to about 1,000:1.

Claim 11

A process in accordance with claim 2 wherein the molar ratio of the surfactant to palladium in the catalyst system is in the range of about 0.01:1 to about 10:1.

Claim 12

A process in accordance with claim 1 wherein said olefinic compound is isobutylene and said monohydric alcohol is methanol.

Claim 13

A process for the preparation of methyl t-butyl ether which comprises contacting in the absence of water and oxygen: (a) isobutylene and (b) methanol, in the presence of (c) a catalyst system comprising palladium chloride, cupric chloride, and lithium chloride, and (d) cetyltrimethylammonium bromide, under such conditions of temperature and pressure as to form methyl t-butyl ether.

Claim 14

A process for the preparation of methyl t-butyl ether which comprises contacting in the absence of water and oxygen: (a) isobutylene and (b) methanol, in the presence of (c) a catalyst system comprising palladium chloride, cupric chloride, and lithium chloride, and (d) cetyltrimethylammonium bromide, under such conditions of temperature and pressure as to form methyl t-butyl ether.