# US 4,391,994 A · Process for the production of ethers

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- Number: US 4,391,994 A
- Document ID: US4391994A
- Status: Granted
- Kind: A
- Application number: 06/312,781
- Filed: 1981-10-19
- Granted: 1983-07-05
- Earliest claimed: 1979-07-04
- Assignees: Nisso Petrochemical Industrie Co., Ltd.
- Inventors: Kiyoshi Kogoma; Yu Ohashi; Jiro Niizeki; Norio Sone; Takashi Tobita
- Web page: https://patentgrep.com/patent/US4391994A

## CPC

- C07C 41/02: from oxiranes
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

Oxyalkylene group of an alkylene oxide is inserted into a chain-type ether compound having at least one lower alkyl group by reacting the latter with the alkylene oxide in the presence of a catalyst prepared by mixing boron trifluoride and/or stannic chloride with an active-hydrogen compound exemplified by water or a lower aliphatic alcohol. The reaction results reduced formation of by-product dimer of the alkylene oxide even under an increased charging ratio of the alkylene oxide to the chain-type ether.

## Claims

### Claim 1

A process for the production of glycol diethers, wherein a chain-type ether compound represented by the formula
R.sup.1 O--(CH.sub.2).sub.m --O].sub.n R.sup.2
wherein
R.sup.1 is an alkyl having 1 to 4 carbon atoms,
R.sup.2 is an alkyl having 1 to 12 carbon atoms, phenyl, phenyl substituted by lower alkyl or lower alkoxy, or aralkyl consisting of lower alkylene and phenyl,
m is an integer from 1 to 4, and
n is an integer from 0 to 8
and an alkylene oxide compound selected from the group consisting of compounds represented by the formulas ##STR12## wherein R.sup.3 is halogen-or non-substituted alkyl having 1 to 5 carbon atoms or phenyl, and
l is an integer from 0 to 5
are reacted in the presence of a catalyst prepared by mixing boron trifluoride and/or stannic chloride with an active-hydrogen compound selected from the group consisting of water, alcohol carboxylic acid, phenol and sulfonic acid with the proviso that mercaptan and hydroxamic acid may be included in the said active-hydrogen compound when boron trifluoride is employed, one equivalent of the said active-hydrogen compound being mixed with 1 to 5 moles of boron trifluoride and/or stannic compound, to form a boron trifluoride and/or stannic chloride complex therewith, the said catalyst being employed in an amount of from 0.05 to 5 mole percent of the chain-type ether compound based on boron trifluoride and/or stannic chloride, and the molar ratio of the alkylene oxide compound to the chain-type ether compound is from 0.5 to 5.

### Claim 2 (depends on 1)

A process according to claim 1, wherein the active-hydrogen compound is water or an aliphatic alcohol having 1 to 4 carbon atoms.

### Claim 3 (depends on 1)

A process according to claim 1, wherein the chain-type ether compound is represented by the formula
R.sup.1 O--(CH.sub.2).sub.m O].sub.n R.sup.2
wherein
R.sup.1 and R.sup.2 are same or different alkyl having 1 to 4 carbon atoms,
m is 1 or 2, and
n is an integer from 0 to 4.

### Claim 4 (depends on 3)

A process according to claim 3, wherein
R.sup.1 and R.sup.2 are methyl,
m is 1, and
n is 0 or 1.

### Claim 5 (depends on 1)

A process according to claim 1, wherein the alkylene oxide compound is ethylene oxide or epichlorohydrin.

### Claim 6 (depends on 1)

A process according to claim 1, wherein the active-hydrogen compound is mixed with in an amount of 1 to 3 per mole of boron trifluoride and/or stannic chloride on the basis of the number of active-hydrogen.