# US 4,395,574 A · Phosphonium phenoxide catalysts for promoting reaction of epoxides with phenols and/or carboxylic acids

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- Number: US 4,395,574 A
- Document ID: US4395574A
- Status: Granted
- Kind: A
- Application number: 06/288,613
- Filed: 1981-07-30
- Granted: 1983-07-26
- Earliest claimed: 1979-05-23
- Assignees: The Dow Chemical Company
- Inventors: George A. Doorakian; James L. Bertram
- Web page: https://patentgrep.com/patent/US4395574A

## CPC

- C07F 9/54: Quaternary phosphonium compounds
- C08G 59/688: {containing phosphorus}
- C08G 65/105: {Onium compounds}
- C08G 65/2621: {containing amine groups}
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

Certain tetrahydrocarbyl phosphonium phenoxide salts are described herein which are novel compounds and/or novel catalysts for promoting the reaction between vicinal epoxides and phenols and/or carboxylic acids or anhydrides. These catalysts are particularly useful in preparing high molecular weight epoxy resins by the advancement reaction of diglycidyl ether of bisphenol A with bisphenol A.

## Claims

### Claim 1

A compound represented by the formula ##STR11## or a complex of the compound represented by Formula I with one or more equivalents of a phenol, H.sub.m X, wherein
(1) R.sub.1 -R.sub.4 each independently is a hydrocarbyl or inertly-substituted hydrocarbyl;
(2) X is a phenoxide anion, said anion being a conjugate base of a polyhydric phenol bearing from 2 to 6 nuclear hydroxyl groups and having from about 12 to about 30 carbon atoms; and
(3) m is the valence of the anion X.

### Claim 2 (depends on 1)

The compound defined by claim 1 wherein R.sub.1 -R.sub.4 each independently is phenyl or C.sub.1 to C.sub.12 alkyl or inertly-substituted alkyl.

### Claim 3 (depends on 1)

The compound defined by claim 1 wherein R.sub.1 -R.sub.4 each independently is phenyl or C.sub.1 to C.sub.4 alkyl.

### Claim 4 (depends on 1)

The compound defined by claim 1 wherein R.sub.1 -R.sub.4 each independently is phenyl or n-butyl.

### Claim 5 (depends on 1)

The compound defined by claim 1 wherein R.sub.1 is an n-butyl or ethyl group and R.sub.2 -R.sub.4 are each phenyl.

### Claim 6 (depends on 1, 2, 5)

The compound defined by claim 1, 2 or 5 wherein X is derived from a polyhydric phenol corresponding to phenolphthalein or to the formula ##STR12## wherein, (1) each R independently is a hydrogen, halogen, hydrocarbyl, inertly-substituted hydrocarbyl or hydrocarbyloxy group;
(2) Y is a single covalent bond, oxygen, sulfur, --CO--, --SO--, --SO.sub.2 -- or lower alkylene or alkylidene of from 1 to 6 carbon atoms, inclusive; and
(3) m is the integer 1 or 2.

### Claim 7 (depends on 6)

The compound defined by claim 6 wherein each R independently is hydrogen, chlorine or bromine.

### Claim 8 (depends on 7)

The compound defined by claim 7 wherein Y is C.sub.1 -C.sub.4 alkylene or alkylidene.

### Claim 9 (depends on 8)

The compound defined by claim 8 wherein Y is methylene or isopropylidene.

### Claim 10 (depends on 6)

The compound defined by claim 6 wherein X is a phenoxide anion or dianion derived from bisphenol A, bisphenol F, phenolphthalein, 2,2',6,6'-tetrachlorobisphenol A, bisphenol S, bis(4-hydroxyphenyl), 2-hydroxyphenylmethane or 2,2',6,6'-tetrabromobisphenol A.

### Claim 11 (depends on 10)

The compound defined by claim 10 wherein X is a phenoxide anion or dianion derived from bisphenol A or 2,2',6,6'-tetrabromobisphenol A.