# US 4,396,774 A · Use of a catalyst to inhibit formation of tar during the "ENE" reaction of an ethylenically unsaturated alpha, beta dicarboxylic acid compound and an ethylenically unsaturated hydrocarbon

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- Number: US 4,396,774 A
- Document ID: US4396774A
- Status: Granted
- Kind: A
- Application number: 06/360,372
- Filed: 1982-03-22
- Granted: 1983-08-02
- Earliest claimed: 1982-03-22
- Assignees: Standard Oil Company (Indiana)
- Inventors: John G. Schaffhausen
- Web page: https://patentgrep.com/patent/US4396774A

## CPC

- C07C 51/567: by reactions not involving carboxylic acid anhydride groups
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

A process for the production of a substituted alpha, beta dicarboxylic acid compound substantially free of tar and other resinous reaction byproducts comprising the reaction of an ethylenically unsaturated long chain compound having at least 10 carbon atoms and an ethylenically unsaturated alpha, beta dicarboxylic acid compound at conditions favoring the ENE reaction in the presence of a catalytically effective amount of an alkyl aluminum halide.

## Claims

### Claim 1

A process for the production of a substituted alpha, beta dicarboxylic acid compound substantially free of tar and resinous reaction byproducts which comprises the reaction of an ethylenically unsaturated alpha, beta dicarboxylic acid compound with an ethylenically unsaturated long chain compound having at least 10 carbon atoms at conditions favoring the "ENE" reaction in the presence of a catalytically effective amount of an alkyl aluminum halide.

### Claim 2 (depends on 1)

The process of claim 1 wherein the alkyl aluminum halide is present in the reaction mixture at a concentration of about 1 to 100,000 parts by weight per million parts by weight of ethylenically unsaturated long chain compound having at least 10 carbon atoms.

### Claim 3 (depends on 2)

The process of claim 2 wherein the alkyl aluminum halide is an alkyl aluminum dihalide.

### Claim 4 (depends on 3)

The process of claim 3 wherein the ethylenically unsaturated long chain compound having at least 10 carbon atoms comprises a substantially linear hydrocarbon having a molecular weight of from 140 to 6,000.

### Claim 5 (depends on 4)

The process of claim 4 wherein the ethylenically unsaturated long chain compound having at least 10 carbon atoms comprises polyisobutylene or polypropene.

### Claim 6 (depends on 1)

The process of claim 1 wherein the ethylenically unsaturated aliphatic dicarboxylic acid compound comprises maleic acid or maleic anhydride.

### Claim 7

The process for the production of substituted succinic acid compound substantially free of tar and resinous reaction byproducts which comprises the reaction at conditions favoring the "ENE" reaction of an ethylenically unsaturated long chain compound having at least 10 carbon atoms and maleic anhydride in the presence of a catalytically effective amount of ethylaluminum dichloride.

### Claim 8 (depends on 7)

The process of claim 7 wherein the ethylenically unsaturated long chain compound having at least 10 carbon atoms is a substantially linear hydrocarbon having a molecular weight from about 140 to 6,000.

### Claim 9 (depends on 6)

The process of claim 6 wherein the ethylenically unsaturated long chain compound comprises polyisobutylene and polypropene.

### Claim 10 (depends on 8)

The process of claim 8 wherein the ethylaluminum dichloride is present at a concentration of about 1 to 100,000 parts by weight per million parts by weight of ethylenically unsaturated long chain compound having at least 10 carbon atoms.