# US 5,347,043 A · Process for preparing Michael addition products

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- Number: US 5,347,043 A
- Document ID: US5347043A
- Status: Granted
- Kind: A
- Application number: 08/169,261
- Filed: 1993-12-20
- Granted: 1994-09-13
- Earliest claimed: 1993-12-20
- Assignees: Albemarle Corporation
- Inventors: Mahmood Sabahi; Robert G. Irwin
- Web page: https://patentgrep.com/patent/US5347043A

## CPC

- C07C 67/343: by increase in the number of carbon atoms
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

Dialkyl malonate/alkyl acrylate Michael addition product mixtures having at least three acceptor moieties in a substantial number of the molecules can be consistently prepared without the need for long reaction times or the use of a large excess of the acceptor when the reaction is effected by gradually adding one molar proportion of a dialkyl malonate to at least three molar proportions of an alkyl acrylate which has been preheated to 60.degree.-80.degree. C. in admixture with an initiator and a phase transfer catalyst. In a preferred embodiment, the preheated mixture is maintained at 60.degree.-80.degree. C. for at least one hour before the dialkyl malonate is added in order to increase the percentage of product composed of the heavier components.

## Claims

### Claim 1

In a process for reacting one molar proportion of a dialkyl malonate with at least three molar proportions of an alkyl acrylate in the presence of a basic initiator and a phase transfer catalyst to prepare a Michael addition product mixture that contains molecules having at least three alkyl acrylate moieties, the improvement which comprises preheating a mixture of the alkyl acrylate, the initiator, and the phase transfer catalyst to 60.degree.-80.degree. C. and then gradually adding the dialkyl malonate to the preheated mixture to effect reaction with the alkyl acrylate.

### Claim 2 (depends on 1)

The process of claim 1 wherein the preheated mixture is maintained at 60.degree.-80.degree. C. for at least one hour before the dialkyl malonate is added thereto.

### Claim 3 (depends on 2)

The process of claim 2 wherein the preheated mixture is maintained at 60.degree.-80.degree. C. for one hour before the dialkyl malonate is added thereto.

### Claim 4 (depends on 1)

The process of claim 1 wherein the alkyl groups of the dialkyl malonate and alkyl acrylate contain 1-10 carbons.

### Claim 5 (depends on 4)

The process of claim 4 wherein the dialkyl malonate is dimethyl malonate.

### Claim 6 (depends on 5)

The process of claim 5 wherein the alkyl acrylate is methyl acrylate.

### Claim 7 (depends on 5)

The process of claim 5 wherein the alkyl acrylate is butyl acrylate.

### Claim 8 (depends on 4)

The process of claim 4 wherein the dialkyl malonate is diethyl malonate.

### Claim 9 (depends on 8)

The process of claim 8 wherein the alkyl acrylate is methyl acrylate.

### Claim 10 (depends on 8)

The process of claim 8 wherein the alkyl acrylate is butyl acrylate.

### Claim 11 (depends on 1)

The process of claim 1 wherein one molar proportion of the dialkyl malonate is added to a preheated mixture containing 3-5 molar proportions of the alkyl acrylate.

### Claim 12 (depends on 11)

The process of claim 11 wherein the alkyl groups of the dialkyl malonate and alkyl acrylate contain 1-10 carbons and the preheated mixture is maintained at 60.degree.-80.degree. C. for one hour before the dialkyl malonate is added thereto.

### Claim 13 (depends on 12)

The process of claim 12 wherein the dialkyl malonate is dimethyl malonate.

### Claim 14 (depends on 13)

The process of claim 13 wherein the alkyl acrylate is methyl acrylate.

### Claim 15 (depends on 13)

The process of claim 13 wherein the alkyl acrylate is butyl acrylate.

### Claim 16 (depends on 12)

The process of claim 12 wherein the dialkyl malonate is diethyl malonate.

### Claim 17 (depends on 16)

The process of claim 16 wherein the alkyl acrylate is methyl acrylate.

### Claim 18 (depends on 16)

The process of claim 16 wherein the alkyl acrylate is butyl acrylate.