# US 5,703,267 A · Process for producing 2-cyanoacrylic acid

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- Number: US 5,703,267 A
- Document ID: US5703267A
- Status: Granted
- Kind: A
- Application number: 08/621,612
- Filed: 1996-03-26
- Granted: 1997-12-30
- Earliest claimed: 1995-03-27
- Assignees: Toagosei Co., Ltd.
- Inventors: Shin Takahashi; Yoshiharu Ohashi; Yushi Ando; Toshio Okuyama
- Web page: https://patentgrep.com/patent/US5703267A

## CPC

- C07C 253/30: by reactions not involving the formation of cyano groups
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

The present invention provides a process for producing 2-cyanoacrylic acid, characterized by subjecting a 2-cyanoacrylate and an organic acid to transesterification reaction. The 2-cyanoacrylic acid obtained by the process of the present invention is useful as a starting material for the preparation of polyfunctional 2-cyanoacrylates.

## Claims

### Claim 1

A process for producing a 2-cyanoacrylic acid which comprises subjecting a 2-cyanoacrylate and an organic acid to a transesterification reaction at a temperature of 40.degree.-90.degree. C.

### Claim 2 (depends on 1)

A process according to claim 1, wherein a cation exchange resin is used as a catalyst.

### Claim 3 (depends on 1)

A process according to claim 1, wherein the organic acid is selected from the group consisting of formic acid, acetic acid, propionic acid and butyric acid.

### Claim 4 (depends on 1)

A process according to claim 1, wherein the organic acid is acetic acid.

### Claim 5 (depends on 1)

A process according to claim 1, wherein the 2-cyanoacrylate is selected from the group consisting of methyl-2-cyanoacrylate, ethyl-2-cyanoacrylate, isopropyl-2-cyanoacrylate, n-propyl-2-cyanoacrylate, n-butyl-2-cyanoacrylate, and isobutyl-2-cyanoacrylate.

### Claim 6 (depends on 1)

A process according to claim 1, wherein the molar ratio of the organic acid/the 2-cyanoacrylate is 50-2.

### Claim 7 (depends on 1)

A process according to claim 1, wherein a cation exchange resin as a catalyst is used in an amount of 20-70% by weight based on the total weight of the 2-cyanoacrylate, the organic acid and the cation exchange resin.

### Claim 8

A process for producing 2-cyanoacrylic acid which comprises subjecting a 2-cyanoacrylate to an acidolysis reaction with an organic acid at a temperature of 10.degree.-90.degree. C.

### Claim 9 (depends on 8)

A process according to claim 8, wherein a cation exchange resin is used as a catalyst.

### Claim 10 (depends on 8)

A process according to claim 8, wherein the organic acid is selected from the group consisting of formic acid, acetic acid, propionic acid and butyric acid.

### Claim 11 (depends on 8)

A process according to claim 8, wherein the organic acid is acetic acid.

### Claim 12 (depends on 8)

A process according to claim 8, wherein the 2-cyanoacrylate is selected from the group consisting of methyl-2-cyanoacrylate, ethyl-2-cyanocacrylate, isopropyl-2-cyanoacrylate, n-propyl-2-cyanoacrylate, n-butyl-2-cyanoacrylate, and isobutyl-2-cyanoacrylate.

### Claim 13 (depends on 8)

A process according to claim 8, wherein the molar ratio of the organic acid/the 2-cyanoacrylate is 50-2.

### Claim 14 (depends on 8)

A process according to claim 8, wherein a cation exchange resin as a catalyst is used in an amount of 20-70% by weight based on the total weight of the 2-cyanoacrylate, the organic acid and the cation exchange resin.

### Claim 15 (depends on 8)

A process according to claim 8, wherein said reaction is carried out at a temperature no greater than about 60.degree. C.