# US 4,393,000 A · Cyclization process for producing aziridine-2-carboxylic acid or its salts

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- Number: US 4,393,000 A
- Document ID: US4393000A
- Status: Granted
- Kind: A
- Application number: 06/214,728
- Filed: 1980-12-09
- Granted: 1983-07-12
- Earliest claimed: 1979-12-12
- Assignees: Mitsui Toatsu Chemicals, Inc.
- Inventors: Ryuichi Mita; Chojiro Higuchi; Toshio Kato; Nobuyuki Kawashima; Akihiro Yamaguchi; Shosuke Nagai; Takao Takano
- Web page: https://patentgrep.com/patent/US4393000A

## CPC

- C07D 203/08: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring nitrogen atom
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

A process for producing aziridine-2-carboxylic acid or its salts is provided which comprises treating an alpha-halogeno-beta-aminopropionitrile or its mineral acid salt with an alkali or alkaline earth metal hydroxide in water or in a water-containing organic solvent. In a preferred embodiment, aziridine-2-carboxylic acid or its salt is produced by treating the reaction mixture containing an alpha-halogeno-beta-aminopropionitrile obtained by reacting an alpha, beta-dihalogenopropionitrile or an alpha-halogenoacrylonitrile with ammonia, with an alkali or alkaline earth metal hydroxide in the presence of water without isolating the alpha-halogeno-beta-aminopropionitrile from the reaction mixture beforehand.

## Claims

### Claim 1

A process for producing aziridine-2-carboxylic acid salt which comprises a step wherein an .alpha.-halogeno-.beta.-aminopropionitrile-containing reaction mixture obtained by reacting an .alpha.,.beta.-dihalogenopropionitrile or an .alpha.-halogenoacrylonitrile with ammonia in water, an organic solvent or a mixture of water and an organic solvent at a temperature of -40.degree. to 30.degree. C., is treated with an alkali or alkaline earth metal hydroxide.

### Claim 2 (depends on 1)

The process of claim 1 wherein the ammonia is used in water in a concentration of 5 to 30% by weight, or in an organic solvent or a water-containing organic solvent in a concentration of 2 to 25% by weight.

### Claim 3 (depends on 1)

The process of claim 1 wherein the alpha-halogeno-beta-aminopropionitrile-containing reaction mixture is obtained by reacting an alpha-halogenoacrylonitrile with ammonia in water and/or an organic solvent.

### Claim 4 (depends on 1)

The process of claim 1 wherein the alpha-halogeno-beta-aminopropionitrile-containing reaction mixture is obtained by reacting an alpha,beta-dihalogenopropionitrile with ammonia in water and/or an organic solvent.

### Claim 5 (depends on 3)

The process of claim 3 wherein the .alpha.-halogeno-acrylonitrile is an .alpha.-chloroacrylonitrile or an .alpha.-bromoacrylonitrile.

### Claim 6 (depends on 4)

The process of claim 4 wherein the .alpha.,.beta.-dihalogenopropionitrile is an .alpha.,.beta.-dichloropropionitrile or .alpha.,.beta.-dibromopropionitrile.

### Claim 7 (depends on 1)

The process of claim 1 wherein the alkali or alkaline earth metal hydroxide is sodium hydroxide, potassium hydroxide or calcium hydroxide.

### Claim 8 (depends on 1)

The process of claim 1 wherein the organic solvent is a compound which dissolves ammonia.

### Claim 9 (depends on 8)

The process of claim 8 wherein the compound which dissolves ammonia is methanol, ethanol, propanol, isopropanol, n-butanol, isobutanol, methyl Cellosolve or Cellosolve.

### Claim 10 (depends on 3)

The process of claim 3 wherein at least 1 mole of ammonia per mole of the .alpha.-halogenoacrylonitrile is reacted.

### Claim 11 (depends on 4)

The process of claim 4 wherein at least 2 moles of ammonia per mole of the .alpha.,.beta.-dihalogenopropionitrile is reacted.

### Claim 12 (depends on 3)

The process of claim 3 wherein the amount of the alkali or alkaline earth metal hydroxide is at least 2 equivalents based on the .alpha.-halogenoacrylonitrile.

### Claim 13 (depends on 4)

The process of claim 4 wherein the amount of the alkali or alkaline earth metal hydroxide is at least 2 equivalents based on the .alpha.,.beta.-dihalogenopropionitrile.