# US 4,398,033 A · 4-Chloro-4-chloromethyloxetan-2-one and a process for its production

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- Number: US 4,398,033 A
- Document ID: US4398033A
- Status: Granted
- Kind: A
- Application number: 06/355,498
- Filed: 1982-03-08
- Granted: 1983-08-09
- Earliest claimed: 1981-03-17
- Assignees: Ciba-Geigy Corporation
- Inventors: John G. Dingwall; Brian Tuck
- Web page: https://patentgrep.com/patent/US4398033A

## CPC

- C07D 305/12: Beta-lactones
- A61P 31/04: Antibacterial agents
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The new compound 4-chloro-4-chloromethyloxetan-2-one can be prepared by reacting diketene with sulphuryl chloride under conditions in which free radicals are formed. The 4-chloro-4-chloromethyloxetan-2-one exhibits antimicrobial activity. It is also useful as an intermediate, for example for the production of pigments and dyestuffs.

## Claims

### Claim 1

A process for producing 4-chloro-4-chloromethyloxetan-2-one, comprising reacting diketene with sulphuryl chloride under conditions in which free radicals are formed.

### Claim 2 (depends on 1)

A process according to claim 1 wherein the free radicals are formed by the application to the reaction mixture of ionising radiation or of ultraviolet radiation.

### Claim 3 (depends on 1)

A process according to claim 1 wherein the reaction is effected in the presence of a chemical compound capable of forming free radicals.

### Claim 4 (depends on 1)

A process according to claim 1 wherein the reaction is effected in the presence of an organic peroxide optionally in conjunction with exposure to ultraviolet radiation or a metal ion catalyst; an inorganic peroxy compound optionally in conjunction with a metal ion catalyst; or an organic azo compound, optionally in conjunction with exposure to ultraviolet radiation.

### Claim 5 (depends on 1)

A process according to claim 1 wherein the reaction is effected in the presence of t-butyl peracetate, t-butyl perbenzoate, acetylperoxide, benzoylperoxide, di-isopropylperdicarbonate, di-t-butylcyclohexylperdicarbonate, di-t-butylperoxide or t-butylhydroperoxide.

### Claim 6 (depends on 1)

A process according to claim 1 wherein the reaction is effected in the presence of hydrogen peroxide or ammonium persulphate.

### Claim 7 (depends on 1)

A process according to claim 1 wherein the reaction is effected in the presence of azobisisobutyronitrile or azobisisopropane.

### Claim 8 (depends on 4)

A process according to claim 4 wherein the metal ion catalyst is copper, vanadium, iron or titanium.

### Claim 9 (depends on 1)

A process according to claim 1 wherein the reaction is effected in the presence of from 0.1 to 10 mol.%, based on the amount used of diketene, of a compound capable of forming free radicals.

### Claim 10 (depends on 1)

A process according to claim 1 wherein the reaction is effected in the presence of from 1 to 5 mol.%, based on the amount used of diketene, of a compound capable of forming free radicals.

### Claim 11 (depends on 1)

A process according to claim 1 wherein the reaction is effected in the presence of a solvent which is inert under the reaction conditions.

### Claim 12 (depends on 1)

A process according to claim 1 wherein the reaction is effected at a temperature within the range of from 0.degree. to 100.degree. C.