# US 5,344,998 A · Preparation of bis(fluoromethy)ether and difluoromethane

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- Number: US 5,344,998 A
- Document ID: US5344998A
- Status: Granted
- Kind: A
- Application number: 08/145,668
- Filed: 1993-11-04
- Granted: 1994-09-06
- Earliest claimed: 1991-11-13
- Assignees: Imperial Chemical Industries PLC
- Inventors: John S. Martin; Thomas A. Ryan; Rachel A. Spooncer
- Web page: https://patentgrep.com/patent/US5344998A

## CPC

- C07C 41/01: Preparation of ethers
- C07C 17/361: by reactions involving a decrease in the number of carbon atoms
- C07C 43/123: {both carbon chains are substituted by halogen atoms}
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

A process for the production of bis(fluoromethyl)ether by contacting formaldehyde with hydrogen fluoride in a reaction/distillation vessel. The reaction/distillation vessel is preferably a reaction/distillation column through which formaldehyde and hydrogen fluoride preferably flow in counter current. The bis(fluoromethyl)ether may be converted to difluoromethane, preferably by heating the bis(fluoromethyl)ether to elevated temperature in the presence of a metal, metal oxide, metal fluoride or metal oxyfluoride catalyst.

## Claims

### Claim 1

A process for the production of bis(fluoromethyl) ether which comprises reacting formaldehyde with hydrogen fluoride in a distillation column operated at a temperature in the reaction section of from about 50.degree. C. to about 80.degree. C. to produce bis(fluoromethyl) ether and water and withdrawing from the column a vapour in which the mole ratio of bis(fluoromethyl) ether to water is greater than 1.

### Claim 2

A process for the production of bis(fluoromethyl) ether which comprises reacting formaldehyde with hydrogen fluoride in a distillation column within which the temperature profile is from 20.degree. C. to 40.degree. C. at the top of the column to 115.degree. C. to 140.degree. C. at the bottom of the column to produce bis(fluoromethyl) ether and water and withdrawing from the column a vapour in which the mole ratio of bis(fluoromethyl) ether to water is greater than 1.

### Claim 3 (depends on 1, 2)

A process as claimed in claim 1 or 2 wherein the bis(fluoromethyl) ether is withdrawn from the top of the column and water is withdrawn from the bottom of the column.

### Claim 4 (depends on 1)

A process as claimed in claim 1 in which the formaldehyde and hydrogen fluoride are caused to flow in counter-current in the column.

### Claim 5 (depends on 4)

A process as claimed in claim 4 in which the formaldehyde and at least a part of the hydrogen fluoride are fed to the column through different inlets.

### Claim 6 (depends on 5)

A process as claimed in claim 5 in which formaldehyde is fed to the distillation column at a position above that at which at least a part of the hydrogen fluoride is fed to the column.

### Claim 7 (depends on 4, 5, 6)

A process as claimed in any one of claims 4 to 6 in which the formaldehyde is fed to the column as a solution of formaldehyde in hydrogen fluoride.

### Claim 8 (depends on 1, 2)

A process for the production of difluoromethane which comprises reacting formaldehyde with hydrogen fluoride in a distillation column as defined in claim 1 or 2 and heating the bis(fluoromethyl) ether withdrawn from the column in the vapour phase at a temperature of from 200.degree. C. to 450.degree. C. in the presence of a catalyst selected from the group consisting of nickel, chromium, aluminum and iron or an alloy of at least one of these metals or an oxide, fluoride or oxyfluoride thereof.

### Claim 9 (depends on 1, 2)

A process for the production of difluoromethane which comprises reacting formaldehyde with hydrogen fluoride in a distillation column as defined in claim 1 or 2 and heating the bis(fluoromethyl) ether withdrawn from the column at elevated temperature of from 200.degree. C. to 400.degree. C. in the vapour phase in the presence of a catalyst selected from the group consisting of nickel, chromium, aluminum and iron or an alloy of at least one of these metals or an oxide, fluoride or oxyfluoride thereof.