# US 4,400,563 A · Process for preparing perfluoro(lower)alkylbenzenes and their derivatives

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- Number: US 4,400,563 A
- Document ID: US4400563A
- Status: Granted
- Kind: A
- Application number: 06/050,212
- Filed: 1979-06-20
- Granted: 1983-08-23
- Earliest claimed: 1976-12-27
- Assignees: Daikin Kogyo Co., Ltd.
- Inventors: Yohnosuke Ohsaka; Uji Hiramatsu; Toshihide Honda
- Web page: https://patentgrep.com/patent/US4400563A

## CPC

- C07B 39/00: Halogenation
- C07C 17/14: in the side-chain of aromatic compounds
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

A process for preparing perfluoro(lower)alkylbenzenes and derivatives thereof which comprises contacting a lower alkylbenzene or the corresponding derivative with hydrogen fluoride in the presence of chlorine in the gaseous phase at an elevated temperature to give the corresponding perfluoro(lower)alkylbenzene or its derivative thereof.

## Claims

### Claim 1

A process for preparing perfluoro(lower)alkylbenzene derivatives which comprises contacting a lower alkylbenzene compound of the formula: ##STR4## wherein R is lower alkyl and R.sub.1, R.sub.2 and R.sub.3 are each hydrogen, trichloromethyl, nitro, cyano or halogen, but wherein all of R.sub.1, R.sub.2 and R.sub.3 are not hydrogen at the same time and when one of R.sub.1, R.sub.2 and R.sub.3 is nitro, each of the other two is not nitro, with hydrogen fluoride in the presence of chlorine in the absence of a catalyst and in the gaseous phase at an elevated temperature to give the corresponding perfluoro(lower)alkylbenzene compound of the formula: ##STR5## wherein R' is perfluoro(lower)alkyl and R.sub.1 ', R.sub.2 ' and R.sub.3 ' are each hydrogen, trifluoromethyl, nitro, cyano or halogen, but all of R.sub.1 ', R.sub.2 ' and R.sub.3 ' are not hydrogen at the same time and when one of R.sub.1 ', R.sub.2 ' and R.sub.3 ' is nitro, each of the other two is not nitro.

### Claim 2 (depends on 1)

The process according to claim 1, wherein hydrogen fluoride is used in a molar ratio of 3 to 15 with respect to the lower alkylbenzene compound.

### Claim 3 (depends on 1)

The process according to claim 1, wherein chlorine is used in a molar ratio of about 2 to 15 with respect to the lower alkylbenzene compound.

### Claim 4 (depends on 1)

The process according to claim 1, wherein the contact is effected at a temperature of about 350.degree. to 600.degree. C.

### Claim 5 (depends on 4)

The process according to claim 4, wherein the temperature is from about 450.degree. to 600.degree. C.

### Claim 6 (depends on 1)

The process according to claim 1, wherein the contact is effected for a period of about 5 to 40 seconds.

### Claim 7 (depends on 1)

The process according to claim 1, wherein the contact is effected in the presence of a gaseous diluent.

### Claim 8 (depends on 1)

The process according to claim 1, wherein R.sub.1, R.sub.2 and R.sub.3 are each hydrogen, trichloromethyl or halogen.