# US 5,347,052 A · Preparation of 3,5-diaminobenzotrifluoride

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- Number: US 5,347,052 A
- Document ID: US5347052A
- Status: Granted
- Kind: A
- Application number: 07/685,106
- Filed: 1991-04-15
- Granted: 1994-09-13
- Earliest claimed: 1991-04-15
- Assignees: Occidental Chemical Corporation
- Inventors: David E. Albright, Jr.
- Web page: https://patentgrep.com/patent/US5347052A

## CPC

- C07C 211/52: the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
- C07C 209/365: {by reduction with preservation of halogen-atoms in compounds containing nitro groups and halogen atoms bound to the same carbon skeleton}
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

3,5-Diaminobenzotrifluoride can be produced, in a single step, by reacting 4-chloro-3,5-dinitrobenzotrifluoride, in methanol, with hydrogen gas, in the presence of magnesium oxide, and in the presence of a catalyst comprising palladium on a carbon support.

## Claims

### Claim 1

A process for the preparation of 3,5-diaminobenzotrifluoride which comprises treating 4-chloro-3,5-dinitrobenzotrifluoride, in a methanol solvent, with hydrogen gas in the presence of magnesium oxide and in the presence of a catalyst which comprises palladium on a carbon support.

### Claim 2 (depends on 1)

A process according to claim 1 in which the catalyst is 5% palladium on carbon.

### Claim 3 (depends on 2)

A process according to claim 2 in which the catalyst is present at a level of 4 g (dry weight) per 100 g of 4-chloro-3,5-dinitrobenzotrifluoride.

### Claim 4 (depends on 3)

A process according to claim 3 run at a temperature up to 90.degree. C.

### Claim 5 (depends on 3)

A process according to claim 3 run at a temperature up to 125.degree. C.

### Claim 6 (depends on 2)

A process according to claim 2 in which the catalyst is present at a level of 6 g (dry weight) per 100 g of 4-chloro3,5-dinitrobenzotrifluoride.

### Claim 7 (depends on 6)

A process according to claim 6 run at a temperature up to 90.degree. C.

### Claim 8 (depends on 6)

A process according to claim 6 run at a temperature up to 125.degree. C.

### Claim 9 (depends on 2)

A process according to claim 2 in which the catalyst is present at a level of 1 g (dry weight) per 100 g of 4-chloro3,5-dinitrobenzotrifluoride.

### Claim 10 (depends on 9)

A process according to claim 9 run at a temperature up to 90.degree. C.

### Claim 11 (depends on 9)

A process according to claim 9 run at a temperature up to 125.degree. C.

### Claim 12 (depends on 2)

A process according to claim 2 in which the catalyst is present at a level of 0.5 g (dry weight) per 100 g of 4-chloro-3,5-dinitrobenzotrifluoride.

### Claim 13 (depends on 12)

A process according to claim 12 run at a temperature up to 90.degree. C.

### Claim 14 (depends on 12)

A process according to claim 12 run at a temperature up to 125.degree. C.

### Claim 15 (depends on 1)

A process according to claim 1 including the additional last step of evaporating said methanol.

### Claim 16 (depends on 1)

A process according to claim 1 wherein the concentration of said 4-chloro-3,5-dinitrobenzotrifluoride in said methanol is up to 0.17 g/mL.

### Claim 17

A method of converting at least 87% of 4-chloro-3,5-dinitrobenzotrifluoride into 3,5-diaminobenzotrifluoride and into less than 0.5% 4-chloro-3,5-diaminobenzotrifluoride comprising
(A) preparing a mixture of a solution of up to 0.17 g/mL 4-chloro-3,5-dinitrobenzotrifluoride in methanol in the presence of hydrogen, a palladium or carbon catalyst, and at least one equivalent of magnesium oxide; and
(B) heating said mixture to a temperature between room temperature and 125.degree. C.

### Claim 18 (depends on 17)

A method according to claim 17 including the additional last step of evaporating said solvent.

### Claim 19 (depends on 17)

A process according to claim 17 in which the catalyst is 5% palladium on carbon.

### Claim 20 (depends on 17)

A method according to claim 17 wherein concentration of said catalyst is 4 to 6 g (dry weight) per 100 g of 4-chloro-3,5-dinitrobenzotrifluoride.