# US 4,394,523 A · Catalytic hydrogenation of di (4-aminophenyl) methane

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- Number: US 4,394,523 A
- Document ID: US4394523A
- Status: Granted
- Kind: A
- Application number: 06/269,200
- Filed: 1981-06-01
- Granted: 1983-07-19
- Earliest claimed: 1981-06-01
- Assignees: Mobay Chemical Corporation
- Inventors: Gary F. Allen
- Web page: https://patentgrep.com/patent/US4394523A

## CPC

- C07C 209/72: by reduction of six-membered aromatic rings
- C07C 2601/14: The ring being saturated
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

The present invention relates to an improved process for the catalytic hydrogenation of di(4-aminophenyl) methane to a liquid di(4-aminocyclohexyl) methane mixture containing from 15 to 40% by weight of the trans, trans isomer. The invention resides in the use of a ruthenium-on-alumina catalyst, the use of an aliphatic alcohol during hydrogenation and the use of ammonia during hydrogenation, with the hydrogenation being conducted under specific process conditions. The hydrogenation reaction is conducted for no more than about sixty minutes at a temperature of from 150.degree. to 217.degree. C. and at a hydrogen pressure of at least 500 psi.

## Claims

### Claim 1

A process for the catalytic hydrogenation of di(4-aminophenyl)methane to a liquid di(4-aminocyclohexyl)methane containing from 15% to 40% by weight of the trans, trans isomer comprising hydrogenating di(4-aminophenyl)methane in the presence of (i) a ruthenium-on-alumina catalyst (ii) at least 25% by weight of an aliphatic alcohol selected from the group consisting of methanol, ethanol, n-propanol, and isopropanol, based on the weight of the total weight of the di(4-aminophenyl)methane and the alcohol, and (iii) ammonia, the amount of ammonia present being such that the molar ratio of ammonia to di(4-aminophenyl)methane is from 0.5:1 to 10:1, the hydrogenation being conducted at a hydrogen pressure of at least 500 psi, at a temperature of from 150.degree. C. to 217.degree. C., and for a time not exceeding 60 minutes.

### Claim 2 (depends on 1)

The process of claim 1 wherein said alcohol is methanol.

### Claim 3 (depends on 4)

The process of claim 4 wherein the pressure is at least 1500 psi.

### Claim 4

A process for the catalytic hydrogenation of di(4-aminophenyl)methane to a liquid di(4-aminocyclohexyl)methane containing from 15% to 40% by weight of the trans, trans isomer comprising hydrogenating di(4-aminophenyl)methane in the presence of (i) a ruthenium-on-alumina catalyst, (ii) at least 25% by weight of an aliphatic alcohol, based on the weight of the total weight of the di(4-aminophenyl)methane and the alcohol, and (iii) ammonia, the amount of ammonia present being such that the mol ratio of ammonia to di(4-aminophenyl)methane is from 0.5:1 to 10:1, the hydrogenation being conducted at a hydrogen pressure of from about 1500 to 4000 psi, at a temperature of from 150.degree. C. to 217.degree. C., and for a time not exceeding sixty minutes.

### Claim 5 (depends on 4)

The process of claim 4 wherein said alcohol contains from 1 to 10 carbon atoms.

### Claim 6 (depends on 2)

The process of claim 2, wherein said alcohol is methanol.

### Claim 7 (depends on 4)

The process of claim 4 wherein the amount of alcohol is from 25 to 60% by weight.

### Claim 8 (depends on 7)

The process of claim 7 wherein the amount of alcohol is from 30 to 50% by weight.

### Claim 9 (depends on 4)

The process of claim 4 wherein said mol ratio 25 is from 0.5:1 to 5:1.

### Claim 10 (depends on 9)

The process of claim 9 wherein said mol ratio is about 1:1.

### Claim 11 (depends on 4)

The process of claim 4 wherein the amount of said catalyst is such that the amount of ruthenium is at least 0.05% by weight of the di(4-aminophenyl)methane.

### Claim 12 (depends on 11)

The process of claim 11 wherein the amount of ruthenium is from 0.1 to 3% by weight of the di(4-aminophenyl)methane.

### Claim 13 (depends on 12)

The process of claim 12 wherein the amount of ruthenium is from 0.1 to 1% by weight of the di(4-aminophenyl)methane.

### Claim 14 (depends on 4)

The process of claim 4 wherein the temperature is from 170.degree. to 200.degree. C.

### Claim 15 (depends on 4)

The process of claim 4 wherein said time is between ten and fifty minutes.