# US 5,347,051 A · Processes for preparing amines

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- Number: US 5,347,051 A
- Document ID: US5347051A
- Status: Granted
- Kind: A
- Application number: 08/179,788
- Filed: 1994-01-11
- Granted: 1994-09-13
- Earliest claimed: 1993-05-28
- Assignees: Hoechst Celanese Corporation
- Inventors: Michael T. Sheehan; James R. Sounik; Bret F. Hann; William W. Wilkison, III
- Web page: https://patentgrep.com/patent/US5347051A

## CPC

- C08G 65/3255: {Ammonia}
- C07C 45/70: by reaction with functional groups containing oxygen only in singly bound form
- C07C 45/71: being hydroxy groups
- C07C 49/825: all hydroxy groups bound to the ring
- C07C 49/84: containing ether groups, [IMAGE cpc-sch-C07C-0958.gif] groups,[IMAGE cpc-sch-C07C-0959.gif] groups, or[IMAGE cpc-sch-C07C-0960.gif] groups
- C07C 217/58: with amino groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain
- C08G 65/2603: {the other compounds containing oxygen}
- C08G 65/2612: {containing aromatic or arylaliphatic hydroxyl groups}
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

Amines endowed with chain extension activity for formulations such as polyureas and polyurethanes are disclosed, which have the general formula: ##STR1## wherein n is 0-1000; R.sub.1 .dbd.R.sub.2, and R.sub.1 and R.sub.2 are from the group --CH.sub.2 --CH.sub.2 --; --CH.sub.2 --C(CH.sub.3)H--; and --C(CH.sub.3)H--CH.sub.2 --; and R.sub.3 and R.sub.4 are each independently selected from the group consisting of H, --CH.sub.3, --CH.sub.2 CH.sub.3, --CH.sub.2 OH, and --CH.sub.2 --CH.sub.2 --OH; and the diasteromeric salts thereof.

## Claims

### Claim 1

A process for preparing amino compounds having the structural formula: ##STR6## wherein n is 0-1000; R.sub.1 equals R.sub.2, and R.sub.1 and R.sub.2 are from the group --CH.sub.2 --CH.sub.2 --; --CH.sub.2 --C(CH.sub.3)H--; and --C(CH.sub.3)H--CH.sub.2 --; and R.sub.3 and R.sub.4 are each independently selected from the group consisting of H, --CH.sub.3, --CH.sub.2 CH.sub.3, --CH.sub.2 OH, and --CH.sub.2 --CH.sub.2 --OH, which comprises the steps of (a) reacting an alkali metal hydroxide with 4-hydroxyacetophenone to form the alkali metal salt of said 4-hydroxyacetophenone, (b) reacting the alkali metal salt of 4-hydroxyacetophenone with an oxide material selected from the group consisting of ethylene oxide and propylene oxide to form an oxylated material, and then, (c) subjecting the oxylated material to reductive amination, under suitable conditions of temperature from about 50.degree. C. to about 150.degree. C. and pressure from about 300 psi to about 600 psi in order to form the amino compounds covered by the structural formula (I) set forth above.

### Claim 2 (depends on 1)

The process as set forth in claim 1 wherein in the reductive amination step there is present a solvent, an acid-promoted catalyst, and a co-catalyst.

### Claim 3 (depends on 2)

The process as set forth in claim 2 wherein the acid-promoted catalyst is present at a concentration of at least five (5) percent by weight, based on the weight of the oxylated material.

### Claim 4 (depends on 3)

The process as set forth in claim 3 wherein the acid-promoted catalyst is present at a concentration of from ten (10) to thirty (30) percent by weight, based on the weight of the oxylated material.

### Claim 5 (depends on 4)

The process as set forth in claim 4 wherein the acid-promoted catalyst is Raney nickel.

### Claim 6 (depends on 2)

The process as set forth in claim 2 wherein the solvent is a polar liquid selected from the group consisting of lower alkanols, cycloalkanols, and asymmetrically halogenated hydrocarbons.

### Claim 7 (depends on 6)

The process as set forth in claim 6 wherein the solvent is a lower alkanol selected from the group consisting of methanol, ethanol, isopropanol, butanol, pentanol, cyclohexanol, cyclobutanol, and mixtures thereof.

### Claim 8 (depends on 1)

The process as set forth in claim 1 wherein the temperature is from about 75.degree. C. to about 150.degree. C.

### Claim 9 (depends on 8)

The process as set forth in claim 8 wherein the pressure is from about 350 psi to about 600 psi.

### Claim 10 (depends on 2)

The process as set forth in claim 2 wherein the co-catalyst is acetic acid and is present in a concentration at least one (1) percent by weight of the oxylated material.

### Claim 11 (depends on 10)

The process as set forth in claim 10 wherein the solvent is isopropanol.

### Claim 12 (depends on 1)

The process as set forth in claim 1 wherein there is provided the further step of contacting the amino compound of structural formula (I) with a chiral acid for a sufficient period of time and temperature to form a diasteromeric salt thereof.

### Claim 13 (depends on 12)

The process as set forth in claim 12 wherein the chiral acid is selected from the group consisting of tartaric acid, malic acid, camphorsulfonic acid, lactic acid, bromocamphorsulfonic acid, mandelic acid, 2-(4-isobutyl-phenyl)-propionic acid, and derivatives thereof.