# US 4,399,308 A · Lewis acid halide catalysts for preparation of polyamines

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- Number: US 4,399,308 A
- Document ID: US4399308A
- Status: Granted
- Kind: A
- Application number: 06/258,251
- Filed: 1981-04-28
- Granted: 1983-08-16
- Earliest claimed: 1981-04-28
- Assignees: Air Products and Chemicals, Inc.
- Inventors: Michael E. Ford; Thomas A. Johnson
- Web page: https://patentgrep.com/patent/US4399308A

## CPC

- C07C 213/08: by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

A process for selectively preparing predominantly non-cyclic polyalkylene polyamine compounds is disclosed wherein an alkylene polyamine compound is contacted with an alkanolamine compound in the presence of a catalytically effective amount of a Lewis acid halide substance at a temperature of from 200.degree. to 350.degree. C. under a pressure sufficient to maintain the reaction mixture essentially in liquid phase. The polyalkylene polyamine thus formed is recovered from the reaction mixture.

## Claims

### Claim 1

A process for preparing a noncyclic polyalkylene polyamine which comprises:
contacting an alkyleneamine compound having two primary amino groups of the general formula: ##STR4## wherein R is hydrogen or a lower alkyl (C.sub.1 -C.sub.4) radical, x is a number from 2 to about 6, and y is a number from 1 to about 4 with an alkanolamine compound having a primary or secondary hydroxyl group of the general formula: ##STR5## wherein R' is hydrogen or a lower alkyl (C.sub.1 -C.sub.4) radical, x' is a number from 2 to about 6; and y' is a number from 0 to about 3;
the contacting being performed in the presence of an effective amount of a Lewis acid halide substance which is tin (IV) chloride, zinc chloride or zinc fluoride at a temperature sufficient to effect reaction between the alkyleneamine and the alkanolamine compounds under a pressure sufficient to maintain the reaction mixture essentially in liquid phase.

### Claim 2 (depends on 1)

The process of claim 1 wherein the level of the Lewis acid halide substance is from about 0.01 to 10.0 mole percent based upon the total amount of alkylenediamine and alkanolamine present in the reaction mixture.

### Claim 3 (depends on 2)

The process of claim 2 wherein the level of the Lewis acid halide substance is from about 0.05 to 5.0 mole percent based upon the total amount of alkylenediamine and alkanolamine present in the reaction mixture.

### Claim 4 (depends on 2)

The process of claim 2 wherein the temperature is from about 200.degree. C. to 350.degree. C.

### Claim 5 (depends on 4)

The process of claim 4 wherein the molar ratio of alkylenediamine to alkanolamine is from 1:10 to 10:1.

### Claim 6 (depends on 5)

The process of claim 5 wherein the molar ratio of alkylenediamine to alkanolamine is from 1:5 to 5:1.

### Claim 7 (depends on 5)

The process of claim 5 wherein the alkylenediamine is ethylenediamine and the alkanolamine is ethanolamine.

### Claim 8 (depends on 7)

The process of claim 7 wherein the temperature is from about 250.degree. to 300.degree. C.

### Claim 9

A process for preparing a linear polyalkylene polyamine which comprises:
contacting an alkyleneamine compound having two primary amino groups of the general formula: ##STR6## wherein R is hydrogen or methyl, x is a number from about 2 to 6, and y is a number from about 1 to 4 with an alkanolamine compound having a primary or secondary hydroxyl group of the general formula: ##STR7## wherein R' is hydrogen or methyl, x' is a number from about 2 to 6, and y' is a number from about 0 to 3, and the molar ratio of alkylenediamine to alkanolamine is at least 1:1;
the contact being performed in the presence of about 0.01 to 10.0 mole percent, based on the total amount of alkylenediamine and alkanolamine present in the reaction mixture, of a Lewis acid halide substance which is tin (IV) chloride, zinc fluoride or zinc chloride at a temperature from about 200.degree. to 350.degree. C. under a pressure sufficient to maintain the reaction mixture essentially in liquid phase.

### Claim 10 (depends on 9)

The invention of claim 9 wherein the catalyst is tin (IV) chloride and the alkylenediamine:alkanolamine molar ratio is about 2:1.