Process for preparation of tertiary alkyl primary amines

Patent metadata

Field	Value
Publication number	US-9617200-B2
Application number	US-201414781627-A
Country	US
Kind code	B2
Filing date	Apr 2, 2014
Priority date	Apr 3, 2013
Publication date	Apr 11, 2017
Grant date	Apr 11, 2017

Abstract

A method for producing an amine. The first step is contacting a cyanide, an acid, water and a substrate compound capable of generating a carbonium ion by reaction with the acid to generate a first reaction intermediate. The second step is contacting the first reaction intermediate with water to form a second reaction intermediate. The third step is removing cyanide present in the second reaction intermediate to a concentration less than 10 ppm. The fourth step is contacting the second reaction intermediate with an alkali metal hydroxide to form the amine.

First claim

The invention claimed is:

1. A method for producing an amine; said method comprising steps of: (a) contacting hydrogen cyanide or a salt thereof, an acid, water and a substrate compound capable of generating a carbonium ion by reaction with the acid to generate a first reaction intermediate; (b) contacting the first reaction intermediate with water to form a second reaction intermediate; (c) removing hydrogen cyanide present in the second reaction intermediate to a concentration less than 10 ppm; and (d) contacting the second reaction intermediate with an alkali metal hydroxide to form the amine; wherein hydrogen cyanide is removed from the second reaction intermediate by a stripper column and hydrogen cyanide removed from the second reaction intermediate is recycled to step (a).

2. The method of claim 1 in which the substrate compound is an alkene oligomer.

3. The method of claim 2 in which the acid is an inorganic acid.

4. The method of claim 3 in which the alkali metal hydroxide is sodium hydroxide or potassium hydroxide.

5. The method of claim 4 in which the alkene oligomer is propylene tetramer, propylene hexamer or isobutylene dimer.

6. The method of claim 5 in which the inorganic acid is a concentrated aqueous solution of sulfuric acid that includes from about 60 wt % to about 100 wt % sulfuric acid.

7. A method for producing an amine; said method comprising steps of: (a) contacting: (i) hydrogen cyanide or a salt thereof, (ii) a concentrated aqueous solution of sulfuric acid that includes from about 60 wt % to about 100 wt % sulfuric acid, (iii) water and (iv) propylene tetramer, propylene hexamer or isobutylene dimer to generate a first reaction intermediate; (b) contacting the first reaction intermediate with water to form a second reaction intermediate; (c) removing cyanide present in the second reaction intermediate to a concentration less than 10 ppm; and (d) contacting the second reaction intermediate with sodium hydroxide or potassium hydroxide to form the amine; wherein hydrogen cyanide is removed from the second reaction intermediate by a stripper column and hydrogen cyanide removed from the second reaction intermediate is recycled to step (a).

Assignees

• Dow Global Technologies Llc
• Rohm & Haas

Inventors

• Chheda Bharati D
• Pendergast Jr John G
• Rangavajjula Sivam
• Trauth Daniel M

Classifications

• C07C209/44

  by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers · CPC title

• C07C209/62 Primary

  by cleaving carbon-to-nitrogen, sulfur-to-nitrogen, or phosphorus-to-nitrogen bonds, e.g. hydrolysis of amides, N-dealkylation of amines or quaternary ammonium compounds (C07C209/24 takes precedence) · CPC title

• C07C211/07

  containing one, two or three alkyl groups, each having the same number of carbon atoms in excess of three · CPC title