Reductive amination of diethanolamine and resulting product mixture

Patent metadata

Field	Value
Publication number	US-9353044-B2
Application number	US-201214369427-A
Country	US
Kind code	B2
Filing date	Nov 14, 2012
Priority date	Dec 22, 2011
Publication date	May 31, 2016
Grant date	May 31, 2016

Abstract

The invention provides a method for the reductive amination of diethanolamine to form a product composition that includes piperazine (PIP) and aminoethylethanolamine (AEEA). A catalyst with a transitional alumina/second metal oxide support and a mixture of catalytic metals is used for the reaction which results in low levels of non-PIP and non-AEEA side products.

First claim

What is claimed is:

1. A method of making a piperazine- and aminoethylethanolamine-containing composition comprising steps of:
(a) providing a reaction composition comprising diethanolamine; and
(b) subjecting the reaction composition to a reductive amination in the presence of ammonia and a catalyst composition, the catalyst composition comprising a support portion and a catalyst portion, the support portion comprising an acidic mixed metal oxide comprising a transitional alumina and a second metal oxide, the catalyst portion comprising a first metal selected from the group consisting of cobalt, nickel, and copper, and a second metal selected from the group consisting of rhenium, ruthenium, rhodium, platinum, palladium, and iridium, wherein reductive amination of diethanolamine forms a product composition comprising piperazine and aminoethylethanolamine; and wherein the transitional alumina is (i) more than 50 weight percent of the alumina contained in the support and (ii) comprises a theta phase alumina, delta phase alumina, or mixtures of theta and delta phase aluminas.

2. The method of claim 1 wherein the catalyst portion is 20 wt. % or less of the catalyst composition.

3. The method of claim 1 where, in the catalyst portion, the first metal is present in an amount greater than the second metal.

4. The method of claim 1 where, in the catalyst portion, the first metal and the second metal are present in a weight ratio in the range of 10:1 to 1:1.

5. The method of claim 1 wherein the catalyst portion comprises nickel.

6. The method of claim 1 wherein the catalyst portion comprises rhenium.

7. The method of claim 1 wherein the reductive amination is carried out at a temperature of 140° C. or greater.

8. The method of claim 1 wherein diethanolamine is present at 80% wt or greater in the reaction composition.

9. The method of claim 1 where, in the product composition, aminoethylethanolamine is present in an amount (wt %) greater than piperazine.

10. The method of claim 1 where, in the product composition, the combined amount of piperazine and aminoethylethanolamine are 75% wt or greater of the products in the product composition.

11. The method of claim 1 wherein piperazine is 10-40% wt of the products in the product composition.

12. The method of claim 1 wherein the product compositions comprises reductive amination products of aminoethylethanolamine that are not piperazine or aminoethylethanolamine which are in an amount that is equal to or less than 25 wt in the product composition.

13. The method of claim 12 wherein the product compositions comprises reductive amination products of aminoethylethanolamine that are not piperazine or aminoethylethanolamine which are in an amount that is equal to or less than 10% wt in the product composition.

Assignees

• Dow Global Technologies Llc
• Dow Global Technologies Llc

Inventors

• King Stephen W
• Onam Sadeka
• Srnak Thomas Z

Classifications

• C07C2529/89

  Silicates, aluminosilicates or borosilicates of titanium, zirconium or hafnium · CPC title

• B01J23/8896

  Rhenium · CPC title

• B01J37/0201

  Impregnation · CPC title

• C07C213/02 Primary

  by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups · CPC title

• C07D295/023

  Preparation; Separation; Stabilisation; Use of additives · CPC title