Method for separating N,N,N'-trimethylbisaminoethylether and/or N,N-dimethylbisaminoethylether from a mixture

Patent metadata

Field	Value
Publication number	US-10100002-B2
Application number	US-201415029647-A
Country	US
Kind code	B2
Filing date	Sep 29, 2014
Priority date	Oct 15, 2013
Publication date	Oct 16, 2018
Grant date	Oct 16, 2018

Abstract

The present invention relates to a method for separating N,N,N′-trimethylbisaminoethylether and/or N,N-dimethylbisaminoethylether, from a mixture A comprising N,N,N′-trimethylbisaminoethylether, and N,N-dimethylbisaminoethylether, wherein said method comprises the steps of:
(a) contacting said mixture A with an acylating agent, to form a mixture B comprising the amides of N,N,N′-trimethylbisaminoethylether and of N,N-dimethylbisaminoethylether, respectively; and (b1) separating the amide of N,N,N′-trimethylbisaminoethylether from mixture B; and (c1) recovering N,N,N′-trimethylbisaminoethylether from its amide by means of a transamidation reaction; and/or (b2) separating the amide of N,N-dimethylbisaminoethylether from mixture B; and (c2) recovering N,N-dimethylbisaminoethylether from its amide by means of a transamidation reaction.

First claim

The invention claimed is:

1. A method for separating at least one of N,N,N′-trimethylbisaminoethylether and N,N-dimethylbisaminoethylether from a mixture A comprising N,N,N′-trimethylbisaminoethylether, N,N-dimethylbisaminoethylether and N,N,N′,N′-tetramethylbisaminoethylether, wherein said method comprises the steps of:
(a) contacting said mixture A with an acylating agent, to form a mixture B comprising N,N,N′,N′-tetramethylbisaminoethylether and the amides of N,N,N′-trimethylbisaminoethylether and N,N-dimethylbisaminoethylether;
(b) at least one of (b1) separating the amide of N,N,N′-trimethylbisaminoethylether from mixture B and (b2) separating the amide of N,N-dimethylbisaminoethylether from said mixture B; and
(c) at least one of (c1) recovering N,N,N′-trimethylbisaminoethylether from its amide by a transamidation reaction and (c2) recovering N,N-dimethylbisaminoethylether from its amide by a transamidation reaction.

2. The method according to claim 1 , further comprising the step (i) of separating N,N,N′,N′-tetramethylbisaminoethylether from mixture B.

3. The method according to claim 1 , wherein said acylating agent is a C 1-6 -carboxylic acid.

4. The method according to claim 1 , wherein step (a) comprises removing water from the mixture.

5. The method according to claim 4 , wherein the water removal process is carried out by azeotropic distillation.

6. The method according to claim 1 , wherein separation step (b) comprises both steps (b1) and (b2), and wherein step (b2) is performed after step (b1).

7. The method according to claim 1 , wherein mixture A further comprises N,N′-dimethylbisaminoethylether, and mixture B comprises the amide of N,N′-dimethylbisam inoethylether.

8. The method according to claim 7 , further comprising the step (b3) of separating the amide of N,N′-dimethylbisaminoethylether from mixture B.

9. The method according to claim 1 , wherein the separation step is carried out by distillation.

10. The method according to claim 1 , wherein the transamidation reaction is performed in the presence of monoethanolamine.

11. The method according to claim 3 , wherein the acylating agent is formic acid.

12. The method according to claim 4 , wherein step (a) comprises continuously removing water from the mixture.

13. A method for separating at least one of N,N,N′-trimethylbisaminoethylether and N, N-dimethylbisaminoethylether from a mixture A comprising N, N, N′-trimethylbisaminoethylether, N, N-dimethylbisaminoethylether and N, N, N′, N′-tetramethylbisaminoethylether, wherein said method comprises the steps of:
(a) contacting said mixture A with an acylating agent, to form a mixture B comprising N,N,N′,N′-tetramethylbisaminoethylether and the amides of N,N,N′-trimethylbisaminoethylether and N, N-dimethylbisaminoethylether;
(b) either (b1) separating the amide of N,N,N′-trimethylbisaminoethylether from mixture B and then separating the amide of N,N-dimethylbisaminoethylether from said mixture B; or (b2) separating the amide of N,N-dimethylbisaminoethylether from mixture B; and
(c) at least one of (c1) recovering N,N,N′-trimethylbisaminoethylether from its amide by a transamidation reaction and (c2) recovering N,N-dimethylbisaminoethylether from its amide by a transamidation reaction.

Assignees

• Huntsman Int Llc
• Huntsman Corp Hungary Zrt

Inventors

• Gaspar Attila
• Gaspar Zsolt
• Herseczki Zsanett Szabone
• Humbert Heiko Heinrich
• Kordas Imre
• Vanderstraeten Petra Emma

Classifications

• B01D3/36

  Azeotropic distillation · CPC title

• C07C213/08 Primary

  by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups · CPC title

• C07C213/02

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

• C07C213/10 Primary

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

• C07C217/08

  the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom · CPC title