Reactive amine catalysts for polyurethane foam
A process for the separation of a first amine having a tertiary amine group and a secondary amine group such as N,N,N′-trimethylbis(aminoethyl)ether from a di-tertiary amine such as N,N,N′,N′-tetramethylbis(aminoethyl)ether, comprising: contacting a mixture of the first amine and the di-tertiary amine with a carbonyl compound capable of forming an enamine such that the carbonyl compound reacts with the first amine to form an enamine; separating the enamine from the di-tertiary amine; and subsequently converting the enamine to the first amine.
1. A process for the separation of a first amine having a tertiary amine group and a secondary amine group from a di-tertiary amine, comprising: contacting a mixture of the first amine and the di-tertiary amine with a carbonyl compound capable of forming an enamine such that the carbonyl compound reacts with the first amine to form an enamine; separating the enamine from the di-tertiary amine; and subsequently converting the enamine to the first amine.
2. The process of claim 1 , wherein the first amine is of formula A:
where R 1 is alkyl or an alkylene alcohol of from 1 to 6 carbons; R 2 is alkyl or an alkylene alcohol of from 1 to 6 carbons; R 3 is alkyl or alkylene alcohol of from 1 to 6 carbons; R 4 is hydrogen; x is an integer between 2 and 5; and y is an integer between 2 and 5.
3. The process of claim 2 , wherein R 1 is CH 3 , CH 2 CH 3 , or CH 2 CH 2 OH.
4. The process of claim 2 , wherein R 2 is CH 3 , CH 2 CH 3 , or CH 2 CH 2 OH.
5. The process of claim 2 , wherein R 3 is CH 3 or CH 2 CH 3 .
6. The process of claim 1 , wherein R 1 is CH 3 , CH 2 CH 3 , or CH 2 CH 2 OH; R 2 is CH 3 , CH 2 CH 3 , or CH 2 CH 2 OH; and R 3 is CH 3 or CH 2 CH 3 .
7. The process of claim 2 , wherein the first amine is N,N,N′-trimethylbis(aminoethyl)ether and the di-tertiary amine is N,N,N′,N′-tetramethylbis(aminoethyl)ether.
8. The process of claim 1 , where the enamine is converted by hydrolysis.
9. The process of claim 1 , wherein the carbonyl compound is a ketone or aldehyde.
10. The process of claim 1 , wherein the carbonyl compound is a ketone or aldehyde having 2 to 20 carbons.
11. The process of claim 1 , wherein the carbonyl compound is cyclohexanone.
12. The process of claim 1 , wherein the di-tertiary amine is of formula A:
where R 1 is alkyl or an alkylene alcohol of from 1 to 6 carbons; R 2 is alkyl or an alkylene alcohol of from 1 to 6 carbons; R 3 is alkyl or alkylene alcohol of from 1 to 6 carbons; R 4 is alkyl or an alkylene alcohol of from 1 to 6 carbons; x is an integer between 2 and 5; and y is an integer between 2 and 5.
13. The process of claim 1 , wherein during the contacting, water is removed as the enamine is formed.
14. The process of claim 1 , wherein the enamine is separated from the di-tertiary amine by distillation.
15. The process of claim 1 , further comprising removing the reformed carbonyl compound after converting the enamine to the first amine.
16. A process for the separation of N,N,N′-trimethylbis(aminoethyl)ether from N,N,N′,N′-tetramethylbis(aminoethyl)ether, comprising: contacting a mixture of the N,N,N′-trimethylbis(aminoethyl)ether and N,N,N′,N′-tetramethylbis(aminoethyl)ether with a carbonyl compound capable of forming an enamine such that the carbonyl compound reacts with the N,N,N′-trimethylbis(aminoethyl)ether to form an enamine; separating the enamine from the N,N,N′,N′-tetramethylbis(aminoethyl)ether; and subsequently converting the enamine to reform the N,N,N′-trimethylbis(aminoethyl)ether.
17. A N,N,N′-trialkylbis(aminoethyl)ether-enamine.
18. The enamine of claim 17 , wherein the enamine is formed from N,N,N′-trimethylbis(aminoethyl)ether and cyclohexanone.