IP Library Granted Patent US 9,409,122
Granted Patent B2
US 9,409,122 · App. 14/112,724 · Granted Aug 9, 2016

Gas capture process

Inventors: Qi Yang (Wheelers Hill, AU); Susan N. James (Rowville, AU); Mathew John Ballard (Glen Waverly, AU); Mark Bown (Clayton North, AU); Paul Feron (Floraville, AU); Graeme Douglas Puxty (Mayfield, AU)
Assignee: Commonwealth Scientific and Industrial Research Organisation
B01D53/62B01D53/1475B01D53/1493C07D211/26C07D211/58B01D2252/20442Y02C10/04Y02C10/06Y02P20/152
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 9,409,122
App. No.
14/112,724
Granted
Aug 9, 2016
Kind
B2
Abstract

A process for the capture of CO 2 from gas streams, the process including contacting a CO 2 containing gas stream with a compound including: a primary or non-sterically hindered secondary amine group and at least one tertiary amine or sterically hindered secondary amine group; wherein the primary or non-sterically hindered secondary amine and the nearest tertiary or sterically hindered secondary amine group are separated by a carbon chain including 3 or 4 carbon atoms and wherein the compound is a compound of Formula (I).

Claims (66)

1. A process for the capture of CO 2 from gas streams, the process including contacting a CO 2 containing gas stream with a compound including:

a primary or non-sterically hindered secondary amine group and

at least one tertiary amine or sterically hindered secondary amine group;

wherein the primary or non-sterically hindered secondary amine and the nearest tertiary or sterically hindered secondary amine group are separated by a carbon chain including 3 or 4 carbon atoms and wherein the compound is a compound of Formula (I)

wherein

R 1 is represented by hydrogen, C 2 to C 6 alkanol or C 1 to C 6 alkyl;

R 2 is represented by hydrogen, C 1 to C 6 alkyl, C 2 to C 6 alkanol, —(CH 2 ) n —NR 6 R 7 , —(CH 2 ) p —COOH, —(CH 2 ) p COOQ, —(CH 2 ) p -heterocyclic ring containing one to four heteroatoms independently selected from nitrogen, oxygen and sulphur;

R 3 and R 5 are independently selected from hydrogen, C 1 to C 4 alkyl, C 2 to C 6 alkanol, —(CH 2 ) n —NR 8 R 9 ;

R 4 is represented by hydrogen, C 1 to C 6 alkyl, C 2 to C 6 alkanol, —(CH 2 ) n —NR 6 R 7 , —(CH 2 ) p —COOH, —(CH 2 ) p COOQ, —(CH 2 ) p —SO 3 H, —(CH 2 ) p SO 3 Q, —(CH 2 ) p —PO 3 H 2 , —(CH 2 ) p PO 3 Q s , —(CH 2 ) p -heterocyclic ring containing one to four heteroatoms independently selected from nitrogen, oxygen and sulphur;

x 0 or 1;

n is 2 to 6;

p is 1 to 6;

Q is hydrogen, a metal ion or R 16 R 17 R 18 R 19 N + ;

s is 1 or 2

R 6 and R 7 are independently selected from hydrogen, alkyl, alkanol, alkylamine or R 6 and R 7 together with the nitrogen atom to which they are attached form a ring structure

R 8 and R 9 are independently selected from C 1 to C 6 alkyl, C 2 to C 6 alkanol, C 2 to C 6 alkylamine, —(CH 2 ) n —NR 6 R 7 , —(CH 2 ) p —COOH, —(CH 2 ) p COOQ, —(CH 2 ) p —SO 3 H, —(CH 2 ) p SO 3 Q, —(CH 2 ) p —PO 3 H 2 , —(CH 2 ) p PO 3 Q s , or R 8 and R 9 together with the nitrogen atom to which they are attached form a ring structure; and

R 16 , R 17 , R 18 and R 19 are independently selected from hydrogen or alkyl;

with the proviso that when R 4 is hydrogen, R 1 and/or R 2 is not hydrogen;

when R 4 is not hydrogen, R 1 and/or R 2 is hydrogen;

when R 4 and R 1 are both hydrogen, R 2 is not methyl; and

when R 4 and R 2 are both hydrogen, R 1 is not methyl.

2. A process according to claim 1 wherein the compound is a compound of formula (I), wherein:

R 1 is represented by hydrogen or C 1 alkyl;

R 2 is represented by hydrogen, —CH 2 CH 3 , —CH 2 CH 2 CH 3 , —(CH 2 ) 2 OH, —(CH 2 ) 3 OH, —(CH 2 ) 6 OH, —CH 2 COOH, —CH 2 COONa, —CH 2 COOK, —(CH 2 ) 2 N(CH 3 ) 2 , —(CH 2 ) 2 N(CH 2 CH 2 ) 2 O, —(CH 2 ) 2 N(CH 2 CH 2 ) 2 S, —CH 2 (5-imidazole) or —(CH 2 ) 2 (5-imidazole);

R 3 is represented by hydrogen;

R 4 is represented by hydrogen, —CH 2 CH 3 , —CH 2 CH 2 CH 3 , —(CH 2 ) 2 OH, —(CH 2 ) 3 OH, —(CH 2 ) 6 OH, —CH 2 COOH, —CH 2 COONa, —CH 2 COOK, —(CH 2 ) 2 N(CH 3 ) 2 , —(CH 2 ) 2 N(CH 2 CH 2 ) 2 O, —(CH 2 ) 2 N(CH 2 CH 2 ) 2 S, —CH 2 (5-imidazole) or —(CH 2 ) 2 (5-imidazole); and

R 5 is represented by hydrogen;

with the proviso that when R 4 is hydrogen, R 2 is not hydrogen;

when R 2 is hydrogen, R 4 is not hydrogen; and

when R 2 is hydrogen, R 1 is hydrogen and x is 0.

3. A process according to claim 2 wherein the compound is a compound of formula (I), wherein:

R 1 is represented by hydrogen or C 1 alkyl;

R 2 is represented by hydrogen, —CH 2 CH 3 , —CH 2 CH 2 CH 3 , —(CH 2 ) 2 OH, —(CH 2 ) 3 OH, —(CH 2 ) 6 OH, —CH 2 COOH, —CH 2 COONa, —CH 2 COOK, —(CH 2 ) 2 N(CH 3 ) 2 , —(CH 2 ) 2 N(CH 2 CH 2 ) 2 O, —(CH 2 ) 2 N(CH 2 CH 2 ) 2 S, —CH 2 (5-imidazole) or —(CH 2 ) 2 (5-imidazole);

R 3 is represented by hydrogen;

R 4 is represented by hydrogen; and

R 5 is represented by hydrogen.

4. A process according to claim 2 wherein the compound is a compound of formula (I), wherein:

x is 0;

R 1 is represented by hydrogen;

R 2 is represented by hydrogen;

R 3 is represented by hydrogen;

R 4 is represented by hydrogen, —CH 2 CH 3 , —CH 2 CH 2 CH 3 , —(CH 2 ) 2 OH, —(CH 2 ) 3 OH, —(CH 2 ) 6 OH, —CH 2 COOH, —CH 2 COONa, —CH 2 COOK, —(CH 2 ) 2 N(CH 3 ) 2 , —(CH 2 ) 2 N(CH 2 CH 2 ) 2 O, —(CH 2 ) 2 N(CH 2 CH 2 ) 2 S, —CH 2 (5-imidazole) or —(CH 2 ) 2 (5-imidazole); and

R 5 is represented by hydrogen.

5. A process according to claim 3 wherein the compound is a compound of formula (I), wherein:

R 1 is represented by hydrogen or C 1 alkyl;

R 2 is represented by —CH 2 CH 3 , —CH 2 CH 2 CH 3 , —(CH 2 ) 2 OH, —(CH 2 ) 3 OH, —(CH 2 ) 6 OH, —CH 2 COOH or —(CH 2 ) 2 N(CH 3 ) 2 ;

R 3 is represented by hydrogen;

R 4 is represented by hydrogen; and

R 5 is represented by hydrogen.

6. A process according to claim 4 wherein the compound is a compound of formula (I), wherein:

R 1 is represented by hydrogen;

R 2 is represented by hydrogen;

R 3 is represented by hydrogen;

R 4 is represented by —CH 2 CH 3 , —CH 2 CH 2 CH 3 , —(CH 2 ) 2 OH, —(CH 2 ) 3 OH or —(CH 2 ) 6 OH; and

R 5 is represented by hydrogen.

7. A process according to claim 2 wherein the compound is a compound of formula (I), wherein:

R 1 is represented by hydrogen or C 1 alkyl;

R 2 is represented by hydrogen, —CH 2 CH 3 , —CH 2 CH 2 CH 3 or —(CH 2 ) 2 N(CH 3 ) 2 ;

R 3 is represented by hydrogen;

R 4 is represented by hydrogen, —CH 2 CH 3 , —CH 2 CH 2 CH 3 or —(CH 2 ) 2 N(CH 3 ) 2 ; and

R 5 is represented by hydrogen;

with the proviso that when R 4 is hydrogen, R 2 is not hydrogen;

when R 2 is hydrogen, R 4 is not hydrogen; and

when R 2 is hydrogen, R 1 is hydrogen and x is 0.

8. A process according to claim 2 wherein the compound is selected from the group consisting of:

9. A process according to claim 2 wherein the compound is selected from the group consisting of:

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 21, 2013
From: YANG, QI; BALLARD, MATHEW JOHN; FERON, PAUL HUBERT MARIA; JAMES, SUSAN N.; BOWN, MARK; PUXTY, GRAEME DOUGLAS
To: COMMONWEALTH SCIENTIFIC AND INDUSTRIAL RESEARCH ORGANISATION
Reel/Frame 031441/0674 →
Priority Claims (1)
AU 2011901448 · Apr 18, 2011 · national
Continuity (1)
Related Publication 20140127103A1 · May 8, 2014