IP Library Granted Patent US 12,290,779
Granted Patent B2
US 12,290,779 · App. 18/353,338 · Granted May 6, 2025

Diamine solvent system for CO

Inventors: Deepika Malhotra (Richland, WA); Phillip K. Koech (Richland, WA); David J. Heldebrant (Richland, WA); Vassiliki-Alexandra Glezakou (Richland, WA); Roger J. Rousseau (Richland, WA); Manh Thuong Nguyen (Richland, WA); Robert Perry (Richland, WA); Jordan P. Page (Richland, WA); David C. Cantu (Richland, WA)
Assignee: Battelle Memorial Institute
B01D53/1493B01D53/1425B01D53/1475C07D295/13B01D2252/2041B01D2252/20426B01D2252/20431B01D2252/20452
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 12,290,779
App. No.
18/353,338
Granted
May 6, 2025
Kind
B2
Abstract

Disclosed herein is a method and system for CO 2 removal from a gas stream using a diamine solvent having a Formula I R 1 (R 2 )N-L 1 -NH—R 3    Formula I. With respect to Formula I, each of R 1 and R 2 independently is aliphatic, cycloaliphatic, or R 1 and R 2 together with the nitrogen to which they are attached, form a heterocyclyl ring; L 1 is aliphatic, cycloaliphatic, or L 1 and R 1 together with the nitrogen to which they are attached form a heterocyclyl ring; and R 3 is aliphatic, cycloaliphatic, cycloalkylalkyl, or alkoxyalkyl. And/or the compound may have a viscosity of less than 75 cP at a CO 2 -loading of 40 mol % and at a temperature of 40° C.

Claims (30)

1. A method, comprising:

contacting a gas stream comprising a first amount of CO 2 with a CO 2 -lean solvent stream comprising a compound according to Formula I, to form a treated gas stream comprising a second amount of CO 2 that is less than the first amount, and to form a CO 2 -rich solvent stream; and

heating the CO 2 -rich solvent stream to form a CO 2 stream and regenerate the CO 2 -lean solvent;

wherein the compound according to Formula I has a structure

R 1 (R 2 )N-L 1 -NH—R 3    Formula I

each of R 1 and R 2 independently is aliphatic, cycloaliphatic, or R 1 and R 2 together with the nitrogen to which they are attached, form a heterocyclyl ring;

L 1 is aliphatic, cycloaliphatic, or L 1 and R 1 together with the nitrogen to which they are attached form a heterocyclyl ring; and

R 3 is aliphatic, cycloaliphatic, cycloalkylalkyl, or alkoxyalkyl; and

wherein

the CO 2 -lean solvent stream consists essentially of the compound of Formula I; and

the compound according to Formula I is not

2. The method of claim 1 , wherein the CO 2 -rich solvent comprises less than 10 wt % water.

3. The method of claim 1 , wherein at least one of R 1 and R 2 is branched alkyl or cycloalkyl.

4. The method of claim 1 , wherein R 1 forms a heterocyclyl with L 1 .

5. The method of claim 1 , wherein R 1 and R 2 together with the nitrogen to which they are attached, forms a heterocyclyl ring.

6. The method of claim 1 , wherein at least one of R 1 and R 2 is not linear alkyl.

7. The method of claim 1 , wherein R 3 is alkoxyalkyl.

8. The method of claim 1 , wherein each of R 1 and R 2 independently is C 1-6 alkyl.

9. The method of claim 1 , wherein R 1 and R 2 together with the nitrogen to which they are attached form a 5- or 6-membered heterocyclyl ring.

10. The method of claim 1 , wherein L 1 is C 2-4 alkyl.

11. The method of claim 1 , wherein L 1 and R 1 together with the nitrogen to which they are attached form a 5- or 6-membered heterocyclyl ring.

12. The method of claim 1 , wherein R 3 is branched C 3-6 alkyl, or alkoxyalkyl.

13. The method of claim 1 , wherein the compound is selected from

14. The method of claim 1 , wherein:

the solvent has a vapor pressure of less than 1 Torr at 40° C. and a residual water content of less than 0.1 wt %;

the solvent has a viscosity of less than 75 cP at a CO 2 -loading of 40 mol % and at a temperature of 40° C.; or

a combination thereof.

15. The method of claim 1 , wherein contacting the gas stream with the CO 2 -lean solvent comprises contacting the gas stream at a first temperature of from 30° C. to 80° C.

16. The method of claim 1 , wherein heating the CO 2 -rich solvent comprises heating the CO 2 -rich solvent to a second temperature of 80° C. to 160° C.

17. The method of claim 1 , further comprising cooling the regenerated CO 2 -lean solvent to a temperature of from 30° C. to 60° C.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 16, 2023
From: MALHOTRA, DEEPIKA; KOECH, PHILLIP K.; HELDEBRANT, DAVID J.; GLEZAKOU, VASSILIKI-ALEXANDRA; ROUSSEAU, ROGER J.; NGUYEN, MANH THUONG; PAGE, JORDAN P.; CANTU, DAVID C.
To: BATTELLE MEMORIAL INSTITUTE
Reel/Frame 064612/0659 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 16, 2023
From: PERRY, ROBERT JAMES
To: GENERAL ELECTRIC COMPANY
Reel/Frame 064612/0700 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 16, 2023
From: GENERAL ELECTRIC COMPANY
To: BATTELLE MEMORIAL INSTITUTE
Reel/Frame 064612/0709 →
Continuity (3)
Division 17584597 · Jan 26, 2022
Continuation 16363672 · Mar 25, 2019
Related Publication 20230356145A1 · Nov 9, 2023
References Cited (18)
US 8765951B2 · Blair et al. · 2014 [cited by applicant]
US 20130011314A1 · Porcheron et al. · 2013 [cited by applicant]
US 20140127103A1 · Yang et al. · 2014 [cited by applicant]
US 20160001220A1 · Higashii et al. · 2016 [cited by applicant]
US 20170246587A1 · Hong et al. · 2017 [cited by applicant]
JP 2006167520 · 2006 [cited by applicant]
JP 2017159288 · 2017 [cited by applicant]
KR 1020160101696 · 2016 [cited by applicant]
Chowdhury et al., “Development of novel tertiary amine absorbents for CO [cited by applicant]
Chowdhury et al., “CO [cited by applicant]
Heldebrant et al., “Reversible zwitterionic liquids, the reaction of alkanol guanidines, alkanol amidines, and diamines with CO [cited by applicant]
Heldebrant et al., “Water-Lean Solvents for Post-Combustion CO [cited by applicant]
International Search Report dated Nov. 2, 2020 from International Application No. PCT/US2020/023153. [cited by applicant]
Lepaumier et al., “New Amines for CO [cited by applicant]
Martin et al., “New Amines for CO [cited by applicant]
Singto et al., “Synthesis of new amines for enhanced carbon dioxide (CO [cited by applicant]
Written Opinion dated Nov. 2, 2020 from International Application No. PCT/US2020/023153. [cited by applicant]
Yang et al., “Toward Intelligent CO [cited by applicant]