Copoly(1,2,4-triazole)s membranes for sour mixed-gas separation applications

Inventors: Ali Hayek (Dhahran, SA); Abdulkarim Alsamah (Dhahran, SA)

C08G61/124 B01D53/228 B01D71/62 C07C7/144 C08G61/123 C08G73/08 C10L3/103 C10L3/104 B01D2256/245 B01D2257/304 B01D2257/504 B01D2323/30 C08G2261/124 C08G2261/148 C08G2261/312 C08G2261/334 C08G2261/72 C08G2261/76 C10L2290/548

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Quick Facts

Patent No.: US 12,668,659
App. No.: 18/335,679
Granted: Jun 30, 2026
Kind: B2

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Abstract

This disclosure relates to polymers and polymeric membranes that incorporate functionalized copoly(1,2,4-triazole)s. The polymers and polymeric membranes can be used in sour natural gas separation applications.

Claims (37)

1 . A polymer comprising:

a monomer unit of Formula VIIa:

and a monomer unit of Formula VIIIa:

wherein

R 1 is hydroxyl;

R 2 -R 5 are hydrogen;

R′ 2 is methyl;

R′ 3 is methyl; and

R′ 1 , R′ 4 , and R′ 5 are each hydrogen, wherein the ratio of min is between 1:10 and 10:1 and wherein the polymer has a number-average molecular weight of about 1,000 g/mol to about 1,000,000 g/mol.

2 . The polymer of claim 1 , wherein the polymer comprises the monomer unit of Formula VIIa and the monomer unit of Formula VIIIa in a molar ratio of about 2:1 to about 1:2.

3 . The polymer of claim 1 , wherein the polymer comprises the monomer unit of Formula VIIa and the monomer unit of Formula VIIIa in a molar ratio of about 1:1.

4 . The polymer of claim 1 , having a number-average molecular weight of about 100,000 g/mol to 500,000 g/mol.

5 . The polymer of claim 1 , wherein the polymer is covalently crosslinked.

6 . A membrane comprising the polymer of claim 1 .

7 . The membrane of claim 6 , wherein the polymer is covalently crosslinked.

8 . The membrane of claim 6 , comprising at least about 80 wt % of the polymer.

9 . A method for separating CO 2 and H 2 S from natural gas, the method comprising:

introducing a natural gas stream to the membrane of claim 6 ; and

separating the CO 2 and H 2 S from the natural gas stream.

10 . A polymer comprising:

a monomer unit of Formula VIIa:

and a monomer unit of Formula VIIIa:

wherein

R 2 is-CH 2 —Br;

R 3 is methyl;

R 1 , R 4 , and R 5 are each hydrogen; and

R′ 1 —R′ 5 are each independently selected from hydrogen, alkyl, hydroxyl, alkoxy, halogen, aromatic, and cyclic functional groups, at least one of R′ 1 —R′ 5 is not hydrogen, and wherein at least one of R 1 -R 5 is different from at least one of R′ 1 —R′ 5 , wherein the ratio of m:n is between 1:10 and 10:1 and wherein the polymer has a number-average molecular weight of about 1,000 g/mol to about 1,000,000 g/mol.

11 . The polymer of claim 10 , wherein the polymer comprises the monomer unit of Formula VIIa and the monomer unit of Formula VIIIa in a molar ratio of about 2:1 to about 1:2.

12 . The polymer of claim 10 , wherein the polymer comprises the monomer unit of Formula VIIa and the monomer unit of Formula VIIIa in a molar ratio of about 1:1.

13 . The polymer of claim 10 , having a number-average molecular weight of about 100,000 g/mol to 500,000 g/mol.

14 . The polymer of claim 10 , wherein the polymer is covalently crosslinked.

15 . A membrane comprising the polymer of claim 10 .

16 . The membrane of claim 15 , wherein the polymer is covalently crosslinked.

17 . The membrane of claim 15 , comprising at least about 80 wt % of the polymer.

18 . A method for separating CO 2 and H 2 S from natural gas, the method comprising:

introducing a natural gas stream to the membrane of claim 15 ; and

separating the CO 2 and H 2 S from the natural gas stream.