Ionic liquid composition for carbon dioxide separation membrane, carbon dioxide separation membrane holding said composition, and carbon dioxide concentration apparatus provided with said carbon dioxide separation membrane

Patent metadata

Field	Value
Publication number	US-12330123-B2
Application number	US-202117798745-A
Country	US
Kind code	B2
Filing date	Feb 16, 2021
Priority date	Feb 25, 2020
Publication date	Jun 17, 2025
Grant date	Jun 17, 2025

Abstract

Provide are an ionic liquid composition for a carbon dioxide separation membrane, a carbon dioxide separation membrane retaining the composition in voids, and a carbon dioxide concentration apparatus provided with the carbon dioxide separation membrane that can be used to separate carbon dioxide from high partial pressure to low partial pressure. The permeability of CO2 and CO2 selectivity ratio of the carbon dioxide separation membrane can be improved, and carbon dioxide from high partial pressure to a low partial pressure of 1 kPa or lower can be selectively separated and recycled by using an ionic liquid composition prepared by combining: an ionic liquid (I) that is an aminium having one or more primary or secondary amino groups and an ethylenediamine or propylenediamine backbone in the cation; and an ionic liquid (II) in which the cation has no primary or secondary amino group and the anion is an oxoacid anion.

First claim

The invention claimed is:

1. A method of separating carbon dioxide by using an ionic liquid composition, comprising:
preparing a membrane having a porous layer; and
retaining the ionic liquid composition in voids in the porous layer;

wherein the ionic liquid composition contains
an ionic liquid (I) and
an ionic liquid (II),

wherein a cation in the ionic liquid (I) is an aminium having:
one or more primary or secondary amino groups; and
an ethylenediamine or propylenediamine backbone,

wherein
an anion in the ionic liquid (I) is bis(trifluoromethylsulfonyl)amide, and
a cation in the ionic liquid (II) has no primary or secondary amino group, and
an anion in the ionic liquid (II) is an oxoacid anion, wherein the oxoacid anion is selected from the group consisting of carboxylates, phosphates, phosphonates, and combinations thereof.

2. The method according to claim 1 , wherein
the aminium is selected from the group consisting of 2-aminoethylaminium, 2-(N-hydroxyethylamino)ethylaminium,3-aminopropylaminium, 3-(N-methylamino)propylaminium, 2-(2-(aminoethyl)amino)ethylaminium, 2-(2-(2-(aminoethyl)aminoethyl)amino)ethylaminium and combinations thereof.

3. The method according to claim 1 , wherein the oxoacid anion is selected from the group consisting of acetate, 2-(1-methoxyethoxy)propionate, methylphosphonate and combinations thereof.

4. The method according to claim 1 , wherein the cation of the ionic liquid (II) is selected from the group consisting of 1-ethyl-3-methylimidazolium, N,N-diethyl-N-methyl-N-heptylammonium, N,N-diethyl-N-methyl-N-(6-hydroxyhexyl)ammonium and combinations thereof.

5. The method according to claim 1 , wherein the carbon dioxide have a partial pressure of 1 kPa or lower.

6. A carbon dioxide separation membrane, comprising:
a porous layer retaining an ionic liquid composition in voids in the porous layer wherein the ionic liquid composition containing
an ionic liquid (I); and
an ionic liquid (II),

wherein a cation in the ionic liquid (I) is an aminium having
one or more primary or secondary amino groups; and
an ethylenediamine or propylenediamine backbone,
wherein
an anion in the ionic liquid (I) is bis(trifluoromethylsulfonyl)amide, and
a cation in the ionic liquid (II) has no primary or secondary amino group, and
an anion in the ionic liquid (II) is an oxoacid anion, wherein the oxoacid anion is selected from the group consisting of carboxylates, phosphates, phosphonates and combinations thereof.

7. The carbon dioxide separation membrane according to claim 6 , wherein the aminium is selected from the group consisting of 2-aminoethylaminium, 2-(N-hydroxyethylamino)ethylaminium, 3-aminopropylaminium, 3-(N-methylamino)propylaminium, 2-(2-(aminoethyl)amino)ethylaminium, 2-(2-(2-(aminoethyl)aminoethyl)amino)ethylaminium and combinations thereof.

8. The carbon dioxide separation membrane according to claim 6 , wherein
the oxoacid anion is selected from the group consisting of acetate, 2-(1-methoxyethoxy)propionate, methylphosphonate and combinations thereof.

9. The carbon dioxide separation membrane according to claim 6 , wherein
the cation of the ionic liquid (II) is selected from the group consisting of 1-ethyl-3-methylimidazolium, N,N-diethyl-N-methyl-N-heptylammonium, N,N-diethyl-N-methyl-N-(6-hydroxyhexyl)ammonium and combinations thereof.

10. The carbon dioxide separation membrane according to claim 6 , wherein the carbon dioxide separation membrane comprises:
an ionic liquid affinitive porous layer retaining the ionic liquid composition for a carbon dioxide separation membrane in voids; and
an ionic liquid non-affinitive porous layer.

11. The carbon dioxide separation membrane according to claim 10 , wherein the ionic liquid affinitive porous layer comprises an inorganic material.

12. The carbon dioxide separation membrane according to claim 11 , wherein the inorganic material comprises metal oxide particles with an average particle size from 0.001 to m on a number basis.

13. The carbon dioxide separation membrane according to claim 10 , wherein an average thickness of the ionic liquid affinitive porous layer is from 0.01 to 10 m.

14. A carbon dioxide concentration apparatus comprising the carbon dioxide separation membrane described in claim 6 .

Assignees

• Aist
• Daicel Corp

Inventors

• Makino Takashi
• Kanakubo Mitsuhiro
• Iwaya Masao
• Yamato Yo

Classifications

• B01D71/05

  Cermet materials · CPC title

• B01D69/1213

  Laminated layers · CPC title

• C07D233/58

  with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms · CPC title

• C07C311/48

  having nitrogen atoms of sulfonamide groups further bound to another hetero atom · CPC title

• C07C211/63

  having quaternised nitrogen atoms bound to acyclic carbon atoms · CPC title