# US 2022/0032268 A1 · Amine-appended chemical sorbent

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- Number: US 2022/0032268 A1
- Document ID: US20220032268A1
- Status: Published application
- Kind: A1
- Application number: 17/380,091
- Filed: 2021-07-20
- Published: 2022-02-03
- Earliest claimed: 2020-07-31
- Applicants: Battelle Memorial Institute
- Inventors: David Hopkinson; Ali K. Sekizkardes
- Web page: https://patentgrep.com/patent/US20220032268A1

## CPC

- B01J 20/265: {modified or post-treated polymers (polymer carriers or substrates subjected to further impregnating or coating B01J20/3208)}
- C08G 59/20: characterised by the epoxy compounds used
- B01J 20/28016: {Particle form}
- B01J 20/28023: {Fibres or filaments (fibres or filaments in the form of membranes B01J20/28038; B01J20/28007 takes precedence)}
- B01J 20/3007: {Moulding, shaping or extruding}
- B01J 20/3085: {Chemical treatments not covered by groups B01J20/3007 - B01J20/3078}
- C08G 65/40: from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
- C08G 65/48: Polymers modified by chemical after-treatment
- Y02C 20/40: of CO2
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- Y02C: CAPTURE, STORAGE, SEQUESTRATION OR DISPOSAL OF GREENHOUSE GASES [GHG]

## Abstract

A chemical structure, and a process for synthesizing the chemical structure, of:

## Claims

### Claim 1

A chemical structure of:

### Claim 2 (depends on 1)

The structure of claim 1, R being one selected from the group consisting of:

### Claim 3

A process comprising:
synthesizing a polymer with intrinsic microscopy (PIM-1) by polycondensation reaction of one-dimensional monomers, the PIM-1 comprising a nitrile (—CN) group, the one-dimensional monomers comprising:
3,3,3′3′-tetramethyl-1,1′-spirobisindane-5,5′,6,6′-tetrol (TTSBI); and
1,3-dicyanotetrafluorobenzene (DCTB);
functionalizing the PIM-1 with a carboxylic acid (—COOH) group by converting the —CN to the —COOH, the functionalizing of the PIM-1 resulting in a hydrolyzed polymer (PIM-1-Cn), a degree of functionalization of the PIM-1 being controlled, in part, by:
adjusting a reaction temperature; and
adjusting a reaction time; and
reacting the PIM-1-Cn through an acid-base interaction, the PIM-1-Cn being reacted with tris(2-aminoehtyl)amine (TAEA), the reacted PIM-1-Cn resulting in a primary amine-appended sorbent (PIM-1-Cn-TA).

### Claim 4 (depends on 3)

The process of claim 3, further comprising:
casting the amine-appended sorbent into a product selected from the group consisting of:
a pellet;
a film;
a solid fiber strand; and
a hollow fiber strand.

### Claim 5 (depends on 3)

The process of claim 3, wherein the amine-appended sorbent has a CO2 uptake capacity of at least thirty-six cubic centimeters per gram (≥36 cc/g).

### Claim 6 (depends on 3)

The process of claim 3, wherein:
the reaction temperature is approximately twenty-five degrees Celsius (25° C.); and
the reaction time is approximately twenty-four (24) hours.

### Claim 7 (depends on 3)

The process of claim 3, wherein:
the reaction temperature is approximately one-hundred-and-twenty degrees Celsius (120° C.); and
the reaction time is approximately ninety (90) minutes.

### Claim 8 (depends on 3)

The process of claim 3, wherein:
the reaction temperature is approximately one-hundred-and-twenty degrees Celsius (120° C.); and
the reaction time is approximately two-hundred-and-ten (210) minutes.

### Claim 9

A process comprising:
functionalizing a polymer with intrinsic microscopy (PIM-1) with a carboxylic acid (—COOH) group, the functionalizing of the PIM-1 resulting in a hydrolyzed polymer (PIM-1-Cn); and
reacting the PIM-1-Cn with a primary amine, the reacted PIM-1-Cn resulting in an amine-appended sorbent (PIM-1-Cn-TA).

### Claim 10 (depends on 9)

The process of claim 9, further comprising synthesizing the PIM-1 by polycondensation reaction of one-dimensional monomers.

### Claim 11 (depends on 10)

The process of claim 10, the one-dimensional monomers comprising:
3,3,3′3′-tetramethyl-1,1′-spirobisindane-5,5′,6,6′-tetrol (TTSBI); and
1,3-dicyanotetrafluorobenzene (DCTB).

### Claim 12 (depends on 9)

The process of claim 9, the PIM-1 comprising a nitrile (—CN) group.

### Claim 13 (depends on 9)

The process of claim 9, the functionalizing of the PIM-1 comprising converting the —CN to the —COOH.

### Claim 14 (depends on 9)

The process of claim 9, further comprising controlling a degree of functionalization of the PIM-1 by:
adjusting a reaction temperature; and
adjusting a reaction time.

### Claim 15 (depends on 14)

The process of claim 14, the controlling of the degree of functionalization of the PIM-1 comprising adjusting a reaction temperature.

### Claim 16 (depends on 15)

The process of claim 15, the reaction temperature being one selected from the group consisting of:
approximately twenty-five degrees Celsius (25° C.); and
approximately 120° C.

### Claim 17 (depends on 14)

The process of claim 14, the controlling of the degree of functionalization of the PIM-1 comprising adjusting a reaction time.

### Claim 18 (depends on 17)

The process of claim 17, the reaction time being one selected from the group consisting of:
approximately twenty-four (24) hours;
approximately ninety (90) minutes; and
approximately two-hundred-and-ten (210) minutes.

### Claim 19 (depends on 9)

The process of claim 9, the PIM-1-Cn being reacted with tris(2-aminoehtyl)amine (TAEA).

### Claim 20 (depends on 9)

The process of claim 9, the PIM-1-Cn being reacted in an acid-base reaction.