# US 2013/0153508 A1 · Phase Selective Gelation With Alkylated Aromatic Acid Compounds

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- Number: US 2013/0153508 A1
- Document ID: US20130153508A1
- Status: Published application
- Kind: A1
- Application number: 13/327,664
- Filed: 2011-12-15
- Published: 2013-06-20
- Earliest claimed: 2011-12-15
- Assignees: National Research Council of Canada; Xerox Corporation
- Inventors: Darren A. Makeiff; Rina Carlini
- Web page: https://patentgrep.com/patent/US20130153508A1

## CPC

- B01D 17/0202: {by ab- or adsorption}
- B01J 13/0065: {containing an organic phase}
- B01D: SEPARATION (separating solids from solids by wet methods B03B, B03D; by pneumatic jigs or tables B03B; by other dry methods B07; magnetic or electrostatic separation of solid materials from solid materials or fluids, separation by high-voltage electric fields B03C; centrifuges, vortex apparatus B04; presses per se for squeezing-out liquid from liquid-containing material B30B9/02; treatment of water C02F, e.g. softening by ion-exchange C02F1/42; {arrangements of air intake cleaners in gas turbine plants F02C7/05} ; arrangements or mounting of filters in air-conditioning, air-humidification or ventilation F24F13/28)
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS

## Abstract

Disclosed is a process which comprises mixing an alkylated aromatic acid with a mixture comprising a first liquid and a second liquid, thereby causing formation of an organogel comprising the alkylated aromatic acid and the first liquid.

## Claims

### Claim 1

A process which comprises mixing an alkylated aromatic acid with a mixture comprising a first liquid and a second liquid, thereby causing formation of an organogel comprising the alkylated aromatic acid and the first liquid.

### Claim 2 (depends on 1)

A process according to claim 1 wherein formation of the organogel causes separation of at least some of the first liquid from the second liquid.

### Claim 3 (depends on 1)

A process according to claim 1 wherein the first liquid and the second liquid are immiscible.

### Claim 4 (depends on 1)

A process according to claim 1 wherein the alkylated aromatic acid is mixed with the first liquid in an amount of at least about 0.05% by weight of the first liquid.

### Claim 5 (depends on 1)

A process according to claim 1 wherein the alkylated aromatic acid is mixed with the first liquid in an amount of no more than about 20% by weight of the first liquid.

### Claim 6 (depends on 1)

A process according to claim 1 wherein the first liquid and the second liquid are present in relative amounts of from about 0.1 to about 1 part by weight first liquid per every 1 part by weight second liquid.

### Claim 7 (depends on 1)

A process according to claim 1 further comprising separating the organogel from the mixture.

### Claim 8 (depends on 7)

A process according to claim 7 wherein the separation process comprises distillation.

### Claim 9 (depends on 1)

A process according to claim 1 wherein the alkylated aromatic acid is of the formula
or mixtures thereof, wherein R1, R2, R3, R4, and R5 each, independently of the other, are:
(i) hydrogen atoms;
(ii) alkyl groups, including substituted and unsubstituted alkyl groups, wherein hetero atoms either may or may not be present in the alkyl group;
(iii) aryl groups, including substituted and unsubstituted aryl groups, wherein hetero atoms either may or may not be present in the aryl group;
(iv) arylalkyl groups, including substituted and unsubstituted arylalkyl groups, wherein hetero atoms either may or may not be present in either or both of the alkyl portion and the aryl portion of the arylalkyl group; or
(v) alkylaryl groups, including substituted and unsubstituted alkylaryl groups, wherein hetero atoms either may or may not be present in either or both of the alkyl portion and the aryl portion of the alkylaryl group;
provided that at least one of R1, R2, R3, R4, and R5 is —X—Rc, wherein:
(vi) —X— is a linking group between Rc and the aromatic group; and
(vii) Rc is an alkyl group, including substituted and unsubstituted alkyl groups, wherein hetero atoms either may or may not be present in the alkyl group.

### Claim 10 (depends on 9)

A process according to claim 9 wherein exactly one of R1, R2, R3, R4, and R5 is —X—Rc.

### Claim 11 (depends on 9)

A process according to claim 9 wherein exactly two of R1, R2, R3, R4, and R5 are each, independently of the other, an —X—Rc group.

### Claim 12 (depends on 9)

A process according to claim 9 wherein exactly one of R1, R2, R3, R4, and R5 is —X—Rc and exactly one of R1, R2, R3, R4, and R5 is —COOH or —CONH2.

### Claim 13 (depends on 9)

A process according to claim 9 wherein the alkylated aromatic acid is of the formula
or mixtures thereof, R1, R3, and R5 are each hydrogen atoms, R2 is —X1—Rc1, and R4 is —COOH or —X2—Rc2, wherein X1 and X2 have the same definition as X and can be either the same as or different from each other and Rc1 and Rc2 have the same definition as Rc and can be either the same as or different from each other.

### Claim 14 (depends on 9)

A process according to claim 9 wherein Rc is:
(a) a linear unsubstituted alkyl group of the formula —(CH2)nCH3, wherein n is an integer;
(b) a branched unsubstituted alkyl group of the formula
wherein m is an integer and p is an integer;
(c) a branched unsubstituted alkyl group of the formula
wherein s is an integer and t is an integer;
(d) a branched unsubstituted alkyl group of the formula
wherein u is an integer and v is an integer;
(e) a multi-branched unsubstituted alkyl group of the formula
wherein q is an integer and r is an integer;
or mixtures thereof.

### Claim 15 (depends on 9)

A process according to claim 9 wherein —X— is:
(i) —O—;
(ii) —S—;
(iii) —SO—;
(iv) —SO2—;
(v) —NH—(C═O) —;
(vi) —(C═O)—NH—;
(vii) —NH—(C═S)—;
(viii) —(C═S)—NH—;
(ix) —NH—;
(x) —NH—(C═O)—NH—;
(xi) —NH—(C═S)—NH—;
(xii) —NH—(C═O)—O—;
(xiii) —O—(C═O)—NH—;
(xiv) —NH—(C═S)—O—;
(xv) —S—(C═O)—NH—;
(xvi) —NH—(C═S)—O—;
(xvii) —NH—(C═S)—S—;
(xviii) —O—(C═S)—NH—;
(xix) —S—(C═S)—NH—;
(xx) —(C═O)—O—;
(xxi) —(C═O)—S—;
(xxii) —O—(C═O) —;
(xxiii) —S—(C═O) —;
(xxiv) —(C═S)—O—;
(xxv) —(C═S)—S—;
(xxvi) —O—(C═S)—;
(xxvii) —S—(C═S)—;
(xxviii) —O—(C═O)—O—;
(xxix) —O—(C═S)—O—; or
(xxx) a combination thereof.

### Claim 16 (depends on 9)

A process according to claim 9 wherein the alkylated aromatic acid is of the formula
wherein R1′ has the same definition as R1 and can be either the same as or different from R1, R2′ has the same definition as R2 and can be either the same as or different from R2, and Rd is a difunctional moiety that bridges the aromatic acid groups.

### Claim 17 (depends on 1)

A process according to claim 1 wherein the alkylated aromatic acid is
or mixtures thereof.

### Claim 18

A method for extracting a first liquid from a second liquid which comprises:
(a) providing a mixture comprising a first liquid and a second liquid; and
(b) contacting the mixture with an alkylated aromatic acid under conditions effective to cause formation of an organogel comprising the alkylated aromatic acid and the first liquid, thereby extracting at least some of the first liquid from the second liquid.

### Claim 19

A process for treating an organic contamination which comprises applying an alkylated aromatic acid to the oil of said oil contamination.

### Claim 20 (depends on 19)

A process according to claim 19 further comprising:
(a) mixing the alkylated aromatic acid with the contamination to form an organogel; and
(b) collecting the resulting organogel.