# US 4,396,755 A · Production of aromatic polyketones

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- Number: US 4,396,755 A
- Document ID: US4396755A
- Status: Granted
- Kind: A
- Application number: 06/367,613
- Filed: 1982-04-12
- Granted: 1983-08-02
- Earliest claimed: 1981-11-12
- Assignees: Imperial Chemical Industries PLC
- Inventors: John B. Rose
- Web page: https://patentgrep.com/patent/US4396755A

## CPC

- C08G 61/127: {derived from carbon dioxide, carbonyl halide, carboxylic acids or their derivatives}
- C08G 61/00: Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule (C08G2/00 - C08G16/00 take precedence)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

Production of an aromatic polyketone by reacting in the presence of a quinquevalent phosphorous halide (preferably PCl.sub.5) and a fluoroalkane sulphonic acid (preferably CF.sub.3 SO.sub.2 OH) the reactants selected from: (a) a mixture of (i) at least one aromatic dicarboxylic acid HO.sub.2 C--Ar--CO.sub.2 H where --Ar'-- is a divalent aromatic radical and CO.sub.2 H is an aromatically bound carboxylic acid group, which dicarboxylic acid is polymerizable with the at least one aromatic compound of (ii), and (ii) at least one aromatic compound H--Ar'--H where --Ar'-- is a divalent aromatic radical and H is an aromatically bound hydrogen atom, which compound is polymerizable with the at least one dicarboxylic acid of (i); (b) at least one aromatic monocarboxylic acid H--Ar"--CO.sub.2 H where --Ar"-- is a divalent aromatic radical and H and CO.sub.2 H are as defined in (a), which monocarboxylic acid is self-polymerizable; and (c) a combination of (a) and (b).

## Claims

### Claim 1

A process for the production of an aromatic polyketone which comprises reacting at a temperature of from 40.degree. to 200.degree. C. in the presence of a quinquevalent phosphorous halide and a fluoroalkane sulphonic acid the reactants selected from the group consisting of:
(a) a mixture of equimolar quantities of
(i) at least one aromatic dicarboxylic acid of formula
HO.sub.2 C--Ar--Co.sub.2 H
where --Ar-- is a divalent aromatic radical and Co.sub.2 H is an aromatically bound carboxylic acid group, which acid is polymerisable with the at least one aromatic compound of (a)(ii),
(ii) at least one aromatic compound of formula
H--Ar'--H
where --Ar'-- is a divalent aromatic radical and H is an aromatically bound hydrogen atom, which compound is polymerisable with the at least one aromatic dicarboxylic acid of (a)(i),
(b) at least one aromatic monocarboxylic acid of formula
H--Ar"--CO.sub.2 H
where --Ar"-- is a divalent aromatic radical and H is an aromatically bound hydrogen atom and CO.sub.2 H is an aromatically bound carboxylic acid group, which acid is self-polymerisable, and
(c) a combination of (a) and (b) said process being carried out with at least as many moles of phosphorous halide being used as are the number of moles of CO.sub.2 H groups used.

### Claim 2 (depends on 1)

A process according to claim 1 wherein the fluoroalkane sulphonic acid used is trifluoromethane sulphonic acid or difluoromethane sulphonic acid.

### Claim 3 (depends on 1)

A process according to claim 1 wherein the amount of the fluoroalkane sulphonic acid used is such that the fluoroalkane sulphonic acid acts as a reaction solvent.

### Claim 4 (depends on 1)

A process according to claim 1 wherein substantially equimolar quantities of phosphorous halide and CO.sub.2 H groups are employed.

### Claim 5 (depends on 1)

A process according to claim 1 wherein the phosphorous halide is phosphorous pentachloride or phosphorous pentabromide.

### Claim 6 (depends on 1)

A process according to claim 1 wherein the at least one aromatic dicarboxylic acid of (a)(i) is selected from the group consisting of: ##STR14## where --Y-- is a direct link, --O--, --S--, --CO--, --SO.sub.2 --, --C(CF.sub.3).sub.2 --, or ##STR15## where n is 1 or 2, m is 1 or 2, k is 0 or 1, --X-- and --X'-- which may be the same or different are each a direct link, --O--, --S--, --CO--, --SO.sub.2 --, or --C(CF.sub.3).sub.2 --, and --Z-- is --CO--, --SO.sub.2 --, or --C(CF.sub.3).sub.2 --.

### Claim 7 (depends on 6)

A process according to claim 6 wherein the at least one aromatic dicarboxylic acid is selected from the group consisting of: ##STR16##

### Claim 8 (depends on 1)

A process according to claim 1 wherein the at least one aromatic compound of (a)(ii) is selected from the group consisting of: ##STR17## where --E-- is a direct link, --O--, --S--, or ##STR18## where x is 1 or 2, y is 1 or 2, z is 0 or 1, --G-- and --G'-- which may be the same or different are each a direct link, --O--, or --S--, and --J-- is --CO--, --SO.sub.2 --, or --C(CF.sub.3).sub.2 --.

### Claim 9 (depends on 1)

A process according to claim 1 wherein the at least one aromatic monocarboxyclic acid of (b) is selected from the group consisting of: ##STR19## where --L-- is a direct link, --O--, --S--, or ##STR20## where p is 1 or 2, q is 1 or 2, r is 0 or 1, --R-- is a direct link, --O--, or --S--, --R'-- is a direct link, --O--, --S--, --CO--, --SO.sub.2 --, or --C(CF.sub.3).sub.2 --, and --Q-- is --CO--, --SO.sub.2 -- or C(CF.sub.3).sub.2.

### Claim 10 (depends on 9)

A process according to claim 9 wherein the at least one aromatic monocarboxylic acid is selected from the group consisting of: ##STR21##