Ionic liquid composition

Patent metadata

Field	Value
Publication number	US-2016107972-A1
Application number	US-201414787963-A
Country	US
Kind code	A1
Filing date	Apr 25, 2014
Priority date	May 14, 2013
Publication date	Apr 21, 2016
Grant date	—

Abstract

The present disclosure provides a composition for preparing aryl carboxylic acid; said composition comprising: at least one ionic liquid, at least one catalyst, at least one non-oxidizable polar solvent, and at least one oxidizable multi-alkylated arylene compound with no two successive ring positions bearing alkyl group. The present disclosure also provides a process for preparing aryl carboxylic acid.

First claim

1 . A composition for preparing aryl carboxylic acid; said composition comprising:
i. at least one ionic liquid of formula I, in an amount of 0.05 to 50% of the total mass of the composition;
[Ar—Z-Q {circle around (+)} -R]A {circle around (−)}   Formula I

wherein,
Ar is substituted or un-substituted aryl group,
Z is (CH 2 ) n , wherein n is an integer from 0 to 10,
Q + is an organic cation selected from the group consisting of quaternary ammonium, cholinium, sulfonium, phosphonium, guanidinium, imidazolium, pyridinium, pyrrolidinium, morpholinium, quinolinium, isoquinolium, pyrazolium and piperidinium;
R is C 1 to C 20 linear or branched alkyl group or Ar—Z,
A − is an anion selected from the group consisting of chlorides, bromides, fluorides, iodides, mesylates, tosylates, sulfates, alkyl sulfonates, phosphates, phosphonates, akyl phosphates, nitrates, nitrites, carbonates, acetates, bicarbonates, hydroxides and oxides;
ii. at least one catalyst, in an amount of 0.01 to 5% of the total mass of the composition; iii. at least one non-oxidizable polar solvent; and iv. at least one oxidizable multi-alkylated arylene compound with no two successive ring positions bearing alkyl group, said composition when used in the preparation of aryl carboxylic acid results in the formation of less than 4000 ppm of partially oxidized derivatives of said multi-alkylated arylene compound; said derivatives comprising at least one carboxylic acid moiety and at least one aldehyde moiety.

2 . The composition as claimed in claim 1 , wherein the proportion of the ionic liquid to the non-oxidizable polar solvent ranges between 1:1 and 1:20.

3 . The composition as claimed in claim 1 , wherein the catalyst comprises at least one metal compound, the metal being selected from the group consisting of cobalt, magnesium, chromium, copper, nickel, vanadium, iron, molybdenum, tin, cerium, zirconium, cesium and titanium.

4 . The composition as claimed in claim 1 , wherein the catalyst is at least one selected from the group consisting of cobalt acetate, manganese acetate, cerium acetate, potassium acetate, cesium acetate, zirconium acetate, copper acetate, cobalt oxalate, manganese oxalate, cerium oxalate, potassium oxalate, cesium oxalate, zirconium oxalate and copper oxalate.

5 . The composition as claimed in claim 1 , wherein the non-oxidizable polar solvent is at least one solvent selected from the group consisting of acetic acid, methyl acetate, ethyl acetate, propyl acetate, benzyl acetate and water.

6 . The composition as claimed in claim 1 , wherein Ar is phenyl, Z is (CH 2 ) n , wherein n is 1, Q + is imidazolium group, R is methyl, and A − is bromide.

7 . The composition as claimed in claim 1 , further comprises at least one bromine source selected from the group consisting of HBr, NaBr, KBr, NH 4 Br, benzylbromide, monobromoacetic acid, di-bromo acetic acid, bromoacetyl bromide, tetrabromomethane and ethylene di-bromide.

8 . The composition as claimed in claim 1 , further comprises at least one mono alkyl ionic liquid comprising an organic cation selected from the group consisting of quaternary ammonium, cholinium, sulfonium, phosphonium, guanidinium, imidazolium, pyridinium, pyrrolidinium, morpholinium, quinolinium, isoquinolium, pyrazolium and piperidinium; and an anion selected from the group consisting of chlorides, bromides, fluorides, iodides, mesylates, tosylates, sulfates, alkyl sulfonates, phosphates, phosphonates, akyl phosphates, nitrates, nitrites, carbonates, acetates, bicarbonates, hydroxides and oxides.

9 . The composition as claimed in claim 1 , wherein the aryl carboxylic acid is at least one compound selected from the group consisting of terephthalic acid, isophthalic acid, p-toluic acid, m-toluic acid, 4-formyl benzoic acid, 3-formyl benzoic acid, Naphthoic acid, Trimesic acid, benzoic acid and substituted benzoic acid.

10 . The composition as claimed in claim 1 , wherein the oxidizable multi-alkylated arylene compound is at least one selected from the group consisting of para-xylene, meta-xylene, methylnaphthalene, mesitylene, toluene and substituted toluene.

11 . The composition as claimed in claim 1 , wherein the partially oxidized derivative is at least one selected from the group consisting of 4-carboxy benzaldehyde, 3-carboxy benzaldehyde, p-tolualdehyde, m-tolualdehyde, naphthalenecarboxaldehyde, 1,5-dicarboxilic, 3-formyl-benzene, benzaldehyde and substituted benzaldehyde.

12 . The composition as claimed in claim 1 , wherein the oxidizable multi-alkylated arylene compound is para-xylene, the non-oxidizable polar solvent is acetic acid, the partially oxidized derivative is 4-carboxy benzaldehyde and the aryl carboxylic acid is terephthalic acid.

13 . A process for obtaining aryl carboxylic acid; said process comprising the following steps:
preparing a composition comprising:
i. at least one ionic liquid of formula I, in an amount of 0.05 to 50% of the total mass of the composition;
[Ar—Z-Q {circle around (+)} -R]A {circle around (−)}   Formula I

wherein,
Ar is substituted or un-substituted aryl group,
Z is (CH 2 ) n , wherein n is an integer from 0 to 10,
Q + is an organic cation selected from the group consisting of quaternary ammonium, cholinium, sulfonium, phosphonium, guanidinium, imidazolium, pyridinium, pyrrolidinium, morpholinium, quinolinium, isoquinolium, pyrazolium and piperidinium;
R is C 1 to C 20 linear or branched alkyl group or Ar—Z,
A − is an anion selected from the group consisting of chlorides, bromides, fluorides, iodides, mesylates, tosylates, sulfates, alkyl sulfonatses, phosphates, phosphonates, akyl phosphates, nitrates, nitrites, carbonates, acetates, bicarbonates, hydroxides and oxides;

ii. at least one catalyst, in an amount of 0.01 to 5% of the total mass of the composition;
iii. at least one non-oxidizable polar solvent; and
iv. at least one oxidizable multi-alkylated arylene compound with no two successive ring positions bearing alkyl group, and
subjecting said composition to oxidation in the presence of an oxidizing agent selected from the group consisting of air and oxygen at a temperature of 100 to 250° C. and at a pressure of 10 to 60 bar to obtain aryl carboxylic acid,
said process resulting in the formation of less than 4000 ppm of partially oxidized derivatives of said multi-alkylated arylene compound; said derivatives comprising at least one carboxylic acid moiety and at least one aldehyde moiety.

14 . The process as claimed in claim 13 , wherein said process is characterized by reduction in the thermo-oxidative loss of the ionic compound.

15 . The process as claimed in claim 13 , wherein said process is characterized in that the oxidation is carried out in a continuous manner for a time period of at least 6 hours without the need of replenishment of the ionic compound.

16 . The process as claimed in claim 13 , further comprises a step of separating and recycling the ionic compound, the carboxylic acid solvent and the catalyst.

Assignees

• Reliance Ind Ltd

Inventors

• Jain Suresh Shantilal
• Aduri Pavankumar
• Ratnaparkhi Uday
• Uppara Parasu Veera

Classifications

• C07C51/265 Primary

  having alkyl side chains which are oxidised to carboxyl groups · CPC title