Ionic liquid compound

Patent metadata

Field	Value
Publication number	US-9624248-B2
Application number	US-201414784742-A
Country	US
Kind code	B2
Filing date	Apr 21, 2014
Priority date	Apr 19, 2013
Publication date	Apr 18, 2017
Grant date	Apr 18, 2017

Abstract

The present disclosure provides an ionic liquid compound of Formula (I) and its application in reactions such as alkylation, arylation, acylation, diels alder and oligomerization,

The present disclosure also provides a process for preparing the ionic liquid compound of Formula (I) which involves preparing an ionic salt complex represented by Formula [(NR 1 R 2 R 3 ) i M 1 ] n+ [X j ] n− by mixing an amine represented by Formula NR 1 R 2 R 3 and a metal salt represented by formula M 1 X j ; and mixing the ionic salt complex and a metal salt represented by formula M 2 Y k to obtain the ionic liquid compound.

First claim

The invention claimed is:

1. An ionic liquid compound of Formula (I):

wherein,
NR 1 R 2 R 3 represents an amine,
R 1 , R 2 and R 3 are independently selected from the group consisting of alkyl, aryl and H,
M 1 or M 2 is a metal selected from the group consisting of Al, Fe, Zn, Mn and Mg, Ti, Sn, Pd, Pt, Rh, Cu, Cr, Co, Ce, Ni, Ga, In, Sb, Zr and combinations thereof,
X or Y is selected from the group consisting of halogen, nitrate, sulphate, sulfonate, carbonate, phosphonate and acetate,
‘n’ represents 1 to 4,
‘i’ represents 1 to 6,
‘j’ represents 1 to 4,
‘k’ represents 1 to 4,
‘L’ represents 1 to 7,
M 1 =M 2 or M 1 ≠M 2 , and
X═Y or X≠Y.

2. The ionic liquid compound as claimed in claim 1 , wherein the alkyl group is selected from the group consisting of methyl, ethyl, propyl, butyl and combinations thereof; the aryl group is selected from the group consisting of benzyl, phenyl, substituted benzenes and combinations thereof; and the halogen is selected from the group consisting of F, Cl, Br and I.

3. The ionic liquid compound as claimed in claim 1 , wherein NR 1 R 2 R 3 is a trialkylamine; M 1 or M 2 is a metal selected from the group consisting of Al, Fe, Zn, Mn, Mg, Ti, Sn, Pd, Pt, Rh, Cu, Cr, Co, Ce, Ni, Ga, In, Sb, Zr and combinations thereof; and X or Y is a halogen.

4. A process for the preparation of an ionic liquid compound of Formula (I),

wherein,
NR 1 R 2 R 3 represents an amine,
R 1 , R 2 and R 3 are independently selected from the group consisting of alkyl, aryl and H,
M 1 or M 2 is a metal selected from the group consisting of Al, Fe, Zn, Mn and Mg, Ti, Sn, Pd, Pt, Rh, Cu, Cr, Co, Ce, Ni, Ga, In, Sb, Zr and combinations thereof,
X or Y is selected from the group consisting of halogen, nitrate, sulphate, sulfonate, carbonate, phosphonate and acetate, ‘n’ represents 1 to 4,
‘i’ represents 1 to 6,
‘j’ represents 1 to 4,
‘k’ represents 1 to 4,
‘L’ represents 1 to 7,
M 1 =M 2 or M 1 ≠M 2 , and
X═Y or X≠Y,

said process comprising the following steps:
i. preparing an ionic salt complex precursor represented by Formula [(NR 1 R 2 R 3 ) i M 1 ] n+ [X j ] n− by mixing an amine represented by Formula NR 1 R 2 R 3 and a metal salt represented by formula M 1 X j ; and
ii. mixing the ionic salt complex precursor and a metal salt represented by formula M 2 Y k to obtain the ionic liquid compound.

5. The process as claimed in claim 4 , wherein the step (i) and/or the step (ii) are carried out at a temperature ranging from −20 to 100° C.

6. The process as claimed in claim 4 , wherein the step (i) is carried out in the presence of a solvent selected from the group consisting of ethyl acetate, ethanol, methanol, methyl iso butyl ketone, methyl ethyl ketone, benzene, toluene, dichloromethane and combinations thereof and the step (ii) is carried out in the presence of a solvent selected from the group consisting of benzene, toluene, dichloromethane, methyl iso butyl ketone, methyl ethyl ketone and combinations thereof.

7. The process as claimed in claim 4 , wherein the mole ratio of the amine to the metal salt ranges from 1:0.1 to 1:0.5 and the mole ratio of the ionic salt complex precursor to the metal salt ranges from 1:3 and 1:6.

8. The process as claimed in claim 4 , wherein ionic liquid compound is [(Et 3 N) 3 —Al] 3+ [(AlCl 3 ) 6 Cl 3 ] 3− prepared by mixing triethylamine and AlCl 3 to form ionic salt complex precursor, [(Et 3 N) 3 —Al] 3+ [(Cl) 3 ] 3− , and complexing said ionic salt complex precursor with AlCl 3 .

9. An ionic salt complex precursor represented by Formula (II)

wherein,
NR 1 R 2 R 3 represents an amine,
R 1 , R 2 and R 3 are independently selected from the group consisting of alkyl, aryl and H,
M 1 or M 2 is a metal selected from the group consisting of Al, Fe, Zn, Mn and Mg, Ti, Sn, Pd, Pt, Rh, Cu, Cr, Co, Ce, Ni, Ga, In, Sb, Zr and combinations thereof,
X or Y is selected from the group consisting of halogen, nitrate, sulphate, sulfonate, carbonate, phosphonate and acetate,
‘n’ represents 1 to 4,
‘i’ represents 1 to 6, and
‘j’ represents 1 to 4.

10. A process for preparing an ionic salt complex precursor as claimed in claim 9 comprises mixing an amine represented by Formula NR 1 R 2 R 3 and a metal salt represented by formula M 1 X j .

11. The process as claimed in claim 10 , wherein said ionic salt complex precursor is [(Et 3 N) 3 —Al] 3+ [(Cl) 3 ] 3− prepared by mixing triethylamine and AlCl 3 .

12. A process for conducting at least one reaction selected from the group consisting of alkylation reaction, arylation reaction, acylation reaction, diels alder reaction and oligomerization reaction of at least one compound selected from the group consisting of C 1 to C 20 aliphatic compounds, C 6 to C 8 aromatic compounds and heteroaryl compounds in the presence of an ionic liquid compound represented by formula [(NR 1 R 2 R 3 ) i M 1 ] n+ [(M 2 Y k ) L X j ] n− and at a temperature of 20 to 100° C.,
wherein,
NR 1 R 2 R 3 represents an amine,
R 1 , R 2 and R 3 are independently selected from the group consisting of alkyl, aryl and H,
M 1 or M 2 is a metal selected from the group consisting of Al, Fe, Zn, Mn and Mg, Ti, Sn, Pd, Pt, Rh, Cu, Cr, Co, Ce, Ni, Ga, In, Sb, Zr and combinations thereof,
X or Y is selected from the group consisting of halogen, nitrate, sulphate, sulfonate, carbonate, phosphonate and acetate,
‘n’ represents 1 to 4,
‘i’ represents 1 to 6,
‘j’ represents 1 to 4,
‘k’ represents 1 to 4,
‘L’ represents 1 to 7,
M 1 =M 2 or M 1 ·M 2 , and
X═Y or X≠Y.

13. The process as claimed in claim 11 , wherein said reaction is carried out using at least one reactant selected from the group consisting of olefins, paraffins, alkyl or aryl halides, dialkyl or diaryl sulfates, dialkyl or diaryl carbonates, alcohols, carboxylic acids, esters, thiols and carbenes.

14. The process as claimed in claim 12 , wherein the reactant is olefin or a mixture of olefins having carbon atoms ranging from 2 to 50.

15. The process as claimed in claim 11 , wherein the volume ratio of ionic liquid compound to the compound ranges from 0.01 to 1.5.

16. The process as claimed in claim 11 , includes a step of recovering and recycling of said ionic liquid compound.

17. The process as claimed in claim 11 , wherein said ionic liquid compound is selected from the group consisting of fresh ionic liquid compound, recycled ionic liquid compound and a combination thereof.

18. The process as claimed in claim 11 , wherein said reaction is an alkylation of benzene; said reaction comprises alkylating benzene at a temperature of 20 to 100° C., preferably at 30 to 60° C. and at a pressure ranging from 1 to 10 atmospheres, preferably 1 to 6 atmospheres, in the presence of an ionic liquid compound represented by formula [(NR 1 R 2 R 3 ) i M 1 ] n+ [(M 2 Y k ) L X j ] n− and at least one alkylating agent to obtain linear alkyl benzene.

19. The process as claimed in claim 17 , wherein the alkylating agent is a mixture of at least one C 2 to C 50 , preferably C 10 to C 14 , olefin and at le

Assignees

• Reliance Ind Ltd

Inventors

• Aduri Pavankumar
• Uppara Parasu Veera
• Kotra Viswanath
• Sakhalkar Mangesh
• Dukhande Vibhuti

Classifications

• C07C67/293

  by isomerisation; by change of size of the carbon skeleton · CPC title

• B01J31/0298

  the ionic liquids being characterised by the counter-anions · CPC title

• C01F7/00

  Compounds of aluminium · CPC title

• B01J2231/20

  Olefin oligomerisation or telomerisation · CPC title

• C07C2527/125

  Compounds comprising a halogen and scandium, yttrium, aluminium, gallium, indium or thallium · CPC title