Organoindate Room Temperature Ionic Liquid: Synthesis, Physicochemical Properties and Application

Brenno A. da Silveira Neto; Gunter Ebeling; Reinaldo S. Gonçalves; Fabio C. Gozzo; Marcos N. Eberlin; Jairton Dupont

doi:10.1055/s-2004-822372

PAPER

Organoindate Room Temperature Ionic Liquid: Synthesis, Physicochemical Properties and Application

Brenno A. da Silveira Neto^a, Gunter Ebeling^a, Reinaldo S. Gonçalves^a, Fabio C. Gozzo^b, Marcos N. Eberlin*^b, Jairton Dupont*^a
^a Laboratory of Molecular Catalysis, Institute of Chemistry - UFRGS, Av. Bento Gonçalves, 9500 Porto Alegre, 91501-970 RS Brazil
Fax: +55(51)33167304; e-Mail: dupont@iq.ufrgs.br;
^b Thomson Mass Spectrometry Laboratory - Institute of Chemistry , State University of Campinas - UNICAMP, 13083-970 Campinas, SP Brazil

Abstract

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Abstract

The combination of equimolar amounts of solid 1-n-butyl-3-methylimidazolum chloride (BMI·Cl) with solid indium trichloride affords the new room temperature and air stable ionic liquid BMI·InCl₄ (mp -6 °C). The major physicochemical properties (density, viscosity, electrical conductivity and electrochemical window) of BMI·InCl₄ are complementary to those of classical tetrafluoroborate or hexafluorophosphate analogues. However, this liquid possesses similar Lewis acidity properties to those of organoaluminate melts and can be used as recyclable media, as demonstrated here for the tetrahydropyranylation of alcohols.

Key words

organoindate - ionic liquid - physicochemical properties - Lewis acid catalysis - tetrahydropyranylation - electrospray ionization mass spectrometry

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References

1 For a recent review, see: Dupont J. de Souza RF. Suarez PAZ. Chem. Rev. 2002, 102: 3667

See for example:

2a Fannin AA. Floreani DA. King LA. Landers JS. Piersma BJ. Stech DJ. Vaughn RL. Wilkes JS. Williams JL. J. Phys. Chem. 1984, 88: 2614

2b Hussey CL. In Advances in Molten Salts Chemistry Vol. 5: Mamantov G. Mamantov C. Elsevier; New York: 1983. p.185

3 Wilkes JS. Levisky JA. Wilson RA. Hussey CL. Inorg. Chem. 1982, 21: 1263

4a Smith GP. Dworkin AS. Pagni RM. Zingg SP. J. Am. Chem. Soc. 1989, 111: 525

4b Smith GP. Dworkin AS. Pagni RM. Zingg SP. J. Am. Chem. Soc. 1989, 111: 5075

4c Riechel TL. Wilkes JS. J. Electrochem. Soc. 1993, 140: 3104

Recent examples:

5a Stenzel O. Brull R. Wahner UM. Sanderson RD. Raubenheimer HG. J. Mol. Catal. A: Chem. 2003, 192: 217

5b Qiao K. Deng YQ. J. Mol. Catal. A: Chem. 2001, 171: 81

5c Deng YQ. Shi F. Beng JJ. Qiao K. J. Mol. Catal. A: Chem. 2001, 165: 33

5d Kumar A. Pawar SS. J. Mol. Catal. A: Chem. 2003, in press

5e DeCastro C. Sauvage E. Valkenberg MH. Holderich WF. J. Catal. 2000, 196: 86

6 Dupont J. Suarez PAZ. Consorti CS. de Souza RF. Org. Synth. 2002, 79: 236

7a For previous phase diagram studies (DSC) for the mixture of 1-n-butyl-3-methylimidazolium chloride with InCl₃, see: Tian P. Yang JZ. Xu WG. Zhang P. Song XM. Liang ZD. Chin. Chem. Lett. 2002, 13: 1061 ; Chem. Abstr. 2002, 16997j

7b For a mixture of 1-n-ethyl-3-methylimidazolium chloride and InCl₃, see: Yang JZ. Tian P. He LL. Xu WG. Fluid Phase Equil. 2003, 204: 295

8 Suarez PAZ. Einloft S. Dullius JEL. de Souza RF. Dupont J. J. Chim. Phys. Phys.-Chim. Biol. 1998, 95: 1626

9 Blanchard LA. Brennecke JF. Ind. Eng. Chem. Res. 2001, 40: 287

10a Tait S. Osteryoung RA. Inorg. Chem. 1984, 23: 4352

10b Dieter MK. Dymek CJ. Heimer NE. Rovang JW. Wilkes JS. J. Am. Chem. Soc. 1988, 110: 2722

11 Elawi A. Hitchcock PB. Seddon KR. Srinivasan N. Tan YM. Welton T. Zora JA. J. Chem. Soc., Dalton Trans. 1995, 3467

12 Suarez PAZ. Dullius JEL. Einloft S. deSouza RF. Dupont J. Polyhedron 1996, 15: 1217

13a Cooks RG. Zhang DX. Koch KJ. Gozzo FC. Eberlin MN. Anal. Chem. 2001, 73: 3646

13b Koch KJ. Gozzo FC. Nanita SC. Takats Z. Eberlin MN. Cooks RG. Angew. Chem. Int. Ed. 2002, 41: 1721

13c Meurer EC. Sabino AA. Eberlin MN. Anal. Chem. 2003, 75: 4701

13d

Gozzo, F. C.; Consorti, C. S.; Dupont, J.; Eberlin, M. N. Chem.-Eur. J.; 2003, submitted.

14

Previous Raman scattering and ab initio calculations also indicated that InCl₄ ^- is the predominant anion in melts resulting from the combination of 1-n-butyl-3-methyl imidazolium chloride with InCl₃ (see Ref. [7] ).

15 Carpenter MK. Verbrugge MW. J. Mater. Res. 1994, 9: 2584

16 Suarez PAZ. Selbach VM. Dullius JEL. Einloft S. Piatnicki CMS. Azambuja DS. de Souza RF. Dupont J. Electrochim. Acta 1997, 42: 2533

17 Wilkes JS. Zaworotko MJ. J. Chem. Soc., Chem. Commun. 1992, 965

For reactions promoted by indium compounds immobilized in ionic liquids, see:

18a Yadav JS. Reddy BVS. Gnaneshwar D. New J. Chem. 2003, 27: 202

18b Gordon CM. Ritchie C. Green Chem. 2002, 4: 124

18c Yadav JS. Reddy BVS. Bhaishya G. Green Chem. 2003, 5: 264

18d Chen SL. Ji SJ. Loh TP. Tetrahedron Lett. 2003, 44: 2405