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Synthesis 2004(8): 1155-1158  
DOI: 10.1055/s-2004-822372
PAPER
© Georg Thieme Verlag Stuttgart · New York

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

Brenno A. da Silveira Netoa, Gunter Ebelinga, Reinaldo S. Gonçalvesa, Fabio C. Gozzob, 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
Further Information

Publication History

Received 29 December 2003
Publication Date:
10 May 2004 (online)

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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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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] ).