Basionic Ionic Liquids

Introduction

Sigma-Aldrich is pleased to present the most recent additions to our Ionic Liquids portfolio. In collaboration with BASF AG we now offer BASIONICS™ to our customers worldwide. Primarily based on imidazolium cations, the BASIONICS™ portfolio is classified into standard (ST), acidic (AC), basic(BC), liquid-at-RT(LQ), and low viscosity (VS) products. Their portfolio opens up a broad range of both basic properties of and possible applications for ionic liquids.

Most importantly, the BASIONICS™ portfolio of ionic liquids is a living portfolio! It will be extended based on customer requests. Both the cation and anion of the molecule can be designed to the requirements of the specific customer application. BASF therefore works with the following concept: once you have identified an ionic liquid as suitable for your process or application, the specifications (purity, by-products, halogenide content, colour, viscosity etc.) can be defined in detail. Based on those specifications, the process for the commercial scale production is designed. With their technological expertise, BASF is in a position to make a broad portfolio of ionic liquids available in commercial quantities and at reasonable prices.

All of these products are provided by Sigma-Aldrich up to kg scale. The BASIONICS™ portfolio is available directly from BASF in 100kg or ton scale.

Applications

The sulfamoylation of arenes with N,N-dialkylsulfamoyl chloride in 1-butyl-3-methylimidazolium chloroaluminate ([bmim]Cl·AlCl3) yields near-quantitative conversions at room temperature within 5-30 minutes (Scheme 1).1 Similarly, a fast and efficient protocol was reported for the synthesis of diaryl sulfoxides in [bmim]Cl·AlCl3 by employing arenes and thionyl chloride (Scheme 2). The ionic liquid plays a dual role of Lewis acid catalyst and solvent in this reaction.2

 

 


 

 

Additionally, [bmim]Cl·AlCl3 and [bmim]Cl·AlCl3 have been used in a new approach for the deep desulfurization of diesel oil. In this approach, traces of sulfur compounds that normally are very difficult to remove by common hydrodesulfurization (HDS) techniques could easily be removed by extraction with the ionic liquids, without employing high temperatures and pressures common to HDS.3

The palladium-phosphine-catalyzed Heck arylation of butyl vinyl ether can readily be accomplished in the ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate ([bmim][BF4]), without necessitating aryl triflates or silver and thallium additives. When performed in [bmim][BF4], the arylation proceeds regioselectively, without observed formation of palladium black during the reaction (Scheme 3).4

Ren and Wu have used 1-n-butyl-3-methylimidazolium halides ([bmim][X]) in the conversion of alcohols to alkyl halides in the presence of acids at room temperature. The product is easily extracted or decanted from the reaction mixture (Scheme 4).5

Additionally, 1-butyl-3-methylimidazolium chloride and 1-ethyl-3-methylimidazolium chloride have been shown to be viable solvent systems for dissolving and regenerating silk fibroin,6 and 1-butyl-3-methylimidazolium chloride and 1-butyl-3-methylimidazolium thiocyanate serve as solvents for the dissolution of cellulose.7

 

References
  1. Naik, P. U. et al. Tetrahedron Lett. 2004, 45, 1933.
  2. Mohile, s. S. et al. Tetrahedron Lett. 2003, 44, 1255.
  3. Bössmann, A. Chem. Comm. 2001, 2494.
  4. Xu, L. et al. Org. Lett., 2001, 3, 295.
  5. Ren, R. X. and Wu, J. X. Org. Lett., 2001, 3, 3727.
  6. Phillips, D. M. et al. J. Am. Chem. Soc. 2004, 126, 14350.
  7. Swatloski, R. P. et al. J. Am. Chem. soc. 2002, 124, 4974.

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