NDLI: Efficient, halide free synthesis of new, low cost ionic liquids: 1,3-dialkylimidazolium salts containing methyl- and ethyl-sulfate anions

Content Provider	Royal Society of Chemistry (RSC)
Author	Swatloski, Richard P. Broker, Grant A. Seddon, Kenneth R. Rogers, Robin D. Holbrey, John D. Pitner, William R. Reichert, W. Matthew
Copyright Year	2002
Abstract	New low-cost ionic liquids containing methyl- and ethyl-sulfate anions can be easily and efficiently prepared under ambient conditions by the reaction of 1-alkylimidazoles with dimethyl sulfate and diethyl sulfate. The preparation and characterization of a series of 1,3-dialkylimidazolium alkyl sulfate and 1,2,3-trialkylimidazolium alkyl sulfate salts are reported. 1,3-Dialkylimidazolium salts containing at least one non-methyl N-alkyl substituent are liquids at, or below room, temperature. Three salts were crystalline at room temperature, the single crystal X-ray structure of 1,3-dimethylimidazolium methyl sulfate was determined and shows the formation of discrete ribbons comprising of two anion–cation hydrogen-bonded chains linked via intra-chain hydrogen-bonding, but little, or no inter-ribbon hydrogen-bonding. The salts are stable, water soluble, inherently ‘chloride-free’, display an electrochemical window of greater than 4 V, and can be used as alternatives to the corresponding halide salts in metathesis reactions to prepare other ionic liquids including 1-butyl-3-methylimidazolium hexafluorophosphate.
Starting Page	407
Ending Page	413
Page Count	7
File Format	HTM / HTML PDF
ISSN	14639262
Volume Number	4
Issue Number	5
Journal	Green Chemistry
DOI	10.1039/b204469b
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Dimethyl sulfate Diethyl sulfate Alkyl Sulfate Substituent X-ray crystallography Methyl bisulfate Electrochemical window Halide Salt metathesis reaction 1-Butyl-3-methylimidazolium hexafluorophosphate
Content Type	Text
Resource Type	Article
Subject	Environmental Chemistry Pollution

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