- Tandem ionic liquid antimicrobial toxicity and asymmetric catalysis study: Carbonyl-ene reactions with trifluoropyruvate
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The asymmetric carbonyl-ene reaction of trifluoropyruvate with five alkenes catalysed by [Pd{(R)-BINAP}](SbF6)2 were carried out in good yields and enantioselectivities (up to 96% yield and 96% ee) in low antimicrobial toxicity C2-substituted imidazolium ionic liquids (ILs). Toxicity data was included in the selection criteria for reaction optimisation after a preliminary IL screen. The Pd(ii) catalyst immobilised in an IL was recycled and reused up to 7 times without decrease of either yield or ee. One IL prepared, which was determined to be of high antimicrobial toxicity was assigned a low priority for future applications.
- Gore, Rohitkumar G.,Truong, Thi-Kim-Thu,Pour, Milan,Myles, Lauren,Connon, Stephen J.,Gathergood, Nicholas
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p. 2727 - 2739
(2013/10/08)
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- Biodegradable, non-bactericidal oxygen-functionalised imidazolium esters: A step towards 'greener' ionic liquids
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A series of imidazolium ionic liquids was prepared and screened against 7 bacterial strains. The incorporation of ether groups into the ester side-chain significantly reduced the toxicity compared with alkyl ester derivatives. Biodegradation data are also presented for 15 of the ionic liquids - including 6 examples which can be classed as readily biodegradable.
- Morrissey, Saibh,Pegot, Bruce,Coleman, Deborah,Garcia, M. Teresa,Ferguson, Damien,Quilty, Brid,Gathergood, Nicholas
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supporting information; experimental part
p. 475 - 483
(2010/04/22)
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- Selective hydrogenation of trans-cinnamaldehyde and hydrogenolysis-free hydrogenation of benzyl cinnamate in imidazolium ILs
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trans-Cinnamaldehyde is selectively hydrogenated to hydrocinnamaldehyde using a commercially available palladium catalyst in novel imidazolium ILs. The selective hydrogenation extends to benzyl cinnamate, in which the ester is protected from hydrogenolysis under similar conditions.
- Morrissey, Saibh,Beadham, Ian,Gathergood, Nicholas
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experimental part
p. 466 - 474
(2010/04/22)
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- BIODEGRADABLE SOLVENTS FOR THE CHEMICAL INDUSTRY
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This invention relates to ionic liquid (ILs) solvents for chemical synthesis based on an alkyl - imidazolium cation core containing ionic liquids which have enhanced biodegradability and reduced toxicity relative to existing imidazolium bases ILs such as 1-butyl-3-methylimidazolium (bmmim) salts. Many of the described ILs produce a score of over 60% biodegradability over 28 days in a biodegradability test such as the Sturm Test, the Closed Bottle Test (OECD 301D) or the CO2 Headspace Test (ISO 14593). The ILs of the invention comprise an alkyl substituted imidazolium cationic core having a -C=OX- side chain in the 3-position of the imidazole ring, wherein X = O, NH, N or S and an associated counteranion characterized in that the -C=OX side chain comprises at least one ether linkage. The biodegradable and non-toxic IL may be used as green solvents for the chemical, pharmaceutical, biofuel and biomass industries. The ILs of the invention are particularly useful in hydrogenation, pericyclic and metathesis reactions.
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Page/Page column 17
(2009/04/25)
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