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US 8,541,598 B2Granted
Biodegradable solvents for the chemical industry
AssigneeDublin City University
InventorsNick Gathergood, Saibh Morrissey, Bruce Pegot
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AssigneeDublin City University
InventorsNick Gathergood, Saibh Morrissey, Bruce Pegot
Estimating the term…
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.
A compound consisting of an alkyl substituted imidazolium cationic core and an associated counter anion, wherein the imidazolium cationic core has a —C═OX— side chain in the 3-position of the imidazole ring, the —C═OX— side chain comprising a straight alkyl chain and at least one ether linkage, wherein X═O or S.
A compound selected from the group consisting of
A method of improving the biodegradability or reducing the toxicity of an imidazole cation containing ionic liquid wherein the imidazole cation comprises an ester or thioester side chain at the 3-position of the imidazole ring, the side chain comprising a straight chain alkyl group, the method comprising the step of introducing at least one ether group into the side chain.
Dependencies are inferred from the claim text.