TY - JOUR

T1 - Tetrabutylammonium prolinate-based ionic liquids

T2 - A combined asymmetric catalysis, antimicrobial toxicity and biodegradation assessment

AU - Ferlin, Nadege

AU - Courty, Matthieu

AU - Van Nhien, Albert Nguyen

AU - Gatard, Sylvain

AU - Pour, Milan

AU - Quilty, Bríd

AU - Ghavre, Mukund

AU - Haiß, A.

AU - Kümmerer, K.

AU - Gathergood, Nicholas

AU - Bouquillon, Sandrine

N1 - This work was supported by the Fondation du Site Paris Reims (post doctoral fellowship for Nad`ege Ferlin) and the FEDER for material funds. This work was also supported by Enterprise Ireland (EI TD/07/328, Ian Beadham and Mukund Ghave). The antibacterial and antifungal screening was supported by the Czech Science Foundation (project no. P207/10/2048) (Milan Pour, 20 Strains).

PY - 2013/12/28

Y1 - 2013/12/28

N2 - Chiral ionic liquids (CILs) tetrabutylammonium-(S)-prolinate, tetrabutylammonium-(R)-prolinate and tetrabutylammonium trans-4-hydroxy-(S)- prolinate were investigated as chiral additives in the Pd-catalyzed enantioselective hydrogenation of α,β-unsaturated ketones. These CILs were easily prepared in one step from the aminoacid and tetrabutylammonium hydroxide and characterized (NMR, IR, optical rotation, elemental analysis, DSC, viscosity, decomposition temperature). The research strategy was to assess the antimicrobial toxicity (>20 strains) and biodegradability (OECD 301D) of the CILs at the same time as undertaking the asymmetric catalysis study. The Pd-catalyzed enantioselective hydrogenation of the carbon-carbon double bond of α,β-unsaturated ketones under mild conditions (room temperature, 1 atm of H 2) in different solvents with CILs present. The best results were obtained in i-PrOH after 18 hours of reaction with a i-PrOH/IL ratio of 5. While all three CILs have low antimicrobial toxicity to a wide range of bacteria and fungi, tetrabutylammonium-(S)-prolinate, tetrabutylammonium-(R)-prolinate and tetrabutylammonium trans-4-hydroxy-(S)-prolinate did not pass the Closed Bottle biodegradation test.

AB - Chiral ionic liquids (CILs) tetrabutylammonium-(S)-prolinate, tetrabutylammonium-(R)-prolinate and tetrabutylammonium trans-4-hydroxy-(S)- prolinate were investigated as chiral additives in the Pd-catalyzed enantioselective hydrogenation of α,β-unsaturated ketones. These CILs were easily prepared in one step from the aminoacid and tetrabutylammonium hydroxide and characterized (NMR, IR, optical rotation, elemental analysis, DSC, viscosity, decomposition temperature). The research strategy was to assess the antimicrobial toxicity (>20 strains) and biodegradability (OECD 301D) of the CILs at the same time as undertaking the asymmetric catalysis study. The Pd-catalyzed enantioselective hydrogenation of the carbon-carbon double bond of α,β-unsaturated ketones under mild conditions (room temperature, 1 atm of H 2) in different solvents with CILs present. The best results were obtained in i-PrOH after 18 hours of reaction with a i-PrOH/IL ratio of 5. While all three CILs have low antimicrobial toxicity to a wide range of bacteria and fungi, tetrabutylammonium-(S)-prolinate, tetrabutylammonium-(R)-prolinate and tetrabutylammonium trans-4-hydroxy-(S)-prolinate did not pass the Closed Bottle biodegradation test.

KW - Chemistry

KW - Asymmetric catalysis

KW - Carbon-carbon double bonds

KW - Chiral ionic liquids

KW - Closed bottle biodegradation tests

KW - Decomposition temperature

KW - Enantioselective hydrogenation

KW - Tetrabutylammonium hydroxides

KW - Unsaturated ketones

UR - http://www.scopus.com/inward/record.url?scp=84887954290&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/6772485b-68b9-36ba-ae02-e65574096761/

U2 - 10.1039/c3ra43785j

DO - 10.1039/c3ra43785j

M3 - Journal articles

AN - SCOPUS:84887954290

VL - 3

SP - 26241

EP - 26251

JO - RSC Advances

JF - RSC Advances

SN - 2046-2069

IS - 48

ER -