Using imidazolium-based ionic liquids as dual solvent-catalysts for sustainable synthesis of vitamin esters: inspiration from bio- and organo-catalysis. Tao, Y., Dong, R., Pavlidis, I. V., Chen, B., & Tan, T. Green Chem., The Royal Society of Chemistry, 2016. ![Using imidazolium-based ionic liquids as dual solvent-catalysts for sustainable synthesis of vitamin esters: inspiration from bio- and organo-catalysis [link]](https://bibbase.org/img/filetypes/link.svg "link")
Paper doi abstract bibtex Vitamin E (VE) has significant biological activities and thus its acylation to increase its stability is of extreme interest. We developed an efficient and sustainable approach using imidazolium-based ionic liquids as dual solvent-catalysts for the esterification between [small alpha]-tocopherol (the most active form of VE) and succinic anhydride. Although in literature it is reported that lipase can catalyze this reaction, hereby we demonstrate that the reaction observed in DMSO and DMF is catalyzed by the histidyl residues of the protein. Histidine and its analogue containing an imidazole ring were tested as organocatalysts for the production of [small alpha]-tocopherol succinate. In light of the imidazole organocatalysis, commercially-available 3-alkyl-1-methyl imidazolium ILs [CnC1Im][X-] were investigated as dual solvent-catalysts for the esterification of [small alpha]-tocopherol with succinic anhydride, and provided satisfactory yields and reaction rates. [C5C1Im][NO3-] can be recycled by water extraction, instead of organic solvent extraction to separate [small alpha]-tocopherol succinate from [C5C1Im][NO3-], with an average yield of 94.1% for 4 subsequent batches, while the catalytic activity of the recycled ILs showed almost no loss after 4 batches. The developed protocol for the synthesis of [small alpha]-tocopherol esters and IL recycling bears industrial potential due to the ease of use and the efficient recycling.
@article{C5GC02557E,
abstract = {Vitamin E (VE) has significant biological activities and thus its acylation to increase its stability is of extreme interest. We developed an efficient and sustainable approach using imidazolium-based ionic liquids as dual solvent-catalysts for the esterification between [small alpha]-tocopherol (the most active form of VE) and succinic anhydride. Although in literature it is reported that lipase can catalyze this reaction{,} hereby we demonstrate that the reaction observed in DMSO and DMF is catalyzed by the histidyl residues of the protein. Histidine and its analogue containing an imidazole ring were tested as organocatalysts for the production of [small alpha]-tocopherol succinate. In light of the imidazole organocatalysis{,} commercially-available 3-alkyl-1-methyl imidazolium ILs [CnC1Im][X-] were investigated as dual solvent-catalysts for the esterification of [small alpha]-tocopherol with succinic anhydride{,} and provided satisfactory yields and reaction rates. [C5C1Im][NO3-] can be recycled by water extraction{,} instead of organic solvent extraction to separate [small alpha]-tocopherol succinate from [C5C1Im][NO3-]{,} with an average yield of 94.1% for 4 subsequent batches{,} while the catalytic activity of the recycled ILs showed almost no loss after 4 batches. The developed protocol for the synthesis of [small alpha]-tocopherol esters and IL recycling bears industrial potential due to the ease of use and the efficient recycling.},
added-at = {2016-01-08T20:54:00.000+0100},
author = {Tao, Y. and Dong, R. and Pavlidis, I. V. and Chen, B. and Tan, T.},
biburl = {http://www.bibsonomy.org/bibtex/225986c1fbe683b452d4c484a2430eec0/biochemie},
description = {Using imidazolium-based ionic liquids as dual solvent-catalysts for sustainable synthesis of vitamin esters: inspiration from bio- and organo-catalysis - Green Chemistry (RSC Publishing)},
doi = {10.1039/C5GC02557E},
interhash = {5888dc3e23903de19e02a5f6090e7124},
intrahash = {25986c1fbe683b452d4c484a2430eec0},
journal = {Green Chem.},
keywords = {myown herberg},
publisher = {The Royal Society of Chemistry},
timestamp = {2016-01-08T21:03:58.000+0100},
title = {Using imidazolium-based ionic liquids as dual solvent-catalysts for sustainable synthesis of vitamin esters: inspiration from bio- and organo-catalysis},
url = {http://dx.doi.org/10.1039/C5GC02557E},
volume = {accepted},
year = 2016
}
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We developed an efficient and sustainable approach using imidazolium-based ionic liquids as dual solvent-catalysts for the esterification between [small alpha]-tocopherol (the most active form of VE) and succinic anhydride. Although in literature it is reported that lipase can catalyze this reaction, hereby we demonstrate that the reaction observed in DMSO and DMF is catalyzed by the histidyl residues of the protein. Histidine and its analogue containing an imidazole ring were tested as organocatalysts for the production of [small alpha]-tocopherol succinate. In light of the imidazole organocatalysis, commercially-available 3-alkyl-1-methyl imidazolium ILs [CnC1Im][X-] were investigated as dual solvent-catalysts for the esterification of [small alpha]-tocopherol with succinic anhydride, and provided satisfactory yields and reaction rates. [C5C1Im][NO3-] can be recycled by water extraction, instead of organic solvent extraction to separate [small alpha]-tocopherol succinate from [C5C1Im][NO3-], with an average yield of 94.1% for 4 subsequent batches, while the catalytic activity of the recycled ILs showed almost no loss after 4 batches. 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