Zwitterionic Hydrobromic Acid Carriers for the Synthesis of 2-Bromopropionic Acid from Lactide

Kehrer M, Mehler J, Taccardi N, Nagengast J, Kadar J, Collias D, Dziezok P, Wasserscheid P, Albert J (2018)


Publication Language: English

Publication Type: Journal article, Online publication

Publication year: 2018

Journal

Book Volume: 11

Pages Range: 1063 - 1072

Journal Issue: 6

DOI: 10.1002/cssc.201702369

Abstract

A convenient and highly efficient way of synthesizing 2‐bromopropionic acid (2‐BrPA) from lactide is presented. The procedure uses ionic liquids obtained from the addition of HBr to ammonium‐based zwitterions as the solvent and bromination agent. The buffered HBr acidity, high polarity, and charge stabilizing character of the ionic liquid (IL) enable the synthesis of 2‐BrPA with excellent selectivity. The best results are obtained with an imidazolium‐based IL, that is, 1‐(4‐butanesulfonic acid)‐3‐methylimidazolium bromide ([MIMBS]Br). The HBr loading and water content of the IL are crucial parameters for the bromination reaction. The formed 2‐BrPA product can be selectively isolated by extraction from the IL, and the unconverted substrate remains in the [MIMBS]Br IL for the next run. Successful recycling of the IL over four cycles is demonstrated.

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How to cite

APA:

Kehrer, M., Mehler, J., Taccardi, N., Nagengast, J., Kadar, J., Collias, D.,... Albert, J. (2018). Zwitterionic Hydrobromic Acid Carriers for the Synthesis of 2-Bromopropionic Acid from Lactide. ChemSusChem, 11(6), 1063 - 1072. https://dx.doi.org/10.1002/cssc.201702369

MLA:

Kehrer, Matthias, et al. "Zwitterionic Hydrobromic Acid Carriers for the Synthesis of 2-Bromopropionic Acid from Lactide." ChemSusChem 11.6 (2018): 1063 - 1072.

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