Synthesis of amides from acid chlorides and amines in the bio-based solvent Cyrene™

Thomas W. Bousfield, Katharine P. R. Pearce, Simbarashe B. Nyamini, Athanasios Angelis-Dimakis, Jason Camp

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Cyrene™ as a bio-alternative dipolar aprotic solvent: a waste minimizing and molar efficient protocol for the synthesis of amides from acid chlorides and primary amines in the bio-available solvent Cyrene™ is disclosed. This protocol removed the use of toxic solvents, such as dimethylformamide and dichloromethane. A simple aqueous work-up procedure for the removal of the high boiling solvent Cyrene™ resulted in up to a 55-fold increase in molar efficiency (Mol E.%) versus standard operating procedures. In order to rapidly compare the molar efficiency of this process against other methodologies an Excel based Mol. E% calculator was developed that automates many of the calculations. An investigation into the hydration of Cyrene™ found that it readily hydrates to form a geminal diol in the presence of water and that this process is exothermic.
Original languageEnglish
Pages (from-to)3675-3681
Number of pages7
JournalGreen Chemistry
Volume21
Issue number13
Early online date17 Jun 2019
DOIs
Publication statusPublished - 7 Jul 2019

ASJC Scopus subject areas

  • Environmental Chemistry
  • Pollution

Cite this

Bousfield, T. W., Pearce, K. P. R., Nyamini, S. B., Angelis-Dimakis, A., & Camp, J. (2019). Synthesis of amides from acid chlorides and amines in the bio-based solvent Cyrene™. Green Chemistry, 21(13), 3675-3681. https://doi.org/10.1039/C9GC01180C

Synthesis of amides from acid chlorides and amines in the bio-based solvent Cyrene™. / Bousfield, Thomas W.; Pearce, Katharine P. R.; Nyamini, Simbarashe B.; Angelis-Dimakis, Athanasios; Camp, Jason.

In: Green Chemistry, Vol. 21, No. 13, 07.07.2019, p. 3675-3681.

Research output: Contribution to journalArticle

Bousfield, TW, Pearce, KPR, Nyamini, SB, Angelis-Dimakis, A & Camp, J 2019, 'Synthesis of amides from acid chlorides and amines in the bio-based solvent Cyrene™', Green Chemistry, vol. 21, no. 13, pp. 3675-3681. https://doi.org/10.1039/C9GC01180C
Bousfield, Thomas W. ; Pearce, Katharine P. R. ; Nyamini, Simbarashe B. ; Angelis-Dimakis, Athanasios ; Camp, Jason. / Synthesis of amides from acid chlorides and amines in the bio-based solvent Cyrene™. In: Green Chemistry. 2019 ; Vol. 21, No. 13. pp. 3675-3681.
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