Jump to main content
Jump to site search

Issue 13, 2019
Previous Article Next Article

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

Author affiliations

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.

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

Back to tab navigation

Supplementary files

Publication details

The article was received on 10 Apr 2019, accepted on 11 Jun 2019 and first published on 17 Jun 2019


Article type: Paper
DOI: 10.1039/C9GC01180C
Green Chem., 2019,21, 3675-3681

  •   Request permissions

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

    T. W. Bousfield, K. P. R. Pearce, S. B. Nyamini, A. Angelis-Dimakis and J. E. Camp, Green Chem., 2019, 21, 3675
    DOI: 10.1039/C9GC01180C

Search articles by author

Spotlight

Advertisements