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

Thomas Bousfield, Katharine Pearce, Simbarashe Nyamini, Athanasios Angelis-Dimakis, Jason Camp

Research output: Contribution to journalArticle

1 Citation (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

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Amides
Amines
Chlorides
chloride
Acids
acid
Dimethylformamide
Poisons
Methylene Chloride
Dichloromethane
Hydrates
hydration
Hydration
Boiling liquids
fold
methodology
amine
Water
water
protocol

Cite this

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

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

Research output: Contribution to journalArticle

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AB - 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.

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