4.5 Article

Trichloroacetic acid fueled practical amine purifications

Journal

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 18, Issue -, Pages 225-231

Publisher

BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.18.26

Keywords

amines; decarboxylation; eco-compatible; out of equilibrium; purification

Funding

  1. Excellence Initiative of Aix-Marseille University A*Midex, a French Investissements d'Avenir programme [A-M-AAP-EI-17-06-170223-13.06-QUINTARD-SAT]
  2. Centre National de la Recherche Scientifique (CNRS)
  3. AixMarseille Universite

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This study presents a purification technique for amines by triggering their salt formation with trichloroacetic acid (TCA) and subsequently liberating pure amines through decarboxylation, reducing the number of operations and waste generation.
Amine purification have for long been dominated by tedious stepwise processes involving the generation of large amounts of undesired waste. Inspired by recent work on out of equilibrium molecular machinery, using trichloroacetic acid (TCA), we disclose a purification technique considerably decreasing the number of operations and the waste generation required for such purifications. At first, TCA triggers the precipitation of the amines through their protonated salt formation, enabling the separation with the impurities. From these amine salts, simple decarboxylation of TCA liberates volatile CO2 and chloroform affording directly the pure amines. Through this approach, a broad range of diversely substituted amines could be isolated with success.

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