Trichloroacetic acid fueled practical amine purifications

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 decreasin...

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Main Authors: Aleena Thomas, Baptiste Gasch, Enzo Olivieri, Adrien Quintard
Format: Article
Language:English
Published: Beilstein-Institut 2022-02-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
Online Access:https://doi.org/10.3762/bjoc.18.26
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author Aleena Thomas
Baptiste Gasch
Enzo Olivieri
Adrien Quintard
author_facet Aleena Thomas
Baptiste Gasch
Enzo Olivieri
Adrien Quintard
author_sort Aleena Thomas
collection DOAJ
description 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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spelling doaj.art-6e0cf9f0f4484a40aa88a074bf01b3c62022-12-21T18:35:55ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972022-02-0118122523110.3762/bjoc.18.261860-5397-18-26Trichloroacetic acid fueled practical amine purificationsAleena Thomas0Baptiste Gasch1Enzo Olivieri2Adrien Quintard3Aix-Marseille Univ, CNRS, Centrale Marseille, iSm2, Marseille, FranceAix-Marseille Univ, CNRS, Centrale Marseille, iSm2, Marseille, FranceAix-Marseille Univ, CNRS, Centrale Marseille, iSm2, Marseille, FranceAix-Marseille Univ, CNRS, Centrale Marseille, iSm2, Marseille, FranceAmine 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.https://doi.org/10.3762/bjoc.18.26aminesdecarboxylationeco-compatibleout of equilibriumpurification
spellingShingle Aleena Thomas
Baptiste Gasch
Enzo Olivieri
Adrien Quintard
Trichloroacetic acid fueled practical amine purifications
Beilstein Journal of Organic Chemistry
amines
decarboxylation
eco-compatible
out of equilibrium
purification
title Trichloroacetic acid fueled practical amine purifications
title_full Trichloroacetic acid fueled practical amine purifications
title_fullStr Trichloroacetic acid fueled practical amine purifications
title_full_unstemmed Trichloroacetic acid fueled practical amine purifications
title_short Trichloroacetic acid fueled practical amine purifications
title_sort trichloroacetic acid fueled practical amine purifications
topic amines
decarboxylation
eco-compatible
out of equilibrium
purification
url https://doi.org/10.3762/bjoc.18.26
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