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Trichloroacetic acid fueled practical amine purifications.

ABSTRACT: 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.

SUBMITTER: Thomas A

PROVIDER: S-EPMC8895030 | biostudies-literature | 2022

REPOSITORIES: biostudies-literature

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Trichloroacetic acid fueled practical amine purifications.

Thomas Aleena A Gasch Baptiste B Olivieri Enzo E Quintard Adrien A

Beilstein journal of organic chemistry 20220224

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 separa ...[more]

PMID: 35280955

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Project description:ImportanceDespite their great potential, medium and deep trichloroacetic acid peels are underused in light-skinned patients and are rarely used in darker-skinned patients because of the widespread fear of pigmentary complications and scarring. This concern has led many physicians to opt for the use of lighter types of peels (glycolic acid peel, Jessner peel, etc) and different lasers and intense light technologies. Trichloroacetic acid peels have been described in numerous publications. However, no study to date has described the precise technique and the practical pearls of a successful trichloroacetic acid peel approach in a clear, detailed, and reproducible manner.ObjectivesTo clarify a practical approach to a universal trichloroacetic acid peel and to offer novice and experienced facial plastic surgeons an organized, easy, and safe technique for medium and deep trichloroacetic acid peels.Design, setting, and participantsThis study was a case series of universal trichloroacetic acid peels in an academic setting. The study dates were January 1, 1996, to November 1, 2015.Main outcomes and methodsThis article discusses the preoperative evaluation for a chemical peel, a previously published genetico-racial skin classification, and the trichloroacetic acid peel technique, which aims at standardizing and controlling the application of the acid to improve results and lessen complications. The "strip" technique is described, which increases the physician's control over the peel depth.ResultsA total of 923 trichloroacetic acid peels in 803 female patients (87.0%) and 120 male patients (13.0%) were reviewed (mean age, 41.59 years). The follow-up period ranged from 6 months to 13 years (mean, 13 months). This case series revealed a low incidence of complications, including 54 patients (5.9%) with persistent hyperpigmentation, 3 patients (0.3%) with mild telangiectasia, 2 patients (0.2%) with acute herpesvirus infection, 2 patients (0.2%) with bacterial Staphylococcus infection, and 1 patient (0.1%) with hypopigmentation.Conclusions and relevanceWhen properly applied, trichloroacetic acid peels are efficient and safe for light and dark skin. The technique can be an easily implementable addition to a physician's cosmetic practice.Level of evidence4.

Project description:Since the coronavirus disease 2019 (COVID-19) pandemic epidemic, the excessive usage of chlorinated disinfectants raised the substantial risks of disinfection by-products (DBPs) exposure. While several technologies may remove the typical carcinogenic DBPs, trichloroacetic acid (TCAA), their application for continuous treatment is limited due to their complexity and expensive or hazardous inputs. In this study, degradation and dechlorination of TCAA induced by an in situ 222 nm KrCl* excimer radiation as well as role of oxygen in the reaction pathway were investigated. Quantum chemical calculation methods were used to help predict the reaction mechanism. Experimental results showed that UV irradiance increased with increasing input power and decreased when the input power exceeded 60 W. Decomposition and dechlorination were simultaneously achieved, where around 78% of TCAA (0.62 mM) can be eliminated and 78% dechlorination within 200 min. Dissolved oxygen showed little effect on the TCAA degradation but greatly boosted the dechlorination as it can additionally generate hydroxyl radical (•OH) in the reaction process. Computational results showed that under 222 nm irradiation, TCAA was excited from S0 to S1 state and then decayed by internal crossing process to T1 state, and a reaction without potential energy barrier followed, resulting in the breaking of C-Cl bond and finally returning to S0 state. Subsequent C-Cl bond cleavage occurred by a barrierless •OH insertion and HCl elimination (27.9 kcal/mol). Finally, the •OH attacked (14.6 kcal/mol) the intermediate byproducts, leading to complete dechlorination and decomposition. The KrCl* excimer radiation has obvious advantages in terms of energy efficiency compared to other competitive methods. These results provide insight into the mechanisms of TCAA dechlorination and decomposition under KrCl* excimer radiation, as well as important information for guiding research toward direct and indirect photolysis of halogenated DBPs.

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Trichloroacetic acid fueled practical amine purifications.

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Trichloroacetic acid fueled practical amine purifications.

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