Photochemical Reactivity of Trifluoromethyl Aromatic Amines: The Example of 3,5-diamino-trifluoromethyl-benzene (3,5-DABTF)

• Published in: Photochemistry and photobiology 2005-11, Vol.81 (6), p.1539-1543
• Main Authors: Chaignon, Philippe, Cortial, Sylvie, Guerineau, Vincent, Adeline, Marie-Thérèse, Giannotti, Charles, Fan, Gérard, Ouazzani, Jamal
• Format: Article
• Language: English
• Subjects: Amines - chemistry; Chromatography, High Pressure Liquid; Equipment Design; Hydrocarbons, Aromatic - chemistry; Magnetic Resonance Spectroscopy; Molecular Structure; Phenylenediamines - analysis; Phenylenediamines - chemistry; Photochemistry; Research s; Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; Water - chemistry
• ISSN: 0031-8655; 1751-1097; 0031-8655
• DOI: 10.1562/2005-08-03-RA-637

This work presents the application of an on-line photoreactor to the detection of 3,5-diamino-trifluoromethyl-benzene (3,5-DABTF) in aqueous solutions. When irradiated at 310 nm, this compound is defluorinated to 3,5-diaminobenzoic acid by a nucleophilic substitution of the fluoride by water. Concomitantly, defluorination intermediates polymerize through amide bonds to give dark-colored compounds. We take advantage of the photocatalyzed defluorination and the subsequent decrease in pH to develop an original and specific photoreactor. Continuous recording of pH and temperature in the outlet of the reactor by a dual electrode gives us an opportunity to optimize the system. In the photoreactor, 3,5-DABTF is immediately and totally transformed as attested by the rapid drop of the flowing solution pH from 6.2 to 3.2 and the chromatographic analysis of the outgoing solutions. The detection remains effective from 1 to 1000 parts per million.