Photochemical reactivity of trifluoromethyl aromatic amines: the example of 3,5-diamino-trifluoromethyl-benzene (3,5-DABTF).
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.
Chaignon
Philippe
P
Institut de Chimie des Substances Naturelles, C.N.R.S, Avenue de la Terrasse, 91198, Gif-sur-Yvette cedex, France.
Cortial
Sylvie
S
Guerineau
Vincent
V
Adeline
Marie-Thérèse
MT
Giannotti
Charles
C
Fan
Gérard
G
Ouazzani
Jamal
J
D000588:Amines / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D004867:Equipment Design; D006841:Hydrocarbons, Aromatic / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010655:Phenylenediamines / Q000032:analysis / Q000737:chemistry*; D010777:Photochemistry; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D014867:Water / Q000737:chemistry
C510785:3,5-diaminotrifluoromethylbenzene; D000588:Amines; D006841:Hydrocarbons, Aromatic; D010655:Phenylenediamines; D014867:Water