Open AccessInvestigation on the Gas-Phase Decomposition of Trichlorfon by GC-MS and Theoretical Calculation
Author(s) -
Kezhi Jiang,
Ningwen Zhang,
Hu Zhang,
Jianmei Wang,
Mingrong Qian
Publication year - 2015
Publication title -
plos one
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.99
H-Index - 332
ISSN - 1932-6203
DOI - 10.1371/journal.pone.0121389
Subject(s) - pyrolytic carbon , chemistry , decomposition , pyrolysis , gas chromatography , intramolecular force , dichlorvos , phosphate , gas chromatography–mass spectrometry , trimethyl phosphate , mass spectrometry , hydrogen atom , gas phase , derivative (finance) , medicinal chemistry , chromatography , organic chemistry , alkyl , pesticide , financial economics , agronomy , economics , biology
The gas phase pyrolysis of trichlorfon was investigated by the on-line gas chromatography – mass spectrometry (GC-MS) pyrolysis and theoretical calculations. Two reaction channels were proposed in the pyrolytic reaction, by analyzing the detected pyrolytic products in the total ion chromatography, including 2,2,2-trichloroacetaldehyde, dimethyl phosphite, and dichlorvos. Theoretical calculations showed that there is an intramolecular hydrogen bond between the hydroxyl group and the phosphate O atom in trichlorfon, through which the hydroxyl H atom can be easily transferred to phosphate O atom to trigger two pyrolytic channels. In path-a, migration of H atom results in direct decomposition of trichlorfon to give 2,2,2-trichloroacetaldehyde and dimethyl phosphite in one step. In path-b, migration of H atom in trichlorfon is combined with formation of the O-P bond to give an intermediate, followed by HCl elimination to afford dichlorvos. Path-a is kinetically more favorable than path-b, which is consistent with the GC-MS results.