Analysis of Thermal Reaction Products of Chlorpyrifos Using LC/MS and GC/MS

Moriwaki, Hiroshi; Sakiyama, Takanori; Yamoto, Yoshinari; Weber, Roland; Behnisch, Peter; Arakawa, Ryuichi; Nakano, Takeshi

doi:10.2116/bunsekikagaku.62.855

Cited by 5 publications

(4 citation statements)

References 4 publications

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“…This agrees with the results of Sakiyama et al, who found higher relative levels of the cis isomer in their products at lower temperatures. Incidentally, Moriwaki et al also indentified structures in their GCMS studies which appear to be the protonated versions of IM4 and IM5 radicals.…”

Section: Resultsmentioning

confidence: 99%

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Mechanism of the Thermal Decomposition of Chlorpyrifos and Formation of the Dioxin Analog, 2,3,7,8-Tetrachloro-1,4-dioxino-dipyridine (TCDDpy)

Kennedy

Mackie

2018

Environ. Sci. Technol.

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Thermal decomposition of the pesticide, chlorpyrifos (CPf) and its major degradation product, 3,5,6-trichloro-2-pyridinol (TCpyol), has been studied by quantum chemical calculation using density functional methods at the M06-2X/GTLarge//M06-2 X/6-31+G(d,p) level of theory. Chlopyrifos was found to undergo a series of unimolecular stepwise elimination reactions releasing two molecules of ethylene and finally HOPOS to form TCpyol. TCpyol underwent oxidative decomposition initiated by abstraction of its phenolic H atom by O. Two phenoxy radicals so produced underwent combination leading to the formation of 2,3,7,8-tetrachloro-[1,4]dioxinodipyridine (TCDDpy). Via Smiles rearrangement both cis and trans TCDDpy are formed. Kinetic models have been constructed to model the decomposition of CPf into TCpyol and of the latter into cis and trans TCDDpy. Modeled results are compared with the experiments of Sakiyama et al. ( Organohalogen Compounds, 2012, 74, 1441-1444).

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Section: Resultsmentioning

confidence: 99%

“…More recently, Moriwaki et al thermally decomposed CPf and studied products by LCMS and GCMS. They established that CPf undergoes a thermal elimination of phosphate and showed that 2,3,7,8-TCDDpy arises from thermal decomposition of CPf.…”

Section: Introductionmentioning

confidence: 99%

Mechanism of the Thermal Decomposition of Chlorpyrifos and Formation of the Dioxin Analog, 2,3,7,8-Tetrachloro-1,4-dioxino-dipyridine (TCDDpy)

Kennedy

Mackie

2018

Environ. Sci. Technol.

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“…The reason might be due to the high hydrophobicity (log Pow 8.88) or highly nucleophilic property of tertiary amine of Nmethyldidecane-1-ylamine. Recently, nucleophilic compounds and hydrophobic compounds have been successfully analyzed by liquid chromatography-tandem mass spectrometry (LC/MS/MS) [9][10][11][12] .…”

Section: N-methyldidecane-1-ylamine Has Been Recognized To Be Harmfulmentioning

confidence: 99%

LC/MS/MS Method for Detection of <i>N</i>-methyldidecane-1-ylamine in Environmental Water

2018

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Summar yA determination method for N-methyldidecane-1-ylamine in environmental water by liquid chromatography tandemmass spectrometry (LC/MS/MS) was developed. The method detection limit (MDL) and method quantification limit (MQL) were 0.00055 µg/L and 0.0014 µg/L, respectively. The average recoveries from river water and sea water were 98% with a relative standard deviation (RSD) of 6.2% and 85% with a RSD of 2.4%, respectively. The concentrations of N-methyldidecane-1-ylamine in rivers and five locations in northern Ise Bay in Nagoya City were below the MDL. The concentrations of N-methyldidecane-1-ylamine added to river water and sea water were almost stable over a three-day preservation period, while the concentrations decreased by 50% after seven days of preservation. In order to discuss the mechanism underlying the aforesaid decrease, the preserved solutions were analyzed by liquid chromatography/high-resolution mass spectrometry. Two compounds were identified as the oxidation products of N-methyldidecane-1-ylamine in the preserved solutions.

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“…Sakiyama et al and Moriwakie et al studied the thermal decomposition and noted that CPF undergoes the thermal elimination of phosphate and forms the 2,3,7,8-tetrachloro-[1,4]dioxinodipyridine (TCDDpy) molecule. The TCDDpy molecule is a nitrogen analogue of the extremely toxic 2,3,7,8-tetrachlorodibenzo-p-dioxin (Moriwaki et al, 2013;Sakiyama, Weber, Behnisch, & Nakano, 2012). Most recently, we developed a potential energy surface (PES) for CPF, TCP and TCDDpy based on quantum chemical techniques.…”

Section: Introductionmentioning

confidence: 99%

Thermal Decomposition of Chlorpyrifos - an Experimental Investigation

Weber¹,

Stockenhuber²,

Dixon³

et al.

Global NEST International Conference on Environmental Science &Amp; Technology

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Organophosphate compounds are a group of chemicals that are commonly used in pest control. One widely used organophosphate is chlorpyrifos (CPF), which has been associated with acetylcholinesterase inhibition (AChE), an acute neurotoxin. Further, under thermal decomposition conditions, such as those that occur in bushfires, CPF has been shown to produce a dioxin-like compound 2,3,7,8-tetrachloro-[1,4]-dioxinodipyridine (TCDDpy). To assist in understanding the reaction of CPF, an experimental methodology was developed which enabled the study of its thermal decomposition. CPF was pyrolysed in a three-zone furnace, leading to the formation of its major degradation product, 3,5,6-trichloro-2-pyridinol (TCP). The study revealed that ethylene gas and a solid sulfur/phosphorous compound were also generated with the TCP product. TCP undergoes further thermal decomposition to form several chlorinated products. Experiments undertaken under oxidative conditions revealed that TCP (at temperatures above 900 K and at a residence time of 9 s) also produced HCl and cis and trans forms of TCDDpy. The results of this study compare favourably with our previous theoretical work.

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Analysis of Thermal Reaction Products of Chlorpyrifos Using LC/MS and GC/MS

Cited by 5 publications

References 4 publications

Mechanism of the Thermal Decomposition of Chlorpyrifos and Formation of the Dioxin Analog, 2,3,7,8-Tetrachloro-1,4-dioxino-dipyridine (TCDDpy)

Mechanism of the Thermal Decomposition of Chlorpyrifos and Formation of the Dioxin Analog, 2,3,7,8-Tetrachloro-1,4-dioxino-dipyridine (TCDDpy)

LC/MS/MS Method for Detection of <i>N</i>-methyldidecane-1-ylamine in Environmental Water

Thermal Decomposition of Chlorpyrifos - an Experimental Investigation

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