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Hydrolysis of methylphosphonic anhydride solid to methylphosphonic acid probed by Raman and infrared reflectance spectroscopies

Journal Article · · Analytical Methods
DOI:https://doi.org/10.1039/d1ay00610j· OSTI ID:1827357

Much is still unknown about the mechanisms and rates of environmental degradation of organophosphorous pesticides and agents. In this study we focus on the degradation of one organophosphorous compound, namely solid methyl phosphonic acid anhydride [CH3P(O)OHOP(O)OHCH3, MPAN] and its rate of conversion to methyl phosphonic acid (MPA) via heterogeneous hydrolysis. Pure MPAN was synthesized and loaded in open sample cups placed inside exposure chambers containing saturated salt solutions to control the relative humidity (RH). The reaction was monitored in the sample cup at various times using both infrared hemispherical reflectance (HRF) spectroscopy and Raman spectroscopy. Calibrated HRF and Raman spectra of both pure reagents as well as gravimetrically prepared mixtures were used to quantify the concentrations of MPAN and MPA throughout the reaction. Results show that both HRF and Raman spectroscopies are convenient non-invasive methods for detection of solid chemicals. The MPAN degradation rate displayed a very strong dependence on relative humidity: At room temperature the reaction showed 50% conversion of the MPAN in 761 ± 54 hours at 33% RH, 33 ± 4 hours at 43% RH, 17 ± 2 hours at 54% RH and just 7 ± 1 hours at 75% RH. Although MPAN hydrolysis is a second-order reaction, the 33 and 43% RH data, at early reaction times, could be fit with a zeroth order reaction, indicating water vapor and MPAN concentrations were not initially rate controlling. The 54 and 75% RH experiments showed significant deliquescence and decay data could only be fit assuming multiple reactions, implying chemical and/or physical processes partially controlled the hydrolysis rate, in contrast to a single process at low relative humidity.

Research Organization:
Pacific Northwest National Lab. (PNNL), Richland, WA (United States)
Sponsoring Organization:
USDOE
DOE Contract Number:
AC05-76RL01830
OSTI ID:
1827357
Report Number(s):
PNNL-SA-160396
Journal Information:
Analytical Methods, Vol. 13, Issue 35
Country of Publication:
United States
Language:
English

References (37)

The Chemical Weapons Convention—disarmament, science and technology June 2014
Lists of Chemical Warfare Agents and Precursors from International Nonproliferation Frameworks: Structural Annotation and Chemical Fingerprint Analysis September 2020
Detection of the organophosphorus nerve agent VX and its hydrolysis products in white mustard plants grown in contaminated soil January 2013
Toxicity of the Organophosphate Chemical Warfare Agents GA, GB, and VX: Implications for Public Protection. January 1994
Fate of Chemical Warfare Agents and Toxic Industrial Chemicals in Landfills June 2006
Analysis of the Precursors, Simulants and Degradation Products of Chemical Warfare Agents March 2018
The Rollback of Libya'S Chemical Weapons Program November 2009
Gas-Phase Hydrolysis of SOCl 2 at 297 and 309 K:  Implications for Its Atmospheric Fate August 2003
Hydrolysis of Phosphoryl Trichloride (POCl 3 ): Characterization, in Situ Detection, and Safe Quenching of Energetic Metastable Intermediates August 2010
Impurity Profiling to Match a Nerve Agent to Its Precursor Source for Chemical Forensics Applications December 2011
Stable-carbon isotope ratios for sourcing the nerve-agent precursor methylphosphonic dichloride and its products August 2018
The inhibition of acetylcholinesterase by organophosphorus compounds containing a PCl bond January 1974
In situ Fourier transform infrared spectroscopy as an efficient tool for determination of reaction kinetics October 2002
Raman Spectral Determination of Chemical Reaction Rate Characteristics September 2017
Kinetics of Moisture-Induced Hydrolysis in Powder Blends Stored at and below the Deliquescence Relative Humidity: Investigation of Sucrose−Citric Acid Mixtures October 2010
Quantifying ternary mixtures of different solid-state forms of indomethacin by Raman and near-infrared spectroscopy November 2007
Time-Resolved Infrared Reflectance Studies of the Dehydration-Induced Transformation of Uranyl Nitrate Hexahydrate to the Trihydrate Form August 2015
Organophosphorus chemistry—I January 1972
Quantitative reflectance spectra of solid powders as a function of particle size January 2015
Methods for quantitative infrared directional-hemispherical and diffuse reflectance measurements using an FTIR and a commercial integrating sphere January 2018
Identification of Uranium Minerals in Natural U-Bearing Rocks Using Infrared Reflectance Spectroscopy October 2017
In situ UV/Vis/near-IR diffuse reflection measurement of catalysts at temperatures up to 673 K February 2002
Infrared diffuse reflectance instrumentation and standards at NIST February 1999
Calculations of the Structure and the Vibrational Infrared Frequencies of some Methylphosphonates March 1992
Vibrational analysis of methylphosphonic acid and its anions February 1973
Low-storage Runge-Kutta schemes March 1980
Application of the fourth-order Runge-Kutta method for the solution of high-order general initial value problems December 1993
Quantitative analysis of mannitol polymorphs. FT-Raman spectroscopy June 2002
Variation of Single Particle Mid-Infrared Emission Spectrum with Particle Size January 1972
Modeling thin layers of analytes on substrates for spectral analysis: use of solid/liquid n and k values to model reflectance spectra June 2020
Infrared backscatter imaging spectroscopy of trace analytes at standoff March 2019
A review on analysis methods for nerve agent hydrolysis products December 2019
A treatise on Organophosphate pesticide pollution: Current strategies and advancements in their environmental degradation and elimination January 2021
Prenatal Exposure to Organophosphates, Paraoxonase 1, and Cognitive Development in Childhood August 2011
Neurotoxicity in acute and repeated organophosphate exposure September 2018
The sources, fate, and toxicity of chemical warfare agent degradation products. December 1999
Fate of Nerve Agent Tabun in Concrete and Soil: Evaporation and Decontamination June 2019