Sub-Equimolar Hydrolysis and Condensation of Organophosphates

Alam, Todd M.; Kinnan, Mark K.; Wilson, Brendan W.; Wheeler, David R.

doi:10.1002/slct.201600498

Title: Sub-Equimolar Hydrolysis and Condensation of Organophosphates

Abstract

We characterized the in-situ hydrolysis and subsequent condensation reaction of the chemical agent simulant diethyl chlorophosphate (DECP) by high-resolution 31P NMR spectroscopy following the addition of water in sub-equimolar concentrations. Moreover, the identification and quantification of the multiple pyrophosphate and larger polyphosphate chemical species formed through a series of self-condensation reactions are reported. Finally, the DECP hydrolysis kinetics and distribution of breakdown species was strongly influenced by the water concentration and reaction temperature.

Authors:

Alam, Todd M. ^[1]; Kinnan, Mark K. ^[1]; Wilson, Brendan W. ^[1]; Wheeler, David R. ^[1]

Sandia National Lab. (SNL-NM), Albuquerque, NM (United States)

Publication Date:: Sat Jul 16 00:00:00 EDT 2016

Research Org.:: Sandia National Lab. (SNL-NM), Albuquerque, NM (United States)

Sponsoring Org.:: USDOE National Nuclear Security Administration (NNSA)

OSTI Identifier:: 1303156

Report Number(s):: SAND2016-4563J
Journal ID: ISSN 2365-6549; 640200

Grant/Contract Number:: AC04-94AL85000

Resource Type:: Accepted Manuscript

Journal Name:: Chemistry Select

Additional Journal Information:: Journal Volume: 1; Journal Issue: 11; Journal ID: ISSN 2365-6549

Publisher:: Wiley

Country of Publication:: United States

Language:: English

Subject:: 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats


                    Alam, Todd M., Kinnan, Mark K., Wilson, Brendan W., and Wheeler, David R. Sub-Equimolar Hydrolysis and Condensation of Organophosphates.  United States: N. p., 2016. 
Web.  doi:10.1002/slct.201600498.

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                    Alam, Todd M., Kinnan, Mark K., Wilson, Brendan W., & Wheeler, David R. Sub-Equimolar Hydrolysis and Condensation of Organophosphates.  United States.  https://doi.org/10.1002/slct.201600498

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                    Alam, Todd M., Kinnan, Mark K., Wilson, Brendan W., and Wheeler, David R. Sat .  
"Sub-Equimolar Hydrolysis and Condensation of Organophosphates".  United States.  https://doi.org/10.1002/slct.201600498.  https://www.osti.gov/servlets/purl/1303156.

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@article{osti_1303156,

  title        = {Sub-Equimolar Hydrolysis and Condensation of Organophosphates},

  author       = {Alam, Todd M. and Kinnan, Mark K. and Wilson, Brendan W. and Wheeler, David R.},

  abstractNote = {We characterized the in-situ hydrolysis and subsequent condensation reaction of the chemical agent simulant diethyl chlorophosphate (DECP) by high-resolution 31P NMR spectroscopy following the addition of water in sub-equimolar concentrations. Moreover, the identification and quantification of the multiple pyrophosphate and larger polyphosphate chemical species formed through a series of self-condensation reactions are reported. Finally, the DECP hydrolysis kinetics and distribution of breakdown species was strongly influenced by the water concentration and reaction temperature.},

  doi          = {10.1002/slct.201600498},

  journal      = {Chemistry Select},

  number       = 11,

  volume       = 1,

  place        = {United States},

  year         = {Sat Jul 16 00:00:00 EDT 2016},

  month        = {Sat Jul 16 00:00:00 EDT 2016}

}

Copy to clipboard

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Works referencing / citing this record:

Challenges in Fluorescence Detection of Chemical Warfare Agent Vapors Using Solid‐State Films
journal, November 2019

Fan, Shengqiang; Zhang, Guanran; Dennison, Genevieve H.
Advanced Materials, Vol. 32, Issue 18
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Coordination‐Cage‐Catalysed Hydrolysis of Organophosphates: Cavity‐ or Surface‐Based?
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Taylor, Christopher G. P.; Metherell, Alexander J.; Argent, Stephen P.
Chemistry – A European Journal, Vol. 26, Issue 14
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Efficient MOF-based degradation of organophosphorus compounds in non-aqueous environments
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Spectroscopic and inclusion properties of G-series chemical warfare agents and their simulants: a DFT study
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Sambrook, Mark R.; Gass, Ian A.; Cragg, Peter J.
Supramolecular Chemistry, Vol. 30, Issue 3
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Cover Feature: Coordination‐Cage‐Catalysed Hydrolysis of Organophosphates: Cavity‐ or Surface‐Based? (Chem. Eur. J. 14/2020)
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Taylor, Christopher G. P.; Metherell, Alexander J.; Argent, Stephen P.
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Title: Sub-Equimolar Hydrolysis and Condensation of Organophosphates

Abstract

Citation Formats

The Preparation of Tetraethyl Pyrophosphate and Other Tetraalkyl Pyrophosphates journal, November 1948

Water-Driven Micromotors for Rapid Photocatalytic Degradation of Biological and Chemical Warfare Agents journal, October 2014

A Kinetic Study of the Reaction of isoPropoxy-methyl-phosphoryl Fluoride (Sarin) with Hydrogen Peroxide. journal, January 1958

Decontamination of chemical warfare agents journal, December 1992

US assistance to Russian chemical weapons destruction: Identifying the next steps journal, December 1999

Potential fate of G-nerve chemical warfare agents in the coastal waters of the Arabian Gulf journal, January 1996

Rate of Decomposition of GB in Seawater journal, December 1970

Oxidative detoxification of phosphonothiolates journal, August 1990

Four what ifs? Evaluation of alternative technologies for the destruction of chemical weapons journal, January 2004

Destruction and Detection of Chemical Warfare Agents journal, September 2011

Destruction of chemical warfare agents VX and soman by ?-nucleophiles as oxidizing agents journal, January 2001

A Kinetic Study of the Copper(II) Chelate-catalyzed Hydrolysis of Isopropyl Methylphosphonofluoridate (Sarin) journal, June 1962

The selective phosphylation of ethanolamine journal, March 1967

Detection of sarin hydrolysis products from sarin-like organophosphorus agent-exposed human erythrocytes journal, November 1997

Sarin-like and Soman-like Organophosphorous Agents Activate PLCγ in Rat Brains journal, April 1999

Chemical Detoxification of Nerve Agent VX journal, February 1999

Rapid Nucleophilic/Oxidative Decontamination of Chemical Warfare Agents journal, April 2002

Base-catalyzed hydrolysis of 1,2,2-trimethylpropyl methylphosphonofluoridate—An examination of the saturation effect journal, March 1988

Formation of pyrophosphate-like adducts from nerve agents sarin, soman and cyclosarin in phosphate buffer: Implications for analytical and toxicological investigations journal, January 2011

Destruction of chemical warfare agents using metal–organic frameworks journal, March 2015

Analysis of O-ethyl S-[2-(diisopropylamino)ethyl] methylphosphonothiolate (VX) by capillary column gas chromatography-mass spectrometry. journal, January 1987

Fate and control of nerve chemical warfare agents in the desalination industry of the Arabian-Persian Gulf journal, January 1995

Characterization of equimolar VX–water reaction product by gas chromatography–mass spectrometry journal, June 1998

Autocatalytic Hydrolysis of V-Type Nerve Agents journal, January 1996

Preparation of Tetramethyl Pyrophosphate journal, June 1949

Dual-Function Metal–Organic Framework as a Versatile Catalyst for Detoxifying Chemical Warfare Agent Simulants journal, October 2015

A Nitrogen-to-Oxygen Phosphoryl Migration: Preparation of dl-Serinephosphoric and Threoninephosphoric Acid journal, November 1953

Michaelis-Arbuzov rearrangement journal, August 1981

The Hydrolysis of Dimethylamido-ethoxy-phosphoryl Cyanide (Tabun). journal, January 1953

Update 1 of: Destruction and Detection of Chemical Warfare Agents journal, December 2015

Nerve Agent Degradation with Polyoxoniobates: Nerve Agent Degradation with Polyoxoniobates journal, April 2014

Challenges in Fluorescence Detection of Chemical Warfare Agent Vapors Using Solid‐State Films journal, November 2019

Coordination‐Cage‐Catalysed Hydrolysis of Organophosphates: Cavity‐ or Surface‐Based? journal, February 2020

Efficient MOF-based degradation of organophosphorus compounds in non-aqueous environments journal, January 2018

Spectroscopic and inclusion properties of G-series chemical warfare agents and their simulants: a DFT study journal, November 2017

Cover Feature: Coordination‐Cage‐Catalysed Hydrolysis of Organophosphates: Cavity‐ or Surface‐Based? (Chem. Eur. J. 14/2020) journal, February 2020

Spectroscopic and inclusion properties of G-series chemical warfare agents and their simulants: a DFT study text, January 2017

Spectroscopic and inclusion properties of G-series chemical warfare agents and their simulants: a DFT study text, January 2017

The Preparation of Tetraethyl Pyrophosphate and Other Tetraalkyl Pyrophosphates
journal, November 1948

Water-Driven Micromotors for Rapid Photocatalytic Degradation of Biological and Chemical Warfare Agents
journal, October 2014

A Kinetic Study of the Reaction of isoPropoxy-methyl-phosphoryl Fluoride (Sarin) with Hydrogen Peroxide.
journal, January 1958

Decontamination of chemical warfare agents
journal, December 1992

US assistance to Russian chemical weapons destruction: Identifying the next steps
journal, December 1999

Potential fate of G-nerve chemical warfare agents in the coastal waters of the Arabian Gulf
journal, January 1996

Rate of Decomposition of GB in Seawater
journal, December 1970

Oxidative detoxification of phosphonothiolates
journal, August 1990

Four what ifs? Evaluation of alternative technologies for the destruction of chemical weapons
journal, January 2004

Destruction and Detection of Chemical Warfare Agents
journal, September 2011

Destruction of chemical warfare agents VX and soman by ?-nucleophiles as oxidizing agents
journal, January 2001

A Kinetic Study of the Copper(II) Chelate-catalyzed Hydrolysis of Isopropyl Methylphosphonofluoridate (Sarin)
journal, June 1962

The selective phosphylation of ethanolamine
journal, March 1967

Detection of sarin hydrolysis products from sarin-like organophosphorus agent-exposed human erythrocytes
journal, November 1997

Sarin-like and Soman-like Organophosphorous Agents Activate PLCγ in Rat Brains
journal, April 1999

Chemical Detoxification of Nerve Agent VX
journal, February 1999

Rapid Nucleophilic/Oxidative Decontamination of Chemical Warfare Agents
journal, April 2002

Base-catalyzed hydrolysis of 1,2,2-trimethylpropyl methylphosphonofluoridate—An examination of the saturation effect
journal, March 1988

Formation of pyrophosphate-like adducts from nerve agents sarin, soman and cyclosarin in phosphate buffer: Implications for analytical and toxicological investigations
journal, January 2011

Destruction of chemical warfare agents using metal–organic frameworks
journal, March 2015

Analysis of O-ethyl S-[2-(diisopropylamino)ethyl] methylphosphonothiolate (VX) by capillary column gas chromatography-mass spectrometry.
journal, January 1987

Fate and control of nerve chemical warfare agents in the desalination industry of the Arabian-Persian Gulf
journal, January 1995

Characterization of equimolar VX–water reaction product by gas chromatography–mass spectrometry
journal, June 1998

Autocatalytic Hydrolysis of V-Type Nerve Agents
journal, January 1996

Preparation of Tetramethyl Pyrophosphate
journal, June 1949

Dual-Function Metal–Organic Framework as a Versatile Catalyst for Detoxifying Chemical Warfare Agent Simulants
journal, October 2015

A Nitrogen-to-Oxygen Phosphoryl Migration: Preparation of dl-Serinephosphoric and Threoninephosphoric Acid
journal, November 1953

Michaelis-Arbuzov rearrangement
journal, August 1981

The Hydrolysis of Dimethylamido-ethoxy-phosphoryl Cyanide (Tabun).
journal, January 1953

Update 1 of: Destruction and Detection of Chemical Warfare Agents
journal, December 2015

Nerve Agent Degradation with Polyoxoniobates: Nerve Agent Degradation with Polyoxoniobates
journal, April 2014

Challenges in Fluorescence Detection of Chemical Warfare Agent Vapors Using Solid‐State Films
journal, November 2019

Coordination‐Cage‐Catalysed Hydrolysis of Organophosphates: Cavity‐ or Surface‐Based?
journal, February 2020

Efficient MOF-based degradation of organophosphorus compounds in non-aqueous environments
journal, January 2018

Spectroscopic and inclusion properties of G-series chemical warfare agents and their simulants: a DFT study
journal, November 2017

Cover Feature: Coordination‐Cage‐Catalysed Hydrolysis of Organophosphates: Cavity‐ or Surface‐Based? (Chem. Eur. J. 14/2020)
journal, February 2020

Spectroscopic and inclusion properties of G-series chemical warfare agents and their simulants: a DFT study
text, January 2017

Spectroscopic and inclusion properties of G-series chemical warfare agents and their simulants: a DFT study
text, January 2017