Organic compounds -- part of the class 532-570 series – Organic compounds – Phosphorus esters
Reexamination Certificate
2011-01-25
2011-01-25
Sullivan, Daniel M (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Phosphorus esters
C558S166000, C558S180000, C558S193000, C564S012000, C568S014000
Reexamination Certificate
active
07875739
ABSTRACT:
Methods and kits for decomposing organophosphorus compounds in non-aqueous media at ambient conditions are described. Insecticides, pesticides, and chemical warfare agents can be quickly decomposed to non-toxic products. The method comprises combining the organophosphorus compound with a non-aqueous solution, preferably an alcohol, comprising metal ions and at least a trace amount of alkoxide ions. In a first preferred embodiment, the metal ion is a lanthanum ion. In a second preferred embodiment, the metal ion is a transition metal.
REFERENCES:
patent: 3079346 (1963-02-01), Jackson
patent: 3725269 (1973-04-01), Wolverton
patent: 5859064 (1999-01-01), Cronce
patent: 7214836 (2007-05-01), Brown et al.
patent: 2004/0096415 (2004-05-01), Franke et al.
patent: 299458 (1992-04-01), None
patent: 0906773 (1999-04-01), None
patent: 0909774 (1999-04-01), None
patent: WO 96/05208 (1996-02-01), None
patent: WO 00/48684 (2000-08-01), None
patent: WO 01/30452 (2001-05-01), None
patent: WO 02/072206 (2002-09-01), None
Yang et al., Decontamination of Chemical Warfare Agents. Chem. Rev. 92:1729-1743, 1992.
Neverov et al., La3+-Catalyzed Methanolysis of Phosphate Diesters. Remarkable Rate Acceleration of the Methanolysis of Diphenyl Phosphate, Methyl p-Nitrophenyl Phosphate, and Bis(p-nitrophenyl) Phosphate, Inorg. Chem.; (Article); 2001; 40(14); 3588-3595.
Yang et al., {Decontamination of Chemical Warfare Agents, Chem. Rev., 1992, 82, 1729-1743}.
Balakrishnan, V.K., et al. “Catalytic Pathways in the Ethanolysis of Fenitrothion, an Organophosphorothioate Pesticide. A Dichotomy in the Behaviour of Crown/Cryptand Cation Complexing Agents”.Can. J. Chem.79: 157-173 (2001).
Bosch, E., et al. “Retention of Ionizable Compounds on HPLC. pH Scale in Methanol-Water and the pKand pH Values of Buffers”.Analytical Chemistry. 68: 3651-3657 (1996).
Bosch, E., et al. “Hammett-Taft and Drago Models in the Prediction of Acidity Constant Values of Neutral and Cationic Acids in Methanol”.J. Chem. Soc., Perkin Trans.2: 1953-1958 (1999).
Brown, R.S., et al. “Hydrolysis of Neutral Phosphate and Phosphonate Esters Catalysed by Co2+-chelates of Tris-imidazolyl Phosphines”.Inorganica Chimica Acta.108: 201-207 (1985).
Brown, R.S., et al. “Acyl and Phosphoryl Transfer to Methanol Promoted by Metal Ions”.J. Chem. Soc., Perkin Trans.2: 1039-1049 (2002).
Brown, R.S., et al. “La3+-Catalyzed Methanolysis of Hydroxypropyl-p-nitrophenyl Phosphate as a Model for the RNA Transesterification Reaction”.39thIUPAC Congress and 86thConference of the Canadian Society for Chemistry. Ottawa, Ontario. Aug. 10-15, 2003 (Abstract).
Buncel, E., et al. “Alkali Metal Ion Catalysis in Nucleophilic Displacement by Ethoxide Ion on p-nitrophenyl Phenylphosphonate: Evidence for Multiple Metal Ion Catalysis”.Can. J. Chem.81: 53-63 (2003).
Clewley, R.G., et al. “Mono and Dinuclear M2+Chelates as Catalysts for the Hydrolysis of Organophosphate Triesters”.Inorganica Chimica Acta.157: 233-238 (1989).
Desloges, W., et al. “Zn2+-Catalyzed Methanolysis of Phosphate Triesters: A Process for Catalytic Degradation of the Organophosphorus Pesticides Paraoxon and Fenitrothion”.Inorganic Chemistry. submitted (2003).
Gans, P., et al. “Investigation of Equilibria in Solution. Determination of Equilibrium Constants with the HYPERQUAD Suite of Programs”.Talanta. 43(10): 1739-1753 (1996).
Gibson, G., et al. “Potentiometric Titration of Metal Ions in Methanol”.Can. J. Chem.81: 495-504 (2003).
Ketelaar, J.A.A., et al. “Metal-catalysed Hydrolysis of Thiophosphoric Esters”.Nature.177: 392-393 (1956).
Khan, A., et al. “Strong Zn2+and Co2+Catalysis of the Methanolysis of Acetyl Imidazole and Acetyl Pyrazole”.Can. J. Chem.77: 1005-1008 (1999).
Nagelkerke, R., et al. “Alkali-metal Ion Catalysis and Inhibition in Nucleophilic Displacement Reactions at Carbon, Phosphorus and Sulfur Centres. IX.p-Nitrophenyl Diphenyl Phosphate”.Org. Biomol. Chem.1: 163-167 (2003).
Neverov, A.A., et al. “Catalysis of the Methanolysis of Acetylimidazole by Lanthanum Triflate”.Can. J. Chem.78: 1247-1250 (2000).
Neverov, A.A., et al. “La3+-Catalyzed Methanolysis of Phosphate Diesters. Remarkable Rate Acceleration of the Methanolysis of Diphenyl Phosphate, Methylp-Nitrophenyl Phosphate, and Bis(p-nitrophenyl) Phosphate”.Inorganic Chemistry. 40: 3588-3595 (2001).
Neverov, A.A., et al. “Catalysis of Transesterification Reactions by Lanthanides—Unprecedented Acceleration of Methanolysis of Aryl and Alkyl Esters Promoted by La(OTf)3at NeutralsspH and Ambient Temperatures”.Can. J. Chem.79: 1704-1710 (2001).
Neverov, A.A., et al. “Catalysis of the Methanolysis of Activated Amides by Divalent and Trivalent Metal Ions. The Effect of Zn2+, Co2+, and La3+on the Methanolysis of Acetylimidazole and Its (NH3)5CoIIIComplex”.J. Am. Chem. Soc.123: 210-217 (2001).
Neverov, A.A., et al. “Europium Ion Catalyzed Methanolysis of Esters at NeutralsspH and Ambient Temperature. Catalytic Involvement of Eu3+(CH3O−)(CH3OH)x”.Inorganic Chemistry. 42: 228-234 (2003).
Okano, T., et al. “Transesterification Catalyzed by Lanthanoid Tri-2-propoxides”.Chemistry Letters. 246-258 (1995).
Rived, F., et al. “Dissociation Constants of Neutral and Charged Acids in Methyl Alcohol. The Acid Strength Resolution”.Analytica Chimica Acta..374: 309-324 (1998).
Tsang, J.S.W., et al. La3+-Catalyzed Methanolysis of Hydropropyl-p-nitrophenyl Phosphate as a Model for the RNA Transesterification Reaction.J. Am. Chem. Soc.125: 1559-1566 (2003).
Tsang, J.S.W., et al. “Billion-fold Acceleration of the Methanolysis of Paraoxon Promoted by La(OTf)3in Methanol”.J. Am. Chem. Soc.125: 7602-7607 (2003).
Yang, Y.-C., et al. “Decontamination of Chemical Warfare Agents”.Chem. Rev.92: 1729-1743 (1992).
Yang, Y.-C., et al. “Chemical Reactions for Neutralizing Chemical Warfare Agents”.Chemistry&Industry(London). 9: 334-337 (1995).
Yang, Y.-C., et al. “Peroxyhydrolysis of Nerve Agent VX and Model Compounds and Related Nucleophilic Reactions”.J. Chem. Soc., Perkin Trans.2: 607-613 (1997).
Yang, Y.-C. “Chemical Detoxification of Nerve Agent VX”.Acc. Chem. Res.32: 109-115 (1999).
Barr, L., et al. “Metallocyclodextrin Catalysts for Hydrolysis of Phosphate Triesters”.Tet. Lett., 43: 7797-7800 (2002).
Bunton, C. A., et al. “Source of Catalysis of Dephosphorylation ofp-nitrophenyldiphenylphosphate by Metallomicelles”.J. Chem. Soc., Perkin Trans.2, 3: 419-425 (1996).
Scrimin, P., et al. “Metallomicelles as Catalysts of the Hydrolysis of Carboxylic and Phosphoric Acid Esters”.J. Org. Chem., 56: 161-166 (1991).
Brown R. Stanley
Neverov Alexei A.
Tsang Josephine S. W.
Lyon Angela
Miernicki Steeg Carol
Nwaonicha Chukwuma O
Queen's University at Kingston
Scribner Stephen J.
LandOfFree
Method of decomposing organophosphorus compounds does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Method of decomposing organophosphorus compounds, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Method of decomposing organophosphorus compounds will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2658853