CA2389081A1 - Composition and method for destroying organophosphorous and/or organosulphurous pollutants - Google Patents

Composition and method for destroying organophosphorous and/or organosulphurous pollutants Download PDF

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Publication number
CA2389081A1
CA2389081A1 CA002389081A CA2389081A CA2389081A1 CA 2389081 A1 CA2389081 A1 CA 2389081A1 CA 002389081 A CA002389081 A CA 002389081A CA 2389081 A CA2389081 A CA 2389081A CA 2389081 A1 CA2389081 A1 CA 2389081A1
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CA
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Prior art keywords
acid
percarboxylic
anhydrous
composition according
composition
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Granted
Application number
CA002389081A
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French (fr)
Other versions
CA2389081C (en
Inventor
Jean-Pierre Schirmann
Christian Pralus
Claude Lion
Louis Da Conceicao
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Arkema France SA
Original Assignee
Atofina
Jean-Pierre Schirmann
Christian Pralus
Claude Lion
Louis Da Conceicao
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Publication of CA2389081A1 publication Critical patent/CA2389081A1/en
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Publication of CA2389081C publication Critical patent/CA2389081C/en
Anticipated expiration legal-status Critical
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Classifications

    • A—HUMAN NECESSITIES
    • A62—LIFE-SAVING; FIRE-FIGHTING
    • A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
    • A62D3/00—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances
    • A62D3/30—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances by reacting with chemical agents
    • A62D3/38—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances by reacting with chemical agents by oxidation; by combustion
    • A—HUMAN NECESSITIES
    • A62—LIFE-SAVING; FIRE-FIGHTING
    • A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
    • A62D2101/00—Harmful chemical substances made harmless, or less harmful, by effecting chemical change
    • A62D2101/02—Chemical warfare substances, e.g. cholinesterase inhibitors
    • A—HUMAN NECESSITIES
    • A62—LIFE-SAVING; FIRE-FIGHTING
    • A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
    • A62D2101/00—Harmful chemical substances made harmless, or less harmful, by effecting chemical change
    • A62D2101/04—Pesticides, e.g. insecticides, herbicides, fungicides or nematocides
    • A—HUMAN NECESSITIES
    • A62—LIFE-SAVING; FIRE-FIGHTING
    • A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
    • A62D2101/00—Harmful chemical substances made harmless, or less harmful, by effecting chemical change
    • A62D2101/20—Organic substances
    • A62D2101/22—Organic substances containing halogen
    • A—HUMAN NECESSITIES
    • A62—LIFE-SAVING; FIRE-FIGHTING
    • A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
    • A62D2101/00—Harmful chemical substances made harmless, or less harmful, by effecting chemical change
    • A62D2101/20—Organic substances
    • A62D2101/26—Organic substances containing nitrogen or phosphorus
    • A—HUMAN NECESSITIES
    • A62—LIFE-SAVING; FIRE-FIGHTING
    • A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
    • A62D2101/00—Harmful chemical substances made harmless, or less harmful, by effecting chemical change
    • A62D2101/20—Organic substances
    • A62D2101/28—Organic substances containing oxygen, sulfur, selenium or tellurium, i.e. chalcogen

Abstract

The invention concerns the use of an acid selected among the C2-C4 percarboxylic acids for decontaminating materials soiled by organophosphorous and/or organosulphurous compounds. The percarboxylic acid is in particular in the form of an anhydrous or substantially anhydrous organic solution of said percarboxylic acid, such as is obtained by reacting an aqueous hydrogen peroxide solution with the corresponding carboxylic acid miscible in water, in the presence of a catalyst and an organic solvent optionally the one whereby water has been continuously eliminated from the reaction medium by azeotropic distillation.

Claims (9)

1 - Utilisation d'un acide choisi parmi les acides percarboxyliques en C2 à C4 dans la décontamination de matériaux souillés par des composés organophosphorés et/ou organosoufrés, ledit acide percarboxylique se présentant sous la forme d'une solution organique anhydre ou sensiblement anhydre dudit acide percarboxylique. 1 - Use of an acid chosen from acids C2 to C4 percarboxylic in the decontamination of materials contaminated with organophosphorus compounds and / or organosulfur, said percarboxylic acid occurring under the form of an anhydrous or substantially organic solution anhydrous of said percarboxylic acid. 2 - Utilisation selon la revendication 1, caractérisée par le fait que la solution organique anhydre ou sensiblement anhydre de l'acide percarboxylique est telle qu'elle a été obtenue par réaction d'une solution aqueuse de peroxyde d'hydrogène avec l'acide carboxylique correspondant miscible à l'eau, en présence d'un catalyseur et d'un solvant organique dont éventuellement celui qui a permis l'élimination continue par distillation azéotropique de l'eau du milieu réactionnel. 2 - Use according to claim 1, characterized by the fact that the anhydrous organic solution or substantially anhydrous percarboxylic acid is such that it was obtained by reaction of an aqueous solution of hydrogen peroxide with the corresponding carboxylic acid miscible with water, in the presence of a catalyst and a solvent organic including possibly the one that allowed the elimination continuous by azeotropic distillation of the middle water reactive. 3 - Utilisation selon l'une des revendications 1 et 2, caractérisée par le fait que l'acide percarboxylique est l'acide perpropionique. 3 - Use according to one of claims 1 and 2, characterized in that the percarboxylic acid is perpropionic acid. 4 - Utilisation selon les revendications 2 et 3 prises simultanément, caractérisée par le fait que la solution organique anhydre ou sensiblement anhydre de l'acide perpropionique comprend de l'acide perpropionique, comme produit, de l'acide propionique comme réactif n'ayant pas réagi, du propionate d'éthyle comme solvant, de l'eau oxygénée comme réactif n'ayant pas réagi, de l'acide sulfurique ou de l'acide borique comme catalyseur, et de l'acide dipicolinique comme stabilisant de la solution peracide fabriquée. 4 - Use according to claims 2 and 3 taken simultaneously, characterized in that the solution organic anhydrous or substantially anhydrous acid perpropionic includes perpropionic acid, such as product, propionic acid as a reagent not having reacted, ethyl propionate as solvent, hydrogen peroxide as unreacted reagent, sulfuric acid or boric acid as catalyst, and dipicolinic acid as stabilizer of the manufactured peracid solution. 5 - Composition utilisable pour la décontamination de matériaux souillés par des composés organophosphorés et/ou organosoufrés, caractérisée par le fait qu'elle est constituée par une solution aqueuse à base d'au moins un acide percarboxylique en C2 à C4, le ou les acides percarboxyliques ayant été introduits dans la composition sous la forme d'une solution organique anhydre ou sensiblement anhydre. 5 - Composition usable for decontamination materials contaminated with organophosphorus compounds and / or organosulfur, characterized in that it is made up with an aqueous solution based on at least one acid C2 to C4 percarboxylic, the percarboxylic acid (s) having been introduced into the composition in the form of a anhydrous or substantially anhydrous organic solution. 6 - Composition selon la revendication 5, caractérisée par le fait que le ou les acides percarboxyliques ont été introduits dans la composition sous la forme d'une solution organique anhydre ou sensiblement anhydre dudit acide percarboxylique, telle qu'elle a été
obtenue par réaction d'une solution aqueuse de peroxyde d'hydrogène avec l'acide carboxylique correspondant miscible à l'eau, en présence d'un catalyseur et d'un solvant organique dont éventuellement celui qui a permis l'élimination continue par distillation azéotropique de l'eau du milieu réactionnel. 6 - Composition according to claim 5, characterized by the fact that the acid (s) percarboxylic were introduced into the composition under the form of an anhydrous or substantially organic solution anhydrous of said percarboxylic acid, as it has been obtained by reaction of an aqueous solution of peroxide of hydrogen with the corresponding miscible carboxylic acid with water, in the presence of a catalyst and a solvent organic including possibly the one that allowed the continuous elimination by azeotropic distillation of water from the reaction medium. 7 - Composition selon l'une des revendications 5 et 6, caractérisée par le fait que l'acide percarboxylique est l'acide perpropionique. 7 - Composition according to one of claims 5 and 6, characterized in that the percarboxylic acid is perpropionic acid. 8 - Composition selon les revendications 6 et 7 prises simultanément, caractérisée par le fait que l'acide percarboxylique a été introduit dans la composition sous la forme d'une solution organique anhydre ou sensiblement anhydre, comprenant de l'acide perpropionique, comme produit, de l'acide propionique comme réactif n'ayant pas réagi, du propionate d'éthyle comme solvant, de l'eau oxygénée comme réactif n'ayant pas réagi, de l'acide sulfurique ou de l'acide borique comme catalyseur, et de l'acide dipicolinique comme stabilisant de la solution peracide fabriquée. 8 - Composition according to Claims 6 and 7 taken simultaneously, characterized in that the acid percarboxylic was introduced into the composition under the as an anhydrous or substantially organic solution anhydrous, including perpropionic acid, such as product, propionic acid as a reagent not having reacted, ethyl propionate as solvent, water oxygenated as unreacted reagent, acid sulfuric or boric acid as a catalyst, and dipicolinic acid as a solution stabilizer peracid manufactured. 9 - Composition selon l'une des revendications 5 à 8, caractérisée par le fait que le ou les acides percarboxyliques sont présents dans la solution aqueuse à
une concentration de 3,78 x 10-4 à 0,15 mole/1.

- Composition selon l'une des revendications 5 à 9, caractérisée par le fait que la solution aqueuse est tamponnée à un pH compris entre 7 et 10.

11 - Composition selon la revendication 10, caractérisée par le fait que la solution aqueuse est tamponnée à un pH compris entre 9 et 10.

12 - Composition selon l'une des revendications 5 à 11, caractérisée par le fait qu'elle comprend également au moins un agent tensio-actif cationique.

13 - Composition selon la revendication 12, caractérisée par le fait que le ou les agents tensio-actifs cationiques sont du type ammonium quaternaire, étant notamment représentés par la formule (I).

dans laquelle :
- R1, R2 et R3, identiques ou différents, représentent chacun un groupe alkyle en C1-C4 ou un groupe hydroxyalkyle en C1-C4 ;
- R4 représente un groupe benzyle ou un groupe alkyle linéaire ou ramifié en C11-C18 ; et - X représente un halogène ou un radical hydroxyle, ou par la formule (II):

dans laquelle :
- R représente un groupe alkyle linéaire en C16 ; et - X1 représente un halogène.
14 - Composition selon la revendication 13, caractérisée par le fait que le ou les agents tensio-actifs sont choisis parmi :
- le bromure de cétyl triméthyl ammonium ;
- le chlorure de cétyl triméthyl ammonium ;
- le bromure de cétyl diméthyl hydroxy-2 éthyl ammonium ;
- le bromure de cétyl méthyl bis (hydroxy-2 éthyl) ammonium ;
- le bromure de benzyl triméthyl ammonium ; et - le bromure de cétyl diaza-1,4-bicyclo [2.2.2] octyl ammonium.
15 - Composition selon l'une des revendications 12 à 14, caractérisée par le fait que le ou les agents tensio-actifs sont présents à raison de 10-3 à 0,1 mole par litre de composition.

16 - Procédé de décontamination de matériaux souillés par des composés organophosphorés et/ou organosoufrés, caractérisé par le fait que l'on applique sur le matériau souillé la composition telle que définie à l'une des revendications 5 à 15, par projection, pulvérisation ou simple lavage, ou que l'on fait tremper ledit matériau souillé dans un bac contenant la composition telle que définie à l'une des revendications 5 à 15. 9 - Composition according to one of claims 5 to 8, characterized in that the acid (s) percarboxylic are present in the aqueous solution to a concentration of 3.78 x 10-4 at 0.15 mol / l.

- Composition according to one of claims 5 to 9, characterized in that the aqueous solution is buffered at a pH between 7 and 10.

11 - Composition according to claim 10, characterized by the fact that the aqueous solution is buffered at a pH between 9 and 10.

12 - Composition according to one of claims 5 to 11, characterized in that it also includes minus a cationic surfactant.

13 - Composition according to claim 12, characterized by the fact that the surfactant (s) cationic are of the quaternary ammonium type, being in particular represented by formula (I).

in which :
- R1, R2 and R3, identical or different, represent each a C1-C4 alkyl group or a group C1-C4 hydroxyalkyl;
- R4 represents a benzyl group or an alkyl group linear or branched in C11-C18; and - X represents a halogen or a hydroxyl radical, or by formula (II):

in which :
- R represents a linear C16 alkyl group; and - X1 represents a halogen.
14 - Composition according to claim 13, characterized by the fact that the surfactant (s) are chosen from:
- cetyl trimethyl ammonium bromide;
- cetyl trimethyl ammonium chloride;
- cetyl dimethyl hydroxy-2 ethyl ammonium bromide;
- cetyl methyl bis (2-hydroxyethyl) bromide ammonium;
- benzyl trimethyl ammonium bromide; and - cetyl diaza-1,4-bicyclo [2.2.2] octyl bromide ammonium.
15 - Composition according to one of claims 12 to 14, characterized in that the surfactant (s) active ingredients are present at 10-3 to 0.1 mole per liter decomposition.

16 - Material decontamination process contaminated with organophosphorus compounds and / or organosulfurized, characterized by the fact that it is applied to the soiled material the composition as defined in one of claims 5 to 15, by spraying, spraying or simple washing, or soaking said material soiled in a container containing the composition such as defined in one of claims 5 to 15.
CA002389081A 1999-10-29 2000-10-25 Composition and method for destroying organophosphorous and/or organosulphurous pollutants Expired - Fee Related CA2389081C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR9913571A FR2800291B1 (en) 1999-10-29 1999-10-29 COMPOSITION AND PROCESS FOR THE DESTRUCTION OF ORGANOPHOSPHORUS AND / OR ORGANOSULFUR POLLUTANTS
FR99/13571 1999-10-29
PCT/FR2000/002967 WO2001030452A1 (en) 1999-10-29 2000-10-25 Composition and method for destroying organophosphorous and/or organosulphurous pollutants

Publications (2)

Publication Number Publication Date
CA2389081A1 true CA2389081A1 (en) 2001-05-03
CA2389081C CA2389081C (en) 2009-12-22

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CA002389081A Expired - Fee Related CA2389081C (en) 1999-10-29 2000-10-25 Composition and method for destroying organophosphorous and/or organosulphurous pollutants

Country Status (7)

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EP (1) EP1237628B1 (en)
AT (1) ATE395106T1 (en)
AU (1) AU1034401A (en)
CA (1) CA2389081C (en)
DE (1) DE60038896D1 (en)
FR (1) FR2800291B1 (en)
WO (1) WO2001030452A1 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7214836B2 (en) 2003-03-12 2007-05-08 Queen's University At Kingston Method of decomposing organophosphorus compounds
FR2930732B1 (en) * 2008-04-30 2010-05-14 Arkema France COMPOSITION AND METHOD FOR THE DESTRUCTION OF ORGANOPHOSPHORUS AND / OR ORGANOSOUFRES POLLUTANTS
EP3085738B1 (en) 2013-12-20 2022-01-19 Mitsui Chemicals, Inc. Semi-aromatic polyamide resin composition and molded article of same

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2464947A1 (en) * 1979-09-07 1981-03-20 Ugine Kuhlmann PROCESS FOR PRODUCING PERCARBOXYLIC ACIDS
FR2519634B1 (en) * 1982-01-13 1986-09-12 Ugine Kuhlmann IMPROVEMENT IN PROCESSES FOR THE SYNTHESIS OF PERCABOXYLIC ACIDS
FR2651133B1 (en) * 1989-08-22 1992-10-23 France Etat Armement PROCESS FOR DECONTAMINATION OF PERACID SOLUTIONS FROM MATERIALS CONTAMINATED WITH TOXIC AGENTS.
FR2676368B1 (en) * 1991-05-15 1994-10-28 France Etat Armement DECONTAMINATION COMPOSITION BASED ON MAGNESIUM MONOPEROXYPHTHALATE AND METHOD FOR DECONTAMINATION OF CONTAMINATED MATERIALS WITH TOXIC AGENTS USING THE SAME.
GB9213059D0 (en) * 1992-06-19 1992-08-05 Laporte Esd Ltd Compositions
FR2761080B1 (en) * 1997-03-21 2002-07-19 Quadrimex COMPOSITION BASED ON PERACIDS FOR THE CLEANING, DISINFECTION AND DECONTAMINATION OF SURFACES STAINED BY TOXIC AGENTS

Also Published As

Publication number Publication date
FR2800291B1 (en) 2004-07-09
EP1237628A1 (en) 2002-09-11
CA2389081C (en) 2009-12-22
ATE395106T1 (en) 2008-05-15
FR2800291A1 (en) 2001-05-04
AU1034401A (en) 2001-05-08
EP1237628B1 (en) 2008-05-14
DE60038896D1 (en) 2008-06-26
WO2001030452A1 (en) 2001-05-03

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