EP1237628A1 - Composition et procede pour la destruction de polluants organophosphores et/ou organosoufres - Google Patents
Composition et procede pour la destruction de polluants organophosphores et/ou organosoufresInfo
- Publication number
- EP1237628A1 EP1237628A1 EP00971499A EP00971499A EP1237628A1 EP 1237628 A1 EP1237628 A1 EP 1237628A1 EP 00971499 A EP00971499 A EP 00971499A EP 00971499 A EP00971499 A EP 00971499A EP 1237628 A1 EP1237628 A1 EP 1237628A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- acid
- composition
- composition according
- percarboxylic
- anhydrous
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
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
Definitions
- the present invention relates to the decontamination of fragile materials contaminated with toxic agents such as organophosphorus compounds and organosulfur compounds without causing significant degradation of said materials. It relates in particular to a new decontamination agent as well as to a composition and a process for destroying these organophosphorus and / or organosulfur pollutants.
- the invention applies more particularly to the treatment of fragile materials contaminated with organophosphorus compounds, such as organophosphates, amidophosphates, organoamidophosphates, phosphorothionates, phosphonothionates and phosphonoamidothionates used in the field of agriculture as insecticides and pesticides , as well as by organosulfur compounds of the RSR ', R and R' type representing in particular hydrocarbon radicals and halogenated hydrocarbon radicals.
- organophosphorus compounds such as organophosphates, amidophosphates, organoamidophosphates, phosphorothionates, phosphonothionates and phosphonoamidothionates used in the field of agriculture as insecticides and pesticides , as well as by organosulfur compounds of the RSR ', R and R' type representing in particular hydrocarbon radicals and halogenated hydrocarbon radicals.
- organophosphorus compounds such as 0, 0-diethyl-Op-nitrophenyl phosphate (Paraoxon®), O, O-diethyl-Op-nitrophenyl phosphonothioate (Parathion®) and 0.0-diethyl- O- (2-isopropyl-4-methyl-6-pyrimidyl) -phosphorothioate
- toxic organosulfur compounds such as 2, 2'-diethyl sulfide or 2-phenyl-2-chlorodiethyl sulfide are also very aggressive chemical agents whose stability allows them to persist on a ground contaminated for several years, without experiencing a significant decrease in toxicity.
- compositions currently available in the decontamination technique are solutions of sodium hydroxide in aqueous medium or in methylglycol in the presence of amine, or of calcium hypochlorite; however, such solutions are corrosive to fragile materials and in particular light metal alloys.
- nucleophilic compounds are effective products for eliminating toxic agents from the organophosphorus and organosulfur series.
- the hydroxyl anion in a strongly basic medium is capable of neutralizing these toxic agents.
- the efficiency obtained is accompanied by a strong aggressiveness with respect to the materials to be decontaminated.
- Another way is to use, in an environment which is not very basic, or even close to neutrality, peroxygen compounds such as hydrogen peroxide, tert-butyl hydroperoxide, perborates and peracids, because of their properties both nucleophilic and oxidising.
- the various peroxygen compounds are used in solutions containing surfactants of the quaternary ammonium type, improving the contact between the peroxygen reagent and the toxic agent during decontamination.
- the peroxides currently proposed in the decontamination of materials soiled by the various families of toxic agents, in particular Paraoxon® and sulfur compounds, are in the form of aqueous solutions of linear peracids with long carbon chain, pH between 6 and 8, or aqueous solutions based on industrial peracids such as magnesium monoperoxyphthalate or phthalimidoperhexanoic acid, these peracids being, in both cases, associated with surfactants in particular of the ammonium salt type quaternary.
- the first peracids are not commercially available and exhibit poor stability and solubility
- the second peracids, although commercially available, are in solid form at room temperature, have poor stability at high temperature and are not easy to handle for their implementation.
- the present invention therefore firstly relates to the use of an acid chosen from percarboxylic acids C2 to C ⁇ in the decontamination of materials contaminated with organophosphorus and / or organosulfur compounds.
- the percarboxylic acid used is in the form of an anhydrous or substantially anhydrous organic solution of said percarboxylic acid, in particular as it was obtained by reaction of an aqueous solution of hydrogen peroxide with the acid corresponding carboxylic acid miscible with water, in the presence of a catalyst and an organic solvent including optionally that which has enabled continuous elimination by azeotropic distillation of water from the reaction medium.
- anhydrous solutions or substantially anhydrous are water-soluble liquids, which allows easier implementation of decontaminating solutions.
- the preferred percarboxylic acid is perpropionic acid, due to its very high stability.
- the anhydrous or substantially anhydrous organic solution of perpropionic acid which may be used includes perpropionic acid as product, propionic acid as unreacted reagent, ethyl propionate as solvent, hydrogen peroxide as unreacted reagent, sulfuric acid or boric acid as catalyst, and dipicolinic acid as stabilizer of the peracid solution produced.
- the present invention also relates to a composition which can be used for the decontamination of materials soiled with organophosphorus and / or organosulfur compounds, this composition being characterized by the fact that it consists of an aqueous solution based on at least one percarboxylic acid. in Co to C ⁇ .
- the percarboxylic acid (s), in particular perpropionic acid, have advantageously been introduced into said composition in the form of an anhydrous or substantially anhydrous organic solution of said percarboxylic acid, as indicated above.
- the percarboxylic acid (s) are present in the aqueous solution at a concentration for example of 3.78 ⁇ 10 ⁇ 4 to 0.15 mol / l.
- the aqueous solution is buffered at a pH of between 7 and 10, in particular at a pH of between 9 and 10.
- the buffers which can be used are commercial solutions of pH 7 to 10.
- pH 9 is obtained from an aqueous solution containing a mixture of boric acid
- the aqueous decontaminating composition also comprises at least one cationic surfactant.
- the cationic surfactant (s) are advantageously of the quaternary ammonium type, being in particular represented by formula (I): R 1
- R 1 R? and R ⁇ , identical or different, each represent a C ⁇ -C ⁇ alkyl group or a C - ⁇ - C ⁇ hydroxyalkyl group;
- - R represents a benzyl group or a linear or branched C ⁇ -C ⁇ g alkyl group;
- - X represents a halogen or a hydroxyl radical
- R represents a linear C g alkyl group
- X represents a halogen
- surfactants are: - cetyl trimethyl ammonium bromide;
- surfactants are known and, for the most part, commercially available. They can be prepared by the methods described by C.A. Bunton et al.,
- the surfactant (s) are present in the aqueous decontaminating composition, in particular at a rate of 10 to 0.1 mole per liter of composition.
- the present invention also relates to a process for decontaminating materials soiled with organophosphorus and / or organosulfur compounds, characterized in that the composition as defined above is applied to the soiled material, by spraying, spraying or simple washing, or soaking said soiled material in a tank containing the composition as defined above.
- the molar ratio of C2 to C ⁇ percarboxylic acid relative to the pollutant is generally from 5 to 10 for organophosphorus pollutants (hydrolysis to phosphate) or from 3 to 5 for organosulfur pollutants (oxidation to sulfone).
- Contaminated fragile materials include electronic circuits (resin, electronic components, soldering), light alloys, polymers (poly (ethyl methacrylate)), etc. These materials have been polluted by deposition of the toxic on the surface: it is therefore a decontamination in heterogeneous phase.
- the tests carried out show a high efficiency of the compositions of the invention for the decontamination of toxic agents, such as Paraoxon® and 2-phenyl-2 '-chlorodiethyl sulfide.
- composition containing C to C4 percarboxylic acid, in particular perpropionic acid, in combination with the surfactant of the quaternary ammonium type allows practically instantaneous degradation of the toxic organophosphorus and organosulfur compounds.
- the composition has excellent stability over time at high temperatures, unlike conventional compositions based on peracids, and that C to C percarboxylic acid is in the form of a water-soluble liquid, which has an advantage when of the use of the composition and which makes it possible to obtain the degradation of the abovementioned toxic agents, in particular the total degradation of the 2-phenyl-2 '-chlorodiethyl sulfide in its non-toxic sulfone form, which is not the case of the other organic peracids which are only available in solid form and which have a low solubility in the aqueous phase.
- dipicolinic acid which had been prepared according to the method described in French patent application FR-A-2 519 634 but with ethyl propionate as solvent.
- Paraoxon® by perpropionic acid solutions is a quick and effective reaction.
- the destruction rates of Paraoxon® are high and quite remarkable.
- Example 2 The same anhydrous solution of perpropionic acid was used as in Example 1.
- Various aqueous solutions buffered to pH 7 or 9 were prepared from the above-mentioned anhydrous solution alone or with the surfactant chloride.
- cetyl trimethyl ammonium, perpropionic acid being at the concentration of 15 x 10 mole / liter and the surfactant, at the concentration of 10 mole / 1.
- the progress of the chemical destruction reaction of 2-phenyl-2 '-chlorodiethyl sulfide is determined by an analysis by gas chromatography, consisting in taking samples over time, analyzed by chromatography after addition of a mineral reducer (sodium thiosulfate).
- Table 2 indicates that the destruction of 2-phenyl-2 '-chlorodiethyl sulfide by perpropionic acid takes place quickly, thus confirming the exceptional properties of perpropionic acid in the decontamination of toxic agents.
Landscapes
- Business, Economics & Management (AREA)
- General Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Emergency Management (AREA)
- Detergent Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Processing Of Solid Wastes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compounds Of Unknown Constitution (AREA)
Description
Claims
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9913571A FR2800291B1 (fr) | 1999-10-29 | 1999-10-29 | Composition et procede pour la destruction de polluants organophosphores et/ou organosoufres |
FR9913571 | 1999-10-29 | ||
PCT/FR2000/002967 WO2001030452A1 (fr) | 1999-10-29 | 2000-10-25 | Composition et procede pour la destruction de polluants organophosphores et/ou organosoufres |
Publications (2)
Publication Number | Publication Date |
---|---|
EP1237628A1 true EP1237628A1 (fr) | 2002-09-11 |
EP1237628B1 EP1237628B1 (fr) | 2008-05-14 |
Family
ID=9551526
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP00971499A Expired - Lifetime EP1237628B1 (fr) | 1999-10-29 | 2000-10-25 | Composition et procede pour la destruction de polluants organophosphores et/ou organosoufres |
Country Status (7)
Country | Link |
---|---|
EP (1) | EP1237628B1 (fr) |
AT (1) | ATE395106T1 (fr) |
AU (1) | AU1034401A (fr) |
CA (1) | CA2389081C (fr) |
DE (1) | DE60038896D1 (fr) |
FR (1) | FR2800291B1 (fr) |
WO (1) | WO2001030452A1 (fr) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10253182B2 (en) | 2013-12-20 | 2019-04-09 | Mitsui Chemicals, Inc. | Semi-aromatic polyamide resin composition and molded article of same |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA2518562C (fr) | 2003-03-12 | 2014-08-05 | Queen's University At Kingston | Procede de decomposition de composes organophosphores |
FR2930732B1 (fr) * | 2008-04-30 | 2010-05-14 | Arkema France | Composition et procede pour la destruction de polluants organophosphores et/ou organosoufres |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2464947A1 (fr) * | 1979-09-07 | 1981-03-20 | Ugine Kuhlmann | Procede de fabrication d'acides percarboxyliques |
FR2519634B1 (fr) * | 1982-01-13 | 1986-09-12 | Ugine Kuhlmann | Perfectionnement aux procedes de synthese des acides percaboxyliques |
FR2651133B1 (fr) * | 1989-08-22 | 1992-10-23 | France Etat Armement | Procede de decontamination par des solutions de peracides de materiaux contamines par des agents toxiques. |
FR2676368B1 (fr) * | 1991-05-15 | 1994-10-28 | France Etat Armement | Composition de decontamination a base de monoperoxyphtalate de magnesium et procede de decontamination de materiaux contamines par des agents toxiques utilisant cette composition. |
GB9213059D0 (en) * | 1992-06-19 | 1992-08-05 | Laporte Esd Ltd | Compositions |
FR2761080B1 (fr) * | 1997-03-21 | 2002-07-19 | Quadrimex | Composition a base de peracides pour le nettoyage, la desinfection et la decontamination de surfaces souillees par des agents toxiques |
-
1999
- 1999-10-29 FR FR9913571A patent/FR2800291B1/fr not_active Expired - Fee Related
-
2000
- 2000-10-25 EP EP00971499A patent/EP1237628B1/fr not_active Expired - Lifetime
- 2000-10-25 DE DE60038896T patent/DE60038896D1/de not_active Expired - Lifetime
- 2000-10-25 AU AU10344/01A patent/AU1034401A/en not_active Abandoned
- 2000-10-25 WO PCT/FR2000/002967 patent/WO2001030452A1/fr active Search and Examination
- 2000-10-25 AT AT00971499T patent/ATE395106T1/de not_active IP Right Cessation
- 2000-10-25 CA CA002389081A patent/CA2389081C/fr not_active Expired - Fee Related
Non-Patent Citations (1)
Title |
---|
See references of WO0130452A1 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10253182B2 (en) | 2013-12-20 | 2019-04-09 | Mitsui Chemicals, Inc. | Semi-aromatic polyamide resin composition and molded article of same |
Also Published As
Publication number | Publication date |
---|---|
AU1034401A (en) | 2001-05-08 |
DE60038896D1 (de) | 2008-06-26 |
FR2800291A1 (fr) | 2001-05-04 |
EP1237628B1 (fr) | 2008-05-14 |
CA2389081C (fr) | 2009-12-22 |
ATE395106T1 (de) | 2008-05-15 |
WO2001030452A1 (fr) | 2001-05-03 |
CA2389081A1 (fr) | 2001-05-03 |
FR2800291B1 (fr) | 2004-07-09 |
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