EP0848628A1 - Composition a base de peracides pour la decontamination de materiaux souilles par des agents toxiques - Google Patents
Composition a base de peracides pour la decontamination de materiaux souilles par des agents toxiquesInfo
- Publication number
- EP0848628A1 EP0848628A1 EP97905197A EP97905197A EP0848628A1 EP 0848628 A1 EP0848628 A1 EP 0848628A1 EP 97905197 A EP97905197 A EP 97905197A EP 97905197 A EP97905197 A EP 97905197A EP 0848628 A1 EP0848628 A1 EP 0848628A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- group
- composition according
- general formula
- cetyl
- peracid
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 37
- 150000004965 peroxy acids Chemical class 0.000 title claims abstract description 25
- 239000000463 material Substances 0.000 title claims abstract description 17
- 231100000167 toxic agent Toxicity 0.000 title description 7
- 239000003440 toxic substance Substances 0.000 title description 7
- 239000004094 surface-active agent Substances 0.000 claims abstract description 18
- 238000005202 decontamination Methods 0.000 claims abstract description 10
- 230000003588 decontaminative effect Effects 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 239000003093 cationic surfactant Substances 0.000 claims abstract description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
- 150000003839 salts Chemical class 0.000 claims abstract 2
- 239000002253 acid Substances 0.000 claims description 12
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- -1 hydroxyethyl group Chemical group 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- GIDDQKKGAYONOU-UHFFFAOYSA-N octylazanium;bromide Chemical compound Br.CCCCCCCCN GIDDQKKGAYONOU-UHFFFAOYSA-N 0.000 claims description 4
- 231100000331 toxic Toxicity 0.000 claims description 4
- 230000002588 toxic effect Effects 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- WOWHHFRSBJGXCM-UHFFFAOYSA-M cetyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)C WOWHHFRSBJGXCM-UHFFFAOYSA-M 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical group [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims description 2
- 150000003254 radicals Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 150000002898 organic sulfur compounds Chemical class 0.000 abstract description 9
- 150000002903 organophosphorus compounds Chemical class 0.000 abstract description 7
- 150000001875 compounds Chemical class 0.000 description 9
- WYMSBXTXOHUIGT-UHFFFAOYSA-N paraoxon Chemical compound CCOP(=O)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 WYMSBXTXOHUIGT-UHFFFAOYSA-N 0.000 description 9
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 8
- 229960004623 paraoxon Drugs 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 230000006378 damage Effects 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 230000000593 degrading effect Effects 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-O ethylaminium Chemical compound CC[NH3+] QUSNBJAOOMFDIB-UHFFFAOYSA-O 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 230000000269 nucleophilic effect Effects 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- 239000003053 toxin Substances 0.000 description 2
- 231100000765 toxin Toxicity 0.000 description 2
- 108700012359 toxins Proteins 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- HNTGIJLWHDPAFN-UHFFFAOYSA-N 1-bromohexadecane Chemical compound CCCCCCCCCCCCCCCCBr HNTGIJLWHDPAFN-UHFFFAOYSA-N 0.000 description 1
- CLWAXFZCVYJLLM-UHFFFAOYSA-N 1-chlorohexadecane Chemical compound CCCCCCCCCCCCCCCCCl CLWAXFZCVYJLLM-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 102100033639 Acetylcholinesterase Human genes 0.000 description 1
- 108010022752 Acetylcholinesterase Proteins 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZKQDCIXGCQPQNV-UHFFFAOYSA-N Calcium hypochlorite Chemical compound [Ca+2].Cl[O-].Cl[O-] ZKQDCIXGCQPQNV-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
- 229940122041 Cholinesterase inhibitor Drugs 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- AXPZGGIIXCYPQK-UHFFFAOYSA-N OS(=O)P(O)(O)=O Chemical class OS(=O)P(O)(O)=O AXPZGGIIXCYPQK-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
- 229960004373 acetylcholine Drugs 0.000 description 1
- 229940022698 acetylcholinesterase Drugs 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- RLGQACBPNDBWTB-UHFFFAOYSA-N cetyltrimethylammonium ion Chemical compound CCCCCCCCCCCCCCCC[N+](C)(C)C RLGQACBPNDBWTB-UHFFFAOYSA-N 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000000544 cholinesterase inhibitor Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 239000012972 dimethylethanolamine Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- LHQIDEFUIPPQFM-UHFFFAOYSA-N ethyl-hexadecyl-bis(2-hydroxyethyl)azanium Chemical compound CCCCCCCCCCCCCCCC[N+](CC)(CCO)CCO LHQIDEFUIPPQFM-UHFFFAOYSA-N 0.000 description 1
- 239000011790 ferrous sulphate Substances 0.000 description 1
- 235000003891 ferrous sulphate Nutrition 0.000 description 1
- ZONYXWQDUYMKFB-UHFFFAOYSA-N flavanone Chemical class O1C2=CC=CC=C2C(=O)CC1C1=CC=CC=C1 ZONYXWQDUYMKFB-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- SURQXAFEQWPFPV-UHFFFAOYSA-L iron(2+) sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Fe+2].[O-]S([O-])(=O)=O SURQXAFEQWPFPV-UHFFFAOYSA-L 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- 238000006075 micellar catalysis Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 239000002581 neurotoxin Substances 0.000 description 1
- 125000000962 organic group Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical class [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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
- A62D2101/26—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 a composition intended for the decontamination of materials soiled by toxic agents, and more particularly a composition based on peracids ensuring the effective decontamination of materials soiled by toxic agents such as organophosphorus or organosulfur compounds, without causing degra ⁇ notable donations of said materials
- organophosphate cholinesterase inhibitor compounds such as organophosphates, amidophosphates, organoamidophosphates, phosphorothionates, phosphonothionates and phosphoroamidothionates, can be used in the field of agriculture as insecticides and pesticides.
- organosulfur compounds are known as vesicants and used as toxic agents of war.
- organophosphorus compounds used as pesticides or insecticides in agriculture there may be mentioned in particular O, O-diethyl-O-p-nitrophenyl phosphate
- compositions currently used in the decontamination technique are sodium hydroxide solutions in ethyl glycol with diethylamine, or calcium hypochlorite, but these solutions are very corrosive.
- nucleophilic compounds have the qualities required to remove toxins from the organophosphate and organosulfur series.
- C.A. Bunton et al., L7. AT . Chem. Soc. 95, 2912 (1973) have demonstrated the properties of the hydroxyl ion for this purpose; other reagents have also been proposed, including hydroxic acids, oximes, mono- and polyphenols, aldehyde hydrates, certain amines, as well as calcium or sodium hypochlorites.
- peroxyanions such as hydrogen peroxide, tert-butyl hydroperoxide, perborates and peracids, due to their both nucleophilic and oxidizing properties.
- surfactants of the quaternary ammonium type accelerates the destruction of toxins by micellar catalysis. So the patent.
- compositions constituted by solutions containing linear peracids with a long carbon chain, of pH between 6 and 8, generally associated with surfactants such as cetyl trimethyl ammonium bromide, bromide of cetyl dimethyl hydroxyethyl-2 ammonium, cetyl methyl bis (hydroxyethyl-2) ammonium bromide or cetyl diaza-1,4 bicyclo (2.2.2) octyl ammonium bromide.
- surfactants such as cetyl trimethyl ammonium bromide, bromide of cetyl dimethyl hydroxyethyl-2 ammonium, cetyl methyl bis (hydroxyethyl-2) ammonium bromide or cetyl diaza-1,4 bicyclo (2.2.2) octyl ammonium bromide.
- Such compositions make it possible to destroy Paraoxon, VX and Yperite.
- the peracids used are not commercially available and the stability of the compositions is not satisfactory.
- the patent FR-A-2,676,368 describes aqueous compositions based on magnesium onoperoxyphthalate and of surface-active agent of the quaternary ammonium salt type, usable for the decontamination of materials soiled with certain neurotoxic agents, in particular VX, and vesicants such as Yperite.
- the present invention relates to a composition of ⁇ '/ e containing a peracid ⁇ t a surfactant, used sand for the decontamination of materials contaminated with toxic organophosphorus or organosulfur agents, comprising
- n is an integer between 3 and 8
- R x identical or different in each group -CHR ⁇ , is an alkyl group or a phenyl group
- R 2 has the same definition as R 1 # -
- the composition consists of an aqueous solution at buffered pH between 8 and 11, and preferably between 9 and 10.
- R x and R 2 preferably represent an alkyl group of 1 to 4 carbon atoms, and by ⁇ xer.ple an ethyl, ethyl or n-prepyl group.
- the imidoperacid of general formula (I) can be for example phthalimidoperpropionic or phthalimidoperpropoic acid.
- the diperacid of general formula (II) can be chosen from, for example, perdidecanoic, perdinonanoic, and perdidodecanoic acids.
- the peracids used in the invention are products available commercially or the preparation of which can be carried out easily by usual techniques, by the action of hydrogen peroxide in an acid medium (for example in cold concentrated sulfuric acid medium) on the corresponding acids.
- a method for preparing such peracids is described by C. Lion et al. Bull. Soc. Chim. Belg. J2 (2) 127 (1990).
- the cationic surfactant of the quaternary ammonium type is preferably represented by the general formula (III):
- R 1 R 2 and R 3 , identical or different, represent an alkyl or hydroxyalkyl group of 1 to 4 carbon atoms
- R 4 represents a linear or branched alkyl group of 11 to 13 carbon atoms
- X represents a halogen or a hydroxyl radical.
- surfactants represented by the general formula (III) above preferably uses those for which R 1r R 2 and R represent an xethyl group, an ethyl group or a hydroxyethyl group, R. represents a cetyl group, and X is chlorine, bromine has a radical - C'A.
- the surfactant of general formula (III) is chosen from bromide or cetyl trimethyl ammonium chloride, cetyl dimethyl hydroxyethyl-2-ammonium bromide, bromide of cetyl ethyl bis (2-hydroxyethyl) ammonium or cetyl diaza-1,4 bicyclo (2.2.2) octyl 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. (cited above) and by L. Horner et al. , Phosohorus and Sulfur. H, 339 (1981).
- cetyl dimethyl hydroxyethyl-2-ammonium bromide can be obtained by refluxing a solution of hexadecyl bromide and dimethylethanolamine in a mixture of acetonitrile and methanol and by recrystallizing the crystals obtained from methanol.
- the composition according to the invention is preferably in the form of a buffered aqueous solution, of pH between 8 and 11, preferably between 9 and 10, for example an aqueous solution of a mixture of baking soda and sodium bicarbonate.
- This aqueous solution is applied to the material to be decontaminated, by spraying, spraying or simple washing, or it is possible to soak the materials in a tank containing a composition according to the invention.
- the peracid and the surfactant of the quaternary ammonium type when X is a hydroxyl, can be combined within the same molecule, to form a tetraalkylammonium percarboxylate.
- Such a CCM can be obtained by the action of the peracid of formula ( ⁇ ) or (II) on a tetraalkylammonium hydroxide, in stoichiometric amounts.
- This variant is particularly advantageous because the percarboxylate can be generated in situ, and thus occurs in aqueous solution, without the need to use a carbonate buffer which is replaced here by 1 * tetraalkylammonium hydroxide.
- Tetraalkylammonium hydroxide can be prepared using the method described by L. Sepulveda et al., J. Phys. ⁇ hem. , 89, 5322 (1985), from carbon sulphide and sodium ethylate, and action of a tetraalkylammonium bromide in sulfuric medium, then treatment with a base such as 1 barium hydroxide.
- compositions according to the invention for the decontamination of materials soiled with toxic organophosphorus or organosulfur compounds was verified by making them act on known compounds such as O, O-diethyl-Op-nitrophenyl phosphate (Paraoxon), in the series of organophosphorus compounds, and 2-phenyl-2 '-chlorodiethyl sulfide, analog of Yperite, in the series of organo ⁇ sulfur.
- compositions of the invention cause the destruction of compounds such as Paraoxon and the analogue of Yperite almost instantaneously.
- This result is obtained with the composition containing the peracid of formula (I) or (II) in combination with the surfactant of the quaternary ammonium type, as well as with the composition cc ⁇ tenar.t a tetraalkylammonium percarboxylate.
- the composition of the invention has excellent stability over time, unlike
- LOCATION SHEET (RULE 26 to conventional compositions based on peracids, and is not aggressive with respect to the various materials currently treated.
- compositions according to the invention comprising either a combination of peracid and surfactant (Example 1), or a percarboxylate tetraalkylammonium (Example 2).
- the destruction kinetics are carried out for Paraoxon according to a usual technique, in UV spectroscopy at 402 nm, corresponding to the maximum absorption of the p-nitrophenate ion released, at 25 ° C.
- the destruction rates of the analog, of the abovementioned Yperite are determined by chromatographic analysis at regular intervals, after addition of a mineral (ferrous sulfate) or organic (triphenylphosphine) reducing agent. We operate at a pH of.
- Table 1 below indicates the half-reaction time (in s.), At 25 ° C., per action of each of the four peracids indicated below, in 2.10 " M solution at pH 9, on the Paraoxon (5.10 "5 M).
- the surfactants used in combination with the above peracids are:
- cetyl chloride tri ⁇ .ethyl ammonium 6.
- cetyl brirride trirr.ethyl ammonium cetyl dimethyl hydroxyethyl-2-ammonium bromide cetyl methyl bis (hydroxyethyl-2) ammonium bromide cetyl diaza-1,4-bicyclo (2.2.2) octyl ammonium bromide
- composition according to the invention provides results equivalent to those obtained with magnesium monoperphthalate (MPPM) which is the best decontaminant currently known with respect to Paraoxon.
- MPPM magnesium monoperphthalate
- the compositions of the invention are also effective against organosulfur compounds.
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- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Business, Economics & Management (AREA)
- Emergency Management (AREA)
- Detergent Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
Description
Claims
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9603204A FR2746020B1 (fr) | 1996-03-14 | 1996-03-14 | Composition a base de peracides pour la decontamination de materiaux souilles par des agents toxiques |
FR9603204 | 1996-03-14 | ||
PCT/FR1997/000274 WO1997033655A1 (fr) | 1996-03-14 | 1997-02-13 | Composition a base de peracides pour la decontamination de materiaux souilles par des agents toxiques |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0848628A1 true EP0848628A1 (fr) | 1998-06-24 |
EP0848628B1 EP0848628B1 (fr) | 2003-04-23 |
Family
ID=9490179
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP97905197A Expired - Lifetime EP0848628B1 (fr) | 1996-03-14 | 1997-02-13 | Procede utilisant une composition a base de peracides pour la decontamination de materiaux souilles par des agents toxiques |
Country Status (8)
Country | Link |
---|---|
US (1) | US6143088A (fr) |
EP (1) | EP0848628B1 (fr) |
CA (1) | CA2218079A1 (fr) |
DE (1) | DE69721197T2 (fr) |
ES (1) | ES2192666T3 (fr) |
FR (1) | FR2746020B1 (fr) |
IL (1) | IL121824A (fr) |
WO (1) | WO1997033655A1 (fr) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7582594B2 (en) | 2003-10-17 | 2009-09-01 | Applied Research Associates, Inc. | Dioxirane formulations for decontamination |
WO2006076334A1 (fr) * | 2005-01-11 | 2006-07-20 | Clean Earth Technologies, Llc | Compositions de peracides/peroxydes et utilisation de ces compositions en tant qu'agents antimicrobiens et photosensibilisants |
WO2006076406A2 (fr) * | 2005-01-11 | 2006-07-20 | Clean Earth Technologies, Llc | Formulations destinees a la decontamination de produits chimiques toxiques |
US8084662B2 (en) * | 2005-05-09 | 2011-12-27 | ChK Group Inc. | Method for degrading chemical warfare agents using Mn(VII) oxide with-and-without solid support |
US20100179368A1 (en) * | 2008-11-07 | 2010-07-15 | Aries Associates, Inc. | Novel Chemistries, Solutions, and Dispersal Systems for Decontamination of Chemical and Biological Systems |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1054473A (fr) * | 1964-05-08 | |||
US3749674A (en) * | 1971-02-22 | 1973-07-31 | Procter & Gamble | Bleach compositions |
US3749673A (en) * | 1971-02-22 | 1973-07-31 | Procter & Gamble | Bleach-fabric softener compositions |
US3996152A (en) * | 1975-03-27 | 1976-12-07 | The Procter & Gamble Company | Bleaching composition |
EP0160342B2 (fr) * | 1984-05-01 | 1992-11-11 | Unilever N.V. | Compositions de blanchiment liquides |
US4902441A (en) * | 1988-03-31 | 1990-02-20 | The United States Of America As Represented By The Secretary Of The Navy | Self moistening composition for deactivating toxic substances and method of use |
DE3823172C2 (de) * | 1988-07-08 | 1998-01-22 | Hoechst Ag | omega-Phthalimidoperoxihexansäure, Verfahren zu dessen Herstellung und dessen Verwendung |
US4992194A (en) * | 1989-06-12 | 1991-02-12 | Lever Brothers Company, Division Of Conopco Inc. | Stably suspended organic peroxy bleach in a structured aqueous liquid |
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. |
-
1996
- 1996-03-14 FR FR9603204A patent/FR2746020B1/fr not_active Expired - Fee Related
-
1997
- 1997-02-13 WO PCT/FR1997/000274 patent/WO1997033655A1/fr active IP Right Grant
- 1997-02-13 EP EP97905197A patent/EP0848628B1/fr not_active Expired - Lifetime
- 1997-02-13 IL IL12182497A patent/IL121824A/en not_active IP Right Cessation
- 1997-02-13 CA CA002218079A patent/CA2218079A1/fr not_active Abandoned
- 1997-02-13 ES ES97905197T patent/ES2192666T3/es not_active Expired - Lifetime
- 1997-02-13 DE DE69721197T patent/DE69721197T2/de not_active Expired - Fee Related
- 1997-02-13 US US08/952,398 patent/US6143088A/en not_active Expired - Fee Related
Non-Patent Citations (1)
Title |
---|
See references of WO9733655A1 * |
Also Published As
Publication number | Publication date |
---|---|
IL121824A0 (en) | 1998-02-22 |
ES2192666T3 (es) | 2003-10-16 |
DE69721197D1 (de) | 2003-05-28 |
IL121824A (en) | 2002-04-21 |
EP0848628B1 (fr) | 2003-04-23 |
FR2746020A1 (fr) | 1997-09-19 |
WO1997033655A1 (fr) | 1997-09-18 |
CA2218079A1 (fr) | 1997-09-18 |
FR2746020B1 (fr) | 1998-04-24 |
US6143088A (en) | 2000-11-07 |
DE69721197T2 (de) | 2004-04-01 |
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