CN102015035A - Composition and process for the destruction of organophosphorus and/or organosulphur pollutants - Google Patents

Composition and process for the destruction of organophosphorus and/or organosulphur pollutants Download PDF

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Publication number
CN102015035A
CN102015035A CN2009801151468A CN200980115146A CN102015035A CN 102015035 A CN102015035 A CN 102015035A CN 2009801151468 A CN2009801151468 A CN 2009801151468A CN 200980115146 A CN200980115146 A CN 200980115146A CN 102015035 A CN102015035 A CN 102015035A
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composition
acid
surfactant
basifier
hydroxy ethylene
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CN102015035B (en
Inventor
J-L·库蒂里耶
J·凯尔韦纳
P·C·戈菲内
C·利昂
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Arkema France SA
Arkema SA
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    • AHUMAN NECESSITIES
    • A62LIFE-SAVING; FIRE-FIGHTING
    • A62DCHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
    • A62D3/00Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances
    • A62D3/30Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances by reacting with chemical agents
    • A62D3/38Processes 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
    • AHUMAN NECESSITIES
    • A62LIFE-SAVING; FIRE-FIGHTING
    • A62DCHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
    • A62D2101/00Harmful chemical substances made harmless, or less harmful, by effecting chemical change
    • A62D2101/02Chemical warfare substances, e.g. cholinesterase inhibitors
    • AHUMAN NECESSITIES
    • A62LIFE-SAVING; FIRE-FIGHTING
    • A62DCHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
    • A62D2101/00Harmful chemical substances made harmless, or less harmful, by effecting chemical change
    • A62D2101/04Pesticides, e.g. insecticides, herbicides, fungicides or nematocides
    • AHUMAN NECESSITIES
    • A62LIFE-SAVING; FIRE-FIGHTING
    • A62DCHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
    • A62D2101/00Harmful chemical substances made harmless, or less harmful, by effecting chemical change
    • A62D2101/20Organic substances
    • A62D2101/26Organic substances containing nitrogen or phosphorus
    • AHUMAN NECESSITIES
    • A62LIFE-SAVING; FIRE-FIGHTING
    • A62DCHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
    • A62D2101/00Harmful chemical substances made harmless, or less harmful, by effecting chemical change
    • A62D2101/20Organic substances
    • A62D2101/28Organic substances containing oxygen, sulfur, selenium or tellurium, i.e. chalcogen

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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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fireproofing Substances (AREA)

Abstract

The invention relates to a decontaminating composition comprising: (i) perpropionic acid, (ii) dipicolinic acid, (iii) a salt of hydroxyethyldiethylphosphonic acid, (iv) a surface-active agent, and (v) an alkalinizing agent. The decontaminating compositions that are the subject of the invention have a high stability and high effectiveness, enabling a rapid destruction of the toxic organophosphorus or organosulphur agents.

Description

Be used to destroy the composition and the method for organophosphor and/or organic sulfur pollutant
The present invention relates to the decontamination of organophosphor or organic sulfur pollutant and/or toxic agents,, for example be used for the decontamination of pesticide especially in chemical warfare reagent field or at agriculture field.It relates to the novel cleansing composition that comprises two kinds of specified stabilisers especially, and the method that is used to destroy these organophosphors and/or organic sulfur pollutant.
In chemical warfare reagent field, there are many organic phosphides that obtain by phosphoric acid and phosphonic acids at present, as tabun, sarin or Suo Man.These compounds are owing to they have high neurotoxicity for the phosphorylation ability of cholinesterase, because acetylcholine gathering in organism, its inhibitory action causes death.
And, also there is poisonous organic sulfur product, as industrial sulfide or war toxic agent, for example mustard gas of vesicant class.
In agriculture field, there is the organophosphor toxic compounds, such as organophosphorus ester as pesticide and pesticide, the acylamino-phosphate, organic acylamino-phosphate, thiophosphate, Thiophosphonate and acylamino-Thiophosphonate, and the organosulfur compound of R-S-R ' type, R and R ' represent especially based on the group of hydrocarbon or based on the group of halogenated hydrocarbons.
In the organic phosphorus compound of knowing most, as O, O-diethyl-O-p-nitrobenzophenone phosphate (Paraoxon), O, O-diethyl-O-p-nitrobenzophenone Thiophosphonate (Parathion) and O, the compound of O-diethyl-O-(2-isopropyl-4-methyl-6-pyrimidine radicals) thiophosphate (Diazinon) plays an important role as pesticide or as agricultural chemicals in agricultural.
And poisonous organosulfur compound is as two chloro-2,2 '-diethyl thioether or 2-phenyl-2-chloro diethyl thioether, also be very corrosive chemical reagent, its stability can make them remaining in contaminated district for many years, and does not know to reduce how significantly toxicity.
It is a problem that a large amount of storages of the product of listing above exist.Removing of they means that especially the use cleansing composition is to be applied on product itself or contaminated material or the individual.Cleansing composition can be in the replacement mode or to use with the physical method compound mode of displacement toxic agents.
Therefore importantly, can have, especially have a mind to or the unexpected situation of using this compound under, the toxicity of can degrading product itself and make the composition of the material decontamination of being polluted fast and effectively by toxic agents.
Now available compositions useful is in the presence of amine or calcium hypochlorite, and NaOH is in aqueous medium or the solution in Propylene Glycol (1, the 2-propane diols); Yet this solution is for fragile material, particularly light-metal alloy is corrosive.
What know is that the protophilic compound is effective product for the toxic agents of removing organophosphor and organic sulfur series.Therefore these toxic agents that can neutralize of the hydroxyl anion in strongly basic medium.Yet the validity of acquisition is attended by the severe corrosive for the material for the treatment of decontamination.
Other method is at more not alkaline medium, even approaches to use snperoxiaized compound in the neutral medium, and as hydrogen peroxide, tert-butyl hydroperoxide, perborate and peracid, this is because the performance of its protophilic and oxidation simultaneously.Various snperoxiaized compounds are to use in the solution of the surfactant that comprises the quaternary ammonium type the most usually, and surfactant improves in the contact between peroxidization agent and toxic agents during the decontamination.
At present, make (especially by all kinds of toxic agents
Figure BPA00001250775000021
) peroxide that proposes in the material decontamination of polluting, being pH with sulfur-containing compound is that the straight chain that comprises long carbochain of 6-8 is crossed the aqueous acid form, perhaps cross caproic acid aqueous solution form based on industrial peracid such as monoperphthalic acid magnesium or phthalimido, these peracid under the two situation with surfactant, quaternary ammonium salt type surfactant combination especially.
Yet, first kind of peracid be seldom can be commercial on industrial level that obtain and have in equistability and moderate solubility, second kind of peracid, though they can commercially obtain, but be solid form at ambient temperature, and at high temperature have middle equistability, and when using, be not easy to handle.
Based on C 2-C 4Percarboxylic acids and be described in the International Application No. WO 01/30452 as detergent based on the Aquo-composition of pyridinedicarboxylic acid.Yet this compositions display goes out stability problem and uses the anhydrous percarboxylic acids that obtains by expensive Azotropic distillation method.
Comprising can be that the Aquo-composition of peroxidating reagent of peracid is described among the patent application EP 0894512 as detergent.Yet this based composition has weak relatively decontamination.
Therefore exist to having than those above-mentioned bigger stability and the reality needs with novel cleansing composition of big validity, this novel cleansing composition can rapid damage organophosphor or organic sulfur toxic agents.
The applicant has developed the composition that can address the above problem, and has developed the composition with excellent stability and excellent validity especially, and it causes the rapid damage of toxic agents.
Therefore theme of the present invention at first is cleansing composition, and it comprises:
(i) Perpropionic Acid
(ii) pyridinedicarboxylic acid
(iii) hydroxy ethylene diphosphonic acid (HEDP or its salt),
(iv) surfactant and
(v) basifier
Surprisingly, have been noted that as top defined composition be sufficiently stable decontamination effectiveness to obtain to prolong.
Surprisingly, have been noted that the theme composition of the present invention that comprises Perpropionic Acid has the decontamination bigger than the composition that comprises peracetic acid (embodiment 2 and 3) and renders a service.
Preferably, the salt of hydroxy ethylene diphosphonic acid is hydroxy ethylene diphosphonic acid sodium (HEDP).
For purposes of the invention, term " cleansing composition " is to be used for representing being used to making the material decontamination of being polluted by organophosphor and/or organosulfur compound or to be used to composition that toxicity product itself is degraded.
Advantageously, the Perpropionic Acid of use is aqueous solution form, and it is as in the presence of catalyst (as sulfuric acid or boric acid) especially, those that the aqueous solution by hydrogen peroxide and the reaction of propionic acid obtain.This preparation method for example is described among the french patent application FR2462425.Different with the anhydrous solution of the Perpropionic Acid of in french patent application No.FR2464947 and FR2519634, describing, this aqueous solution is obtained by straightforward procedure, its unreal step of granting poisonous or inflammable organic solvent (as 1,2-dichloroethanes or cyclohexane) azeotropic distillation.
Thus, the Perpropionic Acid of use is aqueous solution form, and it comprises: as the Perpropionic Acid of product, as the propionic acid of responseless reactant, as the hydrogen peroxide of responseless reactant with as the sulfuric acid or the boric acid of catalyst.
Therefore cleansing composition defined above can also comprise, except compound (i)-(v):
-propionic acid
-hydrogen peroxide and
-sulfuric acid and/or boric acid.
This composition is a water-soluble liquid, and it makes that the cleansing composition of theme of the present invention is easy to use.
In a kind of specific embodiment of the present invention, composition defined above is aqueous solution form.Therefore, theme of the present invention still comprises the aqueous solution as top defined cleansing composition.
The composition of theme of the present invention comprises basifier.Preferably basifier is selected from NaOH, potassium hydroxide, ammonium hydroxide, sodium carbonate or sodium acid carbonate, potash or saleratus, sodium phosphate, potassium phosphate, ammonium phosphate, sodium metasilicate, potassium silicate, ammonium silicate, Boratex, potassium borate, ammonium borate and their mixture.Described one or more basifiers can be regulated the pH of theme composition of the present invention.Advantageously, theme composition of the present invention has and is higher than 7, preferably 8-12, the pH of 8.5-9.5 especially.
Can be buffered in the pH of 7-10 according to composition of the present invention.When being alkaline compositions for the composition of theme of the present invention, pyridinedicarboxylic acid, Perpropionic Acid and HEDP can be the form of their corresponding salt.
The composition of theme of the present invention can also comprise alkaline buffer.For purposes of the invention, term " alkaline buffer " be used for representing single type alkaline buffer and alkaline buffer mixture the two.Composition according to the present invention comprises alkaline buffer, as basic carbonate or alkaline silicate, and potash or sodium carbonate especially.
For purposes of the invention, term " surfactant " is used for representing anionic, cationic, non-ionic or amphoteric surfactant, it is with 0 weight %-25 weight % with respect to the gross weight of said composition, and preferably the ratio of 5 weight %-20 weight % is used.
As cationic surfactant, can mention those of quaternary ammonium type, for example:
-softex kw
-hexadecyltrimethylammonium chloride
-hexadecyldimethyl benzyl ammonium 2-hydroxyethyl ammonium bromide,
Two (2-hydroxyethyl) ammonium bromides of-cetyl methyl,
-benzyltrimethylammonium bromide and
-cetyl diaza-1,4-dicyclo [2.2.2] octyl group ammonium bromide.
These surfactants are known, and the great majority in them can commercially obtain.They can be by by C.A.Bunton etc., J.Am.Chem.Soc., and 95,2912 (1973) and by L.Horner etc., Phosphorus and Sulfur, 11,339 (1981) methods of describing are prepared.
As operable non-ionic surface active agent randomly, can mention, for example:
The alkoxy fatty alcohols of-following formula: R-[(CH 2) 2O] m-[CH 2CH (CH 3) O] n-H
Wherein R comprises 8-22 carbon atom, the preferably alkyl of 12-14 carbon atom or alkenyl; N and m represent the integer of 0-50 independently, its summation n+m>1;
The alkyl poly glucoside of-following formula: R " '-[glucose] n-, R wherein " ' be C 8-C 16Alkyl and n are the integers of 1-3;
The ester of-reduced sugar, the ester of polyalcohol and their ethoxylated derivative, as, for example monostearate sorbitan ester, glycerin monostearate or glycol stearate perhaps comprise the monostearate sorbitan ester of the ethoxylation of 20 oxirane;
The alkylamide of the ethoxylation of-following formula:
Wherein R such as the definition of top institute and r and s are the integers of 0-15, its summation r+s>1;
-alkyl pyrrolidone, its alkyl is C 6-C 20Alkyl; With their mixture.
Preferably, this Perpropionic Acid exists with the described aqueous solution form of for example 0.05-4.5mol/l concentration.
In a preferred embodiment, theme composition of the present invention comprises (representing with the weight with respect to the gross weight of said composition):
-4%-16% Perpropionic Acid,
-0.1%-2% pyridinedicarboxylic acid
-0.5%-5% ethoxy diethyl Alendronate
-5%-20% surfactant
-2%-20% basifier and
The alkaline buffer of-5%-15% weight.
For the solution of theme of the present invention can also comprise at least a component that is selected from hydrotropic agent (as urea or cumene sodium sulfonate), tackifier (as xanthans), modified corn starch, hydroxyethylcellulose or defoamer.
Said composition can be powder, liquid, gel or form of suspension.
Preferably use according to composition of the present invention with the aqueous solution with respect to the concentration of 0.5 weight %-40 weight % Perpropionic Acid of the gross weight of this solution.They can also with organic, not with the miscible solvent of water in emulsion or micro emulsion form after disperseing use, this solvent as, aliphatic series that for example randomly is chlorinated or aromatic hydrocarbon, for example toluene, dimethylbenzene, carrene and tetrachloro-ethylene.
They can by spray, smear, spray, soak, dipping or any operation that other can make described composition and contaminated materials or individual contact come manually or mechanically to use.
Theme of the present invention still makes the method for toxic agents organophosphor or organic sulfur and/or pollutant decontamination, it comprise make described toxic agents and/or pollutant with as top defined composition contact.
Toxic agents described organophosphor or organic sulfur and/or pollutant can be for example in military field; war toxic agent organophosphor or organic sulfur, perhaps in agriculture field, plant protection reagent organophosphor or organic sulfur; pesticide, perhaps industrial pollutants especially.
Theme of the present invention still is used to make the method by compound polluted material decontamination organophosphor and/or organic sulfur, comprise by spray, spraying or simple washing, perhaps described contaminated material is immersed in and comprises as in the container of top defined composition and will be applied on the contaminated material as top defined composition.
Because the pH of theme composition of the present invention, when making this contaminated materials decontamination, described material can be selected from the sclerosis carrier that applies with polyurethane paint, non-sclerosis carrier (glycerine phthalic acid lacquer simultaneously, has highly porous surface, have elastomer) and smart devices (carrier inside, radio, electronic equipment).
Because their low-corrosiveness, these compounds can also be used to make individual decontamination by contacting with skin.
Perpropionic Acid is generally 5-10 with respect to the mol ratio of pollutant for organophosphor pollutant (being hydrolyzed into phosphate), perhaps is generally 3-5 for organic sulfur pollutant (being oxidizing to sulfone).
Theme of the present invention still is used to obtain the method according to cleansing composition of the present invention.This method comprises following consecutive steps:
A) acquisition comprises the composition of Perpropionic Acid, pyridinedicarboxylic acid and hydroxy ethylene diphosphonic acid,
B) composition dissolves that will obtain in step a) is in comprising the Aquo-composition of surfactant, and this surfactant is made up of amine oxide and basifier.
In another embodiment of the invention, the method that is used to obtain cleansing composition comprises following consecutive steps:
A) acquisition comprises the composition of Perpropionic Acid and pyridinedicarboxylic acid
B) composition dissolves that will obtain in step a) is in Aquo-composition, and this Aquo-composition comprises surfactant, basifier and hydroxy ethylene diphosphonic acid and salt, preferably hydroxy ethylene diphosphonic acid sodium.
For instance, the hydroxy ethylene diphosphonic acid of theme composition of the present invention can be by Solutia company with trade (brand) name Dequest
Figure BPA00001250775000061
Product sold is formed and hydroxy ethylene diphosphonic acid sodium can be by Solutia company with trade (brand) name Dequest
Figure BPA00001250775000062
Product sold is formed.Following examples illustrate the present invention and do not limit the scope of the invention.In these embodiments, percentage is by weight, except as otherwise noted.
Embodiment 1
The solution of Perpropionic Acid is prepared by mixing following material: 1000g propionic acid, 500g 70% hydrogen peroxide, 25g sulfuric acid, 7.5g pyridinedicarboxylic acid and 15g hydroxy ethylene diphosphonic acid (Dequest ).Stir this mixture 12 hours at ambient temperature to obtain equilibrium concentration.So the solution of preparation comprises:
Weight %
Perpropionic Acid 38.2**
Hydrogen peroxide 8.3*
Propionic acid 33.8
Water 17.2
Sulfuric acid 1.0
Pyridinedicarboxylic acid 0.5
Hydroxy ethylene diphosphonic acid 1.0
* hydrogen peroxide uses cerous sulfate (IV) to carry out quantitative assay.
* gross activity oxygen carries out quantitative assay by iodometry.Perpropionic Acid is measured by the difference between gross activity oxygen and the hydrogen peroxide.
The solution of the previous preparation of 370g is mixed with following:
-70g Barquat MS 100 (from Lonza)
-100g
Figure BPA00001250775000072
-90g potassium hydroxide
-190g potash and
-900g water
Being used for decontamination uses.
Embodiment 2
The time dependent reactivity of the preparaton of preparation exists in embodiment 1 On decontamination in test.
In the glass reactor that stirs, the preparaton that 1.8g is prepared in embodiment 1 joins 50mg
Figure BPA00001250775000074
In.Therefore initial detergent/toxic agents mol ratio is 5.8.Add after T minute sampling and stop this reaction by adding excessive sodium thiosulfate.Then 8ml is added in the sample with the saturated water of NaCl, 10ml 50/50 ethyl acetate/hexane and 0.1% dibutyl sebacate (interior mark).Take out organic facies and drying and remaining on sodium sulphate
Figure BPA00001250775000075
Carry out quantitative assay by gas chromatography.
In embodiment 1, after the different ageing times of the preparaton of preparation, repeat this process.
The results are shown in the following table:
Figure BPA00001250775000081
Embodiment 3 (not according to the present invention)
The preparaton of describing in embodiment 1 based on Perpropionic Acid is compared with the similar preparaton based on peracetic acid.The process that 39% peracetic acid solution basis and embodiment 1 are consistent is replaced propionic acid with acetate, and other component that adds same amount then is prepared.
Use according to the process of in embodiment 2, describing
Figure BPA00001250775000082
The preparaton that test so obtains.Initial detergent/toxic agents mol ratio is 6.8.The results are shown in the following table:
Figure BPA00001250775000083
Therefore these embodiment demonstrate with respect to the preparaton based on peracetic acid, based on the preparaton of Perpropionic Acid for the advantage that makes the decontamination of organophosphor toxic agents.

Claims (11)

1. cleansing composition, it comprises:
(i) Perpropionic Acid
(ii) pyridinedicarboxylic acid
(iii) hydroxy ethylene diphosphonic acid or its salt is a kind of,
(iv) surfactant and
(v) basifier.
2. according to the composition of claim 1, the salt that is characterised in that hydroxy ethylene diphosphonic acid is hydroxy ethylene diphosphonic acid sodium.
3. according to claim 1 or 2 each compositions, be characterised in that basifier is selected from NaOH, potassium hydroxide, ammonium hydroxide, sodium metasilicate, potassium silicate, ammonium silicate, Boratex, potassium borate, ammonium borate and their mixture.
4. according to each composition of aforementioned claim, be characterised in that it also comprises alkaline buffer, is preferably selected from basic carbonate or alkaline silicate.
5. according to each composition of aforementioned claim, be characterised in that it also comprises non-ionic surface active agent.
6. according to each composition of aforementioned claim, be characterised in that Perpropionic Acid exists with 0.05-4.5mol/l concentration.
7. according to each composition of aforementioned claim, be characterised in that it is buffered in the pH of 7-10.
8. according to each composition of aforementioned claim, be characterised in that it comprises, represent with weight with respect to the gross weight of said composition:
-4%-16% Perpropionic Acid,
-0.1%-2% pyridinedicarboxylic acid
-0.5%-5% ethoxy diethyl Alendronate
-5%-20% surfactant
-2%-20% basifier and
-5%-15% alkaline buffer.
9. make the method for toxic agents organophosphor or organic sulfur and/or pollutant decontamination, it comprises makes described toxic agents and/or pollutant and contacts as each defined composition of front claim.
10. according to each the preparation method of cleansing composition of claim 1-8, be characterised in that it comprises following consecutive steps:
A) acquisition comprises the composition of Perpropionic Acid, pyridinedicarboxylic acid and hydroxy ethylene diphosphonic acid,
B) composition dissolves that will obtain in step a) is in comprising the Aquo-composition of surfactant, and this surfactant is made up of amine oxide and basifier.
11., be characterised in that it comprises following consecutive steps according to each the preparation method of cleansing composition of claim 1-8:
A) acquisition comprises the composition of Perpropionic Acid and pyridinedicarboxylic acid
B) composition dissolves that will obtain in step a) is in Aquo-composition, and this Aquo-composition comprises surfactant, basifier and hydroxy ethylene diphosphonic acid and salt, preferably hydroxy ethylene diphosphonic acid sodium.
CN200980115146.8A 2008-04-30 2009-04-28 Composition and process for the destruction of organophosphorus and/or organosulphur pollutants Expired - Fee Related CN102015035B (en)

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FR0852911 2008-04-30
PCT/FR2009/050779 WO2009141548A2 (en) 2008-04-30 2009-04-28 Composition and process for the destruction of organophosphorus and/or organosulphur pollutants

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RU2669850C1 (en) * 2017-08-28 2018-10-16 Федеральное Государственное бюджетное учреждение "27 Научный центр" Министерства обороны Российской Федерации Foam chloroactive agent and method for its preparation based on fluoro-organic foaming agent and n, n-dichloroarylsulfamides

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EP2271410B1 (en) 2011-10-12
IL208609A (en) 2013-12-31
FR2930732B1 (en) 2010-05-14
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JP5437363B2 (en) 2014-03-12
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