CA1299136C - Decomposition of halogenated organic compounds using a polyoxygenated compound and ultraviolet radiation - Google Patents
Decomposition of halogenated organic compounds using a polyoxygenated compound and ultraviolet radiationInfo
- Publication number
- CA1299136C CA1299136C CA000517186A CA517186A CA1299136C CA 1299136 C CA1299136 C CA 1299136C CA 000517186 A CA000517186 A CA 000517186A CA 517186 A CA517186 A CA 517186A CA 1299136 C CA1299136 C CA 1299136C
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- Prior art keywords
- reagent
- compound
- reaction
- alkali
- decomposition
- Prior art date
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- Expired - Lifetime
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Abstract
Abstract Polyhalogenated organic compounds such as PCB, TCDD, PCDD, PCDF, etc. are rapidly dehalogenated and detoxified under the action of UV radiation and a reagent consisting of a) a polyoxygenated compound, such as polyethyleneglycols, polyhydroxy compounds and products of condensation of ethylene oxide and propylene oxide and b) a base and eventually, c) an oxidizing agent or a source of free radicals.
Description
~299~36 PROCESS FOR THB FAST CHE~ICAL DECOMPOSITION OF HALOGBNATED AND
POLYHALOGENATED ORGANIC COMPOUNDS, SUCH AS POLYCHLORO-BIPHENYLS, POLYCHLORODIBENZOFURANS AND POLYC~LORO-DIBENZODIOXINS, AND FOR THE DECONTAMINATION OF SURFACES OR
FLUIDS.
The present invention relates to a novel method for the decomposition of halogenated and polyhalogenated organic compounds and for the decontamination of surfaces or fluids contaminated by these substances. ~he environmental problem o resulting from the high or very high toxicity of polyhalogenated compounds used in industry, such as polychlorobiphenyls, polyhalogenophenols, inseaticides such as DDT, Kepone~, or their reaction products resulting at a high temperature, fires, explosions in the case of polyhalo-genodibenzodioxins and polyhalogenodibenzofurans, is wellknown. Due to the high stability of the bond between carbon and halogen the polyhalogenated compounds exhibit practically no biodegradability and they remain in the environment for a period of time which has practically no limit with serious problems of pollution and contamination.
8everal methods have been proposed for the degradation of the polyhalogenated compounds. For instance, European Patent 118,858, granted January 7, 1988 describes an effective decontaminating reagent which is active even at room temperature and which may be applied for the decontamination of the soil, parts of installations, buildings, dieleotric fluids or other industrial fluids. This reagent consists ofO
129913Ç;
a) a polyoxygenated compound, sueh as polyethylene-glycol~ (PEG), polyhydroxy compound~, the products of polyeondensation of ethylene exide and propylene oxide (Nlxolen ~R));
b) a ba~e, preferably alkali or alkaline earth earbonate~ or bicarbonates or alkali or alkaline earth alcoholates when component a) is a Nixolen;
e) eventually an oxidizing agent or a source of free radicals such as Na202 or sao2. eomponent c) is not necessary when there are used alkali or alXaline earth aleoholates and Nixolen.
~he reagent may be formulated in various manners with an ample range of viseosity aecording to the different applications. Further, European Application Publication No.
EP-A-0135043, published Mareh 27, 1985, also filed by the applicant, deseribes a device for the continuous deeontamination of industrial fluids by means of the above de~cribed reagent, suitably supported and adsorbed on solid support~.
Other method~ are based on a reductive photodecom-po~ition. The compound to be destroyed is irradiated with W
radiation of variable wave lengths between 280 and 320 nm in the presenoe of a hydrogen donor. (æci. Total Environment 10, 97-104, 1978, Ritchens et al. in "Detoxication of Hazardous Waste", Ann. Axbor Scienee, p. 215-226 and U.S.P.
No. 4,144,152) . The method known under the name LARC (Light Activated Reduetion of Chemicals), described in the same U.~.P. 4,144,152, utilize~ a flow of gaseous hydrogen which ,. .
.
~299136 optimizes the photochemical conditions to carry out the dehalogenation of halogenated organic substances while the other methods on the other hand utilize alcohols which contain very mobile hydrogen atoms.
It has now been found surprisingly and this is the object of the present invention, that the use of W radiation together with the reagent and the device de cribed in the above mentioned European Patent 118,858 and Publication No.
EP-A-0135043 permits one to achieve substantial advantages lo with respect to the known methods. To state the matter in different words, the chemical processes of dehalogenation obtained by means of the reagent described hereinabove, which are based on a radical-anionic mechanism ~ecome much more effective and rapid due to the synergistic action with ultraviolet radiation. In distinction to the known methods, it is not nece~sary to use a specific and effective donor of hydrogen or gaseous hydrogen. The method according to the invention is particularly simple, economical and practical also for application in the field such as, soil, extended surfaces in the open, etc. because it requires the use of reagents which are of little cost, easily available and not dangerous and natural or artificial W sources which are easy to handle and easily available.
It is, for instance, possible to use, in addition to sunlight, high or low pressure mercury vapor lamps and wave length~ between 2~0 and 320 nm.
The proce~s according to the present invention may be used for the decontamination of metallic surfaces, porous ~9136 surfaces, such as plaster, cement, wood, grit, etc. or hydrocarbon fluids, silicone fluids, non-halogenated synthetic fluid~ such as gas oil and oil for transformers, etc.
As already shown in the European Patent No. 118,858, the viscosity of the reagent being used may be regulated essentially by the choice of component a) and depends on the type of material being treated. Therefore, a liquid reagent is particularly suitable for porou~ materials while metallic surfaces require preferably a viscous reagent or a reagent capable of forming a solid film which later may be removed.
A typical example of a reagent may consist of 5-40% by weight of sodium carbonate, 0.1-10% by weight of sodium peroxide or barium peroxide and 50-95% by weight of NixolenR optionally mixed with PEG. Alternately, it is possible to use a reagent consisting exclusively of 80-95% by weight of a Nixolen and 20-5% by weight of an alkali alcoholate such as sodium methylate. The reagent may be applied by spraying, spreading or bru~hing, or in the case of decontamination of fluids, they are simply caused to pas~ on a support on which the reagent previou~ly ha~ been adsorbed. ~his support which may also consist of the same base which is part of the composition of the reagent, may eventually be in~erted in a device of the type described in European PubliGation No. EP-A-0135043.
Further it has been found that the penetration of the reagent into por~u~ materials may be significantly improved by using polyether solvent~, in parti~ular ethylene or propylene glycols ~hich are mono or disubstituted with alkyl groups such a diethylene glyaol dimethyl ether or diglymeR, optionally in the presence of tensioactive agents and surfactants. Finally, always for the purpose of promoting the reaction of dehalogenation, in addition to W radiation it is possible to rely on other synergistic actions, such as thermal sources, infrared, microwave~, electric and ultrasonic fields, the utility of which has already been found and described previously. In the presence of W radiation, the decontamination reaction proceeds rapidly also at room temperature, a fact which is particularly convenient for the application to large surface areas in the open, etc.
The following examples are not intended to limit the invention but merely to illustrate in more detail the process according to the invention and the advantages which may be achieved.
EXAMPLE 1 - SUPPOR~ METAL~IC PLATE CONTAMINATED WITH PCB
A liquid reagent in the amount of 1000 mg/mq i3 spread on two steel plate~ of 100 $ 100 mm size contaminated by 1000 mg/mg of PCB in such a manner to form a continuous film.
~he liquid reagent consists of NixolenR VSl3 and sodium methylate in the proportions of 95-5% by weight.
one plate ~plate A~ is exposed to W radiation from a high pressure mercury vapor lamp with 150 W while the other plate serves as control. The results obtained from the analysis with gas chromatography and with the electron capture det~ctor (GCECD) are summari~ed in the table below.
Experimental Unit of * Plate ~ Plate B
Conditions Measure with W without W
-Initial surface mg/mq 1,000 1,000 co~tamination Quantity of the g/mq 1,000 1,000 reagent Reaction tempera- oc 20 20 ture Reaction time hours 44 336 of plate A
Final surface mg/mq <1 2 contamination * mq = square meter EXAMP~E 2 - POROU8 SUPPORT, MORTAR CONTAMINATED WITH PCB
Two blocks of mortar of composition consisting of 3 parts of sand, 1 part of cement 345, and 0.8 parts of water, of dimensions 35 x 35 x 25 mm are contaminated with 300 mg/mq of PCB.
The contaminated surface is treated with 3000 g/mq of 1 : 1 solution of a mixture of Nixolen~R) VS13 - sodium methylate (95:5 by weight) in diethylene glycol dimethyl ether as a solvent (Diglyme~R)).
one of the block~ ~A) is exposed to W source as in Example 1 and the comparison has been made with the reaction carried out in the absence of UV radiation.
The results are, analyzed with GCECD, and summarized hereinbelow.
Experimental Unit of Support ~ Support B
Conditions Measurewith UV without W
-Initial ~urface mgJmq 300 300 contamination Quantity of the g/mq 3,000 3,000 reagent Reaction tempera- oc 2 0 2 0 ture Reaction time hours 15 328 Fin~l surfa~e mg/m~ 1 75 contamination EXAMPLE 3 - SUPPORT: MINERAL OIL CON~AMINA~ED WITH PCB
In two 500 ac beakers containing ISOVOLTINE(R) mineral oil contaminated with 1,000 ppm of PCB, there is introduced the following reagent: Nixolen~R) VSl3 - sodium methylate ~85:15 by weight) at a concentration of 2,000 ppm per beaker.
I~ one beaker there i9 immersed the W source protected by a quartz shield. The results obtained by GCECD analysis are summarized in the table hereinbelow.
~299136 Experimental Unit ofSupport A Support B
Conditions Measurewith W without W
Initial fluid ppm 1,000 1,000 contamination Quantity of the g/mq 2,000 2,000 reagent Reaction tempera- C 80 80 ture Reaction time hours 3 3 of support A
Final fluid ppm 25 85 contamination EXAMPLE 4 - 8UPPORT: PLASTER CONTAMINATED WITH PCDD AND PCDF
A mixture of Nixolen~R~ VS13 - Sodium methylate ~85:15 by weight) in the amount of 1500 g/mq i9 spread on 1 mq of a wall with a plaster contaminated by PCDD and PCDF as a result of an explosion and a fire of electric condensers which had been impregnated with PCB. The wall is then exposed for 96 hours to an ultraviolet source from a mercury vapor lamp at high pressure operating at 500 W. At the end of the treatment, the wall is washed (wiped) and then it is analyzed by gas mass analyqis ~GCNS) and comparison is made between the initial and the final contamination. The results are reported hereinbelow.
COMPOVNDS IDENTIFIED IN VNIT OF
THE ANALYSIg GC-M8 MEASUREBEFORE AFTER
POLYHALOGENATED ORGANIC COMPOUNDS, SUCH AS POLYCHLORO-BIPHENYLS, POLYCHLORODIBENZOFURANS AND POLYC~LORO-DIBENZODIOXINS, AND FOR THE DECONTAMINATION OF SURFACES OR
FLUIDS.
The present invention relates to a novel method for the decomposition of halogenated and polyhalogenated organic compounds and for the decontamination of surfaces or fluids contaminated by these substances. ~he environmental problem o resulting from the high or very high toxicity of polyhalogenated compounds used in industry, such as polychlorobiphenyls, polyhalogenophenols, inseaticides such as DDT, Kepone~, or their reaction products resulting at a high temperature, fires, explosions in the case of polyhalo-genodibenzodioxins and polyhalogenodibenzofurans, is wellknown. Due to the high stability of the bond between carbon and halogen the polyhalogenated compounds exhibit practically no biodegradability and they remain in the environment for a period of time which has practically no limit with serious problems of pollution and contamination.
8everal methods have been proposed for the degradation of the polyhalogenated compounds. For instance, European Patent 118,858, granted January 7, 1988 describes an effective decontaminating reagent which is active even at room temperature and which may be applied for the decontamination of the soil, parts of installations, buildings, dieleotric fluids or other industrial fluids. This reagent consists ofO
129913Ç;
a) a polyoxygenated compound, sueh as polyethylene-glycol~ (PEG), polyhydroxy compound~, the products of polyeondensation of ethylene exide and propylene oxide (Nlxolen ~R));
b) a ba~e, preferably alkali or alkaline earth earbonate~ or bicarbonates or alkali or alkaline earth alcoholates when component a) is a Nixolen;
e) eventually an oxidizing agent or a source of free radicals such as Na202 or sao2. eomponent c) is not necessary when there are used alkali or alXaline earth aleoholates and Nixolen.
~he reagent may be formulated in various manners with an ample range of viseosity aecording to the different applications. Further, European Application Publication No.
EP-A-0135043, published Mareh 27, 1985, also filed by the applicant, deseribes a device for the continuous deeontamination of industrial fluids by means of the above de~cribed reagent, suitably supported and adsorbed on solid support~.
Other method~ are based on a reductive photodecom-po~ition. The compound to be destroyed is irradiated with W
radiation of variable wave lengths between 280 and 320 nm in the presenoe of a hydrogen donor. (æci. Total Environment 10, 97-104, 1978, Ritchens et al. in "Detoxication of Hazardous Waste", Ann. Axbor Scienee, p. 215-226 and U.S.P.
No. 4,144,152) . The method known under the name LARC (Light Activated Reduetion of Chemicals), described in the same U.~.P. 4,144,152, utilize~ a flow of gaseous hydrogen which ,. .
.
~299136 optimizes the photochemical conditions to carry out the dehalogenation of halogenated organic substances while the other methods on the other hand utilize alcohols which contain very mobile hydrogen atoms.
It has now been found surprisingly and this is the object of the present invention, that the use of W radiation together with the reagent and the device de cribed in the above mentioned European Patent 118,858 and Publication No.
EP-A-0135043 permits one to achieve substantial advantages lo with respect to the known methods. To state the matter in different words, the chemical processes of dehalogenation obtained by means of the reagent described hereinabove, which are based on a radical-anionic mechanism ~ecome much more effective and rapid due to the synergistic action with ultraviolet radiation. In distinction to the known methods, it is not nece~sary to use a specific and effective donor of hydrogen or gaseous hydrogen. The method according to the invention is particularly simple, economical and practical also for application in the field such as, soil, extended surfaces in the open, etc. because it requires the use of reagents which are of little cost, easily available and not dangerous and natural or artificial W sources which are easy to handle and easily available.
It is, for instance, possible to use, in addition to sunlight, high or low pressure mercury vapor lamps and wave length~ between 2~0 and 320 nm.
The proce~s according to the present invention may be used for the decontamination of metallic surfaces, porous ~9136 surfaces, such as plaster, cement, wood, grit, etc. or hydrocarbon fluids, silicone fluids, non-halogenated synthetic fluid~ such as gas oil and oil for transformers, etc.
As already shown in the European Patent No. 118,858, the viscosity of the reagent being used may be regulated essentially by the choice of component a) and depends on the type of material being treated. Therefore, a liquid reagent is particularly suitable for porou~ materials while metallic surfaces require preferably a viscous reagent or a reagent capable of forming a solid film which later may be removed.
A typical example of a reagent may consist of 5-40% by weight of sodium carbonate, 0.1-10% by weight of sodium peroxide or barium peroxide and 50-95% by weight of NixolenR optionally mixed with PEG. Alternately, it is possible to use a reagent consisting exclusively of 80-95% by weight of a Nixolen and 20-5% by weight of an alkali alcoholate such as sodium methylate. The reagent may be applied by spraying, spreading or bru~hing, or in the case of decontamination of fluids, they are simply caused to pas~ on a support on which the reagent previou~ly ha~ been adsorbed. ~his support which may also consist of the same base which is part of the composition of the reagent, may eventually be in~erted in a device of the type described in European PubliGation No. EP-A-0135043.
Further it has been found that the penetration of the reagent into por~u~ materials may be significantly improved by using polyether solvent~, in parti~ular ethylene or propylene glycols ~hich are mono or disubstituted with alkyl groups such a diethylene glyaol dimethyl ether or diglymeR, optionally in the presence of tensioactive agents and surfactants. Finally, always for the purpose of promoting the reaction of dehalogenation, in addition to W radiation it is possible to rely on other synergistic actions, such as thermal sources, infrared, microwave~, electric and ultrasonic fields, the utility of which has already been found and described previously. In the presence of W radiation, the decontamination reaction proceeds rapidly also at room temperature, a fact which is particularly convenient for the application to large surface areas in the open, etc.
The following examples are not intended to limit the invention but merely to illustrate in more detail the process according to the invention and the advantages which may be achieved.
EXAMPLE 1 - SUPPOR~ METAL~IC PLATE CONTAMINATED WITH PCB
A liquid reagent in the amount of 1000 mg/mq i3 spread on two steel plate~ of 100 $ 100 mm size contaminated by 1000 mg/mg of PCB in such a manner to form a continuous film.
~he liquid reagent consists of NixolenR VSl3 and sodium methylate in the proportions of 95-5% by weight.
one plate ~plate A~ is exposed to W radiation from a high pressure mercury vapor lamp with 150 W while the other plate serves as control. The results obtained from the analysis with gas chromatography and with the electron capture det~ctor (GCECD) are summari~ed in the table below.
Experimental Unit of * Plate ~ Plate B
Conditions Measure with W without W
-Initial surface mg/mq 1,000 1,000 co~tamination Quantity of the g/mq 1,000 1,000 reagent Reaction tempera- oc 20 20 ture Reaction time hours 44 336 of plate A
Final surface mg/mq <1 2 contamination * mq = square meter EXAMP~E 2 - POROU8 SUPPORT, MORTAR CONTAMINATED WITH PCB
Two blocks of mortar of composition consisting of 3 parts of sand, 1 part of cement 345, and 0.8 parts of water, of dimensions 35 x 35 x 25 mm are contaminated with 300 mg/mq of PCB.
The contaminated surface is treated with 3000 g/mq of 1 : 1 solution of a mixture of Nixolen~R) VS13 - sodium methylate (95:5 by weight) in diethylene glycol dimethyl ether as a solvent (Diglyme~R)).
one of the block~ ~A) is exposed to W source as in Example 1 and the comparison has been made with the reaction carried out in the absence of UV radiation.
The results are, analyzed with GCECD, and summarized hereinbelow.
Experimental Unit of Support ~ Support B
Conditions Measurewith UV without W
-Initial ~urface mgJmq 300 300 contamination Quantity of the g/mq 3,000 3,000 reagent Reaction tempera- oc 2 0 2 0 ture Reaction time hours 15 328 Fin~l surfa~e mg/m~ 1 75 contamination EXAMPLE 3 - SUPPORT: MINERAL OIL CON~AMINA~ED WITH PCB
In two 500 ac beakers containing ISOVOLTINE(R) mineral oil contaminated with 1,000 ppm of PCB, there is introduced the following reagent: Nixolen~R) VSl3 - sodium methylate ~85:15 by weight) at a concentration of 2,000 ppm per beaker.
I~ one beaker there i9 immersed the W source protected by a quartz shield. The results obtained by GCECD analysis are summarized in the table hereinbelow.
~299136 Experimental Unit ofSupport A Support B
Conditions Measurewith W without W
Initial fluid ppm 1,000 1,000 contamination Quantity of the g/mq 2,000 2,000 reagent Reaction tempera- C 80 80 ture Reaction time hours 3 3 of support A
Final fluid ppm 25 85 contamination EXAMPLE 4 - 8UPPORT: PLASTER CONTAMINATED WITH PCDD AND PCDF
A mixture of Nixolen~R~ VS13 - Sodium methylate ~85:15 by weight) in the amount of 1500 g/mq i9 spread on 1 mq of a wall with a plaster contaminated by PCDD and PCDF as a result of an explosion and a fire of electric condensers which had been impregnated with PCB. The wall is then exposed for 96 hours to an ultraviolet source from a mercury vapor lamp at high pressure operating at 500 W. At the end of the treatment, the wall is washed (wiped) and then it is analyzed by gas mass analyqis ~GCNS) and comparison is made between the initial and the final contamination. The results are reported hereinbelow.
COMPOVNDS IDENTIFIED IN VNIT OF
THE ANALYSIg GC-M8 MEASUREBEFORE AFTER
2, 3, 7,8 TCDF ng/wipe 206 N.D.
TCDD ng/wipeN.D.
TCDF ng/wipe1040 N.D.
PCDD ng/wipe1480 N.D.
PCDF ng/wipe 80 N.D.
HXCDD ng/wipe 659 N.D.
HXCDF ng/wipeN.D. N.D.
OCDD ng/wipe 1,9 N.D.
OCDF ng/wipeN.D. N.D.
(*) N.D. means "not determined~ because less than the amount detected by GCMS
TCDD ng/wipeN.D.
TCDF ng/wipe1040 N.D.
PCDD ng/wipe1480 N.D.
PCDF ng/wipe 80 N.D.
HXCDD ng/wipe 659 N.D.
HXCDF ng/wipeN.D. N.D.
OCDD ng/wipe 1,9 N.D.
OCDF ng/wipeN.D. N.D.
(*) N.D. means "not determined~ because less than the amount detected by GCMS
Claims (7)
1. A method for the decomposition of a polyhalogenated compound by reaction with a reagent consisting of a) a polyoxygenated compound which is a polyethylene glycol, a polyhydroxy compound, or a product formed by condensation of propylene oxide and ethylene oxide, b) an alkali or alkaline earth carbonate or bicarbonate or an alkali or alkaline earth alcoholate when component a) is a polycondensate of ethylene oxide and propylene oxide and c) an oxidizing agent or a source of free radicals, said component c) being used when said component a) is a polyethylene glycol or a polyhydroxy compound and wherein the reaction is carried out in the presence of ultraviolet radiation.
2. The method according to Claim 1 wherein said polyhalogenated compound is on a metallic or porous surface, in a hydrocarbon fluid, a silicone fluid or in a nonhalogenated synthetic fluid.
3. The method according to Claim 1 wherein the reagent consists of 80-95% by weight of a polycondensate of ethylene oxide and propylene oxide and 20 to 5% by weight of an alkali alcoholate in the absence of an oxidizing agent.
4. The method according to Claim 1 wherein said reagent is dissolved in a polar solvent comprising a mono-alkyl or di-alkyl ethylene glycol or propylene glycol, and is applied to a porous surface.
5. The method according to Claim 1 wherein at least one of a tensioactive agent or a surfactant is mixed with said reagent.
6. The method according to Claim 1 wherein said polyhalogenated compound is polychlorobiphenyl (PCB), a polychlorodibenzofuran (PCDF), a polychlorodibenzo-dioxin (PCDD) or bromine or fluorine analogs thereof.
7. The method according to Claim 1 wherein the reaction is carried out in the presence of heat, infra-red, microwave, ultrasonic energy or an electric field.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000517186A CA1299136C (en) | 1984-07-20 | 1986-08-29 | Decomposition of halogenated organic compounds using a polyoxygenated compound and ultraviolet radiation |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US63271884A | 1984-07-20 | 1984-07-20 | |
| CA000517186A CA1299136C (en) | 1984-07-20 | 1986-08-29 | Decomposition of halogenated organic compounds using a polyoxygenated compound and ultraviolet radiation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1299136C true CA1299136C (en) | 1992-04-21 |
Family
ID=25671084
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000517186A Expired - Lifetime CA1299136C (en) | 1984-07-20 | 1986-08-29 | Decomposition of halogenated organic compounds using a polyoxygenated compound and ultraviolet radiation |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA1299136C (en) |
-
1986
- 1986-08-29 CA CA000517186A patent/CA1299136C/en not_active Expired - Lifetime
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