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WO1997034713A1 - Procede de dechloruration de composes chlores organiques - Google Patents

Procede de dechloruration de composes chlores organiques Download PDF

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Publication number
WO1997034713A1
WO1997034713A1 PCT/JP1997/000923 JP9700923W WO9734713A1 WO 1997034713 A1 WO1997034713 A1 WO 1997034713A1 JP 9700923 W JP9700923 W JP 9700923W WO 9734713 A1 WO9734713 A1 WO 9734713A1
Authority
WO
WIPO (PCT)
Prior art keywords
reaction
polar solvent
dechlorination
recovered
tank
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.)
Ceased
Application number
PCT/JP1997/000923
Other languages
English (en)
Japanese (ja)
Inventor
Fumio Tanimoto
Kiyohiko Tsukumo
Atsuhiko Nakamura
Tsuneo Yano
Mitoshi Higashiuchi
Toshinori Toma
Koichi Furuhashi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Neos Co Ltd
Mitsui and Co Ltd
Research Institute for Production Development
Original Assignee
Neos Co Ltd
Mitsui and Co Ltd
Research Institute for Production Development
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Neos Co Ltd, Mitsui and Co Ltd, Research Institute for Production Development filed Critical Neos Co Ltd
Priority to AU19437/97A priority Critical patent/AU703494B2/en
Publication of WO1997034713A1 publication Critical patent/WO1997034713A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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
    • A62D3/34—Dehalogenation using reactive chemical agents able to degrade
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B09—DISPOSAL OF SOLID WASTE; RECLAMATION OF CONTAMINATED SOIL
    • B09B—DISPOSAL OF SOLID WASTE NOT OTHERWISE PROVIDED FOR
    • B09B3/00—Destroying solid waste or transforming solid waste into something useful or harmless
    • 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
    • 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

Definitions

  • the present invention relates to a dechlorination method for safely treating organic chlorinated compounds such as polychlorinated biphenyls and dioxins, which are specific harmful substances.
  • PCB polychlorinated biphenyls
  • the inventors of the present application have conducted many more rigorous experiments, and as a result, have completed a more economical new process. That is, in the present invention, the organochlorine compound and excess alkali are stirred and mixed at 100 ° C. to 300 ° C. in a non-protonic polar solvent to thereby form a mixture in the reaction vessel.
  • organic chlorine compound refers to PCB, polychlorodibenzodioxin, polychlorodibenzofuran, or hardly decomposable organic chlorine such as 1,2,3 trichloro-14,1-nitro-biphenyl ether (CNP).
  • Alkali refers to at least one compound selected from the group consisting of caustic soda, caustic potassium, sodium lower alkoxide, potassium lower alkoxide, calcium hydroxide, and calcium oxide. A compound or a mixture of two or more. Caustic soda is particularly preferred in terms of economy.
  • the present inventors have found that a means for recovering an alkali with a lower alcohol is very effective for a dechlorination reaction. That is, not only the alcohol was sufficiently dissolved in the lower alcohol, but also the alcohol recovered in the lower alcohol increased to the newly added alcohol, which was found to have an effect of promoting the reaction. Was. The scholarly explanation of the reaction mechanism, etc. is currently being explored further and will be elucidated soon.
  • the excess alkali is recovered from the solids separated by filtration of the reaction solution with a lower alcohol or the like, and used for the next dechlorination reaction by a batch reaction. Part or most of it is recovered by distillation for the next batch reaction.
  • the concentration of the organochlorine compound participating in the reaction is relatively high and a solid is formed after cooling the reaction solution subjected to the dechlorination reaction, excess unreacted alkali is separated from the reaction product.
  • the generated solid is separated, and the alkali contained in the solid is dissolved in a lower alcohol, and separated and recovered.
  • the non-protonic polar solvent in the residual liquid from which the solid matter is separated is used as it is, or a part or most of the solvent is distilled and recovered, and reused in the dechlorination reaction.
  • the concentration of the organochlorine compound participating in the reaction is relatively low and the reaction solution that has undergone the dechlorination reaction is cooled, and the amount of solids produced is relatively small, unreacted alcohol
  • the reaction product is distilled without cooling to recover the non-protonic polar solvent, and the alcohol contained in the bottom is converted to lower alcohol. Dissolve, separate and collect.
  • the dechlorination reaction is carried out by dissolving and recovering with a lower alcohol.
  • the reactor is supplied with the recovered alkali that is reused in the reactor and the amount of alcohol that supplements the amount consumed in the dechlorination, and the temperature is raised together with the non-protonic polar solvent to start the reaction. It is preferable to distill most of the lower alcohol out of the system, recover it, and reuse it for the next recovery of the alcohol after the dechlorination reaction.
  • centrifugation, filtration under pressure, filtration under reduced pressure and the like are suitable for filtration of the reaction solution, which are selected in consideration of conditions such as the concentration of the raw material organic chlorine compound and the viscosity of the system.
  • Distillation and recovery of the solvent in the filtrate may be carried out in any form as long as it is an efficient method such as reduced pressure distillation and reduced pressure thin film distillation. If it is convenient for the distillation residue to become a dry solid, perform thorough distillation, crush the solid, filter it, and extract and wash the solid with low-grade alcohol to recover the alcohol.
  • the reaction product and the inorganic salt can be combined at room temperature with this nonprotonic polar solvent. Since it does not dissolve much, it can be separated by filtration without relatively complicated procedures, and only alkali is easily dissolved in lower alcohol, so that extraction and recovery can be performed advantageously.
  • one of the advantages of this process is that the alkali substance recovered with the lower alcohol is much more reactive than the first method used in this method.
  • the water content in the lower alcohol is suppressed to 10% or less, particularly preferably to only the attached water content.
  • a large amount of water was found to inhibit the dehalogenation reaction near the end point of the reaction because it dissolves the reaction product well as well as the corrosion of the equipment.
  • the role of trace water is still clear Although it has not been done, it is considered to play some effective role in the distribution of reaction products.
  • the lower alcohol used to separate and recover the alkali is at least one or two selected from the group consisting of alcohols having 1 to 4 carbon atoms and a water content of 10% or less. It is preferable to use a mixture composed of the above.
  • reaction solution a reaction solution containing a dechlorinated compound (hereinafter referred to as this reaction solution) .
  • the nonprotonic polar solvent is recovered and reused in the next dechlorination reaction. After the dechlorination reaction, it may be used for another purpose.
  • examples of the non-protonic polar solvent include sulfolane, dimethyl sulfoxide (hereinafter abbreviated as DMSO), 1,3-dimethyl-2-imidazolidinone (hereinafter abbreviated as DMI), and dimethyl alcohol.
  • DMSO dimethyl sulfoxide
  • DMI 1,3-dimethyl-2-imidazolidinone
  • dimethyl alcohol Use is made of alkylene glycol, tetramethylurea, N-methylbi-lidone, etc., which contains 50% or more of one or more of the above-mentioned compounds. From the viewpoint of cost and the like, it is particularly preferable to use a solvent containing 50% or more of DMSO, DMI, or dimethylpolyalkylene glycol.
  • a suitable temperature is 100 ° C to 300 ° C, but if the processing temperature is lower than 100 ° C, it may take a very long time, and 300 ° C may be required. If it is higher than C, there is a risk of evaporation of non-protonic solvents and organochlorine compounds and unexpected gelation due to side reactions. Especially when no additive is used, it is 150. It is preferably carried out at C to 250 ° C.
  • the organochlorine compound to be supplied to the reaction tank, the recovered alkali to be reused, the newly supplied alkali, the non-protonic polar solvent to be newly supplied, and the recovered non-protonic polar solvent to be reused about
  • the dechlorination reaction proceeds by the reaction of the solvent dissolved in a non-protonic polar solvent such as DMI with PCB in the liquid phase. Therefore, in order to promote the reaction, the concentration of the alkali dissolved in the DMI must be kept high to promote the association and contact between the molecules and the PCB molecules in the presence of the DMI.
  • the alkali used for the reaction in, ⁇ is dissolved in the DMI consumed in the dechlorination reaction by suspending finely ground solid caustic soda or caustic soda in the DMI to facilitate dissolution in the DMI. It is necessary to make up for the energy that is generated. As a result of various studies on the method, a suspension was made in a mixing tank equipped with a stirrer that mixes DMI and finely ground alkali, and then stirred.
  • a circulation line that extracts the liquid containing PCB from the reaction tank, passes through a static mixer, and returns to the reaction tank Mixing the suspension at the inlet of the static mixer and passing through the static mixer promotes the dissolution of alkali into the DMI and makes operation easier.
  • the reaction tank is heated while or after the suspension is supplied in this way, and the dechlorination reaction proceeds with the reaction temperature kept constant. This is circulated through a stick mixer. By doing so, the dechlorination reaction can proceed and the intended purpose can be achieved.
  • FIG. 1 shows a representative sheet of a process to which the present invention is applied.
  • FIG. 1 A first figure.
  • FIG. 2 is a diagram showing a typical flow sheet of another process to which the present invention is applied.
  • Fig. 3 shows an example of the material balance in the case where there is no recovery of alkali and solvent in the flow test for the process to which the present invention is applied.
  • FIG. 4 is a diagram showing an example of a material balance in a case where an alkali and a solvent are recovered in a flow test on a process to which the present invention is applied.
  • Figure 5 shows that raw materials were supplied to the reaction tank in the process to which the present invention was applied.
  • . 5 is a diagram showing an example of a method of supplying.
  • FIG. 6 is a diagram showing a typical flow sheet of still another process to which the present invention is applied.
  • FIG. 7 is a diagram showing that harmless insulating oil is reused as fuel oil in a flow test of a process to which the present invention is applied.
  • FIG. 8 is a diagram showing the material balance when DMI and the recovered alkali are recycled 15 times and reused as fuel oil in the flow test of the process to which the present invention is applied.
  • Fig. 1, Fig. 2, Fig. 5, Fig. 6, and Fig. 7 show typical flow sheets of this process
  • Fig. 3 shows the case without alkali and solvent recovery
  • Fig. 4 shows the case with alkali and solvent recovery
  • Figure 8 shows the DMI and the material yield for the case of recycling recovered alkali.
  • FIG. 1 shows an example in which the present invention is implemented.
  • 9 is a relatively high-concentration insulating oil containing PCB, which contains about 7% of PCB.
  • 1 is a non-protonic polar solvent (eg DMI)
  • 2 is an alkali (Eg, caustic soda)
  • 14 indicates DMI recovered in the still after the reaction
  • 13 indicates lower alcohol (eg, ethanol) in which alkali is dissolved.
  • DMI non-protonic polar solvent
  • 2 is an alkali (Eg, caustic soda)
  • 14 indicates DMI recovered in the still after the reaction
  • 13 indicates lower alcohol (eg, ethanol) in which alkali is dissolved.
  • This liquid is cooled to room temperature by passing a low-temperature refrigerant through a jacket 5, and the slurry-like reaction liquid 20 containing the solid NaC 1 generated here is filtered by a filter (1) of 6.
  • the filtrate 10 is supplied to the still 8 to recover the solvent and reused in the next batch reaction.
  • the remaining tank 15 obtained in this way was analyzed for PCB.
  • the separated cake (1) of 11 is dissolved in the dissolving tank 19 to dissolve the unreacted alcohol contained in the cake in ethanol, and the filtrate 13 is filtered by the filter (2) 7.
  • the filtrate 13 that separates into the cake (2) in 12 is ethanol that dissolves the recovered alkali and is reused in the next reaction by batch operation.
  • two filters 6 and 7 are shown separately, but the same one can be used separately by batch operation without being divided into two.
  • 3, 14, 16, 17, 18, 18, 36, 37, and 38 are each agitator, recovered DMI, recovered ethanol, ethanol, replenishment ethanol, recovered DMI tank, and first condenser.
  • the second capacitor is one.
  • Fig. 3 shows an example of the mass balance of the first batch operation without the use of alkalis and solvents, in which a relatively high concentration of insulating oil containing PCB is decomposed.
  • 13 ⁇ 44 shows the case of decomposing insulating oil containing PCB at relatively high concentration.
  • An example of the material balance of the embodiment in the case of reusing the alkali and the solvent is shown.
  • the temperature and operating conditions of each part are almost the same as those shown in the first embodiment.
  • FIG. 2 shows another example in which the present invention is implemented.
  • FIG. 5 shows an example of a method for supplying a raw material to a reaction tank.
  • the numbers shown here are the same as in Figures 1 and 2.
  • These raw materials are mixed well in advance in a mixing tank 34 equipped with a stirrer 33, and then mixed into a reaction liquid circulation line 30 through a pipe 31 using a supply pump 32.
  • the mixed reaction circulating liquid is completely mixed by a static mixer 29 equipped with a heater 35, and then the reaction tank 4 with the stirrer 3 (stirred reaction tank) And further subjected to a stirring operation by the stirrer 3.
  • the static mixer 29 extracts a part of the liquid subjected to the stirring operation in the reaction tank 4 through the circulation pump 28, the mixing intensity in the static mixer 29 is limited to the mixing intensity in the stirring reaction tank. Naturally, it is necessary to select something stronger than the mixing strength.
  • Alkali is supplied as a solid, and is heavier than the specific gravity of the liquid.Therefore, a part of the alkali precipitates at the bottom of the agitation reactor, and in the case of a reactor that mainly uses centrifugal agitation, the suspension cannot be maintained. Contact with the reaction solution tends to be incomplete. As a method of improving this, it is possible to maintain and improve the state of suspension in the reaction solution by extracting the precipitated solid from the bottom and passing it through a stick mixer 29. This operation is continued even after the supply of raw materials.
  • reference numeral 35 denotes a heater that heats a part of the static mixer, compensating for the temperature drop due to heat loss in the circulation line and increasing the temperature as needed, thereby increasing the reaction speed. It can be held.
  • the raw material supply method is directly supplied to the reaction tank, and the raw material is supplied using a static mixer. As a result, the following effects were obtained.
  • Example 5 shows an example of processing a relatively low-concentration insulating oil containing PCB by the process flow shown in FIG.
  • a still is provided separately, and the solvent is recovered here. 5
  • DMI is used as a solvent
  • its boiling point is 225.5 ° C at normal pressure, whereas it is 250-470 ° C for insulating oil, so it can be easily separated by simple distillation.
  • the tank can be used as a still. In this way, the process can be simplified, equipment costs can be saved, and processing costs can be reduced. An example of this is shown in Figure 6.
  • the distillation may be performed under reduced pressure in consideration of the temperature of the heating source. For example, at an absolute pressure of 4 OmmHg, DMI can be distilled off from the reaction solution at 150 ° C.
  • PCBs can be removed from TFO (insulating oil) very economically by reusing the recovered DMI and alkali dissolved in alcohol, and it is harmless except for PCB.
  • the converted insulating oil can be reused as fuel oil.
  • Fig. 7 shows the process flow of this example, and Fig. 8 shows the material balance at that time.
  • Fig. 7, 39, 40, 41, 42, 43, 44, and 45 denote the adjustment tank, the cooling tank, the filtrate receiving tank, the distillate (DMI) receiving tank, the separator, and the high-pressure insulating oil (TFO).
  • Receiving tank. 46, 47, 48, 49, 50, 51, 52, 53 are alkali dissolution tanks, alcohol supply tanks, storage tanks containing alkali-containing alcohol solutions, alkali supply tanks, cake storage tanks, and raw materials (TFO containing PCBs) Tank, solvent (DMsI) supply tank, and new supply tank.
  • Reference numerals 54, 55, 56, and 57 denote a drive motor for stirring, a TFO washing tank, a TFO washing tank, and a TFO heavy oil mixing tank.
  • the recovered DMI was recycled 15 times
  • the alkali recovered in the metamorphic alcohol was recycled 15 times or more.
  • the PCB in the new TFO containing 80 ppm of PCB is dechlorinated using new DMI and new caustic soda.
  • the liquid after this is separated into a TFO phase and a DMI phase (solid-liquid phase containing caustic soda solid), and this DMI phase (containing caustic soda) is used again for the reaction.
  • the reaction is first separated and separated into a TFO and DMI phase.
  • a small amount of lower alcohol containing 10% or less of water
  • To further assist in phase separation perform a simple filtration once (pressurized or depressurized) and then separate phases.
  • the TF0 phase is washed with water, it is mixed with heavy oil and reused as fuel oil.
  • the DMI phase DMI and caustic soda are reused to decompose the PCB in the new TFO. Repeat this 15 times. A small amount of DMI and a small amount of caustic soda may be added as needed for the reaction.
  • the DMI phase containing caustic soda, reaction products and sodium chloride is usually first filtered through a centrifugal filter to separate the solid and liquid. Distill the liquid filtrate to recover DMI. This DMI is recycled to the next reaction.
  • solid phase cake
  • an amount of denatured ethyl alcohol that sufficiently dissolves caustic soda is added, and the remaining caustic soda after use in the dechlorination reaction is recovered.
  • most of the reaction product and the generated sodium chloride hardly dissolve in denatured ethyl alcohol, and therefore exist as a solid.
  • These mixtures are filtered through a centrifugal filter, Separate the solid and liquid. Most of the caustic soda transfers to the liquid filtrate and is recycled for the next reaction.
  • the recoveries of DMI and alkali were 99% and 91%, respectively.
  • the material balance of the process is almost the same as in Example 5, except that the solvent used is triethylene glycol dimethyl ether (boiling point 2 16 ° C) or tetraethylene glycol dimethyl ether (boiling point 275) instead of DMI.
  • the solvent used is triethylene glycol dimethyl ether (boiling point 2 16 ° C) or tetraethylene glycol dimethyl ether (boiling point 275) instead of DMI.
  • This is an example of a process in which the reaction was carried out 15 times by using caustic soda as the alkali.
  • the present invention can be applied to the treatment of hydrocarbon oils containing all concentrations of organochlorine compounds, for example, PCB-contaminated transformer oil or 100% PCB, with good results.
  • the hydrocarbon oil mentioned above will be regenerated and reused. Therefore, the method for dechlorinating an organic chlorinated compound according to the present invention relates to a process for dechlorinating and detoxifying an organic chlorinated compound in a very economical manner. As a result, it is possible to safely and economically contribute to the improvement of the environment.

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  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Chemical & Material Sciences (AREA)
  • Business, Economics & Management (AREA)
  • Emergency Management (AREA)
  • Engineering & Computer Science (AREA)
  • Environmental & Geological Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fire-Extinguishing Compositions (AREA)
  • Physical Or Chemical Processes And Apparatus (AREA)
  • Processing Of Solid Wastes (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)

Abstract

De façon à traiter des composés organiques chlorés qui sont généralement difficiles à décomposer, au moyen d'un procédé ne posant aucun problème en termes de déroulement de processus et offrant d'excellentes caractéristiques tant au niveau sécurité qu'économie, on utilise un excédent d'alcali pour compléter le traitement lorsque l'on fait réagir une huile isolante (9) contenant des composés chlorés organiques tels que du PCB avec de l'alcali du type soude caustique (2), au sein d'un solvant polaire aprotique du type 1,3-diméthyl-imidazolidinone (1) aux fins de chloruration. On fait également se dissoudre un excédent d'alcali dans un alcool inférieur du type éthanol (17) et on le récupère, puis on récupère le solvant polaire aprotique. Dans ce procédé, un étape du traitement est perfectionnée en ce qui concerne la sécurité, l'économie et l'utilité et l'on rend l'huile inoffensive, ce qui permet sa ré-utilisation en tant que mazout et analogue et donc une utilisation efficace des ressources.
PCT/JP1997/000923 1996-03-19 1997-03-19 Procede de dechloruration de composes chlores organiques Ceased WO1997034713A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU19437/97A AU703494B2 (en) 1996-03-19 1997-03-19 Dechlorination process of organnochlorine compound

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP11306096A JP3197818B2 (ja) 1996-03-19 1996-03-19 有機塩素化合物の脱塩素化方法
JP8/113060 1996-03-19

Publications (1)

Publication Number Publication Date
WO1997034713A1 true WO1997034713A1 (fr) 1997-09-25

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Application Number Title Priority Date Filing Date
PCT/JP1997/000923 Ceased WO1997034713A1 (fr) 1996-03-19 1997-03-19 Procede de dechloruration de composes chlores organiques

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JP (1) JP3197818B2 (fr)
KR (1) KR100358206B1 (fr)
AU (1) AU703494B2 (fr)
TW (1) TW374755B (fr)
WO (1) WO1997034713A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10304641A1 (de) * 2002-02-07 2003-09-04 Toshiba Kk System zur Entgiftung toxischer chlorierter organischer Verbindungen und Verfahren zum Rezyklieren des entgifteten Abfalls

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4357645B2 (ja) * 1999-07-15 2009-11-04 旭化成ケミカルズ株式会社 １，３−シクロアルカジエンの製造法
KR100697562B1 (ko) * 2006-01-26 2007-03-21 한국원자력연구소 고온의 알칼리 용융염을 이용하여 폴리염화비페닐을함유하는 절연유의 분해 처리하는 방법

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS49126651A (fr) * 1973-04-10 1974-12-04
JPS61500442A (ja) * 1983-10-24 1986-03-13 ナイアガラ・モウホ−ク・パワ−・コ−ポレイシヨン 炭火水素溶液中のハロゲン化芳香族類含量の低減方法
US4910353A (en) * 1983-02-07 1990-03-20 Transformer Service, Inc. Dehalogenation of polychlorinated biphenyls and other related compounds
JPH05200129A (ja) * 1991-03-23 1993-08-10 Metallges Ag ポリハロゲン化有機化合物の分解方法
JPH0625691A (ja) * 1992-06-05 1994-02-01 Res Inst For Prod Dev 炭化水素油よりハロゲン化芳香族化合物を除去する方法
JPH078572A (ja) * 1993-06-24 1995-01-13 Res Inst For Prod Dev ハロゲン化芳香族化合物を分解する方法

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS49126651A (fr) * 1973-04-10 1974-12-04
US4910353A (en) * 1983-02-07 1990-03-20 Transformer Service, Inc. Dehalogenation of polychlorinated biphenyls and other related compounds
JPS61500442A (ja) * 1983-10-24 1986-03-13 ナイアガラ・モウホ−ク・パワ−・コ−ポレイシヨン 炭火水素溶液中のハロゲン化芳香族類含量の低減方法
JPH05200129A (ja) * 1991-03-23 1993-08-10 Metallges Ag ポリハロゲン化有機化合物の分解方法
JPH0625691A (ja) * 1992-06-05 1994-02-01 Res Inst For Prod Dev 炭化水素油よりハロゲン化芳香族化合物を除去する方法
JPH078572A (ja) * 1993-06-24 1995-01-13 Res Inst For Prod Dev ハロゲン化芳香族化合物を分解する方法

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10304641A1 (de) * 2002-02-07 2003-09-04 Toshiba Kk System zur Entgiftung toxischer chlorierter organischer Verbindungen und Verfahren zum Rezyklieren des entgifteten Abfalls

Also Published As

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KR19990014899A (ko) 1999-02-25
AU1943797A (en) 1997-10-10
KR100358206B1 (ko) 2003-01-24
TW374755B (en) 1999-11-21
JPH09253602A (ja) 1997-09-30
JP3197818B2 (ja) 2001-08-13
AU703494B2 (en) 1999-03-25

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