EP0380782B1 - Agents de déshalogénation liquides - Google Patents
Agents de déshalogénation liquides Download PDFInfo
- Publication number
- EP0380782B1 EP0380782B1 EP89122423A EP89122423A EP0380782B1 EP 0380782 B1 EP0380782 B1 EP 0380782B1 EP 89122423 A EP89122423 A EP 89122423A EP 89122423 A EP89122423 A EP 89122423A EP 0380782 B1 EP0380782 B1 EP 0380782B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- liquid
- dehalogenation
- carbon atoms
- alkali metal
- alcohol
- 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.)
- Expired - Lifetime
Links
- 238000005695 dehalogenation reaction Methods 0.000 title claims abstract description 17
- 239000007788 liquid Substances 0.000 title claims abstract description 17
- 239000003921 oil Substances 0.000 claims abstract description 30
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 21
- 229920000570 polyether Polymers 0.000 claims abstract description 16
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 12
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 12
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 12
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 10
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000002699 waste material Substances 0.000 claims description 8
- 239000011734 sodium Substances 0.000 claims description 7
- 229910052708 sodium Inorganic materials 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 abstract description 7
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 7
- 230000003647 oxidation Effects 0.000 abstract description 6
- 238000007254 oxidation reaction Methods 0.000 abstract description 6
- 239000007787 solid Substances 0.000 abstract description 4
- 239000000470 constituent Substances 0.000 abstract description 2
- 238000001816 cooling Methods 0.000 abstract description 2
- 239000010913 used oil Substances 0.000 abstract 1
- 239000003513 alkali Substances 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- 230000007935 neutral effect Effects 0.000 description 10
- 239000000047 product Substances 0.000 description 6
- MXVMODFDROLTFD-UHFFFAOYSA-N 2-[2-[2-(2-butoxyethoxy)ethoxy]ethoxy]ethanol Chemical compound CCCCOCCOCCOCCOCCO MXVMODFDROLTFD-UHFFFAOYSA-N 0.000 description 5
- 150000002334 glycols Chemical class 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 125000000963 oxybis(methylene) group Chemical group [H]C([H])(*)OC([H])([H])* 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 238000009938 salting Methods 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 150000001983 dialkylethers Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 230000009969 flowable effect Effects 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 239000012456 homogeneous solution Substances 0.000 description 2
- 239000010687 lubricating oil Substances 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 2
- 150000003071 polychlorinated biphenyls Chemical class 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical class CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- KSAQCJQZQISASG-UHFFFAOYSA-N 2,4,6-trimethyloctan-1-ol Chemical compound CCC(C)CC(C)CC(C)CO KSAQCJQZQISASG-UHFFFAOYSA-N 0.000 description 1
- FETZOWIQWWEBTN-UHFFFAOYSA-N 3,4-diethylhexan-1-ol Chemical compound CCC(CC)C(CC)CCO FETZOWIQWWEBTN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 125000002704 decyl group Chemical group [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])* 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [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])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000001421 myristyl 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])[H] 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- 150000002896 organic halogen compounds Chemical class 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229940023144 sodium glycolate Drugs 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- JEJAMASKDTUEBZ-UHFFFAOYSA-N tris(1,1,3-tribromo-2,2-dimethylpropyl) phosphate Chemical compound BrCC(C)(C)C(Br)(Br)OP(=O)(OC(Br)(Br)C(C)(C)CBr)OC(Br)(Br)C(C)(C)CBr JEJAMASKDTUEBZ-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- A62D3/34—Dehalogenation using reactive chemical agents able to degrade
-
- 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 invention relates to liquid dehalogenating agents based on alkali alcoholates, the production of the dehalogenating agents and their use for the dehalogenation of waste oils.
- Lubricating oils accumulate metal abrasion and degradation and oxidation products of their components during use. Nonetheless, used lubricating oils are not considered waste products, since they can be processed to such an extent by filtration, distillation or refining with concentrated sulfuric acid that valuable lubricants are formed after additional additives. However, contaminants on chlorinated hydrocarbons, such as polychlorinated biphenyls (PCB), which are toxicologically harmful, are not removed in this way.
- PCB polychlorinated biphenyls
- alkali alcoholates of alcohols with 1 to 5 carbon atoms, polyoxyalkylene glycols with 4 to 20 carbon atoms, polyols with 2 to 5 carbon atoms and 2 to 3 hydroxyl groups, or of monoalkyl ethers of these polyols with alcohols 1 to 4 carbon atoms are suitable as dehalogenating agents.
- the reaction is carried out in the presence of one half to one equivalent of associated free alcohol. It is preferably dehalogenated with sodium glycolate / ethylene glycol and with sodium methylate / methanol.
- DE-A-36 21 175 the dehalogenation of hydrocarbon oils with alkali metal alcoholates with 6 to 25 C atoms is carried out at 120 to 400 ° C.
- the alcoholates can contain small amounts of the associated alcohol.
- the known alcohol enthalogenation agents are sensitive to oxidation and hydrolysis, especially at elevated temperatures. When cooling to room temperature, they also become solid or excrete solid components. To avoid deposits, they have to passed through heated pipes and pumps. They must also always be kept hot until they are used as intended.
- the object of the present invention is to provide easy-to-handle and, moreover, less oxidation- and hydrolysis-sensitive dehalogenating agents.
- liquid dehalogenating agents which contain the following constituents: 30 to 70% alkali alcoholate with 6 to 20 carbon atoms, up to 12% alcohol with 6 to 20 carbon atoms, 5 to 40% polyether of the structure where R1 is hydrogen or alkyl having 1 to 15 C atoms, R2 is hydrogen or alkyl having 1 to 5 C atoms, X is hydrogen or alkyl having 1 to 5 C atoms and n is a number from 2 to 50, and 10 to 65% halogen-free hydrocarbon oil.
- the dehalogenating agents which are liquid even at room temperature, preferably contain 40 to 60% alkali alcoholate, up to 10% related alcohol, 5 to 30% polyethers of structure I and 20 to 55% halogen-free hydrocarbon oil.
- the alcohols on which the alcoholates are based are, for example, hexanol, octanol, 2-ethylhexanol, decanol, 3,4-diethylhexanol, 2,4,6-trimethyloctanol, dodecanol, tetradecanol, hexadecanol or octadecanol.
- the alcoholates preferably contain 8 to 14 carbon atoms.
- Alcoholates of 2-ethylhexanol-1 are very particularly preferred.
- Sodium and potassium alcoholates are preferably used as alkali alcoholates.
- alkali alcoholates can be prepared by all known processes. For example, alkali metal can be reacted with alcohol, alkali hydroxide with alcohol or a lower alcoholate with a higher alcohol, the latter reaction (salting) proceeding at a sufficient rate from about 220 ° C.
- the alkali alcoholate can contain small amounts of the associated free alcohol due to the production process.
- Polyalkylene oxide glycols and their mono- and dialkyl ethers are used as polyethers of structure I in the mixtures.
- Mono- and dialkyl ethers of polyethylene oxide and polypropylene oxide glycols are preferably used.
- Alkyl ethers of copolymers of ethylene oxide and propylene oxide are also suitable.
- R1 is, for example, hydrogen or methyl, ethyl, propyl, isopropyl, butyl, hexyl, octyl, decyl, dodecyl and tetradecyl.
- R 1 is preferably alkyl having 1 to 8 carbon atoms.
- the degree of polymerization n is preferably 3 to 15.
- the polyethers are monobutyl ethers of polyethylene oxide or polypropylene oxide glycols with a degree of polymerization n of 3 to 6.
- the polyethers used generally have a boiling point above 200 ° C.
- Suitable halogen-free hydrocarbon oils are, for example, saturated paraffins, lubricating and insulating oils as well as paraffin, aromatic and naphthene-based neutral oils.
- the alkali alcoholate which may contain small amounts of alcohol, is first dissolved in a polyether of structure I at 100 to 200 ° C.
- the dissolving process is usually spontaneous. It ends after 15 minutes at the latest. Dissolving takes place too slowly at temperatures below 100 ° C. At temperatures above 200 ° C when using polyalkylene oxide glycols and their monoalkyl ethers there is a risk that salting will take place to a significant extent. Then free alcohol and alkali salt of the polyether would be formed.
- the alkali alcoholate is preferably dissolved at 160 to 200 ° C.
- the halogen-free hydrocarbon oil is then mixed in.
- a temperature of 30 to 200 ° C. is generally used, 100 to 160 ° C. being preferred.
- the amounts are chosen so that mixtures with the abovementioned proportions are formed.
- waste oils can be dehalogenated.
- the dehalogenation is generally carried out at 200 to 400 ° C., preferably 0.5 to 10 moles of alkali alcoholate being used per mole of halogen in the waste oil.
Landscapes
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Fire-Extinguishing Compositions (AREA)
- Lubricants (AREA)
Claims (8)
- Agents liquides de déshalogénation, renfermant
de 30 à 70 % d'un alcoolate alcalin comportant de 6 à 20 atomes de carbone,
de 0 à 12 % d'un alcool comportant de 6 à 20 atomes de carbone,
de 5 à 40 % d'un poly-éther de structure
R₁ représente de l'hydrogène ou un alkyle comportant de 1 à 15 atomes de carbone,
R₂ représente de l'hydrogène ou un alkyle comportant de 1 à 5 atomes de carbone,
X représente de l'hydrogène ou un alkyle comportant de 1 à 5 atomes de carbone,
n a une valeur de 2 à 50, et renfermant
de 10 à 65 % d'une huile d'hydrocarbure exempte d'halogène. - Agents liquides de déshalogénation selon la revendication 1, renfermant
de 40 à 60 % d'un alcoolate alcalin,
de 0 à 10 % d'un alcool,
de 5 à 30 % d'un poly-éther de la structure (I)
et
de 20 à 55 % d'une huile d'hydrocarbure exempte d'halogène. - Agents liquides de déshalogénation selon la revendication 1,
caractérisé par le fait que l'alcoolate alcalin et l'alcool comportent de 8 à 14 atomes de carbone et que l'alcoolate alcalin est un alcoolate de sodium et/ou de potassium. - Agents liquides de déshalogénation selon la revendication 1,
caractérisé par le fait que dans le poly-éther de la structure (I)
R₁ est un alkyle comportant de 1 à 8 atomes de carbone,
R₂ représente de l'hydrogène ou un méthyle,
X représente de l'hydrogène ou un méthyle, et
n a une valeur de 3 à 15. - Procédé de préparation d'agents liquides de déshalogénation selon la revendication 1,
caractérisé par le fait que l'on dissout de 30 à 70 parties d'alcoolate alcalin et jusqu'à 12 parties d'alcool dans 5 à 40 parties de poly-éther de la structure (I), à une température de 100 à 200°C, et que l'on ajoute ensuite de 10 à 65 parties d'une huile d'hydrocarbure exempte d'halogène. - Procédé selon la revendication 5,
caractérisé par le fait qu'on effectue la dissolution a une température de 160 à 200°C. - L'utilisation des agents liquides de déshalogénation selon la revendication 1 pour la déshalogénation d'huiles usagées à une température de 200 à 400°C.
- L'utilisation des agents liquides de déshalogénation selon la revendication 7,
caractérisée par le fait que l'on utilise, par mole d'halogène dans l'huile usagée, de 0,5 à 10 moles d'un alcoolate alcalin.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT89122423T ATE90217T1 (de) | 1989-02-02 | 1989-12-05 | Fluessige enthalogenierungsmittel. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3903105A DE3903105A1 (de) | 1989-02-02 | 1989-02-02 | Fluessige enthalogenierungsmittel |
| DE3903105 | 1989-02-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0380782A1 EP0380782A1 (fr) | 1990-08-08 |
| EP0380782B1 true EP0380782B1 (fr) | 1993-06-09 |
Family
ID=6373301
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP89122423A Expired - Lifetime EP0380782B1 (fr) | 1989-02-02 | 1989-12-05 | Agents de déshalogénation liquides |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US5132006A (fr) |
| EP (1) | EP0380782B1 (fr) |
| JP (1) | JPH0390173A (fr) |
| AT (1) | ATE90217T1 (fr) |
| CA (1) | CA2009007A1 (fr) |
| DE (2) | DE3903105A1 (fr) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2611900B2 (ja) * | 1992-06-05 | 1997-05-21 | 財団法人生産開発科学研究所 | 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 |
| US5393394A (en) * | 1992-08-18 | 1995-02-28 | Kabushiki Kaisha Toshiba | Method and apparatus for decomposing organic halogen-containing compound |
| ES2112706B1 (es) * | 1994-05-06 | 1998-10-16 | Centralair Sa | Actuador integral. |
| JP2638483B2 (ja) * | 1994-06-30 | 1997-08-06 | 株式会社関西テック | 多塩素化芳香族化合物の処理方法 |
| US5534124A (en) * | 1995-09-19 | 1996-07-09 | Chem-Pro | On-site electrochemical dehalogenation process and system |
| DE19711762A1 (de) * | 1997-03-21 | 1998-09-24 | Huels Chemische Werke Ag | Verfahren zur Herstellung von Bishydroxymethylverbindungen |
| US6024737A (en) | 1998-02-25 | 2000-02-15 | Advanced Cardiovascular Systems, Inc. | Stent crimping device |
| CN114058433B (zh) * | 2021-12-07 | 2022-11-18 | 湖北润驰环保科技有限公司 | 一种废润滑油脱氯方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4327027A (en) * | 1979-06-15 | 1982-04-27 | Vertac Chemical Corporation | Chemical detoxification of toxic chlorinated aromatic compounds |
| US4351718A (en) * | 1981-06-01 | 1982-09-28 | General Electric Company | Method for removing polyhalogenated hydrocarbons from nonpolar organic solvent solutions |
| US4532028A (en) * | 1983-10-24 | 1985-07-30 | Niagara Mohawk Power Corporation | Method for reducing content of halogenated aromatics in hydrocarbon solutions |
| DE3621175A1 (de) * | 1986-06-25 | 1988-01-07 | Huels Chemische Werke Ag | Verfahren zur enthalogenierung von kohlenwasserstoffoelen |
| DE3900159A1 (de) * | 1989-01-04 | 1990-07-05 | Geut Ag | Verfahren zur aufarbeitung von altoel |
-
1989
- 1989-02-02 DE DE3903105A patent/DE3903105A1/de not_active Withdrawn
- 1989-11-03 US US07/431,437 patent/US5132006A/en not_active Expired - Fee Related
- 1989-12-05 DE DE8989122423T patent/DE58904641D1/de not_active Expired - Fee Related
- 1989-12-05 EP EP89122423A patent/EP0380782B1/fr not_active Expired - Lifetime
- 1989-12-05 AT AT89122423T patent/ATE90217T1/de not_active IP Right Cessation
-
1990
- 1990-01-31 CA CA002009007A patent/CA2009007A1/fr not_active Abandoned
- 1990-02-02 JP JP2022335A patent/JPH0390173A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| US5132006A (en) | 1992-07-21 |
| JPH0390173A (ja) | 1991-04-16 |
| CA2009007A1 (fr) | 1990-08-02 |
| EP0380782A1 (fr) | 1990-08-08 |
| DE3903105A1 (de) | 1990-08-09 |
| ATE90217T1 (de) | 1993-06-15 |
| DE58904641D1 (de) | 1993-07-15 |
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