CA2028879C - Ambient temperature destruction of pcb wastes - Google Patents
Ambient temperature destruction of pcb wastesInfo
- Publication number
- CA2028879C CA2028879C CA 2028879 CA2028879A CA2028879C CA 2028879 C CA2028879 C CA 2028879C CA 2028879 CA2028879 CA 2028879 CA 2028879 A CA2028879 A CA 2028879A CA 2028879 C CA2028879 C CA 2028879C
- Authority
- CA
- Canada
- Prior art keywords
- pcbs
- process according
- halogenated hydrocarbons
- solid
- oxidant
- 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 - Fee Related
Links
- 230000006378 damage Effects 0.000 title claims abstract description 18
- 239000002699 waste material Substances 0.000 title description 2
- 150000003071 polychlorinated biphenyls Chemical class 0.000 claims abstract description 31
- 238000000034 method Methods 0.000 claims abstract description 23
- 239000007787 solid Substances 0.000 claims abstract description 20
- 150000008282 halocarbons Chemical class 0.000 claims abstract description 19
- 239000007800 oxidant agent Substances 0.000 claims abstract description 16
- 239000002253 acid Substances 0.000 claims abstract description 14
- 230000001590 oxidative effect Effects 0.000 claims abstract description 14
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000012286 potassium permanganate Substances 0.000 claims abstract description 11
- 239000012530 fluid Substances 0.000 claims abstract description 9
- 239000005662 Paraffin oil Substances 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 2
- 239000000919 ceramic Substances 0.000 claims description 2
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical class [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 claims description 2
- 229910052804 chromium Inorganic materials 0.000 claims description 2
- 239000011651 chromium Substances 0.000 claims description 2
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 2
- 239000011159 matrix material Substances 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- 229910052720 vanadium Inorganic materials 0.000 claims description 2
- 239000010457 zeolite Substances 0.000 claims description 2
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims 1
- 239000003921 oil Substances 0.000 abstract description 11
- BTAGRXWGMYTPBY-UHFFFAOYSA-N 1,2,3-trichloro-4-(2,3,4-trichlorophenyl)benzene Chemical compound ClC1=C(Cl)C(Cl)=CC=C1C1=CC=C(Cl)C(Cl)=C1Cl BTAGRXWGMYTPBY-UHFFFAOYSA-N 0.000 abstract description 6
- 239000012258 stirred mixture Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 150000002896 organic halogen compounds Chemical class 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 1
- -1 PCBs Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000003915 air pollution Methods 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229940090961 chromium dioxide Drugs 0.000 description 1
- IAQWMWUKBQPOIY-UHFFFAOYSA-N chromium(4+);oxygen(2-) Chemical compound [O-2].[O-2].[Cr+4] IAQWMWUKBQPOIY-UHFFFAOYSA-N 0.000 description 1
- AYTAKQFHWFYBMA-UHFFFAOYSA-N chromium(IV) oxide Inorganic materials O=[Cr]=O AYTAKQFHWFYBMA-UHFFFAOYSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005264 electron capture Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 239000000383 hazardous chemical Substances 0.000 description 1
- 239000002035 hexane extract Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000001473 noxious effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000002910 solid waste Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-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
- A62D3/38—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances by reacting with chemical agents by oxidation; by combustion
-
- A—HUMAN NECESSITIES
- A62—LIFE-SAVING; FIRE-FIGHTING
- A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
- A62D2101/00—Harmful chemical substances made harmless, or less harmful, by effecting chemical change
- A62D2101/20—Organic substances
- A62D2101/22—Organic substances containing halogen
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)
- Fire-Extinguishing Compositions (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
There is disclosed a process for destroying halogenated hydrocarbons such as PCBs and PCBs in PCB containing fluids (e.g., Askarel) and oils (e.g., paraffin oil, transformer oil, etc.) at ambient temperature. The process comprises reacting halogenated hydrocarbons, such as PCB containing fluids or oils with a solid oxidant in the presence of a concentrated acid. Preferably, the solid oxidant is potassium permanganate and the concentrated acid is sulfuric acid. Destruction efficiency is as high as 99.95%.
Description
This invention relates to a process for destroying PCBs and PCBs in PCB containing fluids and oils using solid oxidants in the presence of a concentrated acid at ambient temperature.
Polychlorinated biphenyls (PCBs) have been widely used as insulating materials in electrical equipment, heat exchange liquids, plasticizers and for other industrial applications. It has been determined, however, that PCBs and other polyhalogenated organic compounds are a source of ecological problems including toxic effects on humans, animals, vegetation, soil and air. As a result, the use of PCBs is now banned in many countries including Canada and the U.S. However, safe disposal of waste PCBs still remains a problem due to the very nature of halogenated hydrocarbons, i.e., high stability to chemical and biological degradation and production of toxic compounds.
A number of methods have been proposed to destroy polychlorinated biphenyls and other halogenated hydrocarbons. Some of the proposed methods employ a high temperature treatment and therefore carry the risk of air pollution due to the emission of noxious fumes and vapors in the environment. Also, incineration as a way to dispose of hazardous chemicals in general has a notable drawback in that it requires substantial energy consumption.
A number of patents exist on the decomposition reactions of halogenated organic compounds stimulated by the use of various forms of -
Polychlorinated biphenyls (PCBs) have been widely used as insulating materials in electrical equipment, heat exchange liquids, plasticizers and for other industrial applications. It has been determined, however, that PCBs and other polyhalogenated organic compounds are a source of ecological problems including toxic effects on humans, animals, vegetation, soil and air. As a result, the use of PCBs is now banned in many countries including Canada and the U.S. However, safe disposal of waste PCBs still remains a problem due to the very nature of halogenated hydrocarbons, i.e., high stability to chemical and biological degradation and production of toxic compounds.
A number of methods have been proposed to destroy polychlorinated biphenyls and other halogenated hydrocarbons. Some of the proposed methods employ a high temperature treatment and therefore carry the risk of air pollution due to the emission of noxious fumes and vapors in the environment. Also, incineration as a way to dispose of hazardous chemicals in general has a notable drawback in that it requires substantial energy consumption.
A number of patents exist on the decomposition reactions of halogenated organic compounds stimulated by the use of various forms of -
-2- 2028879 radiation, e.g., UV, microwave, solar energy, etc.
(U.S. patents nos. 4,345,983; 4,632,742; 4,432,344 and 4,549,528).
There is, however, still a need for a safe and efficient process for the destruction of halogenated or polyhalogenated hydrocarbons, where the risks associated with high temperature treatment would be eliminated.
According to this invention, there is provided a process for destroying halogenated hydrocarbons, such as PCBs and PCBs in PCB
containing fluids and oils at ambient temperature.
The process comprises reacting halogenated hydrocarbons, such as PCBs and PCBs containing fluids or oils with a solid oxidant in the presence of a concentrated acid.
The amount of solid oxidant, the volume of concentrated acid, the sequence of addition and the duration of the reaction are not critical. These parameters should only be so as to be sufficient to effect the total destruction of halogenated hydrocarbons, such as PCBs.
For the purpose of the present invention, the destruction of halogenated hydrocarbons, such as PCBs, will be understood to mean a process in which a cleavage of carbon-halogen bands takes place, thus practically eliminating all problems of toxicity.
-The halogenated hydrocarbons, which are preferably destroyed by the process according to the invention, include a PCB, PCBs in fluids, such as Askarel, PCBs in paraffin oil and PCBs in transformer oil.
The preferred oxidant, which is used in the process according to the invention, consists of potassium permanganate, although oxides of manganese, chromium and vanadium, chromates and dichromates may also be used.
Although a large number of concentrated acids may be used, the preferred acid is concentrated sulfuric acid.
According to an embodiment of the invention, the halogenated hydrocarbons may be present in a solid, liquid or gaseous matrix, for reaction with the solid oxidant and concentrated acid.
According to another embodiment of the invention, the solid oxidant and the concentrated acid may be supported on a solid support, such as alumina, titania, silica, zeolites, clays, ceramics or the like.
Although the reaction time is not critical, the reaction usually lasts between about 30 minutes and gO minutes and longer.
The invention will now be illustrated by means of the following examples, which are not intended to limit the scope of the present invention.
~4~ 2028879 The use of solid oxidants in cleaving carbon-halogen bonds is not limited to PCBs and hence the conditions and reagents discussed in examples can be applied to the destruction of halogenated organic compounds in general.
Example 1 A sample of Askarel (O.llg) was mixed with finely ground potassium permanganate (0.55g) in a 250ml Erlenmeyer flask. Concentrated sulfuric acid (5ml) was then added to the mixture and the reaction was allowed to proceed over a total period of approximately 90 minutes. The reaction mixture was then extracted with n-hexane at room temperature.
The destruction efficiency was determined by analyzing n-hexane extract using a gas chromatograph equipped with an electron capture detector. The destruction efficiency was found to be above 99.9%.
Example 2 (In this and the following examples, the apparatus, reaction and analytical conditions were similar to Example 1, except where indicated.) Askarel (O.lg) was added to a mixture of potassium permanganate (0.5g) and concentrated sulfuric acid (5ml), over a period of approximately minutes, with stirring. The destruction efficiency was 99.99~.
-_ --5 20~8879 Example 3 Potassium permanganate (2.2g) was added to a stirred mixture of Askarel (0.4g) in concentrated sulfuric acid (20ml). The destruction efficiency S was 99.99%.
Example 4 Paraffin oil (0.17g) spiked with ~ 500,000 ppm PCB was added dropwise to a stirred mixture of potassium permanganate (2.2g) and concentrated sulfuric acid (20ml) over a period of approximately 20 minutes. Contents were stirred for an additional minutes at 60-65 degrees Celsius. The destruction efficiency was 99.95%.
Example 5 lS Transformer oil (0.2g) spiked with ~ 500,000 ppm PCB was added dropwise to a stirred mixture of potassium permanganate (2.2g) and concentrated sulfuric acid (20ml) over a period of approximately 30 minutes. Contents were stirred for an additional 50 minutes at 70 degrees Celsius. The destruction efficiency was above 99.95%.
Example 6 Transformer oil (0.17g) spiked with 5,000 ppm Aroclor 1254 was added dropwise to a stirred mixture of potassium permanganate (2.6g) and concentrated sulfuric acid (20ml) over a period of approximately 25 minutes. Contents were stirred for an additional 40 minutes at 70 degrees Celsius. The destruction efficiency was 99.95%.
It is evident, therefore, that the solid oxidant - potassium permanganate - in concentrated sulfuric acid at room temperature is effective in accomplishing a substantial and rapid destruction of PCBs and PCBs in PCB containing fluids and oils.
The process according to the present invention, can also be used to destroy a variety of halogenated hydrocarbons beside PCBs. However, for each substance to be decontaminated, optimum amounts of the solid oxidant and the concentrated acid have to be adjusted with the type of halogenated hydrocarbon.
Example 7 Askarel (O.lg) was mixed with chromium dioxide (0.5g) and concentrated sulfuric acid (5 ml) The mixture was maintained at 100 degrees Celsius for 30 minutes. The destruction efficiency was 99.99%.
It should also be noted that the destruction process of the invention is not limited to PCBs and PCBs in fluids or oils. Destruction of halogenated hydrocarbons, by the process according to this invention, may be carried out in diverse matrices such as liquids, solids (PCBs in soil or other types of solid wastes) and gases (PCBs and other halogenated hydrocarbons in air).
(U.S. patents nos. 4,345,983; 4,632,742; 4,432,344 and 4,549,528).
There is, however, still a need for a safe and efficient process for the destruction of halogenated or polyhalogenated hydrocarbons, where the risks associated with high temperature treatment would be eliminated.
According to this invention, there is provided a process for destroying halogenated hydrocarbons, such as PCBs and PCBs in PCB
containing fluids and oils at ambient temperature.
The process comprises reacting halogenated hydrocarbons, such as PCBs and PCBs containing fluids or oils with a solid oxidant in the presence of a concentrated acid.
The amount of solid oxidant, the volume of concentrated acid, the sequence of addition and the duration of the reaction are not critical. These parameters should only be so as to be sufficient to effect the total destruction of halogenated hydrocarbons, such as PCBs.
For the purpose of the present invention, the destruction of halogenated hydrocarbons, such as PCBs, will be understood to mean a process in which a cleavage of carbon-halogen bands takes place, thus practically eliminating all problems of toxicity.
-The halogenated hydrocarbons, which are preferably destroyed by the process according to the invention, include a PCB, PCBs in fluids, such as Askarel, PCBs in paraffin oil and PCBs in transformer oil.
The preferred oxidant, which is used in the process according to the invention, consists of potassium permanganate, although oxides of manganese, chromium and vanadium, chromates and dichromates may also be used.
Although a large number of concentrated acids may be used, the preferred acid is concentrated sulfuric acid.
According to an embodiment of the invention, the halogenated hydrocarbons may be present in a solid, liquid or gaseous matrix, for reaction with the solid oxidant and concentrated acid.
According to another embodiment of the invention, the solid oxidant and the concentrated acid may be supported on a solid support, such as alumina, titania, silica, zeolites, clays, ceramics or the like.
Although the reaction time is not critical, the reaction usually lasts between about 30 minutes and gO minutes and longer.
The invention will now be illustrated by means of the following examples, which are not intended to limit the scope of the present invention.
~4~ 2028879 The use of solid oxidants in cleaving carbon-halogen bonds is not limited to PCBs and hence the conditions and reagents discussed in examples can be applied to the destruction of halogenated organic compounds in general.
Example 1 A sample of Askarel (O.llg) was mixed with finely ground potassium permanganate (0.55g) in a 250ml Erlenmeyer flask. Concentrated sulfuric acid (5ml) was then added to the mixture and the reaction was allowed to proceed over a total period of approximately 90 minutes. The reaction mixture was then extracted with n-hexane at room temperature.
The destruction efficiency was determined by analyzing n-hexane extract using a gas chromatograph equipped with an electron capture detector. The destruction efficiency was found to be above 99.9%.
Example 2 (In this and the following examples, the apparatus, reaction and analytical conditions were similar to Example 1, except where indicated.) Askarel (O.lg) was added to a mixture of potassium permanganate (0.5g) and concentrated sulfuric acid (5ml), over a period of approximately minutes, with stirring. The destruction efficiency was 99.99~.
-_ --5 20~8879 Example 3 Potassium permanganate (2.2g) was added to a stirred mixture of Askarel (0.4g) in concentrated sulfuric acid (20ml). The destruction efficiency S was 99.99%.
Example 4 Paraffin oil (0.17g) spiked with ~ 500,000 ppm PCB was added dropwise to a stirred mixture of potassium permanganate (2.2g) and concentrated sulfuric acid (20ml) over a period of approximately 20 minutes. Contents were stirred for an additional minutes at 60-65 degrees Celsius. The destruction efficiency was 99.95%.
Example 5 lS Transformer oil (0.2g) spiked with ~ 500,000 ppm PCB was added dropwise to a stirred mixture of potassium permanganate (2.2g) and concentrated sulfuric acid (20ml) over a period of approximately 30 minutes. Contents were stirred for an additional 50 minutes at 70 degrees Celsius. The destruction efficiency was above 99.95%.
Example 6 Transformer oil (0.17g) spiked with 5,000 ppm Aroclor 1254 was added dropwise to a stirred mixture of potassium permanganate (2.6g) and concentrated sulfuric acid (20ml) over a period of approximately 25 minutes. Contents were stirred for an additional 40 minutes at 70 degrees Celsius. The destruction efficiency was 99.95%.
It is evident, therefore, that the solid oxidant - potassium permanganate - in concentrated sulfuric acid at room temperature is effective in accomplishing a substantial and rapid destruction of PCBs and PCBs in PCB containing fluids and oils.
The process according to the present invention, can also be used to destroy a variety of halogenated hydrocarbons beside PCBs. However, for each substance to be decontaminated, optimum amounts of the solid oxidant and the concentrated acid have to be adjusted with the type of halogenated hydrocarbon.
Example 7 Askarel (O.lg) was mixed with chromium dioxide (0.5g) and concentrated sulfuric acid (5 ml) The mixture was maintained at 100 degrees Celsius for 30 minutes. The destruction efficiency was 99.99%.
It should also be noted that the destruction process of the invention is not limited to PCBs and PCBs in fluids or oils. Destruction of halogenated hydrocarbons, by the process according to this invention, may be carried out in diverse matrices such as liquids, solids (PCBs in soil or other types of solid wastes) and gases (PCBs and other halogenated hydrocarbons in air).
Claims (9)
1. Process for the destruction of halogenated hydrocarbons, which comprises reacting said halogenated hydrocarbons with a solid oxidant in the presence of a concentrated acid at ambient temperature, until substantially all said halogenated hydrocarbons have been destroyed.
2. Process according to Claim 1, wherein said halogenated hydrocarbons are selected from the group consisting of PCBs, PCBs in fluids, PCBs in paraffin oil and PCBs in transformer oil.
3. Process according to Claim 1, wherein the oxidant is selected from the group consisting of potassium permanganate, oxides of manganese, chromium and vanadium, chromates and dichromates.
4. Process according to Claim 1, wherein said solid oxidant comprises potassium permanganate.
5. Process according to Claim 1, wherein the acid comprises sulfuric acid.
6. Process according to Claim 1, wherein the halogenated hydrocarbons are present in a solid, liquid or gaseous matrix, for reaction with said solid oxidant and said concentrated acid.
7. Process according to Claim 1, wherein the solid oxidant and the concentrated acid are supported on a solid support.
8. Process according to Claim 1, wherein said solid support is selected from the group consisting of alumina, titania, silica, zeolites, clays and ceramics.
9. Process according to Claim 1, wherein the reaction is allowed to proceed between at least about 30 to about 90 minutes.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA 2028879 CA2028879C (en) | 1990-10-30 | 1990-10-30 | Ambient temperature destruction of pcb wastes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA 2028879 CA2028879C (en) | 1990-10-30 | 1990-10-30 | Ambient temperature destruction of pcb wastes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2028879A1 CA2028879A1 (en) | 1992-05-01 |
| CA2028879C true CA2028879C (en) | 1996-06-18 |
Family
ID=4146290
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2028879 Expired - Fee Related CA2028879C (en) | 1990-10-30 | 1990-10-30 | Ambient temperature destruction of pcb wastes |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA2028879C (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0107705D0 (en) | 2001-03-28 | 2001-05-16 | Ineos Fluor Ltd | Purification of saturated halocarbons |
-
1990
- 1990-10-30 CA CA 2028879 patent/CA2028879C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2028879A1 (en) | 1992-05-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |