CA2026506A1 - Process for the reductive dehalogenation of polyhaloaromatics using calcium and methanol - Google Patents
Process for the reductive dehalogenation of polyhaloaromatics using calcium and methanolInfo
- Publication number
- CA2026506A1 CA2026506A1 CA2026506A CA2026506A CA2026506A1 CA 2026506 A1 CA2026506 A1 CA 2026506A1 CA 2026506 A CA2026506 A CA 2026506A CA 2026506 A CA2026506 A CA 2026506A CA 2026506 A1 CA2026506 A1 CA 2026506A1
- Authority
- CA
- Canada
- Prior art keywords
- methanol
- sodium
- calcium
- halogenated aromatics
- aromatics
- 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.)
- Granted
Links
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 title abstract 12
- 238000000034 method Methods 0.000 title abstract 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 title abstract 2
- 239000011575 calcium Substances 0.000 title abstract 2
- 229910052791 calcium Inorganic materials 0.000 title abstract 2
- 238000005695 dehalogenation reaction Methods 0.000 title abstract 2
- 230000002829 reductive effect Effects 0.000 title abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 4
- 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 abstract 4
- 239000011734 sodium Substances 0.000 abstract 4
- 229910052708 sodium Inorganic materials 0.000 abstract 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 230000000382 dechlorinating effect Effects 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 150000003071 polychlorinated biphenyls Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/26—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only halogen atoms as hetero-atoms
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Toxicology (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)
- Fire-Extinguishing Compositions (AREA)
Abstract
A process for the reductive dehalogenation of halogenated aromatics. The process comprises reacting halogenated aromatics with sodium or calcium in the presence of a lower alcohol selected from the group comprising methanol, ethanol or isopropanol and mixtures thereof in order to convert the halogenated aromatics to hydrogenated aromatics. The halogenated aromatics are preferably reacted with sodium in the presence of methanol under reaction conditions whereby said sodium is in molten form. The preferred starting sodium/methanol/halogen molar ratio ranges from 30-40/15-20/1. The process is particularly useful for dechlorinating polychlorinated biphenyls found in electrical transformer oil.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/413,942 | 1989-09-28 | ||
| US07/413,942 US4950833A (en) | 1989-09-28 | 1989-09-28 | Process for the reductive dehalogenation of polyhaloaromatics |
| US07/538,233 US5185488A (en) | 1989-09-28 | 1990-06-14 | Process for the reductive dehalogenation of polyhaloaromatics with sodium or calcium in a lower alcohol |
| US07/538,233 | 1990-06-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2026506A1 true CA2026506A1 (en) | 1991-03-29 |
| CA2026506C CA2026506C (en) | 1999-04-06 |
Family
ID=27022353
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002026506A Expired - Lifetime CA2026506C (en) | 1989-09-28 | 1990-09-28 | Process for the reductive dehalogenation of polyhaloaromatics using calcium and methanol |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US5185488A (en) |
| CA (1) | CA2026506C (en) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5994604A (en) * | 1993-03-17 | 1999-11-30 | Lockheed Martin Idaho Technologies Company | Method and apparatus for low temperature destruction of halogenated hydrocarbons |
| US5951852A (en) * | 1993-12-23 | 1999-09-14 | Commonwealth Scientific And Industrial Research Organisation Et Al. | Destruction of halide containing organics and solvent purification |
| US5672266A (en) * | 1995-10-13 | 1997-09-30 | The Lubrizol Corporation | Treatment of organic compounds to reduce chlorine level |
| US5489390A (en) * | 1995-03-14 | 1996-02-06 | The Lubrizol Corporation | Treatment of organic compounds to reduce chlorine level |
| US5534124A (en) * | 1995-09-19 | 1996-07-09 | Chem-Pro | On-site electrochemical dehalogenation process and system |
| US5674819A (en) * | 1995-11-09 | 1997-10-07 | The Lubrizol Corporation | Carboxylic compositions, derivatives,lubricants, fuels and concentrates |
| DE19903987A1 (en) * | 1999-02-02 | 2000-08-10 | Friedrich Boelsing | Rapid reductive dehalogenation of halohydrocarbons, e.g. for removing toxic chloroaromatic compounds from waste oil or soil, by contacting finely divided solid starting material with reducing metal |
| US6414212B1 (en) | 2000-08-18 | 2002-07-02 | Kinectrics, Inc. | Method for decontamination of low level polyhalogenated aromatic contaminated fluid and simultaneous destruction of high level polyhalogenated aromatics |
| US20030120127A1 (en) * | 2001-11-07 | 2003-06-26 | Wylie Ian Gordon Norman | Process for destruction of halogenated organic compounds in solids |
| US6984768B2 (en) | 2002-05-21 | 2006-01-10 | Battelle Energy Alliance, Llc | Method for destroying halocarbon compositions using a critical solvent |
| US20050056598A1 (en) * | 2003-06-06 | 2005-03-17 | Chowdhury Ajit K. | Method for treating recalcitrant organic compounds |
| CN101230304B (en) * | 2007-01-25 | 2010-05-19 | 钟奇 | Environment-friendly type transformer oil and preparation method thereof |
| DE102008056086A1 (en) * | 2008-11-06 | 2010-05-12 | Gp Solar Gmbh | An additive for alkaline etching solutions, in particular for texture etching solutions and process for its preparation |
| CN112142543B (en) * | 2019-06-26 | 2023-03-28 | 北京工商大学 | Dehalogenation method of covalent organic framework material photocatalytic halogenated aromatic compound |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4351978A (en) * | 1980-07-21 | 1982-09-28 | Osaka Prefectural Government | Method for the disposal of polychlorinated biphenyls |
| US4447667A (en) * | 1982-09-22 | 1984-05-08 | The Goodyear Tire & Rubber Company | Process for the dehalogenation of organic compounds |
| IT1206508B (en) * | 1983-07-22 | 1989-04-27 | Sea Marconi Decontamin Srl | CONTINUOUS PROCESS FOR THE DECOMPOSITION AND DECONTAMINATION OF ORGANIC COMPOUNDS AND HALOGENATED TOXIC AGENTS. |
| CH668709A5 (en) * | 1985-12-06 | 1989-01-31 | Ciba Geigy Ag | METHOD FOR ENTHALOGENATING POLYHALOGENATED ALIPHATIC AND AROMATIC COMPOUNDS. |
| DE3621175A1 (en) * | 1986-06-25 | 1988-01-07 | Huels Chemische Werke Ag | METHOD FOR ENTHALOGENATING HYDROCARBON OILS |
-
1990
- 1990-06-14 US US07/538,233 patent/US5185488A/en not_active Expired - Lifetime
- 1990-09-28 CA CA002026506A patent/CA2026506C/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US5185488A (en) | 1993-02-09 |
| CA2026506C (en) | 1999-04-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |