CA1330808C - Chemical process - Google Patents
Chemical processInfo
- Publication number
- CA1330808C CA1330808C CA000592210A CA592210A CA1330808C CA 1330808 C CA1330808 C CA 1330808C CA 000592210 A CA000592210 A CA 000592210A CA 592210 A CA592210 A CA 592210A CA 1330808 C CA1330808 C CA 1330808C
- Authority
- CA
- Canada
- Prior art keywords
- dibromofluoromethane
- bromofluoromethane
- reaction
- hydride
- reaction mixture
- 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
- 238000001311 chemical methods and process Methods 0.000 title abstract description 3
- LHMHCLYDBQOYTO-UHFFFAOYSA-N bromofluoromethane Chemical compound FCBr LHMHCLYDBQOYTO-UHFFFAOYSA-N 0.000 claims abstract description 41
- LTUTVFXOEGMHMP-UHFFFAOYSA-N dibromofluoromethane Chemical compound FC(Br)Br LTUTVFXOEGMHMP-UHFFFAOYSA-N 0.000 claims abstract description 35
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 claims abstract description 13
- 150000004678 hydrides Chemical class 0.000 claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 23
- 238000010992 reflux Methods 0.000 claims description 14
- 239000011541 reaction mixture Substances 0.000 claims description 12
- 238000004821 distillation Methods 0.000 claims description 10
- 239000003999 initiator Substances 0.000 claims description 6
- 150000003254 radicals Chemical class 0.000 claims description 6
- 238000005286 illumination Methods 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims 2
- 230000005494 condensation Effects 0.000 claims 2
- 238000001704 evaporation Methods 0.000 claims 2
- 238000002360 preparation method Methods 0.000 abstract description 5
- 230000002829 reductive effect Effects 0.000 abstract description 4
- 238000007256 debromination reaction Methods 0.000 abstract description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 18
- 235000011089 carbon dioxide Nutrition 0.000 description 16
- 239000000203 mixture Substances 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 239000000047 product Substances 0.000 description 7
- 238000010926 purge Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- IHZAEIHJPNTART-UHFFFAOYSA-N tribromofluoromethane Chemical compound FC(Br)(Br)Br IHZAEIHJPNTART-UHFFFAOYSA-N 0.000 description 4
- 238000010792 warming Methods 0.000 description 4
- 101150041968 CDC13 gene Proteins 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- XQTSNLDHBNNMLC-UHFFFAOYSA-N C(CCC)[SnH](CCCC)CCCC.C(CCC)[SnH](CCCC)CCCC Chemical compound C(CCC)[SnH](CCCC)CCCC.C(CCC)[SnH](CCCC)CCCC XQTSNLDHBNNMLC-UHFFFAOYSA-N 0.000 description 2
- 241000786363 Rhampholeon spectrum Species 0.000 description 2
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 101100192716 Mus musculus Purg gene Proteins 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- STEPQTYSZVCJPV-UHFFFAOYSA-N metazachlor Chemical compound CC1=CC=CC(C)=C1N(C(=O)CCl)CN1N=CC=C1 STEPQTYSZVCJPV-UHFFFAOYSA-N 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- RONZAEMNMFQXRA-UHFFFAOYSA-N mirtazapine Chemical compound C1C2=CC=CN=C2N2CCN(C)CC2C2=CC=CC=C21 RONZAEMNMFQXRA-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/23—Preparation of halogenated hydrocarbons by dehalogenation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB888804693A GB8804693D0 (en) | 1988-02-29 | 1988-02-29 | Chemical process |
| GB8804693 | 1988-02-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1330808C true CA1330808C (en) | 1994-07-19 |
Family
ID=10632550
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000592210A Expired - Lifetime CA1330808C (en) | 1988-02-29 | 1989-02-27 | Chemical process |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JP2691000B2 (ja) |
| AT (1) | AT397651B (ja) |
| BE (1) | BE1002867A3 (ja) |
| CA (1) | CA1330808C (ja) |
| CH (1) | CH677231A5 (ja) |
| DE (1) | DE3906273C2 (ja) |
| FR (1) | FR2627771B1 (ja) |
| GB (2) | GB8804693D0 (ja) |
| IT (1) | IT1232206B (ja) |
| NL (1) | NL8900490A (ja) |
| SG (1) | SG4792G (ja) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991009000A1 (en) * | 1989-12-15 | 1991-06-27 | Great Lakes Chemical Corporation | Method for the production of bromodifluoromethane |
| EP0508631A1 (en) * | 1991-04-08 | 1992-10-14 | Imperial Chemical Industries Plc | Production of hydrofluorocarbons |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8725839D0 (en) * | 1987-11-04 | 1987-12-09 | Ici Plc | Chemical process |
-
1988
- 1988-02-29 GB GB888804693A patent/GB8804693D0/en active Pending
-
1989
- 1989-02-24 GB GB8904250A patent/GB2216122B/en not_active Expired - Lifetime
- 1989-02-24 FR FR898902425A patent/FR2627771B1/fr not_active Expired - Lifetime
- 1989-02-27 AT AT0043489A patent/AT397651B/de not_active IP Right Cessation
- 1989-02-27 IT IT8947689A patent/IT1232206B/it active
- 1989-02-27 CA CA000592210A patent/CA1330808C/en not_active Expired - Lifetime
- 1989-02-27 CH CH705/89A patent/CH677231A5/de not_active IP Right Cessation
- 1989-02-28 BE BE8900201A patent/BE1002867A3/fr active
- 1989-02-28 NL NL8900490A patent/NL8900490A/nl active Search and Examination
- 1989-02-28 DE DE3906273A patent/DE3906273C2/de not_active Expired - Lifetime
- 1989-02-28 JP JP1045552A patent/JP2691000B2/ja not_active Expired - Lifetime
-
1992
- 1992-01-20 SG SG47/92A patent/SG4792G/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IT1232206B (it) | 1992-01-28 |
| AT397651B (de) | 1994-06-27 |
| SG4792G (en) | 1992-03-20 |
| GB8904250D0 (en) | 1989-04-12 |
| IT8947689A0 (it) | 1989-02-27 |
| JPH01294642A (ja) | 1989-11-28 |
| DE3906273C2 (de) | 1997-08-28 |
| ATA43489A (de) | 1993-10-15 |
| CH677231A5 (ja) | 1991-04-30 |
| DE3906273A1 (de) | 1989-09-07 |
| GB2216122B (en) | 1991-05-08 |
| GB2216122A (en) | 1989-10-04 |
| FR2627771A1 (fr) | 1989-09-01 |
| NL8900490A (nl) | 1989-09-18 |
| JP2691000B2 (ja) | 1997-12-17 |
| BE1002867A3 (fr) | 1991-07-09 |
| GB8804693D0 (en) | 1988-03-30 |
| FR2627771B1 (fr) | 1991-08-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |
Effective date: 20110719 |