JP2691000B2 - ブロモフルオロメタンの製造方法 - Google Patents
ブロモフルオロメタンの製造方法Info
- Publication number
- JP2691000B2 JP2691000B2 JP1045552A JP4555289A JP2691000B2 JP 2691000 B2 JP2691000 B2 JP 2691000B2 JP 1045552 A JP1045552 A JP 1045552A JP 4555289 A JP4555289 A JP 4555289A JP 2691000 B2 JP2691000 B2 JP 2691000B2
- Authority
- JP
- Japan
- 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
- LHMHCLYDBQOYTO-UHFFFAOYSA-N bromofluoromethane Chemical compound FCBr LHMHCLYDBQOYTO-UHFFFAOYSA-N 0.000 title claims description 41
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- LTUTVFXOEGMHMP-UHFFFAOYSA-N dibromofluoromethane Chemical compound FC(Br)Br LTUTVFXOEGMHMP-UHFFFAOYSA-N 0.000 claims description 48
- 238000006243 chemical reaction Methods 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 20
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical group CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 claims description 15
- 239000011541 reaction mixture Substances 0.000 claims description 14
- 238000010992 reflux Methods 0.000 claims description 14
- 150000004678 hydrides Chemical class 0.000 claims description 11
- 238000004821 distillation Methods 0.000 claims description 7
- 239000003999 initiator Substances 0.000 claims description 6
- 150000003254 radicals Chemical class 0.000 claims description 5
- 238000005286 illumination Methods 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims 2
- 230000005494 condensation Effects 0.000 claims 2
- 230000008016 vaporization Effects 0.000 claims 1
- 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 22
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 19
- 235000011089 carbon dioxide Nutrition 0.000 description 17
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 239000000203 mixture Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- IHZAEIHJPNTART-UHFFFAOYSA-N tribromofluoromethane Chemical compound FC(Br)(Br)Br IHZAEIHJPNTART-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000010792 warming Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- QEWYKACRFQMRMB-UHFFFAOYSA-N fluoroacetic acid Chemical class OC(=O)CF QEWYKACRFQMRMB-UHFFFAOYSA-N 0.000 description 2
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- JNUZADQZHYFJGW-JOCHJYFZSA-N (2R)-N-[3-[5-fluoro-2-(2-fluoro-3-methylsulfonylanilino)pyrimidin-4-yl]-1H-indol-7-yl]-3-methoxy-2-(4-methylpiperazin-1-yl)propanamide Chemical compound FC=1C(=NC(=NC=1)NC1=C(C(=CC=C1)S(=O)(=O)C)F)C1=CNC2=C(C=CC=C12)NC([C@@H](COC)N1CCN(CC1)C)=O JNUZADQZHYFJGW-JOCHJYFZSA-N 0.000 description 1
- 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
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 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
- 238000001311 chemical methods and process Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007256 debromination reaction 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
- 238000003682 fluorination reaction Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 239000000383 hazardous chemical Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- KXCAEQNNTZANTK-UHFFFAOYSA-N stannane Chemical compound [SnH4] KXCAEQNNTZANTK-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229910000083 tin tetrahydride Inorganic materials 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
- 238000005292 vacuum distillation Methods 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 |
|---|---|---|---|
| GB8804693 | 1988-02-29 | ||
| GB888804693A GB8804693D0 (en) | 1988-02-29 | 1988-02-29 | Chemical process |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01294642A JPH01294642A (ja) | 1989-11-28 |
| JP2691000B2 true JP2691000B2 (ja) | 1997-12-17 |
Family
ID=10632550
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1045552A Expired - Lifetime JP2691000B2 (ja) | 1988-02-29 | 1989-02-28 | ブロモフルオロメタンの製造方法 |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JP2691000B2 (https=) |
| AT (1) | AT397651B (https=) |
| BE (1) | BE1002867A3 (https=) |
| CA (1) | CA1330808C (https=) |
| CH (1) | CH677231A5 (https=) |
| DE (1) | DE3906273C2 (https=) |
| FR (1) | FR2627771B1 (https=) |
| GB (2) | GB8804693D0 (https=) |
| IT (1) | IT1232206B (https=) |
| NL (1) | NL8900490A (https=) |
| SG (1) | SG4792G (https=) |
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 CH CH705/89A patent/CH677231A5/de not_active IP Right Cessation
- 1989-02-27 CA CA000592210A patent/CA1330808C/en not_active Expired - Lifetime
- 1989-02-27 IT IT8947689A patent/IT1232206B/it active
- 1989-02-27 AT AT0043489A patent/AT397651B/de not_active IP Right Cessation
- 1989-02-28 DE DE3906273A patent/DE3906273C2/de not_active Expired - Lifetime
- 1989-02-28 BE BE8900201A patent/BE1002867A3/fr active
- 1989-02-28 JP JP1045552A patent/JP2691000B2/ja not_active Expired - Lifetime
- 1989-02-28 NL NL8900490A patent/NL8900490A/nl active Search and Examination
-
1992
- 1992-01-20 SG SG47/92A patent/SG4792G/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IT8947689A0 (it) | 1989-02-27 |
| CH677231A5 (https=) | 1991-04-30 |
| IT1232206B (it) | 1992-01-28 |
| DE3906273A1 (de) | 1989-09-07 |
| ATA43489A (de) | 1993-10-15 |
| SG4792G (en) | 1992-03-20 |
| GB2216122B (en) | 1991-05-08 |
| FR2627771A1 (fr) | 1989-09-01 |
| NL8900490A (nl) | 1989-09-18 |
| JPH01294642A (ja) | 1989-11-28 |
| AT397651B (de) | 1994-06-27 |
| GB8804693D0 (en) | 1988-03-30 |
| FR2627771B1 (fr) | 1991-08-16 |
| CA1330808C (en) | 1994-07-19 |
| BE1002867A3 (fr) | 1991-07-09 |
| DE3906273C2 (de) | 1997-08-28 |
| GB2216122A (en) | 1989-10-04 |
| GB8904250D0 (en) | 1989-04-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0733341B2 (ja) | フツ素化ｃ▲下４▼〜ｃ▲下６▼炭化水素の製造方法 | |
| KR19990064328A (ko) | 옥타플루오로-[2,2]파라사이클로판의 제조방법 | |
| JPS63132851A (ja) | フルオルアルキルペルフルオルビニルエーテルの製造方法 | |
| JP2691000B2 (ja) | ブロモフルオロメタンの製造方法 | |
| EP0355978B1 (en) | Process for preparing chf2ochfcf3 and chf2ochclcf3 and novel intermediate compounds employed thereby | |
| US3433838A (en) | Purification of perhaloacetones | |
| JPH0692957A (ja) | 含フッ素ジオキソラン化合物の製造方法 | |
| JP2589108B2 (ja) | ペルフルオルアルカンジエンの合成方法 | |
| US4499024A (en) | Continuous process for preparing bisfluoroxydifluoromethane | |
| JPH0747556B2 (ja) | 含フッ素エーテル化合物の製造方法 | |
| JPH05170693A (ja) | 化学的方法 | |
| US5189229A (en) | Debrominating dibromofluoromethane with tributyltin hydride | |
| KR101284659B1 (ko) | 1,2,2,2-테트라플루오로에틸 디플루오로메틸 에테르의제조방법 | |
| Leitch et al. | Synthesis of Organic Deuterium Compounds: II. PROPYNE-3-d 3 and PROPYNE-d 4 | |
| US4216338A (en) | Synthesis of fluorocarbon esters | |
| JP3873308B2 (ja) | フッ化炭化水素化合物の製造法 | |
| JP2000336057A (ja) | １，１，１−トリフルオロアセトンの製造方法 | |
| John et al. | Oxadiazoles with NF2-containing substituents | |
| EP0497990B1 (en) | Process for producing trifluorinated hydrocarbon compound | |
| US6350926B1 (en) | Chlorofluorohydrocarbon and process thereto | |
| US5185483A (en) | Process for preparing pentafluorodichloropropanes | |
| US2954411A (en) | Process for the preparation of cyclopropanes | |
| JP2500325B2 (ja) | エタン系含フッ素炭化水素化合物の製造法 | |
| JPH05988A (ja) | トリフルオロアニソール類の製造方法 | |
| Nixon et al. | Pentafluoro-λ6-sulfanyl (SF5) perfluoroalkyl iodides-synthesis and reaction with ethylene and tetrafluoroethylene: Crystal structure of SF5 (CF2) 4CH2CH2I |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20070829 Year of fee payment: 10 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20080829 Year of fee payment: 11 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20090829 Year of fee payment: 12 |
|
| EXPY | Cancellation because of completion of term | ||
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20090829 Year of fee payment: 12 |