CA1330808C - Chemical process - Google Patents

Chemical process

Info

Publication number: CA1330808C
Authority: CA; Canada
Prior art keywords: dibromofluoromethane; bromofluoromethane; reaction; hydride; reaction mixture
Prior art date: 1988-02-29
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

Application number

CA000592210A

Other languages

English (en)

French (fr)

Inventor

John Malcolm Robinson

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Glaxo Group Ltd

Original Assignee

Glaxo Group Ltd

Priority date (The priority date 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 date listed.)

1988-02-29

Filing date

1989-02-27

Publication date

1994-07-19

1989-02-27 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

1994-07-19 Application granted granted Critical

1994-07-19 Publication of CA1330808C publication Critical patent/CA1330808C/en

2011-07-19 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

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)

CA000592210A 1988-02-29 1989-02-27 Chemical process Expired - Lifetime CA1330808C (en)

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 (de)
AT (1)	AT397651B (de)
BE (1)	BE1002867A3 (de)
CA (1)	CA1330808C (de)
CH (1)	CH677231A5 (de)
DE (1)	DE3906273C2 (de)
FR (1)	FR2627771B1 (de)
GB (2)	GB8804693D0 (de)
IT (1)	IT1232206B (de)
NL (1)	NL8900490A (de)
SG (1)	SG4792G (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
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 (de) *	1991-04-08	1992-10-14	Imperial Chemical Industries Plc	Herstellung von Fluorkohlenwasserstoffen

Family Cites Families (1)

* Cited by examiner, † Cited by third party
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 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
- 1989-02-27 CH CH705/89A patent/CH677231A5/de not_active IP Right Cessation
- 1989-02-28 JP JP1045552A patent/JP2691000B2/ja not_active Expired - Lifetime
- 1989-02-28 DE DE3906273A patent/DE3906273C2/de not_active Expired - Lifetime
- 1989-02-28 BE BE8900201A patent/BE1002867A3/fr active
- 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
DE3906273C2 (de)	1997-08-28
JPH01294642A (ja)	1989-11-28
SG4792G (en)	1992-03-20
GB2216122B (en)	1991-05-08
FR2627771B1 (fr)	1991-08-16
IT8947689A0 (it)	1989-02-27
JP2691000B2 (ja)	1997-12-17
CH677231A5 (de)	1991-04-30
IT1232206B (it)	1992-01-28
GB2216122A (en)	1989-10-04
BE1002867A3 (fr)	1991-07-09
GB8904250D0 (en)	1989-04-12
FR2627771A1 (fr)	1989-09-01
ATA43489A (de)	1993-10-15
NL8900490A (nl)	1989-09-18
DE3906273A1 (de)	1989-09-07
AT397651B (de)	1994-06-27
GB8804693D0 (en)	1988-03-30

Legal Events

Date	Code	Title	Description
2011-07-19	MKEX	Expiry	Effective date: 20110719

Publication	Publication Date	Title
EP0126569B1 (de)	1986-06-04	Bromierungsverfahren zur Herstellung von Dekabromdiphenylether aus Diphenylether
IE57045B1 (en)	1992-04-08	Hydroxyarylaldehyde preparation
JP3572619B2 (ja)	2004-10-06	ジフルオロメタンの製造方法
US2652432A (en)	1953-09-15	Method of making chlokomethyl
US5189229A (en)	1993-02-23	Debrominating dibromofluoromethane with tributyltin hydride
US4620040A (en)	1986-10-28	Process for the preparation of α-α-α-trifluoroanisoles
GB2216122A (en)	1989-10-04	Preparation of bromofluoromethane
US3060243A (en)	1962-10-23	Method for preparation of
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US4098832A (en)	1978-07-04	Fluorination process catalysed by molybdenum pentachloride
US2934569A (en)	1960-04-26	Preparation of para-fluorophenol
EP0195166B1 (de)	1991-09-18	Verfahren zur Herstellung substituierter Benzaldehyden
US4647695A (en)	1987-03-03	Method of preparing trifluoroacetic acid from trichlorotrifluoroethane
US4334111A (en)	1982-06-08	Process for preparing substituted benzotrihalides
US4183873A (en)	1980-01-15	Liquid phase fluorination process
Sekiya et al.	1979	The reaction of 2-trifluoromethyl-3, 3-difluorooxaziridine with nucleophiles.
US4367349A (en)	1983-01-04	Liquid phase synthesis of hexafluoroisobutylene
US3185737A (en)	1965-05-25	Ortho alkylation of phenols
GB2065656A (en)	1981-07-01	Preparing arylpropionic acids
GB2122193A (en)	1984-01-11	Process of preparing meta-chlorobenzo-trifluoride
US4061688A (en)	1977-12-06	Liquid phase fluorination process
US3607883A (en)	1971-09-21	Bromine chloride-dioxane complex
US3755444A (en)	1973-08-28	Bromination of organic compounds with a bromine chloride dioxane complex
US4130594A (en)	1978-12-19	Liquid phase fluorination process
US3699161A (en)	1972-10-17	Process for the production of thiophosgene