GB1062301A - Fluorination of aromatic compounds - Google Patents
Fluorination of aromatic compoundsInfo
- Publication number
- GB1062301A GB1062301A GB4636/64A GB463664A GB1062301A GB 1062301 A GB1062301 A GB 1062301A GB 4636/64 A GB4636/64 A GB 4636/64A GB 463664 A GB463664 A GB 463664A GB 1062301 A GB1062301 A GB 1062301A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkali metal
- metal fluoride
- aromatic compound
- halogenated aromatic
- compounds
- 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
Links
- 150000001491 aromatic compounds Chemical class 0.000 title abstract 5
- 238000003682 fluorination reaction Methods 0.000 title 1
- 229910001515 alkali metal fluoride Inorganic materials 0.000 abstract 3
- GMAAQKFDAJMAFP-UHFFFAOYSA-N 1,3-dichloro-2,4,6-trifluoro-5-(trifluoromethyl)benzene Chemical compound FC1=C(Cl)C(F)=C(C(F)(F)F)C(F)=C1Cl GMAAQKFDAJMAFP-UHFFFAOYSA-N 0.000 abstract 2
- WFPMVEWSBGBVKV-UHFFFAOYSA-N 1-chloro-2,3,4,6-tetrafluoro-5-(trifluoromethyl)benzene Chemical compound FC1=C(F)C(Cl)=C(F)C(C(F)(F)F)=C1F WFPMVEWSBGBVKV-UHFFFAOYSA-N 0.000 abstract 2
- 229910052794 bromium Inorganic materials 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- TXCAZKMXLKWUTK-UHFFFAOYSA-N 1,2,3,5-tetrafluoro-4-(trifluoromethyl)benzene Chemical compound FC1=CC(F)=C(C(F)(F)F)C(F)=C1F TXCAZKMXLKWUTK-UHFFFAOYSA-N 0.000 abstract 1
- NHSSJMAUKULEMJ-UHFFFAOYSA-N 1-bromo-2,3,4,6-tetrafluoro-5-(trifluoromethyl)benzene Chemical compound FC1=C(F)C(Br)=C(F)C(C(F)(F)F)=C1F NHSSJMAUKULEMJ-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000012530 fluid Substances 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 239000000314 lubricant Substances 0.000 abstract 1
- 239000012430 organic reaction media Substances 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
- C07C17/202—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction
- C07C17/208—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction the other compound being MX
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/093—Preparation of carboxylic acids or their salts, halides or anhydrides by hydrolysis of —CX3 groups, X being halogen
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
- C10M2211/024—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aromatic
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/06—Perfluorinated compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/32—Light or X-ray resistance
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/08—Hydraulic fluids, e.g. brake-fluids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Polyhalogeno - aromatic compounds, e.g 3-chloroheptafluorotoluene, 3,5 - dichlorohexafluorotoluene and 3H-heptafluorotoluene (see Division C2) are used as hydraulic fluids and lubricants.ALSO:Fluorinated aromatic compounds are prepared by reacting a fully halogenated aromatic compound containing as substituents (a) one or more trihalogenomethyl groups and (b) halogen atoms, at least one of which is chlorine, bromine or iodine, with an alkali metal fluoride to replace the higher halogen atoms wholly or partially by fluorine. The halogenated aromatic compound preferably has the formula <FORM:1062301/C2/1> where X = C1, Br or I a = 1, 2, 3,4 and 5 b = 1 or 2 n = 0, 1, 2 or 3 and where (a+b) must not be greater than 6. The starting material may be heated with the alkali metal fluoride (a) in a polar aprotic liquid organic reaction medium inert to the reactants, (b) in a vessel under pressure, e.g. an autoclave at 200 DEG to 600 DEG C. or (c) by passing vapour of the halogenated aromatic compound over a heated bed of the alkali metal fluoride, the latter preferably being finely ground at a temperature in the range of 300 DEG to 600 DEG C. Compounds claimed per se are: 3-chloroheptafluorotoluene; 3,5-dichlorohexafluorotoluene; 3,31 - bis(trifluoromethyl) octafluoro - biphenyl; 3-bromoheptafluorotoluene.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4636/64A GB1062301A (en) | 1964-02-04 | 1964-02-04 | Fluorination of aromatic compounds |
| FR3998A FR1423347A (en) | 1964-02-04 | 1965-02-01 | Fluorination process for aromatic compounds |
| CH148665A CH468321A (en) | 1964-02-04 | 1965-02-03 | Process for the preparation of fluorinated aromatic compounds |
| BE659239D BE659239A (en) | 1964-02-04 | 1965-02-03 | |
| NL6501329A NL6501329A (en) | 1964-02-04 | 1965-02-03 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4636/64A GB1062301A (en) | 1964-02-04 | 1964-02-04 | Fluorination of aromatic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1062301A true GB1062301A (en) | 1967-03-22 |
Family
ID=9780907
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4636/64A Expired GB1062301A (en) | 1964-02-04 | 1964-02-04 | Fluorination of aromatic compounds |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE659239A (en) |
| CH (1) | CH468321A (en) |
| FR (1) | FR1423347A (en) |
| GB (1) | GB1062301A (en) |
| NL (1) | NL6501329A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4937397A (en) * | 1988-11-28 | 1990-06-26 | The Dow Chemical Company | Preparation of halofluorobenzenes |
| US6075165A (en) * | 1993-01-19 | 2000-06-13 | Bayer Aktiengesellschaft | Process for the preparation of polyhalogenated benzotrifluorides, benzotrichlorides and benzoyl chlorides and new trihalogenobenzotrichlorides and -benzoyl chlorides |
| US9212385B2 (en) | 2003-10-31 | 2015-12-15 | Life Technologies Corporation | Fluorinated resorufin compounds and their application |
| CN118791377A (en) * | 2024-09-10 | 2024-10-18 | 山东国邦药业有限公司 | A preparation method of 2,4,5-trifluorophenylacetic acid |
-
1964
- 1964-02-04 GB GB4636/64A patent/GB1062301A/en not_active Expired
-
1965
- 1965-02-01 FR FR3998A patent/FR1423347A/en not_active Expired
- 1965-02-03 BE BE659239D patent/BE659239A/xx unknown
- 1965-02-03 CH CH148665A patent/CH468321A/en unknown
- 1965-02-03 NL NL6501329A patent/NL6501329A/xx unknown
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4937397A (en) * | 1988-11-28 | 1990-06-26 | The Dow Chemical Company | Preparation of halofluorobenzenes |
| US6075165A (en) * | 1993-01-19 | 2000-06-13 | Bayer Aktiengesellschaft | Process for the preparation of polyhalogenated benzotrifluorides, benzotrichlorides and benzoyl chlorides and new trihalogenobenzotrichlorides and -benzoyl chlorides |
| US6114590A (en) * | 1993-01-19 | 2000-09-05 | Bayer Aktiengesellschaft | Process for the preparation of polyhalogenated benzotrifluorides, benzotrichlorides and benzoyl chlorides and new trihalogenobenzotrichlorides and -benzoyl chlorides |
| US9212385B2 (en) | 2003-10-31 | 2015-12-15 | Life Technologies Corporation | Fluorinated resorufin compounds and their application |
| CN118791377A (en) * | 2024-09-10 | 2024-10-18 | 山东国邦药业有限公司 | A preparation method of 2,4,5-trifluorophenylacetic acid |
Also Published As
| Publication number | Publication date |
|---|---|
| BE659239A (en) | 1965-08-03 |
| CH468321A (en) | 1969-02-15 |
| FR1423347A (en) | 1966-01-03 |
| NL6501329A (en) | 1965-08-05 |
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