GB795574A - Process for the alkylation of aromatic compounds - Google Patents
Process for the alkylation of aromatic compoundsInfo
- Publication number
- GB795574A GB795574A GB12642/56A GB1264256A GB795574A GB 795574 A GB795574 A GB 795574A GB 12642/56 A GB12642/56 A GB 12642/56A GB 1264256 A GB1264256 A GB 1264256A GB 795574 A GB795574 A GB 795574A
- Authority
- GB
- United Kingdom
- Prior art keywords
- fluoride
- complex
- boron trifluoride
- thiophenes
- olefine
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/36—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms by addition reactions, i.e. reactions involving at least one carbon-to-carbon unsaturated bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Phenols, thiophenes and furans are alkylated with an olefine acting compound, using a preformed complex of boron trihalide and an iron group metal halide as a catalyst. The catalyst is preferably a preformed complex of boron trifluoride and an iron group metal halide in a low valence state, e.g. ferrous fluoride, cobaltous fluoride, or nickelous fluoride and may be supported on a porous carrier. The complex may be used either in lump form or as preformed pills. Suitable supporting materials are activated charcoal, petroleum coke, coconut char, bone char, metal halides or oxides and other unspecified metal compounds. Suitable phenols, thiophenes and furans which may be subjected to the alkylation are phenol, di and trihydric phenols, halophenols, nitro phenols, naphthol, guiacol, anol, eugenol, thymol; hydroxyacetophenones, hydroxydiphenyls, p-methoxy phenol, cyclohexylphenols, aminophenols, alkyl thiophenes, halo thiophenes, nitrothiophenes, cyanothiophenes, carboxythiophenes, alkyl furans, halofurans, nitrofurans, cyanofurans and carboxyfurans. Suitable olefine acting compounds are alkyl halides or alkyl phosphates which produce olefines under the conditions of the alkylation reaction, and gaseous or liquid olefines such as ethylene, butylene, isobutylenes, olefine polymers having from 6-18 carbon atoms per molecule, cyclopentene, methycyclohexene, butadiene, isoprene. The reaction is carried out at a temperature of from - 60 DEG C. to 300 DEG C. at pressures from about atmospheric pressure to about 100 atmospheres, preferably under sufficient pressure to maintain the reactants and the products in a substantially liquid phase and to maintain the complex as such that no boron trifluoride is lost therefrom. It is preferable to have present from 2 to 10 or more, sometimes up to 20 molecular proportions of alkylatable aromatic hydrocarbon per one molecular proportion of olefine acting compound present. The process may be carried out batchwise or continuously and the reactants added in various ways. Examples are given of the preparation of 2-amyl 5-methyl phenol, by the action of m-cresol with mixed amylenes, amylthiophene from thiophene and 2-pentene, tertiary butyl furan from furan and tertiary butyl chloride. The preparation of 2,6 di-tert.-butyl-4-methyl phenol by the alkylation of p-cresol with tert-butyl chloride or isobutylene is also mentioned.ALSO:Phenols, thiophenes and furans are alkylated with olefine acting compounds in presence of a preformed complex of boron trihalide and an iron group metal halide, preferably a complex of boron trifluoride and ferrous fluoride. The complex may be prepared by either reacting iron with hydrogen fluoride and reacting the ferrous fluoride so formed with boron trifluoride, or contacting the iron simultaneously with hydrogen fluoride and boron trifluoride. The addition of boron trifluoride should take place in an atmosphere of hydrogen fluoride and the iron should preferably be in the finely divided state. Suitable supports are activated charcoal, petroleum coke, coconut char, metal fluorides, e.g. aluminium fluoride, barium fluoride, calcium fluoride, magnesium fluoride, strontium fluoride or metal oxides.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US795574XA | 1955-04-27 | 1955-04-27 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB795574A true GB795574A (en) | 1958-05-28 |
Family
ID=22151287
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB12642/56A Expired GB795574A (en) | 1955-04-27 | 1956-04-25 | Process for the alkylation of aromatic compounds |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB795574A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0041775A1 (en) * | 1980-06-11 | 1981-12-16 | Imperial Chemical Industries Plc | Process for the preparation of alkyl furans |
WO2005073152A2 (en) * | 2004-02-02 | 2005-08-11 | Basf Aktiengesellschaft | Method for producing polyisobutenylphenols |
-
1956
- 1956-04-25 GB GB12642/56A patent/GB795574A/en not_active Expired
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0041775A1 (en) * | 1980-06-11 | 1981-12-16 | Imperial Chemical Industries Plc | Process for the preparation of alkyl furans |
WO2005073152A2 (en) * | 2004-02-02 | 2005-08-11 | Basf Aktiengesellschaft | Method for producing polyisobutenylphenols |
WO2005073152A3 (en) * | 2004-02-02 | 2005-10-06 | Basf Ag | Method for producing polyisobutenylphenols |
US7750193B2 (en) | 2004-02-02 | 2010-07-06 | Basf Aktiengesellschaft | Method for producing polyisobutenylphenols |
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