GB794153A - Process for alkylating aromatic compounds - Google Patents
Process for alkylating aromatic compoundsInfo
- Publication number
- GB794153A GB794153A GB12641/56A GB1264156A GB794153A GB 794153 A GB794153 A GB 794153A GB 12641/56 A GB12641/56 A GB 12641/56A GB 1264156 A GB1264156 A GB 1264156A GB 794153 A GB794153 A GB 794153A
- Authority
- GB
- United Kingdom
- Prior art keywords
- fluoride
- complex
- mol
- benzene
- hydrogen fluoride
- 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
- 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
- C07C37/18—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 condensation involving halogen atoms of halogenated compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/08—Halides
- B01J27/12—Fluorides
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/128—Halogens; Compounds thereof with iron group metals or platinum group metals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/02—Monocyclic hydrocarbons
- C07C15/107—Monocyclic hydrocarbons having saturated side-chain containing at least six carbon atoms, e.g. detergent alkylates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
- C07C2/64—Addition to a carbon atom of a six-membered aromatic ring
- C07C2/66—Catalytic processes
- C07C2/70—Catalytic processes with acids
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/06—Halogens; Compounds thereof
- C07C2527/08—Halides
- C07C2527/12—Fluorides
- C07C2527/1206—Hydrogen fluoride
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/06—Halogens; Compounds thereof
- C07C2527/08—Halides
- C07C2527/12—Fluorides
- C07C2527/1213—Boron fluoride
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/06—Halogens; Compounds thereof
- C07C2527/128—Compounds comprising a halogen and an iron group metal or a platinum group metal
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Aromatic hydrocarbons, and their hydroxy-and halo-derivatives, are alkylated with olefines or alkyl halides in the presence of anhydrous hydrogen fluoride and a preformed complex of boron trifluoride and an iron group metal fluoride. Preferred aromatic compounds are monocyclic such as benzene, toluene, xylenes, ethylbenzene, mesitylene, ethyltoluenes, n-propyl benzene, cumene, C6-C18 alkyl benzenes and toluenes, styrene, vinyl toluenes, allyl benzene, phenol, cresols, chlorophenols, p-bromophenol, 2,4,6-trichloro- and -tribromophenols, guaiacol, and, isoeugenol, eugenol, carvacrol, thymol, o- and p-cyclohexyl phenols, catechol, resorcinol, hydroquinone, pyrogallol, hydroxyhydroquinone, phloroglucinol, fluoro-, chloro-, bromo- and iod0-benzenes, chloro- and bromo - toluenes, p - dichloro, 1,2,4 - trichloro -, 1,2,3,4 - tetrachloro - and 1,2,4,5 - tetrachlorobenzenes, p - dibromobenzene, o- and p-bromochlorobenzenes, o-, and p-bromoiodobenzenes and p - chloroiodobenzene. Polycyclic compounds which may be used include diphenyl, diphenylmethane, triphenylmethane, fluorene, stilbene, naphthalene, anthracene, phenanthrene, naphthacene, rubrene and 2,21- and 4,41-dihydroxy-diphenyl. Olefines which may be used as alkylating agents include ethylene, propylene, 1- and 2-butenes, isobutylene, pentenes, olefine polymers of 6-18 carbon atoms, cyclopentane, cyclohexene, methylcyclopentene, methylcyclohexene, butadiene and isoprene, n-Butyl chloride is also referred to as an alkylating agent. The complex of the catalyst is preferably formed from an iron-group metal in the divalent state and can be prepared by forming the metal fluoride and adding the boron trifluoride in the presence of hydrogen fluoride; the metal fluoride may be formed in situ from the metal and hydrogen fluoride. It may be used in solution in HF when it should be present in an amount of at least one mol. per 150 mols. of HF, as a solid mass or slurry with HF when the HF should be present in an amount of at least 0.5 mol. per mol. of complex, or disposed on a carrier such as activated charcoal, aluminium fluoride, calcium fluoride, magnesium fluoride, strontium fluoride or barium fluoride, when the HF should be present in an amount of at least 0.01 mol. per mol. of complex. The hydrogen fluoride may be replaced by a C2-C6 alkyl fluoride which releases hydrogen fluoride under the reaction conditions. Liquid phase conditions are preferred at -60 DEG to 300 DEG C. The pressure should be sufficient to prevent the complex losing BF3 and may be 1-100 atmospheres. A mol. ratio of alkylating agent to aromatic compound in the range of 1 : 2 to 1 : 20 is preferred. Batch or continuous operations may be used. The examples describe the preparation of a FeF2.BF3 complex and its use with hydrogen fluoride in reactions between (1) propylene and toluene; (2) ethylene and benzene; (3) n-butyl chloride and m-cresol; (4) a propylene tetramer fraction and benzene.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US794153XA | 1955-04-27 | 1955-04-27 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB794153A true GB794153A (en) | 1958-04-30 |
Family
ID=22150401
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB12641/56A Expired GB794153A (en) | 1955-04-27 | 1956-04-25 | Process for alkylating aromatic compounds |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB794153A (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3157459A (en) * | 1961-04-11 | 1964-11-17 | Rohm & Haas | Process of alkylating shaped, oriented linear polymers |
US3217076A (en) * | 1962-04-30 | 1965-11-09 | Rohm & Haas | Hf or hf-bf3 composition treatment of fibers and films of polystyrene and polyvinyl alcohol or polyvinyl alcohol esters and ethers |
FR2540101A1 (en) * | 1983-02-02 | 1984-08-03 | Rhone Poulenc Spec Chim | PROCESS FOR ALKYLATION OF HALOGENIC AND / OR TRIFLUOROMETHYL BENZENE DERIVATIVES |
CN107961779A (en) * | 2017-11-24 | 2018-04-27 | 江西省隆南药化有限公司 | A kind of catalyst for musk ambrette grass phenol and preparation method thereof, and the method using the catalyst preparation thymol |
CN111302880A (en) * | 2020-03-12 | 2020-06-19 | 川北医学院 | Application of iron catalyst in reduction coupling reaction and preparation method of aromatic ring and heterocyclic derivative |
-
1956
- 1956-04-25 GB GB12641/56A patent/GB794153A/en not_active Expired
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3157459A (en) * | 1961-04-11 | 1964-11-17 | Rohm & Haas | Process of alkylating shaped, oriented linear polymers |
US3217076A (en) * | 1962-04-30 | 1965-11-09 | Rohm & Haas | Hf or hf-bf3 composition treatment of fibers and films of polystyrene and polyvinyl alcohol or polyvinyl alcohol esters and ethers |
FR2540101A1 (en) * | 1983-02-02 | 1984-08-03 | Rhone Poulenc Spec Chim | PROCESS FOR ALKYLATION OF HALOGENIC AND / OR TRIFLUOROMETHYL BENZENE DERIVATIVES |
EP0115985A1 (en) * | 1983-02-02 | 1984-08-15 | Rhone-Poulenc Specialites Chimiques | Process for the alkylation of halogenated and/or trifluormethylated benzenederivatives |
US4560814A (en) * | 1983-02-02 | 1985-12-24 | Rhone-Poulenc Specialites Chimiques | Process for alkylating halogenated and trifluoromethylated benzene compounds |
CN107961779A (en) * | 2017-11-24 | 2018-04-27 | 江西省隆南药化有限公司 | A kind of catalyst for musk ambrette grass phenol and preparation method thereof, and the method using the catalyst preparation thymol |
CN107961779B (en) * | 2017-11-24 | 2020-10-23 | 江西省隆南药化有限公司 | Catalyst for synthesizing thymol, preparation method thereof and method for preparing thymol by using catalyst |
CN111302880A (en) * | 2020-03-12 | 2020-06-19 | 川北医学院 | Application of iron catalyst in reduction coupling reaction and preparation method of aromatic ring and heterocyclic derivative |
CN111302880B (en) * | 2020-03-12 | 2022-09-13 | 川北医学院 | Application of iron catalyst in reduction coupling reaction and preparation method of aromatic ring and heterocyclic derivative |
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