US4287376A
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Method for aralkylation
Assignee: Eneos Corp
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Filing: 1979-07-25
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Granted: 1981-09-01
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Expires: 1999-07-25
Abstract
Abstract A method for aralkylation of benzene or alkylbenzenes which is characterized in that an aromatic olefin having a double bond or double bonds which are conjugated with the benzene ring is added to the benzene or alkylbenzenes in the presence of at least one member of catalyst selected from the group consisting of the compounds represented by the general formula: C.sub.n F.sub.2n+1-m Cl.sub.m SO.sub.3 H in which the symbol n is an integer from 1 to 5 and m is 0 or 1. Since the selectivity to the aromatic olefin in the reaction is excellent, the mixture of aromatic olefins and aliphatic olefins can be employed as one of the starting material.
Inventors
- 👤 Isoo Shimizu
- 👤 Okitsugu Tsuji
- 👤 Eiichi Matsuzaka
- 👤 Atsushi Sato
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 06:10
CPC Classifications
C; C07; C07C; C07C2/00; C07C2/54; C07C2/64; C07C2/66; C07C2/70; C07C2531/00; C07C2531/02; C07C2531/025
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
118 words
In a method of aralkylation of at least one member selected from the group consisting of benzene and alkylbenzenes each having an alkyl group or groups of 1 to 18 in total carbon atom number by reacting at least one aromatic olefin each having a double bond or double bonds which are conjugated with the benzene ring thereof with said at least one member, the improvement in said method comprising carrying out said aralkylation in the presence of at least one catalyst selected from the group of compounds represented by the general formula: C.sub.n F.sub.2n+1-m Cl.sub.m SO.sub.3 H, in which the symbol n is an integer from 1 to 5, inclusive, and m is 0 (zero) or 1.
Claim 2
Dependent Claim
118 words
In a method of aralkylation of at least one member selected from the group consisting of benzene and alkylbenzenes each having an alkyl group or groups of 1 to 18 in total carbon atom number by reacting at least one aromatic olefin each having a double bond or double bonds which are conjugated with the benzene ring thereof with said at least one member, the improvement in said method comprising carrying out said aralkylation in the presence of at least one catalyst selected from the group of compounds represented by the general formula: C.sub.n F.sub.2n+1-m Cl.sub.m SO.sub.3 H, in which the symbol n is an integer from 1 to 5, inclusive, and m is 0 (zero) or 1.
Claim 3
Dependent Claim
25 words
The improvement as claimed in claim 1, wherein said aralkylation is carried out at a temperature in the range of 5° to 150° C., inclusive.
Claim 4
Dependent Claim
60 words
The improvement as claimed in claim 1, wherein said at least one member and said at least one aromatic olefin are contained in a feed which is the fraction of thermal cracking by-product oil having a boiling range of 45° to 198° C. which is obtained when petroleum hydrocarbons are thermally cracked at a temperature of 700° C. or higher.
Claim 5
Dependent Claim
23 words
The improvement as claimed in claim 1, wherein a feed containing both aliphatic olefins and said aromatic olefins is used in said aralkylation.
Claim 6
Dependent Claim
60 words
The improvement as claimed in claim 1, wherein said catalyst is at least one member selected from the group consisting of CF 3 SO 3 H, CF 2 ClSO 3 H, C 2 F 5 SO 3 H, C 3 F 7 SO 3 H, C 4 F 9 SO 3 H, and C 5 F 11 SO 3 H.
Claim 7
Dependent Claim
51 words
The improvement as claimed in any one of claims 1, 2, 3, 4, or 5, wherein said allkylbenzenes are selected from the group consisting of toluene, o-xylene, m-xylene, p-xylene, ethylbenzene, 1,2,3-trimethylbenzene, 1,2,4-trimethylbenzene, 1,3,5-trimethylbenzene, o-ethyltoluene, m-ethyltoluene, p-ethyltoluene, n-propylbenzene, cumene, higher alkylbenzenes having alkyl groups of 4 to 18 carbon atoms, and cycloalkylbenzenes.
Claim 8
Dependent Claim
42 words
The improvement as claimed in any one of claims 1, 2, 3, 4, or 5, wherein said at least one aromatic olefin is selected from the group consisting of styrene, α-methylstyrene, β-methylstyrene and vinyltoluene, divinylbenzene and its alkyl derivatives, indene, and alkylindenes.
Claim 9
Dependent Claim
56 words
The improvement as claimed in any one of claims 1, 2, 3, 4, or 5 wherein said aralkylation is carried out at a temperature in the range of 5° C. to 150° C. and at a pressure sufficient to maintain said at least one member and said at least one aromatic olefin in the liquid state.
Claim 10
Dependent Claim
67 words
The improvement as claimed in any one of claims 1, 2, 3, or 4 wherein said catalyst is at least one member selected from the group consisting of CF 3 SO 3 H, CF 2 ClSO 3 H, C 2 F 5 SO 3 H, C 3 F 7 SO 3 H, C 4 F 9 SO 3 H, and C 5 F 11 SO 3 H.
Claim 11
Dependent Claim
79 words
The improvement as claimed in any one of claims 1, 2, 3, 4, or 5 wherein said alkylbenzenes are selected from the group consisting of toluene, o-xylene, m-xylene, p-xylene, ethylbenzene, 1,2,3-trimethylbenzene, 1,2,4-trimethylbenzene, 1,3,5-trimethylbenzene, o-ethyltoluene, m-ethyltoluene, p-ethyltoluene, n-propylbenzene, cumene, higher alkylbenzenes having alkyl groups of 4 to 18 carbon atoms, indane, and tetralin, and wherein said at least one aromatic olefin is selected from the group consisting of styrene, α-methylstyrene, β-methylstyrene, vinyltoluene, divinylbenzene and its alkyl derivatives, indenes and alkylindenes.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-08-31 | 1985-03-02 | 1985-09-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-08-31 | 1989-03-02 | 1989-09-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-08-31 | 1993-03-02 | 1993-09-01 | $7700.00 | Window Closed / Lapsed |