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US4179472A
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Catalytic alkylation of alkyl-substituted aromatics with monoolefins
Assignee: Phillips Petroleum Co
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Filing: 1978-12-14
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Granted: 1979-12-18
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Expires: 1998-12-14
Abstract
Abstract A process whereby alkyl substituted aromatics are alkylated with a monoolefin in the presence of an alkali metal catalyst and a promoter composition selected from the group consisting of (1) biphenyl and a conjugated diene, (2) biphenyl, a conjugated diene, and a tertiary amine, and (3) naphthalene and a tertiary amine.
Inventors
- 👤 Raymond L. Cobb
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 22:22
CPC Classifications
C; C07; C07C; C07C2/00; C07C2/54; C07C2/72; C07C2523/00; C07C2523/02; C07C2523/04; C07C2531/00; C07C2531/02; C07C2531/26
Claims Analysis
Total Claims: 39
Claim 1
Independent Claim
111 words
A process comprising reacting a monoolefin hydrocarbon with an alkyl aromatic compound having a hydrogen atom bonded to at least one benzylic carbon of at least one alkyl group in the presence of a catalytic amount of alkali metal and a conversion promoting amount of a promoter composition selected from the group consisting of (1) biphenyl and a conjugated diene hydrocarbon containing 4 to 12 carbon atoms per molecule, (2) biphenyl, a conjugated diene hydrocarbon containing 4 to 12 carbon atoms per molecule, and a tertiary amine and (3) naphthalene and a tertiary amine under such reaction conditions that at least one benzylic carbon of said alkyl aromatic compound is alkylated.
Claim 2
Dependent Claim
111 words
A process comprising reacting a monoolefin hydrocarbon with an alkyl aromatic compound having a hydrogen atom bonded to at least one benzylic carbon of at least one alkyl group in the presence of a catalytic amount of alkali metal and a conversion promoting amount of a promoter composition selected from the group consisting of (1) biphenyl and a conjugated diene hydrocarbon containing 4 to 12 carbon atoms per molecule, (2) biphenyl, a conjugated diene hydrocarbon containing 4 to 12 carbon atoms per molecule, and a tertiary amine and (3) naphthalene and a tertiary amine under such reaction conditions that at least one benzylic carbon of said alkyl aromatic compound is alkylated.
Claim 3
Dependent Claim
68 words
A process according to claim 1 wherein said tertiary amine is selected from those having the formula ##STR3## or the formula ##STR4## wherein R is a hydrocarbyl radical of 1 to 6 carbon atoms, R' is a divalent hydrocarbyl radical of 1 to 6 carbon atoms, n is an integer in the range of 0 to 6, and each R and R' can be the same or different.
Claim 4
Dependent Claim
25 words
A process according to claim 2 wherein said promoter composition is a biphenyl and a conjugated diene containing 4 to 12 carbon atoms per molecule.
Claim 5
Dependent Claim
29 words
A process according to claim 3 wherein said alkyl aromatic compound is an alkyl aromatic hydrocarbon having 1 to 4 alkyl substituents each having 1 to 20 carbon atoms.
Claim 6
Dependent Claim
16 words
A process according to claim 4 wherein said monoolefin hydrocarbon is selected from propylene and ethylene.
Claim 7
Dependent Claim
12 words
A process according to claim 5 wherein said conjugated diene is 1,3-butadiene.
Claim 8
Dependent Claim
55 words
A process according to claim 6 wherein for each 100 parts by weight of said alkyl aromatic hydrocarbon there is employed about 0.1 to about 1 part by weight of 1-3 butadiene, and about 0.1 to about 2 parts by weight of biphenyl, and about 1 to about 2 parts by weight of alkali metal.
Claim 9
Dependent Claim
36 words
A process according to claim 7 wherein said reaction is carried out at a temperature in the range of about 125° C. to about 225° C. and a pressure of about 50 to about 1000 psig.
Claim 10
Dependent Claim
13 words
A process according to claim 8 wherein said alkyl aromatic hydrocarbon is cumene.
Claim 11
Dependent Claim
11 words
A process according to claim 9 wherein said monoolefin is ethylene.
Claim 12
Dependent Claim
36 words
A process according to claim 10 wherein said reaction is carried out at a temperature in the range of about 140° C. to about 175° C. and a pressure of about 250 to about 600 psig.
Claim 13
Dependent Claim
39 words
A process according to claim 11 wherein for each 100 parts by weight of cumene there is employed about 0.2 to about 0.5 part by weight of 1,3-butadiene and about 0.2 to about 1 part by weight of biphenyl.
Claim 14
Dependent Claim
28 words
A process according to claim 2 wherein said promoter composition is a biphenyl, a conjugated diene containing 4 to 12 carbon atoms per molecule, and said tertiary amine.
Claim 15
Dependent Claim
29 words
A process according to claim 13 wherein said alkyl aromatic compound is an alkyl aromatic hydrocarbon having 1 to 4 alkyl substituents each having 1 to 20 carbon atoms.
Claim 16
Dependent Claim
66 words
A process according to claim 14 wherein for each 100 parts by weight of said alkyl aromatic hydrocarbon there is employed about 0.1 to about 1 part by weight of said conjugated diene, about 0.1 to about 2 parts by weight of biphenyl, about 1 to about 2 parts by weight of alkali metal and up to about 2 parts by weight of said tertiary amine.
Claim 17
Dependent Claim
16 words
A process according to claim 15 wherein said monoolefin hydrocarbon is selected from propylene and ethylene.
Claim 18
Dependent Claim
12 words
A process according to claim 16 wherein said conjugated diene is 1,3-butadiene.
Claim 19
Dependent Claim
36 words
A process according to claim 17 wherein said reaction is carried out at a temperature in the range of about 125° C. to about 225° C. and a pressure of about 50 to about 1000 psig.
Claim 20
Dependent Claim
14 words
A process according to claim 18 wherein said tertiary amine is triethylamine or N,N,N',N'-tetramethylethylenediamine.
Claim 21
Dependent Claim
13 words
A process according to claim 19 wherein said alkyl aromatic hydrocarbon is cumene.
Claim 22
Dependent Claim
11 words
A process according to claim 20 wherein said monoolefin is ethylene.
Claim 23
Dependent Claim
36 words
A process according to claim 21 wherein said reaction is carried out at a temperature in the range of about 140° C. to about 175° C. and a pressure of about 250 to about 600 psig.
Claim 24
Dependent Claim
50 words
A process according to claim 22 wherein for each 100 parts by weight of cumene there is employed about 0.2 to about 0.5 part by weight of 1,3-butadiene, and about 0.2 to about 1 part by weight of biphenyl, and up to about 1 part by weight of tertiary amine.
Claim 25
Dependent Claim
13 words
A process according to claim 23 wherein said tertiary amine is N,N,N',N'-tetramethylethylene diamine.
Claim 26
Dependent Claim
17 words
A process according to claim 2 wherein said promoter composition is a naphthalene and said tertiary amine.
Claim 27
Dependent Claim
29 words
A process according to claim 25 wherein said alkyl aromatic compound is an alkyl aromatic hydrocarbon having 1 to 4 alkyl substituents each having 1 to 20 carbon atoms.
Claim 28
Dependent Claim
56 words
A process according to claim 26 wherein for each 100 parts by weight of said alkyl aromatic hydrocarbon there is employed about 0.1 to about 5 parts by weight of naphthalene, and about 0.1 to about 2 parts by weight of said tertiary amine, and about 1 to about 2 parts by weight of alkali metal.
Claim 29
Dependent Claim
16 words
A process according to claim 27 wherein said monoolefin hydrocarbon is selected from propylene and ethylene.
Claim 30
Dependent Claim
12 words
A process according to claim 28 wherein said conjugated diene is 1,3-butadiene.
Claim 31
Dependent Claim
36 words
A process according to claim 29 wherein said reaction is carried out at a temperature in the range of about 125° C. to about 225° C. and a pressure of about 50 to about 1000 psig.
Claim 32
Dependent Claim
13 words
A process according to claim 30 wherein said alkyl aromatic hydrocarbon is cumene.
Claim 33
Dependent Claim
11 words
A process according to claim 31 wherein said monoolefin is ethylene.
Claim 34
Dependent Claim
36 words
A process according to claim 32 wherein said reaction is carried out at a temperature in the range of about 140° C. to about 175° C. and a pressure of about 250 to about 600 psig.
Claim 35
Dependent Claim
40 words
A process according to claim 33 wherein for each 100 parts by weight of cumene there is employed about 0.2 to about 1 part by weight of naphthalene and about 0.1 to about 1 part by weight of tertiary amine.
Claim 36
Dependent Claim
12 words
A process according to claim 33 wherein said tertiary amine is N,N,N',N'-tetramethylethylenediamine.
Claim 37
Dependent Claim
12 words
A process according to claim 30 wherein said tertiary amine is N,N,N',N'-tetramethylethylenediamine.
Claim 38
Dependent Claim
12 words
A process according to claim 30 wherein said tertiary amine is triethylamine.
Claim 39
Dependent Claim
14 words
A process according to claim 30 wherein said alkali metal is a sodium-potassium alloy.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1982-12-17 | 1983-06-18 | 1983-12-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-12-17 | 1987-06-18 | 1987-12-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-12-17 | 1991-06-18 | 1991-12-18 | $7700.00 | Window Closed / Lapsed |