US3962361A
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Process for alkylating aromatic hydrocarbons
Assignee: Baroid Technology Inc
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Filing: 1974-12-06
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Granted: 1976-06-08
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Expires: 1994-12-06
Abstract
Abstract Alkylatable aromatic hydrocarbons are alkylated with olefins and alkylhalides under anhydrous alkylating conditions in the presence of a metallic cation exchanged synthetic saponite-type catalyst in which the central octahedral layer contains one or more divalent cations selected from the group consisting of Mg, Ni, Co, Zn, Mn, Cu, and mixtures thereof, provided that the octahedral layer contains less than 95 mole % Mg, and in which the metallic cation has a Pauling electronegativity greater than 1.0. In a specific embodiment, 1-dodecene is reacted with benzene by contacting the dodecene and benzene under anhydrous conditions in the liquid phase at the boiling point of the mixture with a catalyst comprising a metallic cation such as Al3<+>, In3<+> and Cr3<+> exchanged onto the surface of a nickeliferous saponite-type clay.
Inventors
- 👤 George E. Stridde
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 19:59
CPC Classifications
C; C07; C07C; C07C2/00; C07C2/86; C07C2/861; B; B01; B01J; B01J21/00; B01J21/16; B01J29/00; B01J29/04; B01J29/049; C07C2/54; C07C2/64; C07C2/66; C07C2/862; B01J2229/00; B01J2229/30; B01J2229/42; C07C2521/00; C07C2521/16
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
113 words
In a process for alkylating in the liquid phase an alkylatable aromatic hydrocarbon with an olefin-acting compound selected from the group consisting of mono-olefins, alkyl bromides, alkyl chlorides, and mixtures thereof, the improvement which comprises contacting said hydrocarbon and said compound under anhydrous alkylating conditions with a catalyst comprising a synthetic saponite-type mineral in which the central octahedral layer contains one or more divalent cations selected from the group consisting of Mg, Ni, Co, Zn, Mn, Cu, and mixtures thereof, provided that the octahedral layer contains less than 95 mole percent Mg, containing a metallic cation having a Pauling electronegativity greater than 1.0 in cation exchange positions on the surface of said mineral.
Claim 2
Dependent Claim
113 words
In a process for alkylating in the liquid phase an alkylatable aromatic hydrocarbon with an olefin-acting compound selected from the group consisting of mono-olefins, alkyl bromides, alkyl chlorides, and mixtures thereof, the improvement which comprises contacting said hydrocarbon and said compound under anhydrous alkylating conditions with a catalyst comprising a synthetic saponite-type mineral in which the central octahedral layer contains one or more divalent cations selected from the group consisting of Mg, Ni, Co, Zn, Mn, Cu, and mixtures thereof, provided that the octahedral layer contains less than 95 mole percent Mg, containing a metallic cation having a Pauling electronegativity greater than 1.0 in cation exchange positions on the surface of said mineral.
Claim 3
Dependent Claim
74 words
The process of claim 1 wherein said catalyst has the structural formula: [(M.sub.6.sup.2.sup.+).sup.VI (Si.sub.8.sub.-x D.sup.3.sup.+.sub.x).sup.IV O.sub.20 (OH).sub.4.sub.-y F.sub.y ]x/z R.sup.z where 0.33 ≦ x ≦ 1 0 ≦ y ≦ 4 M is said divalent cation, D is a trivalent cation selected from the group consisting of Al, Cr, Fe, Ga, and mixtures thereof, and R is at least one of said metallic cations having a Pauling electronegativity greater than 1.0 of valence z.
Claim 4
Dependent Claim
11 words
The process of claim 2 wherein 0 ≦ y ≦ 2.
Claim 5
Dependent Claim
19 words
The process of claim 3 wherein said aromatic hydrocarbon is benzene and wherein said olefin-acting compound is a mono-olefin.
Claim 6
Dependent Claim
10 words
The process of claim 4 wherein said mono-olefin is 1-dodecene.
Claim 7
Dependent Claim
81 words
The process of claim 3 wherein said R is selected from the group consisting of Al 3 + , Cr 3 + , Ga 3 + , In 3 + , Mn 2 + , Fe 3 + , Col 3 + , Co 2 + , Ni 2 + , Cu 2 + , Ag + , Be 2 + , Mg 2 + , La 3 + , Ce 3 + , Pd 2 + , and mixtures thereof.
Claim 8
Dependent Claim
33 words
The process of claim 3 wherein said R is selected from the group consisting of Al 3 + , Cr 3 + , In 3 + , the rare earths and mixtures thereof.
Claim 9
Dependent Claim
16 words
The process of claim 7 wherein said hydrocarbon is benzene and said compound is a mono-olefin.
Claim 10
Dependent Claim
41 words
The process of claim 3 wherein M is a divalent cation selected from the group consisting of Mg, Ni, Co, and mixtures thereof, and D is a trivalent sation selected from the group consisting of Al, Cr, Fe, and mixtures thereof.
Claim 11
Dependent Claim
17 words
The process of claim 9 wherein said hydrocarbon is benzene and wherein said compound is a mono-olefin.
Claim 12
Dependent Claim
119 words
A process for alkylating aromatic hydrocarbons which comprises contacting in the liquid phase an alkylatable aromatic hydrocarbon with an olefin-acting compound selected from the group consisting of monoolefins, alkyl bromides, alkyl chlorides, and mixtures thereof, under alkylating conditions in a reaction zone which is substantially free of water and in the presence of an effective amount of a catalyst, said catalyst comprising a metallic cation exchanged synthetic saponite-type mineral in which the central octahedral layer contains one or more divalent cations selected from the group consisting of Mg, Ni, Co, Zn, Mn, Cu, and mixtures thereof, provided that the octahedral layer contains less than 95 mole percent Mg, wherein said metallic cation has a Pauling electronegativity greater than 1.0.
Claim 13
Dependent Claim
119 words
A process for alkylating aromatic hydrocarbons which comprises contacting in the liquid phase an alkylatable aromatic hydrocarbon with an olefin-acting compound selected from the group consisting of monoolefins, alkyl bromides, alkyl chlorides, and mixtures thereof, under alkylating conditions in a reaction zone which is substantially free of water and in the presence of an effective amount of a catalyst, said catalyst comprising a metallic cation exchanged synthetic saponite-type mineral in which the central octahedral layer contains one or more divalent cations selected from the group consisting of Mg, Ni, Co, Zn, Mn, Cu, and mixtures thereof, provided that the octahedral layer contains less than 95 mole percent Mg, wherein said metallic cation has a Pauling electronegativity greater than 1.0.
Claim 14
Dependent Claim
73 words
The process of claim 11 wherein said mineral has the structural formula: [(Mg.sub.6.sup.2.sup.+).sup.VI (Si.sub.8.sub.-x D.sup.3.sup.+.sub.x).sup.IV O.sub.20 (OH).sub.4.sub.-y F.sub.y ]x/z R.sup.z where 0.33 ≦ x ≦ 1 0 ≦ y ≦ 4 M is said divalent cation, D is a trivalent cation selected from the group consisting of Al, Cr, Fe, Ga, and mixtures thereof, and R is at least one said metallic cations having a Pauling electronegativity greater than 1.0 of valence z.
Claim 15
Dependent Claim
65 words
The process of claim 12 wherein said R is selected from the group consisting of Al 3 + , Cr 3 + , In 3 + , the rare earths, and mixtures thereof, wherein M is a divalent cation selected from the group consisting of Mg, Ni, Co, and mixtures thereof, wherein D is Al 3 + , and wherein 0 ≦ y ≦ 2.
Claim 16
Dependent Claim
17 words
The process of claim 13 wherein said hydrocarbon is benzene and wherein said compound is a mono-olefin.
Claim 17
Dependent Claim
10 words
The process of claim 14 wherein said mono-olefin is 1-dodecene.
Claim 18
Dependent Claim
119 words
A process for alkylating benzene with a mono-olefin which comprises contacting in the liquid phase said benzene and said olefin in a reaction zone under anhydrous alkylating conditions in the presence of an effective amount of a catalyst, said catalyst comprising a metallic cation-exchanged synthetic saponite-type mineral wherein said metallic cation has a Pauling electronegativity greater than 1.0, and wherein said saponite-type mineral has the structural formula: [(M.sub.6.sup.2.sup.+).sup.VI (Si.sub.8.sub.-x Al.sup.3.sup.+.sub.x).sup.IV O.sub.20 (OH).sub.4.sub.-y F.sub.y ]x/z R.sup.z where 0.33 ≦ x ≦ 1 0 ≦ y ≦ 2 M is a divalent cation selected from the group consisting of Mg, Ni, Co, and mixtures thereof, provided that M is less than 95 mole percent Mg, and R is said metallic cation.
Claim 19
Dependent Claim
119 words
A process for alkylating benzene with a mono-olefin which comprises contacting in the liquid phase said benzene and said olefin in a reaction zone under anhydrous alkylating conditions in the presence of an effective amount of a catalyst, said catalyst comprising a metallic cation-exchanged synthetic saponite-type mineral wherein said metallic cation has a Pauling electronegativity greater than 1.0, and wherein said saponite-type mineral has the structural formula: [(M.sub.6.sup.2.sup.+).sup.VI (Si.sub.8.sub.-x Al.sup.3.sup.+.sub.x).sup.IV O.sub.20 (OH).sub.4.sub.-y F.sub.y ]x/z R.sup.z where 0.33 ≦ x ≦ 1 0 ≦ y ≦ 2 M is a divalent cation selected from the group consisting of Mg, Ni, Co, and mixtures thereof, provided that M is less than 95 mole percent Mg, and R is said metallic cation.
Claim 20
Dependent Claim
46 words
The process of claim 16 wherein the pressure is atmospheric, the temperature is the boiling point of benzene, the molar ratio of benzene to olefin is from about 5:1 to 10:1, and the weight ratio of olefin to said catalyst is from about 2:1 to 20:1.
Claim 21
Dependent Claim
32 words
The process of claim 17 wherein R is selected from the group consisting of Al 3 + , Cr 3 + , In 3 + , the rare earths, and mixtures thereof.
Claim 22
Dependent Claim
12 words
The process of claim 17 wherein R is Al 3 + .
Claim 23
Dependent Claim
10 words
The process of claim 19 wherein said olefin is 1-dodecene.
Claim 24
Dependent Claim
24 words
The process of claim 20 wherein water is removed from said catalyst by azeotropic distillation from a catalyst-benzene mixture before additon of said dodecene.
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) | 1979-06-08 | 1979-12-08 | 1980-06-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-06-08 | 1983-12-08 | 1984-06-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-06-08 | 1987-12-08 | 1988-06-08 | $7700.00 | Window Closed / Lapsed |