GB918967A - Process for the alkylation of hydrocarbons and catalyst therefor - Google Patents
Process for the alkylation of hydrocarbons and catalyst thereforInfo
- Publication number
- GB918967A GB918967A GB35694/60A GB3569460A GB918967A GB 918967 A GB918967 A GB 918967A GB 35694/60 A GB35694/60 A GB 35694/60A GB 3569460 A GB3569460 A GB 3569460A GB 918967 A GB918967 A GB 918967A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alumina
- calcined
- alkylation
- pellets
- benzene
- 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
- 230000029936 alkylation Effects 0.000 title abstract 7
- 238000005804 alkylation reaction Methods 0.000 title abstract 7
- 239000003054 catalyst Substances 0.000 title abstract 6
- 229930195733 hydrocarbon Natural products 0.000 title abstract 5
- 150000002430 hydrocarbons Chemical class 0.000 title abstract 5
- 238000000034 method Methods 0.000 title abstract 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 12
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 abstract 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 6
- 239000008188 pellet Substances 0.000 abstract 6
- 239000000203 mixture Substances 0.000 abstract 5
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 abstract 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 4
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 abstract 4
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 abstract 4
- 238000001354 calcination Methods 0.000 abstract 4
- 239000001282 iso-butane Substances 0.000 abstract 4
- 150000005673 monoalkenes Chemical class 0.000 abstract 4
- 239000004215 Carbon black (E152) Substances 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 abstract 3
- 239000000463 material Substances 0.000 abstract 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 abstract 3
- 239000000377 silicon dioxide Substances 0.000 abstract 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 2
- 239000005977 Ethylene Substances 0.000 abstract 2
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 abstract 2
- 230000001476 alcoholic effect Effects 0.000 abstract 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 230000015572 biosynthetic process Effects 0.000 abstract 2
- -1 boria Chemical compound 0.000 abstract 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 abstract 2
- 239000004327 boric acid Substances 0.000 abstract 2
- 230000003197 catalytic effect Effects 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 238000001035 drying Methods 0.000 abstract 2
- SQNZJJAZBFDUTD-UHFFFAOYSA-N durene Chemical compound CC1=CC(C)=C(C)C=C1C SQNZJJAZBFDUTD-UHFFFAOYSA-N 0.000 abstract 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 abstract 2
- 239000000395 magnesium oxide Substances 0.000 abstract 2
- 230000004048 modification Effects 0.000 abstract 2
- 238000012986 modification Methods 0.000 abstract 2
- 229920000098 polyolefin Polymers 0.000 abstract 2
- 239000011148 porous material Substances 0.000 abstract 2
- 239000002243 precursor Substances 0.000 abstract 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 2
- 239000007787 solid Substances 0.000 abstract 2
- ZCUFMDLYAMJYST-UHFFFAOYSA-N thorium dioxide Chemical compound O=[Th]=O ZCUFMDLYAMJYST-UHFFFAOYSA-N 0.000 abstract 2
- 150000004684 trihydrates Chemical class 0.000 abstract 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical class CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 abstract 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N 1-nonene Chemical compound CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract 1
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- HYCOYJYBHKAKGQ-UHFFFAOYSA-N ethylmesitylene Natural products CCC1=C(C)C=C(C)C=C1C HYCOYJYBHKAKGQ-UHFFFAOYSA-N 0.000 abstract 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
- 239000012188 paraffin wax Substances 0.000 abstract 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 abstract 1
- WHFQAROQMWLMEY-UHFFFAOYSA-N propylene dimer Chemical compound CC=C.CC=C WHFQAROQMWLMEY-UHFFFAOYSA-N 0.000 abstract 1
- 239000013638 trimer Substances 0.000 abstract 1
Classifications
-
- 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
-
- 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
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/02—Boron or aluminium; Oxides or hydroxides thereof
- B01J21/04—Alumina
-
- 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
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/12—Silica and alumina
-
- B01J35/615—
-
- 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
- C07C2/56—Addition to acyclic hydrocarbons
- C07C2/58—Catalytic processes
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
- C07C2521/02—Boron or aluminium; Oxides or hydroxides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
- C07C2521/02—Boron or aluminium; Oxides or hydroxides thereof
- C07C2521/04—Alumina
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
- C07C2521/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
- C07C2521/08—Silica
Abstract
Alkylation of aromatic or isoparaffin hydrocarbons with mono-olefins is effected in presence of a solid catalytic material which comprises at least one refractory oxide other than aluminium oxide supported on a base having a large pore structure and being composed essentially of gamma alumina modifications resulting from the drying and calcination of a mixture of precursor hydrous alumina phases containing at least 65% of trihydrate, the base after calcining and before use having a surface area of 350 to 550 sq. metres per gram. Specified refractory oxides include silica, magnesia, thoria, zirconia, and mixtures of these. In an example, an alumina base was prepared as described in Specification 832,200. The alumina gel was washed, dried, and calcined in a current of air at 480 DEG C. The calcined pellets had a surface area of 500 sq. metres per gram. They were impregnated with boric acid solution, dried and calcined. The boria-alumina catalyst was used for the alkylation of benzene with ethylene and for the alkylation of isobutane with propylene. In another example, the alumina pellets were impregnated under vacuum with an alcoholic solution of ethyl orthosilicate and then treated with hydrochloric acid, and the pellets were subsequently dried and calcined to form a silica on alumina catalyst. Specification 735,390 also is referred to.ALSO:An aromatic or isoparaffin hydrocarbon is alkylated with a mono-olefin in the presence of a solid catalytic material which comprises at least one refractory oxide other than aluminium oxide supported on a base having a large pore structure and being composed essentially of gamma alumina modifications resulting from the drying and calcination of a mixture of precursor hydrous alumina phases containing at least 65% of trihydrate, the base after calcining and before use having a surface area of 350 to 550 sq. metres per gram. Specified refractory oxides include silica, magnesia, thoria, boria, zirconia, and mixtures of these. The temperature of alkylation may be in the range 250-650 DEG F. and the pressure may be from atmospheric to 1,000 p.s.i.g. or more. The weight of total feed per weight unit of catalyst per hour may be from 0.1 to 10. The process may be used in the alkylation of isobutane, isopentane, benzene, toluene, or mixtures thereof, with ethylene, propylene, butene, pentene; propylene dimer, trimer or tetramer; or butene dimers. In an example, an alumina base was prepared as described in Specification 832,200. The alumina gel was washed, dried, and calcined in a current of air at 480 DEG C. The calcined pellets had a surface area of 500 sq. metres per gram. They were impregnated with boric acid solution, dried, and calcined. The boria-alumina catalyst was used for the alkylation of benzene with ethylene, ethyl benzene being formed. Isobutane was similarly alkylated with propylene. In another example, the alumina pellets were impregnated while under vacuum with an alcoholic solution of ethyl orthosilicate and then treated with hydrochloric acid, and the pellets were subsequently dried and calcined to form the catalyst material. If desired, there may be introduced into the reaction zone together with the isoparaffin and mono-olefin, an aromatic hydrocarbon of not more than 10 carbon atoms so as to reduce the formation of olefin polymers. In this case lower temperatures e.g. as low as 30 DEG F. may be used. The aromatic hydrocarbon may be benzene, toluene, ethyl benzene, mesitylene, or durene. The formation of olefin polymers may also be substantially reduced by introducing into the reaction zone together with an alkylatable hydrocarbon such as isobutane and the monoolefin, a small proportion of a paraffin hydrocarbon containing 5 or 6 carbon atoms including a tertiary carbon atom e.g. 2-methyl pentane, or diisopropyl. Specification 735,390 also is referred to.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB35694/60A GB918967A (en) | 1960-10-18 | 1960-10-18 | Process for the alkylation of hydrocarbons and catalyst therefor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB35694/60A GB918967A (en) | 1960-10-18 | 1960-10-18 | Process for the alkylation of hydrocarbons and catalyst therefor |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB918967A true GB918967A (en) | 1963-02-20 |
Family
ID=10380533
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB35694/60A Expired GB918967A (en) | 1960-10-18 | 1960-10-18 | Process for the alkylation of hydrocarbons and catalyst therefor |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB918967A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3251902A (en) * | 1963-07-15 | 1966-05-17 | Socony Mobil Oil Co Inc | Isoparaffin-olefin alkylation using crystalline zeolite catalyst |
| US4665256A (en) * | 1983-04-29 | 1987-05-12 | The Dow Chemical Company | Alkylation of aromatic mixtures |
-
1960
- 1960-10-18 GB GB35694/60A patent/GB918967A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3251902A (en) * | 1963-07-15 | 1966-05-17 | Socony Mobil Oil Co Inc | Isoparaffin-olefin alkylation using crystalline zeolite catalyst |
| US4665256A (en) * | 1983-04-29 | 1987-05-12 | The Dow Chemical Company | Alkylation of aromatic mixtures |
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