CA2093511A1 - Process for producing dialkylnaphthalene - Google Patents
Process for producing dialkylnaphthaleneInfo
- Publication number
- CA2093511A1 CA2093511A1 CA2093511A CA2093511A CA2093511A1 CA 2093511 A1 CA2093511 A1 CA 2093511A1 CA 2093511 A CA2093511 A CA 2093511A CA 2093511 A CA2093511 A CA 2093511A CA 2093511 A1 CA2093511 A1 CA 2093511A1
- Authority
- CA
- Canada
- Prior art keywords
- group
- xal2o3
- al2o3
- sio2
- dialkylnaphthalene
- 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.)
- Granted
Links
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 4
- 229910052751 metal Inorganic materials 0.000 abstract 3
- 239000002184 metal Substances 0.000 abstract 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract 2
- 229910052681 coesite Inorganic materials 0.000 abstract 2
- 229910052593 corundum Inorganic materials 0.000 abstract 2
- 229910052906 cristobalite Inorganic materials 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 230000000737 periodic effect Effects 0.000 abstract 2
- 239000000377 silicon dioxide Substances 0.000 abstract 2
- 235000012239 silicon dioxide Nutrition 0.000 abstract 2
- 229910052682 stishovite Inorganic materials 0.000 abstract 2
- 229910052905 tridymite Inorganic materials 0.000 abstract 2
- 229910001845 yogo sapphire Inorganic materials 0.000 abstract 2
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 abstract 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 229910052733 gallium Inorganic materials 0.000 abstract 1
- 239000007789 gas Substances 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 239000007791 liquid phase Substances 0.000 abstract 1
- 150000002739 metals Chemical class 0.000 abstract 1
- 229910052707 ruthenium Inorganic materials 0.000 abstract 1
- 239000011949 solid catalyst Substances 0.000 abstract 1
- 229910052725 zinc Inorganic materials 0.000 abstract 1
- 239000011701 zinc Substances 0.000 abstract 1
Classifications
-
- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/56—Platinum group metals
- B01J23/62—Platinum group metals with gallium, indium, thallium, germanium, tin or lead
-
- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/56—Platinum group metals
- B01J23/60—Platinum group metals with zinc, cadmium or mercury
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/32—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen
- C07C5/373—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen with simultaneous isomerisation
- C07C5/393—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen with simultaneous isomerisation with cyclisation to an aromatic six-membered ring, e.g. dehydrogenation of n-hexane to benzene
- C07C5/41—Catalytic processes
Abstract
A method for for preparing a dialkylnaphthalene in one step by contacting an dialkylbenzene compound with a solid catalyst in a gas or liquid phase in the presence of hydrogen, using a catalyst having composition (I) or (II) below:
(1) (M1)a~(M2)b~(SiO2~XAl2O3)~(Al2O3)c (I) (2) Mixture of II-(i) and II-(ii):
(M3)d~(Al2O3) II-(i) (M4)e~(SiO2~XAl2O3) II-(ii) wherein M1 is a metal selected from the group consisting of metals belonging to group VIII of a periodic table and ruthenium;
M2 is a member selected from the group consisting of zinc, gallium, and oxides thereof;
M3 is a metal belonging to group VIII of a periodic table;
M4 is at least one alkali metal; and a, b, e, d, e, and X represent proportions, respectively.
(1) (M1)a~(M2)b~(SiO2~XAl2O3)~(Al2O3)c (I) (2) Mixture of II-(i) and II-(ii):
(M3)d~(Al2O3) II-(i) (M4)e~(SiO2~XAl2O3) II-(ii) wherein M1 is a metal selected from the group consisting of metals belonging to group VIII of a periodic table and ruthenium;
M2 is a member selected from the group consisting of zinc, gallium, and oxides thereof;
M3 is a metal belonging to group VIII of a periodic table;
M4 is at least one alkali metal; and a, b, e, d, e, and X represent proportions, respectively.
Applications Claiming Priority (9)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP3/222440 | 1991-08-08 | ||
JP22244091 | 1991-08-08 | ||
JP25034191 | 1991-09-04 | ||
JP3/250341 | 1991-09-04 | ||
JP25279391 | 1991-09-05 | ||
JP3/252793 | 1991-09-05 | ||
JP4/57950 | 1992-03-16 | ||
JP05795092A JP3176688B2 (en) | 1992-03-16 | 1992-03-16 | Method for producing dialkylnaphthalene |
PCT/JP1992/001006 WO1993002995A1 (en) | 1991-08-08 | 1992-08-06 | Process for producing dialkylnaphthalene |
Publications (2)
Publication Number | Publication Date |
---|---|
CA2093511A1 true CA2093511A1 (en) | 1993-02-09 |
CA2093511C CA2093511C (en) | 1999-09-21 |
Family
ID=27463592
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002093511A Expired - Lifetime CA2093511C (en) | 1991-08-08 | 1992-08-06 | Process for producing dialkylnaphthalene |
Country Status (5)
Country | Link |
---|---|
US (1) | US5365001A (en) |
EP (1) | EP0594856B1 (en) |
CA (1) | CA2093511C (en) |
DE (1) | DE69218775T2 (en) |
WO (1) | WO1993002995A1 (en) |
Family Cites Families (39)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3244758A (en) * | 1963-03-20 | 1966-04-05 | Sun Oil Co | Reaction of aromatic hydrocarbons with diolefins |
US3431219A (en) * | 1967-03-08 | 1969-03-04 | Mobil Oil Corp | Crystalline galliosilicates |
JPS50665B1 (en) * | 1970-06-13 | 1975-01-10 | ||
JPS504655B1 (en) * | 1970-09-04 | 1975-02-22 | ||
JPS501269B1 (en) * | 1970-10-02 | 1975-01-16 | ||
JPS5022551B1 (en) * | 1970-10-03 | 1975-07-31 | ||
JPS5017985B1 (en) * | 1970-11-05 | 1975-06-25 | ||
US3931348A (en) * | 1972-12-25 | 1976-01-06 | Mitsui Petrochemical Industries, Ltd. | Process for preparing dimethyl naphthalene |
US3811491A (en) * | 1973-03-01 | 1974-05-21 | Jones & Laughlin Steel Corp | Method and apparatus for minimizing surface defects on itr cast strip |
JPS501037A (en) * | 1973-05-07 | 1975-01-08 | ||
JPS50665A (en) * | 1973-05-09 | 1975-01-07 | ||
JPS501269A (en) * | 1973-05-11 | 1975-01-08 | ||
JPS504655A (en) * | 1973-05-16 | 1975-01-18 | ||
JPS5012430A (en) * | 1973-06-05 | 1975-02-08 | ||
JPS531150B2 (en) * | 1973-06-18 | 1978-01-14 | ||
JPS5022551A (en) * | 1973-06-27 | 1975-03-11 | ||
JPS582223B2 (en) * | 1974-07-02 | 1983-01-14 | 三菱化学株式会社 | 2.6- Naphthalene dicarbonate |
JPS5648494B2 (en) * | 1974-07-02 | 1981-11-16 | ||
JPS5929178B2 (en) * | 1978-04-08 | 1984-07-18 | 丸善石油化学株式会社 | Process for producing 2-alkyl-6-acylnaphthalene |
US4530645A (en) * | 1979-09-21 | 1985-07-23 | Hydraunit Venture | Oil well pumping apparatus |
US4392989A (en) * | 1981-05-11 | 1983-07-12 | Mobil Oil Corporation | Zinc-gallium zeolite |
US4458025A (en) * | 1982-09-20 | 1984-07-03 | Chevron Research Company | Method of zeolitic catalyst manufacture |
JPS6045536A (en) * | 1983-08-22 | 1985-03-12 | Teijin Yuka Kk | Trans-methylation of methyl-substituted naphthalene |
JPS60172937A (en) * | 1984-02-16 | 1985-09-06 | Teijin Yuka Kk | Method of methylation of naphthalenes |
JPS60188343A (en) * | 1984-03-07 | 1985-09-25 | Mitsubishi Gas Chem Co Inc | Preparation of aromatic ketone |
US4623632A (en) * | 1984-11-05 | 1986-11-18 | Uop Inc. | Catalytic composite for conversion of hydrocarbons and the method of preparation and use thereof |
JPH0684328B2 (en) * | 1985-08-31 | 1994-10-26 | 三菱瓦斯化学株式会社 | Method for producing aromatic ketone |
US4985384A (en) * | 1986-08-25 | 1991-01-15 | W. R. Grace & Co-Conn. | Cracking catalysts having aromatic selectivity |
JPS649942A (en) * | 1987-07-02 | 1989-01-13 | Nippon Steel Chemical Co | Production of dialkylnaphthalenes |
JPS649943A (en) * | 1987-07-02 | 1989-01-13 | Nippon Steel Chemical Co | Production of alkylnaphthalenes |
US4824816A (en) * | 1987-09-21 | 1989-04-25 | Exxon Research & Engineering Company | Method for producing stabilized zeolite catalysts |
US5030781A (en) * | 1990-06-15 | 1991-07-09 | Amoco Corporation | Preparation of a dimethyltetralin |
US4873386A (en) * | 1988-06-28 | 1989-10-10 | Amoco Corporation | Selective production of 2,6-diethylnaphthalene |
US5008479A (en) * | 1988-09-27 | 1991-04-16 | Mitsubishi Gas Chemical Company, Inc. | Process for production of 2,6-dimethylnaphthalene |
JPH02167237A (en) * | 1988-09-27 | 1990-06-27 | Mitsubishi Gas Chem Co Inc | Production of 1-(alkyl or alkenyl)-6'-methylnaphthalene |
JPH0296540A (en) * | 1988-10-03 | 1990-04-09 | Mitsubishi Gas Chem Co Inc | Production of 2,6-dimethylnaphthalene |
US5003122A (en) * | 1988-10-05 | 1991-03-26 | Catalytica, Inc. | Process for selective diisopropylation of naphthyl compounds using shape selective acidic crystalline molecular sieve catalysts |
DE69004542T2 (en) * | 1989-12-01 | 1994-03-10 | Mitsubishi Gas Chemical Co | Process for the preparation of 2,6-dimethylnaphthalene. |
JPH03251545A (en) * | 1990-02-27 | 1991-11-11 | Mitsubishi Gas Chem Co Inc | Production of 2,6-dimethylnaphthalene |
-
1992
- 1992-08-06 CA CA002093511A patent/CA2093511C/en not_active Expired - Lifetime
- 1992-08-06 US US08/039,067 patent/US5365001A/en not_active Expired - Lifetime
- 1992-08-06 WO PCT/JP1992/001006 patent/WO1993002995A1/en active IP Right Grant
- 1992-08-06 DE DE69218775T patent/DE69218775T2/en not_active Expired - Lifetime
- 1992-08-06 EP EP92916964A patent/EP0594856B1/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
WO1993002995A1 (en) | 1993-02-18 |
DE69218775D1 (en) | 1997-05-07 |
CA2093511C (en) | 1999-09-21 |
EP0594856A4 (en) | 1993-12-22 |
DE69218775T2 (en) | 1997-07-10 |
EP0594856A1 (en) | 1994-05-04 |
US5365001A (en) | 1994-11-15 |
EP0594856B1 (en) | 1997-04-02 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
EEER | Examination request | ||
MKEX | Expiry |