JPS5953249B2 - 芳香族アルコ−ルの製法 - Google Patents
芳香族アルコ−ルの製法Info
- Publication number
- JPS5953249B2 JPS5953249B2 JP50106431A JP10643175A JPS5953249B2 JP S5953249 B2 JPS5953249 B2 JP S5953249B2 JP 50106431 A JP50106431 A JP 50106431A JP 10643175 A JP10643175 A JP 10643175A JP S5953249 B2 JPS5953249 B2 JP S5953249B2
- Authority
- JP
- Japan
- Prior art keywords
- acetophenone
- catalyst
- copper
- weight
- monocyclic aromatic
- 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
- 238000004519 manufacturing process Methods 0.000 title description 5
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 title 1
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 74
- 239000003054 catalyst Substances 0.000 claims description 44
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 24
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 23
- WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical compound CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 claims description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 18
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 229910052802 copper Inorganic materials 0.000 claims description 15
- 239000010949 copper Substances 0.000 claims description 15
- 238000005984 hydrogenation reaction Methods 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- 239000011787 zinc oxide Substances 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- -1 monocyclic aromatic hydrocarbon Chemical class 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- 239000011159 matrix material Substances 0.000 claims description 7
- 239000002245 particle Substances 0.000 claims description 6
- 239000000376 reactant Substances 0.000 claims description 6
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 12
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 9
- 239000011701 zinc Substances 0.000 description 9
- 229910052725 zinc Inorganic materials 0.000 description 9
- 229960004643 cupric oxide Drugs 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000005751 Copper oxide Substances 0.000 description 6
- 229910000431 copper oxide Inorganic materials 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 239000011812 mixed powder Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 150000002927 oxygen compounds Chemical class 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 238000001694 spray drying Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 229910001369 Brass Inorganic materials 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 description 1
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000008365 aromatic ketones Chemical class 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 239000010951 brass Substances 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 229910002090 carbon oxide Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000012018 catalyst precursor Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000001010 compromised effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 239000007862 dimeric product Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- YZYKBQUWMPUVEN-UHFFFAOYSA-N zafuleptine Chemical compound OC(=O)CCCCCC(C(C)C)NCC1=CC=C(F)C=C1 YZYKBQUWMPUVEN-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
- C07C29/145—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones with hydrogen or hydrogen-containing gases
-
- 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
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/80—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with zinc, cadmium or mercury
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US502583 | 1974-09-03 | ||
| US502583A US3927120A (en) | 1974-09-03 | 1974-09-03 | Preparation of phenyl methyl carbinol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5152145A JPS5152145A (en) | 1976-05-08 |
| JPS5953249B2 true JPS5953249B2 (ja) | 1984-12-24 |
Family
ID=23998464
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP50106431A Expired JPS5953249B2 (ja) | 1974-09-03 | 1975-09-02 | 芳香族アルコ−ルの製法 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US3927120A (enExample) |
| JP (1) | JPS5953249B2 (enExample) |
| AR (1) | AR204873A1 (enExample) |
| BE (1) | BE832771A (enExample) |
| BR (1) | BR7505624A (enExample) |
| CA (1) | CA1059151A (enExample) |
| DE (1) | DE2538205A1 (enExample) |
| ES (1) | ES440698A1 (enExample) |
| FR (1) | FR2283880A1 (enExample) |
| GB (1) | GB1510817A (enExample) |
| IN (1) | IN141801B (enExample) |
| IT (1) | IT1041548B (enExample) |
| NL (1) | NL7510047A (enExample) |
| ZA (1) | ZA755286B (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5910256B2 (ja) * | 1979-11-12 | 1984-03-07 | 三菱瓦斯化学株式会社 | メタノ−ル合成触媒の製造法 |
| US4762817A (en) * | 1986-11-03 | 1988-08-09 | Union Carbide Corporation | Aldehyde hydrogenation catalyst |
| US4876402A (en) * | 1986-11-03 | 1989-10-24 | Union Carbide Chemicals And Plastics Company Inc. | Improved aldehyde hydrogenation process |
| US5345005A (en) * | 1989-09-12 | 1994-09-06 | Engelhard Corporation | Hydrogenation catalyst, process for preparing and process of using said catalyst |
| US4996374A (en) * | 1989-12-15 | 1991-02-26 | Arco Chemical Technology, Inc. | Hydrogenation of acetophenone |
| US5214168A (en) * | 1992-04-30 | 1993-05-25 | Arco Chemical Technology, L.P. | Integrated process for epoxide production |
| US5663458A (en) * | 1994-12-02 | 1997-09-02 | Sumitomo Chemical Company, Limited. | Process for producing α-phenylethyl alcohol |
| SG66476A1 (en) * | 1997-07-14 | 1999-07-20 | Sumitomo Chemical Co | Process for producing alpha-phenylethyl alcohol |
| JP3899764B2 (ja) * | 2000-01-19 | 2007-03-28 | 住友化学株式会社 | α−フェニルエチルアルコールの製造方法 |
| EP1608610B1 (en) * | 2003-03-28 | 2013-04-03 | Shell Internationale Research Maatschappij B.V. | Process for the hydrogenation of alkylaryl ketones |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2234100A (en) * | 1938-11-12 | 1941-03-04 | Cities Service Oil Co | Gas pumping |
| US2400959A (en) * | 1940-12-18 | 1946-05-28 | Iowa State College Res Found | Hydrogenation and dehydrogenation catalysts |
| FR1419759A (fr) * | 1964-10-16 | 1965-12-03 | Melle Usines Sa | Procédé pour l'exécution en continu de réactions d'hydrogénation en phase liquide |
-
1974
- 1974-09-03 US US502583A patent/US3927120A/en not_active Expired - Lifetime
-
1975
- 1975-01-01 AR AR260234A patent/AR204873A1/es active
- 1975-08-06 CA CA232,973A patent/CA1059151A/en not_active Expired
- 1975-08-13 GB GB33755/75A patent/GB1510817A/en not_active Expired
- 1975-08-18 ZA ZA00755286A patent/ZA755286B/xx unknown
- 1975-08-19 IN IN1617/CAL/75A patent/IN141801B/en unknown
- 1975-08-26 BE BE159488A patent/BE832771A/xx not_active IP Right Cessation
- 1975-08-26 NL NL7510047A patent/NL7510047A/xx not_active Application Discontinuation
- 1975-08-27 DE DE19752538205 patent/DE2538205A1/de not_active Withdrawn
- 1975-08-28 IT IT51101/75A patent/IT1041548B/it active
- 1975-09-01 FR FR7526758A patent/FR2283880A1/fr active Granted
- 1975-09-02 BR BR7505624*A patent/BR7505624A/pt unknown
- 1975-09-02 JP JP50106431A patent/JPS5953249B2/ja not_active Expired
- 1975-09-03 ES ES440698A patent/ES440698A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5152145A (en) | 1976-05-08 |
| CA1059151A (en) | 1979-07-24 |
| BR7505624A (pt) | 1976-08-03 |
| US3927120A (en) | 1975-12-16 |
| AU8377575A (en) | 1977-02-10 |
| NL7510047A (nl) | 1976-03-05 |
| ZA755286B (en) | 1976-07-28 |
| FR2283880A1 (fr) | 1976-04-02 |
| FR2283880B1 (enExample) | 1979-03-09 |
| IT1041548B (it) | 1980-01-10 |
| BE832771A (fr) | 1975-12-16 |
| IN141801B (enExample) | 1977-04-23 |
| GB1510817A (en) | 1978-05-17 |
| ES440698A1 (es) | 1977-03-01 |
| DE2538205A1 (de) | 1976-03-11 |
| AR204873A1 (es) | 1976-03-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DK167183B1 (da) | Fremgangsmaade til fremstilling af alkoholer ved dampfasehydrogenering af aldehyder | |
| US3689533A (en) | Production of carboxylic acids and esters | |
| US3515514A (en) | Production of hydrogen containing gases | |
| US4780552A (en) | Preparation of furan by decarbonylation of furfural | |
| US4780448A (en) | Preparation of a catalyst containing copper and silica | |
| US4476250A (en) | Catalytic process for the production of methanol | |
| US7435703B2 (en) | Catalyst comprising iron oxide made by heat decomposition of an iron halide and a lanthanide | |
| US4327190A (en) | Process for the production of C1 to C4 oxygenated hydrocarbons | |
| JPH05505975A (ja) | 活性触媒を用いた高転化率及び高選択率のγ―ブチロラクトンへの無水マレイン酸の気相接触水素添加方法 | |
| US4564642A (en) | Process for the manufacture of unsaturated hydrocarbons | |
| JPS5953249B2 (ja) | 芳香族アルコ−ルの製法 | |
| US4579995A (en) | Process for the conversion of methanol to hydrocarbons | |
| US2446132A (en) | Silver catalysts | |
| US3927121A (en) | Phenyl methyl carbinol manufacture by hydrogenation of acetophenone | |
| JPS606925B2 (ja) | 不飽和炭化水素の製法 | |
| JP3237365B2 (ja) | フェノールの製造方法 | |
| JPS6113689B2 (enExample) | ||
| WO2010119448A1 (en) | An 'in-situ' prepared, improved catalyst for low pressure continuous butynediol synthesis | |
| TW460327B (en) | Catalyst for dehydrogenation of cyclohexanol | |
| JPS6228081B2 (enExample) | ||
| US4035428A (en) | Process for production of orthophenylphenol | |
| US4294968A (en) | Method for preparing α-picoline from 5-oxohexanenitrile | |
| JPS62258335A (ja) | メチルイソブチルケトンの製造法 | |
| US4619947A (en) | Chemical process | |
| JPH0247972B2 (enExample) |