CN1099740A - 芳族醛的选择性催化加氢 - Google Patents
芳族醛的选择性催化加氢 Download PDFInfo
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- CN1099740A CN1099740A CN94100192A CN94100192A CN1099740A CN 1099740 A CN1099740 A CN 1099740A CN 94100192 A CN94100192 A CN 94100192A CN 94100192 A CN94100192 A CN 94100192A CN 1099740 A CN1099740 A CN 1099740A
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- carrier
- tio
- catalyzer
- hydrogenation
- aromatic aldehyde
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- 150000003934 aromatic aldehydes Chemical class 0.000 title claims abstract description 22
- 238000009903 catalytic hydrogenation reaction Methods 0.000 title claims abstract description 11
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims abstract description 103
- 238000000034 method Methods 0.000 claims abstract description 73
- 239000003054 catalyst Substances 0.000 claims abstract description 38
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims abstract description 32
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 31
- 229910052751 metal Inorganic materials 0.000 claims abstract description 23
- 239000002184 metal Substances 0.000 claims abstract description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
- 239000001257 hydrogen Substances 0.000 claims abstract description 15
- 239000002904 solvent Substances 0.000 claims abstract description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 150000002367 halogens Chemical class 0.000 claims abstract description 6
- 150000007524 organic acids Chemical class 0.000 claims abstract description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 90
- 238000005984 hydrogenation reaction Methods 0.000 claims description 39
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 36
- -1 methyl compound Chemical class 0.000 claims description 30
- 229910052697 platinum Inorganic materials 0.000 claims description 16
- MGMNPSAERQZUIM-UHFFFAOYSA-N 2-(hydroxymethyl)benzoic acid Chemical compound OCC1=CC=CC=C1C(O)=O MGMNPSAERQZUIM-UHFFFAOYSA-N 0.000 claims description 14
- 229910052763 palladium Inorganic materials 0.000 claims description 14
- 239000004408 titanium dioxide Substances 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- 229910002651 NO3 Inorganic materials 0.000 claims description 10
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 claims description 10
- 239000010948 rhodium Substances 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- 229910052703 rhodium Inorganic materials 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 239000000853 adhesive Substances 0.000 claims description 3
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- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 230000008569 process Effects 0.000 abstract description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 3
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- 235000005985 organic acids Nutrition 0.000 abstract 1
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- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 32
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- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 4
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- 150000004703 alkoxides Chemical class 0.000 description 3
- 230000008859 change Effects 0.000 description 3
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- 239000012535 impurity Substances 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- GPNDARIEYHPYAY-UHFFFAOYSA-N palladium(ii) nitrate Chemical compound [Pd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O GPNDARIEYHPYAY-UHFFFAOYSA-N 0.000 description 3
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- KNEUJTFLMQRIFD-UHFFFAOYSA-N 1-chloro-4-methylcyclohexane Chemical compound CC1CCC(Cl)CC1 KNEUJTFLMQRIFD-UHFFFAOYSA-N 0.000 description 2
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 244000060011 Cocos nucifera Species 0.000 description 2
- 235000013162 Cocos nucifera Nutrition 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
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- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
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- QSSJZLPUHJDYKF-UHFFFAOYSA-N methyl 4-methylbenzoate Chemical compound COC(=O)C1=CC=C(C)C=C1 QSSJZLPUHJDYKF-UHFFFAOYSA-N 0.000 description 1
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
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- SOQBVABWOPYFQZ-UHFFFAOYSA-N oxygen(2-);titanium(4+) Chemical compound [O-2].[O-2].[Ti+4] SOQBVABWOPYFQZ-UHFFFAOYSA-N 0.000 description 1
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- 239000006069 physical mixture Substances 0.000 description 1
- NWAHZABTSDUXMJ-UHFFFAOYSA-N platinum(2+);dinitrate Chemical compound [Pt+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O NWAHZABTSDUXMJ-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
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- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
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- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
-
- 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
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
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- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/0201—Impregnation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
- C07C1/22—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms by reduction
-
- 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
- C07C29/14—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 a —CHO group
- C07C29/141—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 a —CHO group with hydrogen or hydrogen-containing gases
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
- C07C2523/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals of the platinum group metals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
- C07C2523/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals of the platinum group metals
- C07C2523/42—Platinum
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
- C07C2523/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals of the platinum group metals
- C07C2523/44—Palladium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
- C07C2523/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals of the platinum group metals
- C07C2523/46—Ruthenium, rhodium, osmium or iridium
-
- 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
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Materials Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4300297A DE4300297C2 (de) | 1993-01-08 | 1993-01-08 | Verfahren zur selektiven katalytischen Hydrierung der Carbonylgruppe von 4-Carboxylbenzaldehyd |
| DEP4300297.8 | 1993-01-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1099740A true CN1099740A (zh) | 1995-03-08 |
Family
ID=6477865
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN94100192A Pending CN1099740A (zh) | 1993-01-08 | 1994-01-07 | 芳族醛的选择性催化加氢 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US5387726A (enExample) |
| EP (1) | EP0606072B1 (enExample) |
| KR (1) | KR940018338A (enExample) |
| CN (1) | CN1099740A (enExample) |
| BR (1) | BR9400041A (enExample) |
| DE (2) | DE4300297C2 (enExample) |
| ES (1) | ES2118981T3 (enExample) |
| MX (1) | MX9400303A (enExample) |
| TW (1) | TW237446B (enExample) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101844957A (zh) * | 2010-03-30 | 2010-09-29 | 杭州师范大学 | 一种α, β-不饱和酮羰基还原成亚甲基的方法 |
| CN103717555A (zh) * | 2011-07-26 | 2014-04-09 | Sk新技术株式会社 | 由芳族羧酸和/或芳族羧酸烷基酯制备工艺的副产物制备芳族烃的方法 |
| CN105268434A (zh) * | 2014-07-24 | 2016-01-27 | 中国石油化工股份有限公司 | 粗对苯二甲酸加氢精制催化剂 |
| CN106475093A (zh) * | 2015-09-02 | 2017-03-08 | 中国石化扬子石油化工有限公司 | 一种蛋壳型Pd/TiO2催化剂的制备方法 |
| CN117945848A (zh) * | 2022-10-25 | 2024-04-30 | 中国石油化工股份有限公司 | 加氢催化剂及其制备方法和应用和芳香醛加氢制芳香醇的方法 |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GR1002923B (el) * | 1997-01-24 | 1998-06-16 | Καταλυτες για την καυση πτητικων οργανικων ενωσεων (vocs) | |
| US6852667B2 (en) * | 1998-02-16 | 2005-02-08 | Sumitomo Chemical Company Limited | Process for producing chlorine |
| DE19926621A1 (de) * | 1999-06-11 | 2000-12-14 | Bayer Ag | Verfahren zur Herstellung von Benzylalkoholen und deren Verwendung |
| WO2003057209A1 (en) * | 2002-01-09 | 2003-07-17 | Hormos Medical Corporation | Method for the preparation of matairesinol |
| WO2003062174A1 (de) | 2002-01-24 | 2003-07-31 | Basf Aktiengesellschaft | Verfahren zur herstellung von toluolderivaten |
| EP2444150A1 (de) * | 2010-10-22 | 2012-04-25 | crenox GmbH | Trägerkatalysator aus Aufschlussrückständen der titanylsulfathaltigen Schwarzlösung |
| CN103301864B (zh) * | 2012-03-12 | 2014-12-31 | 中国科学院大连化学物理研究所 | 一种Pd/TiO2-C-SiC催化剂及其制备与应用 |
| CN102863331B (zh) * | 2012-09-18 | 2014-09-03 | 中国石油化工股份有限公司 | 对苯二甲酸加氢精制催化剂活性状况判断方法 |
| CN103386303B (zh) * | 2013-07-25 | 2016-03-02 | 中国石油化工股份有限公司 | 一种加氢催化剂及其制备方法 |
| FI128885B (en) * | 2018-11-06 | 2021-02-15 | Teknologian Tutkimuskeskus Vtt Oy | Catalyst for dehydrogenation, method for preparing the catalyst and use |
| JP7840118B2 (ja) * | 2021-04-21 | 2026-04-03 | 千代田化工建設株式会社 | 水素化触媒ならびにこれを用いたフロー式有機合成システム及び水素化有機化合物の製造方法 |
| US20250091036A1 (en) * | 2021-07-28 | 2025-03-20 | Battelle Memorial Institute | Catalyst and method embodiments for making para-xylene and ortho-xylene |
| CN116328795B (zh) * | 2021-12-17 | 2025-05-16 | 南京林业大学 | 一种复合载体负载双金属催化剂的制备用于催化碳氧双键选择性原位加氢的方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1233536A (fr) * | 1958-01-13 | 1960-10-12 | Engelhard Ind Inc | Catalyseur contenant du ruthénium |
| GB1159967A (en) * | 1965-11-15 | 1969-07-30 | Johnson Matthey Co Ltd | Improvements in and relating to the Catalytic Reduction of Aromatic Ketones and Aromatic Aldehydes |
| US3532760A (en) * | 1966-08-15 | 1970-10-06 | Dow Chemical Co | Reduction of chlorophenones |
| GB1578725A (en) * | 1977-03-02 | 1980-11-05 | Johnson Matthey Co Ltd | Catalytic process for the purification of terephthalic acid |
| US4743577A (en) * | 1986-10-14 | 1988-05-10 | Amoco Corporation | Catalyst composition |
| JPH078823B2 (ja) * | 1986-10-20 | 1995-02-01 | 三井石油化学工業株式会社 | 高純度テレフタル酸の製造方法 |
| US4812594A (en) * | 1987-04-21 | 1989-03-14 | Amoco Corporation | Process for purification of crude p-hydroxymethylbenzoic acid |
| US4721808A (en) * | 1987-04-21 | 1988-01-26 | Amoco Corporation | Process for purification of crude p-hydroxymethylbenzoic acid |
| DE4132663C2 (de) * | 1991-10-01 | 1993-10-14 | Degussa | Verfahren zum Herstellen von 1,3-Propandiol durch Hydrieren von Hydroxypropionaldehyd |
-
1993
- 1993-01-08 DE DE4300297A patent/DE4300297C2/de not_active Expired - Fee Related
- 1993-12-21 TW TW082110851A patent/TW237446B/zh active
-
1994
- 1994-01-05 DE DE59406155T patent/DE59406155D1/de not_active Expired - Fee Related
- 1994-01-05 ES ES94100078T patent/ES2118981T3/es not_active Expired - Lifetime
- 1994-01-05 EP EP94100078A patent/EP0606072B1/de not_active Expired - Lifetime
- 1994-01-06 MX MX9400303A patent/MX9400303A/es not_active IP Right Cessation
- 1994-01-06 BR BR9400041A patent/BR9400041A/pt not_active IP Right Cessation
- 1994-01-07 CN CN94100192A patent/CN1099740A/zh active Pending
- 1994-01-07 KR KR1019940000199A patent/KR940018338A/ko not_active Ceased
- 1994-01-07 US US08/179,621 patent/US5387726A/en not_active Expired - Fee Related
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101844957A (zh) * | 2010-03-30 | 2010-09-29 | 杭州师范大学 | 一种α, β-不饱和酮羰基还原成亚甲基的方法 |
| CN101844957B (zh) * | 2010-03-30 | 2012-10-24 | 杭州师范大学 | 一种α, β-不饱和酮羰基还原成亚甲基的方法 |
| CN103717555A (zh) * | 2011-07-26 | 2014-04-09 | Sk新技术株式会社 | 由芳族羧酸和/或芳族羧酸烷基酯制备工艺的副产物制备芳族烃的方法 |
| CN105268434A (zh) * | 2014-07-24 | 2016-01-27 | 中国石油化工股份有限公司 | 粗对苯二甲酸加氢精制催化剂 |
| CN105268434B (zh) * | 2014-07-24 | 2018-07-13 | 中国石油化工股份有限公司 | 粗对苯二甲酸加氢精制催化剂 |
| CN106475093A (zh) * | 2015-09-02 | 2017-03-08 | 中国石化扬子石油化工有限公司 | 一种蛋壳型Pd/TiO2催化剂的制备方法 |
| CN106475093B (zh) * | 2015-09-02 | 2021-07-23 | 中国石化扬子石油化工有限公司 | 一种蛋壳型Pd/TiO2催化剂的制备方法 |
| CN117945848A (zh) * | 2022-10-25 | 2024-04-30 | 中国石油化工股份有限公司 | 加氢催化剂及其制备方法和应用和芳香醛加氢制芳香醇的方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE4300297C2 (de) | 1998-01-29 |
| EP0606072B1 (de) | 1998-06-10 |
| TW237446B (enExample) | 1995-01-01 |
| US5387726A (en) | 1995-02-07 |
| BR9400041A (pt) | 1994-07-26 |
| EP0606072A1 (de) | 1994-07-13 |
| DE59406155D1 (de) | 1998-07-16 |
| DE4300297A1 (de) | 1994-07-21 |
| KR940018338A (ko) | 1994-08-16 |
| MX9400303A (es) | 1994-07-29 |
| ES2118981T3 (es) | 1998-10-01 |
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