RU2190468C2 - Катализатор для дегидрирования циклогексанола в циклогексанон и способ его получения - Google Patents
Катализатор для дегидрирования циклогексанола в циклогексанон и способ его получения Download PDFInfo
- Publication number
- RU2190468C2 RU2190468C2 RU99101934/04A RU99101934A RU2190468C2 RU 2190468 C2 RU2190468 C2 RU 2190468C2 RU 99101934/04 A RU99101934/04 A RU 99101934/04A RU 99101934 A RU99101934 A RU 99101934A RU 2190468 C2 RU2190468 C2 RU 2190468C2
- Authority
- RU
- Russia
- Prior art keywords
- catalyst
- copper
- cyclohexanol
- dehydrogenation
- cyclohexanone
- Prior art date
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 56
- 238000000034 method Methods 0.000 title claims abstract description 14
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 title claims description 28
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 title claims description 23
- 238000006356 dehydrogenation reaction Methods 0.000 title claims description 16
- 238000004519 manufacturing process Methods 0.000 title abstract description 10
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 36
- 229910052802 copper Inorganic materials 0.000 claims abstract description 35
- 239000010949 copper Substances 0.000 claims abstract description 35
- 238000007747 plating Methods 0.000 claims abstract description 6
- 238000007580 dry-mixing Methods 0.000 claims abstract description 5
- 238000005470 impregnation Methods 0.000 claims abstract description 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 12
- 230000008021 deposition Effects 0.000 claims description 2
- 238000000151 deposition Methods 0.000 claims description 2
- 238000000465 moulding Methods 0.000 claims description 2
- 230000000694 effects Effects 0.000 abstract description 7
- 238000001354 calcination Methods 0.000 abstract description 4
- 229910052782 aluminium Inorganic materials 0.000 abstract 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 17
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- 150000001879 copper Chemical class 0.000 description 7
- 229910052763 palladium Inorganic materials 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 239000000654 additive Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- -1 nitric Chemical class 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 2
- 239000005751 Copper oxide Substances 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000002441 X-ray diffraction Methods 0.000 description 2
- 238000005054 agglomeration Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000008139 complexing agent Substances 0.000 description 2
- 229910000431 copper oxide Inorganic materials 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 230000009849 deactivation Effects 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 238000006471 dimerization reaction Methods 0.000 description 2
- 239000010439 graphite Substances 0.000 description 2
- 229910002804 graphite Inorganic materials 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000004280 Sodium formate Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000005202 decontamination Methods 0.000 description 1
- 230000003588 decontaminative effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229940071106 ethylenediaminetetraacetate Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 235000011167 hydrochloric acid Nutrition 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- GPNDARIEYHPYAY-UHFFFAOYSA-N palladium(ii) nitrate Chemical compound [Pd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O GPNDARIEYHPYAY-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
- 235000019254 sodium formate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- NEUOBESLMIKJSB-UHFFFAOYSA-J tetrasodium;tetraacetate Chemical compound [Na+].[Na+].[Na+].[Na+].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O NEUOBESLMIKJSB-UHFFFAOYSA-J 0.000 description 1
Images
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
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/89—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals
- B01J23/8926—Copper and noble metals
-
- 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
- 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
- B01J23/72—Copper
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/002—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by dehydrogenation
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)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19626587A DE19626587A1 (de) | 1996-07-02 | 1996-07-02 | Katalysator zur Dehydrierung von Cyclohexanol |
| DE19626587.8 | 1996-07-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU99101934A RU99101934A (ru) | 2000-12-20 |
| RU2190468C2 true RU2190468C2 (ru) | 2002-10-10 |
Family
ID=7798698
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU99101934/04A RU2190468C2 (ru) | 1996-07-02 | 1997-06-17 | Катализатор для дегидрирования циклогексанола в циклогексанон и способ его получения |
Country Status (15)
| Country | Link |
|---|---|
| EP (1) | EP0909214A1 (cs) |
| JP (1) | JP2000513269A (cs) |
| KR (1) | KR20000022369A (cs) |
| CN (1) | CN1094785C (cs) |
| AU (1) | AU3176497A (cs) |
| BR (1) | BR9710017A (cs) |
| CA (1) | CA2258549A1 (cs) |
| CZ (1) | CZ425498A3 (cs) |
| DE (1) | DE19626587A1 (cs) |
| NO (1) | NO986155D0 (cs) |
| PL (1) | PL330957A1 (cs) |
| RU (1) | RU2190468C2 (cs) |
| SK (1) | SK172198A3 (cs) |
| TW (1) | TW460327B (cs) |
| WO (1) | WO1998000233A1 (cs) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2353425C1 (ru) * | 2008-02-01 | 2009-04-27 | Общество с ограниченной ответственностью "Научно-технический центр "АЛВИГО-М" | Способ приготовления катализатора для дегидрирования циклогексанола в циклогексанон |
| RU2546122C1 (ru) * | 2013-10-10 | 2015-04-10 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования (Российский химико-технологический университет им. Д.И. Менделеева) | Катализатор для дегидрирования циклогексанола в циклогексанон |
| RU2574730C2 (ru) * | 2013-10-10 | 2016-02-10 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования (Российский химико-технологический университет им. Д.И. Менделеева) | Способ приготовления катализатора для дегидрирования циклогексанола в циклогексанон |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6573409B1 (en) | 1999-07-02 | 2003-06-03 | The Nutrasweet Company | Process for the preparation of 3,3-dimethylbutanal |
| KR100409083B1 (ko) * | 2001-03-12 | 2003-12-11 | 주식회사 엘지화학 | 올레핀 제조용 탄화수소의 수증기 분해 촉매 |
| KR100431898B1 (ko) * | 2001-08-04 | 2004-05-17 | 애경유화 주식회사 | 카르보닐기 함유 화합물의 수소화 또는 사이클로알콜의탈수소화 반응에 유용한 구리-실리카 촉매 및 이의 제조방법 |
| CN100360228C (zh) * | 2005-05-31 | 2008-01-09 | 中国石油化工股份有限公司 | 一种醇脱氢制酮催化剂及其制备方法 |
| CN102500420B (zh) * | 2011-11-30 | 2014-03-05 | 大丰海嘉诺药业有限公司 | 一种醇气相脱氢催化剂及其制备方法和应用 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4472593A (en) * | 1981-10-16 | 1984-09-18 | Shell Oil Company | Conversion of isopropyl alcohol to acetone |
| US5202511A (en) * | 1989-08-16 | 1993-04-13 | The Dow Chemical Company | Catalyst diluent for oxychlorination process |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU522853A1 (ru) * | 1974-12-13 | 1976-07-30 | Институт физико-органической химии АН Белорусской ССР | Катализатор дл дегидрировани циклогексанола |
| JPS5620541A (en) * | 1979-07-30 | 1981-02-26 | Mitsubishi Chem Ind Ltd | Preparation of cyclohexanone |
| CN1056067A (zh) * | 1990-04-29 | 1991-11-13 | 王炳炎 | 多组分环己醇脱氢催化剂 |
-
1996
- 1996-07-02 DE DE19626587A patent/DE19626587A1/de not_active Withdrawn
-
1997
- 1997-06-17 SK SK1721-98A patent/SK172198A3/sk unknown
- 1997-06-17 AU AU31764/97A patent/AU3176497A/en not_active Abandoned
- 1997-06-17 PL PL97330957A patent/PL330957A1/xx unknown
- 1997-06-17 EP EP97927189A patent/EP0909214A1/de not_active Withdrawn
- 1997-06-17 CZ CZ984254A patent/CZ425498A3/cs unknown
- 1997-06-17 WO PCT/EP1997/003135 patent/WO1998000233A1/de not_active Ceased
- 1997-06-17 CN CN97196061A patent/CN1094785C/zh not_active Expired - Fee Related
- 1997-06-17 JP JP10503796A patent/JP2000513269A/ja active Pending
- 1997-06-17 BR BR9710017A patent/BR9710017A/pt unknown
- 1997-06-17 CA CA002258549A patent/CA2258549A1/en not_active Abandoned
- 1997-06-17 RU RU99101934/04A patent/RU2190468C2/ru not_active IP Right Cessation
- 1997-06-17 KR KR1019980710800A patent/KR20000022369A/ko not_active Withdrawn
- 1997-06-30 TW TW086109182A patent/TW460327B/zh not_active IP Right Cessation
-
1998
- 1998-12-28 NO NO986155A patent/NO986155D0/no not_active Application Discontinuation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4472593A (en) * | 1981-10-16 | 1984-09-18 | Shell Oil Company | Conversion of isopropyl alcohol to acetone |
| US5202511A (en) * | 1989-08-16 | 1993-04-13 | The Dow Chemical Company | Catalyst diluent for oxychlorination process |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2353425C1 (ru) * | 2008-02-01 | 2009-04-27 | Общество с ограниченной ответственностью "Научно-технический центр "АЛВИГО-М" | Способ приготовления катализатора для дегидрирования циклогексанола в циклогексанон |
| RU2546122C1 (ru) * | 2013-10-10 | 2015-04-10 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования (Российский химико-технологический университет им. Д.И. Менделеева) | Катализатор для дегидрирования циклогексанола в циклогексанон |
| RU2574730C2 (ru) * | 2013-10-10 | 2016-02-10 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования (Российский химико-технологический университет им. Д.И. Менделеева) | Способ приготовления катализатора для дегидрирования циклогексанола в циклогексанон |
Also Published As
| Publication number | Publication date |
|---|---|
| PL330957A1 (en) | 1999-06-21 |
| KR20000022369A (ko) | 2000-04-25 |
| TW460327B (en) | 2001-10-21 |
| CZ425498A3 (cs) | 1999-11-17 |
| EP0909214A1 (de) | 1999-04-21 |
| DE19626587A1 (de) | 1998-01-08 |
| SK172198A3 (en) | 1999-04-13 |
| WO1998000233A1 (de) | 1998-01-08 |
| CN1094785C (zh) | 2002-11-27 |
| AU3176497A (en) | 1998-01-21 |
| NO986155L (no) | 1998-12-28 |
| NO986155D0 (no) | 1998-12-28 |
| CA2258549A1 (en) | 1998-01-08 |
| CN1224371A (zh) | 1999-07-28 |
| BR9710017A (pt) | 1999-08-10 |
| JP2000513269A (ja) | 2000-10-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR920005083B1 (ko) | 담체부착-은촉매의 제조방법 | |
| RU2190468C2 (ru) | Катализатор для дегидрирования циклогексанола в циклогексанон и способ его получения | |
| WO2023134779A1 (zh) | 加氢催化剂及其制备方法和制备异己二醇和甲基异丁基甲醇的方法 | |
| EP0101645A1 (en) | Catalytic process for the production of methanol | |
| JP3237365B2 (ja) | フェノールの製造方法 | |
| JP2632166B2 (ja) | カルボン酸の製造方法 | |
| JP2004500236A (ja) | 不飽和炭化水素を水素化するための触媒 | |
| CN106674173B (zh) | 一种脱氢催化剂及制造δ-戊内酯的方法 | |
| CN112010802B (zh) | 3-甲基吡啶的连续制备方法 | |
| JPS58166936A (ja) | メタクリル酸メチルを製造するための触媒 | |
| JP4069242B2 (ja) | 金属粒子担持体及びカルボン酸エステルの製造方法 | |
| KR19990087753A (ko) | 2급 고리형 알콜의 탈수소화 방법 | |
| JPH0542298B2 (cs) | ||
| CA1259632A (en) | Catalytic reduction process | |
| CN112138724A (zh) | 加氢烷基化催化剂及其方法 | |
| US5872075A (en) | Catalyst for oxidation of hydrogen, method for selective oxidation of hydrogen, and method for dehydrogenation of hydrocarbon | |
| EP0080759B1 (en) | Process for the preparation of 3,5-dimethylphenol | |
| JP2003192632A (ja) | 不飽和カルボン酸エステルと不飽和カルボン酸の混合物の製造方法 | |
| JP3153526B2 (ja) | 芳香族オレフィンの部分水素化用触媒およびその部分水素化方法 | |
| JPH06263668A (ja) | フェノールの製造方法 | |
| JPS62258335A (ja) | メチルイソブチルケトンの製造法 | |
| JPS6046096B2 (ja) | シクロヘキシルベンゼンの製造方法 | |
| JP2003103174A (ja) | 金属粒子担持体及び不飽和カルボニル化合物の製造方法 | |
| US4127508A (en) | Silver-cadmium alloy catalyst | |
| JPH0419984B2 (cs) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20030618 |