EP2480329A2 - Katalysator und verfahren zur katalytischen hydrierung von hydroxycarbonsäureestern in glykole - Google Patents
Katalysator und verfahren zur katalytischen hydrierung von hydroxycarbonsäureestern in glykoleInfo
- Publication number
- EP2480329A2 EP2480329A2 EP10765981A EP10765981A EP2480329A2 EP 2480329 A2 EP2480329 A2 EP 2480329A2 EP 10765981 A EP10765981 A EP 10765981A EP 10765981 A EP10765981 A EP 10765981A EP 2480329 A2 EP2480329 A2 EP 2480329A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- catalyst
- copper
- glycols
- esters
- hydroxysilicate
- 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.)
- Withdrawn
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 63
- 238000000034 method Methods 0.000 title claims abstract description 31
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 150000002334 glycols Chemical class 0.000 title claims abstract description 18
- 238000009903 catalytic hydrogenation reaction Methods 0.000 title claims abstract description 6
- 239000010949 copper Substances 0.000 claims abstract description 61
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 47
- 229910052802 copper Inorganic materials 0.000 claims abstract description 46
- 150000002148 esters Chemical class 0.000 claims abstract description 17
- 239000001257 hydrogen Substances 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 230000002829 reductive effect Effects 0.000 claims abstract description 14
- 239000007789 gas Substances 0.000 claims abstract description 9
- 239000000203 mixture Substances 0.000 claims description 15
- 230000031700 light absorption Effects 0.000 claims description 3
- 238000002371 ultraviolet--visible spectrum Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 11
- 239000002105 nanoparticle Substances 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 3
- 229910052710 silicon Inorganic materials 0.000 abstract description 3
- 239000010703 silicon Substances 0.000 abstract description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical class CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 32
- 238000005984 hydrogenation reaction Methods 0.000 description 23
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 23
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 16
- 235000013772 propylene glycol Nutrition 0.000 description 14
- 229960004063 propylene glycol Drugs 0.000 description 12
- 229910052681 coesite Inorganic materials 0.000 description 10
- 229910052906 cristobalite Inorganic materials 0.000 description 10
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 10
- 229910052682 stishovite Inorganic materials 0.000 description 10
- 229910052905 tridymite Inorganic materials 0.000 description 10
- 239000012071 phase Substances 0.000 description 9
- 238000005034 decoration Methods 0.000 description 8
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- MRABAEUHTLLEML-UHFFFAOYSA-N Butyl lactate Chemical compound CCCCOC(=O)C(C)O MRABAEUHTLLEML-UHFFFAOYSA-N 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- 239000001191 butyl (2R)-2-hydroxypropanoate Substances 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- 229940116333 ethyl lactate Drugs 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- 239000011787 zinc oxide Substances 0.000 description 4
- 235000014692 zinc oxide Nutrition 0.000 description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 3
- LPEKGGXMPWTOCB-UHFFFAOYSA-N 8beta-(2,3-epoxy-2-methylbutyryloxy)-14-acetoxytithifolin Natural products COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 3
- -1 alkyl oxalates Chemical class 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 3
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 229940057867 methyl lactate Drugs 0.000 description 3
- 150000002895 organic esters Chemical class 0.000 description 3
- 238000002198 surface plasmon resonance spectroscopy Methods 0.000 description 3
- 239000002028 Biomass Substances 0.000 description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 2
- 239000008246 gaseous mixture Substances 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 2
- 239000012808 vapor phase Substances 0.000 description 2
- 150000000180 1,2-diols Chemical class 0.000 description 1
- 229910002012 Aerosil® Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical class OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- IUOVJOAPNLRTRK-UHFFFAOYSA-N [Si].OOO Chemical class [Si].OOO IUOVJOAPNLRTRK-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000000274 adsorptive effect Effects 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- 230000002528 anti-freeze Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 239000005431 greenhouse gas Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000010335 hydrothermal treatment Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000029553 photosynthesis Effects 0.000 description 1
- 238000010672 photosynthesis Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- RNWHGQJWIACOKP-UHFFFAOYSA-N zinc;oxygen(2-) Chemical class [O-2].[Zn+2] RNWHGQJWIACOKP-UHFFFAOYSA-N 0.000 description 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
- B01J23/70—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
-
- 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
- B01J21/16—Clays or other mineral silicates
-
- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/30—Catalysts, in general, characterised by their form or physical properties characterised by their physical properties
-
- 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
- B01J37/16—Reducing
- B01J37/18—Reducing with gases containing free hydrogen
-
- 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
- C07C29/147—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 carboxylic acids or derivatives thereof
- C07C29/149—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 carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Dispersion Chemistry (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 |
|---|---|---|---|
| EEP200900073A EE200900073A (et) | 2009-09-22 | 2009-09-22 | Katalsaator ja meetod hdrokskarbokslhapete estrite kataltiliseks hdrogeenimiseks glkoolideks |
| PCT/EP2010/064001 WO2011036189A2 (en) | 2009-09-22 | 2010-09-22 | The catalyst and method of catalytic hydrogenation of hydroxycarboxylic acid esters to glycols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP2480329A2 true EP2480329A2 (de) | 2012-08-01 |
Family
ID=43707761
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP10765981A Withdrawn EP2480329A2 (de) | 2009-09-22 | 2010-09-22 | Katalysator und verfahren zur katalytischen hydrierung von hydroxycarbonsäureestern in glykole |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP2480329A2 (de) |
| EA (1) | EA021350B1 (de) |
| EE (1) | EE200900073A (de) |
| WO (1) | WO2011036189A2 (de) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102011107959A1 (de) | 2011-07-20 | 2013-01-24 | Thyssenkrupp Uhde Gmbh | Herstellung von optisch reinem Propan-1,2-diol |
| GB201617698D0 (en) | 2016-10-19 | 2016-11-30 | Johnson Matthey Davy Technologies Limited | Process |
| RU2734237C1 (ru) * | 2020-01-27 | 2020-10-13 | Андрей Владиславович Курочкин | Установка комплексной подготовки газа путем низкотемпературной конденсации |
| CN112517017B (zh) * | 2020-11-30 | 2023-05-05 | 陕西延长石油（集团）有限责任公司 | 一种醋酸甲酯加氢的掺杂型硅酸铜纳米管催化剂及其制备方法与应用 |
| CN116459846B (zh) * | 2023-05-09 | 2024-03-26 | 中国科学院兰州化学物理研究所 | 一种羟基酯加氢纳米Cu基催化剂及其制备方法与应用 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1190783B (it) | 1981-04-29 | 1988-02-24 | Davy Mckee Oil & Chem | Processo per l'idrogenolisi di esteri di acidi carbossilici |
| JPS60109028A (ja) | 1983-11-17 | 1985-06-14 | Hitachi Maxell Ltd | 磁気記録媒体 |
| US4628129A (en) | 1985-02-04 | 1986-12-09 | Union Carbide Corporation | Process for the preparation of ethylene glycol |
| SU1594138A1 (ru) * | 1988-03-17 | 1990-09-23 | Карагандинский Государственный Университет | Способ получени синтетической хризоколлы |
| AU1628900A (en) | 1998-11-24 | 2000-06-13 | Michigan State University | Condensed phase catalytic hydrogenation of lactic acid to propylene glycol |
| US6455742B1 (en) | 1999-09-02 | 2002-09-24 | Wisconsin Alumni Research Foundation | Method for catalytically reducing carboxylic acid groups to hydroxyl groups in hydroxycarboxylic acids |
| US6479713B1 (en) | 2001-10-23 | 2002-11-12 | Battelle Memorial Institute | Hydrogenolysis of 5-carbon sugars, sugar alcohols, and other methods and compositions for reactions involving hydrogen |
| RU2290994C1 (ru) * | 2005-12-21 | 2007-01-10 | Институт Катализа Им. Г.К. Борескова Сибирского Отделения Российской Академии Наук | Катализатор, способ его приготовления и способ получения дигидроксиалканов |
-
2009
- 2009-09-22 EE EEP200900073A patent/EE200900073A/xx unknown
-
2010
- 2010-09-22 EA EA201200528A patent/EA021350B1/ru not_active IP Right Cessation
- 2010-09-22 WO PCT/EP2010/064001 patent/WO2011036189A2/en active Application Filing
- 2010-09-22 EP EP10765981A patent/EP2480329A2/de not_active Withdrawn
Non-Patent Citations (1)
| Title |
|---|
| See references of WO2011036189A2 * |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2011036189A2 (en) | 2011-03-31 |
| WO2011036189A3 (en) | 2012-02-23 |
| EA021350B1 (ru) | 2015-05-29 |
| EA201200528A1 (ru) | 2012-09-28 |
| EE200900073A (et) | 2011-06-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN108236955B (zh) | 一种草酸二甲酯加氢合成乙醇用催化剂的制备方法以及由此得到的催化剂和其应用 | |
| Wu et al. | Aqueous phase reforming of biodiesel byproduct glycerol over mesoporous Ni-Cu/CeO2 for renewable hydrogen production | |
| CN108144643B (zh) | 一种催化剂及合成气直接转化制低碳烯烃的方法 | |
| Kanuri et al. | An insight of CO2 hydrogenation to methanol synthesis: Thermodynamics, catalysts, operating parameters, and reaction mechanism | |
| US8188321B2 (en) | Process for producing hydrogenolysis products of polyhydric alcohols | |
| RU2450043C2 (ru) | Способ синтеза углеводородов | |
| CN108970638B (zh) | 一种催化剂与合成气直接转化制液体燃料联产低碳烯烃的方法 | |
| CN107774302B (zh) | 一种催化剂及合成气直接转化制液体燃料联产低碳烯烃的方法 | |
| EP2480329A2 (de) | Katalysator und verfahren zur katalytischen hydrierung von hydroxycarbonsäureestern in glykole | |
| WO2017074582A1 (en) | Catalysts prepared from nanostructures of mno2 and wo3 for oxidative coupling of methane | |
| CN109745965B (zh) | 一种含CeZr氧化物的催化剂及一氧化碳加氢直接转化制低碳烯烃的方法 | |
| López et al. | Study of hydrotalcite-supported transition metals as catalysts for crude glycerol hydrogenolysis | |
| Ashokraju et al. | Formic acid assisted hydrogenation of levulinic acid to\upgamma γ-valerolactone over ordered mesoporous Cu/Fe _ 2 O _ 3 Cu/Fe 2 O 3 catalyst prepared by hard template method | |
| US20120203040A1 (en) | Process for the Production of Paraffinic Hydrocarbons | |
| Ahmad et al. | Synthesis of oxymethylene dimethyl ethers (OMEn) via methanol mediated COx hydrogenation over Ru/BEA catalysts | |
| Díaz et al. | Carbon nanofibers and nanospheres-supported bimetallic (Co and Fe) catalysts for the Fischer–Tropsch synthesis | |
| CN108970635B (zh) | 一种催化剂和合成气直接转化制液体燃料联产低碳烯烃的方法 | |
| CN108927132B (zh) | 一种双功能催化剂及一氧化碳加氢制乙烯的方法 | |
| WO2009103682A1 (en) | The catalyst and method of catalytic reduction of esters of hydroxycarboxylic acid to glycols | |
| CN108970637B (zh) | 一种催化剂及合成气直接转化制液体燃料联产低碳烯烃的方法 | |
| Wang et al. | The base-free and selective oxidative transformation of 1, 3-propanediol into methyl esters by different Au/CeO 2 catalysts | |
| CN107661773B (zh) | 一种催化剂及合成气直接转化制液体燃料联产低碳烯烃的方法 | |
| Yin et al. | The influence mechanism of solvent on the hydrogenation of dimethyl oxalate | |
| CN111569894A (zh) | 一种负载型Cu-Fe基催化剂及其制备方法和应用 | |
| Pulungan et al. | The stabilization of bio-oil as an alternative energy source through hydrodeoxygenation using Co and Co-Mo supported on active natural zeolite |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
| 17P | Request for examination filed |
Effective date: 20120423 |
|
| AK | Designated contracting states |
Kind code of ref document: A2 Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO SE SI SK SM TR |
|
| DAX | Request for extension of the european patent (deleted) | ||
| 17Q | First examination report despatched |
Effective date: 20130312 |
|
| STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN |
|
| 18D | Application deemed to be withdrawn |
Effective date: 20140401 |