RU2583055C1 - Катализатор окисления циклоалканов и способ получения спиртов и кетонов - Google Patents
Катализатор окисления циклоалканов и способ получения спиртов и кетонов Download PDFInfo
- Publication number
- RU2583055C1 RU2583055C1 RU2015106498/04A RU2015106498A RU2583055C1 RU 2583055 C1 RU2583055 C1 RU 2583055C1 RU 2015106498/04 A RU2015106498/04 A RU 2015106498/04A RU 2015106498 A RU2015106498 A RU 2015106498A RU 2583055 C1 RU2583055 C1 RU 2583055C1
- Authority
- RU
- Russia
- Prior art keywords
- hydroperoxide
- cycloalkane
- catalyst
- oxygen
- mww
- Prior art date
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 37
- 238000000034 method Methods 0.000 title claims abstract description 27
- 150000001924 cycloalkanes Chemical class 0.000 title claims abstract description 20
- 150000002576 ketones Chemical class 0.000 title claims abstract description 7
- 238000007254 oxidation reaction Methods 0.000 title abstract description 10
- 230000003647 oxidation Effects 0.000 title abstract description 9
- 150000001298 alcohols Chemical class 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 claims abstract description 18
- 239000000203 mixture Substances 0.000 claims abstract description 10
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 230000001590 oxidative effect Effects 0.000 claims abstract description 6
- 239000000126 substance Substances 0.000 claims abstract description 3
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 claims description 24
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 239000012429 reaction media Substances 0.000 claims description 9
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 7
- FGGJBCRKSVGDPO-UHFFFAOYSA-N hydroperoxycyclohexane Chemical compound OOC1CCCCC1 FGGJBCRKSVGDPO-UHFFFAOYSA-N 0.000 claims description 5
- -1 isobutylbenzene hydroperoxide ethylnaphthalene Chemical compound 0.000 claims description 4
- UUUYXCLERBDLEO-UHFFFAOYSA-N 1-hydroperoxy-1-methylcyclohexane Chemical compound OOC1(C)CCCCC1 UUUYXCLERBDLEO-UHFFFAOYSA-N 0.000 claims description 3
- GQNOPVSQPBUJKQ-UHFFFAOYSA-N 1-hydroperoxyethylbenzene Chemical compound OOC(C)C1=CC=CC=C1 GQNOPVSQPBUJKQ-UHFFFAOYSA-N 0.000 claims description 3
- XRXANEMIFVRKLN-UHFFFAOYSA-N 2-hydroperoxy-2-methylbutane Chemical compound CCC(C)(C)OO XRXANEMIFVRKLN-UHFFFAOYSA-N 0.000 claims description 3
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- YWBMNCRJFZGXJY-UHFFFAOYSA-N 1-hydroperoxy-1,2,3,4-tetrahydronaphthalene Chemical compound C1=CC=C2C(OO)CCCC2=C1 YWBMNCRJFZGXJY-UHFFFAOYSA-N 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 2
- GNKTZDSRQHMHLZ-UHFFFAOYSA-N [Si].[Si].[Si].[Ti].[Ti].[Ti].[Ti].[Ti] Chemical compound [Si].[Si].[Si].[Ti].[Ti].[Ti].[Ti].[Ti] GNKTZDSRQHMHLZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000010457 zeolite Substances 0.000 description 13
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 12
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 12
- 229910021536 Zeolite Inorganic materials 0.000 description 11
- 150000002432 hydroperoxides Chemical class 0.000 description 8
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- 239000003921 oil Substances 0.000 description 5
- 229910052723 transition metal Inorganic materials 0.000 description 5
- 150000003624 transition metals Chemical class 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 239000002638 heterogeneous catalyst Substances 0.000 description 4
- 239000011148 porous material Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 3
- 239000001361 adipic acid Substances 0.000 description 3
- 235000011037 adipic acid Nutrition 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 239000011651 chromium Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000002808 molecular sieve Substances 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 239000010936 titanium Substances 0.000 description 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 229910010413 TiO 2 Inorganic materials 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical group [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- IPHFEAMSIOVYCA-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalene;hydrochloride Chemical compound Cl.C1=CC=C2CCCCC2=C1 IPHFEAMSIOVYCA-UHFFFAOYSA-N 0.000 description 1
- IBBSNLXNYXWZOQ-UHFFFAOYSA-N 1-ethylnaphthalene;hydrogen peroxide Chemical compound OO.C1=CC=C2C(CC)=CC=CC2=C1 IBBSNLXNYXWZOQ-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- FPCJKVGGYOAWIZ-UHFFFAOYSA-N butan-1-ol;titanium Chemical compound [Ti].CCCCO.CCCCO.CCCCO.CCCCO FPCJKVGGYOAWIZ-UHFFFAOYSA-N 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 238000003421 catalytic decomposition reaction Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- QUQFTIVBFKLPCL-UHFFFAOYSA-L copper;2-amino-3-[(2-amino-2-carboxylatoethyl)disulfanyl]propanoate Chemical compound [Cu+2].[O-]C(=O)C(N)CSSCC(N)C([O-])=O QUQFTIVBFKLPCL-UHFFFAOYSA-L 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 1
- 239000004914 cyclooctane Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000005350 fused silica glass Substances 0.000 description 1
- 229910052733 gallium Inorganic materials 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
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- WQRUARPAYKIKTP-UHFFFAOYSA-N hydrogen peroxide;2-methylpropylbenzene Chemical compound OO.CC(C)CC1=CC=CC=C1 WQRUARPAYKIKTP-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229910001392 phosphorus oxide Inorganic materials 0.000 description 1
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical class [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/385—Saturated compounds containing a keto group being part of a ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C27/00—Processes involving the simultaneous production of more than one class of oxygen-containing compounds
- C07C27/10—Processes involving the simultaneous production of more than one class of oxygen-containing compounds by oxidation of hydrocarbons
- C07C27/16—Processes involving the simultaneous production of more than one class of oxygen-containing compounds by oxidation of hydrocarbons with other oxidising agents
-
- 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
- C07C29/48—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic
-
- 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
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/28—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of CHx-moieties
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/CN2012/079172 WO2014015491A1 (en) | 2012-07-26 | 2012-07-26 | Cycloalkane oxidation catalysts and method to produce alcohols and ketones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2583055C1 true RU2583055C1 (ru) | 2016-05-10 |
Family
ID=49996500
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2015106498/04A RU2583055C1 (ru) | 2012-07-26 | 2012-07-26 | Катализатор окисления циклоалканов и способ получения спиртов и кетонов |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US9708238B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP2877439B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP6068638B2 (cg-RX-API-DMAC7.html) |
| KR (1) | KR101953948B1 (cg-RX-API-DMAC7.html) |
| CN (1) | CN104736506B (cg-RX-API-DMAC7.html) |
| BR (1) | BR112015001573B1 (cg-RX-API-DMAC7.html) |
| IN (1) | IN2015DN00388A (cg-RX-API-DMAC7.html) |
| RU (1) | RU2583055C1 (cg-RX-API-DMAC7.html) |
| SG (1) | SG11201500522VA (cg-RX-API-DMAC7.html) |
| UA (1) | UA111907C2 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2014015491A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2707291C2 (ru) * | 2014-12-22 | 2019-11-26 | Родиа Операсьон | Катализаторы окисления циклоалканов и способ получения спиртов и кетонов |
| EP3746418A1 (en) | 2018-01-30 | 2020-12-09 | Basf Se | Method for oxidation of cycloalkanes |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002028774A2 (en) * | 2000-09-29 | 2002-04-11 | Showa Denko K. K. | Crystalline mww-type titanosilicate , its preparation and use thereof for producing epoxides |
| RU2280638C2 (ru) * | 2000-04-27 | 2006-07-27 | Шелл Интернэшнл Рисерч Маатсхаппий Б.В. | Способ каталитического гидроксилирования насыщенных или ненасыщенных алифатических соединений (варианты) |
| CN101733164A (zh) * | 2009-12-21 | 2010-06-16 | 中国科学院长春应用化学研究所 | 用于环己烷液相催化氧化制备环己醇和环己酮的催化体系和用法 |
| CN102452895A (zh) * | 2010-10-29 | 2012-05-16 | 中国石油化工股份有限公司 | 一种含锡钛硅分子筛催化环烷烃的方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL9201756A (nl) | 1992-10-09 | 1994-05-02 | Univ Delft Tech | Werkwijze voor de gekatalyseerde ontleding van organische hydroperoxiden. |
| US20040034258A1 (en) * | 2000-09-29 | 2004-02-19 | Showa Denko K.K. | Crystalline MWW-type titanosilicate catalyst for producing oxidized compound, production process for the catalyst, and process for producing oxidized compound by using the catalyst |
| US20040158103A1 (en) | 2003-02-11 | 2004-08-12 | Solutia Inc. | Cyclohexane oxidation catalysts |
| US7081552B2 (en) * | 2004-08-17 | 2006-07-25 | Solutia Inc. | Catalysts for cycloalkanes oxidation and decomposition of cycloalkyl hydroperoxide |
| CA2590668C (en) * | 2004-12-28 | 2015-11-17 | Neste Oil Oyj | Catalytic materials and method for the preparation thereof |
| US7868201B2 (en) | 2005-07-01 | 2011-01-11 | Exxonmobil Research And Engineering Company | Process and catalyst for oxidation of hydrocarbons |
| JP2010159245A (ja) * | 2008-09-19 | 2010-07-22 | Sumitomo Chemical Co Ltd | 酸化化合物の製造方法 |
| JP2010138032A (ja) * | 2008-12-11 | 2010-06-24 | Sumitomo Chemical Co Ltd | チタノシリケートの製造方法 |
| CN102079695B (zh) * | 2009-11-27 | 2014-01-15 | 中国石油化工股份有限公司 | 一种催化氧化环己烷的方法 |
-
2012
- 2012-07-26 IN IN388DEN2015 patent/IN2015DN00388A/en unknown
- 2012-07-26 RU RU2015106498/04A patent/RU2583055C1/ru active
- 2012-07-26 WO PCT/CN2012/079172 patent/WO2014015491A1/en not_active Ceased
- 2012-07-26 KR KR1020157001615A patent/KR101953948B1/ko not_active Expired - Fee Related
- 2012-07-26 EP EP12881881.2A patent/EP2877439B1/en not_active Not-in-force
- 2012-07-26 BR BR112015001573-5A patent/BR112015001573B1/pt not_active IP Right Cessation
- 2012-07-26 CN CN201280074884.4A patent/CN104736506B/zh not_active Expired - Fee Related
- 2012-07-26 UA UAA201501563A patent/UA111907C2/uk unknown
- 2012-07-26 US US14/416,977 patent/US9708238B2/en not_active Expired - Fee Related
- 2012-07-26 SG SG11201500522VA patent/SG11201500522VA/en unknown
- 2012-07-26 JP JP2015523363A patent/JP6068638B2/ja not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2280638C2 (ru) * | 2000-04-27 | 2006-07-27 | Шелл Интернэшнл Рисерч Маатсхаппий Б.В. | Способ каталитического гидроксилирования насыщенных или ненасыщенных алифатических соединений (варианты) |
| WO2002028774A2 (en) * | 2000-09-29 | 2002-04-11 | Showa Denko K. K. | Crystalline mww-type titanosilicate , its preparation and use thereof for producing epoxides |
| CN101733164A (zh) * | 2009-12-21 | 2010-06-16 | 中国科学院长春应用化学研究所 | 用于环己烷液相催化氧化制备环己醇和环己酮的催化体系和用法 |
| CN102452895A (zh) * | 2010-10-29 | 2012-05-16 | 中国石油化工股份有限公司 | 一种含锡钛硅分子筛催化环烷烃的方法 |
Non-Patent Citations (1)
| Title |
|---|
| Peng Wu et al, Unique trans-Selectivity of Ti-MWW in Epoxidation of cis/trans-Alkenes with Hydrogen Peroxide. J.Phys.Chem.B, 2002, 106(4), 748-753. * |
Also Published As
| Publication number | Publication date |
|---|---|
| KR101953948B1 (ko) | 2019-03-04 |
| BR112015001573B1 (pt) | 2020-10-27 |
| WO2014015491A1 (en) | 2014-01-30 |
| CN104736506B (zh) | 2017-04-12 |
| US20150175514A1 (en) | 2015-06-25 |
| EP2877439A1 (en) | 2015-06-03 |
| CN104736506A (zh) | 2015-06-24 |
| KR20150065654A (ko) | 2015-06-15 |
| JP6068638B2 (ja) | 2017-01-25 |
| BR112015001573A2 (pt) | 2017-08-01 |
| JP2015528805A (ja) | 2015-10-01 |
| SG11201500522VA (en) | 2015-04-29 |
| IN2015DN00388A (cg-RX-API-DMAC7.html) | 2015-06-12 |
| EP2877439B1 (en) | 2018-02-14 |
| UA111907C2 (uk) | 2016-06-24 |
| US9708238B2 (en) | 2017-07-18 |
| EP2877439A4 (en) | 2016-03-16 |
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