CN104736506B - 环烷烃氧化催化剂以及生产醇和酮的方法 - Google Patents
环烷烃氧化催化剂以及生产醇和酮的方法 Download PDFInfo
- Publication number
- CN104736506B CN104736506B CN201280074884.4A CN201280074884A CN104736506B CN 104736506 B CN104736506 B CN 104736506B CN 201280074884 A CN201280074884 A CN 201280074884A CN 104736506 B CN104736506 B CN 104736506B
- Authority
- CN
- China
- Prior art keywords
- hydroperoxide
- hydroperoxides
- oxygen
- cycloalkane
- reaction
- 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 - Fee Related
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 33
- 238000000034 method Methods 0.000 title claims abstract description 27
- 150000001924 cycloalkanes Chemical class 0.000 title claims abstract description 19
- 150000002576 ketones Chemical class 0.000 title claims abstract description 8
- 230000003647 oxidation Effects 0.000 title claims description 10
- 238000007254 oxidation reaction Methods 0.000 title claims description 10
- 150000001298 alcohols Chemical class 0.000 title 1
- 150000002432 hydroperoxides Chemical class 0.000 claims abstract description 17
- 239000000203 mixture Substances 0.000 claims abstract description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 7
- FGGJBCRKSVGDPO-UHFFFAOYSA-N hydroperoxycyclohexane Chemical compound OOC1CCCCC1 FGGJBCRKSVGDPO-UHFFFAOYSA-N 0.000 claims abstract description 5
- IBBSNLXNYXWZOQ-UHFFFAOYSA-N 1-ethylnaphthalene;hydrogen peroxide Chemical compound OO.C1=CC=C2C(CC)=CC=CC2=C1 IBBSNLXNYXWZOQ-UHFFFAOYSA-N 0.000 claims abstract description 4
- UUUYXCLERBDLEO-UHFFFAOYSA-N 1-hydroperoxy-1-methylcyclohexane Chemical compound OOC1(C)CCCCC1 UUUYXCLERBDLEO-UHFFFAOYSA-N 0.000 claims abstract description 4
- GQNOPVSQPBUJKQ-UHFFFAOYSA-N 1-hydroperoxyethylbenzene Chemical compound OOC(C)C1=CC=CC=C1 GQNOPVSQPBUJKQ-UHFFFAOYSA-N 0.000 claims abstract description 4
- WQRUARPAYKIKTP-UHFFFAOYSA-N hydrogen peroxide;2-methylpropylbenzene Chemical compound OO.CC(C)CC1=CC=CC=C1 WQRUARPAYKIKTP-UHFFFAOYSA-N 0.000 claims abstract description 4
- XRXANEMIFVRKLN-UHFFFAOYSA-N 2-hydroperoxy-2-methylbutane Chemical compound CCC(C)(C)OO XRXANEMIFVRKLN-UHFFFAOYSA-N 0.000 claims abstract 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 abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 19
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 17
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 239000001301 oxygen Substances 0.000 claims description 15
- 239000000377 silicon dioxide Substances 0.000 claims description 8
- 239000012429 reaction media Substances 0.000 claims description 7
- 229910052681 coesite Inorganic materials 0.000 claims description 6
- 229910052906 cristobalite Inorganic materials 0.000 claims description 6
- 229910052682 stishovite Inorganic materials 0.000 claims description 6
- 229910052905 tridymite Inorganic materials 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 230000000737 periodic effect Effects 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 229910052756 noble gas Inorganic materials 0.000 claims description 2
- 150000002835 noble gases Chemical class 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- TWNQSCQMNSSPFZ-UHFFFAOYSA-N hydrogen peroxide;1,2,3,4-tetrahydronaphthalene Chemical class OO.C1=CC=C2CCCCC2=C1 TWNQSCQMNSSPFZ-UHFFFAOYSA-N 0.000 claims 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 abstract description 8
- 230000001590 oxidative effect Effects 0.000 abstract description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract description 3
- 230000003197 catalytic effect Effects 0.000 abstract 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 abstract 1
- 239000010457 zeolite Substances 0.000 description 19
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 17
- 229910021536 Zeolite Inorganic materials 0.000 description 16
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 11
- 239000002638 heterogeneous catalyst Substances 0.000 description 5
- 239000002808 molecular sieve Substances 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 5
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 238000006555 catalytic reaction Methods 0.000 description 4
- -1 cycloalkyl hydrogen Chemical compound 0.000 description 4
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 4
- 229910052737 gold Inorganic materials 0.000 description 4
- 239000010931 gold Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000010936 titanium Substances 0.000 description 4
- 229910052723 transition metal Inorganic materials 0.000 description 4
- 150000003624 transition metals Chemical class 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
- 235000011037 adipic acid Nutrition 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical group C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 150000003016 phosphoric acids Chemical class 0.000 description 2
- 150000003053 piperidines Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 2
- SUBDBMMJDZJVOS-UHFFFAOYSA-N 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- UGACIEPFGXRWCH-UHFFFAOYSA-N [Si].[Ti] Chemical compound [Si].[Ti] UGACIEPFGXRWCH-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001279 adipic acids Chemical class 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000008901 benefit 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
- 238000001354 calcination Methods 0.000 description 1
- 238000003421 catalytic decomposition reaction Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical group O=C1CCCCC1 JHIVVAPYMSGYDF-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
- 239000012153 distilled water Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229960000381 omeprazole Drugs 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 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
- 230000002194 synthesizing effect Effects 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)
Abstract
Description
Claims (10)
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 (2)
Publication Number | Publication Date |
---|---|
CN104736506A CN104736506A (zh) | 2015-06-24 |
CN104736506B true CN104736506B (zh) | 2017-04-12 |
Family
ID=49996500
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201280074884.4A Expired - Fee Related CN104736506B (zh) | 2012-07-26 | 2012-07-26 | 环烷烃氧化催化剂以及生产醇和酮的方法 |
Country Status (11)
Country | Link |
---|---|
US (1) | US9708238B2 (zh) |
EP (1) | EP2877439B1 (zh) |
JP (1) | JP6068638B2 (zh) |
KR (1) | KR101953948B1 (zh) |
CN (1) | CN104736506B (zh) |
BR (1) | BR112015001573B1 (zh) |
IN (1) | IN2015DN00388A (zh) |
RU (1) | RU2583055C1 (zh) |
SG (1) | SG11201500522VA (zh) |
UA (1) | UA111907C2 (zh) |
WO (1) | WO2014015491A1 (zh) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
PL3237365T3 (pl) * | 2014-12-22 | 2019-05-31 | Rhodia Operations | Katalizatory utleniania cykloalkanu i sposób wytwarzania alkoholi i ketonów |
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 |
CN101039892A (zh) * | 2004-08-17 | 2007-09-19 | 索罗蒂亚公司 | 环烷烃氧化和环烷基氢过氧化物分解的催化剂 |
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 |
CN102079695A (zh) * | 2009-11-27 | 2011-06-01 | 中国石油化工股份有限公司 | 一种催化氧化环己烷的方法 |
Family Cites Families (9)
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---|---|---|---|---|
NL9201756A (nl) | 1992-10-09 | 1994-05-02 | Univ Delft Tech | Werkwijze voor de gekatalyseerde ontleding van organische hydroperoxiden. |
US6548718B2 (en) * | 2000-04-27 | 2003-04-15 | Shell Oil Company | Process for catalytic hydroxylation of, saturated or unsaturated, aliphatic compounds |
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 |
DK1830956T3 (da) * | 2004-12-28 | 2023-02-06 | Neste Oyj | Fremgangsmåde til forberedelse af katalytiske materialer |
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 |
CN102452895B (zh) * | 2010-10-29 | 2015-03-18 | 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 |
-
2012
- 2012-07-26 EP EP12881881.2A patent/EP2877439B1/en not_active Not-in-force
- 2012-07-26 CN CN201280074884.4A patent/CN104736506B/zh not_active Expired - Fee Related
- 2012-07-26 WO PCT/CN2012/079172 patent/WO2014015491A1/en active Application Filing
- 2012-07-26 KR KR1020157001615A patent/KR101953948B1/ko active IP Right Grant
- 2012-07-26 UA UAA201501563A patent/UA111907C2/uk unknown
- 2012-07-26 JP JP2015523363A patent/JP6068638B2/ja active Active
- 2012-07-26 US US14/416,977 patent/US9708238B2/en active Active
- 2012-07-26 RU RU2015106498/04A patent/RU2583055C1/ru active
- 2012-07-26 BR BR112015001573-5A patent/BR112015001573B1/pt not_active IP Right Cessation
- 2012-07-26 IN IN388DEN2015 patent/IN2015DN00388A/en unknown
- 2012-07-26 SG SG11201500522VA patent/SG11201500522VA/en unknown
Patent 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 |
CN101039892A (zh) * | 2004-08-17 | 2007-09-19 | 索罗蒂亚公司 | 环烷烃氧化和环烷基氢过氧化物分解的催化剂 |
CN102079695A (zh) * | 2009-11-27 | 2011-06-01 | 中国石油化工股份有限公司 | 一种催化氧化环己烷的方法 |
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 |
Non-Patent Citations (1)
Title |
---|
Unique trans-Selectivity of Ti-MWW in Epoxidation of cis/trans-alkenes with Hydrogen Peroxide;Peng Wu et al.;《J.Phys.Chem》;20020103;第106卷(第4期);第748-753页 * |
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BR112015001573B1 (pt) | 2020-10-27 |
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JP6068638B2 (ja) | 2017-01-25 |
IN2015DN00388A (zh) | 2015-06-12 |
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WO2014015491A1 (en) | 2014-01-30 |
CN104736506A (zh) | 2015-06-24 |
UA111907C2 (uk) | 2016-06-24 |
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EP2877439A1 (en) | 2015-06-03 |
RU2583055C1 (ru) | 2016-05-10 |
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