JP2004517842A - オキシラン化合物を調製する方法 - Google Patents
オキシラン化合物を調製する方法 Download PDFInfo
- Publication number
- JP2004517842A JP2004517842A JP2002549657A JP2002549657A JP2004517842A JP 2004517842 A JP2004517842 A JP 2004517842A JP 2002549657 A JP2002549657 A JP 2002549657A JP 2002549657 A JP2002549657 A JP 2002549657A JP 2004517842 A JP2004517842 A JP 2004517842A
- Authority
- JP
- Japan
- Prior art keywords
- alkylaryl
- catalyst
- compound
- weight
- reaction product
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 32
- 150000002924 oxiranes Chemical class 0.000 title description 6
- 239000003054 catalyst Substances 0.000 claims abstract description 68
- -1 oxirane compound Chemical class 0.000 claims abstract description 41
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 29
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 16
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
- 239000001257 hydrogen Substances 0.000 claims abstract description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 150000001336 alkenes Chemical class 0.000 claims abstract description 12
- 150000002576 ketones Chemical class 0.000 claims abstract description 11
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 10
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 9
- 230000001590 oxidative effect Effects 0.000 claims abstract description 4
- 238000004064 recycling Methods 0.000 claims abstract description 3
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims description 34
- 150000001875 compounds Chemical class 0.000 claims description 16
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 4
- 239000000377 silicon dioxide Substances 0.000 claims description 4
- 239000010936 titanium Substances 0.000 claims description 4
- 229910052719 titanium Inorganic materials 0.000 claims description 4
- OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 claims description 2
- 150000004996 alkyl benzenes Chemical class 0.000 claims description 2
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- BDCFWIDZNLCTMF-UHFFFAOYSA-N 2-phenylpropan-2-ol Chemical compound CC(C)(O)C1=CC=CC=C1 BDCFWIDZNLCTMF-UHFFFAOYSA-N 0.000 description 13
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 8
- OUVFWIHVZPQHJF-UHFFFAOYSA-N 5-ethenyl-5-methylcyclohexa-1,3-diene Chemical compound C=CC1(C)CC=CC=C1 OUVFWIHVZPQHJF-UHFFFAOYSA-N 0.000 description 8
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 8
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 8
- 229910052802 copper Inorganic materials 0.000 description 8
- 239000010949 copper Substances 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 229910052725 zinc Inorganic materials 0.000 description 8
- 239000011701 zinc Substances 0.000 description 8
- 239000006227 byproduct Substances 0.000 description 7
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- 150000002432 hydroperoxides Chemical class 0.000 description 6
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 5
- 238000006735 epoxidation reaction Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 229910052726 zirconium Inorganic materials 0.000 description 5
- NJWSNNWLBMSXQR-UHFFFAOYSA-N 2-hexyloxirane Chemical compound CCCCCCC1CO1 NJWSNNWLBMSXQR-UHFFFAOYSA-N 0.000 description 4
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 229930003836 cresol Natural products 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- LVBXEMGDVWVTGY-UHFFFAOYSA-N trans-2-octenal Natural products CCCCCC=CC=O LVBXEMGDVWVTGY-UHFFFAOYSA-N 0.000 description 4
- GQNOPVSQPBUJKQ-UHFFFAOYSA-N 1-hydroperoxyethylbenzene Chemical compound OOC(C)C1=CC=CC=C1 GQNOPVSQPBUJKQ-UHFFFAOYSA-N 0.000 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 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 150000002736 metal compounds Chemical class 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- DEDZSLCZHWTGOR-UHFFFAOYSA-N propylcyclohexane Chemical compound CCCC1CCCCC1 DEDZSLCZHWTGOR-UHFFFAOYSA-N 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical compound CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 description 2
- BZOVBIIWPDQIHF-UHFFFAOYSA-N 3-hydroxy-2-methylbenzenesulfonic acid Chemical compound CC1=C(O)C=CC=C1S(O)(=O)=O BZOVBIIWPDQIHF-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- XPNGNIFUDRPBFJ-UHFFFAOYSA-N alpha-methylbenzylalcohol Natural products CC1=CC=CC=C1CO XPNGNIFUDRPBFJ-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 229930007927 cymene Natural products 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-M hydroperoxide group Chemical group [O-]O MHAJPDPJQMAIIY-UHFFFAOYSA-M 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 150000002910 rare earth metals Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- ZXTHWIZHGLNEPG-UHFFFAOYSA-N 2-phenyl-4,5-dihydro-1,3-oxazole Chemical compound O1CCN=C1C1=CC=CC=C1 ZXTHWIZHGLNEPG-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- AVFBYUADVDVJQL-UHFFFAOYSA-N phosphoric acid;trioxotungsten;hydrate Chemical compound O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O AVFBYUADVDVJQL-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 150000003682 vanadium compounds Chemical class 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
- C07D301/19—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with organic hydroperoxides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Epoxy Compounds (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 |
|---|---|---|---|
| US09/736,522 US6455712B1 (en) | 2000-12-13 | 2000-12-13 | Preparation of oxirane compounds |
| PCT/EP2001/014750 WO2002048126A2 (en) | 2000-12-13 | 2001-12-13 | Process for preparing oxirane compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004517842A true JP2004517842A (ja) | 2004-06-17 |
| JP2004517842A5 JP2004517842A5 (https=) | 2009-04-16 |
Family
ID=24960203
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002549657A Pending JP2004517842A (ja) | 2000-12-13 | 2001-12-13 | オキシラン化合物を調製する方法 |
| JP2002549656A Withdrawn JP2004517841A (ja) | 2000-12-13 | 2001-12-13 | オキシラン化合物を調製する方法 |
| JP2002549658A Withdrawn JP2004525870A (ja) | 2000-12-13 | 2001-12-13 | オキシラン化合物を調製する方法 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002549656A Withdrawn JP2004517841A (ja) | 2000-12-13 | 2001-12-13 | オキシラン化合物を調製する方法 |
| JP2002549658A Withdrawn JP2004525870A (ja) | 2000-12-13 | 2001-12-13 | オキシラン化合物を調製する方法 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6455712B1 (https=) |
| EP (3) | EP1366031A2 (https=) |
| JP (3) | JP2004517842A (https=) |
| KR (3) | KR20030075151A (https=) |
| CN (3) | CN1213041C (https=) |
| AU (6) | AU2002217114B2 (https=) |
| BR (3) | BR0116099A (https=) |
| RU (3) | RU2282625C2 (https=) |
| TW (3) | TW593298B (https=) |
| WO (3) | WO2002048125A2 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2020507577A (ja) * | 2017-02-10 | 2020-03-12 | ドラゴンフライ セラピューティクス， インコーポレイテッド | Ｐｓｍａ、ｎｋｇ２ｄおよびｃｄ１６に結合するタンパク質 |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10105527A1 (de) * | 2001-02-07 | 2002-08-08 | Basf Ag | Verfahren zur Herstellung eines Epoxids |
| JP4472355B2 (ja) | 2002-04-03 | 2010-06-02 | ベーリンゲ、イノベイション、アクチボラグ | フロアボード用機械式係止システム |
| US6844454B2 (en) | 2002-04-12 | 2005-01-18 | Shell Oil Company | Process |
| US7294727B2 (en) | 2002-12-02 | 2007-11-13 | Shell Oil Company | Catalyst preparation |
| AU2004256091B2 (en) * | 2003-06-30 | 2008-05-01 | Shell Internationale Research Maatschappij B.V. | Process for producing alkylbenzene |
| US7358411B2 (en) * | 2003-06-30 | 2008-04-15 | Shell Oil Company | Hydrocracking of diphenylalkanes |
| US7193093B2 (en) * | 2003-06-30 | 2007-03-20 | Shell Oil Company | Process for producing alkylene oxide |
| RU2354654C2 (ru) * | 2003-08-19 | 2009-05-10 | Шелл Интернэшнл Рисерч Маатсхаппий Б.В. | Способ получения алкилен-оксида |
| DE202004021867U1 (de) | 2004-10-22 | 2011-12-27 | Välinge Innovation AB | Mechanische Verriegelung für Bodenpaneele |
| US7454875B2 (en) | 2004-10-22 | 2008-11-25 | Valinge Aluminium Ab | Mechanical locking system for floor panels |
| SI1650375T2 (sl) | 2004-10-22 | 2011-04-29 | Vaelinge Innovation Ab | Set talnih panelov |
| US7841144B2 (en) | 2005-03-30 | 2010-11-30 | Valinge Innovation Ab | Mechanical locking system for panels and method of installing same |
| KR100589063B1 (ko) * | 2004-12-15 | 2006-06-12 | 현인기술 주식회사 | 머리 마사지기 구조 |
| US8061104B2 (en) | 2005-05-20 | 2011-11-22 | Valinge Innovation Ab | Mechanical locking system for floor panels |
| AU2007247223A1 (en) | 2006-05-02 | 2007-11-15 | Shell Internationale Research Maatschappij B.V. | Titanium catalyst, its preparation and its use in epoxidation reactions |
| SE533410C2 (sv) | 2006-07-11 | 2010-09-14 | Vaelinge Innovation Ab | Golvpaneler med mekaniska låssystem med en flexibel och förskjutbar tunga samt tunga därför |
| US8689512B2 (en) | 2006-11-15 | 2014-04-08 | Valinge Innovation Ab | Mechanical locking of floor panels with vertical folding |
| SE531111C2 (sv) | 2006-12-08 | 2008-12-23 | Vaelinge Innovation Ab | Mekanisk låsning av golvpaneler |
| WO2009061279A1 (en) | 2007-11-07 | 2009-05-14 | Välinge Innovation AB | Mechanical locking of floor panels with vertical snap folding and an installation method to connect such panels |
| EP2235285B1 (en) | 2008-01-31 | 2019-06-26 | Välinge Innovation AB | Mechanical locking of floor panels |
| CN102066674B (zh) | 2008-05-15 | 2015-06-03 | 瓦林格创新股份有限公司 | 具有通过磁场启动的机械锁定系统的地板镶板及安装镶板的方法 |
| EP3702549B1 (en) | 2010-01-12 | 2023-05-10 | Välinge Innovation AB | Set of floor panels |
| BR112012018285B1 (pt) | 2010-02-04 | 2020-02-18 | Välinge Innovation AB | Conjunto de painéis de piso |
| WO2011127981A1 (en) | 2010-04-15 | 2011-10-20 | Spanolux N.V.- Div. Balterio | Floor panel assembly |
| WO2012010491A1 (en) | 2010-07-19 | 2012-01-26 | Shell Internationale Research Maatschappij B.V. | Epoxidation process |
| UA109938C2 (uk) | 2011-05-06 | 2015-10-26 | Механічна фіксуюча система для будівельних панелей | |
| UA114715C2 (uk) | 2011-07-05 | 2017-07-25 | Сералок Інновейшн Аб | Механічна фіксація панелей настилу підлоги до язичка з нанесеним шаром клею |
| US9725912B2 (en) | 2011-07-11 | 2017-08-08 | Ceraloc Innovation Ab | Mechanical locking system for floor panels |
| US8650826B2 (en) | 2011-07-19 | 2014-02-18 | Valinge Flooring Technology Ab | Mechanical locking system for floor panels |
| US8857126B2 (en) | 2011-08-15 | 2014-10-14 | Valinge Flooring Technology Ab | Mechanical locking system for floor panels |
| US9216541B2 (en) | 2012-04-04 | 2015-12-22 | Valinge Innovation Ab | Method for producing a mechanical locking system for building panels |
| AU2013348454C1 (en) | 2012-11-22 | 2017-11-09 | Ceraloc Innovation Ab | Mechanical locking system for floor panels |
| HUE060779T2 (hu) | 2013-06-27 | 2023-04-28 | Vaelinge Innovation Ab | Mechanikus rögzítõrendszerrel ellátott építõpanel |
| US10246883B2 (en) | 2014-05-14 | 2019-04-02 | Valinge Innovation Ab | Building panel with a mechanical locking system |
| KR102386246B1 (ko) | 2014-05-14 | 2022-04-12 | 뵈린게 이노베이션 에이비이 | 기계식 록킹 시스템이 구비된 빌딩 패널 |
| EP3023402A1 (en) | 2014-11-20 | 2016-05-25 | Shell Internationale Research Maatschappij B.V. | Improvements relating to hydrogenolysis of phenyl alcohols |
| CN107002411B (zh) | 2014-11-27 | 2020-06-16 | 瓦林格创新股份有限公司 | 用于地板镶板的机械锁定系统 |
| CN121892114A (zh) | 2015-11-09 | 2026-04-21 | 国际壳牌研究有限公司 | 催化剂制备 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3350422A (en) | 1966-02-01 | 1967-10-31 | Halcon International Inc | Catalytic epoxidation of an olefinically unsaturated compound using an organic hydroperoxide as an epoxidizing agent |
| US4400558A (en) * | 1981-04-17 | 1983-08-23 | Atlantic Richfield Company | Recovery of 2-phenylethanol |
| GB8813484D0 (en) * | 1988-06-08 | 1988-07-13 | Shell Int Research | Process for preparation of oxirane compound |
| US5017729A (en) * | 1988-09-30 | 1991-05-21 | Mitsui Petrochemical Industries, Ltd. | Phenol preparation process and propylene recovery therefrom |
| MY105602A (en) * | 1988-11-28 | 1994-11-30 | Mitsui Petrochemical Ind | Preparation of cumene through alkylation of an aromatic compound and preparation of phenol through cumene. |
| US5371305A (en) * | 1992-12-31 | 1994-12-06 | Hercules Incorporated | Process for producing phenol from cumene |
| EP0689685A1 (en) | 1993-03-15 | 1996-01-03 | Minnesota Mining And Manufacturing Company | Ballasted leuco dyes and photothermographic element containing same |
| US5475159A (en) | 1994-11-07 | 1995-12-12 | Shell Oil Company | Process for the direct hydrogenation of methyl esters |
| US5723637A (en) * | 1995-12-06 | 1998-03-03 | Sumitomo Chemical Company, Limited | Process for producing propylene oxide |
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| JPH11140068A (ja) * | 1997-11-07 | 1999-05-25 | Sumitomo Chem Co Ltd | プロピレンオキサイドの製造方法 |
| RU2140896C1 (ru) * | 1998-08-17 | 1999-11-10 | ОАО "Нижнекамскнефтехим" | Способ очистки от легкокипящей фракции углеводородов возвратного этилбензола производства оксида пропилена со стиролом |
| JP2001031662A (ja) | 1999-07-14 | 2001-02-06 | Sumitomo Chem Co Ltd | プロピレンオキサイドの製造方法 |
| JP2001270876A (ja) | 2000-03-24 | 2001-10-02 | Sumitomo Chem Co Ltd | プロピレンオキサイドの製造方法 |
| JP2001270871A (ja) | 2000-03-24 | 2001-10-02 | Sumitomo Chem Co Ltd | オキシラン化合物の製造方法 |
| JP2001270879A (ja) | 2000-03-24 | 2001-10-02 | Sumitomo Chem Co Ltd | オキシラン化合物の製造方法 |
| JP2001270877A (ja) | 2000-03-24 | 2001-10-02 | Sumitomo Chem Co Ltd | プロピレンオキサイドの製造方法 |
| JP2001270872A (ja) | 2000-03-24 | 2001-10-02 | Sumitomo Chem Co Ltd | プロピレンオキサイドの製造方法 |
| JP2001270874A (ja) | 2000-03-24 | 2001-10-02 | Sumitomo Chem Co Ltd | プロピレンオキサイドの製造方法 |
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2000
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2001
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2020507577A (ja) * | 2017-02-10 | 2020-03-12 | ドラゴンフライ セラピューティクス， インコーポレイテッド | Ｐｓｍａ、ｎｋｇ２ｄおよびｃｄ１６に結合するタンパク質 |
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