JP2015501842A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2015501842A5 JP2015501842A5 JP2014547414A JP2014547414A JP2015501842A5 JP 2015501842 A5 JP2015501842 A5 JP 2015501842A5 JP 2014547414 A JP2014547414 A JP 2014547414A JP 2014547414 A JP2014547414 A JP 2014547414A JP 2015501842 A5 JP2015501842 A5 JP 2015501842A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- unsaturated
- alkyl
- group
- aryl
- 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.)
- Granted
Links
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 38
- 238000006459 hydrosilylation reaction Methods 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 26
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 claims description 24
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 19
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 18
- 125000003107 substituted aryl group Chemical group 0.000 claims description 18
- -1 unsaturated cycloalkyl epoxide Chemical class 0.000 claims description 17
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 16
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical group CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 claims description 10
- NWRZGFYWENINNX-UHFFFAOYSA-N 1,1,2-tris(ethenyl)cyclohexane Chemical compound C=CC1CCCCC1(C=C)C=C NWRZGFYWENINNX-UHFFFAOYSA-N 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 125000000524 functional group Chemical group 0.000 claims description 8
- 229910052742 iron Inorganic materials 0.000 claims description 8
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 7
- 229920000570 polyether Polymers 0.000 claims description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 7
- SWGZAKPJNWCPRY-UHFFFAOYSA-N methyl-bis(trimethylsilyloxy)silicon Chemical group C[Si](C)(C)O[Si](C)O[Si](C)(C)C SWGZAKPJNWCPRY-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 4
- 150000001336 alkenes Chemical class 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 150000001925 cycloalkenes Chemical class 0.000 claims description 4
- 229910001873 dinitrogen Inorganic materials 0.000 claims description 4
- 229910052748 manganese Inorganic materials 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 229910052759 nickel Inorganic materials 0.000 claims description 4
- 229920001296 polysiloxane Polymers 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 150000004756 silanes Chemical class 0.000 claims description 4
- 229910004283 SiO 4 Inorganic materials 0.000 claims description 3
- 150000001924 cycloalkanes Chemical class 0.000 claims description 3
- GBCKRQRXNXQQPW-UHFFFAOYSA-N n,n-dimethylprop-2-en-1-amine Chemical compound CN(C)CC=C GBCKRQRXNXQQPW-UHFFFAOYSA-N 0.000 claims description 3
- 229920000642 polymer Polymers 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- UWRZIZXBOLBCON-UHFFFAOYSA-N 2-phenylethenamine Chemical compound NC=CC1=CC=CC=C1 UWRZIZXBOLBCON-UHFFFAOYSA-N 0.000 claims description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical class COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 2
- 239000004793 Polystyrene Substances 0.000 claims description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 2
- 150000001345 alkine derivatives Chemical class 0.000 claims description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 150000008378 aryl ethers Chemical class 0.000 claims description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 2
- 229920002223 polystyrene Polymers 0.000 claims description 2
- 229920002635 polyurethane Polymers 0.000 claims description 2
- 239000004814 polyurethane Substances 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- 125000001033 ether group Chemical group 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims 2
- 125000001931 aliphatic group Chemical group 0.000 claims 2
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 claims 1
- VMAWODUEPLAHOE-UHFFFAOYSA-N 2,4,6,8-tetrakis(ethenyl)-2,4,6,8-tetramethyl-1,3,5,7,2,4,6,8-tetraoxatetrasilocane Chemical compound C=C[Si]1(C)O[Si](C)(C=C)O[Si](C)(C=C)O[Si](C)(C=C)O1 VMAWODUEPLAHOE-UHFFFAOYSA-N 0.000 claims 1
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 claims 1
- VLQZJOLYNOGECD-UHFFFAOYSA-N 2,4,6-trimethyl-1,3,5,2,4,6-trioxatrisilinane Chemical compound C[SiH]1O[SiH](C)O[SiH](C)O1 VLQZJOLYNOGECD-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 claims 1
- 239000004698 Polyethylene Substances 0.000 claims 1
- 239000004743 Polypropylene Substances 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 239000000412 dendrimer Substances 0.000 claims 1
- 229920000736 dendritic polymer Polymers 0.000 claims 1
- 150000004678 hydrides Chemical class 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical group 0.000 claims 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 229920000573 polyethylene Polymers 0.000 claims 1
- 229920001155 polypropylene Polymers 0.000 claims 1
- 229910052710 silicon Inorganic materials 0.000 claims 1
- 239000010703 silicon Substances 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 239000000047 product Substances 0.000 description 17
- 239000003054 catalyst Substances 0.000 description 16
- 239000012298 atmosphere Substances 0.000 description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 7
- 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 5
- 238000004821 distillation Methods 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 229910052697 platinum Inorganic materials 0.000 description 4
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- KTRQRAQRHBLCSQ-UHFFFAOYSA-N 1,2,4-tris(ethenyl)cyclohexane Chemical class C=CC1CCC(C=C)C(C=C)C1 KTRQRAQRHBLCSQ-UHFFFAOYSA-N 0.000 description 2
- ZQUCFSJTZVIWRB-UHFFFAOYSA-N 2-cyclohexylethyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)CCC1CCCCC1 ZQUCFSJTZVIWRB-UHFFFAOYSA-N 0.000 description 2
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- KEFOZNJTQPJEOB-UHFFFAOYSA-N pyridine-2,3-diimine Chemical compound N=C1C=CC=NC1=N KEFOZNJTQPJEOB-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- CCEFMUBVSUDRLG-KXUCPTDWSA-N (4R)-limonene 1,2-epoxide Natural products C1[C@H](C(=C)C)CC[C@@]2(C)O[C@H]21 CCEFMUBVSUDRLG-KXUCPTDWSA-N 0.000 description 1
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- WEEGYLXZBRQIMU-UHFFFAOYSA-N 1,8-cineole Natural products C1CC2CCC1(C)OC2(C)C WEEGYLXZBRQIMU-UHFFFAOYSA-N 0.000 description 1
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- FVCDMHWSPLRYAB-UHFFFAOYSA-N 2-ethenyl-2-methyloxirane Chemical compound C=CC1(C)CO1 FVCDMHWSPLRYAB-UHFFFAOYSA-N 0.000 description 1
- UKTHULMXFLCNAV-UHFFFAOYSA-N 2-hex-5-enyloxirane Chemical compound C=CCCCCC1CO1 UKTHULMXFLCNAV-UHFFFAOYSA-N 0.000 description 1
- FCZHJHKCOZGQJZ-UHFFFAOYSA-N 2-oct-7-enyloxirane Chemical compound C=CCCCCCCC1CO1 FCZHJHKCOZGQJZ-UHFFFAOYSA-N 0.000 description 1
- SLJFKNONPLNAPF-UHFFFAOYSA-N 3-Vinyl-7-oxabicyclo[4.1.0]heptane Chemical compound C1C(C=C)CCC2OC21 SLJFKNONPLNAPF-UHFFFAOYSA-N 0.000 description 1
- 0 Cc1c(*)c(*)c(*)c(*)c1* Chemical compound Cc1c(*)c(*)c(*)c(*)c1* 0.000 description 1
- CCEFMUBVSUDRLG-XNWIYYODSA-N Limonene-1,2-epoxide Chemical compound C1[C@H](C(=C)C)CCC2(C)OC21 CCEFMUBVSUDRLG-XNWIYYODSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- GSFXLBMRGCVEMO-UHFFFAOYSA-N [SiH4].[S] Chemical class [SiH4].[S] GSFXLBMRGCVEMO-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- UCAOGXRUJFKQAP-UHFFFAOYSA-N n,n-dimethyl-5-nitropyridin-2-amine Chemical compound CN(C)C1=CC=C([N+]([O-])=O)C=N1 UCAOGXRUJFKQAP-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 238000006884 silylation reaction Methods 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13/325,250 US9782763B2 (en) | 2011-12-14 | 2011-12-14 | Non-precious metal-based hyrdosilylation catalysts exhibiting improved selectivity |
| US13/325,250 | 2011-12-14 | ||
| PCT/US2012/069469 WO2013090548A1 (en) | 2011-12-14 | 2012-12-13 | Non- precious metal -based hydrosilylation catalysts |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015501842A JP2015501842A (ja) | 2015-01-19 |
| JP2015501842A5 true JP2015501842A5 (OSRAM) | 2016-02-04 |
| JP6211531B2 JP6211531B2 (ja) | 2017-10-11 |
Family
ID=47459175
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014547414A Active JP6211531B2 (ja) | 2011-12-14 | 2012-12-13 | 非貴金属系ヒドロシリル化触媒 |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US9782763B2 (OSRAM) |
| EP (1) | EP2790829B1 (OSRAM) |
| JP (1) | JP6211531B2 (OSRAM) |
| KR (1) | KR20140116100A (OSRAM) |
| CN (1) | CN104114278A (OSRAM) |
| BR (1) | BR112014014517A2 (OSRAM) |
| TW (1) | TWI614063B (OSRAM) |
| WO (1) | WO2013090548A1 (OSRAM) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9782763B2 (en) | 2011-12-14 | 2017-10-10 | Momentive Performance Materials Inc. | Non-precious metal-based hyrdosilylation catalysts exhibiting improved selectivity |
| US9447125B2 (en) | 2012-08-16 | 2016-09-20 | Momentive Performance Materials Inc. | Reusable homogeneous cobalt pyridine diimine catalysts for dehydrogenative silylation and tandem dehydrogenative-silylation-hydrogenation |
| US9371340B2 (en) | 2012-08-16 | 2016-06-21 | Momentive Performance Materials Inc. | Dehydrogenative silylation, hydrosilylation and crosslinking using cobalt catalysts |
| US9890182B2 (en) * | 2013-05-06 | 2018-02-13 | Momentive Performance Materials Inc. | Selective 1,2-hydrosilylation of terminally unsaturated 1,3-dienes using iron catalysts |
| US9371339B2 (en) | 2013-05-06 | 2016-06-21 | Momentive Performance Materials Inc. | Saturated and unsaturated silahydrocarbons via iron and cobalt pyridine diimine catalyzed olefin silylation |
| CN105228744B (zh) | 2013-05-15 | 2021-04-06 | 莫门蒂夫性能材料股份有限公司 | 用甲硅烷基氢化物活化金属盐及其在氢化硅烷化反应中的应用 |
| WO2015077306A1 (en) | 2013-11-19 | 2015-05-28 | Momentive Performance Materials Inc. | Cobalt catalysts and their use for hydrosilylation and dehydrogenative silylation |
| TW201538510A (zh) | 2013-11-19 | 2015-10-16 | Momentive Performance Mat Inc | 鈷觸媒及其於矽氫化與脫氫甲矽烷化之用途 |
| EP3071585B1 (en) | 2013-11-19 | 2018-11-07 | Momentive Performance Materials Inc. | Cobalt catalysts and their use for hydrosilylation and dehydrogenative silylation |
| WO2017072084A1 (en) * | 2015-10-26 | 2017-05-04 | Shell Internationale Research Maatschappij B.V. | Mechanically strong catalyst and catalyst carrier, its preparation, and its use |
| EP3272758B1 (de) | 2016-07-22 | 2018-06-27 | Evonik Degussa GmbH | Verfahren zur herstellung von tris[3-(alkoxysilyl)propyl]isocyanuraten |
| EP3372609B1 (de) | 2017-03-08 | 2021-04-28 | Evonik Operations GmbH | Verfahren zur herstellung von tris[3-(alkoxysilyl)propyl]isocyanuraten |
| US10377776B2 (en) | 2017-03-08 | 2019-08-13 | Evonik Degussa Gmbh | Process for preparing tris[3-(alkoxysilyl)propyl]isocyanurates |
| EP3372608B1 (de) | 2017-03-08 | 2021-04-28 | Evonik Operations GmbH | Verfahren zur herstellung von tris[3-(alkoxysilyl)propyl]isocyanuraten |
| CN107511176B (zh) * | 2017-08-15 | 2020-02-14 | 常州大学 | 一种铁基吡咯烷酮离子液体催化不饱和烷基酯硅氢加成反应的方法 |
| PL3473631T3 (pl) | 2017-10-19 | 2020-06-29 | Evonik Operations Gmbh | Nowe alkoksysilany z epoksydowymi grupami funkcyjnymi, sposób ich wytwarzania i ich zastosowanie |
| CN110343128B (zh) * | 2018-04-04 | 2021-02-19 | 中国科学院化学研究所 | 一种通过硅氢化反应制备硅烷的方法 |
| DE102018210886A1 (de) | 2018-07-03 | 2020-01-09 | Evonik Degussa Gmbh | Verfahren zur Herstellung von Alkylalkoxysilanen |
| KR102807413B1 (ko) | 2018-09-13 | 2025-05-13 | 모멘티브 퍼포먼스 머티리얼즈 게엠베하 | 기능성 폴리실록산 |
| IL282699B2 (en) | 2018-11-02 | 2024-05-01 | Shell Int Research | Wastewater separation of oxidative dehydrogenation of ethane |
| EP3915995B1 (en) | 2020-05-29 | 2025-11-26 | Momentive Performance Materials Inc. | Process for the stepwise synthesis of silahydrocarbons |
| TWI888612B (zh) | 2020-08-03 | 2025-07-01 | 荷蘭商蜆殼國際研究公司 | 整合乙烯生產方法 |
Family Cites Families (60)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3159601A (en) | 1962-07-02 | 1964-12-01 | Gen Electric | Platinum-olefin complex catalyzed addition of hydrogen- and alkenyl-substituted siloxanes |
| US3220972A (en) | 1962-07-02 | 1965-11-30 | Gen Electric | Organosilicon process using a chloroplatinic acid reaction product as the catalyst |
| US3296291A (en) | 1962-07-02 | 1967-01-03 | Gen Electric | Reaction of silanes with unsaturated olefinic compounds |
| US3775452A (en) | 1971-04-28 | 1973-11-27 | Gen Electric | Platinum complexes of unsaturated siloxanes and platinum containing organopolysiloxanes |
| GB1476314A (en) | 1973-06-23 | 1977-06-10 | Dow Corning Ltd | Coating process |
| GB2013207B (en) | 1977-11-14 | 1982-10-27 | Spencer J L | Hydrosilylation catalysts |
| US4550152A (en) | 1983-10-28 | 1985-10-29 | General Electric Company | Nickel complex catalyst for hydrosilation reactions |
| US4578497A (en) | 1984-11-30 | 1986-03-25 | Gulf Research & Development Company | Tetraalkylsilane synthetic fluids |
| US4572791A (en) | 1984-12-06 | 1986-02-25 | Gulf Research & Development Company | Production of saturated and unsaturated silahydrocarbon mixtures using rhodium catalyst, and to products produced thereby |
| US4729821A (en) | 1986-11-03 | 1988-03-08 | Board Of Regents, The University Of Texas System | In situ activation of catalysts by applied electrical potentials |
| US4788312A (en) | 1988-03-16 | 1988-11-29 | Technolube Division Lubricating Specialties Co. | Trisilahydrocarbon lubricants |
| FR2641785B1 (fr) | 1989-01-19 | 1992-07-31 | Essilor Int | Composition de polymeres transparents pour lentilles de contact de type rigide, permeables a l'oxygene |
| US5026893A (en) | 1990-06-11 | 1991-06-25 | Lubricating Specialties Company | Polysilahydrocarbon lubricants |
| WO1992010544A1 (en) | 1990-12-13 | 1992-06-25 | Minnesota Mining And Manufacturing Company | Radiation activated hydrosilation reaction |
| CA2080153A1 (en) | 1991-11-29 | 1993-05-30 | Chris A. Sumpter | Heat curable organopolysiloxane compositions, preformed latent platinum catalysts, and methods for making |
| JPH05295269A (ja) | 1991-11-29 | 1993-11-09 | General Electric Co <Ge> | 熱硬化性オルガノポリシロキサン組成物、予備生成済み潜伏性白金触媒およびそれの調製方法 |
| US5880241A (en) | 1995-01-24 | 1999-03-09 | E. I. Du Pont De Nemours And Company | Olefin polymers |
| US5691435A (en) | 1996-01-25 | 1997-11-25 | Wacker-Chemie Gmbh | Crosslinkable compositions |
| US6423848B2 (en) | 1996-12-17 | 2002-07-23 | E. I. Du Pont De Nemours And Company | Tridentate ligand |
| US6432862B1 (en) | 1996-12-17 | 2002-08-13 | E. I. Du Pont De Nemours And Company | Cobalt catalysts for the polymerization of olefins |
| IL129929A0 (en) | 1996-12-17 | 2000-02-29 | Du Pont | Polymerization of ethylene with specific iron or cobalt complexes novel pyridinebis (imines) and novel complexes of pyridinebis(imines) with iron and cobalt |
| US6214761B1 (en) | 1996-12-17 | 2001-04-10 | E. I. Du Pont De Nemours And Company | Iron catalyst for the polymerization of olefins |
| US6417305B2 (en) | 1996-12-17 | 2002-07-09 | E. I. Du Pont De Nemours And Company | Oligomerization of ethylene |
| US6103946A (en) | 1997-07-15 | 2000-08-15 | E. I. Du Pont De Nemours And Company | Manufacture of α-olefins |
| ATE218147T1 (de) | 1997-09-05 | 2002-06-15 | Bp Chem Int Ltd | Polymerisationskatalysatoren |
| WO1999046303A1 (en) | 1998-03-12 | 1999-09-16 | Bp Chemicals Limited | Polymerisation catalysts |
| EP1062249B1 (en) | 1998-03-12 | 2004-10-20 | BP Chemicals Limited | Polymerisation catalysts |
| TWI238833B (en) * | 1998-03-12 | 2005-09-01 | Bp Chem Int Ltd | Catalysts and method for polymerization of olefins |
| ES2203077T3 (es) | 1998-03-12 | 2004-04-01 | Bp Chemicals Limited | Homopolimero de etileno. |
| ID27209A (id) | 1998-03-12 | 2001-03-08 | Bp Chem Int Ltd | Katalis-katalis polimerisasi |
| US6297338B1 (en) | 1998-03-30 | 2001-10-02 | E. I. Du Pont De Nemours And Company | Polymerization of olefins |
| US7906451B2 (en) | 1998-03-30 | 2011-03-15 | E.I. Du Pont De Nemours And Company | Mixed polymerization catalyst component for polymerizing olefins |
| GB9819847D0 (en) | 1998-09-12 | 1998-11-04 | Bp Chem Int Ltd | Novel compounds |
| DE19856115A1 (de) | 1998-12-04 | 2000-06-21 | Wacker Chemie Gmbh | Alkenylgruppen aufweisende Siloxancopolymere |
| US6620895B1 (en) | 1999-03-22 | 2003-09-16 | E. I. Du Pont De Nemours And Company | Processing polyethylenes |
| US6281303B1 (en) | 1999-07-27 | 2001-08-28 | Eastman Chemical Company | Olefin oligomerization and polymerization catalysts |
| US6458905B1 (en) | 1999-08-16 | 2002-10-01 | Phillips Petroleum Company | Complexes of pyridldiimines with vanadium and other transition metals, and their use as olefin oligomerization and polymerization catalysts |
| US6278011B1 (en) | 1999-08-30 | 2001-08-21 | The University Of Dayton | Polysilahydrocarbons as lubricants for aerospace application |
| DE60211884T2 (de) | 2001-04-30 | 2006-11-23 | Ciba Speciality Chemicals Holding Inc. | Verwendung von metallkomplexverbindungen als oxidationskatalysatoren |
| WO2003042131A1 (en) | 2001-11-15 | 2003-05-22 | Stichting Voor De Technische Wetenschappen | Hydrogenation catalyst and catalysed hydrogenation process |
| WO2004007509A1 (en) | 2002-07-17 | 2004-01-22 | Exxonmobil Chemical Patents Inc. | Late transition metal catalysts for olefin polymerization and oligomerization |
| RU2315658C2 (ru) | 2002-09-25 | 2008-01-27 | Шелл Интернэшнл Рисерч Маатсхаппий Б.В. | Каталитические системы для олигомеризации этилена в линейные альфа-олефины |
| DE10258126B3 (de) * | 2002-12-12 | 2004-01-29 | Wacker-Chemie Gmbh | Alkinolgruppen aufweisende Organosiliciumverbindungen sowie diese enthaltend vernetzbare Massen und daraus herstellbare Formkörper |
| CN101010351B (zh) | 2004-07-09 | 2011-06-22 | 纳幕尔杜邦公司 | 用于烯烃聚合或低聚的催化剂 |
| US8062552B2 (en) | 2005-05-19 | 2011-11-22 | Brookhaven Science Associates, Llc | Electrocatalyst for oxygen reduction with reduced platinum oxidation and dissolution rates |
| CN100378111C (zh) | 2005-07-01 | 2008-04-02 | 中国科学院上海有机化学研究所 | 含碳氧醚键有机硅化合物、合成方法及其应用 |
| US7268096B2 (en) | 2005-07-21 | 2007-09-11 | Chevron Phillips Chemical Company Lp | Diimine metal complexes, methods of synthesis, and methods of using in oligomerization and polymerization |
| CN101297004B (zh) | 2005-10-26 | 2014-06-25 | 西巴控股有限公司 | 用于电泳显示器的彩色颗粒 |
| DE102005057460A1 (de) | 2005-12-01 | 2007-06-06 | Wacker Chemie Ag | Zu hochfesten Elastomeren vernetzbare ionisch und/oder organometallisch funktionalisierte Siliconpolymere |
| US7429672B2 (en) | 2006-06-09 | 2008-09-30 | Momentive Performance Materials Inc. | Process for the direct synthesis of trialkoxysilane |
| US7696269B2 (en) | 2006-12-28 | 2010-04-13 | Momentive Performance Materials Inc. | Silated core polysulfides, their preparation and use in filled elastomer compositions |
| US8415443B2 (en) | 2009-07-10 | 2013-04-09 | Momentive Performance Materials Inc. | Hydrosilylation catalysts |
| US8236915B2 (en) * | 2009-07-10 | 2012-08-07 | Momentive Performance Materials Inc. | Hydrosilylation catalysts |
| EP2407187A3 (de) | 2010-07-15 | 2012-06-20 | ECP Entwicklungsgesellschaft mbH | Blutpumpe für die invasive Anwendung innerhalb eines Körpers eines Patienten |
| BR112013012734A2 (pt) | 2010-11-24 | 2016-09-13 | Univ Cornell | mono-hidrossililação catalisada por metal não-precioso seletivo de compostos polinsaturados |
| JP2014503507A (ja) | 2010-11-24 | 2014-02-13 | モメンティブ パフォーマンス マテリアルズ インコーポレイテッド | ヒドロシリル化触媒 |
| JP5991981B2 (ja) | 2010-11-24 | 2016-09-14 | モメンティブ パフォーマンス マテリアルズ インコーポレイテッド | ヒドロシリル化触媒として使用される三座窒素配位子を有する金属錯体のｉｎ−ｓｉｔｕ活性化 |
| CN104024264A (zh) | 2011-09-20 | 2014-09-03 | 道康宁公司 | 含金属的硅氢加成催化剂以及含该催化剂的组合物 |
| CN103946228A (zh) | 2011-09-20 | 2014-07-23 | 道康宁公司 | 含钴硅氢加成催化剂及含有该催化剂的组合物 |
| US9782763B2 (en) | 2011-12-14 | 2017-10-10 | Momentive Performance Materials Inc. | Non-precious metal-based hyrdosilylation catalysts exhibiting improved selectivity |
-
2011
- 2011-12-14 US US13/325,250 patent/US9782763B2/en active Active
-
2012
- 2012-12-13 JP JP2014547414A patent/JP6211531B2/ja active Active
- 2012-12-13 CN CN201280069318.4A patent/CN104114278A/zh active Pending
- 2012-12-13 KR KR1020147019374A patent/KR20140116100A/ko not_active Withdrawn
- 2012-12-13 EP EP12808630.3A patent/EP2790829B1/en active Active
- 2012-12-13 BR BR112014014517A patent/BR112014014517A2/pt not_active Application Discontinuation
- 2012-12-13 WO PCT/US2012/069469 patent/WO2013090548A1/en not_active Ceased
- 2012-12-14 TW TW101147671A patent/TWI614063B/zh active
-
2017
- 2017-09-26 US US15/715,324 patent/US11052383B2/en active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2015501842A5 (OSRAM) | ||
| JP6211531B2 (ja) | 非貴金属系ヒドロシリル化触媒 | |
| EP2698201B1 (en) | Dehydrogenative silylation and crosslinking using cobalt catalysts | |
| JP6019034B2 (ja) | 多価不飽和化合物の金属触媒モノヒドロシリル化 | |
| JP5991981B2 (ja) | ヒドロシリル化触媒として使用される三座窒素配位子を有する金属錯体のｉｎ−ｓｉｔｕ活性化 | |
| JP6486925B2 (ja) | コバルト触媒並びにヒドロシリル化及び脱水素シリル化のためのその使用 | |
| US9447125B2 (en) | Reusable homogeneous cobalt pyridine diimine catalysts for dehydrogenative silylation and tandem dehydrogenative-silylation-hydrogenation | |
| JP2012532885A (ja) | ヒドロシリル化触媒 | |
| JP6515930B2 (ja) | ヒドロシリル化反応触媒 | |
| JP7693180B2 (ja) | 鉄錯体によって触媒されるヒドロシリル化法 | |
| WO2016024607A1 (ja) | ヒドロシリル化反応触媒 | |
| JP6486924B2 (ja) | コバルト触媒並びにヒドロシリル化及び脱水素シリル化のためのその使用 | |
| JP6389297B2 (ja) | コバルト触媒を用いる脱水素シリル化および架橋 | |
| WO2015023328A1 (en) | Reusable homogeneous cobalt pyridine dimine catalysts for dehydrogenative silylation and tandem dehydrogenative-silylation-hydrogenation | |
| EP3590596A1 (en) | Catalyst for hydrosilylation reaction, hydrogenation reaction, and hydrosilane reduction reaction | |
| EP3071583B1 (en) | Dehydrogenative silylation, hydrosilylation and crosslinking using cobalt catalysts | |
| Thompson et al. | · Synthesis of Functional Silicone Architectures via Tris {pentafluorophenyl} borane-Catalyzed Dehydrocarbonative Coupling |