TWI457176B - 使用非貴金屬作為催化劑以製備單矽氫化產物之方法及其製得之組合物 - Google Patents
使用非貴金屬作為催化劑以製備單矽氫化產物之方法及其製得之組合物 Download PDFInfo
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- TWI457176B TWI457176B TW100142961A TW100142961A TWI457176B TW I457176 B TWI457176 B TW I457176B TW 100142961 A TW100142961 A TW 100142961A TW 100142961 A TW100142961 A TW 100142961A TW I457176 B TWI457176 B TW I457176B
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- Prior art keywords
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- hetero atom
- substituted
- formula
- alkyl
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- 238000000034 method Methods 0.000 title claims description 36
- 239000000203 mixture Substances 0.000 title claims description 32
- 239000003054 catalyst Substances 0.000 title description 29
- 239000010970 precious metal Substances 0.000 title description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 53
- 238000005984 hydrogenation reaction Methods 0.000 claims description 53
- NWRZGFYWENINNX-UHFFFAOYSA-N 1,1,2-tris(ethenyl)cyclohexane Chemical compound C=CC1CCCCC1(C=C)C=C NWRZGFYWENINNX-UHFFFAOYSA-N 0.000 claims description 48
- 150000001875 compounds Chemical class 0.000 claims description 41
- 125000003118 aryl group Chemical group 0.000 claims description 39
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 36
- -1 mercaptoalkyl hydride Chemical class 0.000 claims description 32
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 31
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 125000003107 substituted aryl group Chemical group 0.000 claims description 26
- KTRQRAQRHBLCSQ-UHFFFAOYSA-N 1,2,4-tris(ethenyl)cyclohexane Chemical compound C=CC1CCC(C=C)C(C=C)C1 KTRQRAQRHBLCSQ-UHFFFAOYSA-N 0.000 claims description 22
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 claims description 21
- 229940123208 Biguanide Drugs 0.000 claims description 21
- 125000000524 functional group Chemical group 0.000 claims description 20
- 125000003342 alkenyl group Chemical group 0.000 claims description 19
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 125000004122 cyclic group Chemical group 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 229930003658 monoterpene Natural products 0.000 claims description 8
- 150000002773 monoterpene derivatives Chemical class 0.000 claims description 8
- 235000002577 monoterpenes Nutrition 0.000 claims description 8
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 7
- AGGJWJFEEKIYOF-UHFFFAOYSA-N 1,1,1-triethoxydecane Chemical group CCCCCCCCCC(OCC)(OCC)OCC AGGJWJFEEKIYOF-UHFFFAOYSA-N 0.000 claims description 7
- 150000002430 hydrocarbons Chemical group 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 239000012535 impurity Substances 0.000 claims description 5
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 5
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 239000001307 helium Substances 0.000 claims description 4
- 229910052734 helium Inorganic materials 0.000 claims description 4
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 229910052742 iron Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- BCMDUBDPCHPHKQ-UHFFFAOYSA-N CC(CCCCCCCCCOC(OCCCCCCCCCC(C)(C)C)CCCCCCCCC)(C)C Chemical group CC(CCCCCCCCCOC(OCCCCCCCCCC(C)(C)C)CCCCCCCCC)(C)C BCMDUBDPCHPHKQ-UHFFFAOYSA-N 0.000 claims description 3
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 3
- 229910052748 manganese Inorganic materials 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- ZWUBFMWIQJSEQS-UHFFFAOYSA-N 1,1-bis(ethenyl)cyclohexane Chemical class C=CC1(C=C)CCCCC1 ZWUBFMWIQJSEQS-UHFFFAOYSA-N 0.000 claims description 2
- WVAFEFUPWRPQSY-UHFFFAOYSA-N 1,2,3-tris(ethenyl)benzene Chemical compound C=CC1=CC=CC(C=C)=C1C=C WVAFEFUPWRPQSY-UHFFFAOYSA-N 0.000 claims description 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 description 2
- 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 description 2
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 2
- 229910004283 SiO 4 Inorganic materials 0.000 claims description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 150000004678 hydrides Chemical class 0.000 claims description 2
- 125000000466 oxiranyl group Chemical group 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 229910052710 silicon Inorganic materials 0.000 claims description 2
- 239000000047 product Substances 0.000 description 43
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 33
- 238000004817 gas chromatography Methods 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 18
- 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 12
- 238000004821 distillation Methods 0.000 description 11
- 238000002474 experimental method Methods 0.000 description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- 150000002431 hydrogen Chemical class 0.000 description 10
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 10
- 238000009835 boiling Methods 0.000 description 9
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 229920002554 vinyl polymer Polymers 0.000 description 9
- 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 8
- 229910052703 rhodium Inorganic materials 0.000 description 8
- 239000010948 rhodium Substances 0.000 description 8
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 7
- 150000004696 coordination complex Chemical class 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000012298 atmosphere Substances 0.000 description 5
- 229910000510 noble metal Inorganic materials 0.000 description 5
- 229910052697 platinum Inorganic materials 0.000 description 5
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 238000006555 catalytic reaction Methods 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000005100 correlation spectroscopy Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- KCNZJZJZHUZEKI-UHFFFAOYSA-N CCOC(CCCCCCCCCCCC1CCCCC1)(OCC)OCC Chemical compound CCOC(CCCCCCCCCCCC1CCCCC1)(OCC)OCC KCNZJZJZHUZEKI-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000000412 dendrimer Substances 0.000 description 3
- 229920000736 dendritic polymer Polymers 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- JFJNVIPVOCESGZ-UHFFFAOYSA-N 2,3-dipyridin-2-ylpyridine Chemical class N1=CC=CC=C1C1=CC=CN=C1C1=CC=CC=N1 JFJNVIPVOCESGZ-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 229910000071 diazene Inorganic materials 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000005096 rolling process Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 description 1
- CWZQYRJRRHYJOI-UHFFFAOYSA-N 1,1,1-trimethoxydecane Chemical compound CCCCCCCCCC(OC)(OC)OC CWZQYRJRRHYJOI-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- UYVWNPAMKCDKRB-UHFFFAOYSA-N 1,2,4,5-tetraoxane Chemical compound C1OOCOO1 UYVWNPAMKCDKRB-UHFFFAOYSA-N 0.000 description 1
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 description 1
- 239000004912 1,5-cyclooctadiene Substances 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- UYSWTFXPYLWMJS-UHFFFAOYSA-N 2,3-bis(ethenyl)-2,3,5,6-tetramethyl-1,4-dioxane Chemical compound C(=C)C1(C(OC(C(O1)C)C)(C)C=C)C UYSWTFXPYLWMJS-UHFFFAOYSA-N 0.000 description 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 description 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 238000005084 2D-nuclear magnetic resonance Methods 0.000 description 1
- KUZXQXCWRNFIHK-UHFFFAOYSA-N 3,3-diethyldodecane Chemical compound CCCCCCCCCC(CC)(CC)CC KUZXQXCWRNFIHK-UHFFFAOYSA-N 0.000 description 1
- JURLNXPXCMWCHE-UHFFFAOYSA-N 3-ethylidenebicyclo[2.2.1]heptane Chemical compound C1CC2C(=CC)CC1C2 JURLNXPXCMWCHE-UHFFFAOYSA-N 0.000 description 1
- JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-UHFFFAOYSA-N 0.000 description 1
- 229910000619 316 stainless steel Inorganic materials 0.000 description 1
- IHVIGMIHTWLYKV-UHFFFAOYSA-N CC(CCCCCCCCC)(OCCCCCCCCCC(C)(C)C)OCCCCCCCCCC(C)(C)C Chemical compound CC(CCCCCCCCC)(OCCCCCCCCCC(C)(C)C)OCCCCCCCCCC(C)(C)C IHVIGMIHTWLYKV-UHFFFAOYSA-N 0.000 description 1
- YCPDVLQCRQRPPP-UHFFFAOYSA-N CC(CCCCCCCCCOC(OCCCCCCCCCC(C)(C)C)CCCCCCCCCC)(C)C Chemical compound CC(CCCCCCCCCOC(OCCCCCCCCCC(C)(C)C)CCCCCCCCCC)(C)C YCPDVLQCRQRPPP-UHFFFAOYSA-N 0.000 description 1
- ILOVHYKVLKBGKC-UHFFFAOYSA-N CCOC(CCCCCCCCCCCC(C)C1CCCCC1(C=C)C=C)(OCC)OCC Chemical compound CCOC(CCCCCCCCCCCC(C)C1CCCCC1(C=C)C=C)(OCC)OCC ILOVHYKVLKBGKC-UHFFFAOYSA-N 0.000 description 1
- HASIXQULGZYHTA-UHFFFAOYSA-N CCOC(CCCCCCCCCCCC1CCCCC1(C=C)C=C)(OCC)OCC Chemical compound CCOC(CCCCCCCCCCCC1CCCCC1(C=C)C=C)(OCC)OCC HASIXQULGZYHTA-UHFFFAOYSA-N 0.000 description 1
- 101150065749 Churc1 gene Proteins 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 1
- 229910003849 O-Si Inorganic materials 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910003872 O—Si Inorganic materials 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
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- 102100038239 Protein Churchill Human genes 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
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- 229920006362 Teflon® Polymers 0.000 description 1
- CRQCDBGUBUAJJG-UHFFFAOYSA-N [Fe].NC1=CC=CC=N1 Chemical class [Fe].NC1=CC=CC=N1 CRQCDBGUBUAJJG-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
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- 125000001118 alkylidene group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000000998 batch distillation Methods 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 229910000420 cerium oxide Inorganic materials 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
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- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- LMGZGXSXHCMSAA-UHFFFAOYSA-N cyclodecane Chemical class C1CCCCCCCCC1 LMGZGXSXHCMSAA-UHFFFAOYSA-N 0.000 description 1
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 150000002012 dioxanes Chemical class 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005485 electric heating Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- LDLDYFCCDKENPD-UHFFFAOYSA-N ethenylcyclohexane Chemical compound C=CC1CCCCC1 LDLDYFCCDKENPD-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- HDLAKZKIMOHJAH-UHFFFAOYSA-N iron(2+);pyridine Chemical compound [Fe+2].C1=CC=NC=C1 HDLAKZKIMOHJAH-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000000463 material Substances 0.000 description 1
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- 238000002156 mixing Methods 0.000 description 1
- 238000012544 monitoring process Methods 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
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 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
- 239000010412 oxide-supported catalyst Substances 0.000 description 1
- 238000006146 oximation reaction Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000004886 process control Methods 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000007152 ring opening metathesis polymerisation reaction Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 1
- IZLSCNBYGCFOFH-UHFFFAOYSA-N ruthenium trihydride Chemical group [RuH3] IZLSCNBYGCFOFH-UHFFFAOYSA-N 0.000 description 1
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 150000004901 trioxanes Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B61/00—Other general methods
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/02—Iron compounds
- C07F15/025—Iron compounds without a metal-carbon linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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| US41706110P | 2010-11-24 | 2010-11-24 |
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| EP2643335B1 (en) * | 2010-11-24 | 2015-03-11 | Momentive Performance Materials Inc. | Hydrosilylation catalyst |
| JP6101695B2 (ja) | 2011-09-20 | 2017-03-22 | ダウ コーニング コーポレーションＤｏｗ Ｃｏｒｎｉｎｇ Ｃｏｒｐｏｒａｔｉｏｎ | ニッケル含有ヒドロシリル化触媒及びその触媒を含有する組成物 |
| WO2013081794A1 (en) | 2011-12-01 | 2013-06-06 | Dow Corning Corporation | Hydrosilylation reaction catalysts and curable compositions and methods for their preparation and use |
| US9782763B2 (en) | 2011-12-14 | 2017-10-10 | Momentive Performance Materials Inc. | Non-precious metal-based hyrdosilylation catalysts exhibiting improved selectivity |
| US9371340B2 (en) | 2012-08-16 | 2016-06-21 | Momentive Performance Materials Inc. | Dehydrogenative silylation, hydrosilylation and crosslinking using cobalt catalysts |
| 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 |
| 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 |
| WO2014186513A1 (en) | 2013-05-15 | 2014-11-20 | Momentive Performance Materials Inc. | Activation of metal salts with silylhydrides and their use in hydrosilylation reactions |
| JP6486925B2 (ja) | 2013-11-19 | 2019-03-20 | 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 | 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 |
| WO2015077344A1 (en) | 2013-11-19 | 2015-05-28 | The Trustees Of Princeton University | Hydroboration and borylation with cobalt catalysts |
| JP6486924B2 (ja) * | 2013-11-19 | 2019-03-20 | 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 | 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 |
| WO2015171881A1 (en) * | 2014-05-08 | 2015-11-12 | Momentive Performance Materials Inc. | Dialkyl cobalt catalysts and their use for hydrosilylation and dehydrogenative silylation |
| JP2015231965A (ja) * | 2014-06-10 | 2015-12-24 | 国立研究開発法人産業技術総合研究所 | 有機ケイ素化合物の製造方法及び触媒組成物 |
| EP3195932B1 (en) | 2014-08-12 | 2024-08-21 | Kyushu University, National University Corporation | Hydrosilylation reaction catalyst |
| EP3181226B1 (en) | 2014-08-12 | 2024-08-07 | Kyushu University, National University Corporation | Hydrosilylation reaction catalyst |
| JP6761997B2 (ja) | 2014-08-19 | 2020-09-30 | 国立大学法人九州大学 | ヒドロシリル化鉄触媒 |
| US20180200703A1 (en) | 2015-07-14 | 2018-07-19 | Kyushu University, National University Corporation | Hydrosilylation reaction catalyst |
| JP6846423B2 (ja) * | 2015-07-24 | 2021-03-24 | 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Ｍｏｍｅｎｔｉｖｅ Ｐｅｒｆｏｒｍａｎｃｅ Ｍａｔｅｒｉａｌｓ Ｉｎｃ． | ピリジンジイミンコバルトカルボキシレート触媒を用いた脱水素シリル化、ヒドロシリル化および架橋 |
| KR101728308B1 (ko) | 2015-09-14 | 2017-04-19 | 기초과학연구원 | 비전이금속 촉매법 수소규소화 반응을 이용한 규소 고분자 제조방법 |
| CN108473514B (zh) | 2016-01-22 | 2021-08-31 | 信越化学工业株式会社 | 新型异腈化合物和氢化硅烷化反应催化剂 |
| WO2018159595A1 (ja) | 2017-02-28 | 2018-09-07 | 国立大学法人九州大学 | ヒドロシリル化反応、水素化反応およびヒドロシラン還元反応用触媒 |
| JP2019064950A (ja) | 2017-09-29 | 2019-04-25 | 国立大学法人九州大学 | コバルト錯体、その製造方法およびヒドロシリル化反応用触媒 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200902541A (en) * | 2006-12-28 | 2009-01-16 | Momentive Performance Mat Inc | Silated core polysulfides, their preparation and use in filled elastomer compositions |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US5691435A (en) * | 1996-01-25 | 1997-11-25 | Wacker-Chemie Gmbh | Crosslinkable compositions |
| US5756795A (en) * | 1996-12-30 | 1998-05-26 | Dow Corning Corporation | Unsaturated accelerators for hydrosilation |
| US5986022A (en) * | 1998-04-01 | 1999-11-16 | Witco Corporation | Continuous manufacture of silicone coploymers |
| 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 |
| US6278011B1 (en) | 1999-08-30 | 2001-08-21 | The University Of Dayton | Polysilahydrocarbons as lubricants for aerospace application |
| US7429672B2 (en) | 2006-06-09 | 2008-09-30 | Momentive Performance Materials Inc. | Process for the direct synthesis of trialkoxysilane |
| US8236915B2 (en) | 2009-07-10 | 2012-08-07 | Momentive Performance Materials Inc. | Hydrosilylation catalysts |
| US8415443B2 (en) * | 2009-07-10 | 2013-04-09 | Momentive Performance Materials Inc. | Hydrosilylation catalysts |
| WO2012071358A2 (en) * | 2010-11-24 | 2012-05-31 | Momentive Performance Materials Inc. | In-situ activation of metal complexes containing terdentate nitrogen ligands used as hydrosilylation catalysts |
-
2011
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- 2011-11-22 KR KR1020137016391A patent/KR101896423B1/ko active Active
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200902541A (en) * | 2006-12-28 | 2009-01-16 | Momentive Performance Mat Inc | Silated core polysulfides, their preparation and use in filled elastomer compositions |
Non-Patent Citations (2)
| Title |
|---|
| Andrew M. Archer，Marco W. Bouwkamp，Maria-Patricia Cortez，Emil Lobkovsky，and Paul J. Chirik，Arene Coordination in Bis(imino)pyridine Iron Complexes: Identification of Catalyst Deactivation Pathways in Iron-Catalyzed Hydrogenation and Hydrosilation，Organometallics，2006，25(18)，4269–4278 * |
| Suzanne C. Bart，Emil Lobkovsky，and Paul J. Chirik，Preparation and Molecular and Electronic Structures of Iron(0) Dinitrogen and Silane Complexes and Their Application to Catalytic Hydrogenation and Hydrosilation，J. Am. Chem. Soc., 2004, 126 (42), 13794–13807 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN103732599B (zh) | 2016-09-14 |
| CN103732599A (zh) | 2014-04-16 |
| BR112013012734A2 (pt) | 2016-09-13 |
| WO2012071360A1 (en) | 2012-05-31 |
| US20120130105A1 (en) | 2012-05-24 |
| KR101896423B1 (ko) | 2018-10-04 |
| JP6019034B2 (ja) | 2016-11-02 |
| US8895770B2 (en) | 2014-11-25 |
| KR20140035318A (ko) | 2014-03-21 |
| JP2014502271A (ja) | 2014-01-30 |
| EP2643330A1 (en) | 2013-10-02 |
| EP2643330B1 (en) | 2017-01-04 |
| TW201235102A (en) | 2012-09-01 |
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