JP2018504426A - オルガノハロシランを作製する方法 - Google Patents
オルガノハロシランを作製する方法 Download PDFInfo
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- JP2018504426A JP2018504426A JP2017541047A JP2017541047A JP2018504426A JP 2018504426 A JP2018504426 A JP 2018504426A JP 2017541047 A JP2017541047 A JP 2017541047A JP 2017541047 A JP2017541047 A JP 2017541047A JP 2018504426 A JP2018504426 A JP 2018504426A
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- Japan
- Prior art keywords
- catalyst
- formula
- silane
- hydridohalosilanes
- chloro
- 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.)
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- 238000000034 method Methods 0.000 title claims description 63
- 239000003054 catalyst Substances 0.000 claims abstract description 87
- 239000002638 heterogeneous catalyst Substances 0.000 claims abstract description 46
- 239000000203 mixture Substances 0.000 claims abstract description 42
- 229910052796 boron Inorganic materials 0.000 claims abstract description 39
- 229910052719 titanium Inorganic materials 0.000 claims abstract description 28
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 27
- 229910052726 zirconium Inorganic materials 0.000 claims abstract description 27
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 25
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 24
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 24
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 20
- 229910052727 yttrium Inorganic materials 0.000 claims abstract description 18
- 229910052706 scandium Inorganic materials 0.000 claims abstract description 17
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 16
- 229910052732 germanium Inorganic materials 0.000 claims abstract description 15
- 229910052733 gallium Inorganic materials 0.000 claims abstract description 14
- 229910052735 hafnium Inorganic materials 0.000 claims abstract description 14
- 229910052738 indium Inorganic materials 0.000 claims abstract description 14
- 229910052718 tin Inorganic materials 0.000 claims abstract description 14
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 12
- 150000001491 aromatic compounds Chemical class 0.000 claims abstract description 11
- 125000001246 bromo group Chemical group Br* 0.000 claims abstract description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 6
- 125000002346 iodo group Chemical group I* 0.000 claims abstract description 6
- 229910052758 niobium Inorganic materials 0.000 claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 39
- 238000006243 chemical reaction Methods 0.000 claims description 36
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 21
- 239000002131 composite material Substances 0.000 claims description 13
- MROCJMGDEKINLD-UHFFFAOYSA-N dichlorosilane Chemical compound Cl[SiH2]Cl MROCJMGDEKINLD-UHFFFAOYSA-N 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims description 7
- 229910001928 zirconium oxide Inorganic materials 0.000 claims description 7
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- NWKBSEBOBPHMKL-UHFFFAOYSA-N dichloro(methyl)silane Chemical compound C[SiH](Cl)Cl NWKBSEBOBPHMKL-UHFFFAOYSA-N 0.000 claims description 5
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 150000005171 halobenzenes Chemical class 0.000 claims 1
- 229910052745 lead Inorganic materials 0.000 abstract description 9
- -1 boron halide Chemical class 0.000 description 23
- 125000004432 carbon atom Chemical group C* 0.000 description 13
- 238000001165 gas chromatography-thermal conductivity detection Methods 0.000 description 12
- 239000011521 glass Substances 0.000 description 11
- UIUXUFNYAYAMOE-UHFFFAOYSA-N methylsilane Chemical compound [SiH3]C UIUXUFNYAYAMOE-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- 239000011230 binding agent Substances 0.000 description 8
- KTQYJQFGNYHXMB-UHFFFAOYSA-N dichloro(methyl)silicon Chemical compound C[Si](Cl)Cl KTQYJQFGNYHXMB-UHFFFAOYSA-N 0.000 description 8
- 239000005048 methyldichlorosilane Substances 0.000 description 8
- 239000000376 reactant Substances 0.000 description 8
- 229910000077 silane Inorganic materials 0.000 description 8
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 7
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 7
- 239000005052 trichlorosilane Substances 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 229910044991 metal oxide Inorganic materials 0.000 description 6
- 150000004706 metal oxides Chemical class 0.000 description 6
- 238000010306 acid treatment Methods 0.000 description 5
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 229920001971 elastomer Polymers 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000002815 homogeneous catalyst Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000005046 Chlorosilane Substances 0.000 description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 238000010923 batch production Methods 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000010924 continuous production Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 125000003963 dichloro group Chemical group Cl* 0.000 description 3
- 125000003438 dodecyl 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])C([H])([H])C([H])([H])* 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical compound CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000002015 acyclic group Chemical group 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 2
- 229940063655 aluminum stearate Drugs 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-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
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 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 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- BYLOHCRAPOSXLY-UHFFFAOYSA-N dichloro(diethyl)silane Chemical compound CC[Si](Cl)(Cl)CC BYLOHCRAPOSXLY-UHFFFAOYSA-N 0.000 description 2
- OSXYHAQZDCICNX-UHFFFAOYSA-N dichloro(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](Cl)(Cl)C1=CC=CC=C1 OSXYHAQZDCICNX-UHFFFAOYSA-N 0.000 description 2
- XNAFLNBULDHNJS-UHFFFAOYSA-N dichloro(phenyl)silicon Chemical compound Cl[Si](Cl)C1=CC=CC=C1 XNAFLNBULDHNJS-UHFFFAOYSA-N 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 229910002804 graphite Inorganic materials 0.000 description 2
- 239000010439 graphite Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical compound CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000004570 mortar (masonry) Substances 0.000 description 2
- 125000001421 myristyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000001400 nonyl 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])C([H])([H])[H] 0.000 description 2
- 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 2
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000005054 phenyltrichlorosilane Substances 0.000 description 2
- 239000002574 poison Substances 0.000 description 2
- 231100000614 poison Toxicity 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000011027 product recovery Methods 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- 125000002889 tridecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002948 undecyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000005023 xylyl group Chemical group 0.000 description 2
- XWBAPVJGJUDSNR-UHFFFAOYSA-N (3-chlorophenyl)-methylsilane Chemical compound C[SiH2]C1=CC(=CC=C1)Cl XWBAPVJGJUDSNR-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- ZMYIIHDQURVDRB-UHFFFAOYSA-N 1-phenylethenylbenzene Chemical compound C=1C=CC=CC=1C(=C)C1=CC=CC=C1 ZMYIIHDQURVDRB-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000005047 Allyltrichlorosilane Substances 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- CPJPRNWZMGHXQH-UHFFFAOYSA-N C(CCCCCCCCCCCCC)[SiH](Cl)Cl.C(CCCCCCCCCCCCC)[SiH2]Cl Chemical compound C(CCCCCCCCCCCCC)[SiH](Cl)Cl.C(CCCCCCCCCCCCC)[SiH2]Cl CPJPRNWZMGHXQH-UHFFFAOYSA-N 0.000 description 1
- PTKGGTHLFXGPQY-UHFFFAOYSA-N CC1CC(CCC1)[Si](Cl)(C1CC(CCC1)C)C1CC(CCC1)C Chemical compound CC1CC(CCC1)[Si](Cl)(C1CC(CCC1)C)C1CC(CCC1)C PTKGGTHLFXGPQY-UHFFFAOYSA-N 0.000 description 1
- UTYFCZAESSHHRP-UHFFFAOYSA-N CCCCCCCCCC[SiH](Cl)Cl Chemical compound CCCCCCCCCC[SiH](Cl)Cl UTYFCZAESSHHRP-UHFFFAOYSA-N 0.000 description 1
- DMAWHHOICGGPQF-UHFFFAOYSA-N CCCCCC[SiH2]Cl Chemical compound CCCCCC[SiH2]Cl DMAWHHOICGGPQF-UHFFFAOYSA-N 0.000 description 1
- CMAAFULQXXJAHH-UHFFFAOYSA-N C[SiH3].ClC(=CCl)Cl Chemical compound C[SiH3].ClC(=CCl)Cl CMAAFULQXXJAHH-UHFFFAOYSA-N 0.000 description 1
- GUVCMDRCCGKQOH-UHFFFAOYSA-N C[SiH3].ClC(C=C)(Cl)Cl Chemical compound C[SiH3].ClC(C=C)(Cl)Cl GUVCMDRCCGKQOH-UHFFFAOYSA-N 0.000 description 1
- GAJGSWZJVIOXTD-UHFFFAOYSA-N C[SiH3].ClC1=C(CCCC1)Cl Chemical compound C[SiH3].ClC1=C(CCCC1)Cl GAJGSWZJVIOXTD-UHFFFAOYSA-N 0.000 description 1
- ZGPGYFHDRWHILH-UHFFFAOYSA-N C[SiH3].ClC1=C(CCCC1C)Cl Chemical compound C[SiH3].ClC1=C(CCCC1C)Cl ZGPGYFHDRWHILH-UHFFFAOYSA-N 0.000 description 1
- HURKMZVOLCJNDL-UHFFFAOYSA-N C[SiH3].ClC1=C(CCCC1Cl)Cl Chemical compound C[SiH3].ClC1=C(CCCC1Cl)Cl HURKMZVOLCJNDL-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- YGTZIYQAZNIRRT-UHFFFAOYSA-N ClC(CCCCCCCCCCC[Si](CCCCCCCCCCCC)(CCCCCCCCCCCC)CCCCCCCCCCCC)(Cl)Cl Chemical compound ClC(CCCCCCCCCCC[Si](CCCCCCCCCCCC)(CCCCCCCCCCCC)CCCCCCCCCCCC)(Cl)Cl YGTZIYQAZNIRRT-UHFFFAOYSA-N 0.000 description 1
- RJJSMCCHJOBYNZ-UHFFFAOYSA-N ClC1CC(CCC1)[Si](Cl)(C1CC(CCC1)Cl)C1CC(CCC1)Cl Chemical compound ClC1CC(CCC1)[Si](Cl)(C1CC(CCC1)Cl)C1CC(CCC1)Cl RJJSMCCHJOBYNZ-UHFFFAOYSA-N 0.000 description 1
- QUBVGNMQTIREOX-UHFFFAOYSA-N ClC1CC(CCC1)[Si](Cl)(Cl)C1CC(CCC1)Cl Chemical compound ClC1CC(CCC1)[Si](Cl)(Cl)C1CC(CCC1)Cl QUBVGNMQTIREOX-UHFFFAOYSA-N 0.000 description 1
- LCDAEFFPUFPIQB-UHFFFAOYSA-N ClC=1C=C(C=CC=1)[Si](Cl)(C1=CC(=CC=C1)Cl)C1=CC(=CC=C1)Cl Chemical compound ClC=1C=C(C=CC=1)[Si](Cl)(C1=CC(=CC=C1)Cl)C1=CC(=CC=C1)Cl LCDAEFFPUFPIQB-UHFFFAOYSA-N 0.000 description 1
- BORGVFJXGIVVRE-UHFFFAOYSA-N ClCCCC[Si](Cl)(CCCCCl)CCCCCl Chemical compound ClCCCC[Si](Cl)(CCCCCl)CCCCCl BORGVFJXGIVVRE-UHFFFAOYSA-N 0.000 description 1
- IACMWGGGELJMMX-UHFFFAOYSA-N ClCCC[Si](Cl)(CCCCl)CCCCl Chemical compound ClCCC[Si](Cl)(CCCCl)CCCCl IACMWGGGELJMMX-UHFFFAOYSA-N 0.000 description 1
- MPEYLSOUQJBMQC-UHFFFAOYSA-N ClCC[Si](Cl)(CCCl)CCCl Chemical compound ClCC[Si](Cl)(CCCl)CCCl MPEYLSOUQJBMQC-UHFFFAOYSA-N 0.000 description 1
- KCXASDLRNRSEAG-UHFFFAOYSA-N Cl[SiH2]Cl.CCC=C.CCC=C Chemical compound Cl[SiH2]Cl.CCC=C.CCC=C KCXASDLRNRSEAG-UHFFFAOYSA-N 0.000 description 1
- WIJNYKQVIAWWOU-UHFFFAOYSA-N Cl[SiH](C)C1=C(C(=C(C(=C1)Cl)Cl)C)C Chemical compound Cl[SiH](C)C1=C(C(=C(C(=C1)Cl)Cl)C)C WIJNYKQVIAWWOU-UHFFFAOYSA-N 0.000 description 1
- SHAUDEPFKBUFLP-UHFFFAOYSA-N Cl[SiH](C)C1=C(C=CC(=C1Cl)Cl)C Chemical compound Cl[SiH](C)C1=C(C=CC(=C1Cl)Cl)C SHAUDEPFKBUFLP-UHFFFAOYSA-N 0.000 description 1
- DYESBLCNVOBYNO-UHFFFAOYSA-N Cl[SiH](C)Cl.CCC=C Chemical compound Cl[SiH](C)Cl.CCC=C DYESBLCNVOBYNO-UHFFFAOYSA-N 0.000 description 1
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- ZJNIAINGCAHDNZ-UHFFFAOYSA-N Cl[Si](C)(C1=C(C=CC=C1Cl)C)Cl Chemical compound Cl[Si](C)(C1=C(C=CC=C1Cl)C)Cl ZJNIAINGCAHDNZ-UHFFFAOYSA-N 0.000 description 1
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- QAIIYJIIIQZBHN-UHFFFAOYSA-N trichloro-(2-methylphenyl)silane Chemical compound CC1=CC=CC=C1[Si](Cl)(Cl)Cl QAIIYJIIIQZBHN-UHFFFAOYSA-N 0.000 description 1
- ZIILLBRFKOKOGU-UHFFFAOYSA-N trichloro-(3-chlorophenyl)silane Chemical compound ClC1=CC=CC([Si](Cl)(Cl)Cl)=C1 ZIILLBRFKOKOGU-UHFFFAOYSA-N 0.000 description 1
- SDBZAKGEKGKDKR-UHFFFAOYSA-N trichloro-(4-chloronaphthalen-1-yl)silane Chemical compound C1=CC=C2C(Cl)=CC=C([Si](Cl)(Cl)Cl)C2=C1 SDBZAKGEKGKDKR-UHFFFAOYSA-N 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- 238000002424 x-ray crystallography Methods 0.000 description 1
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Abstract
Description
ジフェニルジクロロシラン、ジナフチルジクロロシラン、ビス−(3−クロロフェニル)ジクロロシラン、ビス−(4−クロロナフチル)ジクロロシラン、クロロ(トリメチル)シラン、クロロ(トリエチル)シラン、クロロ(トリプロピル)シラン、クロロ(トリブチル)シラン、クロロ(トリペンチル)シラン、クロロ(トリヘキシル)シラン、クロロ(トリヘプチル)シラン、クロロ(トリオクチル)シラン、クロロ(トリノニル)シラン、クロロ(トリドデシル)シラン、クロロ(トリテトラドデシル)シラン、トリス(クロロメチル)クロロシラン、トリス(2−クロロエチル)クロロシラン、トリス(3−クロロプロピル)クロロシラン、トリス(4−クロロブチル)クロロシラン、(トリシクロヘキシル)クロロシラン、トリス(3−メチルシクロヘキシル)クロロシラン、トリス(3−クロロシクロヘキシル)クロロシラン、クロロ(トリフェニル)シラン、トリス(3−クロロフェニル)クロロシラン、クロロ(トリナフチル)シラン、クロロ(トリ)シラン、クロロ(トリ)シラン、クロロ(トリ)シラン、クロロ(トリ)シラン、クロロ(ジエチル)メチルシラン、クロロ(メチル)ジプロピルシラン、クロロ(ジブチル)メチルシラン、クロロ(メチル)ジペンチルシラン、クロロ(メチル)ジオクチルシラン、クロロ(ジテトラドデシル)メチルシラン、クロロ(ビス−クロロメチル)メチルシラン、クロロ(ビス−2−クロロエチル)メチルシラン、クロロ(ビス−3−クロロプロピル)メチルシラン、クロロ(ビス−4−クロロブチル)メチルシラン、クロロ(シクロヘキシル)メチルシラン、クロロ(ビス−3−クロロシクロヘキシル)メチルシラン、クロロ(ジフェニル)メチルシラン、クロロ(ジナフチル)メチルシラン、クロロ(ジキシリル)メチルシランクロロ(ジ−m−クロロフェニル)メチルシラン、クロロ(ビス−4−クロロナフチル)メチルシラン、クロロ(ジクロロトリル)メチルシラン、クロロ(ジクロロキシリル)メチルシランが挙げられるが、これらに限定されない。
1.91gのH3BO3(乳鉢及び乳棒で予め粉砕したもの)を6.83gのグリセロールとともに磁製皿に加え、均一なペーストが得られるまでスパチュラで攪拌した(5〜10分)。次いで、65.63gのAl(NO3)3・9H2O(乳鉢及び乳棒で予め粉砕したもの)を加え、混合物を数分間攪拌した。4.08gの脱イオン水を加え、均一なペーストが得られるまで攪拌した。次いで、皿をホットプレート上で加熱し、90℃まで加熱すると、その時点で黄色の蒸気(硝酸塩)が観察された。加熱を2時間継続して、水及び硝酸塩を除去した。次いで、150℃の空気循環オーブン中に皿を2時間置いた。オーブンから取り出すと、材料は、ふっくらした黄色の固体であった。次いで、400℃の空気循環オーブン中に皿を一晩置いた。得られた触媒は、15%(w/w)ボリア及び85%(w/w)アルミナであった。実施例に記載のボリアとアルミナの比率をもたらすように試薬の量を変更した点を除き、同じ方法を使用して、アルミナ及びボリアを含む他の触媒を調製した。
TCD検出器並びに内径0.25mm及び膜厚0.50μmを有する30mのDB−210カラムを備えたHP5890及びHP6890ガスクロマトグラフ(GC製)を使用して分析を実施した。
反応混合物はすべてN2パージしたグローブバッグ中で調製した。触媒サンプルは、流動N2中、300〜400℃で一晩乾燥させることによって調製した。触媒サンプルを、温かい状態のままN2パージ下でバイアル瓶に移し、密封した。次いで、触媒を入れたバイアル瓶を、N2パージしたグローブバッグ中のデシケータに移した。触媒を移すためのバイアル瓶は、使用前に、150℃の空気循環オーブン中で一晩乾燥し、使用直前にオーブンから取り出した。
N2パージしたグローブバッグ中で、一端を密封したガラス管中に触媒及び反応混合物を充填し、ゴム製セプタムを使用して一時的に密封した。管は、液体であれば、触媒及び反応物質の重量を基準にして1%(w/w)の触媒を含み、固体であれば、一定の目に見える量(触媒及び反応物質の重量を基準にして約1%(w/w))を含んだ。次いで、充填しゴム製セプタムで密封した管をグローブバッグから取り出し、ゴム栓の下の開放端をガラストーチで密封した。次いで、反応物質及び触媒を入れた密封ガラス管を金属加熱ブロック中で所定の温度及び時間で加熱して反応を実施した。管を加熱ブロックから取り出したら、最初に室温で、次いでドライアイス/アセトン浴中で冷却した。冷却中に管を割り、反応混合物が完全に解けるまで、ゴム製セプタムで一時的に密封した。解凍したら、ガラス管反応器から反応生成物を分析用バイアル瓶に移した。
ベンゼン及びメチルジクロロシランをモル比2:1で含有する混合物を、CS331−4アルミナ触媒をそれぞれ含む一連のガラス管中に入れ、管を密封した。管を、275℃まで、推定内圧10MPa(1500psi)で、以下の表1に記載の時間、加熱した。指定時間で管を冷却し、内容物をGC−TCDによって分析した。結果をGC−TCD分析で定義された曲線下面積パーセントとして示す。
ベンゼン及びメチルジクロロシランをモル比2:1で含有する混合物を、CS331−5アルミナ触媒をそれぞれ含む一連のガラス管中に入れ、管を密封した。管を、175℃まで、推定内圧10MPa(1500psi)で、以下の表2に記載の時間、加熱した。指定時間で管を冷却し、内容物をGC−TCDによって分析した。結果をGC−TCD分析で定義された曲線下面積パーセントとして示す。
ベンゼン及びメチルジクロロシランをモル比2:1で含有する混合物を、高多孔性酸化ジルコニウム(XZO1501/23)触媒をそれぞれ含む一連のガラス管中に入れ、管を密封した。管を、250℃まで、推定内圧10MPa(1500psi)で、以下の表3に記載の時間、加熱した。指定時間で管を冷却し、内容物をGC−TCDによって分析した。結果をGC−TCD分析で定義された曲線下面積パーセントとして示す。
ガラス管中でのベンゼンとMeHSiCl2の反応に、触媒としてγ−アルミナのサンプルを使用した。モル比2:1のベンゼン:MeHSiCl2を使用して、反応を250℃で16時間実施した。反応に使用した触媒は、反応前の触媒処理に関して異なった。2つの触媒サンプルは酸処理なしで乾燥させ、2つのサンプルは酸処理を加えて乾燥させた。酸処理なしで乾燥させた金属酸化物触媒サンプルは、流動He中、300〜325℃で一晩(〜16時間)乾燥させた。酸処理を加えて乾燥させた金属酸化物触媒は、最初にHeと無水HClの50/50流動混合物中、300〜325℃で4〜5時間乾燥させ、次いで、流動He中、300〜325℃で一晩(〜16時間)乾燥させた。2つの処理法による反応結果を以下の表4に示す。すべての反応パラメーターは、反応における触媒として使用する前に触媒を処理した以外、同じであった。結果は、ベンゼンとMeHSiCl2の反応における触媒として使用する前に、乾燥と組み合わせて触媒を酸処理することにより、乾燥のみと比較して、PhMeSiCl2の収率が改善することを示している。
ベンゼン及びメチルジクロロシランをモル比2:1で含有する混合物を、高多孔性酸化ジルコニウム(XZO1501/23)触媒をそれぞれ含む一連のガラス管中に入れ、管を密封した。管を、250℃まで、推定内圧10MPa(1500psi)で、表CE1に記載の時間、加熱した。指定時間で管を冷却し、内容物をGC−TCDによって分析した。結果をGC−TCD分析で定義された曲線下面積パーセントとして示す。
ベンゼン及びメチルジクロロシランをモル比2:1で含有する混合物を、CS331−4アルミナ触媒をそれぞれ含む一連のガラス管中に入れ、管を密封した。管を、250℃まで、推定内圧10MPa(1500psi)で、表CE2に記載の時間、加熱した。指定時間で管を冷却し、内容物をGC−TCDによって分析した。結果をGC−TCD分析で定義された曲線下面積パーセントとして示す。
Claims (16)
- オルガノハロシランを作製するための方法であって、ハロゲン置換又は非置換の芳香族化合物を含む有機化合物を、式(I)RnSiHmX4−m−n(式中、各Rは、独立して、C1−C14ヒドロカルビル又はC1−C14ハロゲン置換ヒドロカルビルであり、Xは、フルオロ、クロロ、ブロモ又はヨードであり、nは、0、1又は2であり、mは、1、2又は3であり、m+nは、1、2又は3である。)の少なくとも2種の異なるヒドリドハロシランを含むヒドリドハロシラン混合物と、元素Sc、Y、Ti、Zr、Hf、Nb、B、Al、Ga、In、C、Si、Ge、Sn又はPbのうち1つ以上を含む触媒の存在下、100℃を超える温度及び少なくとも690kPaの圧力で反応させて、前記オルガノハロシランを含む粗反応生成物を作製することを含み、
ただし、前記少なくとも2種の異なるヒドリドハロシランが、n=0及びm=1である式(I)のヒドリドハロシランと、n=0及びm=2である式(I)のヒドリドハロシランとを含む場合、前記触媒は、元素Sc、Y、Ti、Zr、Hf、B、Al、Ga、In、C、Si、Ge、Sn又はPbのうち1つ以上の酸化物を含む不均一系触媒である、方法。 - 前記触媒が前記不均一系触媒である、請求項1に記載の方法。
- 前記不均一系触媒が、アルミナ、酸化ジルコニウム、又は元素Sc、Y、Ti、Zr、Hf、B、Al、Ga、In、C、Si、Ge、Sn若しくはPbのうち2つ以上の酸化物を含む、請求項2に記載の方法。
- 前記不均一系触媒が、γ−アルミナ、Alと元素B、Zr、Ti若しくはSiのうち1つとを含む複合酸化物、又はZrと元素B、Ti若しくはSiのうちの1つとを含む複合酸化物を含む、請求項3に記載の方法。
- 前記不均一系触媒が、γ−アルミナ、Zr及びBを含む複合酸化物、又はAl及びBを含む複合酸化物を含む、請求項4に記載の方法。
- 前記触媒が式Al9B2O15又はAl4B2O9を有する、請求項1〜5のいずれか一項に記載の方法。
- 前記触媒が前記不均一系触媒であり、前記不均一系触媒が前記反応の前に酸で処理される、請求項1〜6のいずれか一項に記載の方法。
- 前記触媒が式BaZb、NbZ5又はAlZ3を有し、式中、Zは、H、Cl、アルキル又はアリールであり、aは、1又は2であり、bは、3又は6である、請求項1に記載の方法。
- 前記触媒が式PhBCl2、BPh3、B2H6、BCl3、NbCl5又はAlCl3を有する、請求項8に記載の方法。
- 前記触媒が式BCl3、NbCl5又はAlCl3を有する、請求項9に記載の方法。
- 前記オルガノハロシランが、式R’eRfSiHgX4−e−f−g(各R’は、独立して、C1−C14置換又は非置換のアリール又はアルカリルであり、eは、1又は2であり、fは、0、1又は2であり、gは、0、1又は2であり、e+f+g=1、2又は3である。)のものである、請求項1〜10のいずれか一項に記載の方法。
- 前記有機化合物がベンゼン、トルエン、ハロベンゼン、ジハロベンゼン又はナフタレンを含む、請求項1〜11のいずれか一項に記載の方法。
- 前記有機化合物がベンゼンである、請求項1〜12のいずれか一項に記載の方法。
- 前記少なくとも2種のヒドリドハロシランのうち1つに関して、mが0であり、nが1又は2である、請求項1〜13のいずれか一項に記載の方法。
- 前記少なくとも2種のヒドリドハロシランのうち1つに関して、m=0であり、n=1、2又は3である、請求項1〜14のいずれか一項に記載の方法。
- 前記ヒドリドハロシラン混合物がジクロロ(メチル)シラン及びジクロロシランを含む、請求項1〜15のいずれか一項に記載の方法。
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CN107223127B (zh) | 2020-09-11 |
EP3253770A4 (en) | 2018-08-22 |
US20170369514A1 (en) | 2017-12-28 |
US9908903B2 (en) | 2018-03-06 |
CN107223127A (zh) | 2017-09-29 |
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