KR100928942B1 - 직선형이나 고리형의 트리실라알칸의 제조방법 - Google Patents
직선형이나 고리형의 트리실라알칸의 제조방법 Download PDFInfo
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- KR100928942B1 KR100928942B1 KR1020080048681A KR20080048681A KR100928942B1 KR 100928942 B1 KR100928942 B1 KR 100928942B1 KR 1020080048681 A KR1020080048681 A KR 1020080048681A KR 20080048681 A KR20080048681 A KR 20080048681A KR 100928942 B1 KR100928942 B1 KR 100928942B1
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- South Korea
- Prior art keywords
- formula
- carbon atoms
- represented
- group
- chloride
- Prior art date
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- 125000004122 cyclic group Chemical group 0.000 title claims abstract description 22
- 238000002360 preparation method Methods 0.000 title description 4
- 239000003054 catalyst Substances 0.000 claims abstract description 44
- 239000000126 substance Substances 0.000 claims abstract description 22
- 150000004714 phosphonium salts Chemical class 0.000 claims abstract description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229920000620 organic polymer Polymers 0.000 claims abstract description 3
- 239000000377 silicon dioxide Substances 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 42
- 125000004432 carbon atom Chemical group C* 0.000 claims description 30
- 239000000460 chlorine Substances 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical class Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- SLLGVCUQYRMELA-UHFFFAOYSA-N chlorosilicon Chemical compound Cl[Si] SLLGVCUQYRMELA-UHFFFAOYSA-N 0.000 claims description 8
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 8
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 8
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 7
- 229920002050 silicone resin Polymers 0.000 claims description 6
- 150000001336 alkenes Chemical class 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
- 150000004756 silanes Chemical class 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- NEHMKBQYUWJMIP-UHFFFAOYSA-N anhydrous methyl chloride Natural products ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 229940050176 methyl chloride Drugs 0.000 claims description 3
- 125000001930 alkyl chloride group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 239000007810 chemical reaction solvent Substances 0.000 claims description 2
- 229910021432 inorganic complex Inorganic materials 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 5
- -1 inorganic comlex Polymers 0.000 abstract description 21
- 229910052710 silicon Inorganic materials 0.000 abstract description 8
- 239000010703 silicon Substances 0.000 abstract description 8
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- RNRQKQHZWFHUHS-UHFFFAOYSA-N trichloro-[[dichloro(trichlorosilylmethyl)silyl]methyl]silane Chemical compound Cl[Si](Cl)(Cl)C[Si](Cl)(Cl)C[Si](Cl)(Cl)Cl RNRQKQHZWFHUHS-UHFFFAOYSA-N 0.000 description 36
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- ZTNLXKSEJCGJRH-UHFFFAOYSA-N trichloro(dichlorosilylmethyl)silane Chemical compound Cl[SiH](Cl)C[Si](Cl)(Cl)Cl ZTNLXKSEJCGJRH-UHFFFAOYSA-N 0.000 description 28
- NLTXADBUSYWFIA-UHFFFAOYSA-N 1,1,3,3,5,5-hexachloro-1,3,5-trisilinane Chemical compound Cl[Si]1(Cl)C[Si](Cl)(Cl)C[Si](Cl)(Cl)C1 NLTXADBUSYWFIA-UHFFFAOYSA-N 0.000 description 24
- IBWGNZVCJVLSHB-UHFFFAOYSA-M tetrabutylphosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CCCC IBWGNZVCJVLSHB-UHFFFAOYSA-M 0.000 description 22
- 239000000047 product Substances 0.000 description 21
- 101000878457 Macrocallista nimbosa FMRFamide Proteins 0.000 description 19
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 19
- 229910001220 stainless steel Inorganic materials 0.000 description 19
- 239000010935 stainless steel Substances 0.000 description 19
- 238000004458 analytical method Methods 0.000 description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 12
- ILZIHGWXTARXAO-UHFFFAOYSA-N dichloro(dichlorosilylmethyl)silane Chemical compound Cl[SiH](Cl)C[SiH](Cl)Cl ILZIHGWXTARXAO-UHFFFAOYSA-N 0.000 description 12
- 238000005481 NMR spectroscopy Methods 0.000 description 11
- 150000001348 alkyl chlorides Chemical class 0.000 description 9
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 9
- 229940073608 benzyl chloride Drugs 0.000 description 9
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 9
- 229910052799 carbon Chemical group 0.000 description 8
- 239000005052 trichlorosilane Substances 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- MROCJMGDEKINLD-UHFFFAOYSA-N dichlorosilane Chemical compound Cl[SiH2]Cl MROCJMGDEKINLD-UHFFFAOYSA-N 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 229910000077 silane Inorganic materials 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- PPDADIYYMSXQJK-UHFFFAOYSA-N trichlorosilicon Chemical group Cl[Si](Cl)Cl PPDADIYYMSXQJK-UHFFFAOYSA-N 0.000 description 4
- NHBMXLXMVPLQAX-UHFFFAOYSA-N 1,3-disiletane Chemical compound C1[SiH2]C[SiH2]1 NHBMXLXMVPLQAX-UHFFFAOYSA-N 0.000 description 3
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- HGPNUESOTANCNF-UHFFFAOYSA-N dichloro(1-dichlorosilylethyl)silane Chemical compound Cl[SiH](Cl)C(C)[SiH](Cl)Cl HGPNUESOTANCNF-UHFFFAOYSA-N 0.000 description 3
- JAYBZWYBCUJLNQ-UHFFFAOYSA-N dichloro-(chloromethyl)-methylsilane Chemical compound C[Si](Cl)(Cl)CCl JAYBZWYBCUJLNQ-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000005292 vacuum distillation Methods 0.000 description 3
- SYSHGEHAYJKOLC-UHFFFAOYSA-N 1,1,3,3-tetrachloro-1,3-disiletane Chemical compound Cl[Si]1(Cl)C[Si](Cl)(Cl)C1 SYSHGEHAYJKOLC-UHFFFAOYSA-N 0.000 description 2
- PASYEMKYRSIVTP-UHFFFAOYSA-N 1,1-dichlorosiletane Chemical group Cl[Si]1(Cl)CCC1 PASYEMKYRSIVTP-UHFFFAOYSA-N 0.000 description 2
- YHRUOJUYPBUZOS-UHFFFAOYSA-N 1,3-dichloropropane Chemical compound ClCCCCl YHRUOJUYPBUZOS-UHFFFAOYSA-N 0.000 description 2
- MOHYOXXOKFQHDC-UHFFFAOYSA-N 1-(chloromethyl)-4-methoxybenzene Chemical compound COC1=CC=C(CCl)C=C1 MOHYOXXOKFQHDC-UHFFFAOYSA-N 0.000 description 2
- JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 description 2
- MLRVZFYXUZQSRU-UHFFFAOYSA-N 1-chlorohexane Chemical compound CCCCCCCl MLRVZFYXUZQSRU-UHFFFAOYSA-N 0.000 description 2
- 239000005047 Allyltrichlorosilane Substances 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- WCHPXAFAEZGCMB-UHFFFAOYSA-M benzyl(tributyl)phosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CC1=CC=CC=C1 WCHPXAFAEZGCMB-UHFFFAOYSA-M 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- USJRLGNYCQWLPF-UHFFFAOYSA-N chlorophosphane Chemical compound ClP USJRLGNYCQWLPF-UHFFFAOYSA-N 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000006471 dimerization reaction Methods 0.000 description 2
- 230000003100 immobilizing effect Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 description 2
- 150000003961 organosilicon compounds Chemical class 0.000 description 2
- 229920003257 polycarbosilane Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000007142 ring opening reaction Methods 0.000 description 2
- FBOJNMRAZJRCNS-UHFFFAOYSA-M tetraethylphosphanium;chloride Chemical compound [Cl-].CC[P+](CC)(CC)CC FBOJNMRAZJRCNS-UHFFFAOYSA-M 0.000 description 2
- TUQOTMZNTHZOKS-UHFFFAOYSA-O tributylphosphanium Chemical compound CCCC[PH+](CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-O 0.000 description 2
- LFXJGGDONSCPOF-UHFFFAOYSA-N trichloro(hexyl)silane Chemical compound CCCCCC[Si](Cl)(Cl)Cl LFXJGGDONSCPOF-UHFFFAOYSA-N 0.000 description 2
- HKFSBKQQYCMCKO-UHFFFAOYSA-N trichloro(prop-2-enyl)silane Chemical compound Cl[Si](Cl)(Cl)CC=C HKFSBKQQYCMCKO-UHFFFAOYSA-N 0.000 description 2
- CDVJPOXUZPVGOJ-UHFFFAOYSA-N trichloro-[(4-methoxyphenyl)methyl]silane Chemical compound COC1=CC=C(C[Si](Cl)(Cl)Cl)C=C1 CDVJPOXUZPVGOJ-UHFFFAOYSA-N 0.000 description 2
- ABVUXBPCPLBFHM-UHFFFAOYSA-N trichloro-[[dichloro(methyl)silyl]methyl]silane Chemical compound C[Si](Cl)(Cl)C[Si](Cl)(Cl)Cl ABVUXBPCPLBFHM-UHFFFAOYSA-N 0.000 description 2
- NKTAFVCXHYXTQK-UHFFFAOYSA-N 1,1,1-trichloro-3-methylbutane Chemical compound CC(C)CC(Cl)(Cl)Cl NKTAFVCXHYXTQK-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 125000006539 C12 alkyl 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 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- USFRYJRPHFMVBZ-UHFFFAOYSA-M benzyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=C1 USFRYJRPHFMVBZ-UHFFFAOYSA-M 0.000 description 1
- KSBGKOHSBWCTOP-UHFFFAOYSA-N bis(silylmethyl)silane Chemical compound [SiH3]C[SiH2]C[SiH3] KSBGKOHSBWCTOP-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- KTQYJQFGNYHXMB-UHFFFAOYSA-N dichloro(methyl)silicon Chemical compound C[Si](Cl)Cl KTQYJQFGNYHXMB-UHFFFAOYSA-N 0.000 description 1
- BUMGIEFFCMBQDG-UHFFFAOYSA-N dichlorosilicon Chemical group Cl[Si]Cl BUMGIEFFCMBQDG-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- POPACFLNWGUDSR-UHFFFAOYSA-N methoxy(trimethyl)silane Chemical compound CO[Si](C)(C)C POPACFLNWGUDSR-UHFFFAOYSA-N 0.000 description 1
- 239000005048 methyldichlorosilane Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 238000007344 nucleophilic reaction Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000012048 reactive intermediate Substances 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- BJQWBACJIAKDTJ-UHFFFAOYSA-N tetrabutylphosphanium Chemical compound CCCC[P+](CCCC)(CCCC)CCCC BJQWBACJIAKDTJ-UHFFFAOYSA-N 0.000 description 1
- WAGFXJQAIZNSEQ-UHFFFAOYSA-M tetraphenylphosphonium chloride Chemical compound [Cl-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 WAGFXJQAIZNSEQ-UHFFFAOYSA-M 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- KSNFJZGSDIMSME-UHFFFAOYSA-N trichloro(2-trichlorosilylpropan-2-yl)silane Chemical compound Cl[Si](Cl)(Cl)C(C)(C)[Si](Cl)(Cl)Cl KSNFJZGSDIMSME-UHFFFAOYSA-N 0.000 description 1
- GPWLZOISJZHVHX-UHFFFAOYSA-N trichloro(propan-2-yl)silane Chemical compound CC(C)[Si](Cl)(Cl)Cl GPWLZOISJZHVHX-UHFFFAOYSA-N 0.000 description 1
- DOEHJNBEOVLHGL-UHFFFAOYSA-N trichloro(propyl)silane Chemical compound CCC[Si](Cl)(Cl)Cl DOEHJNBEOVLHGL-UHFFFAOYSA-N 0.000 description 1
- ABDDAHLAEXNYRC-UHFFFAOYSA-N trichloro(trichlorosilylmethyl)silane Chemical compound Cl[Si](Cl)(Cl)C[Si](Cl)(Cl)Cl ABDDAHLAEXNYRC-UHFFFAOYSA-N 0.000 description 1
- CQHJBQDGWRDUML-UHFFFAOYSA-N trichloro-[(4-chlorophenyl)methyl]silane Chemical compound ClC1=CC=C(C[Si](Cl)(Cl)Cl)C=C1 CQHJBQDGWRDUML-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B33/00—Silicon; Compounds thereof
- C01B33/08—Compounds containing halogen
- C01B33/107—Halogenated silanes
-
- 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
- C07F7/12—Organo silicon halides
- C07F7/14—Preparation thereof from optionally substituted halogenated silanes and hydrocarbons hydrosilylation reactions
-
- 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
-
- 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
- C07F7/12—Organo silicon halides
-
- 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
- C07F7/12—Organo silicon halides
- C07F7/121—Preparation or treatment not provided for in C07F7/14, C07F7/16 or C07F7/20
- C07F7/122—Preparation or treatment not provided for in C07F7/14, C07F7/16 or C07F7/20 by reactions involving the formation of Si-C linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Claims (9)
- 제 1항에 있어서, 상기 4차 유기 포스포니움염 촉매는 실리콘 레진, 실리카, 무기 착물체, 및 유기 고분자로 이루어진 그룹에서 선택된 1종 이상의 담체 상에 고정화된 구조를 가지는 것을 특징으로 하는 제조방법.
- 제 1항에 있어서, 상기 4차 유기 포스포니움염 촉매는 상기 화학식 1로 표시되는 Si-H 결합을 갖는 비스클로로실릴메탄 1몰에 대하여 0.05 내지 0.5 몰 범위로 포함됨을 특징으로 하는 제조방법.
- 제 1항에 있어서, 상기 반응은 10∼250℃의 온도 범위에서 수행됨을 특징으로 하는 제조방법.
- 제 1항에 있어서, 상기 반응은 반응용매가 존재하지 않는 상태, 또는 방향족 탄화수소 용매 존재 하에서 수행됨을 특징으로 하는 제조방법.
- 제 1항에 있어서, 다음 화학식 5로 표시되는 유기 염화물을 더 포함함을 특징으로 하는 제조방법.화학식 5상기 화학식 5에서, R2는 할로겐 원소; 탄소수 1 내지 6의 직선형 또는 고리 형 알킬기; SiCl3, SiMeCl2, SiHCl2, SiMe2Cl 및 SiMe3로 이루어진 그룹으로부터 선택된 실란 유도체; 불포화 결합을 함유하는 탄소수 2 내지 5의 알켄기; Ar(R')q로 표시되는 방향족기(여기서, Ar은 탄소수 6 내지 14의 방향족 탄화수소, R'은 탄소수 1 내지 4의 알킬기, 할로겐, 알콕시, 또는 비닐기이고, q는 0 내지 5의 정수임); (CH2)pCl로 표시되는 염화알킬기(여기서, p는 1 내지 9의 정수임); 또는 ArCH2Cl로 표시되는 염화메틸 방향족기(여기서, Ar은 탄소수 6 내지 14의 방향족 탄화수소임) 중에서 선택된 것이며,R3는 수소 원자; 탄소수 1 내지 6의 직선형 또는 고리형 알킬기; 또는 Ar(R')q로 표시되는 방향족기(여기서, Ar은 탄소수 6 내지 14의 방향족 탄화수소, R'은 탄소수 1 내지 4의 알킬기, 할로겐, 알콕시, 또는 비닐기이고, q는 0 내지 5의 정수임) 중에서 선택된 것이다.
- 제 7항에 있어서, 다음 화학식 6으로 표시되는 유기 트리클로로실란 유도체가 더 얻어짐을 특징으로 하는 제조방법.화학식 6상기 화학식 6에서, 화학식 5에서와 같이 R3는 수소 원자; 탄소수 1 내지 6의 직선형 또는 고리형 알킬기; 또는 Ar(R')q로 표시되는 방향족기(여기서, Ar은 탄소수 6 내지 14의 방향족 탄화수소, R'은 탄소수 1 내지 4의 알킬기, 할로겐, 알콕시, 또는 비닐기이고, q는 0 내지 5의 정수임) 중에서 선택된 것이고,R4는 탄소수 1 내지 6의 직선형 또는 고리형 알킬기; SiCl3, SiMeCl2, SiHCl2, SiMe2Cl 및 SiMe3로 이루어진 그룹으로부터 선택된 실란 유도체; 불포화 결합을 함유하는 탄소수 2 내지 5의 알켄기; Ar(R')q로 표시되는 방향족기(여기서, Ar은 탄소수 6 내지 14의 방향족 탄화수소, R'은 탄소수 1 내지 4의 알킬기, 할로겐, 알콕시, 또는 비닐기이고, q는 0 내지 5의 정수임); 및 상기 화학식 5의 R2가 (CH2)pCl, ArCH2Cl일 경우 상기 화학식 6의 R4는 각각 (CH2)pSiCl3, ArCH2SiCl3임.)
- 제 7항에 있어서, 상기 화학식 5로 표시되는 유기 염화물은 상기 화학식 1로 표시되는 Si-H 결합을 갖는 비스클로로실릴메탄 1몰에 대하여 0.5 내지 8몰 범위로 반응됨을 특징으로 하는 제조방법.
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CN2009801246773A CN102076700A (zh) | 2008-05-26 | 2009-05-22 | 线性或环状三硅烷的制备方法 |
PCT/KR2009/002696 WO2009145523A2 (ko) | 2008-05-26 | 2009-05-22 | 직선형이나 고리형의 트리실라알칸의 제조방법 |
US12/994,818 US8450515B2 (en) | 2008-05-26 | 2009-05-22 | Production method for linear and cyclic trisilaalkane |
JP2011511502A JP5474945B2 (ja) | 2008-05-26 | 2009-05-22 | 直線状や環状トリシラアルカンの製造方法 |
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CN105899190B (zh) * | 2014-01-09 | 2022-06-14 | 赛诺菲 | 门冬胰岛素的稳定化药物制剂 |
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US4937364A (en) | 1988-11-26 | 1990-06-26 | Shin-Etsu Chemical Co., Ltd. | Novel disilacyclohexane compound and process for preparing the same |
KR940010291B1 (ko) * | 1992-01-23 | 1994-10-22 | 한국과학기술연구원 | 비스실릴알칸 및 그들의 제조방법 |
KR100453211B1 (ko) | 2000-11-01 | 2004-10-15 | 한국과학기술연구원 | 유기 실란의 제조방법 |
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US2381000A (en) * | 1942-03-04 | 1945-08-07 | Gen Electric | Halogenated organosilicon compounds |
KR940007416B1 (en) * | 1991-01-22 | 1994-08-18 | Korea Inst Sci & Tech | Process for the preparation of silaalkane |
KR940007414B1 (ko) * | 1991-06-14 | 1994-08-18 | 한국과학기술연구원 | 1,3-디실라시클로부탄 유도체 및 그 제조방법 |
KR100306574B1 (ko) * | 1999-04-13 | 2001-09-13 | 박호군 | 탈할로겐화수소 반응으로 유기할로겐 화합물에 실란을 결합시키는 방법 |
US5998649A (en) * | 1999-05-17 | 1999-12-07 | Jung; Il Nam | Organosilicon compounds and method for preparation |
US6392077B1 (en) * | 2000-11-01 | 2002-05-21 | Korea Institute Of Science And Technology | Process for preparing organochlorosilanes by dehydrohalogenative coupling reaction of alkyl halides with chlorosilanes |
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US4937364A (en) | 1988-11-26 | 1990-06-26 | Shin-Etsu Chemical Co., Ltd. | Novel disilacyclohexane compound and process for preparing the same |
KR940010291B1 (ko) * | 1992-01-23 | 1994-10-22 | 한국과학기술연구원 | 비스실릴알칸 및 그들의 제조방법 |
KR100453211B1 (ko) | 2000-11-01 | 2004-10-15 | 한국과학기술연구원 | 유기 실란의 제조방법 |
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US8450515B2 (en) | 2013-05-28 |
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