WO2011051133A1 - Verfahren zur herstellung von organosilanen - Google Patents
Verfahren zur herstellung von organosilanen Download PDFInfo
- Publication number
- WO2011051133A1 WO2011051133A1 PCT/EP2010/065668 EP2010065668W WO2011051133A1 WO 2011051133 A1 WO2011051133 A1 WO 2011051133A1 EP 2010065668 W EP2010065668 W EP 2010065668W WO 2011051133 A1 WO2011051133 A1 WO 2011051133A1
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- WO
- WIPO (PCT)
- Prior art keywords
- general formula
- mixture
- radical
- hydrogen
- chlorobenzene
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 8
- 150000001282 organosilanes Chemical class 0.000 title description 3
- 239000000203 mixture Substances 0.000 claims abstract description 39
- -1 hydrocarbon radical Chemical class 0.000 claims abstract description 27
- 239000003999 initiator Substances 0.000 claims abstract description 16
- 239000001257 hydrogen Substances 0.000 claims abstract description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 11
- 150000002367 halogens Chemical class 0.000 claims abstract description 10
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 150000001335 aliphatic alkanes Chemical class 0.000 claims abstract description 7
- 150000008282 halocarbons Chemical class 0.000 claims abstract description 7
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 7
- 150000004756 silanes Chemical class 0.000 claims abstract description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 56
- MROCJMGDEKINLD-UHFFFAOYSA-N dichlorosilane Chemical compound Cl[SiH2]Cl MROCJMGDEKINLD-UHFFFAOYSA-N 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 22
- 150000003254 radicals Chemical class 0.000 claims description 14
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 8
- 229910000077 silane Inorganic materials 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 150000005826 halohydrocarbons Chemical class 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 claims description 4
- 229910000071 diazene Inorganic materials 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000005389 trialkylsiloxy group Chemical group 0.000 claims description 2
- CNJALTWFAHMCKW-UHFFFAOYSA-N C1(=CC=CC=C1)[Si](Cl)(Cl)C1=CC=CC=C1.ClC1=CC=CC=C1 Chemical compound C1(=CC=CC=C1)[Si](Cl)(Cl)C1=CC=CC=C1.ClC1=CC=CC=C1 CNJALTWFAHMCKW-UHFFFAOYSA-N 0.000 claims 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 19
- 239000005052 trichlorosilane Substances 0.000 description 19
- 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 14
- 239000005054 phenyltrichlorosilane Substances 0.000 description 9
- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 description 9
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- XNAFLNBULDHNJS-UHFFFAOYSA-N dichloro(phenyl)silicon Chemical compound Cl[Si](Cl)C1=CC=CC=C1 XNAFLNBULDHNJS-UHFFFAOYSA-N 0.000 description 8
- 238000004821 distillation Methods 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical compound C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 6
- LAXBNTIAOJWAOP-UHFFFAOYSA-N 2-chlorobiphenyl Chemical group ClC1=CC=CC=C1C1=CC=CC=C1 LAXBNTIAOJWAOP-UHFFFAOYSA-N 0.000 description 6
- 239000005046 Chlorosilane Substances 0.000 description 6
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- FDNAPBUWERUEDA-UHFFFAOYSA-N silicon tetrachloride Chemical compound Cl[Si](Cl)(Cl)Cl FDNAPBUWERUEDA-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000005070 sampling Methods 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- KTQYJQFGNYHXMB-UHFFFAOYSA-N dichloro(methyl)silicon Chemical compound C[Si](Cl)Cl KTQYJQFGNYHXMB-UHFFFAOYSA-N 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- 239000005048 methyldichlorosilane Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- 229920002545 silicone oil Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- HGTUJZTUQFXBIH-UHFFFAOYSA-N (2,3-dimethyl-3-phenylbutan-2-yl)benzene Chemical compound C=1C=CC=CC=1C(C)(C)C(C)(C)C1=CC=CC=C1 HGTUJZTUQFXBIH-UHFFFAOYSA-N 0.000 description 1
- RUGHUJBHQWALKM-UHFFFAOYSA-N 1,2,2-triphenylethylbenzene Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C(C=1C=CC=CC=1)C1=CC=CC=C1 RUGHUJBHQWALKM-UHFFFAOYSA-N 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000006043 5-hexenyl group Chemical group 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- SUUAWNZSDXISFO-UHFFFAOYSA-N Cl[SiH2]Cl.Cl[SiH](Cl)Cl Chemical compound Cl[SiH2]Cl.Cl[SiH](Cl)Cl SUUAWNZSDXISFO-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- 229920004482 WACKER® Polymers 0.000 description 1
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 1
- 125000005024 alkenyl aryl group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 150000004074 biphenyls Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- ZKYBKEMNIRTZSB-UHFFFAOYSA-N butyldiazene Chemical compound CCCCN=N ZKYBKEMNIRTZSB-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- QABCGOSYZHCPGN-UHFFFAOYSA-N chloro(dimethyl)silicon Chemical compound C[Si](C)Cl QABCGOSYZHCPGN-UHFFFAOYSA-N 0.000 description 1
- NBWIIOQJUKRLKW-UHFFFAOYSA-N chloro(phenyl)silane Chemical class Cl[SiH2]C1=CC=CC=C1 NBWIIOQJUKRLKW-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- PFMKUUJQLUQKHT-UHFFFAOYSA-N dichloro(ethyl)silicon Chemical compound CC[Si](Cl)Cl PFMKUUJQLUQKHT-UHFFFAOYSA-N 0.000 description 1
- UVQGVNLXTFRLNL-UHFFFAOYSA-N dicyclohexyldiazene Chemical compound C1CCCCC1N=NC1CCCCC1 UVQGVNLXTFRLNL-UHFFFAOYSA-N 0.000 description 1
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- CATWEXRJGNBIJD-UHFFFAOYSA-N n-tert-butyl-2-methylpropan-2-amine Chemical compound CC(C)(C)NC(C)(C)C CATWEXRJGNBIJD-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- 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
-
- 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
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/24—Stationary reactors without moving elements inside
-
- 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
- C07F7/123—Preparation or treatment not provided for in C07F7/14, C07F7/16 or C07F7/20 by reactions involving the formation of Si-halogen 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
- C07F7/121—Preparation or treatment not provided for in C07F7/14, C07F7/16 or C07F7/20
- C07F7/125—Preparation or treatment not provided for in C07F7/14, C07F7/16 or C07F7/20 by reactions involving both Si-C and Si-halogen linkages, the Si-C and Si-halogen linkages can be to the same or to different Si atoms, e.g. redistribution reactions
Definitions
- the invention relates to a process for the preparation of
- Organosilanes of hydrogen silanes and halogenated hydrocarbons in the presence of a radical initiator Organosilanes of hydrogen silanes and halogenated hydrocarbons in the presence of a radical initiator.
- Laid-open publication is i.a. the production of
- the object of the invention is to provide a process for the preparation of diorganyldihalogens lanen with high specific yield, which forms little unwanted by-products and which is safe to handle.
- the invention relates to a process for the preparation of diorganyldihalosilanes of the general formula (1)
- a free radical initiator which is selected from alkanes reacted, diazenes and organodisilanes, wherein R is a monovalent C] _-C] _g hydrocarbon radical,
- R ' is a monovalent Ci-Cig hydrocarbon radical, hydrogen or halogen
- X is halogen
- Trichlorosilane fall e.g. as distillates in the
- Chlorosilane production for the production of hyperpure silicon for the semiconductor or photovoltaic industry in large quantities If one uses these chlorosilane mixtures, we obtain by the inventive method by reaction with
- Radical initiators which are used at 500 ° C. for at least 5 seconds, in particular
- R 1 and R 4 are phenyl and R 2 , R 3 , R 5 and R 6 are hydrogen or alkyl or R 1 and R 4 are phenyl and R 2 and R 5 are phenyl or alkyl and R 3 and R ⁇ Trialkoxysiloxyrest or
- R ⁇ , R 2 , R 4 and R 5 are phenyl and R 3 and R 6 are hydrogen
- R 7 -N NR 8 (6), wherein R7 and R ° C] _-C] _ Q hydrocarbyl may be este, or organodisilanes of the general formula
- alkyl radicals here are C 1 -C -alkyl radicals
- R and C are preferably alkyl, aryl or aralkyl radicals.
- R 1 and R 2 are preferably C 2 -C 5 -alkyl radicals, in particular the methyl or ethyl radical or chlorine.
- Particularly good results are obtained with 1,2-diphenylethane, 2,3-diphenyl-2, 3-dimethylbutane, 1, 1, 2, 2-tetraphenylethane, 3,4-dimethyl-3-diphenylhexane, dicyclohexyl diazene and di-t-butylamine. achieved by butyl diazene.
- X and R 'in the meaning of halogen are preferably fluorine,
- Chlorine and bromine especially chlorine.
- Particularly preferred is it is the silane of the general formula (2) to dichlorosilane.
- radicals R ' are preferably phenyl radicals or C 1 -C -alkyl radicals, in particular methyl or ethyl radicals or chlorine.
- Preferred compounds of the general formula (3) are
- the silane is the
- the radicals R are preferably alkenyl radicals preferably having 2 to 6 carbon atoms, such as vinyl-allyl, methallyl, 1-propenyl, 5-hexenyl, ethynyl, butadienyl, hexadienyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, preferably vinyl and
- Aryl radicals such as phenyl radicals; Alkaryl radicals, aralkyl, alkenylaryl or arylalkenyl radicals; Phenylalkenyl radicals.
- Halogenobenzene especially chlorobenzene.
- the halohydrocarbon of the general formula (4) is reacted with the mixture of the hydrosilanes of the general formulas (2) and (3) in a molar ratio of halogen: Si-bonded hydrogen of not more than 4: 1, in particular not more than 1.5: 1, 0 and at least 1: 4, more preferably at most 3: 1 reacted.
- the amount of alkane or diazene used as radical initiator is preferably at least 0.005 wt .-%, in particular at least 0.01 wt .-% and at most 3% by weight, in particular not more than 0.5% by weight, based on the mixture of halohydrocarbon used
- organodisilanes in particular disilanes (for example the high-boiling fraction from the distillation residue of ochow synthesis of .sup.4) and hydrogensilanes of the general formulas (2) and (3)
- Dichlorodimethylsilane as a radical initiator are preferably at least 1% by weight, in particular at least 2% by weight and at most 15% by weight, in particular at most 10% by weight, based on the mixture of halohydrocarbon of the general formula (4) and hydrogensilanes used the general
- diphenyldichlorosilane is prepared from dichlorosilane by reaction with chlorobenzene by the process according to the invention.
- Dichlorosilane and trichlorosilane in proportions up to preferably not more than 50% other chlorosilanes from the Chlorsilansynthese starting from metallurgical silicon and hydrogen chloride, preferably tetrachlorosilane and methyldichlorosilane.
- metal chlorides such as
- the inventive method is preferably at
- the inventive method is preferably in a
- mixture of chlorobenzene, and dichlorosilane with trichlorosilane and free-radical initiator is preferably fed in vapor.
- these are preferably the liquid
- Components - which are either premixed in a mixing unit (static or active mixer) in the desired ratio or produced directly as a mixture in a process - by an evaporator and the vapors then by a Heat exchanger sent / thus with approximately
- Reaction temperature enter the reactor zone.
- Room temperature solid radical initiators are used in a preferred embodiment in the form of a solution in chlorobenzene.
- the residence time of the reaction mixture in the reactor is preferably at least 2 seconds, in particular at least 5 seconds and at most 80 seconds, in particular at most 50 seconds,
- Reaction mixture is preferably carried out after removal of the volatile constituents, in particular of the hydrogen halide formed in the reaction, by distillation or
- the hydrogen halide formed is preferably bound in a scrubbing system and optionally neutralized or, more preferably, recycled
- the process according to the invention is preferably carried out continuously. It can be e.g. to
- Phenyldichlorosilane which isolated by distillation in a mixture with the educt mixture can be fed back into the reactor.
- the materials in the components must be resistant to the
- Reactor design (volume, pressure loss) can be variably set within limits and can be optimized from an economic point of view. For example, it may be useful to reduce the throughput and thus increase the residence time, if this is to achieve a better space-time yield. Conversely, this can result in undesirable reactions that can lead to the separation of solids in the reactor system.
- Reactions are carried out at an ambient pressure of 0.10 MPa (abs.) And an ambient temperature of 20 ° C.
- a quartz glass apparatus consisting of evaporator flask with an argon or nitrogen inlet valve, attached tube with heating mantle as reaction zone, bridge with cooling jacket, sampling flask for the condensable reaction products and Reactions of dichlorosilane and mixtures of trichlorosilane and dichlorosilane with chlorobenzene can be carried out under different conditions.
- Evaporator flask is heated to 170 ° C, the cooling
- Thermocouple determines which projects into the hot reaction zone.
- the sample is taken from the sampling flask via the bottom valve by means of an evacuated sample vessel and analyzed by gas chromatography.
- the quartz tube After inerting with argon, the quartz tube is brought to the desired temperature with an electric heater. From a storage container is the
- Metered evaporator flask The liquid is metered at a rate such that the metered amount evaporates completely as soon as possible.
- the metered amount evaporates completely as soon as possible.
- Inertization 5 1 / h argon introduced.
- the condensate collects after a few seconds in the sampling flask, Once a representative amount has accumulated, the dosage is interrupted and a sample of the liquid condensate taken under argon and in a
- Reaction zone was 600 ° C, the residence time at 10 seconds, After half an hour, the dosage was terminated. About 40 g of yellowish condensate had collected in the receiver flask. According to gas chromatographic analysis, the condensate contained not only unreacted dichlorosilane (0.28%), trichlorosilane (4.11%) and chlorobenzene (68.9%).
- Reaction zone was 650 ° C, the residence time at 10 seconds. After half an hour, the dosage was stopped. 37 g of yellowish condensate had collected in the receiver flask. According to gas chromatographic analysis, the condensate contained not only unreacted dichlorosilane (0.03%), trichlorosilane (1.22%) and chlorobenzene (60%).
- Reaction zone was 600 ° C, the residence time at 8 seconds. After half an hour, the dosage was stopped. 48 g of yellowish condensate had collected in the receiver flask. According to gas chromatographic analysis, the condensate contained not only unreacted dichlorosilane (0.45%), trichlorosilane (5.29%) and chlorobenzene (68.4%).
- Reaction zone was 600 ° C, the residence time at 8 seconds. After half an hour, the dosage was stopped. 48 g of yellowish condensate had collected in the receiver flask. According to gas chromatographic analysis, the condensate contained not only unreacted dichlorosilane (1.15%), trichlorosilane ⁇ 1.83% ⁇ and chlorobenzene (73.54%).
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JP2012535740A JP5426033B2 (ja) | 2009-10-28 | 2010-10-19 | オルガノシランの製造方法 |
US13/497,673 US20120296106A1 (en) | 2009-10-28 | 2010-10-19 | Process for preparing organosilanes |
EP10765648A EP2493900A1 (de) | 2009-10-28 | 2010-10-19 | Verfahren zur herstellung von organosilanen |
CN2010800493352A CN102596971A (zh) | 2009-10-28 | 2010-10-19 | 有机硅烷的制备方法 |
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DE102009046121A DE102009046121A1 (de) | 2009-10-28 | 2009-10-28 | Verfahren zur Herstellung von Organosilanen |
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US (1) | US20120296106A1 (de) |
EP (1) | EP2493900A1 (de) |
JP (1) | JP5426033B2 (de) |
KR (1) | KR20120048036A (de) |
CN (1) | CN102596971A (de) |
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CN107206355B (zh) * | 2015-02-06 | 2020-07-07 | 美国陶氏有机硅公司 | 制备有机卤代硅烷的方法 |
WO2016126808A1 (en) * | 2015-02-06 | 2016-08-11 | Dow Corning Corporation | Method of producing organohalosilanes |
CN112920214A (zh) * | 2019-12-05 | 2021-06-08 | 新特能源股份有限公司 | 一种苯基氯硅烷、制备方法及装置 |
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US5136071A (en) * | 1991-12-16 | 1992-08-04 | Dow Corning Corporation | Sodium borohydride as activator for phenylborane catalyzed disproportionation of arylsilanes |
KR100306574B1 (ko) * | 1999-04-13 | 2001-09-13 | 박호군 | 탈할로겐화수소 반응으로 유기할로겐 화합물에 실란을 결합시키는 방법 |
US6251057B1 (en) * | 1999-04-13 | 2001-06-26 | Korea Institute Of Science And Technology | Dehydrohalogenative coupling reaction of organic halides with silanes |
JP2003212884A (ja) * | 2002-01-24 | 2003-07-30 | Toagosei Co Ltd | フェニルシランの製造方法 |
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JP2013508433A (ja) | 2013-03-07 |
DE102009046121A1 (de) | 2011-05-05 |
KR20120048036A (ko) | 2012-05-14 |
CN102596971A (zh) | 2012-07-18 |
US20120296106A1 (en) | 2012-11-22 |
EP2493900A1 (de) | 2012-09-05 |
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