GB694526A - Production of organohalosilanes - Google Patents
Production of organohalosilanesInfo
- Publication number
- GB694526A GB694526A GB6384/51A GB638451A GB694526A GB 694526 A GB694526 A GB 694526A GB 6384/51 A GB6384/51 A GB 6384/51A GB 638451 A GB638451 A GB 638451A GB 694526 A GB694526 A GB 694526A
- Authority
- GB
- United Kingdom
- Prior art keywords
- boron
- silicon
- heating
- methyldichlorosilane
- benzene
- 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.)
- Expired
Links
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 21
- 229930195733 hydrocarbon Natural products 0.000 abstract 11
- 239000004215 Carbon black (E152) Substances 0.000 abstract 10
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 abstract 8
- 238000010438 heat treatment Methods 0.000 abstract 8
- KTQYJQFGNYHXMB-UHFFFAOYSA-N dichloro(methyl)silicon Chemical compound C[Si](Cl)Cl KTQYJQFGNYHXMB-UHFFFAOYSA-N 0.000 abstract 7
- 239000005048 methyldichlorosilane Substances 0.000 abstract 7
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 abstract 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 6
- 239000004327 boric acid Substances 0.000 abstract 6
- 229910052796 boron Inorganic materials 0.000 abstract 6
- 150000002430 hydrocarbons Chemical class 0.000 abstract 6
- ZXNKRXWFQRLIQG-UHFFFAOYSA-N silicon(4+);tetraborate Chemical compound [Si+4].[Si+4].[Si+4].[O-]B([O-])[O-].[O-]B([O-])[O-].[O-]B([O-])[O-].[O-]B([O-])[O-] ZXNKRXWFQRLIQG-UHFFFAOYSA-N 0.000 abstract 6
- -1 Aromatic chlorosilanes Chemical class 0.000 abstract 5
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 abstract 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 5
- 125000003545 alkoxy group Chemical group 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- GNEPOXWQWFSSOU-UHFFFAOYSA-N dichloro-methyl-phenylsilane Chemical compound C[Si](Cl)(Cl)C1=CC=CC=C1 GNEPOXWQWFSSOU-UHFFFAOYSA-N 0.000 abstract 4
- 238000011065 in-situ storage Methods 0.000 abstract 4
- 229910000077 silane Inorganic materials 0.000 abstract 4
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 abstract 3
- AYHOQSGNVUZKJA-UHFFFAOYSA-N [B+3].[B+3].[B+3].[B+3].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-] Chemical compound [B+3].[B+3].[B+3].[B+3].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-] AYHOQSGNVUZKJA-UHFFFAOYSA-N 0.000 abstract 3
- 239000003054 catalyst Substances 0.000 abstract 3
- 239000007795 chemical reaction product Substances 0.000 abstract 3
- 239000000460 chlorine Chemical group 0.000 abstract 3
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- 239000011541 reaction mixture Substances 0.000 abstract 3
- 150000004756 silanes Chemical class 0.000 abstract 3
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 abstract 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 2
- 229910004721 HSiCl3 Inorganic materials 0.000 abstract 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract 2
- 229910003910 SiCl4 Inorganic materials 0.000 abstract 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- 229910052801 chlorine Chemical group 0.000 abstract 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 abstract 2
- XNAFLNBULDHNJS-UHFFFAOYSA-N dichloro(phenyl)silicon Chemical compound Cl[Si](Cl)C1=CC=CC=C1 XNAFLNBULDHNJS-UHFFFAOYSA-N 0.000 abstract 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 abstract 2
- 238000010992 reflux Methods 0.000 abstract 2
- 229910052710 silicon Inorganic materials 0.000 abstract 2
- 239000010703 silicon Substances 0.000 abstract 2
- FDNAPBUWERUEDA-UHFFFAOYSA-N silicon tetrachloride Chemical compound Cl[Si](Cl)(Cl)Cl FDNAPBUWERUEDA-UHFFFAOYSA-N 0.000 abstract 2
- LGQXXHMEBUOXRP-UHFFFAOYSA-N tributyl borate Chemical compound CCCCOB(OCCCC)OCCCC LGQXXHMEBUOXRP-UHFFFAOYSA-N 0.000 abstract 2
- 239000005046 Chlorosilane Substances 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 abstract 1
- 150000004996 alkyl benzenes Chemical class 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- 235000010290 biphenyl Nutrition 0.000 abstract 1
- 125000006267 biphenyl group Chemical group 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical class B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 abstract 1
- 150000001639 boron compounds Chemical class 0.000 abstract 1
- 150000001642 boronic acid derivatives Chemical class 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- DHUWBNXXQFWIKW-UHFFFAOYSA-N chloro(diphenyl)borane Chemical compound C=1C=CC=CC=1B(Cl)C1=CC=CC=C1 DHUWBNXXQFWIKW-UHFFFAOYSA-N 0.000 abstract 1
- KWYZNESIGBQHJK-UHFFFAOYSA-N chloro-dimethyl-phenylsilane Chemical compound C[Si](C)(Cl)C1=CC=CC=C1 KWYZNESIGBQHJK-UHFFFAOYSA-N 0.000 abstract 1
- RYNOURCVJXQRTJ-UHFFFAOYSA-N chloro-ethoxy-dimethylsilane Chemical compound CCO[Si](C)(C)Cl RYNOURCVJXQRTJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000013078 crystal Substances 0.000 abstract 1
- 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 abstract 1
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 abstract 1
- YYLGKUPAFFKGRQ-UHFFFAOYSA-N dimethyldiethoxysilane Chemical compound CCO[Si](C)(C)OCC YYLGKUPAFFKGRQ-UHFFFAOYSA-N 0.000 abstract 1
- VIGVRXYWWFPORY-UHFFFAOYSA-N diphenylborinic acid Chemical compound C=1C=CC=CC=1B(O)C1=CC=CC=C1 VIGVRXYWWFPORY-UHFFFAOYSA-N 0.000 abstract 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 230000003993 interaction Effects 0.000 abstract 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
- WIBYPHGWXYLWQX-UHFFFAOYSA-N methyl 2-bromo-2-chloroacetate Chemical compound COC(=O)C(Cl)Br WIBYPHGWXYLWQX-UHFFFAOYSA-N 0.000 abstract 1
- 125000000962 organic group Chemical group 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 1
- 239000005054 phenyltrichlorosilane Substances 0.000 abstract 1
- 229920006389 polyphenyl polymer Polymers 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 abstract 1
- 150000004819 silanols Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 abstract 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 abstract 1
- 239000005052 trichlorosilane Substances 0.000 abstract 1
- 239000005051 trimethylchlorosilane Substances 0.000 abstract 1
- YZYKZHPNRDIPFA-UHFFFAOYSA-N tris(trimethylsilyl) borate Chemical compound C[Si](C)(C)OB(O[Si](C)(C)C)O[Si](C)(C)C YZYKZHPNRDIPFA-UHFFFAOYSA-N 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 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
- 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)
- Catalysts (AREA)
Abstract
Aromatic chlorosilanes are prepared by reacting naphthalene or a benzenoid hydrocarbon free from aliphatic unsaturation in any side chains with an organo-dichloromonohydrosilane of the general formula RHSiCl2, wherein R is a monovalent hydrocarbon radical free from aliphatic unsaturation at a reaction temperature above 150 DEG C., at least a portion of the reaction mixture being in condensed phase, in the presence of a silicon-borate complex selected from the group consisting of (1) the reaction product of a silane of the general formula R14-a-bHaSiXb, where each R1 is a monovalent hydrocarbon radical, each X is alkoxy or chlorine, a is 0 or 1, b is an interger from 1 to 4, the sum of a and b being not greater than 4 with B2O3 or a compound of the general formula (R11O)xBR3-x, where R11 is a monovalent hydrocarbon radical or hydrogen, R is a monovalent hydrocarbon radical and x is 1, 2 or 3, but excluding a reaction product of organo - dichloromono - hydrosilane with B2O3 or H3BO3 formed in situ, and (2) the reaction product of a siloxane or a silanol with a compound of the general formula RyBY3-y, where R has the above significance, Y is a halogen atom and y is 0, 1 or 2, the complex being employed in such a proportion that at least 0.01 per cent by weight of boron is present calculated on the total weight of the reaction mixture. The preferred reaction temperature is from 150 DEG to 250 DEG C. A monosilyl derivative of the hydrocarbon is obtained using a slight excess of the hydrocarbon; the use of more than one molecular equivalent of the silane per mol. of the hydrocarbon increases the yield of polysilyl derivatives of the hydrocarbon, e.g. bis- and tris-silyl derivatives, without appreciable decrease in the amount of monosilyl derivative formed. Benzenoid hydrocarbons which may be used are benzene, polyphenyls such as p diphenyl and alkyl substituted benzenes such as toluene, xylene, cumene and mesitylene. Organo-dichloromonohydrosilanes that may be used are methyldichlorosilane and phenyldichlorosilane. The silicon-borate complex may be formed in situ or may be prepared in advance and added to the reaction mixture. When the complex is formed in situ, it may be formed from the organo-dichloromonohydrosilane used in the reaction, and the boron compound used is preferably of the general formula (R11cO)3B2-c where R11 is a monovalent hydrocarbon radical or hydrogen and c is 0 or 1. H3BO3 and B2O3 may be used for the formation in situ of the silicon-borate complexes. The silicon-borate complexes may be of a simple type, e.g. [(CH3)3SiO]3B, or may be of a more complex type, e.g. compounds containing any of the structures <FORM:0694526/IV (b)/1> , <FORM:0694526/IV (b)/2> , or <FORM:0694526/IV (b)/3> in which the open bonds may be satisfied by any of the group consisting of phenyl, methyl, alkoxy, chlorine and hydrogen, or may be linked to other silicon or boron atoms through oxygen. Examples of suitable silanes which may be used to form the silicon-borate complexes are SiCl4, HSiCl3, CH3HSiCl2, (CH3)2Si(OC2H5)Cl, (CH3)3SiOC2H5, (CH3)3SiCl, C6H5SiCl3, C6H5CH3SiCl2 and C6H5(CH3)2SiCl. If an alkoxy substituted silane is used, it is preferable that the alkoxy group contains less than 5 carbon atoms. The boron employed for the preparation of the complexes may be in the form of boric acid, boric anhydride or organic borates such as tributylborate, phenylboric acid: C6H5B(OH)2, and diphenylboric acid: (C6H5)2BOH. The silicon-borate complexes may also be formed by the interaction of siloxanes or silanols with boron halides or organo-boron halides of the above general formula such as phenylboron dichloride and diphenylboron chloride. When silicon halides are also present, the complexes may be formed from metallic boron or the boron hydrides. When the complex is previously prepared, it may be formed at or below reflux temperature at atmospheric pressure, and an excess of the silane may be used as a solvent for the complex. The use of B2O3 or the use of low-boiling silanes such as SiCl4 and HSiCl3 entails the use of temperatures higher than reflux temperatures with the aid of super-atmospheric pressures. In the examples: (1) benzene, methyldichlorosilane and tris-(trimethylsilyl) borate (prepared by heating boric acid and trimethylchlorosilane) are heated in a sealed bomb to give methyl phenyldichlorosilane; (2) methyl tolyldichlorosilanes are prepared by heating in a sealed bomb toluene, methyldichlorosilane and a boron-silicate catalyst obtained by heating boric acid and phenyldimethylchlorosilane; (3) methyl phenyldichlorosilane is obtained by heating in a sealed bomb benzene, methyldichlorosilane and a boron - silicate catalyst obtained by heating boric acid and methyldichlorosilane; (4) methyl phenyl dichlorosilane is obtained by heating tributylborate, benzene and methyldichlorosilane in a sealed bomb; (5) methyl phenyldichlorosilane is prepared by heating in a sealed bomb benzene, methyldichlorosilane and a boron-silicate catalyst consisting essentially of the compound (Me2EtOSiO)3B and obtained by mixing dimethyldichlorosilane and dimethyldiethoxysilane in the presence of a few crystals of boric acid to form dimethylethoxychlorosilane which is then refluxed with boric acid; (6) phenyl trichlorosilane is prepared by heating benzene containing a small amount of siloxanes, trichlorosilane and boron trichloride; the distillation residue remaining after removing the reactants and desired product contains boron and is distilled to give a boron containing fraction which is heated in a sealed bomb with benzene and phenyldichlorosilane to yield diphenyldichlorosilane.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US692596XA | 1950-04-10 | 1950-04-10 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB694526A true GB694526A (en) | 1953-07-22 |
Family
ID=22087768
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB27962/48A Expired GB646629A (en) | 1950-04-10 | 1947-12-04 | Production of organohalosilanes |
GB6384/51A Expired GB694526A (en) | 1950-04-10 | 1951-03-16 | Production of organohalosilanes |
GB6383/51A Expired GB692596A (en) | 1950-04-10 | 1951-03-16 | Production of organohalosilanes |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB27962/48A Expired GB646629A (en) | 1950-04-10 | 1947-12-04 | Production of organohalosilanes |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB6383/51A Expired GB692596A (en) | 1950-04-10 | 1951-03-16 | Production of organohalosilanes |
Country Status (5)
Country | Link |
---|---|
BE (1) | BE486021A (en) |
DE (1) | DE871302C (en) |
FR (1) | FR1036722A (en) |
GB (3) | GB646629A (en) |
NL (1) | NL70343C (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4255586A (en) | 1978-04-14 | 1981-03-10 | Castrol Limited | Boron-silicon compounds suitable for use as hydraulic fluids |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE522861A (en) * | 1952-09-26 | |||
GB751370A (en) * | 1953-02-27 | 1956-06-27 | Midland Silicones Ltd | A process for the manufacture of phenylhalosilanes |
-
0
- NL NL70343D patent/NL70343C/xx active
- BE BE486021D patent/BE486021A/xx unknown
-
1947
- 1947-12-04 GB GB27962/48A patent/GB646629A/en not_active Expired
-
1951
- 1951-02-24 FR FR1036722D patent/FR1036722A/en not_active Expired
- 1951-03-16 GB GB6384/51A patent/GB694526A/en not_active Expired
- 1951-03-16 GB GB6383/51A patent/GB692596A/en not_active Expired
- 1951-04-10 DE DED8636A patent/DE871302C/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4255586A (en) | 1978-04-14 | 1981-03-10 | Castrol Limited | Boron-silicon compounds suitable for use as hydraulic fluids |
Also Published As
Publication number | Publication date |
---|---|
GB646629A (en) | 1950-11-22 |
DE871302C (en) | 1953-03-23 |
NL70343C (en) | |
BE486021A (en) | |
GB692596A (en) | 1953-06-10 |
FR1036722A (en) | 1953-09-10 |
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