DE1232580B - Verfahren zur Herstellung von Vinylhalogensilanen - Google Patents
Verfahren zur Herstellung von VinylhalogensilanenInfo
- Publication number
- DE1232580B DE1232580B DER39491A DER0039491A DE1232580B DE 1232580 B DE1232580 B DE 1232580B DE R39491 A DER39491 A DE R39491A DE R0039491 A DER0039491 A DE R0039491A DE 1232580 B DE1232580 B DE 1232580B
- Authority
- DE
- Germany
- Prior art keywords
- acetylene
- reaction
- trichlorosilane
- amount
- per hour
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 20
- 229920002554 vinyl polymer Polymers 0.000 title claims description 12
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title description 3
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 26
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 26
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 21
- 239000003054 catalyst Substances 0.000 claims description 17
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 claims description 13
- 239000005052 trichlorosilane Substances 0.000 claims description 13
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 claims description 10
- 229910052697 platinum Inorganic materials 0.000 claims description 10
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims description 8
- KTQYJQFGNYHXMB-UHFFFAOYSA-N dichloro(methyl)silicon Chemical compound C[Si](Cl)Cl KTQYJQFGNYHXMB-UHFFFAOYSA-N 0.000 claims description 8
- 239000003085 diluting agent Substances 0.000 claims description 8
- 239000005048 methyldichlorosilane Substances 0.000 claims description 8
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 claims description 8
- 239000005050 vinyl trichlorosilane Substances 0.000 claims description 8
- 239000012429 reaction media Substances 0.000 claims description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 6
- YLJJAVFOBDSYAN-UHFFFAOYSA-N dichloro-ethenyl-methylsilane Chemical compound C[Si](Cl)(Cl)C=C YLJJAVFOBDSYAN-UHFFFAOYSA-N 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 229910000077 silane Inorganic materials 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- -1 dimethylvinyl Chemical group 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- 229910052710 silicon Inorganic materials 0.000 claims description 4
- 150000003377 silicon compounds Chemical class 0.000 claims description 4
- 238000002474 experimental method Methods 0.000 claims description 3
- 239000011521 glass Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000010703 silicon Substances 0.000 claims description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000007789 gas Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000011148 porous material Substances 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- 239000005046 Chlorosilane Substances 0.000 claims 2
- QABCGOSYZHCPGN-UHFFFAOYSA-N chloro(dimethyl)silicon Chemical compound C[Si](C)Cl QABCGOSYZHCPGN-UHFFFAOYSA-N 0.000 claims 2
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- SUUAWNZSDXISFO-UHFFFAOYSA-N Cl[SiH2]Cl.Cl[SiH](Cl)Cl Chemical compound Cl[SiH2]Cl.Cl[SiH](Cl)Cl SUUAWNZSDXISFO-UHFFFAOYSA-N 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 239000002826 coolant Substances 0.000 claims 1
- XNAFLNBULDHNJS-UHFFFAOYSA-N dichloro(phenyl)silicon Chemical compound Cl[Si](Cl)C1=CC=CC=C1 XNAFLNBULDHNJS-UHFFFAOYSA-N 0.000 claims 1
- VFURVLVRHAMJKG-UHFFFAOYSA-N dichloro-[2-[dichloro(methyl)silyl]ethyl]-methylsilane Chemical compound C[Si](Cl)(Cl)CC[Si](C)(Cl)Cl VFURVLVRHAMJKG-UHFFFAOYSA-N 0.000 claims 1
- QDASGLPLQWLMSJ-UHFFFAOYSA-N dichloro-ethenyl-phenylsilane Chemical compound C=C[Si](Cl)(Cl)C1=CC=CC=C1 QDASGLPLQWLMSJ-UHFFFAOYSA-N 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 150000004756 silanes Chemical class 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000001577 simple distillation Methods 0.000 description 2
- ZOYFEXPFPVDYIS-UHFFFAOYSA-N trichloro(ethyl)silane Chemical compound CC[Si](Cl)(Cl)Cl ZOYFEXPFPVDYIS-UHFFFAOYSA-N 0.000 description 2
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical class [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000270295 Serpentes Species 0.000 description 1
- CYVTYWBDUINCRE-UHFFFAOYSA-N [Si].[SiH3]Cl Chemical compound [Si].[SiH3]Cl CYVTYWBDUINCRE-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical class Cl* 0.000 description 1
- DMZWVCJEOLBQCZ-UHFFFAOYSA-N chloro(ethenyl)silane Chemical class Cl[SiH2]C=C DMZWVCJEOLBQCZ-UHFFFAOYSA-N 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- MROCJMGDEKINLD-UHFFFAOYSA-N dichlorosilane Chemical compound Cl[SiH2]Cl MROCJMGDEKINLD-UHFFFAOYSA-N 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- VDCSGNNYCFPWFK-UHFFFAOYSA-N diphenylsilane Chemical compound C=1C=CC=CC=1[SiH2]C1=CC=CC=C1 VDCSGNNYCFPWFK-UHFFFAOYSA-N 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 239000008246 gaseous mixture Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229920001558 organosilicon polymer Polymers 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000004794 vinyl magnesium halides Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07F7/0896—Compounds with a Si-H linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0801—General processes
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR957652A FR1390999A (fr) | 1963-12-18 | 1963-12-18 | Procédé de préparation de vinylsilanes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1232580B true DE1232580B (de) | 1967-01-19 |
Family
ID=8819166
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DER39491A Pending DE1232580B (de) | 1963-12-18 | 1964-12-18 | Verfahren zur Herstellung von Vinylhalogensilanen |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3404169A (OSRAM) |
| JP (1) | JPS4813095B1 (OSRAM) |
| BE (1) | BE657279A (OSRAM) |
| CH (1) | CH423772A (OSRAM) |
| DE (1) | DE1232580B (OSRAM) |
| FR (1) | FR1390999A (OSRAM) |
| GB (1) | GB1068538A (OSRAM) |
| NL (2) | NL6414746A (OSRAM) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5646326A (en) * | 1994-12-01 | 1997-07-08 | Huels Aktiengesellschaft | Alkylhydrogenchlorosilanes, process for their preparation and their use |
| US5929269A (en) * | 1996-05-11 | 1999-07-27 | Huels Aktiengesellschaft | Process for preparing vinylated organosilicon compounds |
| DE102011076687A1 (de) * | 2011-05-30 | 2012-12-06 | Wacker Chemie Ag | Pt-haltiger Katalysator, dessen Herstellung und dessen Einsatz bei der Hydrosilylierung von Si-H-haltigen Verbindungen |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3933880A (en) * | 1974-12-02 | 1976-01-20 | Dow Corning Corporation | Method of preparing a platinum catalyst inhibitor |
| US3933882A (en) * | 1974-12-02 | 1976-01-20 | Dow Corning Corporation | Tube method for the preparation of olefinic siloxane compounds |
| US4447633A (en) * | 1983-06-14 | 1984-05-08 | North Dakota State University | Ultrasonically promoted hydrosilations |
| US4579965A (en) * | 1985-01-24 | 1986-04-01 | Union Carbide Corporation | Process for preparing vinyl-tri-(tertiary substituted) alkoxysilanes |
| KR910008295B1 (ko) * | 1987-01-28 | 1991-10-12 | 미쯔이도오아쯔가가꾸 가부시기가이샤 | 탄화규소의 제조방법 |
| US5620934A (en) * | 1987-01-28 | 1997-04-15 | Mitsui Toatsu Chemicals, Incorporated | Production process of silicon carbide from organosilicon compounds |
| US5508363A (en) * | 1987-01-28 | 1996-04-16 | Mitsui Toatsu Chemicals, Incorporated | Preparation process of organosilicon compounds and production of silicon carbide |
| US4898961A (en) * | 1989-07-17 | 1990-02-06 | Dow Corning Corporation | Method for preparing alkenylsilanes |
| US5041595A (en) * | 1990-09-26 | 1991-08-20 | Union Carbide Chemicals And Plastics Technology Corporation | Method for manufacturing vinylalkoxysilanes |
| US5416233A (en) * | 1994-01-25 | 1995-05-16 | The Dow Chemical Company | Preparation of vinylsilane-benzocyclobutenes |
| CN102076701B (zh) * | 2008-07-01 | 2014-11-26 | 莫门蒂夫性能材料股份有限公司 | 用于气态不饱和烃的氢化硅烷化方法 |
| FR3000070B1 (fr) | 2012-12-21 | 2015-02-06 | Bluestar Silicones France | Procede de preparation de polyorganosiloxanes fonctionnalises |
| CN112007634B (zh) * | 2019-05-28 | 2023-08-29 | 新特能源股份有限公司 | 乙烯基三氯硅烷新型催化剂及其制备方法、及其催化制备乙烯基三氯硅烷的方法 |
| CN120795014B (zh) * | 2025-09-04 | 2025-12-23 | 鲁东大学 | 一种1,3-二乙烯基-1,1,3,3-四甲基二硅氧烷的制备方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE553159A (OSRAM) * | 1955-12-05 | |||
| US3220972A (en) * | 1962-07-02 | 1965-11-30 | Gen Electric | Organosilicon process using a chloroplatinic acid reaction product as the catalyst |
-
0
- NL NL132148D patent/NL132148C/xx active
-
1963
- 1963-12-18 FR FR957652A patent/FR1390999A/fr not_active Expired
-
1964
- 1964-12-10 US US417471A patent/US3404169A/en not_active Expired - Lifetime
- 1964-12-11 GB GB50615/64A patent/GB1068538A/en not_active Expired
- 1964-12-17 NL NL6414746A patent/NL6414746A/xx unknown
- 1964-12-17 BE BE657279A patent/BE657279A/xx unknown
- 1964-12-18 DE DER39491A patent/DE1232580B/de active Pending
- 1964-12-18 JP JP39071133A patent/JPS4813095B1/ja active Pending
- 1964-12-18 CH CH1638164A patent/CH423772A/fr unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5646326A (en) * | 1994-12-01 | 1997-07-08 | Huels Aktiengesellschaft | Alkylhydrogenchlorosilanes, process for their preparation and their use |
| US5929269A (en) * | 1996-05-11 | 1999-07-27 | Huels Aktiengesellschaft | Process for preparing vinylated organosilicon compounds |
| DE102011076687A1 (de) * | 2011-05-30 | 2012-12-06 | Wacker Chemie Ag | Pt-haltiger Katalysator, dessen Herstellung und dessen Einsatz bei der Hydrosilylierung von Si-H-haltigen Verbindungen |
Also Published As
| Publication number | Publication date |
|---|---|
| CH423772A (fr) | 1966-11-15 |
| NL132148C (OSRAM) | |
| FR1390999A (fr) | 1965-03-05 |
| NL6414746A (OSRAM) | 1965-06-21 |
| BE657279A (OSRAM) | 1965-06-17 |
| GB1068538A (en) | 1967-05-10 |
| JPS4813095B1 (OSRAM) | 1973-04-25 |
| US3404169A (en) | 1968-10-01 |
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