GB847802A - Process for producing cyanoalkylsilanes - Google Patents
Process for producing cyanoalkylsilanesInfo
- Publication number
- GB847802A GB847802A GB38982/56A GB3898256A GB847802A GB 847802 A GB847802 A GB 847802A GB 38982/56 A GB38982/56 A GB 38982/56A GB 3898256 A GB3898256 A GB 3898256A GB 847802 A GB847802 A GB 847802A
- Authority
- GB
- United Kingdom
- Prior art keywords
- gamma
- silane
- bis
- catalyst
- platinum
- 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
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 4
- 239000003054 catalyst Substances 0.000 abstract 3
- 229910052697 platinum Inorganic materials 0.000 abstract 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 abstract 2
- SJNALLRHIVGIBI-UHFFFAOYSA-N allyl cyanide Chemical compound C=CCC#N SJNALLRHIVGIBI-UHFFFAOYSA-N 0.000 abstract 2
- ZXPDYFSTVHQQOI-UHFFFAOYSA-N diethoxysilane Chemical compound CCO[SiH2]OCC ZXPDYFSTVHQQOI-UHFFFAOYSA-N 0.000 abstract 2
- 150000002825 nitriles Chemical class 0.000 abstract 2
- 229910052763 palladium Inorganic materials 0.000 abstract 2
- 229910000077 silane Inorganic materials 0.000 abstract 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- MRCZILRUHBOANV-UHFFFAOYSA-N 3-methyl-4-trichlorosilylbutanenitrile Chemical compound N#CCC(C)C[Si](Cl)(Cl)Cl MRCZILRUHBOANV-UHFFFAOYSA-N 0.000 abstract 1
- CVFGRDOVEFUBES-UHFFFAOYSA-N 4-[dichloro(3-cyanopropyl)silyl]butanenitrile Chemical compound N#CCCC[Si](Cl)(Cl)CCCC#N CVFGRDOVEFUBES-UHFFFAOYSA-N 0.000 abstract 1
- HMFFOEBLYHLRQN-UHFFFAOYSA-N 4-trichlorosilylbutanenitrile Chemical compound Cl[Si](Cl)(Cl)CCCC#N HMFFOEBLYHLRQN-UHFFFAOYSA-N 0.000 abstract 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 239000010425 asbestos Substances 0.000 abstract 1
- 229910000019 calcium carbonate Inorganic materials 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 150000001721 carbon Chemical group 0.000 abstract 1
- 239000003610 charcoal Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 125000004966 cyanoalkyl group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- XNAFLNBULDHNJS-UHFFFAOYSA-N dichloro(phenyl)silicon Chemical compound Cl[Si](Cl)C1=CC=CC=C1 XNAFLNBULDHNJS-UHFFFAOYSA-N 0.000 abstract 1
- CWAFVXWRGIEBPL-UHFFFAOYSA-N ethoxysilane Chemical compound CCO[SiH3] CWAFVXWRGIEBPL-UHFFFAOYSA-N 0.000 abstract 1
- 239000003365 glass fiber Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 abstract 1
- UNAQSRLBVVDYGP-UHFFFAOYSA-N hex-5-enenitrile Chemical compound C=CCCCC#N UNAQSRLBVVDYGP-UHFFFAOYSA-N 0.000 abstract 1
- 150000002431 hydrogen Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- -1 methallyl cyanides Chemical class 0.000 abstract 1
- 229910052895 riebeckite Inorganic materials 0.000 abstract 1
- 150000004756 silanes Chemical class 0.000 abstract 1
- 239000007858 starting material 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
- C07F7/14—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
- 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
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1876—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-C linkages
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Platinum and/or palladium is used as a catalyst in the production of cyanoalkylsilanes by reacting an olefinic nitrile in which the olefinic group is at least one carbon atom removed from the cyano group with a silane of the formula H Si Rn X(3-n), where R is hydrogen, alkyl, cycloalkyl, aryl or alkaryl, X is halogen or alkoxy or aroxy, and n is 0, 1 or 2. Examples of nitriles are allyl and methallyl cyanides and 1-cyano-4-pentene. The platinum or palladium catalyst may be used alone or in combination with an inert support such as asbestos, charcoal or calcium carbonate. They may also form part of a multi-component system, e.g. platinum deposited on gamma alumina. The amount of metal catalyst may be from 0,02 to 2 parts per 100 of the weight of starting materials. Suitable temperatures are from 40 DEG to 350 DEG C and pressures may be superatmospheric. The products include mono-, bis- and tris- (cyanoalkyl) silanes and specific examples are gamma-cyanopropylhydrogendichloro- and diethoxy-silane, bis (gamma-cyanopropyl) hydrogenchloro- and ethoxy-silane, delta-cyanobutylhydrogendichlorosilane, epsilon - cyanopentylhydrogendiethoxy - silane, gamma-cyanopropylmethyldichloro- and diethoxy-silane, gamma-cyanopropyltrichlorosilane, gamma-cyanopropylethyl- and phenyldichlorosilane and beta-methyl-gamma-cyanopropyltrichlorosilane. Bis (gamma-cyanopropyl) dichlorosilane is prepared from allyl cyanide and gamma-cyanopropylhydrogendichlorosilane; and the compounds can be hydrogenated in the presence of a nickel catalyst to produce aminoalkylsilanes which are useful as sizes for fibrous glass materials. Specification 847,803 is referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US847802XA | 1955-12-23 | 1955-12-23 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB847802A true GB847802A (en) | 1960-09-14 |
Family
ID=22187157
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB38982/56A Expired GB847802A (en) | 1955-12-23 | 1956-12-21 | Process for producing cyanoalkylsilanes |
Country Status (4)
Country | Link |
---|---|
BE (1) | BE553605A (en) |
DE (1) | DE1157228B (en) |
FR (1) | FR1169052A (en) |
GB (1) | GB847802A (en) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3020301A (en) * | 1959-12-30 | 1962-02-06 | Union Carbide Corp | Process of making cyanoalkylsilanes |
US3018300A (en) * | 1959-12-30 | 1962-01-23 | Union Carbide Corp | Process of making cyanoalkylsilanes |
US3046292A (en) * | 1959-12-30 | 1962-07-24 | Union Carbide Corp | Process of making cyanoalkylsilanes |
US3030403A (en) * | 1959-12-30 | 1962-04-17 | Union Carbide Corp | Process of making cyanoalkylsilanes |
DE3129272A1 (en) | 1981-07-24 | 1983-02-10 | Bayer Ag, 5090 Leverkusen | METHOD FOR PRODUCING 2-TRIMETHYLSILYLOXY ETHYLAMINE |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2721873A (en) * | 1952-03-11 | 1955-10-25 | Montclair Res Corp | Reaction of silanes with unsaturated aliphatic compounds |
-
0
- BE BE553605D patent/BE553605A/xx unknown
-
1956
- 1956-12-21 GB GB38982/56A patent/GB847802A/en not_active Expired
- 1956-12-22 DE DEU4277A patent/DE1157228B/en active Pending
- 1956-12-22 FR FR1169052D patent/FR1169052A/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
FR1169052A (en) | 1958-12-22 |
DE1157228B (en) | 1963-11-14 |
BE553605A (en) |
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