GB935534A - Method of forming a cyanoalkylsilane and catalyst therefor - Google Patents
Method of forming a cyanoalkylsilane and catalyst thereforInfo
- Publication number
- GB935534A GB935534A GB4151859A GB4151859A GB935534A GB 935534 A GB935534 A GB 935534A GB 4151859 A GB4151859 A GB 4151859A GB 4151859 A GB4151859 A GB 4151859A GB 935534 A GB935534 A GB 935534A
- Authority
- GB
- United Kingdom
- Prior art keywords
- beta
- diamine
- moles
- tri
- alkyl
- 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
- 239000003054 catalyst Substances 0.000 title abstract 4
- 229910052757 nitrogen Inorganic materials 0.000 abstract 8
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 150000004985 diamines Chemical class 0.000 abstract 4
- 239000000203 mixture Substances 0.000 abstract 4
- 125000005270 trialkylamine group Chemical group 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- 239000004215 Carbon black (E152) Substances 0.000 abstract 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 2
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 abstract 2
- 125000004103 aminoalkyl group Chemical group 0.000 abstract 2
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 abstract 2
- KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 abstract 2
- 229940112669 cuprous oxide Drugs 0.000 abstract 2
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 abstract 2
- NAPSCFZYZVSQHF-UHFFFAOYSA-N dimantine Chemical class CCCCCCCCCCCCCCCCCCN(C)C NAPSCFZYZVSQHF-UHFFFAOYSA-N 0.000 abstract 2
- -1 dimethyl butyl- Chemical group 0.000 abstract 2
- 150000004820 halides Chemical class 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- 239000003921 oil Substances 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- 239000004342 Benzoyl peroxide Substances 0.000 abstract 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 abstract 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 abstract 1
- 239000004965 Silica aerogel Substances 0.000 abstract 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 1
- 235000019400 benzoyl peroxide Nutrition 0.000 abstract 1
- 125000004966 cyanoalkyl group Chemical group 0.000 abstract 1
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 abstract 1
- 229920001971 elastomer Polymers 0.000 abstract 1
- 239000000806 elastomer Substances 0.000 abstract 1
- 239000012530 fluid Substances 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 239000000314 lubricant Substances 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 229910052990 silicon hydride Inorganic materials 0.000 abstract 1
- 229920002545 silicone oil Polymers 0.000 abstract 1
- 229920002379 silicone rubber Polymers 0.000 abstract 1
- PPDADIYYMSXQJK-UHFFFAOYSA-N trichlorosilicon Chemical compound Cl[Si](Cl)Cl PPDADIYYMSXQJK-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0235—Nitrogen containing compounds
- B01J31/0237—Amines
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
- B01J31/28—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24 of the platinum group metals, iron group metals or copper
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
- B01J31/28—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24 of the platinum group metals, iron group metals or copper
- B01J31/30—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
- C07F7/0896—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
- C07F7/12—Organo silicon halides
- C07F7/14—Preparation thereof from optionally substituted halogenated silanes and hydrocarbons hydrosilylation reactions
-
- 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
-
- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/32—Addition reactions to C=C or C-C triple bonds
- B01J2231/323—Hydrometalation, e.g. bor-, alumin-, silyl-, zirconation or analoguous reactions like carbometalation, hydrocarbation
-
- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/72—Copper
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Inorganic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Polymerisation Methods In General (AREA)
Abstract
A catalyst composition used in the preparation of beta-cyanoalkylsilanes (see Group IV(a)), comprises (A) a cuprous halide or cuprous oxide, (B) a di- or tri-amine of the formula RR1N(CH2)mN(R1)2 where m is 1 to 6, R is alkyl and R1 is hydrogen, alkyl, aminoalkyl or dialkylaminoalkyl, and preferably (C) a trialkylamine; the total number of nitrogen atoms in the composition being greater than the number of copper atoms. Examples of component (B) include, inter alia, N,N,N1,N1-tetramethylethylene diamine, N,N-dimethyl-N,N1-diethylethylene diamine, N,N-dimethylethylene diamine, N,N,N1-trimethyl-N1-octylethylene diamine, N,N,N1,N11,N11-pentamethyldiethylene triamine, N,N,N1,N1-tetramethyl-methylene and -propylene diamines, N,N,N1-trimethyldiethylene triamine and N-methylhexamethylene diamine. Specified trialkylamines (C) are tri-methyl-, -ethyl, -butyl, -amyl, -octyl amines, methyldiethyl-, dimethyl butyl-, methyl butyloctyl- and dimethyl octadecyl-amines. The preferred proportions are 0,1 to 20 moles each of (A) and (B) and 0 to 20 moles of (C). In (A) the number of moles is based on the formula CuX or CuO 1/2 , X being halogen.ALSO:Beta-cyanoalkyl silanes containing 1 or 2 cyanoalkyl groups, 1 to 3 silicon-bonded halogen atoms, up to 2 silicon-bonded hydrogen atoms and 0 or 1 silicon-bonded hydrocarbon or substituted hydrocarbon radical, are prepared by reacting the appropriate silicon hydride with an alpha-, beta-unsaturated olefinic nitrile in the presence of a catalyst composition comprising (A) a cuprous halide or cuprous oxide, (B) a di- or tri-amine of the formula RR1N(CH2)mN(R1)2 where m is 1 to 6, R is alkyl and R1 is hydrogen, alkyl, aminoalkyl or dialkylaminoalkyl, and preferably (C) a trialkylamine; the total number of nitrogen atoms in the catalyst composition being greater than the number of copper atoms. Examples of component (B) include, inter alia, N,N,N1,N1-tetramethylethylene diamine, N,N-dimethyl-N,N1-diethylethylene diamine, N,N-dimethylethylene diamine, N,N,N1-trimethyl-N1-octylethylene diamine, N,N,N1,N11-N11-pentamethyldiethylene triamine, N,N,N1,-N1-tetramethyl-methylene and -propylene diamines, N,N,N1-trimethyldiethylene triamine and N-methylhexamethylene diamine. Specified trialkylamines (C) are tri-methyl, -ethyl, -butyl, -amyl, -octyl amines, methyldiethyl-, dimethylbutyl-, methylbutyloctyl- and dimethyloctadecylamines. The preferred proportions are 0,1 to 20 moles each of (A) and (B), and 0 to 20 moles of (C). In (A) the number of moles is based on the formula CuX or <FORM:0935534/IV(a)/1> X being halogen. Many examples are given describing the preparation of beta-(CN-Et)MeSiCl2, beta-(CN-Pr)MeSiCl2, beta-(CN-Et)PhSiCl2, and beta-(CN-Et)SiCl3. The difunctional beta-cyanoalkyl silanes may be converted to silicone oils and elastomers; e.g. equal parts of (CN-Et)MeSiCl2 and Me2SiCl2 are cohydrolysed to form an oil which may be converted to a gum by heating with KOH; this gum being milled with silica aerogel and benzoyl peroxide and heated to form a rubber. The beta-cyanoalkyl trichlorosilanes may also be cohydrolysed with other halosilanes to form oils and resins. Uses: Lubricants, hydraulic fluids, gaskets.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US783102A US2971970A (en) | 1958-12-29 | 1958-12-29 | Organosilicon process |
| US802669A US2971972A (en) | 1959-03-30 | 1959-03-30 | Addition reaction |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB935534A true GB935534A (en) | 1963-08-28 |
Family
ID=27120100
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4151859A Expired GB935534A (en) | 1958-12-29 | 1959-12-07 | Method of forming a cyanoalkylsilane and catalyst therefor |
| GB867360A Expired GB935535A (en) | 1958-12-29 | 1960-03-11 | Improvements relating to the preparation of ªâ-cyanoethylphenyl-dichlorosilane |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB867360A Expired GB935535A (en) | 1958-12-29 | 1960-03-11 | Improvements relating to the preparation of ªâ-cyanoethylphenyl-dichlorosilane |
Country Status (3)
| Country | Link |
|---|---|
| DE (2) | DE1156410B (en) |
| FR (3) | FR1118500A (en) |
| GB (2) | GB935534A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106632448A (en) * | 2016-11-16 | 2017-05-10 | 广州天赐高新材料股份有限公司 | Cyano-containing chlorosilane synthesis method |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3109011A (en) * | 1956-12-10 | 1963-10-29 | Union Carbide Corp | Preparation of carboalkoxy alkyl silanes from silanes containing silanic hydrogen and acrylic acid esters |
| US2989559A (en) * | 1958-06-27 | 1961-06-20 | Union Carbide Corp | Carbonyl-containing organopolysiloxanes |
| US2971970A (en) * | 1958-12-29 | 1961-02-14 | Gen Electric | Organosilicon process |
| US2971971A (en) * | 1958-12-29 | 1961-02-14 | Gen Electric | Addition of methyldichloirosilane to acrylonitrile in presence of a diaminetrialkylamine-pdci2 catalyst composition |
| US2971972A (en) * | 1959-03-30 | 1961-02-14 | Gen Electric | Addition reaction |
| US2985679A (en) * | 1959-08-03 | 1961-05-23 | Union Carbide Corp | Chlorocyanoalkyl silanes and siloxanes |
| US2968666A (en) * | 1959-08-03 | 1961-01-17 | Union Carbide Corp | Chlorocyanoalkenylsilicon compounds |
| US3018300A (en) * | 1959-12-30 | 1962-01-23 | Union Carbide Corp | Process of making cyanoalkylsilanes |
| US3020301A (en) * | 1959-12-30 | 1962-02-06 | Union Carbide Corp | Process of making cyanoalkylsilanes |
| US3057902A (en) * | 1960-08-31 | 1962-10-09 | Union Carbide Corp | Ester solvents and basic catalysts employed in an addition process |
| US3153662A (en) * | 1960-09-14 | 1964-10-20 | Union Carbide Corp | Addition process employing nitrile solvents and basic catalysts |
| DE1140577B (en) * | 1960-11-14 | 1962-12-06 | Wacker Chemie Gmbh | Process for the cyanaethylation of monoorganosilanes |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1116726A (en) * | 1953-12-31 | 1956-05-11 | Thomson Houston Comp Francaise | Organosilicon compounds containing both hydrolyzable groups and cyanoalkyl radicals |
| BE553603A (en) * | 1955-12-23 |
-
1954
- 1954-12-29 FR FR1118500D patent/FR1118500A/en not_active Expired
-
1959
- 1959-12-07 GB GB4151859A patent/GB935534A/en not_active Expired
- 1959-12-17 FR FR813296A patent/FR77159E/en not_active Expired
- 1959-12-18 DE DEG28625A patent/DE1156410B/en active Pending
-
1960
- 1960-03-11 GB GB867360A patent/GB935535A/en not_active Expired
- 1960-03-22 DE DEG29283A patent/DE1127898B/en active Pending
- 1960-03-30 FR FR822838A patent/FR1252474A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106632448A (en) * | 2016-11-16 | 2017-05-10 | 广州天赐高新材料股份有限公司 | Cyano-containing chlorosilane synthesis method |
| CN106632448B (en) * | 2016-11-16 | 2019-03-26 | 广州天赐高新材料股份有限公司 | A kind of synthetic method of cyano-containing chlorosilane |
Also Published As
| Publication number | Publication date |
|---|---|
| FR77159E (en) | 1962-01-27 |
| FR1252474A (en) | 1961-01-27 |
| DE1127898B (en) | 1962-04-19 |
| FR1118500A (en) | 1956-06-06 |
| GB935535A (en) | 1963-08-28 |
| DE1156410B (en) | 1963-10-31 |
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