US5124468A
Expired / Lapsed
US
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Method for silylformylating alkynes and products obtained therefrom
Assignee: General Electric Co
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Filing: 1991-08-02
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Granted: 1992-06-23
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Expires: 2011-08-02
Abstract
Abstract Silicon hydrides substituted with oxygen containing radicals such as alkoxy, can be silylformylated with alkynes and carbon monoxide in the presence of a rhodium catalyst to produce silyl alkenyl acetals. The silyl alkenyl acetals are useful as plasticizers for organosilicon copolymers.
Inventors
- 👤 Terry E. Krafft
- 👤 Jonathan D. Rich
- 👤 Timothy B. Burnell
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 14:34
CPC Classifications
C; C07; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/18; C07F7/1804; C07F7/1872; C07F7/188; C07F7/0803; C07F7/081; C07F7/0812; C07F7/0816; C07F7/1876
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
108 words
A method comprising, (1) effecting reaction between an alkyne of the formula, R.sup.2 C.tbd.CR.sup.3 and a silicon hydride of the formula, (R).sub.n (R.sup.1).sub.3-n SiH in the presence of carbon monoxide and an effective amount of a rhodium catalyst and, (2) recovering a silylformylated alkyne reaction product from the mixture of (1), where R is a monovalent radical attached to silicon by a silicon oxygen linkage, R 1 is a C.sub.(1-13) monovalent hydrocarbon radical, R 2 and R 3 are the same or different monovalent radicals selected from the class consisting of hydrogen and a C.sub.(1-3) organic radical and n is an integer equal to 1 to 3 inclusive.
Claim 2
Independent Claim
108 words
A method comprising, (1) effecting reaction between an alkyne of the formula, R.sup.2 C.tbd.CR.sup.3 and a silicon hydride of the formula, (R).sub.n (R.sup.1).sub.3-n SiH in the presence of carbon monoxide and an effective amount of a rhodium catalyst and, (2) recovering a silylformylated alkyne reaction product from the mixture of (1), where R is a monovalent radical attached to silicon by a silicon oxygen linkage, R 1 is a C.sub.(1-13) monovalent hydrocarbon radical, R 2 and R 3 are the same or different monovalent radicals selected from the class consisting of hydrogen and a C.sub.(1-3) organic radical and n is an integer equal to 1 to 3 inclusive.
Claim 3
Dependent Claim
14 words
A method in accordance with claim 1, where the silicon hydride is an ethoxysilane.
Claim 4
Dependent Claim
12 words
A method in accordance with claim 1, where the alkyne is phenylacetylene.
Claim 5
Dependent Claim
12 words
A method in accordance with claim 1, where the alkyne is acetylene.
Claim 6
Dependent Claim
12 words
A method in accordance with claim 1, where the alkyne is diphenylacetylene.
Claim 7
Dependent Claim
12 words
A method in accordance with claim 1, where the alkyne is but-2-yne-1,4-diol.
Claim 8
Dependent Claim
13 words
A method in accordance with claim 1, where the alkyne is dimethylacetylene dicarboxylate.
Claim 9
Dependent Claim
17 words
A method in accordance with claim 1, where the rhodium catalyst is Rh 4 (CO) 12 .
Claim 10
Dependent Claim
14 words
A method in accordance with claim 1, where the rhodium catalyst is rhodium trichloride.
Claim 11
Dependent Claim
83 words
Silyl alkenyl acetals having the formula, ##STR5## where R is a monovalent radical attached to silicon by silicon oxygen linkage, R 1 is a C.sub.(1-13) monovalent hydrocarbon radical, R 2 and R 3 are the same or different monovalent radicals and selected from the class consisting of hydrogen and a C.sub.(1-13) organic radical, R 4 is a monovalent radical selected from the class consisting of C.sub.(1-8) alkyl, C.sub.(6-13) aryl and C.sub.(1-3) triorganosilyl, and m is a whole number equal to 0 to 2.
Claim 12
Dependent Claim
83 words
Silyl alkenyl acetals having the formula, ##STR5## where R is a monovalent radical attached to silicon by silicon oxygen linkage, R 1 is a C.sub.(1-13) monovalent hydrocarbon radical, R 2 and R 3 are the same or different monovalent radicals and selected from the class consisting of hydrogen and a C.sub.(1-13) organic radical, R 4 is a monovalent radical selected from the class consisting of C.sub.(1-8) alkyl, C.sub.(6-13) aryl and C.sub.(1-3) triorganosilyl, and m is a whole number equal to 0 to 2.
Claim 13
Dependent Claim
70 words
Silylalkenyl aldehydes having the formula, ##STR6## where R is a monovalent radical attached to silicon by a silicon-oxygen linkage, such as C.sub.(1-8) alkoxy, C.sub.(6-2) aryloxy, and triorganosiloxy, R 1 is a C.sub.(1-13) monovalent hydrocarbon radical, R 2 and R 3 are the same or different monovalent radicals selected from the class consisting of hydrogen and a C.sub.(1-13) organic radical, and n is an integer equal to 1 to 3 inclusive.
Claim 14
Dependent Claim
70 words
Silylalkenyl aldehydes having the formula, ##STR6## where R is a monovalent radical attached to silicon by a silicon-oxygen linkage, such as C.sub.(1-8) alkoxy, C.sub.(6-2) aryloxy, and triorganosiloxy, R 1 is a C.sub.(1-13) monovalent hydrocarbon radical, R 2 and R 3 are the same or different monovalent radicals selected from the class consisting of hydrogen and a C.sub.(1-13) organic radical, and n is an integer equal to 1 to 3 inclusive.
Claim 15
Dependent Claim
70 words
Silylalkenyl aldehydes having the formula, ##STR7## where R is a monovalent radical attached to silicon by a silicon-oxygen linkage, such as C.sub.(1-8) alkoxy, C.sub.(6-12) aryloxy, and triorganosiloxy, R 1 is a C.sub.(1-13) monovalent hydrocarbon radical, R 2 and R 3 are the same or different monovalent radicals selected from the class consisting of hydrogen and a C.sub.(1-3) organic radical, and n is an integer equal to 1 to 3 inclusive.
Claim 16
Dependent Claim
70 words
Silylalkenyl aldehydes having the formula, ##STR7## where R is a monovalent radical attached to silicon by a silicon-oxygen linkage, such as C.sub.(1-8) alkoxy, C.sub.(6-12) aryloxy, and triorganosiloxy, R 1 is a C.sub.(1-13) monovalent hydrocarbon radical, R 2 and R 3 are the same or different monovalent radicals selected from the class consisting of hydrogen and a C.sub.(1-3) organic radical, and n is an integer equal to 1 to 3 inclusive.
Claim 17
Dependent Claim
7 words
E; 2-ethoxy-2-methyl-4-phenylsilapent-3-enal in accordance with claim 11.
Claim 18
Dependent Claim
7 words
Z; 2-ethoxy-2-methyl-4-phenylsilapent-3-enal in accordance with claim 11.
Claim 19
Dependent Claim
7 words
E; 1,1,1-triethoxy-3-phenylsilabut-2-enal in accordance with claim 11.
Claim 20
Dependent Claim
7 words
Z; 1,1,1-triethoxy-3-phenylsilabut-2-enal in accordance with claim 11.
Claim 21
Dependent Claim
7 words
1,1-dimethyl-2-oxa-3-ethoxy-4-phenyl silacyclopent-4,5-ene, in accordance with claim 10.
Claim 22
Dependent Claim
7 words
1,1-diethoxy-2-oxa-3-ethoxy-4-phenyl silacyclopent-4,5-ene, in accordance with claim 10.
Claim 23
Dependent Claim
7 words
E; 2-ethoxy-2-methyl-3-phenylsilapent-3-enal in accordance with claim 12.
Claim 24
Dependent Claim
7 words
Z; 2-ethoxy-2-methyl-3-phenylsilapent-3-enal in accordance with claim 12.
Claim 25
Dependent Claim
7 words
E; 1,1,1-triethoxy-2-phenylsilabut-2-enal in accordance with claim 12.
Claim 26
Dependent Claim
7 words
Z; 1,1,1-triethoxy-2-phenylsilabut-2-enal in accordance with claim 12.
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