US4709054A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Silylation method and organic silanes made therefrom
Assignee: General Electric Co
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Filing: 1985-08-13
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Granted: 1987-11-24
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Expires: 2005-08-13
Abstract
Abstract A method is provided for silylating organic substrates, utilizing a halogenated polysilane, such as 1,1,2,2-tetrachloro dimethyldisilane and an aromatic acyl halide, for example, trimellitic anhydride acid chloride in the presence of a transition metal catalyst.
Inventors
- 👤 Jonathan D. Rich
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 20:16
CPC Classifications
C; C07; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/12; C07F7/121; C07F7/122
Claims Analysis
Total Claims: 37
Claim 1
Independent Claim
119 words
A method for making organic silanes which comprises (A) effecting reaction between aromatic acyl halide of the formula ##STR6## and halogenated polysilane of the formula ##STR7## in the presence of an effective amount of a transition metal catalyst, and (B) thereafter recovering organic silane from the resulting mixture of (A), where X is a halogen radical, R is selected from X, hydrogen, C.sub.(1-13) monovalent hydrocarbon radicals, substituted C.sub.(1-13) monovalent hydrocarbon radicals and divalent --O--, --S-- radicals and mixtures thereof, which can form .tbd.SiOSi.tbd. and .tbd.SiSSi.tbd. connecting groups, R 1 is a C.sub.(6-20) monovalent or polyvalent aromatic organic radical, n is an integer equal to 1 to 50 inclusive, and m is an integer equal to 1 to 4 inclusive.
Claim 2
Independent Claim
119 words
A method for making organic silanes which comprises (A) effecting reaction between aromatic acyl halide of the formula ##STR6## and halogenated polysilane of the formula ##STR7## in the presence of an effective amount of a transition metal catalyst, and (B) thereafter recovering organic silane from the resulting mixture of (A), where X is a halogen radical, R is selected from X, hydrogen, C.sub.(1-13) monovalent hydrocarbon radicals, substituted C.sub.(1-13) monovalent hydrocarbon radicals and divalent --O--, --S-- radicals and mixtures thereof, which can form .tbd.SiOSi.tbd. and .tbd.SiSSi.tbd. connecting groups, R 1 is a C.sub.(6-20) monovalent or polyvalent aromatic organic radical, n is an integer equal to 1 to 50 inclusive, and m is an integer equal to 1 to 4 inclusive.
Claim 3
Dependent Claim
13 words
A method in accordance with claim 1, where the halogenated polysilane is 1,1,2,2-tetrachlorodimethyldisilane.
Claim 4
Dependent Claim
17 words
A method in accordance with claim 1, where the aromatic acyl halide is trimellitic anhydride acid chloride.
Claim 5
Dependent Claim
15 words
A method in accordance with claim 1, where the aromatic acyl halide is terephthaloyl chloride.
Claim 6
Dependent Claim
13 words
A method in accordance with claim 1, where the halogenated polysilane is 1,2-dichlorotetramethyldisilane.
Claim 7
Dependent Claim
21 words
A method in accordance with claim 1, where the transition metal catalyst is a cocatalyst consisting of bis(benzonitrile)palladium chloride and triphenylphosphine.
Claim 8
Dependent Claim
12 words
A method in accordance with claim 1 conducted in a continuous manner.
Claim 9
Dependent Claim
16 words
A method in accordance with claim 1, where the transition metal catalyst is palladium on carbon.
Claim 10
Dependent Claim
19 words
An organic silane selected from the class consisting of 2-chlorodimethylsilylbenzoylchloride 2-dichloromethylsilylbenzoylchloride, 2-trichlorosilylbenzoylchloride, 3-chlorodimethylsilylbenzoylchloride, 3-dichlorosilylbenzoyl chloride, 3-trichlorosilylbenzoyl chloride, 4-dichloromethylsilylbenzoylchloride, 4-trichlorosilylbenzoylchloride.
Claim 11
Dependent Claim
19 words
An organic silane selected from the class consisting of 2-chlorodimethylsilylbenzoylchloride 2-dichloromethylsilylbenzoylchloride, 2-trichlorosilylbenzoylchloride, 3-chlorodimethylsilylbenzoylchloride, 3-dichlorosilylbenzoyl chloride, 3-trichlorosilylbenzoyl chloride, 4-dichloromethylsilylbenzoylchloride, 4-trichlorosilylbenzoylchloride.
Claim 12
Dependent Claim
6 words
2-chlorodimethylsilylbenzoylchloride in accordance with claim 9.
Claim 13
Dependent Claim
6 words
2-dichloromethylsilylbenzoylchloride in accordance with claim 9.
Claim 14
Dependent Claim
6 words
2-trichlorosilylbenzoylchloride in accordance with claim 9.
Claim 15
Dependent Claim
6 words
3-chlorodimethylsilylbenzoylchloride in accordance with claim 9.
Claim 16
Dependent Claim
6 words
3-dichloromethylsilylbenzoylchloride in accordance with claim 9.
Claim 17
Dependent Claim
6 words
3-trichlorosilylbenzoylchloride in accordance with claim 9.
Claim 18
Dependent Claim
6 words
4-dichloromethylsilylbenzoylchloride in accordance with claim 9.
Claim 19
Dependent Claim
6 words
4-trichlorosilylbenzoylchloride in accordance with claim 9.
Claim 20
Dependent Claim
15 words
Chlorosilylphthalic anhydrides having the formula ##STR8## where n is equal to 1 to 3 inclusive.
Claim 21
Dependent Claim
15 words
Chlorosilylphthalic anhydrides having the formula ##STR8## where n is equal to 1 to 3 inclusive.
Claim 22
Dependent Claim
3 words
The compound ##STR9##
Claim 23
Dependent Claim
3 words
The compound ##STR9##
Claim 24
Dependent Claim
3 words
The compound ##STR10##
Claim 25
Dependent Claim
3 words
The compound ##STR10##
Claim 26
Dependent Claim
3 words
The compound ##STR11##
Claim 27
Dependent Claim
3 words
The compound ##STR11##
Claim 28
Dependent Claim
5 words
Chlorodimethylsilylbenzonitriles having the formula ##STR12##
Claim 29
Dependent Claim
5 words
Chlorodimethylsilylbenzonitriles having the formula ##STR12##
Claim 30
Dependent Claim
13 words
A method in accordance with claim 1, where the aromatic acylhalide is nitrobenzoylchloride.
Claim 31
Dependent Claim
13 words
A method in accordance with claim 1, where the aromatic acylhalide is cyanobenzoylchloride.
Claim 32
Dependent Claim
16 words
A method in accordance with claim 1, where the aromatic acylhalide is N-n-butyltrimelitic imide acid chloride.
Claim 33
Dependent Claim
13 words
A method in accordance with claim 1, where the aromatic acylhalide is allylchloride.
Claim 34
Dependent Claim
13 words
A method in accordance with claim 1, where the aromatic acylhalide is isophthaloylchloride.
Claim 35
Dependent Claim
77 words
A method for making organic silane in accordance with claim 1 having the formula, R.sup.1 [--Si(R.sup.2).sub.2 X].sub.m, where X is a halogen radical, hydrogen, R 1 is a C.sub.(6-20) monovalent or polyvalent aromatic organic radical selected from hydrocarbon radicals and substituted hydrocarbon radicals, R 2 is selected from C.sub.(1-13) monovalent hydrocarbon radicals, substituted C.sub.(1-13) monovalent hydrocarbon radicals, and mixtures thereof, n is an integer equal to 1-15 inclusive, and m is an integer equal to 1-4 inclusive.
Claim 36
Dependent Claim
60 words
A method in accordance with claim 28, where the organic silane has the formula, ##STR13## where X is a halogen radical, R 3 is selected from C.sub.(1-13) monovalent hydrocarbon radicals, substituted C.sub.(1-13) monovalent hydrocarbon radicals, and mixtures thereof, and R 4 is a member selected from the class consisting of C.sub.(6-13) divalent aromatic radicals, and substituted C.sub.(6-13) divalent aromatic radicals.
Claim 37
Dependent Claim
9 words
The method of claim 1 where 1,4-(bis-chlorodimethylsilyl)benzene is produced.
References Cited (Backward Citations)
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US3299101A
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US3391109A
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US3855241A
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1990-11-23 | 1991-05-25 | 1991-11-24 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-11-23 | 1995-05-25 | 1995-11-24 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-11-23 | 1999-05-25 | 1999-11-24 | $7700.00 | Window Closed / Lapsed |