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US4526996A
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Process for the preparation of N-substituted aminoalkylsilanes
Assignee: General Electric Co
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Filing: 1984-06-19
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Granted: 1985-07-02
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Expires: 2004-06-19
Abstract
Abstract N-substituted aminoalkylsilanes are obtained via a selective process which comprises reacting a cyanoalkylsilane with a primary or secondary amine in the presence of a heterogeneous hydrogenation catalyst selected from the group consisting of rhodium, platinum and palladium.
Inventors
- 👤 John A. Kilgour
- 👤 Herbert E. Petty
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 09:01
CPC Classifications
C; C07; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/18; C07F7/1804; C07F7/1872; C07F7/1892
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
40 words
A process for selectively preparing an N-substituted aminoalkylsilane which comprises reacting a primary or secondary amine with a cyanoalkylsilane in the presence of hydrogen gas and a heterogeneous hydrogenation catalyst selected from the group consisting of rhodium, platinum and palladium.
Claim 2
Dependent Claim
40 words
A process for selectively preparing an N-substituted aminoalkylsilane which comprises reacting a primary or secondary amine with a cyanoalkylsilane in the presence of hydrogen gas and a heterogeneous hydrogenation catalyst selected from the group consisting of rhodium, platinum and palladium.
Claim 3
Dependent Claim
127 words
The process of claim 1 wherein the primary or secondary amine is selected from the group of amines having the structural formula: ##STR4## wherein R 1 and R 2 are individually substituted or unsubstituted alkyl or aryl groups having from 1 to 12 carbon atoms; R 3 and R 4 are individually hydrogen or a substituted or unsubstituted alkyl, aryl or alkyleneamine group containing 1 to 12 carbon atoms; A is a divalent 4, 5, or 6 membered chain wherein the chain members are only carbon or carbon and one member selected from the group or oxygen, sulfur, and an amino moiety; x is an integer from 0 to 3; n is an integer from 2 to 4; and z is an integer from 1 to 2.
Claim 4
Dependent Claim
33 words
The process of claim 1 wherein the cyanoalkylsilane is of the formula: (R.sup.1 O).sub.x (R.sup.2).sub.3-x Si(C.sub.n-1 H.sub.2n-2)CN wherein R 1 , R 2 , n and x are as defined in claim 2.
Claim 5
Dependent Claim
19 words
The process of claim 1 wherein the ratio of primary or secondary amine to cyanoalkylsilane is 1 to 10.
Claim 6
Dependent Claim
16 words
The process of claim 1 wherein the hydrogen pressure is from 50 psig to 1000 psig.
Claim 7
Dependent Claim
14 words
The process of claim 1 wherein the reaction temperature is 25° to 180° C.
Claim 8
Dependent Claim
10 words
The process of claim 1 wherein the catalyst is rhodium.
Claim 9
Dependent Claim
10 words
The process of claim 1 wherein the catalyst is platinum.
Claim 10
Dependent Claim
10 words
The process of claim 1 wherein the catalyst is palladium.
Claim 11
Dependent Claim
13 words
The process of claim 1 wherein the reaction takes place in a solvent.
Claim 12
Dependent Claim
15 words
The process of claim 10 wherein the solvent is an aromatic hydrocarbon or aliphatical alcohol.
Claim 13
Dependent Claim
13 words
The process of claim 11 wherein the aliphatic alcohol is methanol or ethanol.
Claim 14
Dependent Claim
215 words
A process for selectively preparing an N-substituted aminoalkylsilane of the formula: ##STR5## which process comprises reacting a primary or secondary amine selected from the group of amines consisting of: ##STR6## with a cyanoalkylsilane of the formula: (R.sup.1 O).sub.x (R.sup.2).sub.3-x Si(C.sub.n-1 H.sub.2n-2)CN wherein R 1 and R 2 are individually substituted or unsubstituted alkyl or aryl groups having from 1 to 12 carbon atoms; R 3 and R 4 are individually hydrogen or a substituted or unsubstituted alkyl, aryl or alkyleneamine group containing 1 to 12 carbon atoms; A is a divalent 4, 5, or 6 membered chain wherein the chain members are only carbon or carbon and one member selected from the group of oxygen, sulfur, and an amino moiety; x is an integer from 0 to 3; n is an integer from 2 to 4; and z is an integer from 1 to 2; at 25° to 180° C. in the presence of hydrogen gas, said hydrogen gas having a pressure of from 50 psig to 1000 psig, and in the presence of a heterogeneous hydrogenation catalyst selected from the group consisting of rhodium, platium and palladium, where the ratio of primary or secondary amine to cyanoalkylsilane is 1 to 10 and where the reaction occurs in an aromatic hydrocarbon or aliphatic alcohol solvent.
Claim 15
Dependent Claim
215 words
A process for selectively preparing an N-substituted aminoalkylsilane of the formula: ##STR5## which process comprises reacting a primary or secondary amine selected from the group of amines consisting of: ##STR6## with a cyanoalkylsilane of the formula: (R.sup.1 O).sub.x (R.sup.2).sub.3-x Si(C.sub.n-1 H.sub.2n-2)CN wherein R 1 and R 2 are individually substituted or unsubstituted alkyl or aryl groups having from 1 to 12 carbon atoms; R 3 and R 4 are individually hydrogen or a substituted or unsubstituted alkyl, aryl or alkyleneamine group containing 1 to 12 carbon atoms; A is a divalent 4, 5, or 6 membered chain wherein the chain members are only carbon or carbon and one member selected from the group of oxygen, sulfur, and an amino moiety; x is an integer from 0 to 3; n is an integer from 2 to 4; and z is an integer from 1 to 2; at 25° to 180° C. in the presence of hydrogen gas, said hydrogen gas having a pressure of from 50 psig to 1000 psig, and in the presence of a heterogeneous hydrogenation catalyst selected from the group consisting of rhodium, platium and palladium, where the ratio of primary or secondary amine to cyanoalkylsilane is 1 to 10 and where the reaction occurs in an aromatic hydrocarbon or aliphatic alcohol solvent.
Claim 16
Dependent Claim
12 words
The process of claim 13 wherein the solvent is methanol or ethanol.
Claim 17
Dependent Claim
28 words
The process of claim 13 wherein the catalyst is rhodium, the temperature is from 100° to 150° C. and the hydrogen pressure is from 400 to 700 psig.
Claim 18
Dependent Claim
28 words
The process of claim 13 wherein the catalyst is platinum, the temperature is from 130° to 170° C. and the hydrogen pressure is from 300 to 750 psig.
Claim 19
Dependent Claim
34 words
The process of claim 13 wherein the catalyst is palladium, the temperature is from 150° to 170° C., the hydrogen pressure is 50 to 750 psig and in the absence of an alkanal solvent.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-07-01 | 1988-12-31 | 1989-07-02 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-07-01 | 1992-12-31 | 1993-07-02 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-07-01 | 1996-12-31 | 1997-07-02 | $7700.00 | Window Closed / Lapsed |