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Process for the preparation of N-substituted aminoalkylsilanes

Assignee: General Electric Co
•
Filing: 1984-06-19
•
Granted: 1985-07-02
•
Expires: 2004-06-19
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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)

US3033815A Cited
US3046295A Cited
US4045460A Cited

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

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