US4556722A
Expired / Lapsed
US
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Process for the preparation of aminopropylalkoxysilanes
Assignee: General Electric Co
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Filing: 1985-03-28
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Granted: 1985-12-03
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Expires: 2005-03-28
Abstract
Abstract A process for the preparation of aminopropylalkoxysilanes comprising the hydrosilation of allylamines (including N-substituted allylamines) with alkoxyhydrosilanes in the presence of a rhodium-triorganophosphorus-complex catalyst. This process significantly increases the gamma- to beta-isomer ratio of the final product of the addition of allylamines to alkoxyhydrosilanes.
Inventors
- 👤 Jennifer M. Quirk
- 👤 Scot Turner
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 03:19
CPC Classifications
C; C07; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/18; C07F7/1804; C07F7/1872; C07F7/1876
Claims Analysis
Total Claims: 31
Claim 1
Independent Claim
159 words
A process for preparing an aminopropylalkoxysilane having the formula ##STR4## wherein R and R 1 individually are C 1 -C 6 alkyl; R 2 and R 3 individually are hydrogen, C 1 -C 10 alkyl, C 1 -C 10 alkenyl, --CH 2 CH 2 NHCH 2 CH 2 NH 2 , --CH 2 CH 2 NH 2 , phenyl or substituted phenyl; R 4 is hydrogen or C 1 -C 6 alkyl; and a is 0, 1 or 2, which process comprises reacting: a. a silane having the formula ##STR5## wherein R, R 1 and a are as defined above; b. with an amine having the following formula: ##STR6## wherein R 2 , R 3 and R 4 are as defined above; c. in the presence of a catalytic amount of a rhodium-triorganophosphorus-complex catalyst comprising rhodium in a complex combination with a triorganophosphorus ligand wherein each organo moiety contains from 1 to 18 carbon atoms, to produce the aminopropylalkoxysilane.
Claim 2
Dependent Claim
159 words
A process for preparing an aminopropylalkoxysilane having the formula ##STR4## wherein R and R 1 individually are C 1 -C 6 alkyl; R 2 and R 3 individually are hydrogen, C 1 -C 10 alkyl, C 1 -C 10 alkenyl, --CH 2 CH 2 NHCH 2 CH 2 NH 2 , --CH 2 CH 2 NH 2 , phenyl or substituted phenyl; R 4 is hydrogen or C 1 -C 6 alkyl; and a is 0, 1 or 2, which process comprises reacting: a. a silane having the formula ##STR5## wherein R, R 1 and a are as defined above; b. with an amine having the following formula: ##STR6## wherein R 2 , R 3 and R 4 are as defined above; c. in the presence of a catalytic amount of a rhodium-triorganophosphorus-complex catalyst comprising rhodium in a complex combination with a triorganophosphorus ligand wherein each organo moiety contains from 1 to 18 carbon atoms, to produce the aminopropylalkoxysilane.
Claim 3
Dependent Claim
16 words
A process as recited in claim 1 wherein the triorganophosphorus ligand is trialkylphosphite, triarylphosphite or triarylphosphine.
Claim 4
Dependent Claim
13 words
A process as recited in claim 2 wherein the triorganophosphorus ligand is triarylphosphine.
Claim 5
Dependent Claim
12 words
A process as recited in claim 3 wherein the triarylphosphine is triphenylphosphine.
Claim 6
Dependent Claim
28 words
A process as recited in claim 1 wherein the process is conducted in the presence of at least 2 equivalents of free triorganophosphorus ligand per equivalent of rhodium.
Claim 7
Dependent Claim
28 words
A process as recited in claim 5 wherein the process is conducted in the presence of at least 10 equivalents of free triorganophosphorus ligand per equivalent of rhodium.
Claim 8
Dependent Claim
28 words
A process as recited in claim 6 wherein the process is conducted in the presence of at least 50 equivalents of free triorganophosphorus ligand per equivalent of rhodium.
Claim 9
Dependent Claim
23 words
A process as recited in claim 1 wherein the reaction is conducted at a temperature of about 100° C. to about 175° C.
Claim 10
Dependent Claim
23 words
A process as recited in claim 8 wherein the reaction is conducted at a temperature of about 110° C. to about 135° C.
Claim 11
Dependent Claim
36 words
A process as recited in claim 1 wherein the rhodium-triorganophosphorus-complex catalyst is present in a concentration of from about 40 to about 200 ppm rhodium based on the total combined weight of the silane and amine.
Claim 12
Dependent Claim
35 words
A process as recited in claim 10 wherein the catalyst is present in a concentration of from about 50 to about 100 ppm rhodium based on the total combined weight of the silane and amine.
Claim 13
Dependent Claim
19 words
A process as recited in claim 1 wherein the ratio of silane to amine is between 1.5:1 to 1:1.5.
Claim 14
Dependent Claim
19 words
A process as recited in claim 1 wherein the ratio of silane to amine is between 1.1:1 to 1:1.1.
Claim 15
Dependent Claim
24 words
A process as recited in claim 1 wherein the gamma- to beta-isomer ratio of the aminopropylalkoxysilane produced is at least about 25 to 1.
Claim 16
Dependent Claim
24 words
A process as recited in claim 1 wherein the gamma- to beta-isomer ratio of the aminopropylalkoxysilane produced is at least about 50 to 1.
Claim 17
Dependent Claim
132 words
A process for preparing an aminopropylalkoxysilane having the formula: ##STR7## wherein R and R 1 individually are C 1 -C 4 alkyl; R 2 and R 3 individually are hydrogen or C 1 -C 4 alkyl; R 4 is hydrogen or methyl; and a is 0, 1 or 2, which process comprises reacting: a. a silane having the formula ##STR8## wherein R, R 1 and a are as defined above; b. with an amine having the formula: ##STR9## wherein R 2 , R 3 and R 4 are as defined above; c. in the presence of a catalytic amount of a rhodium-triphenylphosphine-complex comprising rhodium in a complex combination with triphenylphosphine; and d. in the presence of free triphenylphosphine, e. at a temperature of at least about 100° C., to produce the aminopropylalkoxysilane.
Claim 18
Dependent Claim
132 words
A process for preparing an aminopropylalkoxysilane having the formula: ##STR7## wherein R and R 1 individually are C 1 -C 4 alkyl; R 2 and R 3 individually are hydrogen or C 1 -C 4 alkyl; R 4 is hydrogen or methyl; and a is 0, 1 or 2, which process comprises reacting: a. a silane having the formula ##STR8## wherein R, R 1 and a are as defined above; b. with an amine having the formula: ##STR9## wherein R 2 , R 3 and R 4 are as defined above; c. in the presence of a catalytic amount of a rhodium-triphenylphosphine-complex comprising rhodium in a complex combination with triphenylphosphine; and d. in the presence of free triphenylphosphine, e. at a temperature of at least about 100° C., to produce the aminopropylalkoxysilane.
Claim 19
Dependent Claim
20 words
A process as recited in claim 16 wherein a is 0 and R and R 1 are methyl or ethyl.
Claim 20
Dependent Claim
16 words
A process as recited in claim 17 wherein R 2 and R 3 are both hydrogen.
Claim 21
Dependent Claim
24 words
A process as recited in claim 16 wherein the gamma- to beta-isomer ratio of the aminopropylalkoxysilane produced is at least about 25 to 1.
Claim 22
Dependent Claim
24 words
A process as recited in claim 16 wherein the gamma- to beta-isomer ratio of the aminopropylalkoxysilane produced is at least about 50 to 1.
Claim 23
Dependent Claim
27 words
A process as recited in claim 16 wherein the process is conducted in the presence of at least 50 equivalents of free triphenylphosphine per equivalent of rhodium.
Claim 24
Dependent Claim
27 words
A process as recited in claim 16 wherein the process is conducted at a temperature in the range of from about 100° C. to about 175° C.
Claim 25
Dependent Claim
36 words
A process as recited in claim 16 wherein the rhodium-triphenylphosphine-complex catalyst is present in a concentration of from about 50 to about 100 ppm rhodium based on the total combined weight of the silane and amine.
Claim 26
Dependent Claim
17 words
A process as recited in claim 16 wherein the catalyst is rhodium hydridocarbonyltris-(triphenylphosphine) or rhodium hydrido-tetrakis (triphenylphosphine).
Claim 27
Dependent Claim
27 words
A process as recited in claim 16 wherein the rhodium-triphenylphosphine-complex catalyst is formed by the addition of rhodium dicarbonyl acetylacetonate and free triphenylphosphine to the reaction mixture.
Claim 28
Dependent Claim
22 words
A process as recited in claim 25 wherein at least about 50 equivalents of free triphenylphosphine are added per equivalent of rhodium.
Claim 29
Dependent Claim
22 words
A process as recited in claim 26 wherein at least about 200 equivalents of free triphenylphosphine are added per equivalent of rhodium.
Claim 30
Dependent Claim
28 words
A process as recited in claim 16 wherein the rhodium-triphenylphosphine-complex catalyst is formed by the addition of rhodium carbonyl triphenylphosphine acetylacetonate and free triphenylphosphine to the reaction mixture.
Claim 31
Dependent Claim
21 words
A process as recited in claim 28 wherein at least 50 equivalents of free triphenylphosphine are added per equivalent of rhodium.
References Cited (Backward Citations)
US2762823A
Cited
US3527809A
Cited
US3665027A
Cited
US3657304A
Cited
US3864373A
Cited
US4148830A
Cited
US4481364A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-12-02 | 1989-06-03 | 1989-12-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-12-02 | 1993-06-03 | 1993-12-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-12-02 | 1997-06-03 | 1997-12-03 | $7700.00 | Window Closed / Lapsed |