US5530152A
Expired / Lapsed
US
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Method for manufacturing organosilanes
Assignee: EIDP Inc
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Filing: 1995-02-17
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Granted: 1996-06-25
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Expires: 2015-02-17
Abstract
Abstract Disclosed is a process for manufacturing organosilanes by contacting an olefin with a silane in the presence of an azo compound.
Inventors
- 👤 Hasan Dindi
- 👤 Stuart N. Milligan
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 12:02
CPC Classifications
C; C07; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/12; C07F7/14
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
230 words
A process for preparing an organosilane comprising contacting (i) at least one olefin having an olefinic double bond aliphatic in character between two carbons and having hydrogen on at least one of the doubly bonded carbons, with (ii) at least one silane of the formula: H.sub.a SiR.sub.b X.sub.c wherein H is hydrogen; R is independently selected from the group consisting of alkyl, alkoxy, aryl, aryloxy, oxysilyl, cycloalkyl and perhaloalkyl; X is a halogen selected from the group consisting of fluoride, chloride, bromide and iodide; a is independently 1 to 3; b and c are independently 0 to 3; and a+b+c=4; in the presence of (iii) at least one azo compound of the formula: R1-N=N-R2 wherein R1 and R2 are the same or different and are selected from the group consisting of cyanoalkyl, cyanocycloalkyl, alkoxycyanoalkyl, heterocyclo alkyl, alkyl alkoxy esters, aryl alkoxy esters, alkyl aroyl esters, aryl aroyl ester, substituted and unsubstituted alkyl amides, cyanocarboxylic acids and carbamoyl; wherein (iii) is in the amount of about 5% or less, based on a stoichiometric amount of reactants, under pressure in the range of about 30 to about 400 psig at a temperature in the range of about 50° to 120° C. for about 10 hours or less; and wherein (ii) is supplied in excess of about 0 to about 100% in amount stoichiometrically required for reacting (i) to produce (iv) the organosilane.
Claim 2
Dependent Claim
230 words
A process for preparing an organosilane comprising contacting (i) at least one olefin having an olefinic double bond aliphatic in character between two carbons and having hydrogen on at least one of the doubly bonded carbons, with (ii) at least one silane of the formula: H.sub.a SiR.sub.b X.sub.c wherein H is hydrogen; R is independently selected from the group consisting of alkyl, alkoxy, aryl, aryloxy, oxysilyl, cycloalkyl and perhaloalkyl; X is a halogen selected from the group consisting of fluoride, chloride, bromide and iodide; a is independently 1 to 3; b and c are independently 0 to 3; and a+b+c=4; in the presence of (iii) at least one azo compound of the formula: R1-N=N-R2 wherein R1 and R2 are the same or different and are selected from the group consisting of cyanoalkyl, cyanocycloalkyl, alkoxycyanoalkyl, heterocyclo alkyl, alkyl alkoxy esters, aryl alkoxy esters, alkyl aroyl esters, aryl aroyl ester, substituted and unsubstituted alkyl amides, cyanocarboxylic acids and carbamoyl; wherein (iii) is in the amount of about 5% or less, based on a stoichiometric amount of reactants, under pressure in the range of about 30 to about 400 psig at a temperature in the range of about 50° to 120° C. for about 10 hours or less; and wherein (ii) is supplied in excess of about 0 to about 100% in amount stoichiometrically required for reacting (i) to produce (iv) the organosilane.
Claim 3
Dependent Claim
29 words
The process of claim 1 wherein (i) has 2-20 carbons, (ii) is a halogenated silane and (iii) is selected from the group consisting of 2,2'-azobis(2,4-dimethylpentanenitrile), 2,2'-azobis(2-methylpropanenitrile), 2,2'-azobis(2-methylbutanenitrile), 1,1'-azobis(cyclohexanecarbonitrile), 2,2'-azobis(N,N'-dimethyleneisobutylramidine)dihydrochloride,
Claim 4
Dependent Claim
50 words
2'-azobis(2-amidinopropane)dihydrochloride, 2,2'-azobis(N,N'-dimethyleneisobutylramidine), 4,4'-azobis(4-cyanopentanoic acid), 2,2'-azobis(2-methyl-N-(1,1-bis(hydroxymethyl)-2-hydroxyethyl)propionamide) 2,2'-azobis(2-methyl-N-(1, 1-bis(hydroxymethyl)ethyl)propionamide), 2,2'-azobis(2-methyl-N-(2-hydroxyethyl)propionamide), 2,2'-azobis( isobutyramide )dihydrate, 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile), dimethyl-2,2'-azobisisobutyrate, 2-(carbamoylazo)isobutyronitrile, 2,2'-azobis(2,4,4-dimethylpentane), 2-phenylazo-2,4-dimethyl-4-methoxyvaleronitrile, and 2,2'-azobis(2-methylpropane). wherein the pressure is in the range of about 50 to about 200 psig at a temperature in the range of about 80° to 110° C. for about 8 hours or less.
Claim 5
Dependent Claim
50 words
2'-azobis(2-amidinopropane)dihydrochloride, 2,2'-azobis(N,N'-dimethyleneisobutylramidine), 4,4'-azobis(4-cyanopentanoic acid), 2,2'-azobis(2-methyl-N-(1,1-bis(hydroxymethyl)-2-hydroxyethyl)propionamide) 2,2'-azobis(2-methyl-N-(1, 1-bis(hydroxymethyl)ethyl)propionamide), 2,2'-azobis(2-methyl-N-(2-hydroxyethyl)propionamide), 2,2'-azobis( isobutyramide )dihydrate, 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile), dimethyl-2,2'-azobisisobutyrate, 2-(carbamoylazo)isobutyronitrile, 2,2'-azobis(2,4,4-dimethylpentane), 2-phenylazo-2,4-dimethyl-4-methoxyvaleronitrile, and 2,2'-azobis(2-methylpropane). wherein the pressure is in the range of about 50 to about 200 psig at a temperature in the range of about 80° to 110° C. for about 8 hours or less.
Claim 6
Dependent Claim
43 words
The process of claim 2 wherein (i) is 1-octene, (ii) is trichlorosilane and (iii) is 2,2'-azobis(2-methylpropanenitrile) and the pressure is about 60 to 100 psig at a temperature in the range of about 90° to 95° C. for about 3 to 5 hours.
Claim 7
Dependent Claim
43 words
The process of claim 2 wherein (i) is 1-octene, (ii) is trichlorosilane and (iii) is 1,1'-azobis(cyclohexanecarbonitrile) and the pressure is about 60 to 100 psig at a temperature in the range of about 100° to 105° C. for about 3 to 5 hours.
Claim 8
Dependent Claim
42 words
The process of claim 2 wherein (i) is 1-octene, (ii) is trichlorosilane and (iii) 2,2'-azobis(2-methylbutanenitrile) and the pressure is about 60 to 100 psig at a temperature in the range of about 90° to 95° C. for about 3 to 5 hours.
Claim 9
Dependent Claim
43 words
The process of claim 2 wherein (i) is 1-octadecene, (ii) is trichlorosilane and (iii) is 2,2'-azobis(2-methylpropanenitrile) and the pressure is about 60 to 100 psig at a temperature in the range of about 90° to 950° C. for about 3 to 5 hours.
Claim 10
Dependent Claim
43 words
The process of claim 2 wherein (i) is 1-octadecene, (ii) is trichlorosilane and (iii) is 1,1'-azobis(cyclohexanecarbonitrile) and the pressure is about 60 to 100 psig at a temperature in the range of about 100° to 105° C. for about 3 to 5 hours.
Claim 11
Dependent Claim
42 words
The process of claim 2 wherein (i) is 1-octadecene, (ii) is trichlorosilane and (iii) 2,2'-azobis(2-methylbutanenitrile) and the pressure is about 60 to 100 psig at a temperature in the range of about 90° to 95° C. for about 3 to 5 hours.
Claim 12
Dependent Claim
20 words
The process of any of claims 1-8 wherein the reactants are mixed together in a reaction vessel prior to heating.
Claim 13
Dependent Claim
22 words
The process of any of claims 1-8 wherein the olefin and azo compounds are added slowly to the silane during the reaction.
Claim 14
Dependent Claim
31 words
The process of any of claims 1-8, wherein the organosilane is (iv) an alkylhalosilane and, further comprising the step of reacting (iv) with (v) an alcohol to (vi) a corresponding alkylalkoxysilane.
Claim 15
Dependent Claim
16 words
The process of claim 11 wherein (iv) is octyltrichlorosilane, (v) is ethanol and (vi) is octyltriethoxysilane.
Claim 16
Dependent Claim
100 words
A process for preparing an organolsilane comprising adding, in sequence, a silane of the formula H.sub.a SiR.sub.b X.sub.c wherein H is hydrogen; R is independently selected from the group consisting of alkyl, alkoxy, aryl, aryloxy, oxysilyl, cycloalkyl and perhaloalkyl; X is a halogen selected from the group consisting of fluoride, chloride, bromide and iodide; a is independently 1 to 3; b and c are independently 0 to 3; and a+b+c=4; in excess of 50% or less, and an azo compound selected from the group consisting of 2,2'-azobis(2-methylpropanenitrile) 2,2'-azobis(2-methylbutanenitrile) and 1,1'-azobis(cyclohexanecarbonitrile) to an olefin under pressure of 200 psig and less.
Claim 17
Dependent Claim
100 words
A process for preparing an organolsilane comprising adding, in sequence, a silane of the formula H.sub.a SiR.sub.b X.sub.c wherein H is hydrogen; R is independently selected from the group consisting of alkyl, alkoxy, aryl, aryloxy, oxysilyl, cycloalkyl and perhaloalkyl; X is a halogen selected from the group consisting of fluoride, chloride, bromide and iodide; a is independently 1 to 3; b and c are independently 0 to 3; and a+b+c=4; in excess of 50% or less, and an azo compound selected from the group consisting of 2,2'-azobis(2-methylpropanenitrile) 2,2'-azobis(2-methylbutanenitrile) and 1,1'-azobis(cyclohexanecarbonitrile) to an olefin under pressure of 200 psig and less.
Claim 18
Dependent Claim
119 words
A process for preparing an organosilane comprising contacting (i) an olefin with (ii) a silane of the formula H.sub.a SiR.sub.b X.sub.c wherein H is hydrogen; R is independently selected from the group consisting of alkyl, alkoxy, aryl, aryloxy, oxysilyl, cycloalkyl and perhaloalkyl; X is a halogen selected from the group consisting of fluoride, chloride, bromide and iodide; a is independently 1 to 3; b and c are independently 0 to 3; and a+b+c=4; supplied in excess of 50% or less in an amount stoichoimetrically required for reacting (i), in the presence of (iii) at least one azo compound selected from the group consisting of 2,2'-azobis(2-methylpropanenitrile), 2,2'-azobis(2-methylbutanenitrile) and 1,1'-azobis(cyclohexanecarbonitrile), and (iv) an organosilane, under pressure of 200 psig and less.
Claim 19
Dependent Claim
119 words
A process for preparing an organosilane comprising contacting (i) an olefin with (ii) a silane of the formula H.sub.a SiR.sub.b X.sub.c wherein H is hydrogen; R is independently selected from the group consisting of alkyl, alkoxy, aryl, aryloxy, oxysilyl, cycloalkyl and perhaloalkyl; X is a halogen selected from the group consisting of fluoride, chloride, bromide and iodide; a is independently 1 to 3; b and c are independently 0 to 3; and a+b+c=4; supplied in excess of 50% or less in an amount stoichoimetrically required for reacting (i), in the presence of (iii) at least one azo compound selected from the group consisting of 2,2'-azobis(2-methylpropanenitrile), 2,2'-azobis(2-methylbutanenitrile) and 1,1'-azobis(cyclohexanecarbonitrile), and (iv) an organosilane, under pressure of 200 psig and less.
References Cited (Backward Citations)
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1999-06-25 | 1999-12-25 | 2000-06-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2003-06-25 | 2003-12-25 | 2004-06-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2007-06-25 | 2007-12-25 | 2008-06-25 | $7700.00 | Window Closed / Lapsed |