US5136069A
Expired / Lapsed
US
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Process for preparing vinylically-unsaturated compounds (II)
Assignee: Dow Chemical Co
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Filing: 1991-03-28
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Granted: 1992-08-04
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Expires: 2011-03-28
Abstract
Abstract A process for preparing a vinylically-unsaturated product compound comprises reacting a halogenated organic compound with a hydrolytically-stable, vinylically-unsaturated precursor compound in the presence of (a) a homogeneous zerovalent palladium catalyst complex, (b) an inorganic hydrogen halide acceptor and (c) diluent, wherein the diluent is water or an aqueous solution containing up to 95% by volume of an organic solvent. The halogenated organic compound is selected from aryl halides, benzyl halides or vinylic halides. The hydrolytically-stable, vinylically-unsaturated precursor compound is selected from hydrocarbon compounds or compounds containing at least one of an oxygen atom, a nitrogen atom, a sulfur atom, a phosphorus atom, silicon atom or a combination thereof.
Inventors
- 👤 Robert A. DeVries
- 👤 Hughie R. Frick, deceased
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 13:32
CPC Classifications
C; C07; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/0834; C07F7/0838; C07F7/0872; C07F7/0889; C07F7/20
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
92 words
A process for the preparation of a vinylically-unsaturated organo-silicon product compound, comprising reacting a halogenated organic compound with a hydrolytically-stable allyl, methallyl or vinyl organosilicon precursor compound in the presence of (a) a homogeneous zerovalent catalyst complex, formed from a palladium salt and an organophosphine or organoarsine; (b) an inorganic hydrogen halide acceptor and a diluent comprising water or an aqueous solution, containing up to 95% by volume of an organic solvent; and treating a resulting crude product mixture with an organic peroxide to remove organophosphine or organoarsine present in the mixture.
Claim 2
Dependent Claim
92 words
A process for the preparation of a vinylically-unsaturated organo-silicon product compound, comprising reacting a halogenated organic compound with a hydrolytically-stable allyl, methallyl or vinyl organosilicon precursor compound in the presence of (a) a homogeneous zerovalent catalyst complex, formed from a palladium salt and an organophosphine or organoarsine; (b) an inorganic hydrogen halide acceptor and a diluent comprising water or an aqueous solution, containing up to 95% by volume of an organic solvent; and treating a resulting crude product mixture with an organic peroxide to remove organophosphine or organoarsine present in the mixture.
Claim 3
Dependent Claim
12 words
The process of claim 1, wherein the organic peroxide is tert-butyl hydroperoxide.
Claim 4
Dependent Claim
19 words
The process of claim 1, including the step of chromatographing the thus-treated crude product mixture over silica or alumina.
Claim 5
Dependent Claim
20 words
The process of claim 1, wherein the inorganic hydrogen halide acceptor is an alkali metal acetate, propionate, hydroxide or carbonate.
Claim 6
Dependent Claim
14 words
The process of claim 1, wherein the diluent is an aqueous solution of N,N-dimethylformamide.
Claim 7
Dependent Claim
22 words
The process of claim 1, wherein the hydrolytically-stable, vinylically-unsaturated organosilicon precursor compound is a trialkylvinylsilane, wherein alkyl is of 1-6 carbon atoms.
Claim 8
Dependent Claim
49 words
The process of claim 1, wherein the hydrolytically-stable, vinylically-unsaturated organosilicon precursor compound is of the formula ##STR8## wherein each R is independently alkyl of 1-6 carbon atoms, cycloalkyl, aralkyl or aryl; each R 1 is independently vinyl, allyl or methallyl and n is an integer from 1 to 4500.
Claim 9
Dependent Claim
22 words
The process of claim 1, wherein the hydrolytically-stable, vinylically-unsaturated organosilicon precursor compound is [CH 2 ═CH--Si(CH 3 ) 2 ] 2 O.
Claim 10
Dependent Claim
18 words
The process of claim 1, wherein the vinylically-unsaturated product compound is a reaction product of 4-bromobenzocyclobutene and 1,1'-divinyltetramethyldisiloxane.
Claim 11
Dependent Claim
20 words
The process of claim 1, wherein the vinylically-unsaturated product compound is a reaction product of 4-bromobenzocyclobutene and an alpha,omegadivinyl(dimethylsiloxane) oligomer.
Claim 12
Dependent Claim
18 words
The process of claim 3, wherein the vinylically-unsaturated product compound is a reaction product of 4-bromobenzocyclobutene and 1,1'-divinyltetramethyldisiloxane.
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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) | 1995-08-04 | 1996-02-03 | 1996-08-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1999-08-04 | 2000-02-03 | 2000-08-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2003-08-04 | 2004-02-03 | 2004-08-04 | $7700.00 | Window Closed / Lapsed |