US4634787A
Expired / Lapsed
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Process for preparing (2,2,2-trihalo-1, 1-dihydrocarbyl-ethoxy) trihydrocarbylsilanes
Assignee: Dow Chemical Co
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Filing: 1985-11-08
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Granted: 1987-01-06
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Expires: 2005-11-08
Abstract
Abstract A process for forming trihalomethylsiloxanes by contacting a trihalosilane with a carbonyl in the presence of the fluoride ion. These compounds are used to form α-substituted acid chlorides.
Inventors
- 👤 Pen-Chung Wang
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 00:57
CPC Classifications
C; C07; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/18; C07F7/1804; C07F7/1872; C07F7/188
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
169 words
A process of forming (2,2,2-trihalo-1,1-dihydrocarbylethoxy)trihydrocarbylsilanes (Wang compounds) without forming stoichiometric amounts of by-products comprising contacting (1) a silane of the formula X.sub.3 CSi(R.sup.1).sub.3 (I) in which X is independently halo and each R 1 is independently a monovalent hydrocarbon radical, or one R 1 is a monovalent hydrocarbon radical, and the remaining two R 1 are collectively a divalent hydrocarbon radical, or all three R 1 are collectively a trivalent hydrocarbon radical, with (2) a carbonyl of the formula ##STR15## in which each R 2 is independently hydrogen or a monovalent hydrocarbon radical, provided at the most, one R 2 is hydrogen, or both R 2 are collectively a hydrocarbylene radical, in the presence of a catalytic amount of the fluoride ion under conditions sufficient to produce a Wang compound of the formula, ##STR16## in which X, R 1 and R 2 are as previously defined, said hydrocarbon radicals represented by R 1 and R 2 may contain one or more substituents and may contain one or more heteroatoms.
Claim 2
Dependent Claim
169 words
A process of forming (2,2,2-trihalo-1,1-dihydrocarbylethoxy)trihydrocarbylsilanes (Wang compounds) without forming stoichiometric amounts of by-products comprising contacting (1) a silane of the formula X.sub.3 CSi(R.sup.1).sub.3 (I) in which X is independently halo and each R 1 is independently a monovalent hydrocarbon radical, or one R 1 is a monovalent hydrocarbon radical, and the remaining two R 1 are collectively a divalent hydrocarbon radical, or all three R 1 are collectively a trivalent hydrocarbon radical, with (2) a carbonyl of the formula ##STR15## in which each R 2 is independently hydrogen or a monovalent hydrocarbon radical, provided at the most, one R 2 is hydrogen, or both R 2 are collectively a hydrocarbylene radical, in the presence of a catalytic amount of the fluoride ion under conditions sufficient to produce a Wang compound of the formula, ##STR16## in which X, R 1 and R 2 are as previously defined, said hydrocarbon radicals represented by R 1 and R 2 may contain one or more substituents and may contain one or more heteroatoms.
Claim 3
Dependent Claim
12 words
The process of claim 1 in which each R 1 is methyl.
Claim 4
Dependent Claim
13 words
The process of claim 1 in which X is independently chloro or bromo.
Claim 5
Dependent Claim
17 words
The process of claim 3 in which each X is the same and is chloro or bromo.
Claim 6
Dependent Claim
10 words
The process of claim 4 in which X is chloro.
Claim 7
Dependent Claim
12 words
The process of claim 1 in which one R 2 is hydrogen.
Claim 8
Dependent Claim
19 words
The process of claim 6 in which the carbonyl is selected from the group consisting of benzaldehyde and 4-methoxybenzaldehyde.
Claim 9
Dependent Claim
11 words
The process of claim 7 in which the carbonyl is benzaldehyde.
Claim 10
Dependent Claim
18 words
The process of claim 1 in which the contact is in the presence of one or more diluents.
Claim 11
Dependent Claim
26 words
The process of claim 9 in which the diluents are tetrahydrofuran, acetonitrile, nitromethane, toluene, benzene, the xylenes, chlorobenylene, benzonitrile, glyme, diglyme, methyl tert-butyl ether or hexane.
Claim 12
Dependent Claim
11 words
The process of claim 10 in which the diluent is tetrahydrofuran.
Claim 13
Dependent Claim
12 words
The process of claim 1 in which the reaction mixture is heated.
Claim 14
Dependent Claim
26 words
The process of claim 12 in which the temperature of the reaction mixture is between about 0° C. and the reflux temperature of the reaction mixture.
Claim 15
Dependent Claim
26 words
The process of claim 13 in which the temperature of the reaction mixture is between about 20° C. and the reflux temperature of the reaction mixture.
Claim 16
Dependent Claim
14 words
The process of claim 1 in which the reaction proceeds under a nitrogen blanket.
Claim 17
Dependent Claim
32 words
The process of claim 1 in which the fluoride ion is provided by the use of a salt selected from the group consisting of KF, NaF, CaF 2 and Bu 4 NF.
Claim 18
Dependent Claim
13 words
The process of claim 16 in which the salt is Bu 4 NF.
Claim 19
Dependent Claim
21 words
The process of claim 1 in which the yield is greater than about 70 mole percent based on the combined reactants.
Claim 20
Dependent Claim
23 words
The process of claim 15 in which the silane is trichloromethyl trimethyl silane and the fluoride ion is provided by Bu 4 NF.
Claim 21
Dependent Claim
26 words
The process of claim 19 in which the temperature of the reaction mixture is between about 0° C. and the reflux temperature of the reaction mixture.
Claim 22
Dependent Claim
15 words
The process of claim 1 in which each R 2 is a monovalent hydrocarbon radical.
Claim 23
Dependent Claim
21 words
The process of claim 21 in which the carbonyl is selected from the group consisting of cyclopentanone, cyclohexanone, pentan-3-one and quinone.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1990-01-05 | 1990-07-07 | 1991-01-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-01-05 | 1994-07-07 | 1995-01-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-01-05 | 1998-07-07 | 1999-01-06 | $7700.00 | Window Closed / Lapsed |