Patent US3715407A successfully refreshed from Google Patents.
US3715407A
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US
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Chlorination of ketonic acetyl groups
Assignee: General Electric Co
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Filing: 1971-03-01
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Granted: 1973-02-06
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Expires: 1991-03-01
Abstract
Abstract R3PCl2 converts the carbonyl group of ketones to chlorine containing groups which, combined with dehydrochlorination methods, provides a new synthetic route for the production of acetylenic compounds useful for making polymers. The R3PO produced in the reaction is reconverted to R3PCl2 by reaction with phosgene thus providing an economical process for converting ketones to chlorine derivatives and from thence to acetylenic derivatives. Each R is C1 20 alkyl, phenyl, lower alkylphenyl, halophenyl, phenoxyphenyl or naphthyl.
Inventors
- 👤 H Relles
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 15:51
CPC Classifications
C; C07; C07C; C07C17/00; C07C17/093; C07C17/18; Y; Y10; Y10S; Y10S585/00; Y10S585/929; Y10S585/93; Y10S585/935
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
101 words
The process of converting acetyl substituents to chlorine containing substituents selected from the group consisting of Alpha -chlorovinyl, Alpha -chloroethylidene and Alpha , Alpha -di-chloroethyl substituents in a ketone containing at least one said acetyl substituent as the ketonic moiety, the balance of the molecule having up to 20 carbon atoms and being selected from the group consisting of hydrocarbon, halohydrocarbon, aryl ether and haloaryl ether, which comprises reacting said ketone with a phosphorane having the formula R3PCl2 where each R is independently selected from the group consisting of C1 20 alkyl, phenyl, lower alkyl substituted phenyl, halophenyl, phenoxyphenyl and naphthyl.
Claim 2
Dependent Claim
101 words
The process of converting acetyl substituents to chlorine containing substituents selected from the group consisting of Alpha -chlorovinyl, Alpha -chloroethylidene and Alpha , Alpha -di-chloroethyl substituents in a ketone containing at least one said acetyl substituent as the ketonic moiety, the balance of the molecule having up to 20 carbon atoms and being selected from the group consisting of hydrocarbon, halohydrocarbon, aryl ether and haloaryl ether, which comprises reacting said ketone with a phosphorane having the formula R3PCl2 where each R is independently selected from the group consisting of C1 20 alkyl, phenyl, lower alkyl substituted phenyl, halophenyl, phenoxyphenyl and naphthyl.
Claim 3
Dependent Claim
43 words
The process of converting ketonic acetyl substituents to ethynyl substituents which comprises converting the acetyl substituents to chlorine containing substituents by the process of claim 1 and thereafter dehydrohalogenating the chlorine containing substituents to ethynyl substituents with a dehydrohalogenating agent under dehydrohalogenating conditions.
Claim 4
Dependent Claim
43 words
The process of using phosgene to convert ketonic acetyl substituents to chlorine containing substituents which comprises reacting phosgene with a phosphine oxide having the formula R3PO to produce the dichlorophosphorane which then is reacted with a ketone in the process of claim 1.
Claim 5
Dependent Claim
39 words
The process of using phosgene to convert ketonic acetyl substituents to ethynyl substituents which comprises reacting phosgene with a phosphine oxide having the formula R3PO to produce the dichlorophosphorane which then is used in the process of claim 2.
Claim 6
Dependent Claim
12 words
The process of claim 1 wherein the ketone is an acetyl benzene.
Claim 7
Dependent Claim
14 words
The process of claim 1 wherein the ketone is m-diacetylbenzene, p-diacetylbenzene or mixtures thereof.
Claim 8
Dependent Claim
13 words
The process of claim 1 wherein the ketone is an alkyl methyl ketone.
Claim 9
Dependent Claim
10 words
The process of claim 1 wherein the ketone is acetone.
Claim 10
Dependent Claim
13 words
The process of claim 1 wherein the ketone is an alkenyl methyl ketone.
Claim 11
Dependent Claim
12 words
The process of claim 1 wherein the ketone is methyl vinyl ketone.
Claim 12
Dependent Claim
95 words
The continuous process for using phosgene to convert ketonic acetyl substituents to chlorine containing substituents which comprises (a) reacting phosgene with a phosphine oxide having the formula R3PO to produce a dichlorophosphorane having the formula R3PCl2, (b) using the dichlorophosphorane of (a) in the process of claim 1, using acetonitrile as the solvent for the ketone, (c) extracting the reaction product having chlorine containing substituents from the reaction mixture with a liquid alkane immiscible with acetonitrile, (d) isolating the acetonitrile layer containing the phosphine oxide and (e) recycling the acetonitrile layer to process step (a).
Claim 13
Dependent Claim
11 words
The process of claim 11 wherein the each R is phenyl.
Claim 14
Dependent Claim
11 words
The process of claim 12 wherein the ketone is an acetylbenzene.
Claim 15
Dependent Claim
14 words
The process of claim 12 wherein the ketone is m-diacetylbenzene, p-diacetylbenzene or mixtures thereof.
Claim 16
Dependent Claim
13 words
The process of claim 12 wherein the ketone is an alkyl methyl ketone.
Claim 17
Dependent Claim
10 words
The process of claim 12 wherein the ketone is acetone.
Claim 18
Dependent Claim
13 words
The process of claim 12 wherein the ketone is an alkenyl methyl ketone.
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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) | 1976-02-06 | 1976-08-07 | 1977-02-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1980-02-06 | 1980-08-07 | 1981-02-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1984-02-06 | 1984-08-07 | 1985-02-06 | $7700.00 | Window Closed / Lapsed |