US4028418A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Process for the preparation of cyclobutanones
Assignee: Shell USA Inc
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Filing: 1975-08-25
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Granted: 1977-06-07
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Expires: 1995-08-25
Abstract
Abstract Cyclobutanones and cyclobutenones are prepared by contacting a 2-haloacyl halide with an ethylenically unsaturated compound or an alkyne in an inert aprotic solvent at a temperature above 5° C in the presence of zinc and/or tin.
Inventors
- 👤 Marinus J. van den Brink
- 👤 Helena Austermuhle-Bertola
- 👤 Petrus A. Kramer
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 12:22
CPC Classifications
C; C07; C07C; C07C51/00; C07C49/00; C07C49/29; C07C49/293; C07C69/00; C07C69/62; C07C69/63
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
124 words
A process for the preparation of a cyclobutanone which process comprises contacting a 2-haloacyl halide of the formula ##STR8## in which formula each A represents a halogen atom having an atomic number of not more than 35, a hydrogen atom or an unsubstituted hydrocarbyl group; and each Hal represents a halogen atom having an atomic number of not more than 35, in an alkanone solvent which has at least two branches in the carbon skeleton of the molecule and of which not more than one of the carbon atoms attached to the carbonyl group is quaternary with a straight or branched chain alkene having from 2 to about 20 carbon atoms at a temperature above 5° C in the presence of zinc and/or tin.
Claim 2
Dependent Claim
124 words
A process for the preparation of a cyclobutanone which process comprises contacting a 2-haloacyl halide of the formula ##STR8## in which formula each A represents a halogen atom having an atomic number of not more than 35, a hydrogen atom or an unsubstituted hydrocarbyl group; and each Hal represents a halogen atom having an atomic number of not more than 35, in an alkanone solvent which has at least two branches in the carbon skeleton of the molecule and of which not more than one of the carbon atoms attached to the carbonyl group is quaternary with a straight or branched chain alkene having from 2 to about 20 carbon atoms at a temperature above 5° C in the presence of zinc and/or tin.
Claim 3
Dependent Claim
16 words
A process as claimed in claim 1, in which the 2-haloacyl halide is a 2,2-dihaloacyl halide.
Claim 4
Dependent Claim
15 words
A process as claimed in claim 2, in which the 2,2-dihaloacyl halide is dichloroacetyl chloride.
Claim 5
Dependent Claim
14 words
A process as claimed in claim 1, in which the alkene is 2,3-dimethyl-2-butene, 2-methyl-2
Claim 6
Dependent Claim
20 words
A process as claimed in claim 1, in which diisobutyl ketone or methyl tert-butyl ketone is used as the solvent.
Claim 7
Dependent Claim
31 words
A process as claimed in claim 1, in which the 2-haloacyl halide is applied in a concentration in the range of from 1 to 15 mol per liter of the ketone.
Claim 8
Dependent Claim
22 words
A process as claimed in claim 6 wherein the concentration is in the range of from 3 to 10 mol per liter.
Claim 9
Dependent Claim
26 words
A process as claimed in claim 1, in which the molar ratio of alkene to 2-haloacyl halide is in the range of from 0.5 to 10.
Claim 10
Dependent Claim
20 words
A process as claimed in claim 8 wherein the molar ratio is in the range of from 1 to 2.
Claim 11
Dependent Claim
28 words
A process as claimed in claim 1, in which the molar ratio of zinc or tin to 2-haloacyl halide is in the range of from 1 to 10.
Claim 12
Dependent Claim
20 words
A process as claimed in claim 10 wherein the molar ratio is in the range of from 1 to 5.
Claim 13
Dependent Claim
23 words
A process as claimed in claim 1, which is conducted at a temperature in the range of from 25° C to 60° C.
Claim 14
Dependent Claim
21 words
A process as claimed in claim 12 wherein the temperature is in the range of from 35° C to 50° C.
Claim 15
Dependent Claim
27 words
A process as claimed in claim 1, which is conducted by gradually adding the 2-haloacyl halide to a homogeneous distribution of zinc or tin in an alkene.
Claim 16
Dependent Claim
52 words
A process as claimed in claim 14, in which a suspension of zinc or tin in a solvent containing less than 25% of the total amount of the 2-haloacyl halide to be used is stirred and the alkene and subsequently the balance of the 2-haloacyl halide are added to the stirred suspension.
Claim 17
Dependent Claim
38 words
A process as claimed in claim 1, which is conducted in the presence of 0.1 to 10% mol of an inorganic halide catalyst selected from mercuric iodide, sodium chloride, potassium iodide and ammonium chloride, calculated on 2-haloacyl halide.
Claim 18
Dependent Claim
19 words
A process as claimed in claim 16, which is conducted in the presence of potassium iodide and/or ammonium chloride.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-06-06 | 1980-12-06 | 1981-06-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-06-06 | 1984-12-06 | 1985-06-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-06-06 | 1988-12-06 | 1989-06-07 | $7700.00 | Window Closed / Lapsed |