US4128580A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Process for the production of 1,3-dichloroacetone oxime and its acetate derivative
Assignee: Zeneca Inc
•
Filing: 1976-12-21
•
Granted: 1978-12-05
•
Expires: 1996-12-21
Abstract
Abstract 1,3-dichloroacetone oxime is prepared from 1,3-dichloropropanone by reaction with a hydroxylamine salt in a strongly acidic medium in the presence of a base selected from the group consisting of tertiary amines, lower alkyl amides, alkali metal bicarbonates, alkali metal carbonates and alkaline earth metal carbonates. 1,3-dichloroacetone oxime acetate is advantageously prepared by reaction of the oxime with acetic anhydride. The acetate is obtained in high purity.
Inventors
- 👤 Kent E. Matsumoto
- 👤 Jimmy H. Chan
- 👤 Don R. Baker
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 23:12
CPC Classifications
C; C07; C07C; C07C249/00; C07C249/04; C07C251/00; C07C251/32; C07C251/62; C07C251/64; A; A01; A01N; A01N33/00; A01N33/16; A01N33/24; C07C251/34; C07C251/44
Claims Analysis
Total Claims: 25
Claim 1
Independent Claim
79 words
A process for the production of 1,3-dichloroacetone oxime comprising reacting 1,3-dichloropropanone with a hydroxylamine salt in the presence of a base selected from the group consisting of tertiary amines, lower alkyl amides, alkali metal bicarbonates, alkali metal carbonates, and alkaline earth metal carbonates, establishing the pH of the reaction system at a value of 2 or less and thereafter maintaining the pH of the reaction system at a value of 2 or less throughout the remainder of the reaction.
Claim 2
Dependent Claim
79 words
A process for the production of 1,3-dichloroacetone oxime comprising reacting 1,3-dichloropropanone with a hydroxylamine salt in the presence of a base selected from the group consisting of tertiary amines, lower alkyl amides, alkali metal bicarbonates, alkali metal carbonates, and alkaline earth metal carbonates, establishing the pH of the reaction system at a value of 2 or less and thereafter maintaining the pH of the reaction system at a value of 2 or less throughout the remainder of the reaction.
Claim 3
Dependent Claim
12 words
A process according to claim 1 in which the base is pyridine.
Claim 4
Dependent Claim
13 words
A process according to claim 1 in which the base is sodium carbonate.
Claim 5
Dependent Claim
16 words
A process according to claim 1 in which the base is an alkaline earth metal carbonate.
Claim 6
Dependent Claim
13 words
A process according to claim 4 in which the base is calcium carbonate.
Claim 7
Dependent Claim
15 words
A process according to claim 1 in which the base is an alkali metal bicarbonate.
Claim 8
Dependent Claim
69 words
A process according to claim 1 in which the base is added to the reaction system at a time subsequent to the commencement of the reaction and at which the pH of the reaction system is at a value of 2 or less, and the addition of the base is controlled so as to thereafter maintain the pH of the reaction system at a value of 2 or less.
Claim 9
Dependent Claim
79 words
A process according to claim 1 in which a portion of the base is added to the reaction system at the commencement of the reaction and the remainder is subsequently added in a controlled fashion so as to maintain the pH of the reaction system at a value of 2 or less, and further comprising simultaneously adding a sufficient quantity of a mineral acid to maintain the pH of the reaction system at a value of 2 or less.
Claim 10
Dependent Claim
19 words
A process according to claim 1 in which the temperature is between about 5° C. and about 85° C.
Claim 11
Dependent Claim
21 words
A process according to claim 1 in which the reaction is carried out in the presence of an inert organic solvent.
Claim 12
Dependent Claim
12 words
A process according to claim 10 in which the solvent is toluene.
Claim 13
Dependent Claim
98 words
A process for the production of 1,3-dichloroacetone oxime acetate comprising: (a) reacting 1,3-dichloropropane with a hydroxylamine salt in the presence of a base selected from the group consisting of tertiary amines, lower alkyl amides, alkali metal bicarbonates, alkali metal carbonates, and alkaline earth metal carbonates, establishing the pH of the reaction system at a value of 2 or less and thereafter maintaining the pH of the reaction system at a value of 2 or less throughout the remainder of the reaction, whereby 1,3-dichloroacetone oxime is produced; and (b) reacting the 1,3-dichloroacetone oxime from step (a) with acetic anhydride.
Claim 14
Dependent Claim
98 words
A process for the production of 1,3-dichloroacetone oxime acetate comprising: (a) reacting 1,3-dichloropropane with a hydroxylamine salt in the presence of a base selected from the group consisting of tertiary amines, lower alkyl amides, alkali metal bicarbonates, alkali metal carbonates, and alkaline earth metal carbonates, establishing the pH of the reaction system at a value of 2 or less and thereafter maintaining the pH of the reaction system at a value of 2 or less throughout the remainder of the reaction, whereby 1,3-dichloroacetone oxime is produced; and (b) reacting the 1,3-dichloroacetone oxime from step (a) with acetic anhydride.
Claim 15
Dependent Claim
12 words
A process according to claim 12 in which the base is pyridine.
Claim 16
Dependent Claim
13 words
The process according to claim 12 in which the base is sodium carbonate.
Claim 17
Dependent Claim
16 words
A process according to claim 12 in which the base is an alkaline earth metal carbonate.
Claim 18
Dependent Claim
13 words
A process according to claim 15 in which the base is calcium carbonate.
Claim 19
Dependent Claim
15 words
A process according to claim 12 in which the base is an alkali metal bicarbonate.
Claim 20
Dependent Claim
68 words
A process according to claim 12 in which the base is added to the reaction system at a time subsequent to the commencement of the reaction and at which the pH of the reaction system is at a value of 2 or less, and the addition of the base is controlled so as to thereafter maintain the pH of the system at a value of 2 or less.
Claim 21
Dependent Claim
80 words
A process according to claim 12 in which at least a portion of the base is added to the reaction system at the commencement of the reaction and the remainder is subsequently added in a controlled manner so as to maintain the pH of the system at a value of 2 or less, and further comprising simultaneously adding a sufficient quantity of a mineral acid to maintain the pH of the reaction system at a value of 2 or less.
Claim 22
Dependent Claim
24 words
A process according to claim 12 in which the acetic anhydride is utilized in step (b) in an excess with respect to the oxime.
Claim 23
Dependent Claim
22 words
A process according to claim 12 in which steps (a) and (b) are conducted in the presence of an inert organic solvent.
Claim 24
Dependent Claim
12 words
A process according to claim 21 in which the solvent is toluene.
Claim 25
Dependent Claim
28 words
A process according to claim 21 in which the oxime is introduced into step (b) as a solution of oxime in an organic solvent obtained from step (a).
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) | 1981-12-04 | 1982-06-05 | 1982-12-05 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-12-04 | 1986-06-05 | 1986-12-05 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-12-04 | 1990-06-05 | 1990-12-05 | $7700.00 | Window Closed / Lapsed |