Patent US1728749A successfully refreshed from Google Patents.
Patent US3886215A successfully refreshed from Google Patents.
US3886215A
Expired / Lapsed
US
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Process using metal salt-amine complex catalysts for the preparation of alpha beta-ethylenic ketones such as delta-cis-pseudo ionones
Assignee: Syensqo USA LLC
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Filing: 1973-02-01
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Granted: 1975-05-27
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Expires: 1993-02-01
Abstract
Abstract A process is provided for the preparation of Alpha , Beta ethylenic ketones by the condensation of aliphatic and cycloaliphatic tertiary acetylenic carbinols and especially for the preparation of Delta 3-cis-pseudo ionones by the condensation of dehydrolinalool and derivatives thereof with isoalkenyl ethers in the presence of metal salt-amine complex catalysts. The Delta 3-cis-pseudo ionones can be cyclized to produce the corresponding Alpha -, Beta -, and gamma -cisionones or alkyl ionones. Methods are also described for rearranging the Delta 3-cis-pseudo ionones to the normally encountered trans-pseudo ionones which in turn can be converted to the trans-ionones.
Inventors
- 👤 Robert S Desimone
- 👤 Peter S Gradeff
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 09:51
CPC Classifications
C; C07; C07C; C07C403/00; C07C403/14; C07C403/16; C07C45/00; C07C45/51; C07C45/511; C07C45/513; C07C45/61; C07C45/67; C07C49/00; C07C49/20; C07C49/203; C11; C11B; C11B9/00; C11B9/0026; C11B9/0034; C07C2601/00; C07C2601/12; C07C2601/16
Claims Analysis
Total Claims: 27
Claim 1
Independent Claim
39 words
A PROCESS FOR PREPARING CIS$3-PSEUDO IONONES AND CIS-$3PSUEDO METHYL IONONES FROM DEHYDROLINALOOL AND LOWER ALKYL HOMOLOGUES THEREOF BY CONDENSATION WITH AN ISOPROPENYL OR ISOBUTENYL LOWER ALKYL ETHER, COMPRISING CONDENSING DEHYDROLINALOOL OR A LOWER ALKYL HOMOLOGUE THEREOF HAVING THE FORMULA:
Claim 2
Dependent Claim
39 words
A PROCESS FOR PREPARING CIS$3-PSEUDO IONONES AND CIS-$3PSUEDO METHYL IONONES FROM DEHYDROLINALOOL AND LOWER ALKYL HOMOLOGUES THEREOF BY CONDENSATION WITH AN ISOPROPENYL OR ISOBUTENYL LOWER ALKYL ETHER, COMPRISING CONDENSING DEHYDROLINALOOL OR A LOWER ALKYL HOMOLOGUE THEREOF HAVING THE FORMULA:
Claim 3
Dependent Claim
18 words
A process according to claim 1, in which the reaction time is from 0.2 to abouT 72 hours.
Claim 4
Dependent Claim
11 words
A process according to claim 1, in which dehydrolinalool is condensed.
Claim 5
Dependent Claim
19 words
A process according to claim 1, in which dehydrolinalool is condensed with an isopropenyl ether to form pseudo ionone.
Claim 6
Dependent Claim
23 words
A process according to claim 1, in which dehydrolinalool is condensed with an isobutenyl ether to form iso and normal pseudo methyl ionone.
Claim 7
Dependent Claim
28 words
A process according to claim 1, in which the amount of catalyst is within the range from about 0.1 to about 10% by weight of the reaction mixture.
Claim 8
Dependent Claim
16 words
A process according to claim 1, in which the reaction temperature is from 85* to 120*C.
Claim 9
Dependent Claim
15 words
A process according to claim 1, in which the metal of the catalyst is copper.
Claim 10
Dependent Claim
15 words
A process according to claim 8, in which the metal of the catalyst is chromium.
Claim 11
Dependent Claim
15 words
A process according to claim 8, in which the metal of the catalyst is silver.
Claim 12
Dependent Claim
17 words
A process according to claim 1, in which the amine of the catalyst is an aliphatic amine.
Claim 13
Dependent Claim
14 words
A process according to claim 11, in which the amine is a primary amine.
Claim 14
Dependent Claim
14 words
A process according to claim 12, in which the amine is a secondary amine.
Claim 15
Dependent Claim
14 words
A process according to claim 12, in which the amine is a tertiary amine.
Claim 16
Dependent Claim
17 words
A process according to claim 1, in which the amine of the catlyst is an aromatic amine.
Claim 17
Dependent Claim
17 words
A process according to claim 1, in which the amine of the catalyst is a heterocyclic amine.
Claim 18
Dependent Claim
12 words
A process according to claim 1, in which M is copper, and
Claim 19
Dependent Claim
19 words
A process for preparing Alpha , Beta -ethylenic ketones, which comprises condensing a tertiary acetylenic carbinol having the formula:
Claim 20
Dependent Claim
19 words
A process for preparing Alpha , Beta -ethylenic ketones, which comprises condensing a tertiary acetylenic carbinol having the formula:
Claim 21
Dependent Claim
12 words
A process according to claim 18 in which M is copper and
Claim 22
Dependent Claim
10 words
A process according to claim 18, in which R'' is
Claim 23
Dependent Claim
18 words
A process according to claim 18, in which the reaction time is from 0.2 to about 72 hours.
Claim 24
Dependent Claim
28 words
A process according to claim 18, in which the amount of catalyst is within the range from about 0.1 to about 10% by weight of the reaction mixture.
Claim 25
Dependent Claim
16 words
A process according to claim 18, in which the reaction temperature is from 85* to 120*C.
Claim 26
Dependent Claim
20 words
A process according to claim 18, in which the tertiary acetylenic carbinol is condensed with an isopropenyl lower alkyl ether.
Claim 27
Dependent Claim
20 words
A process according to claim 18, in which the tertiary acetylenic carbinol is condensed with an isobutenyl lower alkyl ether.
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) | 1978-05-26 | 1978-11-25 | 1979-05-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1982-05-26 | 1982-11-25 | 1983-05-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1986-05-26 | 1986-11-25 | 1987-05-27 | $7700.00 | Window Closed / Lapsed |