US4374998A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Aliphatic branched olefin dioxolanes
Assignee: International Flavors and Fragrances Inc
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Filing: 1981-12-10
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Granted: 1983-02-22
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Expires: 2001-12-10
Abstract
Abstract Described is the genus of compound having the structure: ##STR1## wherein R 1 represents C 1 -C 3 lower alkyl; R 2 , R 3 , R 4 and R 5 represent the same or different hydrogen or C 1 -C 3 lower alkyl; X and Y represent the same or different oxygen or sulfur; and one of the dashed lines represents a carbon-carbon double bond and the other of the dashed lines represent carbon-carbon single bonds as well as methods for augmenting or enhancing the aroma and/or taste of consumable materials including foodstuffs, chewing gums, medicinal products, toothpastes, chewing tobaccos, perfume compositions, perfumed articles, smoking tobaccos and smoking tobacco articles using such dioxolanes, oxathiolanes and dithiolanes. The perfumed articles include solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, dryer-added fabric softener articles, hair preparations, deodorant compositions, as well as bleaching compositions containing the same.
Inventors
- 👤 Richard M. Boden
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 14:54
CPC Classifications
A; A24; A24B; A24B15/00; A24B15/18; A24B15/28; A24B15/30; A24B15/36; A24B15/40; A24B15/403; A24B15/406; C; C07; C07D; C07D317/00; C07D317/08; C07D317/10; C07D317/12; C11; C11B; C11B9/00; C11B9/0069; C11B9/0073; C11B9/0076; C11D; C11D1/00; C11D1/02; C11D1/12; C11D1/22; C11D1/24; C11D3/00; C11D3/395; C11D3/3956
Claims Analysis
Total Claims: 8
Claim 1
Independent Claim
77 words
A dioxolane, oxathiolane or dithiolane compound defined according to the structure: ##STR215## wherein R 1 represents C 1 -C 4 lower alkyl; R 2 , R 3 , R 4 and R 5 represent hydrogen or C 1 -C 3 lower alkyl; X and Y are the same and each represents oxygen and wherein one of the dashed lines represents a carbon-carbon double bond and each of the other of the dashed lines represent carbon-carbon single bonds.
Claim 2
Dependent Claim
77 words
A dioxolane, oxathiolane or dithiolane compound defined according to the structure: ##STR215## wherein R 1 represents C 1 -C 4 lower alkyl; R 2 , R 3 , R 4 and R 5 represent hydrogen or C 1 -C 3 lower alkyl; X and Y are the same and each represents oxygen and wherein one of the dashed lines represents a carbon-carbon double bond and each of the other of the dashed lines represent carbon-carbon single bonds.
Claim 3
Dependent Claim
33 words
The compound of claim 1 having the structure: ##STR216## wherein one of the dashed lines represents a carbon-carbon double bond and each of the other of the dashed lines represent carbon-carbon single bonds.
Claim 4
Dependent Claim
33 words
The compound of claim 1 having the structure: ##STR217## wherein one of the dashed lines represents a carbon-carbon double bond and each of the other of the dashed lines represent carbon-carbon single bonds.
Claim 5
Dependent Claim
33 words
The compound of claim 1 having the structure: ##STR218## wherein one of the dashed lines represents a carbon-carbon double bond and each of the other of the dashed lines represent carbon-carbon single bonds.
Claim 6
Dependent Claim
293 words
A composition of matter comprising a major proportion of compounds defined according to a structure selected from the group consisting of: ##STR219## wherein in the mixture in each of the molecules one of the dashed lines represents a carbon-carbon double bond and each of the other of the dashed lines represent carbon-carbon single bonds, said composition of matter produced according to the process comprising the steps of: (a) dimerization of isoamylene having the structure: ##STR220## in the presence of an acid catalyst to form a mixture containing a major proportion of a mixture of compounds defined according to the structure: ##STR221## wherein (i) at least one of R 3 ' and R 4 ' represents methyl; (ii) the sum of the carbon atoms in R 1 ', R 2 ', R 3 ', R 4 ' and R 5 ' is 3; and (iii) R 1 ' and R 2 ' represent hydrogen when R 5 ' is methyl; (b) reacting the resulting diisoamylene mixture with a compound selected from the group consisting of an alkanoyl halide having 2 or 3 carbon atoms and an alkanoic acid anhydride having 4 or 6 carbon atoms to form a mixture containing a major proportion of compounds defined according to the structure: ##STR222## wherein R 1 is C 1 or C 2 alkyl and wherein in the mixtures in each of the molecules one of the dashed lines represents a carbon-carbon double bond and the other of the dashed lines represent carbon-carbon single bonds; and (c) reacting the resulting mixture with a compound selected from the group consisting of 1,2-propylene glycol; 1,2-propylene oxide; 1,2-ethylene glycol; and 1,2-ethylene oxide at a temperature of between 0° C. and 80° C. in the presence of a Lewis acid catalyst.
Claim 7
Dependent Claim
293 words
A composition of matter comprising a major proportion of compounds defined according to a structure selected from the group consisting of: ##STR219## wherein in the mixture in each of the molecules one of the dashed lines represents a carbon-carbon double bond and each of the other of the dashed lines represent carbon-carbon single bonds, said composition of matter produced according to the process comprising the steps of: (a) dimerization of isoamylene having the structure: ##STR220## in the presence of an acid catalyst to form a mixture containing a major proportion of a mixture of compounds defined according to the structure: ##STR221## wherein (i) at least one of R 3 ' and R 4 ' represents methyl; (ii) the sum of the carbon atoms in R 1 ', R 2 ', R 3 ', R 4 ' and R 5 ' is 3; and (iii) R 1 ' and R 2 ' represent hydrogen when R 5 ' is methyl; (b) reacting the resulting diisoamylene mixture with a compound selected from the group consisting of an alkanoyl halide having 2 or 3 carbon atoms and an alkanoic acid anhydride having 4 or 6 carbon atoms to form a mixture containing a major proportion of compounds defined according to the structure: ##STR222## wherein R 1 is C 1 or C 2 alkyl and wherein in the mixtures in each of the molecules one of the dashed lines represents a carbon-carbon double bond and the other of the dashed lines represent carbon-carbon single bonds; and (c) reacting the resulting mixture with a compound selected from the group consisting of 1,2-propylene glycol; 1,2-propylene oxide; 1,2-ethylene glycol; and 1,2-ethylene oxide at a temperature of between 0° C. and 80° C. in the presence of a Lewis acid catalyst.
Claim 8
Dependent Claim
85 words
The composition of matter of claim 5 wherein in the process to produce the composition of matter, the reaction between the alkanoyl halide or the alkanoic acid anhydride with the diisoamylene mixture is carried out in the presence of a Lewis acid or a mineral acid at a temperature of between 0° C. and 50° C. with the mole ratio of diisoamylene mixture:acylating agent being between 1:1.1 and 2:1.0 and the concentration of catalyst being between 5 and 10% by weight of the reaction mass.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1986-02-21 | 1986-08-23 | 1987-02-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-02-21 | 1990-08-23 | 1991-02-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-02-21 | 1994-08-23 | 1995-02-22 | $7700.00 | Window Closed / Lapsed |