US3947405A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Process for making neohesperidine dihydrochalcone
Assignee: Givaudan Roure Corp
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Filing: 1974-12-18
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Granted: 1976-03-30
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Expires: 1994-12-18
Abstract
Abstract The known sweetening agent, neohesperidin dihydrochalcone is manufactured by reacting phloroacetophenone-4'-β-neohesperidoside with isovanillin in the presence of a secondary amine and an organic acid in solution to give neohesperidin or its chalcone and then hydrogenating the reaction product in a manner known per se.
Inventors
- 👤 Jost Wild
- 👤 Ulrich Huber
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 10:09
CPC Classifications
C; C07; C07H; C07H17/00; C07H17/04; C07H17/06; C07H17/065; C07H17/07
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
129 words
A process for the manufacture of neohesperidin dihydrochalcone, which process comprises reacting phloroacetophenone-4'-β-neohesperidoside with isovanillin in the presence of a secondary amine and an organic acid in solution to give neohesperidin or its chalcone and thereafter hydrogenating the reaction product, wherein the secondary amine is a member of the group selected from aliphatic amines such as di(lower alkyl) amines (e.g. dimethylamine, diethylamine, diisopropylamine etc), aliphatic-aromatic amines such as lower alkylarylamines (e.g. methylphenylamine), diaromatic amines (e.g. diphenylamine etc), alkanolamines (e.g. diethanolamine etc) and, cyclic amines (e.g. morpholine, piperidine, pyrrolidine and piperazine) and wherein the organic acid is a member of the group selected from a carboxylic acid such as a lower alkanecarboxylic acid (e.g. acetic acid, propionic acid etc), formic acid or an aromatic carboxylic acid (e.g. benzoic acid etc).
Claim 2
Dependent Claim
129 words
A process for the manufacture of neohesperidin dihydrochalcone, which process comprises reacting phloroacetophenone-4'-β-neohesperidoside with isovanillin in the presence of a secondary amine and an organic acid in solution to give neohesperidin or its chalcone and thereafter hydrogenating the reaction product, wherein the secondary amine is a member of the group selected from aliphatic amines such as di(lower alkyl) amines (e.g. dimethylamine, diethylamine, diisopropylamine etc), aliphatic-aromatic amines such as lower alkylarylamines (e.g. methylphenylamine), diaromatic amines (e.g. diphenylamine etc), alkanolamines (e.g. diethanolamine etc) and, cyclic amines (e.g. morpholine, piperidine, pyrrolidine and piperazine) and wherein the organic acid is a member of the group selected from a carboxylic acid such as a lower alkanecarboxylic acid (e.g. acetic acid, propionic acid etc), formic acid or an aromatic carboxylic acid (e.g. benzoic acid etc).
Claim 3
Dependent Claim
19 words
A process according to claim 1, wherein the molar ratio of reactants phloroacetophenone -4'-β-neohesperidoside and isovanillin is about 1:1.
Claim 4
Dependent Claim
26 words
A process according to claim 1, wherein the molar ratio of secondary amine to organic acid lies within a range of about 5:1 and about 1:20.
Claim 5
Dependent Claim
29 words
A process according to claim 1, wherein the reaction between phloroacetophenone 4'-β-neohesperidoside and isovanillin is carried out at a temperature within the range from about 40°C. to about 100°C.
Claim 6
Dependent Claim
23 words
A process according to claim 1, wherein pyrrolidine is used as the secondary amine and acetic acid is used as the organic acid.
Claim 7
Dependent Claim
55 words
A process according to claim 1, wherein about 2.4 parts of phloroacetophenone 4'-β-neohesperiodoside about 0.76 parts of isovanillin, about 1.07 parts of pyrrolidine and about 0.23 parts of acetic acid are employed in ethanol as solvent and the reaction is conducted under reflux, the parts all being by weight, and using Raney-nickel as hydrogenation catalyst.
Claim 8
Dependent Claim
54 words
A process according to claim 1, wherein about 24 parts of phloroacetophenone 4'-neohesperidoside about 7.6 parts of isovanillin, about 3.55 parts of pyrrolidine and about 3 parts of acetic acid are employed in ethanol as solvent and the reaction is conducted under reflux, the parts being by weight, and using Raney-nickel as hydrogenation catalyst.
Claim 9
Dependent Claim
54 words
A process according to claim 1, wherein about 47.6 parts of phloroacetophenone -4'-β-neohesperidoside about 15.2 parts of isovanillin, about 7.1 parts of pyrrolidine and about 6 parts of acetic acid are employed in isopropanol as solvent, and the reaction is conducted under reflux, the parts being by weight, and using Raney-nickel as hydrogenation catalyst.
References Cited (Backward Citations)
US3375242A
Cited
US3522236A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-03-30 | 1979-09-29 | 1980-03-30 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-03-30 | 1983-09-29 | 1984-03-30 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-03-30 | 1987-09-29 | 1988-03-30 | $7700.00 | Window Closed / Lapsed |