US4131557A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Soap composition
Assignee: International Flavors and Fragrances Inc
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Filing: 1977-10-31
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Granted: 1978-12-26
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Expires: 1997-10-31
Abstract
Abstract Described is a soap composition containing as a key ingredient, a mixture of compounds having a sandalwood aroma produced according to a process which comprises: (1) Reacting catechol with camphene in the presence of a Friedel Crafts Catalyst to form a first alkylation product; and then (2) Treating said first alkylation product with hydrogen in the presence of a hydrogenation catalyst, thus forming, initially, diol intermediates and then, on continuing the hydrogenation, the mixture useful in the perfume compositions of our invention.
Inventors
- 👤 John B. Hall
- 👤 Wilhelmus J. Wiegers
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 20:16
CPC Classifications
C; C07; C07C; C07C37/00; C07C37/11; C07C37/14; C11; C11B; C11B9/00; C11B9/0042; C11B9/0046; C07C2602/00; C07C2602/36; C07C2602/42
Claims Analysis
Total Claims: 4
Claim 1
Independent Claim
246 words
A process for preparing a perfumed soap comprising the step of admixing soap chips with from 1% up to 3% of a product produced by the process which comprises reacting catechol having the structure: ##STR14## with camphene having the structure: ##STR15## in the presence of a Friedel Crafts Catalyst to form a catechol-camphene alkylation product, recovering said alkylation product at a temperature in the range of from 186 up to 236° C. and at a pressure of from 2.3 up to 3.8 mm Hg, hydrogenating the said catechol-camphene alkylation product in the presence of a hydrogenation catalyst to form a hydrogenated catechol-camphene addition product and recovering the said hydrogenated catechol-camphene addition product at a temperature in the range of from 150° C. up to 172° C. and a pressure of about 2.5 mm Hg, the Friedel Crafts Catalyst being selected from the group consisting of boron trifluoride etherate, sulfuric acid, acid clay, aluminum trichloride, boron trifluoride, boron trifluoride-acetic acid, boron trifluoride-phosphoric acid, zinc chloride, aluminosilicate molecular sieve, and ferric chloride, the reaction between catechol and camphene being carried out at a temperature in the range of from about 120° C. up to 175° C. and the mole ratio of catechol to camphene being in the range of from about 0.5:1 up to about 4:1, the hydrogenation reaction being carried out within a temperature range of 100° C. up to 300° C., the latter portion of the reaction time being at from 200 up to 300° C.
Claim 2
Dependent Claim
246 words
A process for preparing a perfumed soap comprising the step of admixing soap chips with from 1% up to 3% of a product produced by the process which comprises reacting catechol having the structure: ##STR14## with camphene having the structure: ##STR15## in the presence of a Friedel Crafts Catalyst to form a catechol-camphene alkylation product, recovering said alkylation product at a temperature in the range of from 186 up to 236° C. and at a pressure of from 2.3 up to 3.8 mm Hg, hydrogenating the said catechol-camphene alkylation product in the presence of a hydrogenation catalyst to form a hydrogenated catechol-camphene addition product and recovering the said hydrogenated catechol-camphene addition product at a temperature in the range of from 150° C. up to 172° C. and a pressure of about 2.5 mm Hg, the Friedel Crafts Catalyst being selected from the group consisting of boron trifluoride etherate, sulfuric acid, acid clay, aluminum trichloride, boron trifluoride, boron trifluoride-acetic acid, boron trifluoride-phosphoric acid, zinc chloride, aluminosilicate molecular sieve, and ferric chloride, the reaction between catechol and camphene being carried out at a temperature in the range of from about 120° C. up to 175° C. and the mole ratio of catechol to camphene being in the range of from about 0.5:1 up to about 4:1, the hydrogenation reaction being carried out within a temperature range of 100° C. up to 300° C., the latter portion of the reaction time being at from 200 up to 300° C.
Claim 3
Dependent Claim
257 words
A process for producing a soap comprising the step of intimately admixing with soap chips from 1% up to 3% of a product produced by the process which comprises reacting catechol having the structure: ##STR16## with camphene having the structure: ##STR17## in the presence of a Friedel Crafts Catalyst to form a catechol-camphene alkylation product, recovering the said catechol-camphene alkylation product at a temperature of from 186 up to 236° C. and a pressure of from 2.3 up to 3.8 mm Hg hydrogenating the said catechol-camphene alkylation product in the presence of a hydrogenation catalyst to form a hydrogenated catechol-camphene addition product, the said hydrogenation being carried out in two consecutive stages: (1) A first stage carried out at a temperature of from 100° C. up to 200° C.; and (2) A second stage carried out at a temperature of from 200° C. up to 300° C., said hydrogenated catechol-camphene addition product being recovered at a temperature in the range of from 154 up to 209° C. and a pressure of from 2.3 up to 2.8 mm Hg, the Friedel Crafts Catalyst being selected from the group consisting of boron trifluoride etherate, sulfuric acid, acid clay, aluminum trichloride, boron trifluoride, boron triflurodie-acetic acid, boron trifluoride-phosphoric acid, zinc chloride, aluminosilicate molecular sieve, and ferric chloride, the reaction between catechol and camphene being carried out at a temperature in the range of from 120° C. up to 175° C. and the mole ratio of catechol to camphene being in the range of from about 0.5:1 up to about 4:1.
Claim 4
Dependent Claim
257 words
A process for producing a soap comprising the step of intimately admixing with soap chips from 1% up to 3% of a product produced by the process which comprises reacting catechol having the structure: ##STR16## with camphene having the structure: ##STR17## in the presence of a Friedel Crafts Catalyst to form a catechol-camphene alkylation product, recovering the said catechol-camphene alkylation product at a temperature of from 186 up to 236° C. and a pressure of from 2.3 up to 3.8 mm Hg hydrogenating the said catechol-camphene alkylation product in the presence of a hydrogenation catalyst to form a hydrogenated catechol-camphene addition product, the said hydrogenation being carried out in two consecutive stages: (1) A first stage carried out at a temperature of from 100° C. up to 200° C.; and (2) A second stage carried out at a temperature of from 200° C. up to 300° C., said hydrogenated catechol-camphene addition product being recovered at a temperature in the range of from 154 up to 209° C. and a pressure of from 2.3 up to 2.8 mm Hg, the Friedel Crafts Catalyst being selected from the group consisting of boron trifluoride etherate, sulfuric acid, acid clay, aluminum trichloride, boron trifluoride, boron triflurodie-acetic acid, boron trifluoride-phosphoric acid, zinc chloride, aluminosilicate molecular sieve, and ferric chloride, the reaction between catechol and camphene being carried out at a temperature in the range of from 120° C. up to 175° C. and the mole ratio of catechol to camphene being in the range of from about 0.5:1 up to about 4:1.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-12-25 | 1982-06-26 | 1982-12-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-12-25 | 1986-06-26 | 1986-12-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-12-25 | 1990-06-26 | 1990-12-26 | $7700.00 | Window Closed / Lapsed |