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US4093667A
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Preparation of 4-n-hexylresorcinol
Assignee: ConocoPhillips Co
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Filing: 1977-03-14
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Granted: 1978-06-06
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Expires: 1997-03-14
Abstract
Abstract Preparation of 4-n-hexylresorcinol is achieved by a two-step process involving: first preparing hexyl resorcyl ethers by reacting resorcinol with a hexylating agent having the general formula 1-C 6 H 13 X in the presence of a base, and second, treating the reaction product obtained with a catalyst to yield 4-n-hexylresorcinol by a rearrangement process. X can be selected from the group consisting of Cl- Br-, I-, ArSO 3 - , and similar materials.
Inventors
- 👤 Charles Masterson Starks
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 11:15
CPC Classifications
C; C07; C07C; C07C37/00; C07C37/01; C07C37/055; C07C37/11; C07C37/16
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
152 words
A process for the preparation of 4-n-hexylresorcinol comprising; a) preparing hexylresorcyl ethers by reacting recorcinol with a hexylating agent having the general formula 1-C 6 H 13 X at a temperature of from about 25° C to about 175° C in the presence of a base selected from the group consisting of the oxides, hydroxides, or carbonates of sodium, potassium, calcium, ammonium, magnesium, tetra-alkyl ammonium, berium, and lithium, and b) heating the reaction product of (a) to a temperature of from about 150° C to about 300° C in the presence of an acidic catalyst to yield 4-n-hexylresorcinol, wherein X is selected from the group consisting of Cl.sup. --, Br -- , CH 3 SO 3 -- , C 2 H 5 SO 3 -- , C 2 H 5 OSO 3 -- , CH 3 OSO 3 -- , ArSO 3 -- , and ONO 3 -- or mixtures of these.
Claim 2
Dependent Claim
152 words
A process for the preparation of 4-n-hexylresorcinol comprising; a) preparing hexylresorcyl ethers by reacting recorcinol with a hexylating agent having the general formula 1-C 6 H 13 X at a temperature of from about 25° C to about 175° C in the presence of a base selected from the group consisting of the oxides, hydroxides, or carbonates of sodium, potassium, calcium, ammonium, magnesium, tetra-alkyl ammonium, berium, and lithium, and b) heating the reaction product of (a) to a temperature of from about 150° C to about 300° C in the presence of an acidic catalyst to yield 4-n-hexylresorcinol, wherein X is selected from the group consisting of Cl.sup. --, Br -- , CH 3 SO 3 -- , C 2 H 5 SO 3 -- , C 2 H 5 OSO 3 -- , CH 3 OSO 3 -- , ArSO 3 -- , and ONO 3 -- or mixtures of these.
Claim 3
Dependent Claim
37 words
A process as described in claim 1 wherein (b) is carried out in the presence of excess resorcinol in a concentration of from about 5 to about 75 weight percent based on the total reaction mixture weight.
Claim 4
Dependent Claim
19 words
A process as described in claim 2 wherein (a) is carried out in the presence of an organic solvent.
Claim 5
Dependent Claim
26 words
A process as described in claim 3 wherein the organic solvent is selected from the group consisting of toluene, hexanol, aceto nitril, N,N'-dimethylformamide, dimethylsulfoxide, and methanol.
Claim 6
Dependent Claim
27 words
A process as described in claim 2 wherein the acidic catalyst of (b) is selected from the group consisting of alumina, silica alumina, titania, and methanesulfonic acid.
Claim 7
Dependent Claim
37 words
A process as described in claim 2 wherein the reaction temperature of (a) is from about 25° C to about 175° C and the reaction temperature of (b) is from about 150° C to about 300° C.
Claim 8
Dependent Claim
23 words
A process as described in claim 1 wherein the mole ratio of resorcinol to hexylating agent ranges from about 1 to about 5.
Claim 9
Dependent Claim
29 words
A process for the preparation of 4-n-hexylresorcinol comprising reacting di-n-hexylether with resorcinol in the presence of alumina catalysts at temperatures of from about 150° C to about 300° C.
Claim 10
Dependent Claim
29 words
A process for the preparation of 4-n-hexylresorcinol comprising reacting di-n-hexylether with resorcinol in the presence of alumina catalysts at temperatures of from about 150° C to about 300° C.
Claim 11
Dependent Claim
22 words
A process as described in claim 8 wherein the mole ratio or di-n-hexylether to resorcinol is from about 1 to about 5.
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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) | 1981-06-05 | 1981-12-05 | 1982-06-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-06-05 | 1985-12-05 | 1986-06-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-06-05 | 1989-12-05 | 1990-06-06 | $7700.00 | Window Closed / Lapsed |