US3950438A
Expired / Lapsed
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Preparation of resorcinol and alkyl-substituted derivatives thereof
Assignee: Stamicarbon BV
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Filing: 1974-03-11
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Granted: 1976-04-13
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Expires: 1994-03-11
Abstract
Abstract Process for the preparation of resorcinols of the general formula: ##SPC1## Wherein R 1 , R 2 , R 3 , and R 4 , which are the same or different, are each hydrogen or an alkyl group containing up to 6 carbon atoms, and the total number of carbon atoms of R 1 , R 2 , R 3 , and R 4 is no more than 12 carbon atoms, which comprises contacting keto esters of the general formula ##EQU1## wherein R 1 , R 2 , R 3 , and R 4 are as defined above, and R 5 is an alkyl, cycloalkyl, or monocyclic or bicyclic aryl or arylalkyl group containing up to 12 carbon atoms, with a dehydrogenation catalyst at a temperature of about 100°C to 500°C.
Inventors
- 👤 Sijbrandus E. Schaafsma
- 👤 Johannes E. L. Claassens
- 👤 Egidius J. M. Verheijen
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 18:07
CPC Classifications
C; C07; C07C; C07C37/00
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
161 words
A process for the preparation of a resorcinol of the general gormula: ##SPC3## wherein R 1 , R 2 , R 3 and R 4 , which are the same or different, are each hydrogen or an alkyl group containing up to 6 carbon atoms, and the total number of carbon atoms of R 1 R 2 , R 3 and R 4 is no more than 12 carbon atoms, which comprises contacting a keto ester of the general formula ##EQU3## wherein R 1 , R 2 , R 3 , and R 4 are as defined above and R 5 is an alkyl, cycloalkyl, or monocyclic or bicyclic aryl or arylalkyl group containing up to 12 carbon atoms, with a dehydrogenation catalyst wherein the dehydrogenation catalyst contains a metal or a compound of a metal selected from the group consisting of iron, cobalt, nickel, ruthenium rhodium, palladium, osmium, iridium, platinum and copper at a temperature of about 100°C to 500°C.
Claim 2
Dependent Claim
161 words
A process for the preparation of a resorcinol of the general gormula: ##SPC3## wherein R 1 , R 2 , R 3 and R 4 , which are the same or different, are each hydrogen or an alkyl group containing up to 6 carbon atoms, and the total number of carbon atoms of R 1 R 2 , R 3 and R 4 is no more than 12 carbon atoms, which comprises contacting a keto ester of the general formula ##EQU3## wherein R 1 , R 2 , R 3 , and R 4 are as defined above and R 5 is an alkyl, cycloalkyl, or monocyclic or bicyclic aryl or arylalkyl group containing up to 12 carbon atoms, with a dehydrogenation catalyst wherein the dehydrogenation catalyst contains a metal or a compound of a metal selected from the group consisting of iron, cobalt, nickel, ruthenium rhodium, palladium, osmium, iridium, platinum and copper at a temperature of about 100°C to 500°C.
Claim 3
Dependent Claim
24 words
The process of claim 1 wherein the temperature is about 200° to 400° C and the reaction is carried out in the gaseous state.
Claim 4
Dependent Claim
23 words
The process of claim 1, wherein the keto ester is contacted with the catalyst in the gaseous state in the presence of hydrogen.
Claim 5
Dependent Claim
23 words
The process of claim 3 wherein the temperature is about 200° to 400°C and the reaction is carried out in the gaseous state.
Claim 6
Dependent Claim
18 words
The process of claim 4 wherein R 5 is an alkyl group of up to 6 carbon atoms.
Claim 7
Dependent Claim
154 words
A process for the preparation of a resorcinol of the general formula: ##SPC4## wherein R 1 , R 2 , R 3 , and R 4 , which are the same or different, are each hydrogen or an alkyl group containing up to 6 carbon atoms, and the total number of carbon atoms of R 1 , R 2 , R 3 and R 4 is no more than 12 carbon atoms, which comprises contacting a keto ester of the general formula ##EQU4## wherein R 1 , R 2 , R 3 , and R 4 are as defined above and R 5 is an alkyl, cycloalkyl, or monocyclic or bicyclic aryl or arylalkyl group containing up to 12 carbon atoms, which keto ester is in the gaseous state, with a dehydrogenation catalyst comprising palladium, platinum, a mixture of palladium and platinum or nickel on a carrier at a temperature of 200°C to 400°C.
Claim 8
Dependent Claim
154 words
A process for the preparation of a resorcinol of the general formula: ##SPC4## wherein R 1 , R 2 , R 3 , and R 4 , which are the same or different, are each hydrogen or an alkyl group containing up to 6 carbon atoms, and the total number of carbon atoms of R 1 , R 2 , R 3 and R 4 is no more than 12 carbon atoms, which comprises contacting a keto ester of the general formula ##EQU4## wherein R 1 , R 2 , R 3 , and R 4 are as defined above and R 5 is an alkyl, cycloalkyl, or monocyclic or bicyclic aryl or arylalkyl group containing up to 12 carbon atoms, which keto ester is in the gaseous state, with a dehydrogenation catalyst comprising palladium, platinum, a mixture of palladium and platinum or nickel on a carrier at a temperature of 200°C to 400°C.
Claim 9
Dependent Claim
16 words
The process of claim 6 wherein the catalyst is palladium or platinum on a carbon carrier.
Claim 10
Dependent Claim
23 words
The process of claim 6 wherein the keto ester is contacted with the catalyst in the gaseous state in the presence of hydrogen.
Claim 11
Dependent Claim
18 words
The process of claim 6 wherein R 5 is an alkyl group of up to 6 carbon atoms.
Claim 12
Dependent Claim
23 words
The process of claim 7 wherein the keto ester is an alkyl 5-oxo-hexanoate containing up to 6 carbon atoms in the alkyl group.
Claim 13
Dependent Claim
23 words
The process of claim 6 wherein the keto ester is an alkyl 5-oxo-4-methylhexanoate containing up to 6 carbon atoms in the alkyl group.
References Cited (Backward Citations)
US3580970A
Cited
US3691102A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-04-13 | 1979-10-13 | 1980-04-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-04-13 | 1983-10-13 | 1984-04-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-04-13 | 1987-10-13 | 1988-04-13 | $7700.00 | Window Closed / Lapsed |