US4091041A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Preparation of 1,4-diols by hydrolysis-hydrogenation of 2-alkoxytetrahydrofurans
Assignee: General Electric Co
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Filing: 1977-06-13
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Granted: 1978-05-23
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Expires: 1997-06-13
Abstract
Abstract 2-ALKOXYTETRAHYDROFURANS ARE CONVERTED TO 1,4-DIOLS UNDER HYDROLYSIS-HYDROGENATION CONDITIONS. The method may be coupled with the synthesis of 2-alkoxytetrahydrofurans to provide a highly efficient, two-step conversion of allylic alcohols to butanediols.
Inventors
- 👤 William Edward Smith
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 17:10
CPC Classifications
C; C07; C07D; C07D315/00; C07C; C07C29/00; C07C29/09; C07C29/10; C07C29/103; C07D307/00; C07D307/02; C07D307/04; C07D307/18; C07D307/20
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
28 words
A process for the production of butanediol or substituted-butanediols which comprises contacting a 2-alkoxy-tetrahydrofuran or 2-alkoxy-substituted tetrahydrofuran with hydrogen in the presence of water and a hydrolysis-hydrogenation catalyst.
Claim 2
Dependent Claim
28 words
A process for the production of butanediol or substituted-butanediols which comprises contacting a 2-alkoxy-tetrahydrofuran or 2-alkoxy-substituted tetrahydrofuran with hydrogen in the presence of water and a hydrolysis-hydrogenation catalyst.
Claim 3
Dependent Claim
17 words
A process as defined in claim 1 including the step of separating the product from the catalyst.
Claim 4
Dependent Claim
13 words
A process as defined in claim 1 carried out in the liquid phase.
Claim 5
Dependent Claim
12 words
A process as defined in claim 1 carried out under super-atmospheric pressure.
Claim 6
Dependent Claim
19 words
A process as defined in claim 4 wherein said pressure is in the range of 300 - 5000 psi.
Claim 7
Dependent Claim
19 words
A process as defined in claim 5 wherein said pressure is in the range of 500 - 2000 psi.
Claim 8
Dependent Claim
13 words
A process as defined in claim 1 carried out at an elevated temperature.
Claim 9
Dependent Claim
19 words
A process as defined in claim 7 wherein said temperature is in the range of 100° - 200° C.
Claim 10
Dependent Claim
29 words
A process as defined in claim 1 wherein the amount of water comprises from at least a trace to a substantial excess based on the amount of said tetrahydrofuran.
Claim 11
Dependent Claim
22 words
A process as defined in claim 9 wherein the amount of water comprises at least one equivalent per equivalent of said tetrahydrofuran.
Claim 12
Dependent Claim
47 words
A process as defined in claim 1 wherein said 2-alkoxytetrahydrofuran or 2-alkoxy-substituted-tetrahydrofuran is selected from a compound of the general formula: ##STR5## wherein R is hydrogen or alkyl of from 1 to 8 carbon atoms and R 1 is alkyl of from 1 to 8 carbon atoms.
Claim 13
Dependent Claim
16 words
A process as defined in claim 11 wherein said compound is 2-methoxytetrahydrofuran, 2-n-propoxytetrahydrofuran, 2-methoxy-4-methyltetrahydrofuran or 2-methoxy-5,5-dimethyltetrahydrofuran.
Claim 14
Dependent Claim
31 words
A process as defined in claim 12 wherein said compound is 2-methoxytetrahydrofuran, and said catalyst comprises ruthenium on carbon and minor amounts of the corresponding lactone are co-produced with said 1,4-diol.
Claim 15
Dependent Claim
19 words
A process as defined in claim 12 wherein said compound is 2-methoxytetrahydrofuran and said catalyst comprises nickel on kieselguhr.
Claim 16
Dependent Claim
19 words
A process as defined in claim 12 wherein said compound is 2-n-propoxytetrahydrofuran and said catalyst comprises nickel on kieselguhr.
Claim 17
Dependent Claim
19 words
A process as defined in claim 12 wherein said compound comprises 2-methoxytetrahydrofuran and said catalyst comprises palladium on alumina.
Claim 18
Dependent Claim
29 words
A process as defined in claim 12 wherein said compound comprises 2-methoxy-4-methyltetrahydrofuran, said catalyst comprises copper chromite and minor amounts of the corresponding lactone are co-produced with said diol.
Claim 19
Dependent Claim
17 words
A process as defined in claim 12 wherein said compound comprises 2-methoxy-5,5-dimethyltetrahydrofuran and said catalyst comprises cobalt.
Claim 20
Dependent Claim
35 words
A process as defined in claim 1 which also includes the step of preparing said 2-alkoxytetrahydrofuran or 2-alkoxy-substituted-tetrahydrofuran by contacting an allylic alcohol, carbon monoxide, hydrogen and a corresponding alkanol with a rhodium hydroformylation catalyst.
Claim 21
Dependent Claim
25 words
A process as defined in claim 19 wherein said allylic alcohol comprises allyl alcohol, methallyl alcohol or 2-methyl-3-buten-2-ol and said alkalol comprises methanol or n-propanol.
References Cited (Backward Citations)
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US2888492A
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US3773842A
Cited
US3671550A
Cited
US3966827A
Cited
US3929915A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-05-22 | 1981-11-21 | 1982-05-23 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-05-22 | 1985-11-21 | 1986-05-23 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-05-22 | 1989-11-21 | 1990-05-23 | $7700.00 | Window Closed / Lapsed |