US4301077A
Expired / Lapsed
US
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Process for the manufacture of 1-4-butanediol and tetrahydrofuran
Assignee: Standard Oil Co
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Filing: 1980-12-22
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Granted: 1981-11-17
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Expires: 2000-12-22
Abstract
Abstract Oxygenated C 4 hydrocarbons, such as maleic anhydride, are hydrogenated to tetrahydrofuran and/or 1,4-butanediol by a process comprising contacting the hydrocarbon with hydrogen at hydrogenation conditions in the presence of less than 25 wt. % water, based on the weight of the hydrocarbon, and a ruthenium-containing hydrogenation catalyst, such as the catalyst of the formula Ru Ni Co Zn.sub.0.4.
Inventors
- 👤 Frederick A. Pesa
- 👤 Anne M. Graham
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 12:00
CPC Classifications
C; C07; C07C; C07C29/00; C07C29/132; C07C29/136; C07C29/147; C07C29/149; B; B01; B01J; B01J23/00; B01J23/38; B01J23/54; B01J23/56; B01J23/60; B01J23/70; B01J23/89; B01J23/8933; B01J23/8953; C07C29/17; C07C29/177; C07D; C07D307/00; C07D307/02; C07D307/04; C07D307/06; C07D307/08
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
153 words
A process for the manufacture of at least one of tetrahydrofuran and 1,4-butanediol from an oxygenated C 4 hydrocarbon selected from the group consisting of maleic anhydride, maleic acid, succinic anhydride, succinic acid, γ-butyrolactone and mixtures comprising at least two of these, the process comprising contacting the oxygenated C 4 hydrocarbon with hydrogen at a temperature of about 175° C. to about 275° C. and a pressure of about 750 psi to about 1500 psi in the presence of less than about 25 wt % water, based on the weight of the oxygenated hydrocarbon, and a catalyst of the formula Ru.sub.0.01-2 M.sub.0.01-2 M'.sub.0.01-2 M".sub.0.01-1 O.sub.x where M is at least one of nickel and palladium, M' is at least one of iron, cobalt, rhodium, osmium, iridium and platinum, M" is at least one of zinc and cadmium, and x is a number sufficient to satisfy the valency requirements of the other elements present.
Claim 2
Dependent Claim
153 words
A process for the manufacture of at least one of tetrahydrofuran and 1,4-butanediol from an oxygenated C 4 hydrocarbon selected from the group consisting of maleic anhydride, maleic acid, succinic anhydride, succinic acid, γ-butyrolactone and mixtures comprising at least two of these, the process comprising contacting the oxygenated C 4 hydrocarbon with hydrogen at a temperature of about 175° C. to about 275° C. and a pressure of about 750 psi to about 1500 psi in the presence of less than about 25 wt % water, based on the weight of the oxygenated hydrocarbon, and a catalyst of the formula Ru.sub.0.01-2 M.sub.0.01-2 M'.sub.0.01-2 M".sub.0.01-1 O.sub.x where M is at least one of nickel and palladium, M' is at least one of iron, cobalt, rhodium, osmium, iridium and platinum, M" is at least one of zinc and cadmium, and x is a number sufficient to satisfy the valency requirements of the other elements present.
Claim 3
Dependent Claim
34 words
The process of claim 1 where the molar ratio of ruthenium is between about 0.01 and 1.5, of M and M' between about 0.1 and 1.5, and of M" between about 0.05 and 0.8.
Claim 4
Dependent Claim
12 words
The process of claim 2 where M' is iron, cobalt, or rhodium.
Claim 5
Dependent Claim
9 words
The process of claim 3 where M" is zinc.
Claim 6
Dependent Claim
9 words
The process of claim 4 where M is nickel.
Claim 7
Dependent Claim
9 words
The process of claim 5 where M' is cobalt.
Claim 8
Dependent Claim
23 words
The process of claim 6 where the oxygenated C 4 hydrocarbon is maleic anhydride, γ-butyrolactone, or a mixture of maleic anhydride and γ-butyrolactone.
Claim 9
Dependent Claim
35 words
The process of claim 7 where the oxygenated C 4 is a mixture of about 1 to about 20 wt %, based on the total weight of the mixture, of maleic anhydride dissolved in γ-butyrolactone.
Claim 10
Dependent Claim
131 words
A process for the manufacture of 1,4-butanediol from maleic anhydride, the process comprising contacting a mixture of about 1 to about 20 wt %, based on the total weight of the mixture, of maleic anhydride dissolved in γ-butyrolactone with hydrogen at a temperature of about 230° C. to about 250° C. and a pressure of about 1000 psi to about 1300 psi in the presence of less than about 10 wt % water, based on the total weight of the oxygenated hydrocarbon mixture, and a catalyst of the formula Ru.sub.0.01-2 M.sub.0.1-2 M'.sub.0.1-2 Zn.sub.0.3-0.5 O.sub.x (IV) where M is at least one of nickel and palladium, M' is at least one of iron, cobalt and rhodium, and x is a number sufficient to satisfy the valency requirements of the other elements present.
Claim 11
Dependent Claim
131 words
A process for the manufacture of 1,4-butanediol from maleic anhydride, the process comprising contacting a mixture of about 1 to about 20 wt %, based on the total weight of the mixture, of maleic anhydride dissolved in γ-butyrolactone with hydrogen at a temperature of about 230° C. to about 250° C. and a pressure of about 1000 psi to about 1300 psi in the presence of less than about 10 wt % water, based on the total weight of the oxygenated hydrocarbon mixture, and a catalyst of the formula Ru.sub.0.01-2 M.sub.0.1-2 M'.sub.0.1-2 Zn.sub.0.3-0.5 O.sub.x (IV) where M is at least one of nickel and palladium, M' is at least one of iron, cobalt and rhodium, and x is a number sufficient to satisfy the valency requirements of the other elements present.
Claim 12
Dependent Claim
104 words
A process for the manufacture of tetrahydrofuran from γ-butyrolactone, the process comprising contacting γ-butyrolactone with hydrogen at a temperature of about 175° C. to about 230° C. and a pressure of about 750 psi to about 1300 psi in the presence of less than about 10 wt. % water, based on the total weight of γ-butyrolactone, and a catalyst of the formula Ru.sub.0.01-2 M.sub.0.1-2 M'.sub.0.1-2 Zn.sub.0.4-1 O.sub.x (V) where M is at least one of nickel and palladium, M' is at least one of iron, cobalt and rhodium, and x is a number sufficient to satisfy the valency requirements of the other elements present.
Claim 13
Dependent Claim
104 words
A process for the manufacture of tetrahydrofuran from γ-butyrolactone, the process comprising contacting γ-butyrolactone with hydrogen at a temperature of about 175° C. to about 230° C. and a pressure of about 750 psi to about 1300 psi in the presence of less than about 10 wt. % water, based on the total weight of γ-butyrolactone, and a catalyst of the formula Ru.sub.0.01-2 M.sub.0.1-2 M'.sub.0.1-2 Zn.sub.0.4-1 O.sub.x (V) where M is at least one of nickel and palladium, M' is at least one of iron, cobalt and rhodium, and x is a number sufficient to satisfy the valency requirements of the other elements present.
References Cited (Backward Citations)
US3853922A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-11-16 | 1985-05-18 | 1985-11-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-11-16 | 1989-05-18 | 1989-11-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-11-16 | 1993-05-18 | 1993-11-17 | $7700.00 | Window Closed / Lapsed |