US4275243A
Expired / Lapsed
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Process for producing hydroxybutyraldehyde
Assignee: Tosoh Corp
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Filing: 1979-08-27
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Granted: 1981-06-23
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Expires: 1999-08-27
Abstract
Abstract An organic tri-substituted phosphine having a boiling point of at least 200 DEG C. and a reaction medium having a boiling point of at least 200 DEG C. are used in a hydroformylation of allyl alcohol with carbon monoxide and hydrogen in the presence of a rhodium complex catalyst. The concentration of the organic phosphine is 5x10-4 to 0.3 mol. per 1 liter of the reaction medium. The reaction medium is distilled at lower than 80 DEG C. under a reduced pressure and the bottom residue as the catalyst solution is recycled. The hydroformylation can be repeated by using the bottom residue as the catalyst solution.
Inventors
- 👤 Toshihiro Saito
- 👤 Shoji Arai
- 👤 Yukihiro Tsutsumi
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 14:22
CPC Classifications
C; C07; C07C; C07C45/00; C07C45/49; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/584
Claims Analysis
Total Claims: 8
Claim 1
Independent Claim
120 words
In a process for producing hydroxybutyraldehyde by reacting allyl alcohol with carbon monoxide and hydrogen in a reaction medium in the presence of a rhodium complex catalyst having an organic tri-substituted phosphine, the improvement wherein the organic tri-substituted phosphine and the reaction medium have a boiling point higher than 200° C., the phosphine is used at a concentration of 5×10 -4 to 0.3 mol. per 1 liter of the reaction medium in the hydroformylation and then a distillative separation of the reaction mixture is carried out in the absence of oxygen at a temperature of 20° C. to 80° C. under a reduced pressure to separate the reaction product from the solution of the rhodium complex in the reaction medium.
Claim 2
Dependent Claim
120 words
In a process for producing hydroxybutyraldehyde by reacting allyl alcohol with carbon monoxide and hydrogen in a reaction medium in the presence of a rhodium complex catalyst having an organic tri-substituted phosphine, the improvement wherein the organic tri-substituted phosphine and the reaction medium have a boiling point higher than 200° C., the phosphine is used at a concentration of 5×10 -4 to 0.3 mol. per 1 liter of the reaction medium in the hydroformylation and then a distillative separation of the reaction mixture is carried out in the absence of oxygen at a temperature of 20° C. to 80° C. under a reduced pressure to separate the reaction product from the solution of the rhodium complex in the reaction medium.
Claim 3
Dependent Claim
121 words
In a process for producing hydroxybutyraldehyde by reacting allyl alcohol with carbon monoxide and hydrogen in a reaction medium in the presence of a rhodium complex catalyst having an organic trisubstituted phosphine, the improvement wherein the organic trisubstituted phosphine and the reaction medium have a boiling point higher than 200° C., the phosphine is used at a concentration of 5×10 -4 to 0.3 mol. per 1 liter of the reaction medium in the hydroformylation, and then a distillative separation of the reaction mixture is carried out in the absence of oxygen at a temperature lower than 80° C. and at a pressure of 1-20 mmHg, to separate the reaction product from the solution of the rhodium complex in the reaction medium.
Claim 4
Dependent Claim
121 words
In a process for producing hydroxybutyraldehyde by reacting allyl alcohol with carbon monoxide and hydrogen in a reaction medium in the presence of a rhodium complex catalyst having an organic trisubstituted phosphine, the improvement wherein the organic trisubstituted phosphine and the reaction medium have a boiling point higher than 200° C., the phosphine is used at a concentration of 5×10 -4 to 0.3 mol. per 1 liter of the reaction medium in the hydroformylation, and then a distillative separation of the reaction mixture is carried out in the absence of oxygen at a temperature lower than 80° C. and at a pressure of 1-20 mmHg, to separate the reaction product from the solution of the rhodium complex in the reaction medium.
Claim 5
Dependent Claim
31 words
The process of claims 1 or 2, wherein said rhodium complex catalyst is used at a concentration ranging from 0.1 to 15 mg atom per 1 liter of the reaction medium.
Claim 6
Dependent Claim
39 words
The process of claims 1 or 2, wherein said organic trisubstituted phosphine has the formula PR 3 , wherein the total number of carbon atoms in the 3R's in said formula PR 3 is in the range of 10-30.
Claim 7
Dependent Claim
31 words
The process of claims 1 or 2, wherein the organic phosphine is used at a ratio of 5 to 200 atoms of phosphorous to 1 atom of rhodium of said catalyst.
Claim 8
Dependent Claim
71 words
The process of claims 1 or 2, wherein said reaction medium is selected from the group consisting of saturated hydrocarbons having at least 12 carbon atoms, aromatic hydrocarbons having at least 9 carbon atoms, alcohols having at least 9 carbon atoms, ethers having at least 10 carbon atoms, ether or ether glycols of polyhydric alcohols having at least 7 carbon atoms, esters having at least 9 carbon atoms, and mixtures thereof.
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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) | 1984-06-22 | 1984-12-22 | 1985-06-23 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-06-22 | 1988-12-22 | 1989-06-23 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-06-22 | 1992-12-22 | 1993-06-23 | $7700.00 | Window Closed / Lapsed |