US4510332A
Expired / Lapsed
US
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Process for producing 1,9-nonanedial
Assignee: Kuraray Co Ltd
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Filing: 1983-02-25
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Granted: 1985-04-09
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Expires: 2003-02-25
Abstract
Abstract A process for producing 1,9-nonanedial which comprises hydroformylating 7-octen-1-al with a mixture of hydrogen and carbon monoxide in an aqueous sulfolane or 1,4-butanediol solution in the presence of a rhodium complex and the sodium, potassium or lithium salt of m-(diphenylphosphino)benzenesulfonic acid, extracting 1,9-nonanedial from the reaction mixture with a primary alcohol or a mixture of a primary alcohol and a saturated aliphatic hydrocarbon, and recycling the extraction residue containing the catalyst components to the 7-octen-1-al hydroformylation step.
Inventors
- 👤 Mitsuo Matsumoto
- 👤 Noriaki Yoshimura
- 👤 Masuhiko Tamura
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 07:30
CPC Classifications
C; C07; C07C; C07C45/00; C07C45/78; C07C45/81; C07C45/82; C07C43/00; C07C43/30; C07C43/317; C07C45/49; C07C45/80; C07C45/85
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
134 words
A process for producing 1,9-nonanedial, which comprises the steps of: (I) hydroformylating 7-octen-1-al with a mixture of hydrogen and carbon monoxide in an aqueous solution of sulfolane or 1,4-butanediol in which the weight ratio of sulfolane or 1,4-butanediol to water is 15/85 to 75/25, in the presence of (a) a rhodium complex and (b) the sodium, potassium or lithium salt of m-(diphenylphosphino)-benzenesulfonic acid at a temperature of 40° C. to 110° C.; (II) extracting 1,9-nonanedial from the reaction mixture obtained in step (I) with a saturated aliphatic primary alcohol containing about 5 to 11 carbon atoms or a mixture of said primary alcohol and a saturated aliphatic hydrocarbon containing about 5 to 10 carbon atoms; and (III) recycling the extraction residue containing the catalyst components obtained in step (II) to the hydroformylation step (I).
Claim 2
Dependent Claim
134 words
A process for producing 1,9-nonanedial, which comprises the steps of: (I) hydroformylating 7-octen-1-al with a mixture of hydrogen and carbon monoxide in an aqueous solution of sulfolane or 1,4-butanediol in which the weight ratio of sulfolane or 1,4-butanediol to water is 15/85 to 75/25, in the presence of (a) a rhodium complex and (b) the sodium, potassium or lithium salt of m-(diphenylphosphino)-benzenesulfonic acid at a temperature of 40° C. to 110° C.; (II) extracting 1,9-nonanedial from the reaction mixture obtained in step (I) with a saturated aliphatic primary alcohol containing about 5 to 11 carbon atoms or a mixture of said primary alcohol and a saturated aliphatic hydrocarbon containing about 5 to 10 carbon atoms; and (III) recycling the extraction residue containing the catalyst components obtained in step (II) to the hydroformylation step (I).
Claim 3
Dependent Claim
55 words
The process of claim 1, wherein, in step (I), said rhodium complex is present in a rhodium concentration of 0.05 to 10 milligram atoms per liter of the reaction mixture and the sodium, potassium or lithium salt of m-(diphenylphosphino)benzenesulfonic acid is present in an amount of at least 10 equivalents per gram atom of rhodium.
Claim 4
Dependent Claim
57 words
The process of claim 1, wherein the extraction in step (II) is carried out at a temperature of 10° to 60° C. with a mixture of a primary alcohol selected from the group consisting of n-pentanol, n-hexanol, n-heptanol, n-octanol and n-nonanol and a saturated aliphatic hydrocarbon selected from the group consisting of pentane, hexane, heptane and octane.
Claim 5
Dependent Claim
23 words
The process of claim 1, wherein the extract layer obtained in step (II) is washed with water and then distilled, thereby obtaining 1,9-nonanedial.
Claim 6
Dependent Claim
109 words
The process of claim 1, wherein the extraction in step (II) is carried out at a temperature of 10° of 60° C. with a primary alcohol selected from the group consisting of n-pentanol, n-hexanol, n-heptanol, n-octanol, n-nonanol and n-decanol or a mixture of said primary alcohol and a saturated aliphatic hydrocarbon selected from the group consisting of pentane, hexane, heptane, octane, nonane and decane, followed by washing the obtained extract layer with water, maintaining the extract layer at a temperature of 0° to 50° C. to precipitate crystals of the dihemiacetal of 1,9-nonanedial with said primary alcohol, separating the crystals from said extract layer and obtaining 1,9-nonanedial by distillation.
Claim 7
Dependent Claim
25 words
The method of claim 1, wherein the hydrogen to CO mole ratio ranges from 0.5 to 5 in the feed gas to the hydroformylation step.
Claim 8
Dependent Claim
29 words
The method of claim 1, wherein said rhodium complex is HRh(CO)(PA 3 ) 3 , wherein A is aryl, Rh 4 (CO) 12 or Rh 6 (CO) 16 .
Claim 9
Dependent Claim
54 words
The method of claim 1, wherein the catalyst activity of step [I] is stabilized by buffering the reaction mixture to within the pH range of 5 to 7 with a mixture of NaH 2 PO 4 and Na 2 HPO 4 or mixture of KH 2 PO 4 and K 2 HPO 4 .
Claim 10
Dependent Claim
25 words
The method of claim 1, wherein the ratio of said primary alcohol to hydrocarbon in extraction step II ranges from 1/20 to 20/1 by volume.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-04-08 | 1988-10-08 | 1989-04-09 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-04-08 | 1992-10-08 | 1993-04-09 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-04-08 | 1996-10-08 | 1997-04-09 | $7700.00 | Window Closed / Lapsed |