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Hydroformylation process

Active Publication Date: 2010-03-18
IND TECH RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, many homogeneous catalyst systems cannot be commercially applied mainly due to difficulties in separating, recovering, and reusing the homogeneous catalysts, as it is well known.
Most homogeneous catalysts, however, are thermal sensitive, such that the homogeneous catalyst may decompose during higher distillation temperatures and fail to be recovered for reuse.
Other methods for recovering the homogeneous catalyst, e.g. chromatography, are inefficient.
Although rhodium catalysts have higher reactivity, their cost is much higher than the cobalt catalysts.
On the other hand, if the volatility of the hydroformylation products is high, the abovementioned distillation method for separation is unfavorable, due to the higher temperatures decomposing the catalyst such that the catalyst cannot be recovered and reused, thus increasing costs.
The efficiency of this method is, however, not good, and a better method for the efficient separation of the hydroformylation products and catalyst is still needed.

Method used

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Examples

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Effect test

example 1

[0022]Rh(acac)(CO)2 (114 mg; 0.435 mmol), tris(2,4-di-tert-butylphenyl) phosphite (5.625 g; 8.7 mmol), and tricyclodecanedialdehyde (5.0 g) were added into a flask, followed by the addition of dry n-hexane (50 g) in the dry box. A high pressure reaction vessel was heated to 80° C., followed by vacuum and recharging with nitrogen for three times, and cooled to room temperature. The aldehyde compound and the rhodium solution were transferred to the high pressure reaction vessel, and the nitrogen in the high pressure reaction vessel was replaced with a mixture of CO / H2(1:1). The pressure inside the vessel was built-up to 40 atm, the reaction vessel was heated to 100° C., and the pressure was then built to 50 atm.

[0023]DCPD (30 g; Fluka) and dry n-hexane (10 g) were weighted and charged into a feeding bottle. The DCPD was then fed into the high pressure reaction vessel (20 mL / hours) from the feeding bottle with a feeding time of about 2 hours. The total pressure of the CO / H2 was maintai...

example 2

[0024]Rh(acac)(CO)2 (107 mg; 0.407 mmol), tris(2,4-di-tert-butylphenyl) phosphite (5.625 g; 8.7 mmol), and tricyclodecanedialdehyde (4.1 g) were added into a flask, followed by the addition of dry n-hexane (50 g) in the dry box. A high pressure reaction vessel was heated to 80° C., followed by vacuum and recharging with nitrogen for three times, and cooled to room temperature. The aldehyde compound and the rhodium solution were transferred to the high pressure reaction vessel, and the nitrogen in the high pressure reaction vessel was replaced with a mixture of CO / H2(1:1). The pressure inside the vessel was built-up to 40 atm, the reaction vessel was heated to 100° C., and the pressure was then built to 50 atm.

[0025]DCPD (30 g; Fluka) and dry n-hexane (10 g) were weighted and charged into a feeding bottle. The DCPD was then fed into the high pressure reaction vessel (20 mL / hours) from the feeding bottle with a feeding time of about 2 hours. The total pressure of the CO / H2 was maintai...

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Abstract

The disclosed is about a hydroformylation of a cyclic olefin with rhodium catalyst, and specifically about the recovering of the rhodium catalyst. Aldehyde and the cyclic olefin are added into a rhodium catalyst solution to process a hydroformylation, thereby forming the product cycloalkyl aldehyde. Afterwards, the result is divided into two layers. The upper layer is substantially rhodium catalyst solution, and the lower layer is substantially cycloalkyl aldehyde and the aldehyde. After separation, the upper layer is reserved to process next hydroformylation reaction with newly added cyclic olefin.

Description

CROSS REFERENCE TO RELATED APPLICATIONS[0001]This Application claims priority of Taiwan Patent Application No. 097135460, filed on Sep. 16, 2008, the entirety of which is incorporated by reference herein.BACKGROUND OF THE INVENTION[0002]1. Field of the Invention[0003]The present invention relates to a hydroformylation process of cyclic olefins in the presence of a metal catalyst, and in particular relates to the separation of the desired products from the metal catalyst by phase separation.[0004]2. Description of the Related Art[0005]It is known in the art that compared to a heterogeneous catalyst, the homogeneous catalyst has advantages such as high reactivity, high selectivity, and a relatively milder reaction condition. However, many homogeneous catalyst systems cannot be commercially applied mainly due to difficulties in separating, recovering, and reusing the homogeneous catalysts, as it is well known.[0006]It is known in the art that distillation is one of the favorable method...

Claims

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Application Information

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IPC IPC(8): C07C45/49
CPCC07C45/50C07C45/80C07C45/82C07C2101/16C07C2103/52C07C47/445C07C47/347C07C47/32C07C2601/16C07C2603/52
Inventor HSUEH, MAO-LINYANG, HAO-HSUNSHIH, KUO-CHENSU, TSAI-TIEN
Owner IND TECH RES INST
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