Hydroformylation process

Details Hydroformylation process Hydroformylation process

1997-05-27

1998-06-30

Geist, Gary

Organic compounds -- part of the class 532-570 series

Organic compounds

Oxygen containing

568451, C07C 4550

Patent

active

057736669

DESCRIPTION:

BRIEF SUMMARY
This is a 371 of PCT/JP96/02771, filed Sep. 26, 1995.


TECHNICAL FIELD

This invention relates to a process for the hydroformylation of an olefinic compound. A hydroformylated product obtained by the present invention is useful as a starting material for fine chemicals such as pharmaceuticals and agricultural chemicals, alcohols for a plasticizer, or starting materials such as diol, dicarboxylic acid, and diamine for the synthesis of a polymer compound.


BACKGROUND ART

A process for preparing an aldehyde by the reaction of an olefinic compound with hydrogen and carbon monoxide using a rhodium compound as a catalyst is called hydroformylation reaction or oxo reaction and it is an industrially useful synthetic process. The rhodium compound is, however, markedly expensive. So, in order to carry out the hydroformylation reaction in an industrially advantageous manner, a technique of recycling the rhodium compound while maintaining its catalytic activity is required.
As a method for separating the reaction mixture into a rhodium catalyst and a product in the hydroformylation reaction, there is a method using distillation. Except the case where an aldehyde having a comparatively low boiling point is produced, the above method using distillation can hardly be regarded as advantageous from the viewpoint of the industrial practice, because the rhodium catalyst is deteriorated by the heat at the time of its separation by distillation. Particularly in the case where an aldehyde to be produced has a high boiling point, the condensation of the product tends to occur under the distillation conditions to form easily by-product of a higher-boiling point condensed material. Such a higher-boiling point condensed material is concentrated in a residual liquid in a still by distillation and is accumulated gradually with the recycling of the catalyst. This increases the viscosity of the residual liquid in the still, so that, even if the catalytic activity of the catalyst is maintained, the operability of the reaction is lost with the proceeding of the production of the aldehyde, which actually prevents the recycling of the catalyst. Furthermore, owing to heat, cross-linking reaction of this higher-boiling point condensed material happens to occur, which solidifies the residual liquid in the still and makes it impossible to carry out recycling of the catalyst.
Owing to such a problem in the operability, it is inevitable to renew the catalyst in a short time in the case of separating the rhodium catalyst from the product by distillation, except the case where an aldehyde having a relatively low boiling point is produced.
As a process for avoiding the above-described problem involved by the separation of the catalyst from the product by distillation, Japanese Patent Application Laid-Open No. SHO 58-157739 provides a process in which, using a water-soluble rhodium catalyst, a hydroformylation reaction is effected in the aqueous solvent and then the product is separated by extraction using an extractant such as a hydrocarbon. In addition, U.S. Pat. No. 5,180,854 discloses a process in which a hydroformylation reaction is effected, with the water-soluble rhodium catalyst dissolved in a reaction mixture using a solubilizing agent such as N-methylpyrrolidone, and then the catalyst is separated by extraction using water as an extractant.
The process disclosed in Japanese Patent Application Laid-Open No. SHO 58-157739 for the separation of the product by extraction is excellent in that (1) the catalyst is free from the heat and deactivation and (2) accumulation of the high-boiling point condensed material is avoided. But, the process is not advantageous for the industrial application, because it requires a large amount of a solvent and therefore a large-scaled reaction apparatus, which lowers a volumetric efficiency of the reaction, and moreover a great amount of energy upon the recovery of the extractant from the extract.
On the other hand, the process disclosed in U.S. Pat. No. 5,180,854 for the extraction of the catalyst is excelle

REFERENCES:
patent: 5180854 (1993-01-01), Abatjoglou et al.

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