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Extraction method for separation of high boiling aldehyde products and recovery of catalyst

一种高沸点、氢甲酰化催化剂的技术，应用在分离方法、物理/化学过程催化剂、溶剂萃取等方向，能够解决生产力不佳、二醛产率降低、缩醛无法通过蒸馏分离等问题

Active Publication Date: 2021-04-13
DALIAN CHEM IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The formation of acetals reduces the yield of dialdehydes and can severely reduce the reaction rate of the hydrogenation reactions used to produce tricyclodecane dimethanol and pentacyclopentadecane dimethanol, resulting in poor productivity
In addition, since the boiling point of acetal is very close to that of tricyclodecane dimethanol and pentacyclopentadecane dimethanol, the acetal cannot be separated by distillation

Method used

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  • Extraction method for separation of high boiling aldehyde products and recovery of catalyst
  • Extraction method for separation of high boiling aldehyde products and recovery of catalyst
  • Extraction method for separation of high boiling aldehyde products and recovery of catalyst

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0263] Example 1: Procedure for the Hydroformylation Process

[0264] The following procedure was performed under an atmosphere with a hydrogen to carbon monoxide ratio of 1:1. 100 grams of methylcyclohexane, 0.015 grams of Rh (acac) (CO) 2 (available from Aldrich) and 4.5 grams of tris(2,4-di-tert-butylphenyl)phosphite (available from BASF) were mixed together to form a hydroformylation mixture. The hydroformylation mixture was heated to 70° C. for 1.5 hours to dissolve uniformly. When the procedure was complete, the hydroformylation mixture was poured into an autoclave at a pressure of 1 kg / cm2 gauge. Thereafter, the temperature and pressure of the autoclave were increased to 80° C. and 50 kg / cm2 gauge, respectively. 50 grams of dicyclopentadiene (available from Zeon) was continuously fed to the autoclave at a rate of 8.3 grams / minute during 30 minutes using a metering pump. The reaction was carried out for 12 hours at a pressure of 50 catties / cm2 gauge. After the react...

Embodiment 2

[0267] Example 2: Procedure of the extraction method

[0268] The non-aqueous hydroformylation product solution (174.5 g) was mixed with an aqueous extraction solvent (MPO: 104.4 g, methanol: 35.0 g, water: 35.1 g) at a mass ratio of 1:1 and the temperature was maintained at 30 ° C. Stir in the vessel. After stirring for 1 hour, the mixture was poured into a glass extractor for 2 hours, and a biphasic mixture (non-aqueous hydroformylation solvent layer (i.e., non-polar phase) and aqueous extraction solvent layer (i.e., polar phase) was obtained. sexuality)). Gas chromatography (Agilent 6980N, column: HP-1 methylsiloxane 30.0 m x 0.32 mm x 1 micron), graphite furnace atomic absorption spectrometer (PerkinElmerAnalyst 600), and inductively coupled plasma atomic emission spectrometer (Agilent) measured the non-polar phase and the polar phase, and the results are shown in Table 2.

[0269] Table 2

[0270]

[0271] a Measured by gas chromatography

[0272] b Measured by ...

Embodiment 3a to 3h

[0293] Examples 3a to 3h: Extraction solvents

[0294] The non-aqueous hydroformylation product solution prepared according to the procedure of Example 1 - Hydroformylation method was extracted using various extraction solvents, as shown in Table 3.

[0295] table 3

[0296]

[0297] In the present invention, partition coefficient Kp=(concentration of high-boiling aldehyde compound in polar phase / concentration of high-boiling aldehyde compound in non-polar phase). For example, Kp=(Concentration of TCDDA in polar phase / Concentration of TCDDA in non-polar phase).

[0298] For example, TCDDA is the high boiling aldehyde compound; the polar phase is the aqueous extraction solvent layer; and the non-polar phase is the non-aqueous hydroformylation solvent layer.

[0299] The extraction solvents of Table 3 (Examples 3a to 3d) are each embodiments of the extraction solvents (ie, aqueous extraction solvents) of the present invention. None of the extraction solvents of Table 3 (Ex...

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Abstract

The invention relates to an extraction method for recovering high-boiling aldehyde products and catalysts from hydroformylation product solutions. The various problems associated with the separation of high boiling aldehyde products from hydroformylation product liquids containing hydroformylation catalysts are solved using the process described in the present invention, while also reducing the formation of acetal compounds, in particular acetal formation amount.

Description

technical field [0001] The invention relates to an extraction method for recovering high-boiling aldehyde products and catalysts from hydroformylation product solutions. Background technique [0002] All publications listed herein are hereby incorporated by reference to the same extent as if each individual publication or patent application was specifically and individually indicated to be incorporated by reference. The following description includes information that is helpful in understanding the present invention and does not constitute an admission that any of the information provided is prior art or relevant to the presently claimed invention, or that any publication specifically or implicitly cited is prior art. [0003] Hydroformylation is a catalytic process known in the art for the conversion of alkenes to aldehydes in which the alkenes are made by adding a formyl group (CHO) and a hydrogen atom to the carbon-carbon double bond of the alkenes. The aldehyde has one ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C45/80C07C47/347B01J38/00B01J23/46B01D11/04
CPCC07C45/80B01J38/00B01J23/464B01D11/0492C07C2603/90C07C47/347C07C45/50C07C2603/68C07C29/141C07C31/278C07C45/86
Inventor 周俊彦王兴运邱仕丰
Owner DALIAN CHEM IND CO LTD
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