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Phosphine ligand compound and preparation method thereof, catalyst composition and application thereof, and vinyl acetate hydroformylation method

A technology of compound and phosphine ligand, which is applied in the field of hydroformylation of vinyl acetate, can solve the problem of low conversion rate of 2-acetoxypropanal and achieve the effect of increased selectivity

Pending Publication Date: 2020-06-23
CHINA PETROLEUM & CHEM CORP +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The purpose of the present invention is to provide a kind of phosphine ligand compound and preparation method thereof, a kind of catalyst composition and its Application in catalyzing vinyl acetate hydroformylation and the method for vinyl acetate hydroformylation, using the phosphine ligand compound provided by the invention can improve vinyl acetate conversion rate and 2-acetoxy propionaldehyde selectivity, and mild reaction conditions

Method used

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  • Phosphine ligand compound and preparation method thereof, catalyst composition and application thereof, and vinyl acetate hydroformylation method
  • Phosphine ligand compound and preparation method thereof, catalyst composition and application thereof, and vinyl acetate hydroformylation method
  • Phosphine ligand compound and preparation method thereof, catalyst composition and application thereof, and vinyl acetate hydroformylation method

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specific Embodiment approach

[0050] According to a preferred embodiment of the present invention, the method for preparing the phosphine ligand comprises:

[0051] 1) Under nitrogen atmosphere, add HO-B-OH into the reactor, then add PCl dropwise while stirring 3 , after the dropwise addition is completed, the temperature is raised to 60-100°C, and the reaction is performed for 1-3h;

[0052] 2) Mix the compound represented by formula (4), DMAP and solvent and add it dropwise to the reactor. After the dropwise addition, heat up to 40-60°C and react for 1-3h; the solvent is tetrahydrofuran; wherein, HO- B-OH and PCl 3 The molar ratio of the compound shown in formula (4) is 1:(4-8):(0.5-2).

[0053] In the present invention, the progress of the reaction can be monitored by chromatography. After the reaction, the obtained product can be post-treated by various post-treatment methods routinely used in the art. The post-processing methods include, but are not limited to: extraction, recrystallization, washi...

preparation example 1

[0079]

[0080] Dissolve 3.3kg of sodium hydroxide (AR) and 83g of sodium dodecylsulfonate (AR) in 15L of distilled water, heat to 60°C, and add 91mol Continue heating to 80°C, use a metering pump to add 2.8L hydrogen peroxide (30% by weight, AR) dropwise, keep the temperature not higher than 90°C during the dropwise addition, add dropwise for 3h, after the dropwise addition, continue to stir for 0.5h, and stir Cool to room temperature, centrifugally filter, wash the filter cake with 15L distilled water in the kettle, centrifugally filter, return the filter cake to the kettle for slurry washing, repeat three times, then use 15L acetonitrile to wash, centrifugal filter, filter cake back to the kettle for slurry washing, repeat three times, and pump the filtrate to the solvent Distillation kettle for distillation and reuse. Oven-dried at 105°C to obtain

[0081] Yield: 85%.

[0082] NMR: 1H NMR (CDCl3 / TMS, 300MHz) δ (ppm): 2.0 (s, 18H, 6CH3), 2.27 (s, 18H, 6CH3), 5.25 (s...

preparation example 2

[0085]

[0086] According to the method of Preparation Example 1, the difference is that replaced by an equimolar amount of get

[0087] Yield: 90%.

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Abstract

The invention relates to the field of vinyl acetate hydroformylation, and discloses a phosphine ligand compound and a preparation method thereof, a catalyst composition and application thereof, and avinyl acetate hydroformylation method. The phosphine ligand compound has a structure shown as a formula (1); wherein A is selected from a substituted or unsubstituted C1-C20 alkylene group; B1 and B2are each independently selected from a substituted or unsubstituted biphenyl group; substituent groups optionally existing in A, B1 and B2 are respectively and independently selected from at least oneof C1-C20 alkyl, halogen, C1-C10 alkoxyl, hydroxyl, carboxyl and aldehyde group; and the provided phosphine ligand compound can effectively improve the conversion rate of vinyl acetate and the selectivity of 2-acetoxy propionaldehyde.

Description

technical field [0001] The invention relates to the field of hydroformylation of vinyl acetate, in particular to a phosphine ligand compound and a preparation method thereof, a catalyst composition and application thereof, and a method for hydroformylation of vinyl acetate. Background technique [0002] Vinyl acetate undergoes hydroformylation reaction with synthesis gas (mixed gas of carbon monoxide and hydrogen) under the action of olefin hydroformylation catalyst to generate 3-acetoxypropionaldehyde and 2-acetoxypropionaldehyde, and its product 3 -Acetoxypropanal and 2-acetoxypropanal react with hydrogen under the action of an aldehyde hydrogenation catalyst to produce 3-acetoxypropanol and 2-acetoxypropanol, under the action of an ester hydrolysis catalyst Hydrolysis produces 1,3-propanediol and 1,2-propanediol. Or its products 3-acetoxypropionaldehyde and 2-acetoxypropionaldehyde generate important industrial products such as lactic acid and 3-hydroxypropionic acid und...

Claims

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Application Information

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IPC IPC(8): C07F9/6574B01J31/22C07C67/29C07C69/14
CPCC07F9/6574B01J31/185C07C67/29
Inventor 徐向亚冯华升赵思源张明森冯静刘红梅姜健准刘东兵
Owner CHINA PETROLEUM & CHEM CORP
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