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Method for hydroformylation of vinyl acetate

A technology of vinyl acetate hydroformyl and vinyl acetate, which is applied in the field of vinyl acetate hydroformylation, can solve the problems of poor 3-acetoxypropionaldehyde selectivity and harsh reaction conditions, achieves high conversion rate, improves selective effect

Active Publication Date: 2017-04-19
CHINA PETROLEUM & CHEM CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] The purpose of the present invention is to provide a vinyl acetate hydroformylation method in order to overcome the relatively poor selectivity of product 3-acetoxy propionaldehyde in the prior art and the relatively harsh reaction conditions. method

Method used

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  • Method for hydroformylation of vinyl acetate
  • Method for hydroformylation of vinyl acetate
  • Method for hydroformylation of vinyl acetate

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Experimental program
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Embodiment approach

[0037] According to a preferred embodiment of the present invention, the temperature at which the vinyl acetate is contacted with carbon monoxide and hydrogen is 20-200°C, more preferably 80-120°C.

[0038] According to a preferred embodiment of the present invention, the pressure at which the vinyl acetate is contacted with carbon monoxide and hydrogen is 0.5-10 MPa, more preferably 3-4 MPa. In the present invention, the pressure refers to gauge pressure.

[0039] According to the present invention, the volume ratio of the solvent to vinyl acetate is preferably (0.01-10):1, more preferably (0.01-8):1. Adopting this preferred ratio can further improve the selectivity of 3-acetoxypropanal at lower reaction temperature and reaction pressure.

[0040] According to the present invention, the solvent refers to a solvent that is inert to the hydroformylation reaction but can effectively dissolve raw materials, reaction products and catalysts.

[0041] According to the present inve...

Embodiment 1

[0053] In a 100ml autoclave, add 6ml vinyl acetate (64.88mmol) as the raw material for hydroformylation, 44ml cyclohexane as solvent, 12.2mg acetylacetonate triphenylphosphinecarbonyl rhodium (0.02mmol) and 26.8mg ( +)-Isopropene-2,3-dihydroxy-1,4-bisdiphenylphosphinobutane (0.05 mmol) was used as catalyst, and the reaction vessel was sealed. Replaced with nitrogen three times, with synthesis gas (CO:H 2 The volume ratio is 1:1) and replaced three times, and the pressure is increased to 4.0MPa with synthesis gas, and the temperature is raised to the reaction temperature of 100°C to start the hydroformylation reaction. The synthesis gas consumed by the reaction is indicated by the pressure change of the gas storage tank until the gas is no longer consumed as the end of the reaction. The reaction kettle was lowered to room temperature, unreacted gas was discharged, and then replaced by nitrogen for 3 times, the reaction kettle was opened, the reaction product was analyzed by ga...

Embodiment 2

[0059] According to the method of Example 1, the difference is that 45ml of methyl tert-butyl ether is used as a solvent, and the catalyst added is 24.4mg of triphenylphosphinecarbonyl rhodium acetylacetonate (0.04mmol) and 35.2mg of (+)-isopropylene- 2,3-dihydroxy-1,4 bis(2-naphthyl)phosphinobutane (0.05 mmol), the reaction pressure is 3.5 MPa, and the temperature is 80°C. The results are shown in Table 1.

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Abstract

The invention relates to a method for hydroformylation of vinyl acetate. The method comprises the step of enabling the vinyl acetate to be in contact with carbon monoxide and hydrogen gas in the presence of a solvent and a catalyst system, wherein the catalyst system contains a rhodium complex and a phosphine ligand; the rhodium complex is one or more selected from rhodium(triphenylphosphine)carbonyl acetylacetonate, rhodium acetylacetone and chlorocarbonylbis(triphenylphosphine)rhodium; and the phosphine ligand is one or more selected from phosphine-containing organic matters represented by the following formulae shown in the description, wherein Ar in the formulae (1, 3 and 4) is substituted or unsubstituted aryl, M in the formula (2) is hydrogen, halogen element or substituted or unsubstituted alkyl, and t in the formula (3) is an integer from 2 to 10. According to the method, the selectivity to 3-acetoxypropanal in a hydroformylation reaction process of the vinyl acetate can be improved while a relatively high conversion ratio is guaranteed under the conditions of relatively low reaction temperature and reaction pressure.

Description

technical field [0001] The invention relates to a method for hydroformylation of vinyl acetate. Background technique [0002] Vinyl acetate reacted with synthesis gas (CO and H) under the action of olefin hydroformylation catalyst 2 Mixed gas) to carry out hydroformylation reaction, generate 3-acetoxy propionaldehyde and 2-acetoxy propionaldehyde, 3-acetoxy propionaldehyde and 2-acetoxy propionaldehyde in the aldehyde group hydrogenation catalyst React with hydrogen under the action to generate 3-acetoxypropanol and 2-acetoxypropanol, 3-acetoxypropanol and 2-acetoxypropanol can be hydrolyzed under the action of ester hydrolysis catalyst to generate 1,3- Propylene glycol and 1,2-propanediol can generate lactic acid and 3-hydroxypropionic acid under the action of an oxidizing agent. 1,3-propanediol, 1,2-propanediol, lactic acid and 3-hydroxypropionic acid are all important chemical raw materials, especially, 1,3-propanediol is an important polyester fiber monomer with high m...

Claims

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Application Information

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IPC IPC(8): C07C67/38C07C69/14
CPCC07C67/38C07C69/14
Inventor 徐向亚张明森刘红梅冯静姜健准
Owner CHINA PETROLEUM & CHEM CORP
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