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A kind of method for preparing 1,3-propanediol by hydration and hydrogenation of acrolein

A technology for the hydration of acrolein and the preparation of hydrogen, which is applied in the preparation of carbon-based compounds, hydroxyl compounds, and organic compounds, etc., can solve the problems of difficult recycling and poor stability of homogeneous catalysts, and achieve low production cost, stability and The effect of stable composition and simple operation

Active Publication Date: 2022-08-05
WANHUA CHEM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The invention uses N-alkyl amino acid homogeneously catalyzed hydration reaction, which solves the problems of poor stability of the composition after the reaction and the difficulty of recovery and application of homogeneous catalysts, and has the advantages of stable production process and low production cost.

Method used

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  • A kind of method for preparing 1,3-propanediol by hydration and hydrogenation of acrolein
  • A kind of method for preparing 1,3-propanediol by hydration and hydrogenation of acrolein
  • A kind of method for preparing 1,3-propanediol by hydration and hydrogenation of acrolein

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-12

[0040] Using acrolein as a raw material, under the action of a homogeneous catalyst N-alkylamino acid, react with water to prepare a hydration reaction solution containing 3-hydroxypropanal:

[0041] Add deionized water, acrolein, and N-alkyl amino acids to a 1L reaction kettle, then add 0.1% mass fraction of polymerization inhibitor hydroquinone to the reaction system, continue stirring for 3h hydration reaction, take samples for analysis and calculate conversion The specific conditions and results of each embodiment are shown in Table 1, wherein the concentration of acrolein and the concentration of catalyst are their percentages in the reaction system.

[0042] Table 1 Hydration reaction

[0043]

Embodiment 13

[0045] The hydration reaction solution is added with a non-polar solvent for extraction and separation:

[0046] The hydration reaction solution of Example 1 and the extraction agent methyl tertiary butyl ether are extracted in countercurrent according to the mass ratio of 1:2, using a rotating disk extraction column with a diameter of 50 mm, the number of plates is 5, and the extraction temperature is 30 ° C. Before extraction The mass percentage content of each component (except the solvent) in the hydration reaction solution, the oil phase after extraction, and the water phase is shown in Table 2.

[0047] Table 2

[0048] Acrolein % 3-Hydroxypropionaldehyde % catalyst% other% Before extraction 4.51 15.26 6.00 1.25 oil phase 2.07 0.35 2.83 0.15 water box 0.15 15.01 0.02 1.03

[0049] The oil phase is separated by rectification, and the N-alkyl amino acids, unreacted acrolein and methyl tert-butyl ether are recovered respecti...

Embodiment 14

[0053] The hydration reaction solution is added with a non-polar solvent for extraction and separation:

[0054] The hydration reaction solution of embodiment 3 and the extraction agent benzene are extracted in countercurrent according to the mass ratio of 1:1, using a rotary disk extraction tower with a diameter of 50 mm, the number of plates is 6, the hydration reaction solution before extraction, the oil phase after extraction, the water phase The mass percentage of each component (except solvent) is shown in Table 3.

[0055] table 3

[0056] Acrolein % 3-Hydroxypropionaldehyde % catalyst% other% Before extraction 2.95 6.32 14.00 0.35 oil phase 2.41 0.32 11.89 0.06 water box 0.15 6.01 0.08 0.29

[0057] The oil phase is separated by rectification, and the N-alkyl amino acids, unreacted acrolein and methyl tert-butyl ether are recovered respectively; benzene.

[0058] Hydrogenation reaction:

[0059] A fixed bed reactor w...

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Abstract

The invention relates to a method for preparing 1,3-propanediol by hydration and hydrogenation of acrolein. Under the action of N-alkyl amino acids, acrolein is homogeneously catalyzed and reacted with water to prepare 3-hydroxypropionaldehyde, and the hydration reaction liquid is extracted and recovered. The reacted acrolein and N-alkylamino acid participate in the hydration reaction again, and the water phase is the 3-hydroxypropionaldehyde aqueous solution directly hydrogenated to prepare 1,3-propanediol. The invention solves the problem of poor composition stability of the reaction liquid outlet in the resin catalyzed production process in the existing production technology, and also overcomes the problem that the catalyst is difficult to separate, recover and apply after the catalysis of inorganic acid or organic acid, and adopts N-alkyl amino acid homogeneous phase The catalysis solves the problems of the stability of the composition after the hydration reaction and the recovery and application of the homogeneous catalyst, the production process is stable, and the production cost is low.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and relates to a method for preparing 1,3-propanediol by hydration and hydrogenation of acrolein. Background technique [0002] 1,3-Propanediol (PDO) is an important chemical raw material. It can be used as an organic solvent in industries such as inks, coatings, lubricants, and antifreeze. It can also be used as an intermediate for pharmaceutical synthesis. It is a polymer material with excellent synthesis performance as a polymer monomer. [0003] Degussa Company uses acrolein hydration hydrogenation process to produce 1,3-PDO. Its patent US 563152 points out that it uses cation exchange resin containing phosphoric acid group, and US5171898 uses chelating resin containing amino carboxyl group, both of which use fixed bed reactors, and are made of propylene 3-Hydroxypropionaldehyde was prepared by heterogeneously catalyzed hydration hydrogenation of aldehydes. In the above method, d...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C29/141C07C31/20C07C45/64C07C47/19B01J31/02
CPCC07C29/141C07C45/64B01J31/0237B01J31/0271C07C31/205C07C47/19Y02P20/584
Inventor 王中华袁帅赵聪黎源
Owner WANHUA CHEM GRP CO LTD