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Method for preparing 3-methyl butyraldehyde from isobutylene

A technology of methylbutyraldehyde and isobutene, which is applied in the direction of carbon monoxide reaction preparation and organic chemistry, can solve the problems of low catalytic activity, difficult self-polymerization of isovaleraldehyde, difficult reaction, etc., and achieves simplified separation process, high conversion rate, The effect of less side effects

Active Publication Date: 2016-10-12
DAQING HI TECH LIHUA ENVIRONMENTAL PROTECTION TECH CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] When isobutene undergoes hydroformylation reaction to generate isovaleraldehyde, due to the presence of methyl branches in isobutene, the reaction space is large, the catalytic activity is low, the reaction is difficult to carry out, and the product isovaleraldehyde is difficult to self-polymerize, so rhodium-based The homogeneous complex catalytic system catalyzes the hydroformylation of isobutene. The catalyst and solvent are very different from the hydroformylation of light olefins, and it is difficult to hydroformylate isobutene with the hydroformylation of light olefins. Preparation of isovaleraldehyde

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] In the 100mL reactor, add 20mL n-decane solvent successively, triphenylphosphine carbonyl rhodium acetylacetonate and triphenylphosphine, the concentration of triphenylphosphine carbonyl rhodium acetylacetonate is 300 μ g / mL, and the phosphine rhodium mol ratio is 15, The air in the reactor was replaced three times with synthesis gas having a molar ratio of hydrogen to carbon monoxide of 1.0, and 0.45 g / (mL solvent) of isobutene was added. Then start heating, and continue to feed synthesis gas after the temperature rises to 90°C, so that the pressure in the reactor reaches 2.0MPa, and finally start stirring and record the time. After 4 hours of reaction, the heating mantle of the reactor was removed, the reactor was cooled to room temperature, and samples were taken for analysis. The conversion rate of isobutene is 44.64%, and the selectivity of isovaleraldehyde is 98.99%.

Embodiment 2

[0031] In a 100mL reactor, add 30mL n-decane solvent, triphenylphosphinecarbonylrhodium acetylacetonate and triphenylphosphine successively, the concentration of triphenylphosphinecarbonylrhodium acetylacetonate is 400 μg / mL, and the phosphine-rhodium mol ratio is 7.5, The air in the reactor was replaced three times with synthesis gas having a molar ratio of hydrogen to carbon monoxide of 1.0, and 0.25 g / (mL solvent) isobutene was added. Then start heating, and continue to feed synthesis gas after the temperature rises to 95°C, so that the pressure in the reactor reaches 4.0 MPa, and finally start stirring and record the time. After 4 hours of reaction, the heating mantle of the reactor was removed, the reactor was cooled to room temperature, and samples were taken for analysis. The conversion rate of isobutene is 68.41%, and the selectivity of isovaleraldehyde is 99.24%.

Embodiment 3

[0033] In a 100mL reactor, add 35mL n-decane solvent, triphenylphosphinecarbonylrhodium acetylacetonate and triphenylphosphine successively, the concentration of triphenylphosphinecarbonylrhodium acetylacetonate is 400 μg / mL, and the phosphine-rhodium mol ratio is 2.5, The air in the reactor was replaced three times with synthesis gas having a molar ratio of hydrogen to carbon monoxide of 1.0, and 0.20 g / (mL solvent) of isobutene was added. After that, start heating, and continue to feed synthesis gas after the temperature rises to 90°C, so that the pressure in the reactor reaches 4.0 MPa, and finally start stirring and record the time. After 4 hours of reaction, the heating mantle of the reactor was removed, the reactor was cooled to room temperature, and samples were taken for analysis. The conversion rate of isobutene is 64.73%, and the selectivity of isovaleraldehyde is 99.17%.

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Abstract

The invention discloses a method for preparing 3-methyl butyraldehyde from isobutylene. According to the method, the isobutylene and synthesis gas are utilized as raw materials, acetylacetonatocarbonyltriphenylp hosphinerhodium(I) is utilized as the catalyst, triphenylphosphine is utilized as a ligan, and n-decane is utilized as a solvent, thereby performing a hydroformylation reaction. According to the method for preparing the 3-methyl butyraldehyde from the isobutylene, performances of the catalyst can be greatly exerted, the conversion rate of the isobutylene is high, and the selectivity of the isovaleraldehyde is high; and side reactions are a few, side products, such as pivaldehyde, isoamyl alcohol and the like, are not detected in products; furthermore, subsequent separation process for the products is simplified.

Description

technical field [0001] The invention relates to a method for preparing 3-methylbutanal by using isobutene as a starting material. technical background [0002] 3-Methylbutyraldehyde, also known as isovaleraldehyde, is a colorless liquid with a disgusting smell, but it has a fruity aroma after dilution. A fruit flavor and tobacco flavoring substance. At the same time, isovaleraldehyde is widely used in the pharmaceutical industry and is an intermediate in the production of many drugs, which can be used to produce vitamin E and anticonvulsant drug pregabalin. Alcohol, acid, amine and other derivatives obtained from further processing of isovaleraldehyde are fine chemicals with high added value, which can be used to make plasticizers, fabric additives, and surfactants. [0003] At present, the method of preparing isovaleraldehyde in China mainly uses isoamyl alcohol as raw material to oxidize it with concentrated sulfuric acid and dichromic acid, but this process has many sid...

Claims

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Application Information

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IPC IPC(8): C07C45/50C07C47/02
CPCC07C45/50C07C47/02
Inventor 张谦温张慧汝孙锦昌宋兆伟杨大奎
Owner DAQING HI TECH LIHUA ENVIRONMENTAL PROTECTION TECH CO LTD
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