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Catalytic synthesis method of unsaturated alcohol

A synthesis method and unsaturated technology, which are applied in the field of catalytic synthesis of unsaturated alcohols, can solve problems such as lack of industrialization conditions, and achieve the effects of high selectivity, simple operation and high product purity.

Active Publication Date: 2013-08-28
DALIAN TRICO CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In a word, although the above-mentioned synthetic methods of unsaturated alcohols have certain advantages, they do not have the conditions for industrialization

Method used

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  • Catalytic synthesis method of unsaturated alcohol
  • Catalytic synthesis method of unsaturated alcohol
  • Catalytic synthesis method of unsaturated alcohol

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Experimental program
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Embodiment 1

[0023] In this embodiment, aluminum isopropoxide is used as a catalyst, LiBr is used as an auxiliary agent, and 3-cyclohexene-1-carbaldehyde is reduced to 3-cyclohexene-1-methanol in a solvent of isopropanol under a nitrogen atmosphere.

[0024] Add 4.8 g of aluminum isopropoxide, 1.2 g of LiBr, and 300 g of isopropanol to a 1 L flask. The temperature was raised to 80°C under nitrogen atmosphere. A solution of 60 g of 3-cyclohexene-1-carbaldehyde (0.55 mol) in isopropanol was added dropwise. During the dropwise addition process, the temperature of the system will decrease due to the generation of acetone with low boiling point. Evaporate the generated acetone while adding dropwise, carefully control the top temperature below 85 degrees, and use a thorn-type distillation column to increase the separation of acetone and isopropanol and control the amount of solvent evaporated. Gas chromatography was followed until the chromatographic content of 3-cyclohexene-1-carbaldehyde was...

Embodiment 2

[0027] In this example, the aluminum isopropoxide derivative derived from dihydric phenol is used as catalyst, and LiBr is used as auxiliary agent. Under nitrogen atmosphere, 3-cyclohexene-1-carbaldehyde is reduced to 3-cyclohexyl in solvent isopropanol En-1-methanol.

[0028] Add 3.0 g of dihydric phenol-derived aluminum isopropoxide derivative, 1.2 g of LiBr, and 300 g of isopropanol in a 1 L flask. The temperature was raised to 60°C under nitrogen atmosphere. A solution of 60 g of 3-cyclohexene-1-carbaldehyde (0.55 mol) in isopropanol was added dropwise. During the dropwise addition process, the temperature of the system will decrease due to the generation of acetone with low boiling point. Evaporate the generated acetone while adding dropwise, carefully control the top temperature below 85 degrees, and use a thorn-type distillation column to increase the separation of acetone and isopropanol and control the amount of solvent evaporated. Gas chromatography was followed u...

Embodiment 3

[0030] In this embodiment, aluminum sec-butoxide is used as a catalyst, and MgBr 2 As an auxiliary agent, reduce cinnamaldehyde to cinnamyl alcohol in the solvent 2-butanol under nitrogen atmosphere.

[0031] In a 1L flask was added 6.6 g of aluminum sec-butoxide, 2.6 g of MgBr 2 , 300 g of 2-butanol. The temperature was raised to 110°C under a nitrogen atmosphere. A solution of 66 g of cinnamaldehyde (0.5 mol) was added dropwise. During the dropwise addition process, the temperature of the system will decrease due to the generation of 2-butanone with low boiling point. Evaporate the generated 2-butanone while adding dropwise, carefully control the top temperature below 100 degrees, and use a thorn-type distillation column to increase the separation of 2-butanone and 2-butanol, and control the amount of solvent evaporated . Gas chromatography followed up until the chromatographic content of cinnamaldehyde was lower than 0.5%, and the reaction time was about 1-2 hours. Af...

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Abstract

The invention discloses a catalytic synthesis method of unsaturated alcohol, relating to the field of chemical synthesis. The enzymatic synthesis method of unsaturated alcohol is characterized in that unsaturated aldehyde is reduced into the unsaturated alcohol in a solvent in a nitrogen atmosphere by using aluminum alcohol or an aluminum alcohol derivative as a catalyst and using a lithium salt or a magnesium salt as an auxiliary agent. In the method, generated low boiling point ketone is continuously evaporated out in an alcohol solvent by using the unsaturated aldehyde as a raw material, the 5-10 percent aluminum alcohol as the catalyst and the lithium salt or the magnesium salt as an auxiliary agent, thereby a new process for synthesizing the unsaturated alcohol with high conversion rate and high selectivity is realized. The method has the characteristics that high-yield and high-purity unsaturated alcohol can be obtained by using a catalytic quantity of the aluminum alcohol, a product with reduced unsaturated bonds is not generated, and the selectivity is high. In the method, the catalyst has the advantages of low price, simplicity in operation, recycling of the solvent and less waste water and waste solvent and meets the requirements of low carbon and environmental protection. Compared with traditional methods, the method has a good industrial prospect.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a catalytic synthesis method for unsaturated alcohols. Background technique [0002] Unsaturated alcohols are a class of important chemical, pharmaceutical and epoxy resin intermediates, and their synthesis research is of great significance. The selective reduction of unsaturated aldehydes to unsaturated alcohols is a hotspot in basic research, and it is also a difficult point that needs to be broken through in the industrial field. Now make an overview according to the different hydrogen sources used. Use LiAlH 4 , red aluminum or NaBH 4 As a hydrogen source, unsaturated alcohols can be obtained with high selectivity (J.Org.Chem., 35, 1041, 1970), but this type of reducing agent has obvious disadvantages due to its instability and a large amount of waste, especially not suitable for industry Production; there are many studies on organosilane as hydrogen source: Matthia...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C29/14C07C33/32C07C33/14C07C33/03C07C33/025
Inventor 王军伟寇伟群于晓东仇敏朱旭
Owner DALIAN TRICO CHEM
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