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A kind of preparation method of butyl caprolactone

A caprolactone and butyl-position technology, which is applied in the field of preparation of butyl-position caprolactone, can solve the problems of high initial cost of carbon capture and sequestration, high environmental protection pressure, skyrocketing temperature, etc., and achieves short steps, low equipment requirements, and easy operation. simple effect

Active Publication Date: 2022-07-05
上海埃农生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this technique needs to use a large excess of methyl acetoacetate to control the Michael monoaddition, resulting in a large waste of materials. The total yield of this document is about 67.7%, and it is easy to produce sudden in the first step Michael reaction process The temperature skyrocketing phenomenon is dangerous in actual industrial production, and the overall reaction takes a long time, requiring an average of more than 16 hours
In addition, when acetobutyric acid is produced, carbon dioxide will be produced at the same time. However, the problem of global warming is serious today, and the pressure on environmental protection is high. The recovery of carbon dioxide requires expensive equipment to process carbon dioxide, and the upfront cost of carbon capture and storage (CCS) is very high.
The final hydrogenation reaction requires the use of precious ruthenium carbon catalysts or palladium carbon catalysts, and requires high temperature and high pressure hydrogenation, which also has certain safety hazards

Method used

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  • A kind of preparation method of butyl caprolactone
  • A kind of preparation method of butyl caprolactone
  • A kind of preparation method of butyl caprolactone

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preparation example Construction

[0046] The invention provides a kind of preparation method of butyl caprolactone, the method comprises:

[0047] 1) Dissolve the β-dicarbonyl compound and the basic catalyst in a solvent for preheating;

[0048] 2) in the reaction system, drip the alkyl acrylate and carry out Michael's addition reaction;

[0049] 3) cooling the system, adding alkali, then heating the reaction system to carry out saponification reaction;

[0050] 4) adding water, cooling the system, adding a reducing agent to react;

[0051] 5) Cool the system, adjust the pH value with acid, and obtain butyl caprolactone through post-treatment.

[0052] Wherein, step 1) and step 2) mainly relate to Michael addition reaction; step 3) relate to saponification reaction; step 4) and step 5) mainly relate to reduction reaction.

[0053] The following will describe each type of reaction one by one.

[0054]

[0055] The present invention obtains a mixed intermediate by performing a Michael addition reaction bet...

Embodiment 1

[0084] Acetylacetone (1050 g, 10.5 mol) and sodium methoxide (16.2 g, 0.3 mol) were dissolved in ethanol (1000 g) and the reaction was heated to 68°C for 5 minutes. Using a constant pressure dropping funnel, methyl acrylate (860 g, 10 mol) was added dropwise to the above system for 0.25 h. After the dropping, the reaction system was heated to 80° C. and kept for 0.5 h. After the reaction, the intermediate product was analyzed by WH-500 chromatographic analyzer, and the results are shown in figure 1 , figure 1 The peak 1.59 is the solvent ethanol peak, the peak 4.85 is methyl 5-oxohexanoate, the peak 8.37 is methyl 4-acetyl-5-oxohexanoate, and the integral area of ​​the two peaks is greater than 95%, thus It can be shown that the conversion of the Michael addition reaction alkyl acrylate of the present invention is greater than 95%.

[0085]It was then cooled to 0°C and 30% sodium hydroxide solution (2670 g, 20 mol) was added. The temperature of the reaction solution was rai...

Embodiment 2

[0087] Acetylacetone (1050 g, 10.5 mol) and sodium methoxide (16.2 g, 0.3 mol) were dissolved in ethanol (1000 g), and the reaction system was heated to 83°C under strong reflux for 5 minutes. Methyl acrylate (860 g, 10 mol) was added dropwise to the above system using a constant pressure dropping funnel for 0.25 h. After the dropping was completed, the temperature controller was heated to maintain the reaction system at 80°C for 0.5 h. After the reaction, the intermediate product was analyzed by WH-500 chromatographic analyzer, and the results are shown in image 3 , image 3 The middle peak 1.61 is the solvent ethanol peak, the peak 4.89 is methyl 5-oxohexanoate, the peak 8.65 is methyl 4-acetyl-5-oxohexanoate, and the integral area of ​​the two peaks is greater than 94%. It can be shown that the conversion of the Michael addition reaction alkyl acrylate of the present invention is greater than 94%.

[0088] It was then cooled to 0°C and 30% sodium hydroxide solution (2670...

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Abstract

The invention relates to a preparation method of butyl-caprolactone, which comprises the following steps: dissolving a beta-dicarbonyl compound and a basic catalyst in a solvent for preheating; adding alkyl acrylate dropwise to a reaction system to carry out a Michaelk Addition reaction; cooling the system, adding alkali, then heating the reaction system to carry out saponification reaction; adding water, cooling the system, adding a reducing agent for reaction; cooling the system, adjusting the pH value with acid, and after post-processing butyl caprolactone. The method of the invention has the advantages of simple process operation, high safety, high utilization rate of raw materials, short overall time consumption, and no carbon dioxide generation.

Description

technical field [0001] The invention belongs to the field of organic chemical synthesis, in particular to a preparation method of butyl caprolactone. Background technique [0002] butyl caprolactone is also known as delta-caprolactone, the molecular formula is C 6 H 10 O 2 , mainly used as food flavor and tobacco flavor. The usual preparation methods include reduction of γ-acetylbutyric acid with sodium amalgam, followed by acidification, or boiling of δ-bromohexanoic acid with water or by Bayer-Villiger reaction with 2-methylcyclopentanone. have to. However, the sodium amalgam releases a highly flammable gas in contact with water, which is toxic to inhalation. It is a dangerous product with a cumulative effect. The raw material of δ-bromohexanoic acid is very expensive, more expensive than the product price, and is not suitable for industrial production. In addition, the existing synthesis process involves multi-step reactions, with many side reactions and many impurit...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D309/30
CPCC07D309/30Y02P20/141
Inventor 徐国俊鲁喜成李云龙
Owner 上海埃农生物科技有限公司