Method for manufacturing delta-valerolactone

A technology of valerolactone and alkyl hydroxyvalerate, which is applied in the field of manufacturing δ-valerolactone, and can solve the problems of low product yield, high price, and increased production cost, etc.

Active Publication Date: 2018-05-04
WANHUA CHEM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Wherein in the Baeyer-Villiger oxidation reaction, cyclopentanone is limited to petrochemical products, and the original source is narrow; Oxidation, due to the high price of organic peroxyacids and the pollution of the environment by the by-product organic acids after the reaction, post-treatment requires a large amount of alkaline reagents such as sodium carbonate, which will undoubtedly increase production costs
In addition, due to the existence of peroxides, if misoperation occurs in the reaction process, it may lead to disastrous consequences. Therefore, the preparation of valerolactone by Baeyer-Villiger method has not been widely used in industry.
The method of dehydrogenating δ-valerolactone using 1,5-pentanediol as a raw material needs to be completed under high temperature conditions (300°C), and the by-product n-valeric acid in the reaction product corrodes the reactor and increases the reaction rate. The input cost of equipment and the difficulty of product separation
[0007] It can be seen that the existing methods cannot meet the demand of industrial mass production of high-quality δ-valerolactone
Therefore need to seek a kind of preparation method of the delta-valerolactone that is suitable for industrialized production, be used to solve low product yield in the prior art, raw material source is limited difficult to obtain and expensive and reaction conditions are sensitive and difficult to control, safety factor is low And other issues

Method used

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  • Method for manufacturing delta-valerolactone
  • Method for manufacturing delta-valerolactone
  • Method for manufacturing delta-valerolactone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] (1). The preparation of methyl 4,5-epoxyvalerate: 42.08g sodium hydroxide (1.01mol, 96%) and 185g methanol are placed in a 500ml four-necked flask, heated to methanol reflux temperature, and then dropwise Add 75.54g methyl acetate (1.01mol, 99%) and 92.50g epichlorohydrin (1.00mol, 99%) dropwise to the liquid funnel at the same time, the time for adding drops is 5h, keep the reaction temperature as the methanol reflux temperature, after the feed is finished, Continue the heat preservation reaction for 1h to obtain 394.99g of the reaction suspension containing white powder precipitate, and use a 50μm filter to filter under reduced pressure at 0.03MPa to obtain 330.89g of the filtrate. The gas chromatography analysis product content is 38.11wt.%. The yield of oxychloropropane is 97.00%.

[0062] (2). Preparation of methyl 5-hydroxyvalerate: The synthetic reaction of methyl 5-hydroxyvalerate was carried out in a stainless steel tubular trickle bed reactor with an inner dia...

Embodiment 2

[0073] (1). The preparation of ethyl 4,5-epoxyvalerate: 218.75g sodium hydroxide (5.25mol, 96%) and 1850.00g ethanol are placed in a 5000ml four-necked flask, heated to ethanol reflux temperature, and then Add 466.95g of ethyl acetate (5.25mol, 99%) and 462.50g of epichlorohydrin (5.0mol, 99%) dropwise to the dropping funnel at the same time, the time for adding is 3h, keep the reaction temperature at the reflux temperature of ethanol, and the feeding is finished Afterwards, the insulation reaction was continued for 1h, and 2987.34g of the reaction suspension containing white powder precipitate was obtained, which was filtered under reduced pressure at 0.03MPa using a 50 μm filter to obtain 2675.60g of the filtrate, and the gas chromatography analysis product content was 26.29wt.%. The yield of oxychloropropane is 97.71%.

[0074] (2). Preparation of ethyl 5-hydroxyvalerate: reactor and catalyst are the same as in Example 1.

[0075] The filtrate containing ethyl 4,5-epoxypen...

Embodiment 3

[0085] (1). The preparation of 4,5-epoxypropyl valerate: 214.58g sodium hydroxide (5.15mol, 96%) and 1387.50g propanol are placed in a 5000ml four-necked flask, heated to propanol reflux temperature, Then adopt dropping funnel to dropwise add 530.97g propyl acetate (5.15mol, 99%) and 462.50g epichlorohydrin (5.0mol, 99%) simultaneously, dropwise time is 4h, keeps reaction temperature to be propanol reflux temperature, After the feed was completed, the heat preservation reaction was continued for 1 hour, and 2587.62 g of the reaction liquid containing a white powder precipitate was obtained, which was filtered with a 50 μm filter under reduced pressure at 0.03 MPa to obtain 2283.15 g of the filtrate, and the product content of gas chromatography analysis was 33.73 wt.%. , The yield is 97.48% in terms of epichlorohydrin.

[0086] (2). Preparation of 5-hydroxypropyl valerate: reactor and catalyst are the same as in Example 1.

[0087] The filtrate containing 4,5-epoxypropyl vale...

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Abstract

The invention provides a method for manufacturing delta-valerolactone. The method comprises the following steps: (1) carrying out nucleophilic substitution reactions between alkyl acetate representedby the formula (I) and epoxy chloropropane to generate 4,5-epoxy alkyl valerate represented by the formula (III); (2) subjecting 4,5-epoxy alkyl valerate obtained in the step (1) to a hydrogenation treatment to generate 5-alkyl hydroxyl valerate represented by the formula (IV); and (3) making 5-alkyl hydroxyl valerate obtained in the step (2) carry out cyclization reactions to generate delta-valerolactone. The total yield of the method can reach 95% or more. The method has the advantages of cheap and easily available raw materials, little environmental pollution, mild reaction conditions, lowcost, high yield, easy purification, and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a method for producing δ-valerolactone. Background technique [0002] δ-valerolactone, also known as 1,5-valerolactone, delta-valerolactone, tetrahydro-2H-2-pyrone, tetrahydro-o-pyrone, tetrahydrocoumarin, the English name is δ -Valerolactone, abbreviated as DVL, is a cyclic lactone compound similar to caprolactone, with a molecular weight of 100.12, a boiling point of 230°C, and a molecular formula of C 5 h 8 o 2 , a colorless transparent liquid at room temperature. The specific structural formula is as follows: [0003] [0004] δ-valerolactone is a multipurpose chemical intermediate used in different fields, mainly used to replace caprolactone in ink and coating additives. Using valerolactone instead of caprolactone in ink and paint additives, the ink and paint produced have the advantages of better viscosity reduction and non-solidification at low temperature than tho...

Claims

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Application Information

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IPC IPC(8): C07D309/30
CPCC07D309/30Y02P20/10
Inventor 刘运海胡江林宋延方杨洋陈永曾伟杨恒东丁可王坤陈长生曹善建黎源华卫琦
Owner WANHUA CHEM GRP CO LTD
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