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Method for producing DVL (delta-valerolactone)

A technology of valerolactone and aldehyde valeronitrile, which is applied in the field of manufacturing δ-valerolactone, can solve problems such as limitations, disasters, and difficult product separation, and achieve the effects of mild reaction conditions, less environmental pollution, and wide sources

Active Publication Date: 2018-04-24
WANHUA CHEM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Wherein the Baeyer-Villiger oxidation reaction oxidation cyclopentanone raw material is limited to petrochemical products, and uses peroxides such as peroxybenzoic acid, anhydrous peracetic acid, acetaldehyde monoperacetic acid etc. to prepare oxidation cyclopentanone, due to organic Peroxy acid is expensive and the by-product organic acid produced after the reaction pollutes the environment. After-treatment requires a large amount of alkaline reagents such as sodium carbonate, which will undoubtedly increase production costs, and if misoperation occurs, it may lead to disastrous consequences. Therefore, there is no Widely used in industry
The method of dehydrogenating 1,5-pentanediol as a raw material to generate δ-valerolactone needs to be completed under high temperature conditions (300°C), and there is a by-product n-valeric acid in the reaction product, which makes it difficult to separate the product
[0007] Visible, existing method can't satisfy the preparation of δ-valerolactone

Method used

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  • Method for producing DVL (delta-valerolactone)
  • Method for producing DVL (delta-valerolactone)
  • Method for producing DVL (delta-valerolactone)

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] (1). Preparation of 5-formyl valeronitrile: 41.88g (1.01mol, 99%) of acetonitrile is placed in a 250ml four-necked flask, warmed up to reflux temperature, and then 0.1822g (0.0005mol, 0.0005mol, 25%) tetramethylammonium hydroxide solution and 56.60g of acrolein (1.00mol, 99%), the dropwise addition time is 5h, the reaction temperature is kept at reflux temperature, and the insulation reaction is continued for 1h after the feeding is completed, and 98.06g of the reaction solution is obtained .

[0042] The reaction solution was subjected to vacuum distillation at 5.0KPa and 130°C after removal of light components at normal pressure and 100°C, and 94.93g of the product at the temperature of 101-104°C / 5.0KPa was collected, and the purity of the gas chromatographic analysis was 99.0%. The yield of the product based on acrolein is 96.89%.

[0043] (2). Preparation of 5-hydroxyvaleronitrile: The synthetic reaction of 5-hydroxyvaleronitrile is carried out in a trickle bed rea...

Embodiment 2

[0054] (1). Preparation of 5-formyl valeronitrile: 434.8g (10.5mol, 99%) of acetonitrile is placed in a 2500ml four-necked flask, warmed up to reflux temperature, and then 36.44g (0.1mol, 25%) tetramethylammonium hydroxide solution and 566.0g acrolein (10.0mol, 99%), the dropwise addition time is 2h, the reaction temperature is kept at the reflux temperature, and the insulation reaction is continued for 1h after the feeding is completed, and 1029.46g of the reaction solution is obtained .

[0055] The product purification was the same as in Example 1, and 955.33 g of a product with a purity of 99.2% was obtained, and the yield of the final product calculated as acrolein was 97.70%.

[0056] (2). Preparation of 5-hydroxyvaleronitrile: The reactor, catalyst and activation process are the same as in Example 1.

[0057] The 5-formyl valeronitrile prepared by reaction step 1) enters continuously through a feed pump, liquid space velocity WHSV=5.0g / gcat / h, hydrogen and 5-formyl val...

Embodiment 3

[0062] (1). Preparation of 5-formyl valeronitrile: 424.5g (10.25mol, 99%) of acetonitrile is placed in a 2500ml four-neck flask, warmed up to reflux temperature, and then 9.11g (0.025mol, 9.11g, 0.025mol, 25%) tetramethylammonium hydroxide solution and 566.0g acrolein (10.0mol, 99%), the dropwise addition time is 4h, keep the reaction temperature at the reflux temperature, continue the insulation reaction for 1h after feeding, and obtain 992.91g reaction liquid .

[0063] The product purification was the same as in Example 1, and 954.34 g of a product with a purity of 99.1% was obtained, and the yield of the final product was 97.50% based on acrolein.

[0064] (2). Preparation of 5-hydroxyvaleronitrile: The reactor and catalyst activation process are the same as in Example 1, and the catalyst is copper-silicon dioxide (Cu: 21.55wt%, based on the total weight of the catalyst based on copper element) catalyst.

[0065] The 5-formyl valeronitrile prepared by reaction step 1) ent...

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Abstract

The invention provides a method for producing DVL (delta-valerolactone). The method comprises the steps as follows: 1) acetonitrile and acraldehyde are subjected to an addition reaction, and a reaction solution containing an intermediate product 5-formyl butylcyanide is obtained; 2) 5-formyl butylcyanide is obtained is obtained after the reaction solution in the step 1) is subjected to reduced pressure distillation and separation purification, 5-formyl butylcyanide is subjected to a hydrogenation reaction, and 5-hydroxyl butylcyanide is produced; 3) 5-hydroxyl butylcyanide obtained in step 2)is subjected to a self-alcoholysis cyclization reaction and DVL is obtained. The total reaction yield is up to 95% or above. Raw materials are cheap and easy to obtain, the method causes small environmental pollution, adopts mild reaction conditions and is high in yield, low in cost and suitable for industrial production, and the product is easy to purify.

Description

technical field [0001] The invention relates to a method for producing δ-valerolactone, which belongs to the field of organic synthesis. 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 multi-purpose chemical intermediate, and it is used in different fields, mainly used to replace caprolactone in ink and coating additives, and valerolactone is used in the production of ink and coating additives instead of caprolactone Compared with the products produced only with caprolactone, the inks and coatings of our p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/33
CPCC07D307/33
Inventor 宋延方刘运海胡江林王磊杨洋陈永曾伟杨恒东陈长生丁可王坤曹善健黎源华卫琦
Owner WANHUA CHEM GRP CO LTD
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