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Delta-dodecalactone synthesis method

A synthetic method, the technology of laurolactone, applied in the direction of organic chemistry, can solve the problems of high risk of organic peroxyacids, inconvenient transportation and storage, and difficult separation of reaction products, so as to improve the utilization rate of atoms and improve the economic efficiency. Benefits and environmental benefits, the effect of simple preparation

Inactive Publication Date: 2015-04-22
NANJING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although peroxyacid oxidizes 2-heptylcyclopentanone to prepare δ-dodecanolide reaction speed, there are following disadvantages with peroxyacid as oxidizing agent: (1) the preparation of this type of oxidizing agent needs to use high-concentration peroxide Hydrogen, and high-concentration hydrogen peroxide has many dangers in transportation and treatment; (2) a large amount of organic carboxylic acid or carboxylate waste will be formed after the reaction, which needs to be recycled or treated; (3) organic peroxyacids are used It is dangerous in the process, and transportation and storage are inconvenient, which limits its application in industrial production; (4) disadvantages such as low selectivity, difficult separation of reaction products and unfriendly environment

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] In a 50 mL three-necked flask, add 0.91 g of 2-heptylcyclopentanone, dropwise add hydrogen peroxide with a mass fraction of 30%, the molar ratio of hydrogen peroxide to 2-heptylcyclopentanone is 2:1, and then Add phosphotungstic acid supported on catalyst silica gel, the mass of which is 5% of the mass of 2-heptylcyclopentanone, stir with magnetic force, and react at 55°C for 8 hours. The mixture was filtered through a glass funnel to remove the catalyst. The filtrate was left standing to separate the organic phase. Take 2 mL of 5% sodium bicarbonate aqueous solution to wash the organic phase three times, then wash with distilled water until the organic phase is neutral, neutralize the aqueous phase with 5% sodium bicarbonate aqueous solution to weak alkalinity and extract with ethyl acetate , the ethyl acetate extract was combined with the organic phase, evaporated in vacuum, weighed, carried out gas chromatography analysis with cyclopentyl lactone as the internal sta...

Embodiment 2

[0016] In a 50 mL three-necked flask, add 0.91 g of 2-heptylcyclopentanone, dropwise add hydrogen peroxide with a mass fraction of 30%, the molar ratio of hydrogen peroxide to 2-heptylcyclopentanone is 1.5:1, and then Add phosphotungstic acid supported on catalyst silica gel, the mass of which is 5% of the mass of 2-heptylcyclopentanone, stir with magnetic force, and react at 70°C for 8 hours. The mixture was filtered through a glass funnel to remove the catalyst. The filtrate was left standing to separate the organic phase. Take 2 mL of 5% sodium bicarbonate aqueous solution to wash the organic phase three times, then wash with distilled water until the organic phase is neutral, neutralize the aqueous phase with 5% sodium bicarbonate aqueous solution to weak alkalinity and extract with ethyl acetate , the ethyl acetate extract was combined with the organic phase, evaporated in vacuum, weighed, carried out gas chromatography analysis with cyclopentyl lactone as the internal s...

Embodiment 3

[0018] In a 50 mL three-necked flask, add 0.91 g of 2-heptylcyclopentanone, dropwise add hydrogen peroxide with a mass fraction of 30%, the molar ratio of hydrogen peroxide to 2-heptylcyclopentanone is 1:1, and then Add phosphotungstic acid supported on catalyst silica gel, the mass of which is 10% of the mass of 2-heptylcyclopentanone, stir with magnetic force, and react at 70°C for 5 hours. The mixture was filtered through a glass funnel to remove the catalyst. The filtrate was left standing to separate the organic phase. Take 2 mL of 5% sodium bicarbonate aqueous solution to wash the organic phase three times, then wash with distilled water until the organic phase is neutral, neutralize the aqueous phase with 5% sodium bicarbonate aqueous solution to weak alkalinity and extract with ethyl acetate , the ethyl acetate extract was combined with the organic phase, evaporated in vacuum, weighed, carried out gas chromatography analysis with cyclopentyl lactone as the internal st...

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Abstract

The invention discloses a new method for preparing delta-dodecalactone with low-concentration hydrogen peroxide oxidized 2-heptyl cyclopentanone. 2-heptyl cyclopentanone is used as a raw material, and hydrogen peroxide with the mass fraction of 30% is used as an oxidant to prepare the delta-dodecalactone. Low-concentration hydrogen peroxide is used to replace traditional peroxy acid or high-concentration hydrogen peroxide, thereby improving the environmental economic performance of industrial preparation reactions and reducing environmental pollution. In addition, heteropoly acid is used as a catalyst, a solvent is not needed, an effective reaction can occur at 25 DEG C to 70 DEG C, and a method for oxidizing a cyclic ketone compound to lactone is provided.

Description

1. Technical field [0001] The invention uses 2-heptylcyclopentanone as a raw material, uses hydrogen peroxide with a mass fraction of 30% as an oxidizing agent, and silica gel-loaded phosphodock acid as a catalyst to synthesize δ-dodecanolide in a solvent-free medium. 2. Background technology [0002] δ-Lauryl lactone is the main ingredient in the formulation of cream flavor. The method of extracting from plants is not economical, therefore, the synthesis of δ-laurolactone is of great significance in the food industry. There are two main ways to synthesize δ-laurolactone: one is to first synthesize the key intermediate 2-heptylcyclopentanone, and then obtain δ-dodecanolide through oxidation; the other is to first synthesize δ-dodecylactone through various methods -Hydroxy acid, and then cyclized to give δ-dodecanolide. The industrial production of δ-laurolactone at home and abroad now mainly adopts the oxidation method of the intermediate 2-heptylcyclopentanone. [0003] ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D309/30
Inventor 彭新华马庆国赵婧如
Owner NANJING UNIV OF SCI & TECH
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