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Method for preparing 2,3-pinene oxide through epoxidation of alpha-pinene

A technology of epoxy pinane and epoxidation, which is applied in chemical instruments and methods, organic chemistry, molecular sieve catalysts, etc., can solve the problems of difficult separation, difficult separation of catalysts, high price, etc., and achieve improved conversion yield and excellent catalytic performance The effect of activity and operation safety

Active Publication Date: 2014-10-29
ZHEJIANG UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In commercially available low concentrations of H 2 o 2 (30% or 27.5%) as the oxidant in the low-temperature oxidation reaction, the homogeneous catalytic process of α-pinene epoxidation has the disadvantages of difficult separation of the catalyst, difficulty in recovery and recycling, etc.
In the heterogeneous catalytic epoxidation system, for the epoxidation of α-pinene with rigid molecular structure and strong hydrophobicity, the conversion rate is low and the reaction effect is not ideal, and some expensive catalysts are used to promote the reaction. Phase transfer reagent, and difficult to separate
Therefore, for using environmentally friendly hydrogen peroxide as an oxygen source, there is still a lack of a more effective epoxidation process that is compatible with the molecular structure of α-pinene

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] In a four-necked flask equipped with a stirrer, a thermometer, a dropping funnel and a condenser, add 1.0 part of α-pinene, 15 parts of acetonitrile, 0.5 part of 0.5mol / L NaHCO 3 , 0.2 parts of catalyst, the catalyst is a Co-containing mesoporous silica molecular sieve with a pore size distribution of 3.74 nm. Under stirring conditions, 1.5 parts of 30% hydrogen peroxide was added dropwise, and the reaction temperature was controlled to 65°C. After 5.0 hours of reaction time, the organic matter was filtered and extracted, and the organic layer was washed with saturated sodium chloride solution to neutrality. After drying, the solvent was removed, and the reaction product at 75-77°C and 2.0 kPa was collected by distillation under reduced pressure. Through gas chromatography analysis, the conversion rate of α-pinene was 58.2%, and the yield of 2,3-epoxypinane was 47.8%.

[0022] The preparation method of the catalyst of this embodiment is as follows: at room temperature,...

Embodiment 2

[0024] In a four-necked flask equipped with a stirrer, a thermometer, a dropping funnel and a condenser, add 1.0 part of α-pinene, 15 parts of acetonitrile, 0.5 part of 0.5mol / L NaHCO 3 , 0.2 parts of catalyst, the catalyst is mesoporous silica molecular sieve containing Cr, the pore size distribution is 3.89nm. Under stirring conditions, 1.5 parts of 30% hydrogen peroxide was added dropwise, and the reaction temperature was controlled to 65°C. After 5.0 hours of reaction time, the organic matter was filtered and extracted, and the organic layer was washed with saturated sodium chloride solution to neutrality. After drying, the solvent was removed, and the reaction product at 75-77°C and 2.0 kPa was collected by distillation under reduced pressure. By gas chromatography analysis, the conversion rate of α-pinene was 44.6%, and the yield of 2,3-epoxypinane was 37.7%.

[0025] The preparation method of the catalyst of this embodiment is as follows: at room temperature, a certain...

Embodiment 3

[0027] In a four-necked flask equipped with a stirrer, a thermometer, a dropping funnel and a condenser, add 1.0 part of α-pinene, 15 parts of acetonitrile, 0.5 part of 0.5mol / L NaHCO 3 , 0.2 parts of catalyst, the catalyst is mesoporous silica molecular sieve containing Mn, and the pore size distribution is 3.46nm. Under stirring conditions, 1.5 parts of 30% hydrogen peroxide was added dropwise, and the reaction temperature was controlled to 65°C. After 5.0 hours of reaction time, the organic matter was filtered and extracted, and the organic layer was washed with saturated sodium chloride solution to neutrality. After drying, the solvent was removed, and the reaction product at 75-77°C and 2.0 kPa was collected by distillation under reduced pressure. Through gas chromatography analysis, the conversion rate of α-pinene was 66.3%, and the yield of 2,3-epoxypinane was 46.4%.

[0028] The preparation method of the catalyst of this embodiment is as follows: at room temperature, ...

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Abstract

The invention discloses a method for preparing 2,3-pinene oxide through epoxidation of alpha-pinene. According to the method, a mesoporous silica molecular sieve containing Ti, Co, Cr and Mn and having a three-dimensional wormhole hexagonal structure is used as a catalyst for epoxidation, the pore size distribution of the catalyst ranges from 3nm to 6nm, the surface is subjected to silanization grafting treatment, the usage amount of the catalyst is 10-50% of the mass of alpha-pinene, an environmentally-friendly commercially available low-concentration hydrogen peroxide is used as an oxidant, and the temperature of catalytic reaction is at 50-80DEG C. The catalyst shows excellent catalysis performance on the epoxidation of alpha-pinene, and provides a new technology for preparing pinene oxide, and the technological method is safe to operate, good in environmentally-friendliness, economic and practical, and suitable for industrial production.

Description

Technical field [0001] The invention belongs to the field of fragrance chemistry, and specifically relates to a method for preparing 2,3-epoxypinane by epoxidation of α-pinene. Background technique [0002] The epoxidation of α-pinene to prepare 2,3-epoxypinane has always been an important research content in the field of terpenes and fragrance chemistry in turpentine. The α-pinene molecule contains a special bicyclic double bond structure and has a high Reactivity and unique reaction diversity. So far, for the epoxidation reaction of α-pinene under mild conditions, organic peroxides such as peracetic acid and tert-butyl hydroperoxide are mostly used to prepare epoxypinene. During the process, due to the high concentration of Peroxide poses safety concerns due to its explosion hazard. [0003] Due to H 2 O 2 The active oxygen content is high, and the by-product after the reaction is only water. It is environmentally friendly, has mild reaction conditions, is easy to oper...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D303/04C07D301/12B01J31/02
CPCC07D301/12C07D303/04B01J29/0308B01J29/0333B01J29/0341B01J2229/32B01J35/647
Inventor 陈平毛建新范宇鹏胡建良
Owner ZHEJIANG UNIV
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