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A kind of method for preparing 2,3-epoxy pinane by epoxidation of α-pinene

A technology of pinane oxide 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 achieves improved conversion yield and excellent catalysis. Active, safe-to-use effects

Active Publication Date: 2016-07-06
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 parts of α-pinene, 15 parts of acetonitrile, and 0.5 parts 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 3.74nm. Under stirring conditions, add 1.5 parts of 30% hydrogen peroxide dropwise, control the reaction temperature at 65°C, and after the reaction time of 5.0 hours, filter and extract the organic matter, then wash the organic layer with saturated sodium chloride solution to neutrality, wash the organic layer with anhydrous sodium sulfate After drying, the solvent was removed, and the reaction product at 75-77°C and 2.0kPa was collected by distillation under reduced pressure. According to gas chromatography analysis, the conversion rate of α-pinene was 58.2%, and the yield of 2,3-epoxy pinane was 47.8%.

[0022] The preparation method of the catalyst of this embo...

Embodiment 2

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

[0025] The preparation method of the catalyst of this embo...

Embodiment 3

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

[0028] The preparation method of the catalyst of this embodime...

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Abstract

The invention discloses a method for preparing 2,3-epoxypinene by epoxidation of α-pinene. The method uses a mesoporous silica molecular sieve with a three-dimensional wormhole hexagonal structure containing Ti, Co, Cr, and Mn as the The epoxidation catalyst has a pore size distribution between 3-6nm, and the surface has been silanized and grafted. The catalyst dosage is 10-50% of the mass of α-pinene, and environmentally friendly commercially available low-concentration hydrogen peroxide is used as the oxidant. The catalytic reaction temperature is 50 to 80°C. The catalyst shows excellent catalytic performance for the epoxidation of α-pinene and provides a new process for the preparation of epoxypinene. This process is safe to operate, environmentally friendly, economical and practical, and suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of flavor chemistry, and in particular relates to a method for preparing 2,3-epoxy pinane by epoxidation of α-pinene. Background technique [0002] The preparation of 2,3-epoxypinane by epoxidation of α-pinene has always been an important research content in the field of terpenoids and fragrance chemistry in turpentine oil. α-pinene molecule contains a special bicyclic double bond structure and has a high Reactivity and unique reactivity 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 pinane epoxy. There are safety concerns with peroxides having an explosion hazard. [0003] due to H 2 o 2 The content of active oxygen is high, the by-product after the reaction is only water, the environmental protection is good, the reaction conditions are mild, the operation is convenient, and the co...

Claims

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Application Information

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Patent Type & Authority Patents(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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