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2-ethyl-2,3-epoxybutanal and method for producing same

A technology of epoxy butyraldehyde and manufacturing method, applied in the direction of organic chemistry method, organic chemistry and the like

Pending Publication Date: 2020-09-15
JNC CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the epoxide of 2-ethylcrotonaldehyde, 2-ethyl-2,3-epoxybutyraldehyde, has not been synthesized so far.

Method used

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  • 2-ethyl-2,3-epoxybutanal and method for producing same
  • 2-ethyl-2,3-epoxybutanal and method for producing same
  • 2-ethyl-2,3-epoxybutanal and method for producing same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Under nitrogen atmosphere, add sodium p-dodecylbenzenesulfonate (3.6mg ), and carried out ice-bath cooling, added 30wt% hydrogen peroxide water (1.0ml). Then, while vigorously stirring, a 50 wt % sodium hydroxide aqueous solution (0.2 ml) was added dropwise at such a rate that the internal temperature did not exceed 10°C. After stirring for 30 minutes under ice-cooling, samples were taken and analyzed by GC. As a result, the main product was obtained with a conversion rate of 100%, a selectivity of 97%, and a diastereomeric ratio of 62 / 38. Sodium bisulfite powder and sodium bicarbonate powder are gradually added in small amounts at a temperature not exceeding 10°C, and excess hydrogen peroxide is decomposed while maintaining neutrality. According to standing and separating the hydrogen spectrum nuclear magnetic resonance of the oily substance of gained ( 1 H-nuclear magnetic resonance, 1 H-NMR) and GC-MS, confirmed to be 2-ethyl-2,3-epoxybutyraldehyde.

[0056] 1 H...

Embodiment 2

[0059] Under nitrogen atmosphere, the mixture of 2-ethyl crotonaldehyde (GC purity 90%, trans / cis=93 / 7, 1.0g) and water (10ml) is carried out ice bath cooling, and adds 30wt% hydrogen peroxide water ( 1.0ml). Then, while vigorously stirring, a 20 wt% sodium hydroxide aqueous solution (0.84 ml) was added dropwise at a rate at which the internal temperature did not exceed 20°C, and then a sample was taken and analyzed by GC. , The diastereomeric ratio of 64 / 36 produced 2-ethyl-2,3-epoxybutyraldehyde.

Embodiment 3

[0061] Under a nitrogen atmosphere, 2-ethylcrotonaldehyde (GC purity 90%, trans / cis=93 / 7, 1.0 g) was cooled in an ice bath, and 30 wt % hydrogen peroxide (1.0 ml) was added. Then, while vigorously stirring, a 50 wt % sodium hydroxide aqueous solution (0.27 ml) was added dropwise at such a rate that the internal temperature did not exceed 10°C. After 10 minutes, the internal temperature rose rapidly from 3°C to 25°C, so the stirring was temporarily stopped. Thereafter, when the internal temperature reached 10° C., stirring was resumed, sampling was performed 30 minutes later, and GC analysis was performed. As a result, it was confirmed that 2 - Ethyl-2,3-epoxybutyraldehyde.

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Abstract

The present invention provides: 2-ethyl-2,3-epoxybutanal, which is considered to be a useful building block in organic synthetic chemistry; and a method for producing the same. In the presence of alkali, 2-ethyl crotonaldehyde is reacted with hydrogen peroxide to obtain 2-ethyl-2,3-epoxybutanal represented by formula (1). A surfactant may be added in this reaction.

Description

technical field [0001] The invention relates to 2-ethyl-2,3-epoxybutyraldehyde and a production method thereof. Background technique [0002] Since ancient times, the epoxidation of α, β-unsaturated aldehydes has been continuously carried out. For example, as the epoxidation of acrolein or methacrolein, it is known that there is a method of making hydrogen peroxide water work under alkaline conditions (non-patent Document 1) etc.; as the epoxidation of crotonaldehyde, under alkaline conditions, the method (non-patent document 2) that makes polyvinylpyrrolidone supported hydrogen peroxide is known; Oxidation, the known method that hydrogen peroxide is reacted in the presence of solid base catalyst and surfactant etc. (non-patent document 3, non-patent document 4, non-patent document 5, non-patent document 6); As 2- The epoxidation of ethyl-2-hexanal is known by the method of making sodium hypochlorite act (Non-Patent Document 7), but the epoxidation of tiglaldehyde (tigliald...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D303/32C07D301/12C07B61/00
CPCC07D303/32C07B61/00C07D301/12
Inventor 川岛正敏
Owner JNC CORP