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Production method of beta-ionone epoxide

A technology of ionone ring and production method, which is applied in the field of production of β-ionone epoxides, can solve problems such as corrosion, high cost, and large energy consumption, and achieve high economic efficiency and low equipment corrosion

Inactive Publication Date: 2015-04-29
YANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Its main synthesis method is the chemical oxidation method using ionone as raw material. The oxidants used include peracetic acid, m-chloroperoxybenzoic acid, tert-butyl chromate, oxygen, etc., but due to the high cost, serious environmental pollution and energy High consumption, corrosion of equipment and acidic ring-opening of epoxy compounds, etc., have not yet been industrialized

Method used

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  • Production method of beta-ionone epoxide
  • Production method of beta-ionone epoxide
  • Production method of beta-ionone epoxide

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Take 1 mmol of β-ionone, under the protection of nitrogen, control the temperature of the reaction system at 0-40°C, use hydrogen peroxide as the oxidant in different solvents, and catalyze the oxidation of β-ionone, as listed in the table below, using different dose and temperature conditions. The solvent can be one of ethanol, N,N-dimethylformamide, water, dichloromethane, acetonitrile, acetone, and tetrahydrofuran. The reaction time was 24 hours. After the reaction, the solvent was evaporated to dryness and separated by preparative thin layer chromatography to obtain the epoxidized product 4-[2,2,6-trimethyl-7-oxabicyclo[4.1.0 ]hept-1-yl]-3-buten-2-one.

[0022] Its reaction formula is as follows:

[0023]

[0024] Table 1 shows the reactions at different temperatures

[0025] Numbering

temperature(℃)

Yield(%)

1

0

54

2

10

66

3

25

72

4

30

70

5

40

63

[0026] Fro...

Embodiment 2

[0045] Under the protection of nitrogen, 50 mmol of β-ionone, 150 mmol of hydrogen peroxide (30w / w% aqueous solution), 0.5 mmol of bis(3,5-bistrifluoromethylphenyl)diselenide were dissolved in 50 mL of diselenide Stir in methyl chloride at room temperature (25°C) for 24 hours. The solvent was evaporated to dryness, and the epoxidized product 4-[2,2,6-trimethyl-7-oxabicyclo[4.1.0]hept-1-yl]-3- Buten-2-one. The catalyst residue is put into the next round of use, and the effect of catalyst recovery and use is checked, and the results are shown in Table 7

[0046] Numbering

[0047] It can be seen from the above results that the catalyst is stable and can be recycled and used many times.

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Abstract

The invention discloses a production method of beta-ionone epoxide in the field of flavor production, which comprises the following steps: in a nitrogen protective atmosphere, oxidizing beta-ionone in a solvent by using di(3,5-ditrifluoromethylphenyl)diselenide as a catalyst and hydrogen peroxide as an oxidizer while controlling the temperature of the reaction system at 0-40 DEG C to obtain the epoxidation product 4-[2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptyl-1-yl]-3-butenyl-2-one. The method can synthesize the 4-[2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptyl-1-yl]-3-butenyl-2-one at high selectivity. The oxidizer is clean, has high economical efficiency, and is harmless to the environment since the reduction byproduct of the oxidizer is only water. The method does not use any metal catalyst, and the used organic selenium catalyst is ecologically friendly. The reaction is performed under mild conditions in a neutral environment, and has small corrosivity for equipment, so the equipment is durable; and the catalyst is recoverable, and thus, is more suitable for industrial production.

Description

technical field [0001] The invention relates to a production method of a spice, in particular to a production method of β-ionone epoxide. Background technique [0002] In the prior art, there is a kind of β-ionone, its structural formula is: 4-(2,6,6-trimethyl-1-cyclohexenyl)-3-buten-2-one, and its molecular formula is: C 13 h 20 O, CAS: 14901-07-6; the substance is a natural fragrance with a characteristic aroma at room temperature. The oxidized product of β-ionone also has aroma and can be widely used in the field of perfume synthesis. [0003] The β-ionone epoxide in the oxidation product has the molecular formula: C 13 h 20 o 2 [0004] Chinese name: 4-[2,2,6-trimethyl-7-oxabicyclo[4.1.0]hept-1-yl]-3-buten-2-one [0005] English name: 4-(2,2,6-trimethyl-7-oxabicyclo[4.1.0]hept-1-yl)-3-buten-2-one [0006] CAS: 23267-57-4 [0007] The β-ionone epoxide is also an important fragrance, which is mainly used in tobacco, essence or additives, can enhance flavor and tas...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D303/32C07D301/12
CPCY02P20/584C07D303/32C07D301/12
Inventor 俞磊柏增炳张旭叶剑青徐清
Owner YANGZHOU UNIV
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