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Preparation method of beta-damascenone spice

A damascenone fragrance and raw material technology, applied in the field of preparation of β-damascenone fragrance, can solve the problems of unsuitability for industrial production, harsh reaction conditions, high cost, etc., and achieve low cost, short synthesis route and easy operation Effect

Active Publication Date: 2014-08-27
INST OF PROCESS ENG CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The problem to be solved by the present invention is to provide a four-step method for preparing β-damascenone spices with β-ionone as the starting material, so as to overcome the harsh reaction conditions, low yield and high cost, which are not suitable for industrial production and other shortcomings

Method used

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  • Preparation method of beta-damascenone spice
  • Preparation method of beta-damascenone spice
  • Preparation method of beta-damascenone spice

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Example 1: Synthesis of β-ionone oxime

[0044] Add 3.85g (0.06mol) of hydroxylamine hydrochloride, 6.25g (0.07mol) of sodium acetate, and 10mL of distilled water into a 50mL round-bottomed flask, stir and add 10.00g (0.05mol) of β-ionone and 20mL of ethanol. Heating in a water bath, stirring the reaction for 2h and ending the reaction. Extract with diethyl ether, extract three times, combine the extracts, wash with 10mL of 10% sodium bicarbonate, and then dry, suction filter and rotary evaporate to finally obtain β-ionone oxime with a yield of about 99.0%.

Embodiment 2

[0045] Example 2: Synthesis of β-violet isoxazole derivatives

[0046] Add 26.50g (0.19mol) of potassium carbonate, 100mL of distilled water, 50mL of tetrahydrofuran and 10.00g (0.05mol) of β-ionone oxime into a 250mL round bottom flask, and add 12.20g (0.05mol) of iodine and 27.60 g (0.17 mol) potassium iodide. Reflux at 66°C for 6h, extract with ether, extract 3 times, wash with 7.5mL saturated sodium sulfite solution at the same time, combine the extracts, then dry, filter and rotary evaporate to obtain β-violet isoxazole derivatives, the yield About 89.5%.

Embodiment 3

[0047] Embodiment three: the synthesis of β-dihydrodamascenone

[0048] Vacuumize the 500mL three-neck round bottom flask first, then keep it at a low temperature of -40°C, and pass ammonia gas into it until there is about 100mL of liquid ammonia in the round bottom flask, then stop the flow of ammonia gas. At room temperature, add 5.00g (0.024mol) of β-violet isoxazole derivatives, 58mL of tetrahydrofuran and 5.38mL (0.07mol) of tert-butanol into about 100mL of liquid ammonia, and add metal sodium fragments under stirring Until the solution turns blue, the stirring reaction is continued for 15 min after turning blue. Add NH to the reaction solution 4 Cl until the solution turns white. Extracted with ether, anhydrous Na 2 SO 4 Dry for 12h. Then through suction filtration, rotary steaming. 40 mL of toluene was added to the concentrated solution, and the mixed solution was refluxed and stirred at 120° C. for 24 hours, and then rotary-evaporated to obtain the final product ...

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Abstract

The invention discloses a preparation method of beta-damascenone spice. The preparation method comprises the following steps: (1) by taking beta-ionone as an initial raw material, carrying out a reaction with hydroxylamine hydrochloride in an alkaline environment to obtain beta-ionone oxime; (2) carrying out a reaction on beta-ionone oxime and halogens and metal salt thereof to obtain a beta-ionone oxime isoxazole derivative; (3) acting on the eta-ionone oxime isoxazole derivative and sodium to generate beta-dihydrodamascenone; and (4) carrying out an oxidizing halogenating reaction on beta-dihydrodamascenone and free radicals of halogens and carrying out an elimination reaction of removing halogen hydride under the alkaline environment to obtain the beta-damascenone. The preparation method disclosed by the invention is cheap and easily available in raw materials, simple to operate, mild in reaction condition, high in yield of reactions and low in cost, and the solvent used can be recycled, so that the preparation method is a method suitable for industrially producing beta-damascenone spice.

Description

technical field [0001] The invention belongs to the technical field of fragrance fine chemicals, and in particular relates to a method for preparing β-damascenone fragrance by using β-ionone as a starting material. Background technique [0002] β-Damascenone (β-Damascenone), also known as β-Turkelenone, is named 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-2 -Buten-1-one, light yellow to yellow liquid, easily soluble in ethyl acetate, ether, acetone and other organic solvents, miscible with 95% ethanol in any ratio, hardly soluble in water. It is a trace component isolated from Bulgarian rose oil by Demole et al. in 1970. It has a strong floral and fruity aroma and smells of roses, plums, grapes, raspberries, candies, and strong natural floral and fruity aromas. . β-Damascenone not only soothes and coordinates mood, increases self-confidence, improves blood circulation, improves heart and liver function, suppresses nausea, and helps skin moisturizing and antibacterial effect...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/543C07C45/65
CPCC07C45/56C07C45/65C07C249/08C07C2601/16C07D261/04C07C49/543C07C251/40
Inventor 张锁江程莹莹徐宝华任天鹭
Owner INST OF PROCESS ENG CHINESE ACAD OF SCI
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