Method for preparing and purifying watermelon ketone

A purification method, the technology of watermelon ketone, applied in the direction of organic chemistry, etc., can solve problems such as unfavorable industrial production, and achieve the effect of reasonable and feasible synthetic route, reduced content of impurities, and mild reaction conditions

Inactive Publication Date: 2012-07-18
WUHAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore this process is also unfavorable for industrialized production

Method used

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  • Method for preparing and purifying watermelon ketone
  • Method for preparing and purifying watermelon ketone
  • Method for preparing and purifying watermelon ketone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] 1) Preparation of crude watermelon ketone

[0059] Add 120ml of ethanol to a 250ml three-necked round-bottomed flask equipped with a thermometer, a reflux condenser, and a stirrer. Under nitrogen protection, add 18g of triethylamine, 3g of potassium iodide, and 15g of 4-methylcatechol in sequence, heat to 50°C, and slowly Add 50ml of 15g of ethanol solution of 1,3-dichloroacetone dropwise, after the dropwise addition, keep warm and reflux for 5h; during the reaction process, take samples for GC analysis, cool down, filter with suction to obtain the crude watermelon ketone, the yield is 90%, and recover the solvent;

[0060] 2), preparation of watermelon ketoxime

[0061] Add 150ml of isopropanol to dissolve 5.00g of crude watermelon ketone in a 250ml three-necked round-bottomed flask equipped with a thermometer, reflux condenser, and stirrer, then add 4g of hydroxylamine hydrochloride and 15g of sodium carbonate, stir at room temperature for 6 hours, and TLC detects tha...

Embodiment 2

[0065] 1) Preparation of crude watermelon ketone

[0066] Add 280ml of acetone to a 500ml three-necked round-bottomed flask equipped with a thermometer, a reflux condenser, and a stirrer, and under nitrogen protection, add 26g of sodium carbonate, 7g of sodium iodide, and 35g of 4-methylcatechol in turn, and heat to 40°C. Slowly add a mixed solution of 35g of 1,3-dichloroacetone and 60ml of methanol dropwise. After the dropwise addition, keep warm and reflux for 5h; during the reaction process, take samples for GC analysis, cool down, and filter with suction to obtain the crude watermelon ketone, with a yield of 90%, and recover the solvent ;

[0067] 2), preparation of watermelon ketoxime

[0068] Add 160ml of ethyl acetate and ethylene glycol (volume ratio 10:1) to dissolve 25.00g of crude watermelon ketone in a 250ml three-necked round-bottomed flask equipped with a thermometer, reflux condenser, and stirrer, then add 22g of hydroxylamine hydrochloride and 40g of bicarbona...

Embodiment 3

[0072] 1) Preparation of crude watermelon ketone

[0073] Add 140ml tetrahydrofuran into a 250ml three-necked round-bottomed flask equipped with a thermometer, a reflux condenser, and an agitator, and protect it under nitrogen. Then add 8 g sodium carbonate, 1.47 g sodium iodide, and 11 g 4-methylcatechol in sequence, and heat to 65 ℃, slowly dropwise add a mixed solution of 12.38g of 1,3-dichloroacetone and 40ml of tetrahydrofuran, after the dropwise addition, keep warm and reflux for 5h; during the reaction process, take samples for GC analysis, cool down, and suction filter to obtain the crude watermelon ketone, with a yield of 84% , to recover the solvent;

[0074] 2), preparation of watermelon ketoxime

[0075] Add 120ml of methanol to dissolve 13.00g of crude watermelon ketone in a 250ml three-necked round-bottomed flask equipped with a thermometer, reflux condenser, and stirrer, then add 8g of hydroxylamine hydrochloride and 15g of sodium acetate, stir at room temperat...

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Abstract

The invention relates to a method for preparing and purifying watermelon ketone. According to the method, 4-methylcatechol and 1,3-dichloroacetone are used as raw materials to prepare a watermelon ketone rough product, and the watermelon ketoxime with the high purity is obtained by carrying out oximation, crystallization and purification on the watermelon ketone rough product; and then, the watermelon ketone with high purity is obtained by carrying out oxime removing on the watermelon ketone through oxidization or reduction or hydrolysis. The method disclosed by the invention has the advantages of good selectivity, high yield, wide raw material source, low price, and reasonable and feasible process design.

Description

technical field [0001] The invention relates to a method for preparing and purifying spice compounds, in particular to a method for preparing and purifying watermelon ketone. Background technique [0002] Watermelon ketone, foreign trade name is Calone / watermelon ketone, chemical name is 7-methyl-3,4-dihydro(2H)-1,5-benzodioxepene-3-one, cas: 28940- 11-6. [0003] As a flavor and fragrance, watermelon ketone has been widely used in the daily chemical products and cosmetics market in recent years. Watermelon ketone itself not only has a fresh, fruit-like, soft and sweet smell, but also has a marine, algae, and dreamlike feeling, which can bring a new concept to the formulation of perfume. At present, only a few enterprises in the world produce watermelon ketone, and my country's demand for watermelon ketone mainly depends on imports, which provides a broad market for the development and application of watermelon ketone. [0004] There are few reports about the synthesis a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D321/10
Inventor 岳智洲梁玉坤徐波
Owner WUHAN UNIV OF TECH
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