Preparation method of neohesperidin dihydrochalcone

A technology of neohesperidin dihydrochalcone and neohesperidin, which is applied in the field of preparation of neohesperidin dihydrochalcone, can solve the problem of high power consumption, product purity of only 96%, low yield, etc. problem, to achieve the effect of improving utilization, low cost and simple method

Active Publication Date: 2016-12-14
HUNAN HUACHENG BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are also disadvantages: the yield is low, no more than 65%; the product purity is only 96%; a large amount of electric energy is consumed

Method used

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  • Preparation method of neohesperidin dihydrochalcone

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] (1) Carbonyl protection: Dissolve 50g of neohesperidin in 500g of ethanol with a mass concentration of 99%, add 20g of triethyl orthoformate and 2.5g of ketal catalyst lithium tetrafluoroborate, and perform ketalization at 25°C Reacted for 2 hours, concentrated under reduced pressure, cooled and crystallized, filtered and dried to obtain 51.6 g of compound Ⅰ;

[0034] (2) Hydrolysis reaction: 51.6 g of compound I obtained in step (1) was dissolved in 516 g of potassium hydroxide aqueous solution with a mass concentration of 2%, to obtain a potassium hydroxide solution of compound II;

[0035](3) Hydrogenation reaction: Add 5 g of hydrogenation catalyst palladium carbon into the potassium hydroxide solution of compound II obtained in step (2), first pass nitrogen protection into the reaction vessel, and then at a temperature of 25 ° C and a pressure of 0.01 MPa, Pass hydrogen into the potassium hydroxide solution of compound II, carry out the hydrogenation reaction for 1...

Embodiment 2

[0038] (1) Carbonyl protection: Dissolve 100g neohesperidin in 1100g methanol with a mass concentration of 99%, add 45g trimethyl orthoformate and 7.5g ketal catalyst decane boron, and carry out ketal reaction at 65°C 6h, concentrated under reduced pressure, cooled and crystallized, filtered and dried to obtain 103.1g of compound Ⅰ;

[0039] (2) Hydrolysis reaction: 103.1 g of compound I obtained in step (1) was dissolved in 1200 g of 5% sodium carbonate aqueous solution to obtain a sodium carbonate solution of compound II;

[0040] (3) Hydrogenation reaction: Add 15g of hydrogenation catalyst Raney nickel to the sodium carbonate solution of compound II obtained in step (2), first pass nitrogen protection into the reaction vessel, and then at a temperature of 35°C and a pressure of 0.5MPa, Pass hydrogen into the sodium carbonate solution of compound II, carry out the hydrogenation reaction for 20 h, filter and recover the hydrogenation catalyst Raney nickel, and obtain the sod...

Embodiment 3

[0043] (1) Carbonyl protection: Dissolve 100g neohesperidin in 1200g ethanol with a mass concentration of 95%, add 40g triethyl orthoformate and 5g ketal catalyst indium trichloride, and carry out ketal reaction at 70°C 3h, concentrated under reduced pressure, cooled and crystallized, filtered and dried to obtain 102.7g of compound Ⅰ;

[0044] (2) Hydrolysis reaction: 102.7 g of compound I obtained in step (1) was dissolved in 1800 g of aqueous sodium hydroxide solution with a mass concentration of 2.5%, to obtain a sodium hydroxide solution of compound II;

[0045] (3) Hydrogenation reaction: Add 1.5 g of hydrogenation catalyst platinum carbon to the sodium hydroxide solution of compound II obtained in step (2), first pass nitrogen protection into the reaction vessel, and then at a temperature of 50 ° C and a pressure of 2 MPa, Pass hydrogen into the sodium hydroxide solution of compound II, carry out the hydrogenation reaction for 5 hours, filter and recover the hydrogenatio...

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Abstract

The invention discloses a preparation method of neohesperidin dihydrochalcone. The method comprises the following steps: (1) carbonyl protection: dissolving the neohesperidin in an organic solvent or organic solvent aqueous solution, adding trimethyl orthoformate or triethyl orthoformate and ketal catalyst to perform the ketal reaction, reducing pressure and concentrating, cooling and crystallizing, filtering and drying to obtain a compound I; (2) hydrolysis reaction: dissolving the compound I in an aqueous alkali of the compound II; (3) hydrogenation reaction: adding the hydrogenation catalyst, introducing nitrogen to protect, and introducing the hydrogen to perform the hydrogenation reaction, filtering to obtain the aqueous alkali of the compound III; (4) acidification and crystallization: regulating pH value, cooling and crystallizing, filtering and drying to obtain the neohesperidin dihydrochalcone. The yield of the neohesperidin dihydrochalcone prepared through the method disclosed by the invention could reach 97.2%, the purity can reach 98.5%. The method disclosed by the invention is simple, mild in reaction condition and low in cost, and is capable of partially recycling the catalyst and suitable for the industrial production.

Description

technical field [0001] The invention relates to a preparation method of neohesperidin dihydrochalcone, in particular to a method for synthesizing neohesperidin dihydrochalcone from neohesperidin. Background technique [0002] Neohesperidin dihydrochalcone (NHDC for short) is a dihydroflavonoid compound obtained by hydrogenation of neohesperidin. It is a functional sweetener with bitterness suppression and flavor improvement. It has high sweetness , low calorie, long-lasting sweetness, good stability, non-toxic characteristics, widely used in food, medicine and feed industries. [0003] The traditional method uses neohesperidin as a raw material to prepare neohesperidin dihydrochalcone, which is usually prepared by dissolving neohesperidin in alkaline water, using palladium carbon or Raney nickel as a catalyst, introducing hydrogen, and hydrogenation reduction. Since the group that can be hydrogenated in the structure of neohesperidin has a carbonyl group in addition to the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/203C07H1/00
CPCY02P20/584C07H15/203C07H1/00
Inventor 李伟龙伟岸黄华学
Owner HUNAN HUACHENG BIOTECH
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