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Method for synthesizing neohesperidin by taking naringin as raw material

A technology of neohesperidin and neohesperidin, applied in chemical instruments and methods, preparation of sugar derivatives, sugar derivatives, etc., can solve the problems of difficult removal, low hydrolysis yield, expensive price, etc., and shorten the reaction time The effect of shortening the time, shortening the reaction time and reducing the production cost

Active Publication Date: 2017-02-22
HUNAN HUACHENG BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the condensation step in the method does not require anhydrous reaction conditions, the amount of alkali used in the hydrolysis step is too large, which seriously pollutes the environment; the alkali concentration is high, and the side reaction of carbonyl reduction to hydroxyl is prone to occur during hydrolysis, resulting in hydrolysis and yield. The rate is low, only 70%; and the amount of catalyst proline is large, expensive, too much, and the production cost is very high; due to the addition of a large amount of catalyst, it is difficult to completely remove after treatment, resulting in the purity of the final product neohesperidin Low, only 97%

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] (1) Hydrolysis: Dissolve 100g of naringin in 1000mL of potassium hydroxide aqueous solution with a mass concentration of 5%, hydrolyze it for 1 hour at 110°C and a pressure of 0.1MPa, cool to room temperature, and dissolve it with 30% hydrochloric acid Adjust the pH value of the solution to 6, cool to room temperature, crystallize for 6 hours, filter and dry to obtain 75.3g of hydrolyzate——PN (purity 95.3%, yield 87.6%);

[0037] (2) Condensation: Dissolve 75.3g of PN obtained in step (1) in 400g of ethanol (volume concentration: 95%), add 23.87g of isovanillin and 4.52g of histidine, reflux at 85°C for 5 hours, and the reaction is complete Finally, the reaction solution was placed at 0°C, frozen and crystallized for 12 hours, filtered, and dried to obtain 94.39 g of crude neohesperidin (purity 95.6%, yield 93.4%);

[0038] (3) Refining: 94.39g of crude neohesperidin obtained in step (2) was dissolved in 900g of ethanol aqueous solution with a volume concentration of 50...

Embodiment 2

[0041] (1) Hydrolysis: Dissolve 200g of naringin in 2200mL of potassium hydroxide aqueous solution with a mass concentration of 4%, hydrolyze for 1 hour at 120°C and a pressure of 0.2MPa, cool to room temperature, and use 20% sulfuric acid Adjust the pH value of the solution to 5.5, cool to room temperature, crystallize for 6 hours, filter and dry to obtain 152.1 g of hydrolyzed product PN (purity 93.7%, yield 86.9%);

[0042] (2) Condensation: Dissolve 152.1g PN obtained in step (1) in 1500g methanol (volume concentration: 90%), add 48.22g isovanillin and 10.6g histidine, and reflux at 80°C for 6h. After completion, the reaction solution was placed at 2°C, frozen and crystallized for 20 hours, filtered, and dried to obtain 191.8 g of crude neohesperidin (purity 93.9%, yield 92.3%);

[0043] (3) Refining: 191.8g of crude neohesperidin obtained in step (2) was dissolved in 1500g of isopropanol aqueous solution with a volume concentration of 60% by heating to 80°C, cooled to 20°...

Embodiment 3

[0046] (1) Hydrolysis: Dissolve 100g of naringin in 1200mL of 3% sodium hydroxide aqueous solution, hydrolyze for 0.5h at 130°C and pressure of 0.3MPa, cool to room temperature, and use 10% Adjust the pH value to 5 with citric acid, cool to room temperature, crystallize for 6 hours, filter and dry to obtain 74.7g of hydrolyzate PN (purity 93.6%, yield 85.3%);

[0047] (2) Condensation: Dissolve 74.7g of PN obtained in step (1) in 740g of isopropanol (90% volume concentration), add 23.87g of isovanillin and 5.92g of histidine, and reflux at 90°C for 8h After the reaction was complete, the reaction solution was placed at 2°C, frozen and crystallized for 20 hours, filtered, and dried to obtain 92.3 g of crude neohesperidin (purity 93.6%, yield 90.1%);

[0048] (3) Refining: 92.3g of crude neohesperidin obtained in step (2) was dissolved in 923g of 55% aqueous methanol solution by heating to 70°C, cooled to 20°C, crystallized for 18 hours, filtered, and the filter cake was dried ...

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Abstract

The invention provides a method for synthesizing neohesperidin by taking naringin as a raw material. The method comprises the following steps: (1) hydrolyzing: dissolving the naringin into an aqueous alkali; heating, pressurizing and hydrolyzing; cooling to room temperature and adjusting the pH (Potential of Hydrogen) value with an acid; cooling and crystallizing; filtering and drying to obtain a hydrolyzed product-PN; (2) carrying out condensation: dissolving the PN into an organic solvent; adding isovanillin and histidine; carrying out a refluxing reaction; freezing and crystallizing; filtering and drying to obtain a neohesperidin crude product; (3) refining: heating and dissolving the neohesperidin crude product with a low-carbon alcohol water solution; cooling and crystallizing; filtering and drying a filter cake to obtain a neohesperidin fine product. According to the method provided by the invention, the purity of the neohesperidin in the product can reach 99.5 percent, the content of impurities is less and the yield of the neohesperidin is high; the dosage of an alkali and a catalyst in the method is less, the reaction time is short and the cost is low; in a technological process, protection of inert gas is not needed and anhydrous reaction conditions are not needed, so that the method is suitable for industrial production.

Description

technical field [0001] The invention relates to a method for synthesizing neohesperidin, in particular to a method for synthesizing neohesperidin by using naringin as a raw material. Background technique [0002] Neohesperidin is an important dihydroflavonoid compound, and its main use is to synthesize neohesperidin dihydrochalcone, a new type of sweetener, whose sweetness is 1500-1800 times that of sucrose. High sweetness, low calorie, long-lasting sweetness, good stability, non-toxic characteristics, widely used in food, medicine and feed industries. At present, the demand for neohesperidin dihydrochalcone in domestic and foreign markets is increasing day by day, but the raw materials for synthesizing neohesperidin dihydrochalcone are difficult to meet the market demand. [0003] The existing methods to obtain a large amount of neohesperidin mainly include extraction and synthesis. The extraction and isolation of neohesperidin from natural plants is limited by resources ...

Claims

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Application Information

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IPC IPC(8): C07H17/07C07H1/00
CPCC07H1/00C07H17/07
Inventor 李伟龙伟岸黄华学
Owner HUNAN HUACHENG BIOTECH
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