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Synthetic method of neotame

A synthetic method, neotame technology, applied in the field of food additives, achieves the effect of low cost, simple experimental steps, and beneficial to industrial production

Active Publication Date: 2014-09-17
JINAN CHENGHUI SHUANGDA CHEM +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] There are many synthetic methods of neotame. These methods have their own advantages, but there are also deficiencies, such as high cost, low product purity, low yield, experimental operation cumbersome etc.
U.S. Patent No. 5,480,668 provides a method for preparing neotame by reducing a mixed solution of aspartame and 3,3-dimethylbutyraldehyde with sodium cyanoborohydride as a reducing agent. In the reaction, when the acidity is strong, there will be The danger of cyanide is unfavorable for suitability for industrialized production; The mixture of 3,3-dimethylbutyraldehyde precursor and aspartame is hydrogenated in methanol with catalyst such as platinum carbon or palladium carbon to synthesize Neotame, acetic acid must be added to the reaction system to adjust the pH of the solution

Method used

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  • Synthetic method of neotame

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Experimental program
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Effect test

Embodiment 1

[0031] N-α-L-aspartame-L-phenylalanine 1-methyl ester 45 g, 3,3-dimethylbutyraldehyde 15 g, absolute ethanol 200 g, 5% Pd / C (based on Wet basis) 0.2 g was added to a 500 ml autoclave, sealed, tested for leaks with hydrogen gas, and replaced three times; hydrogen gas was passed to 0.7 Mpa, stirring and heating were started; during the hydrogenation process, the temperature was controlled at 35~40 °C, and the pressure was controlled at 0.4~ 0.7 MPa. The reaction consumes hydrogen faster in the early stage and slower in the later stage. After the reaction basically does not consume hydrogen, the reaction is carried out with heat preservation and pressure for 6 hours to ensure complete reaction.

[0032] The reaction solution was taken out, filtered with suction, and the catalyst was recovered; the reaction solution was concentrated by a rotary evaporator until it became viscous. Add 30 g of absolute ethanol to the above concentrate, stir in a water bath at 40°C until dissolved, ...

Embodiment 2

[0035] 43.5 g of N-α-L-aspartame-L-phenylalanine 1-methyl ester, 14.5 g of 3,3-dimethylbutyraldehyde, 190 g of absolute ethanol, 5% Pd / C (based on Wet basis) 0.2 g was added to a 500 ml autoclave, sealed, tested for leaks with hydrogen gas, and replaced three times; hydrogen gas was passed to 0.7 Mpa, stirring and heating were started; during the hydrogenation process, the temperature was controlled at 35~40 °C, and the pressure was controlled at 0.4~ 0.7 MPa. The reaction consumes hydrogen faster in the early stage and slower in the later stage. After the reaction basically does not consume hydrogen, the reaction is carried out with heat preservation and pressure for 6 hours to ensure complete reaction.

[0036] The reaction solution was taken out, filtered with suction, and the catalyst was recovered; the reaction solution was concentrated by a rotary evaporator until it became viscous. Add 27 g of absolute ethanol to the above concentrate, stir in a water bath at 40°C unti...

Embodiment 3

[0039] N-α-L-aspartame-L-phenylalanine 1-methyl ester 90 g, 3,3-dimethylbutyraldehyde 34 g, absolute ethanol 450 g, 5% Pd / C (based on Wet basis) 0.6 g was added to a 1 L autoclave, sealed, tested for leaks with hydrogen, and replaced three times; hydrogen was passed to 0.7 Mpa, stirring and heating were started; during the hydrogenation process, the temperature was controlled at 35~40°C, and the pressure was controlled at 0.4~ 0.7 MPa. The reaction consumes hydrogen faster in the early stage, and slower in the later stage. After the reaction basically does not consume hydrogen, the reaction is carried out under heat preservation and pressure for 6 hours to ensure complete reaction.

[0040] The reaction solution was taken out, filtered with suction, and the catalyst was recovered; the reaction solution was concentrated by a rotary evaporator until it became viscous. Add 65 g of absolute ethanol to the above concentrate, stir in a water bath at 40°C until dissolved, add 305 g ...

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Abstract

The invention belongs to the field of food additives, particularly relates to a sweetening agent, and more particularly relates to a method for synthesizing neotame through catalytic hydrogenation of N-alpha-L-aspartic phthalein-L-phenylalanine 1-methyl ester and 3,3-dimethyl butyraldehyde. A synthetic method of neotame is characterized in that Pd / C is taken as a catalyst to perform the catalytic hydrogenation of an ethanol solution of N-alpha-L-aspartic phthalein-L-phenylalanine 1-methyl ester and 3,3-dimethyl butyraldehyde so as to synthesize neotame. The synthetic method disclosed by the invention has the beneficial effects that neotame prepared by the method disclosed by the invention has a yield as high as 83% and liquid-phase purity as high as 98.7%; moreover, in comparison with the synthetic method in the background art, the method disclosed by the invention is beneficial for industrial production, low in cost and simple in experimental procedures.

Description

technical field [0001] The invention belongs to the field of food additives, in particular to a sweetener, in particular to a kind of N-α-L-aspartame-L-phenylalanine 1-methyl ester and 3,3-dimethylbutyraldehyde A method for synthesizing neotame by catalytic hydrogenation. Background technique [0002] Neotame is a new type of non-nutritive high-efficiency sweetener, its chemical name is N-[N-(3,3-dimethylbutyl)-L-α-aspartyl]-L -Phenylalanine 1-methyl ester, its structural formula is as follows: [0003] [0004] In recent years, people have devoted themselves to developing low-calorie or non-caloric sweeteners that can replace sucrose. Among them, aspartame is widely used as a high-sweet and safe sweetener, but the thermal stability of aspartame No, its application is limited; U.S. Patent No. 5,480,668 discloses a new compound, neotame, whose sweetness is 7,000 to 13,000 times that of sucrose and 50 times that of aspartame, and neotame has a similar The pure sweetness...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K5/075C07K1/107
Inventor 王庭见杨金红葛正全李跃东
Owner JINAN CHENGHUI SHUANGDA CHEM
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