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Preparation method of L-Ornithine-Malic Acid

A technology of malic acid and citrulline, which is applied in the preparation of carboxylate, organic chemistry, etc., can solve the problems of unsuitability for industrial production, large amount of solvent in preparation solution, and high preparation cost.

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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] However, regarding the salt crystallization method of malic acid and L-citrulline reaction, there is only CA Abstract V82: P144952c, which briefly provides a crystallization method. The amount of solvent is large, which makes the preparation cost high and is not suitable for industrial production

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  • Preparation method of L-Ornithine-Malic Acid
  • Preparation method of L-Ornithine-Malic Acid

Examples

Experimental program
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Embodiment 1

[0032] In a 500ml reaction bottle, add 140ml of 25% L-citrulline solution (equivalent to 0.2mol), stir, slowly add 13.4g (0.1mol) of L-malic acid, react at room temperature for 10mins, then concentrate under reduced pressure, The temperature of the water bath is 55°C, the total volume of the concentrated reaction solution is about 95ml, and the cooling temperature is 23°C. Slowly add 95% ethanol dropwise while stirring until a small amount of crystals are precipitated, stir for 10mins, and then continue to add 95% ethanol dropwise, the total amount of ethanol It is about 180ml, and the dropping time is 2hr. Then lower the temperature of the crystallization solution to 5-10°C, and place it for 30mins to completely crystallize the crystals, filter, wash the crystals with 95% ethanol, and dry them in vacuum at 60°C to obtain white flaky crystals of L-citrulline-L-apple Acid acid (2:1) (39.4 g, yield: 81.4%).

[0033] [a] D +19.5 (c=4, 6N HCl)

[0034] Elemental analysis: (C 6...

Embodiment 2

[0039] In a 500ml reaction bottle, add 70ml of 25% L-citrulline solution (equivalent to 0.1mol), stir, slowly add 13.4g (0.1mol) DL-malic acid, react at room temperature for 10mins, then concentrate under reduced pressure, The temperature of the water bath is 55°C, the total volume of the concentrated reaction solution is about 44ml, and the temperature is cooled to 23°C. Slowly add anhydrous methanol dropwise while stirring until a small amount of crystals precipitate, stir for 10mins, and then continue to add dropwise anhydrous methanol, the total amount of methanol It is about 90ml, and the dropping time is 2hr. Then lower the temperature of the crystallization solution to 5-10°C and let it stand for 30mins to completely crystallize the crystals, filter, wash the crystals with anhydrous methanol, and dry them in vacuum at 60°C to obtain white flaky crystals of L-citrulline-DL-apple acid salt (1:1) (24.8 g, yield: 80.4%).

[0040] [a] D +15.6° (c=4, 6N HCl)

[0041] Element...

Embodiment 3

[0046] In a 500ml reaction bottle, add 70ml of 25% L-citrulline solution (equivalent to 0.1mol), stir, slowly add 13.4g (0.1mol) L-malic acid, react at room temperature for 10mins, then concentrate under reduced pressure, The water bath temperature is 55°C, concentrate the total volume of the reaction solution to about 45ml, cool the temperature to 23°C, slowly add isobutanol dropwise while stirring until a small amount of crystals precipitate, stir for 10mins, and then continue to drop isobutanol, isobutanol The total amount is about 100ml, and the dropping time is 2hr. Then lower the temperature of the crystallization solution to 5-10°C, and place it for 30mins to completely crystallize the crystals, filter, wash the crystals with isobutanol, and dry them in vacuum at 60°C to obtain white flaky crystals of L-citrulline-L-apple acid salt (1:1) (25.6 g, yield: 82.8%).

[0047] [a] D +16.0° (c=4, 6N HCl)

[0048] Elemental Analysis: C 6 h 13 N 3 o 3 ·C 4 h 6 o 5

[0...

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Abstract

The invention relates to a producing method for L-citrulline-malate, comprising the steps of: slowly adding 20-30% L-citrulline into malate with a molar rate of 1:1 or 2:1; in 50-80 DEG C, decompress and concentrating and cooling down to 20-30 DEG C; slowly adding organic solvent or a mixing solvent of polar hydrophilic solvent and non-polar solvent, cooling crystallization, filtering and washing, drying in vaccum to get finished product. The method has simple steps, a high product purity, a high yield and is not tending to agglomeration, facilitates to transportation and application and fits for industrialisation.

Description

technical field [0001] The invention relates to a crystallization method of L-malic acid and amino acid, in particular to a preparation method of L-citrulline-malic acid. Background technique [0002] L-citrulline-malate is an amino acid salt health product with increasing sales in the international market, mainly used in weight loss products. With the increasing demand in the international market, the research on the crystallization method of L-citrulline salts has become the focus of attention, especially the research on the method of salt crystallization of L-citrulline-L-malic acid . [0003] Patents such as Japanese publications 54-143603, 54-42378, US4420432, and US4438044 have reported a series of methods for reacting L-malic acid and various amino acids to form salts and crystallize them. Wherein the salt-forming crystallization method of L-malic acid and other amino acids, such as the salt-forming reaction formula of L-arginine-DL-malate (2: 1) is as follows: [...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C275/42C07C59/245C07C51/41
Inventor 苏建勇郑南华苏迎春
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