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A production and purification process of lauroyl arginine ethyl ester hydrochloride

A technology of lauroyl arginine ethyl ester hydrochloride and lauroyl arginine ethyl ester, which is applied in the production field of lauroyl arginine ethyl ester hydrochloride, can solve problems such as incomplete repeatable realization, and avoid The effect of the hydrolysis problem

Active Publication Date: 2020-12-25
AK BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] The small-scale reaction of Example 2 and Example 4 in WO 2013 / 098659 A1 cannot be completely repeated in the scale-up production process

Method used

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  • A production and purification process of lauroyl arginine ethyl ester hydrochloride
  • A production and purification process of lauroyl arginine ethyl ester hydrochloride
  • A production and purification process of lauroyl arginine ethyl ester hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] This example is implemented according to the technical solution disclosed in Example 2 of the patent WO 2013 / 098659 A1, as a comparative example of the patent of the present invention.

[0043] Weigh 27.5kg (100mol) of L-arginine ethyl ester dihydrochloride and add it into 100L tetrahydrofuran and stir until it dissolves completely, then add 20.2kg of triethylamine (200mol) slowly into the system and stir for 30min. 22 kg of lauroyl chloride (100 mol) was added dropwise under the conditions, and the reaction was continued for 2 hours. After adding 10.1 kg of triethylamine (100 mol), the temperature was raised to 40° C. until the reaction was complete. Remove triethylamine hydrochloride by filtration, concentrate the dry system to obtain the crude product, add 250L of water, cool the system to below 10°C and adjust the pH to acidic with 10% dilute hydrochloric acid. Add 250L of ethyl acetate, heat up to 30°C to dissolve the extracted product as much as possible, add 25L ...

Embodiment 2

[0045] The production and purification process of a kind of lauroyl arginine ethyl ester hydrochloride provided by the present invention adopts the following steps to prepare and purify lauroyl arginine ethyl ester hydrochloride:

[0046] Step A: Add 10.5kg (60.3mol) of L-arginine and 95kg of ethanol to a 200L reactor at room temperature, and slowly add 26kg (218.48mol) of thionyl chloride dropwise. Within 25°C, after the dropwise addition, the system was dissolved and clarified, and the reaction was completed at 45°C for 10 hours. Concentrate dry ethanol to obtain ethyl arginine dihydrochloride, and proceed to the next step of reaction.

[0047] Step B: Add 120 kg of chloroform to the reaction product of the previous step, cool down to 5°C in the kettle, add 12 kg (118.8 mol) of triethylamine dropwise, stir for 1 h until the system is dissolved and clear, then add 13.45 kg (61.48 mol) of lauroyl chloride dropwise ), the reaction is exothermic, and the temperature is controlle...

Embodiment 3

[0051] This embodiment further carries out process enlargement on the basis of embodiment 2, and its production purification process adopts the following steps to prepare and purify lauroyl arginine ethyl ester hydrochloride:

[0052] Step A: Add 50kg (287.35mol) of L-arginine and 450kg of ethanol to a 1000L reaction kettle at room temperature, slowly add 130kg (1092.43mol) of thionyl chloride dropwise, the dropping process releases heat, and the dropping temperature is controlled to 25°C Within a period of time, after the dropwise addition, the system was dissolved and clarified, and the reaction was completed at 30°C for 18 hours. Concentrate dry ethanol to obtain ethyl arginine dihydrochloride, and proceed to the next step of reaction.

[0053] Step B: Add 750 kg of dichloromethane to the reaction product of the previous step, lower the temperature in the kettle to 5°C, add 60 kg (594 mol) of triethylamine dropwise, stir for 1 h until the system is dissolved and clear, then ...

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Abstract

The invention discloses a production and purification process of ethyl lauroyl arginate hydrochloride. The process comprises the following steps: step A, esterfying in ethyl alcohol to obtain ethyl arginate dihydrochloride; step B, adding lauroyl chloride into ethyl arginate dihydrochloride in an organic system in the presence of organic alkali, and carrying out condensation to obtain ethyl lauroyl arginate; step C, acidifying ethyl lauroyl arginate into hydrochloride in the organic system, and purifying the product; and step D, carrying out recrystallization and precipitating solid out, and drying the solid to obtain ethyl lauroyl arginate hydrochloride. Through the production and purification process of ethyl lauroyl arginate hydrochloride, the hydrolysis of the product can be effectively avoided; the product is high in stability in industrial production; the mole yield of the product is 97% or higher; the purity of the product is 97% or higher; compared with the existing productiontechnology, the molar yield and the purity of the product are obviously improved.

Description

technical field [0001] The invention belongs to the technical field of producing lauroyl arginine ethyl ester hydrochloride, in particular to a production and purification process of lauroyl arginine ethyl ester hydrochloride. Background technique [0002] Food preservatives are additives that can prevent spoilage caused by microorganisms and prolong the shelf life of food. Its main function is to inhibit the reproduction of microorganisms in food. Conventional food preservatives, such as sodium benzoate, potassium sorbate, etc., have been proved by toxicological safety evaluation that long-term use of sodium benzoate will cause harm to human liver and can cause cancer; potassium sorbate also has certain side effects on the human body, so It has become an inevitable trend to develop new and safer antibacterial preservatives instead of conventional antibacterial preservatives. [0003] Lauroyl arginine ethyl ester hydrochloride is an amino acid preservative, a new type of an...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C277/08C07C279/14
CPCC07C277/08C07C279/14
Inventor 赵林吉张卓张翔洪程悦
Owner AK BIOTECH
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