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CN-122010759-A - Separation and purification process of oleoyl monoethanolamine

CN122010759ACN 122010759 ACN122010759 ACN 122010759ACN-122010759-A

Abstract

The invention discloses a separation and purification process of oleoyl monoethanolamine, which comprises the following steps of (1) dispersing a crude product a of oleoyl monoethanolamine obtained after reaction of ethanolamine and methyl oleate in low-carbon alcohol, heating, stirring for dissolution, filtering to remove insoluble substances to obtain filtrate, (2) adding deionized water into the obtained filtrate, cooling, standing for crystallization, filtering, discarding filter cakes to obtain filtrate, (3) adding ethanolamine into the filtrate, freezing, standing for crystallization, filtering, drying to obtain a crude product b of solid crystals of oleoyl monoethanolamine, (4) dissolving the crude product b in a low-carbon alcohol aqueous solution, adding an organic acid to adjust the pH value of a system, standing for crystallization at low temperature, filtering, and drying to obtain a flaky-shaped oleoyl monoethanolamine crystal product.

Inventors

  • DU YANGJI
  • CHEN SIWEI
  • ZHOU WEIGUO

Assignees

  • 广东广业清怡食品科技股份有限公司
  • 翁源广业清怡食品科技有限公司

Dates

Publication Date
20260512
Application Date
20251216

Claims (10)

  1. 1. The separation and purification process of the oleoyl monoethanolamine is characterized by comprising the following steps of: (1) Dispersing an oleoyl monoethanolamine crude product a obtained after the reaction of ethanolamine and methyl oleate crude product in low-carbon alcohol, heating, stirring for dissolution, and filtering to remove insoluble substances to obtain filtrate; (2) Adding deionized water into the filtrate obtained in the step (1), cooling, standing for crystallization, filtering, and removing a filter cake to obtain filtrate; (3) Adding ethanolamine into the filtrate obtained in the step (2), freezing, standing for crystallization, filtering, and drying a filter cake to obtain an oleoyl monoethanolamine solid crystal crude product b; (4) Dissolving the solid crystal crude product b of the oleoylethanolamide in a low-carbon alcohol aqueous solution, adding an organic acid to adjust the pH value of the system, standing at a low temperature for crystallization, filtering, and drying a filter cake to obtain a flaky-luster oleoylethanolamide crystal product.
  2. 2. The process for separating and purifying oleoyl monoethanolamine according to claim 1, wherein in the step (1), the mass percentage of methyl oleate in the crude methyl oleate is 25-60%, and the main impurities contained in the crude methyl oleate are methyl stearate, methyl linoleate and methyl linolenate.
  3. 3. The process for separating and purifying oleoyl monoethanolamine according to claim 1, wherein the lower alcohol in step (1) is methanol or ethanol, and the amount of the lower alcohol and the crude product a of oleoyl monoethanolamine is 5-10ml:1g.
  4. 4. The process for separating and purifying oleoyl monoethanolamine according to claim 1, wherein in step (1) is heated to 40-45 ℃.
  5. 5. The process for separating and purifying oleoyl monoethanolamine according to claim 1, wherein the deionized water is used in the amount of 10-15% of the total volume of the lower alcohol in the step (1).
  6. 6. The process for separating and purifying oleoyl monoethanolamine according to claim 1, wherein in step (2), cooling is performed to 10-15 ℃, and standing crystallization is performed for 8-10 hours.
  7. 7. The process for separating and purifying oleoyl monoethanolamine of claim 1, wherein the concentration of ethanolamine added in step (3) is 0.15-0.2g/mL.
  8. 8. The process for separating and purifying oleoyl monoethanolamine according to claim 1, wherein in step (3), the mixture is cooled to 0-5 ℃ and left to stand for crystallization for 5-8 hours.
  9. 9. The process for separating and purifying oleoylethanolamide according to claim 1, wherein in the step (4), the crude product b of solid crystals of oleoylethanolamide is dissolved in a low-carbon alcohol aqueous solution at a temperature of 30-35 ℃, the dosage relationship between the low-carbon alcohol aqueous solution and the crude product b of solid crystals of oleoylethanolamide is 5-8 mL/1 g, the volume percentage of the low-carbon alcohol in the low-carbon alcohol aqueous solution is 75% -80%, and the low-carbon alcohol is methanol or ethanol.
  10. 10. The process for separating and purifying the oleoyl monoethanolamine according to claim 1, wherein in the step (4), an organic acid is added to adjust the pH value of a system to 6.9-7.1, the organic acid is formic acid or acetic acid, and the system is subjected to standing crystallization at a low temperature of 0-5 ℃ for 5-8 hours.

Description

Separation and purification process of oleoyl monoethanolamine Technical Field The invention belongs to the technical field of grease, and particularly relates to a separation and purification process of oleoyl monoethanolamine. Background Oleoyl monoethanolamine (Oleamide MEA), also known as N- (2-hydroxyethyl) -9-octadecenamide, oleic acid monoethanolamide, etc., with the English name N- (2-Hydroxyethyl) -9-octadecenamide, CAS number 111-58-0, molecular formula C 20H39NO2, molecular weight 325.53. Oleoyl monoethanolamine is an important nonionic surfactant and is widely used in the fields of lubricants, surfactants, detergents, and the like. In recent years, fatty acid monoethanolamides have also received attention as a novel endogenous signal molecule and lipid mediators in animal and plant tissues. Such as oleoyl monoethanolamine, can be used to control appetite and improve lipid metabolism. The mechanism is that the oleoyl monoethanolamine not only can inhibit fat absorption of intestinal tracts, but also can accelerate beta oxidation of fatty acid by promoting hydrolysis of triglyceride by peripheral tissues (liver and fat), and finally reduce fat accumulation, thereby realizing weight control. In general, the synthesis of oleic acid monoethanolamides can be achieved by reacting oleic acid chloride (Koutek et al, journal of Biological Chemistry, 1994,269, 22937-22940), free oleic acid (Wang et al, journal of Agricultural and Food Chemistry,2012,60,451-457) or methyl (or ethyl) oleate (Wang et al, journal of Oleo Science, 2013,62,427-433) with ethanolamine. Wherein, the reaction of methyl oleate or ethyl oleate and ethanolamine can be carried out by using enzyme as a catalyst or chemical catalyst. Also, high purity methyl oleate is more expensive and costly to synthesize than vegetable oils. Methyl oleate is sold in the market at present as a mixture of main impurities of methyl oleate (molecular formula C 19H36O2), methyl linoleate (molecular formula C 19H34O2), methyl linolenate (molecular formula C 19H32O2) and methyl stearate (molecular formula C 19H38O2), wherein the actual content of the methyl oleate is 20% -60%, and the refining process of the methyl oleate above 90% is complex, the cost price is extremely high, and the methyl oleate needs to be imported from Japan at present, and the market price is high. If the method is used for synthesizing the oleoyl monoethanolamine by taking the complex low-content methyl oleate of the component as a raw material, the chemical property and physical property parameters of the fatty acid monoethanolamine with the same carbon number and different saturation degrees are smaller, so that the difficulty of preparing the high-purity oleoyl monoethanolamine by subsequent separation and purification is quite large, and no related report is yet available at present. High purity methyl oleate is expensive (more than 95%) because of its high price and reliance on importation. Therefore, development of a preparation process of oleoyl monoethanolamine, especially a process for preparing high-purity oleoyl monoethanolamine by using mixed fatty acid methyl ester with low oleic acid methyl ester (content of 20-60%) as raw material after reaction is urgent, and meanwhile, a production method with good process consistency, low raw material regeneration cost, high reaction conversion rate, high purification quality and yield, low overall process production cost and easy realization of industrialization is a problem to be solved urgently by those skilled in the art. Disclosure of Invention The invention aims to provide a separation and purification process of oleoyl monoethanolamine. The process of the invention takes low-content methyl oleate as raw material to react to obtain the crude product of the oleoyl monoethanolamine, and the crude product of the oleoyl monoethanolamine is separated and purified subsequently, so the process is simple, the cost and the energy consumption are low, the product purity is high, and the industrial production is easy to realize. The aim of the invention can be achieved by the following technical scheme that the separation and purification process of the oleoyl monoethanolamine comprises the following steps: (1) Dispersing an oleoyl monoethanolamine crude product a obtained after the reaction of ethanolamine and methyl oleate crude product in low-carbon alcohol, heating, stirring for dissolution, and filtering to remove insoluble substances to obtain filtrate; (2) Adding deionized water into the filtrate obtained in the step (1), cooling, standing for crystallization, filtering, and removing a filter cake to obtain a filtrate; (3) Adding ethanolamine into the filtrate obtained in the step (2), freezing, standing for crystallization, filtering, and drying a filter cake to obtain an oleoyl monoethanolamine solid crystal crude product b; (4) Dissolving the solid crystal crude product b of the oleoylethanolamide in a low-carbon alcohol aqueous