Process for refining a series of glyceryl oleate products

Abstract

The application discloses a refining method of glyceryl oleate series products. The glyceryl oleate mixture is used as raw material, the mixture is melted by heating, then the melted liquid is flowed through a panel containing different temperature zones, and crystals are separated in the corresponding temperature zones by using the difference of solidification points of different components, so that glyceryl monooleate, glycerol, glyceryl dioleate and glyceryl trioleate are obtained respectively. The separation of each component in the glyceryl oleate mixture is realized. The method does not introduce solvent and adsorbent, is green and environment-friendly, and the obtained products can meet the demand of high-purity glyceryl monooleate and glyceryl dioleate for biological products.

Description

TECHNICAL FIELD

[0001] The application belongs to the technical field of product refining and purification, and particularly relates to a refining method of glyceryl oleate series products. BACKGROUND

[0002] The glyceryl oleate mixture is prepared by esterification of oleic acid and glycerol under the conditions of temperature rise and dehydration according to a certain molar ratio (glycerol excess). The obtained product mainly contains glyceryl monooleate, glyceryl dioleate, glyceryl trioleate and glycerol.

[0003] The glyceryl monooleate and glyceryl dioleate obtained by direct esterification are only mixtures with glyceryl monooleate or glyceryl dioleate > 50%, which cannot be applied to biological products. The glyceryl monooleate and glyceryl dioleate used in biological products have high requirements for their content, and therefore the separation of different components needs to be realized.

[0004] Since the melting points of glyceryl monooleate, glyceryl dioleate, glyceryl trioleate and glycerol are significantly different (glyceryl monooleate (freezing point 35-37°C), glyceryl dioleate (freezing point 12°C), glyceryl trioleate (freezing point -5°C), glycerol (freezing point 20°C)), the application designs a panel with different gradient temperatures to realize the separation of each component by the difference in freezing point. However, there are the following key points in the operation process: one is accurate temperature control, two is slow flow rate, and three is as thin as possible. Accurate temperature control is to ensure the separation effect, and slow flow rate and thin cloth are to fully realize heat exchange.

[0005] The method has not been reported in the literature, and high-purity series glycerides can be prepared without adding solvents and adsorbents, so the refining method of glyceryl oleate series products has important significance. SUMMARY

[0006] Based on the above problems, the purpose of the application is to provide a refining method of glyceryl oleate series products. The method does not introduce solvents and adsorbents, is green and environmentally friendly, and the obtained product can meet the demand of high-purity glyceryl monooleate and glyceryl dioleate for biological products.

[0007] To achieve the above purpose, the application provides the following technical scheme.

[0008] One of the applications provides a refining method of glyceryl oleate series products, which comprises the following steps:

[0009] The method comprises the following steps: taking an oleic acid glyceride mixture as raw material, melting the raw material by heating, and then making the melted liquid flow through a panel comprising different temperature zones, wherein crystals are precipitated in the corresponding temperature zones, and the liquid flow rate is controlled, and the oleic acid glyceride, glycerol, dioleic acid glyceride and trioleic acid glyceride products are obtained on the panel in the different temperature zones respectively.

[0010] Preferably, the oleic acid glyceride mixture comprises oleic acid glyceride, dioleic acid glyceride, trioleic acid glyceride and glycerol.

[0011] Preferably, the melting temperature is 40-50 DEG C.

[0012] Preferably, the panel temperature in the different temperature zones is 33-35 DEG C, 18-20 DEG C, 10-12 DEG C and -7 to -5 DEG C respectively.

[0013] Preferably, the products obtained in the panel temperature of 33-35 DEG C, 18-20 DEG C, 10-12 DEG C and -7 to -5 DEG C correspond to oleic acid glyceride, glycerol, dioleic acid glyceride and trioleic acid glyceride respectively.

[0014] Preferably, the liquid flow rate is extremely slow feeding, and the feeding height is not higher than 1 mm each time, and there is still liquid after the liquid flows through the panel, and the extremely slow feeding flow rate is maintained from the beginning.

[0015] Preferably, the feeding speed is 3-10 g / min.

[0016] Preferably, the feeding height is the height of the crystals precipitated during the feeding process.

[0017] Preferably, the content of the oleic acid glyceride, glycerol, dioleic acid glyceride and trioleic acid glyceride is greater than 90%.

[0018] Compared with the prior art, the method of the present application has the advantages of no solvent and adsorbent introduction, green environmental protection, and the obtained products can meet the demand of high-purity oleic acid glyceride and dioleic acid glyceride for biological products, and can also prepare oleic acid glyceride, glycerol, dioleic acid glyceride and trioleic acid glyceride with a content greater than 90% at the same time. BRIEF DESCRIPTION OF DRAWINGS

[0019] Figure 1 The figure is a schematic diagram of the panel structure of the present application. EMBODIMENT

[0020] With reference to the embodiments of the present application, the technical solutions in the embodiments of the present application will be clearly and completely described. Obviously, the described embodiments are only part of the embodiments of the present application, rather than all the embodiments of the present application. Based on the embodiments of the present application, all the other embodiments obtained by a person of ordinary skill in the art without creative work, fall within the protection scope of the present application.

[0021] Example 1: 5 kg of glyceryl oleate mixture (in which the total content of glyceryl monooleate, glycerol, glyceryl dioleate and glyceryl trioleate is 100%) is warmed to 50°C and melted into a uniform state, and then the molten liquid produced after melting is flowed through a panel comprising different temperature zones, the panel temperatures are 33-35°C, 18-20°C, 10-12°C and -7--5°C respectively, crystals are precipitated in the corresponding temperature zones, the temperature is controlled from high to low, the liquid flow rate is controlled to be 3 g / min, and the distribution height is <0.5 mm, glyceryl monooleate, glycerol, glyceryl dioleate and glyceryl trioleate are obtained in the 33-35°C, 18-20°C, 10-12°C and -7--5°C zones respectively. The content is detected by high performance liquid chromatography to be 95%, 96%, 94% and 97% respectively.

[0022] Example 2: 5 kg of glyceryl oleate mixture (in which the total content of glyceryl monooleate, glycerol, glyceryl dioleate and glyceryl trioleate is 100%) is warmed to 40°C and melted into a uniform state, and then the molten liquid produced after melting is flowed through a panel comprising different temperature zones, the panel temperatures are 33-35°C, 18-20°C, 10-12°C and -7--5°C respectively, crystals are precipitated in the corresponding temperature zones, the temperature is controlled from high to low, the liquid flow rate is controlled to be 5 g / min, and the distribution height is <1 mm, glyceryl monooleate, glycerol, glyceryl dioleate and glyceryl trioleate are obtained in the 33-35°C, 18-20°C, 10-12°C and -7--5°C zones respectively. The content is detected by high performance liquid chromatography to be 90%, 91%, 90% and 92% respectively.

[0023] Example 3: 5 kg of glyceryl oleate mixture (in which the total content of glyceryl monooleate, glycerol, glyceryl dioleate, and glyceryl trioleate is 100%) is heated to 45℃ and melted into a uniform state, and then the melted liquid is passed through a panel containing different temperature zones, the panel temperatures are 33-35℃, 18-20℃, 10-12℃, and -7--5℃, respectively, and crystals are precipitated in the corresponding temperature zones, the liquid flow rate is controlled to be 10 g / min, and the distribution height is <0.1 mm, glyceryl monooleate, glycerol, glyceryl dioleate, and glyceryl trioleate are obtained in the 33-35℃, 18-20℃, 10-12℃, and -7--5℃ zones, respectively. The content is detected by high performance liquid chromatography to be 92%, 92%, 93%, and 95%, respectively.

[0024] Comparative Example 1: 20 g of high-purity conjugated linoleic acid and 7 g of glycerol are reacted at 190℃ for 3 hours, the reaction product is dissolved with 50 mL (n-hexane: petroleum ether = 1:1), the reaction product is washed with 10 mL of 10% sodium bicarbonate each time, and the washing is performed three times, and the reaction product is washed with deionized water twice, the upper organic phase is concentrated by rotary evaporation, dissolved with a mixed solvent of n-hexane: ethyl acetate: methanol: formic acid, separated on a silica gel column, and 170 mL of conjugated linoleic acid monoglyceride is collected, and the yield is 64%.

[0025] As can be seen from the above, a large amount of solvent is used to separate glycerides in Comparative Example 1, and a method for separating glycerides without using a solvent is provided in the embodiments of the present application, and compared with the prior art, the present application is more green, environmentally friendly, and effective.

[0026] The details not described in the present application are known to those skilled in the art.

[0027] Finally, it should be pointed out that the above specific embodiments are only used to illustrate the technical solutions of the present application and are not limiting, although the present application has been described in detail with reference to the embodiments, those skilled in the art should understand that the technical solutions of the present application can be modified and replaced equivalently without departing from the spirit and scope of the technical solutions of the present application, and they should be covered in the scope of the claims of the present application.

Claims

1. A method for refining a series of glyceryl oleate products, characterized by, The method comprises the following steps: The method comprises the following steps: The method comprises the following steps: The temperature of the panel in the different temperature zones is 33-35 DEG C, 18-20 DEG C, 10-12 DEG C and -7 to -5 DEG C respectively.

2. The refining method of the glyceryl oleate series product according to claim 1, characterized by, The glyceryl oleate mixture comprises glyceryl monooleate, glyceryl dioleate, glyceryl trioleate and glycerol.

3. The refining method of glyceryl oleate series products according to claim 1, characterized by, The products obtained at the temperatures of 33-35 DEG C, 18-20 DEG C, 10-12 DEG C and -7 to -5 DEG C on the panel in the different temperature zones correspond to glyceryl monooleate, glycerol, glyceryl dioleate and glyceryl trioleate respectively.

4. The refining method of glyceryl oleate series products according to claim 1, characterized by, The liquid flow rate is extremely slow feeding, and the feeding height should not be higher than 1 mm each time.

5. The refining method of glyceryl oleate series products according to claim 4, characterized by, The feeding speed is 3-10 g / min.

6. The refining method of the glyceryl oleate series product according to claim 4, characterized by, The feeding height is the height of the crystals precipitated during the feeding process.

7. The refining method of glyceryl oleate series products according to claim 1, characterized by, The content of the glyceryl monooleate, glycerol, glyceryl dioleate and glyceryl trioleate is greater than 90%.

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