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Method for synthesizing and separating phytosterol saturated fatty acid esters and phytosterol unsaturated fatty acid esters

A technology of phytosterols and fatty acid esters, which is applied in the field of phytosterols and mixed fatty acids to synthesize phytosterol esters, and the separation of phytosterol saturated fatty acid esters and unsaturated fatty acid esters. It can solve the problem of separation and purification, no separation and purification methods, Can not remove fat-soluble impurities and other problems, to achieve the effect of simple operation and high product purity

Active Publication Date: 2012-07-25
XIAN HEALTHFUL BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

CN101235067B discloses the method for synthesizing phytosterol ester with fatty acid, phytosterol direct esterification, and its described catalyst is calcium oxide, magnesium oxide, lanthanum oxide etc., and wherein calcium oxide, magnesium oxide etc. show alkalinity, easy saponification reaction occurs with fatty acid , forming soap, affecting the reaction and separation and purification
CN101985460A discloses a method for directly esterifying phytosterol esters with fatty acids and phytosterols, but there is no specific and feasible separation and purification method in this method
CN102190700A discloses a method for directly esterifying phytosterol esters with fatty acids and phytosterols. The catalyst molecular sieve and silica gel described in it are suitable for laboratory experiments, and there are limitations in industrial scale production; secondly, its described separation and purification molecule Free fatty acids are recovered by distillation, and the heavy phase is collected to obtain the product. The phytosterol ester obtained by this method cannot remove some fat-soluble impurities with a molecular weight greater than that of the phytosterol ester, which affects the color and purity of the product.
None of the synthetic methods of the above-mentioned phytosterol esters separates and purifies them according to the functional distinction between phytosterol saturated fatty acid esters and unsaturated fatty acid esters

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Phytosterol 136.5g (mixed sterol containing brassicasterol 2.17%, campesterol 25.65%, stigmasterol 21.03%, β-sitosterol 46.50%, the purity of mixed sterol is 95.35%), fatty acid 65mL (containing stearic acid 7.25 %, 80.57% oleic acid, 10.98% linoleic acid) were added into a 500mL three-necked flask filled with 65mL toluene and brought back to the water diversion device. After all the phytosterols and fatty acids were dissolved, 0.88g of sodium bisulfate was added, and the , The mol ratio of sodium bisulfate is 1: 0.66: 0.02, is heated to 145 ℃, constant temperature reflux reaction 7 hours, records the transformation efficiency of fatty acid 93.5%, removes catalyst sodium bisulfate by filtration after reaction finishes, and in vacuum tightness is- Under the conditions of 0.09MPa and 120-150℃, distill and recover toluene under reduced pressure until no condensate is formed, add 180mL of ethanol aqueous solution with a volume fraction of 95%, stir at 80℃ for 10 minutes, let...

Embodiment 2

[0016] Add β-sitosterol 138.0g (purity 90%), fatty acid 63mL (used as palm oil fatty acid, which contains 50.20% stearic acid, 38.13% oleic acid, 10.57% linoleic acid) into a 500mL belt filled with 63mL toluene In the three-necked flask of backflow water separator, after treating that β-sitosterol and fatty acid are all dissolved, add 0.83g sodium bisulfate, the mol ratio of β-sitosterol and fatty acid, sodium bisulfate is 1: 0.66: 0.02, other steps and Same as Example 1, the conversion rate of fatty acid was recorded as 93.1%, and the obtained purity was 71g of 94.3% beta-sitosteryl stearate and 60g of 96.6% beta-sitosterol oleic acid (linoleic acid) ester.

Embodiment 3

[0018] Add 170g of phytosterol (containing 0.82% brassicasterol, 25.17% campesterol, 14.31% stigmasterol, 54.13% β-sitosterol), 95mL fatty acid (containing 46.27% palmitic acid, 50.35% oleic acid) into 95mL xylene In the 500mL three-necked flask with backflow water separation device, after the phytosterols and fatty acids are completely dissolved, add 1.33g of potassium bisulfate, the molar ratio of phytosterols, fatty acids, and potassium bisulfate is 1:0.77:0.025, and heat to 140°C , constant temperature reflux reaction for 8 hours, and the conversion rate of fatty acid was 90.5%. After the reaction, the catalyst potassium bisulfate was removed by filtration, and the xylene was recovered by distillation under reduced pressure at a vacuum degree of -0.09MPa and a temperature of 120-150°C. Until no condensate is generated, add 200mL of ethanol aqueous solution with a volume fraction of 95%, stir at 80°C for 10 minutes, let stand to separate layers to remove the ethanol phase, a...

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Abstract

The invention relates to a method for synthesizing and separating phytosterol saturated fatty acid esters and phytosterol unsaturated fatty acid esters. The method comprises the following steps: reacting phytosterol and a mixture of saturated fatty acid esters and unsaturated fatty acid esters, sequentially washing the obtained products by a 70-80DEG C aqueous ethanol solution with the volume fraction of above 95% and an -10-10DEG C aqueous methanol solution with the volume fraction of above 80%, filtering, washing the obtained filter cake by the -10-10DEG C aqueous methanol solution with the volume fraction of above 80% to obtain the phytosterol saturated fatty acid esters with the purity of above 90%, carrying out reduced pressure distillation on the obtained filtrate, and carrying out film evaporation and molecular distillation to obtain the phytosterol unsaturated fatty acid esters with the purity of above 90%. According to the invention, the method is simple, conversion rates of raw materials are high, and the obtained products have the advantages of high purity and good color, and the phytosterol saturated fatty acid esters which can be used for antibiosis and anti-inflammation can be applied to the cosmetic field; and the phytosterol unsaturated fatty acid esters which have the antioxidation and cholesterol reduction effects can be applied to medicine and food fields.

Description

technical field [0001] The invention belongs to the technical field of the general preparation process of steroids, and in particular relates to a method for synthesizing phytosterol esters from phytosterols and mixed fatty acids, in particular to a method for separating saturated fatty acid esters and unsaturated fatty acid esters of phytosterols. Background technique [0002] With the improvement of people's living standards and changes in diet structure, the incidence of "three highs" is getting higher and higher, and there is a trend of younger people. A large number of studies have shown that the high concentration of cholesterol in the blood, especially the high concentration of low-density lipoprotein cholesterol, is the main factor causing various cardiovascular and cerebrovascular diseases. Therefore, reducing the concentration of cholesterol in the blood can significantly reduce the risk of cardiovascular and cerebrovascular diseases. morbidity. Because direct dru...

Claims

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Application Information

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IPC IPC(8): C07J9/00C07J75/00
Inventor 孟永宏陈卫锋牛永洁孟利军
Owner XIAN HEALTHFUL BIOTECH
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