CN112159320A - Production method of high-purity linolenic acid - Google Patents
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- CN112159320A CN112159320A CN202011026389.9A CN202011026389A CN112159320A CN 112159320 A CN112159320 A CN 112159320A CN 202011026389 A CN202011026389 A CN 202011026389A CN 112159320 A CN112159320 A CN 112159320A
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- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
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- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
- C07C51/44—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
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Abstract
The invention belongs to the field of food processing, and particularly relates to a production method of high-efficiency high-purity linolenic acid. The production method comprises cleaning semen Lini/fructus Perillae, removing shell, and squeezing to obtain oleum Lini/fructus Perillae oil. And (3) saponifying linseed oil/perilla seed oil, ultrasonically dissolving fatty acid salt crystals, acidifying, carrying out high-pressure homogeneous urea inclusion, rectifying, and carrying out three-stage molecular distillation to obtain the high-purity linolenic acid. The invention uses the flaxseed/perilla seed to squeeze and obtain the flaxseed oil/perilla seed oil, and then prepares the linolenic acid, the content of the obtained linolenic acid is high (more than 95 percent), the content of saturated fatty acid is almost 0, the content of monounsaturated fatty acid is less than 1, the efficiency is high, the by-products are few, and the invention is more suitable for industrialized production.
Description
Technical Field
The invention belongs to the field of food processing, and particularly relates to a production method of high-purity linolenic acid.
Background
Linolenic acid, belonging to omega-3 series of polyene fatty acids, is all cis-9, 12, 15 octadecatrienoic acid, exists in dark green plants in the form of glyceride, is a main component forming human tissue cells, can be synthesized and metabolized in vivo, and is converted into vital active factors DHA and EPA necessary for the organism. Alpha-linolenic acid is a basic substance constituting cell membranes and biological enzymes and plays a decisive role in human health. However, it cannot be synthesized in humans and must be taken in vitro. It is an essential nutrient which is necessary for human health, but is generally deficient and urgently needed to be supplemented.
The conventional methods for purifying fatty acids mainly include: metal ion complexation, molecular distillation, column chromatography, adsorption separation, lipase concentration, low temperature crystallization, and urea inclusion. The urea inclusion method is simple and easy to operate, urea can be recycled, and environmental pollution is low, so that the urea inclusion method becomes a preferred mixed fatty acid purification process for more and more enterprises. However, the purity obtained by the urea inclusion method alone is not very high because of uneven contact, loss of part of the desired polyunsaturated fatty acids, and incomplete inclusion of saturated fatty acids. The conventional low temperature crystallization method is to reduce the temperature of raw materials to-80 ℃ to-20 ℃, which is difficult to reach in normal factory production and has high cost.
Disclosure of Invention
The invention provides a method for producing high-purity linolenic acid, which has low cost and high efficiency and is suitable for industrial production in order to make up for the defects of the prior art.
The invention is realized by the following technical scheme:
a production method of high-purity linoleic acid is characterized by comprising the following steps: firstly, cleaning and shelling the flaxseed/perilla seed, and squeezing to obtain the flaxseed oil/perilla seed oil. The method comprises the steps of taking linseed oil/perilla seed oil as a raw material, saponifying, ultrasonically dissolving fatty acid salt, crystallizing, separating out, acidifying, carrying out high-pressure homogeneous urea inclusion, rectifying, and carrying out three-stage molecular distillation to obtain the high-purity alpha-linolenic acid.
The preparation process comprises the following steps:
1. selecting linseed oil/perilla seed oil, cleaning, shelling and pressing to obtain the linseed oil/perilla seed oil.
2. Calculating theoretical alkali amount of oleum Lini/Perilla seed oil, mixing with 18-30% NaOH-ethanol (40-80% by mass) at 70-90 deg.C, stirring for 1-1.5 hr, and cooling to room temperature to obtain saponification solution.
3. Adding 93-97% ethanol into the soap solution at a mass ratio of 1:2-5, dissolving for 1-5h under ultrasonic treatment of 100KHz and 200KHz, cooling in gradient manner, cooling at 0-10 deg.C for 1-3h, keeping the temperature at-8-0 deg.C for 1-3h, filtering, and removing the residue. The filter residue is saturated fatty acid sodium salt, partial linoleic acid sodium salt and partial monounsaturated fatty acid sodium salt. Gradient cooling, wherein the first step of cooling removes saturated fat, and the second step of cooling removes monounsaturated fat and linoleic acid.
4. And (3) adding 10-15% hydrochloric acid into the filtrate to adjust the pH to 2-3, stirring for 1-1.5h at normal temperature, standing for layering, collecting 1-fold volume of water of the upper fatty acid layer, and washing to neutrality. The collected fatty acids include monounsaturated fatty acids, saturated fatty acids, linoleic acid, and polyunsaturated fatty acids.
5. Dissolving urea by using ethanol water (with the concentration of 80-99 percent) in proportion to the ratio of urea: 1:3-6 of ethanol, heating to 70-80 ℃, refluxing until urea is dissolved, adding fatty acid (the weight of urea: fatty acid =1: 0.3-0.5), shaking, heating and refluxing for 1h, pumping into a homogenizer, homogenizing for 1-4 times under 20-40Mpa, cooling to room temperature, stirring for 10-25h at 0-20 ℃, pumping the reactant into a centrifuge, and centrifuging to separate out crystals of saturated fatty acid, partial monounsaturated fatty acid and partial linoleic acid; filtering, adding 5-10% salt water (25-35% of the material), separating the upper oil layer, washing with water (removing urea and partial ethanol), vacuum-pumping (vacuum degree of 0-500 Pa), heating (80-95 deg.C) for dehydration, and removing ethanol.
6. Taking the oil layer product, rectifying, wherein the feeding amount is 200-300kg/h, and the primary rectification conditions are as follows: rectifying at 75-95 ℃ and under the pressure of 100 and 350Pa to separate water and low-boiling-point substances; and (3) secondary rectification conditions: rectifying at 105 ℃ and 130 ℃ under 50-100Pa to separate saturated fatty acid, monounsaturated fatty acid and partial linoleic acid.
7. Taking the product, and performing primary molecular distillation at the distillation temperature of 120-135 ℃; the secondary molecular distillation is carried out at the temperature of 130-160 ℃, and the tertiary molecular distillation is carried out at the temperature of 160-180 ℃; the pressure is 10-250Pa, the feeding amount is 30-300ml/min, and the rotating speed of the film scraper is 100-500 r/min. Separating the monounsaturated fatty acids and linoleic acid.
The invention has the beneficial effects that: the method has the advantages of low cost, high yield, simple process and high purity of the obtained linolenic acid, and is more suitable for industrial production.
The invention uses the flaxseed/perilla seed to squeeze and obtain flaxseed oil/perilla seed oil, and then prepares linolenic acid, the content of the obtained alpha-linolenic acid is high (more than 95 percent), the content of saturated fatty acid is almost 0, the content of monounsaturated fatty acid is less than 1, polyunsaturated fatty acid is well preserved, the efficiency is high, the by-product is less, and the invention is more suitable for industrialized production.
According to the production method of the high-purity linolenic acid, the urea ethanol oil is dissolved through a homogenizer process by adopting high-pressure homogenization, so that the materials are contacted more fully, and the loss of required polyunsaturated fatty acid is reduced; the soap solution dissolving and crystallizing process is adopted, so that the content of linolenic acid is greatly improved under the condition of low energy consumption; gradient cooling, wherein the first step of cooling removes saturated fat, and the second step of cooling removes monounsaturated fat and linoleic acid. The raw material is subjected to a rectification and molecular distillation combined process to substantially remove saturated fatty acid and monounsaturated fatty acid in the linolenic acid product, so that the linolenic acid with the content of more than 95 percent is obtained.
The high-pressure homogenization process is added in the urea inclusion and dissolution process to improve the uniformity of liquid mixing; the fatty acid sodium salt is adopted for dissolving and crystallizing, so that the crystallization temperature is increased, and the cost required under the low-temperature condition is reduced; the low-temperature purification also effectively keeps the nutrition of the oil product.
Detailed Description
Example 1:
a method for producing high-purity linoleic acid comprises cleaning semen Lini, removing hull, and squeezing to obtain oleum Lini. Taking 50kg of linseed oil, calculating the theoretical alkali amount to be 6.8kg, preparing 18% NaOH-70% ethanol, stirring for 1.5h at 70 ℃, and cooling to room temperature. Adding 3 times of 95% ethanol, dissolving in 200KHz ultrasonic for 2 hr, cooling to room temperature, cooling at 10 deg.C for 1 hr, holding at-4 deg.C for 2 hr, and vacuum filtering. And (3) adding 15% hydrochloric acid into the filtrate to adjust the pH value to 2-3, stirring for 1h at normal temperature, standing for layering, collecting 1 volume of water of the upper fatty acid layer, and washing with water to be neutral. Dissolving urea by using ethanol water (volume concentration is 95 percent), comparing the urea: 1:4 of ethanol, heating to 75 ℃, refluxing until urea is dissolved, adding fatty acid (the weight ratio of urea to fatty acid =1: 0.3), shaking, heating and refluxing for 1h, pumping into a homogenizer, homogenizing for 2 times at 25MPa, returning into a reaction kettle, cooling to room temperature, stirring for 10h at 4 ℃ in the reaction kettle, pumping the reactant into a centrifuge, centrifugally separating out saturated fatty acid, partial monounsaturated fatty acid and partial linoleic acid crystals, performing suction filtration, adding saline solution (the saline solution with the concentration of 7 percent accounting for 30 percent of the mass of the material) into the filtrate, separating an upper oil layer, washing, vacuumizing (the vacuum degree of 500 Pa), heating (80 ℃) for dehydration, and removing ethanol. Taking the product, and rectifying under the first-stage rectification condition: rectifying at 75 ℃ under 100 Pa; and (3) secondary rectification conditions: rectifying at 130 ℃ under 100 Pa; the feed rate was 200 kg/h. Performing primary molecular distillation at the distillation temperature of 125 ℃; the second-stage molecular distillation is 140 ℃, the third-stage molecular distillation is 170 ℃, the pressure is 80Pa, the feeding amount is 100ml/min, and the rotating speed of a film scraper is 100 r/min. The purity of the obtained linolenic acid is 97.2 percent.
Example 2:
a method for producing high-purity linoleic acid comprises cleaning fructus Perillae, removing shell, and squeezing to obtain fructus Perillae oil. Taking 100kg of perilla seed oil, calculating the theoretical alkali amount to be 19.5kg, preparing 25% NaOH-80% ethanol, stirring for 1.5h at 80 ℃, and cooling to room temperature. Adding 93% ethanol 5 times the mass of the soap solution, dissolving under ultrasonic condition of 150KHz for 3h, cooling to room temperature, cooling in gradient manner for 3h at 8 deg.C, keeping the temperature constant at-2 deg.C for 1h, and vacuum filtering. Adding 12% hydrochloric acid into the filtrate to adjust pH to 2-3, stirring at room temperature for 1h, standing for layering, collecting upper layer fatty acid 1 times volume of water, and washing with water to neutrality. Dissolving urea by using ethanol water (the volume concentration is 88 percent), comparing the urea: 1:5 of ethanol, heating to 80 ℃, refluxing, adding fatty acid (the weight ratio of urea to fatty acid =1: 0.4) after urea is dissolved, shaking, heating and refluxing for 1h, pumping into a homogenizer, homogenizing for 2 times under 20MPa, returning into a reaction kettle, cooling to room temperature, stirring for 24h at 15 ℃ in the reaction kettle, pumping the reactant into a centrifuge, centrifugally separating out saturated fatty acid, partial monounsaturated fatty acid and partial linoleic acid crystals, performing suction filtration, adding saline solution (the saline solution with the concentration of 5 percent accounting for 35 percent of the mass of the material) into the filtrate, separating an upper oil layer, washing, vacuumizing (the vacuum degree of 50 Pa), heating (95 ℃) for dehydration, and removing ethanol. Taking the product, and rectifying under the first-stage rectification condition: rectifying at 85 ℃ under 200 Pa; and (3) secondary rectification conditions: rectifying at 105 ℃ under 50 Pa; the feed rate was 300 kg/h. Performing primary molecular distillation at 135 deg.C; the second molecular distillation is carried out at 155 ℃, and the third molecular distillation is carried out at 180 ℃; the pressure was 150Pa, the feed rate was 300ml/min, and the speed of the knifing device was 500 r/min. The purity of the obtained linolenic acid is 98.5 percent.
Example 3:
a method for producing high-purity linoleic acid comprises cleaning semen Lini, removing hull, and squeezing to obtain oleum Lini. Taking 50kg of linseed oil, calculating the theoretical alkali amount to be 6.8kg, preparing 30% NaOH-50% ethanol, stirring for 1.5h at 90 ℃, and cooling to room temperature. Adding 97% ethanol 2 times the mass of the soap solution, dissolving under ultrasonic 100KHz for 5h, cooling to room temperature, cooling in gradient manner for 3h at 5 deg.C, keeping the temperature constant for 3h at-8 deg.C, and vacuum filtering. And (3) adding 10% hydrochloric acid into the filtrate to adjust the pH value to 2-3, stirring for 1.5h at normal temperature, standing for layering, collecting 1 volume of water of the upper fatty acid layer, and washing to neutrality. Dissolving urea by using ethanol water (the volume concentration is 80 percent), comparing the urea: heating ethanol at a weight ratio of 1:6, refluxing at 70 ℃ until urea is dissolved, adding fatty acid (weight ratio of urea: fatty acid =1: 0.5), shaking, heating and refluxing for 1h, pumping into a homogenizer, homogenizing at 40MPa for 4 times, returning into a reaction kettle, cooling to room temperature, stirring at 10 ℃ in the reaction kettle for 10h, pumping the reactant into a centrifuge, centrifuging to separate out saturated fatty acid, partial monounsaturated fatty acid and partial linoleic acid crystals, performing suction filtration, adding saline solution (10% saline solution with the concentration of 25% of the mass of the material) into the filtrate, separating an upper oil layer, washing with water, vacuumizing (the vacuum degree of 250 Pa), heating (at 90 ℃) to dehydrate, and removing ethanol. Taking the product, and rectifying under the first-stage rectification condition: rectifying at 95 ℃ and 350 Pa; and (3) secondary rectification conditions: rectification is carried out at 115 ℃ and 80Pa, and the feeding amount is 250 kg/h. Performing primary molecular distillation at the distillation temperature of 120 ℃; the secondary molecular distillation is 130 ℃, the tertiary molecular distillation is 160 ℃, the pressure is 250Pa, the feeding amount is 200ml/min, and the rotating speed of a film scraper is 300 r/min. The purity of the obtained linolenic acid is 99.2 percent.
Claims (6)
1. A production method of high-purity linolenic acid is characterized by comprising the following steps: the method comprises the following steps:
(1) cleaning semen Lini or fructus Perillae, removing shell, and squeezing to obtain oleum Lini or fructus Perillae oil;
(2) saponification: calculating theoretical alkali amount according to linseed oil or perilla seed oil, preparing into NaOH-ethanol solution, adding into oil, stirring at 70-90 deg.C for 1-1.5 hr, and cooling to room temperature to obtain saponified solution;
(3) ultrasonically dissolving fatty acid salt crystals: adding ethanol into the soap solution, dissolving for 1-5h under ultrasonic treatment of 100KHz and 200KHz, cooling, gradient cooling, cooling at 0-10 deg.C for 1-3h, keeping the temperature at-8-0 deg.C for 1-3h, filtering, and removing the filter residue;
(4) acidifying: adding 10-15% hydrochloric acid by mass into the filtrate to adjust pH to 2-3, stirring at room temperature for 1-1.5h, standing for layering, collecting upper layer fatty acid, and washing with 1-fold volume of water to neutrality;
(5) high-pressure homogeneous urea inclusion: dissolving urea with ethanol water, heating to 70-80 deg.C for refluxing, adding fatty acid after urea is dissolved, shaking, heating for refluxing for 1h, placing into a homogenizer, homogenizing for 1-4 times at 20-40Mpa, returning to the reaction kettle, cooling to room temperature, stirring at 0-20 deg.C for 10-24h, centrifuging to separate out crystals, vacuum filtering, adding salt water into filtrate, separating upper oil layer, washing with water, vacuum-pumping, heating for dehydration, and removing ethanol.
(6) Secondary rectification;
(7) and performing three-stage molecular distillation to obtain the high-purity alpha-linolenic acid.
2. The method for producing linolenic acid with high purity according to claim 1, characterized in that: in the step (2), the NaOH-ethanol solution is prepared by dissolving sodium hydroxide with ethanol with the concentration of 40-80%, and the mass concentration of the dissolved sodium hydroxide is 18-30%.
3. The method for producing linolenic acid with high purity according to claim 1, characterized in that: in the step (3), ethanol with the volume concentration of 93-97% is added into the soap solution, and the mass ratio of the soap solution to the ethanol is 1: 2-5.
4. The method for producing linolenic acid with high purity according to claim 1, characterized in that: in the step (5), ethanol water with volume concentration of 80-99% is adopted to dissolve urea, and the weight ratio of urea is as follows: ethanol =1: 3-6, heating to 70-80 ℃ for reflux, adding fatty acid after urea is dissolved, wherein the weight ratio of urea is as follows: 0.3-0.5 of fatty acid =1, shaking up, heating and refluxing for 1h, pumping into a homogenizer, homogenizing for 1-4 times under 20-40Mpa, returning into the reaction kettle, cooling to room temperature, stirring for 10-24h at 0-20 ℃ in the reaction kettle, pumping the reactant into a centrifuge, and centrifuging to separate out crystals of saturated fatty acid, partial monounsaturated fatty acid and partial linoleic acid; filtering, adding 5-10% salt water 25-35% of the filtrate, separating the upper oil layer, washing with water to remove urea and part of ethanol, vacuumizing to 0-500Pa, heating to 80-95 deg.C, dehydrating, and removing ethanol.
5. The method for producing linolenic acid with high purity according to claim 1, characterized in that: and (6) rectification: primary rectification conditions: the feeding amount is 200 plus materials for 300kg/h, the temperature is 75-95 ℃, and the rectification is carried out under the pressure of 100 plus materials for 350Pa, so as to separate the water and the low-boiling-point substances; and (3) secondary rectification conditions: 105-130 ℃ and 50-100 Pa; separating saturated fatty acid, monounsaturated fatty acid and partial linoleic acid.
6. The method for producing linolenic acid with high purity according to claim 1, characterized in that: in the step (7), primary molecular distillation is carried out at the distillation temperature of 120-; the secondary molecular distillation is carried out at the temperature of 130-160 ℃, and the tertiary molecular distillation is carried out at the temperature of 160-180 ℃; the pressure is 10-250Pa, the feeding amount is 30-300ml/min, and the rotating speed of the wiped film evaporator is 100-500 r/min; separating the monounsaturated fatty acids and linoleic acid.
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| CN112876350A (en) * | 2021-02-18 | 2021-06-01 | 淳安天龙生物科技有限公司 | Process for preparing plant water-soluble omega 3 from flaxseeds |
| CN113185398A (en) * | 2021-05-17 | 2021-07-30 | 武汉轻工大学 | Enrichment method of high-content conjugated linolenic acid alpha-eleostearic acid in bitter gourd seed oil |
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| CN113185398A (en) * | 2021-05-17 | 2021-07-30 | 武汉轻工大学 | Enrichment method of high-content conjugated linolenic acid alpha-eleostearic acid in bitter gourd seed oil |
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| CN112159320B (en) | 2022-05-20 |
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