CN110845335A - Method for preparing conjugated linoleic acid ethyl ester by using safflower seed oil as raw material - Google Patents
Method for preparing conjugated linoleic acid ethyl ester by using safflower seed oil as raw material Download PDFInfo
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- CN110845335A CN110845335A CN201911110796.5A CN201911110796A CN110845335A CN 110845335 A CN110845335 A CN 110845335A CN 201911110796 A CN201911110796 A CN 201911110796A CN 110845335 A CN110845335 A CN 110845335A
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- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07C67/00—Preparation of carboxylic acid esters
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- C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
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Abstract
The invention provides a method for preparing conjugated ethyl linoleate by using safflower seed oil as a raw material, which is characterized in that the safflower seed oil is used as a main raw material, the content of linoleic acid is up to 69-79%, the safflower seed oil is subjected to ethylation reaction with absolute ethyl alcohol and potassium hydroxide, then liquid separation, washing and drying are carried out, conjugation is carried out by a solvent-free method, then washing and distillation are carried out to prepare the conjugated ethyl linoleate, only 0.993 ton of safflower seed oil is consumed per ton of finished products, the consumption of the raw material is greatly reduced, and the utilization rate and the production efficiency are improved.
Description
Technical Field
The invention relates to the field of conjugated linoleic acid preparation, in particular to a method for preparing conjugated linoleic acid ethyl ester by using safflower seed oil as a raw material.
Background
Ethyl linoleate is colorless to yellowish oily liquid, has the functions of reducing cholesterol and blood fat in blood, and is mainly used as a pharmaceutical raw material for preventing and treating atherosclerosis. The traditional preparation method of ethyl linoleate is to esterify linoleic acid and ethanol in the presence of sulfuric acid, put linoleic acid (iodine value is more than 168), absolute ethyl alcohol and concentrated sulfuric acid into a reactor, stir, heat and reflux for 4 hours; distilling and recovering ethanol until no ethanol is distilled; cooling, washing with water until the water layer is not acidic to Fengfuhong test paper, distilling under reduced pressure to remove water, and collecting 195 deg.C (0.93 kPa) fraction to obtain the final product.
The linoleic acid required for preparing the ethyl linoleate is generally extracted from soybean oil or sunflower seed oil, the content of linoleic acid in the soybean oil is 43-56%, 1 ton of ethyl linoleate can be produced only by 5-5.9 tons of soybean oil soap horns, the usage amount of raw materials is large, and correspondingly, the production efficiency is low.
Therefore, a method for preparing conjugated ethyl linoleate by using safflower seed oil as a raw material is needed, and the problem of low production efficiency caused by large raw material consumption in the traditional preparation process of ethyl linoleate can be solved.
Disclosure of Invention
The invention aims to provide a method for preparing conjugated ethyl linoleate by using safflower seed oil as a raw material, and the method is used for solving the problem of low production efficiency caused by large raw material consumption in the preparation process of the traditional ethyl linoleate.
In order to achieve the purpose, the invention provides the following scheme:
the invention provides a method for preparing conjugated linoleic acid ethyl ester by using safflower seed oil as a raw material, which comprises the following steps:
(1) b, esterification: dissolving 0.6-3 parts by mass of potassium hydroxide in 15-30 parts by mass of absolute ethyl alcohol to prepare an absolute ethyl alcohol-potassium hydroxide solution, mixing all the absolute ethyl alcohol-potassium hydroxide solution with 100 parts by mass of safflower seed oil, and reacting at room temperature for 3-6 hours to carry out an ethylation reaction;
(2) liquid separation: standing the mixture after ethyl esterification overnight, discharging the lower layer after layering, and keeping the upper layer;
(3) washing with water: adding water into the upper-layer mixture after liquid separation, slowly stirring, standing, discharging the lower-layer water washing liquid, and repeatedly washing for 2-3 times until the lower-layer water washing liquid is clear;
(4) and (3) vacuum drying: dehydrating the washed mixture for 2-2.5 h in an environment of 0.08-0.09 MPa and 90-105 ℃;
(5) conjugation: conjugating the dried mixture by a solvent-free method;
(6) and (3) washing with water again: adding water into the conjugated mixture, slowly stirring, standing, and discharging lower-layer water washing liquid to obtain an upper-layer conjugated linoleic acid ethyl ester crude product;
(7) and (3) distillation: and distilling the crude product of the conjugated linoleic acid to remove residual solvent, dehydrating, decoloring, deodorizing and deodorizing to obtain a finished product of the conjugated linoleic acid ethyl ester.
Preferably, in step (1), the purity of the potassium hydroxide is analytical grade.
Preferably, in the step (3), the amount of water added during the water washing is 10-20% of the mass of the upper layer mixture.
Preferably, in step (5), the solvent-free method is conjugated to: and heating the dried mixture to 110-140 ℃, adding a potassium hydroxide catalyst, and carrying out conjugation reaction for 3-7 hours.
Preferably, in the step (6), the amount of water added at the time of the second washing is 10% to 20% of the amount of the conjugated mixture.
Preferably, in the step (7), the distillation temperature is 115-125 ℃.
Compared with the prior art, the invention has the following beneficial technical effects:
the invention provides a method for preparing conjugated ethyl linoleate by using safflower seed oil as a raw material, which is characterized in that the safflower seed oil is used as a main raw material, the content of linoleic acid is up to 69-79%, the safflower seed oil is subjected to ethylation reaction with absolute ethyl alcohol and potassium hydroxide, then liquid separation, washing and drying are carried out, conjugation is carried out by a solvent-free method, then washing and distillation are carried out to prepare the conjugated ethyl linoleate, only 0.993 ton of safflower seed oil is consumed per ton of finished products, the consumption of the raw material is greatly reduced, and the utilization rate and the production efficiency are improved.
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In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings needed to be used in the embodiments will be briefly described below, and it is obvious that the drawings in the following description are only some embodiments of the present invention, and it is obvious for those skilled in the art to obtain other drawings without inventive exercise.
FIG. 1 is a flow chart of a method for preparing conjugated linoleic acid ethyl ester by using safflower seed oil as a raw material according to the present invention;
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The invention aims to provide a method for preparing conjugated ethyl linoleate by using safflower seed oil as a raw material, and the method is used for solving the problem of low production efficiency caused by large raw material consumption in the preparation process of the traditional ethyl linoleate.
In order to make the aforementioned objects, features and advantages of the present invention comprehensible, embodiments accompanied with figures are described in further detail below.
Example 1:
the embodiment provides a method for preparing conjugated linoleic acid ethyl ester by using safflower seed oil as a raw material, as shown in fig. 1, the preparation method comprises the following steps: dissolving 0.6kg of potassium hydroxide in 15kg of absolute ethanol to prepare an absolute ethanol-potassium hydroxide solution, wherein the purity of the potassium hydroxide is analytically pure, mixing the 15.6kg of absolute ethanol-potassium hydroxide solution and 100kg of safflower seed oil, and carrying out an ethylation reaction in a reaction kettle at room temperature for 6 hours; the second step is that: standing the mixture after esterification overnight, discharging the lower layer after layering, and performing additional treatment to keep the upper layer; the third step: adding water accounting for 12% of the mass of the upper-layer mixture after liquid separation, slowly stirring at a rotating speed of 10r/min, standing for 3 hours, discharging lower-layer water washing liquid, and repeatedly washing for 2-3 times until the lower-layer water washing liquid is clear; the fourth step: dehydrating the washed mixture for 2h in an environment of 0.08MPa and 100 ℃; the fifth step: conjugating the dried mixture by a solvent-free method, specifically heating the dried mixture to 120 ℃, adding a potassium hydroxide catalyst, and performing conjugation reaction for 4 hours; and a sixth step: adding water with the mass percent of 10% of the conjugated mixture into the conjugated mixture, slowly stirring the mixture at the speed of 10r/min, standing the mixture, and discharging the lower-layer water washing liquid to obtain an upper-layer conjugated linoleic acid ethyl ester crude product; the seventh step: distilling the crude product of the conjugated linoleic acid to remove residual solvent, dehydrating, decoloring, deodorizing and deodorizing, wherein the distillation temperature is 120 ℃, and obtaining a finished product of the conjugated linoleic acid ethyl ester.
Example 2:
the embodiment provides a method for preparing conjugated linoleic acid ethyl ester by using safflower seed oil as a raw material, as shown in fig. 1, the preparation method comprises the following steps: dissolving 1.5kg of potassium hydroxide in 20kg of absolute ethanol to obtain an absolute ethanol-potassium hydroxide solution, wherein the purity of the potassium hydroxide is analytically pure, mixing 21.5kg of the absolute ethanol-potassium hydroxide solution and 100kg of safflower seed oil, and performing an ethylation reaction in a reaction kettle at room temperature for 5 hours; the second step is that: standing the mixture after esterification overnight, discharging the lower layer after layering, and performing additional treatment to keep the upper layer; the third step: adding 15% of water by mass into the upper-layer mixture after liquid separation, slowly stirring at a rotating speed of 10r/min, standing for 3h, discharging lower-layer water washing liquid, and repeatedly washing for 2-3 times until the lower-layer water washing liquid is clear; the fourth step: dehydrating the washed mixture for 2h in an environment of 0.08MPa and 100 ℃; the fifth step: conjugating the dried mixture by a solvent-free method, specifically heating the dried mixture to 120 ℃, adding a potassium hydroxide catalyst, and performing conjugation reaction for 4 hours; and a sixth step: adding water with the mass percent of 10% of the conjugated mixture into the conjugated mixture, slowly stirring the mixture at the speed of 10r/min, standing the mixture, and discharging the lower-layer water washing liquid to obtain an upper-layer conjugated linoleic acid ethyl ester crude product; the seventh step: distilling the crude product of the conjugated linoleic acid to remove residual solvent, dehydrating, decoloring, deodorizing and deodorizing, wherein the distillation temperature is 120 ℃, and obtaining a finished product of the conjugated linoleic acid ethyl ester.
Example 3:
the embodiment provides a method for preparing conjugated linoleic acid ethyl ester by using safflower seed oil as a raw material, as shown in fig. 1, the preparation method comprises the following steps: dissolving 2kg of potassium hydroxide in 27kg of absolute ethanol to obtain an absolute ethanol-potassium hydroxide solution, wherein the purity of the potassium hydroxide is analytically pure, mixing the 27kg of absolute ethanol-potassium hydroxide solution and 100kg of safflower seed oil, and carrying out an ethylation reaction in a reaction kettle at room temperature for 4 hours; the second step is that: standing the mixture after esterification overnight, discharging the lower layer after layering, and performing additional treatment to keep the upper layer; the third step: adding 15% of water by mass into the upper-layer mixture after liquid separation, slowly stirring at a rotating speed of 10r/min, standing for 3h, discharging lower-layer water washing liquid, and repeatedly washing for 2-3 times until the lower-layer water washing liquid is clear; the fourth step: dehydrating the washed mixture for 2h in an environment of 0.08MPa and 100 ℃; the fifth step: conjugating the dried mixture by a solvent-free method, specifically heating the dried mixture to 120 ℃, adding a potassium hydroxide catalyst, and performing conjugation reaction for 4 hours; and a sixth step: adding water with the mass percent of 10% of the conjugated mixture into the conjugated mixture, slowly stirring the mixture at the speed of 10r/min, standing the mixture, and discharging the lower-layer water washing liquid to obtain an upper-layer conjugated linoleic acid ethyl ester crude product; the seventh step: distilling the crude product of the conjugated linoleic acid to remove residual solvent, dehydrating, decoloring, deodorizing and deodorizing, wherein the distillation temperature is 120 ℃, and obtaining a finished product of the conjugated linoleic acid ethyl ester.
Example 4:
the embodiment provides a method for preparing conjugated linoleic acid ethyl ester by using safflower seed oil as a raw material, as shown in fig. 1, the preparation method comprises the following steps: dissolving 3kg of potassium hydroxide in 30kg of absolute ethanol to obtain an absolute ethanol-potassium hydroxide solution, wherein the purity of the potassium hydroxide is analytically pure, mixing 33kg of the absolute ethanol-potassium hydroxide solution and 100kg of safflower seed oil, and carrying out an ethylation reaction in a reaction kettle at room temperature for 3 hours; the second step is that: standing the mixture after esterification overnight, discharging the lower layer after layering, and performing additional treatment to keep the upper layer; the third step: adding 15% of water by mass into the upper-layer mixture after liquid separation, slowly stirring at a rotating speed of 10r/min, standing for 3h, discharging lower-layer water washing liquid, and repeatedly washing for 2-3 times until the lower-layer water washing liquid is clear; the fourth step: dehydrating the washed mixture for 2h in an environment of 0.08MPa and 100 ℃; the fifth step: conjugating the dried mixture by a solvent-free method, specifically heating the dried mixture to 120 ℃, adding a potassium hydroxide catalyst, and performing conjugation reaction for 4 hours; and a sixth step: adding water with the mass percent of 10% of the conjugated mixture into the conjugated mixture, slowly stirring the mixture at the speed of 10r/min, standing the mixture, and discharging the lower-layer water washing liquid to obtain an upper-layer conjugated linoleic acid ethyl ester crude product; the seventh step: distilling the crude product of the conjugated linoleic acid to remove residual solvent, dehydrating, decoloring, deodorizing and deodorizing, wherein the distillation temperature is 120 ℃, and obtaining a finished product of the conjugated linoleic acid ethyl ester.
The inventor produces four batches of conjugated linoleic acid ethyl ester aiming at the four embodiments respectively, and records the mass of the consumed safflower seed oil and the produced conjugated linoleic acid ethyl ester of each batch, and the recorded results are as follows:
| batches of | Consumption of safflower seed oil quality (ton) | Yield conjugated linoleic acid ethyl ester quality (ton) |
| Example 1 | 3 | 3.026 |
| Example 2 | 2 | 2.014 |
| Example 3 | 2 | 2.015 |
| Example 4 | 2.5 | 2.517 |
According to the method for preparing the conjugated linoleic acid ethyl ester by using the safflower oil as the raw material, the safflower oil, the absolute ethyl alcohol and the potassium hydroxide are subjected to an ethylation reaction, then liquid separation, water washing and drying are carried out, conjugation is carried out by a solvent-free method, then washing and distillation are carried out to prepare the conjugated linoleic acid ethyl ester, only 0.993 ton of safflower oil is consumed per ton of finished products, the consumption of the raw material is greatly reduced, and the utilization rate and the production efficiency are improved compared with the conventional method for preparing the linoleic acid ethyl ester by using the soybean oil.
The principle and the implementation mode of the invention are explained by applying specific examples, and the description of the above examples is only used for helping understanding the method and the core idea of the invention; meanwhile, for a person skilled in the art, according to the idea of the present invention, the specific embodiments and the application range may be changed. In summary, this summary should not be construed to limit the present invention.
Claims (6)
1. A method for preparing conjugated linoleic acid ethyl ester by using safflower seed oil as a raw material is characterized by comprising the following steps: the method comprises the following steps:
(1) b, esterification: dissolving 0.6-3 parts by mass of potassium hydroxide in 15-30 parts by mass of absolute ethyl alcohol to prepare an absolute ethyl alcohol-potassium hydroxide solution, mixing all the absolute ethyl alcohol-potassium hydroxide solution with 100 parts by mass of safflower seed oil, and reacting at room temperature for 3-6 hours to carry out an ethylation reaction;
(2) liquid separation: standing the mixture after ethyl esterification overnight, discharging the lower layer after layering, and keeping the upper layer;
(3) washing with water: adding water into the upper-layer mixture after liquid separation, slowly stirring, standing, discharging the lower-layer water washing liquid, and repeatedly washing for 2-3 times until the lower-layer water washing liquid is clear;
(4) and (3) vacuum drying: dehydrating the washed mixture for 2-2.5 h in an environment of 0.08-0.09 MPa and 90-105 ℃;
(5) conjugation: conjugating the dried mixture by a solvent-free method;
(6) and (3) washing with water again: adding water into the conjugated mixture, slowly stirring, standing, and discharging lower-layer water washing liquid to obtain an upper-layer conjugated linoleic acid ethyl ester crude product;
(7) and (3) distillation: and distilling the crude product of the conjugated linoleic acid to remove residual solvent, dehydrating, decoloring, deodorizing and deodorizing to obtain a finished product of the conjugated linoleic acid ethyl ester.
2. The method for preparing conjugated linoleic acid ethyl ester by using safflower seed oil as a raw material according to claim 1, which is characterized in that: in the step (1), the purity of the potassium hydroxide is analytical grade.
3. The method for preparing conjugated linoleic acid ethyl ester by using safflower seed oil as a raw material according to claim 1, which is characterized in that: in the step (3), the amount of water added during water washing is 10-20% of the mass of the upper layer mixture.
4. The method for preparing conjugated linoleic acid ethyl ester by using safflower seed oil as a raw material according to claim 1, which is characterized in that: in the step (5), the solvent-free method comprises the following steps: and heating the dried mixture to 110-140 ℃, adding a potassium hydroxide catalyst, and carrying out conjugation reaction for 3-7 hours.
5. The method for preparing conjugated linoleic acid ethyl ester by using safflower seed oil as a raw material according to claim 1, which is characterized in that: in the step (6), the amount of water added during the second water washing is 10-20% of the mass of the conjugated mixture.
6. The method for preparing conjugated linoleic acid ethyl ester by using safflower seed oil as a raw material according to claim 1, which is characterized in that: in the step (7), the distillation temperature is 115-125 ℃.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101565373A (en) * | 2009-05-27 | 2009-10-28 | 沈琳 | Method for preparing conjugated linoleic acid ethyl ester |
| CN104673499A (en) * | 2013-11-28 | 2015-06-03 | 丰益(上海)生物技术研发中心有限公司 | Method for preparing conjugated linoleic acid |
| CN106565454A (en) * | 2016-10-20 | 2017-04-19 | 武汉藤欣生物工程有限公司 | Preparation method for conjugated linoleic acid |
| CN106565473A (en) * | 2016-10-20 | 2017-04-19 | 武汉藤欣生物工程有限公司 | Preparation method for conjugated alkyl linoleate |
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- 2019-11-05 CN CN201911110796.5A patent/CN110845335A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101565373A (en) * | 2009-05-27 | 2009-10-28 | 沈琳 | Method for preparing conjugated linoleic acid ethyl ester |
| CN104673499A (en) * | 2013-11-28 | 2015-06-03 | 丰益(上海)生物技术研发中心有限公司 | Method for preparing conjugated linoleic acid |
| CN106565454A (en) * | 2016-10-20 | 2017-04-19 | 武汉藤欣生物工程有限公司 | Preparation method for conjugated linoleic acid |
| CN106565473A (en) * | 2016-10-20 | 2017-04-19 | 武汉藤欣生物工程有限公司 | Preparation method for conjugated alkyl linoleate |
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Application publication date: 20200228 |