CN108823255B - Preparation method of tri-saturated fatty acid glyceride - Google Patents
Preparation method of tri-saturated fatty acid glyceride Download PDFInfo
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Abstract
The invention relates to the technical field of glyceride synthesis and processing, in particular to a preparation method of trisaturated fatty acid glyceride, which comprises the following steps: carrying out catalytic reaction on glyceride containing saturated fatty acid residue and saturated fatty acid salt under the action of lipase to obtain the trisaturated fatty acid glyceride. Wherein the saturated fatty acid residue is the same as the corresponding saturated fatty acid in the saturated fatty acid salt, and the glyceride containing the saturated fatty acid residue has at least one ester bond or hydroxyl group which is not bonded to the saturated fatty acid residue. On the basis that the glyceride part has saturated fatty acid residues, a sufficient amount of saturated fatty acid residues are provided through corresponding saturated fatty acid salts, and the catalytic action of lipase is utilized, so that the reaction conditions are mild, side reactions are few, and the purity of the generated trisaturated fatty acid glyceride is high.
Description
Technical Field
The invention relates to the technical field of glyceride synthesis and processing, and particularly relates to a preparation method of trisaturated fatty acid glyceride.
Background
The synthesis method of the trisaturated fatty acid glyceride mainly comprises the following steps: the random transesterification of triglycerides and the reaction of glycerol with saturated fatty acids at high temperatures (180 ℃ to 200 ℃) are carried out under the action of chemical catalysts. The purity of the trisaturated fatty acid glycerides prepared by random transesterification of triglycerides with the help of chemical catalysts is not high. The glycerol and saturated fatty acid react at high temperature (180-200 ℃) and have the defects of high reaction temperature, harsh technological reaction conditions and more side reactions.
Disclosure of Invention
The purpose of the present invention is to provide a method for producing a trisaturated fatty acid glyceride, which can achieve a high purity of the trisaturated fatty acid glyceride, a high content of saturated fatty acids at the sn-2 position, simple reaction conditions, and a small number of side reactions.
The technical problem to be solved by the invention is realized by adopting the following technical scheme.
The invention provides a preparation method of tri-saturated fatty glyceride, which comprises the following steps: carrying out catalytic reaction on glyceride containing saturated fatty acid residue and saturated fatty acid salt under the action of lipase to obtain the trisaturated fatty acid glyceride. Wherein the saturated fatty acid residue is the same as the corresponding saturated fatty acid in the saturated fatty acid salt, and the glyceride containing the saturated fatty acid residue has at least one ester bond or hydroxyl group which is not bonded to the saturated fatty acid residue.
On the basis that the glyceride part has saturated fatty acid residues, a sufficient amount of saturated fatty acid residues are provided through corresponding saturated fatty acid salts, and the catalytic action of lipase is utilized, so that the reaction conditions are mild, side reactions are few, and the purity of the generated trisaturated fatty acid glyceride is high.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present invention more apparent, the technical solutions of the embodiments of the present invention will be clearly and completely described below. Those whose specific conditions are not specified in the embodiment or examples are carried out according to the conventional conditions or conditions recommended by the manufacturer. The reagents or instruments used are not indicated by the manufacturer, and are all conventional products available commercially.
The method for producing a trisaturated fatty acid glyceride according to the embodiment of the present invention will be specifically described below.
Some embodiments of the present invention provide a method for preparing a tri-saturated fatty acid glyceride, comprising: carrying out catalytic reaction on glyceride containing saturated fatty acid residue and saturated fatty acid salt under the action of lipase to obtain trisaturated fatty acid glyceride.
Where the saturated fatty acid residue is the same as the corresponding saturated fatty acid in the saturated fatty acid salt, e.g., where the glyceride contains saturated fatty acid residues that are palmitic acid residues (other types of saturated fatty acid residues that contain non-palmitic acid residues are not excluded), then the corresponding saturated fatty acid salt is a palmitate salt. And the glyceride containing a saturated fatty acid residue has at least one ester bond or hydroxyl group which is not bonded to the saturated fatty acid residue. That is, the glyceride as a raw material includes at least one of a monoglyceride, a diglyceride and a triglyceride, and a part of the ester bond thereof is an ester bond obtained by bonding a saturated fatty acid (specified above). For example, the glyceride may be a monoglyceride, a diglyceride, or a triglyceride, or a mixture of a diglyceride and a triglyceride.
It is noted that the catalytic reaction includes a transesterification reaction and an esterification reaction, and when the glyceride is mainly a triglyceride, the transesterification reaction is mainly performed, and when the glyceride includes a partial diglyceride or monoglyceride, the esterification reaction is also present.
On the basis that glyceride has partial ester bond of specific saturated fatty acid residue, by introducing specific fatty acid salt which can provide a large amount of specific fatty acid residue, the glyceride can generate ester exchange and esterification reaction under the catalysis of enzyme, so that the reaction condition is reduced, the side reaction is less, the purity of the generated trisaturated fatty acid glyceride is high, and the content of saturated fatty acid on sn-2 position is high.
According to some embodiments, the ratio of glycerides to saturated fatty acid salts is added in an amount such that the proportion of saturated fatty acid residues in the reaction system to the total fatty acid residues is greater than or equal to 90%, preferably greater than 92%, more preferably greater than 95%. For example, the saturated fatty acid salt may be added so that the proportion of saturated fatty acid residues in the reaction system to the total fatty acid residues is 90%, 91%, 92%, 93%, 94%, 95%, 96%, 97%, 98%, or the like.
Through the arrangement of the proportion of the reactants, the transesterification or esterification can be fully satisfied, and then the reactants can be fully contacted, so that a reaction product with higher purity can be obtained.
According to some embodiments, the Lipase is added in an amount of 0.05-10%, preferably 0.1-8%, further preferably, the amount of Novozym 435 is 4-8%, the amount of Lipase DF "Amano" 15 is 0.1-1%, the amount of LipozymeTLIM is 4-8%, and the amount of LipaseAY30G is 0.1-1%. For example, the amount of lipase added may be 0.05%, 0.1%, 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, or 9%. The addition amount of lipase has an important influence on the reaction process, the catalysis effect cannot be achieved when the addition amount is too low, the cost is increased when the addition amount is too high, and the contact between reactants in the reaction process is influenced to a certain extent, so that the reaction effect is poor. Therefore, the catalytic action of the reaction can be sufficiently achieved by the addition amount of the non-directional lipase in the above range, so that the reaction proceeds more thoroughly within a predetermined reaction time.
In some embodiments, the Lipase comprises at least one of a non-directed Lipase, a directed Lipase, preferably the Lipase is a non-directed Lipase comprising at least one of Novozym 435, Lipase DF "Amano" 15, lipozyme tlim, and Lipase ay 30G. For example, the non-directional Lipase may be Novozym 435 or Lipase DF "Amano" 15, or a mixture of Novozym 435 and Lipase DF "Amano" 15. Preferably, the non-directional Lipase is Lipase DF "Amano" 15.
According to some embodiments, the temperature of the catalytic reaction is 30-90 ℃, preferably 35-85 ℃, further preferably, the lipozyme TLIM reaction temperature is 65-70 ℃, the Novozym 435 reaction temperature is 75-85 ℃, the reaction temperature of Lipase DF "Amano" 15 is 35-40 ℃, and the reaction temperature of Lipase AY30G is 35-40 ℃; the time of the catalytic reaction is 0.5-9 hours, and the preferable reaction time is 1-4 hours. Under this reaction temperature, reaction temperature is lower for traditional chemical catalyst's reaction temperature ratio, and its reaction goes on more easily, can keep reaction temperature invariable through the mode of water bath heating, and it is heated more evenly in the water bath heating, and heat transfer is effectual, and then makes the reaction go on more easily. Of course, other heating methods such as furnace heating may be selected to maintain the reaction temperature.
According to some embodiments, the corresponding saturated fatty acid of the saturated fatty acid residue and the saturated fatty acid salt is selected from palmitic acid, stearic acid, caprylic acid, capric acid, lauric acid, myristic acid or arachidic acid, for example, the reactant may be a glyceride and a palmitate containing a palmitic acid residue, a glyceride and a stearate containing a stearic acid residue, or a glyceride and a laurate containing a lauric acid residue. Palmitic acid or stearic acid is preferred, and palmitic acid is more preferred.
The fatty acid salt is selected as a strong base weak acid salt, has strong ionization capacity and strong fatty acid residue activity, and has the fatty acid residue providing capacity far larger than that of free fatty acid or fatty acid ester, so that the ester exchange reaction rate is accelerated, the reaction time is shortened, the lipase dosage can be reduced, and the cost is reduced.
According to some embodiments, the glyceride containing saturated fatty acid residues may be cocoa butter, coconut oil, palm kernel oil, palm stearin, or 58-degree palm oil. Preferably, the glyceride containing saturated fatty acid residues is palm oil stearin, which is a palm oil with a high melting point (melting point 44-56 ℃) generated in the process of producing edible palm oil.
According to some embodiments, the saturated fatty acid salt is a saturated fatty acid alkali metal salt, preferably the saturated fatty acid salt is a saturated fatty acid sodium or a saturated fatty acid potassium.
According to some embodiments, the catalytic reaction specifically comprises mixing a glyceride containing saturated fatty acid residues with a saturated fatty acid salt, adding lipase, and stirring under the condition of introducing an inert gas. The protection through inert gas can avoid the outside air to cause the influence to its reaction to the stirring can make and fully contact between the reactant, makes the reaction more abundant quick.
In some embodiments, the stirring speed during the reaction is 300 to 600r/min, preferably 400 to 500 r/min.
In some embodiments, the inert gas may be selected from nitrogen, neon, argon, etc., preferably, the inert gas is nitrogen.
According to some embodiments, the reaction system further comprises a solvent, and the reactants and the reaction product can be dissolved in the solvent by adding the solvent into the reaction system, so that phase flow between the reactants is facilitated, a good mass transfer effect is achieved in the reaction process, and the reaction effect is better. Meanwhile, after the reaction is finished, the solvent can also extract the product. The solvent may be added to the reaction system together with the reactants or may be gradually added to the reaction system during the reaction. In some embodiments, the solvent is n-hexane. In some embodiments, the solvent is added in an amount of 1 to 2 times the mass of the raw glyceride.
According to some embodiments, the catalyzed reaction is followed by removal of the soap from the organic phase by adsorption on silica gel and concentration. For example, after the catalytic reaction, the reaction mixture may be filtered and then adsorbed on silica gel to remove the soap from the organic phase.
Some embodiments of the present invention provide a method for preparing tripalmitin, comprising: and carrying out catalytic reaction on the glyceride containing palmitic acid residues and palmitate under the action of lipase to obtain tripalmitin. Wherein the raw material is triglyceride.
In some embodiments, trisaturated fatty acid glycerides may also be used to synthesize USU-type triglycerides, such as 1, 3-dioleate-2-palmitate triglyceride (OPO).
The features and properties of the present invention are described in further detail below with reference to examples.
Example 1
The potassium palmitate was weighed based on the amount of palmitic acid residues in the palm oil stearin so that the ratio of palmitic acid residues to the total fatty acid residues in the reaction system was 90%, 1000g of palm oil stearin and 1000ml of n-hexane were placed in a four-necked flask, heated in a water bath until dissolved, and then mixed with the potassium palmitate. After nitrogen is introduced, under the conditions that the temperature of a water bath is 35 ℃ and the rotating speed is 400r/min, stirring is carried out until the mixture is uniform, 1g of non-directional Lipase DF Amano 15 is added, and the mixture is stirred and reacted for 4.5 hours under the condition of heat preservation. Centrifuging to obtain organic phase supernatant, adsorbing with silica gel to remove soap, and concentrating to obtain light yellow solid with tripalmitin content of 81.5% and palmitic acid content of 89.5% at sn-2 position.
Example 2
The potassium palmitate was weighed based on the amount of palmitic acid residues in the palm oil stearin so that the ratio of palmitic acid residues to the total fatty acid residues in the reaction system was 92%, 1000g of palm oil stearin and 1200ml of n-hexane were placed in a four-necked flask, heated in a water bath until dissolved, and then mixed with the potassium palmitate. After nitrogen is introduced, stirring is carried out until the water bath temperature is 38 ℃ and the rotating speed is 350r/min, 10g of non-directional lipase Lipase AY30G is added, and the reaction is carried out for 1 hour under the conditions of heat preservation and stirring. Centrifuging to obtain organic phase supernatant, adsorbing with silica gel to remove soap, and concentrating to obtain light yellow solid with tripalmitin content of 81.8% and palmitic acid content of 90.6% at sn-2 position.
Example 3
Sodium palmitate was weighed based on the amount of palmitic acid residues in palm oil stearin so that the ratio of palmitic acid residues to total fatty acid residues in the reaction system was 94%, 1000g of palm oil stearin and 1500ml of n-hexane were placed in a four-necked flask, heated in a water bath until dissolved, and then mixed with sodium palmitate. After nitrogen is introduced, under the conditions that the water bath temperature is 80 ℃ and the rotating speed is 500r/min, stirring is carried out until the mixture is uniform, 50g of non-directional lipase Novozym 435 is added, and the reaction is carried out for 1.5 hours under the condition of heat preservation and stirring. Centrifuging to obtain organic phase supernatant, adsorbing with silica gel to remove soap, and concentrating to obtain light yellow solid with tripalmitin content of 82.1% and palmitic acid content of 92.3% at sn-2 position.
Example 4
Sodium palmitate was weighed based on the amount of palmitic acid residues in palm oil stearin so that the ratio of palmitic acid residues to total fatty acid residues in the reaction system was 94%, 1000g of palm oil stearin and 1500ml of n-hexane were placed in a four-necked flask, heated in a water bath until dissolved, and then mixed with sodium palmitate. After nitrogen is introduced, under the conditions that the water bath temperature is 65 ℃ and the rotating speed is 400r/min, stirring is carried out until the mixture is uniform, 40g of non-directional lipase lipozyme TLIM is added, and the mixture is stirred and reacted for 2 hours under the condition of heat preservation. Centrifuging to obtain organic phase supernatant, adsorbing with silica gel to remove soap, and concentrating to obtain light yellow solid with tripalmitin content of 84.6% and sn-2 upper palmitic acid content of 93.5%.
Example 5
Potassium palmitate was weighed based on the amount of palmitic acid residues in the palm oil stearin so that the ratio of palmitic acid residues to the total fatty acid residues in the reaction system was 96%, 1000g of palm oil stearin and 2000ml of n-hexane were placed in a four-necked flask, heated in a water bath until dissolved, and then mixed with the potassium palmitate. After nitrogen is introduced, under the conditions that the temperature of the water bath is 40 ℃ and the rotating speed is 380r/min, stirring is carried out until the mixture is uniform, 10g of non-directional Lipase DF Amano 15 is added, and the mixture is stirred and reacted for 2 hours under the condition of heat preservation. Centrifuging to obtain organic phase supernatant, adsorbing with silica gel to remove soap, and concentrating to obtain light yellow solid with tripalmitin content of 85.7% and sn-2 upper palmitic acid content of 94.8%.
Example 6
Potassium laurate was weighed based on the amount of lauric acid residues in palm kernel oil so that the ratio of lauric acid residues to total fatty acid residues in the reaction system was 90%, 1000g of palm kernel oil and 1000ml of n-hexane were placed in a four-necked flask, heated in a water bath until dissolved, and then mixed with potassium laurate. After nitrogen is introduced, under the conditions that the temperature of a water bath is 85 ℃ and the rotating speed is 400r/min, stirring is carried out until the mixture is uniform, 80g of non-directional lipase Novozym 435 is added, and the reaction is carried out for 0.5 hour under the condition of heat preservation and stirring. Centrifuging to obtain supernatant of organic phase, adsorbing with silica gel to remove soap, and concentrating to obtain solid with trilaurin content of 80.5% and lauric acid content of 89.4% at sn-2 position.
Example 7
Weighing potassium laurate according to the amount of lauric acid residues in palm kernel oil so that the ratio of lauric acid residues to total fatty acid residues in the reaction system is 92%, placing 1000g of palm kernel oil and 1200ml of n-hexane in a four-necked flask, heating in a water bath until dissolved, and mixing with potassium laurate. After nitrogen is introduced, under the conditions that the temperature of a water bath is 35 ℃ and the rotating speed is 300r/min, stirring is carried out until the mixture is uniform, 10g of non-directional Lipase DF Amano 15 is added, and the mixture is stirred and reacted for 2 hours under the condition of heat preservation. Centrifuging to obtain supernatant of organic phase, adsorbing with silica gel to remove soap, and concentrating to obtain solid with trilaurin content of 82.4% and lauric acid content of 91.3% in sn-2 position.
Example 8
Sodium laurate was weighed based on the amount of lauric acid residues in palm kernel oil so that the ratio of lauric acid residues to the total fatty acid residues in the reaction system was 97%, 1000g of palm kernel oil and 2000ml of n-hexane were placed in a four-necked flask, heated in a water bath until dissolved, and then mixed with sodium laurate. After nitrogen is introduced, under the conditions that the temperature of the water bath is 40 ℃ and the rotating speed is 350r/min, stirring is carried out until the mixture is uniform, 1g of non-directional Lipase DF Amano 15 is added, and the mixture is stirred and reacted for 5 hours under the condition of heat preservation. Centrifuging to obtain supernatant of organic phase, adsorbing with silica gel to remove soap, and concentrating to obtain solid with trilaurin content of 86.1% and lauric acid content of sn-2 position of 95.4%.
Example 9
Potassium stearate was weighed based on the amount of stearic acid residues in cacao butter so that the proportion of stearic acid residues in the reaction system to the total fatty acid residues was 93%, 1000g of cacao butter and 1500ml of n-hexane were placed in a four-necked flask, heated in a water bath until dissolved, and then mixed with potassium stearate. After nitrogen is introduced, under the conditions that the water bath temperature is 40 ℃ and the rotating speed is 400r/min, stirring is carried out until the mixture is uniform, 5g of non-directional Lipase DF Amano 15 is added, and the mixture is stirred and reacted for 2 hours under the condition of heat preservation. Centrifuging to obtain organic phase supernatant, adsorbing with silica gel to remove soap, and concentrating to obtain solid with tristearin content of 82.3% and sn-2 stearic acid content of 91.6%.
Example 10
Potassium stearate was weighed based on the amount of stearic acid residues in cacao butter so that the proportion of stearic acid residues in the reaction system to the total fatty acid residues was 93%, 1000g of cacao butter and 1500ml of n-hexane were placed in a four-necked flask, heated in a water bath until dissolved, and then mixed with potassium stearate. After nitrogen is introduced, under the conditions that the water bath temperature is 75 ℃ and the rotating speed is 440r/min, 60g of non-directional lipase Novozym 435 is added after stirring to be uniform, and the reaction is carried out for 1 hour under the condition of heat preservation and stirring. Centrifuging to obtain organic phase supernatant, adsorbing with silica gel to remove soap, and concentrating to obtain solid with tristearin content of 87.3% and sn-2 stearic acid content of 91.3%.
Example 11
The potassium palmitate was weighed based on the amount of palmitic acid residues in the palm oil stearin so that the ratio of palmitic acid residues to the total fatty acid residues in the reaction system was 85%, 1000g of palm oil stearin and 2000ml of n-hexane were placed in a four-necked flask, heated in a water bath until dissolved, and then mixed with the potassium palmitate. After nitrogen is introduced, under the conditions that the temperature of the water bath is 40 ℃ and the rotating speed is 380r/min, stirring is carried out until the mixture is uniform, 10g of non-directional Lipase DF Amano 15 is added, and the mixture is stirred and reacted for 1.5 hours under the condition of heat preservation. Centrifuging to obtain organic phase supernatant, adsorbing with silica gel to remove soap, and concentrating to obtain light yellow solid with tripalmitin content of 65.5% and palmitic acid content of 81.4% on sn-2 position.
Example 12
Potassium palmitate was weighed based on the amount of palmitic acid residues in palm oil stearin such that the ratio of palmitic acid residues to the total fatty acid residues in the reaction system was 94%, 1000g of palm oil stearin was placed in a four-necked flask, heated in a water bath until dissolved, and then mixed with potassium palmitate. After nitrogen is introduced, stirring is carried out until the water bath temperature is 85 ℃ and the rotating speed is 500r/min, 50g of non-directional lipase Novozym 435 is added, and the reaction is carried out for 1 hour under the condition of heat preservation and stirring. Extracting with 1500ml n-hexane, centrifuging to obtain organic phase supernatant, adsorbing with silica gel to remove soap, and concentrating to obtain light yellow solid with tripalmitin content of 73.3% and palmitic acid content of 88.2% in sn-2 position.
Example 13
Potassium palmitate was weighed based on the amount of palmitic acid residues in the palm oil stearin so that the ratio of palmitic acid residues to the total fatty acid residues in the reaction system was 96%, 1000g of palm oil stearin and 2000ml of n-hexane were placed in a four-necked flask, heated in a water bath until dissolved, and then mixed with the potassium palmitate. After nitrogen is introduced, 60g of immobilized 1, 3-bit specific lipase RMIM is added after stirring to be uniform under the conditions that the water bath temperature is 65 ℃ and the rotating speed is 380r/min, and the mixture is stirred and reacted for 2 hours under the heat preservation condition. Centrifuging to obtain organic phase supernatant, adsorbing with silica gel to remove soap, and concentrating to obtain light yellow solid with tripalmitin content of 67.8% and palmitic acid content of 74.6% at sn-2 position.
Example 14
This example differs from example 5 only in that 0.5g of the non-directional Lipase DF "Amano" 15 was added. The content of tripalmitin in the product obtained by the reaction is 75.4%, and the content of palmitic acid on the sn-2 position is 85.3%.
Example 15
This example differs from example 5 only in that 100g of the non-directional Lipase DF "Amano" 15 was added. The content of tripalmitin in the product obtained by the reaction is 85.2%, and the content of palmitic acid on the sn-2 position is 94.8%.
Example 16
This example differs from example 5 only in that the temperature of the water bath for the catalytic reaction was 30 ℃. The content of tripalmitin in the product obtained by the reaction is 65.3%, and the content of palmitic acid on the sn-2 position is 80.2%.
Example 17
This example differs from example 5 only in that the temperature of the water bath for the catalytic reaction was 90 ℃. The content of tripalmitin in the product obtained by the reaction is 42.8%, and the content of palmitic acid on the sn-2 position is 60.8%.
Comparative example 1
30kg of palm oil stearin was weighed into a 100L pilot reactor, 5kg of sodium palmitate was added, nitrogen gas was introduced, and the mixture was heated with stirring. Then, the reaction temperature is stabilized at 180 ℃, the rotating speed is 300r/min, and the reaction lasts for 12 hours. Cooling to 50 deg.C, adding n-hexane to dissolve solid, centrifuging to obtain organic phase supernatant, adsorbing with silica gel to remove soap, and concentrating to obtain light yellow solid with tripalmitin content of 40.7% and palmitic acid content of 63.6% at sn-2 position.
Comparative example 2
30kg of palm oil stearin was weighed into a 100L pilot reactor, 5kg of sodium palmitate was added, nitrogen gas was introduced, and the mixture was heated with stirring. Then, the reaction temperature is stabilized at 185 ℃, the rotating speed is 400r/min, and the reaction is carried out for 20 hours. Cooling to 50 deg.C, adding n-hexane to dissolve solid, and adding water to adsorb soap. Filtering, adsorbing with silica gel to remove soap in organic phase, and concentrating to obtain light yellow solid with tripalmitin content of 41.2% and palmitic acid content of 64.2% at sn-2 position.
Comparative example 3
The palmitic acid was weighed based on the amount of palmitic acid residues of the palm oil so that the ratio of the palmitic acid residues to the total fatty acid residues in the reaction system was 96%, 1000g of palm stearin and 1500ml of n-hexane were placed in a four-necked flask, heated in a water bath until dissolved, and then mixed with the palmitic acid. After nitrogen is introduced, under the conditions that the temperature of the water bath is 40 ℃ and the rotating speed is 380r/min, stirring is carried out until the mixture is uniform, 10g of non-directional Lipase DF Amano 15 is added, and the mixture is stirred and reacted for 2 hours under the condition of heat preservation. Centrifuging to obtain organic phase supernatant, adsorbing with silica gel to remove soap, and concentrating to obtain light yellow solid with tripalmitin content of 51.2% and palmitic acid content of 78% at sn-2 position.
Through the examples 1 to 10, it can be seen that the trisaturated fatty acid glyceride prepared by the embodiment of the invention has the purity of more than 80%, the reaction condition is mild, and the side reaction is less. As is clear from comparison between comparative example 5 and example 11, the amount of the saturated fatty acid salt added has a large influence on the purity of the obtained trisaturated fatty acid glyceride, and when the amount is added so that the proportion of saturated fatty acid residues in the reaction system to the total fatty acid residues is 90%, a product having a high purity can be obtained. As can be seen from comparison of example 3 and example 12, the addition of a solvent to the reaction system is advantageous in terms of the effect of catalyzing the reaction and the purity of the product. Comparing example 5 with example 13, it can be seen that the non-directional lipase has a very good catalytic effect with respect to the directional lipase in the preparation method according to the embodiment of the present invention. By comparing example 5 with examples 14 and 15, it can be seen that the lipase is not added in more amount, and the content of the tri-saturated fatty acid glyceride is higher. By comparing example 5 with examples 16 and 17, it can be seen that the catalytic reaction effect is significantly deteriorated when the temperature is too high and too low. By comparing examples 1-10 with comparative examples 1-3, it can be seen that the method of the embodiment of the present invention has mild reaction conditions, reduced side reactions and greatly improved purity compared to the method of producing trisaturated fatty acid glycerides only under the action of the lipase or the chemical catalysis of the fatty acid salts.
In conclusion, on the basis that the glyceride part has saturated fatty acid residues, a sufficient number of saturated fatty acid residues are provided through corresponding saturated fatty acid salts, and the catalytic action of the non-directional lipase is utilized, so that the reaction conditions are mild, side reactions are few, and the purity of the generated trisaturated fatty acid glyceride is high.
The embodiments described above are some, but not all embodiments of the invention. The detailed description of the embodiments of the present invention is not intended to limit the scope of the invention as claimed, but is merely representative of selected embodiments of the invention. 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.
Claims (13)
1. A preparation method of tri-saturated fatty glyceride is characterized by comprising the following steps:
carrying out catalytic reaction on glyceride containing saturated fatty acid residue and saturated fatty acid salt under the action of lipase to obtain the trisaturated fatty acid glyceride; wherein the saturated fatty acid residue is the same as the corresponding saturated fatty acid in the saturated fatty acid salt, and the glyceride containing the saturated fatty acid residue has at least one ester bond or hydroxyl group which is not bonded to the saturated fatty acid residue, and the proportion of the saturated fatty acid residue in the reaction system of the glyceride and the saturated fatty acid salt to the total fatty acid residue is 90% or more; the lipase is non-directional lipase, and the addition amount of the lipase is 0.05-10% of that of the glyceride; the temperature of the catalytic reaction is 35-85 ℃, and the time of the catalytic reaction is 1-4 hours; the saturated fatty acid salt is saturated fatty acid sodium or saturated fatty acid potassium.
2. The method for producing triglycerides of saturated fatty acids according to claim 1, wherein the ratio of saturated fatty acid residues in the reaction system of the glycerides with the saturated fatty acid salts to the total fatty acid residues is more than 92%.
3. The method for producing triglycerides of saturated fatty acids according to claim 1, wherein the ratio of saturated fatty acid residues in the reaction system of the glycerides with the saturated fatty acid salts to the total fatty acid residues is more than 95%.
4. The method for producing trisaturated fatty acid glycerides according to claim 1, wherein the amount of lipase added is 0.1 to 8%.
5. The method for producing trisaturated fatty acid glycerides according to claim 1, wherein said non-directional Lipase comprises at least one of Novozym 435, Lipase DF "Amano" 15, LipozymeTLIM, and Lipase AY 30G.
6. The method for producing triglycerides of claim 1, wherein the glycerides comprise at least one of mono-, di-and tri-glycerides.
7. The method for producing trisaturated fatty acid glycerides according to claim 1, wherein the saturated fatty acid residue and the corresponding saturated fatty acid in the saturated fatty acid salt are selected from palmitic acid, stearic acid, caprylic acid, capric acid, lauric acid, myristic acid, and arachidic acid.
8. The method for producing trisaturated fatty acid glycerides according to claim 1, wherein the saturated fatty acid residue and the corresponding saturated fatty acid in the saturated fatty acid salt are selected from palmitic acid or stearic acid.
9. The method for producing trisaturated fatty acid glycerides according to claim 1, wherein the saturated fatty acid residue and the corresponding saturated fatty acid in the saturated fatty acid salt is palmitic acid.
10. The method according to claim 1, wherein the catalytic reaction comprises mixing the glyceride containing saturated fatty acid residues with the saturated fatty acid salt, adding the lipase, and reacting with stirring under an inert gas atmosphere.
11. The method for producing trisaturated fatty acid glycerides according to claim 1, wherein the reaction system further comprises a solvent.
12. The method for producing trisaturated fatty acid glycerides according to claim 11, wherein the solvent is n-hexane.
13. The method for producing trisaturated fatty acid glycerides according to claim 1, wherein after the catalytic reaction, the soap in the organic phase is removed by silica gel adsorption and then concentrated.
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