CN111733193B - Production method of phospholipid with good water solubility and high temperature resistance - Google Patents
Production method of phospholipid with good water solubility and high temperature resistance Download PDFInfo
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- 150000003904 phospholipids Chemical class 0.000 title claims abstract description 105
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 37
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 51
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 34
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000000203 mixture Substances 0.000 claims abstract description 26
- 238000003756 stirring Methods 0.000 claims abstract description 17
- 239000004310 lactic acid Substances 0.000 claims abstract description 15
- 235000014655 lactic acid Nutrition 0.000 claims abstract description 15
- 102100037611 Lysophospholipase Human genes 0.000 claims abstract description 14
- 108010058864 Phospholipases A2 Proteins 0.000 claims abstract description 14
- ZIIUUSVHCHPIQD-UHFFFAOYSA-N 2,4,6-trimethyl-N-[3-(trifluoromethyl)phenyl]benzenesulfonamide Chemical compound CC1=CC(C)=CC(C)=C1S(=O)(=O)NC1=CC=CC(C(F)(F)F)=C1 ZIIUUSVHCHPIQD-UHFFFAOYSA-N 0.000 claims abstract description 13
- 102000015439 Phospholipases Human genes 0.000 claims abstract description 13
- 108010064785 Phospholipases Proteins 0.000 claims abstract description 13
- 238000010438 heat treatment Methods 0.000 claims abstract description 8
- 239000000243 solution Substances 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 13
- 230000018044 dehydration Effects 0.000 claims description 5
- 238000006297 dehydration reaction Methods 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 abstract description 22
- 230000033444 hydroxylation Effects 0.000 abstract description 6
- 238000005805 hydroxylation reaction Methods 0.000 abstract description 6
- 230000004048 modification Effects 0.000 abstract description 5
- 238000012986 modification Methods 0.000 abstract description 5
- 239000003054 catalyst Substances 0.000 abstract description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 3
- 238000006386 neutralization reaction Methods 0.000 abstract description 3
- 230000000052 comparative effect Effects 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 229910052740 iodine Inorganic materials 0.000 description 9
- 239000011630 iodine Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- 238000012545 processing Methods 0.000 description 5
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 102000011420 Phospholipase D Human genes 0.000 description 2
- 108090000553 Phospholipase D Proteins 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 230000007071 enzymatic hydrolysis Effects 0.000 description 2
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 230000000640 hydroxylating effect Effects 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 239000012263 liquid product Substances 0.000 description 2
- 229940042880 natural phospholipid Drugs 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000004904 shortening Methods 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- 150000003626 triacylglycerols Chemical class 0.000 description 2
- JLPULHDHAOZNQI-ZTIMHPMXSA-N 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC JLPULHDHAOZNQI-ZTIMHPMXSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 239000008347 soybean phospholipid Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P9/00—Preparation of organic compounds containing a metal or atom other than H, N, C, O, S or halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/10—Phosphatides, e.g. lecithin
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
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Abstract
The invention discloses a production method of phospholipid with good water solubility and high temperature resistance, which comprises the following steps: s1, heating crude phospholipid; s2, mixing the lactic acid solution with the mixture, controlling the temperature and stirring the mixture; s3, mixing with hydrogen peroxide in a certain time, heating and stirring; s4, mixing with sodium hydroxide water solution in a certain time, controlling the temperature and stirring; s5, adjusting the temperature, adding phospholipase, and reacting for a period of time; and S6, vacuumizing and dehydrating to obtain the modified phospholipid. The production method of the phospholipid with good water solubility and high temperature resistance firstly hydroxylates and then carries out enzymolysis to modify the phospholipid so as to obtain the modified phospholipid with good water solubility and high temperature resistance. In hydroxylation of phospholipid, lactic acid is used as a catalyst to catalyze the reaction of phospholipid and hydrogen peroxide, and sodium hydroxide is used for neutralization reaction. In the enzymolysis, phospholipase A2 is added to carry out enzymolysis on the hydroxyl modified phospholipid for further modification, and the finally obtained modified phospholipid has excellent water solubility and high temperature resistance.
Description
Technical Field
The invention belongs to the technical field of phospholipid processing, and relates to a production method of phospholipid with good water solubility and high temperature resistance.
Background
Phospholipids (phospholipids), also known as phospholipids or phospholipids, are lipids containing phosphoric acid and belong to complex lipids. Phospholipids are amphiphilic molecules with a hydrophilic nitrogen or phosphorus containing head at one end and a long hydrophobic (lipophilic) hydrocarbyl chain at the other end. Phospholipids are widely used in the feed industry, food industry, pharmaceutical and health products, cosmetics industry, textile industry, leather industry.
Natural phospholipid is easy to darken at high temperature, cannot resist high temperature and is generally insoluble in water. This severely limits the use of phospholipids in aqueous, high temperature processing processes. Modification of natural phospholipids is an important direction of research in phospholipid processing.
Disclosure of Invention
Aiming at the problems, the invention provides a production method of phospholipid with good water solubility and high temperature resistance, which comprises the steps of hydroxylating crude phospholipid and then carrying out enzymolysis, wherein the obtained phospholipid can be well dissolved in water, and the color value is not changed at high temperature. So that the modified phospholipid can be widely applied to aqueous solution and high-temperature processing technology.
The invention discloses a production method of phospholipid with good water solubility and high temperature resistance, which comprises the following steps:
s1, heating crude phospholipid;
s2, mixing the lactic acid solution with the mixture, controlling the temperature and stirring the mixture;
s3, mixing with hydrogen peroxide in a certain time, heating and stirring;
s4, mixing with sodium hydroxide water solution in a certain time, controlling the temperature and stirring;
s5, adjusting the temperature, adding phospholipase A2, and reacting for a period of time;
and S6, vacuumizing and dehydrating to obtain the modified phospholipid.
The production method of the phospholipid with good water solubility and high temperature resistance adopts a method of firstly hydroxylating and then carrying out enzymolysis to modify the phospholipid so as to obtain the modified phospholipid with good water solubility and high temperature resistance. In hydroxylation of phospholipid, lactic acid is used as a catalyst to catalyze the reaction of phospholipid and hydrogen peroxide, and sodium hydroxide is used for neutralization reaction. In the enzymolysis, phospholipase A2 is added to carry out enzymolysis on the hydroxyl modified phospholipid for further modification, and the finally obtained modified phospholipid has excellent water solubility and high temperature resistance.
In some embodiments of the invention, the temperature is raised to 50-60 ℃ in step S1.
In some embodiments of the present invention, in the step of S2, the temperature is controlled to be 50 to 60 ℃, and the stirring is performed for 1.5 to 2.5 hours.
In some embodiments of the present invention, in the S2 step, the lactic acid is 3-4% by weight of the crude phospholipid, and the lactic acid solution has a concentration of 30% by weight.
In some embodiments of the invention, in the step S3, the mixture is mixed with hydrogen peroxide for more than 30min, the temperature is raised to 68-72 ℃, and the mixture is stirred for 3.5-4.5 h.
In some embodiments of the present invention, in the step S3, the hydrogen peroxide is 8-10% by weight of the crude phospholipid, and the concentration of the hydrogen peroxide is 35% by weight.
In some embodiments of the present invention, in the step of S4, the mixture is mixed with the aqueous solution of sodium hydroxide for more than 30min, the temperature is controlled between 68 ℃ and 72 ℃, and the mixture is stirred for 4.5 to 5.5 h.
In some embodiments of the present invention, in the step of S4, the sodium hydroxide is 3-5% by weight of the crude phospholipid, and the sodium hydroxide solution has a concentration of 32% by weight.
In some embodiments of the present invention, in the step of S5, the temperature is adjusted to 56-60 ℃, phospholipase A2 is added, and the mixture is stirred and reacted for 9-11 h.
In some embodiments of the present invention, in the S5 step, the phospholipase is added in an amount of 0.02 to 0.04% by weight based on the crude phospholipid.
In some embodiments of the present invention, in the step of S6, the temperature during the vacuum dehydration is less than 80 ℃ and the dehydration is carried out until the moisture is less than or equal to 1.5%.
In some embodiments of the present invention, before the step of S5, a step of adding EDTA-Ca and modified phospholipids is further included.
Phospholipase A2 is a key factor in enzymatic hydrolysis. Ca2+And Mg2+The enzyme activity of phospholipase A2 can be improved, and EDTA can reduce the enzyme activity of phospholipase A2. When EDTA-Ca and modified phospholipid are added into the enzymolysis step, the surprising discovery shows that the enzymolysis time can be greatly shortened. Meanwhile, the effect is greatly improved by the treatment of the EDTA-Ca and the modified phospholipid, and the synergistic effect is realized.
In some preferred embodiments of the present invention, the concentration of EDTA-Ca added to the system is 0.5 to 5 mmol/L.
In some preferred embodiments of the present invention, the modified phospholipid is added in an amount of 0.1 to 1% by weight based on the crude phospholipid.
When the concentration of EDTA-Ca in the system is 0.5-5mmol/L, the added modified phospholipid is 0.1-1% of the crude phospholipid by weight, the effect of EDTA-Ca and the modified phospholipid for shortening the enzymolysis time is obvious, and when the concentration of EDTA-Ca in the system is less than 0.1mmol/L or the added modified phospholipid is less than 0.05% of the crude phospholipid, the effect of shortening the enzymolysis time is not obvious.
In some preferred embodiments of the present invention, in step S5, the portion of the phospholipase may be controlled by the reaction rate, which comprises the following steps:
step a1, the reaction rate is determined according to the following equation:
wherein R represents the heating rate, T represents the reaction temperature, the molecular diameter of the phospholipase d, M represents the rate constant, and V represents the reaction rate obtained by solving;
and A2, according to the reaction rate V obtained in the step A1, reducing the amount of the phospholipase when the reaction rate V is greater than a preset threshold, and increasing the amount of the phospholipase when the reaction rate V is less than the preset threshold.
The beneficial technical effects of the invention are as follows:
the production method of the phospholipid with good water solubility and high temperature resistance firstly hydroxylates and then carries out enzymolysis to modify the phospholipid so as to obtain the modified phospholipid with good water solubility and high temperature resistance. In hydroxylation of phospholipid, lactic acid is used as a catalyst to catalyze the reaction of phospholipid and hydrogen peroxide, and sodium hydroxide is used for neutralization reaction. In the enzymolysis, phospholipase A2 is added to carry out enzymolysis on the hydroxyl modified phospholipid for further modification, and the finally obtained modified phospholipid has excellent water solubility and high temperature resistance.
According to the production method of the phospholipid with good water solubility and high temperature resistance, EDTA-Ca and the modified phospholipid are added, so that the enzymolysis time can be obviously shortened.
Detailed Description
The embodiments of the present invention are described below with reference to specific embodiments, and other advantages and effects of the present invention will be easily understood by those skilled in the art from the disclosure of the present specification. The invention is capable of other and different embodiments and of being practiced or of being carried out in various ways, and its several details are capable of modification in various respects, all without departing from the spirit and scope of the present invention.
The following examples and comparative examples are parallel runs, with the same processing steps and parameters, unless otherwise indicated. The weight percentage concentration of the lactic acid solution is 30%, the weight percentage concentration of the hydrogen peroxide is 35%, and the weight percentage concentration of the sodium hydroxide solution is 32%. The crude phospholipid is oil residue separated in the soybean oil refining process or edible soybean phospholipid, and is obtained by dehydration, decolorization and impurity removal steps, wherein the content of acetone insoluble phospholipid is about 60% by weight, and the content of triglyceride and free fatty acid is about 40% by weight. The product obtained was a viscous liquid product except that in example 5, the product was defatted to a solid powder with acetone. The enzyme activity of the phospholipase A2 is 12000U/ml.
Example 1
A production method of phospholipid with good water solubility and high temperature resistance comprises the following steps:
1. the crude phospholipid (AI64.2, iodine number 96) was pumped in 4T and the temperature was raised to 50 ℃.
2. 128kg of prepared 30% lactic acid solution (3.2% of the weight of the crude phospholipid) is added uniformly within 30min, the temperature is adjusted to 50 ℃, and the mixture is stirred for 2 h.
3. Adding 360kg (9% of crude phospholipid weight) of hydrogen peroxide uniformly in 30min or more, adjusting temperature to 70 deg.C, and stirring for 4 hr.
4. 160kg of sodium hydroxide solution (4% by weight of the crude phospholipid) was added uniformly over 30min or more, the temperature was adjusted to 70 ℃ and the mixture was stirred for 5 hours.
5. The temperature was adjusted to 56 ℃ and 1.2kg of phospholipase A2 (0.03% by weight of crude phospholipid) was added, and the reaction was stirred for 10 hours.
6. Vacuumizing and dewatering at a temperature lower than 80 deg.C until the water content is less than or equal to 1.5%. 4 tons of product are obtained (AI59.6, iodine number 68).
Example 2
A production method of phospholipid with good water solubility and high temperature resistance comprises the following steps:
1. the crude phospholipid (AI64.2, iodine number 96) was pumped in 4T and the temperature was raised to 60 ℃.
2. 128kg of prepared 30% lactic acid solution (3.2% of the weight of the crude phospholipid) is added uniformly within 30min, the temperature is adjusted to 60 ℃, and the mixture is stirred for 2 h.
3. Adding 360kg (9% of crude phospholipid weight) of hydrogen peroxide uniformly in 30min or more, adjusting temperature to 70 deg.C, and stirring for 4 hr.
4. 160kg of sodium hydroxide solution (4% by weight of the crude phospholipid) was added uniformly over 30min or more, the temperature was adjusted to 70 ℃ and the mixture was stirred for 5 hours.
5. The temperature was adjusted to 60 ℃ and 1.2kg of phospholipase A2 (0.03% by weight of crude phospholipid) was added, and the reaction was stirred for 10 hours.
6. Vacuumizing and dewatering at a temperature lower than 80 deg.C until the water content is less than or equal to 1.5%. 4 tons of product (AI58.6, iodine number 63) are obtained.
Example 3
A production method of phospholipid with good water solubility and high temperature resistance comprises the following steps:
1. the crude phospholipid (AI64.2, iodine number 96) was pumped in 4T and the temperature was raised to 60 ℃.
2. 128kg of prepared 30% lactic acid solution (3.2% of the weight of the crude phospholipid) is added uniformly within 30min, the temperature is adjusted to 60 ℃, and the mixture is stirred for 2 h.
3. Adding 360kg (9% of crude phospholipid weight) of hydrogen peroxide uniformly in 30min or more, adjusting temperature to 70 deg.C, and stirring for 4 hr.
4. 160kg of sodium hydroxide solution (4% by weight of the crude phospholipid) was added uniformly over 30min or more, the temperature was adjusted to 70 ℃ and the mixture was stirred for 5 hours.
5. The temperature was adjusted to 60 ℃ and 20kg of the modified phospholipid obtained in example 1 was added, EDTA-Ca was added so that the concentration in the reaction system became 1mmol/L, 1.2kg of phospholipase A2 (0.03% by weight based on the crude phospholipid) was added, and the mixture was stirred and reacted for 5 hours.
6. Vacuumizing and dewatering at a temperature lower than 80 deg.C until the water content is less than or equal to 1.5%. 4 tons of product (AI57.5, iodine number 65) are obtained.
Example 4
A method for producing high-temperature resistant phospholipid with good water solubility controls the weight of phospholipase through reaction rate, and comprises the following steps:
step a1, the reaction rate is determined according to the following equation:
wherein R represents the heating rate, T represents the reaction temperature, the molecular diameter of the phospholipase d, M represents the rate constant, and V represents the reaction rate obtained by solving;
and A2, according to the reaction rate V obtained in the step A1, reducing the amount of the phospholipase when the reaction rate V is greater than a preset threshold, and increasing the amount of the phospholipase when the reaction rate V is less than the preset threshold.
By the method, the usage amount of the phospholipase is controlled at a certain reaction speed, so that the effect of the phospholipase can be exerted to the maximum extent, the product is improved, the usage amount of the phospholipase is reduced, and the cost is reduced.
Example 5
A production method of phospholipid with good water solubility and high temperature resistance comprises the following steps:
1. the crude phospholipid (AI64.2, iodine number 96) was pumped in 4T and the temperature was raised to 50 ℃.
2. 128kg of prepared 30% lactic acid solution (3.2% of the weight of the crude phospholipid) is added uniformly within 30min, the temperature is adjusted to 50 ℃, and the mixture is stirred for 2 h.
3. Adding 360kg (9% of crude phospholipid weight) of hydrogen peroxide uniformly in 30min or more, adjusting temperature to 70 deg.C, and stirring for 4 hr.
4. 160kg of sodium hydroxide solution (4% by weight of the crude phospholipid) was added uniformly over 30min or more, the temperature was adjusted to 70 ℃ and the mixture was stirred for 5 hours.
5. The temperature was adjusted to 56 ℃ and 1.2kg of phospholipase A2 (0.03% by weight of crude phospholipid) was added, and the reaction was stirred for 10 hours.
6. Vacuumizing and dewatering at a temperature lower than 80 deg.C until the water content is less than or equal to 1.5%. 4 tons of product are obtained (AI59.6, iodine number 68).
7. Acetone degreasing:
taking 600kg of the liquid product, adding 2400L of acetone with the purity of more than 99.5%, and stirring for 30 min;
b, standing and layering, extracting 1000L of upper-layer oil-containing mother liquor, adding 1000L of acetone with the purity of more than 99.5%, and stirring for 30 minutes;
c, repeating B5 times;
and D, performing centrifugal separation to obtain 600kg of filter cake, performing vacuum drying, crushing, and sieving by a 40-mesh sieve to obtain 320kg of powdery phospholipid (AI97.6, water content of 1.2, PV 2.3).
Before defatting, phospholipids accounted for 60% by weight, triglycerides and fatty acids accounted for 40%. After defatting, the content of triglycerides and fatty acids was reduced from 40% to 1.2%. The degreased phospholipid has stronger high-temperature resistance.
Comparative example 1
The difference from example 1 is that there is only an enzymatic step and no hydroxylation step, i.e. steps 1, 5, 6 are included, not steps 2-4.
Comparative example 2
The difference from example 1 is that only the hydroxylation step and no enzymatic hydrolysis step, i.e. steps 1, 2, 3, 4, 6, are included, not step 5.
Comparative example 3
The difference from example 3 was that 20kg of the modified phospholipid obtained in example 1 was added without adding EDTA-Ca.
Comparative example 4
The difference from example 3 was that EDTA-Ca alone was added without adding the modified phospholipid obtained in example 1 so that the concentration in the reaction system was 1 mmol/L.
Examples of the experiments
1 high temperature resistance comparative experiment
The modified phospholipids obtained in the comparative example and example were stored at 115 ℃ and the color value was measured, plus the specific value. The peroxide number was determined by the method of GB 28401-2012. The results are shown in Table 1.
TABLE 1 high temperature resistance
As can be seen from Table 1, the peroxide numbers of examples 1, 2, 3, 5 increased gradually with time at 115 ℃ with much less magnitude and rate than comparative examples 1 and 2. The colour values of examples 1, 2, 3, 5 remained unchanged over 30h, whereas comparative examples 1 and 2 increased significantly. Shows the synergistic effect of the enzymolysis step and the hydroxylation step on the high-temperature resistance.
2 comparative Water solubility test
Water solubility is characterized by two parameters, solubility and HLB. In the solubility test, 6g of each of the modified phospholipids obtained in comparative example and example was added to 100ml of water at room temperature, and the mixture was stirred. HLB values were determined by the emulsification method. The results are shown in Table 2.
TABLE 2 Water solubility
| Solubility in water | HLB | |
| Example 1 | Completely dissolve | 12 |
| Example 2 | Completely dissolve | 13 |
| Example 3 | Completely dissolve | 13 |
| Example 5 | Completely dissolve | 15 |
| Comparative example 1 | With residues | 7 |
| Comparative example 2 | With residues | 9 |
3 comparative enzymolysis test
Example 3 compared with examples 1 and 2, a similar (AI and iodine value similar) modified phospholipid was obtained, and the reaction time was shortened from 10h to 5 h. In contrast, in comparative examples 3 and 4, the reaction time was not significantly shortened as compared with examples 1 and 2.
While the preferred embodiments and examples of the present invention have been described in detail, the present invention is not limited to the embodiments and examples, and various changes can be made without departing from the spirit of the present invention within the knowledge of those skilled in the art.
Claims (7)
1. A production method of phospholipid with good water solubility and high temperature resistance comprises the following steps:
s1, heating crude phospholipid;
s2, mixing the lactic acid solution with the mixture, controlling the temperature and stirring the mixture;
s3, mixing with hydrogen peroxide in a certain time, heating and stirring;
s4, mixing with sodium hydroxide water solution in a certain time, controlling the temperature and stirring;
s5, adjusting the temperature, adding phospholipase, and reacting for a period of time;
s6, vacuumizing and dehydrating to obtain modified phospholipid;
before the step of S5, the method also comprises the step of adding EDTA-Ca and modified phospholipid;
the concentration of the added EDTA-Ca in the system is 0.5-5 mmol/L;
the modified phospholipid is added in an amount of 0.1-1% by weight based on the crude phospholipid.
2. The method according to claim 1, wherein the temperature is increased to 50-60 ℃ in the step of S1.
3. The method according to claim 1 or 2, wherein in the step of S2, the temperature is controlled to be 50-60 ℃, and stirring is performed for 1.5-2.5 h;
and/or, in the step S2, the lactic acid solution is 3-4% by weight of the crude phospholipid, and the concentration of the lactic acid solution is 30% by weight.
4. The method according to any one of claims 1 to 3, wherein in the step S3, the mixture is mixed with hydrogen peroxide within more than 30min, the temperature is raised to 68-72 ℃, and the mixture is stirred for 3.5-4.5 h;
and/or in the step S3, hydrogen peroxide accounts for 8-10% of the crude phospholipid by weight, and the concentration of the hydrogen peroxide by weight is 35%.
5. The method according to any one of claims 1 to 4, wherein in the step S4, the mixture is mixed with the sodium hydroxide aqueous solution for more than 30min, the temperature is controlled between 68 ℃ and 72 ℃, and the mixture is stirred for 4.5 to 5.5 hours;
and/or, in the step S4, the weight percentage of the sodium hydroxide is 3-5% of that of the crude phospholipid, and the weight percentage of the sodium hydroxide solution is 32%.
6. The method according to any one of claims 1 to 5, wherein in the step of S5, the temperature is adjusted to 56 to 60 ℃, phospholipase A2 is added, and the mixture is stirred and reacted for 9 to 11 hours;
and/or, in the step of S5, the phospholipase is added in an amount of 0.02-0.04% by weight based on the crude phospholipid.
7. The method according to any one of claims 1 to 6, wherein in the step S6, the temperature during vacuum dehydration is less than 80 ℃ and the dehydration is carried out until the moisture is less than or equal to 1.5%.
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| CN104054895A (en) * | 2014-06-20 | 2014-09-24 | 天津鹤喜园磷脂科技有限公司 | Method for producing water-soluble modified phospholipid and formula thereof |
| CN105087696A (en) * | 2015-10-13 | 2015-11-25 | 李桂华 | Preparation method suitable for industrialized continuous production of enzyme modified soybean phospholipids |
| CN105622665A (en) * | 2016-03-16 | 2016-06-01 | 北京美亚斯磷脂技术有限公司 | Preparation method of modified soybean phospholipids |
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| CN1632127A (en) * | 2003-12-25 | 2005-06-29 | 黑龙江省大豆技术开发研究中心 | Method for producing enzyme modified soybean lecithin |
| CN104054895A (en) * | 2014-06-20 | 2014-09-24 | 天津鹤喜园磷脂科技有限公司 | Method for producing water-soluble modified phospholipid and formula thereof |
| CN105087696A (en) * | 2015-10-13 | 2015-11-25 | 李桂华 | Preparation method suitable for industrialized continuous production of enzyme modified soybean phospholipids |
| CN105622665A (en) * | 2016-03-16 | 2016-06-01 | 北京美亚斯磷脂技术有限公司 | Preparation method of modified soybean phospholipids |
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