CN104862350B - A kind of method for preparing bis- oleic acid -2- palmitic acids of 1,3-, three ester - Google Patents
A kind of method for preparing bis- oleic acid -2- palmitic acids of 1,3-, three ester Download PDFInfo
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- CN104862350B CN104862350B CN201510227309.9A CN201510227309A CN104862350B CN 104862350 B CN104862350 B CN 104862350B CN 201510227309 A CN201510227309 A CN 201510227309A CN 104862350 B CN104862350 B CN 104862350B
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- 235000021314 Palmitic acid Nutrition 0.000 title claims abstract description 36
- 238000000034 method Methods 0.000 title claims abstract description 19
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 title claims abstract description 17
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 title claims abstract description 17
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 title claims abstract description 17
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 239000005642 Oleic acid Substances 0.000 title claims abstract description 17
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 150000002148 esters Chemical class 0.000 title abstract description 11
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims abstract description 54
- 235000019198 oils Nutrition 0.000 claims abstract description 50
- 241001233037 catfish Species 0.000 claims abstract description 48
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims abstract description 23
- 239000007787 solid Substances 0.000 claims abstract description 20
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims abstract description 17
- 239000003054 catalyst Substances 0.000 claims abstract description 7
- 239000002253 acid Substances 0.000 claims description 27
- 125000001931 aliphatic group Chemical group 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 238000000199 molecular distillation Methods 0.000 claims description 9
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 108010048733 Lipozyme Proteins 0.000 claims description 6
- 238000001704 evaporation Methods 0.000 claims description 5
- 239000000758 substrate Substances 0.000 claims description 5
- 235000019484 Rapeseed oil Nutrition 0.000 claims description 4
- 241001417930 Siluridae Species 0.000 claims description 4
- 238000002425 crystallisation Methods 0.000 claims description 2
- 230000008025 crystallization Effects 0.000 claims description 2
- 230000008020 evaporation Effects 0.000 claims 1
- 239000012535 impurity Substances 0.000 claims 1
- 239000003921 oil Substances 0.000 abstract description 44
- 239000002994 raw material Substances 0.000 abstract description 7
- 235000015112 vegetable and seed oil Nutrition 0.000 abstract description 5
- 239000008158 vegetable oil Substances 0.000 abstract description 5
- 108090001060 Lipase Proteins 0.000 abstract description 4
- 102000004882 Lipase Human genes 0.000 abstract description 4
- 239000004367 Lipase Substances 0.000 abstract description 4
- 235000019421 lipase Nutrition 0.000 abstract description 4
- 235000013336 milk Nutrition 0.000 abstract description 3
- 239000008267 milk Substances 0.000 abstract description 3
- 210000004080 milk Anatomy 0.000 abstract description 3
- 239000000654 additive Substances 0.000 abstract description 2
- 230000000996 additive effect Effects 0.000 abstract description 2
- 238000001914 filtration Methods 0.000 abstract description 2
- 239000012530 fluid Substances 0.000 abstract description 2
- 235000013350 formula milk Nutrition 0.000 abstract description 2
- 239000000843 powder Substances 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 description 14
- 238000009826 distribution Methods 0.000 description 11
- 150000003626 triacylglycerols Chemical class 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 10
- 150000002943 palmitic acids Chemical class 0.000 description 7
- 108090000790 Enzymes Proteins 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 4
- 229940088598 enzyme Drugs 0.000 description 4
- 241000894007 species Species 0.000 description 4
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 4
- 235000020256 human milk Nutrition 0.000 description 3
- 210000004251 human milk Anatomy 0.000 description 3
- 229940040461 lipase Drugs 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 235000019486 Sunflower oil Nutrition 0.000 description 2
- 230000009102 absorption Effects 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000004519 grease Substances 0.000 description 2
- FCCDDURTIIUXBY-UHFFFAOYSA-N lipoamide Chemical group NC(=O)CCCCC1CCSS1 FCCDDURTIIUXBY-UHFFFAOYSA-N 0.000 description 2
- 150000004671 saturated fatty acids Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000002600 sunflower oil Substances 0.000 description 2
- PVNIQBQSYATKKL-UHFFFAOYSA-N tripalmitin Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCC PVNIQBQSYATKKL-UHFFFAOYSA-N 0.000 description 2
- 206010067484 Adverse reaction Diseases 0.000 description 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- 206010010774 Constipation Diseases 0.000 description 1
- 102100031416 Gastric triacylglycerol lipase Human genes 0.000 description 1
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical group [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 description 1
- 108050006759 Pancreatic lipases Proteins 0.000 description 1
- 102000019280 Pancreatic lipases Human genes 0.000 description 1
- 230000006838 adverse reaction Effects 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940099352 cholate Drugs 0.000 description 1
- BHQCQFFYRZLCQQ-OELDTZBJSA-N cholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 BHQCQFFYRZLCQQ-OELDTZBJSA-N 0.000 description 1
- 210000001268 chyle Anatomy 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 108010091264 gastric triacylglycerol lipase Proteins 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 210000002490 intestinal epithelial cell Anatomy 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 229940116369 pancreatic lipase Drugs 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 125000005471 saturated fatty acid group Chemical group 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229960001947 tripalmitin Drugs 0.000 description 1
- 239000010913 used oil Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
- A23C11/00—Milk substitutes, e.g. coffee whitener compositions
- A23C11/02—Milk substitutes, e.g. coffee whitener compositions containing at least one non-milk component as source of fats or proteins
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
- A23D9/02—Other edible oils or fats, e.g. shortenings, cooking oils characterised by the production or working-up
-
- 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
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
Abstract
The invention discloses one kind to prepare 1, the method of 3 two oleic acid, 2 palmitic acid, three ester, it includes, by catfish oil in 50~60 DEG C of fusings, 30~60min is kept, and 15~30 DEG C are cooled to the rate of temperature fall of 1~5 DEG C/min, after catfish oil is kept 5~48h at this temperature, fluid oil is removed by the way of filtering, is obtained in 2 solid fat components of catfish oil rich in palmitic acid of sn；With 1,3 specific lipases of sn for catalyst, using the free fatty of high oleic acid vegetable oil source as acry radical donor, the solid fat component of catfish oil described in acidolysis, the product rich in 1,3 two oleic acid, 2 palmitic acid, three ester is obtained after removing free fatty.The present invention is raw materials used cheap, and 1,3 two oleic acid of products obtained therefrom, 2 palmitic acid, three ester content is high, can be widely used in as additive in baby formula milk powder fat.
Description
Technical field
The invention belongs to grease technical field, and in particular to a kind of acidolysis prepares sweet rich in 1,3-, bis- oleic acid -2- palmitic acids
The method of oily three ester products.
Background technology
Breast milk is the optimal food of infant, there is provided including the almost all of nutriment needed for infant, wherein fat
Fat occupies 3~5% of breast milk or so, and about more than 50% energy is but provided for infant.In these fat, triglycerides
Content is more than 98%.The content of palmitic acid is 20~30% in breast milk, and substantial amounts of saturated fatty acid (palmitic acid) is in glycerine three
The sn-2 positions of ester, and unrighted acid is in sn-1,3, therefore it is saturated fatty acid to form substantial amounts of sn-2, sn-1,3 are
The triglycerides of unrighted acid, such as 1,3-Dioleic acid-2-palmitoyl triglyceride (OPO).
After infant's intake, about 10~30% can be hydrolyzed into fat by tongue lipase and gastric lipase first
For sn-2,3 diglycerides, then become sn-2 monoglycerides and aliphatic acid, sn- by the effect hydrolysis of pancreatic lipase and cholate again
2 monoglycerides can directly be absorbed by intestinal epithelial cell, be esterified as triglycerides, be then converted to chyle milk particle and be transported to body
Each position provide energy.The absorption of aliphatic acid is with its saturation degree and chain with important relationship.Chain saturated fatty acids are easily same
Internal calcium ions and magnesium ions form dystectic soap, excrete.For infant, it can so cause the loss of energy, together
When be also possible to cause constipation or the consequences such as intestines are rotten.Therefore, palmitic acid can avoid these adverse reactions at sn-2.Correlation is ground
Study carefully and also report, carry out feeding infant by using the fat of high sn-2 palmitic acids and the fat of random distribution palmitic acid, palmitic acid exists
The excrement of the fatty baby of sn-2 is more soft.Meanwhile relevant report displays that, using OPO feeding infants, than using OPO
Isomer 1, bis- oleic acid -3- palmitic acids of 2-, three ester (OOP) feed, the transfer velocity of OPO is faster.Therefore, it is this
Triglycerides of the palmitic acid of special construction at sn-2, there is digestion, absorption and metabolism of the fat in infants
Significance.
At present, the method that some document reports prepare OPO products using tripalmitin and lard.Palm stearin
Although having palmitic acid on sn-2, it also has same amount of palmitic acid in sn-1,3, it is therefore desirable to using larger
Substrate ratio prepares OPO products.Also someone uses palm stearin as raw material, with the method for alcoholysis and resterification come be prepared compared with
The OPO of high-purity, but technics comparing is complicated, it is difficult to obtain industrialized production.Therefore, one kind is found at sn-2 with higher
Palmitic acid content, relatively low total palmitic acid content, while general grease can be obtained again, just have for exploitation OPO products
Particularly important meaning.
The content of the invention
The purpose of this part is to summarize some aspects of the embodiment of the present invention and briefly introduce some preferably to implement
Mode.It may do a little simplified or be omitted to avoid this is made in this part and the description of the present application summary and denomination of invention
Partly, the purpose of specification digest and denomination of invention obscures, and this simplification or omission cannot be used for limiting the scope of the invention.
In view of problem present in the above-mentioned and/or existing method for preparing 1,3-Dioleic acid-2-palmitoyl triglyceride, carries
The present invention is gone out.
Therefore, it is an object of the present invention to provide a kind of economically viable oil of 1,3- bis- using catfish oil as raw material
The preparation method of three ester of acid -2- palmitic acids.
In order to solve the above technical problems, according to an aspect of the present invention, the present invention provides following technical solution：It is a kind of
The method for preparing 1,3-Dioleic acid-2-palmitoyl triglyceride, it includes, and catfish oil is melted at 50~60 DEG C, and holding 30~
60min, and 15~30 DEG C are cooled to the rate of temperature fall of 1~5 DEG C/min, after catfish oil is kept 5~48h at this temperature,
Fluid oil is removed by the way of filtering, is obtained in the sn-2 solid fat components of catfish oil rich in palmitic acid；It is special with sn-1,3
Different in nature lipase is catalyst, and using the free fatty of high oleic acid vegetable oil source as acry radical donor, catfish oil is solid described in acidolysis
Fat component, the product rich in 1,3-Dioleic acid-2-palmitoyl triglyceride is obtained after removing free fatty.
As it is of the present invention preparation 1,3-Dioleic acid-2-palmitoyl triglyceride method a kind of preferred solution,
Wherein：The catalyst is Lipozyme RM IM and/or Lipozyme TL IM.
As it is of the present invention preparation 1,3-Dioleic acid-2-palmitoyl triglyceride method a kind of preferred solution,
Wherein：The high oleic acid vegetable oil is the one or more in high oleic acid rapeseed oil, high oleic sunflower oil and olive oil.
As it is of the present invention preparation 1,3-Dioleic acid-2-palmitoyl triglyceride method a kind of preferred solution,
Wherein：The acidolysis, its reaction temperature are 40 DEG C~70 DEG C.
As it is of the present invention preparation 1,3-Dioleic acid-2-palmitoyl triglyceride method a kind of preferred solution,
Wherein：The molar ratio of the catfish oil and free fatty is 1：1~10.
As it is of the present invention preparation 1,3-Dioleic acid-2-palmitoyl triglyceride method a kind of preferred solution,
Wherein：The acidolysis is intermittent reaction, its enzyme concentration is 3%~15wt%, and the reaction time is 1h~5h, and stir speed (S.S.) is
300r/min~800r/min.
As it is of the present invention preparation 1,3-Dioleic acid-2-palmitoyl triglyceride method a kind of preferred solution,
Wherein：The acidolysis is successive reaction, its substrate residence time is in 0.5h~3h.
As it is of the present invention preparation 1,3-Dioleic acid-2-palmitoyl triglyceride method a kind of preferred solution,
Wherein：The removing free fatty is centrifugation.
As it is of the present invention preparation 1,3-Dioleic acid-2-palmitoyl triglyceride method a kind of preferred solution,
Wherein：The removing free fatty is molecular distillation, its evaporating temperature is 180 DEG C~190 DEG C, and rotating speed is 110~130rpm,
Absolute pressure is 2~3Pa.
As it is of the present invention preparation 1,3-Dioleic acid-2-palmitoyl triglyceride method a kind of preferred solution,
Wherein：The removing free fatty is vacuum distillation.
Beneficial effects of the present invention：The raw materials used catfish oil of the present invention is cheap, derives from a wealth of sources, simultaneously because catfish is oily
Itself containing higher sn-2 palmitic acids and relatively low total palmitic acid content, free fatty ratio used is small in acidolysis reaction,
Thus there are larger market prospects.
Embodiment
In order to make the foregoing objectives, features and advantages of the present invention clearer and more comprehensible, below by the specific of the present invention
Embodiment is described in detail.
Many details are elaborated in the following description to facilitate a thorough understanding of the present invention, still the present invention can be with
Implemented using other different from other manner described here, those skilled in the art can be without prejudice to intension of the present invention
In the case of do similar popularization, therefore the present invention is from the limitation of following public specific embodiment.
Example 1：
Refined freshwater catfish oil is melted at 60 DEG C, and keeps 30min, then by catfish oil with the cooling speed of 5 DEG C/min
Rate is cooled at 30 DEG C, and crystallize 8 it is small when, solid fat in catfish oil is into analyzing.By catfish oil by vacuum filter, consolidate
Fat component.Point carry solid fat and contain sn-2 palmitic acids and total palmitic acid compared with catfish oil higher.Catfish used oil and its point carry solid fat
Aliphatic acid composition and be distributed as shown in the table：
1. catfish of table is oily and its divides the aliphatic acid composition for carrying solid fat and distribution
Acidolysis catfish consolidates fat component in batch reactor, is catalysis with 1,3 specific lipase Lipozyme RMIM
Agent, uses the aliphatic acid for coming from high oleic sunflower oil as acry radical donor, and the molar ratio of catfish oil and aliphatic acid is 1:6, reaction
Temperature DEG C is 50 DEG C, enzyme concentration 10wt%, and stir speed (S.S.) is 500 turns/min.After reaction, removed by centrifuging in reaction mixture
Lipase.
Gained reaction mixture is removed into free fatty by way of molecular distillation, molecular distillation condition used is：
Evaporating temperature, 185 DEG C；Heat exchanger temperature, 60 DEG C；Rotating speed, 120rpm；Absolute pressure, 2Pa.The aliphatic acid group of products obtained therefrom
Into and distribution it is as shown in the table：
The aliphatic acid composition of 2. enzymolysis product of table and distribution
| FA species | FA | sn-2FA | %sn-2FA | sn-1,3FA |
| C14:0 | 3.59 | 4.10 | 38.07 | 3.34 |
| C16:0 | 22.39 | 57.80 | 86.05 | 4.69 |
| C18:0 | 5.62 | 5.30 | 31.44 | 5.78 |
| C18:1 | 60.10 | 21.88 | 12.14 | 79.21 |
| C18:2 | 7.03 | 8.40 | 39.83 | 6.35 |
| C18:3 | 0.30 | 0.40 | 44.44 | 0.25 |
The triglycerides composition contrast of products therefrom and fish oil and its solid fat fraction leach-s/tive is as shown in table 3.
The triglycerides composition of 3. enzymolysis product of table
Example 2：
Refined freshwater catfish oil is melted at 50 DEG C, keeps 60min, then by catfish oil with the rate of temperature fall of 3 DEG C/min
It is down to 20 DEG C, when crystallization 7 is small, solid fat is into analyzing in catfish oil.By catfish oil vacuum filter, solid fat component is obtained.Divide and carry admittedly
Fat contains the sn-2 palmitic acids and total palmitic acid compared with catfish oil higher.Gained catfish oil proposes aliphatic acid composition and the distribution of solid fat
It is as shown in table 4 below：
4.20 DEG C of catfish oils of table propose aliphatic acid composition and the distribution of solid fat
Acidolysis catfish consolidates fat component in packed bed flow reactor, with 1,3 specific lipase Lipozyme TL
IM is catalyst, uses the aliphatic acid for coming from high oleic acid rapeseed oil as acry radical donor, and the molar ratio of catfish oil and aliphatic acid is 1:
5, reaction temperature is 40 DEG C, when the substrate residence time is 2 small.After reaction, remove in reaction mixture and may have by centrifuging
Mechanical admixture.
Gained reaction mixture is removed into free fatty by way of molecular distillation, molecular distillation condition used is：
Evaporating temperature, 180 DEG C；Heat exchanger temperature, 60 DEG C；Rotating speed, 130rpm；Absolute pressure, 3Pa.The aliphatic acid group of products obtained therefrom
Into and distribution it is as shown in table 5 below：
The aliphatic acid composition of 5. enzymolysis product of table and distribution
| FA species | FA | sn-2FA | %sn-2FA | sn-1,3FA |
| C14:0 | 3.42 | 4.15 | 40.45 | 3.06 |
| C16:0 | 23.39 | 57.10 | 81.37 | 6.54 |
| C18:0 | 5.67 | 5.51 | 32.39 | 5.75 |
| C18:1 | 59.60 | 21.17 | 11.84 | 78.82 |
| C18:2 | 7.22 | 8.86 | 40.90 | 6.40 |
| C18:3 | 0.30 | 0.40 | 44.44 | 0.25 |
The triglycerides composition of products therefrom is as shown in table 6：
The triglycerides composition of 6. enzymolysis product of table
Example 3：
Refined freshwater catfish oil is melted at 55 DEG C, and keeps 50min, then by catfish oil with the cooling speed of 2 DEG C/min
Rate is cooled to 25 DEG C, and crystallize 10 it is small when, solid fat in catfish oil is into analyzing.By catfish oil by vacuum filter, consolidate
Fat component.Point carry solid fat and contain sn-2 palmitic acids and total palmitic acid compared with catfish oil higher.Gained catfish oil carries the fat of solid fat
Fat acid is formed and is distributed as shown in table 7 below：
7.25 DEG C of catfish oils of table propose aliphatic acid composition and the distribution of solid fat
| FA species | FA | sn-2FA | %sn-2FA | sn-1,3FA |
| C12:0 | 0.33 | 0.59 | 59.60 | 0.20 |
| C14:0 | 4.72 | 4.38 | 30.93 | 4.89 |
| C16:0 | 34.88 | 58.89 | 56.28 | 22.88 |
| C16:1 | 0.49 | 0.62 | 42.18 | 0.43 |
| C18:0 | 9.22 | 4.88 | 17.64 | 11.39 |
| C18:1 | 37.57 | 18.93 | 16.80 | 46.89 |
| C18:2 | 8.62 | 8.74 | 33.80 | 8.56 |
| C18:3 | 0.52 | 0.41 | 26.28 | 0.58 |
| C20:0 | 0.51 | 0.39 | 25.49 | 0.57 |
| C20:1 | 1.28 | 0.35 | 9.11 | 1.75 |
| C20:2 | 0.23 | 0.12 | 17.39 | 0.29 |
| C20:3 | 0.32 | 0.21 | 21.88 | 0.38 |
| C20:4 | 0.17 | 0.10 | 19.61 | 0.21 |
| C22:0 | 0.35 | 0.15 | 14.29 | 0.45 |
| C22:1 | 0.31 | 0.08 | 8.60 | 0.43 |
| C22:2 | 0.08 | 0.06 | 25.00 | 0.09 |
| C24:1 | 0.11 | 0.05 | 15.15 | 0.14 |
| C22:4 | 0.05 | 0.07 | 46.67 | 0.04 |
| C22:5 | 0.09 | 0.10 | 37.04 | 0.09 |
| C22:6 | 0.08 | 0.08 | 33.33 | 0.08 |
The solid fat component of acidolysis catfish oil in packed bed flow reactor, with 1,3 specific lipase Lipozyme TL
IM is catalyst, uses the aliphatic acid for coming from high oleic acid rapeseed oil as acry radical donor, and the molar ratio of catfish oil and aliphatic acid is 1:
4, reaction temperature is 60 DEG C, when the substrate residence time is 0.5 small., may in removal reaction mixture by centrifuging after reaction
Some mechanical admixtures.
Gained reaction mixture is removed into free fatty by way of molecular distillation, molecular distillation condition used is：
Evaporating temperature, 185 DEG C；Heat exchanger temperature, 60 DEG C；Rotating speed, 120rpm；Absolute pressure, 2Pa.The aliphatic acid group of products obtained therefrom
Into and distribution it is as shown in table 8 below：
The aliphatic acid composition of 8. enzymolysis product of table and distribution
| FA species | FA | sn-2FA | %sn-2FA | sn-1,3FA |
| C14:0 | 3.48 | 4.01 | 38.41 | 3.22 |
| C16:0 | 24.49 | 57.3 | 77.99 | 8.09 |
| C18:0 | 5.43 | 5.62 | 34.50 | 5.34 |
| C18:1 | 58.33 | 21.07 | 12.04 | 76.96 |
| C18:2 | 7.42 | 9.02 | 40.52 | 6.62 |
| C18:3 | 0.2 | 0.4 | 66.67 | 0.10 |
The triglycerides composition of products therefrom is as shown in table 9：
The triglycerides composition of 9. enzymolysis product of table
Thus, found by analysis, the total palmitic acid content of catfish oil is 30% or so, about more than 40% palmitic acid
It is the very good material for preparing OPO at sn-2.Formed and be distributed according to the aliphatic acid of catfish oil, enrichment catfish oil is carried by point
In be rich in the parts of sn-2 palmitic acids, then with sn-1,3 selected fat enzymes are catalyst, with high oleic acid vegetable oil source
Aliphatic acid is acry radical donor, and acidolysis point carries catfish oil, can obtain the product of high OPO contents.
The present invention refers to that enzyme process acidolysis is prepared rich in 1,3-, bis- oleic acid -2- first using catfish oil as raw material, with reference to point
Three ester product of palmitic acid, the triglycerides component containing sn-2 palmitic acids in enrichment catfish oil is carried by point, then with high oil
The free fatty of sour vegetable oil source is acry radical donor, obtains being rich in 1,3-, bis- oleic acid -2- palmitic acids three by acidolysis
Ester product.The present invention is raw materials used cheap, and products obtained therefrom 1,3-Dioleic acid-2-palmitoyl triglyceride content is high, can make
It is widely used in for additive in baby formula milk powder fat.
It should be noted that the above embodiments are merely illustrative of the technical solutions of the present invention and it is unrestricted, although with reference to preferable
The present invention is described in detail in embodiment, it will be understood by those of ordinary skill in the art that, can be to the technology of the present invention
Scheme technical scheme is modified or replaced equivalently, without departing from the spirit and scope of technical solution of the present invention, it should all cover in this hair
Among bright right.
Claims (1)
- A kind of 1. method for preparing 1,3-Dioleic acid-2-palmitoyl triglyceride, it is characterised in that：Refined freshwater catfish oil is existed Melted at 50 DEG C, keep 60min, then catfish oil is down to 20 DEG C, when crystallization 7 is small, in catfish oil with the rate of temperature fall of 3 DEG C/min Gu fat into analyzing, by catfish oil vacuum filter, obtains solid fat component, point carry solid fat and contain the sn-2 palms compared with catfish oil higher Sour and total palmitic acid；Acidolysis catfish consolidates fat component in packed bed flow reactor, is with 1,3 specific lipase Lipozyme TL IM Catalyst, uses the aliphatic acid for coming from high oleic acid rapeseed oil as acry radical donor, and the molar ratio of catfish oil and aliphatic acid is 1:5, instead It is 40 DEG C to answer temperature, when the substrate residence time is 2 small, after reaction, passes through and centrifuges presumable machine in removal reaction mixture Tool impurity；Gained reaction mixture is removed into free fatty by way of molecular distillation, molecular distillation condition used is：Evaporation Temperature, 180 DEG C；Heat exchanger temperature, 60 DEG C；Rotating speed, 130rpm；Absolute pressure, 3Pa.
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| CN201510227309.9A CN104862350B (en) | 2015-05-06 | 2015-05-06 | A kind of method for preparing bis- oleic acid -2- palmitic acids of 1,3-, three ester |
| PCT/CN2015/096269 WO2016176987A1 (en) | 2015-05-06 | 2015-12-03 | Preparation method for structured lipid rich in 1,3-dioleate-2-palmitic acid triglyceride |
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| CN201510227309.9A CN104862350B (en) | 2015-05-06 | 2015-05-06 | A kind of method for preparing bis- oleic acid -2- palmitic acids of 1,3-, three ester |
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| CN104862350B (en) * | 2015-05-06 | 2018-05-01 | 江南大学 | A kind of method for preparing bis- oleic acid -2- palmitic acids of 1,3-, three ester |
| CN110724716B (en) * | 2018-07-16 | 2021-07-20 | 浙江贝家生物科技有限公司 | A method for preparing composition containing 1, 3-dioleoyl-2-palmitic acid triglyceride |
| CN111838676A (en) * | 2019-12-17 | 2020-10-30 | 浙江大学 | Medium-long chain fatty acid grease rich in 1, 3-dilaurate-2-palmitic acid triglyceride and preparation and application thereof |
| CN111317068A (en) * | 2020-01-15 | 2020-06-23 | 广州市优百特饲料科技有限公司 | Feeding OPO breast milk structure fat and preparation method and application thereof |
| CN111961527B (en) * | 2020-09-03 | 2021-12-03 | 广州白云山汉方现代药业有限公司 | Accurate control method for palmitic acid content in olive oil |
| CN112522330B (en) * | 2020-11-27 | 2023-04-18 | 江南大学 | Medium-long carbon chain triglyceride for breast milk to replace fat and preparation method thereof |
| CN113712084A (en) * | 2021-07-23 | 2021-11-30 | 暨南大学 | Special oil base material oil for food and preparation method thereof |
| CN113575696B (en) * | 2021-07-30 | 2022-07-19 | 江南大学 | Preparation method of structural lipid based on breast milk triglyceride composition |
| CN113584094B (en) * | 2021-07-30 | 2022-07-19 | 江南大学 | Preparation method of triglyceride with 1,3 unsaturated-2-saturated fatty acid structure based on milk fat |
| CN113481248B (en) * | 2021-07-30 | 2022-04-15 | 江南大学 | Method for preparing 1, 3-dioleoyl-2-palmitic acid triglyceride |
| CN113584093B (en) * | 2021-07-30 | 2022-07-19 | 江南大学 | Preparation method of structured lipid with high DHA content and product thereof |
| CN113575697B (en) * | 2021-07-30 | 2022-10-18 | 江南大学 | Preparation method of breast milk fat substitute based on animal milk fat |
| CN113832200B (en) * | 2021-07-30 | 2023-12-01 | 江南大学 | Preparation method of breast milk structured fat |
| CN113615743B (en) * | 2021-07-30 | 2022-04-15 | 江南大学 | Preparation method of human milk substitute fat simulating breast milk fat structure |
| CN113584095B (en) * | 2021-07-30 | 2022-09-02 | 江南大学 | Product rich in 1, 3-unsaturated-2-saturated fatty acid structured fat and preparation method thereof |
| CN113416755B (en) * | 2021-07-30 | 2022-04-15 | 江南大学 | Industrial production method of 1, 3-dioleic acid-2-palmitic acid triglyceride and product thereof |
| CN114907209B (en) * | 2022-05-13 | 2023-10-13 | 江西师范大学 | Breast milk-like OMO structural ester and preparation method thereof |
| CN115191492A (en) * | 2022-07-14 | 2022-10-18 | 江南大学 | Green and efficient method for preparing human milk substitute lipid and application |
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| CN101940241B (en) * | 2010-07-12 | 2013-05-08 | 深圳精益油脂技术有限公司 | Pangasianodon gigas lipid, application and method for preparing breast milk lipid substitutes thereof |
| CN104862350B (en) * | 2015-05-06 | 2018-05-01 | 江南大学 | A kind of method for preparing bis- oleic acid -2- palmitic acids of 1,3-, three ester |
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