CN113832200A - Preparation method of breast milk structure fat - Google Patents
Preparation method of breast milk structure fat Download PDFInfo
- Publication number
- CN113832200A CN113832200A CN202110878001.6A CN202110878001A CN113832200A CN 113832200 A CN113832200 A CN 113832200A CN 202110878001 A CN202110878001 A CN 202110878001A CN 113832200 A CN113832200 A CN 113832200A
- Authority
- CN
- China
- Prior art keywords
- oil
- acidolysis
- fatty acid
- fat
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 235000020256 human milk Nutrition 0.000 title claims description 43
- 210000004251 human milk Anatomy 0.000 title claims description 42
- 239000000194 fatty acid Substances 0.000 claims abstract description 100
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 99
- 229930195729 fatty acid Natural products 0.000 claims abstract description 99
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 99
- 238000000034 method Methods 0.000 claims abstract description 45
- 238000005194 fractionation Methods 0.000 claims abstract description 24
- 230000008569 process Effects 0.000 claims abstract description 18
- 238000004821 distillation Methods 0.000 claims abstract description 16
- 238000002425 crystallisation Methods 0.000 claims abstract description 9
- 230000008025 crystallization Effects 0.000 claims abstract description 9
- 239000003921 oil Substances 0.000 claims description 74
- 235000019198 oils Nutrition 0.000 claims description 74
- 235000019197 fats Nutrition 0.000 claims description 66
- DCXXMTOCNZCJGO-UHFFFAOYSA-N Glycerol trioctadecanoate Natural products CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 claims description 59
- 238000006243 chemical reaction Methods 0.000 claims description 50
- 239000004519 grease Substances 0.000 claims description 25
- 239000007788 liquid Substances 0.000 claims description 23
- 239000013078 crystal Substances 0.000 claims description 18
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 18
- 235000019484 Rapeseed oil Nutrition 0.000 claims description 15
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 claims description 15
- 239000003549 soybean oil Substances 0.000 claims description 15
- 235000012424 soybean oil Nutrition 0.000 claims description 15
- 238000001914 filtration Methods 0.000 claims description 14
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 13
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 13
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 13
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 13
- 239000005642 Oleic acid Substances 0.000 claims description 13
- 238000010438 heat treatment Methods 0.000 claims description 13
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 13
- 235000021313 oleic acid Nutrition 0.000 claims description 13
- 235000019864 coconut oil Nutrition 0.000 claims description 12
- 239000003240 coconut oil Substances 0.000 claims description 12
- 150000004667 medium chain fatty acids Chemical class 0.000 claims description 12
- 239000002994 raw material Substances 0.000 claims description 12
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 12
- 238000000926 separation method Methods 0.000 claims description 11
- 239000000758 substrate Substances 0.000 claims description 11
- 108090001060 Lipase Proteins 0.000 claims description 10
- 102000004882 Lipase Human genes 0.000 claims description 10
- 239000004367 Lipase Substances 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 10
- 235000019421 lipase Nutrition 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 10
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 9
- 235000021388 linseed oil Nutrition 0.000 claims description 9
- 239000000944 linseed oil Substances 0.000 claims description 9
- 235000019865 palm kernel oil Nutrition 0.000 claims description 9
- 239000003346 palm kernel oil Substances 0.000 claims description 9
- 235000020238 sunflower seed Nutrition 0.000 claims description 9
- 235000020661 alpha-linolenic acid Nutrition 0.000 claims description 7
- 229960004488 linolenic acid Drugs 0.000 claims description 7
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 claims description 7
- 239000008158 vegetable oil Substances 0.000 claims description 7
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 claims description 5
- 240000001548 Camellia japonica Species 0.000 claims description 3
- 235000018597 common camellia Nutrition 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 2
- 230000001681 protective effect Effects 0.000 claims description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 claims 1
- 235000021588 free fatty acids Nutrition 0.000 abstract description 11
- 239000000126 substance Substances 0.000 abstract description 9
- 230000009931 harmful effect Effects 0.000 abstract description 8
- 238000005265 energy consumption Methods 0.000 abstract description 3
- 230000000050 nutritive effect Effects 0.000 abstract description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 178
- 235000021314 Palmitic acid Nutrition 0.000 description 86
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 86
- 239000000047 product Substances 0.000 description 72
- 239000000203 mixture Substances 0.000 description 37
- 238000009826 distribution Methods 0.000 description 23
- 235000013350 formula milk Nutrition 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- PVNIQBQSYATKKL-UHFFFAOYSA-N tripalmitin Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCC PVNIQBQSYATKKL-UHFFFAOYSA-N 0.000 description 19
- 125000002252 acyl group Chemical group 0.000 description 14
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 13
- 230000014759 maintenance of location Effects 0.000 description 12
- 238000012546 transfer Methods 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 150000004671 saturated fatty acids Chemical group 0.000 description 10
- 239000000839 emulsion Substances 0.000 description 9
- 239000012535 impurity Substances 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- 229960001947 tripalmitin Drugs 0.000 description 9
- 229940040461 lipase Drugs 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- 238000005119 centrifugation Methods 0.000 description 7
- 235000020778 linoleic acid Nutrition 0.000 description 7
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 7
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 7
- 239000012467 final product Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 125000005456 glyceride group Chemical group 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 230000009102 absorption Effects 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 239000010495 camellia oil Substances 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 230000029087 digestion Effects 0.000 description 4
- -1 glycidyl ester Chemical class 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- 108010048733 Lipozyme Proteins 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- 229940088598 enzyme Drugs 0.000 description 3
- FCCDDURTIIUXBY-UHFFFAOYSA-N lipoamide Chemical compound NC(=O)CCCCC1CCSS1 FCCDDURTIIUXBY-UHFFFAOYSA-N 0.000 description 3
- 235000013336 milk Nutrition 0.000 description 3
- 239000008267 milk Substances 0.000 description 3
- 210000004080 milk Anatomy 0.000 description 3
- 235000016709 nutrition Nutrition 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 235000005593 Camellia sinensis f parvifolia Nutrition 0.000 description 2
- 244000041840 Camellia sinensis f. parvifolia Species 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000002255 enzymatic effect Effects 0.000 description 2
- 230000007071 enzymatic hydrolysis Effects 0.000 description 2
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 2
- 150000003626 triacylglycerols Chemical class 0.000 description 2
- 206010010774 Constipation Diseases 0.000 description 1
- 102100031416 Gastric triacylglycerol lipase Human genes 0.000 description 1
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [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
- 239000002253 acid Substances 0.000 description 1
- 235000008452 baby food Nutrition 0.000 description 1
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 235000020247 cow milk Nutrition 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 210000002919 epithelial cell Anatomy 0.000 description 1
- 235000020774 essential nutrients Nutrition 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 108010091264 gastric triacylglycerol lipase Proteins 0.000 description 1
- 235000020251 goat milk Nutrition 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000000383 hazardous chemical Substances 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 229910001425 magnesium ion Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- 125000003729 nucleotide group Chemical group 0.000 description 1
- 235000021315 omega 9 monounsaturated fatty acids Nutrition 0.000 description 1
- 235000020660 omega-3 fatty acid Nutrition 0.000 description 1
- 229940116369 pancreatic lipase Drugs 0.000 description 1
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229960003080 taurine Drugs 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 125000005457 triglyceride group Chemical group 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
Classifications
-
- 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
- C12P7/6436—Fatty acid esters
- C12P7/6445—Glycerides
-
- 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
- A23C9/00—Milk preparations; Milk powder or milk powder preparations
- A23C9/152—Milk preparations; Milk powder or milk powder preparations containing additives
- A23C9/1528—Fatty acids; Mono- or diglycerides; Petroleum jelly; Paraffine; Phospholipids; Derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Microbiology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Fats And Perfumes (AREA)
Abstract
The invention provides a preparation method of a mother emulsified structure fat, which comprises the following steps: acidolysis, fractionation, circulation and reduced pressure distillation. The obtained product has higher quality and higher safety, can recycle free fatty acid, has lower cost and energy consumption, lower generation amount of harmful substances and higher nutritive value, and can preferentially avoid the crystallization of the carbon-chain fatty acid in the low-temperature fractionation process in the preparation process.
Description
Technical Field
The invention relates to the technical field of grease, in particular to a preparation method of a grease with a primary emulsion structure.
Background
Breast milk is a natural biocolloid system that provides dietary energy, essential nutrients, and bioactive molecules to infants. The breast milk contains 3-5% of fat, wherein the content of triglyceride is more than 98%, and the breast milk provides important functional fatty acid for infants while supplying energy. The distribution of fatty acids in triglyceride in the mother milk fat is unique, more than 60% of palmitic acid is in sn-2 position, and other fatty acids such as oleic acid and linoleic acid are mainly in sn-1 and 3 positions. Thus, the configuration of the major triglycerides in breast milk fat is sn-1, 3-unsaturated fatty acid-sn-2 palmitic acid triglyceride, which has a significant impact on the digestion, absorption and metabolism of fat. After fat is ingested by the human body, free fatty acid and sn-2 monoglyceride are generated by digestion with gastric lipase and pancreatic lipase. sn-2 monoglycerides are directly absorbed by small intestinal villous epithelial cells, but absorption of free fatty acids is related to their chain length and unsaturation. The long-chain saturated fatty acids form insoluble soaps with calcium and magnesium ions in the small intestine, and thus have very poor absorption rate, resulting in loss of energy and calcium, and dry stools, resulting in constipation. Therefore, the long-chain saturated fatty acid at the sn-2 position of triglyceride forms sn-2 monoglyceride in the process of digestion, which facilitates the absorption of saturated fatty acid by infants, and prevents the side effect caused by the formation of saturated free fatty acid soap.
When infants cannot obtain breast feeding, the infant formula becomes a good substitute for breast milk. The infant formula milk powder takes breast milk as a gold standard, generally adopts cow milk or goat milk as a main raw material to regulate protein and fat composition, content or structure according to the chemical composition of the breast milk, and simultaneously adds various fat-soluble and water-soluble vitamins, trace mineral substances, nucleotide, taurine, long-carbon-chain polyunsaturated fatty acid (LCPUFAs) grease and other functional substances. Because the infant formula milk powder is dehydrated food, the fat content is about 25 percent. Therefore, the composition and structure of fat in the formula has a significant impact on the impact and development of the infant. High-end formula milk powder manufacturers all adjust the fat structure of formula milk powder by adding substitute fat simulating the fat structure of breast milk, so that palmitic acid in the milk powder is mainly in the sn-2 position.
Since infants belong to a particular group and are not well developed in their own digestive, metabolic and immune systems, the potential harmful factors may be infinitely amplified for their harmful effects. Any raw materials used in infant food and the production process are subject to the most stringent evaluation. At present, the raw material for commercially preparing the breast milk substitute fat mainly comprises high-melting-point palm stearin, the production process comprises the steps of taking fatty acid mainly comprising oleic acid as an acyl donor, taking sn-1, 3-position specific lipase as a catalyst, and reducing the content of sn-1, 3-palmitic acid of the palm stearin through acidolysis reaction to obtain the breast milk substitute fat. However, in the production process, most of products obtained by one-time acidolysis reaction have high sn-1, 3-palmitic acid content, so that the total palmitic acid content is higher than that of breast milk fat, and the process needs to adopt a high substrate ratio. The process reduces the nutritive value of the product and causes burden on the digestion of the infant, and on the other hand, the higher substrate ratio requires harsher deacidification conditions, thereby increasing the production cost and simultaneously generating more harmful substances, such as trans-fatty acid, glycidyl ester, chloropropanol ester and the like. Therefore, the technology of the patent firstly proposes that the enzyme catalysis acidolysis is coupled with the low-temperature program fractionation, the palmitic acid and the tripalmitin in the mixed oil are fractionated and separated by the low-temperature program using the melting point difference after the enzyme catalysis acidolysis reaction, and the cyclic acidolysis and fractionation are carried out according to the separation, so that the obtained product has lower palmitic acid content, higher sn-2 palmitic acid relative content and less harmful substance generation amount, and therefore, the product has higher nutritional value and safety, and meanwhile, the process realizes the cyclic utilization of unsaturated fatty acid, thereby reducing the production process cost and energy consumption.
Disclosure of Invention
This section is for the purpose of summarizing some aspects of embodiments of the invention and to briefly introduce some preferred embodiments. In this section, as well as in the abstract and the title of the invention of this application, simplifications or omissions may be made to avoid obscuring the purpose of the section, the abstract and the title, and such simplifications or omissions are not intended to limit the scope of the invention.
The present invention has been made in view of the above and/or problems occurring in the product of the marbled structure fat.
It is therefore one of the objects of the present invention. Overcomes the defects of the prior breast-milk fat product and provides a preparation method of breast-milk fat structure fat.
The technical problem is not solved, and according to one aspect of the present invention, the present invention provides the following technical solutions: a preparation method of a mother emulsified structural fat comprises the following steps:
acid hydrolysis: adding catalyst into fatty acid from palm hard and fat vegetable oil as raw material, and performing acidolysis;
separating and extracting: performing low-temperature program fractionation on the acidolysis product to separate out crystals and obtain liquid oil;
and (3) circulation: the steps of acidolysis and fractionation are circulated;
and (3) reduced pressure distillation: the fatty acid was removed by distillation under reduced pressure.
As a preferable embodiment of the method for preparing the resin with a structure of a mother emulsion of the present invention, wherein: in the acidolysis, the catalyst is one or more of commercial sn-1,3 selective Lipase, such as Lipzyme RM IM, Lipzyme TL IM, Lipase DF and NS 40086.
As a preferable embodiment of the method for preparing the resin with a structure of a mother emulsion of the present invention, wherein: the vegetable oil comprises one or more of soybean oil rich in oleic acid and linoleic acid, rapeseed oil, camellia seed oil, sunflower seed oil, linseed oil rich in linolenic acid, coconut oil rich in medium-chain fatty acid, palm kernel oil, etc.
As a preferable embodiment of the method for preparing the resin with a structure of a mother emulsion of the present invention, wherein: the circulating step is that the steps of acidolysis and fractionation are repeated for 2-3 times.
As a preferable embodiment of the method for preparing the resin with a structure of a mother emulsion of the present invention, wherein: in the acidolysis process, the reaction conditions are that in a packed bed reactor, the molar ratio of the fatty acid to the palm stearin substrate is 4:1-10:1, the temperature is 55-65 ℃, and the time is 1-4 h; carrying out first low-temperature program fractionation after the first enzymolysis reaction, wherein the conditions comprise that the oil is heated to 55-65 ℃ and maintained for 20-30min, then the temperature is reduced to 35-40 ℃ at the speed of 4-10 ℃ per hour, the crystal is grown for 3-5h, then the temperature is reduced to 26-33 ℃ at the speed of 3-5 ℃ per hour, the crystal is grown for 2-10h, and after the fractionation crystallization is finished, the solid fat is filtered or centrifugally separated, so that the liquid oil is obtained.
As a preferable embodiment of the method for preparing the resin with a structure of a mother emulsion of the present invention, wherein: circulating in the circulating process, and introducing the liquid oil obtained by the first fractionation into a packed bed reactor at the reaction temperature of 45-60 ℃ for 1-4h when the first acidolysis is substantially the second acidolysis in the circulating process; and the second low-temperature separation is carried out by heating the oil to 50-55 deg.C for 25-30min, cooling to 20-25 deg.C at 6-15 deg.C/h, growing crystal for 4-8h, and filtering or centrifuging to separate solid fat to obtain liquid oil.
As a preferable embodiment of the method for preparing the resin with a structure of a mother emulsion of the present invention, wherein: and circulating in the circulating process, wherein when the second acidolysis is actually the third acidolysis, the condition of the third enzyme catalysis acidolysis is that the liquid oil obtained by the second fractionation is introduced into the packed bed reactor, the reaction temperature is 50-60 ℃, and the reaction time is 1-3 h.
As a preferable embodiment of the method for preparing the resin with a structure of a mother emulsion of the present invention, wherein: coconut oil or palm kernel oil fatty acid is added in the last acidolysis reaction.
As a preferable embodiment of the method for preparing the resin with a structure of a mother emulsion of the present invention, wherein: in acidolysis, fractionation and reduced pressure distillation, the oil is placed in a protective atmosphere.
Compared with other existing processes, the preparation method of the breast-emulsifying structure fat provided by the invention has the advantages that the obtained product is higher in quality and better in safety, and the following advantages are achieved: 1. after the acidolysis reaction, saturated fatty acid and tripalmitin in the mixed oil are separated and removed by using the melting point difference and adopting a low-temperature procedure, and cyclic acidolysis and separation are performed according to the method, so that compared with the traditional method for removing fatty acid by reduced pressure distillation, free fatty acid is recycled, the cost is lower, the energy consumption is lower, and the generation amount of harmful substances is less; 2. the multi-cycle acidolysis reaction is carried out on the basis of coupled low-temperature program fractionation, so that the sn-1, 3-palmitic acid substitution amount is higher, the amount of acyl transfer of the product is less, and the relative content of the sn-2-palmitic acid is higher, so that the product has higher nutritional value; 3. in the process, the composition of oleic acid, linoleic acid and palmitic acid of the grease is adjusted through the first 1 or 2 steps of acidolysis, and the composition of medium-chain fatty acid is adjusted through the last step of acidolysis, so that the crystallization separation of the medium-chain fatty acid in low-temperature program fractionation is effectively avoided.
Detailed Description
In order to make the aforementioned objects, features and advantages of the present invention more comprehensible, specific embodiments thereof are described in detail below with reference to examples of the specification.
In the following description, numerous specific details are set forth in order to provide a thorough understanding of the present invention, but the present invention may be practiced in other ways than those specifically described and will be readily apparent to those of ordinary skill in the art without departing from the spirit of the present invention, and therefore the present invention is not limited to the specific embodiments disclosed below.
Furthermore, reference herein to "one embodiment" or "an embodiment" means that a particular feature, structure, or characteristic described in connection with the embodiment is included in at least one implementation of the invention. The appearances of the phrase "in one embodiment" in various places in the specification are not necessarily all referring to the same embodiment, nor are separate or alternative embodiments mutually exclusive of other embodiments.
Through measurement, the content of C6:0 in breast milk fat is 0.01-0.12%, the content of C8:0 is 0.1-1%, the content of C10:0 is 0.1-2.8%, the content of C12:0 is 2-10%, the content of C14:0 is 2-10%, the content of C16:0 is 20-30%, the content of C18:0 is 2-9%, the content of C18:1 omega-9 is 25-37%, the content of C18:2 omega-6 is 14-27%, and the relative content of dipalmitic acid (% sn-2C16:0) > 60%; the content of C18:2 omega-6/C18: 3 omega-3 is between 5 and 15.
Example 1
The 52-degree palm stearin extract is selected as a raw material, the palmitic acid content is 82.4 percent, and the sn-2 palmitic acid content is 75.5 percent. Compared with breast milk fat, the palm stearin is lack of linoleic acid, oleic acid, linolenic acid and medium-chain fatty acid, and meanwhile, the relative content of the palmitic acid at the sn-2 position is far lower than that of the breast milk fat. Therefore, by selecting proper fatty acid from vegetable oil and carrying out continuous acidolysis on the palm stearin, the content of the palmitic acid at the sn-1 and the sn-3 positions is reduced, the relative content of the palmitic acid at the sn-2 positions is increased, and the composition of the sn-1 and the sn-3 fatty acid is adjusted. Therefore, in order to improve the fatty acid composition of palm stearin, firstly, a soybean oil rich in linoleic acid and a rapeseed oil-derived fatty acid rich in oleic acid were selected as acyl donors, a ratio of the soybean oil to the rapeseed oil fatty acid was 1:3(mol/mol) and a substrate ratio of the fatty acid to the palm stearin was 4:1(mol/mol) using Lipozyme RM IM as a catalyst, and an acid hydrolysis reaction was performed in a packed bed reactor. Before the oil and the oil enter the packed bed reactor, firstly introducing nitrogen into the packed bed reactor, replacing air in the packed bed reactor with nitrogen, mixing fatty acid and palm stearin, heating the mixed oil to 60 ℃, keeping the temperature for 20min to completely melt the mixed oil, then introducing the mixed oil into the packed bed reactor, keeping the temperature of the packed bed at 55 ℃, keeping the retention time of the oil in the packed bed at 3h, and obtaining an acidolysis product after the reaction is finished. After the reaction, possible impurities were removed by filtration or centrifugation, and the fatty acid composition and distribution of the obtained primary acid hydrolysis product were as shown in the following table.
TABLE 1 fatty acid composition and distribution of primary acidolysis products
The% sn-2 PA represents the ratio of sn-2 palmitic acid to total palmitic acid, and is calculated by the formula: sn-2 palmitic acid/(3X Total palmitic acid). times.100%
As can be seen from the above table, after one-time acidolysis, the% sn-2 PA of the acidolysis product is improved, but is not in the range of breast milk fat, and the content of palmitic acid is much higher than that of breast milk fat, so that the product needs to be subjected to secondary acidolysis. Separating and crystallizing by using a low-temperature program to remove palmitic acid, saturated triglyceride and partial glyceride in the primary acidolysis product, wherein the separation condition is to heat the grease to 60 ℃ and maintain the temperature for 25min, reduce the temperature to 40 ℃ at the speed of 10 ℃ per hour, grow crystals for 3h, reduce the temperature to 33 ℃ at the speed of 3 ℃ per hour, grow crystals for 8h at the rotating speed of 40 r/min, and after the separation and crystallization are finished, filtering or centrifugally separating solid fat to obtain liquid oil.
Coconut oil fatty acid is selected as a source of medium-chain fatty acid, the coconut oil fatty acid, soybean oil and rapeseed oil fatty acid are added into a reaction system according to the proportion that the sum of the coconut oil fatty acid, the soybean oil and the rapeseed oil fatty acid is 1:4, oil is heated to 50 ℃ and kept for 30min, then the oil is introduced into a packed bed reactor, the temperature of the packed bed is kept at 45 ℃, the retention time of the oil in the packed bed is 4h, and an acidolysis product is obtained after the reaction is finished. And after the reaction is finished, removing possible impurities by filtering or centrifuging to obtain a secondary acidolysis product.
The free fatty acids were removed by distillation under reduced pressure, and the fatty acid composition and distribution of the obtained secondary enzymatic hydrolysis product were as follows.
TABLE 2 fatty acid composition and distribution of secondary acidolysis products
The% sn-2 PA represents the ratio of sn-2 palmitic acid to total palmitic acid, and is calculated by the formula: sn-2 palmitic acid/(3X Total palmitic acid). times.100%
The trans fatty acid content of the final product was 0.16g/100 g.
As can be seen from the above table, after the secondary acidolysis, the composition of the obtained acidolysis product is within the range of main indexes of breast milk fat, and the obtained acidolysis product can be used as breast milk substitute fat to be added into formula milk powder.
Example 2
58-degree palm stearin is selected as a raw material, the palmitic acid content is 70.3%, and the sn-2 palmitic acid content is 58.3%. Compared with breast milk fat, the palm stearin is lack of linoleic acid, oleic acid, linolenic acid and medium-chain fatty acid, and meanwhile, the relative content of the palmitic acid at the sn-2 position is far lower than that of the breast milk fat. Therefore, by selecting proper fatty acid from vegetable oil and carrying out continuous acidolysis on the palm stearin, the content of the palmitic acid at the sn-1 and the sn-3 positions is reduced, the relative content of the palmitic acid at the sn-2 positions is increased, and the composition of the sn-1 and the sn-3 fatty acid is adjusted. Therefore, in order to improve the fatty acid composition of palm stearin, firstly, a soybean oil rich in linoleic acid and a rapeseed oil-derived fatty acid rich in oleic acid were selected as acyl donors, the ratio of the soybean oil to the rapeseed oil fatty acid was 1:2(mol/mol), the substrate ratio of the fatty acid to the palm stearin was 6:1(mol/mol), and acidolysis reaction was performed in a packed bed reactor with NS40086 as a catalyst. Before the grease enters a packed bed reactor, firstly introducing nitrogen into the packed bed reactor, replacing air in the packed bed reactor with the nitrogen, mixing fatty acid with palm stearin, heating the mixed grease to 55 ℃, keeping the temperature for 30min to completely melt the mixed grease, then introducing the mixed grease into the packed bed reactor, keeping the temperature of the packed bed at 60 ℃, keeping the retention time of the grease in the packed bed at 2h, and obtaining an acidolysis product after the reaction is finished. After the reaction, possible impurities were removed by filtration or centrifugation, and the fatty acid composition and distribution of the obtained primary acid hydrolysis product were as shown in the following table.
TABLE 3 fatty acid composition and distribution of palm stearin and primary acidolysis product
The% sn-2 PA represents the ratio of sn-2 palmitic acid to total palmitic acid, and is calculated by the formula: sn-2 palmitic acid/(3X Total palmitic acid). times.100%
As can be seen from the above table, after one-time acidolysis, the% sn-2 PA of the acidolysis product is improved, but is not in the range of breast milk fat, and the content of palmitic acid is much higher than that of breast milk fat, so that the product needs to be subjected to secondary acidolysis. Separating and removing palmitic acid, tripalmitin and partial glyceride in the primary acidolysis product by using a low-temperature program, wherein the separation condition is that the oil is heated to 55 ℃ and maintained for 30min, the temperature is reduced to 37 ℃ at the speed of 8 ℃ per hour, crystal growth is carried out for 5h, the temperature is reduced to 26 ℃ at the speed of 5 ℃ per hour, crystal growth is carried out for 2h at the rotating speed of 50 r/min, and after the separation and crystallization are finished, solid fat is filtered or centrifugally separated, so that liquid oil is obtained.
Heating the liquid oil to 50 ℃, keeping the temperature for 30min, then introducing the liquid oil into a packed bed reactor, keeping the temperature of the packed bed at 50 ℃, keeping the retention time of the grease in the packed bed at 3h, and obtaining an acidolysis product after the reaction is finished. After the reaction, possible impurities were removed by filtration or centrifugation, and the fatty acid composition and distribution of the obtained secondary acidolysis product were as shown in the following table.
TABLE 4 fatty acid composition and distribution of secondary acidolysis product
Fatty acid (mol%) | General assembly | sn-2 | sn-1,3 |
C14:0 | 0.3 | 0.4 | 0.3 |
C16:0 | 30.0 | 53.7 | 18.2 |
C18:0 | 3.7 | 4.1 | 3.5 |
C18:1n-9 | 34.8 | 27.0 | 38.7 |
C18:2n-6 | 27.7 | 14.1 | 34.5 |
C18:3 | 3.4 | 0.7 | 4.8 |
%sn-2 PA* | 59.6 | ||
C18:2/C18:3 | 8.1 | ||
Palmitic acid acyl transfer ratio (%) | 1.70 |
The% sn-2 PA represents the ratio of sn-2 palmitic acid to total palmitic acid, and is calculated by the formula: sn-2 palmitic acid/(3X Total palmitic acid). times.100%
As can be seen from the above table, after the secondary acidolysis, the acidolysis product% sn-2 PA reaches 59.6%, and the content of palmitic acid is close to that of breast milk fat, but the contents of C6:0, C8:0, C10:0 and C12:0 in the acidolysis product are greatly different from that of breast milk fat. Therefore, three acid hydrolysis processes are required for the product.
And (3) carrying out fractionation by utilizing a low-temperature procedure to remove saturated fatty acid in the system, wherein the fractionation condition is that the oil is heated to 50 ℃ and maintained for 30min, the temperature is reduced to 20 ℃ at the speed of 15 ℃ per hour, the crystal is grown for 4 hours, the rotating speed is 40 r/min, and after the fractionation crystallization is finished, filtering or centrifugally separating solid fat to obtain liquid oil.
Coconut oil fatty acid is selected as a source of medium-chain fatty acid, the coconut oil fatty acid, soybean oil and rapeseed oil fatty acid are added into a reaction system according to the proportion of 1:2, oil is heated to 50 ℃ and kept for 30min, then the oil is introduced into a packed bed reactor, the temperature of the packed bed is kept at 50 ℃, the retention time of the oil in the packed bed is 3h, and an acidolysis product is obtained after the reaction is finished. And after the reaction is finished, removing possible impurities by filtering or centrifuging to obtain a third acidolysis product. The fatty acid was distilled off under reduced pressure, and the fatty acid obtained as the third acidolysis product and the distribution composition thereof were as shown in the following table.
TABLE 5 fatty acids and distribution of the product of the third acid hydrolysis
Fatty acid (mol%) | General assembly | sn-2 | sn-1,3 |
C6:0 | 0.03 | 0.02 | 0.03 |
C8:0 | 0.6 | 0.2 | 0.8 |
C10:0 | 0.5 | 0.1 | 0.7 |
C12:0 | 5.9 | 0.7 | 8.5 |
C14:0 | 1.6 | 0.3 | 2.2 |
C16:0 | 26.2 | 51.5 | 13.5 |
C18:0 | 3.1 | 3.1 | 3.1 |
C18:1n-9 | 32.8 | 28.5 | 34.9 |
C18:2n-6 | 26.4 | 14.7 | 32.2 |
C18:3 | 3.0 | 0.9 | 4.1 |
%sn-2 PA* | 65.6 | ||
C18:2/C18:3 | 8.7 | ||
Palmitic acid acyl transfer ratio (%) | 2.2 | ||
Acyl transfer ratio (%) of triply acidolyzed palmitic acid | 6.9 | ||
Tripalmitin (%) | 0.88 |
The% sn-2 PA represents the ratio of sn-2 palmitic acid to total palmitic acid, and is calculated by the formula: sn-2 palmitic acid/(3X Total palmitic acid). times.100%
The trans fatty acid content of the final product was 0.22g/100 g.
As can be seen from the table above, after three times of acidolysis, the composition of the obtained acidolysis product is within the range of main indexes of breast milk fat, and the obtained acidolysis product can be used as breast milk substitute fat to be added into formula milk powder.
Example 3
The 58-degree palm stearin extract is selected as a raw material, the palmitic acid content is 91.2%, and the sn-2 palmitic acid content is 84.3%. Compared with breast milk fat, the palm stearin is lack of linoleic acid, oleic acid, linolenic acid and medium-chain fatty acid, and meanwhile, the relative content of the palmitic acid at the sn-2 position is far lower than that of the breast milk fat. Therefore, by selecting proper fatty acid from vegetable oil and carrying out continuous acidolysis on the palm stearin, the content of the palmitic acid at the sn-1 and the sn-3 positions is reduced, the relative content of the palmitic acid at the sn-2 positions is increased, and the composition of the sn-1 and the sn-3 fatty acid is adjusted. Therefore, in order to improve the fatty acid composition of the palm stearin, firstly, oil tea seed oil rich in oleic acid, sunflower seed oil rich in linoleic acid and fatty acid of linseed oil rich in linolenic acid are selected as acyl donors, the ratio of the oil tea seed oil, the sunflower seed oil and the linseed oil is 1:1:0.3(mol/mol), Lipozyme TL IM is used as a catalyst, the substrate ratio of the fatty acid to the palm stearin is 10:1(mol/mol), and the acidolysis reaction is carried out in a packed bed reactor. Before the grease enters a packed bed reactor, firstly introducing nitrogen into the packed bed reactor, replacing air in the packed bed reactor with the nitrogen, mixing fatty acid with palm stearin, heating the mixed grease to 65 ℃, keeping the temperature for 20min to completely melt the mixed grease, then introducing the mixed grease into the packed bed reactor, keeping the temperature of the packed bed at 65 ℃, keeping the retention time of the grease in the packed bed at 1h, and obtaining an acidolysis product after the reaction is finished. The fatty acid composition and distribution of the primary acidolysis product obtained by removing possible impurities by filtration or centrifugation are shown in the table below.
TABLE 6 fatty acids and distribution composition of primary acidolysis products
The% sn-2 PA represents the ratio of sn-2 palmitic acid to total palmitic acid, and is calculated by the formula: sn-2 palmitic acid/(3X Total palmitic acid). times.100%
As can be seen from the above table, after one-time acidolysis, the% sn-2 PA of the acidolysis product is improved, but is not in the range of breast milk fat, and the content of palmitic acid is much higher than that of breast milk fat, so that the product needs to be subjected to secondary acidolysis. Separating and removing palmitic acid, tripalmitin and partial glyceride in the primary acidolysis product by using a low-temperature program, wherein the separation condition is that the oil is heated to 65 ℃ and maintained for 20min, the temperature is reduced to 35 ℃ at the speed of 4 ℃/h, crystal growth is carried out for 4h, the temperature is reduced to 28 ℃ at the speed of 5 ℃/h, crystal growth is carried out for 5h, the rotating speed is 30 r/min, and after the separation and crystallization are finished, saturated fatty acid and solid fat are filtered and separated to obtain liquid oil.
Heating the liquid oil to 55 ℃, keeping the temperature for 25min, then introducing the liquid oil into a packed bed reactor, keeping the temperature of the packed bed at 55 ℃, keeping the retention time of the grease in the packed bed at 2h, and obtaining an acidolysis product after the reaction is finished. After the reaction, possible impurities were removed by filtration or centrifugation, and the fatty acid composition and distribution of the obtained secondary acidolysis product were as shown in the following table.
TABLE 7 fatty acid composition and distribution of enzymatic products
The% sn-2 PA represents the ratio of sn-2 palmitic acid to total palmitic acid, and is calculated by the formula: sn-2 palmitic acid/(3X Total palmitic acid). times.100%
As can be seen from the table above, after the secondary acidolysis, the acidolysis product% sn-2 PA reaches 69.9%, the content of palmitic acid is higher than that of breast milk fat, and the content of C6:0, C8:0, C10:0 and C12:0 in the acidolysis product is greatly different from that of breast milk fat. Therefore, three acid hydrolysis processes are required for the product. And (3) carrying out fractionation by utilizing a low-temperature program to remove saturated fatty acid in the system, wherein the fractionation condition is that the oil is heated to 55 ℃ and maintained for 25min, the temperature is reduced to 25 ℃ at the speed of 6 ℃ per hour, the crystal is grown for 8 hours, the rotating speed is 20 r/min, and after the fractionation crystallization is finished, filtering or centrifugally separating solid fat to obtain liquid oil.
Selecting palm kernel oil fatty acid as a source of medium-chain fatty acid, adding the palm kernel oil fatty acid and camellia seed oil, sunflower seed oil and linseed oil fatty acid in a ratio of 1:2 into a reaction system, heating the oil to 55 ℃, keeping the temperature for 20min, introducing the oil into a packed bed reactor, keeping the temperature of the packed bed at 60 ℃, keeping the retention time of the oil in the packed bed at 1h, and obtaining an acidolysis product after the reaction is finished. The free fatty acids were removed by distillation under reduced pressure, and the fatty acid composition and distribution of the obtained tertiary enzymatic products were as follows.
TABLE 8 fatty acid composition and distribution of the triple enzymolysis products
Fatty acid (mol%) | General assembly | sn-2 | sn-1,3 |
C6:0 | 0.02 | 0.01 | 0.02 |
C8:0 | 0.5 | 0.1 | 0.5 |
C10:0 | 0.5 | 0.1 | 0.6 |
C12:0 | 6.9 | 0.8 | 9.7 |
C14:0 | 2.8 | 0.7 | 3.5 |
C16:0 | 29.1 | 71.3 | 12.8 |
C18:0 | 2.4 | 2.2 | 2.4 |
C18:1n-9 | 33.6 | 16.2 | 39.5 |
C18:2n-6 | 20.8 | 7.3 | 26.7 |
C18:3 | 3.4 | 1.3 | 4.3 |
%sn-2 PA* | 81.7 | ||
C18:2/C18:3 | 6.1 | ||
Palmitic acid acyl transfer ratio (%) | 4.9 | ||
Acyl transfer ratio (%) of triply acidolyzed palmitic acid | 13 | ||
Tripalmitin (%) | 1.17 |
The% sn-2 PA represents the ratio of sn-2 palmitic acid to total palmitic acid, and is calculated by the formula: sn-2 palmitic acid/(3X Total palmitic acid). times.100%
The trans fatty acid content of the final product was 0.21g/100 g.
As can be seen from the table above, after three times of acidolysis, the composition of the obtained acidolysis product is within the range of main indexes of breast milk fat, and the obtained acidolysis product can be used as breast milk substitute fat to be added into formula milk powder.
Example 4
The method comprises the steps of taking a 52-degree palm stearin fraction as a raw material, wherein the palmitic acid content of the palm stearin fraction is 82.4%, the sn-2 palmitic acid content of the palm fraction is 75.5%, taking 1, 3-site specific lipase DF as a catalyst, selecting soybean oil rich in linoleic acid and rapeseed oil-derived fatty acid rich in oleic acid as acyl donors, the ratio of the soybean oil to the rapeseed oil fatty acid is 1:3(mol/mol), the molar ratio of free fatty acid to palm stearin is 8:1, heating the mixed oil at 60 ℃ for 25min, completely melting the mixed oil, reacting the mixed oil in a packed bed reactor, wherein the reaction temperature is 50 ℃, the retention time of the oil in the packed column 1 is 4h, and the fatty acid composition and distribution of a primary acidolysis product are shown as follows. Before the grease enters the packed bed reactor, nitrogen is firstly introduced into the packed bed reactor, and the nitrogen is used for replacing the air inside the packed bed reactor.
TABLE 9 fatty acid composition and distribution of primary acidolysis product
The% sn-2 PA represents the ratio of sn-2 palmitic acid to total palmitic acid, and is calculated by the formula: sn-2 palmitic acid/(3X Total palmitic acid). times.100%
After the reaction is finished, carrying out low-temperature program fractionation on the acidolysis mixed oil to remove high-melting-point saturated fatty acid and tripalmitin in the acidolysis mixed oil, wherein the fractionation conditions are as follows: heating the grease to 55 ℃ and maintaining for 30min, reducing the temperature to 37 ℃ at the speed of 4 ℃/h, growing crystals for 4h, reducing the temperature to 30 ℃ at the speed of 4 ℃/h, growing crystals for 10h at the rotation speed of 20 rpm, and separating solid fat to obtain liquid oil.
Coconut oil fatty acid is selected as a source of medium-chain fatty acid, the coconut oil fatty acid, the soybean oil and the rapeseed oil fatty acid are added into liquid oil according to the proportion that the sum of the coconut oil fatty acid, the soybean oil and the rapeseed oil fatty acid is 1:4, the mixed oil is heated for 20min at 60 ℃, after the mixed oil is completely melted, the mixture is continuously introduced into a packed bed reactor 2 for secondary acidolysis reaction, the reaction temperature is 60 ℃, and the retention time is 1 h. After the secondary acidolysis reaction, free fatty acids were removed by reduced pressure distillation, and the fatty acid composition and distribution of the obtained secondary enzymatic hydrolysis product were as follows.
TABLE 10 fatty acid composition and distribution of secondary acidolysis products
Fatty acid (mol%) | General assembly | sn-2 | sn-1,3 |
C6:0 | 0.02 | 0.01 | 0.02 |
C8:0 | 0.4 | 0.1 | 0.6 |
C10:0 | 0.5 | 0.1 | 0.7 |
C12:0 | 4.1 | 0.6 | 5.9 |
C14:0 | 1.7 | 0.2 | 2.4 |
C16:0 | 29.8 | 68.5 | 10.5 |
C18:0 | 2.5 | 2.6 | 2.4 |
C18:1n-9 | 31.3 | 19.5 | 37.2 |
C18:2n-6 | 25.5 | 7.4 | 34.48 |
C18:3 | 4.2 | 0.9 | 5.8 |
%sn-2 PA* | 76.5 | ||
C18:2/C18:3 | 6.1 | ||
Palmitic acid acyl transfer ratio (%) | 4.3 | ||
Acyl transfer ratio (%) of twice acidolysis palmitic acid | 7 | ||
Tripalmitoyl triglyceride (%) | 1.32 |
The% sn-2 PA represents the ratio of sn-2 palmitic acid to total palmitic acid, and is calculated by the formula: sn-2 palmitic acid/(3X Total palmitic acid). times.100%
The trans fatty acid content of the final product was 0.18g/100 g.
As can be seen from the above table, after the secondary acidolysis, the composition of the obtained acidolysis product is within the range of main indexes of breast milk fat, and the obtained acidolysis product can be used as breast milk substitute fat to be added into formula milk powder.
Comparative example 1
Based on example 3, the fatty acids were removed by distillation under reduced pressure after the acid hydrolysis without low-temperature fractionation. The method comprises the following specific steps: taking palm stearin with palmitic acid content of 91.2% and sn-2 palmitic acid content of 84.3% as a starting material, firstly, selecting oil tea seed oil rich in oleic acid, sunflower seed oil rich in linoleic acid and fatty acid of linseed oil rich in linolenic acid as acyl donors, wherein the proportion of the oil tea seed oil, the sunflower seed oil and the linseed oil fatty acid is 1:1:0.3(mol/mol/mol), taking Lipozyme TL IM as a catalyst, and the molar ratio of the fatty acid to the palm stearin substrate is 10:1, and carrying out acidolysis reaction in a packed bed reactor. Before the grease enters a packed bed reactor, firstly introducing nitrogen into the packed bed reactor, replacing air in the packed bed reactor with the nitrogen, mixing fatty acid with palm stearin, heating the mixed grease to 65 ℃, keeping the temperature for 20min to completely melt the mixed grease, then introducing the mixed grease into the packed bed reactor, keeping the temperature of the packed bed at 65 ℃, keeping the retention time of the grease in the packed bed at 1h, and obtaining an acidolysis product after the reaction is finished. Removing possible impurities by filtration or centrifugation, deacidifying a primary enzymolysis product by adopting reduced pressure distillation, adding camellia oleosa seed oil, heating liquid oil to 55 ℃ to keep for 25min, introducing the liquid oil into a packed bed reactor, keeping the temperature of the packed bed at 55 ℃, keeping the oil in the packed bed for 2h, and obtaining an acidolysis product after the reaction is finished, wherein the ratio of sunflower seed oil to linseed oil fatty acid is 1:1:0.3(mol/mol), and the molar ratio of the fatty acid to a palm stearin substrate is 10: 1. After the reaction is finished, removing possible impurities through filtration or centrifugation, deacidifying the secondary enzymolysis product by adopting reduced pressure distillation, in the third step of acidolysis reaction, adding camellia oleosa seed oil, mixed fatty acid of sunflower seed oil and linseed oil into the secondary enzymolysis product according to the molar ratio of the first two acidolysis substrates, selecting palm kernel oil fatty acid as a medium-chain fatty acid source, adding the palm kernel oil fatty acid, soybean oil and rapeseed oil fatty acid into a reaction system according to the proportion that the sum of the palm kernel oil fatty acid, the soybean oil and the rapeseed oil is 1:2, heating the oil to 55 ℃, keeping the temperature for 20min, introducing the oil into a packed bed reactor, keeping the temperature of the packed bed at 60 ℃, keeping the retention time of the oil in the packed bed at 1h, and obtaining the acidolysis product after the reaction is finished. The fatty acid composition and distribution of the final product is shown below.
TABLE 11 fatty acid composition and distribution of final product
The% sn-2 PA represents the ratio of sn-2 palmitic acid to total palmitic acid, and is calculated by the formula: sn-2 palmitic acid/(3X Total palmitic acid). times.100%
TABLE 12 amount of harmful substance produced
Example 3 | Comparative example 3 | |
Glycidyl ester (mg/kg) | 0.35 | 2.27 |
Chloropropanol ester (mg/kg) | 0.58 | 1.88 |
Trans fatty acid (%) | 0.21 | 0.94 |
The acidolysis reaction process is that the lipase firstly produces diglyceride from triglyceride through hydrolysis reaction, and then inserts fatty acid into diglyceride through esterification reaction to generate triglyceride. Since the reaction process uses sn-1, 3-position obligate lipase, the generated diglyceride is sn-1,2/2,3 diglyceride. sn-1,2/2,3 diglyceride is unstable, and acyl transfer occurs at a higher temperature, and the conversion occurs into sn-1,3 diglyceride, thereby causing the change of synthesized triglyceride sn-2 fatty acid during acidolysis. In the traditional method for removing fatty acid by reduced pressure distillation, sn-1,2/2,3 diglyceride in the reaction mixture is converted due to higher temperature of deacidification conditions, so that the acyl transfer amount in the subsequent acidolysis process is higher, and the generation amount of hazardous substances is increased due to repeated use of reduced pressure distillation. In the invention, through a low-temperature program fractionation method, palmitic acid, tripalmitin and partial glyceride with high melting points are separated by utilizing melting point difference, and then cyclic acidolysis is carried out by utilizing lipase, so that on one hand, saturated fatty acid, tripalmitin and partial glyceride are removed at low temperature, and simultaneously sn-1,2/2 and 3 diglyceride byproducts possibly existing in a system are ensured not to undergo acyl transfer, and when the acidolysis reaction is carried out again, the lipase can further synthesize triglyceride by using sn-1,2/2 and 3 diglyceride as a substrate, so that the acyl transfer of the product is reduced, the nutritional value of the product is ensured, and the generation amount of harmful substances in the reaction product is greatly reduced due to the reduction of a high-temperature treatment link, thereby improving the safety of the product. Saturated fatty acid is removed through low-temperature fractionation, the unsaturation degree of free fatty acid is increased, and the free fatty acid is recycled in the continuous acidolysis process, so that the cost is reduced, and the production process is simpler and more convenient.
It should be noted that the above-mentioned embodiments are only for illustrating the technical solutions of the present invention and not for limiting, and although the present invention has been described in detail with reference to the preferred embodiments, it should be understood by those skilled in the art that modifications or equivalent substitutions may be made on the technical solutions of the present invention without departing from the spirit and scope of the technical solutions of the present invention, which should be covered by the claims of the present invention.
Claims (9)
1. A preparation method of a mother emulsified structural fat is characterized by comprising the following steps: the method comprises the following steps:
acid hydrolysis: adding catalyst into fatty acid from palm hard and fat vegetable oil as raw material, and performing acidolysis;
separating and extracting: performing low-temperature program fractionation on the acidolysis product to separate out crystals and obtain liquid oil;
and (3) circulation: the steps of acidolysis and fractionation are circulated;
and (3) reduced pressure distillation: the fatty acid was removed by distillation under reduced pressure.
2. The method for preparing a marbled structured fat as claimed in claim 1, wherein: in the acidolysis, the catalyst is one or more of commercial sn-1,3 selective Lipase, such as Lipzyme RM IM, Lipzyme TL IM, Lipase DF and NS 40086.
3. The method for preparing a marbled structured fat as claimed in claim 1, wherein: the vegetable oil comprises one or more of soybean oil rich in oleic acid and linoleic acid, rapeseed oil, camellia seed oil, sunflower seed oil, linseed oil rich in linolenic acid, coconut oil rich in medium-chain fatty acid, palm kernel oil and the like.
4. The method for preparing a marbled structured fat as claimed in claim 1, wherein: the circulating step is that the steps of acidolysis and fractionation are repeated for 2-3 times.
5. The method for preparing a marbled structured fat as claimed in claim 1, wherein: in the acidolysis process, the reaction conditions are that in a packed bed reactor, the molar ratio of the fatty acid to the palm stearin substrate is 4:1-10:1, the temperature is 55-65 ℃, and the time is 1-4 hours; carrying out first low-temperature program fractionation after the first enzymolysis reaction, wherein the conditions comprise that the oil is heated to 55-65 ℃ and maintained for 20-30min, then the temperature is reduced to 35-40 ℃ at the speed of 4-10 ℃ per hour, the crystal is grown for 3-5h, then the temperature is reduced to 26-33 ℃ at the speed of 3-5 ℃ per hour, the crystal is grown for 2-10h, and after the fractionation crystallization is finished, the solid fat is filtered or centrifugally separated, so that the liquid oil is obtained.
6. The method for preparing a marbled structured fat as claimed in claim 1, wherein: when acidolysis is carried out in the circulating process, the liquid oil obtained in the fractionation step is introduced into a packed bed reactor, the reaction temperature is 45-60 ℃, and the reaction time is 1-4 h; and the second low-temperature separation is carried out by heating the oil to 50-55 deg.C for 25-30min, cooling to 20-25 deg.C at 6-15 deg.C/h, growing crystal for 4-8h, and filtering or centrifuging to separate solid fat to obtain liquid oil.
7. The method for preparing a marbled structured fat as claimed in claim 1, wherein: in the circulation process, during the third acidolysis, the condition of the third enzyme-catalyzed acidolysis is that the liquid oil obtained by the second fractionation is introduced into the packed bed reactor, the reaction temperature is 50-60 ℃, and the reaction time is 1-3 h.
8. The method for preparing human milk substitute fat and the method for preparing the same according to claim 1, wherein: coconut oil or palm kernel oil fatty acid is added in the last acidolysis reaction.
9. The method for preparing human milk substitute fat and the method for preparing the same according to claim 1, wherein: in the acidolysis, fractionation and reduced pressure distillation, the grease is placed in protective gas.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202110878001.6A CN113832200B (en) | 2021-07-30 | 2021-07-30 | Preparation method of breast milk structured fat |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202110878001.6A CN113832200B (en) | 2021-07-30 | 2021-07-30 | Preparation method of breast milk structured fat |
Publications (2)
Publication Number | Publication Date |
---|---|
CN113832200A true CN113832200A (en) | 2021-12-24 |
CN113832200B CN113832200B (en) | 2023-12-01 |
Family
ID=78963112
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202110878001.6A Active CN113832200B (en) | 2021-07-30 | 2021-07-30 | Preparation method of breast milk structured fat |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN113832200B (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114921291A (en) * | 2022-06-13 | 2022-08-19 | 东北农业大学 | Preparation method of breast milk structure fat |
Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5658768A (en) * | 1993-05-13 | 1997-08-19 | Loders Croklaan B.V. | Process for production of human milk fat replacers by enzymatic conversion of triglycerides |
US20080193624A1 (en) * | 2005-04-27 | 2008-08-14 | Enzymotec Ltd. | Human Milk Fat Substitutes |
CN104855542A (en) * | 2015-05-06 | 2015-08-26 | 江南大学 | Preparation method of human milk alternative fat combining enzymatic acidolysis and physical mixing |
CN104862350A (en) * | 2015-05-06 | 2015-08-26 | 江南大学 | Method for preparing 1, 3-dilinolein-2-palmitic acid triglyceride |
CN107164084A (en) * | 2017-05-15 | 2017-09-15 | 乌鲁木齐上善元生物科技有限公司 | A kind of production method of the vegetable oil rich in high content unrighted acid |
CN107751418A (en) * | 2017-09-13 | 2018-03-06 | 华南理工大学 | A kind of preparation method of human milk fat structure fat substitutes |
CN108841880A (en) * | 2018-08-01 | 2018-11-20 | 浙江汇能生物股份有限公司 | A kind of preparation method of 1,3-Dioleic acid-2-palmitoyl triglyceride |
US20210002681A1 (en) * | 2018-03-02 | 2021-01-07 | Fuji Oil Holdings Inc. | Production method for oil/fat composition rich in palmitic acid at position 2 |
CN112314710A (en) * | 2020-08-21 | 2021-02-05 | 南昌大学 | Preparation method and application of Chinese breast milk triglyceride substitute fat |
-
2021
- 2021-07-30 CN CN202110878001.6A patent/CN113832200B/en active Active
Patent Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5658768A (en) * | 1993-05-13 | 1997-08-19 | Loders Croklaan B.V. | Process for production of human milk fat replacers by enzymatic conversion of triglycerides |
US20080193624A1 (en) * | 2005-04-27 | 2008-08-14 | Enzymotec Ltd. | Human Milk Fat Substitutes |
CN104855542A (en) * | 2015-05-06 | 2015-08-26 | 江南大学 | Preparation method of human milk alternative fat combining enzymatic acidolysis and physical mixing |
CN104862350A (en) * | 2015-05-06 | 2015-08-26 | 江南大学 | Method for preparing 1, 3-dilinolein-2-palmitic acid triglyceride |
CN107164084A (en) * | 2017-05-15 | 2017-09-15 | 乌鲁木齐上善元生物科技有限公司 | A kind of production method of the vegetable oil rich in high content unrighted acid |
CN107751418A (en) * | 2017-09-13 | 2018-03-06 | 华南理工大学 | A kind of preparation method of human milk fat structure fat substitutes |
US20210002681A1 (en) * | 2018-03-02 | 2021-01-07 | Fuji Oil Holdings Inc. | Production method for oil/fat composition rich in palmitic acid at position 2 |
CN108841880A (en) * | 2018-08-01 | 2018-11-20 | 浙江汇能生物股份有限公司 | A kind of preparation method of 1,3-Dioleic acid-2-palmitoyl triglyceride |
CN112314710A (en) * | 2020-08-21 | 2021-02-05 | 南昌大学 | Preparation method and application of Chinese breast milk triglyceride substitute fat |
Non-Patent Citations (2)
Title |
---|
张艳: "Candida sp.99-125脂肪酶催化合成高纯人乳脂替代品的研究", 《中国优秀硕士学位论文全文数据库 工程科技I辑》 * |
熊志琴: "母乳脂替代品的酶法制备及性质研究", 《中国优秀硕士学位论文全文数据库 工程科技I辑》 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114921291A (en) * | 2022-06-13 | 2022-08-19 | 东北农业大学 | Preparation method of breast milk structure fat |
Also Published As
Publication number | Publication date |
---|---|
CN113832200B (en) | 2023-12-01 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN104855542B (en) | The human milk of a kind of combination enzyme process acidolysis and physical mixed substitutes the preparation method of fat | |
CN104862350B (en) | A kind of method for preparing bis- oleic acid -2- palmitic acids of 1,3-, three ester | |
CN104186701B (en) | Preparation method of human milk substitute fat based on triglyceride composition and evaluating method of human milk substitute fat | |
CN108244273A (en) | A kind of fat or oil composition and preparation method thereof | |
CN102845537A (en) | Preparation method of human milk fat substitute | |
CN102827885A (en) | Composition containing 1,3-di-unsaturated fatty acyl-2-saturated fatty acyl glyceryl ester as well as preparation method and application thereof | |
CN104186705A (en) | Enzymatic acidolysis-based method for synthesizing structured lipids from palmitic acid triglycerides | |
CN111172210A (en) | Method for preparing arachidonic acid glyceride rich by two-step enzyme method and product thereof | |
CN114836483A (en) | Preparation method of oil composition rich in OPL and OPO | |
CN113832200B (en) | Preparation method of breast milk structured fat | |
CN111363766B (en) | Preparation method of structural lipid for improving DHA bioavailability and product thereof | |
CN106359663A (en) | Breast milk fat substitute prepared from oil of tilapia, application and method | |
CN112841313A (en) | Preparation method of oil rich in OPL and OPO and product thereof | |
CN103027133A (en) | Zero- or low-trans-fatty-acid structured lipid for artificial cream and vegetable shortening | |
CN115024367B (en) | Breast milk structured fat simulating triglyceride composition and preparation method thereof | |
CN113481248B (en) | Method for preparing 1, 3-dioleoyl-2-palmitic acid triglyceride | |
CN113615743B (en) | Preparation method of human milk substitute fat simulating breast milk fat structure | |
CN113416755B (en) | Industrial production method of 1, 3-dioleic acid-2-palmitic acid triglyceride and product thereof | |
CN113575697B (en) | Preparation method of breast milk fat substitute based on animal milk fat | |
EP3750405A1 (en) | Production method for oil/fat composition rich in palmitic acid at position 2 | |
CN113575696A (en) | Preparation method of structural lipid based on breast milk triglyceride composition | |
CN113337551A (en) | Preparation method of structural triglyceride | |
CN113621660B (en) | Preparation method of structural lipid for regulating lipid composition of infant formula milk powder | |
CN113584094B (en) | Preparation method of triglyceride with 1,3 unsaturated-2-saturated fatty acid structure based on milk fat | |
CN113584095B (en) | Product rich in 1, 3-unsaturated-2-saturated fatty acid structured fat and preparation method thereof |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant |