CN104651424A - Preparation method of structure grease - Google Patents
Preparation method of structure grease Download PDFInfo
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- CN104651424A CN104651424A CN201510067260.5A CN201510067260A CN104651424A CN 104651424 A CN104651424 A CN 104651424A CN 201510067260 A CN201510067260 A CN 201510067260A CN 104651424 A CN104651424 A CN 104651424A
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- structure grease
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- 239000004519 grease Substances 0.000 title claims abstract description 66
- 238000002360 preparation method Methods 0.000 title claims abstract description 27
- DCXXMTOCNZCJGO-UHFFFAOYSA-N Glycerol trioctadecanoate Natural products CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 claims abstract description 76
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 25
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 25
- 239000011630 iodine Substances 0.000 claims abstract description 25
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims abstract description 17
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims abstract description 9
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims abstract description 9
- 230000002255 enzymatic effect Effects 0.000 claims abstract description 7
- 238000009884 interesterification Methods 0.000 claims abstract description 7
- 238000005516 engineering process Methods 0.000 claims abstract description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 11
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 10
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 9
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 9
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 9
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 9
- 239000005642 Oleic acid Substances 0.000 claims description 9
- 235000019482 Palm oil Nutrition 0.000 claims description 9
- 238000005194 fractionation Methods 0.000 claims description 9
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 9
- 239000002540 palm oil Substances 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 claims description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 3
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 claims description 3
- HXWJFEZDFPRLBG-UHFFFAOYSA-N Timnodonic acid Natural products CCCC=CC=CCC=CCC=CCC=CCCCC(O)=O HXWJFEZDFPRLBG-UHFFFAOYSA-N 0.000 claims description 3
- JAZBEHYOTPTENJ-JLNKQSITSA-N all-cis-5,8,11,14,17-icosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O JAZBEHYOTPTENJ-JLNKQSITSA-N 0.000 claims description 3
- 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 3
- 235000020661 alpha-linolenic acid Nutrition 0.000 claims description 3
- 229940114079 arachidonic acid Drugs 0.000 claims description 3
- 235000021342 arachidonic acid Nutrition 0.000 claims description 3
- 239000001273 butane Substances 0.000 claims description 3
- DVSZKTAMJJTWFG-UHFFFAOYSA-N docosa-2,4,6,8,10,12-hexaenoic acid Chemical compound CCCCCCCCCC=CC=CC=CC=CC=CC=CC(O)=O DVSZKTAMJJTWFG-UHFFFAOYSA-N 0.000 claims description 3
- MBMBGCFOFBJSGT-KUBAVDMBSA-N docosahexaenoic acid Natural products CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O MBMBGCFOFBJSGT-KUBAVDMBSA-N 0.000 claims description 3
- 229960005135 eicosapentaenoic acid Drugs 0.000 claims description 3
- 235000020673 eicosapentaenoic acid Nutrition 0.000 claims description 3
- 229960004232 linoleic acid Drugs 0.000 claims description 3
- 229960004488 linolenic acid Drugs 0.000 claims description 3
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 3
- 239000003921 oil Substances 0.000 claims description 3
- 235000019198 oils Nutrition 0.000 claims description 3
- 229960002969 oleic acid Drugs 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 238000009776 industrial production Methods 0.000 abstract description 5
- 239000000047 product Substances 0.000 abstract description 5
- 239000002994 raw material Substances 0.000 abstract description 4
- 230000009286 beneficial effect Effects 0.000 abstract description 3
- 239000006227 byproduct Substances 0.000 abstract description 3
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 abstract 2
- 125000005456 glyceride group Chemical group 0.000 abstract 1
- 102000004882 Lipase Human genes 0.000 description 18
- 108090001060 Lipase Proteins 0.000 description 18
- 239000004367 Lipase Substances 0.000 description 18
- 235000019421 lipase Nutrition 0.000 description 18
- 238000007670 refining Methods 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 13
- 238000000034 method Methods 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 238000010792 warming Methods 0.000 description 10
- 238000009835 boiling Methods 0.000 description 9
- 238000004332 deodorization Methods 0.000 description 9
- 238000000199 molecular distillation Methods 0.000 description 9
- 238000004809 thin layer chromatography Methods 0.000 description 9
- 235000021588 free fatty acids Nutrition 0.000 description 8
- 239000008367 deionised water Substances 0.000 description 7
- 229910021641 deionized water Inorganic materials 0.000 description 7
- 239000003925 fat Substances 0.000 description 7
- 235000019197 fats Nutrition 0.000 description 6
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 5
- 229910052791 calcium Inorganic materials 0.000 description 5
- 239000011575 calcium Substances 0.000 description 5
- 235000020256 human milk Nutrition 0.000 description 5
- 210000004251 human milk Anatomy 0.000 description 5
- 150000004671 saturated fatty acids Chemical class 0.000 description 5
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 5
- 102000004190 Enzymes Human genes 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000002632 lipids Chemical class 0.000 description 3
- 125000005457 triglyceride group Chemical group 0.000 description 3
- 206010010774 Constipation Diseases 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 206010000087 Abdominal pain upper Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
- 239000008157 edible vegetable oil Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000009886 enzymatic interesterification Methods 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- TYLNXKAVUJJPMU-UHFFFAOYSA-N ethyl docosa-2,4,6,8,10,12-hexaenoate Chemical compound CCCCCCCCCC=CC=CC=CC=CC=CC=CC(=O)OCC TYLNXKAVUJJPMU-UHFFFAOYSA-N 0.000 description 1
- 235000013350 formula milk Nutrition 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 208000003243 intestinal obstruction Diseases 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 230000005195 poor health Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 238000005809 transesterification reaction Methods 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
- C12P7/6472—Glycerides containing polyunsaturated fatty acid [PUFA] residues, i.e. having two or more double bonds in their backbone
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Zoology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Microbiology (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Lubricants (AREA)
- Fats And Perfumes (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
The invention relates to a preparation method of structure grease. The preparation method comprises the following steps: preparing stearin with iodine value of 14-25 and rich in palmitic acid residues; and performing Sn-1,3 enzymatic directed interesterification on the stearin and rich in palmitic acid residues and unsaturated fatty acid or non-glyceride. According to the preparation method of the structure grease, the cost for obtaining the raw materials is low, raw materials can be directly purchased or obtained through simple processing, and the large-scale industrial production is facilitated; secondly, the technology is simple, the needed equipment is less, and the production cost of the product can be lowered; again, the side products obtained in the preparation are fewer, thus being beneficial to environment protection.
Description
Technical field
The present invention relates to a kind of preparation method of Structure grease, particularly a kind of preparation method of the Structure grease containing 1.3-bis-unsaturated fatty acids-2-palmitinic acid.
Background technology
Triglyceride level is the main grease composition of human consumption.Modern nutriology is verified, and human body is in the process of devil's brew three ester, and meeting selective hydrolysis Sn-1, the lipid acid on 3, forms 2-mono-glycerides and a large amount of free fatty acidies.These free fatty acidies there will be two kinds of reactions in vivo: 1, by own absorption; 2, with after other substance reactions in body be discharged.Research shows, compared with free unsaturated fatty acid, free saturated fatty acid uptake rate is slow, and easier and calcium reacts, and forms insoluble soap calcium, and then is excreted.As can be seen here, relative to the triglyceride level producing free saturated fatty acid, the triglyceride level producing free unsaturated fatty acid is more conducive to the absorption of human body.
Edible oil commercially available is at present mainly derived from plant, and its saturated fatty acid is mainly distributed in sn-1,3, human body, in digestive process, not only lost a large amount of fat and calcium, and its soap calcium generated can increase the hardness of ight soil, cause part population constipation and stomachache, even cause intestinal obstruction.If saturated fatty acid to be concentrated on the sn-2 position (also referred to as " 2 ") of triglyceride level, then can effectively address this problem, especially in poor health, the crowd that functions of intestines and stomach is bad, effect is more obvious.
In breast milk, the fat of about 98% exists with the form of triglyceride level, and wherein the content of palmitinic acid (Palmitic acid, C16:0, saturated fatty acid) accounts for 20-25%, and oleic acid (oleic acid, C18:1, unsaturated fatty acids) content accounts for 30-38%.Further, most palmitinic acid is distributed in 2 of triglyceride level, and oleic acid is then mainly distributed on Sn-1 and Sn-3 position.A large amount of human trials and experimentation on animals confirm all, and the easy of human milk fat is absorbed by infant, and one of them major reason is just the triglyceride structure of this uniqueness in breast milk.
By the inspiration of triglyceride structure unique in breast milk, part manufacturer has been had to utilize the Structure grease modification of natural fats and oils being taken to production simulation breast milk at present, and added in baby milk powder and special diet, this not only can improve human body to assimilated efficiency that is fatty and calcium, the hardness of ight soil can also be reduced, reduce constipation and ileac probability of occurrence.In this Structure grease, sn-1,3 are mainly unsaturated fatty acids, and 2 are mainly palmitinic acid, are therefore also referred to as 1.3-bis-unsaturated fatty acids-2-palmitinic acid Structure grease.
Chinese Patent Application No. be 200880006607.3 application discloses that a kind of production structure grease method, key step comprises: will comprise three palmitoyl glycerides and the palm oil stearin fractions that iodine number is 18-40 carries out random transesterify under chemical catalyst or the effect of nonspecific lipid enzyme, again with oleic acid or its nonglyceride 1, enzymatic interesterification procedure is carried out, the obtained composition comprising OPO glyceryl ester after being separated under the effect of 3 specificity enzymes.But the technique of this preparation method is comparatively loaded down with trivial details, the effect of random transesterify is difficult to accurate control, and the product quality otherness therefore produced is larger.On the other hand, this technique needs the equipment of use more, and therefore the cost compare of products production is high, is unfavorable for carrying out large-scale industrial production.
Chinese Patent Application No. be 200680033013.2 application discloses that a kind of by making the ester of palm oil stearin that iodine number (IV) is 8-12 and oleic acid or its nonglyceride carry out the method that enzymatic transesterification obtains OPO Structure grease.But existing commercially available palm oil stearin iodine number (IV) is general all more than 20, is translated into the palm oil stearin that iodine number (IV) is 8-12, need to carry out repeatedly winterization and divide and carry, cost is high, and energy consumption is large.Further, carry even if divide through repeatedly winterization, can not guarantee that palm oil stearin iodine number drops to 8-12 completely, therefore, this preparation method is difficult to be applied to large-scale industrial production.
Summary of the invention
The object of this invention is to provide a kind of technique simple, the with low cost and preparation method of environmentally friendly Structure grease.
For achieving the above object, the preparation method of Structure grease of the present invention, comprises the steps; Obtain the tristearin being rich in palmitic acid residues that iodine number is 14 to 25; The tristearin being rich in palmitic acid residues by above-mentioned and unsaturated fatty acids or its nonglyceride carry out Sn-1, and 3 enzymatic directed inter-esterification, obtain Structure grease.
Further, in step (1), commercially available plam oil or palm oil stearin can be divided by dry fractionation or solvent and carry, obtain the tristearin being rich in palmitic acid residues that iodine number is 14 to 25.
Optionally, in step (1), directly buy commercially available iodine number be 14 to 25 the palm oil stearin being rich in palmitic acid residues slightly oily.
Further, in the enzymatic directed inter-esterification system of step (2), add solvent, described solvent comprises butane, hexane, acetone, hexanaphthene, octane or octane-iso.
Further, in step (2), unsaturated fatty acids comprises oleic acid, linolic acid, linolenic acid, arachidonic acid, timnodonic acid and docosahexenoic acid.
Further, this preparation method comprises step (3) further: by step (2) obtain Structure grease and carry out refinement treatment.
Further, the refinement treatment of step (3) comprises fractionation technology.
The preparation method of Structure grease of the present invention has following beneficial effect: first, and the cost compare that raw material obtains is low, can directly buy, or can obtain through simple processing, is conducive to large-scale industrial production; Secondly, technique is simple, needs the equipment of use less, can reduce the cost of products production; Again, in preparation process, by product is less, is conducive to environmental protection.
Embodiment
Below in conjunction with specific examples, the present invention is described in further detail.
embodiment 1 (comparative examples)
(1) provide a kind of iodine number be 42 palm stearin.
(2) reaction substrate palm stearin 25g, nonspecific lipid enzyme 1.25g are placed in flask, stir and be warming up to 60 DEG C and keep constant, sustained reaction, after 8 hours, is crossed and is filtered enzyme, obtain fat A.
(3) mixed with oleic acid 75g by fat A 25g, be placed in four-hole boiling flask, stir and be warming up to 50 DEG C and keep constant, add sn-1,3 specific lipase 2.5g, back flow reaction 3 hours (directed inter-esterification, lower same), obtains rough Structure grease.
(4) aforementioned rough Structure grease is carried out refinement treatment, refining step comprises: cross and filter lipase, and molecular distillation removing free fatty acids, obtains the Structure grease of refining after deodorization.By GC(high temperature capillary post, fid detector, lower same) and thin-layer chromatography detection, in Structure grease, the content of 2-palmitin is the content of 39.0%, 1,3-bis-oleic acid-2-palmitin (also known as " OPO ") is 25.9%.
embodiment 2
(1) from the market directly buy iodine number be the palm stearin of 25.
(2) palm stearin 25g, oleic acid 13g are mixed, be placed in four-hole boiling flask, stir and be warming up to 50 DEG C and keep constant, add sn-1,3 specific lipase 0.94g, back flow reaction 3 hours, obtains rough Structure grease.
(3) aforementioned rough Structure grease is carried out refinement treatment, refining step includes but not limited to: cross and filter lipase, and molecular distillation removing free fatty acids, obtains the Structure grease of refining after deodorization.Detected by GC and thin-layer chromatography, in Structure grease, the content of 2-palmitin is the content of 51.0%, 1,3-bis-oleic acid-2-palmitin (also known as " OPO ") is 33.1%.
embodiment 3
(1) from the market directly buy iodine number be the palm stearin of 23.
(2) palm stearin 200g, linolic acid 200g, deionized water 0.4g mixed and add 800ml butane, being placed in four-hole boiling flask, stirring and be warming up to 50 DEG C and keep constant, add sn-1,3 specific lipase 16g, back flow reaction 3 hours, obtains rough Structure grease.
(3) aforementioned rough Structure grease is carried out refinement treatment, refining step comprises: cross and filter lipase, and molecular distillation removing free fatty acids, obtains the Structure grease of refining after deodorization.Detected by GC and thin-layer chromatography, in Structure grease, the content of 2-palmitin is the content of 58.2%, 1,3-dilinoleic acid-2-palmitin is 37.3%.
embodiment 4
(1) from the market directly buy iodine number be the palm stearin of 21.
(2) palm stearin 240g, linolenic acid 360g, deionized water 0.6g mixed and add 1200ml hexane, being placed in four-hole boiling flask, stirring and be warming up to 55 DEG C and keep constant, add sn-1,3 specific lipase 30g, back flow reaction 4 hours, obtains rough Structure grease.
(3) aforementioned rough Structure grease is carried out refinement treatment, refining step comprises: cross and filter lipase, and molecular distillation removing free fatty acids, carries out dry fractionation further after deodorization, obtain the Structure grease of refining.Detected by GC and thin-layer chromatography, in Structure grease, the content of 2-palmitin is the content of 65.5%, 1,3-bis-linolenic acid-2-palmitin is 42.5%.
embodiment 5
(1) from the market directly buy iodine number be the palm stearin of 19.
(2) palm stearin 2500g, arachidonic acid 5000g, deionized water 15g mixed and add 15000ml acetone, being placed in four-hole boiling flask, stirring and be warming up to 60 DEG C and keep constant, add sn-1,3 specific lipase 375g, back flow reaction 4 hours, obtains rough Structure grease.
(3) aforementioned rough Structure grease is carried out refinement treatment, refining step comprises: cross and filter lipase, and molecular distillation removing free fatty acids, carries out dry fractionation further after deodorization, obtain the Structure grease of refining.Detected by GC and thin-layer chromatography, in Structure grease, the content of 2-palmitin is 68.0%, 1,3-bis-arachidonic acid-2-palmitic acid ester content is 47.8%.
embodiment 6
(1) from buying the palm stearin that iodine number is 25-30 on the market, by dry fractionation, obtaining iodine number is the palm stearin of 19.
(2) palm stearin 200g, timnodonic acid 600g, deionized water 1.6g mixed and add 1600ml hexanaphthene, being placed in four-hole boiling flask, stirring and be warming up to 60 DEG C and keep constant, add sn-1,3 specific lipase 40g, back flow reaction 5 hours, obtains rough Structure grease.
(3) aforementioned rough Structure grease is carried out refinement treatment, refining step comprises: cross and filter lipase, and molecular distillation removing free fatty acids, carries out dry fractionation further after deodorization, obtain the Structure grease of refining.Detected by GC and thin-layer chromatography, in Structure grease, the content of 2-palmitin is the content of 70.9%, 1,3-bis-timnodonic acid-2-palmitin is 48.6%.
embodiment 7
(1) from buying the palm stearin that iodine number is 25-30 on the market, being divided by solvent and carrying, obtain the palm stearin that iodine number is 18.
(2) palm stearin 500g, docosahexenoic acid 2000g, deionized water 7.5g are mixed and add 5000ml octane, be placed in four-hole boiling flask, stirring is warming up to 65 DEG C and keeps constant, add sn-1,3 specific lipase 150g, back flow reaction 5 hours, obtains rough Structure grease.
(3) aforementioned rough Structure grease is carried out refinement treatment, refining step comprises: cross and filter lipase, and molecular distillation removing free fatty acids, carries out solvent further and divide and carry, obtain the Structure grease of refining after deodorization.Detected by GC and thin-layer chromatography, in Structure grease, the content of 2-palmitin is the content of 68.8%, 1,3-bis-docosahexenoic acid-2-palmitin is 44.9%.
embodiment 8
(1) from buying the palm stearin that iodine number is 25-30 on the market, by dry fractionation, the palm stearin that iodine number is 16 is obtained.
(2) palm stearin 1000g, Witconol 2301 4000g, deionized water 20g mixed and add 10000ml octane-iso, being placed in four-hole boiling flask, stirring and be warming up to 70 DEG C and keep constant, add sn-1,3 specific lipase 400g, back flow reaction 6 hours, obtains rough Structure grease.
(3) aforementioned rough Structure grease is carried out refinement treatment, refining step comprises: cross and filter lipase, and molecular distillation removing free fatty acid methyl esters, carries out solvent further and divide and carry, obtain the Structure grease of refining after deodorization.Detected by GC and thin-layer chromatography, in Structure grease, 2-palmitic acid ester content is 67.5%, 1,3-bis-oleic acid-2-palmitic acid ester content is 39.9%.
embodiment 9
(1) from buying the palm stearin that iodine number is 25-30 on the market, being divided by solvent and carrying, obtain the palm stearin that iodine number is 14.
(2) palm stearin 2500g, docosahexenoic acid ethyl ester 12500g, deionized water 75g are mixed and add 30000ml hexane, be placed in four-hole boiling flask, stirring is warming up to 75 DEG C and keeps constant, add sn-1,3 specific lipase 1500g, back flow reaction 6 hours, obtains rough Structure grease.
(3) aforementioned rough Structure grease is carried out refinement treatment, refining step comprises: cross and filter lipase, molecular distillation removing free-fat acetoacetic ester, carries out solvent further and divides and carry, obtain the Structure grease of refining after deodorization.Detected by GC and thin-layer chromatography, in Structure grease, the content of 2-palmitin is the content of 67.7%, 1,3-bis-docosahexenoic acid-2-palmitin is 35.8%.
The preparation method of Structure grease of the present invention has following beneficial effect, and first, the cost compare that raw material obtains is low, can directly buy, or can obtain through simple processing, is conducive to large-scale industrial production; Secondly, technique is simple, needs the equipment of use less, can reduce the cost of products production; Again, in preparation process, by product is less, is conducive to environmental protection.
Claims (9)
1. a preparation method for Structure grease, comprises the steps:
Obtain the tristearin being rich in palmitic acid residues that iodine number is 14 to 25;
The tristearin being rich in palmitic acid residues by above-mentioned and unsaturated fatty acids or its nonglyceride carry out Sn-1, and 3 enzymatic directed inter-esterification, obtain Structure grease.
2. the preparation method of a kind of Structure grease according to claim 1, it is characterized in that: step (1) comprising: commercially available plam oil or palm oil stearin are divided by dry fractionation or solvent and carries, obtain the tristearin being rich in palmitic acid residues that iodine number is 14 to 25.
3. the preparation method of a kind of Structure grease according to claim 1, is characterized in that: step (1) comprising: directly buy commercially available iodine number be 14 to 25 the palm oil stearin being rich in palmitic acid residues slightly oily.
4. the preparation method of a kind of Structure grease according to claim 1, is characterized in that: in the enzymatic directed inter-esterification system of step (2), add appropriate water.
5. the preparation method of a kind of Structure grease according to claim 1, is characterized in that: in the enzymatic directed inter-esterification system of step (2), and add solvent, described solvent comprises butane, hexane, acetone, hexanaphthene, octane or octane-iso.
6. the preparation method of a kind of Structure grease according to claim 1, is characterized in that: in step (2), unsaturated fatty acids comprises oleic acid, linolic acid, linolenic acid, arachidonic acid, timnodonic acid and docosahexenoic acid.
7. the preparation method of a kind of Structure grease according to claim 1, is characterized in that: this preparation method comprises step (3) further: by step (2) obtain Structure grease and carry out refinement treatment.
8. the preparation method of a kind of Structure grease according to claim 7, is characterized in that: the refinement treatment of step (3) comprises fractionation technology.
9. the composition containing Structure grease, is characterized in that: described Structure grease is obtained by preparation method arbitrary in claim 1-8.
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| CN201510067260.5A CN104651424B (en) | 2015-02-10 | 2015-02-10 | A kind of preparation method of Structure grease |
| CN201610289497.2A CN105861579A (en) | 2015-02-10 | 2015-02-10 | Composition containing structural grease |
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| CN201510067260.5A CN104651424B (en) | 2015-02-10 | 2015-02-10 | A kind of preparation method of Structure grease |
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| CN201610289497.2A Division CN105861579A (en) | 2015-02-10 | 2015-02-10 | Composition containing structural grease |
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| CN201510067260.5A Active CN104651424B (en) | 2015-02-10 | 2015-02-10 | A kind of preparation method of Structure grease |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108265089A (en) * | 2016-12-30 | 2018-07-10 | 中粮集团有限公司 | A kind of fat or oil composition containing bis- oleic acid -2- palmitic acids of 1,3-, three ester and preparation method thereof |
| CN108265089B (en) * | 2016-12-30 | 2021-06-11 | 中粮集团有限公司 | Oil and fat composition containing 1, 3-dioleoyl-2-palmitic acid triglyceride and preparation method thereof |
| CN109984205A (en) * | 2017-12-29 | 2019-07-09 | 中粮集团有限公司 | A kind of fat or oil composition and preparation method thereof |
| CN109247397A (en) * | 2018-09-18 | 2019-01-22 | 湖北福星生物科技有限公司 | A kind of Sn-2 Structure grease and preparation method thereof rich in docosahexaenoic acid |
| CN110150666A (en) * | 2019-06-14 | 2019-08-23 | 广东省农业科学院蚕业与农产品加工研究所 | A kind of fat or oil composition and preparation method thereof |
| CN116287036A (en) * | 2023-03-21 | 2023-06-23 | 安徽森那贝生物科技有限公司 | Method for producing 1, 3-dioleoyl 2-palmitoyl glycerol |
| CN116287036B (en) * | 2023-03-21 | 2023-10-20 | 安徽森那贝生物科技有限公司 | Method for producing 1, 3-dioleoyl 2-palmitoyl glycerol |
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|---|---|
| CN104651424B (en) | 2018-08-17 |
| CN105861579A (en) | 2016-08-17 |
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