CN104862350B - 一种制备1,3-二油酸-2-棕榈酸甘油三酯的方法 - Google Patents
一种制备1,3-二油酸-2-棕榈酸甘油三酯的方法 Download PDFInfo
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- 235000021314 Palmitic acid Nutrition 0.000 title claims abstract description 36
- 238000000034 method Methods 0.000 title claims abstract description 19
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 title claims abstract description 17
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 title claims abstract description 17
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 title claims abstract description 17
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 239000005642 Oleic acid Substances 0.000 title claims abstract description 17
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 150000002148 esters Chemical class 0.000 title abstract description 11
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims abstract description 54
- 235000019198 oils Nutrition 0.000 claims abstract description 50
- 241001233037 catfish Species 0.000 claims abstract description 48
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims abstract description 23
- 239000007787 solid Substances 0.000 claims abstract description 20
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims abstract description 17
- 239000003054 catalyst Substances 0.000 claims abstract description 7
- 239000002253 acid Substances 0.000 claims description 27
- 125000001931 aliphatic group Chemical group 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 238000000199 molecular distillation Methods 0.000 claims description 9
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 108010048733 Lipozyme Proteins 0.000 claims description 6
- 238000001704 evaporation Methods 0.000 claims description 5
- 239000000758 substrate Substances 0.000 claims description 5
- 235000019484 Rapeseed oil Nutrition 0.000 claims description 4
- 241001417930 Siluridae Species 0.000 claims description 4
- 238000002425 crystallisation Methods 0.000 claims description 2
- 230000008025 crystallization Effects 0.000 claims description 2
- 230000008020 evaporation Effects 0.000 claims 1
- 239000012535 impurity Substances 0.000 claims 1
- 239000003921 oil Substances 0.000 abstract description 44
- 239000002994 raw material Substances 0.000 abstract description 7
- 235000015112 vegetable and seed oil Nutrition 0.000 abstract description 5
- 239000008158 vegetable oil Substances 0.000 abstract description 5
- 108090001060 Lipase Proteins 0.000 abstract description 4
- 102000004882 Lipase Human genes 0.000 abstract description 4
- 239000004367 Lipase Substances 0.000 abstract description 4
- 235000019421 lipase Nutrition 0.000 abstract description 4
- 235000013336 milk Nutrition 0.000 abstract description 3
- 239000008267 milk Substances 0.000 abstract description 3
- 210000004080 milk Anatomy 0.000 abstract description 3
- 239000000654 additive Substances 0.000 abstract description 2
- 230000000996 additive effect Effects 0.000 abstract description 2
- 238000001914 filtration Methods 0.000 abstract description 2
- 239000012530 fluid Substances 0.000 abstract description 2
- 235000013350 formula milk Nutrition 0.000 abstract description 2
- 239000000843 powder Substances 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 description 14
- 238000009826 distribution Methods 0.000 description 11
- 150000003626 triacylglycerols Chemical class 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 10
- 150000002943 palmitic acids Chemical class 0.000 description 7
- 108090000790 Enzymes Proteins 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 4
- 229940088598 enzyme Drugs 0.000 description 4
- 241000894007 species Species 0.000 description 4
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 4
- 235000020256 human milk Nutrition 0.000 description 3
- 210000004251 human milk Anatomy 0.000 description 3
- 229940040461 lipase Drugs 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 235000019486 Sunflower oil Nutrition 0.000 description 2
- 230000009102 absorption Effects 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000004519 grease Substances 0.000 description 2
- FCCDDURTIIUXBY-UHFFFAOYSA-N lipoamide Chemical group NC(=O)CCCCC1CCSS1 FCCDDURTIIUXBY-UHFFFAOYSA-N 0.000 description 2
- 150000004671 saturated fatty acids Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000002600 sunflower oil Substances 0.000 description 2
- PVNIQBQSYATKKL-UHFFFAOYSA-N tripalmitin Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCC PVNIQBQSYATKKL-UHFFFAOYSA-N 0.000 description 2
- 206010067484 Adverse reaction Diseases 0.000 description 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- 206010010774 Constipation Diseases 0.000 description 1
- 102100031416 Gastric triacylglycerol lipase Human genes 0.000 description 1
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical group [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 description 1
- 108050006759 Pancreatic lipases Proteins 0.000 description 1
- 102000019280 Pancreatic lipases Human genes 0.000 description 1
- 230000006838 adverse reaction Effects 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940099352 cholate Drugs 0.000 description 1
- BHQCQFFYRZLCQQ-OELDTZBJSA-N cholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 BHQCQFFYRZLCQQ-OELDTZBJSA-N 0.000 description 1
- 210000001268 chyle Anatomy 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 108010091264 gastric triacylglycerol lipase Proteins 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 210000002490 intestinal epithelial cell Anatomy 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 229940116369 pancreatic lipase Drugs 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 125000005471 saturated fatty acid group Chemical group 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229960001947 tripalmitin Drugs 0.000 description 1
- 239000010913 used oil Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
- A23C11/00—Milk substitutes, e.g. coffee whitener compositions
- A23C11/02—Milk substitutes, e.g. coffee whitener compositions containing at least one non-milk component as source of fats or proteins
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
- A23D9/02—Other edible oils or fats, e.g. shortenings, cooking oils characterised by the production or working-up
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Fats And Perfumes (AREA)
- Edible Oils And Fats (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
Description
FA种类 | FA | sn-2FA | %sn-2FA | sn-1,3FA |
C14:0 | 3.59 | 4.10 | 38.07 | 3.34 |
C16:0 | 22.39 | 57.80 | 86.05 | 4.69 |
C18:0 | 5.62 | 5.30 | 31.44 | 5.78 |
C18:1 | 60.10 | 21.88 | 12.14 | 79.21 |
C18:2 | 7.03 | 8.40 | 39.83 | 6.35 |
C18:3 | 0.30 | 0.40 | 44.44 | 0.25 |
FA种类 | FA | sn-2FA | %sn-2FA | sn-1,3FA |
C14:0 | 3.42 | 4.15 | 40.45 | 3.06 |
C16:0 | 23.39 | 57.10 | 81.37 | 6.54 |
C18:0 | 5.67 | 5.51 | 32.39 | 5.75 |
C18:1 | 59.60 | 21.17 | 11.84 | 78.82 |
C18:2 | 7.22 | 8.86 | 40.90 | 6.40 |
C18:3 | 0.30 | 0.40 | 44.44 | 0.25 |
FA种类 | FA | sn-2FA | %sn-2FA | sn-1,3FA |
C12:0 | 0.33 | 0.59 | 59.60 | 0.20 |
C14:0 | 4.72 | 4.38 | 30.93 | 4.89 |
C16:0 | 34.88 | 58.89 | 56.28 | 22.88 |
C16:1 | 0.49 | 0.62 | 42.18 | 0.43 |
C18:0 | 9.22 | 4.88 | 17.64 | 11.39 |
C18:1 | 37.57 | 18.93 | 16.80 | 46.89 |
C18:2 | 8.62 | 8.74 | 33.80 | 8.56 |
C18:3 | 0.52 | 0.41 | 26.28 | 0.58 |
C20:0 | 0.51 | 0.39 | 25.49 | 0.57 |
C20:1 | 1.28 | 0.35 | 9.11 | 1.75 |
C20:2 | 0.23 | 0.12 | 17.39 | 0.29 |
C20:3 | 0.32 | 0.21 | 21.88 | 0.38 |
C20:4 | 0.17 | 0.10 | 19.61 | 0.21 |
C22:0 | 0.35 | 0.15 | 14.29 | 0.45 |
C22:1 | 0.31 | 0.08 | 8.60 | 0.43 |
C22:2 | 0.08 | 0.06 | 25.00 | 0.09 |
C24:1 | 0.11 | 0.05 | 15.15 | 0.14 |
C22:4 | 0.05 | 0.07 | 46.67 | 0.04 |
C22:5 | 0.09 | 0.10 | 37.04 | 0.09 |
C22:6 | 0.08 | 0.08 | 33.33 | 0.08 |
FA种类 | FA | sn-2FA | %sn-2FA | sn-1,3FA |
C14:0 | 3.48 | 4.01 | 38.41 | 3.22 |
C16:0 | 24.49 | 57.3 | 77.99 | 8.09 |
C18:0 | 5.43 | 5.62 | 34.50 | 5.34 |
C18:1 | 58.33 | 21.07 | 12.04 | 76.96 |
C18:2 | 7.42 | 9.02 | 40.52 | 6.62 |
C18:3 | 0.2 | 0.4 | 66.67 | 0.10 |
Claims (1)
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CN201510227309.9A CN104862350B (zh) | 2015-05-06 | 2015-05-06 | 一种制备1,3-二油酸-2-棕榈酸甘油三酯的方法 |
PCT/CN2015/096269 WO2016176987A1 (zh) | 2015-05-06 | 2015-12-03 | 一种富含1,3-二油酸-2-棕榈酸甘油三酯结构脂的制备方法 |
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CN201510227309.9A CN104862350B (zh) | 2015-05-06 | 2015-05-06 | 一种制备1,3-二油酸-2-棕榈酸甘油三酯的方法 |
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CN104862350B true CN104862350B (zh) | 2018-05-01 |
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CN104862350B (zh) * | 2015-05-06 | 2018-05-01 | 江南大学 | 一种制备1,3-二油酸-2-棕榈酸甘油三酯的方法 |
CN110724716B (zh) * | 2018-07-16 | 2021-07-20 | 浙江贝家生物科技有限公司 | 一种含有1,3-二油酸-2-棕榈酸甘油三酯的组合物的制备方法 |
CN111838676A (zh) * | 2019-12-17 | 2020-10-30 | 浙江大学 | 富含1,3-二月桂酸-2-棕榈酸甘油三酯的中长链脂肪酸油脂及其制备和应用 |
CN111317068A (zh) * | 2020-01-15 | 2020-06-23 | 广州市优百特饲料科技有限公司 | 饲用opo母乳结构脂及其制备方法及其应用 |
CN111961527B (zh) * | 2020-09-03 | 2021-12-03 | 广州白云山汉方现代药业有限公司 | 一种橄榄油中棕榈酸含量的精准控制方法 |
CN112522330B (zh) * | 2020-11-27 | 2023-04-18 | 江南大学 | 一种用于母乳替代脂的中长碳链甘油三酯及其制备方法 |
CN113712084B (zh) * | 2021-07-23 | 2024-05-24 | 暨科优脂(佛山)科技研发有限公司 | 一种食品专用油脂基料油及其制备方法 |
CN113832200B (zh) * | 2021-07-30 | 2023-12-01 | 江南大学 | 一种母乳化结构脂的制备方法 |
CN113584094B (zh) * | 2021-07-30 | 2022-07-19 | 江南大学 | 一种基于乳脂肪的1,3不饱和-2-饱和脂肪酸结构甘油三酯的制备方法 |
CN113575697B (zh) * | 2021-07-30 | 2022-10-18 | 江南大学 | 一种基于动物乳脂肪的母乳脂肪替代品的制备方法 |
CN113416755B (zh) * | 2021-07-30 | 2022-04-15 | 江南大学 | 一种1,3-二油酸-2-棕榈酸甘油三酯的工业化生产方法及其产品 |
CN113584095B (zh) * | 2021-07-30 | 2022-09-02 | 江南大学 | 一种富含1,3-不饱和-2-饱和脂肪酸结构脂的产品及其制备方法 |
CN113615743B (zh) * | 2021-07-30 | 2022-04-15 | 江南大学 | 一种模拟母乳脂肪结构的人乳替代脂的制备方法 |
CN113584093B (zh) * | 2021-07-30 | 2022-07-19 | 江南大学 | 一种高dha含量的结构脂质的制备方法及其产品 |
CN113481248B (zh) * | 2021-07-30 | 2022-04-15 | 江南大学 | 一种制备1,3-二油酸-2-棕榈酸甘油三酯的方法 |
CN113575696B (zh) * | 2021-07-30 | 2022-07-19 | 江南大学 | 一种基于母乳甘油三酯组成的结构脂质的制备方法 |
CN114907209B (zh) * | 2022-05-13 | 2023-10-13 | 江西师范大学 | 一种类母乳omo型结构酯及其制备方法 |
CN115191492A (zh) * | 2022-07-14 | 2022-10-18 | 江南大学 | 一种绿色高效制备人乳替代脂的方法及应用 |
CN118126822A (zh) * | 2024-05-07 | 2024-06-04 | 南昌大学 | 母乳结构脂类似物的连续化合成设备及其合成工艺 |
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CN102113574B (zh) * | 2009-12-30 | 2012-12-12 | 嘉里特种油脂(上海)有限公司 | 一种婴幼儿食品用油脂组合物的制备方法 |
CN101940241B (zh) * | 2010-07-12 | 2013-05-08 | 深圳精益油脂技术有限公司 | 采用来源于湄公河三角洲鲶鱼的油脂制备母乳脂肪替代物的方法 |
CN104862350B (zh) * | 2015-05-06 | 2018-05-01 | 江南大学 | 一种制备1,3-二油酸-2-棕榈酸甘油三酯的方法 |
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Inventor after: Zou Xiaoqiang Inventor after: Sun Cong Inventor after: Huang Lei Inventor after: Qin Jie Inventor after: Lv Songtai Inventor before: Wang Xingguo Inventor before: Zou Xiaoqiang Inventor before: Jin Qingzhe Inventor before: Huang Jianhua Inventor before: Liu Ruijie Inventor before: Chang Ming Inventor before: Wang Xiaosan Inventor before: Pan Qiuqin |
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Inventor after: Zou Xiaoqiang Inventor after: Qin Jie Inventor after: Huang Jianhua Inventor after: Liu Ruijie Inventor after: Chang Ming Inventor after: Wang Xiaosan Inventor before: Zou Xiaoqiang Inventor before: Sun Cong Inventor before: Huang Lei Inventor before: Qin Jie Inventor before: Lv Songtai |
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Inventor after: Wang Xingguo Inventor after: Zou Xiaoqiang Inventor after: Jin Qingzhe Inventor after: Huang Jianhua Inventor after: Liu Ruijie Inventor after: Chang Ming Inventor after: Wang Xiaosan Inventor after: Pan Qiuqin Inventor before: Zou Xiaoqiang Inventor before: Qin Jie Inventor before: Huang Jianhua Inventor before: Liu Ruijie Inventor before: Chang Ming Inventor before: Wang Xiaosan |
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Address after: 214122 Liangxi Food Park, South Building, 898 Tongsha Road, Liangxi District, Wuxi City, Jiangsu Province Patentee after: Jiangnan University Address before: Room A231, 214122 Jiangsu city of Wuxi Province Lake Road No. 1800, Jiangnan University College of chemistry and materials engineering Patentee before: Jiangnan University |