CN102277237B - 一种甘油酯型鱼油的制备方法 - Google Patents
一种甘油酯型鱼油的制备方法 Download PDFInfo
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- CN102277237B CN102277237B CN 201110165890 CN201110165890A CN102277237B CN 102277237 B CN102277237 B CN 102277237B CN 201110165890 CN201110165890 CN 201110165890 CN 201110165890 A CN201110165890 A CN 201110165890A CN 102277237 B CN102277237 B CN 102277237B
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- Prior art keywords
- fish oil
- reactor
- type fish
- glyceride type
- preparation
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- 235000021323 fish oil Nutrition 0.000 title claims abstract description 60
- 125000005456 glyceride group Chemical group 0.000 title claims abstract description 32
- 238000002360 preparation method Methods 0.000 title claims abstract description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 38
- 238000006243 chemical reaction Methods 0.000 claims abstract description 32
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 19
- 239000000463 material Substances 0.000 claims abstract description 15
- 239000003513 alkali Substances 0.000 claims abstract description 14
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 claims abstract description 14
- 239000012044 organic layer Substances 0.000 claims abstract description 13
- 238000005406 washing Methods 0.000 claims abstract description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000010791 quenching Methods 0.000 claims abstract description 8
- 230000000171 quenching effect Effects 0.000 claims abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000012043 crude product Substances 0.000 claims abstract description 7
- 238000002156 mixing Methods 0.000 claims abstract description 7
- 239000002253 acid Substances 0.000 claims abstract description 5
- 125000004494 ethyl ester group Chemical group 0.000 claims description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 239000000243 solution Substances 0.000 claims description 13
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 12
- 235000019198 oils Nutrition 0.000 claims description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 6
- 230000006837 decompression Effects 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- 239000000284 extract Substances 0.000 claims description 6
- 238000000605 extraction Methods 0.000 claims description 6
- 239000000706 filtrate Substances 0.000 claims description 6
- 235000011187 glycerol Nutrition 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- 239000010813 municipal solid waste Substances 0.000 claims description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- 239000000843 powder Substances 0.000 claims description 3
- 239000011701 zinc Substances 0.000 claims description 3
- 229910052725 zinc Inorganic materials 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 abstract description 13
- 238000004519 manufacturing process Methods 0.000 abstract description 13
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 abstract description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 4
- 239000003208 petroleum Substances 0.000 abstract 2
- 239000012295 chemical reaction liquid Substances 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 238000000034 method Methods 0.000 description 15
- 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 description 12
- 235000020673 eicosapentaenoic acid Nutrition 0.000 description 12
- 239000002994 raw material Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 230000007812 deficiency Effects 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 2
- HXWJFEZDFPRLBG-UHFFFAOYSA-N Timnodonic acid Natural products CCCC=CC=CCC=CCC=CCC=CCCCC(O)=O HXWJFEZDFPRLBG-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 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 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229960005135 eicosapentaenoic acid Drugs 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
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- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
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CN 201110165890 CN102277237B (zh) | 2011-06-20 | 2011-06-20 | 一种甘油酯型鱼油的制备方法 |
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CN 201110165890 CN102277237B (zh) | 2011-06-20 | 2011-06-20 | 一种甘油酯型鱼油的制备方法 |
Publications (2)
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CN102277237A CN102277237A (zh) | 2011-12-14 |
CN102277237B true CN102277237B (zh) | 2013-04-24 |
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Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
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TW201334808A (zh) * | 2012-02-29 | 2013-09-01 | Braun Melsungen Ag | 含有荷爾蒙之包含磷蝦磷脂質的乳劑 |
EP2819650A1 (en) * | 2012-02-29 | 2015-01-07 | B. Braun Melsungen AG | Hormone containing emulsion comprising krill phospholipids |
CN103242969B (zh) * | 2013-05-24 | 2014-11-19 | 四川欣美加生物医药有限公司 | 甘油三酯型鱼油制备方法及制备的甘油三酯型鱼油 |
CN103396303B (zh) * | 2013-07-25 | 2014-12-17 | 浙江大学 | 一种从微藻油或鱼油中分离纯化二十碳五烯酸和二十二碳六烯酸的方法 |
CN105566103B (zh) | 2014-10-13 | 2019-02-19 | 浙江医药股份有限公司新昌制药厂 | 一种甘油酯型多不饱和脂肪酸的制备方法 |
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GB9701705D0 (en) * | 1997-01-28 | 1997-03-19 | Norsk Hydro As | Purifying polyunsatured fatty acid glycerides |
CN101255380B (zh) * | 2007-03-03 | 2010-11-03 | 苑洪德 | 甘油三酯型鱼油及其制作方法 |
CN101348807B (zh) * | 2008-08-26 | 2011-07-27 | 江南大学 | 一种从鱼油中富集n-3多不饱和脂肪酸甘油酯的方法 |
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Denomination of invention: Preparation method of high-purity glyceride type fish oil Effective date of registration: 20170427 Granted publication date: 20130424 Pledgee: Bank of Dezhou Limited by Share Ltd. Yucheng branch Pledgor: SHANDONG YUWANG PHARMACEUTICAL CO.,LTD. Registration number: 2017370000049 |
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Date of cancellation: 20200608 Granted publication date: 20130424 Pledgee: Bank of Dezhou Limited by Share Ltd. Yucheng branch Pledgor: SHANDONG YUWANG PHARMACEUTICAL Co.,Ltd. Registration number: 2017370000049 |
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Denomination of invention: Preparation method of high-purity glyceride type fish oil Effective date of registration: 20200612 Granted publication date: 20130424 Pledgee: Bank of Dezhou Limited by Share Ltd. Yucheng branch Pledgor: SHANDONG YUWANG PHARMACEUTICAL Co.,Ltd. Registration number: Y2020370000103 |
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Date of cancellation: 20230621 Granted publication date: 20130424 Pledgee: Bank of Dezhou Limited by Share Ltd. Yucheng branch Pledgor: SHANDONG YUWANG PHARMACEUTICAL CO.,LTD. Registration number: Y2020370000103 |
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Denomination of invention: A preparation method of glycerol ester type fish oil Effective date of registration: 20230803 Granted publication date: 20130424 Pledgee: Bank of Dezhou Limited by Share Ltd. Yucheng branch Pledgor: SHANDONG YUWANG PHARMACEUTICAL CO.,LTD. Registration number: Y2023980050841 |
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