CN102241586B - Method for synthesizing and purifying high-purity fatty acyl monoglyceride - Google Patents
Method for synthesizing and purifying high-purity fatty acyl monoglyceride Download PDFInfo
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- CN102241586B CN102241586B CN201110122225.0A CN201110122225A CN102241586B CN 102241586 B CN102241586 B CN 102241586B CN 201110122225 A CN201110122225 A CN 201110122225A CN 102241586 B CN102241586 B CN 102241586B
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- glycerine
- free fatty
- fatty acids
- fatty acyl
- purity
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- -1 fatty acyl monoglyceride Chemical compound 0.000 title claims abstract description 65
- 230000002194 synthesizing effect Effects 0.000 title claims abstract 3
- 238000000034 method Methods 0.000 title abstract description 22
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 224
- 238000000199 molecular distillation Methods 0.000 claims abstract description 81
- 235000021588 free fatty acids Nutrition 0.000 claims abstract description 55
- 230000032050 esterification Effects 0.000 claims abstract description 39
- 238000005886 esterification reaction Methods 0.000 claims abstract description 39
- 238000010992 reflux Methods 0.000 claims abstract description 39
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims abstract description 35
- 239000011949 solid catalyst Substances 0.000 claims abstract description 26
- 238000006243 chemical reaction Methods 0.000 claims abstract description 21
- 238000004821 distillation Methods 0.000 claims abstract description 19
- 239000000203 mixture Substances 0.000 claims abstract description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000000498 cooling water Substances 0.000 claims abstract description 12
- 238000003756 stirring Methods 0.000 claims abstract description 12
- 235000011187 glycerol Nutrition 0.000 claims description 104
- 125000005908 glyceryl ester group Chemical group 0.000 claims description 68
- 238000002360 preparation method Methods 0.000 claims description 30
- 238000005809 transesterification reaction Methods 0.000 claims description 25
- 239000003921 oil Substances 0.000 claims description 22
- 235000019198 oils Nutrition 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 21
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 20
- 229930195729 fatty acid Natural products 0.000 claims description 20
- 239000000194 fatty acid Substances 0.000 claims description 20
- 150000004665 fatty acids Chemical class 0.000 claims description 19
- 150000002632 lipids Chemical class 0.000 claims description 19
- 239000004519 grease Substances 0.000 claims description 17
- 239000003054 catalyst Substances 0.000 claims description 16
- 238000000746 purification Methods 0.000 claims description 14
- 238000013517 stratification Methods 0.000 claims description 13
- 239000007795 chemical reaction product Substances 0.000 claims description 11
- 239000007787 solid Substances 0.000 claims description 11
- 239000003930 superacid Substances 0.000 claims description 11
- 235000021355 Stearic acid Nutrition 0.000 claims description 9
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 9
- 239000008117 stearic acid Substances 0.000 claims description 9
- 239000002131 composite material Substances 0.000 claims description 8
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 8
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 claims description 7
- DCXXMTOCNZCJGO-UHFFFAOYSA-N Glycerol trioctadecanoate Natural products CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 claims description 7
- 235000020238 sunflower seed Nutrition 0.000 claims description 7
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 6
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 6
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 6
- 239000005642 Oleic acid Substances 0.000 claims description 6
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 6
- 229910006404 SnO 2 Inorganic materials 0.000 claims description 6
- 235000021323 fish oil Nutrition 0.000 claims description 6
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 6
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 6
- 235000013311 vegetables Nutrition 0.000 claims description 6
- 238000010025 steaming Methods 0.000 claims description 5
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 4
- 229910010413 TiO 2 Inorganic materials 0.000 claims description 4
- 239000002826 coolant Substances 0.000 claims description 4
- 239000008187 granular material Substances 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- 235000012424 soybean oil Nutrition 0.000 claims description 4
- 239000003549 soybean oil Substances 0.000 claims description 4
- 235000019484 Rapeseed oil Nutrition 0.000 claims description 3
- 238000001914 filtration Methods 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 2
- 235000019483 Peanut oil Nutrition 0.000 claims description 2
- GEIAQOFPUVMAGM-UHFFFAOYSA-N ZrO Inorganic materials [Zr]=O GEIAQOFPUVMAGM-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 235000020661 alpha-linolenic acid Nutrition 0.000 claims description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 2
- 229960004488 linolenic acid Drugs 0.000 claims description 2
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 claims description 2
- 239000000312 peanut oil Substances 0.000 claims description 2
- 238000010792 warming Methods 0.000 claims description 2
- 229960002969 oleic acid Drugs 0.000 claims 2
- 229960004232 linoleic acid Drugs 0.000 claims 1
- 125000005456 glyceride group Chemical group 0.000 abstract description 7
- 125000004185 ester group Chemical group 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 238000002156 mixing Methods 0.000 abstract 1
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 23
- 239000002994 raw material Substances 0.000 description 23
- 238000009833 condensation Methods 0.000 description 18
- 230000005494 condensation Effects 0.000 description 18
- 239000006227 byproduct Substances 0.000 description 17
- 239000000047 product Substances 0.000 description 16
- 239000007789 gas Substances 0.000 description 13
- 239000011973 solid acid Substances 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 9
- 238000004587 chromatography analysis Methods 0.000 description 9
- 239000002245 particle Substances 0.000 description 9
- 125000005457 triglyceride group Chemical group 0.000 description 9
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 235000003084 food emulsifier Nutrition 0.000 description 6
- 229920000223 polyglycerol Polymers 0.000 description 6
- 235000010469 Glycine max Nutrition 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 235000019482 Palm oil Nutrition 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 239000002540 palm oil Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000003828 vacuum filtration Methods 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000005815 base catalysis Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 150000002190 fatty acyls Chemical group 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000002811 oleoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
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CN201110122225.0A CN102241586B (en) | 2011-05-12 | 2011-05-12 | Method for synthesizing and purifying high-purity fatty acyl monoglyceride |
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CN102241586B true CN102241586B (en) | 2014-04-09 |
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Families Citing this family (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5944303B2 (en) * | 2011-12-08 | 2016-07-05 | 花王株式会社 | A method for producing a fatty acid monoglyceride-containing mixture. |
CN103205315B (en) * | 2012-01-12 | 2017-12-22 | 江西益普畅新材料应用研究推广有限公司 | A kind of production technology of monoglyceride and the separation purifying technique of slag charge |
CN102864023B (en) * | 2012-09-14 | 2014-10-29 | 暨南大学 | Method for synthesizing and purifying high-purity fatty acyl monoglyceride |
CN102993009B (en) * | 2012-11-28 | 2015-01-07 | 广州嘉德乐生化科技有限公司 | Preparation method of glycerin monostearate alpha crystal |
CN102964245B (en) * | 2012-11-28 | 2014-04-09 | 广州嘉德乐生化科技有限公司 | Preparation method of high-quality glycerin monostearate |
CN103074164B (en) * | 2013-01-11 | 2014-07-30 | 江南大学 | Method for preparing lauric acid monoglyceride by immobilized lipase |
CN104531365B (en) * | 2014-12-10 | 2018-01-16 | 柳州高通食品化工有限公司 | A kind of preparation method of polyglycerol ester |
CN105523934B (en) * | 2015-12-16 | 2017-09-29 | 江南大学 | A kind of synthetic method of oligomeric glycerin mono-fatty acid ester |
CN105418417B (en) * | 2015-12-22 | 2017-08-25 | 杭州富春食品添加剂有限公司 | A kind of preparation method of high-purity glyceryl monolaurate |
CN107227322A (en) * | 2017-06-11 | 2017-10-03 | 河南工业大学 | Industrial molecular distillation prepares 3 chloropropanol esters in diglyceride and abatement diglyceride |
CN108018127A (en) * | 2017-11-30 | 2018-05-11 | 广州美晨科技实业有限公司 | A kind of preparation method of unsaturation mono-fatty acid glyceride |
CN108586246A (en) * | 2018-07-12 | 2018-09-28 | 佳力士添加剂(海安)有限公司 | A kind of method of presence of acidic ionic liquid catalyst synthesis monoglyceride |
CN108977471B (en) * | 2018-08-27 | 2021-07-02 | 潘志杰 | Method for converting natural glyceride type deep sea fish oil into concentrated glyceride through non-ethyl ester type approach |
CN109293476B (en) * | 2018-11-29 | 2021-08-10 | 浙江工业大学 | Glycerol separation process and device in glyceride production wastewater |
CN111187174A (en) * | 2020-01-16 | 2020-05-22 | 广东丽臣奥威实业有限公司 | Production and purification method of fatty acyl glycinate or fatty derivative acyl glycinate |
CN111499509A (en) * | 2020-04-09 | 2020-08-07 | 佳格食品(中国)有限公司 | Production process of high-purity monoglyceride |
CN114456066A (en) * | 2022-01-29 | 2022-05-10 | 山东成武易信环保科技有限公司 | Distillation method for purifying glycerol monobutyrate |
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CN1928016A (en) * | 2006-09-28 | 2007-03-14 | 张海军 | Preparation method of biological diesel oil |
CN101230309A (en) * | 2008-01-11 | 2008-07-30 | 四川大学 | Method for preparing biodiesel by lowering value of high acid palm oil |
CN101880602A (en) * | 2010-06-17 | 2010-11-10 | 暨南大学 | Method for preparing biodiesel by using high acid value oil |
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2011
- 2011-05-12 CN CN201110122225.0A patent/CN102241586B/en active Active
Patent Citations (3)
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CN1928016A (en) * | 2006-09-28 | 2007-03-14 | 张海军 | Preparation method of biological diesel oil |
CN101230309A (en) * | 2008-01-11 | 2008-07-30 | 四川大学 | Method for preparing biodiesel by lowering value of high acid palm oil |
CN101880602A (en) * | 2010-06-17 | 2010-11-10 | 暨南大学 | Method for preparing biodiesel by using high acid value oil |
Non-Patent Citations (5)
Title |
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M. da S. Machado等.Selective synthesis of glycerol monolaurate with zeolitic molecular sieves.《Applied Catalysis A:General》.2000,第203卷(第2期), * |
单甘酯的制备与分离;湛日景等;《中国油脂》;19930501(第2期);第26-29页 * |
湛日景等.单甘酯的制备与分离.《中国油脂》.1993,(第2期), |
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