CN117623848A - Preparation method for simultaneously obtaining high-purity squalene and phytosterol - Google Patents
Preparation method for simultaneously obtaining high-purity squalene and phytosterol Download PDFInfo
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- CN117623848A CN117623848A CN202311555836.3A CN202311555836A CN117623848A CN 117623848 A CN117623848 A CN 117623848A CN 202311555836 A CN202311555836 A CN 202311555836A CN 117623848 A CN117623848 A CN 117623848A
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- squalene
- phytosterol
- oil
- waste residue
- oil absorption
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- YYGNTYWPHWGJRM-UHFFFAOYSA-N (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C YYGNTYWPHWGJRM-UHFFFAOYSA-N 0.000 title claims abstract description 71
- BHEOSNUKNHRBNM-UHFFFAOYSA-N Tetramethylsqualene Natural products CC(=C)C(C)CCC(=C)C(C)CCC(C)=CCCC=C(C)CCC(C)C(=C)CCC(C)C(C)=C BHEOSNUKNHRBNM-UHFFFAOYSA-N 0.000 title claims abstract description 71
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N dodecahydrosqualene Natural products CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 title claims abstract description 71
- 229940031439 squalene Drugs 0.000 title claims abstract description 71
- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 title claims abstract description 71
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 239000002699 waste material Substances 0.000 claims abstract description 47
- 239000003463 adsorbent Substances 0.000 claims abstract description 43
- 239000012141 concentrate Substances 0.000 claims abstract description 31
- 238000000034 method Methods 0.000 claims abstract description 31
- 239000003921 oil Substances 0.000 claims abstract description 28
- 235000019198 oils Nutrition 0.000 claims abstract description 28
- 238000001035 drying Methods 0.000 claims abstract description 25
- 238000010521 absorption reaction Methods 0.000 claims abstract description 23
- 239000003960 organic solvent Substances 0.000 claims abstract description 22
- 235000015112 vegetable and seed oil Nutrition 0.000 claims abstract description 20
- 238000001816 cooling Methods 0.000 claims abstract description 14
- 238000010438 heat treatment Methods 0.000 claims abstract description 14
- 238000010992 reflux Methods 0.000 claims abstract description 14
- 239000008158 vegetable oil Substances 0.000 claims abstract description 14
- 239000003513 alkali Substances 0.000 claims abstract description 10
- 239000007788 liquid Substances 0.000 claims abstract description 8
- 238000003756 stirring Methods 0.000 claims abstract description 5
- 230000005526 G1 to G0 transition Effects 0.000 claims abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 45
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 32
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 31
- 239000000741 silica gel Substances 0.000 claims description 21
- 229910002027 silica gel Inorganic materials 0.000 claims description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 13
- 238000010828 elution Methods 0.000 claims description 13
- 229920002401 polyacrylamide Polymers 0.000 claims description 13
- 238000001179 sorption measurement Methods 0.000 claims description 11
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 10
- 238000001914 filtration Methods 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- -1 amino silica gel Chemical compound 0.000 claims description 8
- 239000004927 clay Substances 0.000 claims description 8
- 229940068065 phytosterols Drugs 0.000 claims description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- 235000005687 corn oil Nutrition 0.000 claims description 6
- 239000002285 corn oil Substances 0.000 claims description 6
- 239000000377 silicon dioxide Substances 0.000 claims description 6
- 244000185386 Thladiantha grosvenorii Species 0.000 claims description 5
- 235000011171 Thladiantha grosvenorii Nutrition 0.000 claims description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 4
- 229960000892 attapulgite Drugs 0.000 claims description 4
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 4
- 229910052625 palygorskite Inorganic materials 0.000 claims description 4
- 239000010476 amaranth oil Substances 0.000 claims description 3
- 239000000440 bentonite Substances 0.000 claims description 3
- 229910000278 bentonite Inorganic materials 0.000 claims description 3
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 claims description 3
- 239000010495 camellia oil Substances 0.000 claims description 3
- 229910052570 clay Inorganic materials 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000004006 olive oil Substances 0.000 claims description 3
- 235000008390 olive oil Nutrition 0.000 claims description 3
- 239000003208 petroleum Substances 0.000 claims description 3
- 241001221716 Jasminum fruticans Species 0.000 claims description 2
- 235000006484 Paeonia officinalis Nutrition 0.000 claims description 2
- 244000170916 Paeonia officinalis Species 0.000 claims description 2
- 235000019774 Rice Bran oil Nutrition 0.000 claims description 2
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 claims description 2
- 150000002009 diols Chemical class 0.000 claims description 2
- 239000000944 linseed oil Substances 0.000 claims description 2
- 235000021388 linseed oil Nutrition 0.000 claims description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 2
- 239000008171 pumpkin seed oil Substances 0.000 claims description 2
- 239000008165 rice bran oil Substances 0.000 claims description 2
- 235000012239 silicon dioxide Nutrition 0.000 claims description 2
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 claims description 2
- 239000000047 product Substances 0.000 description 34
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- 238000000605 extraction Methods 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- 229930182558 Sterol Natural products 0.000 description 8
- 229930003427 Vitamin E Natural products 0.000 description 8
- 239000003480 eluent Substances 0.000 description 8
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 8
- 238000000926 separation method Methods 0.000 description 8
- 235000003702 sterols Nutrition 0.000 description 8
- 150000003432 sterols Chemical class 0.000 description 8
- 239000011709 vitamin E Substances 0.000 description 8
- 235000019165 vitamin E Nutrition 0.000 description 8
- 229940046009 vitamin E Drugs 0.000 description 8
- 125000000129 anionic group Chemical group 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 5
- 235000011187 glycerol Nutrition 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 235000002378 plant sterols Nutrition 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 238000004332 deodorization Methods 0.000 description 3
- 239000004519 grease Substances 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 238000007670 refining Methods 0.000 description 3
- 238000007127 saponification reaction Methods 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 238000000638 solvent extraction Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000000975 bioactive effect Effects 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000002035 hexane extract Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 229930003799 tocopherol Natural products 0.000 description 2
- 229960001295 tocopherol Drugs 0.000 description 2
- 239000011732 tocopherol Substances 0.000 description 2
- 235000010384 tocopherol Nutrition 0.000 description 2
- 150000003626 triacylglycerols Chemical class 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 2
- KZJWDPNRJALLNS-VPUBHVLGSA-N (-)-beta-Sitosterol Natural products O[C@@H]1CC=2[C@@](C)([C@@H]3[C@H]([C@H]4[C@@](C)([C@H]([C@H](CC[C@@H](C(C)C)CC)C)CC4)CC3)CC=2)CC1 KZJWDPNRJALLNS-VPUBHVLGSA-N 0.000 description 1
- CSVWWLUMXNHWSU-UHFFFAOYSA-N (22E)-(24xi)-24-ethyl-5alpha-cholest-22-en-3beta-ol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(CC)C(C)C)C1(C)CC2 CSVWWLUMXNHWSU-UHFFFAOYSA-N 0.000 description 1
- KLEXDBGYSOIREE-UHFFFAOYSA-N 24xi-n-propylcholesterol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CCC)C(C)C)C1(C)CC2 KLEXDBGYSOIREE-UHFFFAOYSA-N 0.000 description 1
- 206010003211 Arteriosclerosis coronary artery Diseases 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- LPZCCMIISIBREI-MTFRKTCUSA-N Citrostadienol Natural products CC=C(CC[C@@H](C)[C@H]1CC[C@H]2C3=CC[C@H]4[C@H](C)[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C LPZCCMIISIBREI-MTFRKTCUSA-N 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- ARVGMISWLZPBCH-UHFFFAOYSA-N Dehydro-beta-sitosterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)CCC(CC)C(C)C)CCC33)C)C3=CC=C21 ARVGMISWLZPBCH-UHFFFAOYSA-N 0.000 description 1
- 208000035150 Hypercholesterolemia Diseases 0.000 description 1
- 239000004367 Lipase Substances 0.000 description 1
- 102000004882 Lipase Human genes 0.000 description 1
- 108090001060 Lipase Proteins 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- MJVXAPPOFPTTCA-UHFFFAOYSA-N beta-Sistosterol Natural products CCC(CCC(C)C1CCC2C3CC=C4C(C)C(O)CCC4(C)C3CCC12C)C(C)C MJVXAPPOFPTTCA-UHFFFAOYSA-N 0.000 description 1
- LGJMUZUPVCAVPU-UHFFFAOYSA-N beta-Sitostanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 LGJMUZUPVCAVPU-UHFFFAOYSA-N 0.000 description 1
- NJKOMDUNNDKEAI-UHFFFAOYSA-N beta-sitosterol Natural products CCC(CCC(C)C1CCC2(C)C3CC=C4CC(O)CCC4C3CCC12C)C(C)C NJKOMDUNNDKEAI-UHFFFAOYSA-N 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 201000006612 cervical squamous cell carcinoma Diseases 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 208000029078 coronary artery disease Diseases 0.000 description 1
- 208000026758 coronary atherosclerosis Diseases 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 235000013376 functional food Nutrition 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 201000002364 leukopenia Diseases 0.000 description 1
- 231100001022 leukopenia Toxicity 0.000 description 1
- 235000019421 lipase Nutrition 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000000199 molecular distillation Methods 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000010773 plant oil Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000011085 pressure filtration Methods 0.000 description 1
- 238000001959 radiotherapy Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- KZJWDPNRJALLNS-VJSFXXLFSA-N sitosterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]1(C)CC2 KZJWDPNRJALLNS-VJSFXXLFSA-N 0.000 description 1
- 235000015500 sitosterol Nutrition 0.000 description 1
- 229950005143 sitosterol Drugs 0.000 description 1
- NLQLSVXGSXCXFE-UHFFFAOYSA-N sitosterol Natural products CC=C(/CCC(C)C1CC2C3=CCC4C(C)C(O)CCC4(C)C3CCC2(C)C1)C(C)C NLQLSVXGSXCXFE-UHFFFAOYSA-N 0.000 description 1
- 201000010106 skin squamous cell carcinoma Diseases 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 238000002137 ultrasound extraction Methods 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
- Y02W30/00—Technologies for solid waste management
- Y02W30/50—Reuse, recycling or recovery technologies
- Y02W30/74—Recovery of fats, fatty oils, fatty acids or other fatty substances, e.g. lanolin or waxes
Landscapes
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a preparation method for simultaneously obtaining high-purity squalene and phytosterol, which comprises the following steps: A. taking oil absorption waste residues, and adding the oil absorption waste residues in a volume mass ratio of 2-10L: the mass ratio of 1kg of the first organic solvent to the oil absorption waste residue is 0.06-2 kg:1kg of alkali, heating, refluxing and stirring, standing, cooling, separating liquid, and concentrating to obtain concentrate; B. taking the concentrate as a stationary phase by using a chromatographic column filled with a mixed adsorbent, wherein the volume mass ratio of the concentrate to the oil absorption waste residue is 0.5-3L: eluting with 1kg of first organic solvent as mobile phase, collecting eluting fraction, concentrating, and drying to obtain squalene product; C. the volume mass ratio of the oil absorption waste residue to the oil absorption waste residue is 1-4L: and (3) taking 1kg of a second organic solvent as a mobile phase, eluting the chromatographic column again, collecting the eluted fraction, concentrating, and drying to obtain a phytosterol product. The invention provides a novel method for extracting high-purity squalene and phytosterol, and simultaneously comprehensively utilizes adsorbent waste residues after vegetable oil is adsorbed, so that resource waste is reduced.
Description
Technical Field
The invention relates to the field of manufacturing of functional food raw materials and medicine raw materials, in particular to a preparation method for simultaneously obtaining high-purity squalene and phytosterol.
Background
In the refining process of vegetable oil, in order to make the oil have higher quality, the oil needs to be adsorbed by an adsorbent to remove impurities, for example, the oil needs to be decolorized by an adsorbent such as activated carbon, activated clay, attapulgite, bentonite and the like, and in medicinal oil, the oil needs to be further purified by an adsorbent such as silica gel, alumina and the like. However, the adsorbent can absorb impurities and also can inevitably absorb partial beneficial oil components such as triglyceride, squalene, tocopherol, phytosterol and the like. The adsorbent after adsorbing the grease is generally treated as waste residue, and if the adsorbent is not recycled, the beneficial components in the waste residue of the adsorbent are separated, so that great resource waste can be caused.
Squalene and phytosterol are accompanying nutritional ingredients in vegetable oil, wherein squalene is colorless liquid, has various pharmacological activities, can improve cell activity, improve anoxic state of cardiovascular and cerebrovascular diseases, and can be used for hypercholesterolemia and leukopenia caused by radiotherapy and chemotherapy. The plant sterol is a substance with a cyclic alcohol structure, can reduce the cholesterol level in serum, prevent and treat heart diseases such as coronary atherosclerosis, and has obvious curative effects on ulcers, skin squamous cell carcinoma, cervical cancer and the like.
In the prior art, squalene and phytosterol mainly take vegetable oil or vegetable oil deodorization distillate and the like as raw materials, and adopt esterification, saponification, molecular distillation, column chromatography and supercritical C0 2 The preparation method comprises the steps of extraction, inclusion, crystallization and other technologies.
Patent CN202111131385 (method for recovering bioactive components from waste activated clay subjected to vegetable oil decolorization) discloses a method for recovering bioactive components from waste activated clay by means of ultrasonic extraction and gradient elution with an organic solvent, wherein the tocopherol, squalene and phytosterol obtained by the method are low in content and are a mixture.
Patent CN201610717836, "method for recovering squalene, vitamin E and/or sterol", discloses a method for extracting squalene, sterol and vitamin E from a residue from vitamin E production, by adsorption using a polar adsorbent and a nonpolar solvent, a polar solvent, solid-liquid phase separation and crystallization process, a squalene-containing product and/or a sterol-containing crystalline product and/or a vitamin E-containing product are obtained. But the content of squalene in the extracted squalene-containing product is more than 30%, the content of sterols in the sterol-containing crystal product is more than 75%, and the content of vitamin E in the vitamin E-containing product is more than 30%.
Patent CN201611125250, "a method for extracting squalene from grease", adopts a method of glycerolysis of lipase, inclusion of cyclodextrin and adsorption separation of alumina to extract squalene from grease, and the method only obtains high-purity squalene.
Patent CN202010728500 (method for separating squalene from fructus Siraitiae Grosvenorii extract residue) comprises extracting with alkaline low-carbon alcohol, drying, mixing with silica gel, extracting with supercritical carbon dioxide, and extracting with solvent to obtain squalene; the sitosterol and the momordica grosvenori are respectively obtained by the operations of silica gel column chromatography and the like after the sample is mixed, and the operations are complex.
Patent CN202211106716 (method for enriching polyunsaturated fatty acid esters, squalene, natural vitamin E and plant sterols) from plant deodorization distillate, wherein the plant deodorization distillate is added with short-chain alcohol and an emulsifying agent or an auxiliary emulsifying agent for emulsification, low-temperature enzymatic esterification, gradient freezing crystallization, pressure filtration, multistage rectification, urea complexation and other operations to respectively obtain the plant sterols, the squalene, the natural vitamin E and the polyunsaturated fatty acid esters. The operation is complex, and the content of squalene and phytosterol is below 70%.
Patent CN202011168092, "a method for extracting squalene from plant deodorizer distillate", uses plant oil deodorizer distillate as raw material, uses the combined technological process of saponification with alkali alcoholic solution, organic solvent extraction, crystallization and macroporous resin chromatography to extract high-purity and high-yield squalene, and said method can separate sterol, but has no clear sterol content.
Disclosure of Invention
The invention aims to provide a novel method for extracting high-purity squalene and phytosterol, and simultaneously comprehensively utilizes adsorbent waste residues after vegetable oil absorption, so that resource waste is reduced.
In order to solve the technical problems, the invention adopts the following technical scheme:
a preparation method for simultaneously obtaining high-purity squalene and phytosterol comprises the following steps:
A. taking oil absorption waste residues, and adding the oil absorption waste residues in a volume mass ratio of 2-10L: the mass ratio of 1kg of the first organic solvent to the oil absorption waste residue is 0.06-2 kg:1kg of alkali, heating, refluxing and stirring, standing, cooling, separating liquid, and concentrating to obtain concentrate;
B. the concentrate takes a chromatographic column filled with a mixed adsorbent as a stationary phase, and the volume mass ratio of the concentrate to the adsorption waste residue is 0.5-3L: eluting with 1kg of first organic solvent as mobile phase, collecting eluting fraction, concentrating, and drying to obtain squalene product;
C. the volume mass ratio of the oil absorption waste residue to the oil absorption waste residue is 1-4L: and (3) taking 1kg of a second organic solvent as a mobile phase, eluting the chromatographic column again, collecting the eluted fraction, concentrating, and drying to obtain a phytosterol product.
Some vegetable oils have high levels of squalene and phytosterols, and some of these vegetable oils inevitably become adsorbed by the adsorbent and remain in the adsorbent waste residue during the refining process. However, the presence of triglycerides can affect subsequent separation of squalene and phytosterols. In the prior art, the hydrolysis of saponified triglycerides to form fatty acid salts and glycerin is typically carried out using an alcoholic solution of a base. However, since the fatty acid salt, glycerin, phytosterol, squalene, and the rest of alkali are all soluble in the alcohol solution, the subsequent operations such as multi-step solvent extraction and back extraction, water washing and the like are required, and a large amount of solvents are required to be consumed and a large amount of wastewater is generated. In the technical scheme, alkane solvents are selected as extraction solvents, so that excessive alkali, fatty acid salts and glycerol can be well prevented from being dissolved in the extraction solvents, and plant sterols and squalene can be selectively extracted. In addition, experiments show that the hydrolyzed glycerol has larger polarity, so that sterol components are promoted to be resolved from adsorbent waste residues, and the extraction efficiency of the alkane solvent is further improved.
Therefore, the invention discards the traditional extraction mode adopting alcohol solvent, changes the low-polarity alkane solvent into the low-polarity alkane solvent, avoids the residual fatty acid salt, glycerol and redundant alkali in the extraction solvent, avoids the subsequent operations of further extraction, water washing and the like, and can be realized through simple separation operation.
Preferably, in the step B, the mixed adsorbent comprises polyacrylamide accounting for 1-8% of the total mass of the mixed adsorbent.
A small amount of free fatty acid and its salt generated by hydrolysis are inevitably remained in the preparation process. Polyacrylamide is a high molecular organic polymer, has good adsorption characteristics, and particularly has strong adsorption and fixation capacity on large polar substances and anionic substances.
Preferably, in the step B, the mixed adsorbent further comprises one or more of silica gel, amino silica gel, diol silica gel and silica.
The invention uses a small amount of polyacrylamide and silica gel adsorbent as mixed adsorbent, which unexpectedly enhances the separation effect of the concentrate, reduces the use amount of solvent, and ensures that the purities of squalene and phytosterol are more than 95 percent, thus obtaining unexpected effect.
Preferably, the first organic solvent comprises one or more of pentane, hexane, heptane, octane, petroleum ether; the second organic solvent comprises one or more of dichloromethane, chloroform, diethyl ether, ethyl acetate, methanol, ethanol, isopropanol and acetone.
Preferably, the specific operation of step a includes: the volume mass ratio of the first organic solvent, the alkali and the oil absorption waste residue is controlled to be 2-10L: 0.06-2 kg:1kg, heating, refluxing and stirring for 0.5-3 hours, standing, naturally cooling, separating out liquid, and concentrating to obtain the concentrate; in the step B, the mass ratio of the mixed adsorbent to the oil absorption waste residue is 0.05-0.18 kg:1kg.
Preferably, step a further comprises: the first organic solvent is recovered during concentration and used in the elution of step B.
Preferably, in the step a, the oil absorption waste residue includes adsorbent waste residue obtained by separating after adsorbing vegetable oil.
Preferably, the vegetable oil comprises one or more of olive oil, rice bran oil, tea oil, linseed oil, momordica grosvenori seed oil, wild jasmine seed oil, pumpkin seed oil, amaranth oil, peony seed oil and corn oil; the adsorbent in the adsorbent waste residue comprises one or more of active carbon, activated clay, bentonite, attapulgite, diatomite, florisil silica, silica gel, silicon dioxide, aluminum oxide and aluminum silicate; the method for separating out the liquid comprises one or more of standing and layering, centrifuging and filtering.
A squalene product obtained according to the above process for producing squalene and phytosterols simultaneously having high purity.
A phytosterol product obtained according to the above process for the preparation of squalene and phytosterols simultaneously obtained in high purity.
Compared with the prior art, the implementation of the invention has the following beneficial effects:
(1) The invention avoids complex operation, large amount of solvent use and wastewater generation by combining one-step alkali hydrolysis-solvent extraction with column separation technology.
(2) The invention improves the squalene and the phytosterol which are obtained in high purity by improving the column separation capability.
(3) The invention takes the waste residue of the adsorbent generated in refining vegetable oil as raw material, which can improve the utilization rate of resources.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention will be described in further detail with reference to specific embodiments.
Example 1
Taking 2kg of active carbon waste residue obtained by separating after corn oil adsorption, adding 5L of n-hexane and 0.16kg of sodium hydroxide, heating and refluxing for 2 hours, standing for cooling, filtering, and concentrating filtrate to obtain a concentrate. Adding the concentrate to the upper end of a chromatographic column filled with a mixed adsorbent of 10g polyacrylamide and 190g silica gel, eluting with 2L of n-hexane, discarding the front-stage eluent, collecting the elution fraction containing squalene, concentrating, and drying to obtain squalene product with purity of 99.4%; eluting with 4L dichloromethane, collecting dichloromethane eluate, concentrating, and drying to obtain phytosterol product with purity of 97.8%.
Example 2
Taking 2kg of activated clay waste residue obtained by separating after tea oil absorption, adding 10L of n-heptane and 0.2kg of sodium hydroxide, heating and refluxing for 2.5 hours, standing still for cooling, filtering, and concentrating filtrate to obtain a concentrate. Adding the concentrate to the upper end of a chromatographic column filled with a mixed adsorbent of 6g of anionic polyacrylamide and 290g of silica gel, eluting with 4L of n-heptane, discarding the front-end eluent, collecting the elution fraction containing squalene, concentrating, and drying to obtain squalene product with the purity of 99.1%; eluting with 2L chloroform, collecting chloroform eluate, concentrating, and drying to obtain phytosterol product with purity of 97.2%.
Example 3
Taking 2kg of activated clay waste residue obtained by separating the absorbed momordica grosvenori kernel oil, adding 8L of n-hexane and 0.3kg of potassium hydroxide, heating and refluxing for 1.5 hours, standing still for cooling, filtering, and concentrating filtrate to obtain a concentrate. Adding the concentrate to the upper end of a chromatographic column filled with a mixed adsorbent of 2g of anionic polyacrylamide and 98g of amino silica gel, eluting with 1L of n-hexane, discarding the front-stage eluent, collecting an elution fraction containing squalene, concentrating, and drying to obtain a squalene product with the purity of 99.1%; eluting with 2L of dichloromethane, collecting dichloromethane eluting fraction, concentrating, and drying to obtain phytosterol product with purity of 97.2%.
Example 4
Taking 2kg of activated carbon and silica gel waste residue obtained by separating after the adsorption of olive oil, adding 15L of n-hexane and 0.4kg of potassium hydroxide, heating and refluxing for 2 hours, standing still for cooling, filtering, and concentrating the filtrate to obtain a concentrate. Adding the concentrate to the upper end of a chromatographic column filled with a mixed adsorbent of 10g of anionic polyacrylamide and 190g of glycol-based silica gel, eluting with 5L of n-octane, discarding the eluent at the front stage, collecting the elution fraction containing squalene, concentrating, and drying to obtain squalene product with the purity of 98.3%; eluting with 6L ethanol, collecting methanol eluate, concentrating, and drying to obtain phytosterol product with purity of 97.5%.
Example 5
2kg of attapulgite waste residue obtained by separating amaranth oil is taken, 10L of n-octane-diethyl ether (1:1) and 0.4kg of calcium hydroxide are added, heating reflux is carried out for 2 hours, standing still for cooling, centrifugation is carried out, and filtrate is concentrated to obtain a concentrate. Adding the concentrate to the upper end of a chromatographic column filled with a mixed adsorbent of 12g of anionic polyacrylamide and 138g of glycol-based silica gel, eluting with 3L of petroleum ether, discarding the eluent of the previous stage, collecting the elution fraction containing squalene, concentrating, and drying to obtain squalene product with the purity of 98.3%; eluting with 8L methanol, collecting methanol eluate, concentrating, and drying to obtain phytosterol product with purity of 97.5%.
Comparative example 1
Taking 2kg of active carbon waste residue obtained by separating after corn oil adsorption, adding 5L of ethanol and 0.16kg of sodium hydroxide, heating and refluxing for 2 hours, standing still for cooling, filtering, adding 5L of water into filtrate, extracting 3 times with n-hexane for 10L each time, washing n-hexane extract with water for 3 times with 10L each time, and concentrating the n-hexane extract to obtain a concentrate. Adding the concentrate to the upper end of a chromatographic column filled with 200g of silica gel mixed adsorbent, eluting with 2L of n-hexane, discarding the front-stage eluent, collecting the elution fraction containing squalene, concentrating, and drying to obtain squalene product with purity of 94.0%; eluting with 4L dichloromethane, collecting dichloromethane eluate, concentrating, and drying to obtain phytosterol product with purity of 78.5%.
As can be seen from comparative example 1, the saponification treatment with an alcoholic solution of a base requires removal of impurities by multiple extractions and water washes, consumes a large amount of extraction solvent and water, and is separated and purified using conventional silica gel column chromatography, while a squalene product of higher purity can be obtained, the phytosterol product is of lower purity.
Comparative example 2
Taking 2kg of active carbon waste residue obtained by separating after corn oil adsorption, adding 5L of n-hexane and 0.16kg of sodium hydroxide, heating and refluxing for 2 hours, standing for cooling, filtering, and concentrating filtrate to obtain a concentrate. Adding the concentrate to the upper end of a chromatographic column filled with 200g of silica gel adsorbent, eluting with 2L of n-hexane, discarding the front-stage eluent, collecting the elution fraction containing squalene, concentrating, and drying to obtain squalene product with purity of 95.4%; eluting with 4L dichloromethane, collecting dichloromethane eluate, concentrating, and drying to obtain phytosterol product with purity of 87.8%.
As can be seen from comparative example 2, the concentrate obtained by the present technical scheme can be separated and purified by silica gel column chromatography without polyacrylamide to obtain squalene product with higher purity, and the purity of the phytosterol product is improved (compared with comparative example 1), but more than 95% of the phytosterol product can not be obtained.
Comparative example 3
Taking 2kg of active carbon waste residue obtained by separating after corn oil adsorption, adding 5L of n-hexane and 0.16kg of sodium hydroxide, heating and refluxing for 2 hours, standing for cooling, filtering, and concentrating filtrate to obtain a concentrate. Adding the concentrate to the upper end of a chromatographic column filled with a mixed adsorbent of 18g polyacrylamide and 182g silica gel, eluting with 2L of n-hexane, discarding the front-stage eluent, collecting the elution fraction containing squalene, concentrating, and drying to obtain squalene product with the purity of 97.6%; eluting with 10L of dichloromethane, collecting dichloromethane eluting fraction, concentrating, and drying to obtain phytosterol product with purity of 90.1%.
As can be seen from comparative example 3, when the amount of polyacrylamide exceeds 8% of the mass of the mixed adsorbent, more of the second organic solvent is required for elution, and the purity of the obtained phytosterol product is lowered.
Comparative example 4
Taking 2kg of activated clay waste residue obtained by separating the absorbed momordica grosvenori kernel oil, adding 8L of n-hexane and 0.3kg of potassium hydroxide, heating and refluxing for 1.5 hours, standing still for cooling, filtering, and concentrating filtrate to obtain a concentrate. Adding the concentrate to the upper end of a chromatographic column filled with a mixed adsorbent of 2g of anionic polyacrylamide and 98g of amino silica gel, eluting with 2L of dichloromethane, collecting dichloromethane elution fraction, concentrating and drying to obtain a squalene and phytosterol mixed product, wherein the squalene content is 63.7% and the phytosterol content is 15.2%; eluting with 1L of n-hexane, concentrating, drying, and collecting sample containing small amount of phytosterol with purity of 33.9%.
As can be seen from comparative example 4, the mixed product of squalene and phytosterol is obtained by eluting with dichloromethane, and the purity is low, so that the separation and purification effects are not achieved. It can be seen that the order of use of the first organic solvent and the second organic solvent can have a significant impact on the separation and purification effect.
The foregoing disclosure is merely illustrative of the preferred embodiments of the present invention and is not intended to limit the scope of the claims herein, as equivalent changes may be made in the claims herein without departing from the scope of the invention.
Claims (10)
1. The preparation method for simultaneously obtaining high-purity squalene and phytosterol is characterized by comprising the following steps of:
A. adding a first organic solvent and alkali into the oil absorption waste residue, heating, refluxing and stirring, standing, cooling, separating liquid, and concentrating to obtain a concentrate;
B. the concentrate takes a chromatographic column filled with a mixed adsorbent as a stationary phase, and the volume mass ratio of the concentrate to the adsorption waste residue is 0.5-3L: eluting with 1kg of first organic solvent as mobile phase, collecting eluting fraction, concentrating, and drying to obtain squalene product;
C. the volume mass ratio of the oil absorption waste residue to the oil absorption waste residue is 1-4L: and (3) taking 1kg of a second organic solvent as a mobile phase, eluting the chromatographic column again, collecting the eluted fraction, concentrating, and drying to obtain a phytosterol product.
2. The method for preparing squalene and phytosterol simultaneously with high purity according to claim 1, wherein in the step B, the mixed adsorbent comprises polyacrylamide accounting for 1-8% of the mass of the mixed adsorbent.
3. The method for preparing squalene and phytosterol simultaneously with high purity according to claim 2, wherein in step B, the mixed adsorbent further comprises one or more of silica gel, amino silica gel, diol-based silica gel, and silica.
4. The method for preparing squalene and phytosterol simultaneously with high purity according to claim 1, wherein the first organic solvent comprises one or more of pentane, hexane, heptane, octane, petroleum ether; the second organic solvent comprises one or more of dichloromethane, chloroform, diethyl ether, ethyl acetate, methanol, ethanol, isopropanol and acetone.
5. The process for the preparation of squalene and phytosterols simultaneously obtained in high purity according to claim 1, characterized in that the specific operations of step a comprise: the volume mass ratio of the first organic solvent, the alkali and the oil absorption waste residue is controlled to be 2-10L: 0.06-2 kg:1kg, heating, refluxing and stirring for 0.5-3 hours, standing, naturally cooling, separating out liquid, and concentrating to obtain the concentrate; in the step B, the mass ratio of the mixed adsorbent to the oil absorption waste residue is 0.05-0.18 kg:1kg.
6. The process for preparing squalene and phytosterols simultaneously in high purity according to claim 1, wherein step a further comprises: the first organic solvent is recovered during concentration and used in the elution of step B.
7. The method for preparing squalene and phytosterol simultaneously with high purity according to claim 1, wherein in the step a, the oil absorption waste residue comprises adsorbent waste residue separated after vegetable oil absorption.
8. The method for preparing squalene and phytosterol simultaneously with high purity according to claim 7, wherein the vegetable oil comprises one or more of olive oil, rice bran oil, tea oil, linseed oil, momordica grosvenori seed oil, wild jasmine seed oil, pumpkin seed oil, amaranth oil, peony seed oil and corn oil; the adsorbent in the adsorbent waste residue comprises one or more of active carbon, activated clay, bentonite, attapulgite, diatomite, florisil silica, silica gel, silicon dioxide, aluminum oxide and aluminum silicate; the method for separating out the liquid comprises one or more of standing and layering, centrifuging and filtering.
9. A squalene product obtainable by the process according to claim 1, wherein high purity squalene and phytosterols are simultaneously obtained.
10. A phytosterol product obtainable by the process of claim 1 by a process for the simultaneous obtaining of squalene and phytosterols in high purity.
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