CN1958596A - Method for extracting cholesterol from lanoline - Google Patents
Method for extracting cholesterol from lanoline Download PDFInfo
- Publication number
- CN1958596A CN1958596A CN 200610154755 CN200610154755A CN1958596A CN 1958596 A CN1958596 A CN 1958596A CN 200610154755 CN200610154755 CN 200610154755 CN 200610154755 A CN200610154755 A CN 200610154755A CN 1958596 A CN1958596 A CN 1958596A
- Authority
- CN
- China
- Prior art keywords
- cholesterol
- lanolin
- crude product
- step described
- product
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 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 title claims abstract description 198
- 235000012000 cholesterol Nutrition 0.000 title claims abstract description 95
- 238000000034 method Methods 0.000 title claims abstract description 37
- 239000004166 Lanolin Substances 0.000 claims abstract description 39
- 235000019388 lanolin Nutrition 0.000 claims abstract description 39
- 229940039717 lanolin Drugs 0.000 claims abstract description 39
- 239000000047 product Substances 0.000 claims abstract description 26
- 238000000526 short-path distillation Methods 0.000 claims abstract description 17
- 239000012043 crude product Substances 0.000 claims abstract description 16
- 238000005809 transesterification reaction Methods 0.000 claims abstract description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 48
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- 238000004587 chromatography analysis Methods 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 239000003480 eluent Substances 0.000 claims description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 9
- 238000004821 distillation Methods 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 9
- 239000000741 silica gel Substances 0.000 claims description 9
- 229910002027 silica gel Inorganic materials 0.000 claims description 9
- 238000001179 sorption measurement Methods 0.000 claims description 9
- 238000002425 crystallisation Methods 0.000 claims description 8
- 238000010828 elution Methods 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 239000002994 raw material Substances 0.000 claims description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 6
- 230000008025 crystallization Effects 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 2
- GHVZOJONCUEWAV-UHFFFAOYSA-N [K].CCO Chemical compound [K].CCO GHVZOJONCUEWAV-UHFFFAOYSA-N 0.000 claims description 2
- 239000003463 adsorbent Substances 0.000 claims description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 2
- 238000004440 column chromatography Methods 0.000 claims description 2
- 238000011068 loading method Methods 0.000 claims description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 2
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 claims description 2
- 239000011347 resin Substances 0.000 claims description 2
- 229920005989 resin Polymers 0.000 claims description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 2
- 238000006386 neutralization reaction Methods 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 238000010898 silica gel chromatography Methods 0.000 abstract 1
- 238000007127 saponification reaction Methods 0.000 description 17
- 238000010438 heat treatment Methods 0.000 description 15
- 238000013375 chromatographic separation Methods 0.000 description 11
- 239000000843 powder Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000012071 phase Substances 0.000 description 8
- BQPPJGMMIYJVBR-UHFFFAOYSA-N (10S)-3c-Acetoxy-4.4.10r.13c.14t-pentamethyl-17c-((R)-1.5-dimethyl-hexen-(4)-yl)-(5tH)-Delta8-tetradecahydro-1H-cyclopenta[a]phenanthren Natural products CC12CCC(OC(C)=O)C(C)(C)C1CCC1=C2CCC2(C)C(C(CCC=C(C)C)C)CCC21C BQPPJGMMIYJVBR-UHFFFAOYSA-N 0.000 description 7
- CHGIKSSZNBCNDW-UHFFFAOYSA-N (3beta,5alpha)-4,4-Dimethylcholesta-8,24-dien-3-ol Natural products CC12CCC(O)C(C)(C)C1CCC1=C2CCC2(C)C(C(CCC=C(C)C)C)CCC21 CHGIKSSZNBCNDW-UHFFFAOYSA-N 0.000 description 7
- XYTLYKGXLMKYMV-UHFFFAOYSA-N 14alpha-methylzymosterol Natural products CC12CCC(O)CC1CCC1=C2CCC2(C)C(C(CCC=C(C)C)C)CCC21C XYTLYKGXLMKYMV-UHFFFAOYSA-N 0.000 description 7
- FPTJELQXIUUCEY-UHFFFAOYSA-N 3beta-Hydroxy-lanostan Natural products C1CC2C(C)(C)C(O)CCC2(C)C2C1C1(C)CCC(C(C)CCCC(C)C)C1(C)CC2 FPTJELQXIUUCEY-UHFFFAOYSA-N 0.000 description 7
- BKLIAINBCQPSOV-UHFFFAOYSA-N Gluanol Natural products CC(C)CC=CC(C)C1CCC2(C)C3=C(CCC12C)C4(C)CCC(O)C(C)(C)C4CC3 BKLIAINBCQPSOV-UHFFFAOYSA-N 0.000 description 7
- LOPKHWOTGJIQLC-UHFFFAOYSA-N Lanosterol Natural products CC(CCC=C(C)C)C1CCC2(C)C3=C(CCC12C)C4(C)CCC(C)(O)C(C)(C)C4CC3 LOPKHWOTGJIQLC-UHFFFAOYSA-N 0.000 description 7
- CAHGCLMLTWQZNJ-UHFFFAOYSA-N Nerifoliol Natural products CC12CCC(O)C(C)(C)C1CCC1=C2CCC2(C)C(C(CCC=C(C)C)C)CCC21C CAHGCLMLTWQZNJ-UHFFFAOYSA-N 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- QBSJHOGDIUQWTH-UHFFFAOYSA-N dihydrolanosterol Natural products CC(C)CCCC(C)C1CCC2(C)C3=C(CCC12C)C4(C)CCC(C)(O)C(C)(C)C4CC3 QBSJHOGDIUQWTH-UHFFFAOYSA-N 0.000 description 7
- CAHGCLMLTWQZNJ-RGEKOYMOSA-N lanosterol Chemical compound C([C@]12C)C[C@@H](O)C(C)(C)[C@H]1CCC1=C2CC[C@]2(C)[C@H]([C@H](CCC=C(C)C)C)CC[C@@]21C CAHGCLMLTWQZNJ-RGEKOYMOSA-N 0.000 description 7
- 229940058690 lanosterol Drugs 0.000 description 7
- 239000011259 mixed solution Substances 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 229930182558 Sterol Natural products 0.000 description 6
- 230000032683 aging Effects 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000012046 mixed solvent Substances 0.000 description 6
- 150000003432 sterols Chemical class 0.000 description 6
- 235000003702 sterols Nutrition 0.000 description 6
- 238000005303 weighing Methods 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 5
- 230000003472 neutralizing effect Effects 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000002351 wastewater Substances 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- 229920000858 Cyclodextrin Polymers 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 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 3
- -1 sodium alkoxide Chemical class 0.000 description 3
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 238000000199 molecular distillation Methods 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003648 triterpenes Chemical class 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- ZBFPGLKEWSMWSG-BQNIITSRSA-N (3S,5R,10S,13R,14R,17R)-4,4,10,13,14-pentamethyl-17-[(2R)-6-methylhept-5-en-2-yl]-2,3,5,6,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-3-ol Chemical compound CC1(C)[C@@H](O)CC[C@]2(C)C3=CC[C@]4(C)[C@@H]([C@@H](CCC=C(C)C)C)CC[C@@]4(C)C3=CC[C@H]21 ZBFPGLKEWSMWSG-BQNIITSRSA-N 0.000 description 1
- QYIXCDOBOSTCEI-QCYZZNICSA-N (5alpha)-cholestan-3beta-ol Chemical compound C([C@@H]1CC2)[C@@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@H](C)CCCC(C)C)[C@@]2(C)CC1 QYIXCDOBOSTCEI-QCYZZNICSA-N 0.000 description 1
- MBZYKEVPFYHDOH-BQNIITSRSA-N 24,25-dihydrolanosterol Chemical compound C([C@@]12C)C[C@H](O)C(C)(C)[C@@H]1CCC1=C2CC[C@]2(C)[C@@H]([C@H](C)CCCC(C)C)CC[C@]21C MBZYKEVPFYHDOH-BQNIITSRSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- ZBFPGLKEWSMWSG-UHFFFAOYSA-N agnosterone Natural products CC1(C)C(O)CCC2(C)C3=CCC4(C)C(C(CCC=C(C)C)C)CCC4(C)C3=CCC21 ZBFPGLKEWSMWSG-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- QYIXCDOBOSTCEI-UHFFFAOYSA-N alpha-cholestanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 QYIXCDOBOSTCEI-UHFFFAOYSA-N 0.000 description 1
- 210000001557 animal structure Anatomy 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 210000000133 brain stem Anatomy 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 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
- 239000003054 catalyst Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 210000004907 gland Anatomy 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- BYTCDABWEGFPLT-UHFFFAOYSA-L potassium;sodium;dihydroxide Chemical compound [OH-].[OH-].[Na+].[K+] BYTCDABWEGFPLT-UHFFFAOYSA-L 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002594 sorbent Substances 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 238000000194 supercritical-fluid extraction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 210000001835 viscera Anatomy 0.000 description 1
- 229940046008 vitamin d Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Steroid Compounds (AREA)
Abstract
This invention discloses a method for extracting high-purity cholesterol from lanolin. The method comprises: (1) dissociating cholesterol from lanolin by transesterification reaction; (2) performing short-path distillation to obtain cholesterol crude product; (3) purifying by silica gel column chromatography; (4) crystallizing to obtain refined cholesterol with purity higher than 95% and yield higher than 70%. The method has such advantages as high product consumption, little pollution, simple process and easy operation, thus is suitable for mass production.
Description
Technical field
This patent relates to a kind of extracting method of cholesterol, and is specifically a kind of from adopting transesterificationization-short-path distillation-column chromatography-new crystalline technology, extracts the method for high net cholesterol from lanolin.
Background technology
Cholesterol is a kind of important medicine intermediate, can synthesis of vitamin d 3 by it, and a series of steroidal anti-inflammatory class medicine; In addition because cholesterol makes it become indispensable substance in the cosmetics of super quality to the skin excellent lubricating properties.At present the approach of producing of cholesterol roughly has two: the one, from the brain stem of animal, internal organ, extract; The one, from lanolin, extract.Because there is doubt in Disease-causing gene among the animal organ to the mankind's potential hazard, and last approach is subjected to the restriction of world market day by day and is replaced by the latter gradually.
Lanolin is to be secreted and be attached on Ester on the wool by the sheepskin adipose gland, can reclaim acquisition from waste water from washing wool.The lanolin fatty acid of separating from lanolin has kind more than 30 approximately, and wherein straight-chain acid content is less, and branched acids content is more, accounts for about 9.5% and 60% of fatty acid total amount respectively.Also have alcohol acid in addition, account for 28% of fatty acid total amount.Contained fatty acid carbon chain is all longer, and carbon number is generally more than 10, have in addition up to more than 30.Separable pure about kind more than 70 of coming out can be divided into Fatty Alcohol(C12-C14 and C12-C18), sterol and triterpene alcohol three classes from lanolin.Fatty Alcohol(C12-C14 and C12-C18) accounts for the 30-50% of pure total amount, based on branched-chain alcoho.Sterol accounts for about 30% of pure total amount, and wherein cholesterol level is the highest.Triterpene alcohol accounts for the 25-30% of pure total amount.These materials all are in conjunction with forming lanolin with ester bond, can or change esterification method by saponification disconnects ester bond, thereby the acquisition cholesterol, see for details Koresawa T at " Hashimoto R.Journal of SCCJ " the 274th~2788 page of the 29th phase of nineteen ninety-five and Nakajima M. the 84th~95 page of " Fragrance Journal " 1993 the 21st phase.Therefore the general technology route that extracts cholesterol from lanolin is: at first lanolin is carried out saponification or transesterification, make cholesterol dissociate out, adopt suitable separation means that cholesterol is purified then.
Iuchi K, Dezawa K. are open in Japanese Patent JP 76,139,806,1976: the saponification of early stage lanolin is generally carried out in alkali aqueous solution, and the alkali of employing is sodium hydroxide (potassium) or calcium hydroxide.But because the sour and pure carbochain of lanolin is all very long, the solubleness of its saponification resultant in lanolin is bigger, and lanolin is had certain emulsifying effect, and all is insoluble in water, makes that saponification is difficult to thoroughly finish.Thereby the saponification of lanolin is more much more difficult than common grease, need adopt comparatively exacting terms just can finish.Use instead among the Czech patents CS 231912 and in pure alkaline solution, carry out saponification reaction, with lower alcohol (methyl alcohol or ethanol) is solvent, saponification under the effect of sodium hydroxide (potassium), because lanolin has certain solubleness in lower alcohol, make saponification reaction in homogeneous phase, carry out substantially, improved saponification speed and saponification degree.But increased consumption of organic solvent, and emulsion is still quite serious, for follow-up extracting and separating work brings great difficulty.Also having a kind of feasible method is to adopt the thought of transesterificationization, promptly under the effect of strong alkaline substance sodium alkoxide (normally methyl alcohol) lanolin is converted into the lanolin fatty acid low-carbon-ester, makes lanosterol (cholesterol) dissociate out.Compare with saponification method, the transesterification method has following advantage: the one, and the yield height, cholesterol does not go up substantially and loses, and cholesterol has certain loss in the sepn process of method for saponification product; Transesterification process does not in addition make water, and waste water, the waste residue of generation are less; More crucial is that the transesterification product is more easily handled, and lanolin fatty acid methyl esters and cholesterol can be separated by supercritical extraction.
Very complicated through the alcohols material in the lanolin after saponification or the transesterificationization, except that containing cholesterol, also have the materials close such as more beta-cholestanol, lanosterol, agnosterol and lanostenol, make that therefore the mask work of cholesterol is comparatively difficult with cholesterol character.The simplest method is to adopt solvent extration or solvent crystallization, utilizes cholesterol to separate with other sterols material difference of solubleness in organic solvent.As described in Chinese patent CN 1594350, the contriver adopts all kinds of organic solvents that the saponification resultant of lanolin is carried out multi-stage solvent extraction, and recrystallization has finally obtained purity and surpassed 90% cholesterol product then.But it is huge that this operational path solvent expends, and total recovery is extremely low, thereby do not have industrial value substantially.European patent EP 53415 adopts the method for traditional column chromatography that cholesterol is separated with U.S. Pat 4977243, with silica gel is sorbent material, the mixed solution of heptane and acetone is an elutriant, and the yield that obtains cholesterol thus can reach more than 90%, and purity can reach more than 70%.This method gained cholesterol yield is higher, and product can reach more than 90% through purity behind the recrystallization, is a route that industrial prospect is arranged therefore.Patent documentation CZ 237195 and PL164762 have reported that another operational path with industrial value is divalent metal muriate (calcium chloride, magnesium chloride, zinc chloride an etc.) complexometry, utilize the interaction realization of cholesterol and divalent-metal ion uniqueness and separating of other lanosterol, and then the complex compound decomplexing can be obtained cholesterol.But a defective of this method is the metal chloride large usage quantity, and yield is not high, in addition, if adopt zinc chloride also can produce reluctant waste water owing to the introducing of heavy metal ion, causes environmental pollution.The cavity that Japanese Patent JP 07278181 (1995) adopts cyclodextrin separates sterol in the lanolin to the special complex ability of sterols material, but because the price of cyclodextrin own is higher, and the cyclodextrin loss is comparatively serious in the decomplexing process, so this method only is suitable for a small amount of separation of sterols material in the lanolin.
Czech patents CZ 279,996 (1995) adopts molecular distillation technique to extract lanosterol from lanolin.It at first adopts the saponified method with sodium hydroxide lanolin to be hydrolyzed to obtain the trip cholesterol, isolate organic phase with the method for thin film evaporation after with mineral acid saponification resultant being neutralized then, then organic phase is carried out molecular distillation under 200-280 ℃, 0.1-0.01Pa, obtain 72% light constituent at last.This light constituent is handled, promptly obtained lanosterol (mixture of cholesterol and other other lanosterol) behind the acetone extract with CaO.But this patent is not further segmented out cholesterol to lanosterol.
Summary of the invention
The present invention adopts transesterificationization-short-path distillation-column chromatography-crystalline novel process, extracts high-purity cholesterol from lanolin.
Specifically comprise the steps:
1. under 50~85 ℃ of the temperature of reaction, to carry out transesterification in lanolin raw material and the catalyzer adding lower alcohol, used lower alcohol can be a methyl alcohol, ethanol, a kind of in Virahol or the propyl carbinol, the lower alcohol consumption is 1~3L/kg lanolin raw material, employed catalyzer can be a sodium hydroxide, potassium hydroxide, sodium methylate, potassium methylate, a kind of in sodium ethylate or the potassium ethylate, catalyst levels is 1.6~5.0% of a lanolin raw material weight, reaction times 1~3h, be reflected under the normal pressure and carry out, cholesterol is dissociated out from the lanolin fatty acid cholesterol ester, the reaction solution that must contain free cholesterol, reaction solution neutralizes with mineral acid, for example sulfuric acid, phosphoric acid or hydrochloric acid.
2. the reaction solution after will neutralizing is preheated to 100~120 ℃, enters short-distance distiller cholesterol is carried out extracting, and short-distance distiller can adopt rotation scraped film type short-distance distiller.The operational condition of short-path distillation is: one-level short-path distillation temperature is 120~200 ℃, vacuum tightness 100~300Pa; 180 ℃~280 ℃ of secondary short-path distillation temperature, vacuum tightness 0.1~10Pa.Blade applicator rotating speed 350~600rpm, cold-boundary temperature is 30~60 ℃, the light phase part that obtains behind the short-path distillation of the second stage, i.e. cholesterol crude product.
3. the cholesterol cut is further separated with chromatography, used separating medium is silica gel or γ-activated alumina or macroporous adsorbent resin, and used eluent is the mixture of sherwood oil and toluene, and the volume proportion of composing of sherwood oil and toluene is 95: 5~70: 30.30~60 ℃ are dissolved in 2. middle gained cholesterol crude product in the eluent down, the loading capacity of cholesterol crude product is 0.01-0.1kg cholesterol crude product/kg adsorption stuffing, speed with 0.1-0.2BV/h uploads on the chromatography column, carry out wash-out with eluent with the flow velocity of 1.5BV/h~4.5BV/h then, total elution volume is 4.5~5.5BV, collect the effluent liquid of 3~3.5BV, be the cholesterol crude product behind the evaporate to dryness.
4. the cholesterol product that obtains behind the chromatography is made into saturated solution with organic solvent 56~78 ℃ of dissolvings, organic solvent can be a kind of or wherein several mixture in acetone, normal hexane, hexanaphthene, ethyl acetate, methyl alcohol, ethanol, isopropyl acetone, the propyl carbinol, and the consumption of organic solvent ratio is 15~30L/kg cholesterol product.With the solution crystallisation by cooling of lowering the temperature.The whole temperature of crystallisation by cooling is 20~25 ℃, crystalline product filters, after the oven dry promptly.
The present invention compares with the existing technology of extracting cholesterol from lanolin, has following advantage:
1, patent of the present invention adopts transesterificationization-short-path distillation-column chromatography-crystalline novel process, obtained purity first up to 95% cholesterol product, and yield is up to more than 70%.
2, the present invention adopts the transesterification method to substitute method for saponification in the document and realizes dissociating of cholesterol in the lanolin, has the yield height, and waste water, the waste residue of generation are few, and the easier characteristics of product postprocessing.
3, the present invention adopt the short-path distillation technique to high-efficiency removal lower boiling and the high-boiling-point impurity in the separation system, reduce the processing load of later separation step, helped the raising of output, also made treatment scheme simple, easy handling is suitable for scale operation; In addition, compare with technologies such as solvent extractions, separating obtained cholesterol crude product color and luster is light, and viscosity is low, also helps follow-up chromatography implementation of processes.
Embodiment
Embodiment 1:
Transesterification: in the there-necked flask of 2500ml, drop into 500g lanolin raw material and 1000ml anhydrous methanol, the heating in water bath holding temperature is 70 ℃, the methanol solution of sodium methylate that slowly adds 50g 40%, mixing speed 25rpm get brown viscous liquid behind the reaction 2h down.After the stopping of reaction, in reaction solution, add in the 13g phosphoric acid and excessive alkali.
Short-path distillation: the reaction solution after will neutralizing is preheated to 110 ℃, enters short course distillation device with the speed of 0.18L/h.The short-path distillation operational condition is: 130 ℃ of one-level Heating temperatures, vacuum tightness 150Pa; 200 ℃ of secondary Heating temperatures, vacuum tightness 0.1Pa, short-distance distiller scraper plate rotating speed 400rpm, 50 ℃ of condensing temperatures.Collect the light phase fraction 218g of secondary distillation, be faint yellow cholesterol crude product, analyze and know that cholesterol level is 23.3%.
Chromatographic separation I: take by weighing the thick product 36g of cholesterol and under 30 ℃, be dissolved in 300ml sherwood oil/toluene (85/15, v/v) in the mixed solution, speed with 0.1BV/h uploads on the chromatography column of φ 5cm * 25cm, and the adsorption stuffing that chromatography column adopts is 90~120 order silica gel 500g.After last sample finishes, sherwood oil and toluene mixed solvent with 85: 15 (v/v) carry out wash-out, elution rate is 1.5BV/h, eluent consumption 4.5BV, the effluent liquid of collecting 3~3.5BV is the cholesterol product, and evaporate to dryness gets white powder 10.2g, wherein cholesterol purity is 90.1%, and once through yield is 91.2%.
Chromatographic separation II: other takes by weighing the thick product 36g of cholesterol and be dissolved in 300ml sherwood oil/toluene (95/5 under 30 ℃, v/v) in the mixed solution, speed with 0.2BV/h uploads on the chromatography column of φ 5cm * 25cm, and the adsorption stuffing that chromatography column adopts is 90~120 order silica gel 500g.After last sample finishes, sherwood oil and toluene mixed solvent with 95: 5 (v/v) carry out wash-out, elution rate is 2.0BV/h, eluent consumption 5.5BV, the effluent liquid of collecting 3~3.5BV is the cholesterol product, and evaporate to dryness gets white powder 10.3g, wherein cholesterol purity is 88.0%, and once through yield is 90.2%.
Chromatographic separation I and chromatographic separation II gained cholesterol white powder are mixed, with evaporate to dryness behind the petroleum ether dissolution, get white powder 20.1g, cholesterol purity is 89.1%.
Get above-mentioned cholesterol 20.1g in there-necked flask, heating in water bath is dissolved in 430ml ethanol under 78 ℃.Then in airbath, be cooled to eventually 30 ℃ of temperature under the 10rpm mixing speed, and keep 30 ℃ end temperature 3h make crystallisate aging.At last, will get cholesterol white needle crystals thing 16.1g after crystallisate filtration, the oven dry, purity is 95.5%, and yield is 85.9%.
Embodiment 2:
Transesterification: with embodiment 1.
Short-path distillation: the reaction solution after will neutralizing is preheated to 110 ℃, enters short course distillation device with the speed of 0.18L/h.The short-path distillation operational condition is: 130 ℃ of one-level Heating temperatures, vacuum tightness 150Pa; 200 ℃ of secondary Heating temperatures, vacuum tightness 0.1Pa, short-distance distiller scraper plate rotating speed 400rpm, 50 ℃ of condensing temperatures.Collect the light phase fraction 218g of secondary distillation, be the thick product of faint yellow cholesterol, analyze and know that cholesterol level is 22.9%.
Chromatographic separation: take by weighing the thick product 36g of cholesterol and under 30 ℃, be dissolved in 300ml sherwood oil/toluene (70/30, v/v) in the mixed solution, speed with 0.1BV/h uploads on the chromatography column of φ 5cm * 25cm, and the adsorption stuffing that chromatography column adopts is 90~120 order silica gel 500g.After last sample finishes, sherwood oil and toluene mixed solvent with 70: 30 (v/v) carry out wash-out, elution rate is 4.5BV/h, eluent consumption 5.0BV, the effluent liquid of collecting 3~3.5BV is the cholesterol product, and evaporate to dryness gets white powder 11.0g, wherein cholesterol purity is 78.0%, and once through yield is 85.1%.
Get above-mentioned cholesterol crude product 11.0g in there-necked flask, heating in water bath is dissolved in the 222ml ethyl acetate under 77 ℃.Then in airbath, be cooled to eventually 30 ℃ of temperature under the 10rpm mixing speed, and keep 30 ℃ end temperature 3h make crystallisate aging.At last, will get cholesterol white needle crystals thing 7.3g after crystallisate filtration, the oven dry, purity is 88.1%, and yield is 82.3%.
Embodiment 3:
Transesterification, short-path distillation and chromatographic separation step are with embodiment 1 operation.
Chromatographic separation I among the embodiment 1 and chromatographic separation II gained cholesterol white powder are mixed, with evaporate to dryness behind the petroleum ether dissolution, get white powder 20.1g, cholesterol purity is 89.1%.
Get above-mentioned cholesterol 10.0g in there-necked flask, heating in water bath is dissolved in 255ml acetone under 56 ℃.Then in airbath, be cooled to eventually 30 ℃ of temperature under the 10rpm mixing speed, and keep 30 ℃ end temperature 3h make crystallisate aging.At last, will get cholesterol white needle crystals thing 7.2g after crystallisate filtration, the oven dry, purity is 93.1%, and yield is 75.2%.
Embodiment 4:
Transesterification: with embodiment 1.
Short-path distillation: the reaction solution after will neutralizing is preheated to 110 ℃, enters short course distillation device with the speed of 0.18L/h.The short-path distillation operational condition is: 150 ℃ of one-level Heating temperatures, vacuum tightness 165Pa; 250 ℃ of secondary Heating temperatures, vacuum tightness 0.15Pa, short-distance distiller scraper plate rotating speed 500rpm, 50 ℃ of condensing temperatures.Collect the light phase fraction 220g of secondary distillation, be faint yellow cholesterol crude product.
Chromatographic separation: take by weighing the thick product 36g of cholesterol and under 30 ℃, be dissolved in 300ml sherwood oil/toluene (85/15, v/v) in the mixed solution, speed with 0.1BV/h uploads on the chromatography column of φ 5cm * 25cm, and the adsorption stuffing that chromatography column adopts is 90~120 order silica gel 500g.After last sample finishes, sherwood oil and toluene mixed solvent with 85: 15 (v/v) carry out wash-out, elution rate is 2.5BV/h, eluent consumption 5.0BV, the effluent liquid of collecting 3~3.5BV is the cholesterol product, and evaporate to dryness gets white powder 10.9g, wherein cholesterol purity is 90.5%, and once through yield is 91.9%.
Crystallization: above-mentioned cholesterol 10.9g is placed there-necked flask, under 78 ℃ of heating in water bath, be dissolved in 225ml ethanol.Then in airbath, be cooled to eventually 30 ℃ of temperature under the 10rpm mixing speed, and keep 30 ℃ end temperature 3h make crystallisate aging.At last, will get cholesterol white needle crystals thing 7.8g after crystallisate filtration, the oven dry, purity is 95.4%, and yield is 81.7%.
Embodiment 5:
Transesterification: with embodiment 1.
Short-path distillation: the reaction solution after will neutralizing is preheated to 110 ℃, enters short course distillation device with the speed of 0.18L/h.The short-path distillation operational condition is: 180 ℃ of one-level Heating temperatures, vacuum tightness 190Pa; 280 ℃ of secondary Heating temperatures, vacuum tightness 0.25Pa, short-distance distiller scraper plate rotating speed 500rpm, 50 ℃ of condensing temperatures.Collect the light phase fraction 230g of secondary distillation, be faint yellow cholesterol crude product, analyze and know that cholesterol level is 22.2%.
Chromatographic separation: take by weighing the thick product 110g of cholesterol and under 30 ℃, be dissolved in 1000ml sherwood oil/toluene (85/15, v/v) in the mixed solution, speed with 0.1BV/h uploads on the chromatography column of φ 8cm * 80cm, and the adsorption stuffing that chromatography column adopts is 90~120 order silica gel 4000g.After last sample finishes, sherwood oil and toluene mixed solvent with 85: 15 (v/v) carry out wash-out, elution rate is 2.5BV/h, eluent consumption 5.0BV, the effluent liquid of collecting 3~3.5BV is the cholesterol product, and evaporate to dryness gets white powder 23.9g, wherein cholesterol purity is 91.1%, and once through yield is 89.9%.
Crystallization: above-mentioned cholesterol 23.9g is placed there-necked flask, under 78 ℃ of heating in water bath, be dissolved in 495ml ethanol.Then in airbath, be cooled to eventually 30 ℃ of temperature under the 10rpm mixing speed, and keep 30 ℃ end temperature 3h make crystallisate aging.At last, will get cholesterol white needle crystals thing 18.8g after crystallisate filtration, the oven dry, purity is 95.8%, and yield is 83.2%.
Embodiment 6:
Transesterification, short-path distillation: with embodiment 5.
Chromatographic separation: take by weighing the thick product 110g of cholesterol and under 30 ℃, be dissolved in 1000ml sherwood oil/toluene (85/15, v/v) in the mixed solution, speed with 0.1BV/h uploads on the chromatography column of φ 8cm * 80cm, and the adsorption stuffing that chromatography column adopts is 90~120 order silica gel 4000g.After last sample finishes, sherwood oil and toluene mixed solvent with 85: 15 (v/v) carry out wash-out, elution rate is 2.0BV/h, eluent consumption 5.5BV, the effluent liquid of collecting 3~3.5BV is the cholesterol product, and evaporate to dryness gets white powder 22.9g, wherein cholesterol purity is 91.8%, and once through yield is 89.0%.
Crystallization: above-mentioned cholesterol 22.9g is placed there-necked flask, under 78 ℃ of heating in water bath, be dissolved in 580ml ethanol.Then in airbath, be cooled to eventually 30 ℃ of temperature under the 10rpm mixing speed, and keep 30 ℃ end temperature 3h make crystallisate aging.At last, will get cholesterol white needle crystals thing 16.8g after crystallisate filtration, the oven dry, purity is 96.0%, and yield is 77.7%.
Claims (7)
1. method of extracting cholesterol from lanolin is characterized in that: may further comprise the steps:
1. transesterification: the lanolin raw material is mixed with lower alcohol, keeps 50~85 ℃ of temperature of reaction, add catalyzer, normal pressure stir down react down reaction solution, the adding mineral acid neutralizes in reaction solution;
2. short-path distillation: distill after the reaction solution preheating after the neutralization, cholesterol is carried out extracting, the light phase that obtains after the distillation partly is the cholesterol crude product;
3. column chromatography: the cholesterol crude product is dissolved in the eluent, the loading capacity of cholesterol crude product is 0.01~0.1kg cholesterol crude product/kg adsorption stuffing, speed with 0.1~0.2BV/h uploads on the chromatography column, carry out wash-out with eluent with the flow velocity of 1.5BV/h~4.5BV/h then, total elution volume is 4.5~5.5BV, collect the effluent liquid of 3~3.5BV, be the cholesterol crude product behind the evaporate to dryness;
4. crystallization: the cholesterol product that obtains behind the chromatography is dissolved in the organic solvent, crystallisation by cooling, crystalline product filter, after the oven dry promptly.
2. method according to claim 1 is characterized in that: the lower alcohol of step described in 1. is methyl alcohol, ethanol, Virahol or propyl carbinol, and the lower alcohol consumption is 1~5L/kg lanolin raw material.
3. method according to claim 1 is characterized in that: the catalyzer of step described in 1. is sodium hydroxide, potassium hydroxide, sodium methylate, potassium methylate, sodium ethylate or potassium ethylate, and the weight of catalyzer accounts for 1.6~5.0% of lanolin raw material gross weight.
4. method according to claim 1 is characterized in that: the mineral acid of step described in 1. is sulfuric acid, phosphoric acid or hydrochloric acid.
5. method according to claim 1 is characterized in that: the adsorption stuffing of step described in 3. is a kind of in silica gel, γ-activated alumina or the macroporous adsorbent resin.
6. method according to claim 1 is characterized in that: the eluent of step described in 3. is the mixture of sherwood oil and toluene, and the volume proportion of composing of sherwood oil and toluene is 95: 5~70: 30.
7. method according to claim 1, it is characterized in that: the organic solvent of step described in 4. is a kind of or wherein several mixture in acetone, normal hexane, hexanaphthene, ethyl acetate, methyl alcohol, ethanol, isopropyl acetone, the propyl carbinol, and consumption of organic solvent is 15~30L/kg cholesterol product.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 200610154755 CN1958596A (en) | 2006-11-22 | 2006-11-22 | Method for extracting cholesterol from lanoline |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 200610154755 CN1958596A (en) | 2006-11-22 | 2006-11-22 | Method for extracting cholesterol from lanoline |
Publications (1)
Publication Number | Publication Date |
---|---|
CN1958596A true CN1958596A (en) | 2007-05-09 |
Family
ID=38070461
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN 200610154755 Pending CN1958596A (en) | 2006-11-22 | 2006-11-22 | Method for extracting cholesterol from lanoline |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN1958596A (en) |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101817859A (en) * | 2010-06-02 | 2010-09-01 | 天津大学 | Method for separating and extracting cholesterol in lanolin alcohol |
CN102676626A (en) * | 2012-05-24 | 2012-09-19 | 河南利伟生物药业股份有限公司 | Method for preparing cholesterol by microbial conversion method |
CN102690312A (en) * | 2012-05-24 | 2012-09-26 | 河南利伟生物药业股份有限公司 | Purification method for lanolin cholesterol |
CN102731602A (en) * | 2012-07-04 | 2012-10-17 | 浙江大学 | Method for separating cholesteryl ester from lanolin |
CN103012535A (en) * | 2012-12-28 | 2013-04-03 | 广州白云山汉方现代药业有限公司 | Method for preparing refined cholesterol by separating cholesterol from egg oil |
CN103554207A (en) * | 2013-10-30 | 2014-02-05 | 吉安荣威生物科技有限公司 | Lanolin cholesterol production technology |
CN103627519A (en) * | 2012-08-29 | 2014-03-12 | 丰益(上海)生物技术研发中心有限公司 | Method for removing total cholesterol in animal fat |
CN103626820A (en) * | 2013-10-25 | 2014-03-12 | 杭州下沙生物科技有限公司 | Method for preparing high-purity lanolin cholesterol |
CN114196480A (en) * | 2020-09-17 | 2022-03-18 | 武汉华谱生物科技有限公司 | Preparation method of ultrapure lanolin |
CN114426566A (en) * | 2022-01-25 | 2022-05-03 | 淮北师范大学 | Method for separating lanosterol from lanolin |
-
2006
- 2006-11-22 CN CN 200610154755 patent/CN1958596A/en active Pending
Cited By (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101817859A (en) * | 2010-06-02 | 2010-09-01 | 天津大学 | Method for separating and extracting cholesterol in lanolin alcohol |
CN101817859B (en) * | 2010-06-02 | 2012-07-18 | 天津大学 | Method for separating and extracting cholesterol in lanolin alcohol |
CN102676626A (en) * | 2012-05-24 | 2012-09-19 | 河南利伟生物药业股份有限公司 | Method for preparing cholesterol by microbial conversion method |
CN102690312A (en) * | 2012-05-24 | 2012-09-26 | 河南利伟生物药业股份有限公司 | Purification method for lanolin cholesterol |
CN102731602A (en) * | 2012-07-04 | 2012-10-17 | 浙江大学 | Method for separating cholesteryl ester from lanolin |
CN103627519B (en) * | 2012-08-29 | 2016-06-08 | 丰益(上海)生物技术研发中心有限公司 | A kind of de-method except total cholesterol in animal tallow |
CN103627519A (en) * | 2012-08-29 | 2014-03-12 | 丰益(上海)生物技术研发中心有限公司 | Method for removing total cholesterol in animal fat |
CN103012535A (en) * | 2012-12-28 | 2013-04-03 | 广州白云山汉方现代药业有限公司 | Method for preparing refined cholesterol by separating cholesterol from egg oil |
CN103626820B (en) * | 2013-10-25 | 2015-08-19 | 杭州下沙生物科技有限公司 | A kind of high purity lanolin cholesterol preparation method |
CN103626820A (en) * | 2013-10-25 | 2014-03-12 | 杭州下沙生物科技有限公司 | Method for preparing high-purity lanolin cholesterol |
CN103554207A (en) * | 2013-10-30 | 2014-02-05 | 吉安荣威生物科技有限公司 | Lanolin cholesterol production technology |
CN114196480A (en) * | 2020-09-17 | 2022-03-18 | 武汉华谱生物科技有限公司 | Preparation method of ultrapure lanolin |
CN114196480B (en) * | 2020-09-17 | 2023-11-07 | 武汉华谱生物科技有限公司 | Preparation method of ultrapure lanolin |
CN114426566A (en) * | 2022-01-25 | 2022-05-03 | 淮北师范大学 | Method for separating lanosterol from lanolin |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN1958596A (en) | Method for extracting cholesterol from lanoline | |
CN101817859B (en) | Method for separating and extracting cholesterol in lanolin alcohol | |
CN102850248A (en) | Technology for preparing vitamin D3 | |
CN107501045B (en) | Method for separating and purifying butanetriol from fermentation liquor by using macroporous adsorption resin | |
CN101049980A (en) | Method for comprehensive utilization for benzene extracting concentrated solution of residue wastewater | |
CN107778277B (en) | Process for the recovery of squalene, vitamin E and/or sterols | |
CN110283034B (en) | Method for obtaining high-purity squalene from vegetable oil deodorized distillate | |
CN1594350A (en) | Method for separating and extracting cholesterol from lanolin | |
CN102993134B (en) | A kind of method of purification of Lipstatin | |
CN102675108B (en) | Refining method of pyrethrin crude extract | |
CN102633768B (en) | Method for transforming cisconfiguration of oxane compounds to transconfiguration | |
CN113348160A (en) | Fish oil cholesterol | |
CN101648957B (en) | Preparation method of sesamin phenol | |
CN1911881A (en) | Method of separating wool acid and lanonol from wool grease | |
CN101386637A (en) | Method for refining cholesterin by activated carbon fixed bed adsorption process | |
CN1418877A (en) | Process for extracting vitamin E from plant-oil debrominated distillate | |
CN101486951A (en) | Method for separating oleate, linolic acid, oleate and linoleate | |
CN1944375A (en) | Method for extracting isostearic acid from monoacid | |
JP4914113B2 (en) | Method for producing sterols | |
CN1295244C (en) | Method for extracting stigmasterol from plant sterol | |
CN112079713B (en) | Method for treating mixtures containing long-chain dibasic acids and use thereof | |
CN1763072A (en) | Process for extracting active component ursolic acid from persimmon leaf | |
TWI653331B (en) | Method for extracting sesame lignan from by-products produced by producing sesame oil | |
CN104098510B (en) | Method for extracting lappaconitine from aconitum sinomontanum plant roots | |
CN114380661B (en) | Synthetic method of (+/-) -lavender alcohol |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
WD01 | Invention patent application deemed withdrawn after publication |
Open date: 20070509 |