CN103113446B - The method of separation and Extraction sterol from lanolin - Google Patents
The method of separation and Extraction sterol from lanolin Download PDFInfo
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Abstract
The invention discloses a kind of method of separation and Extraction high purity sterol from lanolin, comprise the steps: that 1. lanolin carries out saponification reaction in alkali alcoholic solution; 2. utilize calcium chloride and upper step product to carry out saponification metathesis, obtain calcium soap and lanosterol; 3. the filtrate that obtains of suction filtration, utilizes lower aliphatic alcohols to filter residue reflux extraction, collects filtrate, adds lipid acid, the calcium ion that removing is residual; 4. filter cake obtains lanolin fatty acid after acidifying bleaching; 5. recrystallization obtains purified product.After above each step, the cholesterol purity obtained is higher than 93%, and yield is greater than 78%.The method advantage obtains product purity and yield is high, color and luster and crystal formation is good, free from extraneous odour, and technical process is simple, easy handling, and solvent, all recyclable recycling of chromatography media in technical process, essentially no waste produces, thus make this process costs cheap, can suitability for industrialized production.
Description
Technical field
The invention belongs to bio-chemistry separation direction, for separation and Extraction sterol from lanolin, specifically refer to through techniques such as saponification → metathesis → solvent slective extraction → column chromatography → recrystallizations, obtain the method for the sterols such as high quality cholesterol, lanosterol.
Background technology
The natural materials that cholesterol is known as a kind of people, owing to having multifrequency nature, makes it be widely used at makeup, material, biomedicine field.1. analyze from biological factor aspect, cholesterol cell membrane has affinity interaction, and can change the character of cytolemma, and this is significant for the application of polymkeric substance in Thermosensitive Material Used for Controlled Releasing of Medicine and organizational project.2. important pharmaceutical intermediate, is mainly used in synthesis of vitamin d
3, steroid drugs and dependency hormone etc.3. cholesterol has mulitiple chiral centers, and its derivative (ethers, ester class, halogenide, carbonic ether etc.) can form the aggregate of various uniqueness, comprises liquid crystal, organogel and unimolecular layer, special cholest-class liquid crystal molecule.4. cholesterol has oilness to skin, and the structure of its uniqueness can absorb free radical, and therefore cholesterol can be used as the additive of makeup and sunscreen.
1. the production technique of current cholesterol has extracts from animal brain and myeloid tissue.Because leaching process cost is high, not environmentally, and the product obtained is limited, limits it and further develops; 2. extract from wool washing waste water, its complex process, benefit are low; 3. extract from lanolin, its raw material sources are extensive, with low cost, are easy to produce.
Lanolin is the smegma thing of sheep, is deposited on wool fiber.Degras is a kind of brown, dope frowzy, is that yellow is translucent, the thickness body of paste of oiliness after refining.Fusing point is 39 ~ 42 DEG C; Water-soluble hardly, but the moisture being equivalent to own wt 2 times can be absorbed; Lanolin is soluble in ether, benzene, chloroform, acetone, sherwood oil, hard to tolerate in cold alcohol, dissolves in hot alcohol, can be used as cosmetic emollients, permeate agent, emulsifying agent etc.; The higher fatty acid for automobile chassis coating can be obtained after refining; Also can be used as gas-chromatography low-pole stationary liquid, for the analysis of non-polar compound.
Lanolin is known as again " soft gold ", and its each composition all has a wide range of applications.Lanolin composition can be divided into lanolin fatty acid and the large class of lanosterol two.In lanosterol except cholesterol and fatty alcohol, lanosterol has good perviousness, water-absorbent and lubricity etc., mainly as the additive of the cosmetics of super quality, lipstick, fragrant body cream, lipstick etc., and its considerable cost, be the product of high value.
Last century, at home lanolin mainly after refining as lubricant or rudimentary cosmetics additive, value added is very low.As mentioned above, the materials such as the cholesterol that lanolin obtains after separation and purification, lipid acid, lanosterol, are all the products with high additive value, are more conducive to the future development of this industrial chain.With regard to current progress of research, the general step of cholesterol separation and purification in lanolin is: saponification/transesterification → alcohol soap is separated → is separated cholesterol → recrystallizing and refining.
According to current domestic and international progress, in lanolin, the separating and extracting method of cholesterol is a feast for the eyes, see report and just have about 8 kinds, be respectively molecular distillation, supercritical fluid extraction, bromination method, solvent selective freezing, adsorpting column chromatography, partition column chromatography, adduct process cyclodextrin method etc.
Be separated at lanosterol and lanolin fatty acid, product Extraction parts: Xiamen Jin Dawei house journal CN101085716A describes a kind of method completing lanosterol and lanolin fatty acid and be separated, contriver utilizes liquid-liquid extraction column, continuous extraction is carried out to lanolin saponification resultant, reach both to be separated, experimental procedure is simple, but Solvent quantity is large, and recovery utilization rate is low, and does not further study the further separation of crude product.Solvent slective extraction is utilized to complete being separated of lanosterol and lanolin fatty acid in Zhejiang University patent CN1594350A, then utilize the method for solvent selective freezing to be separated and obtain thick cholesterol, the major defect of the method wants controling parameters more in experimentation, and the more difficult control of major part, as experiment service temperature, the screening of solvent for use, solvent load and crystallization operation parameter etc.Patent CN1884460A is the problem avoiding using in experimentation acid base catalysator, utilizes in critical aqueous medium, and lanosterol and lanolin fatty acid are prepared in hydrolysis, and process is simple, but service temperature is too high.University Of Tianjin patent CN101817859A directly adopts Wool wax alcohol to be starting raw material, utilizes molecular distillation to obtain refining lanosterol, then with methyl alcohol and acetone for solvent, regulate ratio, after multistep selective freezing, obtain cholesterol.The consumption of the method chemical adjuvant is few, but molecule rectifying device is expensive, and solvent slective extraction conditional parameter difficulty controls.Zhejiang University patent CN1958596A describes column chromatography method to reach product separation, first transesterification is carried out to lanolin, then short-path distillation is carried out, obtain cholesterol crude product, then wet method loading, with 90 ~ 120 order silica gel for chromatography media, toluene and sherwood oil (ratio is 70:30 ~ 95:5) carry out wash-out for moving phase, obtain the cholesterol that purity is 88% ~ 90%, in experimentation, transesterification portion obtains the easy emulsification of soda soap, makes soap and alcohol separation difficulty; Short-path distillation relates to gradient increased temperature, and outlet temperature is at 200 DEG C, operational hazards in industrialization; Column chromatography steps, adopts operate continuously, isocratic elution, can complete the separation of sterols, but purity is not high, and manipulation require carries out again under 30 DEG C of constant temperature, further requirement is just proposed to the design of chromatography column, larger challenge is proposed to the design of pillar in industrialization.
For solving soda soap to the emulsification of reaction solution, column chromatography sample thickness, column chromatography constant temperature method, the not high in esse problem of product separation purity, therefore this patent relates to and overcomes the above problems and obtain the method for high purity sterol.
Summary of the invention
Content of the present invention relates to " lanolin saponification → metathesis → alcohol soap separation → calcium soap acidifying/solvent slective extraction → column chromatography for separation sterol → product recrystallization " this product separation such as cholesterol, lanosterol purifying technique.
Cholesterol separation purifying technique in the present invention, comprises the following steps:
1) lanolin saponification: the alkali (lanolin and alkali mol ratio are 1:1.3 ~ 1:2) taking respective amount is added in reaction vessel, and add appropriate amount fatty alcohol (6 ~ 10mL/g lanolin) and water (0 ~ 4mL/g lanolin) as solvent, add the lanolin of brown molten state while stirring, stirring reaction 3 ~ 8 hours under 78 ~ 85 DEG C of conditions, reaction solution color is deepened gradually, obtains brownish black mixing solutions after terminating.
2) calcium soap transforms: cool between above-mentioned reaction solution to 40 ~ 55 DEG C, and utilizes mineral acid adjust ph to be after about 8.5, and take the calcium salt of 0.5 times (relative to sodium hydroxide concentration), stirring reaction 1 ~ 2 hour, obtains dark brown mixture.
3) alcohol soap is separated: after mixture suction filtration, utilized by residue dehydrated alcohol to carry out twice extraction, merges the dark brown filtrate and khaki color filter residue that obtain.
4) calcium soap acidifying: after being dissolved in lower paraffin hydrocarbons by the lanolin fatty acid soap obtained, and be heated to 50 ~ 60 DEG C, add the mineral acid of specified quantitative, stirring reaction 15 ~ 30min, carry out suction filtration while hot, obtains white or faint yellow solid and dark brown liquid.
5) lanolin fatty acid is refined: be divided into three layers after dark brown liquid washes with water, upper strata (dark-brown) and middle level (light yellow), obtains light yellow solid, be accredited as lanolin fatty acid after concentrated; Lower floor is water.
6) solvent slective extraction: lanosterol is dissolved in lower paraffin hydrocarbons, be heated to backflow, add acetic acid (acetic acid and lower paraffin hydrocarbons ratio are 1:4 ~ 1:8), after stirring, obtain light brown liquid and partial white solid, after suction filtration, filtrate is concentrated, obtain yellow solid (lanosterol).
7) column chromatography: add a small amount of silica-gel powder after the lanosterol moving phase obtained being dissolved, revolves and steams to dry.Dry method loading, or directly with paste substance loading, with lower paraffin hydrocarbons and ethyl acetate for moving phase, adjust its ratio from 100%, 30:1,20:1,10:1 carry out gradient elution, carry out thin-layer chromatography qualification simultaneously, collect same composition and also concentrate.Non-saponification lanolin, fatty alcohol, lanosterol, cholesterol, unknown sterol etc. can be obtained successively.
8) product purification: by the component such as cholesterol, lanosterol, utilizes lower alcohol or complex solvent to carry out recrystallization with the ratio of 1:5 ~ 1:10, obtains white needle-like crystals, carry out corresponding construction qualification after drying.
Lower aliphatic hydrocarbon described in the present invention is sherwood oil, normal hexane, Skellysolve A etc.; Lower fatty acid extraction agent is acetic acid; Mineral acid refers to 30% ~ 38% hydrochloric acid, the vitriol oil, phosphoric acid etc.; Step 8) in lower alcohol used refer to 90 ~ 98% ethanol, dehydrated alcohol, methyl alcohol etc., complex solvent refers to the composite use of the lower paraffin hydrocarbonss such as sherwood oil, normal hexane, Skellysolve A and ethyl acetate, methyl alcohol etc.
Other method known with prior art is compared, this programme at least tool have the following advantages in one or all:
1) operational path is simple and easy to operate.Present method co-exists in three large operating units: saponification unit, separating unit, refined unit, and whole operation completes only needs about 18 ~ 24 hours, and in general, route is simple and do not have complicated operation.
2) solve soda soap in saponification reaction and, to the emulsification of reaction system, make the problem of later separation difficulty.
3) recrystallization makes that product yield is high, crystal formation is good, color and luster is good, meets medical production requirement.The current lab scale craft of present method, the cholesterol purity obtained, higher than 93%, meets drug manufacture requirement.
4) productive rate is high, and production cost is low, is convenient to suitability for industrialized production.More than 80%, and there is larger room for promotion in the productive rate of the cholesterol that present method obtains at present; And the solvent used in technique, chromatography media are all recyclable, running cost is reduced greatly, thus ensure that it is convenient to scale-up in the future and suitability for industrialized production.
Accompanying drawing explanation
Fig. 1: lanolin process for separating and purifying schema.
Embodiment
The following examples can make professional and technical personnel more understand the present invention.
embodiment 1
1. take 25.000g lanolin (containing cholesterol about 11%), put into 250mL there-necked flask, add 150mL ethanol and 2.679g sodium hydroxide and 10mL deionized water, be heated to reflux temperature (80 DEG C), mechanic whirl-nett reaction 3-8 hour, reaction end obtains brownish black mixing solutions.
2. reducing reacting liquid temperature is 40 ~ 55 DEG C, and regulate reacting liquid pH value to be about 8.5 ~ 9, take the calcium chloride of 0.5 times of molar weight (relative to sodium hydroxide concentration), stirring reaction 1 ~ 2 hour, reaction solution color shoals gradually, obtain dark yellow mixture (more than 70 DEG C can obtain black residue, are unfavorable for that reaction is carried out).
3. after mixture suction filtration, residue is recycled dehydrated alcohol (200mL × 3) and extract, obtain khaki color calcium soap powder, merge all deep yellow filtrate and carry out concentrated obtaining deep yellow thick liquid.
4. the khaki color calcium soap powder lanolin fatty acid soap obtained is dissolved in sherwood oil, and be heated to 40 ~ 50 DEG C, 8 ~ 10mL36% hydrochloric acid is added under Keep agitation, after stirring reaction 15 ~ 20min, carry out suction filtration while hot, obtain white solid (carrying out infrared identification after solid drying, is fatty acid calcium) and dark brown liquid.
5. dark brown liquid is divided into three layers after washing with water, and upper strata (dark-brown) and middle level (yellow) forms colloidal solid at low temperatures, is accredited as lanolin fatty acid, and molten state is brownish black; Lower floor is water.
6. lanosterol (the deep yellow thick liquid that the 3rd step obtains) is dissolved in sherwood oil, be heated to backflow, add 50mL acetic acid, after stirring, obtain light brown liquid and a small amount of white solid (after dry, infrared identification is calcium acetate), after suction filtration, filtrate is concentrated, obtain refining lanosterol.
7. add a small amount of silica-gel powder by after refining lanosterol petroleum ether dissolution, revolve and steam to dry.Dry method loading, with sherwood oil and ethyl acetate for moving phase, adjustment sherwood oil carries out gradient elution with ethyl acetate ratio, time first with 100% sherwood oil wash-out, can obtain non-saponification lanolin after consuming 500ml; After thin-layer chromatography qualification, use 30:1(all proportions instead and all refer to sherwood oil: ethyl acetate) carry out wash-out, approximately consume popular phase 3L, can fatty alcohol component be obtained; Next is used 20:1 moving phase instead and carries out wash-out, carries out thin-layer chromatography detection simultaneously, ensures that cholesterol components does not flow out, approximately consumes 1.5L moving phase, can obtain lanosterol component; Then use 10:1 moving phase instead and carry out wash-out, approximately consume 2.0L moving phase, can cholesterol components be obtained; Finally carry out wash-out by 100% ethyl acetate of about 1L, carry out thin-layer chromatography qualification at any time, see and whether also have product to be washed out (thin-layer chromatography display washes out without product).
8. lanosterol component previous step (the 7th step) obtained and cholesterol components, dehydrated alcohol (5mL/g) is utilized to carry out recrystallization, cholesterol/crude lanosterol product is put into round-bottomed flask, first add a small amount of ethanol, then backflow is heated to, after dropping ethanol to all powder dissolves completely, then add into 10 ~ 20%(total amount), naturally cooling or subcooling in refrigerator.Finally obtain 2.15g cholesterol, purity 92.6%(productive rate > 78%), and 0.801g lanosterol.
embodiment 2
The step 1-7 of same example 1 is operated before recrystallization step.By the cholesterol crude product obtained, be heated to backflow and be dissolved in (8mL/g) in ethyl acetate, when after solution clarification, dropwise add sherwood oil again, when adding sherwood oil and just making solution muddy, be heated to clarification, be cooled to crystal to separate out, finally obtain 2.07g cholesterol, purity 92.2%.
embodiment 3
The step 1-7 of same example 1 is operated before recrystallization step.By the cholesterol crude product obtained, be heated to backflow and be dissolved in (5mL/g) in dehydrated alcohol, when after solution clarification, dropwise add water again, when adding sherwood oil and just making solution muddy, be heated to clarification, be cooled to crystal to separate out, finally obtain 2.21g cholesterol, purity 93.0%.
embodiment 4
The step 1-7 of same example 1 is operated before recrystallization step.By the cholesterol crude product obtained, be heated to backflow and be dissolved in (10mL/g) in anhydrous methanol, after dropping methyl alcohol to all powder dissolves completely, then add into 10%(total amount), naturally cool to crystal and separate out, finally obtain 1.93g cholesterol, purity 95.2%.
It is to be understood that: although above-mentioned example to be contrasted detailed description to the present invention; but these describe the simple description just to thinking of the present invention; instead of the restriction to this novel thinking of sterol in column chromatography for separation lanolin; any combination not exceeding thinking of the present invention, increases or amendment all falls into protection scope of the present invention.
Claims (5)
1. the method for separation and Extraction sterol from lanolin, is characterized in that comprising the steps:
1. saponification reaction: using lower aliphatic alcohols as solvent, takes alkali, and control temperature, at 50 ~ 60 DEG C, is added dropwise to the lanolin of molten state, optionally drips a small amount of water, is warming up to 78 ~ 85 DEG C, and under normal pressure, stirring reaction 3 ~ 8h obtains dark brown mixture;
2. saponification metathesis: cool above-mentioned reaction solution 40 ~ 55 DEG C, regulates pH to 8-9, adds calcium salt, stirring obtains calcium soap, and centrifugal or suction filtration carries out solid-liquid separation, recycles lower aliphatic alcohols simultaneously and carries out 2 ~ 3 reflux extraction to filter residue, then suction filtration collect filtrate, merges all filtrate and concentrated;
3. filter residue is at 50 ~ 60 DEG C, obtains crude product lanolin fatty acid after mineral acid acidified, common and braid wool acid carry out refining after obtain refining lanolin fatty acid;
4. the residual calcium ion of removing, reduces lanosterol viscosity: by filtrate concentrated solution lower paraffin hydrocarbons, ethyl acetate, methyl alcohol or ether dissolution, adds lower fatty acid and stirs, obtain white solid, after suction filtration, oil phase is washed, to aqueous phase pH in neutral, collect oil phase and concentrate; Described lower paraffin hydrocarbons is normal hexane or Skellysolve A; The 4. described lower fatty acid of step is acetic acid;
5. a small amount of silica-gel powder is added by after the concentrated oil phase petroleum ether dissolution of upper step, revolve and steam to dry, dry method loading, with sherwood oil and ethyl acetate for moving phase, adjustment sherwood oil carries out gradient elution with ethyl acetate ratio, first obtains non-saponification lanolin with 100% sherwood oil wash-out; With 30:1 volume ratio sherwood oil: ethyl acetate is carried out wash-out and obtained fatty alcohol component; Next uses 20:1 volume ratio sherwood oil instead: ethyl acetate flowing carries out wash-out mutually, obtains lanosterol component; Then 10:1 volume ratio sherwood oil is used instead: ethyl acetate flowing carries out wash-out mutually, obtains cholesterol components;
6. the lanosterol component upper step obtained and cholesterol components utilize lower aliphatic alcohols to carry out recrystallizing and refining, obtain the finished product; The 1. 2. 6. described lower aliphatic alcoholic solvent of step is dehydrated alcohol or 90-98% ethanol.
2. the method for separation and Extraction sterol from lanolin as claimed in claim 1, is characterized in that: the 2. described calcium salt of step is Calcium Chloride Powder Anhydrous and/or calcium chloride hydrate.
3. the method for separation and Extraction sterol from lanolin as claimed in claim 1, is characterized in that: the 3. described mineral acid of step is 30% ~ 38% hydrochloric acid, sulfuric acid or phosphoric acid.
4. the method for separation and Extraction sterol from lanolin as claimed in claim 1, is characterized in that: chromatography media is 100 ~ 200 order silica gel.
5. the method for separation and Extraction sterol from lanolin as claimed in claim 1, it is characterized in that the process for refining described in step 3. comprises the steps: common and braid wool acid water extracting and separating, wherein gluey lanolin fatty acid solid is formed in dark brown upper and yellow middle level at low temperatures; Lower floor is water, is separated and removes lower floor.
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| CN107325144B (en) * | 2017-06-30 | 2019-11-05 | 安徽科宝生物工程有限公司 | The extracting method of cholesterol in a kind of lanolin |
| CN107141331A (en) * | 2017-07-07 | 2017-09-08 | 赵厚发 | The extracting method of cholesterol in a kind of marine organisms byproduct |
| CN108485821B (en) * | 2018-05-29 | 2021-03-26 | 浙江花园生物高科股份有限公司 | Method for synthesizing refined lanolin by base catalysis |
| CN108840795A (en) * | 2018-08-08 | 2018-11-20 | 江南大学 | A method of lanolin fatty acid and lanonol are prepared by lanolin |
| CN109761867B (en) * | 2019-02-28 | 2021-02-26 | 四川健腾生物技术有限公司 | Vitamin D production by using lanolin as raw material3Is a new method for industrialization |
| CN109776646B (en) * | 2019-03-04 | 2021-06-04 | 河南省科学院高新技术研究中心 | Method for preparing high-purity cholesterol by continuous countercurrent micro-channel extraction |
| CN111686132B (en) * | 2020-06-15 | 2022-06-24 | 中山大学 | Syngnathus sterol solid dispersion and application thereof in treating cerebral apoplexy |
| CN113135972B (en) * | 2021-03-25 | 2022-04-19 | 江西天新药业股份有限公司 | Method for purifying 24-dehydrocholesterol |
| CN113201407A (en) * | 2021-05-21 | 2021-08-03 | 浙江中谱生物科技有限公司 | Method for preparing ultrapure lanolin and synchronously enriching cholesterol ester |
| CN113735931B (en) * | 2021-08-27 | 2022-06-14 | 浙江花园营养科技有限公司 | Method for separating cholesterol and 24-dehydrocholesterol by complexing crystallization |
| CN114456221B (en) * | 2022-01-25 | 2023-05-23 | 淮北师范大学 | Cholesterol separation method |
| CN114426566B (en) * | 2022-01-25 | 2023-07-21 | 淮北师范大学 | Separation method of lanosterol in lanolin |
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