CN101307087A - Process for adsorbing and purifying 3beta-cholest-5,24-diene-3-alcohol by fixed bed - Google Patents
Process for adsorbing and purifying 3beta-cholest-5,24-diene-3-alcohol by fixed bed Download PDFInfo
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- CN101307087A CN101307087A CNA2008100629817A CN200810062981A CN101307087A CN 101307087 A CN101307087 A CN 101307087A CN A2008100629817 A CNA2008100629817 A CN A2008100629817A CN 200810062981 A CN200810062981 A CN 200810062981A CN 101307087 A CN101307087 A CN 101307087A
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Abstract
The invention discloses a method for absorbing and purifying 3 beta- cholest-5,24-diene-3-alcohol through a fixed bed. The method takes a 3 beta- cholest-5,24-diene-3-alcohol crude product extracted from lanolin as a raw material, and obtains a 3 beta- cholest-5,24-diene-3-alcohol product with a purity of above 60 percent through the absorption and separation carried out by the active carbon fixed bed with a 3 beta- cholest-5,24-diene-3-alcohol yield of above 85 percent. The method which is characterized by low production cost, low consumption and little pollution, etc. is suitable for industrialized production with simple process and easy operation.
Description
Technical field
The present invention relates to the chemical engineering isolation technique, especially relate to a kind of ADSORPTION IN A FIXED BED purifying 3 β-courage steroid-5, the method for 24-diene-3-alcohol.
Background technology
3 β-courage steroid-5,24-diene-3-alcohol (3 β-cholesta-5,24-dien-3-ol, Desmosterol, CAS:313-04-2) being to extract a kind of sterols material that obtains serum, liver and some other animal tissuess from blended plant sterol, marine alga, animal, is the biosynthetic direct precursor of cholesterol.Domestic and international research is verified, 3 β-courage steroid-5,24-diene-3-alcohol not only has some physiological actions of cholesterol, also in mammiferous sexual maturity, played vital role, sperm motility also there is material impact, 3 β-courage steroid-5,24-diene-3-alcohol also is important medicine intermediate simultaneously, can be used as many synthetic initial feed, such as moulting hormone with sterol of physiologically active.Therefore, 3 β-courage steroid-5,24-diene-3-alcohol has important economic value.
3 β-courage steroid-5,24-diene-3-alcohol can carry out complete synthesis or semi-synthetic (U.S. Pat 3846455, J.Org.Chem.1958 by organic reaction, 23,459), but production cost is higher, less economical, and used more soda acid solvent, easily environment is produced and pollute.
3 β-courage steroid-5,24-diene-3-alcohol also can obtain by extraction separation from animals and plants.Usually the solvent extraction techniques that adopts can obtain 3 β-courage steroid-5, the crude product of 24-diene-3-alcohol, but 3 β-courage steroid-5, and 24-diene-3-alcohol purity is lower, generally below 10%, does not meet commerce with requiring, and therefore need be further purified processing.
Raw material influences later separation method and cost, and U.S. Pat 3803184 adopts solvent extraction-aluminum oxide chromatogram-acetylization reaction-AgNO
3Complexing chromatogram-chromatography-multistep methods such as saponification obtain 3 β-courage steroid-5 from the separation of wild rubber seeds, 24-diene-3-alcohol, and this method must be with 3 β-courage steroid-5, and the 24-diene-pre-acetylization reaction of 3-alcohol adopts expensive AgNO then
3The complexing chromatogram, change into 25 hydroxycholesterols with mercury salt again, chromatography or the crystallization again of 25 hydroxycholesterols, saponification just can obtain higher degree 3 β-courage steroid-5,24-diene-3-alcohol, its method is comparatively loaded down with trivial details, and the production cycle is long, and 3 β in wild rubber seeds-courage steroid-5,24-diene-3-alcohol content is low, and production cost is bigger, is not suitable for industrialization.
Summary of the invention
The object of the present invention is to provide a kind of ADSORPTION IN A FIXED BED purifying 3 β-courage steroid-5, the method of 24-diene-3-alcohol, from lanolin, extract the 3 β-courage steroid-5 that obtains by activated carbon fixed bed absorption, separate preparation high level 3 β-courage steroid-5,24-diene-3-alcohol in 24-diene-3-alcohol crude product.
For realizing the object of the invention, by the following technical solutions:
(1) with 3 β-courage steroid-5,24-diene-3-alcohol crude product and last sample solvent are mixed with stock liquid, under 20-60 ℃, it is activated carbon fixed bed with the flow velocity of 0.5-2.0BV/h stock liquid to be flow through, remove strong polar impurity, make 3 β-courage steroid-5,24-diene-3-alcohol is adsorbed on the activated carbon.
(2) under 20-60 ℃, make the last sample solvent streams of 1-2 times of bed volume activated carbon fixed bed excessively with the flow velocity of 0.5-3.0BV/h, stock liquid in the fixed bed space and strong polar impurity are developed.
(3) under 20-60 ℃, it is activated carbon fixed bed with the flow velocity of 0.5-3.0BV/h the eluting solvent of 2-4 times of bed volume to be flow through, with 3 β-courage steroid-5,24-diene-3-alcohol elutes, collect elutriant, concentrating under reduced pressure obtains 3 β-courage steroid-5,24-diene-3-alcohol product.
(4) under 20-60 ℃, it is activated carbon fixed bed with the flow velocity of 1.0BV/h the regenerated solvent of 2 times of bed volume to be flow through, and low-pole impurity is eluted, and makes activated carbon obtain regeneration.
(5) under 20-60 ℃, make the last sample solvent streams of 2 times of bed volume cross solid activated carbon fixed bed with the flow velocity of 1.0BV/h, make the system balance, enter next fractionation by adsorption circulation.
Described 3 β-courage steroid-5,24-diene-3-alcohol crude product is 3 β that extraction separation obtains in the lanolin-courage steroid-5,24-diene-3-alcohol crude product, 3 β-courage steroid-5 wherein, 24-diene-3-alcohol mass content is 10-30%, the cholesterol mass content is less than 3%, and major impurity is the grease and the triterpene alcohol of polar lipid acid, Fatty Alcohol(C12-C14 and C12-C18), sterol and low-pole.
Described upward sample solvent is the mixed solvent of a kind of or first alcohol and water in methyl alcohol, the ethanol or the mixed solvent of second alcohol and water, 3 β-courage steroid-5, and 24-diene-3-alcohol crude product and last sample solvent ratios are 0.05-0.2kg crude product/L solvent.
Described activated carbon is the gross porosity grain active carbon.
Described eluent is a kind of or sherwood oil in acetone, ethyl acetate, the chloroform and mixed solvent or the sherwood oil and the ethanol mixed solvent of methyl alcohol.
Described regenerator is normal hexane or sherwood oil.
Described 3 β-courage steroid-5,24-diene-3-alcohol quality product content is greater than 60%.
Adopt method provided by the invention, 3 β-courage steroid-5, the yield of 24-diene-3-alcohol is greater than 85%.
The beneficial effect that the present invention has is:
(1) the present invention adopts the gross porosity grain active carbon to make sorbent material, and to 3 β-courage steroid-5, the adsorptive capacity of 24-diene-3-alcohol is big, separation selectivity is high.And grain active carbon is regenerated easily, can repeatedly recycle, and reduces sorbent material consumption.
(2) the inventive method has characteristics such as production cost is low, consumption is low, pollution is few, and flow process is simple, and is easy to operate, is suitable for suitability for industrialized production.
Embodiment
Below with embodiment method of the present invention is described further.Protection scope of the present invention is not subjected to the restriction of embodiment, and protection scope of the present invention is determined by claim.
Embodiment 1:
With 0.1kg 3 β-courage steroid-5,24-diene-3-alcohol crude product (mass content 10.0%, cholesterol level 0.9%) and the dissolving of 1L methanol mixed are made into stock liquid.Fixed bed size φ 5cm * 25cm, inner filling gross porosity grain active carbon.Stock liquid flow velocity with 0.5BV/h under 20 ℃ passes through fixed bed, continues the washed with methanol fixed bed with 1.0BV, flow velocity 1.0BV/h.Down carry out wash-out with the acetone of 3.0BV at 60 ℃, flow velocity is 1.0BV/h, collects elutriant, 60 ℃ of following concentrating under reduced pressure oven dry, 3 β-courage steroid-5,24-diene-3-alcohol product 16.7g, 3 β-courage steroid-5 wherein, the pure purity of 24-diene-3-is 60%, yield is 91%.Under 60 ℃, it is activated carbon fixed bed with the flow velocity of 1BV/h the sherwood oil of 2 times of bed volume to be flow through, regeneration activity carbon.Under 60 ℃, with the methyl alcohol of 2.0BV activated carbon is carried out balance with the flow velocity of 1.0BV/h.
Embodiment 2:
With 0.1kg 3 β-courage steroid-5,24-diene-3-alcohol crude product (mass content 10.0%, cholesterol level 0.9%) and the dissolving of 1L methanol mixed are made into stock liquid.Fixed bed adopts the pillar that embodiment 1 uses and the regeneration balance is crossed.Stock liquid flow velocity with 0.5BV/h under 20 ℃ passes through fixed bed, continues the washed with methanol fixed bed with 1.0BV, flow velocity 1.0BV/h.Down carry out wash-out with the acetone of 3.0BV at 60 ℃, flow velocity is 1.0BV/h, collects elutriant, 60 ℃ of following concentrating under reduced pressure oven dry, 3 β-courage steroid-5,24-diene-3-alcohol product 17.0g, 3 β-courage steroid-5 wherein, the pure purity of 24-diene-3-is 60%, yield is 93%.Under 40 ℃, it is activated carbon fixed bed with the flow velocity of 1BV/h the sherwood oil of 2 times of bed volume to be flow through, regeneration activity carbon.Under 40 ℃, with the methyl alcohol of 2.0BV activated carbon is carried out balance with the flow velocity of 1.0BV/h.Illustrate that activated carbon can be recycled.
Embodiment 3:
With 0.06kg 3 β-courage steroid-5,24-diene-3-alcohol crude product (mass content 23.5%, cholesterol level 2.0%) and 0.5L aqueous ethanolic solution (ethanol and water volume ratio are 9: 1) mixed dissolution is made into stock liquid.Fixed bed size φ 5cm * 25cm, inner filling gross porosity grain active carbon.Stock liquid flow velocity with 1.0BV/h under 40 ℃ passes through fixed bed, continues aqueous ethanolic solution (ethanol and water volume ratio are 90: 10) the flushing fixed bed with 3.0BV, flow velocity 1.0BV/h.Carry out wash-out with the ethyl acetate of 3.0BV down at 40 ℃, flow velocity is 0.5BV/h, collects elutriant, 60 ℃ of following concentrating under reduced pressure oven dry get 3 β-courage steroid-5,24-diene-3-alcohol product 22.7g, 3 β-courage steroid-5 wherein, 24-diene-3-alcohol purity is 72%, yield is 86%.Under 40 ℃, it is activated carbon fixed bed with the flow velocity of 1BV/h the sherwood oil of 2 times of bed volume to be flow through, regeneration activity carbon.Under 40 ℃, with the methyl alcohol of 2.0BV activated carbon is carried out balance with the flow velocity of 1.0BV/h.
Embodiment 4:
With 0.1Kg 3 β-courage steroid-5,24-diene-3-alcohol crude product (mass content 30.0%, cholesterol level 2.7%) and the dissolving of 0.5L methanol mixed are made into stock liquid.Fixed bed size φ 5cm * 25cm, inner filling gross porosity grain active carbon.Stock liquid flow velocity with 2.0BV/h under 40 ℃ passes through fixed bed, continues the washed with methanol fixed bed with 2.0BV, flow velocity 3.0BV/h.At 40 ℃ of following wash-outs that carry out with 3.0BV methyl alcohol petroleum ether solution (methyl alcohol sherwood oil volume ratio is 9: 1), flow velocity is 0.5BV/h, collect elutriant, 60 ℃ of following concentrating under reduced pressure oven dry, get 3 β-courage steroid-5,24-diene-3-alcohol product 38.0g, wherein 3 β-courage steroid-5,24-diene-3-alcohol purity is 70%, and yield is 89%.Under 20 ℃, it is activated carbon fixed bed with the flow velocity of 1BV/h the normal hexane of 2 times of bed volume to be flow through, regeneration activity carbon.Under 20 ℃, with the methyl alcohol of 2.0BV activated carbon is carried out balance with the flow velocity of 1.0BV/h.
Embodiment 5:
With 0.06kg 3 β-courage steroid-5,24-diene-3-alcohol crude product (mass content 23.5%, cholesterol level 2.0%) and 1200L methanol aqueous solution (methyl alcohol and water volume ratio are 95: 5) mixed dissolution is made into stock liquid.Fixed bed size φ 5cm * 25cm, inner filling gross porosity grain active carbon.Stock liquid flow velocity with 1.0BV/h under 40 ℃ passes through fixed bed, continues methanol aqueous solution (methyl alcohol and water volume ratio are 95: 5) the flushing fixed bed with 1.0BV, flow velocity 0.5BV/h.Down carry out wash-out with the chloroform of 4.0BV at 40 ℃, flow velocity is 2.0BV/h, collects elutriant, 60 ℃ of following concentrating under reduced pressure oven dry, 3 β-courage steroid-5,24-diene-3-alcohol product 20.4g, 3 β-courage steroid-5 wherein, the pure purity of 24-diene-3-is 65%, yield is 94%.Under 40 ℃, it is activated carbon fixed bed with the flow velocity of 1BV/h the sherwood oil of 2 times of bed volume to be flow through, regeneration activity carbon.Under 40 ℃, with the methanol aqueous solution of 2.0BV activated carbon is carried out balance with the flow velocity of 1.0BV/h.
Embodiment 6:
With 0.1Kg 3 β-courage steroid-5,24-diene-3-alcohol crude product (mass content 30.0%, cholesterol level 2.7%) and the dissolving of 0.5L methanol mixed are made into stock liquid.Fixed bed size φ 5cm * 25cm, inner filling gross porosity grain active carbon.Stock liquid flow velocity with 2.0BV/h under 40 ℃ passes through fixed bed, continues the washed with methanol fixed bed with 2.0BV, flow velocity 3.0BV/h.At 40 ℃ of following wash-outs that carry out with 3.0BV methyl alcohol petroleum ether solution (methyl alcohol sherwood oil volume ratio is 8: 2), flow velocity is 0.5BV/h, collect elutriant, 60 ℃ of following concentrating under reduced pressure oven dry, get 3 β-courage steroid-5,24-diene-3-alcohol product 38.4g, wherein 3 β-courage steroid-5,24-diene-3-alcohol purity is 68%, and yield is 90%.Under 20 ℃, it is activated carbon fixed bed with the flow velocity of 1BV/h the normal hexane of 2 times of bed volume to be flow through, regeneration activity carbon.Under 20 ℃, with the methyl alcohol of 2.0BV activated carbon is carried out balance with the flow velocity of 1.0BV/h.
Claims (7)
1. ADSORPTION IN A FIXED BED purifying 3 β-courage steroid-5, the method for 24-diene-3-alcohol is characterized in that may further comprise the steps:
(1) with 3 β-courage steroid-5,24-diene-3-alcohol crude product and last sample solvent are mixed with stock liquid, under 20-60 ℃, it is activated carbon fixed bed with the flow velocity of 0.5-2.0BV/h stock liquid to be flow through, remove strong polar impurity, make 3 β-courage steroid-5,24-diene-3-alcohol is adsorbed on the activated carbon;
(2) under 20-60 ℃, make the last sample solvent streams of 1-2 times of bed volume activated carbon fixed bed excessively with the flow velocity of 0.5-3.0BV/h, stock liquid in the fixed bed space and strong polar impurity are developed;
(3) under 20-60 ℃, it is activated carbon fixed bed with the flow velocity of 0.5-3.0BV/h the eluting solvent of 2-4 times of bed volume to be flow through, with 3 β-courage steroid-5,24-diene-3-alcohol elutes, collect elutriant, concentrating under reduced pressure obtains 3 β-courage steroid-5,24-diene-3-alcohol product;
(4) under 20-60 ℃, it is activated carbon fixed bed with the flow velocity of 1.0BV/h the regenerated solvent of 2 times of bed volume to be flow through, and low-pole impurity is eluted, and makes activated carbon obtain regeneration;
(5) under 20-60 ℃, make the last sample solvent streams of 2 times of bed volume cross solid activated carbon fixed bed with the flow velocity of 1.0BV/h, make the system balance, enter next fractionation by adsorption circulation.
2. a kind of ADSORPTION IN A FIXED BED purifying 3 β according to claim 1-courage steroid-5, the method of 24-diene-3-alcohol, it is characterized in that: described 3 β-courage steroid-5,24-diene-3-alcohol crude product is 3 β that extraction separation obtains in the lanolin-courage steroid-5,24-diene-3-alcohol crude product, 3 β-courage steroid-5 wherein, 24-diene-3-alcohol mass content is 10-30%, the cholesterol mass content is less than 3%.
3. a kind of ADSORPTION IN A FIXED BED purifying 3 β according to claim 1-courage steroid-5, the method of 24-diene-3-alcohol, it is characterized in that: described upward sample solvent is the mixed solvent of a kind of or first alcohol and water in methyl alcohol, the ethanol or the mixed solvent of second alcohol and water, 3 β-courage steroid-5,24-diene-3-alcohol crude product and last sample solvent ratios are 0.05-0.2kg crude product/L solvent.
4. method according to claim 1 is characterized in that, described activated carbon is the gross porosity grain active carbon.
5. a kind of ADSORPTION IN A FIXED BED purifying 3 β according to claim 1-courage steroid-5, the method of 24-diene-3-alcohol is characterized in that: described eluent is a kind of or sherwood oil in acetone, ethyl acetate, the chloroform and mixed solvent or the sherwood oil and the ethanol mixed solvent of methyl alcohol.
6. a kind of ADSORPTION IN A FIXED BED purifying 3 β according to claim 1-courage steroid-5, the method for 24-diene-3-alcohol is characterized in that: described regenerator is normal hexane or sherwood oil.
7. a kind of ADSORPTION IN A FIXED BED purifying 3 β according to claim 1-courage steroid-5, the method for 24-diene-3-alcohol is characterized in that: described 3 β-courage steroid-5,24-diene-3-alcohol quality product content is greater than 60%.
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