CN101318988B - Sterol extracted from crude glycerine and extracting method thereof - Google Patents
Sterol extracted from crude glycerine and extracting method thereof Download PDFInfo
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- CN101318988B CN101318988B CN2008100482102A CN200810048210A CN101318988B CN 101318988 B CN101318988 B CN 101318988B CN 2008100482102 A CN2008100482102 A CN 2008100482102A CN 200810048210 A CN200810048210 A CN 200810048210A CN 101318988 B CN101318988 B CN 101318988B
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Abstract
The invention discloses sterol extracted from crude glycerol and an extraction method thereof. The sterol is extracted through the following steps that: crude glycerol is added to alkaline ethanol aqueous solution with the concentration between 0.5-1.25 mol/L as extracting solution according to the solid-liquid ratio between 1:0.05 and 1:50 g/ml, and then saponification treatment is carried out with the stirring speed between 100 and 500 r/m at a temperature between 10 and 50 DEG C; extracting agent 2-10 times the volume of saponified-cooled solution is added to saponified-cooled solution, and is well stirred for 10-50 min under the stirring speed between 100 and 500 r/min at a temperature between 10 and 50 DEG C; mixed liquid is kept to stand and layered or centrifuged to remove saponification solution; extracting liquid is repeatedly washed for a plurality of times by using water and alkaline ethanol solution with the concentration between 0.1 and 1 mol/L, has the extracting agent recovered, and is dried, and then crude sterol can be obtained. The extraction method adopts a saponification method, uses the alkaline ethanol solution as the saponification solution, is simple and convenient in extraction condition, high in yield of extracted sterol, capable of greatly improving the added value of the processing and utilization of glycerol which is a byproduct of biodiesel, and has good popularization and application prospects in industry.
Description
Technical field
The present invention relates to a kind of sterol that from raw glycerine, extracts and extracting method, belong to biochemical field.
Background technology
Biofuel is a fatty acid methyl ester, is a kind of renewable, environment-friendly type fuel, is typical green energy resource.In recent years, in the world particularly European and American countries government all in the development of carrying forward vigorously the biofuel industry.China is also actively developing the biofuel development, but does not have a family to realize industrialization so far.Subject matter is that product price is compared with petrifaction diesel, lacks competitiveness.Current, to the research of biofuel, no matter be production technology and material choice both at home and abroad, or level of application, deepen continuously.Along with to biofuel research actively deeply and the mass production of biofuel, the output of its by product-glycerine also increases sharply.Yet the research dynamics of current high value added product for glycerine also is nowhere near, and therefore, the comprehensive utilization of biological diesel oil byproduct glycerin has good prospect.Plant sterol is that a class extensively is present in the biologically active substance in the plant, alcohol compound with 28 or 29 carbon atoms, on function and structure with the intravital cholesterol of vertebrates seemingly, plant sterol has reducing cholesterol, anti-inflammatory, brings down a fever on clinical medicine, antiulcer agent, antitumor action, all has extensively in fields such as makeup, growth of animal agent, plant growth hormones and chemical industry, weavings and all uses.Sterol is the component that exists naturally in the Vegetable oil lipoprotein, and China is the first in the world Semen Brassicae campestris: big producing country, and Semen Brassicae campestris is the main raw material of production biofuel, therefore extracting sterol from glycerine can effectively increase its utility value.
Summary of the invention
The object of the present invention is to provide a kind of sterol and extracting method thereof that extracts from biodiesel byproduct product glycerine, this method is simply effective, and cost is low, and higher with the yield of this method extraction sterol.
Realize that the object of the invention technical scheme is a kind of sterol that extracts from glycerine, extract by the following method and get:
(1) get the raw glycerine raw material, by 1: 0.05-1: the concentration that the solid-liquid ratio of 50g/ml adds as extracting solution is the alkaline ethanol aqueous solution of 0.5-1.25mol/L, and 60-150 ℃ is heated saponification 30 minutes-75 minutes then; Alkaline ethanol aqueous solution neutral and alkali material is potassium hydroxide, sodium hydroxide, amine, carboxylic acid sodium, carboxylic acid potassium, potassium sulfonate, sodium sulfonate, tetra-alkyl ammonium hydroxide, ammoniacal liquor, saleratus, salt of wormwood, potassium sulfite, POTASSIUM PHYTATE, sodium bicarbonate, yellow soda ash, S-WAT or sodium phytate, perhaps two or more mixture in them.
(2) extraction agent with gained saponification cooled solution adding 2-10 volume is to stir fully extraction under the 100-500r/min at 10 ℃-50 ℃ with stirring velocity, and extraction agent is a sherwood oil;
(3) with mixed solution standing demix or the centrifugal saponification liquor of removing, the water and the 0.1-1mol/L alkaline ethanol aqueous solution repetitive scrubbing extraction liquid respectively reclaim extraction agent for several times, are drying to obtain thick sterol.
The ethanol concentration of volume percent is more than or equal to 80% and less than 100% in the above-mentioned alkaline ethanol aqueous solution.
Adopt variable color experiment quantitative assay sterol yield: get a little product in test tube. add diacetyl oxide 2ml, jolting mixes, and drips a vitriol oil, and after the vibration, the solution becomes yellow becomes emerald green then, in the 500nm colorimetric, calculates the sterol yield by typical curve.The concentration of extracting solution, saponification time, extraction temperature, extraction time, stirring velocity and extraction agent consumption condition are to the influence of sterol yield significantly in this technical scheme.
The present invention adopts saponification method as shown from the above technical solution, as saponification liquor, extraction conditions is simple and convenient with alkali commonly used, and the sterol yield is higher, can improve the added value of the processing and utilization of biodiesel byproduct product glycerine greatly, good popularization and application prospect be arranged industrial.
The present invention is at first by 1: 0.05-1: the concentration that the solid-liquid ratio of 50g/ml adds in biodiesel byproduct product raw glycerine as extracting solution is the alkaline ethanol aqueous solution of 0.5-1.25mol/L, wherein in the alkaline ethanol aqueous solution ethanol concentration of volume percent more than or equal to 80% and less than 100%.60-150 ℃ of saponification reaction 30-75min., one or more mixed solutions in 10-50 ℃, the benzene of stirring velocity 100-500r/m, extraction agent consumption 2-10 volume, toluene, hexane, hexanaphthene, ethyl acetate, the trimethyl carbinol, diisopropyl ether, No. 6 solvents or sherwood oil fully extract the back and take out then, standing demix, remove the sub-cloud saponification liquor, use twice of distilled water wash extraction liquid earlier, use 10-80ml 0.1-1mol/L alkaline ethanol solution washing more once, then for several times with distilled water.
Embodiment
Below the invention will be further described by specific embodiment.
Embodiment 1
With the raw glycerine adding 0.25ml ethanol volume percent of 5g is 95%, concentration is the potassium hydroxide-ethanol aqueous solution of 0.5mol/L, take out behind 60 ℃ of heating 45min, the sherwood oil that adds 42.5ml, in 30 ℃ water-bath, stirring velocity is to take out behind the 300r/m extraction 20min, standing demix, remove the sub-cloud saponification liquor, use twice of 40ml distilled water wash extraction liquid earlier, use 40ml 0.5mol/L potassium hydroxide-ethanol solution washing more once, use the 40ml distilled water wash for several times then, be drying to obtain thick sterol.Because saponification is incomplete, the sterol yield can't be calculated.
Embodiment 2
With the raw glycerine adding 250ml ethanol volume percent of 5g is 95%, concentration is the potassium hydroxide-ethanol aqueous solution of 0.75mol/L, take out behind 150 ℃ of heating 45min, the sherwood oil that adds 508ml, in 30 ℃ water-bath, stirring velocity is to take out behind the 300r/m extraction 20min, standing demix, remove the sub-cloud saponification liquor, use twice of 40ml distilled water wash extraction liquid earlier, use 40ml 0.5mol/L potassium hydroxide-ethanol solution washing more once, use the 40ml distilled water wash for several times then, be drying to obtain thick sterol.The sterol yield is more than the 3mg/g under this condition after measured.
Embodiment 3
With the raw glycerine adding 50ml ethanol concentration of volume percent of 5g is 95%, concentration is the potassium hydroxide-ethanol aqueous solution of 1mol/L, take out behind 100 ℃ of heating 45min, the sherwood oil that adds 300ml, in 30 ℃ water-bath, stirring velocity is to take out behind the 300r/m extraction 20min, standing demix, remove the sub-cloud saponification liquor, earlier with 40ml distilled water extraction liquid washed twice, use 0.1mol/L potassium hydroxide-ethanol solution washing more once, use the 40ml distilled water wash for several times then, be drying to obtain thick sterol.The sterol yield is more than the 3.5mg/g under this condition after measured.
Embodiment 4
With the glycerine adding 50ml ethanol concentration of volume percent of 5g is 95%, concentration is the potassium hydroxide-ethanol aqueous solution of 1.25mol/L, takes out behind 80 ℃ of heating 45min, adds the sherwood oil of 300ml, in 30 ℃ water-bath, stirring velocity is to take out behind the 300r/m extraction 20min, and standing demix removes the sub-cloud saponification liquor, use twice of 10ml distilled water wash extraction liquid earlier, use 1mol/L potassium hydroxide-ethanol solution washing more once, use the 10ml distilled water wash for several times then, be drying to obtain thick sterol.The sterol yield is more than the 2.5mg/g under this condition after measured.
Embodiment 5
With the raw glycerine adding 50ml ethanol concentration of volume percent of 5g is 95%, concentration is the potassium hydroxide-ethanol aqueous solution of 1mol/L, take out behind 80 ℃ of heating 45min, the sherwood oil that adds 300ml, in 30 ℃ water-bath, stirring velocity is to take out behind the 300r/m extraction 20min, standing demix, remove the sub-cloud saponification liquor, use twice of 40ml distilled water wash extraction liquid earlier, use 40ml0.5mol/L potassium hydroxide-ethanol solution washing more once, use the 40ml distilled water wash for several times then, be drying to obtain thick sterol.The sterol yield is more than the 3.5mg/g under this condition after measured.
Embodiment 6
With the raw glycerine adding 200ml ethanol concentration of volume percent of 5g is 95%, concentration is the potassium hydroxide-ethanol aqueous solution of 1mol/L, take out behind 80 ℃ of heating 60min, the sherwood oil that adds 500ml, in 30 ℃ water-bath, stirring velocity is to take out behind the 300r/m extraction 20min, standing demix, remove the sub-cloud saponification liquor, use twice of 40ml distilled water wash extraction liquid earlier, use 40ml 0.5mol/L potassium hydroxide-ethanol solution washing more once, use the 40ml distilled water wash for several times then, be drying to obtain thick sterol.The sterol yield is more than the 3mg/g under this condition after measured.
Embodiment 7
With the raw glycerine adding 50ml ethanol concentration of volume percent of 5g is 95%, concentration is the potassium hydroxide-ethanol aqueous solution of 1mol/L, take out behind 80 ℃ of heating 75min, the sherwood oil that adds 300ml, in 30 ℃ water-bath, stirring velocity is to take out behind the 300r/m extraction 20min, standing demix, remove the sub-cloud saponification liquor, use twice of 40ml distilled water wash extraction liquid earlier, use 10ml 0.5mol/L potassium hydroxide-ethanol solution washing more once, use the 40ml distilled water wash for several times then, be drying to obtain thick sterol.The sterol yield is more than the 2.5mg/g under this condition after measured.
Embodiment 8
With the raw glycerine adding 50ml ethanol concentration of volume percent of 5g is 95%, concentration is the potassium hydroxide-ethanol aqueous solution of 1mol/L, take out behind 80 ℃ of heating 45min, the sherwood oil that adds 100ml, in 30 ℃ water-bath, stirring velocity is to take out behind the 300r/m extraction 20min, standing demix, remove the sub-cloud saponification liquor, use twice of 70ml distilled water wash extraction liquid earlier, use 40ml 0.5mol/L potassium hydroxide-ethanol solution washing more once, use the 70ml distilled water wash for several times then, be drying to obtain thick sterol.The sterol yield is more than the 1.5mg/g under this condition after measured.
Embodiment 9
The raw glycerine of 5g is added 250ml, the ethanol concentration of volume percent is 95%, concentration is the potassium hydroxide-ethanol aqueous solution of 1mol/L, take out behind 80 ℃ of heating 45min, the sherwood oil that adds 600ml, in 30 ℃ water-bath, stirring velocity is to take out behind the 300r/m extraction 20min, standing demix, remove the sub-cloud saponification liquor, with 80ml distilled water extraction liquid washed twice, use 80ml 0.5mol/L potassium hydroxide-ethanol solution washing more once earlier, use the 80ml distilled water wash for several times then, be drying to obtain thick sterol.The sterol yield is more than the 3mg/g under this condition after measured.
Embodiment 10
With the raw glycerine adding 150ml ethanol concentration of volume percent of 5g is 95%, concentration is the potassium hydroxide-ethanol aqueous solution of 1mol/L, take out behind 80 ℃ of heating 45min, the sherwood oil that adds 300ml, in 30 ℃ water-bath, stirring velocity is to take out behind the 300r/m extraction 50min, standing demix, remove the sub-cloud saponification liquor, use twice of 40ml distilled water wash extraction liquid earlier, use 40ml 0.6mol/L potassium hydroxide-ethanol solution washing more once, use the 40ml distilled water wash for several times then, be drying to obtain thick sterol.The sterol yield is more than the 2mg/g under this condition after measured.
Embodiment 11
With the raw glycerine adding 50ml concentration of 5g is the potassium hydroxide-ethanol solution of 1mol/L, take out behind the heating 45min, 80 ℃ of sherwood oils that add 400ml, in 30 ℃ water-bath, stirring velocity is to take out behind the 300r/m extraction 20min, standing demix, remove the sub-cloud saponification liquor, with 40ml distilled water wash extraction liquid twice, use 40ml 0.5mol/L potassium hydroxide-ethanol solution washing more once earlier, use the 40ml distilled water wash for several times then, be drying to obtain thick sterol.The sterol yield is more than the 3.5mg/g under this condition after measured.
Embodiment 12
With the raw glycerine adding 50ml ethanol concentration of volume percent of 5g is 85%, concentration is the potassium hydroxide-ethanol aqueous solution of 1mol/L, take out behind 80 ℃ of heating 45min, the sherwood oil that adds 500ml, in 30 ℃ water-bath, stirring velocity is to take out behind the 300r/m extraction 40min, standing demix, remove the sub-cloud saponification liquor, use twice of 40ml distilled water wash extraction liquid earlier, use 40ml 0.5mol/L potassium hydroxide-ethanol solution washing more once, use the 40ml distilled water wash for several times then, be drying to obtain thick sterol.The sterol yield is more than the 2.5mg/g under this condition after measured.
Embodiment 13
With the raw glycerine adding 50ml ethanol concentration of volume percent of 5g is 80%, concentration is the alkaline ethanol aqueous solution of 1mol/L, take out behind 80 ℃ of heating 45min, the sherwood oil that adds 300ml, in 10 ℃ water-bath, stirring velocity is to take out behind the 300r/m extraction 20min, standing demix, remove the sub-cloud saponification liquor, use twice of 40ml distilled water wash extraction liquid earlier, use 40ml 0.8mol/L potassium hydroxide-ethanol solution washing more once, use the 40ml distilled water wash for several times then, be drying to obtain thick sterol.The sterol yield is more than the 1mg/g under this condition after measured.
And wherein the alkaline matter of the alkaline ethanol aqueous solution comprises potassium hydroxide, sodium hydroxide, amine, carboxylic acid sodium, carboxylic acid potassium, potassium sulfonate, sodium sulfonate, tetra-alkyl ammonium hydroxide, ammoniacal liquor, saleratus, salt of wormwood, potassium sulfite, POTASSIUM PHYTATE, sodium bicarbonate, yellow soda ash, S-WAT or sodium phytate, perhaps two or more mixture in them.
Embodiment 14
With the raw glycerine adding 50ml concentration of 5g is the potassium hydroxide-ethanol solution of 1mol/L, take out behind 80 ℃ of heating 45min, the sherwood oil that adds 300ml, in 20 ℃ water-bath, stirring velocity is to take out behind the 300r/m extraction 20min, standing demix, remove the sub-cloud saponification liquor, with 60ml distilled water wash extraction liquid twice, use 40ml 0.9mol/L potassium hydroxide-ethanol solution washing more once earlier, use the 60ml distilled water wash for several times then, be drying to obtain thick sterol.The sterol yield is more than the 2.5mg/g under this condition after measured.
Embodiment 15
With the raw glycerine adding 50ml ethanol concentration of volume percent of 5g is 90%, concentration is the potassium hydroxide-ethanol aqueous solution of 1mol/L, take out behind 80 ℃ of heating 45min, the sherwood oil that adds 300ml, in 30 ℃ water-bath, stirring velocity is to take out behind the 300r/m extraction 30min, standing demix, remove the sub-cloud saponification liquor, use twice of 40ml distilled water wash extraction liquid earlier, use 40ml 0.5mol/L potassium hydroxide-ethanol solution washing more once, use the 40ml distilled water wash for several times then, be drying to obtain thick sterol.The sterol yield is more than the 3mg/g under this condition after measured.
Embodiment 16
With the raw glycerine adding 100ml ethanol concentration of volume percent of 5g is 95%, concentration is the potassium hydroxide-ethanol aqueous solution of 1mol/L, take out behind 80 ℃ of heating 45min, the sherwood oil that adds 300ml, in 40 ℃ water-bath, stirring velocity is to take out behind the 300r/m extraction 20min, standing demix, remove the sub-cloud saponification liquor, use twice of 40ml distilled water wash extraction liquid earlier, use 40ml 0.4mol/L potassium hydroxide-ethanol solution washing more once, use the 40ml distilled water wash for several times then, be drying to obtain thick sterol.The sterol yield is more than the 3mg/g under this condition after measured.
Embodiment 17
With the raw glycerine adding 150ml ethanol concentration of volume percent of 5g is 95%, concentration is the potassium hydroxide-ethanol aqueous solution of 1mol/L, take out behind 80 ℃ of heating 45min, the sherwood oil that adds 300ml, in 50 ℃ water-bath, stirring velocity is to take out behind the 300r/m extraction 20min, standing demix, remove the sub-cloud saponification liquor, use twice of 40ml distilled water wash extraction liquid earlier, use 40ml 0.5mol/L potassium hydroxide-ethanol solution washing more once, use the 40ml distilled water wash for several times then, be drying to obtain thick sterol.The sterol yield is more than the 2.5mg/g under this condition after measured.
Embodiment 18
With the raw glycerine adding 50ml ethanol concentration of volume percent of 5g is 95%, concentration is the potassium hydroxide-ethanol aqueous solution of 1mol/L, take out behind 80 ℃ of heating 45min, the sherwood oil that adds 300ml, in 30 ℃ water-bath, stirring velocity is to take out behind the 100r/m extraction 20min, standing demix, remove the sub-cloud saponification liquor, use twice of 40ml distilled water wash extraction liquid earlier, use 40ml 0.5mol/L potassium hydroxide-ethanol solution washing more once, with 40ml washing distilled water for several times, be drying to obtain thick sterol then.The sterol yield is more than the 2.5mg/g under this condition after measured.
Embodiment 19
With the raw glycerine adding 50ml ethanol concentration of volume percent of 5g is 95%, concentration is the potassium hydroxide-ethanol aqueous solution of 1mol/L, take out behind 80 ℃ of heating 45min, the sherwood oil that adds 300ml, in 30 ℃ water-bath, stirring velocity is to take out behind the 200r/m extraction 20min, standing demix, remove the sub-cloud saponification liquor, use twice of 40ml distilled water wash extraction liquid earlier, use 30ml 0.5mol/L potassium hydroxide-ethanol solution washing more once, with 40ml washing distilled water for several times, be drying to obtain thick sterol then.The sterol yield is more than the 3mg/g under this condition after measured.
Embodiment 20
With the raw glycerine adding 50ml ethanol concentration of volume percent of 5g is 95%, concentration is the potassium hydroxide-ethanol aqueous solution of 1mol/L, take out behind 80 ℃ of heating 45min, the sherwood oil that adds 300ml, in 30 ℃ water-bath, stirring velocity is to take out behind the 300r/m extraction 20min, standing demix, remove the sub-cloud saponification liquor, use twice of 40ml distilled water wash extraction liquid earlier, use 40ml 0.5mol/L potassium hydroxide-ethanol solution washing more once, use the 40ml distilled water wash for several times then, be drying to obtain thick sterol.The sterol yield is more than the 3.5mg/g under this condition after measured.
Embodiment 21
With the raw glycerine adding 50ml ethanol concentration of volume percent of 5g is 95%, concentration is the potassium hydroxide-ethanol aqueous solution of 1mol/L, take out behind 80 ℃ of heating 45min, the sherwood oil that adds 300ml, in 30 ℃ water-bath, stirring velocity is to take out behind the 400r/m extraction 20min, standing demix, remove the sub-cloud saponification liquor, use twice of 40ml distilled water wash extraction liquid earlier, use 40ml 0.5mol/L potassium hydroxide-ethanol solution washing more once, with 40ml washing distilled water for several times, be drying to obtain thick sterol then.The sterol yield is more than the 3mg/g under this condition after measured.
Embodiment 22
With the raw glycerine adding 50ml ethanol concentration of volume percent of 5g is 95%, concentration is the potassium hydroxide-ethanol aqueous solution of 1mol/L, take out behind 80 ℃ of heating 45min, the sherwood oil that adds 300ml, in 30 ℃ water-bath, stirring velocity is to take out behind the 500r/m extraction 20min, standing demix, remove the sub-cloud saponification liquor, use twice of 70ml distilled water wash extraction liquid earlier, use 40ml 0.6mol/L potassium hydroxide-ethanol solution washing more once, use the 70ml distilled water wash for several times then, be drying to obtain thick sterol.The sterol yield is more than the 3mg/g under this condition after measured.
Embodiment 23
With the raw glycerine adding 50ml ethanol concentration of volume percent of 5g is 90%, concentration is the potassium hydroxide-ethanol aqueous solution of 1mol/L, take out behind 80 ℃ of reacting by heating 45min, the sherwood oil that adds 300ml, in 30 ℃ water-bath, stirring velocity is to take out behind the 300r/m extraction 10min, standing demix, remove the sub-cloud saponification liquor, use twice of 40ml distilled water wash extraction liquid earlier, use 80ml 0.5mol/L potassium hydroxide-ethanol solution washing more once, use the 40ml distilled water wash for several times then, be drying to obtain thick sterol.The sterol yield is more than the 3mg/g under this condition after measured.
Claims (3)
1. extracting method that extracts sterol from raw glycerine is characterized in that adopting following concrete steps:
(1) the by product raw glycerine of getting biofuel is a raw material, and by 1: 0.05-1: it is the alkaline ethanol aqueous solution of 0.5-1.25mol/L that the solid-liquid ratio of 50g/ml adds concentration, then 60-150 ℃ of heating saponification 30 minutes-75 minutes down;
(2) in gained saponification cooled solution, the extraction agent that adds 2-10 times of volume is to stir fully extraction under the 100-500r/min at 10 ℃-50 ℃ with stirring velocity, and extraction agent is a sherwood oil;
(3) with mixed solution standing demix or the centrifugal saponification liquor of removing, the water and the 0.1-1mol/L alkaline ethanol aqueous solution repetitive scrubbing extraction liquid respectively reclaim extraction agent for several times, are drying to obtain thick sterol.
2. according to the described used extracting method of sterol that from raw glycerine, extracts of claim 1, it is characterized in that: alkaline ethanol aqueous solution neutral and alkali material is potassium hydroxide, sodium hydroxide, amine, carboxylic acid sodium, carboxylic acid potassium, potassium sulfonate, sodium sulfonate, tetra-alkyl ammonium hydroxide, ammoniacal liquor, saleratus, salt of wormwood, potassium sulfite, POTASSIUM PHYTATE, sodium bicarbonate, yellow soda ash, S-WAT or sodium phytate, perhaps two or more mixture in them.
3. according to claim 1 or the 2 described used extracting method of sterol that extract from raw glycerine, it is characterized in that: the ethanol concentration of volume percent is more than or equal to 80% and less than 100% in the alkaline ethanol aqueous solution.
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