CN107827947A - The method that high-purity sterol is extracted from the residual oil containing sterol ester - Google Patents
The method that high-purity sterol is extracted from the residual oil containing sterol ester Download PDFInfo
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- CN107827947A CN107827947A CN201711139288.0A CN201711139288A CN107827947A CN 107827947 A CN107827947 A CN 107827947A CN 201711139288 A CN201711139288 A CN 201711139288A CN 107827947 A CN107827947 A CN 107827947A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
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Abstract
The method that high-purity sterol is extracted from the residual oil containing sterol ester：Residual oil first passes through saponification, wherein will be converted into sterol by sterol ester, and obtain saponification liquor.PH value is adjusted to neutral by saponification liquor by neutralization, then by freezing and crystallizing and separation of solid and liquid, obtains filter cake sterol crude product.Then sterol crude product is passed through into complex reaction, sterol is changed into solid complex, then carry out separation of solid and liquid, obtain cake solids complex compound.Solid complex obtains the sterol finished product of purity 97% by hydrolysis, freezing and crystallizing, separation of solid and liquid and after being dried under reduced pressure.The method that high-purity sterol is extracted from the residual oil containing sterol ester of the present invention, the high content natural phytosterin of purity 97% can be extracted from residual oil discarded before.
Description
Technical field
The present invention relates to natural additive for foodstuff production technical field, and in particular to is extracted from the leftover bits and pieces containing sterol ester
The method of sterol.
Background technology
Natural phytosterin, it is to be obtained from corn and soybean and vegetable seed by physical purification, has nutritive value high, raw
The features such as reason activity is strong, is widely used for the fields such as feed addictive at present.In salad oil process, its deodorization distillates
For thing because the influence of the factor such as temperature, some sterol is combined with aliphatic acid is changed into sterol ester, in addition, being deodorized from salad oil
During extracting vitamin E in distillate, also some sterol is changed into sterol ester.Due to fatty acid sterols ester boiling point compared with
Height, so these final sterol esters are remained in the residual oil of short-path distillation.Sterol ester can be reduced into sterol and be reclaimed, have compared with
Big recycling value.In order to improve the rate of recovery of sterol, the method that sterol is extracted from the residual oil containing sterol ester need to be researched and developed.
The content of the invention
The technical problem to be solved in the present invention is the method that sterol is extracted from the leftover bits and pieces containing sterol ester, is specially：Carry
For a kind of method that high-purity sterol is extracted from the residual oil containing sterol ester of rate of recovery for improving sterol.
To achieve the above object, the technical scheme is that：
Residual oil first passes through saponification, wherein will be converted into sterol by sterol ester, and obtain saponification liquor.Saponification liquor will by neutralizing
PH value is adjusted to neutral, then by freezing and crystallizing and separation of solid and liquid, obtains filter cake sterol crude product.Then sterol crude product is passed through into network
Reaction is closed, sterol is changed into solid complex, then carries out separation of solid and liquid, obtains cake solids complex compound.Solid complex passes through
Hydrolysis, freezing and crystallizing, separation of solid and liquid and after being dried under reduced pressure are crossed, obtains the sterol finished product of purity 97%.
The method that high-purity sterol is extracted from the residual oil containing sterol ester：
(A) residual oil (sterol ester content 25-30%) and a certain amount of highly basic methanol solution are added in reactor, one
Determine to be stirred reaction at temperature, saponification liquor is obtained after reacting certain time.
Described highly basic methanol solution, can be that the methanol of one or both of sodium hydroxide, potassium hydroxide mixing is molten
Liquid, concentration 20%.The addition of highly basic methanol solution is to add 30g to 40g per 100g residual oil.
Described temperature is 60 DEG C to 70 DEG C.
The described reaction time is 2 to 3 hours.
(B) inorganic acid is instilled in above-mentioned saponification liquor, pH value is adjusted to neutrality, stand makes its layering afterwards, by lower floor
Solution separates, and upper liquid carries out freezing and crystallizing certain time at a certain temperature, obtains crude crystalline liquid, then by crude crystalline liquid
Separation of solid and liquid is carried out, obtains filter cake sterol crude product.
Described inorganic acid is the one or both mixing therein of the concentrated sulfuric acid, concentrated hydrochloric acid, and addition is to adjust material pH
It is standard to neutrality.
Described freezing and crystallizing temperature is 10 DEG C to 15 DEG C.
The described freezing and crystallizing time is 10 hours to 18 hours.
(C) above-mentioned sterol crude product is added in reactor, then put into reactor a certain amount of organic aprotic solvents and
Complexing agent, open stirring and rise to certain reacting initial temperature simultaneously.Backward reactor in add a certain amount of organic proton
Solvent, carry out complex reaction.Complex reaction controls certain temperature, after certain time is reacted, terminates to react and drop material
To certain temperature, separation of solid and liquid is carried out again afterwards, obtain filter cake sterol complex compound.
Described organic aprotic solvents are one kind in n-hexane, petroleum ether, ethyl acetate or butanone, and addition is steroid
1.5-2 times of alcohol crude product quality.
Described complexing agent is anhydrous calcium chloride, and addition is sterol content in sterol crude product (with sterol content 100%
Meter) 0.6-1.0 times.
Described reacting initial temperature is 45-50 DEG C.
Described organic proton solvent is one kind in methanol or ethanol, and addition is sterol content in sterol crude product
0.3-0.5 times.
It is 50-60 DEG C that described complex reaction, which controls temperature,.
The described complex reaction time is 2-3 hours.
The temperature that described complex reaction reduces after terminating is 30-35 DEG C.
(D) above-mentioned sterol complex compound is added in reactor, adds a certain amount of organic solvent and a certain amount of water, is opened
It is stirred and heated to certain temperature and reaction is hydrolyzed.After hydrolysis carries out certain time, stratification, lower floor's water is separated
Go out, upper materials carry out the freezing and crystallizing regular hour at a certain temperature, obtain finished product crystal solution.Finished product crystal solution is by solid
Liquid separates, and obtained filter cake, which entered to be dried under reduced pressure, obtains sterol finished product.
Described organic solvent is identical with the organic aprotic solvents described in step (C), and addition is sterol complex compound
1-1.5 times of quality.
The water of described addition is 0.5-1 times of sterol complex compound.
Described hydrolysising reacting temperature is 55-60 DEG C.
Described hydrolysis time is 1-1.5 hours.
Described freezing and crystallizing temperature is 10 to 15 DEG C.
The method that high-purity sterol is extracted from the residual oil containing sterol ester of the present invention, can be from residual oil discarded before
The high content natural phytosterin of purity 97% is extracted, is turned waste into wealth, economic benefit has not only been improved but also has reduced discarded object
Quantity, and the natural phytosterin of gained meets the requirement of client.
Embodiment
With reference to embodiment, the present invention is further illustrated, and following each embodiments are merely to illustrate the present invention, but
The present invention is not limited.
Embodiment one
1st, the sodium hydrate methanol solution 30g of 100g residual oil (sterol ester content 25%) and mass fraction 20% is added to
In reactor, control 65 DEG C of temperature to carry out reaction 2 hours under agitation, obtain saponification liquor.
2nd, toward the concentrated sulfuric acid is instilled in saponification liquor, pH value is adjusted to neutrality, stand makes its layering afterwards, by lower floor's solution point
Freezing and crystallizing is carried out at 15 DEG C of temperature 15 hours, obtain crude crystalline liquid from, upper liquid.Crude crystalline liquid is by solid-liquid point
From obtaining filter cake sterol crude product 44g (sterol content 30%).
3rd, 44g sterols crude product is added in reactor, then 80g petroleum ethers and 13g anhydrous calcium chlorides is put into reactor,
Open stirring and be warming up to 45 DEG C simultaneously.Backward reactor add 6g absolute methanols, carry out complex reaction.Complex reaction control temperature
Spend for 55 DEG C, after reaction continues 2 hours, terminate to react and material is down to 32 DEG C, carry out separation of solid and liquid afterwards, obtain filter cake
Sterol complex compound 60g.
4th, 60g sterol complex compounds are added in reactor, add 60g petroleum ethers and 30g water.Unlatching is stirred and heated to
55 DEG C are hydrolyzed reaction.After hydrolysis is carried out 1 hour, stratification, lower floor's moisture is separated out, upper materials are at 15 DEG C
At a temperature of carry out freezing and crystallizing 10 hours, obtain finished product crystal solution.Finished product crystal solution passes through separation of solid and liquid, and obtained filter cake passes through
It is dried under reduced pressure, final to obtain sterol finished product 11g, purity is 97.5% after testing.
Embodiment two
1st, the sodium hydrate methanol solution 40g of 100g residual oil (sterol ester content 25%) and mass fraction 20% is added to
In reactor, control 70 DEG C of temperature to carry out reaction 2 hours under agitation, obtain saponification liquor.
2nd, toward concentrated hydrochloric acid is instilled in saponification liquor, pH value is adjusted to neutrality, stand makes its layering afterwards, by lower floor's solution point
Freezing and crystallizing is carried out at 12 DEG C of temperature 16 hours, obtain crude crystalline liquid from, upper liquid.Crude crystalline liquid is by solid-liquid point
From obtaining filter cake sterol crude product 44.5g (sterol content 30%).
3rd, 44.5g sterols crude product is added in reactor, then 80g n-hexanes and the anhydrous chlorinations of 13g is put into reactor
Calcium, open stirring and be warming up to 50 DEG C simultaneously.Backward reactor add 6g absolute ethyl alcohols, carry out complex reaction.Complex reaction control
Temperature processed is 55 DEG C, after reaction continues 3 hours, terminates to react and material is down into 30 DEG C, carry out separation of solid and liquid afterwards, obtain
Filter cake sterol complex compound 61g.
4th, 61g sterol complex compounds are added in reactor, add 70g petroleum ethers and 50g water.Unlatching is stirred and heated to
58 DEG C are hydrolyzed reaction.After hydrolysis is carried out 1.5 hours, stratification, lower floor's moisture is separated out, upper materials are at 12 DEG C
At a temperature of carry out freezing and crystallizing 10 hours, obtain finished product crystal solution.Finished product crystal solution passes through separation of solid and liquid, obtained filter cake warp
Cross and be dried under reduced pressure, final to obtain sterol finished product 11.7g, purity is 97.3% after testing.
Embodiment three
1st, the sodium hydrate methanol solution 35g of 100g residual oil (sterol ester content 25%) and mass fraction 20% is added to
In reactor, control 65 DEG C of temperature to carry out reaction 3 hours under agitation, obtain saponification liquor.
2nd, toward the concentrated sulfuric acid is instilled in saponification liquor, pH value is adjusted to neutrality, stand makes its layering afterwards, by lower floor's solution point
Freezing and crystallizing is carried out at 10 DEG C of temperature 18 hours, obtain crude crystalline liquid from, upper liquid.Crude crystalline liquid is by solid-liquid point
From obtaining filter cake sterol crude product 44.9g (sterol content 30%).
3rd, 44.9g sterols crude product is added in reactor, then 80g petroleum ethers and the anhydrous chlorinations of 13g is put into reactor
Calcium, open stirring and be warming up to 50 DEG C simultaneously.Backward reactor add 6g absolute ethyl alcohols, carry out complex reaction.Complex reaction control
Temperature processed is 60 DEG C, after reaction continues 2 hours, terminates to react and material is down into 30 DEG C, carry out separation of solid and liquid afterwards, obtain
Filter cake sterol complex compound 60.8g.
4th, 60.8g sterol complex compounds are added in reactor, add 60g ethyl acetate and 60g water.Open and stir and add
Hot to 60 DEG C are hydrolyzed reaction.After hydrolysis is carried out 1.5 hours, stratification, lower floor's moisture is separated out, upper materials exist
Freezing and crystallizing is carried out at a temperature of 15 DEG C 10 hours, obtain finished product crystal solution.Finished product crystal solution passes through separation of solid and liquid, obtained filter
Cake is final to obtain sterol finished product 11.2g by being dried under reduced pressure, and purity is 97.2% after testing.
Claims (7)
- A kind of 1. method that high-purity sterol is extracted from the residual oil containing sterol ester, it is characterised in that comprise the following steps：(A) residual oil and a certain amount of highly basic methanol solution are added in reactor, are stirred reaction at a certain temperature, instead Saponification liquor is obtained after answering certain time；The addition of highly basic methanol solution is to add 30g to 40g per 100g residual oil；Described temperature is 60 DEG C to 70 DEG C；The described reaction time is 2 to 3 hours；(B) inorganic acid is instilled in above-mentioned saponification liquor, pH value is adjusted to neutrality, stand makes its layering afterwards, by lower floor's solution Separation, upper liquid carry out freezing and crystallizing certain time, obtain crude crystalline liquid, then crude crystalline liquid is carried out at a certain temperature Separation of solid and liquid, obtain filter cake sterol crude product；The addition of described inorganic acid with adjust material pH to neutrality for standard；Described freezing and crystallizing temperature is 10 DEG C to 15 DEG C；The described freezing and crystallizing time is 10 hours to 18 hours；(C) above-mentioned sterol crude product is added in reactor, then a certain amount of organic aprotic solvents and complexing are put into reactor Agent, open stirring and rise to certain reacting initial temperature simultaneously；Backward reactor in add a certain amount of organic proton solvent, Carry out complex reaction；Complex reaction controls certain temperature, after certain time is reacted, terminates to react and be down to material necessarily Temperature, carry out separation of solid and liquid again afterwards, obtain filter cake sterol complex compound；Described organic aprotic solvents addition is 1.5-2 times of sterol crude product quality；Described complexing agent is anhydrous calcium chloride, and addition is 0.6-1.0 times of sterol content in sterol crude product；Described reacting initial temperature is 45-50 DEG C；Described organic proton solvent addition is 0.3-0.5 times of sterol content in sterol crude product；It is 50-60 DEG C that described complex reaction, which controls temperature,；The described complex reaction time is 2-3 hours；The temperature that described complex reaction reduces after terminating is 30-35 DEG C；(D) above-mentioned sterol complex compound is added in reactor, adds a certain amount of organic solvent and a certain amount of water, opens stirring And it is heated to certain temperature and reaction is hydrolyzed；After hydrolysis carries out certain time, stratification, lower floor's moisture is separated out, Upper materials carry out the freezing and crystallizing regular hour at a certain temperature, obtain finished product crystal solution；Finished product crystal solution passes through solid-liquid Separation, obtained filter cake, which entered to be dried under reduced pressure, obtains sterol finished product；Described organic solvent addition is 1-1.5 times that sterol is complexed amount of substance；The water of described addition is 0.5-1 times of sterol complex compound；Described hydrolysising reacting temperature is 55-60 DEG C；Described hydrolysis time is 1-1.5 hours；Described freezing and crystallizing temperature is 10 to 15 DEG C.
- 2. a kind of method that high-purity sterol is extracted from the residual oil containing sterol ester according to claim 1, its feature exist In described highly basic methanol solution is the methanol solution that one or both of sodium hydroxide, potassium hydroxide mix, and concentration is 20%.
- 3. a kind of method that high-purity sterol is extracted from the residual oil containing sterol ester according to claim 1, its feature exist In described inorganic acid is the concentrated sulfuric acid, concentrated hydrochloric acid one or both mixing therein.
- 4. a kind of method that high-purity sterol is extracted from the residual oil containing sterol ester according to claim 1, its feature exist In,；Described organic aprotic solvents or organic solvent are one kind in n-hexane, petroleum ether, ethyl acetate or butanone；It is described Organic proton solvent be one kind in methanol or ethanol.
- 5. a kind of method that high-purity sterol is extracted from the residual oil containing sterol ester according to claim 1, its feature exist In,；Described organic aprotic solvents or organic solvent are one kind in n-hexane, petroleum ether, ethyl acetate or butanone.
- 6. a kind of method that high-purity sterol is extracted from the residual oil containing sterol ester according to claim 1, its feature exist In described organic proton solvent is one kind in methanol or ethanol.
- 7. a kind of method that high-purity sterol is extracted from the residual oil containing sterol ester according to claim 1, its feature exist In described highly basic methanol solution is the methanol solution that one or both of sodium hydroxide, potassium hydroxide mix, and concentration is 20%；Described inorganic acid is the concentrated sulfuric acid, concentrated hydrochloric acid one or both mixing therein；Described organic aprotic solvents or Organic solvent is one kind in n-hexane, petroleum ether, ethyl acetate or butanone；Described organic proton solvent is methanol or ethanol In one kind.
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Cited By (5)
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| CN110818762A (en) * | 2019-11-19 | 2020-02-21 | 福建省格兰尼生物工程股份有限公司 | Residual oil treatment method for recovering sterol and refining sylvite |
| CN111686132A (en) * | 2020-06-15 | 2020-09-22 | 中山大学 | Syngnathus sterol solid dispersion and application thereof in treating cerebral apoplexy |
| CN111777655A (en) * | 2020-07-27 | 2020-10-16 | 福建省格兰尼生物工程股份有限公司 | Method for extracting wood sterol from tall oil pitch |
| CN113753860A (en) * | 2021-09-27 | 2021-12-07 | 宜春大海龟生命科学有限公司 | Method for recovering divalent metal chloride in complexing process |
| CN114213496A (en) * | 2021-11-25 | 2022-03-22 | 浙江花园生物高科股份有限公司 | Method for separating lanosterol and dihydrolanosterol |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110818762A (en) * | 2019-11-19 | 2020-02-21 | 福建省格兰尼生物工程股份有限公司 | Residual oil treatment method for recovering sterol and refining sylvite |
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| CN111686132B (en) * | 2020-06-15 | 2022-06-24 | 中山大学 | Syngnathus sterol solid dispersion and application thereof in treating cerebral apoplexy |
| CN111777655A (en) * | 2020-07-27 | 2020-10-16 | 福建省格兰尼生物工程股份有限公司 | Method for extracting wood sterol from tall oil pitch |
| CN113753860A (en) * | 2021-09-27 | 2021-12-07 | 宜春大海龟生命科学有限公司 | Method for recovering divalent metal chloride in complexing process |
| CN114213496A (en) * | 2021-11-25 | 2022-03-22 | 浙江花园生物高科股份有限公司 | Method for separating lanosterol and dihydrolanosterol |
| CN114213496B (en) * | 2021-11-25 | 2023-12-22 | 浙江花园生物高科股份有限公司 | Method for separating lanosterol and dihydro lanosterol |
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