CN113480514B - Method for extracting sesamin - Google Patents
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- CN113480514B CN113480514B CN202110935519.9A CN202110935519A CN113480514B CN 113480514 B CN113480514 B CN 113480514B CN 202110935519 A CN202110935519 A CN 202110935519A CN 113480514 B CN113480514 B CN 113480514B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring
- C07D317/64—Oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
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Abstract
The invention relates to a method for extracting sesamin. The method realizes the separation of the sesamin through the steps of extraction, concentration, filtration, crystallization, recrystallization, centrifugation, drying and the like, has high degree of continuity of the whole set of extraction process, and is suitable for a matched automatic production line to improve the production efficiency and reduce the production cost.
Description
Technical Field
The invention relates to a method for extracting sesamin.
Background
The main active substance in sesame is sesame lignan, the sesame lignan content in sesame varies according to different sesame, and the sesame lignan mainly comprises: sesamin, episesamin, sesamol, sesamolin, etc. Sesamol is naturally present in sesame oil, and its content is very small, and the product is aromatic phenolic compound, and can be reacted with acid, aldehyde and alcohol (phenol) to produce ester and ether derivatives, and is slightly soluble in water, and can be continuously decomposed by sesamolin in the course of thermal processing, and in the course of thermal processing, it can be up to above 60 mg/(100 g) in sesame oil.
Therefore, sesaminol and sesamolin and derivatives decomposed during heating must be completely separated to obtain high-purity sesamin.
Disclosure of Invention
The present invention has completed the following in order to obtain high-purity sesamin.
The method specifically comprises the following steps:
step S10, putting sesame into extraction equipment, and adding ethanol for extraction to obtain primary extraction liquid;
step S20, concentrating the primary extract to obtain a concentrated solution;
step S30, filtering the concentrated solution to obtain filtrate;
step S40, transferring the filtrate into a crystallizing tank for crystallization treatment to obtain a crude product;
step S50, transferring the crude product into a crystallization tank, and carrying out recrystallization treatment to obtain a fine product;
step S60, carrying out centrifugal separation on the competitive product, and drying to obtain sesamin;
optionally, the step S10 includes:
step S11, a first-stage extraction step, namely transferring sesame and ethanol into first extraction equipment, mixing according to the mass-volume ratio (kg: L) of 1:2, adjusting the pH value to 5.5-6.5 by using glacial acetic acid, and processing for 1 hour to obtain an extracting solution;
adding ethanol into a first extraction device while producing an extracting solution, adjusting the pH value of the ethanol to be 5.5-6.5 by using glacial acetic acid, adjusting the mass-to-volume ratio (kg: L) of the adding amount of the sesame to the ethanol to be 1:1, treating the produced solution for 3 hours, and keeping the speed of producing the extracting solution and the speed of adding the ethanol of the first extraction device equal to each other to achieve the dynamic balance of the liquid in the first extraction device;
the first extraction equipment completes the output of the extracting solution to obtain a first-stage extracting solution;
step S12, a second-stage extraction step, namely adding ethanol into first extraction equipment, mixing sesame and the ethanol according to the mass-volume ratio (kg: L) of 1:1, adjusting the pH value to 4.5-5.5 by using glacial acetic acid, treating for 0.5 hour, and enabling the first extraction equipment to produce an extracting solution to second extraction equipment;
after the first extraction equipment finishes the production of the extracting solution, adding ethanol into the first extraction equipment, mixing the sesame and the ethanol according to the mass-volume ratio (kg: L) of 1:1, adjusting the pH value to 4.5-5.5 by using glacial acetic acid, and treating for 0.5 hour; adding sesame into second extraction equipment, wherein the adding amount of the sesame is equal to that of the first extraction equipment, extracting by using the output liquid of the first extraction equipment, and treating for 0.5 hour;
the first extraction equipment and the second extraction equipment simultaneously produce extracting solution, and the specific extracting solution producing mode is that ethanol is added into the first extraction equipment while the first extraction equipment produces the extracting solution, the pH value of the ethanol is adjusted to 4.5-5.5 by using glacial acetic acid, and the mass-to-volume ratio (kg: L) of the added sesame to the ethanol is 1: 1;
the first extraction equipment outputs the extracting solution to the second extraction equipment, the produced solution is treated for 3 hours, the speed of the extracting solution output by the second extraction equipment is kept equal to the speed of ethanol added by the first extraction equipment, and the dynamic balance of the liquid in the first extraction equipment and the second extraction equipment is achieved;
the second extraction equipment completes the output of the extracting solution to obtain a second-level extracting solution;
carrying out deslagging treatment by first extraction equipment, and discharging sesame in the equipment;
step S13, a third-stage extraction step, namely adding ethanol into second extraction equipment, mixing sesame and the ethanol according to the mass-volume ratio (kg: L) of 1:1, adjusting the pH value to 4.5-5.5 by using glacial acetic acid, treating for 0.5 hour, and enabling the second extraction equipment to start to produce an extracting solution to third extraction equipment;
after the second extraction equipment finishes the production of the extracting solution, adding ethanol into the second extraction equipment, mixing the sesame and the ethanol according to the mass-volume ratio (kg: L) of 1:1, adjusting the pH value to 4.5-5.5 by using glacial acetic acid, and treating for 0.5 hour; adding sesame into a third extraction device, wherein the adding amount of the sesame is equal to that of the second extraction device, extracting by using the output liquid of the second extraction device, and treating for 0.5 hour;
the second extraction equipment and the third extraction equipment simultaneously produce extracting solution, and the specific extracting solution producing mode is that ethanol is added into the second extraction equipment while the second extraction equipment produces the extracting solution, the pH value of the ethanol is adjusted to 4.5-5.5 by using glacial acetic acid, and the mass-to-volume ratio (kg: L) of the added sesame to the ethanol is 1: 1;
the second extraction equipment outputs the extracting solution to the third extraction equipment, the produced solution is treated for 3 hours, the speed of the extracting solution output by the third extraction equipment is kept equal to the speed of the ethanol added by the second extraction equipment, and the dynamic balance of the liquid in the second extraction equipment and the third extraction equipment is achieved;
the third extraction equipment finishes the output of the extracting solution to obtain a third-level extracting solution;
the second extraction equipment carries out deslagging treatment and discharges the sesame in the equipment;
and step S14, mixing the primary extract, the secondary extract and the tertiary extract to obtain a primary extract.
Optionally, the extraction temperature of the step S11, the step S12 and the step S13 is 78 ℃ to 82 ℃.
Optionally, the step S20 includes: and (3) carrying out reduced pressure concentration on the primary extract, controlling the pressure to be 0.01-0.06Mpa, and concentrating to 1/8-1/4 of the volume of the primary extract.
Optionally, the step S30 includes: the concentrated solution is filtered by using acid modified active carbon firstly and then non-woven fabrics, and the aperture size is 280-320 meshes, thus obtaining the filtrate.
Optionally, the step 50 includes: and transferring the crude product into a crystallization tank, dissolving the crude product by using 95% ethanol, heating the crude product and the ethanol for dissolving according to the mass-volume ratio (kg: L) of 1 (3-5), cooling to room temperature after complete dissolution, adding seed crystals, and separating the mixture liquid after 36-48 hours to obtain a refined product.
According to the invention, the sesame is extracted by weak acid glacial acetic acid, so that the sesamolin is decomposed while the pH value more suitable for extracting effective components is provided, and sesamol is subjected to chemical conversion to generate derivatives thereof, so that the subsequent separation is simpler and more convenient; the extraction process adopts dynamic gradient extraction, the extraction efficiency is high, and the use amount of a solvent is small; during concentration, acid modified activated carbon is adopted for treatment, so that the adsorption capacity of the activated carbon is improved, and the sesamol and the sesamolin are separated more thoroughly. The whole set of extraction process has high degree of continuity, and is suitable for matching with an automatic production line to improve the production efficiency and reduce the production cost.
Drawings
Fig. 1 is a flow chart of a method for extracting sesamin according to an embodiment of the present invention.
Detailed Description
The present invention will be described in more detail with reference to the following embodiments.
Example 1
Step S10, putting 1600kg of sesame into an extraction tank I, adding 3200L of 80% ethanol, adjusting the pH value to 5.5 by using glacial acetic acid, extracting for 1 hour at 80 ℃, and beginning to produce an extracting solution to an extracting solution storage tank; adding 1600L of 80% ethanol with pH value adjusted to 5.5 by glacial acetic acid into the extraction tank I while producing the extracting solution, continuously producing the extracting solution at 80 ℃ for 3 hours, and keeping the speed of producing the extracting solution in the extraction tank I equal to the speed of adding the ethanol to achieve dynamic balance of the liquid in the extraction tank I; the extraction tank I finishes the extraction of the extracting solution to obtain a first-level extracting solution.
Adding 1600L of 80% ethanol with pH adjusted to 4.5 by glacial acetic acid into the extraction tank I, and extracting at 80 deg.C for 0.5 hr; 1600kg of sesame is put into the extraction tank II; the extraction tank I starts to produce an extracting solution to the extraction tank II, sesame in the extraction tank II is extracted by using the produced solution of the extraction tank I, and the extraction is carried out for 0.5 hour at 80 ℃; after the extraction of the extracting solution is finished in the extraction tank I, 1600L of 80% ethanol with the pH value adjusted to 4.5 by glacial acetic acid is added into the extraction tank I, and the extraction is carried out for 0.5 hour at the temperature of 80 ℃; draw jar I and draw jar II simultaneous output extract, produce the liquid mode and be: while the extracting solution is produced in the extracting tank I, 1600L of 80% ethanol with pH value adjusted to 4.5 by glacial acetic acid is added into the extracting tank I; the extracting solution is output from the extracting tank I to an extracting tank II, the extracting tank II is continuously processed for 3 hours at the temperature of 80 ℃, the speed of the extracting solution output from the extracting tank II is kept equal to the speed of the extracting tank I for adding the ethanol, and the dynamic balance of the liquid in the extracting tank I and the extracting tank II is achieved; and the extraction tank II finishes the output of the extracting solution to obtain a secondary extracting solution. Sesame is discharged from the extraction tank I.
Adding 1600L of 80% ethanol with pH value adjusted to 4.5 by glacial acetic acid into the extraction tank II, and extracting at 80 deg.C for 0.5 hr; 1600kg of sesame is put into the extraction tank III; the extraction tank II starts to produce an extracting solution to the extraction tank III, sesame in the extraction tank III is extracted by using the produced solution of the extraction tank II, and the extraction is carried out for 0.5 hour at 80 ℃; after the extraction liquid is produced in the extraction tank II, 1600L of 80% ethanol with pH value adjusted to 4.5 by glacial acetic acid is added into the extraction tank II, and the extraction is carried out for 0.5 hour at 80 ℃; draw jar II and draw jar III and produce the extract simultaneously, produce the liquid mode and be: while the extracting solution is produced in the extracting tank II, 1600L of 80% ethanol with pH value adjusted to 4.5 by glacial acetic acid is added into the extracting tank III; the extracting tank II outputs extracting solution to the extracting tank III, the extracting solution is continuously processed for 3 hours at the temperature of 80 ℃, the speed of the extracting solution output by the extracting tank III is kept equal to the speed of the extracting tank II for adding ethanol, and the dynamic balance of the liquid in the extracting tank II and the extracting tank III is achieved; and the extraction tank III is used for completing the production of the extracting solution, so that a third-level extracting solution is obtained. And discharging the sesame from the extraction tank II.
Mixing the first-stage extract, the second-stage extract and the third-stage extract to obtain about 12000L of primary extract.
And step S20, concentrating the primary extract by using a triple-effect evaporator at 55 ℃ under 0.01Mpa for 6 hours, and concentrating the primary extract to obtain 3000L of the residual concentrated solution.
And step S30, filtering the concentrated solution, firstly, treating the concentrated solution by using acid modified activated carbon, and then, filtering the concentrated solution by using non-woven fabrics, wherein the pore size is 320 meshes, so as to obtain filtered solution.
And step S40, transferring the filtrate into a crystallizing tank, crystallizing at 20 ℃ for 24 hours to obtain 84.6g of crude product.
And step S50, transferring the crude product into a crystallizing tank, adding 500L of 95% ethanol for dissolving, cooling to room temperature after complete dissolution, adding seed crystals, and separating the mixture liquid after 48 hours to obtain refined 80.62 kg.
And step S60, carrying out centrifugal separation on the refined product, and drying to obtain the sesame extract with the weight of 65.14 kg.
Through detection, the purity of the sesamin is 99.20%.
It will be understood that the above embodiments are merely exemplary embodiments adopted to illustrate the principles of the present invention, and the present invention is not limited thereto. It will be apparent to those skilled in the art that various modifications and improvements can be made without departing from the spirit and substance of the invention, and these modifications and improvements are also considered to be within the scope of the invention.
Claims (5)
1. A method for extracting sesamin is characterized by comprising the following steps:
step S10, putting sesame into extraction equipment, adding ethanol for extraction, and obtaining an initial extraction solution;
step S20, concentrating the primary extract to obtain a concentrated solution;
step S30, filtering the concentrated solution to obtain a filtrate;
step S40, transferring the filtrate into a crystallizing tank for crystallization to obtain a crude product;
step S50, transferring the crude product into a crystallizing tank for recrystallization treatment to obtain a fine product;
step S60, carrying out centrifugal separation on the competitive product, and drying to obtain sesamin;
step S10 includes:
step S11, a first-stage extraction step, namely transferring sesame and ethanol into first extraction equipment, mixing according to the mass-volume ratio (kg: L) of 1:2, adjusting the pH value to 5.5-6.5 by using glacial acetic acid, and processing for 1 hour to obtain an extracting solution;
adding ethanol into the first extraction equipment while producing the extracting solution, adjusting the pH value of the ethanol to 5.5-6.5 by using glacial acetic acid, adjusting the mass-to-volume ratio (kg: L) of the added sesame to the ethanol to be 1:1, treating the produced solution for 3 hours, and keeping the speed of producing the extracting solution and the speed of adding the ethanol of the first extraction equipment equal to each other to achieve the dynamic balance of the liquid in the first extraction equipment;
the first extraction equipment completes the output of the extracting solution to obtain a first-stage extracting solution;
step S12, a second-stage extraction step, namely adding ethanol into first extraction equipment, mixing sesame and the ethanol according to the mass-volume ratio (kg: L) of 1:1, adjusting the pH value to 4.5-5.5 by using glacial acetic acid, and processing for 0.5 hour, wherein the first extraction equipment starts to produce an extracting solution to second extraction equipment;
after the first extraction equipment finishes the production of the extracting solution, adding ethanol into the first extraction equipment, mixing the sesame and the ethanol according to the mass-volume ratio (kg: L) of 1:1, adjusting the pH value to 4.5-5.5 by using glacial acetic acid, and treating for 0.5 hour; adding sesame into second extraction equipment, wherein the adding amount of the sesame is equal to that of the first extraction equipment, extracting by using the output liquid of the first extraction equipment, and treating for 0.5 hour;
the first extraction equipment and the second extraction equipment simultaneously produce extracting solution, and the specific extracting solution producing mode is that ethanol is added into the first extraction equipment while the first extraction equipment produces the extracting solution, the pH value of the ethanol is adjusted to 4.5-5.5 by using glacial acetic acid, and the mass-to-volume ratio (kg: L) of the added sesame to the ethanol is 1: 1;
the first extraction equipment outputs the extracting solution to the second extraction equipment, the produced solution is treated for 3 hours, the speed of the extracting solution output by the second extraction equipment is kept equal to the speed of the ethanol added by the first extraction equipment, and the dynamic balance of the liquid in the first extraction equipment and the second extraction equipment is achieved;
the second extraction equipment finishes the output of the extracting solution to obtain a secondary extracting solution;
carrying out deslagging treatment by first extraction equipment, and discharging sesame in the equipment;
step S13, a third-stage extraction step, namely adding ethanol into second extraction equipment, mixing sesame and the ethanol according to the mass-volume ratio (kg: L) of 1:1, adjusting the pH value to 4.5-5.5 by using glacial acetic acid, treating for 0.5 hour, and enabling the second extraction equipment to start to produce an extracting solution to third extraction equipment;
after the second extraction equipment finishes the production of the extracting solution, adding ethanol into the second extraction equipment, mixing the sesame and the ethanol according to the mass-volume ratio (kg: L) of 1:1, adjusting the pH value to 4.5-5.5 by using glacial acetic acid, and treating for 0.5 hour; adding sesame into a third extraction device, wherein the adding amount of the sesame is equal to that of the second extraction device, extracting by using the output liquid of the second extraction device, and treating for 0.5 hour;
the second extraction equipment and the third extraction equipment simultaneously produce extracting solution, and the specific extracting solution producing mode is that ethanol is added into the second extraction equipment while the second extraction equipment produces the extracting solution, the pH value of the ethanol is adjusted to 4.5-5.5 by using glacial acetic acid, and the mass-to-volume ratio (kg: L) of the added sesame to the ethanol is 1: 1;
the second extraction equipment outputs the extracting solution to the third extraction equipment, the produced solution is treated for 3 hours, the speed of the extracting solution output by the third extraction equipment is kept equal to the speed of the ethanol added by the second extraction equipment, and the dynamic balance of the liquid in the second extraction equipment and the third extraction equipment is achieved;
the third extraction equipment completes the output of the extracting solution to obtain a third-level extracting solution;
the second extraction equipment carries out deslagging treatment and discharges the sesame in the equipment;
and step S14, mixing the primary extract, the secondary extract and the tertiary extract to obtain a primary extract.
2. The method of claim 1, wherein the extraction temperature of the steps S11, S12, S13 is 78-82 ℃.
3. The method according to claim 1, wherein step S20 includes: and (3) carrying out reduced pressure concentration on the primary extract, controlling the pressure to be 0.01-0.06Mpa, and concentrating to 1/8-1/4 of the volume of the primary extract.
4. The method according to claim 1, wherein step S30 includes: the concentrated solution is filtered by firstly using acid modified activated carbon and then using non-woven fabrics, and the aperture size is 280-320 meshes, so as to obtain the filtrate.
5. The method of claim 1, wherein step 50 comprises: and transferring the crude product into a crystallizing tank, dissolving the crude product by using 95% ethanol, heating the crude product and the ethanol to dissolve according to the mass-volume ratio (kg: L) of 1 (3-5), cooling to room temperature after complete dissolution, adding seed crystals, and separating the mixture liquid after 36-48 hours to obtain a fine product.
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