CN1680220A - Agent of extracting polyphenol from rape seed cakes or husks and its preparation - Google Patents
Agent of extracting polyphenol from rape seed cakes or husks and its preparation Download PDFInfo
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Abstract
An extracting agent for extracting polyphenol from rapeseed cakes or rapeseed shell and its production are disclosed. It is carried out by breaking rapeseed cakes or rapeseed shell, degreasing, using extracting agent, leaching, steaming out alcohol at vacuum, purifying polyphenol by column chromatography, vacuum concentrating, and drying; or purifying the polyphenol solution by resin or glucose gel or polyamide column. The obtaining ratio of polyphenol can reach to 1.7%-2.3%, the purification can reach above 40%-70% and 98%.
Description
Technical field
The invention belongs to the extraction field of the chemistry of agriculture natural product, relate in particular to a kind of extraction agent that extracts plant polyphenol that is applicable to, utilizing the by product of this extraction agent after making oil is the method for extracting polyphenol the coleseed kind skin after dregs of rapeseed cake or the vegetable seed shelling.
Background technology
Semen Brassicae campestris (rapeseed) is China and the main in the world oil crops of cultivating, and its main application is to be used for system oil.After the system oil, the dregs of rapeseed cake of generation, vegetable seed skin the like waste account for more than 60% of Semen Brassicae campestris total mass.According to statistics, China can produce ten thousand tons of dregs of rapeseed cake 600-700 every year.There is data to show rapeseed cake dregs inner protein about 40%, contains polyphenol 2-4%, contain phytic acid 3%-7%.The gal4 amino acid compositional model and the idealized model of rapeseed meal are very approaching.But, add and contain that dregs of rapeseed cake is difficult to be fully utilized preferably always to compositions such as the deleterious sulphur glucosides of people and animals owing to mix with antinutritional factor such as polyphenol, phytic acid.
Studies show that in recent years extracted oil behind the rapeseed peeling, helps improving the quality of oil and the comprehensive utilization of grouts.Oil expression will be the developing direction of Semen Brassicae campestris processing from now on behind the rapeseed peeling.
Also contain polyphenols in the Semen Brassicae campestris skin, compare with rapeseed meal, the content of the condensed tannin in the Semen Brassicae campestris skin (a class polyphenols) is higher, and the value of condensed tannin is higher.
Discover that plant polyphenol has purposes very widely at field of food and other field.For example, test verified: polyphenol can be anti-oxidant, anticancer, preventing cardiovascular disease, radioprotective, beauty treatment or the like, thereby the people is arranged even plant polyphenol is regarded as the 8th nutrient substance of human body, plant polyphenol has also become the focus of international and domestic research in recent years, and the bibliographical information that extracts polyphenol from each plant material is constantly arranged.
From rapeseed meal or vegetable seed skin, extract polyphenol, not only can utilize polyphenol, and help proteinic development and use in the grouts.
To the comprehensive utilization of rapeseed meal, existing research mainly concentrates on proteinic extraction aspect.A kind of route is to utilize its protein after taking out polyphenol with organic solvent extracting, does not examine the utilization of filter polyphenol; The solvent that is adopted is harmful often, and is disagreeableness to environment.The shortcoming of this technological line is not utilize polyphenol from rapeseed, and contaminate environment (Wu Moucheng, Zhang Yan etc., the research of the extraction of tannin, composition and character in the Semen Brassicae campestris, Chinese grain and oil journal, 1998,13 (2): 17-21; Ceng Xiaobo, Wu Moucheng etc., acetone method is produced rapeseed protein concentrate, Chinese grain and oil journal, 2001,16 (4): 10-13).Another technological line is that employing adds metal-salt or urea makes protein form micella and (E.Donald Murray that protein separation is come out, Semen Brassicae campestris: a kind of global high quality vegetable protein source that has potentiality, the Asia-Pacific grocery trade, the 4th phase of calendar year 2001,28-32).This technological line is not examined the utilization of filter polyphenol yet, and the consumption of salt is big, the method complexity of separated salt, and the cost height is difficult to use in scale operation.
From plant, extract the existing relevant patent documentation of polyphenol, wherein maximum is about extract the report of tea-polyphenol from tealeaves, and for example the patent No. is the 9119901.8 open technological lines that extract tea-polyphenol from tealeaves: its method comprises boiling water extraction, filtration, precipitation, acidifying, extraction, separation, depickling and drying.It is characterized in that in extracting solution, adding and to make the sedimentary soluble inorganic salt of tea-polyphenol such as aluminum chloride, zinc sulfate, bariumchloride or calcium chloride etc., transfer pH to neutrality or weakly alkaline with weakly alkaline solution, behind the precipitation separation, dissolving makes acidizing fluid to precipitating fully to add strong acid or middle strong acid in precipitation, use ethyl acetate extraction again, obtain the tea-polyphenol raw product through the precipitation drying.Number of patent application 01106878.7 document has been introduced a kind of green extraction method of tea-polyphenol, saltouts with sodium-chlor in the extracting solution again, and with the polymeric amide sorbent material, acid citric acid is that washing composition makes tea-polyphenol separate with pigment.Number of patent application is 03128215.6 bibliographical information extracts the method for lotus rhizome polyphenol from lotus rhizome, in the lotus rhizome raw material of pulverizing, add ethanolic soln, extract, filter the concentrated and purified then ethanol evaporation that makes, adding ethyl acetate extraction, is the lotus rhizome polyphenol with the concentrated solution drying at last.Above-mentioned patent or patent application and theme of the present invention have very big difference, and concrete extracting method also has very big difference.
Do not extract the extraction agent of polyphenol and the report of extracting method thereof at present by retrieval about being exclusively used in from the coleseed kind skin after rapeseed cake dregs and the shelling.
Summary of the invention
The objective of the invention is to overcome the defective of prior art, develop a kind of extraction agent that particularly the extraction polyphenol is used from coleseed grouts and coleseed shelling kind of skin from plant, also comprise the economic benefit and the social benefit of the comprehensive utilization of the by product after the method for utilizing this extraction agent particularly to extract polyphenol from plant from coleseed grouts and coleseed shelling kind of skin is processed with the raising Semen Brassicae campestris, reduce harm environment.
The present invention is achieved through the following technical solutions:
The general plotting of method of the present invention is, with raw material pulverizing such as the dregs of rapeseed cake of polyphenol to be extracted or Semen Brassicae campestris kind skins to the 40-80 order, adding special-purpose extraction agent extracts, vacuum removal ethanol, flow through then Zeo-karb, anionite-exchange resin, macroporous resin column are flowed through behind the vacuum removal organic solvent or without dextrane gel or polyamide column, are used the organic solvent stepwise elution, vacuum concentration is dry for making with extra care polyphenol or polyphenol fraction respectively.
The concrete technical scheme of invention is as follows:
A kind of being used for from the extraction agent of rapeseed cake dregs or coleseed kind skin extraction polyphenol, it comprises following component:
Neutral calcium salt or analogue be 0.10-5.50g/100ml by weight percentage,
Ethanolic soln is 30%-85% by weight percentage,
Water is supplemented to 100,
It prepares in accordance with the following methods:
A, the preparation ethanolic soln before in advance adjust pH to 2-5,
B, described neutral calcium salt or analogue are added in the ethanolic soln.
Neutral calcium salt in the described extraction agent is selected wherein a kind of from calcium sulfate, calcium chloride, calcium phosphate, calcium lactate or nitrocalcite; Described analogue is selected wherein a kind of from bariumchloride, magnesium chloride, zinc chloride, sal epsom, zinc sulfate, aluminum chloride.
Extract the preparation method of polyphenol from rapeseed cake dregs and Semen Brassicae campestris kind skin, it may further comprise the steps:
1) will pulverize and degreasing after rapeseed cake dregs or Semen Brassicae campestris kind skin powder join extraction agent as claimed in claim 1, raw material is 1: 5 to 1: 15 with the ratio of extraction agent, under 45-85 ℃, handled 30 minutes-2 hours, intermittently stir extraction, obtain feed liquid 1, perhaps filter residue is extracted under the same conditions again 1-3 all over after obtain feed liquid 2, merge feed liquid 1 and 2;
2) the merging feed liquid that step 1) is obtained is removed the following impurity of 200 orders, gets filtrate 1;
3) with step 2) filtrate 1 that obtains puts vacuum concentration below 50 ℃, reclaims ethanol, obtains concentrated solution 1;
4) concentrated solution 1 that step 3) is obtained is successively crossed cation exchange resin column and anion-exchange resin column, removes the impurity in the concentrated solution 1, obtains the polyphenol solution of preliminary purification;
5) the polyphenol solution of the preliminary purification that step 4) is obtained is crossed the macroporous resin adsorption post, wash with water remove impurity after, with the ethanolic soln wash-out of 10%-76% percent by volume; The perhaps methanol solution wash-out of 20%-80% percent by volume, the polyphenol solution that obtains being further purified;
6) the polyphenol solution that is further purified that step 5) is obtained reclaims solvent at vacuum concentration below 50 ℃, obtains concentrated solution 2;
With concentrated solution 2 dryings that step 6) obtains, drying mode can adopt lyophilize or spraying drying or vacuum-drying, promptly obtains refining polyphenol.
Can also take another kind of technical scheme in above-mentioned preparation method, its step comprises:
1) with above-mentioned steps 6) dextrane gel or polyamide column on the concentrated solution 2 that obtains, use methyl alcohol successively: water=1: 3,1: 1,3: 1; 100% methyl alcohol; Methyl alcohol: acetone=1: 1; 50% acetone soln wash-out is collected elutriant respectively;
Also can replace methyl alcohol with ethanol, the ratio of its interpolation is identical with methyl alcohol.
2) with the elutriant vacuum concentration of step 1) gained, get concentrated solution 3;
3) with step 2) concentrated solution 3 dryings of gained, the polyphenol fraction.
The refining employed macroporous resin column of purifying is the macroporous resin to the selective absorption of polyphenol from rapeseed in the said extracted method.The solution stream that contains polyphenol is crossed the energy adsorbing polyphenols, and washing can be removed polysaccharide, protein, and polyphenol then is retained on the post.
The refining employed positively charged ion of purifying, anionite-exchange resin can be removed metal ion, sinapinic acid, sinapic acid choline ester in the polyphenol in the described extracting method;
The present invention preferably resolves two hang-ups that prior art exists; The one, contain more low-molecular-weight sinapinic acid, sinapic acid choline ester etc. in the Semen Brassicae campestris polyphenol, must from polyphenol, separate, the present invention utilizes dedicated ion exchange resin to realize this point quickly and easily.The 2nd, the extraction agent that the present invention uses belongs to neutral calcium salt and analogue thereof, and its principle and prior art are had any different in itself, and its effect can increase the stripping quantity of polyphenol.And in the concentration range of selecting, precipitated phytic acid, polysaccharide and the protein substance that in task of the present invention, does not need and need later on to extract, very favourable to follow-up method.Because utilize the difference of principle, calcium salt used herein is more much lower than the concentration of prior art, has avoided post precipitation to bring up again get loaded down with trivial details.The present invention also goes for the extraction of other polyphenol.
Positively effect of the present invention is:
1) compared with prior art, extraction agent of the present invention and extracting method have not only increased the yield of plant polyphenol, but also have reduced the loss of other utilizable materials.
2) polyphenol yield of the present invention is higher: according to surveying and determination, in pure polyphenol, the yield of extracting polyphenol from rapeseed cake dregs reaches 1.7-2.3%, and the yield of extracting polyphenol from Semen Brassicae campestris kind skin reaches 0.1-0.9%.
3) purity of the refining polyphenol of the present invention's extraction reaches 40%-70%; Polyphenol fraction purity reaches more than 98%.
4): content≤5% of sinapinic acid, sinapic acid choline ester in the refining polyphenol; The content of sinapinic acid, sinapic acid choline ester≤0.5% in the polyphenol fraction
5) production method of the present invention is pollution-free substantially to environment.
Description of drawings
Fig. 1 is a method flow 1 of the present invention.
Fig. 2 is a method flow 2 of the present invention.
Embodiment
Embodiment 1: extract polyphenol from rapeseed cake dregs
The proportioning of extraction agent: 810 liters of the ethanol of volume percent 95%, 990 liters of domestic waters.14.1 kilograms in magnesium chloride adds stirring and dissolving in the entry with magnesium chloride earlier, and transferring pH is 5, then with 95% ethanol mixing.
The double centner rapeseed cake dregs is pulverized, crossed 40 mesh sieves, drop into extraction vessel, add 1800 liters of extraction agents, adjust the temperature to 45 ℃, stirring and leaching 2 hours is used the plate-and-frame filter press press filtration, and gained filtrate is filtered with fine filting machine again, removes the above impurity of 200 orders.
The filtrate of smart filter uses vacuum decker immediately under 45 ℃, and vacuum tightness is not less than 0.85 normal atmosphere under and concentrates, and steaming must polyphenol concentrated solution 1 behind the ethanol.
The polyphenol concentrated solution is flow through cation exchange resin column, anion-exchange resin column successively with 1.5 cubic metres/hour flow velocity, the macroporous resin column group of flowing through then and contacting, when the volume of the polyphenol concentrated solution that flows through when a macroporous resin column reaches 10 times of resin column bed volume, wash resin column with domestic water with 0.75 cubic metre/hour flow velocity, wash the post water and be the resin column bed volume 1.5 times.After having washed, with the methyl alcohol of the volume percent 45% flow velocity desorb polyphenol with 1.5 cubic metres/hour, it is 3.5 times of resin column column volume that desorb spends the methanol solution volume.Collect methanol solution and use vacuum decker under 50 ℃, vacuum tightness is not less than under 0.85 normal atmosphere and concentrates, and gets polyphenol concentrated solution 2.With polyphenol concentrated solution 2 spraying dryings, get 5.2 kilograms of polyphenol products, its purity is 46.1%.
Embodiment 2: extract polyphenol from rapeseed cake dregs
The proportioning of extraction agent: 800 liters of 70% ethanolic solns, add 9.6 kilograms of zinc chloride, stir and make its dissolving, adjust pH to 2.
The double centner rapeseed cake dregs is pulverized, crossed 60 mesh sieves, drop into extraction vessel, add 800 liters of extraction agents, adjust the temperature to 55 ℃, stirring and leaching 45 minutes is used the plate-and-frame filter press press filtration, and filter residue extracts 2 times under the same conditions again.Merging filtrate filters with fine filting machine, removes the above impurity of 200 orders.
The filtrate of smart filter uses vacuum decker immediately under 50 ℃, and vacuum tightness is not less than 0.85 normal atmosphere under and concentrates, and steaming must polyphenol concentrated solution 1 behind the ethanol.
The polyphenol concentrated solution flows through cation exchange resin column, anion-exchange resin column successively with 1.5 cubic metres/hour flow velocity, the macroporous resin column group of flowing through then and contacting, when the volume of the polyphenol concentrated solution that flows through when a macroporous resin column reaches 10 times of resin column bed volume, wash resin column with domestic water with 0.75 cubic metre/hour flow velocity, wash the post water and be the resin column bed volume 1.5 times.After having washed, with the ethanol of the volume percent 75% flow velocity desorb polyphenol with 1.5 cubic metres/hour, it is 4 times of resin column column volume that desorb spends the ethanol volume.Collect ethanol liquid and use vacuum decker under 50 ℃, vacuum tightness is not less than under 0.85 normal atmosphere and concentrates, and gets polyphenol concentrated solution 2.Polyphenol concentrated solution 2 is added on the sephadex column, and the volume of the polyphenol concentrated solution 2 of adding is 20% of a dextrane gel column volume, with the washing post of 1.2 times of dextrane gel column volumes, uses 75% alcohol desorption polyphenol more earlier.Collect stripping liquid, under 50 ℃, vacuum tightness is not less than 0.85 normal atmosphere under and concentrates with vacuum decker, and steaming must polyphenol concentrated solution 3 behind the ethanol.With 3 lyophilizes of polyphenol concentrated solution, get 2.3 kilograms of polyphenol products, its purity is 98.2%.
Embodiment 3: extract polyphenol from rapeseed cake dregs
The proportioning of extraction agent: earlier 2.4 kilo sulfuric acid calcium are joined in 80% 1200 liters the ethanolic soln, stirring and dissolving is transferred pH to 3.5.
The double centner rapeseed cake dregs is pulverized, crossed 80 mesh sieves, drop into extraction vessel, add 1200 liters of extraction agents, adjust the temperature to 85 ℃, stirring and leaching 30 minutes is used the plate-and-frame filter press press filtration, and filter residue extracts 1 time under the same conditions again.Merging filtrate filters with fine filting machine, removes the above impurity of 200 orders.
The filtrate of smart filter uses vacuum decker immediately under 45 ℃, and vacuum tightness is not less than 0.85 normal atmosphere under and concentrates, and steaming must polyphenol concentrated solution 1 behind the ethanol.
The polyphenol concentrated solution flows through cation exchange resin column, anion-exchange resin column successively with 1.5 cubic metres/hour flow velocity, the macroporous resin column group of flowing through then and contacting, when the volume of the polyphenol concentrated solution that flows through when a macroporous resin column reaches 10 times of resin column bed volume, wash resin column with domestic water with 0.75 cubic metre/hour flow velocity, wash the post water and be the resin column bed volume 1.5 times.After having washed, with the ethanol of the volume percent 15% flow velocity desorb polyphenol with 1.5 cubic metres/hour, it is 4 times of resin column column volume that desorb spends the ethanol volume.Collect ethanol liquid and use vacuum decker under 50 ℃, vacuum tightness is not less than under 0.85 normal atmosphere and concentrates, and gets polyphenol concentrated solution 2.Polyphenol concentrated solution 2 is not less than 0.90 normal atmosphere, temperature in vacuum tightness is not higher than 60 ℃ of dryings down, get 2.25 kilograms of products, its purity is 44.2%.
Embodiment 4: extract polyphenol from rapeseed cake dregs or Semen Brassicae campestris kind skin
The proportioning of extraction agent: earlier 12.9 kilograms of calcium chloride are joined in 66.5% 1000 liters the ethanolic soln, stirring and dissolving is transferred pH to 5.
The raw material consumption: the Semen Brassicae campestris kind skin of double centner or the rapeseed cake dregs of double centner, its treatment step is shown in embodiment 1.
Embodiment 5: extract polyphenol from rapeseed cake dregs or Semen Brassicae campestris kind skin
The proportioning of extraction agent: earlier 45.2 kilograms of calcium phosphate are joined in 73% 1000 liters the ethanolic soln stirring and dissolving, adjust pH to 3.
The raw material consumption: the Semen Brassicae campestris kind skin of double centner or the rapeseed cake dregs of double centner, its treatment step is shown in embodiment 1.
Embodiment 6: extract polyphenol from rapeseed cake dregs or Semen Brassicae campestris kind skin
The proportioning of extraction agent: earlier 1.7 kilograms of calcium lactates are joined in 45% 1000 liters the ethanolic soln stirring and dissolving, adjust pH to 2.
The raw material consumption: the Semen Brassicae campestris kind skin of double centner or the rapeseed cake dregs of double centner, its treatment step is shown in embodiment 1.
Embodiment 7: extract polyphenol from rapeseed cake dregs or Semen Brassicae campestris kind skin
The proportioning of extraction agent: earlier 22.2 kilograms of nitrocalcite are joined in 85% 1000 liters the ethanolic soln stirring and dissolving, adjust pH to 4.
The raw material consumption: the Semen Brassicae campestris kind skin of double centner or the rapeseed cake dregs of double centner, its treatment step is shown in embodiment 1.
Embodiment 8: extract polyphenol from the residue kind skin after the Semen Brassicae campestris processing
The proportioning of extraction agent: earlier 29.5 kilograms of bariumchlorides are joined in 45% 1100 liters the ethanolic soln, stirring and dissolving is regulated adjust pH to 4.
The raw material consumption: the Semen Brassicae campestris kind skin of double centner or the rapeseed cake dregs of double centner, its treatment step is shown in embodiment 1.
Embodiment 9: extract polyphenol from rapeseed cake dregs or Semen Brassicae campestris kind skin
The proportioning of extraction agent: earlier 36.2 kilo sulfuric acid magnesium are joined in 55% 1200 liters the ethanolic soln stirring and dissolving, adjust pH to 4.
The raw material consumption: the Semen Brassicae campestris kind skin of double centner or the rapeseed cake dregs of double centner, its treatment step is shown in embodiment 1.
Embodiment 10: extract polyphenol from rapeseed cake dregs or Semen Brassicae campestris kind skin
The proportioning of extraction agent: earlier 40.6 kilo sulfuric acid zinc are joined in 75% 1200 liters the ethanolic soln stirring and dissolving, adjust pH to 4.5.
The raw material consumption: the Semen Brassicae campestris kind skin of double centner or the rapeseed cake dregs of double centner, its treatment step is shown in embodiment 1.
Embodiment 11: extract polyphenol from rapeseed cake dregs or Semen Brassicae campestris kind skin
The proportioning of extraction agent: earlier 23.4 kilograms of aluminum chloride are joined in 75% 1100 liters the ethanolic soln stirring and dissolving, adjust pH to 2.5.
The raw material consumption: the Semen Brassicae campestris kind skin of double centner or the rapeseed cake dregs of double centner, its treatment step is shown in embodiment 1.
Claims (7)
1, a kind of being used for from the extraction agent of rapeseed cake dregs or coleseed kind skin extraction polyphenol, it comprises following component:
Neutral calcium salt or analogue be 0.10-5.50g/100ml by weight percentage,
Ethanolic soln is 30%-85% by weight percentage,
Water is supplemented to 100,
It prepares in accordance with the following methods:
A, the preparation ethanolic soln before in advance adjust pH to 2-5,
B, described neutral calcium salt or analogue are added in the ethanolic soln.
2, extraction agent according to claim 1 is characterized in that said neutral calcium salt selects wherein a kind of from calcium sulfate, calcium chloride, calcium phosphate, calcium lactate or nitrocalcite; Described analogue is selected wherein a kind of from bariumchloride, magnesium chloride, zinc chloride, sal epsom, zinc sulfate, aluminum chloride.
3, extract the preparation method of polyphenol from rapeseed cake dregs and Semen Brassicae campestris kind skin, its feature may further comprise the steps:
1) will pulverize and degreasing after rapeseed cake dregs or Semen Brassicae campestris kind skin powder join extraction agent as claimed in claim 1, raw material is 1: 5 to 1: 15 with the ratio of extraction agent, under 45-85 ℃, handled 30 minutes-2 hours, intermittently stir extraction, obtain feed liquid 1, perhaps filter residue is extracted under the same conditions again 1-3 all over after obtain feed liquid 2, merge feed liquid 1 and 2;
2) the merging feed liquid that step 1) is obtained is removed the following impurity of 200 orders, gets filtrate 1;
3) with step 2) filtrate 1 that obtains puts vacuum concentration below 50 ℃, reclaims ethanol, obtains concentrated solution 1;
4) concentrated solution 1 that step 3) is obtained is successively crossed cation exchange resin column and anion-exchange resin column, removes the impurity in the concentrated solution 1, obtains the polyphenol solution of preliminary purification;
5) the preliminary purification polyphenol solution that step 4) is obtained is crossed the macroporous resin adsorption post, wash with water remove impurity after, with the ethanolic soln wash-out of 10%-76% percent by volume; Perhaps use the methanol solution wash-out of 20%-80% percent by volume, the polyphenol solution that obtains being further purified;
6) the polyphenol solution that is further purified that step 5) is obtained reclaims solvent at vacuum concentration below 50 ℃, obtains concentrated solution 2;
7) concentrated solution 2 dryings that step 6) obtained obtain refining polyphenol.
4, according to claim 1 or 3 described methods, its step comprises:
1) with above-mentioned steps 6) dextrane gel or polyamide column on the concentrated solution 2 that obtains, use methyl alcohol successively: water=1: 3,1: 1,3: 1; 100% methyl alcohol; Methyl alcohol: acetone=1: 1; 50% acetone soln wash-out is collected elutriant respectively;
2) with the elutriant vacuum concentration of step 1) gained, get concentrated solution 3;
3) with step 2) concentrated solution 3 dryings of gained, the polyphenol fraction.
5, method according to claim 4 is characterized in that, the methyl alcohol in the step 1) can replace with ethanol.
6, extracting method according to claim 3 is characterized in that: the refining employed macroporous resin column of purifying is the macroporous resin to the selective absorption of polyphenol from rapeseed.
7, method according to claim 3 is characterized in that: adopt lyophilize or spraying drying or vacuum-drying.
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| CNB2004100129803A CN100415697C (en) | 2004-04-06 | 2004-04-06 | Agent of extracting polyphenol from rape seed cakes or husks and its preparation |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103820218A (en) * | 2014-03-07 | 2014-05-28 | 张家界金绿油脂有限责任公司 | Method for microwave extracting rapeseed grease |
| CN103820219A (en) * | 2014-03-07 | 2014-05-28 | 张家界金绿油脂有限责任公司 | Method for extracting various active substances from rapeseed hull |
| CN104644717A (en) * | 2015-01-09 | 2015-05-27 | 河南省中医药研究院 | Extraction technology for extracting hypotensive substances from rapeseed meal |
| CN105038976A (en) * | 2015-09-22 | 2015-11-11 | 罗春燕 | Method for making Chinese prickly ash seed oil through chemical extraction |
| CN107445807A (en) * | 2017-08-25 | 2017-12-08 | 成都欣捷高新技术开发股份有限公司 | A kind of method for removing foreign pigment in phloroglucin synthesis technique |
| CN108354962A (en) * | 2018-04-26 | 2018-08-03 | 江苏大学 | A method of based on nitrogen protection and ultrasound assisted extraction polyphenol from rapeseed |
| CN112998181A (en) * | 2021-03-18 | 2021-06-22 | 中国科学院近代物理研究所 | High-activity sweet sorghum polyphenol and preparation method and application thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1070088A (en) * | 1991-09-09 | 1993-03-24 | 湖南轻工研究所 | The method of compound extracting and detoxicating of rapeseed cake |
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2004
- 2004-04-06 CN CNB2004100129803A patent/CN100415697C/en not_active Expired - Fee Related
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103820218A (en) * | 2014-03-07 | 2014-05-28 | 张家界金绿油脂有限责任公司 | Method for microwave extracting rapeseed grease |
| CN103820219A (en) * | 2014-03-07 | 2014-05-28 | 张家界金绿油脂有限责任公司 | Method for extracting various active substances from rapeseed hull |
| CN103820219B (en) * | 2014-03-07 | 2015-03-11 | 张家界金绿油脂有限责任公司 | Method for extracting various active substances from rapeseed hull |
| CN104644717A (en) * | 2015-01-09 | 2015-05-27 | 河南省中医药研究院 | Extraction technology for extracting hypotensive substances from rapeseed meal |
| CN105038976A (en) * | 2015-09-22 | 2015-11-11 | 罗春燕 | Method for making Chinese prickly ash seed oil through chemical extraction |
| CN107445807A (en) * | 2017-08-25 | 2017-12-08 | 成都欣捷高新技术开发股份有限公司 | A kind of method for removing foreign pigment in phloroglucin synthesis technique |
| CN107445807B (en) * | 2017-08-25 | 2020-04-17 | 成都欣捷高新技术开发股份有限公司 | Method for removing colored impurities in phloroglucinol synthesis process |
| CN108354962A (en) * | 2018-04-26 | 2018-08-03 | 江苏大学 | A method of based on nitrogen protection and ultrasound assisted extraction polyphenol from rapeseed |
| CN112998181A (en) * | 2021-03-18 | 2021-06-22 | 中国科学院近代物理研究所 | High-activity sweet sorghum polyphenol and preparation method and application thereof |
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| Publication number | Publication date |
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| CN100415697C (en) | 2008-09-03 |
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