CN100393710C - Method for extracting soybean isoflavone from soybean whey liquid - Google Patents
Method for extracting soybean isoflavone from soybean whey liquid Download PDFInfo
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- CN100393710C CN100393710C CNB2005101011220A CN200510101122A CN100393710C CN 100393710 C CN100393710 C CN 100393710C CN B2005101011220 A CNB2005101011220 A CN B2005101011220A CN 200510101122 A CN200510101122 A CN 200510101122A CN 100393710 C CN100393710 C CN 100393710C
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- 235000010469 Glycine max Nutrition 0.000 title claims abstract description 69
- 244000068988 Glycine max Species 0.000 title claims abstract description 69
- CJWQYWQDLBZGPD-UHFFFAOYSA-N isoflavone Natural products C1=C(OC)C(OC)=CC(OC)=C1C1=COC2=C(C=CC(C)(C)O3)C3=C(OC)C=C2C1=O CJWQYWQDLBZGPD-UHFFFAOYSA-N 0.000 title claims abstract description 40
- 235000008696 isoflavones Nutrition 0.000 title claims abstract description 40
- 108010046377 Whey Proteins Proteins 0.000 title claims abstract description 34
- 102000007544 Whey Proteins Human genes 0.000 title claims abstract description 34
- 239000005862 Whey Substances 0.000 title claims abstract description 32
- 238000000034 method Methods 0.000 title claims abstract description 22
- 239000007788 liquid Substances 0.000 title claims description 51
- GOMNOOKGLZYEJT-UHFFFAOYSA-N isoflavone Chemical compound C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC=C1 GOMNOOKGLZYEJT-UHFFFAOYSA-N 0.000 title abstract description 6
- 238000000108 ultra-filtration Methods 0.000 claims abstract description 15
- 238000000605 extraction Methods 0.000 claims abstract description 11
- 238000004821 distillation Methods 0.000 claims abstract description 6
- 239000012528 membrane Substances 0.000 claims abstract description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 57
- 150000002515 isoflavone derivatives Chemical class 0.000 claims description 34
- 238000001728 nano-filtration Methods 0.000 claims description 23
- 238000001471 micro-filtration Methods 0.000 claims description 8
- 238000010612 desalination reaction Methods 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 6
- 239000012141 concentrate Substances 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- 238000002203 pretreatment Methods 0.000 claims description 4
- 230000002787 reinforcement Effects 0.000 claims description 4
- 238000005507 spraying Methods 0.000 claims description 4
- 230000001954 sterilising effect Effects 0.000 claims description 4
- 238000004659 sterilization and disinfection Methods 0.000 claims description 4
- 239000004695 Polyether sulfone Substances 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 229920002492 poly(sulfone) Polymers 0.000 claims description 2
- 229920002647 polyamide Polymers 0.000 claims description 2
- 229920006393 polyether sulfone Polymers 0.000 claims description 2
- 238000005096 rolling process Methods 0.000 claims description 2
- 238000005516 engineering process Methods 0.000 abstract description 6
- 108010073771 Soybean Proteins Proteins 0.000 abstract description 5
- 238000001914 filtration Methods 0.000 abstract description 5
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 230000008901 benefit Effects 0.000 abstract description 3
- 238000000926 separation method Methods 0.000 abstract description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 2
- 229910052708 sodium Inorganic materials 0.000 abstract 2
- 239000011734 sodium Substances 0.000 abstract 2
- 239000006227 byproduct Substances 0.000 abstract 1
- 238000011010 flushing procedure Methods 0.000 abstract 1
- 238000009776 industrial production Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 108090000623 proteins and genes Proteins 0.000 abstract 1
- 102000004169 proteins and genes Human genes 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229940001941 soy protein Drugs 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 235000019710 soybean protein Nutrition 0.000 description 4
- 235000019764 Soybean Meal Nutrition 0.000 description 3
- 238000001179 sorption measurement Methods 0.000 description 3
- 239000004455 soybean meal Substances 0.000 description 3
- 239000002351 wastewater Substances 0.000 description 3
- 208000001132 Osteoporosis Diseases 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 229920001542 oligosaccharide Polymers 0.000 description 2
- 150000002482 oligosaccharides Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000001223 reverse osmosis Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- 238000002798 spectrophotometry method Methods 0.000 description 2
- 235000021119 whey protein Nutrition 0.000 description 2
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 229930187719 Soyasaponin Natural products 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- 238000011033 desalting Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 238000000909 electrodialysis Methods 0.000 description 1
- 238000007701 flash-distillation Methods 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 210000001161 mammalian embryo Anatomy 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 229930000044 secondary metabolite Natural products 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
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Abstract
The present invention relates to a method for extracting soybean isoflavone from soybean whey liquor. A byproduct in the production process of soy protein separation, namely soybean whey liquor, is processed by the steps: first, separating proteins by air flushing reinforced dynamic ultrafiltration; then, concentrating the whey liquor by sodium filtration and eliminating salt; afterwards, extracting the concentrated liquor after sodium filtration; finally, concentrating extract liquor by using a reduced pressure distillation method to obtain a soybean isoflavone product with purity of more than 40%. The method of the present invention adopts a membrane technology and an extraction technology and has the advantages of easy operation and high economic benefit; the present invention is suitable for industrial production.
Description
[technical field]
The present invention relates to soybean deep processing and waste water reclaiming technical field, particularly from soybean whey liquid, extract the method for soybean isoflavones.
[background technology]
Soybean isoflavones is the secondary metabolite that forms in the soybeans they grow process, it is physiologically active substance main in the soybean, have faint female hormone character and anti-oxidant activity, and be a kind of natural anticancer compound, have significant curative effect for diseases such as women breast cancer, climacteric syndrome, middle aged and aged women osteoporosises, and have fine health-care effect at aspects such as anti-curing cancers, osteoporosis, cardiovascular disordeies.At present, it is all having purposes very widely aspect protective foods and the drug manufacture, and demand is very big.
Occurring in nature isoflavones resource is very limited, and soybean is unique isoflavones and content significant food resource on trophology of containing.The content range of soybean isoflavones is about the dried soybean of 0.5～7.0mg/g in the soybean, mainly be distributed in the cotyledon and plumular axis of soybean seeds, be about 0.1～0.3% in the cotyledon, institute's isoflavone-containing kind is more and concentration is higher in the plumular axis, being about 1%～2%, is the main raw material of producing soybean isoflavones at present.The disclosed method of extracting soybean isoflavones from soybean plumular axis has CN1375492A (patent publication No., down together), CN1422856A, CN1327983A, CN1372836A etc.But because embryo only accounts for 2% of seed total mass, although therefore dense, proportion is (10%～20%) seldom, and the soybean isoflavones of the overwhelming majority is present in the soybean cotyledon.Soybean cotyledon becomes soybean meal through the degreasing post-treatment, so can extract more soybean isoflavones from soybean meal, disclosed as patent CN1284503A (patent publication No., down together), CN 1448394A, CN1349987, CN1422855, CN1422856A, CN1456557A etc. all is the method for extracting soybean isoflavones from the skimmed soy beans dregs of beans.
Defatted soybean meal is a raw material of producing soybean protein isolate, in the production process of soybean protein isolate, can produce a large amount of soybean whey liquids, and the soybean isoflavones in the soybean cotyledon mainly just is present in the soybean whey liquid.China normally handles soybean whey liquid at present with the form of waste water, not only intractability is big, and has wasted the multiple useful resources that is contained in the waste water.So it is the problem of an environment and economic benefit doulbe-sides' victory that the soybean isoflavones in the soybean whey liquid is extracted.Patent CN1590385A and CN1552703A provide the method that adopts soybean isoflavones in the macroporous resin adsorption soybean whey liquid, to directly adsorbing through pretreated soybean whey liquids of measure such as micro-filtrations, extract soybean isoflavones wherein.Adopt cross-flow ultrafiltration separation whey-protein wherein in this method, be easy to cause film to stop up; Handled soybean whey liquid is without effective concentration, and the water yield is bigger, and isoflavones concentration is lower in the whey liquid; And when adopting the macroporous resin adsorption isoflavones, have that operation is intermittent, solvent load is more, have the problem of aspect such as residual, industrial implementation is complicated.CN1315322A discloses a kind of method of extracting soybean isoflavones from soybean whey, wherein adopt the high temperature flash distillation that whey liquid is concentrated, adopt electrodialysis and Zeo-karb desalination, adopt macroporous adsorbent resin that isoflavones and Soyasaponin are adsorbed.But because the whey liquid salinity generally is lower than 1.0%, so adopt the electrodialytic desalting expense higher; And adopt macroporous resin adsorption inevitable exist also that operation is intermittent, solvent load is more, it is residual to have and industrial implementation than the problem of aspects such as complexity.
[summary of the invention]
Purpose of the present invention just provides a kind of novel method of extracting soybean isoflavones from soybean whey liquid, adopts technology such as membrane sepn and organic solvent extraction in the method, and is easy and simple to handle, is easy to realize industrialization.
This method adopts gas to dash the whey-protein of strengthening in the dynamic ultra-filtration and separation soybean whey liquid, has greatly improved the contamination resistance of ultra-filtration membrane; After adopting nanofiltration to concentrate to the whey liquid after the uf processing, further adopt the organic solvent extraction soybean isoflavones, technology is simple, has good operability.The soybean isoflavones purity of being extracted is more than 40%.
The concrete implementation step of the inventive method is described below:
(1) pre-treatment:
A) the pH value of adjusting soybean whey liquid is 4.5～7.0, and carries out high-temperature sterilization (85 ℃～115 ℃) and handle; Carry out micro-strainer and filter, obtain micro-filtration and see through liquid A2;
B) adopt gas to dash the dynamic ultra-filtration technique of reinforcement micro-filtration is carried out filtration treatment through liquid A1, cycles of concentration gets ultrafiltration and concentration liquid B1 and ultrafiltration and sees through liquid B2 more than 7.
(2) nanofiltration and desalination
At working pressure is under the condition of 0.35～2.0MPa, ultrafiltration is seen through liquid B2 carry out the nanofiltration processing, and cycles of concentration is 5～20, and adds pure water and carry out desalination, repeats to filter 1～5 time, gets nanofiltration concentrated solution C1 and nanofiltration and sees through liquid C2; The material of used nanofiltration membrane can be polysulfones, polyethersulfone or polyamide-based, and kit form can be board-like, rolling, tubular type or tubular fibre form, and molecular weight cut-off is 200～1000 dalton.
(3) extraction
Nanofiltration concentrated solution C1 mixed with ethyl acetate carry out extracting operation, the volume ratio of nanofiltration concentrated solution and ethyl acetate is 0.3～10: 1, tells upper strata ethyl acetate phase D1 and lower aqueous solution D2 mutually behind contact 5min～500min;
(4) aftertreatment
A) be that 50 ℃～70 ℃, operation negative pressure are under 0.08MPa～0.095MPa ethyl acetate phase D1 to be carried out underpressure distillation in Heating temperature, reclaim ethyl acetate, obtain soybean isoflavones concentrated solution E1;
B) soybean isoflavones concentrated solution E1 is carried out spraying drying, obtain soybean isoflavones product P 1;
C) the lower aqueous solution phase D2 to extraction carries out the underpressure distillation processing, reclaims ethyl acetate wherein.
[description of drawings]
Fig. 1 is the process flow sheet of the inventive method
[embodiment]
The present invention is further illustrated below in conjunction with accompanying drawing and specific embodiment.
Embodiment one:
Step 1): the pre-treatment of soybean whey liquid
A) soybean whey liquid directly comes from the soybean protein isolate production line, and wherein isoflavone content is 0.11mg/mL, to 105 ℃ of sterilizations of its heating, keeps the pH value of whey liquid 4.5, enters receiver then, staticly settles more than the 60min;
B) adopt micro-strainer to filter to above-mentioned whey liquid, concentrated solution A1 is back to receiver, sees through liquid A2 and enters ultra-fine filter;
C) adopt gas to dash the dynamic ultra-fine filter of reinforcement micro-filtration is carried out filtration treatment through liquid A2, concentrated solution B1 is back to receiver, sees through liquid B2 and enters nanofiltration device;
Step 2): the soybean whey liquid nanofiltration concentrates and desalination
Adjust the pH value to 7.0 that ultrafiltration sees through liquid B2, get wherein 20L ultrafiltration and see through liquid, inject the nanofiltration device and carry out the nanofiltration processing, under the pressure of 0.8MPa, be concentrated to 2L; Add pure water and repeat to filter to 20L, so cyclical operation is 2 times, and gained can discharge through liquid C2 or produce pure water to be used for the technology reuse with reverse-osmosis treated, and gained 2L concentrated solution C1 then is used for continuing to extract soybean isoflavones;
Step 3): extraction
C1 mixes with isopyknic ethyl acetate with 2L nanofiltration concentrated solution, and upper strata ethyl acetate phase D1 and lower aqueous solution D2 is mutually told in contact behind the 120min;
Step 4): aftertreatment
A) Heating temperature be 50 ℃, operation negative pressure be under the 0.08MPa to extraction on phase D1 carry out concentrating under reduced pressure, reclaim ethyl acetate, obtain concentrated solution E1;
B) concentrated solution E1 is carried out spraying drying, obtain soybean isoflavones product 3.51g, this product is adopted the ultraviolet spectrophotometry analysis, purity is 45.6%, and the yield of soybean isoflavones is 72.7%;
C) be to carry out concentrating under reduced pressure under the 0.075MPa to handle to the solution phase D2 of lower floor of extraction at 50 ℃, operation negative pressure, reclaim ethyl acetate wherein, remaining solution can be used to produce soybean oligosaccharide mutually.
Embodiment two:
Step 1): pre-treatment
1. soybean whey liquid directly comes from the soybean protein isolate production line, and wherein isoflavone content is 0.126mg/mL, to 115 ℃ of sterilizations of its heating, adjusts the pH value to 7.0 of whey liquid, enters receiver then, staticly settles more than the 60min;
2. adopt micro-strainer to filter to above-mentioned whey liquid, concentrated solution A1 is back to receiver, sees through liquid A2 and enters ultra-fine filter;
3. adopt gas to dash the dynamic ultra-fine filter of reinforcement micro-filtration is carried out filtration treatment through liquid A2, concentrated solution B1 is back to receiver, sees through liquid B2 and enters nanofiltration device;
Step 2): nanofiltration concentrates and desalination
Get wherein 30L ultrafiltration and see through liquid B2, under the pressure of 1.2MPa, be concentrated to 2L by nanofiltration, adding pure water again repeats to filter to 20L, so cyclical operation is 3 times, must see through that liquid C2 can discharge or produce pure water to be used for the technology reuse with reverse-osmosis treated, gained 2L concentrated solution C1 then is used for continuing to extract soybean isoflavones;
Step 3): extraction
Nanofiltration concentrated solution component C 1 is mixed with the ethyl acetate of 1.2 times of volumes, and upper strata ethyl acetate phase D1 and lower aqueous solution D2 is mutually told in contact behind the 300min;
Step 4): aftertreatment
A) Heating temperature be 70 ℃, operation negative pressure be under the 0.095MPa to extraction on phase D1 carry out concentrating under reduced pressure, reclaim ethyl acetate, obtain concentrated solution E1;
B) concentrated solution E1 is carried out spraying drying, obtain soybean isoflavones product 6.51g, adopt the ultraviolet spectrophotometry analysis, purity is 43.3%, and the yield of soybean isoflavones is 74.6%;
C) be to carry out underpressure distillation under the 0.075MPa to handle to the lower aqueous solution phase D2 of extraction at 50 ℃, operation negative pressure, reclaim ethyl acetate wherein, remaining solution can be used for producing soybean oligosaccharide.
More than be preferred forms of the present invention, according to content disclosed by the invention, some identical, replacement schemes that those of ordinary skill in the art can expect apparently all should fall into protection scope of the present invention.
Claims (2)
1. a method of extracting soybean isoflavones from soybean whey liquid is characterized in that, may further comprise the steps:
(1) pre-treatment:
A) the pH value of adjusting soybean whey liquid is 4.5～7.0, and carries out high-temperature sterilization and handle, and carries out micro-filtration then, obtains micro-filtration and sees through liquid A2;
B) adopt gas to dash the dynamic ultra-filtration technique of reinforcement micro-filtration is carried out uf processing through liquid A2, get ultrafiltration and concentration liquid B1 and ultrafiltration and see through liquid B2;
(2) nanofiltration concentrates and desalination:
Under the condition of working pressure 0.35～2.0MPa, ultrafiltration is seen through liquid B2 carry out the nanofiltration concentration, and desalination, get nanofiltration concentrated solution C1 and nanofiltration and see through liquid C2;
(3) extraction:
Is 0.3～10: 1 mixed with nanofiltration concentrated solution C1 and ethyl acetate with volume ratio, through the abundant contact of 5min～500min, tells upper strata ethyl acetate phase D1 and lower floor solution D2 mutually;
(4) aftertreatment:
A) be that 50～70 ℃, operation negative pressure are under the condition of 0.08～0.095MPa ethyl acetate phase D1 to be carried out underpressure distillation in Heating temperature, reclaim ethyl acetate, obtain concentrated solution E1 simultaneously;
B) concentrated solution E1 is carried out spraying drying, obtain soybean isoflavones product P 1;
C) the solution phase D2 of lower floor to extraction carries out the underpressure distillation processing, reclaims ethyl acetate.
2. the method for from soybean whey liquid, extracting soybean isoflavones according to claim 1, it is characterized in that, in the described step (2), the material of nanofiltration membrane is polysulfones or polyethersulfone or polyamide-based, kit form is board-like or rolling or tubular type or tubular fibre form, and molecular weight cut-off is 200～1000 dalton.
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| Application Number | Priority Date | Filing Date | Title |
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| CNB2005101011220A CN100393710C (en) | 2005-11-03 | 2005-11-03 | Method for extracting soybean isoflavone from soybean whey liquid |
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| CNB2005101011220A CN100393710C (en) | 2005-11-03 | 2005-11-03 | Method for extracting soybean isoflavone from soybean whey liquid |
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| CN100393710C true CN100393710C (en) | 2008-06-11 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103719533A (en) * | 2013-12-27 | 2014-04-16 | 山东禹王生态食业有限公司 | Production method of high-calcium whey protein |
| CN110128387B (en) * | 2019-06-17 | 2021-05-11 | 山东师范大学 | Method for extracting soybean isoflavone aglycone |
| CN110204523B (en) * | 2019-06-17 | 2021-05-11 | 山东师范大学 | Preparation method of pure glycitein |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1552703A (en) * | 2003-06-04 | 2004-12-08 | 清华同方股份有限公司 | Extraction of soya isoflavone from waste soybean serum |
| CN1590385A (en) * | 2003-09-05 | 2005-03-09 | 清华同方股份有限公司 | Method of extracting soyabean isoflavone and soya bean saponin for soya bean whey waste water |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1552703A (en) * | 2003-06-04 | 2004-12-08 | 清华同方股份有限公司 | Extraction of soya isoflavone from waste soybean serum |
| CN1590385A (en) * | 2003-09-05 | 2005-03-09 | 清华同方股份有限公司 | Method of extracting soyabean isoflavone and soya bean saponin for soya bean whey waste water |
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