CN106946662A - The method that hydroxytyrosol is extracted from processing olive oil waste water - Google Patents
The method that hydroxytyrosol is extracted from processing olive oil waste water Download PDFInfo
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- CN106946662A CN106946662A CN201710195465.0A CN201710195465A CN106946662A CN 106946662 A CN106946662 A CN 106946662A CN 201710195465 A CN201710195465 A CN 201710195465A CN 106946662 A CN106946662 A CN 106946662A
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- hydroxytyrosol
- olive oil
- waste water
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/005—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by obtaining phenols from products, waste products or side-products of processes, not directed to the production of phenols, by conversion or working-up
- C07C37/009—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by obtaining phenols from products, waste products or side-products of processes, not directed to the production of phenols, by conversion or working-up from waste water
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/685—Processes comprising at least two steps in series
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/82—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by solid-liquid treatment; by chemisorption
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Environmental & Geological Engineering (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
Abstract
The invention belongs to technical field of bioengineering, the method that hydroxytyrosol is extracted in more particularly to a kind of olive oil waste water from processing, including following preparation process：1) waste water for taking processing olive oil to produce, ultrafiltration is carried out with the milipore filter of 20000~40000 molecular weight of retention, then carries out micro-filtration, obtains filtrate；2) filtrate enters macroporous adsorbent resin column chromatography, and the mixed solution with ethanol solution and ethyl acetate is that eluant, eluent is eluted, and collects eluent；3) eluent is crossed into the hollow-fibre membrane that molecular cut off is 16~280,000, obtains concentrate；4) dry, obtain hydroxytyrosol.Hydroxytyrosol purity is extracted from processing olive oil waste water using the inventive method and recovery rate is high, bioactivity can be also kept in digestive system.
Description
Technical field
The invention belongs to technical field of bioengineering, hydroxytyrosol is extracted in more particularly to a kind of olive oil waste water from processing
Method.
Background technology
Olive oil has " liquid golden " in the world, " oil of beauty ", the good reputation such as " Mediterranean sweet dew ".In western countries,
Either nutritionist, physician, food scientific research personnel, or consumer generally acknowledge that olive oil is the oil of health.It is many
Advancing of disease is directed to substantial amounts of fat diet, and the phenols that some laboratory researches are already indicated above in olive oil is same with other
Race's Substance P hydrolysis produces the small phenolic component with strong active anticancer.Aldehydes matter has very many biological actions, particularly
Hydroxytyrosol has the effect of effective anti-oxidation protection to low-density lipoprotein (LDL), suppresses platelet aggregation.Hydroxytyrosol is
A kind of natural polyphenol class compound, with a variety of biological and pharmacological activity, applied to cosmetics health products, can effectively strengthen skin
Skin is elastic and moist, the effect of having smoothing wrinkle anti-aging；Contribute to absorption of the human body to mineral matter, without replenishing the calcium, absorb, protect naturally
Bone density is held, skeleton bulking is reduced, while improving internal system function, enhanced metabolism, promotes wound healing, body is eliminated
Interior free radical, recovers the health status of viscera organ, prevents cerebral senility, anti-aging retains youthful vitality；Lung can be prevented and treated
Cancer, breast cancer, the cancer of the uterus, prostate cancer etc., promote the cancer later stage to recover and improve chemotherapy effect；Preventing and treating is more caused by smoking
Plant lesion；There is special effect to the prevention and treatment of artery sclerosis, hypertension, heart disease, cerebral hemorrhage etc., better than similar drug；In addition,
Hydroxytyrosol can be used for agricultural as natural antibacterial, antiviral and fungicidal products and insect pest controls purposes.Therefore with huge
Big medical function prospect.
In the waste water that hydroxytyrosol can be produced from olive oil and processing olive oil.And how to be produced from processing olive oil
The hydroxytyrosol that raw waste water extracts high-purity is the emphasis studied at present.
The content of the invention
The technical problems to be solved by the invention are to provide the method that hydroxytyrosol is extracted from processing olive oil waste water, should
The hydroxytyrosol that method is prepared has higher purity, and realization is turned waste into wealth.
To achieve the above object, technical scheme to be solved by this invention is：
The present invention provides the method that hydroxytyrosol is extracted from processing olive oil waste water, including following preparation process：
1) waste water for taking processing olive oil to produce, ultrafiltration is carried out with the milipore filter of 20000~40000 molecular weight of retention, then
Micro-filtration is carried out, filtrate is obtained；
2) filtrate enters macroporous adsorbent resin column chromatography, and the mixed solution with ethanol solution and ethyl acetate is that eluant, eluent is carried out
Elution, collects eluent；
3) eluent is crossed into the hollow-fibre membrane that molecular cut off is 16~280,000, obtains concentrate；
4) dry, obtain hydroxytyrosol.
Step 1 of the present invention) in, the membrane aperture that micro-filtration is used is 0.02~0.06 μm.It can be removed very by micro-filtration
Many sediments and harmful substance, are conducive to the alcoholization of hydroxytyrosol.
Step 2 of the present invention) in, the volume ratio of ethanol solution and ethyl acetate is 6~10:1.Such solvent is matched somebody with somebody
Than being conducive to improving the recovery rate and purity of hydroxytyrosol, the hydroxytyrosol in processing olive oil waste water can be extracted to greatest extent.
Step 2 of the present invention) in, the volumetric concentration of ethanol solution is 40%~60%.Volumetric concentration is adapted to, and improves hydroxyl
The solubility of base tyrosol.
Step 2 of the present invention) in, the consumption of mixed solution is 6~8 times of resin bed volume.The consumption of eluant, eluent
Suitably, while hydroxytyrosol purity is ensured, effectively prevent that resource from abusing.
Step 3 of the present invention) in, eluent crosses the hollow-fibre membrane that molecular cut off is 200,000, can be at utmost
Ground goes the removal of impurity and pigment, to ensure finished product purity and color and luster, and the purity of hydroxytyrosol is improved to greatest extent.
Step 4 of the present invention) in, vacuum freeze drying.Be conducive to improving the biology of hydroxytyrosol using freeze-drying
Activity.
Compared with prior art, the inventive method preparation technology is simple, manufacturing cycle can be greatly shortened, in macroporous absorption
Resin carries out separation and carries out ultrafiltration and microfiltration processing before purification, and hollow-fibre membrane again, can significantly improve purity, and carry afterwards
Take gentle, the bioactivity of hydroxytyrosol in can effectively keeping.The hydroxytyrosol prepared by this quadrat method is in digestion
Not degradable in system, its molecule still keeps activated state, can still play original activity, can significantly extend it to disease
Action effect, significantly improve the health-care efficacies such as its anti-oxidant, anticancer, anti-cancer, anti-aging.
Embodiment
The invention will be further described with reference to embodiments, but the invention is not limited in these embodiments.
Embodiment 1
The method that hydroxytyrosol is extracted from processing olive oil waste water, including following preparation process：
1) waste water for taking processing olive oil to produce, carries out ultrafiltration, the film reused with the milipore filter of 30000 molecular weight of retention
Aperture is 0.02 μm of progress micro-filtration, obtains filtrate；
2) filtrate enters macroporous adsorbent resin column chromatography, is 10 with volume ratio:Ethanol solution and second of 1 volumetric concentration for 40%
The mixed solution of acetoacetic ester is eluted for eluant, eluent, collects eluent, the consumption of the mixed solution is resin bed volume
6 times；
3) eluent is crossed into the hollow-fibre membrane that molecular cut off is 160,000, obtains concentrate；
4) vacuum freeze drying, obtains hydroxytyrosol.
Detected through HPLC, the purity for obtaining hydroxytyrosol is 96.5%.It is computed, recovery rate is 93.2%.
Embodiment 2
The method that hydroxytyrosol is extracted from processing olive oil waste water, including following preparation process：
1) waste water for taking processing olive oil to produce, carries out ultrafiltration, the film reused with the milipore filter of 40000 molecular weight of retention
Aperture is 0.03 μm of progress micro-filtration, obtains filtrate；
2) filtrate enters macroporous adsorbent resin column chromatography, is 9 with volume ratio:Ethanol solution and second of 1 volumetric concentration for 45%
The mixed solution of acetoacetic ester is eluted for eluant, eluent, collects eluent, the consumption of the mixed solution is resin bed volume
7 times；
3) eluent is crossed into the hollow-fibre membrane that molecular cut off is 190,000, obtains concentrate；
4) vacuum freeze drying, obtains hydroxytyrosol.
Detected through HPLC, the purity for obtaining hydroxytyrosol is 96.6%.It is computed, recovery rate is 90.2%.
Embodiment 3
The method that hydroxytyrosol is extracted from processing olive oil waste water, including following preparation process：
1) waste water for taking processing olive oil to produce, carries out ultrafiltration, the film reused with the milipore filter of 30000 molecular weight of retention
Aperture is 0.04 μm of progress micro-filtration, obtains filtrate；
2) filtrate enters macroporous adsorbent resin column chromatography, is 8 with volume ratio:Ethanol solution and second of 1 volumetric concentration for 50%
The mixed solution of acetoacetic ester is eluted for eluant, eluent, collects eluent, the consumption of the mixed solution is resin bed volume
8 times；
3) eluent is crossed into the hollow-fibre membrane that molecular cut off is 280,000, obtains concentrate；
4) vacuum freeze drying, obtains hydroxytyrosol.
Detected through HPLC, the purity for obtaining hydroxytyrosol is 96.5%.It is computed, recovery rate is 90.2%.
Embodiment 4
The method that hydroxytyrosol is extracted from processing olive oil waste water, including following preparation process：
1) waste water for taking processing olive oil to produce, ultrafiltration is carried out with the milipore filter of 20000~40000 molecular weight of retention, then
The membrane aperture used is 0.05 μm of progress micro-filtration, obtains filtrate；
2) filtrate enters macroporous adsorbent resin column chromatography, is 7 with volume ratio:Ethanol solution and second of 1 volumetric concentration for 55%
The mixed solution of acetoacetic ester is eluted for eluant, eluent, collects eluent, the consumption of the mixed solution is resin bed volume
7 times；
3) eluent is crossed into the hollow-fibre membrane that molecular cut off is 250,000, obtains concentrate；
4) vacuum freeze drying, obtains hydroxytyrosol.
Detected through HPLC, the purity for obtaining hydroxytyrosol is 96.5%.It is computed, recovery rate is 91.3%.
Embodiment 5
The method that hydroxytyrosol is extracted from processing olive oil waste water, including following preparation process：
1) waste water for taking processing olive oil to produce, carries out ultrafiltration, the film reused with the milipore filter of 20000 molecular weight of retention
Aperture is 0.06 μm of progress micro-filtration, obtains filtrate；
2) filtrate enters macroporous adsorbent resin column chromatography, is 6 with volume ratio:Ethanol solution and second of 1 volumetric concentration for 60%
The mixed solution of acetoacetic ester is eluted for eluant, eluent, collects eluent, the consumption of the mixed solution is resin bed volume
6 times；
3) eluent is crossed into the hollow-fibre membrane that molecular cut off is 200,000, obtains concentrate；
4) vacuum freeze drying, obtains hydroxytyrosol.
Detected through HPLC, the purity for obtaining hydroxytyrosol is 96.5%.It is computed, recovery rate is 94.6%.
Embodiment 6
The method that hydroxytyrosol is extracted from processing olive oil waste water, including following preparation process：
1) waste water for taking processing olive oil to produce, carries out ultrafiltration, the film reused with the milipore filter of 30000 molecular weight of retention
Aperture is 0.04 μm of progress micro-filtration, obtains filtrate；
2) filtrate enters macroporous adsorbent resin column chromatography, is 8 with volume ratio:Ethanol solution and second of 1 volumetric concentration for 50%
The mixed solution of acetoacetic ester is eluted for eluant, eluent, collects eluent, the consumption of the mixed solution is resin bed volume
8 times；
3) eluent is crossed into the hollow-fibre membrane that molecular cut off is 260,000, obtains concentrate；
4) vacuum freeze drying, obtains hydroxytyrosol.
Detected through HPLC, the purity for obtaining hydroxytyrosol is 96.4%.
Embodiment 7
The method that hydroxytyrosol is extracted from processing olive oil waste water, including following preparation process：
1) waste water for taking processing olive oil to produce, carries out ultrafiltration, the film reused with the milipore filter of 30000 molecular weight of retention
Aperture is 0.04 μm of progress micro-filtration, obtains filtrate；
2) filtrate enters macroporous adsorbent resin column chromatography, is 8 with volume ratio:Ethanol solution and second of 1 volumetric concentration for 50%
The mixed solution of acetoacetic ester is eluted for eluant, eluent, collects eluent, the consumption of the mixed solution is resin bed volume
8 times；
3) eluent is crossed into the hollow-fibre membrane that molecular cut off is 240,000, obtains concentrate；
4) vacuum freeze drying, obtains hydroxytyrosol.
Detected through HPLC, the purity for obtaining hydroxytyrosol is 96.7%.
Embodiment 8
The method that hydroxytyrosol is extracted from processing olive oil waste water, including following preparation process：
1) waste water for taking processing olive oil to produce, carries out ultrafiltration, the film reused with the milipore filter of 30000 molecular weight of retention
Aperture is 0.04 μm of progress micro-filtration, obtains filtrate；
2) filtrate enters macroporous adsorbent resin column chromatography, is 8 with volume ratio:Ethanol solution and second of 1 volumetric concentration for 50%
The mixed solution of acetoacetic ester is eluted for eluant, eluent, collects eluent, the consumption of the mixed solution is resin bed volume
8 times；
3) eluent is crossed into the hollow-fibre membrane that molecular cut off is 220,000, obtains concentrate；
4) vacuum freeze drying, obtains hydroxytyrosol.
Detected through HPLC, the purity for obtaining hydroxytyrosol is 97.3%.
Embodiment 9
The method that hydroxytyrosol is extracted from processing olive oil waste water, including following preparation process：
1) waste water for taking processing olive oil to produce, carries out ultrafiltration, the film reused with the milipore filter of 30000 molecular weight of retention
Aperture is 0.04 μm of progress micro-filtration, obtains filtrate；
2) filtrate enters macroporous adsorbent resin column chromatography, is 8 with volume ratio:Ethanol solution and second of 1 volumetric concentration for 50%
The mixed solution of acetoacetic ester is eluted for eluant, eluent, collects eluent, the consumption of the mixed solution is resin bed volume
8 times；
3) eluent is crossed into the hollow-fibre membrane that molecular cut off is 200,000, obtains concentrate；
4) vacuum freeze drying, obtains hydroxytyrosol.
Detected through HPLC, the purity for obtaining hydroxytyrosol is 99.5%.
Embodiment 10
The method that hydroxytyrosol is extracted from processing olive oil waste water, including following preparation process：
1) waste water for taking processing olive oil to produce, carries out ultrafiltration, the film reused with the milipore filter of 30000 molecular weight of retention
Aperture is 0.04 μm of progress micro-filtration, obtains filtrate；
2) filtrate enters macroporous adsorbent resin column chromatography, is 8 with volume ratio:Ethanol solution and second of 1 volumetric concentration for 50%
The mixed solution of acetoacetic ester is eluted for eluant, eluent, collects eluent, the consumption of the mixed solution is resin bed volume
8 times；
3) eluent is crossed into the hollow-fibre membrane that molecular cut off is 180,000, obtains concentrate；
4) vacuum freeze drying, obtains hydroxytyrosol.
Detected through HPLC, the purity for obtaining hydroxytyrosol is 97.8%.
Embodiment 11
The method that hydroxytyrosol is extracted from processing olive oil waste water, including following preparation process：
1) waste water for taking processing olive oil to produce, carries out ultrafiltration, the film reused with the milipore filter of 30000 molecular weight of retention
Aperture is 0.04 μm of progress micro-filtration, obtains filtrate；
2) filtrate enters macroporous adsorbent resin column chromatography, is 8 with volume ratio:Ethanol solution and second of 1 volumetric concentration for 50%
The mixed solution of acetoacetic ester is eluted for eluant, eluent, collects eluent, the consumption of the mixed solution is resin bed volume
8 times；
3) eluent is crossed into the hollow-fibre membrane that molecular cut off is 160,000, obtains concentrate；
4) vacuum freeze drying, obtains hydroxytyrosol.
Detected through HPLC, the purity for obtaining hydroxytyrosol is 96.5%.
Claims (7)
1. the method for hydroxytyrosol is extracted from processing olive oil waste water, it is characterised in that including following preparation process：
1) waste water for taking processing olive oil to produce, carries out ultrafiltration, then carry out with the milipore filter of 20000~40000 molecular weight of retention
Micro-filtration, obtains filtrate；
2) filtrate enters macroporous adsorbent resin column chromatography, and the mixed solution with ethanol solution and ethyl acetate is that eluant, eluent is washed
It is de-, collect eluent；
3) eluent is crossed into the hollow-fibre membrane that molecular cut off is 16~280,000, obtains concentrate；
4) dry, obtain hydroxytyrosol.
2. the method for hydroxytyrosol is extracted in the olive oil waste water according to claim 1 from processing, it is characterised in that：It is described
Step 1) in, the membrane aperture that micro-filtration is used is 0.02~0.06 μm.
3. the method for hydroxytyrosol is extracted in the olive oil waste water according to claim 1 from processing, it is characterised in that：It is described
Step 2) in, the volume ratio of ethanol solution and ethyl acetate is 6~10:1.
4. the method for hydroxytyrosol is extracted in the olive oil waste water according to claim 3 from processing, it is characterised in that：It is described
Step 2) in, the volumetric concentration of ethanol solution is 40%~60%.
5. the method for hydroxytyrosol is extracted in the olive oil waste water according to claim 1 from processing, it is characterised in that：It is described
Step 2) in, the consumption of mixed solution is 6~8 times of resin bed volume.
6. the method for hydroxytyrosol is extracted in the olive oil waste water according to claim 1 from processing, it is characterised in that：It is described
Step 3) in, eluent crosses the hollow-fibre membrane that molecular cut off is 200,000.
7. the method for hydroxytyrosol is extracted in the olive oil waste water according to claim 1 from processing, it is characterised in that：It is described
Step 4) in, vacuum freeze drying.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007074490A1 (en) * | 2005-12-29 | 2007-07-05 | Universita' Degli Studi Di Napoli Federico Ii | Process for producing triacξtylhydroxytyrosol from olive oil mill waste waters for use as stabilized antioxidant |
| CN101631758A (en) * | 2007-01-26 | 2010-01-20 | 普罗贝尔特医药公司 | Process and apparatus for the production of hydroxytyrosol containing extract from olives and solids containing residues of olive oil extraction |
| CN101652130A (en) * | 2007-04-18 | 2010-02-17 | 帝斯曼知识产权资产管理有限公司 | Novel use of hydroxytyrosol and olive extracts/concentrates containing it |
-
2017
- 2017-03-29 CN CN201710195465.0A patent/CN106946662A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007074490A1 (en) * | 2005-12-29 | 2007-07-05 | Universita' Degli Studi Di Napoli Federico Ii | Process for producing triacξtylhydroxytyrosol from olive oil mill waste waters for use as stabilized antioxidant |
| CN101631758A (en) * | 2007-01-26 | 2010-01-20 | 普罗贝尔特医药公司 | Process and apparatus for the production of hydroxytyrosol containing extract from olives and solids containing residues of olive oil extraction |
| CN101652130A (en) * | 2007-04-18 | 2010-02-17 | 帝斯曼知识产权资产管理有限公司 | Novel use of hydroxytyrosol and olive extracts/concentrates containing it |
Non-Patent Citations (2)
| Title |
|---|
| DIMITRIS P. ZAGKLIS等: "Purification of olive mill wastewater phenols through membrane filtration and resin adsorption/desorption", 《JOURNAL OF HAZARDOUS MATERIALS》 * |
| M.D. VÍCTOR-ORTEGA等: "Performance and modeling of continuous ion exchange processes for phenols recovery from olive mill wastewater", 《PROCESS SAFETY AND ENVIRONMENTAL PROTECTION》 * |
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Application publication date: 20170714 |