CN107596734A - A kind of preparation method of graphite oxide alkene polymer continuous bed, using and a kind of method of separation and concentration phytosterol - Google Patents
A kind of preparation method of graphite oxide alkene polymer continuous bed, using and a kind of method of separation and concentration phytosterol Download PDFInfo
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- CN107596734A CN107596734A CN201710998810.4A CN201710998810A CN107596734A CN 107596734 A CN107596734 A CN 107596734A CN 201710998810 A CN201710998810 A CN 201710998810A CN 107596734 A CN107596734 A CN 107596734A
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Abstract
The invention provides a kind of preparation method of graphite oxide alkene polymer continuous bed, using and a kind of method of separation and concentration phytosterol, graphite oxide alkene polymer continuous bed be to be prepared by adding the big graphene oxide of high mechanical strength, specific surface area in organic polymer continuous bed preparation process.The preparation method of the present invention is simple, economical and practical, and the specific surface area and pore structure of resulting continuous bed are improved, and add its active force with phytosterol, enrichment can be effectively separated to phytosterol, extend the application of macromolecule integral material.Extract phytosterol using the organic polymer continuous bed prepared by the present invention, can obtain the natural medicine of high added value, and reduce discharged due to distillate caused by environmental pollution, have broad application prospects and economic benefit.
Description
Technical field
The present invention relates to a kind of organic polymer continuous bed, and it is continuous to concretely relate to a kind of graphite oxide alkene polymer
The preparation method of bed, the method for application and separation and concentration phytosterol.
Background technology
Phytosterol is a kind of natural active matter being present in vegetable fat, and obtained plant is purified from vegetable fat
Thing sterol mainly has cupreol（β-sitosterol）, stigmasterol, campesterol and brassicasterol.Phytosterol has very
Important physiological function, since l9l5 Peterson prove that the chicken that phytosterol is fed with to high cholesterol has reduction lipids contents
Function since, massive epidemiology data and laboratory research are shown, take in many slow of more phytosterol and crowd
The incidence of venereal disease is relatively low relevant, such as coronary arteriosclerotic cardiopathy, cancer, benign prostatauxe, therefore plants at present
Thing sterol receives increasing attention.
Proved by years of researches and substantial amounts of zoopery, phytosterol is athero- in reduction cholesterol, improvement artery
Hardening, suppress tumour, mitigate hepar damnification and anti-oxidant etc. all play an important role.Phytosterol is described as by scientists
" key of life ".The one kind of cupreol as phytosterol, there is obvious the effect of reducing serum cholesterol, substituted with it
Cholesterol has special meaning as liposome membrane material for functional food, therefore, research and application for cupreol
Receive significant attention.
China is the big country for producing grease and consuming grease, and oil resource enriches.The purifying of phytosterol uses molten at present
The methods of agent crystallisation, complexometry, dry type saponification method, molecularly distilled, supercritical carbon dioxide extraction method, column chromatography.It is molten
Agent crystallisation needs multiple fractionation to crystallize, complex steps, and needs a large amount of organic solvents, causes environmental pollution.Dry type saponification
Method raw material availability is low, and the rate of recovery is low.Molecularly distilled is cumbersome, and products obtained therefrom purity is low.Therefore, the above method is not
It is adapted to laboratory research and industrialized production, it is necessary to develop a kind of new material and method is used for purifying phytosterols.
The content of the invention
An object of the present invention is to provide a kind of preparation method of graphite oxide alkene polymer continuous bed, to prepare oxidation
The organic polymer continuous bed of graphene modified.
The second object of the present invention is to provide a kind of application of graphite oxide alkene polymer continuous bed, and it can be applied to dividing
From in terms of, enriching plant sterol.
The third object of the present invention is to provide a kind of method of separation and concentration phytosterol, to solve existing phytosterol point
From enrichment method complex steps, the problems such as rate of recovery is low, and environment is unfriendly.
What an object of the present invention was realized in：
A kind of preparation method of graphite oxide alkene polymer continuous bed, by graphene oxide, octene, polyvinylpyrrolidone, three
Glycol diacrylate, pore-foaming agent and benzoyl peroxide ultrasonic disperse it is uniform after, add DMA, be sufficiently mixed
And after removing bubble, obtain mixed liquor；Mixed liquor is poured into stainless steel gc column tube, reacts 2.5 ~ 3.5h in 20 ~ 30 DEG C,
The both ends installation column cap of stainless steel gc column tube, is then attached on efficient liquid-phase chromatographic pump, using methanol as mobile phase by post
Pore-foaming agent, solvent and unreacted DDGS in body rinse, and produce the organic polymer continuous bed of graphene oxide modification.
The graphene oxide, octene, polyvinylpyrrolidone, triethylene glycol diacrylate, pore-foaming agent and benzoyl peroxide
The ratio of formyl is：0.1~0.8mg∶0.30~0.36mL∶20~40mg∶0.30~0.36mL∶0.30~0.36mL∶20mg.It is preferred that
Ground, the graphene oxide, octene, polyvinylpyrrolidone, triethylene glycol diacrylate, pore-foaming agent and benzoyl peroxide
Ratio is 0.1 ~ 0.8mg: 0.36mL: 20 ~ 40mg: 0.36mL: 0.36mL: 20mg.Preferably, the graphene oxide, octene,
Polyvinylpyrrolidone, triethylene glycol diacrylate, the ratio of pore-foaming agent and benzoyl peroxide are 0.8mg: 0.36mL: 20mg
∶0.36mL∶0.36mL∶20mg。
The pore-foaming agent is the mixture of normal propyl alcohol and laruyl alcohol.
The volume ratio of the normal propyl alcohol and laruyl alcohol is 1.25 ~ 8: 1.
The column length of the stainless steel gc column tube is 50mm, and internal diameter is 4.6 mm.
What the second object of the present invention was realized in：
Application of the aforementioned oxidation graphene polymer continuous bed in terms of separation, enriching plant sterol, particularly in separation, enrichment
Application in terms of cupreol.
What the third object of the present invention was realized in：
A kind of method of separation and concentration phytosterol, aforementioned oxidation graphene polymer continuous bed is connected to high performance liquid chromatography
On instrument, using methanol-water mixed solution as mobile phase, if the methanol solution sample introduction by the enriched sample to be separated containing phytosterol
Dry time, enriching and purifying is carried out to phytosterol.
In the methanol-water mixed solution, the volume ratio of methanol and water is 13: 87.
The flow velocity of mobile phase is 1mL/min, and each sampling volume is 20 μ L.
The concentration of the enriched sample solution to be separated is 1mg/mL.
The present invention in organic polymer continuous bed preparation process by adding the big oxidation of high mechanical strength, specific surface area
Graphene, the organic polymer continuous bed of graphene oxide modification is prepared, preparation method is simple, economical and practical, gained
Specific surface area and pore structure to continuous bed are improved, and are taken full advantage of special possessed by high polymer material and nano-particle
Property, resulting continuous bed has excellent chemical property, and adds its active force with phytosterol, can using this material
To carry out efficiently separating enrichment to phytosterol, also there is purification effect to the phytosterol in actual sample, extend height
The application of molecule integral material.
The present invention uses the organic polymer continuous bed of prepared graphene oxide modification as liquid-phase chromatographic column, can be with
The phytosterol in deodorization distillate is extracted, on the one hand can obtain the natural medicine of high added value, meets life, the doctor of people
The demand of medicine and daily chemical industry, increase economic benefit；On the other hand, the comprehensive utilization to deodorization distillate can be reduced due to distillating
Environmental pollution caused by thing discharge, has broad application prospects and economic benefit.
Brief description of the drawings
Fig. 1 is the scanning electron microscope (SEM) photograph of the graphite oxide alkene polymer continuous bed prepared by embodiment 1.
Fig. 2 is the scanning electron microscope (SEM) photograph of the organic polymer continuous bed prepared by comparative example 1.
Fig. 3 is embodiment 1 and the comparison of N2 adsorption-desorption curve of the continuous bed prepared by comparative example 1.
Fig. 4 is elution chromatography figure of the different mobile phases to cupreol, wherein, a represents that mobile phase is that volume ratio is 13: 87
Methanol-water mixed solution when, to the elution chromatography figure of cupreol, b represents that mobile phase when being methanol, is washed to cupreol
Decolouring spectrogram.
Fig. 5 is using embodiment 1 and the graphite oxide alkene polymer continuous bed prepared by comparative example 1, cupreol sample introduction
Amount and continuous bed are to the graph of a relation between cupreol adsorbance.
Fig. 6 is to β-paddy in peanut oil cake extract using the graphite oxide alkene polymer continuous bed prepared by embodiment 1
The enrichment figure of sterol, wherein, the sample size of the represented enrichment figure line of a, b, c is respectively 20 μ L, 100 μ L and 1000 μ L.
Fig. 7 is the richness to cupreol in peanut oil using the graphite oxide alkene polymer continuous bed prepared by embodiment 1
Collection figure, wherein, the sample size of the represented enrichment figure line of a, b, c is respectively 20 μ L, 100 μ L and 1000 μ L.
Embodiment
With reference to embodiment, the present invention is further elaborated, and following embodiments are only as explanation, not with any
Mode limits the scope of the invention.
Agents useful for same is to analyze pure or chromatographically pure in embodiment, and commercially available or pass through those of ordinary skill in the art
It is prepared by well known method.Following embodiments realize the purpose of the present invention.
Embodiment 1
By 0.8mg graphene oxides（GO）, 20mg benzoyl peroxides, 20mg polyvinylpyrrolidones（PVP), 0.36mL octenes
（C8）, 0.36mL triethylene glycol diacrylates（TEGDMA）, 0.2mL normal propyl alcohols, 0.16mL laruyl alcohols mixing, ultrasonic disperse
More than 30min, after being uniformly dispersed, 200 μ L DMA is added, is sufficiently mixed, will be mixed after ultrasound removes bubble
Close liquid to be poured into the mm I.D. of 50 mm × 4.6 stainless steel gc column tube, after 30 DEG C of water-bath 2.5h, stainless steel colored
The both ends installation column cap of column jecket is composed, is then attached on efficient liquid-phase chromatographic pump, using methanol as mobile phase by the cause in cylinder
Other unreacted DDGSs such as hole agent are rinsed well, produce the organic polymer continuous bed of graphene oxide modification.
The microscopic appearance of continuous bed prepared by SEM is observed, acquired results such as Fig. 1.Can from Fig. 1
Go out, the aperture of prepared organic polymer continuous bed material is big, pore size distribution is more, and skeleton structure is compact.
Comparative example 1
By 20mg benzoyl peroxides, 20mg polyvinylpyrrolidones, 0.36mL octenes, 0.36mL triethylene glycol diacrylates,
0.2mL normal propyl alcohols, the mixing of 0.16mL laruyl alcohols, more than ultrasonic disperse 30min, after being uniformly dispersed, add 200 μ L N, N- bis-
Methylaniline, it is sufficiently mixed, after ultrasound removes bubble, mixed liquor is poured into the mm I.D. of 50 mm × 4.6 stainless steel chromatogram
In column jecket, after 30 DEG C of water-bath 2.5h, column cap is installed at the both ends of stainless steel gc column tube, is then attached to high-efficient liquid phase color
Compose on pump, other unreacted DDGSs such as the pore-foaming agent in cylinder are rinsed well using methanol as mobile phase, produce anaerobic
The organic polymer continuous bed of graphite alkene modification.
The microscopic appearance of continuous bed prepared by SEM is observed, acquired results such as Fig. 2.Comparison diagram 2 and figure
1, it is found that the aperture of continuous bed integral material is smaller relative to Fig. 1 in Fig. 2, and skeleton structure is fine and close, and hole is relatively fewer.By
This understands that the addition of graphene oxide can improve the pore structure of continuous bed material.
Embodiment 2
By 0.1mg graphene oxides, 20mg benzoyl peroxides, 40mg polyvinylpyrrolidones, 0.30mL octenes, 0.30mL
Triethylene glycol diacrylate, 0.2mL normal propyl alcohols, the mixing of 0.16mL laruyl alcohols, more than ultrasonic disperse 30min, after being uniformly dispersed, then
200 μ L DMA is added, is sufficiently mixed, after ultrasound removes bubble, mixed liquor is poured into the mm of 50 mm × 4.6
I.D. in stainless steel gc column tube, after 30 DEG C of water-bath 2.5h, column cap is installed at the both ends of stainless steel gc column tube, then
It is connected on efficient liquid-phase chromatographic pump, is rushed other unreacted DDGSs such as the pore-foaming agent in cylinder using methanol as mobile phase
Wash clean, produce the organic polymer continuous bed of graphene oxide modification.
Embodiment 3
By 0.4mg graphene oxides, 20mg benzoyl peroxides, 40mg polyvinylpyrrolidones, 0.36mL octenes, 0.36mL
Triethylene glycol diacrylate, 0.16mL normal propyl alcohols, the mixing of 0.14mL laruyl alcohols, more than ultrasonic disperse 30min, after being uniformly dispersed,
200 μ L DMA is added, is sufficiently mixed, after ultrasound removes bubble, mixed liquor is poured into 50 mm × 4.6
In mm I.D. stainless steel gc column tube, after 30 DEG C of water-bath 2.5h, column cap is installed at the both ends of stainless steel gc column tube,
It is then attached on efficient liquid-phase chromatographic pump, using methanol as mobile phase by other unreacteds such as the pore-foaming agent in cylinder and solvent
DDGS rinse well, produce graphene oxide modification organic polymer continuous bed.
Embodiment 4
By 0.8mg graphene oxides, 20mg benzoyl peroxides, 20mg polyvinylpyrrolidones, 0.36mL octenes, 0.36mL
Triethylene glycol diacrylate, 0.32mL normal propyl alcohols, the mixing of 0.04mL laruyl alcohols, more than ultrasonic disperse 30min, after being uniformly dispersed,
200 μ L DMA is added, is sufficiently mixed, after ultrasound removes bubble, mixed liquor is poured into 50 mm × 4.6
In mm I.D. stainless steel gc column tube, after 20 DEG C of water-bath 3.5h, column cap is installed at the both ends of stainless steel gc column tube,
It is then attached on efficient liquid-phase chromatographic pump, it is using methanol as mobile phase that the pore-foaming agent in cylinder etc. is other unreacted solvable
Thing is rinsed well, produces the organic polymer continuous bed of graphene oxide modification.
Embodiment 5
Polyalcohol integral pole prepared in embodiment 1 and comparative example 1 is connected on high pressure pump respectively, with high flow rate,
High pressure is gone out, and is placed in 60 DEG C of baking ovens and is dried 48h, it is characterized using specific surface area Porosimetry, gained
As a result such as Fig. 3.As a result show, the specific surface area of prepared polymer continuous bed is 11.4640m in embodiment 12/ g, comparative example 1
In the specific surface area of prepared polymer continuous bed be 5.5919m2/g.It follows that the addition of graphene oxide can increase
The specific surface area of continuous bed material.
Embodiment 6
Prepare cupreol sample：The accurate cupreol for weighing 25mg adds the dissolving of 10mL methanol in 50mL beakers, rear to turn
Move in 25mL volumetric flasks, with a small amount of methanol rinse beaker, and rinse liquid is transferred in volumetric flask three times, be finally settled to
25mL, produce 1mg/mL cupreol sample.
Continuous bed prepared by embodiment 1 is connected to high performance liquid chromatograph, using volume ratio as 13: 87 methanol-water
Mixed solution and methanol are respectively mobile phase, the μ L cupreols of sample introduction 100（1mg/mL）, different mobile phases are tested to β-paddy steroid
The eluting power of alcohol, as a result as shown in Figure 4.From fig. 4, it can be seen that ought be by 13: 87 methanol-water mixed solution of volume ratio
During mobile phase, cupreol absorption completely changes mobile phase after methanol, can to wash it completely in prepared continuous bed
It is de-.
Embodiment 7
Continuous bed prepared by embodiment 1 is connected to high performance liquid chromatograph, using volume ratio as 13:87 methanol-water mixing
Solution is mobile phase, and with 1mg/mL cupreol continuous sample introduction, phytosterol is enriched with；Then using methanol as mobile phase
Eluted, obtain phytosterol sample size and the graph of a relation of adsorbance, as shown in Figure 5.From fig. 5, it can be seen that work as sample size
During less than 30mL, the continuous bed prepared by embodiment 1 gradually increases with the increase of sample size the adsorbance of cupreol；When
After sample size is more than 30mL, adsorbance no longer increases with the increase of sample introduction, reaches adsorption saturation.When sample size is less than 20mL
When, the continuous bed prepared by comparative example 1 gradually increases with the increase of sample size the adsorbance of cupreol, when sample size surpasses
After crossing 20mL, adsorbance no longer increases with the increase of sample size, reaches adsorption saturation.In summary, graphene oxide plus
Enter to improve accumulation ability of the continuous bed to phytosterol.
Embodiment 8
Prepare peanut oil cake sample：By dry peanut oil cake in pulverizer ground into end, cross 80 mesh standard inspection sieves.Accurately
The sample after 20g sievings is weighed, the methanol that about 100mL is added in three-neck flask is dried in 500mL, is placed on 40oC thermostatted waters
In bath after heating stirring 2h, transfer them to 250mL and dry in beaker, after standing separates out oil reservoir, separate oil reservoir and methanol
Layer, 10mL methanol is added after methanol layer solution is volatilized and is dissolved again, as stock sample solution.Stock sample solution is diluted 100
It is stand-by as sample solution after times.
Continuous bed prepared by embodiment 1 is connected on high performance liquid chromatograph, using volume ratio as 13: 87 methanol-water
Mixed solution is mobile phase, and the oil cake extract prepared using experiment continuous sample introduction, carries out the enrichment of phytosterol as sample.It is rich
After collecting a certain amount of, C18 posts are accessed after continuous bed, are eluted by mobile phase of methanol, obtain sample size with continuous bed to flower
The graph of a relation of phytosterol enriching quantity in oil generation cake extract, as shown in Figure 6.From fig. 6, it can be seen that as sample size increases,
Continuous bed substantially increases the adsorbance of cupreol in oil cake sample, illustrates the continuous bed prepared by embodiment 1 to oil cake sample
Cupreol in product has enrichment.
Embodiment 9
Prepare peanut oil samples：Precise 0.5g edible peanut oil samples, are poured into 50 mL three-neck flasks, add 15 mL without
Water-ethanol, the potassium hydroxide solutions of 5 mL 50%, are placed in 60 DEG C of waters bath with thermostatic control, and stirring 60min makes its reaction complete.By reaction product
It is placed at room temperature, pH regulations is then placed in refrigerator to neutrality with glacial acetic acid.After freezing after 2h, 10 are centrifuged with 10000 r/min
Min, take supernatant to be transferred in 50 mL centrifuge tubes, stored in 4 DEG C of refrigerators stand-by.
Continuous bed prepared by embodiment 1 is connected on high performance liquid chromatograph, using volume ratio as 13: 87 methanol-water
Mixed solution is mobile phase, using foregoing prepared peanut oil samples as sample, continuous sample introduction, carries out the enrichment of phytosterol.
Be enriched with it is a certain amount of after, after continuous bed access C18 posts, eluted by mobile phase of methanol, obtain sample size and continuous bed pair
The graph of a relation of the enriching quantity of phytosterol in peanut oil extract, as shown in Figure 7.From figure 7 it can be seen that as sample size increases
Add, continuous bed substantially increases the adsorbance of cupreol in peanut oil samples, illustrates the continuous bed prepared by embodiment 1 to flower
Cupreol in oil generation sample has enrichment.
Claims (10)
1. a kind of preparation method of graphite oxide alkene polymer continuous bed, it is characterised in that by graphene oxide, octene, poly- second
Alkene pyrrolidone, triethylene glycol diacrylate, pore-foaming agent and benzoyl peroxide ultrasonic disperse it is uniform after, add N, N- dimethyl
Aniline, after being sufficiently mixed and removing bubble, obtain mixed liquor；Mixed liquor is poured into stainless steel gc column tube, it is anti-in 20 ~ 30 DEG C
2.5 ~ 3.5h is answered, column cap is installed at the both ends of stainless steel gc column tube, is then attached on efficient liquid-phase chromatographic pump, is made with methanol
Unreacted DDGS in cylinder is rinsed for mobile phase, produces the organic polymer continuous bed of graphene oxide modification.
2. the preparation method of graphite oxide alkene polymer continuous bed according to claim 1, it is characterised in that the oxidation
Graphene, octene, polyvinylpyrrolidone, triethylene glycol diacrylate, the ratio of pore-foaming agent and benzoyl peroxide for 0.1 ~
0.8mg∶0.30~0.36mL∶20~40mg∶0.30~0.36mL∶0.30~0.36mL∶20mg。
3. the preparation method of graphite oxide alkene polymer continuous bed according to claim 2, it is characterised in that the oxidation
Graphene, octene, polyvinylpyrrolidone, triethylene glycol diacrylate, the ratio of pore-foaming agent and benzoyl peroxide for 0.1 ~
0.8mg∶0.36mL∶20~40mg∶0.36mL∶0.36mL∶20mg。
4. the preparation method of graphite oxide alkene polymer continuous bed according to claim 1, it is characterised in that the pore
Agent is the mixture of normal propyl alcohol and laruyl alcohol.
5. the preparation method of graphite oxide alkene polymer continuous bed according to claim 3, it is characterised in that described positive third
The volume ratio of alcohol and laruyl alcohol is 1.25 ~ 8: 1.
6. the preparation method of graphite oxide alkene polymer continuous bed according to claim 1, it is characterised in that described stainless
The column length of steel gc column tube is 50mm, and internal diameter is 4.6 mm.
A kind of 7. application of the graphite oxide alkene polymer continuous bed in terms of separation, enriching plant sterol described in claim 1.
A kind of 8. method of separation and concentration phytosterol, it is characterised in that by the graphite oxide alkene polymer described in claim 1
Continuous bed is connected on high performance liquid chromatograph, using methanol-water mixed solution as mobile phase, will contain the to be separated of phytosterol
Enriched sample solution sample introduction carries out enriching and purifying several times, to phytosterol.
9. the method for separation and concentration phytosterol according to claim 8, it is characterised in that the methanol-water mixing is molten
In liquid, the volume ratio of methanol and water is 13: 87；The flow velocity of mobile phase is 1mL/min, and each sampling volume is 20 μ L.
10. the method for separation and concentration phytosterol according to claim 8, it is characterised in that the enrichment sample to be separated
The concentration of product solution is 1mg/mL.
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| CN106268714A (en) * | 2016-08-18 | 2017-01-04 | 河北大学 | A kind of preparation method of functionalized carbon nano-tube integral post |
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| CN106268714A (en) * | 2016-08-18 | 2017-01-04 | 河北大学 | A kind of preparation method of functionalized carbon nano-tube integral post |
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| 李雅萍等: ""基于功能化氧化石墨烯交联剂的聚合物整体柱的制备及应用"", 《第十届全国生物医药色谱及相关技术学术交流会论文集》 * |
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