CN109336990B - Method for removing plant polysaccharide pigment from protonated amino graphene and application - Google Patents
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Abstract
本发明公开了一种质子化氨基石墨烯脱除植物多糖色素的方法及应用，该方法开创性的使用了质子化氨基石墨烯作为脱色剂进行植物多糖脱色处理，操作简单，速度快捷，生产成本低，适用于工业化生产；整个制备过程安全可靠，不使用酸碱及有毒试剂等，不产生污染，得到的多糖结构不会被破坏。试验验证，将通过质子化氨基石墨烯用于对植物多糖进行脱色处理，脱色效率大于90％，多糖保留率也在85％以上。
The invention discloses a method and application for decolorizing plant polysaccharide pigments by protonated aminographene. The method innovatively uses protonated aminographene as a decolorizing agent to decolorize plant polysaccharides, and has the advantages of simple operation, fast speed and low production cost. Low, suitable for industrial production; the whole preparation process is safe and reliable, does not use acid and alkali and toxic reagents, etc., does not cause pollution, and the obtained polysaccharide structure will not be destroyed. Experiments have verified that the protonated aminographene will be used to decolorize plant polysaccharides, the decolorization efficiency is greater than 90%, and the polysaccharide retention rate is also above 85%.
Description
[ technical field ] A method for producing a semiconductor device
The invention belongs to the field of refining processing methods for plant active ingredients, and relates to a method for removing plant polysaccharide pigment from protonated amino graphene and application of the method.
[ background of the invention ]
The saccharide is a natural product, widely distributed, and accounts for about 80-90% of the dry weight of the plant. The saccharide compounds not only serve as storage nutrients for plants, but also constitute the skeleton components of plant cells. At present, many documents report that saccharides have various biological activities such as anti-tumor, anti-hepatitis, anti-cardiovascular disease, anti-aging and the like, and are also effective components in certain natural medicines. Polysaccharides, containing at least 10 monosaccharides. Usually, the number of monosaccharides is over one hundred, and some monosaccharides are up to thousands, and the properties of monosaccharides have great differences. Like proteins, the biological activity of polysaccharides is not only largely related to their structures, but also related to proteins, metal ions, pigments, and the like bound thereto, and has been a focus of recent research.
At present, polysaccharides with physiological functions are mainly extracted from plants, wherein polysaccharides extracted from aqueous solutions are the most important. Purified natural polysaccharide is white and has no sweet taste, but crude polysaccharide extract obtained by using aqueous solution as solvent extraction often contains pigment substances, the polysaccharide color is darkened due to oxidation, the quality of the polysaccharide is influenced, and subsequent research is carried out, so that the decolorization of the polysaccharide is an indispensable link in the polysaccharide refining process. Currently, common depigmentation methods include an activated carbon method, an oxidation method, a resin method and the like. The activated carbon adsorption decoloration mainly utilizes the porosity of the activated carbon, and can adsorb a large amount of polysaccharide while adsorbing the pigment, thereby reducing the retention rate of the polysaccharide. The oxidation method has chemical reaction, so that the degradation of polysaccharide can be caused while pigment is oxidized and degraded, thereby influencing the structure and subsequent physiological activity. While effective pigment removal and polysaccharide retention can be achieved by resin decolorization, time and money costs are not negligible. Therefore, it is necessary to invent a novel decolorization method which is economical and efficient and is suitable for industrial production.
[ summary of the invention ]
The invention aims to overcome the defects of the prior art and provides a method for removing plant polysaccharide pigment by using protonated amino graphene and application thereof.
In order to achieve the purpose, the invention adopts the following technical scheme to realize the purpose:
a method for removing plant polysaccharide pigment from protonated amino graphene comprises the following steps: mixing water solutions of protonated amino graphene and plant polysaccharide crude extracts to prepare mixed turbid liquid, wherein the ratio of the mixed material to the liquid is (1-10) mg: 10mL, the concentration of the water solution of the crude plant polysaccharide extract is 8 mg/mL; and magnetically stirring the mixed suspension uniformly, centrifuging to obtain a supernatant and a precipitate F, and freeze-drying the supernatant to obtain the plant polysaccharide without the pigment.
The invention is further improved in that:
preferably, the magnetic stirring time is 1-30 min; the centrifugal stirring speed is 10000-12000 r/min, and the centrifugal stirring time is 10-20 min.
Preferably, the preparation process of the protonated amino graphene comprises the following steps: mixing the graphene oxide solution, ethylenediamine and ammonia water to obtain a mixed solution A, refluxing the mixed solution A, centrifuging the mixed solution A, and removing the centrifugal filtrate to obtain a precipitate-aminographene; and (3) washing the amino graphene, immersing the amino graphene in HCl overnight to obtain a precipitate, and washing the precipitate to obtain the protonated amino graphene.
Preferably, the mixing ratio of the graphene oxide solution, the ethylenediamine and the ammonia water is 200: 2.4: 0.6; the concentration of the graphene oxide solution is 1mg/mL, and the graphene oxide in the graphene oxide solution is prepared by a Hummers method.
Preferably, the reflux temperature of the mixed solution A is 95 ℃, and the reflux time is 6 h; the HCl concentration was 0.1 mol/L.
Preferably, the process for preparing the aqueous solution of the crude extract of plant polysaccharide comprises the following steps: mixing plants and absolute ethyl alcohol in a Soxhlet extractor according to the proportion of 1g to 10mL, extracting for 2 times by refluxing, and drying the extract in the sun; dissolving the dried extract in distilled water, wherein the mixture liquid ratio is 1g: (10-20) mL to obtain a mixture C; ultrasonically extracting the mixture C for 3 times, mixing the extractive solutions obtained by 3 times, performing alcohol precipitation treatment on the mixed extractive solutions, collecting precipitate obtained by alcohol precipitation, wherein the precipitate is polysaccharide crude product, and dissolving the polysaccharide crude product in water to obtain polysaccharide crude product water solution with concentration of 8 mg/mL.
Preferably, the reflux time in the Soxhlet extractor is 4h each time; the ultrasonic extraction time of the mixture C is 2 h.
Preferably, the alcohol precipitation comprises dissolving the combined extractive solutions in ethanol at a volume ratio of 1:4, and treating the mixture at 4 deg.C overnight to obtain precipitate, which is polysaccharide extract.
Preferably, the protonated amino graphene can be regenerated by the following steps: soaking the precipitate F in 0.1mol/L NaOH, and centrifuging until the supernatant is colorless to obtain a precipitate G; and soaking the precipitate G in 0.1mol/L HCl overnight for treatment to prepare a precipitate which is regenerated protonated amino graphene.
The application of protonated amino graphene in removing plant polysaccharide pigment is disclosed.
Compared with the prior art, the invention has the following beneficial effects:
the invention discloses a method for removing plant polysaccharide pigment by protonated amino graphene, which creatively uses the protonated amino graphene as a decolorizing agent to decolorize plant polysaccharide, has simple operation, fast speed and low production cost and is suitable for industrial production; the whole preparation process is safe and reliable, acid and alkali, toxic reagents and the like are not used, pollution is not generated, and the structure of the obtained polysaccharide cannot be damaged. Experiments prove that the plant polysaccharide is decolorized by the method, the decolorization efficiency is more than 90%, and the polysaccharide retention rate is more than 85%.
Furthermore, the graphene oxide is prepared by a classical Hummers method, the preparation process of the method is safe and reliable, and the graphene oxide prepared by the method has good timeliness; and (3) reacting ethylenediamine, ammonia water and graphene oxide to perform amination modification, and performing acidic treatment on the amino graphene to obtain protonated amino graphene.
Further, extracting the plants twice by a soxhlet extractor to remove fat-soluble pigments, and performing ultrasonic extraction and alcohol precipitation treatment on the dried extract to obtain the plant polysaccharide crude product.
Furthermore, the pigment of the finally obtained precipitate is removed by NaOH washing, and then the material is regenerated by HCl, so that the decolorizing agent can be recycled, and the method is suitable for industrial production.
The invention also discloses an application of the protonated amino graphene in removing plant polysaccharide pigments, the application and removal process is simple, the cost is low, the applicability is wide, and most of plant polysaccharides can be removed; the pigment removal efficiency in the application process is high, and experiments prove that the decolorization efficiency of the plant polysaccharide is more than 90 percent, and the polysaccharide retention rate is more than 85 percent.
[ description of the drawings ]
FIG. 1 is a graph showing the effect of depigmenting agent dosage on the depigmenting rate of plant polysaccharides in accordance with the present invention.
FIG. 2 is a graph showing the effect of time for which the depigmenting agent of the present invention binds to plant polysaccharides on the polysaccharide depigmentation rate.
Fig. 3 is a graph showing the effect of depigmenting agents according to the invention on the depigmentation and retention of different plant polysaccharides.
Examples for different plants are example 4, example 9 and example 10.
FIG. 4 is a comparison graph of the actual color before and after decolorization of different plant polysaccharides according to the present invention.
[ detailed description ] embodiments
The invention is further described in detail with reference to the following embodiments and accompanying drawings, and provides a method for removing plant polysaccharide pigment by protonated amino graphene and an application thereof, wherein the method specifically comprises the following steps:
And 3, decoloring the polysaccharide crude extract: according to the feed-liquid ratio (1-10) mg: adding 10mL of the material protonated amino graphene prepared in the step (1) into the aqueous solution of the polysaccharide crude extract obtained in the step (2) to prepare a mixed suspension E; magnetically stirring the mixed suspension E for 1-30 min, and centrifuging for 10-20 min by a high-speed centrifuge under the condition of 10000-12000 r/min to obtain supernatant which is decolorized polysaccharide solution and precipitate F;
and 4, drying: and (4) freeze-drying the decolorized polysaccharide solution obtained in the step (3) in a freeze dryer to obtain the decolorized polysaccharide.
And 5, recycling the decolorizing materials: soaking the precipitate F obtained in the step 3 in 0.1mol/L NaOH, centrifuging by a high-speed centrifuge at 10000-12000 r/min until the supernatant is colorless, collecting a precipitate G, and washing by NaOH to remove pigments; and immersing the precipitate G in 0.1mol/L HCl for overnight treatment to regenerate the decolorizing agent, so as to obtain the decolorizing agent, namely the protonated amino graphene.
Example 1
And 2, carrying out reflux extraction on the cleaned medlar in a Soxhlet extractor for 4 hours by using absolute ethyl alcohol with the ratio of 1g to 10mL, extracting twice to remove fat-soluble pigment, drying the extract in the sun to remove the ethyl alcohol, and obtaining a process product according to the material-liquid ratio of 1g: dissolving 15mL of the extract in distilled water, performing ultrasonic extraction for 3 times, extracting for 2 hours each time, collecting and combining the extracting solutions extracted for 3 times to obtain an extracting solution; adding 4 times volume of anhydrous ethanol into the extractive solution, mixing, treating at 4 deg.C overnight to obtain precipitate, collecting precipitate as crude plant polysaccharide extract, and dissolving the crude plant polysaccharide extract in water to obtain polysaccharide crude extract water solution with concentration of 8 mg/mL.
and 4, measuring the retention rate of the plant polysaccharide after decolorization by a phenol-sulfuric acid method, and measuring the light absorption value of the polysaccharide before and after decolorization under the condition of 420nm of an ultraviolet spectrophotometer by an absorbance method, thereby obtaining the decolorization rate.
And 5, soaking the precipitate F obtained in the step 3 in 0.1mol/L NaOH, centrifuging by a high-speed centrifuge at 10000r/min until the supernatant is colorless, collecting the precipitate, immersing the precipitate in 0.1mol/L HCl overnight for treatment, and regenerating a decolorizing agent to obtain the regenerated decolorizing agent.
In the embodiment, the decolorization rate of the lycium barbarum polysaccharide is 45.9%, and the polysaccharide retention rate is 99.2%.
Example 2
and 4, measuring the retention rate of the plant polysaccharide after decolorization by a phenol-sulfuric acid method, and measuring the light absorption value of the polysaccharide before and after decolorization under the condition of 420nm of an ultraviolet spectrophotometer by an absorbance method, thereby obtaining the decolorization rate.
And 5, soaking the precipitate F obtained in the step 3 in 0.1mol/L NaOH, centrifuging by using a high-speed centrifuge at 12000r/min until the supernatant is colorless, collecting the precipitate, and immersing the precipitate in 0.1mol/L HCl overnight for treatment to regenerate the decolorizing agent to obtain the regenerated decolorizing agent.
In the example, the decolorization rate of the lycium barbarum polysaccharide is 62.4%, and the polysaccharide retention rate is 97.5%.
Example 3
and 4, measuring the retention rate of the plant polysaccharide after decolorization by a phenol-sulfuric acid method, and measuring the light absorption value of the polysaccharide before and after decolorization under the condition of 420nm of an ultraviolet spectrophotometer by an absorbance method, thereby obtaining the decolorization rate.
And 5, soaking the precipitate F obtained in the step 3 in 0.1mol/L NaOH, centrifuging by using a high-speed centrifuge at 11000r/min until the supernatant is colorless, collecting the precipitate, immersing the precipitate in 0.1mol/L HCl overnight for treatment, and regenerating a decolorizing agent to obtain the regenerated decolorizing agent.
In the example, the decolorization rate of the lycium barbarum polysaccharide is 86.6%, and the polysaccharide retention rate is 93.6%.
Example 4
and 4, measuring the retention rate of the plant polysaccharide after decolorization by a phenol-sulfuric acid method, and measuring the light absorption value of the polysaccharide before and after decolorization under the condition of 420nm of an ultraviolet spectrophotometer by an absorbance method, thereby obtaining the decolorization rate.
And 5, soaking the precipitate F obtained in the step 3 in 0.1mol/L NaOH, centrifuging by using a high-speed centrifuge at 12000r/min until the supernatant is colorless, collecting the precipitate, and immersing the precipitate in 0.1mol/L HCl overnight for treatment to regenerate the decolorizing agent to obtain the regenerated decolorizing agent.
In the embodiment, the decolorization rate of the lycium barbarum polysaccharide is 98.6%, and the polysaccharide retention rate is 92.7%.
Example 5
and 4, measuring the retention rate of the plant polysaccharide after decolorization by a phenol-sulfuric acid method, and measuring the light absorption value of the polysaccharide before and after decolorization under the condition of 420nm of an ultraviolet spectrophotometer by an absorbance method, thereby obtaining the decolorization rate.
And 5, soaking the precipitate F obtained in the step 3 in 0.1mol/L NaOH, centrifuging by using a high-speed centrifuge at 11000r/min until the supernatant is colorless, collecting the precipitate, immersing the precipitate in 0.1mol/L HCl overnight for treatment, and regenerating a decolorizing agent to obtain the regenerated decolorizing agent.
In the embodiment, the decolorization rate of the lycium barbarum polysaccharide is 98.2%, and the polysaccharide retention rate is 89.3%.
Example 6
and 4, measuring the retention rate of the plant polysaccharide after decolorization by a phenol-sulfuric acid method, and measuring the light absorption value of the polysaccharide before and after decolorization under the condition of 420nm of an ultraviolet spectrophotometer by an absorbance method, thereby obtaining the decolorization rate.
And 5, soaking the precipitate F obtained in the step 3 in 0.1mol/L NaOH, centrifuging by using a high-speed centrifuge at 12000r/min until the supernatant is colorless, collecting the precipitate, and immersing the precipitate in 0.1mol/L HCl overnight for treatment to regenerate the decolorizing agent to obtain the regenerated decolorizing agent.
In the embodiment, the decolorization rate of the lycium barbarum polysaccharide is 98.9%, and the polysaccharide retention rate is 87.6%.
Example 7
and 4, measuring the retention rate of the plant polysaccharide after decolorization by a phenol-sulfuric acid method, and measuring the light absorption value of the polysaccharide before and after decolorization under the condition of 420nm of an ultraviolet spectrophotometer by an absorbance method, thereby obtaining the decolorization rate.
And 5, soaking the precipitate F obtained in the step 3 in 0.1mol/L NaOH, centrifuging by using a high-speed centrifuge at 12000r/min until the supernatant is colorless, collecting the precipitate, and immersing the precipitate in 0.1mol/L HCl overnight for treatment to regenerate the decolorizing agent to obtain the regenerated decolorizing agent.
In the embodiment, the decolorization rate of the lycium barbarum polysaccharide is 98.9%, and the polysaccharide retention rate is 87.6%.
Example 8
and 4, measuring the retention rate of the plant polysaccharide after decolorization by a phenol-sulfuric acid method, and measuring the light absorption value of the polysaccharide before and after decolorization under the condition of 420nm of an ultraviolet spectrophotometer by an absorbance method, thereby obtaining the decolorization rate.
And 5, soaking the precipitate F obtained in the step 3 in 0.1mol/L NaOH, centrifuging by using a high-speed centrifuge at 12000r/min until the supernatant is colorless, collecting the precipitate, and immersing the precipitate in 0.1mol/L HCl overnight for treatment to regenerate the decolorizing agent to obtain the regenerated decolorizing agent.
In the embodiment, the decolorization rate of the lycium barbarum polysaccharide is 95.9%, and the polysaccharide retention rate is 82.6%.
Example 9
and 4, measuring the retention rate of the plant polysaccharide after decolorization by a phenol-sulfuric acid method, and measuring the light absorption value of the polysaccharide before and after decolorization under the condition of 420nm of an ultraviolet spectrophotometer by an absorbance method, thereby obtaining the decolorization rate.
And 5, soaking the precipitate F obtained in the step 3 in 0.1mol/L NaOH, centrifuging by using a high-speed centrifuge at 11000r/min until the supernatant is colorless, collecting the precipitate, immersing the precipitate in 0.1mol/L HCl overnight for treatment, and regenerating a decolorizing agent to obtain the regenerated decolorizing agent.
In this example, the decolorization rate of green tea polysaccharide was 90.66%, and the polysaccharide retention rate was 97.42%.
Example 10
and 4, measuring the retention rate of the plant polysaccharide after decolorization by a phenol-sulfuric acid method, and measuring the light absorption value of the polysaccharide before and after decolorization under the condition of 420nm of an ultraviolet spectrophotometer by an absorbance method, thereby obtaining the decolorization rate.
And 5, soaking the precipitate F obtained in the step 3 in 0.1mol/L NaOH, centrifuging by using a high-speed centrifuge at 11000r/min until the supernatant is colorless, collecting the precipitate, immersing the precipitate in 0.1mol/L HCl overnight for treatment, and regenerating a decolorizing agent to obtain the regenerated decolorizing agent.
In the embodiment, the decolouring rate of the red date polysaccharide is 97.75, and the polysaccharide retention rate is 85.97%.
Referring to fig. 1, which is a graph showing the effect of the amount of decolorizing agent on the decolorization rate, wherein the numbers are example numbers, it can be seen that the decolorization rate is gradually increased as the amount of decolorizing agent is increased.
Referring to fig. 2, the effect of the binding time (magnetic stirring time) on the decolorization rate is shown, and it can be seen that the effect of the magnetic stirring for 1min and the long-time magnetic stirring on the decolorization rate is not great.
Referring to fig. 3, a graph showing the influence of the decolorizing agent on the decolorizing rate and the retention rate of different plant polysaccharides illustrates that the method for removing pigments in plant polysaccharides by using protonated amino graphene provided by the present invention is suitable for most of various plants.
Referring to FIG. 4, the comparison of actual colors before and after decolorization of different plant polysaccharides is shown, wherein the bottle contains a transparent yellow liquid as polysaccharide crude body aqueous solution, and the bottle contains a transparent color liquid as decolorized polysaccharide solution; the leftmost of the graph is a comparison graph before and after Chinese wolfberry decolorization, the middle is a comparison graph before and after green tea decolorization, and the right is a comparison graph before and after red date decolorization; as is obvious from the figure, the protonated amino graphene can remove pigments in the plant polysaccharide.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.
Claims (8)
1. A method for removing plant polysaccharide pigment from protonated amino graphene is characterized by comprising the following steps: mixing water solutions of protonated amino graphene and plant polysaccharide crude extracts to prepare mixed turbid liquid, wherein the ratio of the mixed material to the liquid is (1-10) mg: 10mL, the concentration of the water solution of the crude plant polysaccharide extract is 8 mg/mL; magnetically stirring the mixed suspension uniformly, centrifuging to obtain supernatant and precipitate F, and freeze-drying the supernatant to obtain plant polysaccharide without pigment; .
The preparation process of the protonated amino graphene comprises the following steps: mixing the graphene oxide solution, ethylenediamine and ammonia water to obtain a mixed solution A, refluxing the mixed solution A, centrifuging the mixed solution A, and removing the centrifugal filtrate to obtain a precipitate-aminographene; washing the amino graphene, immersing the amino graphene in HCl overnight to obtain a precipitate, and washing the precipitate to obtain protonated amino graphene;
the preparation process of the water solution of the crude plant polysaccharide comprises the following steps: mixing the plant and anhydrous ethanol at a ratio of 1g:10mL in a Soxhlet extractor, reflux-extracting for 2 times to obtain extract, and sun-drying the extract; dissolving the dried extract in distilled water, wherein the mixture liquid ratio is 1g: (10-20) mL to obtain a mixture C; ultrasonically extracting the mixture C for 3 times, combining the extracting solutions obtained by the 3 times of extraction, carrying out alcohol precipitation treatment on the combined extracting solutions, collecting precipitates obtained by alcohol precipitation, wherein the precipitates are polysaccharide crude extracts, and dissolving the polysaccharide crude extracts in water to prepare polysaccharide crude extract water solution with the concentration of 8 mg/mL;
the plant polysaccharide is decolorized by the method, the decolorization efficiency is more than 90%, and the polysaccharide retention rate is more than 85%.
2. The method for removing plant polysaccharide pigment from protonated amino graphene as claimed in claim 1, wherein the magnetic stirring time is 1-30 min; after magnetic stirring, the centrifugal stirring speed is 10000-12000 r/min, and the centrifugal stirring time is 10-20 min.
3. The method for removing plant polysaccharide pigment from protonated amino graphene as claimed in claim 1, wherein the mixing ratio of the graphene oxide solution, the ethylenediamine and the ammonia water is 200: 2.4: 0.6; the concentration of the graphene oxide solution is 1mg/mL, and the graphene oxide in the graphene oxide solution is prepared by a Hummers method.
4. The method for removing the plant polysaccharide pigment from the protonated amino graphene as claimed in claim 1, wherein the reflux temperature of the mixed solution A is 95 ℃, and the reflux time is 6 h; the HCl concentration was 0.1 mol/L.
5. The method for removing plant polysaccharide pigment from protonated amino graphene according to claim 1, wherein the reflux time in the Soxhlet extractor is 4h each time; the ultrasonic extraction time of the mixture C is 2 h.
6. The method for removing plant polysaccharide pigments by using protonated amino graphene as claimed in claim 5, wherein the alcohol precipitation treatment comprises dissolving the combined extract in ethanol according to a volume ratio of 1:4, and treating the mixed solution at 4 ℃ overnight to obtain a precipitate, wherein the precipitate is a polysaccharide crude extract.
7. The method for removing plant polysaccharide pigment from protonated amino-graphene according to claim 1, wherein the protonated amino-graphene can be regenerated by the steps of: soaking the precipitate F in 0.1mol/L NaOH, and centrifuging until the supernatant is colorless to obtain a precipitate G; and soaking the precipitate G in 0.1mol/L HCl overnight for treatment to prepare a precipitate which is regenerated protonated amino graphene.
8. Use of protonated amino graphene prepared by the method of any one of claims 1 to 7 for depigmenting plant polysaccharides.
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| CN102895938A (en) * | 2012-11-13 | 2013-01-30 | 武汉大学 | Preparation method of graphene covered silica gel |
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