CN103113536A - Preparation method of molecularly imprinted polymer separating monosaccharide - Google Patents
Preparation method of molecularly imprinted polymer separating monosaccharide Download PDFInfo
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Abstract
The invention provides a preparation method of a molecularly imprinted polymer separating monosaccharide and relates to a method for preparing a molecularly imprinted polymer which separates monosaccharide and the preparation method is used for solving the problem of low adsorption efficiency of monosaccharide by existing molecularly imprinted polymer separating monosaccharide. The method comprises the following processes: a first process of surface pretreatment of silica gel; a second process of silylanization of the silica gel; and a third process of preparation of the molecularly imprinted polymer. The maximum saturation adsorption capacities for glucose, galactose and fructose of the molecularly imprinted polymer orderly are about 85.5mg/g, 78.75mg/g and 45.45mg/g, which are improved respectively by 2.8-3.4 times, 2.6-2.9 times and 2.2-4.5 times than existing molecularly imprinted polymer. The preparation method of the molecularly imprinted polymer separating monosaccharide disclosed by the invention is high in adsorption efficiency and simple in preparation method and operation, is capable of simplifying the separation and extraction processes of the monosaccharide molecules and reducing the application cost, and is applied to separation and purification of the monosaccharide.
Description
Technical field
The present invention relates to a kind of preparation method who separates the molecularly imprinted polymer of monose.
Background technology
Glucose is the indispensable nutritive substance of organism intracellular metabolic.Its oxidizing reaction liberated heat is the important sources of human life activity institute energy requirement.Can directly use on food, medicine industry, make reductive agent in the printing and dyeing tanning industry, glucose commonly used is made reductive agent in mirror industry processed and the glass liner of a thermos flask silver plating process.Industrial is also raw material synthesise vitamins C (xitix) with glucose in a large number.It is reported that glucose also has important application prospect through photocatalysis hydrogen production.Extracting now glucose, generally all to adopt purified starch be raw material, and acid technological process is produced, but technical process is very complicated, and the expense of taking a lot of work is expected the problems such as cost rising that cause.To play the material of simplifying effect be that very high economic worth is arranged therefore develop a kind of separation and Extraction process to glucose, and good application prospect is arranged
molecular imprinting refers to that preparation is to a certain template molecule (target molecule) process of polymkeric substance selectively, the preparation of molecularly imprinted polymer first interacts by microsphere and function monomer and forms supramolecular complex, then form polymkeric substance under crosslinked effect, last wash-out template molecule, make the hole with multiple action that forms in polymkeric substance with the complementation of microsphere space structure, can select to adsorb the microsphere in mixture to be separated, thereby reach separation, the purpose of purifying, the molecularly imprinted polymer of separation monose is 25～30mg/g to the maximum saturation adsorptive capacity of glucose at present, maximum saturation adsorptive capacity to semi-lactosi is 20～30mg/g, maximum saturation adsorptive capacity to fructose is 10～20mg/g, adsorption efficiency is low, therefore the molecularly imprinted polymer for preparing the high separation monose of a kind of adsorption efficiency is very important.
Summary of the invention
The present invention will solve the molecularly imprinted polymer of the existing separation monose technical problem low to the adsorption efficiency of monose, and the preparation method of the molecularly imprinted polymer that separates monose is provided.
The preparation method of the molecularly imprinted polymer of separation monose of the present invention carries out according to the following steps:
One, Silica Surface pre-treatment: it is in 15%～20% hydrochloric acid that silica gel is joined massfraction, under the condition of room temperature and stirring, wash 3～5 times, after then being washed till neutrality with deionized water, be dry under the vacuum condition of 100～120 ℃ in temperature, complete the preprocessing process of silica gel;
two, the silanization of silica gel: the ratio by the volume of the quality of silica gel and toluene is 1g: (8～12) mL, take the silica gel of toluene and step 1, and silica gel is dissolved in toluene, the ratio of pressing again the volume of the quality of silica gel and 3-aminopropyl triethoxysilane is (8～12) g: 10mL, add wherein the 3-aminopropyl triethoxysilane, under the nitrogen protection protection, it is 80～100 ℃ in temperature, under the condition that stirs, back flow reaction 10～14h, then filter and discard liquid, solid formation is first washed under the condition of stirring at room 2～4 times with toluene, wash under the condition of stirring at room 2～4 times with acetone again, be vacuum-drying 10～14h under the condition of 35～45 ℃ in temperature again, complete the silanization of silica gel, obtain amination silica gel,
three, the preparation of molecularly imprinted polymer: the volume ratio of pressing acetonitrile and water is (3～5): 1, to both mix, take ultrasonic frequency as 30～50KHz, reaction 9～11min obtains mixed system, be 0.03～0.07mol/L by the volumetric molar concentration of glucose in this mixed system, be 0.12～0.27mol/L by the volumetric molar concentration of acrylamide in this mixed system, the mass concentration of amination silica gel in this mixed system by step 2 is 0.03～0.07g/mL, with glucose, the amination silica gel of acrylamide and step 2 joins in this mixed system, shake 5～7h under the condition of room temperature, then press N, the mass ratio of N-methylene-bis propionic acid amide and glucose is (4～6): 9, with N, N-methylene-bis propionic acid amide adds, under the nitrogen atmosphere protection, take ultrasonic frequency as 30～50Hz, reaction 9～11min, the mass ratio of pressing again ammonium persulphate and glucose is (0.5～1.5): 9, ammonium persulphate is added, react 12～24h under room temperature condition, after reaction is completed, be centrifugal 10～20min under the condition of 3500～4500r/min at rotating speed, abandoning supernatant, with methyl alcohol and acetic acid mixed solution, solid matter is washed, in methyl alcohol and acetic acid mixed solution, the volume ratio of methyl alcohol and acetic acid is (3～5): 1, wash three times, wash for the first time 5～7h, wash for the second time 11～13h, 11～13h for the third time, centrifugal abandoning supernatant after each washing, wash next time, completing after carrying out washing treatment in temperature is that the Water Under of 35～45 ℃ is bathed evaporate to dryness, be vacuum-drying under the condition of 35～45 ℃ in temperature again, obtain separating the molecularly imprinted polymer of monose.
Embodiment
Technical scheme of the present invention is not limited to following embodiment, also comprises the arbitrary combination between each embodiment.
Embodiment one: the preparation method of the molecularly imprinted polymer of the separation monose of present embodiment carries out according to the following steps:
One, Silica Surface pre-treatment: it is in 15%～20% hydrochloric acid that silica gel is joined massfraction, under the condition of room temperature and stirring, wash 3～5 times, after then being washed till neutrality with deionized water, be dry under the vacuum condition of 100～120 ℃ in temperature, complete the preprocessing process of silica gel;
two, the silanization of silica gel: the ratio by the volume of the quality of silica gel and toluene is 1g: (8～12) mL, take the silica gel of toluene and step 1, and silica gel is dissolved in toluene, the ratio of pressing again the volume of the quality of silica gel and 3-aminopropyl triethoxysilane is (8～12) g: 10mL, add wherein the 3-aminopropyl triethoxysilane, under the nitrogen protection protection, it is 80～100 ℃ in temperature, under the condition that stirs, back flow reaction 10～14h, then filter and discard liquid, solid formation is first washed under the condition of stirring at room 2～4 times with toluene, wash under the condition of stirring at room 2～4 times with acetone again, be vacuum-drying 10～14h under the condition of 35～45 ℃ in temperature again, complete the silanization of silica gel, obtain amination silica gel,
three, the preparation of molecularly imprinted polymer: the volume ratio of pressing acetonitrile and water is (3～5): 1, to both mix, take ultrasonic frequency as 30～50KHz, reaction 9～11min obtains mixed system, be 0.03～0.07mol/L by the volumetric molar concentration of glucose in this mixed system, be 0.12～0.27mol/L by the volumetric molar concentration of acrylamide in this mixed system, the mass concentration of amination silica gel in this mixed system by step 2 is 0.03～0.07g/mL, with glucose, the amination silica gel of acrylamide and step 2 joins in this mixed system, shake 5～7h under the condition of room temperature, then press N, the mass ratio of N-methylene-bis propionic acid amide and glucose is (4～6): 9, with N, N-methylene-bis propionic acid amide adds, under the nitrogen atmosphere protection, take ultrasonic frequency as 30～50Hz, reaction 9～11min, the mass ratio of pressing again ammonium persulphate and glucose is (0.5～1.5): 9, ammonium persulphate is added, react 12～24h under room temperature condition, after reaction is completed, be centrifugal 10～20min under the condition of 3500～4500r/min at rotating speed, abandoning supernatant, with methyl alcohol and acetic acid mixed solution, solid matter is washed, in methyl alcohol and acetic acid mixed solution, the volume ratio of methyl alcohol and acetic acid is (3～5): 1, wash three times, wash for the first time 5～7h, wash for the second time 11～13h, 11～13h for the third time, centrifugal abandoning supernatant after each washing, wash next time, completing after carrying out washing treatment in temperature is that the Water Under of 35～45 ℃ is bathed evaporate to dryness, be vacuum-drying under the condition of 35～45 ℃ in temperature again, obtain separating the molecularly imprinted polymer of monose.
Embodiment two: what present embodiment was different from embodiment one is: in step 2, the volume ratio of silica gel quality and toluene is 1g: 10mL, and other step is identical with embodiment one with parameter.
Embodiment three: what present embodiment was different from embodiment one or two is: in step 2, the volume ratio of the quality of silica gel and 3-aminopropyl triethoxysilane is 1g: 1mL, and other step is identical with embodiment one or two with parameter.
Embodiment four: what present embodiment was different from one of embodiment one to three is: in step 3, the volume ratio of acetonitrile and water is 4: 1, and other step is identical with one of parameter and embodiment one to three.
Embodiment five: what present embodiment was different from one of embodiment one to four is: in step 3, the volumetric molar concentration of glucose in mixed system is 0.05mol/L, and other step is identical with one of parameter and embodiment one to four.
Embodiment six: what present embodiment was different from one of embodiment one to five is: in step 3, the volumetric molar concentration of acrylamide in mixed system is 0.2mol/L, and other step is identical with one of parameter and embodiment one to five.
Embodiment seven: what present embodiment was different from one of embodiment one to six is: in step 3, the mass concentration of amination silica gel in mixed system of step 2 is 0.05g/mL, and other step is identical with one of parameter and embodiment one to six.
Embodiment eight: what present embodiment was different from one of embodiment one to seven is: N in step 3, the mass ratio of N-methylene-bis propionic acid amide and glucose are 5: 9, and other step is identical with one of parameter and embodiment one to seven.
Embodiment nine: what present embodiment was different from one of embodiment one to eight is: the mass ratio of crossing ammonium persulphate and glucose in step 3 is 1: 9, and other step is identical with one of parameter and embodiment one to eight.
Embodiment ten: what present embodiment was different from one of embodiment one to nine is: in step 3 in methyl alcohol and acetic acid mixed solution the volume ratio of methyl alcohol and acetic acid be 4: 1, other step is identical with one of parameter and embodiment one to nine.
With following verification experimental verification beneficial effect of the present invention:
The preparation method of the molecularly imprinted polymer of the separation monose of embodiment 1, the present embodiment carries out according to the following steps:
One, Silica Surface pre-treatment: taking 13g silica gel, to join the 100ml massfraction be in 20% hydrochloric acid, under the condition of room temperature and stirring, wash 5 times, after then being washed till neutrality with deionized water, be dry under the vacuum condition of 110 ℃ in temperature, complete the preprocessing process of silica gel;
Two, the silanization of silica gel: add 100mL toluene in the 500mL container, then get the silica gel after the 10g step 1 is processed and it is dissolved in toluene, add again the 10mL3-aminopropyl triethoxysilane, under the nitrogen protection protection, it is 90 ℃ in temperature, under the condition that stirs, back flow reaction 12h, then filter and discard liquid, solid formation is first washed 3 times under the condition of stirring at room with toluene, then wash 3 times under the condition of stirring at room with acetone, then be vacuum-drying 12h under the condition of 40 ℃ in temperature, complete the silanization of silica gel, obtain amination silica gel;
three, the preparation of molecularly imprinted polymer: the acetonitrile and the 4mL water that take 16mL will both mix, reaction 10min obtains mixed system take ultrasonic frequency as 40KHz, then add 1mmol glucose in this mixed system, the amination silica gel of the acrylamide of 4mmol and 1g step 2, shake 6h under room temperature condition, and then add 100mg N, N-methylene-bis propionic acid amide, under the nitrogen atmosphere protection, take ultrasonic frequency as 40K Hz, reaction 10min, the ammonium persulphate that adds again 20mg, react 12h under room temperature condition, after reaction is completed, be centrifugal 15min under the condition of 4000r/min at rotating speed, abandoning supernatant, with methyl alcohol and acetic acid mixed solution, solid matter is washed, in methyl alcohol and acetic acid mixed solution, the volume ratio of methyl alcohol and acetic acid is 4: 1, wash three times, wash for the first time 6h, wash for the second time 12h, 12h for the third time, be centrifugal 15min abandoning supernatant under the condition of 4000r/min at rotating speed after each washing, wash next time, completing after carrying out washing treatment in temperature is that the Water Under of 40 ℃ is bathed evaporate to dryness, be vacuum-drying under the condition of 40 ℃ in temperature again, obtain separating the molecularly imprinted polymer of monose.
test one, the molecularly imprinted polymer that takes 1g embodiment 1 joins in the acetonitrile solution that 20mL is dissolved with 9mg/mL glucose, wherein the volume ratio of acetonitrile and water is 4: 1, Static Adsorption 12h, be that to get supernatant liquor after centrifugal 15min under the condition of 4000r/min be evaporate to dryness under 40 ℃ of conditions in temperature at rotating speed, then being configured to mass concentration is the 0.9mg/mL D/W, then be the twin-beam ultraviolet-visible photometer of TU-1900 with model, adopt dinitrosalicylic acid method (DNS), test absorbance under the 540nm wavelength, measure glucose in this D/W concentration be 0.472mg/mL, the molecularly imprinted polymer that embodiment 1 is described is 85.5mg/g to the adsorptive capacity of glucose, existing molecularly imprinted polymer to 2.8～3.4 times of the adsorptive capacity of glucose, adsorption efficiency is high.
test two, the molecularly imprinted polymer that takes 1g embodiment 1 joins in the acetonitrile solution that 20mL is dissolved with the 9mg/mL semi-lactosi, wherein the volume ratio of acetonitrile and water is 4: 1, Static Adsorption 12h, be that to get supernatant liquor under the condition of 4000r/min after centrifugal 15min be evaporate to dryness under the condition of 40 ℃ in temperature at rotating speed, then being configured to mass concentration is the 0.9mg/mL semi-lactosi aqueous solution, then be the twin-beam ultraviolet-visible photometer of TU-1900 with model, adopt dinitrosalicylic acid method (DNS), test absorbance under the 540nm wavelength, measure semi-lactosi in this semi-lactosi aqueous solution concentration be 0.556mg/mL, the molecularly imprinted polymer that embodiment 1 is described is 78.75mg/g to the adsorptive capacity of semi-lactosi, existing molecularly imprinted polymer to 2.6～2.9 times of the adsorptive capacity of semi-lactosi, adsorption efficiency is high.
test three, the molecularly imprinted polymer that takes 1g embodiment 1 joins in the acetonitrile solution that 20mL is dissolved with 9mg/mL fructose, wherein the volume ratio of acetonitrile and water is 4: 1, Static Adsorption 12h, be that to get supernatant liquor under the condition of 4000r/min after centrifugal 15min be evaporate to dryness under the condition of 40 ℃ in temperature at rotating speed, then being configured to mass concentration is 0.9mg/mL fructose water solution, then be the Double-bundle ultraviolet-visible photometer of TU-1900 with model, adopt dinitrosalicylic acid method (DNS), test absorbance under the 540nm wavelength, measure fructose in this fructose water solution concentration be 0.673mg/mL, the molecularly imprinted polymer that embodiment 1 is described is 45.45mg/g to the adsorptive capacity of fructose, existing molecularly imprinted polymer to 2.2～4.5 times of the adsorptive capacity of fructose, adsorption efficiency is high.
Claims (10)
1. the preparation method who separates the molecularly imprinted polymer of monose, the preparation method who it is characterized in that separating the molecularly imprinted polymer of monose carries out according to the following steps:
One, Silica Surface pre-treatment: it is in 15%～20% hydrochloric acid that silica gel is joined massfraction, under the condition of room temperature and stirring, wash 3～5 times, after then being washed till neutrality with deionized water, be dry under the vacuum condition of 100～120 ℃ in temperature, complete the preprocessing process of silica gel;
two, the silanization of silica gel: the ratio by the volume of the quality of silica gel and toluene is 1g: (8～12) mL, take the silica gel of toluene and step 1, and silica gel is dissolved in toluene, the ratio of pressing again the volume of the quality of silica gel and 3-aminopropyl triethoxysilane is (8～12) g: 10mL, add wherein the 3-aminopropyl triethoxysilane, under the nitrogen protection protection, it is 80～100 ℃ in temperature, under the condition that stirs, back flow reaction 10～14h, then filter and discard liquid, solid formation is first washed under the condition of stirring at room 2～4 times with toluene, wash under the condition of stirring at room 2～4 times with acetone again, be vacuum-drying 10～14h under the condition of 35～45 ℃ in temperature again, complete the silanization of silica gel, obtain amination silica gel,
three, the preparation of molecularly imprinted polymer: the volume ratio of pressing acetonitrile and water is (3～5): 1, to both mix, take ultrasonic frequency as 30～50KHz, reaction 9～11min obtains mixed system, be 0.03～0.07mol/L by the volumetric molar concentration of glucose in this mixed system, be 0.12～0.27mol/L by the volumetric molar concentration of acrylamide in this mixed system, the mass concentration of amination silica gel in this mixed system by step 2 is 0.03～0.07g/mL, with glucose, the amination silica gel of acrylamide and step 2 joins in this mixed system, shake 5～7h under the condition of room temperature, then press N, the mass ratio of N-methylene-bis propionic acid amide and glucose is (4～6): 9, with N, N-methylene-bis propionic acid amide adds, under the nitrogen atmosphere protection, take ultrasonic frequency as 30～50Hz, reaction 9～11min, the mass ratio of pressing again ammonium persulphate and glucose is (0.5～1.5): 9, ammonium persulphate is added, react 12～24h under room temperature condition, after reaction is completed, be centrifugal 10～20min under the condition of 3500～4500r/min at rotating speed, abandoning supernatant, with methyl alcohol and acetic acid mixed solution, solid matter is washed, in methyl alcohol and acetic acid mixed solution, the volume ratio of methyl alcohol and acetic acid is (3～5): 1, wash three times, wash for the first time 5～7h, wash for the second time 11～13h, 11～13h for the third time, centrifugal abandoning supernatant after each washing, wash next time, completing after carrying out washing treatment in temperature is that the Water Under of 35～45 ℃ is bathed evaporate to dryness, be vacuum-drying under the condition of 35～45 ℃ in temperature again, obtain separating the molecularly imprinted polymer of monose.
2. the preparation method of the molecularly imprinted polymer of separation monose according to claim 1 is characterized in that the ratio of the volume of silica gel quality and toluene in step 2 is 1g: 10mL.
3. the preparation method of the molecularly imprinted polymer of separation monose according to claim 1 and 2 is characterized in that the ratio of the volume of the quality of silica gel in step 2 and 3-aminopropyl triethoxysilane is 1g: 1mL.
4. the preparation method of the molecularly imprinted polymer of separation monose according to claim 3 is characterized in that in step 3, the volume ratio of acetonitrile and water is 4: 1.
5. the preparation method of the molecularly imprinted polymer of separation monose according to claim 3, is characterized in that in step 3, the volumetric molar concentration of glucose in mixed system is 0.05mol/L.
6. the preparation method of the molecularly imprinted polymer of separation monose according to claim 3, is characterized in that in step 3, the volumetric molar concentration of acrylamide in mixed system is 0.2mol/L.
7. the preparation method of the molecularly imprinted polymer of separation monose according to claim 3, is characterized in that the mass concentration of amination silica gel in mixed system of step 2 in step 3 is 0.05g/mL.
8. the preparation method of the molecularly imprinted polymer of separation monose according to claim 3, is characterized in that N in step 3, and the mass ratio of N-methylene-bis propionic acid amide and glucose is 5: 9.
9. the preparation method of the molecularly imprinted polymer of separation monose according to claim 3, the mass ratio that it is characterized in that crossing in step 3 ammonium persulphate and glucose is 1: 9.
10. the preparation method of the molecularly imprinted polymer of separation monose according to claim 3 is characterized in that in step 3 that in methyl alcohol and acetic acid mixed solution, the volume ratio of methyl alcohol and acetic acid is 4: 1.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104262524A (en) * | 2014-09-12 | 2015-01-07 | 哈尔滨工业大学 | Process for preparing modified silica nanometer molecularly imprinted polymer capable of separating saccharin sodium |
| CN106861661A (en) * | 2015-12-14 | 2017-06-20 | 中国科学院大连化学物理研究所 | Monosaccharide polymer enrichment material and its preparation and the application in glycopeptide enrichment |
| CN115266889A (en) * | 2022-08-01 | 2022-11-01 | 江南大学 | GaN sensor for detecting glucose concentration and detection method |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20070122375A1 (en) * | 2005-09-12 | 2007-05-31 | Council Of Scientific And Industrial Research | Bile acid sequestrant and process for preparation thereof |
| CN101914189A (en) * | 2010-08-04 | 2010-12-15 | 上海交通大学 | Preparation method and application of molecular imprinted polymer on silica surface for specifically adsorbing patulin |
-
2013
- 2013-02-25 CN CN201310058721.3A patent/CN103113536B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20070122375A1 (en) * | 2005-09-12 | 2007-05-31 | Council Of Scientific And Industrial Research | Bile acid sequestrant and process for preparation thereof |
| CN101914189A (en) * | 2010-08-04 | 2010-12-15 | 上海交通大学 | Preparation method and application of molecular imprinted polymer on silica surface for specifically adsorbing patulin |
Non-Patent Citations (2)
| Title |
|---|
| 宁振鑫等: "硅胶表面接枝引发转移终止剂制备牛血红蛋白分子印迹聚合物及性能评价", 《化工时刊》 * |
| 郭敏杰等: "在硅胶表面制备牛血红蛋白分子印迹聚合物", 《化学学报》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104262524A (en) * | 2014-09-12 | 2015-01-07 | 哈尔滨工业大学 | Process for preparing modified silica nanometer molecularly imprinted polymer capable of separating saccharin sodium |
| CN106861661A (en) * | 2015-12-14 | 2017-06-20 | 中国科学院大连化学物理研究所 | Monosaccharide polymer enrichment material and its preparation and the application in glycopeptide enrichment |
| CN106861661B (en) * | 2015-12-14 | 2019-06-25 | 中国科学院大连化学物理研究所 | Monosaccharide polymer enrichment material and its preparation and the application in glycopeptide enrichment |
| CN115266889A (en) * | 2022-08-01 | 2022-11-01 | 江南大学 | GaN sensor for detecting glucose concentration and detection method |
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