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Preparation method of molecularly imprinted polymer microspheres mimicking enzymes for organophosphate hydrolysis

A technology of molecular imprinting and imitating enzymes, which is applied in the fields of alkali metal compounds, chemical instruments and methods, inorganic chemistry, etc., can solve the problems of difficult removal of template molecules, too deep embedding of template molecules, low activity of imitating enzymes, etc., and achieve low cost , Uniform particles, large adsorption effect

Inactive Publication Date: 2016-06-15
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
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Problems solved by technology

However, the functional monomer 4(5)-vinylimidazole used in this method is not commercially available and needs to be synthesized from urocanic acid. also lower cost
In addition, the polymer mimetic enzyme prepared by the bulk polymerization method has large particles, and the catalytic active center is embedded in the polymer. Due to the influence of mass transfer resistance, the activity of the mimetic enzyme is low. Grinding, crushing and sieving of polymer imitating enzymes is not only a cumbersome process, but also a large number of irregular particles will be produced during the grinding process, and the superfine particles after sieving need to be removed, which is labor-intensive and time-consuming, and the yield is greatly improved. Decline (generally less than 50%)
In addition, due to the high concentration of the cross-linking agent, the resulting polymer is highly cross-linked, resulting in too deep embedding of the template molecules, making the removal of the template molecules very difficult.

Method used

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  • Preparation method of molecularly imprinted polymer microspheres mimicking enzymes for organophosphate hydrolysis
  • Preparation method of molecularly imprinted polymer microspheres mimicking enzymes for organophosphate hydrolysis
  • Preparation method of molecularly imprinted polymer microspheres mimicking enzymes for organophosphate hydrolysis

Examples

Experimental program
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Effect test

Embodiment 1

[0021] 0.1530g (1.125mmol) ZnCl 2 , 96 μL (1.125 mmol) methacrylic acid, 408 μL (4.5 mmol) 1-vinylimidazole and 99 μL (0.45 mmol) (4-nitrobenzyl) diethyl phosphate were dissolved in 80 mL of acetonitrile and methanol with a volume ratio of 9: 1, add 2.4mL (16.8mmol) divinylbenzene and 0.2624g (1.6mmol) 2,2'-azobisisobutyronitrile, and then use a wavelength of 365nm under nitrogen protection and room temperature Ultraviolet light irradiation for 12 hours, then centrifuged at 8000 rpm for 10 minutes with a centrifuge, and the resulting solid was shaken and washed with 100 mmol / L bipyridyl methanol solution for 7 hours to remove (4-nitrobenzyl) diethyl phosphate ester, and then washed 3 times with methanol, each time for 30 minutes, and then washed with 100mmol / LZnCl 2 The methanol solution was incubated for 4 hours, centrifuged at 8000 rpm for 10 minutes, the supernatant was discarded, and vacuum-dried at 45°C to obtain molecularly imprinted polymer microspheres of organophosph...

Embodiment 2

[0025] 0.1224g (0.9mmol) ZnCl 2 , 77 μL (0.9 mmol) of methacrylic acid, 326 μL (3.6 mmol) of 1-vinylimidazole and 99 μL (0.45 mmol) of (4-nitrobenzyl) diethyl phosphate were dissolved in 50 mL of acetonitrile and methanol at a volume ratio of 9: 1, add 1.9mL (13.5mmol) divinylbenzene and 0.2214g (1.35mmol) 2,2'-azobisisobutyronitrile, and then under nitrogen protection and room temperature, use a wavelength of 365nm Ultraviolet light irradiation for 12 hours, then centrifuged at 8000 rpm for 10 minutes with a centrifuge, and the resulting solid was shaken and washed with 100 mmol / L bipyridyl methanol solution for 7 hours to remove (4-nitrobenzyl) diethyl phosphate ester, and then washed 3 times with methanol, each time for 30 minutes, and then washed with 100mmol / LZnCl 2 The methanol solution was incubated for 4 hours, centrifuged at 8000 rpm for 10 minutes, the supernatant was discarded, and vacuum-dried at 45°C to obtain molecularly imprinted polymer microspheres of organop...

Embodiment 3

[0027] 0.1836g (1.35mmol) ZnCl 2 , 115 μL (1.35 mmol) of methacrylic acid, 612 μL (6.75 mmol) of 1-vinylimidazole and 99 μL (0.45 mmol) of (4-nitrobenzyl) diethyl phosphate were dissolved in 100 mL of acetonitrile and methanol at a volume ratio of 9: 1, add 3.2mL (22.5mmol) divinylbenzene and 0.3690g (2.25mmol) 2,2'-azobisisobutyronitrile, and then under nitrogen protection and room temperature, use a wavelength of 365nm Ultraviolet light irradiation for 24 hours, then centrifuged at 8000 rpm for 10 minutes with a centrifuge, and the resulting solid was shaken and washed with 100 mmol / L bipyridyl methanol solution for 7 hours to remove (4-nitrobenzyl) diethyl phosphate ester, and then washed 3 times with methanol, each time for 30 minutes, and then washed with 100mmol / LZnCl 2The methanol solution was incubated for 4 hours, centrifuged at 8000 rpm for 10 minutes, the supernatant was discarded, and vacuum-dried at 45°C to obtain molecularly imprinted polymer microspheres of org...

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Abstract

The invention discloses a method for preparing molecularly imprinted polymer microspheres of organophosphorus hydrolysis simulating enzymes. The paraoxon transition state analogue (4-nitrobenzyl) diethyl phosphate is used as a template molecule, and 1-vinylimidazole 1. Methacrylic acid is the functional monomer, and molecular imprinting technology is used to prepare molecularly imprinted polymer microspheres with good dispersion and uniform particle size of organophosphorus hydrolysis imitating enzymes by precipitation polymerization. Compared with the spontaneous hydrolysis of paraoxon, the paraoxon hydrolase activity of the molecularly imprinted polymer microspheres prepared by the present invention can increase the hydrolysis efficiency by a maximum of 188 times, which is higher than that of the non-imprinted polymer synthesized under the condition of no template molecules. Also improved by a factor of 2.3, the measured K m and V max The values ​​are 0.064mmol / L·min and 2.41mmol / L respectively, K cat 0.237S -1 . The organophosphorus hydrolysis mimetic enzyme molecularly imprinted polymer microspheres prepared by the invention can be used not only for the efficient degradation of organophosphorus pesticides, but also for the degradation and destruction of organophosphorus nerve agent chemical weapons.

Description

technical field [0001] The invention belongs to the technical field of degradation of organophosphorus compounds, and in particular relates to a method for preparing molecularly imprinted polymer microspheres of organophosphorus hydrolysis simulating enzymes. Background technique [0002] Organophosphorus pesticides are widely used because of their unstable chemical properties, easy decomposition, short half-life, and difficult accumulation in crops, animals and humans. However, since organophosphorus is used in a wider and wider range, the frequency of use is higher and higher, and the amount of application is increasing, it has become the most serious problem of food contamination. At the same time, organophosphorus compounds can also be used as nerve agents in wars and terrorist attacks. In order to effectively control organophosphorus pesticide residues and organophosphorus chemical weapons, in addition to strengthening the management and restriction of pesticides and n...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F226/06C08F220/06C08F212/36C08F2/48C08J9/26B01J20/26B01J20/28B01J20/30
Inventor 张耀东马珂珂徐吉秀岳宣峰张林李梦凡王丽慧
Owner SHAANXI NORMAL UNIV
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