Volume 45 Issue 3
May  2023
Turn off MathJax
Article Contents
MA Rong, YUAN Longmiao, LIU Yanhong, WANG Zhiyu, WU Yingqin. Screening of functional monomers and preparation of molecularly imprinted polymers (MIPs) in molecularly imprinted polymers of steranes[J]. PETROLEUM GEOLOGY & EXPERIMENT, 2023, 45(3): 537-548. doi: 10.11781/sysydz202303537
Citation: MA Rong, YUAN Longmiao, LIU Yanhong, WANG Zhiyu, WU Yingqin. Screening of functional monomers and preparation of molecularly imprinted polymers (MIPs) in molecularly imprinted polymers of steranes[J]. PETROLEUM GEOLOGY & EXPERIMENT, 2023, 45(3): 537-548. doi: 10.11781/sysydz202303537

Screening of functional monomers and preparation of molecularly imprinted polymers (MIPs) in molecularly imprinted polymers of steranes

doi: 10.11781/sysydz202303537
  • Received Date: 2022-11-17
  • Rev Recd Date: 2023-03-30
  • Publish Date: 2023-05-28
  • To prepare molecularly imprinted polymers (MIPs) with specific selectivity for steranes, the prepolyme-rization system was screened by UV spectroscopy to determine the type, proportion and mode of action of functional monomers. In this study, the interaction intensities between three template molecules (cholesterol, β-sitosterol, deoxycholic acid) and four functional monomers (acrylic acid (AA), methacrylic acid (MAA), methyl methacrylate (MMA), and acrylamide (AM)) are compared respectively. The results show that the functional monomer AA can interact strongly with the three template molecules and form a stable prepolymerization system, so AA is selected as the functional monomer of MIPs. In addition, the UV spectral absorbance change and differential UV spectral analysis of different proportions of AA show that the optimal concentration ratios of the three template molecules to functional monomer AA are all 1:4, and the stable complex configurations formed are cholesterol-1AA, β-sitosterol-1AA and deoxycholic acid-3AA, respectively. The MIPs are successfully synthesized by precipitation polymerization using EDGMA as dispersant and AIBN as initiator, and the results of FTIR show that MIPs are well prepared. Therefore, this method can be used for the screening and preparation of MIPs functional monomers with specific selectivity for steranes, and provide technical support for the study of oil-source correlation between deep and ultra-deep source rocks.

     

  • loading
  • [1]
    SHIRNESHAN G, BAKHTIARI A R, MEMARIANI M. Distribution and origins of n-alkanes, hopanes, and steranes in rivers and marine sediments from southwest Caspian coast, Iran: implications for identifying petroleum hydrocarbon inputs[J]. Environmental Science and Pollution Research, 2016, 23(17): 17484-17495. doi: 10.1007/s11356-016-6825-8
    [2]
    LIU Shiju, GAO Gang, JIN Jun, et al. Source rock with high abundance of C28 regular sterane in typical brackish-saline lacustrine sediments: biogenic source, depositional environment and hydrocarbon generation potential in Junggar Basin, China[J]. Journal of Petroleum Science and Engineering, 2022, 208: 109670. doi: 10.1016/j.petrol.2021.109670
    [3]
    万涛, 张洪安, 张宝君, 等. C29重排谷甾烷在油源对比研究中的应用: 以银额盆地查干凹陷为例[J]. 断块油气田, 2021, 28(2): 173-178. https://www.cnki.com.cn/Article/CJFDTOTAL-DKYT202102007.htm

    WAN Tao, ZHANG Hongan, ZHANG Baojun, et al. The application of C29 rearranged sitostane in oil source correlation research: taking Chagan Depression of Yingen-Ejinaqi Basin for example[J]. Fault-Block Oil and Gas Field, 2021, 28(2): 173-178. https://www.cnki.com.cn/Article/CJFDTOTAL-DKYT202102007.htm
    [4]
    KASHIRTSEV V A, DOLZHENKO K V, FOMIN A N, et al. Hydrocarbon composition of bitumen from deeply buried terrestrial organic matter (zone of apocatagenesis)[J]. Russian Geology and Geophysics, 2017, 58(6): 702-710. doi: 10.1016/j.rgg.2016.03.018
    [5]
    MEN Jiying, DONG Chengya, SHI Hongxing, et al. Surface molecular imprinted membranes as a "gate" for selective transdermal release of chiral drug amlodipine[J]. Journal of Membrane Science, 2022, 664: 121059. doi: 10.1016/j.memsci.2022.121059
    [6]
    LI Aimin, HUANG Xiaolan, YAN Ling, et al. Pseudo-template molecularly imprinted polymeric fiber solid-phase microextraction coupled to gas chromatography for ultrasensitive determination of 2, 4, 6-trihalophenol disinfection by-products[J]. Journal of Chromatography A, 2022, 1678: 463322. doi: 10.1016/j.chroma.2022.463322
    [7]
    RAMANAVICIUS S, SAMUKAITE-BUBNIENE U, RATAUTAITE V, et al. Electrochemical molecularly imprinted polymer based sensors for pharmaceutical and biomedical applications (review)[J]. Journal of Pharmaceutical and Biomedical Analysis, 2022, 215: 114739. doi: 10.1016/j.jpba.2022.114739
    [8]
    WANG Xingguo, LIU Zhixiang, LU Jian, et al. Highly selective membrane for efficient separation of environmental determinands: enhanced molecular imprinting in polydopamine-embedded porous sleeve[J]. Chemical Engineering Journal, 2022, 449: 137825. doi: 10.1016/j.cej.2022.137825
    [9]
    WANG Xuemei, HUANG Pengfei, MA Xiaomin, et al. Enhanced in-out-tube solid-phase microextraction by molecularly imprinted polymers-coated capillary followed by HPLC for Endocrine Disrupting Chemicals analysis[J]. Talanta, 2019, 194: 7-13. doi: 10.1016/j.talanta.2018.10.027
    [10]
    YUAN Ya, WANG Yuzhi, HUANG Meidong, et al. Development and characterization of molecularly imprinted polymers for the selective enrichment of podophyllotoxin from traditional Chinese medicines[J]. Analytica Chimica Acta, 2011, 695(1/2): 63-72. http://www.sciencedirect.com/science/article/pii/S0003267011005290
    [11]
    KARIM K, BRETON F, ROUILLON R, et al. How to find effective functional monomers for effective molecularly imprinted polymers?[J]. Advanced Drug Delivery Reviews, 2005, 57(12): 1795-1808. doi: 10.1016/j.addr.2005.07.013
    [12]
    银珍红, 陈小明. 2, 4-二氯苯氧乙酸分子印迹整体柱的制备、表征及色谱性能研究[J]. 分析测试学报, 2009, 28(8): 949-953. https://www.cnki.com.cn/Article/CJFDTOTAL-TEST200908018.htm

    YING Zhenhong, CHEN Xiaoming. Synthesis and characterization of 2, 4-dichlorophenoxyacetic acid molecularly imprinted monolithic column and its chromatographic property[J]. Journal of Instrumental Analysis, 2009, 28(8): 949-953. https://www.cnki.com.cn/Article/CJFDTOTAL-TEST200908018.htm
    [13]
    MA Xingbin, LIN Hongling, ZHANG Jiyu, et al. Preparation and characterization of dummy molecularly imprinted polymers for separation and determination of farrerol from Rhododendronaganniphum using HPLC[J]. Green Chemistry Letters and Reviews, 2018, 11(4): 513-522. doi: 10.1080/17518253.2018.1541481
    [14]
    李璐, 周刘梅, 解新安, 等. 溴氰菊酯农药残留检测的分子印迹预聚体系筛选及吸附性能[J]. 农业工程学报, 2019, 35(1): 269-277. https://www.cnki.com.cn/Article/CJFDTOTAL-NYGU201901034.htm

    LI Lu, ZHOU Liumei, XIE Xinan, et al. Screening of molecularly imprinted pre-assembly system for detection of deltamethrin pesticide residues and its specific adsorption properties[J]. Transactions of the Chinese Society of Agricultural Engineering, 2019, 35(1): 269-277. https://www.cnki.com.cn/Article/CJFDTOTAL-NYGU201901034.htm
    [15]
    WANG Liping, SHE Xuhui, CHEN Zhi, et al. Preparation and characterization of a chiral molecularly imprinted polymer with a novel functional monomer for controlled release of S-sulpiride[J]. International Journal of Pharmaceutics, 2021, 601: 120526. doi: 10.1016/j.ijpharm.2021.120526
    [16]
    高博, 杨宏伟, 宋文琦, 等. 分子模拟辅助设计L-苯丙氨酸分子印迹聚合物及其性能研究[J]. 化学通报, 2019, 82(3): 251-257. https://www.cnki.com.cn/Article/CJFDTOTAL-HXTB201903010.htm

    GAO Bo, YANG Hongwei, SONG Wenqi, et al. Molecular simulation-aided design of L-phenylalanine-imprinted polymers and its properties[J]. Chemistry, 2019, 82(3): 251-257. https://www.cnki.com.cn/Article/CJFDTOTAL-HXTB201903010.htm
    [17]
    SÁNCHEZ-GONZÁLEZ J, PEÑA-GALLEGO Á, SANMARTÍN J, et al. NMR spectroscopy for assessing cocaine-functional monomer interactions when preparing molecularly imprinted polymers[J]. Microchemical Journal, 2019, 147: 813-817. doi: 10.1016/j.microc.2019.03.088
    [18]
    杨俊, 朱晓兰, 苏庆德, 等. 可天宁印迹聚合物分子识别特性的光谱与XPS研究[J]. 光谱学与光谱分析, 2007, 27(6): 1152-1155. https://www.cnki.com.cn/Article/CJFDTOTAL-GUAN200706031.htm

    YANG Jun, ZHU Xiaolan, SU Qingde, et al. Spectroscopy and XPS studies on molecular recognition of a molecularly imprinted cotinine-specific polymer[J]. Spectroscopy and Spectral Analysis, 2007, 27(6): 1152-1155. https://www.cnki.com.cn/Article/CJFDTOTAL-GUAN200706031.htm
    [19]
    WADIE M, ABDEL-MOETY EM, REZK M R, et al. Electro-polymerized poly-methyldopa as a novel synthetic mussel-inspired molecularly imprinted polymeric sensor for darifenacin: computational and experimental study[J]. Applied Materials Today, 2022, 29: 101595. doi: 10.1016/j.apmt.2022.101595
    [20]
    GARCIA L L C, FIGUEIREDO-FILHO L C S, OLIVEIRA G G, et al. Square-wave voltammetric determination of paraquat using a glassy carbon electrode modified with multiwalled carbon nanotubes within a dihexadecyl hydrogen phosphate (DHP) film[J]. Sensors and Actuators B: Chemical, 2013, 181: 306-311. doi: 10.1016/j.snb.2013.01.091
    [21]
    林秋明, 何建峰, 刘岚, 等. 不同功能单体合成的分子印迹聚合物识别性能的研究[J]. 化学研究与应用, 2007, 19(10): 1084-1088. https://www.cnki.com.cn/Article/CJFDTOTAL-HXYJ200710005.htm

    LIN Qiuming, HE Jianfeng, LIU Lan, et al. Study on the effect of recognized characteristics of quercetin imprinted polymers with different functional monomers[J]. Chemical Research and Application, 2007, 19(10): 1084-1088. https://www.cnki.com.cn/Article/CJFDTOTAL-HXYJ200710005.htm
    [22]
    朱淮武. 有机分子结构波谱解析[M]. 北京: 化学工业出版社, 2005.

    ZHU Huaiwu. Organic molecular structure spectra analysis[M]. Beijing: Chemical Industry Press, 2005.
    [23]
    张晓. 番红花红T分子印迹聚合物的制备及其性能研究[D]. 兰州: 兰州交通大学, 2021.

    ZHANG Xiao. Preparation and properties of safranin T molecular imprinted polymer[D]. Lanzhou: Lanzhou Jiaotong University, 2021.
    [24]
    刘婷婷, 卢春霞. 齐墩果酸分子印迹体系优化[J]. 江苏农业科学, 2021, 49(2): 139-145. https://www.cnki.com.cn/Article/CJFDTOTAL-JSNY202102025.htm

    LIU Tingting, LU Chunxia. Optimization of molecularly imprinted system for oleanolic acid[J]. Jiangsu Agricultural Sciences, 2021, 49(2): 139-145. https://www.cnki.com.cn/Article/CJFDTOTAL-JSNY202102025.htm
    [25]
    张孝刚, 朱秋劲, 胡萍. 三聚氰胺分子印迹预组装体系紫外光谱研究[J]. 食品科学, 2011, 32(21): 128-132. https://www.cnki.com.cn/Article/CJFDTOTAL-SPKX201121025.htm

    ZHANG Xiaogang, ZHU Qiujin, HU Ping. Ultraviolet spectroscopic investigations into melamine molecular imprinting pre-assembly system[J]. Food Science, 2011, 32(21): 128-132. https://www.cnki.com.cn/Article/CJFDTOTAL-SPKX201121025.htm
    [26]
    CHEN Changbao, CHEN Yanjun, ZHOU Jie, et al. A 9-vinyladenine-based molecularly imprinted polymeric membrane for the efficient recognition of plant hormone 1H-indole-3-acetic acid[J]. Analytica Chimica Acta, 2006, 569(1/2): 58-65. http://www.sciencedirect.com/science/article/pii/S0003267006006362
  • 加载中

Catalog

    通讯作者: 陈斌, bchen63@163.com
    • 1. 

      沈阳化工大学材料科学与工程学院 沈阳 110142

    1. 本站搜索
    2. 百度学术搜索
    3. 万方数据库搜索
    4. CNKI搜索

    Figures(15)  / Tables(4)

    Article Metrics

    Article views (442) PDF downloads(40) Cited by()
    Proportional views
    Related

    /

    DownLoad:  Full-Size Img  PowerPoint
    Return
    Return