Preparation of MIL-53-NH-L-mal nanocrystals and its application in the separation of 1-phenylethanol

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Abstract The PSM method was successfully applied to graft L-mal to the uncoordinated amino group of metal-organic frameworks (MOFs) to prepare homochiral MIL-53-NH-L-mal nanocrystals. FT-IR, PXRD, SEM and TGA were utilized to explore the structure and properties of the synthesized nanocrystals. In order to obtain the enantiomers of 1-phenylethanol, the as-prepared MIL-53-NH-L-mal nanocrystals were used as solid phase extraction (SPE) column packing. The parameters such as sample concentration and volume of 1-phenylethanol, dosage of SPE agent, eluent composition and volume for the separation of 1-phenylethanol were investigated. Meanwhile, the recovery and recycling properties of MIL-53-NH-L-mal nanocrystals were also studied. When the column packing was 200 mg, the sample volume and concentration were 1.0 mL and 200 mg·L^-1, respectively and the eluent was hexane/DCM (volume ratio 95/5), the enantiomeric excess value(ee) of separation of 1-phenylethanol can reach 15.86%.

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	Articles by authors
	XU Yue
	FU Yujia
	ZHANG Lijuan
	LU Jie

Keywords： chiral resolution metal-organic frameworks (MOF) post-synthetic modification solid phase extraction 1-phenylethanol

Received 2022-08-15;

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XU Yue, FU Yujia, ZHANG Lijuan, LU Jie.Preparation of MIL-53-NH-L-mal nanocrystals and its application in the separation of 1-phenylethanol[J] Chemcial Industry and Engineering, 2023,V40(1): 104-111

[1] 慕洋洋. 新型生物印迹脂肪酶及其在1-苯乙醇拆分中的应用[D]. 天津:天津大学, 2014 MU Yangyang. The improved bio-imprinted lipase and its application in the resolution of 1-phenylethanol[D]. Tianjin:Tianjin University, 2014 (in Chinese)
[2] XU Z, LIU L, ZHANG J. Synthesis of metal-organic zeolites with homochirality and high porosity for enantioselective separation[J]. Inorganic Chemistry, 2016, 55(13):6355-6357
[3] 赵慧玲. 纤维素的手性分离特性研究[D]. 昆明:云南师范大学, 2016 ZHAO Huiling. Study on chiral separation characteristics of cellulose[D]. Kunming:Yunnan Normal University, 2016 (in Chinese)
[4] YE F, ZHANG Z, ZHAO W, et al. Two methods for the preparation of sitagliptin phosphate via chemical resolution and asymmetric hydrogenation[J]. RSC Advances, 2021, 11(8):4805-4809
[5] 刘亚茹. 天冬氨酸的结晶行为与手性分离[D]. 广州:华南理工大学, 2019 LIU Yaru. Study on the crystallization and chiral resolution of aspartic acid[D]. Guangzhou:South China University of Technology, 2019 (in Chinese)
[6] GHOSH S, BADRUDDOZA A Z M, UDDIN M S, et al. Adsorption of chiral aromatic amino acids onto carboxymethyl-β-cyclodextrin bonded Fe₃O₄/SiO₂ core-shell nanoparticles[J]. Journal of Colloid and Interface Science, 2011, 354(2):483-492
[7] 梁谦, 王恒山. 手性表面活性剂在手性合成、识别及拆分中的应用[J]. 广东化工, 2009, 36(9):67-68 LIANG Qian, WANG Hengshan. The applications of chiral surfactants in chiral synthesis, recognition and separation[J]. Guangdong Chemical Industry, 2009, 36(9):67-68(in Chinese)
[8] ZHAO J, LI H, HAN Y, et al. Chirality from substitution:Enantiomer separation via a modified metal-organic framework[J]. Journal of Materials Chemistry A, 2015, 3(23):12145-12148
[9] SUTTIPAT D, BUTCHA S, ASSAVAPANUMAT S, et al. Chiral macroporous MOF surfaces for electroassisted enantioselective adsorption and separation[J]. ACS Applied Materials & Interfaces, 2020, 12(32):36548-36557
[10] CONNOLLY B M, MADDEN D G, WHEATLEY A E H, et al. Shaping the future of fuel:Monolithic metal-organic frameworks for high-density gas storage[J]. Journal of the American Chemical Society, 2020, 142(19):8541-8549
[11] KOU W, YANG C, YAN X. Post-synthetic modification of metal-organic frameworks for chiral gas chromatography[J]. Journal of Materials Chemistry A, 2018, 6(37):17861-17866
[12] LU Y, ZHANG H, CHAN J, et al. Homochiral MOF-polymer mixed matrix membranes for efficient separation of chiral molecules[J]. Angewandte Chemie (International Ed in English), 2019, 58(47):16928-16935
[13] 张新. 后功能化修饰金属-有机框架材料的制备及其荧光传感性能[D]. 杭州:浙江大学, 2019 ZHANG Xin. Preparation and fluorescence sensing properties of post-functionalization modified metal-organic frameworks[D]. Hangzhou:Zhejiang University, 2019 (in Chinese)
[14] HU X, HUANG G, ZHANG S, et al. An easy and low-cost method of embedding chiral molecules in metal-organic frameworks for enantioseparation[J]. Chemical Communications (Cambridge, England), 2020, 56(54):7459-7462
[15] 魏凯凯. 手性金属-有机骨架材料应用于固相萃取手性分析研究[D]. 昆明:云南师范大学, 2018 WEI Kaikai. Chiral analysis by solid phase extraction with chiral metal-organic frameworks[D]. Kunming:Yunnan Normal University, 2018 (in Chinese)
[16] GASCON J, AKTAY U, HERNANDEZ-ALONSO M D, et al. Amino-based metal-organic frameworks as stable, highly active basic catalysts[J]. Journal of Catalysis, 2009, 261(1):75-87
[17] BEHBAHANI M, MOHABATKAR H, NOSRATI M. Analysis and comparison of lignin peroxidases between fungi and bacteria using three different modes of Chou's general pseudo amino acid composition[J]. Journal of Theoretical Biology, 2016, 411:1-5
[18] LI J, WU Y, LI Z, et al. Characteristics of arsenate removal from water by metal-organic frameworks (MOFs)[J]. Water Science and Technology:A Journal of the International Association on Water Pollution Research, 2014, 70(8):1391-1397
[19] COUCK S, DENAYER J F M, BARON G V, et al. An amine-functionalized MIL-53 metal-organic framework with large separation power for CO₂ and CH₄[J]. Journal of the American Chemical Society, 2009, 131(18):6326-6327
[20] CHENG X, ZHANG A, HOU K, et al. Size- and morphology-controlled NH₂-MIL-53(Al) prepared in DMF-water mixed solvents[J]. Dalton Transactions (Cambridge, England:2003), 2013, 42(37):13698-13705
[21] ALQADAMI A A, KHAN M A, SIDDIQUI M R, et al. Development of citric anhydride anchored mesoporous MOF through post synthesis modification to sequester potentially toxic lead (Ⅱ) from water[J]. Microporous and Mesoporous Materials, 2018, 261:198-206
[22] DA SILVA M R, MAURO LANÇAS F. Evaluation of ionic liquids supported on silica as a sorbent for fully automated online solid-phase extraction with LC-MS determination of sulfonamides in bovine milk samples[J]. Journal of Separation Science, 2018, 41(10):2237-2244
[23] 刘敏. 固定化离子液体拆分氨氯地平对映体研究[D]. 杭州:浙江大学, 2020 LIU Min. Study on enantioseparation of amlodipine by immobilized chiral ionic liquids[D]. Hangzhou:Zhejiang University, 2020 (in Chinese)