Zeolitic Imidazolate Framework-67 Efficiently Catalyzes the Ring-Opening Polymerization of L-Lactide
- Corresponding author: Verpoort Francis, francis.verpoort@urgent.be
Citation:
ZHU Chenyang, LUO Zhixiong, CHEN Cheng, Chaemchuen Somboon, Verpoort Francis. Zeolitic Imidazolate Framework-67 Efficiently Catalyzes the Ring-Opening Polymerization of L-Lactide[J]. Chinese Journal of Applied Chemistry,
;2019, 36(4): 414-422.
doi:
10.11944/j.issn.1000-0518.2019.04.180398
Gupta A P, Kumar V. New Emerging Trends in Synthetic Biodegradable Polymers-Polylactide:A Critique[J]. Eur Polym J, 2007,43(10):4053-4074. doi: 10.1016/j.eurpolymj.2007.06.045
Lim L T, Auras R, Rubino M. Processing Technologies for Poly(Lactic Acid)[J]. Prog Polym Sci, 2008,33(8):820-852. doi: 10.1016/j.progpolymsci.2008.05.004
Van Wouwe P, Dusselier M, Vanleeuw E. Lactide Synthesis and Chirality Control for Polylactic Acid Production[J]. ChemSusChem, 2016,9(9):907-921. doi: 10.1002/cssc.201501695
Terrade F G, Van Krieken J, Verkuijl B J V. Catalytic Cracking of Lactide and Poly(Lactic acid) to Acrylic Acid at Low Temperatures[J]. ChemSusChem, 2017,10(9):1904-1908. doi: 10.1002/cssc.201700108
Dechy-Cabaret O, Martin-Vaca B, Bourissou D. Controlled Ring-Opening Polymerization of Lactide and Glycolide[J]. Chem Rev, 2004,104(12):6147-6176. doi: 10.1021/cr040002s
Kricheldorf H R. Synthesis and Application of Polylactide[J]. Chemosphere, 2001,43(1):49-54. doi: 10.1016/S0045-6535(00)00323-4
Platel R H, Hodgson L M, Williams C K. Biocompatible Initiators for Lactide Polymerization[J]. Polym Rev, 2008,48(1):11-63. doi: 10.1080/15583720701834166
Tschan M J L, Brule E, Haquette P. Synthesis of Biodegradable Polymer from Renewable Resource[J]. Polym Chem, 2012,3(4):836-851. doi: 10.1039/C2PY00452F
Achmad F, Yamanishi K, Liu Z Y. The Effect of the Impurities in Refinery Process from Fermentation Broth on Lactic Acid Polymerization[J]. J Chem Eng Jpn, 2009,42(8):632-635. doi: 10.1252/jcej.09we101
Abdel-Fattah T M, Pinnavaia T J. Tin-Substituted Mesoporous Silica Molecular Sieve(Sn-HMS):Synthesis and Properties as a Heterogeneous Catalyst for Lactide Ring-Opening Polymerization[J]. Chem Commun, 1996(5):665-666. doi: 10.1039/cc9960000665
Yu K, Jones C W. Elucidating the Role of Silica Surfaces in the Ring-Opening Polymerization of Lactide:Catalytic Behavior of Silica-Immobilized Zinc β-Diiminate Complexes[J]. J Catal, 2004,222(2):558-564. doi: 10.1016/j.jcat.2003.12.004
Jones M D, Davidson M G, Keir C G. Heterogeneous Catalysts for the Controlled Ring-Opening Polymerization of rac-Lactide and Homogeneous Silsesquioxane Model Complexes[J]. Dalton Trans, 2008(28):3655-3657. doi: 10.1039/b805274c
Kim E, Shin E W, Yoo I K. Characteristics of Heterogeneous Titanium Alkoxide Catalysts for Ring-Opening Polymerization of Lactide to Produce Polylactide[J]. J Mol Catal A:Chem, 2009,298(1/2):36-39.
Jones M D, Davidson M G, Keir C G. Zinc(Ⅱ) Homogeneous and Heterogeneous Species and Their Application for the Ring-Opening Polymerization of rac-Lactide[J]. Eur J Inorg Chem, 2009(5):635-642.
Jones M D, Keir C G, Johnson A L. Crystallographic Characterization of Novel Zn(Ⅱ) Silsesquioxane Complexes and Their Application as Initiators for the Production of Polylactide[J]. Polyhedron, 2010,29(1):312-316. doi: 10.1016/j.poly.2009.05.024
Di Iulio C, Jones M D, Mahon M F. Zinc(Ⅱ) Silsesquioxane Complexes and Their Application for the Ring-Opening Polymerization of rac-Lactide[J]. Inorg Chem, 2010,49(22):10232-10234. doi: 10.1021/ic101809r
Di Iulio C, Jones M D, Mahon M F. Synthesis of Al(Ⅲ) Silsesquioxane Complexes and Their Exploitation for the Ring Opening Polymerization of rac-Lactide[J]. J Organomet Chem, 2012,718:96-100. doi: 10.1016/j.jorganchem.2012.05.036
Wanna N, Kraithong T, Khamnaen T. Aluminum-and Calcium-Incorporated MCM-41-Type Silica as Supports for the Immobilization of Titanium(Ⅳ) Isopropoxide in Ring-Opening Polymerization of L-Lactide and ε-Caprolactone[J]. Catal Commun, 2014,45:118-123. doi: 10.1016/j.catcom.2013.11.009
Lee E J, Lee K M, Jang J. Characteristics of Silica-Supported Tin(Ⅱ) Methoxide Catalysts for Ring-Opening Polymerization(ROP) of L-Lactide[J]. J Mol Catal A:Chem, 2014,385:68-72. doi: 10.1016/j.molcata.2014.01.008
Chaemchuen S, Kabir N A, Zhou K. Metal-Organic Frameworks for Upgrading Biogas via CO2 Adsorption to Biogas Green Energy[J]. Chem Soc Rev, 2013,42(24):9304-9332. doi: 10.1039/c3cs60244c
XIAO Fan, CUI Yuanjing, QIAN Guodong. Metal-Organic Frameworks for Fluorescence Detection Applications[J]. Chinese J Appl Chem, 2018,35(9):1113-1125.
Chaemchuen S, Luo Z, Zhou K. Defect Formation in Metal-Organic Frameworks Initiated by the Crystal Growth-Rate and Effect on Catalytic Performance[J]. J Catal, 2017,354:84-91. doi: 10.1016/j.jcat.2017.08.012
Chughtai A H, Ahmad N, Younns H A. Metal-Organic Frameworks:Versatile Heterogeneous Catalysts for Efficient Catalytic Organic Transformations[J]. Chem Soc Rev, 2015,44(19):6804-6849. doi: 10.1039/C4CS00395K
Chuck C J, Davidson M G, Jones M D. Air-Stable Titanium Alkoxide Based Metal-Organic Frameworks as an Initiator for Ring-Opening Polymerization of Cyclic Esters[J]. Inorg Chem, 2006,45(17):6595-6597. doi: 10.1021/ic060969+
Wu C Y, Raja D S, Yang C C. Evaluation of Structural Transformation in 2D Metal-Organic Frameworks Based on a 4, 4'-Sulfonyldibenzoate Linker:Microwave-assisted Solvothermal Synthesis, Characterization and Applications[J]. CrystEngComm, 2014,16(39):9308-9319. doi: 10.1039/C4CE01201A
Luo Z, Chaemchuen S, Zhou K. Influence of Lactic Acid on the Catalytic Performance of MDABCO for Ring-Opening Polymerization of L-Lactide[J]. Appl Catal A:Gen, 2017,546:15-21. doi: 10.1016/j.apcata.2017.08.007
Luo Z, Chaemchuen S, Zhou K. Ring-Opening Polymerization of L-Lactide to Cyclic Poly(Lactide) by Zeolitic Imidazole Framework ZIF-8 Catalyst[J]. ChemSusChem, 2017,10(21):4135-4139. doi: 10.1002/cssc.v10.21
Phan A, Doonan C J, Uribe-Romo F J. Synthesis, Structure, and Carbon Dioxide Capture Properties of Zeolitic Imidazolate Frameworks[J]. Acc Chem Res, 2010,43(1):58-67. doi: 10.1021/ar900116g
Chen B, Yang Z, Zhu Y. Zeolitic Imidazolate Framework Materials:Recent Progress in Synthesis and Applications[J]. J Mater Chem A, 2004,2(40):16811-16831.
Chizallet C, Lazare S, Bazer-Bachi D. Catalysis of Transesterification by a Nonfunctionalized Metal-Organic Framework:Acido-Basicity at the External Surface of ZIF-8 Probed by FTIR and Ab Initio Calculations[J]. J Am Chem Soc, 2010,132(35):12365-12377. doi: 10.1021/ja103365s
Tran U P N, Le K K A, Phan N T S. Expanding Applications of Metal-Organic Frameworks:Zeolite Imidazolate Framework ZIF-8 as an Efficient Heterogeneous Catalyst for the Knoevenagel Reaction[J]. ACS Catal, 2011,1(2):120-127. doi: 10.1021/cs1000625
Kalidindi S B, Esken D, Fischer R A. B-N Chemistry@ZIF-8:Dehydrocoupling of Dimethylamine Borane at Room Temperature by Size-Confinement Effects[J]. Chem Eur J, 2011,17(24):6594-6597. doi: 10.1002/chem.v17.24
Mousavi B, Chaemchuen S, Moosavi B. Zeolitic Imidazole Framework-67 as an Efficient Heterogeneous Catalyst for the Conversion of CO2 to Cyclic Carbonates[J]. New J Chem, 2016,40(6):5170-5176. doi: 10.1039/C6NJ00128A
Lin K Y A, Chang H A. Zeolitic Imidazole Framework-67(ZIF-67) as a Heterogeneous Catalyst to Activate Peroxymonosulfate for Degradation of Rhodamine B in Water[J]. J Taiwan Inst Chem Eng, 2015,53:40-45. doi: 10.1016/j.jtice.2015.02.027
Coulembier O, Meyer F, Dubois P. Controlled Room Temperature ROP of L-Lactide by ICl3:A Simple Halogen-Bonding Catalyst[J]. Polym Chem, 2010,1(4):434-437. doi: 10.1039/c0py00013b
Pietrangelo A, Hillmyer M A, Tolman W B. Stereoselective and Controlled Polymerization of DL-Lactide Using Indium(Ⅲ) Trichloride[J]. Chem Commun, 2009(19):2736-2737. doi: 10.1039/b902968k
Pietrangelo A, Knight S C, Gupta A K. Mechanistic Study of the Stereoselective Polymerization of D, L-Lactide Using Indium(Ⅲ) Halides[J]. J Am Chem Soc, 2010,132(33):11649-11657. doi: 10.1021/ja103841h
Kricheldorf H R, Lomadze N, Schwarz G. Cyclic Polylactides by Imidazole-Catalyzed Polymerization of L-Lactide[J]. Macromolecules, 2008,41(21):7812-7816. doi: 10.1021/ma801519t
Blakey I, Yu A, Howdle S M. Controlled Polymerization of Lactide Using an Organo-Catalyst in Supercritical Carbon Dioxide[J]. Green Chem, 2011,13(8):2032-2037. doi: 10.1039/c1gc15344g
Coulembier O, Josse T, Guillerm B. An Imidazole-Based Organocatalyst Designed for Bulk Polymerization of Lactide Isomers:Inspiration from Nature[J]. Chem Commun, 2012,48(95):11695-11697. doi: 10.1039/c2cc37061a
Nederberg F, Connor E F, Moeller M. New Paradigms for Organic Catalysts:The First Organocatalytic Living Polymerization[J]. Angew Chem Int Ed, 2001,40(14):2712-2715. doi: 10.1002/(ISSN)1521-3773
Chizallet C, Bats N. External Surface of Zeolite Imidazolate Frameworks Viewed Ab Initio:Multifunctionality at the Organic-Inorganic Interface[J]. J Phys Chem Lett, 2010,1(1):349-353. doi: 10.1021/jz900192x
Kuruppathparambil R R, Babu R, Jeong H M. A Solid Solution Zeolitic Imidazolate Framework as a Room Temperature Efficient Catalyst for the Chemical Fixation of CO2[J]. Green Chem, 2016,18(23):6349-6356. doi: 10.1039/C6GC01614F
Zhou K, Mousavi B, Luo Z. Characterization and Properties of Zn/Co Zeolitic Imidazolate Frameworks vs. ZIF-8 and ZIF-67[J]. J Mater Chem A, 2017,5(3):952-957. doi: 10.1039/C6TA07860E
Chen Y Z, Wang C, Wu Z Y. From Bimetallic Metal-Organic Framework to Porous Carbon:High Surface Area and Multicomponent Active Dopants for Excellent Electrocatalysis[J]. Adv Mater, 2015,27(34):5010-5016. doi: 10.1002/adma.201502315
Kowalski A, Duda A, Penczek S. Polymerization of L, L-Lactide Initiated by Aluminum Isopropoxide Trimer or Tetramer[J]. Macromolecules, 1998,31(7):2114-2122. doi: 10.1021/ma971737k
Katiyar V, Nanavati H. Ring-Opening Polymerization of L-Lactide Using N-Heterocyclic Molecules:Mechanistic, Kinetics and DFT Studies[J]. Polym Chem, 2010,1(9):1491-1500. doi: 10.1039/c0py00125b
Frediani M, Semeril D, Mariotti A. Ring Opening Polymerization of Lactide Under Solvent-Free Conditions Catalyzed by a Chlorotitanium Calix[J]. Macromol Rapid Commun, 2008,29(18):1554-1560. doi: 10.1002/marc.v29:18
Zhang M, Ni X, Shen Z. Synthesis of Bimetallic Bis(phenolate) N-Heterocyclic Carbene Lanthanide Complexes and Their Applications in the Ring-Opening Polymerization of L-Lactide[J]. Organometallics, 2014,33(23):6861-6867. doi: 10.1021/om500930m
Yuanyi Lu , Jun Zhao , Hongshuang Li . Silver-Catalyzed Ring-Opening Minisci Reaction: Developing a Teaching Experiment Suitable for Undergraduates. University Chemistry, 2024, 39(11): 225-231. doi: 10.3866/PKU.DXHX202401088
Guang Huang , Lei Li , Dingyi Zhang , Xingze Wang , Yugai Huang , Wenhui Liang , Zhifen Guo , Wenmei Jiao . Cobalt’s Valor, Nickel’s Foe: A Comprehensive Chemical Experiment Utilizing a Cobalt-based Imidazolate Framework for Nickel Ion Removal. University Chemistry, 2024, 39(8): 174-183. doi: 10.3866/PKU.DXHX202311051
Xingyang LI , Tianju LIU , Yang GAO , Dandan ZHANG , Yong ZHOU , Meng PAN . A superior methanol-to-propylene catalyst: Construction via synergistic regulation of pore structure and acidic property of high-silica ZSM-5 zeolite. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1279-1289. doi: 10.11862/CJIC.20240026
Xin Han , Zhihao Cheng , Jinfeng Zhang , Jie Liu , Cheng Zhong , Wenbin Hu . Design of Amorphous High-Entropy FeCoCrMnBS (Oxy) Hydroxides for Boosting Oxygen Evolution Reaction. Acta Physico-Chimica Sinica, 2025, 41(4): 100033-. doi: 10.3866/PKU.WHXB202404023
Ruitong Zhang , Zhiqiang Zeng , Xiaoguang Zhang . Improvement of Ethyl Acetate Saponification Reaction and Iodine Clock Reaction Experiments. University Chemistry, 2024, 39(8): 197-203. doi: 10.3866/PKU.DXHX202312004
Qiuyu Xiang , Chunhua Qu , Guang Xu , Yafei Yang , Yue Xia . A Journey beyond “Alum”. University Chemistry, 2024, 39(11): 189-195. doi: 10.12461/PKU.DXHX202404094
Shuying Zhu , Shuting Wu , Ou Zheng . Improvement and Expansion of the Experiment for Determining the Rate Constant of the Saponification Reaction of Ethyl Acetate. University Chemistry, 2024, 39(4): 107-113. doi: 10.3866/PKU.DXHX202310117
Heng Zhang . Determination of All Rate Constants in the Enzyme Catalyzed Reactions Based on Michaelis-Menten Mechanism. University Chemistry, 2024, 39(4): 395-400. doi: 10.3866/PKU.DXHX202310047
Youlin SI , Shuquan SUN , Junsong YANG , Zijun BIE , Yan CHEN , Li LUO . Synthesis and adsorption properties of Zn(Ⅱ) metal-organic framework based on 3, 3', 5, 5'-tetraimidazolyl biphenyl ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1755-1762. doi: 10.11862/CJIC.20240061
Zhifang SU , Zongjie GUAN , Yu FANG . Process of electrocatalytic synthesis of small molecule substances by porous framework materials. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2373-2395. doi: 10.11862/CJIC.20240290
Yifeng TAN , Ping CAO , Kai MA , Jingtong LI , Yuheng WANG . Synthesis of pentaerythritol tetra(2-ethylthylhexoate) catalyzed by h-MoO3/SiO2. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2155-2162. doi: 10.11862/CJIC.20240147
Yue Zhao , Yanfei Li , Tao Xiong . Copper Hydride-Catalyzed Nucleophilic Additions of Unsaturated Hydrocarbons to Aldehydes and Ketones. University Chemistry, 2024, 39(4): 280-285. doi: 10.3866/PKU.DXHX202309001
Hong Lu , Yidie Zhai , Xingxing Cheng , Yujia Gao , Qing Wei , Hao Wei . Advancements and Expansions in the Proline-Catalyzed Asymmetric Aldol Reaction. University Chemistry, 2024, 39(5): 154-162. doi: 10.3866/PKU.DXHX202310074
Guojie Xu , Fang Yu , Yunxia Wang , Meng Sun . Introduction to Metal-Catalyzed β-Carbon Elimination Reaction of Cyclopropenones. University Chemistry, 2024, 39(8): 169-173. doi: 10.3866/PKU.DXHX202401060
Zhuoyan Lv , Yangming Ding , Leilei Kang , Lin Li , Xiao Yan Liu , Aiqin Wang , Tao Zhang . Light-Enhanced Direct Epoxidation of Propylene by Molecular Oxygen over CuOx/TiO2 Catalyst. Acta Physico-Chimica Sinica, 2025, 41(4): 100038-. doi: 10.3866/PKU.WHXB202408015
Jingzhao Cheng , Shiyu Gao , Bei Cheng , Kai Yang , Wang Wang , Shaowen Cao . 4-氨基-1H-咪唑-5-甲腈修饰供体-受体型氮化碳光催化剂的构建及其高效光催化产氢研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2406026-. doi: 10.3866/PKU.WHXB202406026
Meng Lin , Hanrui Chen , Congcong Xu . Preparation and Study of Photo-Enhanced Electrocatalytic Oxygen Evolution Performance of ZIF-67/Copper(I) Oxide Composite: A Recommended Comprehensive Physical Chemistry Experiment. University Chemistry, 2024, 39(4): 163-168. doi: 10.3866/PKU.DXHX202308117
Ke QIAO , Yanlin LI , Shengli HUANG , Guoyu YANG . Advancements in asymmetric catalysis employing chiral iridium (ruthenium) complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2091-2104. doi: 10.11862/CJIC.20240265
You Wu , Chang Cheng , Kezhen Qi , Bei Cheng , Jianjun Zhang , Jiaguo Yu , Liuyang Zhang . ZnO/D-A共轭聚合物S型异质结高效光催化产H2O2及其电荷转移动力学研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2406027-. doi: 10.3866/PKU.WHXB202406027
Yingchun ZHANG , Yiwei SHI , Ruijie YANG , Xin WANG , Zhiguo SONG , Min WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078
Conditions:160 ℃, n(L-LA)/n(ZIFs)=100
Conditions:160 ℃, n(L-LA)/n(ZIFs)=100