Synthesis of Poly(isosorbide carbonate) via Melt Polycondensation Catalyzed by Ca/SBA-15 Solid Base
- Corresponding author: Gong-Ying Wang, wanggongying1102@126.com
Citation: Xiao-Long Shen, Zi-Qing Wang, Qing-Yin Wang, Shao-Ying Liu, Gong-Ying Wang. Synthesis of Poly(isosorbide carbonate) via Melt Polycondensation Catalyzed by Ca/SBA-15 Solid Base[J]. Chinese Journal of Polymer Science, ;2018, 36(9): 1027-1035. doi: 10.1007/s10118-018-2137-4
Oyarzabal, A.; Cristiano-Tassi, A.; Laredo, E.; Newman, D.; Bello, A.; Etxeberría, A.; Eguiazabal, J. I.; Zubitur, M.; Mugica, A.; Müller, A. J. Dielectric, mechanical and transport properties of bisphenol A polycarbonate/graphene nanocomposites prepared by melt blending. J. Appl. Polym. Sci. 2017, 134(13), 44654−44667
doi: 10.1002/APP.44654
Zhao, H. M.; Jiang, M. J.; Tian, H. S. NaOH and TEAH catalyzed polycarbonate synthesis through melt transesterification and the rearrangement prodouts in both processes. Acta Polymerica Sinica (in Chinese) 2011, (2), 192−197
doi: 10.3724/SP.J.1105.2011.10025
Song, Q. L.; Wen, H. Y.; Christiansen, J. D.; Yu, D. H.; Chen, C. S.; Jiang, S. C. Analysis of structure transition and compatibility of PTT/PC blend without transesterification. Chinese J. Polym. Sci. 2016, 34(9), 1172−1182
doi: 10.1007/s10118-016-1820-6
Hao, Y. P.; Yang, H. L.; Zhang, G. B.; Zhang, H. L.; Gao, G.; Dong, L. S. Rheological, thermal and mechanical properties of biodegradable poly(propylene carbonate)/polylactide/poly(1,2-propylene glycol adipate) blown films. Chinese J. Polym. Sci. 2015, 33(12), 1702−1712
doi: 10.1007/s10118-015-1714-z
Geens, T.; Aerts, D.; Berthot, C.; Bourguignon, J. P.; Goeyens, L.; Lecomte, P.; Maghuin-Rogister, G.; Pironnet, A. M.; Pussemier, L.; Scippo, M. L. A review of dietary and non-dietary exposure to bisphenol-A. Fd. Chem. Toxicol. 2012, 50(10), 3725−3740
doi: 10.1016/j.fct.2012.07.059
Gubbels, E.; Jasinska-Walc, L.; Koning, C. E. Synthesis and characterization of novel renewable polyesters based on 2,5-furandicarboxylic acid and 2,3-butanediol. J. Polym. Sci., Part A: Polym. Chem. 2013, 51(4), 890−898
doi: 10.1002/pola.26446
Li, C.; Dai, J. Y.; Liu, X. Q.; Jiang, Y. H.; Ma, S. Q.; Zhu, J. Green synthesis of a bio-based epoxy curing agent from isosorbide in aqueous condition and shape memory properties investigation of the cured resin. Macromol. Chem. Phys. 2016, 217(13), 1439−1447
doi: 10.1002/macp.v217.13
Wang, J. G.; Liu, X. Q.; Zhang, Y. J.; Liu, F.; Zhu, J. Modification of poly(ethylene 2,5-furandicarboxylate) with 1,4-cyclohexanedimethylene: Influence of composition on mechanical and barrier properties. Polymer 2016, 103, 1−8
doi: 10.1016/j.polymer.2016.09.030
Deng, J.; Liu, X. Q.; Li, C.; Jiang, Y. H.; Zhu, J. Synthesis and properties of a bio-based epoxy resin from 2,5-furandicarboxylic acid (FDCA). RSC Adv. 2015, 5(21), 15930−15939
doi: 10.1039/C5RA00242G
Dai, J. Y.; Ma, S. Q.; Teng, N.; Dai, X. Y.; Shen, X. B.; Wang, S.; Liu, X. Q.; Zhu, J. 2,5-Furandicarboxylic acid- and itaconic acid-derived fully biobased unsaturated polyesters and their cross-linked networks. Ind. Eng. Chem. Res. 2017, 56(10), 2650−2657
doi: 10.1021/acs.iecr.7b00049
Kricheldorf, H. R. " Sugar diols” as building blocks of polycondensates. J. Macromol. Sci. Rev. Macromol. Chem. Phys. 1997, C37(4), 599−631
doi: 10.1080/15321799708009650
Fenouillot, F. F.; Rousseau, A.; Colomines, G.; Saint-Loup, R.; Pascault, J. P. Polymers from renewable 1,4:3,6-dianhydrohexitols (isosorbide, isomannide and isoidide): A review. Prog. Polym. Sci. 2010, 35(5), 578−622
doi: 10.1016/j.progpolymsci.2009.10.001
Bersot, J. C.; Jacquel, D.; Saint-Loup, P.; Fuertes, P.; Rousseau, A.; Pascault, J. P.; Spitz, R.; Fenouillot, F.; Monteil, V. Efficiency increase of poly(ethylene terephthalate-co-isosorbide terephthalate) synthesis using bimetallic catalytic systems. Macromol. Chem. Phys. 2011, 212(19), 2114−2120
doi: 10.1002/macp.v212.19
Gioia, C.; Vannini, M.; Marchese, P.; Minesso, A.; Cavalieri, R.; Colonna, M.; Celli, A. Sustainable polyesters for powder coating applications from recycled PET, isosorbide and succinic acid. Green Chem. 2014, 16(4), 1807−1815
doi: 10.1039/C3GC42122H
Caouthar, A. A.; Loupy, A.; Bortolussi, M.; Blais, J. C.; Dubreucq, L.; Meddour, A. Synthesis and characterization of new polyamides based on diphenylaminoisosorbide. Polym. Chem. 2005, 43(24), 6480−6491
doi: 10.1002/pola.21116
Wroblewska, A.; Zych, A.; Thiyagarajan, S.; Dudenko, D.; van Es, D.; Hansen, M. R.; Koning, C.; Duchateau, R.; Jasinska-Walc, L. Towards sugar-derived polyamides as environmentally friendly materials. Polym. Chem. 2015, 6(22), 4133−4143
doi: 10.1039/C5PY00521C
Lee, C. H.; Kato, M.; Usuki, A. Preparation and properties of bio-based polycarbonate/clay nanocomposites. J. Mater. Chem. A 2011, 21(19), 6844−6847
doi: 10.1039/c1jm10087d
Chatti, S.; Schwarz, S.; Kricheldorf, H. R. Crclic and noncylic polycarbonates of isosorbide (1,4:3,6-dianhydro-D-glucitol). Macromolecules 2006, 39(26), 9064−9070
doi: 10.1021/ma0606051
Feng, L.; Zhu, W. X.; Li, C. C.; Guan, G. H.; Zhang, D.; Xiao, Y. N.; Zheng, L. C. A high-molecular-weight and high-Tg poly(ester carbonate) partially based on isosorbide: synthesis and structure-property relationships. Polym. Chem. 2014, 6(4), 633−642
doi: 10.1039/c4py00976b
Park, J. H.; Jeon, J. Y.; Lee, J. J.; Jang, Y.; Varghese, J. K.; Lee, B. Y. Preparation of high-molecular-weight aliphatic polycarbonates by condensation polymerization of diols and dimethyl carbonate. Macromolecules 2013, 46(9), 3301−3308
doi: 10.1021/ma400360w
Li, Q.; Zhu, W. X.; Li, C. C.; Guan, G. H.; Zhang, D.; Xiao, Y. N.; Zheng, L. C. A non-phosgene process to homopolycarbonate and copolycarbonates of isosorbide using dimethyl carbonate: synthesis, characterization, and properties. J. Polym. Sci., Part A: Polym. Chem. 2013, 51(6), 1387−1397
doi: 10.1002/pola.26507
Eo, Y. S.; Rhee, H. W.; Shin, S. H. Catalyst screening for the melt polymerization of isosorbide-based polycarbonate. J. Ind. Eng. Chem. 2016, 37, 42−46
doi: 10.1016/j.jiec.2016.03.007
Sun, W.; Xu, F.; Cheng, W. G.; Sun, J.; Ning, G. Q.; Zhang, S. J. Synthesis of isosorbide-based polycarbonates via melt polycondensation catalyzed by quaternary ammonium ionic liquids. Chin. J. Catal. 2017, 38(5), 908−917
doi: 10.1016/S1872-2067(17)62822-5
Chrysanthos, M.; Galy, J.; Pascault, J. P. Preparation and properties of bio-based epoxy networks derived from isosorbide diglycidyl ether. Polymer 2011, 52, 3611−3620
doi: 10.1016/j.polymer.2011.06.001
Hu, F. S.; La Scala, J. J.; Sadler, J. M.; Palmese, G. R. Synthesis and characterization of thermosetting furan-based epoxy systems. Macromolecules 2014, 47(10), 3332−3342
doi: 10.1021/ma500687t
Li, C.; Dai, J. Y.; Liu, X. Q.; Jiang, Y. H.; Ma, S. Q.; Zhu, J. Green Synthesis of a bio-based epoxy curing agent from isosorbide in aqueous condition and shape memory properties investigation of the cured resin. Macromol. Chem. Phys. 2016, 217(13), 1439−1447
doi: 10.1002/macp.v217.13
Zhao, D. Y.; Feng, J. L.; Huo, Q. S.; Melosh, N.; Fredrickson, G. H.; Chmelka, B. F.; Stucky, G. D. Triblock copolymer syntheses of mesoporous silica with periodic 50 to 300 angstrom pores. Science 1998, 279(5350), 548−552
doi: 10.1126/science.279.5350.548
Zhao, D. Y.; Huo, Q. S.; Feng, J. L.; Chmelka, B. F.; Stucky, G. D. Nonionic triblock and star diblock copolymer and oligomeric surfactant syntheses of highly ordered, hydrothermally stable, mesoporous silica structures. J. Am. Chem. Soc. 1998, 120(24), 6024−6036
doi: 10.1021/ja974025i
Chen, S. Y.; Huang, C. Y.; Yokoi, T.; Tang, C. Y.; Huang, S. J.; Lee, J. J.; Chan, J. C. C.; Tatsumi, T.; Cheng, S. Synthesis and catalytic activity of amino-functionalized SBA-15 materials with controllable channel lengths and amino loadings. J. Mater. Chem. 2012, 22(5), 2233−2243
doi: 10.1039/C2JM14393C
Liu, X. Y.; Sun, L. B.; Lu, F.; Liu, X. D.; Liu, X. Q. Low-temperature generation of strong basicity via an unprecedented guest-host redox interaction. Chem. Commun. 2013, 49(73), 8087−8089
doi: 10.1039/c3cc44721a
Albuquerque, M. C. G.; Jiménez-Urbistondo, I.; Santamaría-González, J.; Mérida-Robles, J. M.; Moreno-Tost, R.; Rodríguez-Castellón, E.; Jiménez-López, A.; Azevedo, D. C. S.; Cavalcante, C. L.; Maireles-Torres, P. CaO supported on mesoporous silicas as basic catalysts for transesterification reactions. Appl. Catal. A-Gen. 2008, 334(1-2), 35−43
doi: 10.1016/j.apcata.2007.09.028
Sun, L. B.; Kou, J. H.; Chun, Y.; Yang, J.; Gu, F. N.; Wang, Y.; Zhu, J. H.; Zou, Z. G. New attempt at directly generating superbasicity on mesoporous silica SBA-15. Inorg. Chem. 2008, 47(10), 4199−4208
doi: 10.1021/ic702223b
Arumugam, A.; Ponnusami, V. Optimization of recovery of silica from sugarcane leaf ash and Ca/SBA-15 solid base for transesterification of Calophyllum inophyllum oil. J. Sol-Gel. Sci. Technol. 2015, 74(1), 132−142
doi: 10.1007/s10971-014-3586-z
Tantirungrotechai, J.; Thananupappaisal, P.; Yoosuk, B.; Viriya-empikul, N.; Faungnawakij, K. One-pot synthesis of calcium-incorporated MCM-41 as a solid base catalyst for transesterification of palm olefin. Catal. Commun. 2011, 16(1), 25−29
doi: 10.1016/j.catcom.2011.09.002
Sun, H.; Han, J. X.; Ding, Y. Q.; Li, W.; Duan, J. Z.; Chen, P.; Lou, H.; Zheng, X. M. One-pot synthesized mesoporous Ca/SBA-15 solid base for transesterification of sunflower oil with methanol. Appl. Catal. A-Gen. 2010, 390(1-2), 26−34
doi: 10.1016/j.apcata.2010.09.030
Nair, P. A.; Ramesh, P. Synthesis and characterization of poly(urethane-ether)s from calcium salt of p-hydroxybenzoic acid. J. Appl. Polym. Sci. 2011, 122(3), 1946−1952
doi: 10.1002/app.33906
Wang, Z. Q.; Yang, X. G.; Li, J. G.; Liu, S. Y.; Wang, G. Y. Synthesis of high-molecular-weight aliphatic polycarbonates from diphenyl carbonate and aliphatic diols by solid base. J. Mol. Catal. A-Chem. 2016, 424, 77−84
doi: 10.1016/j.molcata.2016.08.017
Zhu, W. X.; Huang, X.; Li, C. C.; Xiao, Y. N.; Zhang, D.; Guan, G. H. High-molecular-weight aliphatic polycarbonates by melt polycondensation of dimethyl carbonate and aliphatic diols: synthesis and characterization. Polym. Int. 2011, 60(7), 1060−1067
doi: 10.1002/pi.v60.7
Liu, F.; Yang, X. G.; Li, J. G.; Liu, S. Y.; Yao, J.; Chen, T.; Wang, G. Y. Synthesis of poly (butylene carbonate) by melt transesterification of diphenyl carbonate and 1,4-butanediol. Acta Polymerica Sinica (in Chinese) 2014, (5), 628−635
doi: 10.3724/SP.J.1105.2014.13335
Naik, P. U.; Refes, K.; Sadaka, F.; Brachais, C. H.; Boni, G.; Couvercelle, J. P.; Picquet, M.; Plasseraud, L. Organo-catalyzed synthesis of aliphatic polycarbonates in solvent-free conditions. Polym. Chem. 2012, 3(6), 1475−1480
doi: 10.1039/c2py20056b
Wang, Z. Q.; Bai, Y. S.; Jiang, W.; Yang, X. G.; Liu, S. Y.; Wang, G. Y. Structure-activity correlations of calcined Mg-Al hydrocalcites for aliphatic polycarbonate synthesis via transesterification process. Chinese J. Polym. Sci. 2017, 35(1), 130−140
doi: 10.1007/s10118-017-1887-8
Wang, Z. Q.; Yang, X. G.; Li, S. Y.; Hu, J.; Zhang, H.; Wang, G. Y. One-pot synthesis of high-molecular-weight aliphatic polycarbonates via melt transesterification of diphenyl carbonate and diols using Zn(OAc)2 as a catalyst. RSC Adv. 2015, 5(106), 87311−89319
doi: 10.1039/C5RA18275A
Kresge, C. T.; Leonowicz, M. E.; Roth, W. J.; Vartuli, J. C.; Beck, J. S. Ordered mesoporous molecular sieves synthesized by a liquid-crystal template mechanism. Nature 1992, 359(6397), 710−712
doi: 10.1038/359710a0
Radwan, N. R. E. Influence of La2O3 and ZrO2 as promoters on surface and catalytic properties of CuO/MgO system prepared by sol-gel method. Appl. Catal. A-Gen. 2006, 299(17), 103−121
doi: 10.1016/j.apcata.2005.10.008
Tian, B. Z.; Liu, X. Y.; Yu, C. Z.; Gao, F.; Luo, Q; Xie, S. H.; Tu, B.; Zhao, D. Y. Microwave assisted template removal of siliceous porous materials. Chem. Commun. 2002, 11, 1186−1187
doi: 10.1039/b202180c
Jiang, Q.; Wu, Z. Y.; Wang, Y. M.; Cao, Y.; Zhou, C. F.; Zhu, J. H. Fabrication of photoluminescent ZnO/SBA-15 through directly dispersing zinc nitrate into the as-prepared mesoporous silica occluded with template. J. Mater. Chem. 2006, 16(16), 1536−1542
doi: 10.1039/b516061h
Di Cosimo, J. I.; Díez, V. K.; Xu, M.; Iglesia, E.; Apesteguía, C. R. Structure and surface and catalytic properties of Mg-Al basic oxide. J. Catal. 1998, 178(2), 499−510
doi: 10.1006/jcat.1998.2161
Zheng, L. P.; Xia, S. X.; Hou, Z. T.; Zhang, M. Y.; Hou, Z. Y. Transesterification of glycerol with dimethyl carbonate over Mg-Al hydrotalcites. Chin. J. Catal. 2014, 35(3), 310−318
doi: 10.1016/S1872-2067(12)60738-4
Hájek, M.; Kutálek, P.; Smolákováet, L.; Troppová, I.; Čapek, L.; Kubička, D.; Kocík, J.; Thanh, D. N. Transesterification of rapeseed oil by Mg-Al mixed oxides with various Mg/Al molar ratio. Chem. Eng. J. 2015, 263, 160−167
doi: 10.1016/j.cej.2014.11.006
Xinyu You , Xin Zhang , Shican Jiang , Yiru Ye , Lin Gu , Hexun Zhou , Pandong Ma , Jamal Ftouni , Abhishek Dutta Chowdhury . Efficacy of Ca/ZSM-5 zeolites derived from precipitated calcium carbonate in the methanol-to-olefin process. Chinese Journal of Structural Chemistry, 2024, 43(4): 100265-100265. doi: 10.1016/j.cjsc.2024.100265
Guihuang Fang , Wei Chen , Hongwei Yang , Haisheng Fang , Chuang Yu , Maoxiang Wu . Improved performance of LiMn0.8Fe0.2PO4 by addition of fluoroethylene carbonate electrolyte additive. Chinese Chemical Letters, 2024, 35(6): 108799-. doi: 10.1016/j.cclet.2023.108799
Zhenjie Yang , Chenyang Hu , Xuan Pang , Xuesi Chen . Sequence design in terpolymerization of ε-caprolactone, CO2 and cyclohexane oxide: Random ester-carbonate distributions lead to large-span tunability. Chinese Chemical Letters, 2024, 35(5): 109340-. doi: 10.1016/j.cclet.2023.109340
Kunyao Peng , Xianbin Wang , Xingbin Yan . Converting LiNO3 additive to single nitrogenous component Li2N2O2 SEI layer on Li metal anode in carbonate-based electrolyte. Chinese Chemical Letters, 2024, 35(9): 109274-. doi: 10.1016/j.cclet.2023.109274
Zhenchun Yang , Bixiao Guo , Zhenyu Hu , Kun Wang , Jiahao Cui , Lina Li , Chun Hu , Yubao Zhao . Molecular engineering towards dual surface local polarization sites on poly(heptazine imide) framework for boosting H2O2 photo-production. Chinese Chemical Letters, 2024, 35(8): 109251-. doi: 10.1016/j.cclet.2023.109251
Chuan-Zhi Ni , Ruo-Ming Li , Fang-Qi Zhang , Qu-Ao-Wei Li , Yuan-Yuan Zhu , Jie Zeng , Shuang-Xi Gu . A chiral fluorescent probe for molecular recognition of basic amino acids in solutions and cells. Chinese Chemical Letters, 2024, 35(10): 109862-. doi: 10.1016/j.cclet.2024.109862
Xiaotao Jin , Yanlan Wang , Yingping Huang , Di Huang , Xiang Liu . Percarbonate activation catalyzed by nanoblocks of basic copper molybdate for antibiotics degradation: High performance, degradation pathways and mechanism. Chinese Chemical Letters, 2024, 35(10): 109499-. doi: 10.1016/j.cclet.2024.109499
Haojie Song , Laiyu Luo , Siyu Wang , Guo Zhang , Baojiang Jiang . Advances in poly(heptazine imide)/poly(triazine imide) photocatalyst. Chinese Chemical Letters, 2024, 35(10): 109347-. doi: 10.1016/j.cclet.2023.109347
Longlong Geng , Huiling Liu , Wenfeng Zhou , Yong-Zheng Zhang , Hongliang Huang , Da-Shuai Zhang , Hui Hu , Chao Lv , Xiuling Zhang , Suijun Liu . Construction of metal-organic frameworks with unsaturated Cu sites for efficient and fast reduction of nitroaromatics: A combined experimental and theoretical study. Chinese Chemical Letters, 2024, 35(8): 109120-. doi: 10.1016/j.cclet.2023.109120
Bin Dong , Ning Yu , Qiu-Yue Wang , Jing-Ke Ren , Xin-Yu Zhang , Zhi-Jie Zhang , Ruo-Yao Fan , Da-Peng Liu , Yong-Ming Chai . Double active sites promoting hydrogen evolution activity and stability of CoRuOH/Co2P by rapid hydrolysis. Chinese Chemical Letters, 2024, 35(7): 109221-. doi: 10.1016/j.cclet.2023.109221
Qian-Qian Tang , Li-Fang Feng , Zhi-Peng Li , Shi-Hao Wu , Long-Shuai Zhang , Qing Sun , Mei-Feng Wu , Jian-Ping Zou . Single-atom sites regulation by the second-shell doping for efficient electrochemical CO2 reduction. Chinese Chemical Letters, 2024, 35(9): 109454-. doi: 10.1016/j.cclet.2023.109454
Runze Liu , Yankai Bian , Weili Dai . Qualitative and quantitative analysis of Brønsted and Lewis acid sites in zeolites: A combined probe-assisted 1H MAS NMR and NH3-TPD investigation. Chinese Journal of Structural Chemistry, 2024, 43(4): 100250-100250. doi: 10.1016/j.cjsc.2024.100250
Ruiying Liu , Li Zhao , Baishan Liu , Jiayuan Yu , Yujie Wang , Wanqiang Yu , Di Xin , Chaoqiong Fang , Xuchuan Jiang , Riming Hu , Hong Liu , Weijia Zhou . Modulating pollutant adsorption and peroxymonosulfate activation sites on Co3O4@N,O doped-carbon shell for boosting catalytic degradation activity. Chinese Journal of Structural Chemistry, 2024, 43(8): 100332-100332. doi: 10.1016/j.cjsc.2023.100332
Weijian Zhang , Xianyu Deng , Liying Wang , Jian Wang , Xiuting Guo , Lianggui Huang , Xinyi Wang , Jun Wu , Linjia Jiang . Poly(ferulic acid) nanocarrier enhances chemotherapy sensitivity of acute myeloid leukemia by selectively targeting inflammatory macrophages. Chinese Chemical Letters, 2024, 35(9): 109422-. doi: 10.1016/j.cclet.2023.109422
Chen Lian , Si-Han Zhao , Hai-Lou Li , Xinhua Cao . A giant Ce-containing poly(tungstobismuthate): Synthesis, structure and catalytic performance for the decontamination of a sulfur mustard simulant. Chinese Chemical Letters, 2024, 35(10): 109343-. doi: 10.1016/j.cclet.2023.109343
Zhili Li , Qijun Wo , Dongdong Huang , Dezhong Zhou , Lei Guo , Yeqing Mao . Improving gene transfection efficiency of highly branched poly(β-amino ester)s through the in-situ conversion of inactive terminal groups. Chinese Chemical Letters, 2024, 35(8): 109737-. doi: 10.1016/j.cclet.2024.109737
Shuangxi Li , Huijun Yu , Tianwei Lan , Liyi Shi , Danhong Cheng , Lupeng Han , Dengsong Zhang . NOx reduction against alkali poisoning over Ce(SO4)2-V2O5/TiO2 catalysts by constructing the Ce4+–SO42− pair sites. Chinese Chemical Letters, 2024, 35(5): 108240-. doi: 10.1016/j.cclet.2023.108240
Ningning Gao , Yue Zhang , Zhenhao Yang , Lijing Xu , Kongyin Zhao , Qingping Xin , Junkui Gao , Junjun Shi , Jin Zhong , Huiguo Wang . Ba2+/Ca2+ co-crosslinked alginate hydrogel filtration membrane with high strength, high flux and stability for dye/salt separation. Chinese Chemical Letters, 2024, 35(5): 108820-. doi: 10.1016/j.cclet.2023.108820
Ming ZHENG , Yixiao ZHANG , Jian YANG , Pengfei GUAN , Xiudong LI . Energy storage and photoluminescence properties of Sm3+-doped Ba0.85Ca0.15Ti0.90Zr0.10O3 lead-free multifunctional ferroelectric ceramics. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 686-692. doi: 10.11862/CJIC.20230388