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Synthesis of Poly(isosorbide carbonate) via Melt Polycondensation Catalyzed by Ca/SBA-15 Solid Base
- Chinese Journal of Polymer Science Vol. 36, Issue 9, Pages: 1027-1035(2018)
- Affiliations：
a.Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China
b.University of Chinese Academy of Sciences, Beijing 100049, China
c.Changzhou Institute of Chemistry, Changzhou 213164, China
- Author bio：
wanggongying1102@126.com
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DOI：10.1007/s10118-018-2137-4
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Xiao-Long Shen, Zi-Qing Wang, Qing-Yin Wang, et al. Synthesis of Poly(isosorbide carbonate) via Melt Polycondensation Catalyzed by Ca/SBA-15 Solid Base. [J]. Chinese Journal of Polymer Science 36(9):1027-1035(2018)
Xiao-Long Shen, Zi-Qing Wang, Qing-Yin Wang, et al. Synthesis of Poly(isosorbide carbonate) via Melt Polycondensation Catalyzed by Ca/SBA-15 Solid Base. [J]. Chinese Journal of Polymer Science 36(9):1027-1035(2018) DOI： 10.1007/s10118-018-2137-4.
摘要
Abstract
Ca/SBA-15 solid bases with different Ca/Si atomic ratios were prepared by a one-pot route and employed as catalysts for the production of poly(isosorbide carbonate) (PIC) from diphenyl carbonate and isosorbide ,via, a transesterification polymerization process. The relationship between physicochemical properties and catalytic performance for Ca/SBA-15 in this melt process was investigated by means of various characterization techniques. It was found that basic site amount and strength were responsible for this transesterification process; the weak and medium basic sites inclined to promote polycondensation reaction. It was worth noting that strong basic sites could favor the decomposition of the resultant PIC, resulting in the decrease of weight-average molecular weight (,M,w,) and yield, and the sample with Ca/Si atomic ratio of 0.4 exhibited the best catalytic performance, giving PIC with ,M,w, of 4.88 × 10,4, g/mol and ,T,g, of 169 °C at the optimal conditions. This excellent activity can be ascribed to the presence of rich basic sites and specific basic strength on the surface of 0.4Ca/SBA-15.
关键词
Keywords
Ca/SBA-15Poly(isosorbide carbonate)Diphenyl carbonateTransesterificationBasic sites
references
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.44654http://doi.org/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.1105.2011.10025http://doi.org/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/s10118-016-1820-6http://doi.org/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-zhttp://doi.org/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.2012.07.059http://doi.org/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.26446http://doi.org/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.v217.13http://doi.org/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.2016.09.030http://doi.org/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/C5RA00242Ghttp://doi.org/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.7b00049http://doi.org/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:10.1080/15321799708009650http://doi.org/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.2009.10.001http://doi.org/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.v212.19http://doi.org/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/C3GC42122Hhttp://doi.org/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.21116http://doi.org/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/C5PY00521Chttp://doi.org/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/c1jm10087dhttp://doi.org/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/ma0606051http://doi.org/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/c4py00976bhttp://doi.org/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/ma400360whttp://doi.org/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.26507http://doi.org/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.2016.03.007http://doi.org/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)62822-5http://doi.org/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.2011.06.001http://doi.org/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/ma500687thttp://doi.org/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.v217.13http://doi.org/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.279.5350.548http://doi.org/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/ja974025ihttp://doi.org/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/C2JM14393Chttp://doi.org/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/c3cc44721ahttp://doi.org/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.2007.09.028http://doi.org/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/ic702223bhttp://doi.org/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-zhttp://doi.org/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.2011.09.002http://doi.org/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.2010.09.030http://doi.org/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.33906http://doi.org/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.2016.08.017http://doi.org/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.v60.7http://doi.org/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.1105.2014.13335http://doi.org/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/c2py20056bhttp://doi.org/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/s10118-017-1887-8http://doi.org/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/C5RA18275Ahttp://doi.org/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:10.1038/359710a0http://doi.org/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.2005.10.008http://doi.org/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/b202180chttp://doi.org/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/b516061hhttp://doi.org/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.1998.2161http://doi.org/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)60738-4http://doi.org/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.2014.11.006http://doi.org/10.1016/j.cej.2014.11.006 .
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