Synthesis of Poly(isosorbide carbonate) via Melt Polycondensation Catalyzed by Ca/SBA-15 Solid Base

Xiao-Long Shen; Zi-Qing Wang; Qing-Yin Wang; Shao-Ying Liu; Gong-Ying Wang

doi:10.1007/s10118-018-2137-4

Your Location：

Home >

Browse articles >

Synthesis of Poly(isosorbide carbonate) via Melt Polycondensation Catalyzed by Ca/SBA-15 Solid Base

ARTICLE | Updated：2021-02-18

- 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
- Funds：
- DOI：10.1007/s10118-018-2137-4
  CLC：
- Received：05 December 2017，
  
  Revised：2018-3-22，
  
  Accepted：26 March 2018，
  
  Online First：25 April 2018，
  
  Published：2018-09
- Accepted：
Scan QR Code
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, 2018, 36(9): 1027-1035.
DOI：

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, 2018, 36(9): 1027-1035. 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 (

) and yield

and the sample with Ca/Si atomic ratio of 0.4 exhibited the best catalytic performance

giving PIC with

of 4.88 × 10

g/mol and

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

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.44654 http://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.1105.2011.10025 http://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/s10118-016-1820-6 http://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-z http://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.2012.07.059 http://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.26446 http://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.v217.13 http://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.2016.09.030 http://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/C5RA00242G http://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.7b00049 http://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: 10.1080/15321799708009650 http://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.2009.10.001 http://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.v212.19 http://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/C3GC42122H http://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.21116 http://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/C5PY00521C http://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/c1jm10087d http://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/ma0606051 http://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- T g poly(ester carbonate) partially based on isosorbide: synthesis and structure-property relationships . Polym. Chem. , 2014 . 6 ( 4 ): 633 - 642 . DOI: 10.1039/c4py00976b http://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/ma400360w http://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.26507 http://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.2016.03.007 http://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)62822-5 http://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.2011.06.001 http://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/ma500687t http://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.v217.13 http://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.279.5350.548 http://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/ja974025i http://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/C2JM14393C http://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/c3cc44721a http://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.2007.09.028 http://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/ic702223b http://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-z http://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.2011.09.002 http://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.2010.09.030 http://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.33906 http://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.2016.08.017 http://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.v60.7 http://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.1105.2014.13335 http://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/c2py20056b http://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/s10118-017-1887-8 http://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/C5RA18275A http://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: 10.1038/359710a0 http://doi.org/10.1038/359710a0 .

Radwan, N. R. E . Influence of La 2 O 3 and ZrO 2 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 http://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/b202180c http://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/b516061h http://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.1998.2161 http://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)60738-4 http://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.2014.11.006 http://doi.org/10.1016/j.cej.2014.11.006 .

Views

1080

Downloads

CSCD

Alert me when the article has been cited

Submit

Tools

Publicity Resources

Structure-Activity Correlations of Calcined Mg-Al Hydrocalcites for Aliphatic Polycarbonate Synthesis via Transesterification Process

Analysis of Structure Transition and Compatibility of PTT/PC Blend without Transesterification

Sequence-encoded Conformation Pathways in Viscoelastic Microphase Separation of Multiblock Copolymers

Alternating Poly(ether-alt-ester)s with High Glass Transition Temperature Enabled by Rotationally Constrained Biaryl Units

Advances in Polymer-based Circularly Polarized Luminescent Materials

Related Author

Yuan-sheng Bai

Wei Jiang

Xian-gui Yang

Song Qing-long

Wen Hui-ying

de Claville Christiansen Jesper

Yu Dong-hong

Chen Chun-sheng

Related Institution

College of Engineering and Technology, Northeast Forestry University

Department of Mechanical and Manufacturing Engineering, Aalborg University, DK-9220, Aalborg

Department of Biotechnology, Chemistry, and Environmental Engineering, Aalborg University, DK-9220, Aalborg

School of Materials Science and Engineering, Tianjin University

⁰