2022, Volume 16, Issue 9
Engineering >> 2022, Volume 16, Issue 9 doi: 10.1016/j.eng.2021.07.031
Implementing An “Impracticable” Copolymerization to Fabricate A Desired Polymer Precursor for N-doped Porous Carbons
State Key Laboratory of Materials-Oriented Chemical Engineering, Jiangsu National Synergetic Innovation Center for Advanced Material (SICAM), College of Chemical Engineering, Nanjing Tech University, Nanjing 211816, China
Next Previous
Abstract
It is common that a proof-of-concept of a desired reaction, which might generate materials with new functions or application potential, is eventually proved impracticable or commercially unfeasible. Considerable efforts have been made but wasted in searching for unknown reaction conditions in solvent environments because it was believed that the activity of reactants can be enhanced to facilitate reactions by dissolving them in solvents. However, an abnormal case was discovered in this study. A desired copolymerization reaction between 1,3,5-tris(chloromethyl)-2,4,6-trimethylbenzene and melamine was confirmed to be impracticable under various solvent conditions; however, it was successfully implemented using a solvent-free method. Using first-principle calculations and molecular dynamics simulations, two decisive factors that the reaction in solvents cannot possess, namely the reaction equilibrium being pushed by the timely release of by-products and the confined thermal motions of the activated monomer molecules in the solid phase, were demonstrated to make the copolymerization successful in the solvent-free method. Owing to the high aromaticity and azacyclo-content, the as-synthetic copolymer exhibited good application potential as a precursor to fabricate N-doped porous carbons with satisfactory carbon yields, ideal N contents, desired textural properties, and competitive CO2 capture abilities compared to other representative counterparts reported recently.
Keywords
Solvent-free method ; Solvent effect ; Copolymerization ; N-doped porous carbon
Figures
Fig. 1
Fig. 2
Fig. 3
Fig. 4
References
[ 1 ] Walker TW, Chew AK, Li HX, Demir B, Zhang ZC, Huber GW, et al. Universal kinetic solvent effects in acid-catalyzed reactions of biomass-derived oxygenates. Energy Environ Sci 2018;11(3):617–28. Corrected in: Energy Environ Sci 2018;11(6):1639.
[ 2 ] Zhou T, Song Z, Sundmacher K. Big data creates new opportunities for materials research: a review on methods and applications of machine learning for materials design. Engineering 2019;5(6):1017–26.
[ 3 ] Sherwood J, Clark JH, Fairlamb IJS, Slattery JM. Solvent effects in palladium catalysed cross-coupling reactions. Green Chem 2019;21(9):2164–213.
[ 4 ] Gao ZG, Rohani S, Gong JB, Wang JK. Recent developments in the crystallization process: toward the pharmaceutical industry. Engineering 2017;3(3):343–53.
[ 5 ] Qi SC, Hayashi JI, Kudo S, Zhang L. Catalytic hydrogenolysis of kraft lignin to monomers at high yield in alkaline water. Green Chem 2017;19(11):2636–45.
[ 6 ] Wang YQ, Wu QM, Meng XJ, Xiao FS. Insights into the organotemplate-free synthesis of zeolite catalysts. Engineering 2017;3(4):567–74.
[ 7 ] Yu L, Qian RR, Deng X, Wang F, Xu Q. Calcium-catalyzed reactions of element– H bonds. Sci Bull 2018;63(15):1010–6.
[ 8 ] Zhu Y, Ji Y, Ju Z, Yu K, Ferreira PJ, Liu Y, et al. Ultrafast intercalation enabled by strong solvent–host interactions: understanding solvent effect at the atomic level. Angew Chem Int Ed Engl 2019;58(48):17205–9.
[ 9 ] Savoo N, Laloo JZA, Rhyman L, Ramasami P, Bickelhaupt FM, Poater J. Activation strain analyses of counterion and solvent effects on the ion-pair SN2 reaction of NH 2 and CH3Cl. J Comput Chem 2020;41(4):317–27.
[10] Tang W, Yu H, Cai C, Zhao T, Lu C, Zhao S, et al. Solvent effects on a derivative of 1,3,4-oxadiazole tautomerization reaction in water: a reaction density functional theory study. Chem Eng Sci 2020;213:115380.
[11] Ji X, Li Y, Zheng J, Liu Q. Solvent effects of ethyl methacrylate characterized by FTIR. Mater Chem Phys 2011;130(3):1151–5.
[12] Feng C, Li Y, Yang D, Hu J, Zhang X, Huang X. Well-defined graft copolymers: from controlled synthesis to multipurpose applications. Chem Soc Rev 2011;40(3):1282–95.
[13] Uhrig D, Mays J. Synthesis of well-defined multigraft copolymers. Polym Chem 2011;2(1):69–76.
[14] Zhang Q, Ko NR, Oh JK. Recent advances in stimuli-responsive degradable block copolymer micelles: synthesis and controlled drug delivery applications. Chem Commun 2012;48(61):7542–52.
[15] Jennings J, He G, Howdle SM, Zetterlund PB. Block copolymer synthesis by controlled/living radical polymerisation in heterogeneous systems. Chem Soc Rev 2016;45(18):5055–84.
[16] Feng H, Lu X, Wang W, Kang NG, Mays JW. Block copolymers: synthesis, selfassembly, and applications. Polymers 2017;9(10):494.
[17] Hu JM, Zhang GY, Ge ZS, Liu SY. Stimuli-responsive tertiary amine methacrylate-based block copolymers: synthesis, supramolecular selfassembly and functional applications. Prog Polym Sci 2014;39(6):1096–143.
[18] Wang MQ, Tang C, Ye C, Duan J, Li C, Chen Y, et al. Engineering the nanostructure of molybdenum nitride nanodot embedded N-doped porous hollow carbon nanochains for rapid all pH hydrogen evolution. J Mater Chem A 2018;6(30):14734–41.
[19] Zhu D, Jiang J, Sun D, Qian X, Wang Y, Li L, et al. A general strategy to synthesize high-level N-doped porous carbons via Schiff-base chemistry for supercapacitors. J Mater Chem A 2018;6(26):12334–43.
[20] Li Y, Yang C, Zheng F, Ou X, Pan Q, Liu Y, et al. High pyridine N-doped porous carbon derived from metal–organic frameworks for boosting potassium-ion storage. J Mater Chem A 2018;6(37):17959–66.
[21] Yang F, Wang J, Liu L, Zhang P, Yu W, Deng Q, et al. Synthesis of porous carbons with high N-content from shrimp shells for efficient CO2-capture and gas separation. ACS Sustain Chem Eng 2018;6(11):15550–9.
[22] Qi SC, Liu Y, Peng AZ, Xue DM, Liu X, Liu XQ, et al. Fabrication of porous carbons from mesitylene for highly efficient CO2 capture: a rational choice improving the carbon loop. Chem Eng J 2019;361:945–52.
[23] Peng AZ, Qi SC, Liu X, Xue DM, Peng SS, Yu GX, et al. N-doped porous carbons derived from a polymer precursor with a record-high N content: efficient adsorbents for CO2 capture. Chem Eng J 2019;372:656–64.
[24] Xue DM, Qi SC, Zeng QZ, Lu RJ, Long JH, Luo C, et al. Fabrication of nitrogendoped porous carbons derived from ammoniated copolymer precursor: record-high adsorption capacity for indole. Chem Eng J 2019;374:1005–12.
[25] Xue DM, Qi SC, Liu X, Li YX, Liu XQ, Sun LB. N-doped porous carbons with increased yield and hierarchical pore structures for supercapacitors derived from an N-containing phenyl-riched copolymer. J Ind Eng Chem 2019;80:568–75.
[26] Zhao JH, Shu Y, Zhang PF. Solid-state CTAB-assisted synthesis of mesoporous Fe3O4 and Au@Fe3O4 by mechanochemistry. Chin J Catal 2019;40(7):1078–84.
[27] Shu Y, Chen H, Chen N, Duan X, Zhang P, Yang S, et al. A principle for highly active metal oxide catalysts via NaCl-based solid solution. Chem 2020;6 (7):1723–41.
[28] Hou ST, Sun YH, Jiang XG, Zhang PF. Nitrogen-rich isoindoline-based porous polymer: promoting Knoevenagel reaction at room temperature. Green Energy Environ 2020;5(4):484–91.
[29] Grimme S, Ehrlich S, Goerigk L. Effect of the damping function in dispersion corrected density functional theory. J Comput Chem 2011;32(7):1456–65.
[30] Canneaux S, Bohr F, Henon E. KiSThelP: a program to predict thermodynamic properties and rate constants from quantum chemistry results. J Comput Chem 2014;35(1):82–93.
[31] Lin TJ, Heinz H. Accurate force field parameters and pH resolved surface models for hydroxyapatite to understand structure, mechanics, hydration, and biological interfaces. J Phys Chem C 2016;120(9):4975–92.
[32] Lange J, de Souza FG, Nele M, Tavares FW, Segtovich ISV, da Silva GCQ, et al. Molecular dynamic simulation of oxaliplatin diffusion in poly(lactic acid-coglycolic acid). Part A: parameterization and validation of the force-field CVFF. Macromol Theory Simul 2016;25(1):45–62.
[33] Zhang J, Wang Z, Li L, Zhao J, Zheng J, Cui H, et al. Self-assembly of CNH nanocages with remarkable catalytic performance. J Mater Chem A 2014;2 (22):8179.
[34] Liu X, Qi SC, Peng AZ, Xue DM, Liu XQ, Sun LB. Foaming effect of a polymer precursor with a low N content on fabrication of N-doped porous carbons for CO2 capture. Ind Eng Chem Res 2019;58(25):11013–21.
[35] Tian K, Wu Z, Xie F, Hu W, Li L. Nitrogen-doped porous carbons derived from triarylisocyanurate-cored polymers with high CO2 adsorption properties. Energy Fuels 2017;31(11):12477–86.
[36] Ren X, Li H, Chen J, Wei L, Modak A, Yang H, et al. N-doped porous carbons with exceptionally high CO2 selectivity for CO2 capture. Carbon 2017;114:473–81.
[37] Rao L, Liu S, Wang L, Ma C, Wu J, An L, et al. N-doped porous carbons from lowtemperature and single-step sodium amide activation of carbonized water chestnut shell with excellent CO2 capture performance. Chem Eng J 2019;359:428–35.
[38] Shao L, Liu M, Huang J, Liu YN. CO2 capture by nitrogen-doped porous carbons derived from nitrogen-containing hyper-cross-linked polymers. J Colloid Interface Sci 2018;513:304–13.
[39] Chang BB, Zhang SR, Yin H, Yang BC. Convenient and large-scale synthesis of nitrogen-rich hierarchical porous carbon spheres for supercapacitors and CO2 capture. Appl Surf Sci 2017;412:606–15.
[40] Yue L, Xia Q, Wang L, Wang L, DaCosta H, Yang J, et al. CO2 adsorption at nitrogen-doped carbons prepared by K2CO3 activation of urea-modified coconut shell. J Colloid Interface Sci 2018;511:259–67.
[41] Puthiaraj P, Lee YR, Ahn WS. Microporous amine-functionalized aromatic polymers and their carbonized products for CO2 adsorption. Chem Eng J 2017;319:65–74.
[42] Li X, Sui ZY, Sun YN, Xiao PW, Wang XY, Han BH. Polyanilinederived hierarchically porous nitrogen-doped carbons as gas adsorbents for carbon dioxide uptake. Microporous Mesoporous Mater 2018;257: 85–91.
[43] Pan Y, Zhao Y, Mu S, Wang Y, Jiang C, Liu Q, et al. Cation exchanged MOFderived nitrogen-doped porous carbons for CO2 capture and supercapacitor electrode materials. J Mater Chem A 2017;5(20):9544–52.
[44] Wei H, Qian W, Fu N, Chen H, Liu J, Jiang X, et al. Facile synthesis of nitrogendoped porous carbons for CO2 capture and supercapacitors. J Mater Sci 2017;52(17):10308–20.
[45] Fu N, Wei HM, Lin HL, Li L, Ji CH, Yu NB, et al. Iron nanoclusters as template/ activator for the synthesis of nitrogen doped porous carbon and its CO2 adsorption application. ACS Appl Mater Interfaces 2017;9(11):9955–63.
[46] Qi SC, Wu JK, Lu J, Yu GX, Zhu RR, Liu Y, et al. Underlying mechanism of CO2 adsorption onto conjugated azacyclo-copolymers: N-doped adsorbents capture CO2 chiefly through acid-base interaction? J Mater Chem A 2019;7 (30):17842–53.
[47] Smith AL, D’Angelo ND, Bo YY, Booker SK, Cee VJ, Herberich B, et al. Structurebased design of a novel series of potent, selective inhibitors of the class I phosphatidylinositol 3-kinases. J Med Chem 2012;55(11):5188–219.
京公网安备 11010502051620号
