Reaction kinetics determination based on microfluidic technology

doi:10.1016/j.cjche.2021.08.023

摘要/Abstract

摘要： Microfluidic technology has been successfully applied to determine the reaction kinetics relying on its great characteristics including narrow residence time distribution, fast mixing, high mass and heat transfer rates and very low consumption of materials. In this review, the recent progresses about the reaction kinetics measured in microreactors are comprehensively organized, and the kinetic modeling thoughts, determination methods and essential kinetic regularities contained in these studies are summarized according to the reaction types involving nitration, oxidation, hydrogenation, photochemical reaction, polymerization and other reactions. Besides, the significant advances in the innovation of microplatform are also covered. The novel reactor configuration methods were established mainly to achieve rapid and efficient data collection and analysis. Finally, the advantages of microfluidic technology for the kinetic measurement are summarized, and a perspective for the future development is provided.

关键词: Microfluidics, Microreactor, Kinetics, Chemical reaction

Abstract: Microfluidic technology has been successfully applied to determine the reaction kinetics relying on its great characteristics including narrow residence time distribution, fast mixing, high mass and heat transfer rates and very low consumption of materials. In this review, the recent progresses about the reaction kinetics measured in microreactors are comprehensively organized, and the kinetic modeling thoughts, determination methods and essential kinetic regularities contained in these studies are summarized according to the reaction types involving nitration, oxidation, hydrogenation, photochemical reaction, polymerization and other reactions. Besides, the significant advances in the innovation of microplatform are also covered. The novel reactor configuration methods were established mainly to achieve rapid and efficient data collection and analysis. Finally, the advantages of microfluidic technology for the kinetic measurement are summarized, and a perspective for the future development is provided.

Key words: Microfluidics, Microreactor, Kinetics, Chemical reaction

Zifei Yan, Jiaxin Tian, Chencan Du, Jian Deng, Guangsheng Luo. Reaction kinetics determination based on microfluidic technology[J]. 中国化学工程学报, 2022, 41(1): 49-72.

Zifei Yan, Jiaxin Tian, Chencan Du, Jian Deng, Guangsheng Luo. Reaction kinetics determination based on microfluidic technology[J]. Chinese Journal of Chemical Engineering, 2022, 41(1): 49-72.

参考文献

[1] S. Lu, K. Wang, Kinetic study of TBD catalyzed d-valerolactone polymerization using a gas-driven droplet flow reactor, React. Chem. Eng. 4(2019) 1189–1194.
[2] Z. Yao, X. Xu, Y. Dong, X. Liu, B. Yuan, K. Wang, K. Cao, G. Luo, Kinetics on thermal dissociation and oligomerization of dicyclopentadiene in a high temperature & pressure microreactor, Chem. Eng. Sci. 228(2020) 115892.
[3] X. Lin, K. Wang, B. Zhou, G. Luo, A microreactor-based research for the kinetics of polyvinyl butyral (PVB) synthesis reaction, Chem. Eng. J. 383(2020) 123181.
[4] M. Guo, Q. Chen, Y. Liang, Y. Wang, G. Luo, H. Yu, Experimental and modelbased study of biohydration of acrylonitrile to acrylamide in a microstructured chemical system, AIChE J. 66(2020) e16298.
[5] A. Hommes, A.J. ter Horst, M. Koeslag, H.J. Heeres, J. Yue, Experimental and modeling studies on the Ru/C catalyzed levulinic acid hydrogenation to cvalerolactone in packed bed microreactors, Chem. Eng. J. 399(2020) 125750.
[6] Z. Yan, Z. Ma, J. Deng, G. Luo, Mechanism and kinetics of epoxide ring-opening with carboxylic acids catalyzed by the corresponding carboxylates, Chem. Eng. Sci. 242(2021) 116746.
[7] Z. Yan, J. Tian, K. Wang, K.D.P. Nigam, G. Luo, Microreaction processes for synthesis and utilization of epoxides: A review, Chem. Eng. Sci. 229(2021) 116071.
[8] J. Deng, J. Zhang, K. Wang, G. Luo, Microreaction Technology for Synthetic Chemistry, Chinese J. Chem. 37(2019) 161–170.
[9] Y. Lu, D. Xin, J. Zhang, G. Luo, Modeling ethyl diazoacetate synthesis in an adiabatic microchemical system, Chem. Eng. J. 273(2015) 406–412.
[10] C. Shen, M. Shang, H. Zhang, Y. Su, A UV-LEDs based photomicroreactor for mechanistic insights and kinetic studies in the norbornadiene photoisomerization, AIChE J. 66(2020) e16841.
[11] H. Keles, F. Susanne, H. Livingstone, S. Hunter, C. Wade, R. Bourdon, A. Rutter, Development of a robust and reusable microreactor employing laser based mid-IR chemical imaging for the automated quantification of reaction kinetics, Org. Process Res. Dev. 21(2017) 1761–1768.
[12] D. Russo, G. Tomaiuolo, R. Andreozzi, S. Guido, A.A. Lapkin, I. Di Somma, Heterogeneous benzaldehyde nitration in batch and continuous flow microreactor, Chem. Eng. J. 377(2019) 120346.
[13] M.N. Kashid, A. Renken, L. Kiwi-Minsker, Gas–liquid and liquid–liquid mass transfer in microstructured reactors, Chem. Eng. Sci. 66(2011) 3876– 3897.
[14] Z. Wen, M. Yang, S. Zhao, F. Zhou, G. Chen, Kinetics study of heterogeneous continuous-flow nitration of trifluoromethoxybenzene, React. Chem. Eng. 3(2018) 379–387.
[15] P. Wang, K. Wang, J. Zhang, G. Luo, Kinetic study of reactions of aniline and benzoyl chloride in a microstructured chemical system, AIChE J. 61(2015) 3804–3811.
[16] N. Padoin, L. Andrade, J. Ângelo, A. Mendes, R.D.F.P. Moreira, C. Soares, Intensification of photocatalytic pollutant abatement in microchannel reactor using TiO₂ and TiO₂-graphene, AIChE J. 62(2016) 2794–2802.
[17] C. Dong, K. Wang, J.S. Zhang, G.S. Luo, Reaction kinetics of cyclohexanone ammoximation over TS-1 catalyst in a microreactor, Chem. Eng. Sci. 126(2015) 633–640.
[18] M. Krivec, A. Pohar, B. Likozar, G. Dražić, Hydrodynamics, mass transfer, and photocatalytic phenol selective oxidation reaction kinetics in a fixed TiO₂ microreactor, AIChE J. 61(2015) 572–581.
[19] J.P. Mcmullen, K.F. Jensen, Rapid determination of reaction kinetics with an automated microfluidic system, Org. Process Res. Dev. 15(2011) 398–407.
[20] N.T. Nguyen, Z.G. Wu, Micromixers-a review, J. Micromech. Microeng. 15(2005) R1–R16.
[21] K. Wang, G. Luo, Microflow extraction: A review of recent development, Chem. Eng. Sci. 169(2017) 18–33.
[22] J. Zhang, K. Wang, A.R. Teixeira, K.F. Jensen, G. Luo, Design and scaling up of microchemical systems: a review, Annu. Rev. Chem. Biomol. 8(2017) 285–305.
[23] J. Sui, J. Yan, D. Liu, K. Wang, G. Luo, Continuous synthesis of nanocrystals via flow chemistry technology, Small 16(2020) 1902828.
[24] F. Benito-Lopez, W. Verboom, M. Kakuta, J.H.G.E. Gardeniers, R.J.M. Egberink, E. R. Oosterbroek, A. van den Berg, D.N. Reinhoudt, Optical fiber-based on-line UV/Vis spectroscopic monitoring of chemical reaction kinetics under high pressure in a capillary microreactor, Chemical communications (Cambridge, England) (2005) 2857-2859
[25] A. Muto, M. Ebata, A. Inoue. Development of a microreactor for rapid analysis of chemical reaction kinetics with absorption specrtoscopy, IEEE, 2008.
[26] X. Duan, J. Tu, A.R. Teixeira, L. Sang, K.F. Jensen, J. Zhang, An automated flow platform for accurate determination of gas-liquid-solid reaction kinetics, React. Chem. Eng. 5(2020) 1751–1758.
[27] J.S. Moore, C.D. Smith, K.F. Jensen, Kinetics analysis and automated online screening of aminocarbonylation of aryl halides in flow, React. Chem. Eng. 1(2016) 272–279.
[28] Y.F. Han, M.J. Kahlich, M. Kinne, R.J. Behm, Kinetic study of selective CO oxidation in H₂-rich gas on a Ru/c-Al₂O₃ catalyst, Phys. Chem. Chem. Phys. 4(2002) 389–397.
[29] J.S. Moore, K.F. Jensen, “Batch” Kinetics in flow: online IR analysis and continuous control, Angewandte Chemie International Edition 53(2014) 470– 473.
[30] K. Wang, Y.C. Lu, Y. Xia, H.W. Shao, G.S. Luo, Kinetics research on fast exothermic reaction between cyclohexanecarboxylic acid and oleum in microreactor, Chem. Eng. J. 169(2011) 290–298.
[31] C. Zhang, J. Zhang, G. Luo, Kinetics determination of fast exothermic reactions with infrared thermography in a microreactor, J. Flow Chem. 10(2020) 219– 226.
[32] J.S. Zhang, C.Y. Zhang, G.T. Liu, G.S. Luo, Measuring enthalpy of fast exothermal reaction with infrared thermography in a microreactor, Chem. Eng. J. 295(2016) 384–390.
[33] Z. Lan, Y. Lu, Continuous nitration of o-dichlorobenzene in micropacked-bed reactor: process design and modelling, J. Flow Chem. 11(2021) 171–179.
[34] J. Grant, P.T.O. Kane, B.R. Kimmel, M. Mrksich, Using microfluidics and imaging SAMDI-MS to characterize reaction kinetics, ACS Cent. Sci. 5(2019) 486–493.
[35] E. Fradet, P. Abbyad, M.H. Vos, C.N. Baroud, Parallel measurements of reaction kinetics using ultralow-volumes, Lab Chip 13(2013) 4326–4330.
[36] C. Zheng, B. Zhao, K. Wang, G. Luo, Determination of kinetics of CO₂ absorption in solutions of 2-amino-2-methyl-1-propanol using a microfluidic technique, AIChE J. 61(2015) 4358–4366.
[37] A.A. Kulkarni, Continuous flow nitration in miniaturized devices, Beilstein J. Org. Chem. 10(2014) 405–424.
[38] L. Li, C. Yao, F. Jiao, M. Han, G. Chen, Experimental and kinetic study of the nitration of 2-ethylhexanol in capillary microreactors, Chem. Eng. Process. Process Intensif. 117(2017) 179–185.
[39] C. Zhang, J. Zhang, G. Luo, Kinetic study and intensification of acetyl guaiacol nitration with nitric acid—acetic acid system in a microreactor, J. Flow Chem. 6(2016) 309–314.
[40] J. Tan, L. Du, Y.C. Lu, J.H. Xu, G.S. Luo, Development of a gas–liquid microstructured system for oxidation of hydrogenated 2-ethyltetrahydroanthraquinone, Chem. Eng. J. 171(2011) 1406–1414.
[41] K. Bawornruttanaboonya, N. Laosiripojana, A.S. Mujumdar, S. Devahastin, Catalytic partial oxidation of CH₄ over bimetallic Ni-Re/Al₂O₃: Kinetic determination for application in microreactor, AIChE J. 64(2018) 1691–1701.
[42] R.H. Nibbelke, M.A.J. Campman, J.H.B.J. Hoebink, G.B. Marin, Kinetic Study of the CO Oxidation over Pt/c-Al₂O₃ and Pt/Rh/CeO₂/c-Al₂O₃ in the Presence of H₂O and CO₂, J. Catal. 171(1997) 358–373.
[43] G. Nikolaidis, T. Baier, R. Zapf, G. Kolb, V. Hessel, W.F. Maier, Kinetic study of CO preferential oxidation over Pt–Rh/c-Al₂O₃ catalyst in a micro-structured recycle reactor, Catal. Today 145(2009) 90–100.
[44] V. Russo, T. Kilpiö, J. Hernandez Carucci, M. Di Serio, T.O. Salmi, Modeling of microreactors for ethylene epoxidation and total oxidation, Chem. Eng. Sci. 134(2015) 563–571.
[45] F. Ebrahimi, E. Kolehmainen, A. Laari, H. Haario, D. Semenov, I. Turunen, Determination of kinetics of percarboxylic acids synthesis in a microreactor by mathematical modeling, Chem. Eng. Sci. 71(2012) 531–538.
[46] H. Zhao, S. Liu, M. Shang, Y. Su, Direct oxidation of benzene to phenol in a microreactor: Process parameters and reaction kinetics study, Chem. Eng. Sci. 246(2021) 116907.
[47] G. Li, S. Liu, X. Dou, H. Wei, M. Shang, Z.H. Luo, Y. Su, Synthesis of adipic acid through oxidation of K/A oil and its kinetic study in a microreactor system, AIChE J. 66(2020) e16289.
[48] T.A. Nijhuis, J. Chen, S.M.A. Kriescher, J.C. Schouten, The direct epoxidation of propene in the explosive regime in a microreactor-a study into the reaction kinetics, Ind. Eng. Chem. Res. 49(2010) 10479–10485.
[49] Z. Vajglová, N. Kumar, K. Eränen, M. Peurla, D.Y. Murzin, T. Salmi, Ethene oxychlorination over CuCl₂/c-Al₂O₃ catalyst in micro- and millistructured reactors, J. Catal. 364(2018) 334–344.
[50] G. Wu, E. Cao, P. Ellis, A. Constantinou, S. Kuhn, A. Gavriilidis, Continuous flow aerobic oxidation of benzyl alcohol on Ru/Al₂O₃ catalyst in a flat membrane microchannel reactor: An experimental and modelling study, Chem. Eng. Sci. 201(2019) 386–396.
[51] J. Singh, N. Kockmann, K.D.P. Nigam, Novel three-dimensional microfluidic device for process intensification, Chem. Eng. Process. Process Intensif. 86(2014) 78–89.
[52] Y. Maralla, S.H. Sonawane, Process intensification by using a helical capillary microreactor for a continuous flow synthesis of peroxypropionic acid and its kinetic study, Periodica Polytechnica Chem. Eng. 64(2019) 9–19.
[53] A. Tušek, A. Aalić, B. Zelić Kurtanjek, Modeling and kinetic parameter estimation of alcohol dehydrogenase-catalyzed hexanol oxidation in a microreactor, Eng. Life Sci. 12(2012) 49–56.
[54] A.A. Mirzaei, A. Pourdolat, M. Arsalanfar, H. Atashi, A.R. Samimi, Kinetic study of CO hydrogenation on the MgO supported Fe–Co–Mn sol–gel catalyst, J. Ind. Eng. Chem. 19(2013) 1144–1152.
[55] N. Mahata, V. Vishwanathan, Kinetics of phenol hydrogenation over supported palladium catalyst, J. Mol. Catal. A: Chem. 120(1997) 267–270.
[56] N. Joshi, A. Lawal, Hydrodeoxygenation of 4-propylguaiacol (2-methoxy-4-propylphenol) in a microreactor: performance and kinetic studies, Ind. Eng. Chem. Res. 52(2013) 4049–4058.
[57] S. Vahid, A.A. Mirzaei, An investigation of the kinetics and mechanism of Fischer-Tropsch synthesis on Fe–Co–Ni supported catalyst, J. Ind. Eng. Chem. 20(2014) 2166–2173.
[58] A.A. Mirzaei, E. Rezazadeh, M. Arsalanfar, M. Abdouss, M. Fatemi, M. Sahebi, Study on the reaction mechanism and kinetics of CO hydrogenation on a fused Fe-Mn catalyst, RSC Adv. 5(2015) 95287–95299.
[59] A. Tanimu, S.A. Ganiyu, O. Muraza, K. Alhooshani, Palladium nanoparticles supported on ceria thin film for capillary microreactor application, Chem. Eng. Res. Des. 132(2018) 479–491.
[60] K. Maresz, A. Ciemięga, J. Mrowiec-Białoń, Monolithic microreactors of different structure as an effective tool for in flow MPV reaction, Chem. Eng. J. 379(2020) 122281.
[61] A.A. Mirzaei, M. Farahi, M. Akbari, Effect of reduction and reaction conditions on the catalytic performance of Co–Ni/Al₂O₃ catalyst in CO hydrogenation: modeling of surface reaction rate, Chem. Pap. 75(2021) 2087–2103.
[62] V. Vishwanathan, V. Jayasri, P. Mahaboob Basha, Vapor phase hydrogenation of o-chloronitrobenzene (o-CNB) over alumina supported palladium catalyst — a kinetic study, React. Kinet. Catal. Lett. 91(2007) 291–298.
[63] F.E. Massoth, P. Politzer, M.C. Concha, J.S. Murray, J. Jakowski, J. Simons, Catalytic hydrodeoxygenation of methyl-substituted phenols: correlations of kinetic parameters with molecular properties, J. Phys. Chem. B 110(2006) 14283–14291.
[64] P.E. Savage, S. Gopalan, T.I. Mizan, C.J. Martino, E.E. Brock, Reactions at supercritical conditions: Applications and fundamentals, AIChE J. 41(1995) 1723–1778.
[65] E. Ramírez, F. Recasens, M. Fernández, M.A. Larrayoz, Sunflower oil hydrogenation on Pd/C in SC propane in a continuous recycle reactor, AIChE J. 50(2004) 1545–1555.
[66] E.V. Rebrov, A. Berenguer-Murcia, H.E. Skelton, B.F.G. Johnson, A.E.H. Wheatley, J.C. Schouten, Capillary microreactors wall-coated with mesoporous titania thin film catalyst supports, Lab Chip 9(2009) 503–506.
[67] S. Chatani, C.J. Kloxin, C.N. Bowman, The power of light in polymer science: photochemical processes to manipulate polymer formation, structure, and properties, Polym. Chem.-UK 5(2014) 2187–2221.
[68] Y. Su, V. Hessel, T. Noel, A compact photomicroreactor design for kinetic studies of gas-liquid photocatalytic transformations, AIChE J. 61(2015) 2215– 2227.
[69] M.L. Satuf, J. Macagno, A. Manassero, G. Bernal, P.A. Kler, C.L.A. Berli, Simple method for the assessment of intrinsic kinetic constants in photocatalytic microreactors, Appl. Catal. B 241(2019) 8–17.
[70] G. Yu, N. Wang, Gas-liquid-solid interface enhanced photocatalytic reaction in a microfluidic reactor for water treatment, Appl. Catal. A 591(2020) 117410.
[71] X. Shi, S. Liu, C. Duanmu, M. Shang, M. Qiu, C. Shen, Y. Yang, Y. Su, Visible-light photooxidation of benzene to phenol in continuous-flow microreactors, Chem. Eng. J. 420(2021) 129976.
[72] D.D. Phan, F. Babick, T.H.T. Tr nh, M.T. Nguyen, W. Samhaber, M. Stintz, Investigation of fixed-bed photocatalytic membrane reactors based on submerged ceramic membranes, Chem. Eng. Sci. 191(2018) 332–342.
[73] T. Aillet, K. Loubière, L. Prat, O. Dechy-Cabaret, Impact of the diffusion limitation in microphotoreactors, AIChE J. 61(2015) 1284–1299.
[74] N. El Achi, F. Gelat, N.P. Cheval, A. Mazzah, Y. Bakkour, M. Penhoat, L. ChaussetBoissarie, C. Rolando, Sensitized [2+2] intramolecular photocycloaddition of unsaturated enones using UV LEDs in a continuous flow reactor: kinetic and preparative aspects, React. Chem. Eng. 4(2019) 828–837.
[75] Y. Takahashi, A. Nagaki, Anionic polymerization using flow microreactors, Molecules 24(2019) 1532.
[76] C.O.C. López, Z. Fejes, B. Viskolcz, Microreactor assisted method for studying isocyanate–alcohol reaction kinetics, J. Flow Chem. 9(2019) 199–204.
[77] L. Qiu, K. Wang, S. Zhu, Y. Lu, G. Luo, Kinetics study of acrylic acid polymerization with a microreactor platform, Chem. Eng. J. 284(2016) 233– 239.
[78] L. Xiang, Y. Song, M. Qiu, Y. Su, Synthesis of branched poly(butyl acrylate) using the strathclyde method in continuous-flow microreactors, Ind. Eng. Chem. Res. 58(2019) 21312–21322.
[79] P. Wang, K. Wang, J. Zhang, G. Luo, Preparation of poly(p-phenylene terephthalamide) in a microstructured chemical system, RSC Adv. 5(2015) 64055–64064.
[80] S.S. Cutie, P.B. Smith, D.E. Henton, T.L. Staples, C. Powell, Acrylic acid polymerization kinetics, J. Polym. Sci. Pol. Phys. 35(1997) 2029–2047.
[81] J. Huang, F. Sang, G. Luo, J. Xu, Continuous synthesis of Gabapentin with a microreaction system, Chem. Eng. Sci. 173(2017) 507–513.
[82] C. Du, J. Zhang, G. Luo, Organocatalyzed Beckmann rearrangement of cyclohexanone oxime in a microreactor: Kinetic model and product inhibition, AIChE J. 64(2018) 571–577.
[83] L. Li, J. Zhang, C. Du, K. Wang, G. Luo, Kinetics study of sulfuric acid alkylation of isobutane and butene using a microstructured chemical system, Ind. Eng. Chem. Res. 58(2018) 1150–1158.
[84] M. Shang, T. Noël, Y. Su, V. Hessel, Kinetic study of hydrogen peroxide decomposition at high temperatures and concentrations in two capillary microreactors, AIChE J. 63(2017) 689–697.
[85] J.S. Zhang, Y.C. Lu, Q.R. Jin, K. Wang, G.S. Luo, Determination of kinetic parameters of dehydrochlorination of dichloropropanol in a microreactor, Chem. Eng. J. 203(2012) 142–147.
[86] K. Shibatani, K. Fujii, Reaction of poly(vinyl alcohol) with formaldehyde and polymer stereoregularity-model compounds, J. Polym. Sci. Part A-1-Polym. Chem. 8(1970) 1647.