Ultrafast flow chemistry for the acid-catalyzed conversion of fructose

Desir, Pierre; Saha, Basudeb; Vlachos, Dionisios G.

doi:10.1039/c9ee01189g

Title: Ultrafast flow chemistry for the acid-catalyzed conversion of fructose

Journal Article · Tue May 28 00:00:00 EDT 2019 · Energy & Environmental Science

DOI:https://doi.org/10.1039/c9ee01189g· OSTI ID:1613478

Desir, Pierre ^[1];

^[2];

^[1]

Univ. of Delaware, Newark, DE (United States); Energy Frontier Research Centers (EFRC) (United States). Catalysis Center for Energy Innovation (CCEI)
Energy Frontier Research Centers (EFRC) (United States). Catalysis Center for Energy Innovation (CCEI)

Biomass conversion to chemicals and fuels has been epitomized by batch processing and long reaction times that limit the economic viability of future biorefineries and prevent modular manufacturing near the source-production site that is necessary due to the biomass’ large water content. Herein we introduce a continuous flow microreactor to enable process intensification and one thousand-fold device miniaturization for remote chemical processing. We demonstrate the approach in HCl-catalyzed fructose dehydration in water. We characterize and quantify the mixing using laser induced fluorescence (LIF) of fluorescent dyes and particle image velocimetry (PIV) of fluorescent microspheres. The estimated mixing times ranged from 0.03 to 4.8 s for residence times from 1 to 120 s, respectively. Moreover, a curved channel geometry induces secondary (Dean) vortices that produce a three-fold increase in mixing by diffusion through advection along the cross-sectional direction of the channel, creating dissipative chaotic mixing under laminar flow. We then obtain for the first time isothermal kinetics of fructose dehydration at short contact times and high temperatures and compare to a previously published, hybrid ab initio and data-driven kinetic model. Rigorous model optimization is carried out and an optimal HMF yield of 54% is attained in a single aqueous phase. High temperatures and low pH improve the reactor throughput by increasing the HMF space-time yield. We demonstrate the highest ever productivity (HMF yield per unit time). Importantly, this can be achieved at ~100% fructose conversion, eliminating the need for recycling to improve economics. Furthermore, optimization of the reactor dimensions and the specific energy dissipation rate results in ~60% pressure-drop related energy savings. We describe a methodology to scale-up microreactors to millimeter size and increase productivity 16-fold under optimal conditions. The energy efficiency and cost analysis for HMF production from corn stover of a typical corn farm indicate an optimal strategy for numbering-up millimeter size reactors and, importantly, they underscore the potential feasibility of producing bioproducts in a distributed manner.

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Research Organization:: American Institute of Chemical Engineers (AIChE), New York, NY (United States)

Sponsoring Organization:: USDOE Office of Energy Efficiency and Renewable Energy (EERE); National Science Foundation (NSF)

Grant/Contract Number:: EE0007888; 1434456

OSTI ID:: 1613478

Alternate ID(s):: OSTI ID: 1525502

Journal Information:: Energy & Environmental Science, Vol. 12, Issue 8; ISSN 1754-5692

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 40 works

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References (82)

A DFT study of the acid-catalyzed conversion of 2,5-dimethylfuran and ethylene to p-xylene Nikbin, Nima; Do, Phuong T.; Caratzoulas, Stavros Journal of Catalysis, Vol. 297 https://doi.org/10.1016/j.jcat.2012.09.017	journal	January 2013
Dehydration of fructose into 5-hydroxymethylfurfural in the presence of ionic liquids Lansalot-Matras, Clément; Moreau, Claude Catalysis Communications, Vol. 4, Issue 10 https://doi.org/10.1016/S1566-7367(03)00133-X	journal	October 2003
Reaction media dominated product selectivity in the isomerization of glucose by chromium trichloride: From aqueous to non-aqueous systems Jia, Songyan; Liu, Kairui; Xu, Zhanwei Catalysis Today, Vol. 234 https://doi.org/10.1016/j.cattod.2014.02.038	journal	October 2014
Adsorption of the Compounds Encountered in Monosaccharide Dehydration in Zeolite Beta León, Marta; Swift, T. Dallas; Nikolakis, Vladimiros Langmuir, Vol. 29, Issue 22 https://doi.org/10.1021/la401138g	journal	May 2013
Enhanced production of hydroxymethylfurfural from fructose with solid acid catalysts by simple water removal methods Shimizu, Ken-ichi; Uozumi, Rie; Satsuma, Atsushi Catalysis Communications, Vol. 10, Issue 14, p. 1849-1853 https://doi.org/10.1016/j.catcom.2009.06.012	journal	August 2009
Tandem Diels-Alder Reaction of Dimethylfuran and Ethylene and Dehydration to para -Xylene Catalyzed by Zeotypic Lewis Acids Patet, Ryan E.; Fan, Wei; Vlachos, Dionisios G. ChemCatChem, Vol. 9, Issue 13 https://doi.org/10.1002/cctc.201601584	journal	May 2017
Efficient Production of 5-Hydroxymethylfurfural Enhanced by Liquid–Liquid Extraction in a Membrane Dispersion Microreactor Zhou, Caijin; Shen, Chun; Ji, Kaiyue ACS Sustainable Chemistry & Engineering, Vol. 6, Issue 3 https://doi.org/10.1021/acssuschemeng.7b04368	journal	January 2018
Catalytic conversion of biomass-derived carbohydrates into fuels and chemicals via furanic aldehydes Hu, Lei; Zhao, Geng; Hao, Weiwei RSC Advances, Vol. 2, Issue 30 https://doi.org/10.1039/c2ra21811a	journal	January 2012
Oxidation of 5-hydroxymethylfurfural over supported Pt, Pd and Au catalysts Davis, Sara E.; Houk, Levi R.; Tamargo, Erin C. Catalysis Today, Vol. 160, Issue 1, p. 55-60 https://doi.org/10.1016/j.cattod.2010.06.004	journal	February 2011
A kinetic study on the decomposition of 5-hydroxymethylfurfural into levulinic acid Girisuta, B.; Janssen, L. P. B. M.; Heeres, H. J. Green Chemistry, Vol. 8, Issue 8 https://doi.org/10.1039/b518176c	journal	January 2006
Elucidating the Roles of Zeolite H-BEA in Aqueous-Phase Fructose Dehydration and HMF Rehydration Kruger, Jacob S.; Choudhary, Vinit; Nikolakis, Vladimiros ACS Catalysis, Vol. 3, Issue 6 https://doi.org/10.1021/cs4002157	journal	April 2013
Fuel Oil Quality of Biomass Pyrolysis OilsState of the Art for the End Users Oasmaa, Anja; Czernik, Stefan Energy & Fuels, Vol. 13, Issue 4 https://doi.org/10.1021/ef980272b	journal	July 1999
Converting fructose to 5-hydroxymethylfurfural: a quantum mechanics/molecular mechanics study of the mechanism and energetics Caratzoulas, Stavros; Vlachos, Dionisios G. Carbohydrate Research, Vol. 346, Issue 5 https://doi.org/10.1016/j.carres.2011.01.029	journal	April 2011
Renewable lubricants with tailored molecular architecture Liu, Sibao; Josephson, Tyler R.; Athaley, Abhay Science Advances, Vol. 5, Issue 2 https://doi.org/10.1126/sciadv.aav5487	journal	February 2019
Kinetics of the Decomposition of Fructose Catalyzed by Hydrochloric Acid in Subcritical Water: Formation of 5-Hydroxymethylfurfural, Levulinic, and Formic Acids Asghari, Feridoun Salak; Yoshida, Hiroyuki Industrial & Engineering Chemistry Research, Vol. 46, Issue 23 https://doi.org/10.1021/ie061673e	journal	November 2007
Introduction: mixing in microfluidics Ottino, Julio M.; Wiggins, Stephen Philosophical Transactions of the Royal Society of London. Series A: Mathematical, Physical and Engineering Sciences, Vol. 362, Issue 1818 https://doi.org/10.1098/rsta.2003.1355	journal	May 2004
Solvent system for effective near-term production of hydroxymethylfurfural (HMF) with potential for long-term process improvement Motagamwala, Ali Hussain; Huang, Kefeng; Maravelias, Christos T. Energy & Environmental Science, Vol. 12, Issue 7 https://doi.org/10.1039/C9EE00447E	journal	January 2019
Kinetics and Reaction Engineering of Levulinic Acid Production from Aqueous Glucose Solutions Weingarten, Ronen; Cho, Joungmo; Xing, Rong ChemSusChem, Vol. 5, Issue 7 https://doi.org/10.1002/cssc.201100717	journal	June 2012
Biomass into chemicals: Conversion of sugars to furan derivatives by catalytic processes Tong, Xinli; Ma, Yang; Li, Yongdan Applied Catalysis A: General, Vol. 385, Issue 1-2 https://doi.org/10.1016/j.apcata.2010.06.049	journal	September 2010
Norms and standards for fast pyrolysis liquids Oasmaa, Anja; Meier, Dietrich Journal of Analytical and Applied Pyrolysis, Vol. 73, Issue 2 https://doi.org/10.1016/j.jaap.2005.03.003	journal	June 2005
Acid-Catalyzed Production of 5-Hydroxymethyl Furfural from d -Fructose in Subcritical Water Salak Asghari, Feridoun; Yoshida, Hiroyuki Industrial & Engineering Chemistry Research, Vol. 45, Issue 7 https://doi.org/10.1021/ie051088y	journal	March 2006
Inhibition of Xylene Isomerization in the Production of Renewable Aromatic Chemicals from Biomass-Derived Furans Williams, C. Luke; Vinter, Katherine P.; Patet, Ryan E. ACS Catalysis, Vol. 6, Issue 3 https://doi.org/10.1021/acscatal.5b02329	journal	February 2016
Cycloaddition of Biomass-Derived Furans for Catalytic Production of Renewable p -Xylene Williams, C. Luke; Chang, Chun-Chih; Do, Phuong ACS Catalysis, Vol. 2, Issue 6 https://doi.org/10.1021/cs300011a	journal	April 2012
The influence of the initial and catalyst concentrations on the dehydration of d-fructose Kuster, Ben F. M.; S. van der Baan, Hessel Carbohydrate Research, Vol. 54, Issue 2 https://doi.org/10.1016/S0008-6215(00)84806-5	journal	April 1977
Techno-economic analysis of dimethylfuran (DMF) and hydroxymethylfurfural (HMF) production from pure fructose in catalytic processes Kazi, Feroz Kabir; Patel, Akshay D.; Serrano-Ruiz, Juan Carlos Chemical Engineering Journal, Vol. 169, Issue 1-3 https://doi.org/10.1016/j.cej.2011.03.018	journal	May 2011
Kinetics of Homogeneous Brønsted Acid Catalyzed Fructose Dehydration and 5-Hydroxymethyl Furfural Rehydration: A Combined Experimental and Computational Study Swift, T. Dallas; Bagia, Christina; Choudhary, Vinit ACS Catalysis, Vol. 4, Issue 1 https://doi.org/10.1021/cs4009495	journal	December 2013
Formation and Growth of Humins via Aldol Addition and Condensation during Acid-Catalyzed Conversion of 5-Hydroxymethylfurfural Patil, Sushil K. R.; Lund, Carl R. F. Energy & Fuels, Vol. 25, Issue 10 https://doi.org/10.1021/ef2010157	journal	October 2011
Reactions of d-fructose in water at temperatures up to 400°C and pressures up to 100MPa Aida, Taku Michael; Tajima, Kiyohiko; Watanabe, Masaru The Journal of Supercritical Fluids, Vol. 42, Issue 1 https://doi.org/10.1016/j.supflu.2006.12.017	journal	August 2007
Kinetic regimes in the tandem reactions of H-BEA catalyzed formation of p-xylene from dimethylfuran Williams, C. Luke; Vinter, Katherine P.; Chang, Chun-Chih Catalysis Science & Technology, Vol. 6, Issue 1 https://doi.org/10.1039/C5CY01320H	journal	January 2016
Quantitative Chemical Imaging of Nonplanar Microfluidics Gelber, Matthew K.; Kole, Matthew R.; Kim, Namjung Analytical Chemistry, Vol. 89, Issue 3 https://doi.org/10.1021/acs.analchem.6b03943	journal	January 2017
Biomass-Derived Butadiene by Dehydra-Decyclization of Tetrahydrofuran Abdelrahman, Omar A.; Park, Dae Sung; Vinter, Katherine P. ACS Sustainable Chemistry & Engineering, Vol. 5, Issue 5 https://doi.org/10.1021/acssuschemeng.7b00745	journal	March 2017
Transient micromixing: Examples of laminar and chaotic stirring Gleeson, James P. Physics of Fluids, Vol. 17, Issue 10 https://doi.org/10.1063/1.1928627	journal	January 2005
Quantification of chaotic strength and mixing in a micro fluidic system Kim, Ho Jun; Beskok, Ali Journal of Micromechanics and Microengineering, Vol. 17, Issue 11 https://doi.org/10.1088/0960-1317/17/11/005	journal	October 2007
Efficient production of the liquid fuel 2,5-dimethylfuran from 5-hydroxymethylfurfural over Ru/Co3O4 catalyst Zu, Yanhong; Yang, Panpan; Wang, Jianjian Applied Catalysis B: Environmental, Vol. 146 https://doi.org/10.1016/j.apcatb.2013.04.026	journal	March 2014
Efficient microwave-assisted synthesis of 5-hydroxymethylfurfural from concentrated aqueous fructose Hansen, Thomas S.; Woodley, John M.; Riisager, Anders Carbohydrate Research, Vol. 344, Issue 18 https://doi.org/10.1016/j.carres.2009.09.036	journal	December 2009
A two-step approach for the catalytic conversion of glucose to 2,5-dimethylfuran in ionic liquids Chidambaram, Mandan; Bell, Alexis T. Green Chemistry, Vol. 12, Issue 7 https://doi.org/10.1039/c004343e	journal	January 2010
Kinetic Regime Change in the Tandem Dehydrative Aromatization of Furan Diels–Alder Products Patet, Ryan E.; Nikbin, Nima; Williams, C. Luke ACS Catalysis, Vol. 5, Issue 4 https://doi.org/10.1021/cs5020783	journal	March 2015
Mixing Evaluation of a Passive Scaled-Up Serpentine Micromixer With Slanted Grooves Cook, Kristina J.; Fan, YanFeng; Hassan, Ibrahim Journal of Fluids Engineering, Vol. 135, Issue 8 https://doi.org/10.1115/1.4024146	journal	June 2013
General Acid-Type Catalysis in the Dehydrative Aromatization of Furans to Aromatics in H-[Al]-BEA, H-[Fe]-BEA, H-[Ga]-BEA, and H-[B]-BEA Zeolites Patet, Ryan E.; Koehle, Maura; Lobo, Raul F. The Journal of Physical Chemistry C, Vol. 121, Issue 25 https://doi.org/10.1021/acs.jpcc.7b02344	journal	June 2017
Microreactor Process for the Optimized Synthesis of 5-Hydroxymethylfurfural: A Promising Building Block Obtained by Catalytic Dehydration of Fructose Tuercke, T.; Panic, S.; Loebbecke, S. Chemical Engineering & Technology, Vol. 32, Issue 11 https://doi.org/10.1002/ceat.200900427	journal	November 2009
Fructose Dehydration to 5-Hydroxymethylfurfural over Solid Acid Catalysts in a Biphasic System Ordomsky, Vitaly V.; van der Schaaf, John; Schouten, Jaap C. ChemSusChem, Vol. 5, Issue 9 https://doi.org/10.1002/cssc.201200072	journal	July 2012
Tandem Lewis acid/Brønsted acid-catalyzed conversion of carbohydrates to 5-hydroxymethylfurfural using zeolite beta Swift, T. Dallas; Nguyen, Hannah; Erdman, Zachary Journal of Catalysis, Vol. 333 https://doi.org/10.1016/j.jcat.2015.10.009	journal	January 2016
Continuous production of 5-hydroxymethylfurfural from fructose: a design case study Torres, Ana I.; Daoutidis, Prodromos; Tsapatsis, Michael Energy & Environmental Science, Vol. 3, Issue 10 https://doi.org/10.1039/c0ee00082e	journal	January 2010
A new approach for the production of 2,5-furandicarboxylic acid by in situ oxidation of 5-hydroxymethylfurfural starting from fructose Kröger, Martin; Prüße, Ulf; Vorlop, Klaus‐Dieter Topics in Catalysis, Vol. 13, Issue 3, p. 237-242 https://doi.org/10.1023/A:1009017929727	journal	August 2000
p- Xylene Formation by Dehydrative Aromatization of a Diels–Alder Product in Lewis and Brønsted Acidic Zeolites Nikbin, Nima; Feng, Shuting; Caratzoulas, Stavros The Journal of Physical Chemistry C, Vol. 118, Issue 42 https://doi.org/10.1021/jp506027f	journal	October 2014
Top ten fundamental challenges of biomass pyrolysis for biofuels Mettler, Matthew S.; Vlachos, Dionisios G.; Dauenhauer, Paul J. Energy & Environmental Science, Vol. 5, Issue 7 https://doi.org/10.1039/c2ee21679e	journal	January 2012
A First Principles-Based Microkinetic Model for the Conversion of Fructose to 5-Hydroxymethylfurfural Nikbin, Nima; Caratzoulas, Stavros; Vlachos, Dionisios G. ChemCatChem, Vol. 4, Issue 4 https://doi.org/10.1002/cctc.201100444	journal	February 2012
Catalytical conversion of fructose and glucose into 5-hydroxymethylfurfural in hot compressed water by microwave heating Qi, Xinhua; Watanabe, Masaru; Aida, Taku M. Catalysis Communications, Vol. 9, Issue 13 https://doi.org/10.1016/j.catcom.2008.04.025	journal	July 2008
Continuous D-Fructose Dehydration to 5- Hydroxymethylfurfural Under Mild Conditions Aellig, Christof; Hermans, Ive ChemSusChem, Vol. 5, Issue 9 https://doi.org/10.1002/cssc.201200279	journal	July 2012
Dehydration of d-fructose to hydroxymethylfurfural in sub- and supercritical fluids Bicker, M.; Kaiser, D.; Ott, L. The Journal of Supercritical Fluids, Vol. 36, Issue 2, p. 118-126 https://doi.org/10.1016/j.supflu.2005.04.004	journal	December 2005
Solvent-tuned hydrophobicity for faujasite-catalyzed cycloaddition of biomass-derived dimethylfuran for renewable p-xylene Xiong, Ruichang; Sandler, Stanley I.; Vlachos, Dionisios G. Green Chemistry, Vol. 16, Issue 9 https://doi.org/10.1039/C4GC00727A	journal	January 2014
Glucose reactions with acid and base catalysts in hot compressed water at 473K Watanabe, Masaru; Aizawa, Yuichi; Iida, Toru Carbohydrate Research, Vol. 340, Issue 12 https://doi.org/10.1016/j.carres.2005.06.017	journal	September 2005
Chemical conversion and liquid-liquid extraction of 5-hydroxymethylfurfural from fructose by slug flow microreactor Shimanouchi, Toshinori; Kataoka, Yoshitaka; Tanifuji, Tatsuya AIChE Journal, Vol. 62, Issue 6 https://doi.org/10.1002/aic.15201	journal	February 2016
Microwave assisted rapid conversion of carbohydrates into 5-hydroxymethylfurfural catalyzed by mesoporous TiO2 nanoparticles Dutta, Saikat; De, Sudipta; Patra, Astam K. Applied Catalysis A: General, Vol. 409-410 https://doi.org/10.1016/j.apcata.2011.09.037	journal	December 2011
Renewable p -Xylene from 2,5-Dimethylfuran and Ethylene Using Phosphorus-Containing Zeolite Catalysts Cho, Hong Je; Ren, Limin; Vattipalli, Vivek ChemCatChem, Vol. 9, Issue 3 https://doi.org/10.1002/cctc.201601294	journal	January 2017
Chaotic Mixer for Microchannels Stroock, A. D. Science, Vol. 295, Issue 5555 https://doi.org/10.1126/science.1066238	journal	January 2002
Simple and selective conversion of fructose into HMF using extractive-reaction process in microreactor Lueckgen, Janine; Vanoye, Laurent; Philippe, Régis Journal of Flow Chemistry, Vol. 8, Issue 1 https://doi.org/10.1007/s41981-018-0004-7	journal	March 2018
Sulfated zirconia as a solid acid catalyst for the dehydration of fructose to 5-hydroxymethylfurfural Qi, Xinhua; Watanabe, Masaru; Aida, Taku M. Catalysis Communications, Vol. 10, Issue 13 https://doi.org/10.1016/j.catcom.2009.05.029	journal	July 2009
Process flowsheet optimization of chemicals production from biomass derived glucose solutions Lin, Zhaojia; Wang, Jingyao; Nikolakis, Vladimiros Computers & Chemical Engineering, Vol. 102 https://doi.org/10.1016/j.compchemeng.2016.09.012	journal	July 2017
Lewis acid zeolites for tandem Diels–Alder cycloaddition and dehydration of biomass-derived dimethylfuran and ethylene to renewable p-xylene Chang, Chun-Chih; Je Cho, Hong; Yu, Jingye Green Chemistry, Vol. 18, Issue 5 https://doi.org/10.1039/C5GC02164B	journal	January 2016
Tunable Oleo-Furan Surfactants by Acylation of Renewable Furans Park, Dae Sung; Joseph, Kristeen E.; Koehle, Maura ACS Central Science, Vol. 2, Issue 11 https://doi.org/10.1021/acscentsci.6b00208	journal	October 2016
Rapid Microfluidic Mixing Johnson, Timothy J.; Ross, David; Locascio, Laurie E. Analytical Chemistry, Vol. 74, Issue 1 https://doi.org/10.1021/ac010895d	journal	January 2002
Heterogeneous Catalysis for the Conversion of Sugars into Polymers Davis, Mark E. Topics in Catalysis, Vol. 58, Issue 7-9 https://doi.org/10.1007/s11244-015-0386-9	journal	April 2015
Tandem Lewis/Brønsted homogeneous acid catalysis: conversion of glucose to 5-hydoxymethylfurfural in an aqueous chromium( iii ) chloride and hydrochloric acid solution Dallas Swift, T.; Nguyen, Hannah; Anderko, Andrzej Green Chemistry, Vol. 17, Issue 10 https://doi.org/10.1039/C5GC01257K	journal	January 2015
Tin-containing zeolites are highly active catalysts for the isomerization of glucose in water Moliner, M.; Roman-Leshkov, Y.; Davis, M. E. Proceedings of the National Academy of Sciences, Vol. 107, Issue 14, p. 6164-6168 https://doi.org/10.1073/pnas.1002358107	journal	March 2010
Biomass to chemicals: Design of an extractive-reaction process for the production of 5-hydroxymethylfurfural Torres, A. I.; Tsapatsis, M.; Daoutidis, P. Computers & Chemical Engineering, Vol. 42 https://doi.org/10.1016/j.compchemeng.2011.12.013	journal	July 2012
Greener Approaches to Organic Synthesis Using Microreactor Technology Mason, Brian P.; Price, Kristin E.; Steinbacher, Jeremy L. Chemical Reviews, Vol. 107, Issue 6 https://doi.org/10.1021/cr050944c	journal	June 2007
Continuous particle separation in spiral microchannels using dean flows and differential migration Bhagat, Ali Asgar S.; Kuntaegowdanahalli, Sathyakumar S.; Papautsky, Ian Lab on a Chip, Vol. 8, Issue 11 https://doi.org/10.1039/b807107a	journal	January 2008
Glucose Isomerization by Enzymes and Chemo-catalysts: Status and Current Advances Li, Hu; Yang, Song; Saravanamurugan, Shunmugavel ACS Catalysis, Vol. 7, Issue 4 https://doi.org/10.1021/acscatal.6b03625	journal	March 2017
Phase Modifiers Promote Efficient Production of Hydroxymethylfurfural from Fructose Roman-Leshkov, Yuriy; Chheda, Juben N.; Dumesic, James A. Science, Vol. 312, Issue 5782, p. 1933-1937 https://doi.org/10.1126/science.1126337	journal	June 2006
Scale-out of Microreactor Stacks for Portable and Distributed Processing: Coupling of Exothermic and Endothermic Processes for Syngas Production Mettler, Matthew S.; Stefanidis, Georgios D.; Vlachos, Dionisios G. Industrial & Engineering Chemistry Research, Vol. 49, Issue 21 https://doi.org/10.1021/ie100459b	journal	November 2010
On the mechanism of selective oxidation of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid over supported Pt and Au catalysts Davis, Sara E.; Zope, Bhushan N.; Davis, Robert J. Green Chemistry, Vol. 14, Issue 1, p. 143-147 https://doi.org/10.1039/C1GC16074E	journal	January 2012
Chemistry in Microstructured Reactors Jähnisch, Klaus; Hessel, Volker; Löwe, Holger Angewandte Chemie International Edition, Vol. 43, Issue 4 https://doi.org/10.1002/anie.200300577	journal	January 2004
Almost-invariant sets and invariant manifolds — Connecting probabilistic and geometric descriptions of coherent structures in flows Froyland, Gary; Padberg, Kathrin Physica D: Nonlinear Phenomena, Vol. 238, Issue 16 https://doi.org/10.1016/j.physd.2009.03.002	journal	August 2009
Universality and imaginary potentials in advection–diffusion equations in closed flows Giona, M.; Cerbelli, S.; Vitacolonna, V. Journal of Fluid Mechanics, Vol. 513 https://doi.org/10.1017/S002211200400984X	journal	January 1999
Low-cost small scale processing technologies for production applications in various environments—Mass produced factories Bramsiepe, C.; Sievers, S.; Seifert, T. Chemical Engineering and Processing: Process Intensification, Vol. 51 https://doi.org/10.1016/j.cep.2011.08.005	journal	January 2012
Dean Flow Dynamics in Low-Aspect Ratio Spiral Microchannels Nivedita, Nivedita; Ligrani, Phillip; Papautsky, Ian Scientific Reports, Vol. 7, Issue 1 https://doi.org/10.1038/srep44072	journal	March 2017
Ultra-selective cycloaddition of dimethylfuran for renewable p-xylene with H-BEA Chang, Chun-Chih; Green, Sara K.; Williams, C. Luke Green Chem., Vol. 16, Issue 2 https://doi.org/10.1039/C3GC40740C	journal	January 2014
Production and upgrading of 5-hydroxymethylfurfural using heterogeneous catalysts and biomass-derived solvents Gallo, Jean Marcel R.; Alonso, David Martin; Mellmer, Max A. Green Chem., Vol. 15, Issue 1 https://doi.org/10.1039/C2GC36536G	journal	January 2013
Renewable lubricants with tailored molecular architecture Liu, Sibao; Josephson, Tyler R.; Athaley, Abhay American Association for the Advancement of Science https://doi.org/10.13016/m2rspk-oayh	collection	January 2019
Dean Flow Dynamics in Low-Aspect Ratio Spiral Microchannels Phillip, Ligrani,; Nivedita, Nivedita,; Ian, Papautsky, The University of North Carolina at Chapel Hill University Libraries https://doi.org/10.17615/05m2-3573	text	January 2017
Greener Approaches to Organic Synthesis Using Microreactor Technology Mason, Brian P.; Price, Kristin E.; Steinbacher, Jeremy L. ChemInform, Vol. 38, Issue 36 https://doi.org/10.1002/chin.200736259	journal	September 2007

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