Flow chemistry experiments in the undergraduate teaching laboratory: synthesis of diazo dyes and disulfides
Tóm tắt
By embedding flow technology in the early phases of academic education, students are exposed to both the theoretical and practical aspects of this modern and widely-used technology. Herein, two laboratory flow experiments are described which have been carried out by first year undergraduate students at Eindhoven University of Technology. The experiments are designed to be relatively risk-free and they exploit widely available equipment and cheap capillary flow reactors. The experiments allow students to develop a hands-on understanding of continuous processing and gives them insights in both organic chemistry and chemical engineering. Furthermore, they learn about the benefits of microreactors, continuous processing, multistep reaction sequences and multiphase chemistry. Undoubtedly, such skills are highly valued in both academia and the chemical industry.
Tài liệu tham khảo
Plutschack MB, Pieber B, Gilmore K, Seeberger PH (2017) The Hitchhiker’s guide to flow chemistry. Chem Rev 117:11796–11893
Govaerts S, Nyuchev A, Noel T (2020) Pushing the boundaries of C–H bond functionalization chemistry using flow technology. J Flow Chem 10:13–71
Sambiagio C, Noël T (2020) Flow photochemistry: Shine some light on those tubes! Trends in Chemistry 2:92–106
Noël T (2017) A personal perspective on the future of flow photochemistry. J Flow Chem 7:87–93
Cambié D, Bottecchia C, Straathof NJW, Hessel V, Noël T (2016) Applications of continuous-flow photochemistry in organic synthesis, material science, and water treatment. Chem Rev 116:10276–10341
Noël T, Cao Y, Laudadio G (2019) The fundamentals behind the use of flow reactors in electrochemistry. Acc Chem Res 52:2858–2869
Pletcher D, Green RA, Brown RCD (2018) Flow electrolysis cells for the synthetic organic chemistry laboratory. Chem Rev 118:4573–4591
Folgueiras-Amador AA, Wirth T (2017) Perspectives in flow electrochemistry. J Flow Chem 7:94–95
Liu Y, Chen G, Yue J (2020) Manipulation of gas-liquid-liquid systems in continuous flow microreactors for efficient reaction processes. J Flow Chem 103:103–121
Yue J (2018) Multiphase flow processing in microreactors combined with heterogeneous catalysis for efficient and sustainable chemical synthesis. Catal Today 308:3–19
Mallia CJ, Baxendale IR (2016) The use of gases in flow synthesis. Org Process Res Dev 20:327–360
Ramezani M, Kashfipour MA, Abolhasani M (2020) Minireview: flow chemistry studies of high-pressure gas-liquid reactions with carbon monoxide and hydrogen. J Flow Chem 10:93–101
Gutmann B, Cantillo D, Kappe CO (2015) Continuous-flow technology - a tool for the safe manufacturing of active pharmaceutical ingredients. Angew Chem Int Ed 54:6688–6728
Movsisyan M, Delbeke EIP, Berton JKET, Battilocchio C, Ley SV, Stevens CV (2016) Taming hazardous chemistry by continuous flow technology. Chem Soc Rev 45:4892–4928
Dallinger D, Gutmann B, Kappe CO (2020) The concept of chemical generators: on-site on-demand production of hazardous reagents in continuous-flow. Acc Chem Res 53:1330–1341
Gutmann B, Kappe CO (2017) Forbidden chemistries — paths to a sustainable future engaging continuous processing. J Flow Chem 7:65–71
Kockmann N, Thenée P, Fleischer-Trebes C, Laudadio G, Noël T (2017) Safety assessment in development and operation of modular continuous-flow processes. React Chem Eng 2:258–280
Baumann M, Moody TS, Smyth M, Wharry S (2020) A perspective on continuous flow chemistry in the pharmaceutical industry. Org Process Res Dev. https://doi.org/10.1021/acs.oprd.9b00524
May SA (2017) Flow Chemistry, Continuous processing, and continuous manufacturing: a pharmaceutical perspective. J Flow Chem 3–4:137–145
Leibfarth FA, Russell MG, Langley DM, Seo H, Kelly LP, Carney DW, Sello JK, Jamison TF (2018) Continuous-flow chemistry in undergraduate education: sustainable conversion of reclaimed vegetable oil into biodiesel. J Chem Educ 95:1371–1375
König B, Kreitmeier P, Hilgers P, Wirth T (2013) Flow chemistry in undergraduate organic chemistry education. J Chem Educ 90:934–936
Santandrea J, Kairouz V, Collins SK (2018) Continuous flow science in an undergraduate teaching laboratory: Photocatalytic Thiol-Ene reaction using visible light. J Chem Educ 95:1073–1077
Kairouz V, Collins SK (2018) Continuous flow science in an undergraduate teaching laboratory: bleach-mediated oxidation in a biphasic system. J Chem Educ 95:1069–1072
Simeonov SP, Afonso CAM (2013) Batch and flow synthesis of 5-hydroxymethylfurfural (HMF) from fructose as a bioplatform intermediate: an experiment for the organic or analytical laboratory. J Chem Educ 90:1373–1375
Volpe K, Podlesny EE (2020) Modernization of a photochemical reaction for the undergraduate laboratory: continuous flow Photopinacol coupling. J Chem Educ 97:586–591
Feng ZV, Edelman KR, Swanson BP (2015) Student-fabricated microfluidic devices as flow reactors for organic and inorganic synthesis. J Chem Educ 92:723–727
Vié C, Fattaccioli J, Jacq P (2019) Introduction to droplet-based Millifluidic chemistry using a macroscopic-droplet generator. J Chem Educ 96:797–800
Chia MC, Sweeney CM, Odom TW (2011) Chemistry in microfluidic channels. J Chem Educ 88:461–464
Hemling M, Crooks JA, Oliver PM, Brenner K, Gilbertson J, Lisensky GC, Weibel DB (2014) Microfluidics for high school chemistry students. J Chem Educ 91:112–115
Fernandez Rivas D et al (2020) Process intensification education contributes to sustainable development goals. Part 1. Educ Chem Eng 32 1–14
Fernandez Rivas D et al (2020) Process intensification education contributes to sustainable development goals. Part 2. Educ Chem Eng 32 15–24
Berton M, de Souza JM, Abdiaj I, McQuade DT, Snead DR (2020) Scaling continuous API synthesis from milligram to kilogram: extending the enabling benefits of micro to the plant. J Flow Chem 10:73–92
Britton J, Raston CL (2017) Multi-step continuous-flow synthesis. Chem Soc Rev 46:1250–1271
Bloemendal VRLJ, Janssen MACH, van Hest JCM, Rutjes FPJT (2020) Continuous one-flow multi-step synthesis of active pharmaceutical ingredients. React Chem Eng 5:1186–1197
Webb D, Jamison TF (2010) Continuous flow multi-step organic synthesis. Chem Sci 1:675–680
Oger N, Le Grognec E, Felpin FX (2015) Handling diazonium salts in flow for organic and material chemistry. Org Chem Front 2:590–614
Hu T, Baxendale IR, Baumann M (2016) Exploring flow procedures for diazonium formation. Molecules 91:918
Straathof NJW, Su Y, Hessel V, Noël T (2016) Accelerated gas-liquid visible light photoredox catalysis with continuous-flow photochemical microreactors. Nat Protoc 11:10–21
Britton J, Jamison TF (2017) The assembly and use of continuous-flow systems for chemical synthesis. Nat Protoc 12:2423–2446
Noel T, Su Y, Hessel V (2016) Beyond organometallic flow chemistry: the principles behind the use of continuous-flow reactors for synthesis. Top Organomet Chem 57:1–41
Talla A, Driessen B, Straathof NJW, Milroy L-G, Brunsveld L, Hessel V, Noel T (2015) Metal-free Photocatalytic aerobic oxidation of Thiols to disulfides in batch and continuous-flow. Adv Synth Catal 357:2180–2186
Su Y, Hessel V, Noël T (2015) A compact photomicroreactor design for kinetic studies of gas-liquid photocatalytic transformations. AICHE J 61:2215–2227
Bottecchia C, Erdmann N, Tijssen PMA, Milroy L-G, Brunsveld L, Hessel V, Noel T (2016) Batch and flow synthesis of disulfides by visible-light-induced TiO2 Photocatalysis. ChemSusChem 9:1781–1785
Laudadio G, Straathof NJW, Lanting MD, Knoops B, Hessel V, Noel T (2017) An environmentally benign and selective electrochemical oxidation of sulfides and thiols in a continuous-flow microreactor. Green Chem 19:4061–4066
Su Y, Talla A, Hessel V, Noël T (2015) Controlled Photocatalytic aerobic oxidation of Thiols to disulfides in an energy-efficient Photomicroreactor. Chem Eng Technol 38:1733–1742