Optimization of continuous-flow diphenyldiazomethane synthesis: an integrated undergraduate chemistry experiment

被引:1
作者
van Summeren, Luuk T. C. G. [1 ]
Gerretzen, Jan [2 ]
Rutjes, Floris P. J. T. [1 ,3 ]
Bloemberg, Tom G. [1 ,3 ]
机构
[1] Radboud Univ Nijmegen, Educ Inst Mol Sci, Heyendaalsweg 135, NL-6525 AJ Nijmegen, Netherlands
[2] Nouryon Chem BV, Integrated Supply Chain Adv Analyt & Control, Zutphenseweg 10, NL-7418 AJ Deventer, Netherlands
[3] Radboud Univ Nijmegen, Inst Mol & Mat, Heyendaalsweg 135, NL-6525 AJ Nijmegen, Netherlands
关键词
Diphenyldiazomethane; Chemical education; Flow chemistry; Experimental design; DoE; SULFOXIDE-CARBODIIMIDE REACTIONS; ACID ANHYDRIDE MIXTURES; DIMETHYL-SULFOXIDE; SELECTIVE METHOD; SWERN OXIDATION; DIAZO-COMPOUNDS; ALCOHOLS; CONVERSION; HYDRAZONES; CARBONYLS;
D O I
10.1007/s41981-020-00107-4
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We present a challenging flow-chemistry experiment concerning the synthesis of diphenyldiazomethane using the Omura-Sharma-Swern oxidation, that we have developed and used in our second-year undergraduate lab classes over the past seven years. The experiment integrates a number of different aspects and concepts of chemistry that are traditionally taught as separate subjects in undergraduate chemical education: organic synthesis, quantitative chemical analysis, design of experiments, optimization, statistical modelling, computer programming and continuous-flow processes.
引用
收藏
页码:59 / 66
页数:8
相关论文
共 50 条
  • [1] Optimization of continuous-flow diphenyldiazomethane synthesis: an integrated undergraduate chemistry experiment
    Luuk T. C. G. van Summeren
    Jan Gerretzen
    Floris P. J. T. Rutjes
    Tom G. Bloemberg
    Journal of Flow Chemistry, 2021, 11 : 59 - 66
  • [2] Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid
    Aw, Alex
    Fritz, Marshall
    Napoline, Jonathan W.
    Pollet, Pamela
    Liotta, Charles L.
    JOVE-JOURNAL OF VISUALIZED EXPERIMENTS, 2017, (129):
  • [3] A Continuous-Flow Process for the Synthesis of Artemisinin
    Kopetzki, Daniel
    Levesque, Francois
    Seeberger, Peter H.
    CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (17) : 5450 - 5456
  • [4] The Continuous-Flow Synthesis of Ibuprofen
    Bogdan, Andrew R.
    Poe, Sarah L.
    Kubis, Daniel C.
    Broadwater, Steven J.
    McQuade, D. Tyler
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (45) : 8547 - 8550
  • [5] Beyond Organometallic Flow Chemistry: The Principles Behind the Use of Continuous-Flow Reactors for Synthesis
    Noel, Timothy
    Su, Yuanhai
    Hessel, Volker
    ORGANOMETALLIC FLOW CHEMISTRY, 2016, 57 : 1 - 41
  • [6] Toward a Continuous-Flow Synthesis of Boscalid®
    Glasnov, Toma N.
    Kappe, C. Oliver
    ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (17) : 3089 - 3097
  • [7] Continuous-Flow Synthesis of Tramadol from Cyclohexanone
    Monos, Timothy M.
    Jaworski, Jonathan N.
    Stephens, John C.
    Jamison, Timothy F.
    SYNLETT, 2020, 31 (19) : 1888 - 1893
  • [8] Multistep Continuous-Flow Synthesis of Condensed Benzothiazoles
    Loevei, Klara
    Greiner, Istvan
    Eles, Janos
    Szigetvari, Aron
    Dekany, Miklos
    Levai, Sandor
    Novak, Zoltan
    Turos, Gyoergy Istvan
    JOURNAL OF FLOW CHEMISTRY, 2015, 5 (02) : 74 - 81
  • [9] Synthesis of γ-valerolactone using a continuous-flow reactor
    Tukacs, Jozsef M.
    Jones, Richard V.
    Darvas, Ferenc
    Dibo, Gabor
    Lezsak, Gabor
    Mika, Laszlo T.
    RSC ADVANCES, 2013, 3 (37): : 16283 - 16287
  • [10] Multistep Continuous-Flow Synthesis of Condensed Benzothiazoles
    Klára Lövei
    István Greiner
    János Éles
    Áron Szigetvári
    Miklós Dékány
    Sándor Lévai
    Zoltán Novák
    György István Túrós
    Journal of Flow Chemistry, 2015, 5 : 74 - 81