5-(hydroperoxymethyl)-2-phenyloxazole ....Safe and Fast Flow Synthesis of Functionalized Oxazoles with Molecular Oxygen in a Microstructured Reactor

The synthesis of hydroperoxymethyl oxazoles by oxidation of alkylideneoxazoles with molecular oxygen was implemented in a microstructured reactor for increased safety and larger-scale applications. Elaborate studies on the influence of pressure and temperature were performed, and the apparent activation energy for the oxidation reaction was determined. Elevated temperatures up to 100 °C and pressures up to 18 bar(a) led to a conversion rate of approximately 90% within 4 h of the reaction time, thus displaying the high potential and beneficial effect of using a microreactor setup with liquid recycle loop for this oxidation. The in situ reduction of the generated hydroperoxide functionality shows the capability of this setup for follow-up transformations.

5-(hydroperoxymethyl)-2-phenyloxazole

Oxazole–hydroperoxide 3as a colorless solid. R_f (PE/EA 3:1 = 0.31).

¹H NMR (30 MHz, CDCl₃) δ = 4.98 (s, 2H), 7.12 (s, 1H), 7.49–7.29 (m, 3H), 7.88–7.75 (m, 2H), 10.16 (s, 1H). GC-MS (EI) m/z = 173.1 (M – OH), 144.1 (M – CH₂OOH), 116.1 (M – C₆H₅ + 2H), 89.1.

Safe and Fast Flow Synthesis of Functionalized Oxazoles with Molecular Oxygen in a Microstructured Reactor

Sarah Bay^†, Tobias Baumeister^‡, A. Stephen K. Hashmi^†§, and Thorsten Röder^*‡

^† Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg,Germany

^‡ Institute of Chemical Process Engineering, Mannheim University of Applied Sciences, Paul-Wittsack-Str. 10, 68163 Mannheim, Germany

^§ Chemistry Department, Faculty of Science, King Abdulaziz University (KAU), 21589 Jeddah, Saudi Arabia

Org. Process Res. Dev., Article ASAP

DOI: 10.1021/acs.oprd.6b00118

*E-mail: t.roeder@hs-mannheim.de. Telephone: +49 621 292 6800.

http://pubs.acs.org/doi/abs/10.1021/acs.oprd.6b00118

Organisch-Chemisches Institut                                     
Im Neuenheimer Feld 270
69120 Heidelberg
Germany

Institute of Chemical Process Engineering, Mannheim University of Applied Sciences, Paul-Wittsack-Str. 10, 68163 Mannheim, Germany

Panorama picture of the Campus in July 2006

Thorsten Röder

Prof. Dr.

Professor (Full)

Hochschule Mannheim, Mannheim · Institute of Chemical Process Engineering

Research experience

• Sep 2009–present

  Professor (Full)

  Hochschule Mannheim · Institute of Chemical Process Engineering
  Germany · Mannheim
• Sep 2005–Aug 2009

  Laboratory Head

  Novartis · Chemical and Analytical Process Development
  Switzerland · Basel
• Sep 1999–Aug 2004

  PhD Student

  Universität Paderborn · Department of Chemistry · Physical Chemistry Prof. Kitzerow
  Germany · Paderborn

 Teaching experience

• Sep 2009–present

  Professor (Full)

  Hochschule Mannheim · Institute of Chemical Process Engineering
  Germany
  Lectures in: Chemical Reaction Engineering Thermodynamic Microreactors & Nanotechnology CFD Practical Course: Chemical Reaction Engineering

Education

• Oct 1999–Oct 2004

  Universität Paderborn

  Physical Chemistry · Dr. rer. nat.
  Germany · Paderborn
• Sep 1994–Sep 1999

  Universität Paderborn

  Chemistry · Diplom Chemiker
  Germany

Prof. Dr. A. Stephen K. Hashmi

E-Mail hashmi@hashmi.de

/////////Safe and Fast,  Flow Synthesis, Functionalized Oxazoles, Molecular Oxygen, Microstructured Reactor






TIBET FOOD
.























/////////