Pushing Flow Chemistry to New Limits: Development of a Flow Process towards Spirangien A

ChemCatChem ◽  
2014 ◽  
Vol 6 (10) ◽  
pp. 2798-2800 ◽  
Author(s):  
Gerrit Jürjens ◽  
Andreas Kirschning
Keyword(s):  
Flow Chemistry ◽  
Flow Process

Flow Chemistry

2015 ◽  
Author(s):  
Tristan H. Lambert
Keyword(s):  
Continuous Flow ◽  
Flow Chemistry ◽  
Photochemical Oxidation ◽  
Max Planck ◽  
Chemical Research ◽  
Flow Process ◽  
Batch Reaction ◽  
Photocatalytic Reactions ◽  
Catalyzed Reactions ◽  
Reliable Solution

Although photocatalytic chemistry has been the subject of intense interest recently, the rate of these reactions is often slow due to the limited penetration of light into typical reaction media. Peter H. Seeberger at the Max-Planck Institute for Colloids and Surfaces in Potsdam and the Free University of Berlin showed (Chem. Sci. 2012, 3, 1612) that Ru(bpy)32+-catalyzed reactions such as the reduction of azide 1 to 2 can be achieved in as little as 1 min residence time using continuous flow, as opposed to the 2 h batch reaction time previously reported. The benefits of flow on a number of strategic photocatalytic reactions, including the coupling of 3 and 4 to produce 5, was also demonstrated (Angew. Chem. Int. Ed. 2012, 51, 4144) by Corey R.J. Stephenson at Boston University and Timothy F. Jamison at MIT. In this case, a reaction throughput of 0.914 mmol/h compares favorably with 0.327 mmol/h for the batch reaction. Professor Seeberger has also reported (Angew. Chem. Int. Ed. 2012, 51, 1706) a continuous-flow synthesis of Artemisinin 7, a highly effective antimalarial drug, starting from dihydroartemisinic acid 6. The conversion occurs by a sequence of photochemical oxidation with singlet oxygen, acidic Hock cleavage of the O–O bond, and oxidation with triplet oxygen, a process calculated to be capable of furnishing up to 200 g/day per reactor. A scalable intramolecular [2 + 2] photocycloaddition of 8 to produce 9 was reported (Tetrahedron Lett. 2012, 53, 1363) by Matthias Nettekoven of Hoffmann-La Roche in Basel, Switzerland. Stephen L. Buchwald at MIT developed (Angew. Chem. Int. Ed. 2012, 51, 5355) a flow process for the enantioselective β-arylation of ketones that involved lithiation of aryl bromide 10, borylation, and rhodium-catalyzed conjugate addition to cycloheptenone. For continuous flow production of enantioenriched alcohols such as 14, Miquel A. Pericás of the Institute of Chemical Research of Catalonia developed (Org. Lett. 2012, 14, 1816) the robust polystyrene-supported aminoalcohol 13 for diethylzinc addition to aldehydes. Professor Jamison found (Org. Lett. 2012, 14, 568) that flow chemistry provides a convenient and reliable solution to the reduction of esters to aldehydes with DIBALH (e.g., 15 to 16) that occurs rapidly and without the usual problem of overreduction.

15.1 Flow Chemistry in the Pharmaceutical Industry: Part 1

2018 ◽  
Author(s):  
A. G. O’Brien
Keyword(s):  
Pharmaceutical Industry ◽  
Large Scale ◽  
Flow Chemistry ◽  
Active Pharmaceutical Ingredients ◽  
Flow Process ◽  
Pharmaceutical Ingredients ◽  
Multistep Synthesis

Abstract The use of flow chemistry in the single- and multistep synthesis of active pharmaceutical ingredients has been well demonstrated. The pharmaceutical industry is now taking the next steps towards integration of flow chemistry into large-scale commercialized processes, which can effectively supply patient populations. This chapter details advances in this area, and outlines the data and knowledge required to select, develop, scale, and commercialize an efficient flow process.

Surfactant free synthesis of monodisperse styrenic nanoparticle colloids via flow chemistry

2020 ◽  
Author(s):  
Marta Antoniv ◽  
Shitong Zhu ◽  
Sehoon Chang ◽  
Nouf AlJabri
Keyword(s):  
Flow Chemistry

MATERIAL HANDLING MACHINES AND SYSTEMS – UMI-TWINN PROJECT CONTRIBUTION

2019 ◽  
Vol 12 (1) ◽  
pp. 7-20
Author(s):  
Péter Telek ◽  
Béla Illés ◽  
Christian Landschützer ◽  
Fabian Schenk ◽  
Flavien Massi
Keyword(s):  
Material Handling ◽  
Digital Data ◽  
Flow Process ◽  
Research Directions ◽  
Scientific Excellence ◽  
Research Activities ◽  
New Research ◽  
Eu Project ◽  
The University

Nowadays, the Industry 4.0 concept affects every area of the industrial, economic, social and personal sectors. The most significant changings are the automation and the digitalization. This is also true for the material handling processes, where the handling systems use more and more automated machines; planning, operation and optimization of different logistic processes are based on many digital data collected from the material flow process. However, new methods and devices require new solutions which define new research directions. In this paper we describe the state of the art of the material handling researches and draw the role of the UMi-TWINN partner institutes in these fields. As a result of this H2020 EU project, scientific excellence of the University of Miskolc can be increased and new research activities will be started.

Scalable Synthesis of Functionalized Ferrocenyl Azides and Amines Enabled by Flow Chemistry

2019 ◽  
Author(s):  
Merlin Kleoff ◽  
Johannes Schwan ◽  
Lisa Boeser ◽  
Bence Hartmayer ◽  
Mathias Christmann ◽  
...  
Keyword(s):  
Reaction Time ◽  
Heterogeneous Reaction ◽  
Reduction Process ◽  
Flow Chemistry ◽  
Subsequent Reaction ◽  
Scalable Synthesis ◽  
High Yields ◽  
Reactor Section

A scalable access to functionalized 1,1’- and 1,2-ferrocenyl azides has been realized in flow. By halogen‒lithium exchange of ferrocenyl halides and subsequent reaction with tosyl azide, a variety of functionalized ferrocenyl azides was obtained in high yields. To allow a scalable preparation of these potentially explosive compounds, an efficient flow protocol was developed accelerating the reaction time to minutes and circumventing accumulation of potentially hazardous intermediates. Switching from homogeneous to triphasic flow amidst process was key for handling a heterogeneous reaction mixture formed after a heated reactor section. The corresponding and synthetically versatile ferrocenyl amines were then prepared by a reliable reduction process.

Room Temperature Flow Electrochemistry as a Means of Retaining the “Memory of Chirality” via Hofer Moest Type Reaction

2020 ◽  
Author(s):  
Tomas Hardwick ◽  
Rossana Cicala ◽  
Nisar Ahmed
Keyword(s):  
Continuous Flow ◽  
Room Temperature ◽  
Biological Activities ◽  
Supporting Electrolyte ◽  
Enantiomeric Excess ◽  
Flow Chemistry ◽  
Batch Processes ◽  
Enabling Technology ◽  
Chiral Compounds ◽  
Memory Of Chirality

<p>Many chiral compounds have become of great interest to the pharmaceutical industry as they possess various biological activities. Concurrently, the concept of “memory of chirality” has been proven as a powerful tool in asymmetric synthesis, while flow chemistry has begun its rise as a new enabling technology to add to the ever increasing arsenal of techniques available to the modern day chemist. Here, we have employed a new simple electrochemical microreactor design to oxidise an L-proline derivative at room temperature in continuous flow. Flow performed in microreactors offers up a number of benefits allowing reactions to be performed in a more convenient and safer manner, and even allow electrochemical reactions to take place without a supporting electrolyte due to a very short interelectrode distance. By the comparison of electrochemical oxidations in batch and flow we have found that continuous flow is able to outperform its batch counterpart, producing a good yield (71%) and a better enantiomeric excess (64%) than batch with a 98% conversion. We have, therefore, provided evidence that continuous flow chemistry has the potential to act as a new enabling technology to replace some aspects of conventional batch processes. </p>

Flow Chemistry Controls Both Self-Assembly and the Entrapped Oscillatory Cargo in Belousov-Zhabotinsky Driven Polymerization-Induced Self-Assembly

2019 ◽  
Author(s):  
Liman Hou ◽  
Marta Dueñas-Diez ◽  
Rohit Srivastava ◽  
Juan Perez-Mercader
Keyword(s):  
Self Assembly ◽  
Flow Chemistry ◽  
Batch Reactors ◽  
Equilibrium Conditions ◽  
One Pot ◽  
Bz Reaction ◽  
Polymer Vesicles ◽  
Simultaneous Control ◽  
Novel Method ◽  
Continuously Stirred Tank Reactor

<p></p><p>Belousov-Zhabotinsky (B-Z) reaction driven polymerization-induced self-assembly (PISA), or B-Z PISA, is a novel method for the autonomous one-pot synthesis of polymer vesicles from a macroCTA (macro chain transfer agent) and monomer solution (“soup”) containing the above and the BZ reaction components. In it, the polymerization is driven (and controlled) by periodically generated radicals generated in the oscillations of the B-Z reaction. These are inhibitor/activator radicals for the polymerization. Until now B-Z PISA has only been carried out in batch reactors. In this manuscript we present the results of running the system using a continuously stirred tank reactor (CSTR) configuration which offers some interesting advantages.Indeed, by controlling the CSTR parameters we achieve reproducible and simultaneous control of the PISA process and of the properties of the oscillatory cargo encapsulated in the resulting vesicles. Furthermore, the use of flow chemistry enables a more precise morphology control and chemical cargo tuning. Finally, in the context of biomimetic applications a CSTR operation mimics more closely the open non-equilibrium conditions of living systems and their surrounding environments.</p><p></p>

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