References of "Monbaliu, Jean-Christophe"
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See detailIntegrated continuous flow photoreactors: Photooxidation of (L)-methionine with singlet oxygen
Emmanuel, Noémie ULiege; Monbaliu, Jean-Christophe ULiege

Conference (2017, July 06)

Development of photochemistry in macroscopic batch reaction vessels is hampered due to inherent limitations: light penetration remains superficial, resulting in inhomogeneous irradiation and hence to side ... [more ▼]

Development of photochemistry in macroscopic batch reaction vessels is hampered due to inherent limitations: light penetration remains superficial, resulting in inhomogeneous irradiation and hence to side-reactions or product degradation due to overexposure. The recent implementation of photochemical processes in microreactors under continuous-flow conditions appeared to be much more powerful than its batch analogue in terms of irradiation efficiency and light penetration. Furthermore, the fine control of residence time ensures an accurate control of the irradiation time, avoiding side-reactions and degradation. The scalable photooxidation of (L)-methionine with singlet oxygen using Rose Bengal as a sensitizer was successfully implemented in a microreactor setup and led to total and selective conversion into methionine sulfoxide, an important building block for the organic synthesis of peptides or functionalized amino acid. The reaction was performed in less than 1 min while the same reaction in batch took 2 h. Other substrates as α-terpinene or citronellol were also photooxidized into high added value compounds using the same conditions. [less ▲]

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See detailIntegrated continuous flow photoreactors: Photooxidation of (L)-methionine derivatives with singlet oxygen
Emmanuel, Noémie ULiege; Monbaliu, Jean-Christophe ULiege

Conference (2017, May 09)

Development of photochemistry in macroscopic batch reaction vessels is hampered due to inherent limitations: light penetration remains superficial, resulting in inhomogeneous irradiation and hence to side ... [more ▼]

Development of photochemistry in macroscopic batch reaction vessels is hampered due to inherent limitations: light penetration remains superficial, resulting in inhomogeneous irradiation and hence to side-reactions or product degradation due to overexposure. The recent implementation of photochemical processes in microreactors under continuous-flow conditions appeared to be much more powerful than its batch analogue in terms of irradiation efficiency and light penetration. Furthermore, the fine control of residence time ensures an accurate control of the irradiation time, avoiding side-reactions and degradation. The photooxidation of (L)-methionine with singlet oxygen using Rose Bengal as a sensitizer was successfully implemented in a microreactor setup and led to total and selective conversion into methionine sulfoxide, an important building block for the organic synthesis of peptides or functionalized amino acid. The reaction was performed in 1 min while the same reaction in batch took 2 h. [less ▲]

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See detailProcess intensification of the synthesis of glycerol carbonate under microwave irradiation or continuous-flow conditions
Estager, Julien; Pleck, Julie; Gerardy, Romaric ULiege et al

Conference (2017, May)

Despite low crude oil prices and the increasing access to shale gas, the establishment of a biobased economy remains a worldwide priority. An integrated biobased economy would not only consider renewable ... [more ▼]

Despite low crude oil prices and the increasing access to shale gas, the establishment of a biobased economy remains a worldwide priority. An integrated biobased economy would not only consider renewable biobased resources to provide industrially relevant chemicals, but would also redefine chemical processing by using greener, safer and more selective process technologies. The last few decades have witnessed the emergence of promising alternative energy sources such as microwave irradiation and alternative process technology such as continuous-flow reactors. Even if biobased chemicals are still marginal on the marklet compared to petrochemicals, many biorefineries are now able to convert biomass into biobased chemical building blocks of good purity on large scales. Amongst these products, glycerol – a side product of the biodiesel industry – is a particularly appealing chemical platform thanks to its high functionality and its wide availability. Various high-value added chemicals can be obtained from glycerol, among which glycerol carbonate retained our attention. Glycerol carbonate is an attractive glycerol derivative that can be used in many applications ranging from low-VOC solvent to polymer synthesis. Many publications describe its synthesis using different catalysts or alternative activation methods such as microwave. Our research effort in process intensification for the industrial valorization of biomass led us to develop an intensified carbonation process of glycerol under microwave irradiation, affording an unprecedented reactivity with short reaction times and high selectivity towards glycerol carbonate. Based on this preliminary study, and using the microwave-to-flow paradigm, continuous-flow processes using mesofluidic reactors have been developed to obtain glycerol carbonate in good yield and high purity. [less ▲]

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See detailReinventing chemical manufacturing: toward a compact and mobile factory?
Monbaliu, Jean-Christophe ULiege

Scientific conference (2017, April 27)

Detailed reference viewed: 21 (1 ULiège)
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See detailExpanding chemistry's horizon with continuous-flow reactors - part II
Monbaliu, Jean-Christophe ULiege

Conference (2017, April 20)

Continuous-flow micro- and mesofluidic reactors come with inherent properties that can be advantageously utilized for expanding the horizon of synthetic organic chemistry. Accurate control over local ... [more ▼]

Continuous-flow micro- and mesofluidic reactors come with inherent properties that can be advantageously utilized for expanding the horizon of synthetic organic chemistry. Accurate control over local process parameters, even under extreme conditions, inherent safety, production homogeneity and seamless scale-up are amongst the most important assets of continuous-flow chemistry. Besides, flow chemistry enables the design of efficient multistep processes with significantly reduced footprints. In this lecture, we will discuss some of the most fascinating aspects of continuous-flow micro- and mesofluidic reactors in the specific context of preparative organic chemistry. Multiple examples illustrating the development and implementation of continuous-flow multistep strategies for the synthesis of high-value added organic targets will be presented. [less ▲]

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See detailFlow-Chemistry Education Seminar
Monbaliu, Jean-Christophe ULiege

Scientific conference (2017, March 07)

This seminar presents the efforts for implementing flow-chemistry in early chemistry curricula and academic research labs. We will illustrate the key concepts that are integrated in a series of lectures ... [more ▼]

This seminar presents the efforts for implementing flow-chemistry in early chemistry curricula and academic research labs. We will illustrate the key concepts that are integrated in a series of lectures organized at the Department of Chemistry, University of Liège (Belgium). These lectures are complemented by workshops that successfully convey the subject matter at hand through practice in the lab. Some practical aspects for a successful curricular implementation will be thoroughly discussed. [less ▲]

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See detailExpanding chemistry's horizon with continuous-flow reactors
Monbaliu, Jean-Christophe ULiege

in Corning Reactor Technologies Annual Conference (2017) (2017, March)

Continuous-flow micro- and mesofluidic reactors come with inherent properties that can be advantageously utilized for expanding the horizon of synthetic organic chemistry. Accurate control over local ... [more ▼]

Continuous-flow micro- and mesofluidic reactors come with inherent properties that can be advantageously utilized for expanding the horizon of synthetic organic chemistry. Accurate control over local process parameters, even under extreme conditions, inherent safety, production homogeneity and seamless scale-up are amongst the most important assets of continuous-flow chemistry. Besides, flow chemistry enables the design of efficient multistep processes with significantly reduced footprints. In this lecture, we will discuss some of the most fascinating aspects of continuous-flow micro- and mesofluidic reactors in the specific context of preparative organic chemistry. Multiple examples illustrating the development and implementation of continuous-flow multistep strategies for the synthesis of high-value added organic targets will be presented. [less ▲]

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See detailExploring molecular antipodes with flow chemistry
Monbaliu, Jean-Christophe ULiege

in Monbaliu, Jean-Christophe (Ed.) FROST 6 (2017)

This lecture illustrates our work in flow chemistry with chemicals at the antipodes of molecular complexity. The first example deals with the valorization of biomass-derived small platform molecules, and ... [more ▼]

This lecture illustrates our work in flow chemistry with chemicals at the antipodes of molecular complexity. The first example deals with the valorization of biomass-derived small platform molecules, and in particular the implementation of a deoxydehydration (DODH) reaction of glycerol towards allyl alcohol under continuous-flow conditions. The combination of a unique reactive dynamic feed solution approach and short exposure to high temperature gave high yield and excellent selectivity in the presence of formic acid, triethyl orthoformate, or a combination of both. The second example deals with the preparation of large bio macromolecules, and in particular the implementation of chemical native ligation towards peptide constructs under continuous-flow conditions. The combination of the unique assets of microfluidic reactors and the development of new reagents/conditions were exploited to perform extremely fast ligations at difficult junctions that are notoriously time-consuming. Ligation times down to 2 min were achieved, with excellent conversion and overall isolated yields for a range of macrocylic peptides bearing up to 29 residues. The reaction conditions were also amenable, upon minor adjustments, to less hindered junctions. [less ▲]

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See detailExpanding Chemistry’s Horizon with Continuous-Flow Reactors - part III
Monbaliu, Jean-Christophe ULiege

Conference (2017)

Continuous-flow micro- and mesofluidic reactors come with inherent properties that can be advantageously utilized for expanding the horizon of synthetic organic chemistry. Accurate control over local ... [more ▼]

Continuous-flow micro- and mesofluidic reactors come with inherent properties that can be advantageously utilized for expanding the horizon of synthetic organic chemistry. Accurate control over local process parameters, even under extreme conditions, inherent safety, production homogeneity and seamless scale-up are amongst the most important assets of continuous-flow chemistry. Besides, flow chemistry enables the design of efficient multistep processes with significantly reduced footprints. In this lecture, we will discuss some of the most fascinating aspects of continuous-flow micro- and mesofluidic reactors in the specific context of preparative organic chemistry. Multiple examples illustrating the development and implementation of continuous-flow multistep strategies for the synthesis of high-value added organic targets will be presented. [less ▲]

Detailed reference viewed: 31 (1 ULiège)
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See detailScalable Photocatalytic Oxidation of Methionine under Continuous-Flow Conditions
Emmanuel, Noémie ULiege; Mendoza Gallego, Carlos ULiege; Winter, Marc et al

in Organic Research Process & Development (2017)

Highly efficient and chemoselective singlet oxygen oxidation of unprotected methionine was performed in water using a continuous mesofluidic reactor. Sustainable process engineering and conditions were ... [more ▼]

Highly efficient and chemoselective singlet oxygen oxidation of unprotected methionine was performed in water using a continuous mesofluidic reactor. Sustainable process engineering and conditions were combined to maximize process efficiency and atom-economy, with virtually no waste generation and safe operating conditions. Three water soluble metal-free photosensitizers (Rose Bengal, Methylene Blue, and tetrakis(4-carboxyphenyl)porphyrin) were assessed. The best results were obtained with Rose Bengal (0.1 mol%) at room temperature under white light irradiation and a slight excess of oxygen. Process and reaction parameters were monitored in real-time with in-line NMR. Other classical organic substrates (alpha-terpinene and citronellol) were oxidized under similar conditions with excellent performances. [less ▲]

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See detailExploring the Fundamentals of Microreactor Technology with Multidisciplinary Lab Experiments Combining the Synthesis and Characterization of Inorganic Nanoparticles
Emmanuel, Noémie ULiege; Emonds-Alt, Gauthier ULiege; Lismont, Marjorie et al

in Journal of Chemical Education (2017)

Multidisciplinary lab experiments combining microfluidics, nanoparticle synthesis and characterization are presented. These experiments rely on the implementation of affordable yet efficient microfluidic ... [more ▼]

Multidisciplinary lab experiments combining microfluidics, nanoparticle synthesis and characterization are presented. These experiments rely on the implementation of affordable yet efficient microfluidic setups based on PFA capillary coils and standard HPLC connectors in upper undergraduate chemistry labs. Fundamental principles and concepts, as well as practical tips for the rapid deployment of microfluidics are presented. In-line membrane separation, segmented-flow regime, high temperature experiments, and in-line analytical techniques are illustrated with the preparation of inorganic nanoparticles (silver, gold, cadmium selenide or telluride) in microreactors. Besides microfluidics, analytical techniques for nanoparticle analysis are also illustrated. [less ▲]

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See detailRevisiting the deoxydehydration of glycerol towards allyl alcohol under continuous-flow conditions
Ntumba Tshibalonza, Nelly; Monbaliu, Jean-Christophe ULiege

in Green Chemistry (2017)

The deoxydehydration (DODH) of glycerol towards allyl alcohol was revisited under continuous-flow conditions combining a microfluidic reactor setup and a unique reactive dynamic feed solution approach ... [more ▼]

The deoxydehydration (DODH) of glycerol towards allyl alcohol was revisited under continuous-flow conditions combining a microfluidic reactor setup and a unique reactive dynamic feed solution approach. Short reaction times, high yield and excellent selectivity were achieved at high temperature and moderate pressure in the presence of formic acid, triethyl orthoformate, or a combination of both. Triethyl orthoformate appeared as a superior reagent for the DODH of glycerol, with shorter reaction times, lower reaction temperatures and more robust conditions. In-line IR spectroscopy and computations provided different perspectives on the unique reactivity of glycerol O,O,O-orthoesters. [less ▲]

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See detailAssessing Inter- and Intramolecular Continuous-Flow Strategies towards Methylphenidate Hydrochloride
Gerardy, Romaric ULiege; Winter, Marc; Vizza, Alessandra et al

in Reaction Chemistry and Engineering (2017), 2(2), 149-158

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See detailAssessing Inter-and Intramolecular Continuous-Flow Strategies towards Methylphenidate Hydrochloride
Gerardy, Romaric ULiege; Winter, Marc; Vizza, Alessandra et al

in Reaction Chemistry and Engineering (2017)

The batch-to-flow translation of inter- and intramolecular strategies for the diastereoselective preparation of the active pharmaceutical ingredient threo-methylphenidate hydrochloride is presented. Both ... [more ▼]

The batch-to-flow translation of inter- and intramolecular strategies for the diastereoselective preparation of the active pharmaceutical ingredient threo-methylphenidate hydrochloride is presented. Both inter- and intramolecular strategies imply the telescoping of multiple processing steps and the generation of unstable diazospecies under continuous-flow conditions. The intermolecular strategy relies on an unprecedented continuous-flow Rh-catalyzed intermolecular C-H carbene insertion, providing enriched threo-N-Boc methylphenidate in 38% or 19% isolated yield according to sequential or fully telescoped processes, respectively. Quantitative Boc-deprotection is carried out off-line. The intramolecular strategy relies on a continuous-flow thermal intramolecular C-H carbene insertion, providing enriched threo-methylphenidate hydrochloride in 70% isolated yield. A continuous-flow photochemical alternative is also presented. The critical step of the most promising intramolecular strategy is implemented on mesoscale in a pilot-scale continuous-flow reactor. [less ▲]

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See detailAssessing inter- and intramolecular continuous-flow strategies towards methylphenidate (Ritalin) hydrochloride
Gerardy, Romaric ULiege; Winter, Marc; Vizza, Alessandra et al

in Reaction Chemistry and Engineering (2017)

The batch-to-flow translation of inter- and intramolecular strategies for the diastereoselective preparation of the active pharmaceutical ingredient threo-methylphenidate hydrochloride is presented. Both ... [more ▼]

The batch-to-flow translation of inter- and intramolecular strategies for the diastereoselective preparation of the active pharmaceutical ingredient threo-methylphenidate hydrochloride is presented. Both inter- and intramolecular strategies imply the telescoping of multiple processing steps and the generation of unstable diazo species under continuous-flow conditions. The intermolecular strategy relies on an unprecedented continuous-flow Rh-catalyzed intermolecular C–H carbene insertion, providing enriched threo-N-Boc methylphenidate in 38% or 19% isolated yield according to sequential or fully telescoped processes, respectively. Quantitative Boc-deprotection is carried out off-line. The intramolecular strategy relies on a continuous-flow thermal intramolecular C–H carbene insertion, providing enriched threo-methylphenidate hydrochloride in 70% isolated yield. A continuous-flow photochemical alternative is also presented. The critical step of the most promising intramolecular strategy is implemented on the mesoscale in a pilot-scale continuous-flow reactor. [less ▲]

Detailed reference viewed: 34 (8 ULiège)
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See detailIntegrated microfluidic device for the synthesis of SERS substrates
Emonds-Alt, Gauthier ULiege; Malherbe, Cédric ULiege; Monbaliu, Jean-Christophe ULiege et al

Poster (2016, December 19)

The goal of this work is to develop a quantitative analytical method for the glyphosate and its major metabolite the aminomethylphosphonic acid (AMPA) by coupling microfluidics with surface enhanced Raman ... [more ▼]

The goal of this work is to develop a quantitative analytical method for the glyphosate and its major metabolite the aminomethylphosphonic acid (AMPA) by coupling microfluidics with surface enhanced Raman spectroscopy (SERS). This work is divided into 4 axes : (a) bimetallic nanoparticles synthesis in a microreactor, (b) nanoparticles functionnalisation, (c) SERS quantification of glyphosate/AMPA and (d) miniature prototype development composed of axes a to c. The first section aims at the synthesis of bimetallic nanoparticles (Au-Ag, Au-Cu and Ag-Cu) in a microfluidic device. This microfluidic device integrates a first section for the synthesis of monometallic nanoparticles (core) and a second section for the reductive deposition of a second metal (shell). The second axe of this work deals with the functionnalisation of nanoparticles to improve the selectivity of this method for the selected analytes. Two types of functionnalisation are studied : PEGylation (a) with multi-arm PEG ending with -SH and/or (b) with linear heterobifunctionnal PEG. The third axe consists in measuring quantitatively glyphosate and AMPA in different matrices, such as water, urine and fruit juice. Finally, the forth axe deals with the development of a portable detection system to perform on-site analysis. This prototype integrates the microfluidic device for nanoparticles synthesis, their functionnalisation, an injection port followed by a mixing section for the sample and an integrated Raman spectrometer for in-line analysis. [less ▲]

Detailed reference viewed: 30 (5 ULiège)
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See detailIntegrated continuous flow photoreactors: Photooxidation of (L)-methionine with singlet oxygen
Emmanuel, Noémie ULiege; Mendoza Gallego, Carlos ULiege; Lismont, Marjorie ULiege et al

Poster (2016, December 08)

Development of photochemistry in macroscopic batch reaction vessels is hampered due to inherent limitations: light penetration remains superficial, resulting in inhomogeneous irradiation and hence to side ... [more ▼]

Development of photochemistry in macroscopic batch reaction vessels is hampered due to inherent limitations: light penetration remains superficial, resulting in inhomogeneous irradiation and hence to side-reactions or product degradation due to overexposure. The recent implementation of photochemical processes in microreactors under continuous-flow conditions appeared to be much more powerful than its batch analogue in terms of irradiation efficiency and light penetration. Furthermore, the fine control of residence time ensures an accurate control of the irradiation time, avoiding side-reactions and degradation. The photooxidation of (L)-methionine with singlet oxygen using Rose Bengal as a sensitizer was successfully implemented in a microreactor setup and led to total and selective conversion into methionine sulfoxide, an important building block for the organic synthesis of peptides or functionalized amino acid. The reaction was performed in 2 min while the same reaction in batch took 2h. [less ▲]

Detailed reference viewed: 37 (16 ULiège)
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See detailExpanding chemistry’s horizon with continuous-flow reactors  
Monbaliu, Jean-Christophe ULiege; Emmanuel, Noémie ULiege; Gerardy, Romaric ULiege

in Chimie Nouvelle (2016), 122

Continuous-flow micro- and mesofluidic reactors come with inherent properties that can be advantageously utilized for expanding the horizon of preparative chemistry. Accurate control over local process ... [more ▼]

Continuous-flow micro- and mesofluidic reactors come with inherent properties that can be advantageously utilized for expanding the horizon of preparative chemistry. Accurate control over local process parameters, even under extreme conditions, inherent safety, production homogeneity and seamless scale-up are amongst the most important assets of continuous-flow chemistry. Besides, flow chemistry enables the design of efficient multistep processes with significantly reduced footprints. In this note, we discuss some of the most fascinating aspects of continuous-flow micro- and mesofluidic reactors in the specific context of preparative organic chemistry. [less ▲]

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See detailIntramolecular continuous-flow strategy towards methylphenidate (Ritalin) hydrochloride
Gerardy, Romaric ULiege; Winter, Marc; Vizza, Alessandra et al

Poster (2016, December)

threo-Methylphenidate hydrochloride is the most widely prescribed drug to treat attention deficit hyperactivity disorder (ADHD). Herein we present the batch-to-flow translation of a carbene-based ... [more ▼]

threo-Methylphenidate hydrochloride is the most widely prescribed drug to treat attention deficit hyperactivity disorder (ADHD). Herein we present the batch-to-flow translation of a carbene-based intramolecular strategy for the diastereoselective preparation of this active pharmaceutical ingredient. The process relies on the thermal generation and decomposition of a hazardous diazospecies, its thermal intramolecular C-H insertion reaction yielding an intermediate β-lactam, and its subsequent acidic methanolysis, giving enriched threo-methylphenidate hydrochloride in 70% isolated yield. The automated microfluidic setup telescopes 2 chemical transformations, 1 intermediate in-line purification and sustains a daily productivity of 20.4 g/day of methylphenidate hydrochloride. The preparation of the β-lactam is implemented on mesoscale in a pilot-scale continuous-flow reactor, providing 4.25 kg of this key intermediate per day. [less ▲]

Detailed reference viewed: 22 (3 ULiège)