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PEOPLE@HES-SO – Annuaire et Répertoire des compétences
PEOPLE@HES-SO – Annuaire et Répertoire des compétences

PEOPLE@HES-SO
Annuaire et Répertoire des compétences

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Allemann Christophe

Allemann Christophe

Professeur HES ordinaire/Responsable d'institut

Compétences principales

Synthesis and Catalysis

Process chemistry and scale-up

Flow chemistry (microreactors)

Chemical Production

Photochemistry

HAZOP, Risk Analysis, COST

  • Contact

  • Enseignement

  • Publications

Contrat principal

Professeur HES ordinaire/Responsable d'institut

Téléphone: +41 26 429 67 97

Bureau: HEIA_B10.09

Haute école d'ingénierie et d'architecture de Fribourg
Boulevard de Pérolles 80, 1700 Fribourg, CH
HEIA-FR
BSc HES-SO en Chimie - Haute école d'ingénierie et d'architecture de Fribourg
  • • Chimie organique avancé (OC-6 : Pd chemistry)
BA HES-SO en Architecture - Haute école d'ingénierie et d'architecture de Fribourg
  • • Pré-commissioning (SOP
BSc HES-SO en Chimie - Haute école d'ingénierie et d'architecture de Fribourg
  • Analyses Spectrales (RMN, MS, IR)

2024

Up-scaling a sol-gel process for the production of a multi-component xerogel powder
Article scientifique ArODES

Barbara Pföss, Jonathan Caldi, Sutida Jansod, Christophe Allemann, Pierre Brodard, Roger Marti

CHIMIA,  2024, 78, 3, 142-147

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Résumé:

A sol-gel process for the synthesis of a multi-component oxide material from the system SiO2-ZrO2-Al2O3underwent optimization and up-scaling. Initially, on a laboratory scale, components including precursors, catalysts, and additives were methodically evaluated to ensure a safe and efficient transition to larger volumes. Subsequently, the equipment for the whole setup of the sol-gel process was strategically selected. Leveraging insights from these optimizations, the process was successfully scaled-up to pilot-scale operation, conducting hydrolysis, condensation reactions, gelation, aging, and drying within a single, integrated conical dryer system for an 80 L batch. A visual test and FTIR spectroscopy were applied for process control and monitoring.

2023

Education in flow chemistry
Article professionnel ArODES

Christophe Allemann, Roger Marti

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Résumé:

Flow chemistry is a growing and promising technology that can be used in research, development, and production. Nowadays, properly trained staff in flow chemistry is lacking in industry. To efficiently work with this technology, a mix of engineering and chemical skills is required. Although, this dual education is well addressed in the chemistry major given at the Haute Ecole d’Ingénierie et d’Architecture de Fribourg, a school of the University of Applied Sciences and Arts, Western Switzerland, the teaching in flow chemistry should be enhanced and reinforced.

2022

A Rapid, highly sensitive and selective phosgene sensor based on 5,6-pinenepyridine
Article scientifique ArODES

Atena B. Solea, Christophe Curty, Katharina M. Fromm, Christophe Allemann, Olimpia Mamula Steiner

Chemistry – A European Journal,  2022, vol. 28, no. 55

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Résumé:

The toxicity of phosgene (COCl2) combined with its extensive use as a reactant and building block in the chemical industry make its fast and accurate detection a prerequisite. We have developed a carboxylic derivative of 5,6-pinenepyridine which is able to act as colorimetric and fluorimetric sensor for phosgene in air and solution. For the first time, the formation of a pyrido-[2,1-a]isoindolone was used for this purpose. In solution, the sensing reaction is extremely fast (under 5 s), selective and highly sensitive, with a limit of detection (LOD) of 9.7 nM/0.8 ppb. When fixed on a solid support, the sensor is able to detect the presence of gaseous phosgene down to concentrations of 0.1 ppm, one of the lowest values reported to date.

2021

Complexation behavior of pinene–bipyridine ligands towards lanthanides :
Article scientifique ArODES
the influence of the carboxylic arm

Atena B. Solea, Liangru Yang, Aurélien Crochet, Katharina M. Fromm, Christophe Allemann, Olimpia Mamula Steiner

Chemistry,  2021, vol. 4, pp. 18-30

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Résumé:

The complexation behavior of two novel, chiral pinene–bipyridine-type ligands ((–)-HL1 and (–)-HL2) containing a carboxylic arm towards lanthanide Ln(III) (Ln = La, Eu, Lu) ions was investigated through spectroscopic methods. The association constants of the mononuclear complexes determined from the UV-Vis titrations indicated that the ligand (–)-HL1 possessing a shorter carboxylic arm formed more stable complexes compared with (–)-HL2, whose carboxylic arm had one more methylene unit. This is due to the formation of more stable seven-member metal chelate rings in the first case as compared with the eight-member metal chelate rings in the second. IR and fluorescence spectroscopy provided additional information about the structure of these complexes.

Jet colliding and mixing efficiency
Article scientifique ArODES

Christophe Allemann, Massimo Varisco, Gianni De Luca, Richard-Emmanuel Estes

CHIMIA,  2021, vol. 75, no. 12

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Résumé:

Two experimental methods, the Nile Red dye extraction and the Williamson ether synthesis in biphasic conditions, were used to characterize the mixing performance of a new cheap impinging jet colliding mixer from Gjosa and to compare it to other commercial micromixers (Caterpillar CPMM-R300, T-mixer, LTF MR-MX and LTF MR-MS). The Nile Red method shows that the Caterpillar mixer is the best one. Excellent results are also achieved with two Gjosa mixers in series. These results are not reflected in the Williamson ether synthesis, where the best mixer is the Gjosa one.

Efficient synthesis of isoindolones by intramolecular cyclisation of pyridinylbenzoic acids
Article scientifique ArODES

Atena B. Solea, Sining Wang, Xiao-Song Xue, Aurelien Crochet, Katharina M. Fromm, Kendall N. Houk, Olimpia Mamula Steiner, Christophe Allemann

Organic Biomolecular Chemistry,  2021, vol. 19, no. 37, pp. 8025-8029

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Résumé:

A straightforward one-pot method for the synthesis of unreported pyrido-[2,1-a]isoindolones in excellent yield is described. Two novel isoindolones were synthesized and fully characterized. The alkyl substituents on the pyridine play an important role in the outcome of the reaction. The mechanism, investigated through DFT calculations, features an unprecendented intramolecular cyclization reaction involving a carboxylic acid activated by tosyl chloride and an electron-poor pyridinic nitrogen. This protocol completes the known strategies to obtain functionalized isoindolones.

Impact of solvent and their contaminants on Pd/C catalyzed Suzuki-Miyaura cross-coupling reactions
Article scientifique ArODES

Alexandre de Lambert de Boisjan, Christophe Allemann, Luca Fadini

Helvetica Chimica Acta,  2021, vol. 104, no. 6, article no. e2100035

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Résumé:

The aim of this work was to understand if solvent contaminants can interfere in Suzuki’s cross-coupling reactions and if it can explain the lack of robustness in industrial processes. For this purpose, several parameters were tested on the industrial model reaction between 2-bromonaphthalene and phenylboronic acid catalyzed by Pd/C. Best results were obtained using THF as solvent. Traces of the precursors of the used solvents, such as 2,3-dihydrofurane or maleic anhydride (100–300 ppm related to the solvent) strongly poisoned the reaction, decreasing the conversion significantly. This means that to ensure robust production, solvent quality must be analyzed at the ppm level. Fortunately, addition of triphenylphosphine can circumvent the catalyst poisoning.

125th anniversary of the School of Engineering and Architecture of Fribourg (HEIA-FR)
Article professionnel ArODES

Véronique Breguet Mercier, Christophe Allemann, Olivier Nicolet

Chimia,  2021, vol. 75, no. 3, p. 246

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Résumé:

This year, on the 14th of January 2021 the School of Engineering and Architecture (HEIA-FR)[1] celebrated its 125th anniversary. To celebrate, many interactive events are organized from February to September 2021.

2020

Tautomerism and Self-Association in the Solution of New Pinene-Bipyridine and Pinene-Phenanthroline Derivatives
Article scientifique ArODES

Atena B. Solea, Ivan Cornu, Vera Deveva, Aurélien Crochet, Katharina M. Fromm, Liudmil Antonov, Christophe Allemann, Olimpia Mamula Steiner

Molecules,  2020, vol. 25, no. 5, article no. 298

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Résumé:

Two novel pinene-type ligands have been synthesized and their tautomeric and self-associating behavior studied in solution and in the solid state. The first ligand, an acetylated derivative of 5,6-pinene-bipyridine, displays keto-enol tautomerism in solution. This tautomeric equilibrium was studied by NMR and UV-Vis spectroscopy in various solvents, and the results were compared with the ones obtained through DFT calculations. The second ligand was obtained by an unusual oxidation of the phenanthroline unit of a pinene-phenanthroline derivative. This compound exists as a single tautomer in solution and aggregates both in solution (as observed by NMR) and in the solid state through H-bonding as observed by X-ray structure determination and confirmed by DFT studies.

• Tautomerism and self-association in the solution of new pinene-bipyridine and pinene-phenanthroline derivatives
Article scientifique

Allemann Christophe

Molecules, 2020 , vol.  25(2), pp.  1-13

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Résumé:

Two novel pinene-type ligands have been synthesized and their tautomeric and self-associating behavior studied in solution and in the solid state. The first ligand, an acetylated derivative of 5,6-pinene-bipyridine, displays keto-enol tautomerism in solution. This tautomeric equilibrium was studied by NMR and UV-Vis spectroscopy in various solvents, and the results were compared with the ones obtained through DFT calculations. The second ligand was obtained by an unusual oxidation of the phenanthroline unit of a pinene-phenanthroline derivative. This compound exists as a single tautomer in solution and aggregates both in solution (as observed by NMR) and in the solid state through H-bonding as observed by X-ray structure determination and confirmed by DFT studies.

2017

Continuous processes and flow chemistry at the Universities of Applied Sciences in Switzerland
Article scientifique ArODES

Christophe Allemann, Roger Marti, Olivier Vorlet, Oliver Martin, Peter Riedlberger, Tobias Leonhardt, Angelo Gössi, Wolfgang Riedl, Jean-Manuel Segura, Simon Crelier

CHIMIA International Journal for Chemistry,  2017, vol. 71, no. 7/8, pp. 525-527

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Résumé:

This article provides an overview of activities in the fields of continuous processes, flow chemistry and microreactors at the Universities of Applied Sciences in Switzerland.

Continuous Processes and Flow Chemistry at the Universities of Applied Sciences in Switzerland
Article scientifique

Allemann Christophe, Vorlet Olivier, Marti Roger

CHIMIA, 2017 , vol.  71, pp.  525-527

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2010

• Computational investigations of the stereoselectivities of proline-related catalysts for aldol reactions.
Article scientifique

Allemann Christophe

Journal of Molecular Catalysis A: Chemical, 2010 , vol.  1-2 (324), pp.  31-38

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Résumé:

Computational investigation of the aldol reaction of benzaldehyde with acetone catalyzed by various proline derivatives and 2-azetidine carboxylic acid reveal the origins of stereoselectivities of these reactions. Structural differences between catalysts and transition states were analyzed with density functional theory geometries in order to establish the key factors that will help in the design of new catalysts.

2004

• Theory of Asymmetric Organocatalysis of Aldol and Related Reactions: Rationalizations and Predictions.
Article scientifique

Allemann Christophe

Accounts of Chemical Research, 2004 , vol.  37 (8), pp.  558-569

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Résumé:

Computational studies have led to models to understand some classic and contemporary asymmetric reactions involving organocatalysts. The Hajos−Parrish−Eder−Sauer−Wiechert reaction and intermolecular aldol reactions as well as Mannich reactions and oxyaminations catalyzed by proline and other amino acids, and Diels−Alder reactions catalyzed by MacMillan's chiral amine organocatalysts have been studied with density functional theory. Quantitative predictions for several new catalysts and reactions are provided.

2002

• Synthesis and Application of an Electronically Chiral Mimic of CpFe
Thèse de doctorat

Allemann Christophe

2002,  Fribourg (Switzerland) : University of Fribourg

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