Jonathan Gagnon

Homogeneous asymmetric transfer hydrogenation of ketones using a ruthenium catalyst anchored on chitosan: natural chirality at work

A pivaloyl functionalized chitosan biopolymer was used as a polyligand for the [Ru(p-cymene)Cl2] moiety. The functionalized biopolymer containing a metal to saccharide ratio of 0.33 was used as a catalyst for the asymmetric transfer hydrogenation of ketones. The reactions gave yields up to 80% and enantiomeric excesses up to 72%, with the intrinsic chirality of chitosan being the only source of enantioselection.

FT-IR/ATR univariate and multivariate calibration models for in situ monitoring of sugars in complex microalgal culture media

The objective of this work is to develop a quick and simple method for the in situ monitoring of sugars in biological cultures. A new technology based on Attenuated Total Reflectance-Fourier Transform Infrared (FT-IR/ATR) spectroscopy in combination with an external light guiding fiber probe was tested, first to build predictive models from solutions of pure sugars, and secondly to use those models to monitor the sugars in the complex culture medium of mixotrophic microalgae. Quantification results from the univariate model were correlated with the total dissolved solids content (R(2)=0.74). A vector normalized multivariate model was used to proportionally quantify the different sugars present in the complex culture medium and showed a predictive accuracy of >90% for sugars representing >20% of the total. This method offers an alternative to conventional sugar monitoring assays and could be used at-line or on-line in commercial scale production systems.

Regioselective pivaloylation of N-phthaloylchitosan: a promising soluble intermediate for chitosan chemistry

A simple and efficient pivaloylation of primary alcohols was realized on N-phthaloylchitosan that was regioselectively and entirely protected. The selectivity of this mild esterification was demonstrated by comparison with (1)H NMR chemical shifts of H-1 and H-3 of complete 3,6-O-dipivaloylated derivatives. The selective hydrazinolysis of N-phthaloyl groups in the presence of pivaloyl ester was achieved in ethanol/water. High molecular weight 6-O-pivaloylchitosan, purified by ultrafiltration, with solubility in organic solvents was obtained. The selective introduction of a phosphorus moiety in O-3 using chlorodiphenylphosphine has led to 3-O-diphenylphosphinito-N-phthaloyl-6-O-pivaloylchitosan with a ds of 0.97 from energy dispersive X-ray spectroscopy, which demonstrates the potential applications of O-6 pivaloyl protection. The pivaloylation of O-6 alcohols can enhance the solubility of some chitosan derivatives and therefore contributes to the development of applications involving chitosan through regioselective modifications of alcohol and amino groups.

Development and treatment procedure of arsenic-contaminated water using a new and green chitosan sorbent: kinetic, isotherm, thermodynamic and dynamic studies

Abstract Arsenic is classified as one of the most toxic elements for humans by the World Health Organization (WHO). With the tightening drinking water regulation to 10 μg L−1 by the WHO, it is necessary to find efficient sorbent materials for arsenic. In this work, the removal of arsenic(V) from water is achieved with an insoluble chitosan sorbent in the protonated form obtained by a simple heating process. Kinetic studies show a very fast sorption (less than 10 min). The Langmuir isotherm model is best describing experimental data with a capacity of 42 mg g−1 at pH 8. The sorption process is based on anion exchange (chemisorption) determined from the Dubinin-Radushkevich model. The sorption efficiency of the chitosan sorbent is 97% at low concentrations (e.g. 100 μg L−1). Thermodynamic analysis reveals that the sorption process is exothermic and is controlled by enthalpic factors. Breakthrough curves (BTC) were acquired in real-time by instrumental chromatography and was better described by the Thomas model. BTC from column sorption and desorption with a salt solution suggest that this sorbent is relevant for large scale applications. With this new renewable product, it will be possible to treat arsenic contaminated water at low cost and with little waste (concentration factor of 1500).