Feasibility of Using 2,3,3,3-Tetrafluoropropene (R1234yf) as a Solvent for Solid–Liquid Extraction of Biopharmaceuticals

Abstract

Tetrafluoropropene (R1234yf) is the most likely replacement for tetrafluoroethane (R134a), a widely used refrigerant, propellant, and solvent, characterized by a very high global warming potential. In this study, solvation properties of R1234yf were studied experimentally and computationally for solubility of artemisinin, a precursor to the important biopharmaceutical API, and extraction of artemisinin from biomass. R1234yf was shown to be a poorer solvent than R134a for artemisinin. COSMO-RS calculations of solvation in R1234yf suggest that the decrease in performance is likely due to entropic effects. However, R1234yf was effectively used in solid−liquid extraction of Artemisia annua. The new solvent has shown an increased selectivity to the target metabolite artemisinin. This should allow for design of more selective separation processes based on the new solvent molecule with a low global warming potential of 4 relative to CO 2 .

An original approach for lipophilic natural products extraction: Use of liquefied n-butane as alternative solvent to n-hexane

“…This approach combines quantum chemical with thermodynamical statistics for the determination and prediction of the chemical potential of a molecule in a liquid without any experimental data. Thus, COSMO-RS can be used as a decision-making tool for solvent screening (Filly et al, 2015;Sicaire, Vian, Fine, Joffre et al, 2015;Suberu et al, 2016).…”

“…Many studies have been performed on natural product extraction using supercritical CO 2 , but the high working pressure (7.5e45 MPa) has limited the industrial applications (Baysal, Ersus, & Starmans, 2000;Ben Rahal, Barba, Barth, & Chevalot, 2015;Coelho et al, 2012;Couto et al, 2010;Hubert & Vitzthum, 1978;Koubaa et al, 2015;Koubaa et al, 2016;Xu et al, 2011). More recently, some studies have been focused on extraction processes involving liquefied gases at lower pressure (200e1000 kPa), such as n-propane (da Sekhon, Maness, & Jones, 2015;Zanqui et al, 2015), n-butane (Novello et al, 2015;Yang, Teo, & Xu, 2004), dimethyl ether (Kanda & Li, 2011;Kanda & Makino, 2009;Oshita et al, 2015), tetrafluoropropene (Suberu, Yamin, Cornell, Sam, & Lapkin, 2016), tetrafluoroethane (Lapkin, Plucinski, & Cutler, 2006;Mustapa, Manan, Mohd Azizi, Nik Norulaini, & Omar, 2009), eventually with co-solvents (Jesus et al, 2013;Pessoa et al, 2015). All these studies describe a dynamic process with continuous solvent recirculation using pumps and/or compressors which are prone to cavitation issues (Brennen, 1995;Franc & Michel, 2005).…”

Machine learning and molecular descriptors enable rational solvent selection in asymmetric catalysis

“…Apart from descriptor databases available in the literature, a source of descriptors can be computational software, such as COSMO therm , which combines quantum chemistry and thermodynamics to predict properties. COSMO therm has been used since the 1990s for a range of applications, such as the evaluation of new solvents for solid–liquid extraction of biopharmaceuticals,36 partitioning of organic substances into different phases,37 and predicting solute partition in multiphase complex fluids 38. Among the descriptors computed in this study, we explored screening charge density profiles 39,40.…”

Feasibility of using liquefied gas HFO-1234ze (trans-1,3,3,3-tetrafluoroprop-1-ene) as an alternative to conventional solvents for solid–liquid extraction of food ingredients and natural products

“…For now, their use is still limited by their flammability (alkanes, ethers …). Only 1,1,1,2-tetrafluoroethane is nonflammable but its use will be progressively phased out due to its impact on the greenhouse effect (Suberu, Yamin, Cornell, Sam, & Lapkin, 2016).…”

“…HFOs were initially developed for refrigerant purpose, but their interesting properties make them suitable for LGE. In 2016, a promising research has been achieved by Suberu et al (2016) on the extraction of artemisinin, an antimalarial substance, using HFO-1234yf as alternative to R134a.…”