Enabling industrial deployment of deep eutectic solvents through manufacturing tools

Lead Research Organisation: University of Bern
Department Name: Chem, Biochem and Pharmaceutical Sci

Abstract

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Description Organolithium and Grignard reagents are commodity reagents which find widespread applications in synthesis, being used in laboratories and industrial settings on a daily basis across the world. Typically, due to their high reactivity, they require the use of cryogenic conditions, under inert atmospheres and employing toxic volatile organic solvents. This project has introduced the use of Deep Eutectic Solvents, which are made up by a combination of two biorenewable, biodegradable and naturally occurring components and inspired by nature. These solvents not only minimise considerably the environmental footprint of the transformations studied but also allow in some case for better performances, while operating at room temperature and in the presence of air. These are conditions that for decades have been disallowed for polar organometallic reagents. Towards the end of the project we have also develop new methods using these types of reagents in DES in continuous flow, which has opened new avenues of research towards high scale synthesis and also possible applications for chemical manufacturing.
Exploitation Route Fine chemical manufacture: Deep eutectic solvents have obvious benefits for replacing volatile organic compounds (VOCs) in synthesis. It has been estimated that up to 85% of the total mass involved in typical pharmaceutical syntheses is solvents,1 but VOC recovery is usually only 50 to 80%,2-3 causing waste and presenting environmental hazards. Replacing toxic VOCs with renewable, safer alternatives is one major aim of Green Chemistry,4 alongside reduction of waste and minimisation of energy requirements. DES not only are safer but may be active in the syntheses to assist control of chirality and selectivity of reactions. Our research in the project has shown that we can use commodity organometallic reagents such as organolithium and Grignard reagents in DES for the efficient generation of C-C bonds. These are key reactions in synthesis with a myriad of applications for chemical manufacturing.
Sectors Chemicals,Manufacturing, including Industrial Biotechology
URL https://people.bath.ac.uk/chske/research/indes/
 
Title CCDC 2009657: Experimental Crystal Structure Determination, 2020 
Description Cambridge crystallographic data set 
Type Of Material Database/Collection of data 
Year Produced 2020 
Provided To Others? Yes  
Impact data from structural determination 
 
Title Dataset for: "Ultrafast Amidation of Esters using Lithium Amides under Aerobic Ambient Temperature Conditions in Sustainable Solvents" 
Description Spectroscopic and synthetic details 
Type Of Material Database/Collection of data 
Year Produced 2020 
Provided To Others? Yes  
Impact not applicable 
 
Description Development of new bimetallic catalyst for ring opening polymerisation in DES 
Organisation Universidad de Alcala
Department Department of Organic and Inorganic Chemistry
Country Spain 
Sector Academic/University 
PI Contribution We are experts in the synthesis and characterisation of a variety of s-block bimetallic systems with potential to promote ring opening polymerisation. We have already started to study the use of some of these systems oil DES
Collaborator Contribution The group of Prof. Marta E Gonzalez Mosquera has complementary expertise in the use of main group complexes as initiators for the ring opening polymerisation reactions as well as the design of unique ligand scaffolds to maximise efficiency and selectivity
Impact no outputs yet interdisciplinary collaboration: inorganic synthesis, green Chemistry (Hevia, Bern) and catalysis and polymerisation (Gonzalez Mosquera, Alcala)
Start Year 2020
 
Description Studying organometallic chemistry in Deep Eutectic Solvents 
Organisation University of Oviedo
Country Spain 
Sector Academic/University 
PI Contribution We performed all the synthesis and characterization of the organometallic species involved in the transformations, focusing on addition reactions to unsaturated organic molecules.
Collaborator Contribution The partner in Spain provided expertise in the design of the special deep eutectic solvents employed in the work.
Impact A joint publication has already emerged from this collaborative work in Chem Eur. J 2018, 24, 1720.
Start Year 2019