Presentation on theme: "Ionic Liquids for Natural Product Extraction"— Presentation transcript:
1 Ionic Liquids for Natural Product Extraction Adam WalkerBioniqs Ltd.
2 Ionic Liquids - Introduction NaCl (mp 801°C)BMIm PF6 (mp -79°C)Ionic liquids are salts, with melting points below ambient temperatureThey are composed solely of anions and cations – no water is presentTheir regular, ordered structure gives them very different properties to conventional liquidsIonic liquids based on imidazole have been well studied as novel solvents
3 Ionic Liquids - Properties Extremely good solvents for many compounds – organic, inorganic, mineral, polymeric and biologicalNon-volatile – do not evaporateNon-flammableStabilize sensitive compoundsMany possible combinations of ions – can design the solvent for a particular application
4 Applications Solvents for chemical and biochemical reactions Extraction media for natural product isolationCleaning agentsStorage media for unstable compoundsLubricantsElectrochemical/battery materials
5 “First Generation” Ionic Liquids - Disadvantages Expensive in comparison with molecular solvents.Very few commercially available.ViscousPoorly biodegradable and potentially toxic.
6 “Second Generation” Ionic Liquids Bioniqs has developed new types of simple ionic liquids, based on ammonium salts.These retain the advantages of ionic liquids, but also offer:- reduced viscosity.- low cost.- straightforward preparation from sustainable precursors.- minimal toxicity and environmental impact.- recyclability and biodegradability.
7 Example Applications Stabilization of enzymes for biocatalysis Dissolution and processing of biomassNatural product isolation and purificationReactor decontamination
8 Stabilization of Biomolecules Activity of alcohol dehydrogenase enzyme after storage in water compared to standard (purple) and optimized (red) ionic liquids.H2OAEFF-390AAFF-015Enzyme in water deactivated after 10 days at room temperature.Enzyme in AEFF-390 retains activity after 90 days at room temperature.
9 Biomass ProcessingIonic liquids can dissolve numerous polymers, including biological macromolecules such as:-Cellulose (up to 10% wt. solutions)LigninProteinsDNA/RNABioprocessing requires solvent to dissolve substrate without denaturing enzyme.Ionic liquid can be designed accordingly.
10 Natural Product Extraction & Processing H2O0.15Et2O1.2CHCl33.3BMIm PF677.6Morphine (free base) – solubility (gL-1)Solubility of natural products in ionic liquids often very much higher than in conventional solvents.Can be used to extract high concentrations from natural sources, using small extractor volumes.
11 Natural Product Extraction & Processing Dissolution of penicillin in ionic liquids – varies between solvent formulationsSolubility limit ranges from g/LCan design solvent to optimize extraction efficiency
12 Natural Product Extraction & Processing With support from MMV, Bioniqs has developed ionic liquids for artemisinin extraction, from both wet and dry plant material.Extraction up to 4 times faster than in hexaneSolubility in ionic liquids up to °C.Artemisinin may be recovered by adding water, precipitating and filtering off.Residual solvent content of recovered artemisinin <0.001%.Solvent may then be recycled and re-usedImage provided courtesy of
13 Decontamination & Cleaning Solubility of two nitroaromatic pollutants in ionic liquids compared to water.Ionic liquid may be designed to dissolve one compound even in presence of structurally similar materials.
14 Decontamination & Cleaning ILs designed to remove specified contaminant (amoxicillin)All ILs tested dissolve contaminant to >300g/L; several to >500g/L
15 Ecotoxicity and Biodegradation ILs have been widely touted as “green” solventsrecyclablenon-flammablenon-volatileBUT early imidazole-based ILs werepoorly biodegradabletoxic to micro-organismsmay form hazardous hydrolysis productsBiodegradability must be “built in” to an ionic liquid at the design stage.
16 Biodegradation of Ionic Liquids Ordinary soil organisms can grow on Bioniqs ionic liquids and completely degrade them within 48 hours (above).Degradation products are water, carbon dioxide and ammonium ion.No significant toxic effects at concentrations below 80mM.
17 SummaryIonic liquids are not a panacea, but can offer major benefits in certain key areas:-Can now compete on comparable cost footing with conventional solvents for bulk applications.Reduced pollution and wasteImproved process safetyEnhanced efficiency of reaction and extraction processesFacilitate improved processes.Increased solubilities – smaller volumesImproved turnover rates and yieldsStabilization of sensitive moleculesApplication to poorly soluble substrates