Deepak Tapriyal1, Robert M. Enick2, Yang Wang3, Karl Johnson2, Liu Jun4, Mark . A McHugh4, Jacob M. Crosthwaite5, Mark C. Thies5, Ik-Hyeon Paik6, and Andrew. D. Hamilton7. (1) Chemical and Petroleum Engineering, University of Pittsburgh, Benedum hall, Chemical and Petroleum Engineering department, Pittsburgh, PA 15213, (2) University of Pittsburgh, 1249 Benedum Hall, Department of Chemical Engineering, Pittsburgh, PA 15261, (3) Chemical Engineering, University of Pittsburgh, 1249 Benedum Hall, Department of Chemical Engineering, Pittsburgh, PA 15261, (4) Dept. of Chemical Engineering, Virginia Commonwealth University, 601 West Main Street, Richmond, VA 23284, (5) Chemical & Biomolecular Engineering, Clemson University, 127 Earle Hall, Clemson, SC 29634, (6) Yale University, 225 Prospect st, New Haven, CT 06520, (7) Department of Chemistry, Yale University, 225 Prospect st, New Haven, CT 06520
In an attempt to generate CO2-soluble compounds that may enhance the performance of scCO2 processes, several novel, non-fluorous CO2-philic compounds have been identified. Oligo(vinyl acetate) is a particularly effective CO2-phile for the design of ionic surfactants, and poly(vinyl acetate), PVAc, remains the most CO2-soluble high molecular weight, non-fluorous polymer that has yet been identified. We have synthesized a high molecular weight, low melting point polymer with per-acetylated monosaccharide side chains, poly (1-O-(vinyloxy)ethyl - 2,3,4,6 tetra O acetyl b D - glucopyranoside), P(AcGIcVE). P(AcGIcVE) is slightly less CO2-soluble than PVAc, but is more CO2-soluble than any other known polymer composed solely of C, H and O. Oligo(lactic acid) and poly(lactic acid) have been shown to be highly CO2 soluble over a broad range of molecular weight, but the pressure required for dissolution of this biodegradable amorphous polymer is slightly more than twice that required for PVAc. Linear poly(acetoxy oxetane), PAO, has also been synthesized because ab initio calculations have indicated that this polymer exhibits more favourable Lewis acid:Lewis base interactions with CO2 than PVAc. Ab initio computational results for mixtures of CO2 with PLA, PVAc or PAO will also be presented. Methoxy acetate oligomers are also quite CO2-philic, and have been successfully incorporated into the CO2-philic arms of bis-urea hydrogen bonding compounds and as the CO2-phile of small CO2-soluble dendrimers.