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154 E.J. Beckman / J. of Supercritical Fluids 28 (2004) 121–191 Fig. 6. Time profile of formation of ethyl benzene from hydrogenation of styrene performed in biphasic water/toluene (), biphasic water/CO2 () and in emulsions using PFPE MW=2500 (), PFPE MW=740 (), Lodyne 106A () or PBO-PEO () as surfactants. Reaction conditions: 50/50 wt.% water/CO2, 1.5% surfactant, 80 mM styrene, 1 mol.% catalyst (to substrate), Rh/L=1/6, 40C, 4000 psi. TOF values at 50% conversion are given as a comparison for biphasic H2O/toluene, H2O/CO2 and H2O/CO2 emulsion systems [310]. interactions with fluorine [138], suggesting that flu- orine’s role in the design of CO2-philic materials is simply to lower the cohesive energy density. McHugh has recently suggested that fluorination can signifi- cantly enhance the ‘CO2-philicity’ of polymers if the fluorination creates a dipole in the material, provid- ing a locus for quadrupole–dipole interactions with CO2 [136a]. This appears to be an area where more fundamental research would help to create a clearer picture of the underlying phenomena. As interest in applications for CO2-philic poly- mers exploded in the 1990s [139], a small group of researchers continued to probe the fundamentals of CO2 behavior with special regards to polymer solubility. Johnston’s and Eckert’s groups, using IR spectroscopy and computer calculations, proposed that Lewis acid-base interactions between CO2 and carbonyl groups could explain the high swelling of polyacrylates by carbon dioxide [140,141]. Calcula- tions using various levels of theory tend to support the experimental evidence, at least where carbonyl groups are concerned [142]. Further, the specific interactions between Lewis base groups and CO2 ex- hibits a much more significant effect on polymer–CO2 phase behavior than small molecule–CO2 phase be- havior. McHugh’s group published several seminal papers [128,143] on the phase behavior of CO2 and various homo- and copolymers in the mid-1990s. Conventional wisdom of the time would suggest that because CO2 is a low dielectric, low cohesive en- ergy density solvent, it should only solvate polymers of similar characteristics. However, for the case of ethylene–acrylate copolymers, McHugh found that increasing the acrylate content lowered miscibility pressures, despite the fact that the acrylate is the polar comonomer. McHugh postulated quadrupole–dipole interactions as the cause; clearly Lewis acid-base interactions could have played a role as well. For the case of n-alkyl acrylates, McHugh found that in- creasing the side chain length of the polymer initially would lower miscibility pressures, ostensibly due to the increased polymer free volume (and hence entropyPDF Image | Supercritical and near-critical CO2 in green chemical synthesis and processing
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