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E.J. Beckman / J. of Supercritical Fluids 28 (2004) 121–191 153 Fig. 5. Qualitative P-x diagram of a polymer–CO2 binary mixture, both above and below the critical temperature of the solvent [125]. This fiigure includes liquid–liquid (LL), vapor–liquid (VL) and three-phase vapor–liquid–liquid (VLL) types of phase envelopes. polymers that would dissolve in pyridine were not soluble in carbon dioxide. Subsequent calculations performed during the early 1980s (see, for example, Ref. [129]) using CO2’s equation of state strongly suggested that CO2 ’s solubility parameter should approach that of normal alkanes. However, experi- mental work by Heller’s group on the phase behavior of polymers performed during that time [130] clearly demonstrated that CO2’s solvent power is inferior to that of n-alkanes—very few polymers tested by Heller showed any significant solubility in carbon dioxide at moderate (<200 bar) pressures. Experimental work by Johnston et al. [131] suggested that solubility parameter was not the best means by which to charac- terize the solvent power of compressible fluids, such as carbon dioxide. Johnston suggested instead that polarizability/volume is a better measure of solvent power; by this standard CO2 is judged to be a feeble solvent, in line with experimental evidence. During this same time period, a number of re- searchers found that silicones [132] and fluorinated materials [1,75,133] exhibited miscibility with CO2 at pressures well below those of alkanes of comparable chain length. Indeed, a calculation of the solubility parameter of CO2 using the heat of vaporization and molar volume (of the liquid) would suggest values similar to those of fluoroalkanes or silicones [134]. In 1992, DeSimone et al. published the first reports that describe a truly ‘CO2-philic’ polymer, a fluori- nated polyacrylate [79]. Further work [135] showed that block copolymers of fluorinated acrylates and ‘CO2-phobic’ polymers were both soluble and able to form micelles in carbon dioxide. It is interesting that the role of fluorine in the design of CO2-philic materials has not been com- pletely established. For example, while the poly (perfluoroacrylates) are the most CO2 -philic polymers known, it is also true that more poorly soluble fluo- ropolymers have been identified than highly soluble variants [128,136]. Samulski et al. [137] have found experimentally that fluorine interacts specifically with the electron-poor carbon on CO2, which would ex- plain why addition of one or two fluorine atoms to aryl phosphine ligands or chelating agents tends to enhance CO2 -solubility significantly. Calculations us- ing various levels of theory tend to predict no specificPDF Image | Supercritical and near-critical CO2 in green chemical synthesis and processing
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