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and operate such a process economically, given a good design. Regarding scientific milestones, in the 1980s con- ventional wisdom claimed that CO2’s solvent power resembled that of n-alkanes, despite a large body of experimental evidence to the contrary. During the pe- riod 1988–1992, a number of research groups (Smith, Johnston, Enick and Brady, Beckman) reported that fluorinated materials, as well as silicones, exhib- ited significantly better thermodynamic compatibil- ity with CO2 than alkanes. The paper in Science by the DeSimone group on the CO2-philicity of poly(perfluoroacrylates) in 1992 was a milestone both from the scientific standpoint and from a dissemina- tion perspective, as this publication served to quash the ‘CO2 is like hexane’ heuristic and introduce a wide audience to the notion that true CO2-philes did indeed exist. Interestingly, it was not for another 3 years be- fore the information of the CO2-philicity of fluorinated materials found its way into the synthetic organic chemistry community. With publications by Leitner’s and Tumas’ groups, showing the use of fluorinated lig- ands in homogeneous catalysis in CO2, green chem- istry in CO2 began to rapidly permeate the chemistry community. Once it was demonstrated that effectively any catalyst could ultimately be rendered CO2-soluble, CO2 was applied broadly as a solvent in organic transformations by both the academic and industrial communities. In 1999, Brennecke published a study demonstrating the potential for use of ionic liquid/CO2 biphasic mixtures as media for green chemistry—the first papers exploiting this biphasic system appeared in 2001. A number of researchers examined the strong potential for CO2 to plasticize polymers, with sev- eral important papers appearing between 1985 and 1994 (the work by Wang and Kramer introduced the concept). Exploitation of this science appeared in 1996 through 2001, as both industry (Ferro, PPG) and academia (Howdle, Eckert) employed the plasticizing effect to enhance mixing in polymer systems. Regarding commercial successes, the introduction of the CarDio process for continuous production of polyurethane foam using CO2 as the blowing agent has been extremely important, in that it is both green chemistry and commercially successful. However, because the development of CarDio was conducted entirely by industry, with no R&D support from academia, it is little known within academic cir- cles. Much more widely known is the construction (by Dupont) of a semi works facility to polymer- ize fluorinated monomers in carbon dioxide, as this technology was transferred (in part) from academia (work by DeSimone’s group at North Carolina). The same is probably true for the cleaning of fabrics (dry cleaning) using CO2 . The introduction of CO2 to microelectronics pro- cessing began with preliminary work by the Phasex Corporation and IBM in 1995–1996, given the DeS- imone Science paper showing that perfluoroacrylate polymers are readily miscible with CO2. Again, be- cause the preliminary work was conducted primarily by industry and was disseminated to a relatively nar- row audience (the microelectronics industry), exten- sive interest in this topic did not begin until several years later, when both Ober’s group (Cornell Univer- sity) and the DeSimone group (UNC) began to play active roles. Now, the use of CO2 in microelectron- ics processing is considered sufficiently noteworthy to merit an article in Chemical and Engineering News. The work by Watkins on creation of thin metal films via chemistry in CO2 [96] will likely enhance interest still further. Another series of commercial milestones occurred in late 2000 to early 2001, when the pharmaceutical industry purchased (either in their entirety or substan- tial portions) Bradford Particle Design, Separex and Phasex—three of the more significant commercial en- terprises relying primarily on supercritical fluids tech- nology. It will be interesting to see whether this leads to more rapid commercialization of CO2-based pro- cesses or the reverse. In summary, milestones in green chemistry using CO2 have occurred upon scientific achievement, as was the case with the discovery of CO2-philic poly- mers by DeSimone in 1992, and also the dissemination of fundamental science to industries or communities for whom CO2 had previously been considered an ex- otic technology. In this report a number of technical hurdles to increased use of CO2 in green chemistry have been outlined—it is hoped that future milestones will occur by overcoming these hurdles. Finally, it should be noted that some scientific milestones that have occurred in this field might be considered the re- sult of a particular researcher recognizing the broader E.J. Beckman / J. of Supercritical Fluids 28 (2004) 121–191 181PDF Image | Supercritical and near-critical CO2 in green chemical synthesis and processing
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