.Soybean oil triglycerides (SOT) can be used for the synthesis of rigid polymers. This research investigates the potential of using dense (sub/supercritical) CO2 in the reaction medium for the addition of functional groups to SOT. As an alternative and novel method, the reaction of SOT with KMnO4 in the presence of water and dense CO2 is presented. Dense CO2 is utilized to bring the soybean oil and aqueous KMnO4 solution into contact. Experiments are done at 10, 25, 34.5, 50 oC and 2.5, 5, 7, 11, 16MPa. Effects of temperature, pressure, NaHCO3 addition, and KMnO4 amount on the conversion (depletion by bond opening) of soybean-triglyceride double bonds (STDB) are investigated. The highest STDB conversions, about 40%, are obtained at the near-critical conditions of CO2. The addition of NaHCO3 enhances the conversion; one mole of NaHCO3 per mole of KMnO4 gives the highest benefit. Increasing KMnO4 up to 10% increases the conversion of STDB.
Akgerman A, Lin B, Homogeneous and catalytic reactions in supercritical fluids, in: Bertucco, A., ed., CISF-99 5th Conference on Supercritical Fluids and Their Applications, 289, 1999
Buback M, Kinetics and selectivity of chemical processes in fluid phases, in: Kiran, E. and Levelt Sengers, J.M. H., eds., Supercritical Fluids, Kluwer Academic Publishers, Netherlands, 481, 1994
Clifford AA, Reactions in supercritical fluids, in: Kiran, E. and Levelt Sengers, J. M. H., eds., Supercritical Fluids, Kluwer Academic Publishers, Netherlands, 449, 1994
Dinjus E, Fornika R, Scholz M, Organic chemistry in supercritical fluids, in: van Eldik, R. and Hubbard, C. D., eds., Chemistry Under Extreme or Non-Classical Conditions, Wiley, New York, 219, 1997
Eckert CA, Ziger DH, Johnston KP, Kim S, J. Phys. Chem., 90, 2738, 1986
Jessop PG, Leitner W, Supercritical fluids as media for chemical reactions in: Jessop, P.G. and Leitner, W., eds., Chemical Synthesis Using Supercritical Fluids, Wiley-VCH, New York, 1, 1999
Knutson BL, Dillow AK, Liotta CL, Eckert CA, Kinetics of a diels-alder reaction in supercritical propane, in: Hutchenson, K.W. and Foster, N. R., eds., Innovations in Supercritical Fluids, ACS Symposium Series 608, American Chemical Society: Washington,166, 1995
Lapworth A, Mottram EN, J. Chem. Soc., 127, 1628, 1925
Poliakoff M, George MW, Howdle SM, Inorganic and related chemical reactions in supercritical fluids, in: van Eldik, R. and Hubbard, C. D., eds., Chemistry Under Extreme or Non-Classical Conditions, Wiley, New York, 189, 1997
Poliakoff M, George MW, Chemical reactions as a continuous process in supercritical fluids, in: Perrut, M. and Subra, P. eds., Proceedings of the 5th Meeting on Supercritical Fluids, Materials and Natural Products Processing, Tome 2: Natural Products, Advanced Processes Reactions and Various, 833, 1998
Stahl E, Quirin KW, Gerard D, Dense gases for extraction and refining, Translation from the German Edition by Ashworth M.R. F., Springer-Verlag, Berlin, 1988