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Carbonation of epoxidized castor oil: a new bio‐based building block for the chemical industry
Author(s) -
Guzmán Andrés F,
Echeverri David A,
Rios Luis A
Publication year - 2017
Publication title -
journal of chemical technology and biotechnology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.64
H-Index - 117
eISSN - 1097-4660
pISSN - 0268-2575
DOI - 10.1002/jctb.5104
Subject(s) - carbonation , castor oil , epoxide , isocyanate , chemistry , epoxidized soybean oil , organic chemistry , monomer , chemical engineering , materials science , polymer chemistry , polymer , catalysis , polyurethane , raw material , engineering
BACKGROUND Cyclic fatty carbonates can be obtained from epoxidized vegetable oils and CO 2 under mild conditions. The main application of these bio‐derivatives is the production of thermoset polymers and non‐isocyanate polyurethanes. Castor oil has a different chemical structure from the other oils that have been used for carbonation. In this work, a kinetic model was developed for high CO 2 pressure carbonation of epoxidized castor oil. RESULTS The highest epoxide group conversion (93%) was obtained at 130 °C and 480 min. However, the highest content of carbonate groups (1.5 carbonates/molecule) was obtained at 115 °C and 180 min. A kinetic model was proposed which included carbonation of epoxide as well as etherification of the oxirane ring as a competitive reaction. Both reactions were best fitted to pseudo‐first‐order kinetics. Activation energy of carbonation and etherification of the oxirane ring were estimated as 37.41 and 33.25 kJ mol −1 , respectively. CONCLUSION Carbonated castor oil was produced from the epoxidized oil at 100–130 °C and a constant pressure of CO 2 (0.5 MPa ). Because of the polyfunctional character of the product, it could find applications as a monomer and as a synthetic building block for other bio‐based chemicals. This product and the reaction pathway have not previously been disclosed. © 2016 Society of Chemical Industry