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ARS Home » Midwest Area » Peoria, Illinois » National Center for Agricultural Utilization Research » Renewable Product Technology Research » Research » Publications at this Location » Publication #355245
Research Project: Technologies for Producing Biobased Chemicals

Location: Renewable Product Technology Research

Title: Microbial conversion of vegetable oil to hydroxy fatty acid and its application to bio-based polyurethane synthesis

Author
item TRAN, TUAN - Chungbuk National University
item KUMAR, PRASUN - Chungbuk National University
item KIM, HAK-RYUL - Kyungpook National University
item Hou, Ching
item KIM, BEOM SOO - Chungbuk National University

Submitted to: Polymers
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 8/17/2018
Publication Date: 8/19/2018
Citation: Tran, T.K., Kumar, P., Kim, H., Hou, C.T., Kim, B. 2018. Microbial conversion of vegetable oil to hydroxy fatty acid and its application to bio-based polyurethane synthesis. Polymers. 10(8) https://doi.org/10.3390/polym10080927.
DOI: https://doi.org/10.3390/polym10080927

Interpretive Summary: Previously, we discovered a new microbial culture PR3 that produced oxygenated fatty acids from oleic acid and linoleic acid. Hydroxy fatty acids are useful as starting materials for the synthesis of specialty chemicals, special military nylon, plastisizers, coating materials, and possibly as antimicrobial and other bioactive (such as enzyme inhibitor) agents. Industry needs polyol oil to synthesize polymers. We produced dihydroxy fatty acid (DOD) from olive oil by strain PR3 and used this DOD to synthesize polyurethane. These polyurethanes displayed higher elongation at breaking and good thermal stability. This is the first report on the synthesis of polyurethanes based on DOD-containing polyol oil produced by microbial conversion of vegetable oil. This study demonstrates that natural oils can be effectively bioconverted to hydroxyl fatty acids, which can act as building blocks to synthesize bio-based polyurethanes. This finding could benefit U.S. soybean farmers.

Technical Abstract: Novel polyurethanes based on dihydroxy fatty acid obtained by microbial conversion of olive oil were synthesized. Monounsaturated 7,10-dihydroxy-8(E)-octadecenoic acid (DOD) was produced from olive oil by Pseudomonas aeruginosa PR3 and reacted with hexamethylene diisocyanate (HMDI) at different ratios to form polyurethanes. Fourier transform-infrared spectroscopy and gas chromatography/mass spectrometry confirmed the synthesis of DOD. The thermal and tensile properties of the polyurethanes were investigated by X-ray diffraction, differential scanning calorimetry, thermogravimetric analysis, and universal testing machine. At an isocyanate/hydroxyl ratio of 1.4, the polyurethane exhibited an elongation at break of 59.2% and a high tensile strength of 37.9 MPa. DOD was also mixed with polycaprolactone diol or polyethylene glycol at different weight ratios and then reacted with HMDI to produce novel polyurethanes of various properties. These polyurethanes displayed higher elongation at break and good thermal stability. This is the first report on the synthesis of polyurethanes based on DOD produced by microbial conversion of vegetable oil.