Submitted to: Journal of the American Oil Chemists' Society
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 8/12/2013
Publication Date: 1/14/2014
Citation: Biswas, A., Cheng, H.N., Kim, S., Liu, Z. 2014. Modified triglyceride oil through reactions with phenyltriazolinedione. Journal of the American Oil Chemists' Society. 91:125-131.
Interpretive Summary: There has been a constant demand for environmentally friendly lubricants. The interest intensified during the last decade due to strict government and environmental regulations. Most of the current lubricants originate from petroleum stock, which is toxic to environment and difficult to dispose of. Vegetable oils with high oleic content are considered to be potential candidates to substitute conventional mineral oil-based lubricating oils and synthetic esters. Vegetable oils are preferred to synthetic fluids because they are renewable resources and potentially cheaper. A novel synthetic approach for chemical modification of vegetable oils is presented. We have developed a novel solvent/catalyst less green pathway to modify vegetable oil by incorporating nitrogen into the triglyceride structure by using 4-Phenyl-1,2,4-Triazoline-3,5-Dione (PTAD). At room temperature the reaction can be achieved in a few hours. These new materials perhaps can be used as sealants, high performance caulks or lubricants and coatings. This method that produced no byproducts will benefit industrial chemical manufacturers especially those in sealants and high performance caulks industries. This work will generate new markets for soybean oil and thus, help the soybean growers.
Technical Abstract: The synthesis of a modified triglyceride oil was achieved through the reactions with 4-phenyl-1,2-4-triazoline-3,5-dione (PTAD). 1H NMR was used for structure determination and to monitor the reactions. Several reaction products were produced, and their relative yields depended on the stoichiometry and temperature of reaction. The reaction product mixture exhibited a self-curing behavior as a function of time. Thus, the viscosity of a mixture containing PTAD and triglyceride in a 3:10 weight ratio increased 100-fold in about 1.5 hours at room temperature, suggesting its possible use as additive in adhesive and thickener applications.