Skip to main content
ARS Home » Midwest Area » Peoria, Illinois » National Center for Agricultural Utilization Research » Plant Polymer Research » Research » Publications at this Location » Publication #310761
Title: Polymerization of epoxidized triglycerides with fluorosulfonic acid

Author
item Biswas, Atanu
item Liu, Zengshe - Kevin
item Cheng, Huai

Submitted to: International Journal of Polymer Analysis and Characterization
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 10/16/2015
Publication Date: 4/1/2016
Citation: Biswas, A., Liu, Z., Cheng, H.N. 2016. Polymerization of epoxidized triglycerides with fluorosulfonic acid. International Journal of Polymer Analysis and Characterization. 21(1):85-93.

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 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 new method of polymerizing epoxidized soybean oil has been devised with the use of fluorosulfonic acid. Depending on the reaction conditions, we can get a viscous oil or a solid as the reaction product. The reaction mechanism has been studied through a systematic examination of the fluorosulfonic acid-initiated reaction of epoxidized methyl oleate and epoxidized methyl linoleate. The major species in these reactions have been identified through 13C NMR spectroscopy. In this way, the polymer structure derived from fluorosulfonic acid-initiated polymerization of epoxidized soybean oil has been determined. The effects of temperature, initiator dosage and reaction time have been studied and shown to affect the nature of polymer products obtained and the distribution of different chemical functional groups present. These polymers prepared by our novel catalyst may be used as caulks, lubricants and as ingredients in coatings, cosmetics, biodiesel fuel. These may also be used as a possible additive in lubricant formulations in order to increase their viscosities, or as a thickener in various commercial formulations that involve mineral or vegetable oils. This discovery will benefit bio oil growers everywhere.

Technical Abstract: The use of triglycerides as agri-based renewable raw materials for the development of new products is highly desirable in view of uncertain future petroleum prices. A new method of polymerizing epoxidized soybean oil has been devised with the use of fluorosulfonic acid. Depending on the reaction conditions, one can get a viscous oil or a solid as the reaction product. The reaction mechanism has been studied through a systematic examination of the fluorosulfonic acid-initiated reaction of epoxidized methyl oleate and epoxidized methyl linoleate. Through 13C NMR spectroscopy, the major species derived from fluorosulfonic acid-initiated polymerization of epoxidized soybean oil have been determined. The effects of temperature, initiator dosage, and reaction time have been studied and shown to affect the nature of polymer products obtained and the distribution of different chemical species present.