Biobased lubricant additives derived from limonene

Authors: Biresaw, Girma; Bantchev, Grigor; Murray, Rex

Submitted to: Society of Tribologists and Lubrication Engineers
Publication Type: Abstract Only
Publication Acceptance Date: 12/29/2015
Publication Date: 5/15/2016
Citation: Biresaw, G., Bantchev, G.B., Murray, R.E. 2016. Biobased lubricant additives derived from limonene [abstract]. Society of Tribologists and Lubrication Engineers Annual Meeting & Expo, Session 5F: Non-Ferrous Metals II: Biobased Lubricants. p. 115

Interpretive Summary:

Technical Abstract: Limonene is a natural product widely found in many plants as a constituent of “essential oils.” It is commercially produced as a byproduct of the citrus industry from processing of fruits such as oranges, lemons, lime, tangerines, mandarins, and grapefruits. Limonene is a C10 hydrocarbon with a complex structure that includes a six-membered cyclic ring, branching, two double bonds, and a chiral carbon. It is relatively inert under mild temperature conditions and is used for a variety of industrial and medical applications. However, applications under severe conditions will require structural modifications and/or the use of stabilizing additives. In this work, we describe the chemical modification of limonene by free radical reaction with dialkyl phosphites of varying alkyl structures under inert atmosphere. The mono- and di-adduct reaction product mixtures were positively identified and characterized using a combination of gas chromatography-mass spectroscopy, infrared spectroscopy, and nuclear magnetic resonance spectroscopy (1H, 13C, 31P). The results of investigations into the physical and tribological properties of the limonene phosphonate product mixtures is discussed.