NDLI: Tribological Properties of Limonene Bisphosphonates

Content Provider	Springer Nature Link
Author	Biresaw, Girma Bantchev, Grigor B.
Copyright Year	2015
Abstract	Limonene was chemically modified by reacting it with dialkyl phosphites of varying alkyl structures under inert atmosphere in the presence of free radical initiators. The reaction gave a mixture of mono- and di-adduct products and was optimized to produce only the di-adduct product limonene bisphosphonate by forcing both limonene double bonds to react completely. The product mixture was carefully characterized using a combination of gas chromatography–mass spectroscopy, infrared spectroscopy, and nuclear magnetic resonance spectroscopy ($^{1}$H, $^{13}$C, $^{31}$P). The bisphosphonates were investigated for their physical and tribological properties. The alkyl bisphosphonates displayed density and viscosity that was a function of the alkyl structure (methyl, ethyl, n-butyl) and much higher than the values for the unreacted limonene. They also displayed improved oxidation stability but lower viscosity index and solubility in polyalphaolefin (PAO6) and high-oleic sunflower oil (HOSuO) base oils. Tribological characterization of the neat modified oils on a four-ball tribometer showed improved extreme-pressure weld point by all three di-adducts and improved anti-wear coefficient of friction (COF) and wear scar diameter (WSD) by the n-butyl di-adduct only. The limonene bisphosphonates also displayed improved COF and WSD as additives in PAO6 and HOSuO base oils at low concentrations. The effects of chemical modifications on physical and tribological properties can be explained in terms of increased polarity of the modified products, insertion of heavy atoms (from PO$_{3}$) into the limonene structure, and complete absence of unsaturation in the modified products.
Starting Page	1
Ending Page	15
Page Count	15
File Format	PDF
ISSN	10238883
Journal	Tribology Letters
Volume Number	60
Issue Number	1
e-ISSN	15732711
Language	English
Publisher	Springer US
Publisher Date	2015-09-09
Publisher Place	New York
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Limonene Bisphosphonates Chemical modification Synthesis Polarity Four-ball tribometer Anti-wear Extreme pressure Weld point Coefficient of friction Wear scar diameter PDSC Onset temperature Peak temperature GC–MS NMR FTIR Tribology, Corrosion and Coatings Surfaces and Interfaces, Thin Films Theoretical and Applied Mechanics Physical Chemistry Nanotechnology
Content Type	Text
Resource Type	Article
Subject	Surfaces, Coatings and Films Mechanics of Materials Mechanical Engineering Surfaces and Interfaces

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