Synthesis,evaluation and applications of complex esters as lubricants: A basic study

This paper reports the synthesis of various complex esters, describing their physical, chemical, and tribological properties. Specifically, an attempt is made to study the effects of changing the central polyol backbone, of varying chain length of diacids, and of different endcapping alcohols on various properties.     

Investigations into the epoxidation and alcoholysis of oleochemicals for use as lubricants

Most lubricants and functional fluids worldwide are based on mineral oil. These fluids contain up to 10% of a wide variety of additives for the improvement of their tribological properties. Several of these are still ecologically hazardous. From an environmental point of view, the use of renewable feedstock is of great interest. In Europe rape seed oil is available in substantial amounts and its esters (triglycerides, esters with saturated or partly unsaturated acids) to some extent display better tribological properties than conventional lubricants. The aim of the work which is presented here has been to improve the stability of these types of ester and their derivatives with regard to oxidation and hydrolysis. This can be done by the addition of different carboxylic acids and alcohols, of various complexities, to the double bonds. This paper deals with the indirect addition of different alcohols, such as methanol, isobutanol, and neopentanol, to the double bond of methyl oleate, and the addition of methanol to the double bonds of glycerin trioleate using the corresponding epoxides as intermediates. The reactions were carried out with environmentally friendly heterogeneous catalysts. Several tests, such as for viscosity, oxidation stability, and biodegradability, were carried out to demonstrate the potential of these newly developed fluids for use as lubricants.     

Synthesis and characterisation of antioxidant‐modified esters of dipentaerythritol as lubricating base oil

In this paper, five antioxidant‐modified esters were synthesised through two steps of simple esterification. Antioxidant‐modified multi‐hydroxyl compound was synthesised at the first step, and antioxidant‐modified esters were synthesised at the second step. This kind of esters is useful in many fields, such as lubricating oil and cutting compound, because of two important functions (antioxidant and lubricant) in the same compound. The active antioxidant group attached to these esters was 3‐(3,5‐di‐tert‐butyl‐4‐hydroxy‐phenyl)‐propionic acid. The esters were characterised with Fourier transform infrared spectroscopy (FTIR) and thermogravimetric (TG) analysis. The analytical results of FTIR demonstrates the changes of alcoholic hydroxyl and carboxyl and suggests that this synthesis was feasible. The TG analysis and rotating pressure vessel method show that this kind of esters has excellent oxidative stability. The physical properties of lubricating base oil, such as viscosity, viscosity index, pour point and flash point, suggested that this kind of esters can be used as lubricating base oil. Copyright © 2012 John Wiley & Sons, Ltd.     

Influence of fatty acid additives on the tribological performance of sunflower oil

Vegetable oils are potential substitutes for petroleum‐based lubricants because they are environmentally friendly, renewable, less toxic and readily biodegradable. The addition of free fatty acids has been shown to increase the lubrication performance of vegetable oils at elevated temperatures. The purpose of this study was to evaluate the relationship between the length of the carbon chain in the fatty acid and its effectiveness as an additive for a range of elevated temperatures. Stearic, arachidic and behenic fatty acid additives were added to commercial sunflower oil. All fatty acid additives were shown to be effective in lowering the wear rate and coefficient of friction in ball‐on‐disc tribological tests. The overall carbon chain length was not observed to have a consistent influence on the effectiveness of the additive. All additives were less effective at temperatures above 100°C. Copyright © 2010 John Wiley & Sons, Ltd.     

A study of the tribological behaviour of heterocyclic derivatives as additives in rape seed oil and mineral oil

The tribological properties of two novel heterocyclic derivatives as additives in rape seed oil and in mineral oil were investigated using a four‐ball machine. The morphologies and chemical features of the worn steel surfaces were observed and examined by means of X‐ray photoelectron spectroscopy and scanning electron microscopy. Both heterocyclic compounds improved the load‐carrying and extreme‐pressure capacities and the friction‐reducing and antiwear properties of rape seed oil more than they improved those of the mineral oil. Surface analyses of the rubbed surfaces revealed the formation of a protective film containing FeSO₄, organosulphur compound, FeS₂, polymerised ester, and organonitrogen compound when the surfaces were lubricated by rape seed oil containing the additives. The protective film formed during sliding processes contributed to the increase in the wear resistance.