Process for preparing a synthetic ester from a vegetable oil

Solid anti-friction devices – materials therefor – lubricant or se – Lubricants or separants for moving solid surfaces and... – Organic -co- compound

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Details

554167, 554168, 554169, C10M10538, C08G 6378

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active

058859462

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BRIEF SUMMARY
This application is a 371 of PCT/FI95/00477 filed Sep. 7, 1995.
The objects of the present invention are a process for preparing a synthetic ester from a vegetable oil and lubricants which contain a synthetic ester prepared by said process.
Natural fats and oils have been used as lubricants already for thousands of years. With industrialization mineral based lubricants came also to the market. The applications of lubricants and thus also the requirements set for them have changed and developed with the advance of technology. Various types of synthetic esters and lubricants containing the same have been developed to meet the new requirements.
The purpose of a lubricant is to minimize friction and wear of metals. Lubricants are developed according to the use and they consist of a base fluid and additives improving the lubricative properties. With the development of technology, lubricants are used under more and more severe conditions, such as at very low or very high temperatures (e.g. the turbine engines of aeroplanes). At the same time biodegradability, non-accumulation to the environment, non-toxicity and the use of renewable raw materials have emerged -as new requirements. The use of biodegradable lubricants is of particular importance in the machines and devices used in the fields of agriculture, forestry and building, as the oil used may be left in the environment.
By the synthetic esters developed as lubricants are meant esters prepared from mono-, di- or trialcohols and mono- or dicarboxylic acids by known esterification and transesterification methods. Usually the process comprises combining all the reactants and letting the reaction happen in one stage. The reaction may be carried out in the presence of catalysts, such as acids, bases or metal oxides.
The structure of the synthetic ester used has a profound effect on the stability of the lubricant. Esters decompose by the effect of heat and/or oxygen. It is known to increase the thermal stability of synthetic esters by using in the preparation no beta hydrogen alcohols. Oxidative properties on the other hand can be improved by deuteration of esters.
Synthetic esters intended for a lubricative use are classified by structure as monocarboxylic acid, dicarboxylic acid, polyol and complex esters. Due to their low viscosity and high volatility monoesters are poorly suitable as lubricants. Polyol esters are chemically more stable than for example diesters due to the structure of the polyols used in the preparation of said esters, wherein no hydrogen atom is attached to the .beta. carbon atom. Complex esters have promising lubricative properties but the manufacture thereof on an industrial scale is difficult because of the severe conditions required by the reaction, especially if said esters are prepared from purified fatty acids and alcohols.
If polyol esters are prepared by using no alfa hydrogen acids, the stability properties of the esters can be further improved. Metro et al. (CA 859 771) have shown that the no alfa hydrogen carboxylic acids increase the thermal and oxidative stability of esters prepared from no beta hydrogen alcohols, as well as slow down the hydrolysis of the esters.
As the low viscosity polyol esters are not suitable for traditional uses wherein high viscosity is required, it has been aimed at preparing polyol esters of higher viscosity from for example trimethylol propane (TMP). However, it has been found that it is difficult to obtain simple TNT esters with both high viscosity and a low pour point (cf. for example U.S. Pat. No. 4,061,581).
Products based on vegetable oils are nowadays used more and more as lubricants because of their safety to the environment. Natural vegetable and animal oils are glyceride diesters, i.e. tri-, di- or monoesters of glycerol and straight chain saturated and unsaturated fatty acids. The lubricant industry uses for instance rapeseed, rape, soybean, castor, olive, coconut, palm and tall oils.
The advantageous properties of vegetable oils include user friendliness and non-toxicity. In addition to thi

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