Ester based oils.... https://www.bobistheoilguy.com/forums/ubbthreads.php?ubb=showflat&Number=1501525
High Ester based oils https://www.bobistheoilguy.com/forums/ubbthreads.php?ubb=showflat&Number=51664
What is better? PAO Only or Pao/Ester Oil? https://www.bobistheoilguy.com/forums/ubbthreads.php?ubb=showflat&Number=2152848
PAO vs. ESTER oils? which one is better? https://www.bobistheoilguy.com/forums/ubbthreads.php?ubb=showflat&Number=145740
Elf Tech Team - PAO vs Ester https://www.bobistheoilguy.com/forums/ubbthreads.php?ubb=showflat&Number=199762
Wondering about the esters used in High Mileage oils... https://www.bobistheoilguy.com/forums/ubbthreads.php?ubb=showflat&Number=74430
PAO or Ester ? https://www.bobistheoilguy.com/forums/ubbthreads.php?ubb=showflat&Number=1864057
TBN and TAN in ester oils, excellent info! https://www.bobistheoilguy.com/forums/ubbthreads.php?ubb=showflat&Number=1583684
Esters In Synthetic Lubricantshttps://www.bobistheoilguy.com/esters-in-synthetic-lubricants/
By T. G. Schaefer (Tom NJ)
In the simplest terms, esters can be defined as the reaction products of acids and alcohols. Thousands of different kinds of esters are commercially produced for a broad range of applications. Within the realm of synthetic lubrication, a relatively small but still substantial family of esters have been found to be very useful in severe environment applications. This paper shall provide a general overview of the more common esters used in synthetic lubricants and discuss their important benefits and utilities.
Esters have been used successfully in lubrication for more than 60 years and are the preferred stock in many severe applications where their benefits solve problems or bring value. For example, esters have been used exclusively in jet engine lubricants worldwide for over 50 years due to their unique combination of low temperature flowability with clean high temperature operation. Esters are also the preferred stock in the new synthetic refrigeration lubricants used with CFC replacement refrigerants. Here the combination of branching and polarity make the esters miscible with the HFC refrigerants and improves both low and high temperature performance characteristics. In automotive applications, the first qualified synthetic crankcase motor oils were based entirely on ester formulations and these products were quite successful when properly formulated. Esters have given way to PAOs in this application due to PAOs lower cost and their formulating similarities to mineral oil. Nevertheless, esters are often used in combination with PAOs in full synthetic motor oils in order to balance the effect on seals, solubilize additives, reduce volatility, and improve energy efficiency through higher lubricity. The percentage of ester used can vary anywhere from 5 to 25% depending upon the desired properties and the type of ester employed.
The new frontier for esters is the industrial marketplace where the number of products, applications, and operating conditions is enormous. In many cases, the very same equipment which operates satisfactorily on mineral oil in one plant could benefit greatly from the use of an ester lubricant in another plant where the equipment is operated under more severe conditions. This is a marketplace where old problems or new challenges can arise at any time or any location. The high performance properties and custom design versatility of esters is ideally suited to solve these problems. Ester lubricants have already captured certain niches in the industrial market such as reciprocating air compressors and high temperature industrial oven chain lubricants. When one focuses on temperature extremes and their telltale signs such as smoking and deposits, the potential applications for the problem solving ester lubricants are virtually endless.
In many ways esters are very similar to the more commonly known and used synthetic hydrocarbons or PAOs. Like PAOs, esters are synthesized from relatively pure and simple starting materials to produce predetermined molecular structures designed specifically for high performance lubrication. Both types of synthetic basestocks are primarily branched hydrocarbons which are thermally stable, have high viscosity indices, and lack the undesirable and unstable impurities found in conventional petroleum based oils. The primary structural difference between esters and PAOs is the presence of oxygen in the hydrocarbon molecules in the form of multiple ester linkages (COOR) which impart polarity to the molecules. This polarity affects the way esters behave as lubricants in the following ways:
Volatility: The polarity of the ester molecules causes them to be attracted to one another and this intermolecular attraction requires more energy (heat) for the esters to transfer from a liquid to a gaseous state. Therefore, at a given molecular weight or viscosity, the esters will exhibit a lower vapor pressure which translates into a higher flash point and a lower rate of evaporation for the lubricant. Generally speaking, the more ester linkages in a specific ester, the higher its flash point and the lower its volatility.
Lubricity: Polarity also causes the ester molecules to be attracted to positively charged metal surfaces. As a result, the molecules tend to line up on the metal surface creating a film which requires additional energy (load) to wipe them off. The result is a stronger film which translates into higher lubricity and lower energy consumption in lubricant applications.
Detergency/Dispersency: The polar nature of esters also makes them good solvents and dispersants. This allows the esters to solubilize or disperse oil degradation by-products which might otherwise be deposited as varnish or sludge, and translates into cleaner operation and improved additive solubility in the final lubricant.
Biodegradability: While stable against oxidative and thermal breakdown, the ester linkage provides a vulnerable site for microbes to begin their work of biodegrading the ester molecule. This translates into very high biodegradability rates for ester lubricants and allows more environmentally friendly products to be formulated.
Another important difference between esters and PAOs is the incredible versatility in the design of ester molecules due to the high number of commercially available acids and alcohols from which to choose. For example, if one is seeking a 6 cSt synthetic basestock, the choices available with PAOs are a straight cut 6 cSt or a “dumbbell” blend of a lighter and heavier PAO. In either case, the properties of the resulting basestock are essentially the same. With esters, literally dozens of 6 cSt products can be designed each with a different chemical structure selected for the specific desired property. This allows the “ester engineer” to custom design the structure of the ester molecules to an optimized set of properties determined by the end customer or application. The performance properties that can be varied in ester design include viscosity, viscosity index, volatility, high temperature coking tendencies, biodegradability, lubricity, hydrolytic stability, additive solubility, and seal compatibility.
As with any product, there are also downsides to esters. The most common concern when formulating with ester basestocks is compatibility with the elastomer material used in the seals. All esters will tend to swell and soften most elastomer seals however, the degree to which they do so can be controlled through proper selection. When seal swell is desirable, such as in balancing the seal shrinkage and hardening characteristics of PAOs, more polar esters should be used such as those with lower molecular weight and/or higher number of ester linkages. When used as the exclusive basestock, the ester should be designed for compatibility with seals or the seals should be changed to those types which are more compatible with esters.
Another potential disadvantage with esters is their ability to react with water or hydrolyze under certain conditions. Generally this hydrolysis reaction requires the presence of water and heat with a relatively strong acid or base to catalyze the reaction. Since esters are usually used in very high temperature applications, high amounts of water are usually not present and hydrolysis is rarely a problem in actual use. Where the application environment may lead to hydrolysis, the ester structure can be altered to greatly improve its hydrolytic stability and additives can be selected to minimize any effects.
The following is a discussion of the structures and features of the more common ester families used in synthetic lubrication.