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 substantial family of esters have been
found to be very useful in severe environment applications.
Esters have been used successfully in lubrication for more
than 50 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 40 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 esters and these products were quite successful
when properly formulated.
Esters have given way to PAOs (Polyalphaolefins) in this
application due to PAOs lower cost and their formulating
similarities to mineral oil. Nevertheless, esters are nearly
always 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 in
motor oils can vary anywhere form 5 to 25% depending upon
the desired properties and the type of ester employed.
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 high temperature extremes and their telltale
signs such as smoking, wear, 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 form relatively
pure and simple starting materials to produce predetermined
molecular structures designed specifically for high performance
lubrication. Both types of synthetic base stocks are primarily
branched hydrocarbons which are thermally and oxidatively
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 multiple ester linkages (COOR) in esters
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 penetrate.
The result is a stronger film which translates into higher
lubricity and lower energy consumption on 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.