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1. CHE 321 - Blended
Learning Week 12

2. FATTY ESTERS

3. What is Fatty Esters?
• Fatty esters (FEs) are a type of ester that resulted from the
combination of an oil or fat with an alcohol.
• An organic chemistry - RCOOR′
A fatty acid in which the alkyl group (R′) of a monohydric alcohol
replaces the active hydrogen; for example, RCOOCH3 from
reaction of RCOOH with methane.
• Biodiesels are typically fatty esters produced by the
transesterification of vegetable fats and oils which results in the
replacement of the glycerol component with a different alcohol.

4. • The most common fatty esters contained in biodiesel are those of
palmitic (hexadecanoic) acid, stearic (octadecanoic) acid, oleic
(9(Z)-octadecenoic) acid, linoleic (9(Z),12(Z)-octadecadienoic)
acid, and linolenic (9(Z),12(Z),15(Z)-octadecatrienoic) acid.
• This holds for biodiesel feedstocks, such as soybean, sunflower,
rapeseed (as canola), palm, and peanut oils. Some tropical oils,
such as coconut oil, contain significant amounts of shorter chain
acids, such as lauric (dodecanoic) acid.
• A variety of other fatty acids are found in minor amounts in
virtually all oils and fats used as biodiesel feedstocks.

5. The Uses And Application
Of Fatty Ester

6. The Uses and Application Of Fatty Ester
• As synthethic lubricants with desirable characteristics such as high
thermal and oxidation stability and low volatility.
• In pharmaceuticals - as antifoaming agents, emulsifiers, thickening
agents in ointment.
• Palm based methyl esters - as diesel substitutes for taxis, buses, lorries
and tractors, etc.
• Used in a broad variety of different industrial applications such as
cosmetics, toiletries, pharmaceuticals, food, metal working fluids, and
etc.
• Properties like lubrication, mould release, consistency promotion,
emolliency, stability enhancement, spreading or fatty, solvency and
cleaning demonstrate the large variety of functions offered by these
unique products.

7. Production Processes Of
Fatty Esters and Its
Derivatives

8. Production of Fatty Esters
o Fatty alcohols are the derivatives of fatty ester
o For the production of C12–C14 alcohols, only coconut oil and palm kernel oil can
be used. Palm oil, soybean oil and tallow are the main sources for C16–C18
alcohols. Rapeseed oil is mainly for fatty alcohols with 20 or 22 carbon atoms.
o Contaminants such as phosphatides, sterols or oxidation products and impurities
such as seed particles, dirt and water were removed during pre-treatment of
triglyceride.
o The refined triglycerides are then transesterified with lower alcohols to yield
fatty acid esters. The refined fatty acid esters (mostly methyl esters and, more
rarely, butylesters) are used for hydrogenation to produce fatty alcohols.

9. • Transesterification of Triglycerides.
• This reaction is carried out continuously with alkaline catalysts.
• Tansesterification is an equilibrium reaction and is shifted toward the
desired ester by excess methanol or removal of glycerol in order to produce
more fatty alcohols.

10. • Fatty esters is produced from the route production of fatty acids.
Meaning that, producing fatty acids, glycerine and fatty alcohols can
also yield fatty esters as the derivatives through some processes.
• Fatty esters is the derivative of fatty acid and fatty alcohols is the
derivative of fatty esters.

11. • Thermal splitting of fats and oils
Fats and oils, the naturally occurring triglycerides of fatty
acids, can be hydrolyzed to fatty acids and glycerin by
thermal splitting. The process is highly efficient and easy to
operate.

12. Types of Fatty Esters
 Fatty Acid Methyl Esters
 Polyol Esters
 Sorbitan Esters
 Sucrose Esters
 And others..

13. Fatty Acid Methyl Esters
• Fatty Acid Methyl Esters (FAME) are esters of fatty acids. The
physical characteristics of fatty acid esters are closer to those of
fossil diesel fuels than pure vegetable oils, but properties depend
on the type of vegetable oil.
• A mixture of different fatty acid methyl esters is commonly
referred to as biodiesel, which is a renewable alternative fuel.
FAME has physical properties similar to those of conventional
diesel. It is also non-toxic and biodegradable.

14. Production of Fatty Acid Methyl Esters
• FAME is produced from vegetable oils, animal fats or waste
cooking oils by transesterification.
• Transesterification process
 glyceride reacts with an alcohol in the presence of a catalyst, forming a
mixture of fatty acids esters and an alcohol. Using triglycerides results in
the production of glycerol.
Transesterification is a reversible reaction and is carried out by mixing the
reactants. A strong base or a strong acid can be used as a catalyst. At the
industrial scale, sodium or potassium methanolate is mostly used.

16. Polyol Esters
• Polyolester oil (POE oil) - a type of Synthetic oil used in refrigeration compressors
that is compatible with the refrigerants R-134a, R410A and R-12. Recommended
by experts as a replacement for HFC's (Hydrofluorocarbon). Along with R134A
mineral oil, recommended as a replacement for R12 mineral oil as R134A does not
mix well with mineral oil.
• These wax free oils are suggested for usage with chlorine free HFC systems as
they provide better lubrication and stability and are more miscible with HFC
refrigerants.
• They can meet the lubricity requirements to those of mineral oils used with CFC's
(Chlorofluorocarbon) and HFC's. They are compatible with most lubricants in the
market.
• It is noted that the viscosity of the oil increases with temperature. The dispersion
behavior of this oil has also been the subject of a lot of study and also considered
by some to be a good additive to engine oil.

17. Uses of Polyol Esters
• The use of this type of oil is in the process of being phased-in by
manufacturers who use compressors in their products. The need
to replace the old oils has arisen due to environmental
restrictions causing incompatibility of the old oils with the new
refrigerants.
• POE oils are very good solvents and easily dissolve most of the
residual mineral oils that they may be replacing. So even though
small amounts of the old oil may remain, it won't clog the
system.
• Polyolester oil is used exclusively in jet turbine engines and
often used in moving picture film cameras.

18. Sorbitan Esters
• (Also known as Spans) are lipophilic nonionic surfactants that are
used as emulsifying agents in the preparation of emulsions,
creams, and ointments for pharmaceutical and cosmetic use.
• When used alone they produce stable water-in-oil emulsions but
they are frequently used with a polysorbate in varying proportions
to produce water-in-oil or oil-in-water emulsions or creams with a
variety of different textures and consistencies.
• Sorbitan esters are also used as emulsifiers and stabilisers in food.

19. • The derivative types of Sorbitan esters are :-
Sorbitan Laurate
Sorbitan Stearate
Sorbitan Oleate
Sorbitan Tristearate
And so on..

20. Sucrose Esters
• Sucrose esters are obtained by esterifying sucrose with methyl fatty acids. By
varying the degree of esterification of the sucrose molecule it is possible to
obtain emulsifiers with HLB values ranging from 1 up to 16.
• Used in many food categories such as bakery, confectionery, cereals, dairy, ice
cream and sauces.
• Manufacturers have multiple reasons to work with sucrose esters, for example it
can improve the production process by reducing mixing time or keeping
viscosities low.
• Sucrose esters are also more used in low fat alternatives. In these products the
mouth feel provided by fat has to be maximized, an emulsifier makes the fat
globules much smaller and therefore provides good eating properties.
• A bakery product will have a finer crumb structure and a softer texture, the
stability of dairy or sauces will be improved, the texture of a mousse finer and
ice cream a better flavor.

21. • Although sucrose esters are categorized as emulsifiers their
function is not only emulsification.
• Functions such as
Aeration
Texturization
protein protection
or starch interaction
and fat or sugar crystallization
are often used.
• Sucrose esters are unique in a way that they can boost other
emulsifiers and improve the air bubble structure or prevent
proteins from browning or keep starches from early staling.
• The effect on sugar and fat crystallization is primarily used in
confections to prevent fat bloom in chocolate and to accelerate
crystallization in fine grained sugar confection.

22. References
• http://en.wikipedia.org/wiki/Fatty_acid_ester
• http://en.wikipedia.org/wiki/Fatty_acid_methyl_ester
• https://www.mitsui.com/jp/en/release/2015/1203968_6041.html
• http://pubs.acs.org/doi/pdf/10.1021/ef700639e
• http://www.klkoleo.com/brand/palmester%C2%AE-fatty-esters
• http://www.ccur.iastate.edu/biorenewables/publications/fattyacidoverview0105/f
attyacidoverview180804.htm
• http://www.ebi.ac.uk/chebi/searchId.do?chebiId=35748
• http://www.biofuelstp.eu/factsheets/fame-fact-sheet.pdf
• http://encyclopedia2.thefreedictionary.com/fatty+ester
• http://www.drugfuture.com/chemdata/sorbitan-esters.html
• http://en.wikipedia.org/wiki/Sorbitan
• http://en.wikipedia.org/wiki/Polyolester
• http://www.sisterna.com/index.php/sucrose-esters/food/
• http://www.molecularrecipes.com/hydrocolloid-guide/sucrose-ester-sucro-2/