Oleochemical

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Oleochemicals (from Latin: oleum olive oil) are chemicals derived from plant and animal fats. They are
analogous to petrochemicals derived from petroleum.
The formation of basic oleochemical substances like fatty acids, fatty acid methyl esters (FAME), fatty alcohols,
fatty amines and glycerols are by various chemical and enzymatic reactions. Intermediate chemical substances
produced from these basic oleochemical substances include alcohol ethoxylates, alcohol sulfates, alcohol ether
sulfates, quaternary ammonium salts, monoacylglycerols (MAG), diacylglycerols (DAG), structured triacylglycerols
(TAG), sugar esters, and other oleochemical products.
As the price of crude oil rose in the late 1970s,[1] manufacturers switched from petrochemicals to oleochemicals[2]
because plant-based lauric oils processed from palm kernel oil were cheaper. Since then, palm kernel oil is
predominantly used in the production of laundry detergent and personal care items like toothpaste, soap bars,
shower cream and shampoo.[3]

Contents
1 Processes
1.1 Hydrolysis
1.2 Transesterification
1.3 Hydrogenation
2 Applications
3 Oleochemical industry development
3.1 Europe
3.2 Southeast Asia
4 References

Processes
Important processeses in oleochemical manufacturing include hydrolosis and transesterification, among others.

Hydrolysis
The splitting (or hydrolysis) of the triglycerides produces fatty acids and glycerol:
RCO2CH2CHO2CRCH2O2CR + 3 H2O 3 RCOOH + HOCH2CHOHCH2OH
The addition of base helps the reaction proceed more quickly, the process being saponification.

Transesterification

Fats react with alcohols (R'OH) instead of with water in hydrolysis) in a process called transesterification. Glycerol
is produced together with the fatty acid esters. Most typically, the reaction entails the use of methanol (MeOH) to
give fatty acid methyl esters:
RCO2CH2CHO2CRCH2O2CR + 3 MeOH 3 RCO2Me + HOCH2CHOHCH2OH
FAMEs are less viscous than the precursor fats and can be purified to give the individual fatty acid esters, e.g.
methyl oleate vs methyl palmitate.

Hydrogenation
The fatty acid or fatty esters produced by these methods may be transformed. For example, hydrogenation
converts unsaturated fatty acids into saturated fatty acids. The acids or esters can also be reduced to the fatty
alcohols. For some applications, fatty acids are converted to fatty nitriles. Hydrogenated of these nitriles gives fatty
amines, which have a variety of applications.[4]

Applications
The largest application for oleochemicals, about 30% of market share for fatty acids and 55% for fatty alcohols, is
for making soaps and detergents.[5]:21 Lauric acid, used to produce sodium lauryl sulfate and related compounds,
which are used to make soaps and other personal care products.
Other applications of oleochemicals include the production of lubricants, solvents, biodiesel and bioplastics. Due to
the use of methyl esters in biodiesel production, they represent the fastest growing sub-sector of oleochemical
production in recent years.[5]:15
Oleochemicals are important raw material for polymeric resins specially alkyd based because of possible functional
group modifications. These modifications are based on reaction of vegetable oil with excess glycerol to obtain
monoglyceride, which is then converted into polymeric resins i.e. alkyd by reacting with dicarboxylic acids or
anhydrides. Recently polyesteramide resins are also prepared using vegetable oil as an oleochemical.[6][7]

Oleochemical industry development

Europe
Through the 1996 creation of Novance and the 2008 acquisition of Oleon, Avril Group has dominated the
European market of oleochemistry[8]

Southeast Asia
Southeast Asian countries' rapid production growth of palm oil and palm kernel oil in the 1980s spurred the
oleochemical industry in Malaysia, Indonesia, and Thailand. Many oleochemical plants were built. Though a nascent
and small industry when pitted against big detergent giants in the US and Europe, oleochemical companies in
southeast Asia had competitive edge in cheap ingredients.[9] The US fatty chemical industry found it difficult to
consistently maintain acceptable levels of profits. Competition was intense with market shares divided among many

companies there where neither imports nor exports played a significant role.[10] By the late 1990s, giants like
Henkel, Unilever, and Petrofina sold their oleochemical factories to focus on higher profit activities like retail of
consumer goods. Since the Europe outbreak of 'mad cow disease' or (bovine spongiform encephalopathy) in 2000,
tallow is replaced for many uses by vegetable oleic fatty acids, such as palm kernel and coconut oils.[5]:24

References
1. Haupt, D. E.; Drinkard, G.; Pierce, H. F. (1984).
"Future of petrochemical raw materials in
oleochemical markets". Journal of the American Oil
Chemists' Society. 61 (2): 276.
doi:10.1007/BF02678781.
2. Akaike, Yoshiteru (1985). "Other oleochemical uses:
Palm oil products". Journal of the American Oil
Chemists' Society. 62 (2): 335.
doi:10.1007/BF02541401.
3. Dewaet, F. (1985). "Quality requirements from a
consumer's point of view (oleochemical products)".
Journal of the American Oil Chemists' Society. 62
(2): 366. doi:10.1007/BF02541406.
4. Karsten Eller, Erhard Henkes, Roland Rossbacher,
Hartmut Hke "Amines, Aliphatic" in Ullmann's
Encyclopedia of Industrial Chemistry, Wiley-VCH,
Weinheim, 2005. doi:10.1002/14356007.a02_001 (ht
tps://dx.doi.org/10.1002%2F14356007.a02_001)
5. The Changing World of Oleochemicals (http://palmoi
lis.mpob.gov.my/publications/POD/pod44-wolfgang.
pdf) Wolfgang Rupilius and Salmiah Ahmad, Palm
Oil Developments 44, 2005

6. Ravindra Marathe, Pyus Tatiya, Ashok Chaudhari,

Jeongwook Lee, Pramod Mahulikar, Daewon Sohn,
Vikas Gite, Neem acetylated polyester polyol
Renewable source based smart PUcoatings
containing quinoline (corrosion inhibitor)
encapsulatedpolyurea microcapsules for enhance
anticorrosive property Industrial Crops and Products
77 (2015) 239250.
7. Sandip D. Rajput, Vikas V. Gite, Pramod P.
Mahulikar, Viresh R. Thamke, Kisan M. Kodam,
Anil S. Kuwar, Renewable Source Based Nonbiodegradable Polyurethane Coatings from
Polyesteramide Prepared in One-Pot Using Oleic
Acid, J Am Oil Chem Soc (2014) 91:10551063
8. (Avril Group : Activity Report 2014, p. 41)
9. The Future of Palm Oil in Oleochemicals (http://pal
moilis.mpob.gov.my/publications/POD/pod14-3.pdf)
Appalasami & de Vries, Palm Oil Developments 143, 1990
10. Leonard, E. Charles; Kapald, S L (1984).
"Challenges to a mature industry: Marketing and
economics of oleochemicals in the United States".
Journal of the American Oil Chemists' Society. 61
(2): 176. doi:10.1007/BF02678763.

6. Ravindra Marathe, Pyus Tatiya, Ashok Chaudhari,

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Categories: Lipids
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