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, manufacturers switched from petrochemicals to oleochemicals 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.
Important processeses in oleochemical manufacturing include hydrolosis and transesterification, among others.
- RCO2CH2–CHO2CR–CH2O2CR + 3 H2O → 3 RCOOH + HOCH2–CHOH–CH2OH
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:
- RCO2CH2–CHO2CR–CH2O2CR + 3 MeOH → 3 RCO2Me + HOCH2–CHOH–CH2OH
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.
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.
The largest application for oleochemicals, about 30% of market share for fatty acids and 55% for fatty alcohols, is for making soaps and detergents.: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.: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.
Oleochemical industry development
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. 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. 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.:24
- 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.
- Akaike, Yoshiteru (1985). "Other oleochemical uses: Palm oil products". Journal of the American Oil Chemists' Society. 62 (2): 335. doi:10.1007/BF02541401.
- 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.
- Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke "Amines, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005. doi:10.1002/14356007.a02_001
- The Changing World of Oleochemicals Wolfgang Rupilius and Salmiah Ahmad, Palm Oil Developments 44, 2005
- 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) 239–250.
- Sandip D. Rajput, Vikas V. Gite, Pramod P. Mahulikar, Viresh R. Thamke, Kisan M. Kodam, Anil S. Kuwar, Renewable Source Based Non-biodegradable Polyurethane Coatings from Polyesteramide Prepared in One-Pot Using Oleic Acid, J Am Oil Chem Soc (2014) 91:1055–1063
- (Avril Group : Activity Report 2014, p. 41)
- The Future of Palm Oil in Oleochemicals Appalasami & de Vries, Palm Oil Developments 14-3, 1990
- 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.