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Oleochemistry is the study of
vegetable oil Vegetable oils, or vegetable fats, are oils extracted from seeds or from other parts of fruits. Like animal fats, vegetable fats are ''mixtures'' of triglycerides. Soybean oil, grape seed oil, and cocoa butter are examples of seed oils, or fat ...
s and animal oils and
fat In nutrition science, nutrition, biology, and chemistry, fat usually means any ester of fatty acids, or a mixture of such chemical compound, compounds, most commonly those that occur in living beings or in food. The term often refers spec ...
s, and oleochemicals derived from these fats and oils. The resulting product can be called oleochemicals (from Latin: oleum "olive oil"). The major product of this industry is soap, approximately 8.9×106 tons of which were produced in 1990. Other major oleochemicals include
fatty acids In chemistry, particularly in biochemistry, a fatty acid is a carboxylic acid with an aliphatic chain, which is either saturated or unsaturated. Most naturally occurring fatty acids have an unbranched chain of an even number of carbon atoms, f ...
,
fatty acid methyl esters Fatty acid methyl esters (FAME) are a type of fatty acid ester that are derived by transesterification of fats with methanol. The molecules in biodiesel are primarily FAME, usually obtained from vegetable oils by transesterification. They are used ...
,
fatty alcohol Fatty alcohols (or long-chain alcohols) are usually high-molecular-weight, straight-chain primary alcohols, but can also range from as few as 4–6 carbons to as many as 22–26, derived from natural fats and oils. The precise chain length varies ...
s and
fatty amine In chemistry, a fatty amine is loosely defined as any amine possessing a mostly linear hydrocarbon chain of eight or more carbon atoms. They are typically prepared from the more abundant fatty acids, with vegetable or seed-oils being the ultimate ...
s. Glycerol is a side product of all of these processes. Intermediate chemical substances produced from these basic oleochemical substances include
alcohol ethoxylates Ethoxylation is a chemical reaction in which ethylene oxide adds to a substrate. It is the most widely practiced alkoxylation, which involves the addition of epoxides to substrates. In the usual application, alcohols and phenols are converted ...
, alcohol sulfates, alcohol ether sulfates,
quaternary ammonium salts In chemistry, quaternary ammonium cations, also known as quats, are positively charged polyatomic ions of the structure , R being an alkyl group or an aryl group. Unlike the ammonium ion () and the primary, secondary, or tertiary ammonium cations ...
,
monoacylglycerols Monoglycerides (also: acylglycerols or monoacylglycerols) are a class of glycerides which are composed of a molecule of glycerol linked to a fatty acid via an ester bond. As glycerol contains both primary and secondary alcohol groups two differen ...
(MAG),
diacylglycerols A diglyceride, or diacylglycerol (DAG), is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Two possible forms exist, 1,2-diacylglycerols and 1,3-diacylglycerols. DAGs can act as sur ...
(DAG), structured
triacylglycerols A triglyceride (TG, triacylglycerol, TAG, or triacylglyceride) is an ester derived from glycerol and three fatty acids (from ''tri-'' and ''glyceride''). Triglycerides are the main constituents of body fat in humans and other vertebrates, as we ...
(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.


Processes

Important process in oleochemical manufacturing include hydrolysis and transesterification, among others.


Hydrolysis

The splitting (or hydrolysis) of the
triglyceride A triglyceride (TG, triacylglycerol, TAG, or triacylglyceride) is an ester derived from glycerol and three fatty acids (from ''tri-'' and ''glyceride''). Triglycerides are the main constituents of body fat in humans and other vertebrates, as w ...
s produces
fatty acid In chemistry, particularly in biochemistry, a fatty acid is a carboxylic acid with an aliphatic chain, which is either saturated or unsaturated. Most naturally occurring fatty acids have an unbranched chain of an even number of carbon atoms, fr ...
s and
glycerol Glycerol (), also called glycerine in British English and glycerin in American English, is a simple triol compound. It is a colorless, odorless, viscous liquid that is sweet-tasting and non-toxic. The glycerol backbone is found in lipids known ...
follows this equation: :RCO2CH2–CHO2CR–CH2O2CR + 3 H2O → 3 RCOOH + HOCH2–CHOH–CH2OH To this end, hydrolysis is conducted in water at 250 °C. The cleavage of triglycerides with base proceeds more quickly than hydrolysis, the process being
saponification Saponification is a process of converting esters into soaps and alcohols by the action of aqueous alkali (for example, aqueous sodium hydroxide solutions). Soaps are salts of fatty acids, which in turn are carboxylic acids with long carbon chains. ...
. Saponification however produces soap, whereas the desired product of hydrolysis are the fatty acids.


Transesterification

Fats react with
alcohol Alcohol most commonly refers to: * Alcohol (chemistry), an organic compound in which a hydroxyl group is bound to a carbon atom * Alcohol (drug), an intoxicant found in alcoholic drinks Alcohol may also refer to: Chemicals * Ethanol, one of sev ...
s (R'OH) instead of with water in hydrolysis) in a process called
transesterification In organic chemistry, transesterification is the process of exchanging the organic group R″ of an ester with the organic group R' of an alcohol. These reactions are often catalyzed by the addition of an acid or base catalyst. The reaction can ...
. Glycerol is produced together with the
fatty acid ester Fatty acid esters (FAEs) are a type of ester that result from the combination of a fatty acid with an alcohol. When the alcohol component is glycerol, the fatty acid esters produced can be monoglycerides, diglycerides, or triglycerides. Dietary f ...
s. Most typically, the reaction entails the use of
methanol Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical and the simplest aliphatic alcohol, with the formula C H3 O H (a methyl group linked to a hydroxyl group, often abbreviated as MeOH). It is a ...
(MeOH) to give
fatty acid methyl ester Fatty acid methyl esters (FAME) are a type of fatty acid ester that are derived by transesterification of fats with methanol. The molecules in biodiesel are primarily FAME, usually obtained from vegetable oils by transesterification. They are used ...
s: :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.


Hydrogenation

The fatty acid or fatty esters are susceptible to
hydrogenation Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a Catalysis, catalyst such as nickel, palladium or platinum. The process is commonly employed to redox, reduce or S ...
converts
unsaturated fatty acids In nutrition science, nutrition, biology, and chemistry, fat usually means any ester of fatty acids, or a mixture of such chemical compound, compounds, most commonly those that occur in living beings or in food. The term often refers spec ...
into
saturated fatty acids A saturated fat is a type of fat in which the fatty acid chains have all single bonds. A fat known as a glyceride is made of two kinds of smaller molecules: a short glycerol backbone and fatty acids that each contain a long linear or branched ch ...
. The acids or esters can also be reduced to the
fatty alcohols Fatty alcohols (or long-chain alcohols) are usually high-molecular-weight, straight-chain primary alcohols, but can also range from as few as 4–6 carbons to as many as 22–26, derived from natural fats and oils. The precise chain length varies ...
. For some applications, fatty acids are converted to fatty nitriles. Hydrogenated of these nitriles gives
fatty amine In chemistry, a fatty amine is loosely defined as any amine possessing a mostly linear hydrocarbon chain of eight or more carbon atoms. They are typically prepared from the more abundant fatty acids, with vegetable or seed-oils being the ultimate ...
s, which have a variety of applications.Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke "Amines, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.


Gelation

Liquid oil can also be immobilized in a 3D-network provided by various molecules called oleogelators.


Applications

The largest application for oleochemicals, about 30% of market share for fatty acids and 55% for fatty alcohols, is for making
soaps Soap is a surfactant cleaning compound used for personal or other cleaning. Soap may also refer to: Education * Supplemental Offer and Acceptance Program, for medical students who were not initially matched with U.S. residencies by the Nationa ...
and detergents.The Changing World of Oleochemicals
Wolfgang Rupilius and Salmiah Ahmad, Palm Oil Developments 44, 2005
Lauric acid Lauric acid, systematically dodecanoic acid, is a saturated fatty acid with a 12-carbon atom chain, thus having many properties of medium-chain fatty acids. It is a bright white, powdery solid with a faint odor of bay oil or soap. The salts and es ...
, used to produce
sodium lauryl sulfate Sodium dodecyl sulfate (SDS) or sodium lauryl sulfate (SLS), sometimes written sodium laurilsulfate, is an organic compound with the formula . It is an anionic surfactant used in many cleaning and hygiene products. This compound is the sodium salt ...
and related compounds, which are used to make soaps and other personal care products. Other applications of oleochemicals include the production of
lubricant A lubricant (sometimes shortened to lube) is a substance that helps to reduce friction between surfaces in mutual contact, which ultimately reduces the heat generated when the surfaces move. It may also have the function of transmitting forces, t ...
s,
solvent A solvent (s) (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for ...
s,
biodiesel Biodiesel is a form of diesel fuel derived from plants or animals and consisting of long-chain fatty acid esters. It is typically made by chemically reacting lipids such as animal fat (tallow), soybean oil, or some other vegetable oil with ...
and
bioplastics Bioplastics are plastic materials produced from renewable biomass sources, such as vegetable fats and oils, corn starch, straw, woodchips, sawdust, recycled food waste, etc. Some bioplastics are obtained by processing directly from natural bio ...
. Due to the use of
methyl ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides are fa ...
s in biodiesel production, they represent the fastest growing sub-sector of oleochemical production in recent years.


Oleochemical industry development


Europe

Through the 1996 creation of Novance and the 2008 acquisition of Oleon,
Avril Group Avril is an international agro-industrial group based in France, specialising in food, animal feed, energy and sustainable chemistry. It was founded in 1983, on the initiative of a collective group of leaders in the French farming sector, and w ...
has dominated the European market of oleochemistry.


Southeast Asia

Southeast Asian countries' rapid production growth of
palm oil Palm oil is an edible vegetable oil derived from the mesocarp (reddish pulp) of the fruit of the oil palms. The oil is used in food manufacturing, in beauty products, and as biofuel. Palm oil accounted for about 33% of global oils produced from ...
and
palm kernel oil Palm kernel oil is an edible plant oil derived from the kernel of the oil palm tree ''Elaeis guineensis''. It is related to other two edible oils: ''palm oil'', extracted from the fruit pulp of the oil palm, and ''coconut oil'', extracted from th ...
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 AG & Co. KGaA, commonly known as Henkel, is a German multinational chemical and consumer goods company headquartered in Düsseldorf, Germany. It is active in both the consumer and industrial sectors. Founded in 1876, the DAX company is organi ...
,
Unilever Unilever plc is a British multinational consumer goods company with headquarters in London, England. Unilever products include food, condiments, bottled water, baby food, soft drink, ice cream, instant coffee, cleaning agents, energy drink, t ...
, and
Petrofina Petrofina was a Belgian oil company. It merged with Total in 1999 to form TotalFina, which after subsequent mergers has changed its name back to Total. In the United States, Fina's former refining and marketing operations are now owned by De ...
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 Bovine spongiform encephalopathy (BSE), commonly known as mad cow disease, is an incurable and invariably fatal neurodegenerative disease of cattle. Symptoms include abnormal behavior, trouble walking, and weight loss. Later in the course of t ...
) in 2000,
tallow Tallow is a rendering (industrial), rendered form of beef or mutton fat, primarily made up of triglycerides. In industry, tallow is not strictly defined as beef or mutton fat. In this context, tallow is animal fat that conforms to certain techn ...
is replaced for many uses by vegetable oleic fatty acids, such as palm kernel and coconut oils.


References


External links

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