Mason Delacroix
Fatty alcohols are an important class of olive oil minor constituents and are widely used in industry. They are usually high-molecular mass, straight-chain primary alcohols, but can also range from as few as 4–6 carbon atoms to as many as 22–26, derived from natural fats and oils. They are produced by bacteria, plants, and animals for purposes of buoyancy, as a source of metabolic water and energy, biosonar lenses, and for thermal insulation in the form of waxes. Plants have microsomal and plastidial alcohol-forming fatty acyl reductases (FARs), which have distinct acyl chain-length and chain-saturation substrate specificities. The extraction of linear saturated fatty alcohols from plant matter can be achieved through various methods, and this article will explore the different processes and their effectiveness in detail.
| Characteristics | Values |
|---|---|
| Sources | Plants, animals, bacteria |
| Traditional sources | Vegetable oils |
| Historical sources | Animal fats (tallow), whale oil |
| Chain length | C4-C26 |
| Biodegradability | Chains up to C16 biodegrade within 10 days |
| Toxicity | Low level of toxicity from inhalation, oral or dermal exposure |
| Acute lethal concentration | Greater than saturated vapour pressure |
| Health effects | Longer-chain fatty alcohols (C12-C16) produce fewer health effects than short-chain (smaller than C12) |
| Industrial value | High |
| Applications | Surfactants, detergents, cosmetics, agrochemical and pharmaceutical formulations, food products |
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What You'll Learn
Fatty alcohols in plants
Fatty alcohols are an important class of minor constituents of olive oil. They are used as a criterion to differentiate various olive oil designations. The main linear alcohols present in olive oil are docosanol, tetracosanol, hexacosanol, and octacosanol. Fatty alcohols are also found in other vegetable oils, which remain a large-scale feedstock. The alcohols are obtained from the triglycerides (fatty acid triesters), which form the bulk of the oil. The process involves the transesterification of the triglycerides to give methyl esters, which are then hydrogenated to produce fatty alcohols.
Fatty alcohols are usually high-molecular-mass, straight-chain primary alcohols, but they can also range from as few as 4–6 carbon atoms to as many as 22–26, derived from natural fats and oils. The precise chain length varies with the source. Some commercially important fatty alcohols are lauryl, stearyl, and oleyl alcohol. They are colourless oily liquids (for smaller carbon numbers) or waxy solids, although impure samples may appear yellow. Fatty alcohols usually have an even number of carbon atoms and a single alcohol group (–OH) attached to the terminal carbon. Some are unsaturated and some are branched. They are widely used in industry, particularly in the production of detergents and surfactants.
Plants have microsomal and plastidial alcohol-forming fatty acyl reductases (FARs). FARs have distinct acyl chain-length and chain-saturation substrate specificities. Free and combined fatty alcohols are common components of surface lipid barriers. Fatty alcohols and wax esters are of high industrial value. Fatty alcohols and/or derived compounds are also likely to have direct functions in plant biotic and abiotic interactions.
Primary fatty alcohols are found throughout the biological world, either in free form or in a combined state. They are common components of plant surface lipids (i.e. cutin, suberin, sporopollenin, and associated waxes) and their absence can significantly perturb these essential barriers. Fatty alcohols are mainly used in the production of detergents and surfactants. They are also used in cosmetics, agrochemical and pharmaceutical formulations, as well as in food products, typically acting as thickening agents, emulsifiers, or emollients.
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Extraction methods
Conventional Extraction
This method involves the use of solvents to separate fatty alcohols from plant matter. Solvents such as hexane or petroleum ether are commonly used due to their ability to dissolve lipids effectively. The plant material is typically ground or crushed to increase the surface area and then mixed with the solvent. After the fatty alcohols dissolve in the solvent, the mixture is filtered, and the solvent is evaporated, leaving behind the extracted fatty alcohols.
Microwave-Assisted Extraction (MAE)
MAE is a modern technique that utilizes microwaves to enhance the extraction process. Microwaves provide a rapid and controlled heating source, improving the efficiency of solvent extraction. Plant material is placed in a container with a suitable solvent and subjected to microwave radiation. The microwaves cause the solvent molecules to move more rapidly, increasing their interaction with the plant material and facilitating the extraction of fatty alcohols.
Ultrasonic-Assisted Extraction (UAE)
UAE employs ultrasonic waves to assist in the extraction process. Ultrasonic waves create cavitation bubbles in the solvent, which collapse and generate localized heat and pressure. This process disrupts the plant cell walls, releasing fatty alcohols into the solvent. UAE is often used in conjunction with traditional solvent extraction methods to improve yield and reduce extraction time.
Supercritical Fluid Extraction (SFE)
SFE utilizes supercritical fluids, substances in a state with gas-like and liquid-like properties, such as supercritical carbon dioxide (SC-CO2). In this method, the supercritical fluid acts as a solvent and exhibits excellent solvating properties. It can penetrate plant material and efficiently extract fatty alcohols. SFE is a versatile and environmentally friendly technique as it reduces the need for organic solvents.
Biotechnological Approaches
Biotechnological methods involve the use of microbes or oilseed crops expressing alcohol-forming fatty acyl reductases (FARs). FARs are enzymes that produce fatty alcohols and have specificities for chain length and saturation. By expressing these enzymes in transgenic organisms, it becomes possible to obtain valuable fatty alcohols through biotechnological processes. This approach offers a novel and sustainable way to produce fatty alcohols without the need for traditional extraction methods.
These extraction methods can be further optimized and tailored to the specific plant material and requirements of the extraction process. The choice of method depends on various factors, including efficiency, cost, and the availability of equipment and resources.
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Chain length
The chain length of fatty alcohols varies depending on the source. They can range from as few as 4–6 carbon atoms to as many as 22–26 carbon atoms. The length of the carbon chain is important as it determines the solubility of the fatty alcohol in water. Longer-chain fatty alcohols are insoluble in water. Fatty alcohols usually have an even number of carbon atoms and a single alcohol group (–OH) attached to the terminal carbon.
Longer-chain fatty alcohols (C12–C16) produce fewer health effects than short-chain fatty alcohols (smaller than C12). Short-chain fatty alcohols are considered eye irritants, while long-chain alcohols are not. Longer-chain fatty alcohols are also less toxic than shorter-chain fatty alcohols.
Fatty alcohols with chain lengths of C10 and greater are predicted to partition into sediment when in water. Lengths C14 and above are predicted to stay in the air upon release.
In plants, fatty alcohols are produced by microsomal and plastidial alcohol-forming fatty acyl reductases (FARs). FARs have distinct substrate specificities with regard to chain length and chain saturation.
The traditional sources of fatty alcohols have been various vegetable oils, which remain a large-scale feedstock. Animal fats (tallow) were historically important, particularly whale oil, but are no longer used on a large scale. Tallows produce a narrow range of alcohols, predominantly C16–C18, while plant sources produce a wider range of alcohols (C6–C24), making them the preferred source.
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Industrial applications
Fatty alcohols, particularly the saturated varieties, have a large range of industrial applications. They are mainly used in the production of detergents and surfactants. Due to their amphipathic nature, fatty alcohols behave as non-ionic surfactants and are used as co-emulsifiers, emollients, and thickeners in cosmetics and the food industry. They are also used in agrochemical and pharmaceutical formulations, as well as in food products.
Fatty alcohols are usually high-molecular-mass, straight-chain primary alcohols, but can range from as few as 4–6 carbon atoms to as many as 22–26, derived from natural fats and oils. The precise chain length varies with the source. Some commercially important fatty alcohols are lauryl, stearyl, and oleyl alcohol. They are colourless oily liquids (for smaller carbon numbers) or waxy solids, although impure samples may appear yellow.
Long-chain primary alcohols are of high industrial value, serving mostly as surfactants in detergents and other cleaning products. They are also used in cosmetics, agrochemicals, and pharmaceutical formulations, as well as in food products, typically acting as thickening agents, emulsifiers, or emollients. For example, Western Europe used more than 450 thousand tons of fatty alcohols in 2006 to produce non-ionic polyglycol surfactants via the process of ethoxylation.
Fatty alcohols are mainly produced from natural sources or synthesized using chemical and biotechnological methods. The traditional sources of fatty alcohols have been various vegetable oils, which remain a large-scale feedstock. Animal fats (tallow) were historically important, particularly whale oil, but are no longer used on a large scale. Plant sources are preferred because they produce a wider range of alcohols (C6–C24), whereas tallow produces a narrower range (C16–C18).
The oleochemicals market, which includes fatty alcohols, is projected to reach 52.27 billion in 2031, with a predicted CAGR of 7.5%. The application of oleochemicals will be dominated by the personal care and cosmetics markets. Fatty alcohols are also prepared from petrochemical sources, such as the Ziegler process, and through biological routes, although they are produced in trace amounts naturally.
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Health effects
Fatty alcohols are an important class of olive oil minor constituents because they are used as a criterion to differentiate various olive oil designations. The main linear alcohols present in olive oil are docosanol, tetracosanol, hexacosanol, and octacosanol. They are found with normal, branched (mono- or isoprenoid), saturated or unsaturated carbon chains of various lengths and sometimes with secondary or tertiary alcoholic functions.
Fatty alcohols are widely used in industry, particularly in the production of detergents and surfactants. They are also used in personal care and cosmetics. They are effectively eliminated from the body when exposed, limiting the possibility of retention or bioaccumulation. They are biodegradable, with chains up to C16 biodegrading within 10 days completely. Field studies at wastewater treatment plants have shown that 99% of fatty alcohols of lengths C12–C18 are removed.
Tests of acute and repeated exposures have revealed a low level of toxicity from inhalation, oral, or dermal exposure to fatty alcohols. Longer-chain (C12–C16) fatty alcohols produce fewer health effects than short-chain (smaller than C12) alcohols. Short-chain fatty alcohols are considered eye irritants, while long-chain alcohols are not. Repeated exposure to fatty alcohols can produce low-level toxicity, and certain compounds in this category can cause local irritation on contact or low-grade liver effects. No effects on the central nervous system have been observed with inhalation and oral exposure.
There is no evidence that fatty alcohols are mutagenic or cause reproductive toxicity or infertility. However, it is important to note that not all fatty alcohols are the same, and some specific compounds may have different health effects. For example, avocatin B, a mixture of avocadene and avocadyne found in avocado, has been shown to possess novel anticancer properties. Persin, another compound found in avocado, is toxic, and the consumption of any part of the plant is dangerous for several animals. However, its relatively low concentrations in the ripe pulp of the fruit are generally considered harmless to humans, except for some allergic individuals.
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Frequently asked questions
Fatty alcohols are usually high-molecular mass, straight-chain primary alcohols, with an even number of carbon atoms and a single alcohol group attached to the terminal carbon. They are colourless oily liquids or waxy solids.
Traditional sources of fatty alcohols have been various vegetable oils, which remain a large-scale feedstock. The process involves the transesterification of triglycerides to give methyl esters, which are then hydrogenated to produce fatty alcohols.
Modern methods for extracting fatty alcohols from plant matter include the use of transgenic microbes or oilseed crops expressing alcohol-forming fatty acyl reductases (FARs). FARs are enzymes that act on acyl-coenzyme A (acyl-CoA) or acyl-acyl carrier protein (acyl-ACP) substrates to produce fatty alcohols.
Fatty alcohols are widely used in industry, particularly in the production of detergents and surfactants. They are also used in cosmetics, agrochemicals, and pharmaceutical formulations, as well as in food products as thickening agents, emulsifiers, or emollients.
