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 with the source. Some commercially important fatty alcohols are lauryl, stearyl, and oleyl alcohols. 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. As with fatty acids, they are often referred to generically by the number of carbon atoms in the molecule, such as "a C12 alcohol", that is an alcohol having 12 carbons, for example dodecanol. Production and occurrence Fatty alcohols became commercially available in the early 1900s. They were originally obtained by reduction of wax esters with sodium by the Bouveault–Blanc reduction process. In the 1930s catalytic hydrogenation was commercialized, which allowed the conversion of fatty acid esters, typically tallow, to the alcohols. In the 1940s and 1950s, petrochemicals became an important source of chemicals, and Karl Ziegler had discovered the polymerization of ethylene. These two developments opened the way to synthetic fatty alcohols. From natural sources Most fatty alcohols in nature are found as waxes, which are esters of fatty acids and fatty alcohols. They are produced by bacteria, plants and animals for purposes of buoyancy, as source of metabolic water and energy, biosonar lenses (marine mammals) and for thermal insulation in the form of waxes (in plants and insects). The traditional sources of fatty alcohols have largely been various vegetable oils, which remain a large-scale feedstock. Animal fats (tallow) were of historic importance, particularly whale oil, however they are no longer used on a large scale. Tallows produce a fairly narrow range of alcohols, predominantly C16–C18, while plant sources produce a wider range of alcohols from (C6–C24), making them the preferred source. 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 the fatty alcohols. Higher alcohols (C20–C22) can be obtained from rapeseed oil or mustard seed oil. Midcut alcohols are obtained from coconut oil (C12–C14) or palm kernel oil (C16–C18).