Fatty Alcohols
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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 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 Most fatty alcohols in nature are found as waxes which are esters of fatty acids and fatty alcohols. T ...
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Oleyl Alcohol Structural Formula V1
Oleyl alcohol , or ''cis''-9-octadecen-1-ol, is an Unsaturated compound, unsaturated fatty alcohol with the molecular formula or the condensed structural formula . It is a colorless oil, mainly used in cosmetics. It can be produced by the hydrogenation of oleic acid esters by Bouveault–Blanc reduction, which avoids reduction of the C=C group (as would occur with usual catalytic hydrogenation). The required oleate esters are obtained from beef fat, fish oil, and, in particular, olive oil (from which it gains its name). The original procedure was reported by Louis Bouveault in 1904 and subsequently refined. It has uses as a nonionic surfactant, emulsifier, emollient and thickener in Cream (pharmaceutical), skin creams, lotions and many other Cosmetics, cosmetic products including shampoos and hair conditioners. It has also been investigated as a carrier for delivering medications through the skin or mucus membranes; particularly the lungs. See also * Oleic acid - the corresp ...
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Ethylene
Ethylene (IUPAC name: ethene) is a hydrocarbon which has the formula or . It is a colourless, flammable gas with a faint "sweet and musky" odour when pure. It is the simplest alkene (a hydrocarbon with carbon-carbon double bonds). Ethylene is widely used in the chemical industry, and its worldwide production (over 150 million tonnes in 2016) exceeds that of any other organic compound. Much of this production goes toward polyethylene, a widely used plastic containing polymer chains of ethylene units in various chain lengths. Ethylene is also an important natural plant hormone and is used in agriculture to force the ripening of fruits. The hydrate of ethylene is ethanol. Structure and properties This hydrocarbon has four hydrogen atoms bound to a pair of carbon atoms that are connected by a double bond. All six atoms that comprise ethylene are coplanar. The H-C-H angle is 117.4°, close to the 120° for ideal sp² hybridized carbon. The molecule is also relatively weak: rota ...
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Ziegler Process
In organic chemistry, the Ziegler process (also called the Ziegler-Alfol synthesis) is a method for producing fatty alcohols from ethylene using an organoaluminium compound. The reaction produces linear primary alcohols with an even numbered carbon chain. The process uses an aluminum compound to oligomerize ethylene and allow the resulting alkyl group to be oxygenated. The usually targeted products are fatty alcohols, which are otherwise derived from natural fats and oils. Fatty alcohols are used in food and chemical processing. They are useful due to their amphipathic nature. The synthesis route is named after Karl Ziegler, who described the process in 1955.Zerong Wang "Ziegler Alcohol Synthesis (Ziegler Higher Alcohol Synthesis, Alfol Process, Ziegler-Alfol Process, Ziegler-Alfol Synthesis)" in Comprehensive Organic Name Reactions and Reagents, 2010, John Wiley & Sons, Inc. Online Process details The Ziegler alcohol synthesis involves oligomerization of ethylene using triethylalum ...
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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 the kernel of the coconut. Palm kernel oil, palm oil, and coconut oil are three of the few highly saturated vegetable fats; these oils give the name to the 16-carbon saturated fatty acid palmitic acid that they contain. Palm kernel oil, which is semi-solid at room temperature, is more saturated than palm oil and comparable to coconut oil. History Oil from the African oil palm ''Elaeis guineensis'' has long been recognized in West African countries. European merchants trading with West Africa occasionally purchased palm oil for use in Europe, but palm kernel oil remained rare outside West Africa. The USDA has published historical production figures for palm kernel oil for years beginning October 1 and ending September 30: Re ...
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Coconut Oil
frameless , right , alt = A cracked coconut and a bottle of coconut oil Coconut oil (or coconut butter) is an edible oil derived from the wick, meat, and milk of the coconut palm fruit. Coconut oil is a white solid fat; in warmer climates during the summer months it is a clear thin liquid oil, melting at warmer room temperatures of around . Unrefined varieties have a distinct coconut aroma. It is used as a food oil, and in industrial applications for cosmetics and detergent production. Due to its high levels of saturated fat, numerous health authorities recommend limiting its consumption as a food.Media summary: Production Oil production is dependent upon palm cultivation. Oil production is thus threatened by coconut pest The coconut tree (''Cocos nucifera'') is a member of the palm tree family (Arecaceae) and the only living species of the genus ''Cocos''. The term "coconut" (or the archaic "cocoanut") can refer to the whole coconut palm, the seed, or the f ...s. ...
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Mustard Seed Oil
Mustard oil can mean either the pressed oil used for cooking, or a pungent essential oil also known as volatile oil of mustard. The essential oil results from grinding mustard seed, mixing the grounds with water, and extracting the resulting volatile oil by distillation. It can also be produced by dry distillation of the seed. Pressed mustard oil is used as cooking oil in some cultures, but sale is restricted in some countries due to high levels of erucic acid. Varieties of mustard seed also exist that are low in erucic acid. Pressed oil Oil makes up about 30% of mustard seeds. It can be produced from black mustard (''Brassica nigra''), brown mustard ('' B. juncea''), and white mustard ('' B. alba''). Having a distinctive pungent taste, the oil is used for cooking in India, Pakistan, Nepal and Bangladesh. Its pungent flavor is due to allyl isothiocyanate, a phytochemical of plants in the mustard family, Brassicaceae (for example, cabbage, horseradish or wasabi). Mustard oil h ...
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Rapeseed Oil
Close-up of canola blooms Canola flower Rapeseed oil is one of the oldest known vegetable oils. There are both edible and industrial forms produced from rapeseed, the seed of several cultivars of the plant family Brassicaceae. Historically, it was eaten in limited quantities due to high levels of erucic acid, which is damaging to the cardiac muscle of animals and imparts a bitter taste, and glucosinolates, which made it less nutritious in animal feed. Rapeseed oil can contain up to 54% erucic acid. Canola oil is a food-grade version derived from rapeseed cultivars bred for low erucic acid content. Also known as low erucic acid rapeseed (LEAR) oil, it has been generally recognized as safe by the United States Food and Drug Administration. Canola oil is limited by government regulation to a maximum of 2% erucic acid by weight in the US and the EU, with special regulations for infant food. These low levels of erucic acid do not cause harm in humans. In commerce, non-food variet ...
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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 Saturated and unsaturated compounds, saturate organic compounds. Hydrogenation typically constitutes the addition of pairs of hydrogen atoms to a molecule, often an alkene. Catalysts are required for the reaction to be usable; non-catalytic hydrogenation takes place only at very high temperatures. Hydrogenation reduces Double bond, double and Triple bond, triple bonds in hydrocarbons. Process Hydrogenation has three components, the Saturated and unsaturated compounds, unsaturated substrate, the hydrogen (or hydrogen source) and, invariably, a catalyst. The redox, reduction reaction is carried out at different temperatures and pressures depending upon the substrate and the activity of the catalyst. Related or competing reactions The same ca ...
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Esters
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 fatty acid esters of glycerol; they are important in biology, being one of the main classes of lipids and comprising the bulk of animal fats and vegetable oils. Esters typically have a pleasant smell; those of low molecular weight are commonly used as fragrances and are found in essential oils and pheromones. They perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Polyesters are important plastics, with monomers linked by ester moieties. Phosphoesters form the backbone of DNA molecules. Nitrate esters, such as nitroglycerin, are known for their explosive properties. '' Nomenclature Etymology The ...
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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 also be accomplished with the help of other enzymes, particularly lipases (one example is the lipase E.C.3.1.1.3). Strong acids catalyse the reaction by donating a proton to the carbonyl group, thus making it a more potent electrophile, whereas bases catalyse the reaction by removing a proton from the alcohol, thus making it more nucleophilic. If the alcohol produced by the reaction can be separated from the reactants by distillation this will drive the equilibrium toward the products, this means that esters with larger alkoxy groups can be made from methyl or ethyl esters in high purity by heating the mixture of ester, acid/base, and large alcohol. Mechanism In the transesterification mechanism, the carbonyl carbon of the starting e ...
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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 well as vegetable fat. They are also present in the blood to enable the bidirectional transference of adipose fat and blood glucose from the liver, and are a major component of human skin oils. Many types of triglycerides exist. One specific classification focuses on saturated and unsaturated types. Saturated fats have ''no'' C=C groups; unsaturated fats feature one or more C=C groups. Unsaturated fats tend to have a lower melting point than saturated analogues; as a result, they are often liquid at room temperature. Chemical structure Triglycerides are tri-esters consisting of a glycerol bound to three fatty acid molecules. Alcohols have a hydroxyl (HO–) group. Organic acids have a carboxyl (–COOH) group. Alcohols and organ ...
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Whale Oil
Whale oil is oil obtained from the blubber of whales. Whale oil from the bowhead whale was sometimes known as train oil, which comes from the Dutch word ''traan'' ("tears, tear" or "drop"). Sperm oil, a special kind of oil obtained from the head cavities of sperm whales, differs chemically from ordinary whale oil: it is composed mostly of liquid wax. Its properties and applications differ from those of regular whale oil, and it was sold for a higher price. Source and use Emerging industrial societies used whale oil in oil lamps and to Soap#History, make soap. In the 20th century it was made into margarine. With the commercial development of the petroleum industry and vegetable oils, the use of whale oils declined considerably from its peak in the 19th century into the 20th century. This is said to have saved whales from extinction. In the 21st century, with most countries having banned whaling, the sale and use of whale oil has practically ceased. Whale oil was obtained by ...
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