Waxes are a diverse class of organic compounds that are lipophilic solids that are malleable near ambient temperatures. They include higher alkanes and lipids, typically with melting points above about 40 °C (104 °F), melting to give low viscosity liquids. Waxes are insoluble in water but soluble in nonpolar organic solvents such as hexane, benzene and chloroform. Natural waxes of various types are produced by plants and animals and occur in petroleum.
Chemistry
Waxes are organic compounds that characteristically consist of long aliphatic alkyl chains, although aromatic compounds may also be present. Natural waxes may contain unsaturated bonds and include various functional groups such as fatty acids, primary and secondary alcohols, ketones, aldehydes and fatty acid esters. Synthetic waxes often consist of homologous series of long-chain aliphatic hydrocarbons (alkanes or paraffins) that lack functional groups.
Plant and animal waxes Waxes are synthesized by both plants and animals. Those of animal origin typically consist of wax esters derived from a variety of fatty acids and carboxylic alcohols. In waxes of plant origin, characteristic mixtures of unesterified hydrocarbons may predominate over esters. The composition depends not only on species, but also on geographic location of the organism.
Animal waxes The best-known animal wax is beeswax, used in constructing the honeycombs of beehives, but other insects also secrete waxes. A major component of beeswax is myricyl palmitate which is an ester of triacontanol and palmitic acid. Its melting point is 62–65 °C (144–149 °F). Spermaceti occurs in large amounts in the head oil of the sperm whale. One of its main constituents is cetyl palmitate, another ester of a fatty acid and a fatty alcohol. Lanolin is a wax obtained from wool, consisting of esters of sterols.
Plant waxes Plants secrete waxes into and on the surface of their cuticles as a way to control evaporation, wettability and hydration. The epicuticular waxes of plants are mixtures of substituted long-chain aliphatic hydrocarbons, containing alkanes, alkyl esters, fatty acids, primary and secondary alcohols, diols, ketones and aldehydes. From the commercial perspective, the most important plant wax is carnauba wax, a hard wax obtained from the Brazilian palm Copernicia prunifera. Containing the ester myricyl cerotate, its many applications include confectionery and other food coatings, car and furniture polish, floss coating, and surfboard wax. Other more specialized vegetable waxes include jojoba oil, candelilla wax and ouricury wax.
Modified plant and animal waxes Plant and animal based waxes or oils can undergo selective chemical modifications to produce waxes with more desirable properties than are available in the unmodified starting material. This approach has relied on green chemistry approaches including olefin metathesis and enzymatic reactions and can be used to produce waxes from inexpensive starting materials like vegetable oils.
Petroleum derived waxes
Although many natural waxes contain esters, paraffin waxes are hydrocarbons, mixtures of alkanes usually in a homologous series of chain lengths. These materials represent a significant fraction of petroleum. They are refined by vacuum distillation. Paraffin waxes are mixtures of saturated n- and iso- alkanes, naphthenes, and alkyl- and naphthene-substituted aromatic compounds. A typical alkane paraffin wax chemical composition comprises hydrocarbons with the general formula CnH2n+2, such as hentriacontane, C31H64. The degree of branching has an important influence on the properties. Microcrystalline wax is a lesser produced petroleum based wax that contains higher percentage of isoparaffinic (branched) hydrocarbons and naphthenic hydrocarbons. Millions of tons of paraffin waxes are produced annually. They are used in foods (such as chewing gum and cheese wrapping), in candles and cosmetics, as non-stick and waterproofing coatings and in polishes.
Montan wax Montan wax is a fossilized wax extracted from coal and lignite. It is very hard, reflecting the high concentration of saturated fatty acids and alcohols. Although dark brown and odorous, they can be purified and bleached to give commercially useful products.
Polyethylene and related derivatives As of 1995, about 200 million kilograms of polyethylene waxes were consumed annually. Polyethylene waxes are manufactured by one of three methods:
The direct polymerization of ethylene, potentially including co-monomers; The thermal degradation of high molecular weight polyethylene resin; The recovery of low molecular weight fractions from high molecular weight resin production. Each production technique generates products with slightly different properties. Key properties of low molecular weight polyethylene waxes are viscosity, density and melt point. Polyethylene waxes produced by means of degradation or recovery from polyethylene resin streams contain very low molecular weight materials that must be removed to prevent volatilization and potential fire hazards during use. Polyethylene waxes manufactured by this method are usually stripped of low molecular weight fractions to yield a flash point >500 °F (>260 °C). Many polyethylene resin plants produce a low molecular weight stream often referred to as low polymer wax (LPW). LPW is unrefined and contains volatile oligomers, corrosive catalyst and may contain other foreign material and water. Refining of LPW to produce a polyethylene wax involves removal of oligomers and hazardous catalyst. Proper refining of LPW to produce polyethylene wax is especially important when being used in applications requiring FDA or other regulatory certification.
Uses Waxes are mainly consumed industrially as components of complex formulations, often for coatings. The main use of polyethylene and polypropylene waxes is in the formulation of colourants for plastics. Waxes confer matting effects (i.e., to confer non-glossy finishes) and wear resistance to paints. Polyethylene waxes are incorporated into inks in the form of dispersions to decrease friction. They are employed as release agents, find use as slip agents in furniture, and confer corrosion resistance.
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