Wax

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Cetyl palmitate, a typical wax ester.
Commercial honeycomb foundation, made by pressing beeswax between patterned metal rollers.

Waxes are a class of chemical compounds that are plastic (malleable) near ambient temperatures. They are also a type of lipid. Characteristically, they melt above 45 °C (113 °F) to give a low viscosity liquid. Waxes are insoluble in water but soluble in organic, nonpolar solvents. All waxes are organic compounds, both synthetic and naturally occurring.

Types[edit]

Ceroline brand wax for floors and ceilings, first half of 20th century. From the Museo del Objeto del Objeto collection

Waxes are organic compounds that characteristically consist of long alkyl chains. Natural waxes are typically esters of fatty acids and long chain alcohols. Synthetic waxes are long-chain hydrocarbons lacking functional groups.

Plant and animal waxes[edit]

Waxes are biosynthesized by many plants and animals. Those of animal origin typically consist of wax esters derived from a variety of carboxylic acids and fatty alcohols. Those of plant origin also contain characteristic mixtures of unesterified hydrocarbons.[1] The composition depends not only on species, but also on geographic location of the organism. Because they are mixtures, naturally produced waxes are softer and melt at lower temperatures than the pure components.

Animal waxes[edit]

The most commonly known animal wax is beeswax, but other insects secrete waxes. A major component of beeswax is the ester myricyl palmitate which is used in constructing their honeycombs. Its melting point is 62-65 °C. 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.[2]

Plant waxes[edit]

Especially in warm climates, plants secrete waxes as a way to control evaporation and hydration.[3] From the commercial perspective, the most important wax is Carnauba wax, a hard wax obtained from the Brazilian palm Copernicia prunifera. Containing the ester myricyl cerotate, it has many applications. Other more specialized vegetable waxes include candelilla wax, ouricury wax, sugarcane wax, retamo wax. The epicuticular waxes of plants are mixtures of substituted long-chain aliphatic hydrocarbons, containing alkanes, fatty acids, primary and secondary alcohols, diols, ketones, aldehydes.[1]

Petroleum derived waxes[edit]

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 isoalkanes, naphthenes, and alkyl- and naphthene-substituted aromatic compounds. The degree of branching has an important influence on the properties. 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[edit]

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, not esters that characterize softer waxes. Although dark brown and smelly, they can be purified and bleached to give commercially useful products.

Polyethylene and related derivatives[edit]

Some waxes are obtained by cracking polyethylene at 400 °C. The products have the formula (CH2)nH2, where n ranges between about 50 and 100. As of 1995, about 200 million kilograms/y were consumed.[3]

Uses[edit]

Waxes are mainly consumed industrially as components of complex formulations, often for coatings.[3] The main use of polyethylene and polypropylene waxes is in the formulation of colourants for plastics. Waxes confer matting effects 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. They are also used as slip agents, e.g. in furniture, and corrosion resistance.

Candles[edit]

Waxes and hard fats such as tallow are used to make candles, used for lighting and decoration.

Wood products[edit]

Waxes are used as finishes and coatings for wood products.[4] Some waxes are considered food-safe and are used to coat wooden cutting boards and other items that come into contact with food.

Beeswax is frequently used as a lubricant on drawer slides where wood to wood contact occurs.

Other uses[edit]

Sealing wax was used to close important documents in the Middle Ages. Wax tablets were used as writing surfaces. There were different types of wax in the Middle Ages, namely four kinds of wax (Ragusan, Montenegro, Byzantine and Bulgarian), "ordinary" waxes from Spain, Poland and Riga, unrefined waxes and colored waxes (red, white and green).[5][6] Waxes are used to make wax paper, impregnating and coating paper and card to waterproof it or make it resistant to staining, or to modify its surface properties. Waxes are also used in shoe polishes, wood polishes, and automotive polishes, as mold release agents in mold making, as a coating for many cheeses, and to waterproof leather and fabric. Wax has been used since antiquity as a temporary, removable model in lost-wax casting of gold, silver and other materials.

Wax with colorful pigments added has been used as a medium in encaustic painting, and is used today in the manufacture of crayons and colored pencils. Carbon paper, used for making duplicate typewritten documents was coated with carbon black suspended in wax, typically montan wax, but has largely been superseded by photocopiers and computer printers. In another context, lipstick and mascara are blends of various fats and waxes colored with pigments, and both beeswax and lanolin are used in other cosmetics. Ski wax is used in skiing and snowboarding. Also, the sports of surfing and skateboarding often use wax to enhance the performance. Beeswax or coloured synthetic wax is used to decorate Easter eggs in Ukraine, Poland and the Czech Republic. Paraffin wax is used in making chocolate covered bon-bons. Wax is also used in wax bullets, which are used as simulation aids.

Specific examples[edit]

Animal waxes[edit]

Vegetable waxes[edit]

Mineral waxes[edit]

Petroleum waxes[edit]

Synthetic waxes[edit]

See also[edit]

References[edit]

  1. ^ a b EA Baker (1982) Chemistry and morphology of plant epicuticular waxes. In The Plant Cuticle. Ed. DF Cutler, KL Alvin, CE Price. Academic Press. ISBN 0-12-199920-3
  2. ^ Wilhelm Riemenschneider1 and Hermann M. Bolt "Esters, Organic" Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim. doi:10.1002/14356007.a09_565.pub2
  3. ^ a b c Uwe Wolfmeier, Hans Schmidt, Franz-Leo Heinrichs, Georg Michalczyk, Wolfgang Payer, Wolfram Dietsche, Klaus Boehlke, Gerd Hohner, Josef Wildgruber "Waxes" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2002. doi:10.1002/14356007.a28_103.
  4. ^ "Minwax® Paste Finishing Wax | Specialty Products". Minwax.com. 2012-01-31. Retrieved 2012-12-15. 
  5. ^ The rational arts of living: Ruth and Clarence Kennedy Conference in the Renaissance, 1982, page 187, Studies in History, No 50, Alistair Cameron Crombie, Nancy G. Siraisi, Dept. of History of Smith College, 1987.
  6. ^ Handbook To Life In The Medieval World, Volume 2, page 202, Handbook to Life, Facts on File Library of World History, Madeline Pelner Cosman, Linda Gale Jones, Infobase Publishing, 2008. ISBN 9780816048878

External links[edit]