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Waxes are a diverse class of
organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...
s that are
lipophilic Lipophilicity (from Greek language, Greek λίπος "fat" and :wikt:φίλος, φίλος "friendly") is the ability of a chemical compound to dissolve in fats, oils, lipids, and non-polar solvents such as hexane or toluene. Such compounds are c ...
, malleable solids near ambient temperatures. They include higher alkanes and
lipid Lipids are a broad group of organic compounds which include fats, waxes, sterols, fat-soluble vitamins (such as vitamins A, D, E and K), monoglycerides, diglycerides, phospholipids, and others. The functions of lipids include storing ...
s, typically with
melting point The melting point (or, rarely, liquefaction point) of a substance is the temperature at which it changes state of matter, state from solid to liquid. At the melting point the solid and liquid phase (matter), phase exist in Thermodynamic equilib ...
s above about 40 °C (104 °F), melting to give low
viscosity Viscosity is a measure of a fluid's rate-dependent drag (physics), resistance to a change in shape or to movement of its neighboring portions relative to one another. For liquids, it corresponds to the informal concept of ''thickness''; for e ...
liquids. Waxes are insoluble in water but soluble in nonpolar organic solvents such as
hexane Hexane () or ''n''-hexane is an organic compound, a straight-chain alkane with six carbon atoms and the molecular formula C6H14. Hexane is a colorless liquid, odorless when pure, and with a boiling point of approximately . It is widely used as ...
,
benzene Benzene is an Organic compound, organic chemical compound with the Chemical formula#Molecular formula, molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar hexagonal Ring (chemistry), ring with one hyd ...
and
chloroform Chloroform, or trichloromethane (often abbreviated as TCM), is an organochloride with the formula and a common solvent. It is a volatile, colorless, sweet-smelling, dense liquid produced on a large scale as a precursor to refrigerants and po ...
. Natural waxes of different types are produced by plants and animals and occur in
petroleum Petroleum, also known as crude oil or simply oil, is a naturally occurring, yellowish-black liquid chemical mixture found in geological formations, consisting mainly of hydrocarbons. The term ''petroleum'' refers both to naturally occurring un ...
.


Chemistry

Waxes are organic compounds that characteristically consist of long aliphatic
alkyl In organic chemistry, an alkyl group is an alkane missing one hydrogen. The term ''alkyl'' is intentionally unspecific to include many possible substitutions. An acyclic alkyl has the general formula of . A cycloalkyl group is derived from a cy ...
chains, although aromatic compounds may also be present. Natural waxes may contain unsaturated bonds and include various
functional group In organic chemistry, a functional group is any substituent or moiety (chemistry), moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions r ...
s such as
fatty acids In chemistry, in particular in biochemistry, a fatty acid is a carboxylic acid with an aliphatic chain, which is either saturated or unsaturated. Most naturally occurring fatty acids have an unbranched chain of an even number of carbon atoms, ...
, primary and secondary alcohols, ketones, aldehydes and fatty acid
ester In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...
s. Synthetic waxes often consist of homologous series of long-chain aliphatic hydrocarbons ( alkanes or paraffins) that lack
functional group In organic chemistry, a functional group is any substituent or moiety (chemistry), moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions r ...
s.


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
honeycomb A honeycomb is a mass of Triangular prismatic honeycomb#Hexagonal prismatic honeycomb, hexagonal prismatic cells built from beeswax by honey bees in their beehive, nests to contain their brood (eggs, larvae, and pupae) and stores of honey and pol ...
s of beehives, but other insects also secrete waxes. A major component of beeswax is myricyl palmitate which is an
ester In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...
of
triacontanol 1-Triacontanol (''n''-triacontanol) is a fatty alcohol of the general formula C30H62O, also known as melissyl alcohol or myricyl alcohol. It is found in plant cuticle waxes and in beeswax. Triacontanol is a growth stimulant for many plants, mo ...
and
palmitic acid Palmitic acid (hexadecanoic acid in IUPAC nomenclature) is a fatty acid with a 16-carbon chain. It is the most common saturated fatty acid found in animals, plants and microorganisms.Gunstone, F. D., John L. Harwood, and Albert J. Dijkstra. The ...
. Its melting point is . Spermaceti occurs in large amounts in the head oil of the
sperm whale The sperm whale or cachalot (''Physeter macrocephalus'') is the largest of the toothed whales and the largest toothed predator. It is the only living member of the Genus (biology), genus ''Physeter'' and one of three extant species in the s ...
. One of its main constituents is cetyl palmitate, another ester of a
fatty acid In chemistry, in particular in biochemistry, a fatty acid is a carboxylic acid with an aliphatic chain, which is either saturated and unsaturated compounds#Organic chemistry, saturated or unsaturated. Most naturally occurring fatty acids have an ...
and a fatty alcohol. Lanolin is a wax obtained from wool, consisting of esters of
sterol A sterol is any organic compound with a Skeletal formula, skeleton closely related to Cholestanol, cholestan-3-ol. The simplest sterol is gonan-3-ol, which has a formula of , and is derived from that of gonane by replacement of a hydrogen atom on ...
s.Wilhelm Riemenschneider1 and Hermann M. Bolt (2005). "Esters, Organic". ''Ullmann's Encyclopedia of Industrial Chemistry''. Wiley-VCH, Weinheim. .


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.EA Baker (1982) Chemistry and morphology of plant epicuticular waxes. In The Plant Cuticle. Ed. DF Cutler, KL Alvin, CE Price. Academic Press. 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, it has many applications, such as 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 In organic chemistry, an alkyl group is an alkane missing one hydrogen. The term ''alkyl'' is intentionally unspecific to include many possible substitutions. An acyclic alkyl has the general formula of . A cycloalkyl group is derived from a cy ...
- and naphthene-substituted aromatic compounds. A typical alkane paraffin wax chemical composition comprises hydrocarbons with the general formula C''n''H2''n''+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 acid In chemistry, in particular in biochemistry, a fatty acid is a carboxylic acid with an aliphatic chain, which is either saturated and unsaturated compounds#Organic chemistry, saturated or unsaturated. Most naturally occurring fatty acids have an ...
s and alcohols. Although dark brown and odorous, they can be purified and bleached to give commercially useful products.


Polyethylene and related derivatives

, 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
plastic Plastics are a wide range of synthetic polymers, synthetic or Semisynthesis, semisynthetic materials composed primarily of Polymer, polymers. Their defining characteristic, Plasticity (physics), plasticity, allows them to be Injection moulding ...
s. 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.Uwe Wolfmeier, Mr. 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. .


Candles

Waxes such as
paraffin wax Paraffin wax (or petroleum wax) is a soft colorless solid derived from petroleum, coal, or oil shale that consists of a mixture of hydrocarbon molecules containing between 20 and 40 carbon atoms. It is solid at room temperature and melting poi ...
or beeswax, and hard fats such as tallow are used to make
candle A candle is an ignitable candle wick, wick embedded in wax, or another flammable solid substance such as tallow, that provides light, and in some cases, a Aroma compound, fragrance. A candle can also provide heat or a method of keeping time. ...
s, used for lighting and decoration. Another fuel type used in candle manufacturing includes soy. Soy wax is made by the hydrogenation process using soybean oil.


Wood products

Waxes are used as finishes and coatings for wood products. Beeswax is frequently used as a lubricant on drawer slides where wood to wood contact occurs.


Other uses

Sealing wax was used to close important documents in the
Middle Ages In the history of Europe, the Middle Ages or medieval period lasted approximately from the 5th to the late 15th centuries, similarly to the post-classical period of global history. It began with the fall of the Western Roman Empire and ...
.
Wax tablet A wax tablet is a tablet (disambiguation), tablet made of wood and covered with a layer of wax, often linked loosely to a cover tablet, as a "double-leaved" diptych. It was used as a reusable and portable writing surface in classical antiquity, ...
s were used as writing surfaces. There were different types of wax in the Middle Ages, namely four kinds of wax ( Ragusan,
Montenegro , image_flag = Flag of Montenegro.svg , image_coat = Coat of arms of Montenegro.svg , coa_size = 80 , national_motto = , national_anthem = () , image_map = Europe-Mont ...
,
Byzantine The Byzantine Empire, also known as the Eastern Roman Empire, was the continuation of the Roman Empire centred on Constantinople during late antiquity and the Middle Ages. Having survived the events that caused the fall of the Western Roman E ...
, and
Bulgaria Bulgaria, officially the Republic of Bulgaria, is a country in Southeast Europe. It is situated on the eastern portion of the Balkans directly south of the Danube river and west of the Black Sea. Bulgaria is bordered by Greece and Turkey t ...
n), "ordinary" waxes from
Spain Spain, or the Kingdom of Spain, is a country in Southern Europe, Southern and Western Europe with territories in North Africa. Featuring the Punta de Tarifa, southernmost point of continental Europe, it is the largest country in Southern Eur ...
,
Poland Poland, officially the Republic of Poland, is a country in Central Europe. It extends from the Baltic Sea in the north to the Sudetes and Carpathian Mountains in the south, bordered by Lithuania and Russia to the northeast, Belarus and Ukrai ...
, and
Riga Riga ( ) is the capital, Primate city, primate, and List of cities and towns in Latvia, largest city of Latvia. Home to 591,882 inhabitants (as of 2025), the city accounts for a third of Latvia's total population. The population of Riga Planni ...
, unrefined waxes and colored waxes (red, white, and green). Waxes are used to make waxed 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 polish Shoe polish, also known as boot polish and shoeshine, is a waxy paste (rheology), paste, cream (pharmaceutical), cream, or liquid that is used to polish, polishing, shine, and waterproofing, waterproof leather shoes or boots to extend the footwe ...
es, wood polishes, and automotive polishes, as mold release agents in mold making, as a coating for many
cheese Cheese is a type of dairy product produced in a range of flavors, textures, and forms by coagulation of the milk protein casein. It comprises proteins and fat from milk (usually the milk of cows, buffalo, goats or sheep). During prod ...
s, and to waterproof leather and fabric. Wax has been used since antiquity as a temporary, removable model in lost-wax casting of
gold Gold is a chemical element; it has chemical symbol Au (from Latin ) and atomic number 79. In its pure form, it is a brightness, bright, slightly orange-yellow, dense, soft, malleable, and ductile metal. Chemically, gold is a transition metal ...
,
silver Silver is a chemical element; it has Symbol (chemistry), symbol Ag () and atomic number 47. A soft, whitish-gray, lustrous transition metal, it exhibits the highest electrical conductivity, thermal conductivity, and reflectivity of any metal. ...
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, china markers 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
photocopier A photocopier (also called copier or copy machine, and formerly Xerox machine, the generic trademark) is a machine that makes copies of documents and other visual images onto paper or plastic film quickly and cheaply. Most modern photocopiers ...
s and computer printers. In another context,
lipstick Lipstick is a cosmetics, cosmetic product used to apply coloration and texture to lips, often made of wax and oil. Different pigments are used to produce color, and minerals such as silica may be used to provide texture. The use of lipstick ...
and mascara are blends of various fats and waxes colored with pigments, and both beeswax and lanolin are used in other
cosmetics Cosmetics are substances that are intended for application to the body for cleansing, beautifying, promoting attractiveness, or altering appearance. They are mixtures of chemical compounds derived from either Natural product, natural source ...
. Ski wax is used in
skiing Skiing is the use of skis to glide on snow for basic transport, a recreational activity, or a competitive winter sport. Many types of competitive skiing events are recognized by the International Olympic Committee (IOC), and the International S ...
and
snowboarding Snowboarding is a recreational and competitive activity that involves descending a snow-covered surface while standing on a snowboard that is almost always attached to a rider's feet. It features in the Winter Olympic Games and Winter Paralym ...
. Also, the sports of surfing and
skateboarding Skateboarding is an extreme sport, action sport that involves riding and Skateboarding trick, performing tricks using a skateboard, as well as a recreational activity, an art form, an entertainment industry Profession, job, and a method of tr ...
often use wax to enhance the performance. Some waxes are considered food-safe and are used to coat wooden cutting boards and other items that come into contact with food. Beeswax or coloured synthetic wax is used to decorate Easter eggs in Romania, Ukraine, Poland, Lithuania and the Czech Republic.
Paraffin wax Paraffin wax (or petroleum wax) is a soft colorless solid derived from petroleum, coal, or oil shale that consists of a mixture of hydrocarbon molecules containing between 20 and 40 carbon atoms. It is solid at room temperature and melting poi ...
is used in making chocolate covered sweets. Wax is also used in wax bullets, which are used as simulation aids, and for wax sculpturing.


Specific examples


Animal waxes

* Beeswax – produced by
honey bee A honey bee (also spelled honeybee) is a eusocial flying insect within the genus ''Apis'' of the bee clade, all native to mainland Afro-Eurasia. After bees spread naturally throughout Africa and Eurasia, humans became responsible for the ...
s * Chinese wax – produced by the scale insect ''Ceroplastes ceriferus'' * Lanolin (wool wax) – from the sebaceous glands of sheep * Shellac wax – from the lac insect ''
Kerria lacca ''Kerria lacca'' is a species of insect in the family Kerriidae, the lac insects. These are in the superfamily scale insect, Coccoidea, the scale insects. This species is perhaps the most commercially important lac insect, being a main source of ...
'' * Spermaceti – from the head cavities and blubber of the
sperm whale The sperm whale or cachalot (''Physeter macrocephalus'') is the largest of the toothed whales and the largest toothed predator. It is the only living member of the Genus (biology), genus ''Physeter'' and one of three extant species in the s ...


Vegetable waxes

* Bayberry wax – from the surface wax of the fruits of the bayberry shrub, '' Myrica faya'' or sister species '' Myrica cerifera'' or '' Myrica pensylvanica'' * Candelilla wax – from the Mexican shrubs '' Euphorbia cerifera'' and '' Euphorbia antisyphilitica'' * Carnauba wax – from the leaves of the carnauba palm, '' Copernicia cerifera'' * Castor wax – catalytically hydrogenated castor oil * Esparto wax – a byproduct of making paper from esparto grass (''Macrochloa tenacissima'') * Japan wax – a vegetable
triglyceride A triglyceride (from '' tri-'' and '' glyceride''; also TG, triacylglycerol, TAG, or triacylglyceride) is an ester derived from glycerol and three fatty acids. Triglycerides are the main constituents of body fat in humans and other vertebrates ...
(not a true wax), from the berries of ''Rhus'' and ''Toxicodendron'' species * Jojoba oil – a liquid wax ester, from the seed of ''Simmondsia chinensis''. * Ouricury wax – from the Brazilian feather palm, '' Syagrus coronata''. * Rice bran wax – obtained from
rice Rice is a cereal grain and in its Domestication, domesticated form is the staple food of over half of the world's population, particularly in Asia and Africa. Rice is the seed of the grass species ''Oryza sativa'' (Asian rice)—or, much l ...
bran Bran, also known as miller's bran, is the component of a Cereal, cereal grain consisting of the hard layersthe combined aleurone and Fruit anatomy#Pericarp layers, pericarpsurrounding the endosperm. Maize, Corn (maize) bran also includes the p ...
(''Oryza sativa'') * Soy wax – from soybean oil * Tallow tree wax – from the seeds of the tallow tree ''Triadica sebifera''.


Mineral waxes

* Ceresin waxes * Montan wax – extracted from lignite and brown coal * Ozocerite – found in lignite beds * Peat waxes


Petroleum waxes

*
Paraffin wax Paraffin wax (or petroleum wax) is a soft colorless solid derived from petroleum, coal, or oil shale that consists of a mixture of hydrocarbon molecules containing between 20 and 40 carbon atoms. It is solid at room temperature and melting poi ...
– made of long-chain alkane
hydrocarbon In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and Hydrophobe, hydrophobic; their odor is usually fain ...
s * Microcrystalline wax – with very fine crystalline structure


See also

* Slip melting point * Wax acid * Wax argument, or the "ball of wax example", is a thought experiment originally articulated by Renė Descartes.


References


External links


Waxes
{{Authority control Petroleum products Plant products Animal products Lipids Esters Soft matter