Pentaerythritol is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

with the

formula In science, a formula is a concise way of expressing information symbolically, as in a mathematical formula or a ''chemical formula''. The informal use of the term ''formula'' in science refers to the general construct of a relationship betwee ...

C(CH₂OH)₄. Classified as a

polyol In organic chemistry, a polyol is an organic compound containing multiple hydroxyl groups (). The term "polyol" can have slightly different meanings depending on whether it is used in food science or polymer chemistry. Polyols containing two, thr ...

, it is a white solid. Pentaerythritol is a building block for the synthesis and production of

explosive An explosive (or explosive material) is a reactive substance that contains a great amount of potential energy that can produce an explosion if released suddenly, usually accompanied by the production of light, heat, sound, and pressure. An expl ...

plastic Plastics are a wide range of synthetic or semi-synthetic materials that use polymers as a main ingredient. Their plasticity makes it possible for plastics to be moulded, extruded or pressed into solid objects of various shapes. This adaptab ...

paint Paint is any pigmented liquid, liquefiable, or solid mastic composition that, after application to a substrate in a thin layer, converts to a solid film. It is most commonly used to protect, color, or provide texture. Paint can be made in many ...

s, appliances,

cosmetics Cosmetics are constituted mixtures of chemical compounds derived from either natural sources, or synthetically created ones. Cosmetics have various purposes. Those designed for personal care and skin care can be used to cleanse or protect ...

, and many other commercial products. The word pentaerythritol is a blend of ''penta-'' in reference to its 5 carbon atoms and ''

erythritol Erythritol is an organic compound, a four-carbon sugar alcohol (or polyol) with no optical activity, used as a food additive and sugar substitute. It is naturally occurring. It can be made from corn using enzymes and fermentation. Its formula i ...

'', which also possesses 4 alcohol groups.

Synthesis

Pentaerythritol was first reported in 1891 by German chemist

Bernhard Tollens Bernhard Christian Gottfried Tollens (30 July 184131 January 1918) was a German chemist. Life and work Tollens attended school at the Gelehrtenschule des Johanneums in Hamburg where he was influenced by his science teacher, Karl Möbius. After gr ...

and his student P. Wigand. It may be prepared via a base-catalyzed multiple-

addition reaction In organic chemistry, an addition reaction is, in simplest terms, an organic reaction where two or more molecules combine to form a larger one (the adduct).. Addition reactions are limited to chemical compounds that have multiple bonds, such as ...

between

acetaldehyde Acetaldehyde (IUPAC systematic name ethanal) is an organic chemical compound with the formula CH3 CHO, sometimes abbreviated by chemists as MeCHO (Me = methyl). It is a colorless liquid or gas, boiling near room temperature. It is one of the mos ...

and 3 equivalents of

formaldehyde Formaldehyde ( , ) (systematic name methanal) is a naturally occurring organic compound with the formula and structure . The pure compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde (refer to section F ...

to give pentaerythrose (CAS: 3818-32-4), followed by a

Cannizzaro reaction The Cannizzaro reaction, named after its discoverer Stanislao Cannizzaro, is a chemical reaction which involves the base-induced disproportionation of two molecules of a non-enolizable aldehyde to give a primary alcohol and a carboxylic acid. : ...

with a fourth equivalent of

to give the final product.

Uses

Pentaerythritol is a versatile building block for the preparation of many compounds, particularly polyfunctionalized derivatives. applications include

alkyd An alkyd is a polyester resin modified by the addition of fatty acids and other components. Alkyds are derived from polyols and organic acids including dicarboxylic acids or carboxylic acid anhydride and triglyceride oils. The term ''alkyd'' is a m ...

resin In polymer chemistry and materials science, resin is a solid or highly viscous substance of plant or synthetic origin that is typically convertible into polymers. Resins are usually mixtures of organic compounds. This article focuses on natu ...

varnish Varnish is a clear transparent hard protective coating or film. It is not a stain. It usually has a yellowish shade from the manufacturing process and materials used, but it may also be pigmented as desired, and is sold commercially in various ...

es, polyvinyl chloride stabilizers, tall oil

ester 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 ar ...

antioxidant Antioxidants are compounds that inhibit oxidation, a chemical reaction that can produce free radicals. This can lead to polymerization and other chain reactions. They are frequently added to industrial products, such as fuels and lubricant ...

s (e.g. Anox 20). Such derivatives are found in

, and many other products.

Ester 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 ar ...

s of pentaerythitol are

biodegradable Biodegradation is the breakdown of organic matter by microorganisms, such as bacteria and fungi. It is generally assumed to be a natural process, which differentiates it from composting. Composting is a human-driven process in which biodegradati ...

, and they are used as

transformer oil Transformer oil or insulating oil is an oil that is stable at high temperatures and has excellent electrical insulating properties. It is used in oil-filled transformers (wet transformers), some types of high-voltage capacitors, fluorescent lamp b ...

s. Due to a very high

flash point The flash point of a material is the "lowest liquid temperature at which, under certain standardized conditions, a liquid gives off vapours in a quantity such as to be capable of forming an ignitable vapour/air mixture". (EN 60079-10-1) The fl ...

they also find some use in lubricating

gas turbine A gas turbine, also called a combustion turbine, is a type of continuous flow internal combustion engine. The main parts common to all gas turbine engines form the power-producing part (known as the gas generator or core) and are, in the directi ...

Polyester derivatives

Pentaerythritol is a precursor to esters of the type C(CH₂OX)₄. Such derivatives are

pentaerythritol tetranitrate Pentaerythritol tetranitrate (PETN), also known as PENT, PENTA, (ПЕНТА, primarily in Russian) TEN, corpent, or penthrite (or, rarely and primarily in German, as nitropenta), is an explosive material. It is the nitrate ester of pentaerythri ...

(PETN), a

vasodilator Vasodilation is the widening of blood vessels. It results from relaxation of smooth muscle cells within the vessel walls, in particular in the large veins, large arteries, and smaller arterioles. The process is the opposite of vasoconstriction, ...

and

, the trinitrate

derivative In mathematics, the derivative of a function of a real variable measures the sensitivity to change of the function value (output value) with respect to a change in its argument (input value). Derivatives are a fundamental tool of calculus. F ...

pentrinitrol (Petrin), the tetraacetate normosterol (PAG), and the

polymer A polymer (; Greek '' poly-'', "many" + ''-mer'', "part") is a substance or material consisting of very large molecules called macromolecules, composed of many repeating subunits. Due to their broad spectrum of properties, both synthetic a ...

cross-linking agent

pentaerythritol tetraacrylate Pentaerythritol tetraacrylate (PETA or sometimes PETTA,PETRA) is an organic compound. It is a tetrafunctional acrylate ester used as a monomer in the manufacture of polymers. As it is a polymerizable acrylate monomer it is nearly always supplied wi ...

Fire retardants

Pentaerythritol is used as a fire retardant, such as in plastics and

intumescent An intumescent is a substance that swells as a result of heat exposure, leading to an increase in volume and decrease in density. Intumescent materials are typically used in passive fire protection and require listing, approval, and compliance in ...

paints and coatings. It releases water upon heating and leaves a deposit of thermally insulating char.

References

{{Reflist Tetrols

Synthesis

Uses

Polyester derivatives

Fire retardants

See also

References