Pentaerythritol is the organic compound

Organic compound

An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...

 with the formula

Chemical formula

A chemical formula or molecular formula is a way of expressing information about the atoms that constitute a particular chemical compound....

 C₅H₁₂O₄. This white, crystalline polyol

Polyol

A polyol is an alcohol containing multiple hydroxyl groups. In two technological disciplines the term "polyol" has a special meaning: food science and polymer chemistry.- Polyols in food science :...

 with the neopentane

Neopentane

Neopentane, also called dimethylpropane, is a double-branched-chain alkane with five carbon atoms. Neopentane is an extremely flammable gas at room temperature and pressure which can condense into a highly volatile liquid on a cold day, in an ice bath, or when compressed to a higher...

 backbone is a versatile building block for the preparation of many polyfunctionalized compounds such as the explosive PETN

PETN

Pentaerythritol tetranitrate , also known as PENT, PENTA, TEN, corpent, penthrite , is the nitrate ester of pentaerythritol. Penta refers to the five carbon atoms of the neopentane skeleton.PETN is most well known as an explosive...

 and pentaerythritol tetraacrylate. Derivatives of pentaerythritol are components of alkyd

Alkyd

An alkyd is a polyester modified by the addition of fatty acids and other components. They are derived from polyols and a dicarboxylic acid or carboxylic acid anhydride. The term alkyd is a modification of the original name "alcid", reflecting the fact that they are derived from alcohol and...

 resin

Resin

Resin in the most specific use of the term is a hydrocarbon secretion of many plants, particularly coniferous trees. Resins are valued for their chemical properties and associated uses, such as the production of varnishes, adhesives, and food glazing agents; as an important source of raw materials...

s, varnish

Varnish

Varnish is a transparent, hard, protective finish or film primarily used in wood finishing but also for other materials. Varnish is traditionally a combination of a drying oil, a resin, and a thinner or solvent. Varnish finishes are usually glossy but may be designed to produce satin or semi-gloss...

es, PVC

Polyvinyl chloride

Polyvinyl chloride, commonly abbreviated PVC, is a thermoplastic polymer. It is a vinyl polymer constructed of repeating vinyl groups having one hydrogen replaced by chloride. Polyvinyl chloride is the third most widely produced plastic, after polyethylene and polypropylene. PVC is widely used in...

 stabilizers, tall oil

Tall oil

Tall oil, also called "liquid rosin" or tallol, is a viscous yellow-black odorous liquid obtained as a by-product of the Kraft process of wood pulp manufacture when pulping mainly coniferous trees. The name originated as an anglicization of the Swedish "tallolja"...

 ester

Ester

Esters are chemical compounds derived by reacting an oxoacid with a hydroxyl compound such as an alcohol or phenol. Esters are usually derived from an inorganic acid or organic acid in which at least one -OH group is replaced by an -O-alkyl group, and most commonly from carboxylic acids and...

s, and olefin antioxidant

Antioxidant

An antioxidant is a molecule capable of inhibiting the oxidation of other molecules. Oxidation is a chemical reaction that transfers electrons or hydrogen from a substance to an oxidizing agent. Oxidation reactions can produce free radicals. In turn, these radicals can start chain reactions. When...

s.

Halogen-free pentaerythritol esters are also environmentally friendly alternative to conventional electrical transformer fluids

Transformer oil

Transformer oil or insulating oil is usually a highly-refined mineral oil that is stable at high temperatures and has excellent electrical insulating properties. It is used in oil-filled transformers, some types of high voltage capacitors, fluorescent lamp ballasts, and some types of high voltage...

, being both readily biodegradable and non-hazardous in water. They advantageously replace polychlorobiphenyl (PCB), and even silicone

Silicone

Silicones are inert, synthetic compounds with a variety of forms and uses. Typically heat-resistant and rubber-like, they are used in sealants, adhesives, lubricants, medical applications , cookware, and insulation....

-based or fluorinated hydrocarbon

Fluorocarbon

Fluorocarbons, sometimes referred to as perfluorocarbons or PFCs, are organofluorine compounds that contain only carbon and fluorine bonded together in strong carbon–fluorine bonds. Fluoroalkanes that contain only single bonds are more chemically and thermally stable than alkanes...

s, as dielectric fluid in transformers. Their low volatility and high flash point

Flash point

The flash point of a volatile material is the lowest temperature at which it can vaporize to form an ignitable mixture in air. Measuring a flash point requires an ignition source...

 give them an excellent resistance to ignition

Combustion

Combustion or burning is the sequence of exothermic chemical reactions between a fuel and an oxidant accompanied by the production of heat and conversion of chemical species. The release of heat can result in the production of light in the form of either glowing or a flame...

 in case of major electrical failure and transformer rupture.

Synthesis

Pentaerythritol can be prepared by condensation of acetaldehyde

Acetaldehyde

Acetaldehyde is an organic chemical compound with the formula CH3CHO or MeCHO. It is one of the most important aldehydes, occurring widely in nature and being produced on a large scale industrially. Acetaldehyde occurs naturally in coffee, bread, and ripe fruit, and is produced by plants as part...

 and formaldehyde

Formaldehyde

Formaldehyde is an organic compound with the formula CH2O. It is the simplest aldehyde, hence its systematic name methanal.Formaldehyde is a colorless gas with a characteristic pungent odor. It is an important precursor to many other chemical compounds, especially for polymers...

 in a basic

Base (chemistry)

For the term in genetics, see base A base in chemistry is a substance that can accept hydrogen ions or more generally, donate electron pairs. A soluble base is referred to as an alkali if it contains and releases hydroxide ions quantitatively...

 environment (Tollens' reaction). The process occurs by successive aldol reaction

Aldol reaction

The aldol reaction is a powerful means of forming carbon–carbon bonds in organic chemistry.Discovered independently by Charles-Adolphe Wurtz and Alexander Porfyrevich Borodin in 1872, the reaction combines two carbonyl compounds to form a new β-hydroxy carbonyl compound...

s followed by a Cannizzaro reaction

Cannizzaro reaction

The Cannizzaro reaction, named after its discoverer Stanislao Cannizzaro, is a chemical reaction that involves the base-induced disproportionation of an aldehyde lacking a hydrogen atom in the alpha position...

. Impurities include dipentaerythritol and tripentaerythritol.

2 CH₃CHO + 8 CH₂O + Ca(OH)₂ → 2 C(CH₂OH)₄ + (HCOO)₂Ca