Durene, or 1,2,4,5-tetramethylbenzene, 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 C₆H₂(CH₃)₄. It is a colourless solid with a sweet odor. The compound is classified as an

alkylbenzene The alkylbenzenes are derivatives of benzene, in which one or more hydrogen atoms are replaced by alkyl groups of different sizes. They are a subset of the aromatic hydrocarbons. The simplest member is toluene, in which a hydrogen atom of the benze ...

. It is one of three isomers of tetramethylbenzene, the other two being

prehnitene Prehnitene or 1,2,3,4-tetramethylbenzene is an organic compound with the formula C6H2(CH3)4, classified as an aromatic hydrocarbon. It is a flammable colorless liquid which is nearly insoluble in water but soluble in organic solvents. It occurs n ...

(1,2,3,4-tetramethylbenzene) and

isodurene Isodurene or 1,2,3,5-tetramethylbenzene is an organic compound with the formula C6H2(CH3)4, classified as an aromatic hydrocarbon. It is a flammable colorless liquid which is nearly insoluble in water but soluble in organic solvents. It occurs na ...

(1,2,3,5-tetramethylbenzene). Durene has an unusually high melting point (79.2 °C), reflecting its high molecular symmetry.

Production

It is a component of coal tar and was first prepared from pseudocumene in 1870. It is produced by

methylation In the chemical sciences, methylation denotes the addition of a methyl group on a substrate, or the substitution of an atom (or group) by a methyl group. Methylation is a form of alkylation, with a methyl group replacing a hydrogen atom. These t ...

of other methylated benzene compounds such as ''p''-xylene and pseudocumene. :C₆H₄(CH₃)₂ + 2 CH₃Cl → C₆H₂(CH₃)₄ + 2 HCl In industry, a mixture of

xylene In organic chemistry, xylene or xylol (; IUPAC name: dimethylbenzene) are any of three organic compounds with the formula . They are derived from the substitution of two hydrogen atoms with methyl groups in a benzene ring; which hydrogens are sub ...

s and trimethylbenzenes is alkylated with

methanol Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical and the simplest aliphatic alcohol, with the formula C H3 O H (a methyl group linked to a hydroxyl group, often abbreviated as MeOH). It is a ...

. Durene can be separated from its isomers by selective crystallization, exploiting its high melting point. The original synthesis of durene involved a similar reaction starting from

toluene Toluene (), also known as toluol (), is a substituted aromatic hydrocarbon. It is a colorless, water-insoluble liquid with the smell associated with paint thinners. It is a mono-substituted benzene derivative, consisting of a methyl group (CH3) at ...

. Durene is a significant byproduct of the production of gasoline from

via the "MTG (Methanol to Gasoline) process".

Reactions and uses

It is a relatively easily oxidized benzene derivative, with E_1/2 of 2.03 V vs NHE. Its nucleophilicity is comparable to that of

phenol Phenol (also called carbolic acid) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile. The molecule consists of a phenyl group () bonded to a hydroxy group (). Mildly acidic, it req ...

. It is readily halogenated on the ring for example. Nitration gives the dinitro derivative, a precursor to

duroquinone Duroquinone is an organic oxidant (C6(CH3)4O2). It is related to 1,4-benzoquinone by replacement of four H centres with methyl (Me) groups. The C10O2 core of this molecule is planar with two pairs of C=O and C=C bonds.J.-M. Lü, S. V. Rosokha, I. ...

. In industry, it is the precursor to

pyromellitic dianhydride Pyromellitic dianhydride (PMDA) is an organic compound with the formula C6H2(C2O3)2. It is the double carboxylic acid anhydride that is used in the preparation of polyimide polymers such as Kapton. It is a white, hygroscopic solid. It forms a ...

, which is used for manufacturing curing agents, adhesives, coating materials. It is used in the manufacture of some raw materials for engineering plastics (

polyimides Polyimide (sometimes abbreviated PI) is a polymer containing imide groups belonging to the class of high-performance plastics. With their high heat-resistance, polyimides enjoy diverse applications in roles demanding rugged organic materials, e.g. ...

) and

cross-linking agent In chemistry and biology a cross-link is a bond or a short sequence of bonds that links one polymer chain to another. These links may take the form of covalent bonds or ionic bonds and the polymers can be either synthetic polymers or natural ...

for

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 ...

s. It is also a suitable starting material for the synthesis of

hexamethylbenzene Hexamethylbenzene, also known as mellitene, is a hydrocarbon with the molecular formula C12H18 and the condensed structural formula C6(CH3)6. It is an aromatic compound and a derivative of benzene, where benzene's six hydrogen atoms have each ...

. With a simple proton NMR spectrum comprising two signals due to the 2 aromatic hydrogens (2H) and four methyl groups (12H), durene is used as an internal standard.

Safety

Durene is not a skin irritant nor a skin sensitizer or eye irritant. Durene is only slightly toxic on an acute toxicologic basis and only poses an acute health hazard when ingested in excessive quantities. Dennis W. Lynch, Vernon B. Perone, Ronald L. Schuler, William B. Ushry & Trent R. Lewis, Journal Drug and Chemical Toxicology Volume 1, 1978 - Issue 3, Pages 219-230 (2008)

References

{{Hydrocarbons Hydrocarbon solvents Alkylbenzenes C4-Benzenes