Durene

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Durene
Durene.png
Durene 3D ball.png
Names
Preferred IUPAC name
1,2,4,5-Tetramethylbenzene
Other names
Durol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.002.242 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C10H14/c1-7-5-9(3)10(4)6-8(7)2/h5-6H,1-4H3 Yes check.svgY
    Key: SQNZJJAZBFDUTD-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C10H14/c1-7-5-9(3)10(4)6-8(7)2/h5-6H,1-4H3
    Key: SQNZJJAZBFDUTD-UHFFFAOYAJ
  • c1c(c(cc(c1C)C)C)C
Properties
C10H14
Molar mass 134.21816
Density 0.868 g/cm3
Melting point 79.2 °C (174.6 °F; 352.3 K)
Boiling point 192 °C (378 °F; 465 K) at 760mmHg
-101.2·10−6 cm3/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Flammable
Flash point 73.9 °C (165.0 °F; 347.0 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Durene, or 1,2,4,5-tetramethylbenzene, is an organic compound with the formula C6H2(CH3)4. It is a colourless solid with a sweet odor. The compound is classified as an alkylbenzene. It is one of three isomers of tetramethylbenzene, the other two being prehnitene (1,2,3,4-tetramethylbenzene) and isodurene (1,2,3,5-tetramethylbenzene). Durene has an unusually high melting point (79.2 °C), reflecting its high molecular symmetry.

Contents

Production

It is a component of coal tar and was first prepared from pseudocumene in 1870. [1] It is produced by methylation of other methylated benzene compounds such as p-xylene and pseudocumene. [2]

C6H4(CH3)2 + 2 CH3Cl → C6H2(CH3)4 + 2 HCl

In industry, a mixture of xylenes and trimethylbenzenes is alkylated with methanol. Durene can be separated from its isomers by selective crystallization, exploiting its high melting point. [3] The original synthesis of durene involved a similar reaction starting from toluene. [4]

Durene is a significant byproduct of the production of gasoline from methanol via the "MTG (Methanol to Gasoline) process". [5]

Reactions and uses

It is a relatively easily oxidized benzene derivative, with E1/2 of 2.03 V vs NHE. [6] Its nucleophilicity is comparable to that of phenol. [7] It is readily halogenated on the ring for example. Nitration gives the dinitro derivative, a precursor to duroquinone. In industry, it is the precursor to pyromellitic dianhydride, which is used for manufacturing curing agents, adhesives, coating materials. It is used in the manufacture of some raw materials for engineering plastics (polyimides) and cross-linking agent for alkyd resins. [8] It is also a suitable starting material for the synthesis of hexamethylbenzene. [2]

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. [9]

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. [10]

Related Research Articles

<span class="mw-page-title-main">Acenaphthene</span> Chemical compound

Acenaphthene is a polycyclic aromatic hydrocarbon (PAH) consisting of naphthalene with an ethylene bridge connecting positions 1 and 8. It is a colourless solid. Coal tar consists of about 0.3% of this compound.

<span class="mw-page-title-main">Acenaphthylene</span> Chemical compound

Acenaphthylene, a polycyclic aromatic hydrocarbon is an ortho- and peri-fused tricyclic hydrocarbon. The molecule resembles naphthalene with positions 1 and 8 connected by a -CH=CH- unit. It is a yellow solid. Unlike many polycyclic aromatic hydrocarbons, it has no fluorescence.

<span class="mw-page-title-main">Acenaphthoquinone</span> Chemical compound

Acenaphthoquinone is a quinone derived from acenaphthene. It is a water-insoluble yellow solid. It is a precursor to some agrichemicals and dyes.

1,2,4-Trimethylbenzene, also known as pseudocumene, is an organic compound with the chemical formula C6H3(CH3)3. Classified as an aromatic hydrocarbon, it is a flammable colorless liquid with a strong odor. It is nearly insoluble in water but soluble in organic solvents. It occurs naturally in coal tar and petroleum (about 3%). It is one of the three isomers of trimethylbenzene.

<span class="mw-page-title-main">1-Octadecene</span> Chemical compound

1-Octadecene is a long-chain hydrocarbon and an alkene with the molecular formula CH2=CH(CH2)15CH3. It is one of many isomers of octadecene. Classified as an alpha-olefin, 1-octadecene is the longest alkene that is liquid at room temperature.

<span class="mw-page-title-main">Indane</span> Chemical compound

Indane or indan is an organic compound with the formula C6H4(CH2)3. It is a colorless liquid hydrocarbon. It is a petrochemical, a bicyclic compound. It occurs at the level of about 0.1% in coal tar. It is usually produced by hydrogenation of indene.

1,2,3-Trimethylbenzene is an organic compound with the chemical formula C6H3(CH3)3. Classified as an aromatic hydrocarbon, it is a flammable colorless liquid. It is nearly insoluble in water but soluble in organic solvents. It occurs naturally in coal tar and petroleum. It is one of the three isomers of trimethylbenzene. It is used in jet fuel, mixed with other hydrocarbons, to prevent the formation of solid particles which might damage the engine.

In organic chemistry, transalkylation is a chemical reaction involving the transfer of an alkyl group from one organic compound to another. The reaction is used for the transfer of methyl and ethyl groups between benzene rings. This is of particular value in the petrochemical industry to manufacture p-xylene, styrene, and other aromatic compounds. Motivation for using transalkylation reactions is based on a difference in production and demand for benzene, toluene, and xylenes. Transalkylation can convert toluene, which is overproduced, into benzene and xylene, which are under-produced. Zeolites are often used as catalysts in transalkylation reactions.

<span class="mw-page-title-main">Prehnitene</span> Organic compound

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 naturally in coal tar. Prehnitene is one of three isomers of tetramethylbenzene, the other two being isodurene (1,2,3,5-tetramethylbenzene) and durene (1,2,4,5-tetramethylbenzene). It is a relatively easily oxidized benzene derivative, with E1/2 of 2.0 V vs NHE.

<span class="mw-page-title-main">Isodurene</span> Organic compound

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 naturally in coal tar. Isodurene is one of three isomers of tetramethylbenzene, the other two being prehnitene (1,2,3,4-tetramethylbenzene) and durene (1,2,4,5-tetramethylbenzene).

Pentamethylbenzene is an organic compound with the formula C6H(CH3)5. It is a colourless solid with a sweet odor. The compound is classified as an aromatic hydrocarbon. It is a relatively easily oxidized benzene derivative, with E1/2 of 1.95 V vs NHE.

1-Dodecene is an alkene with the formula C10H21CH=CH2, consisting of a chain of twelve carbon atoms ending with a double bond. While there are many isomers of dodecene depending on which carbon the double bond is placed, this isomer is of greater commercial importance. It is classified as an alpha-olefin. Alpha-olefins are distinguished by having a double bond at the primary or alpha (α) position. This location of a double bond enhances the reactivity of the compound and makes it useful for a number of applications, especially for the production of detergents.

<span class="mw-page-title-main">Alkylbenzenes</span> Family of organic compounds

An alkylbenzene is a chemical compound that contains a monocyclic aromatic ring attaching to one or more saturated hydrocarbon chains. Alkylbenzenes are derivatives of benzene, in which one or more hydrogen atoms are replaced by alkyl groups. The simplest member, toluene, has the hydrogen atom of the benzene ring replaced by a methyl group. The chemical formula of alkylbenzenes is CnH2n-6.

<span class="mw-page-title-main">Phenanthrenequinone</span> Chemical compound

Phenanthrenedione is a quinone derivative of a polycyclic aromatic hydrocarbon. It is an orange, water-insoluble solid.

<span class="mw-page-title-main">4-Ethyltoluene</span> Chemical compound

4-Ethyltoluene is an organic compound with the formula CH3C6H4C2H5. It is one of three isomers of ethyltoluene, the other two isomers being 3-ethyltoluene and 2-ethyltoluene. All are colorless liquids and all are used for the production of specialty polystyrenes.

<span class="mw-page-title-main">1-Hexadecene</span> Chemical compound

1-Hexadecene, also known as 1-cetene, is a long-chain hydrocarbon and an alkene with the molecular formula CH2=CH(CH2)13CH3. It is one of many isomers of hexadecene. Classified as an alpha-olefin, 1-hexadecene is a colorless liquid.

<i>o</i>-Cymene Organic compound

o-Cymene is an organic compound classified as an aromatic hydrocarbon. Its structure consists of a benzene ring ortho-substituted with a methyl group and an isopropyl group. It is a flammable colorless liquid which is nearly insoluble in water but soluble in organic solvents.

<i>m</i>-Cymene Organic compound

m-Cymene is an organic compound classified as an aromatic hydrocarbon. Its structure consists of a benzene ring meta-substituted with a methyl group and an isopropyl group. It is a flammable colorless liquid which is nearly insoluble in water but soluble in organic solvents.

<i>tert</i>-Butylbenzene Organic compound

tert-Butylbenzene is an organic compound classified as an aromatic hydrocarbon. Its structure consists of a benzene ring substituted with a tert-butyl group. It is a flammable colorless liquid which is nearly insoluble in water but miscible with organic solvents.

<span class="mw-page-title-main">1,8-Naphthalic anhydride</span> Chemical compound

1,8-Naphthalic anhydride is an organic compound with the formula C10H6(C2O3). It is one of three isomers of naphthalic anhydride, the other two being the 1,2- and the 2,3-derivatives. The 1,8-isomer is prepared by aerobic oxidation of acenaphthene. 2,6-naphthalenedicarboxylic acid can be prepared from this anhydride. 1,8-Naphthalic anhydride is a precursor to the 4-chloro and 4,5-dichloro derivatives. These chloride groups are susceptible to displacement by amines and alkoxides, giving rise, ultimately, to a large family of naphthalimides, which are used as optical brighteners.

References

  1. ↑ Jannasch, Paul; Fittig, Rudolph (1870). "Ueber das Tetramethylbenzol" [On tetramethylbenzene]. Zeitschrift für Chemie . 6: 161–162.
  2. 1 2 Smith, Lee Irvin (1930). "Durene". Organic Syntheses . 10: 32. doi:10.15227/orgsyn.010.0032.; Collective Volume, vol. 2, p. 248
  3. ↑ Griesbaum, Karl; Behr, Arno; Biedenkapp, Dieter; Voges, Heinz-Werner; Garbe, Dorothea; Paetz, Christian; Collin, Gerd; Mayer, Dieter; Höke (2002). "Hydrocarbons". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a13_227.
  4. ↑ Ador, E.; Rilliet, A. (1879). "Ueber durch Einwirkung von Chlormethyl auf Benzol in Gegenwart von Aluminiumchlorid erhaltene Kohlenwasserstoffe" [Hydrocarbons obtained by the action of methyl chloride on benzene in the presence of aluminum chloride]. Chem. Ber. 12: 329–332. doi:10.1002/cber.18790120191.
  5. ↑ Packer, John; Kooy, P.; Kirk, C. M.; Wrinkles, Claire. "The Production of Methanol and Gasoline" (PDF). New Zealand Institute of Chemistry. Archived (PDF) from the original on September 28, 2006.
  6. ↑ Howell, J. O.; Goncalves, J. M.; Amatore, C.; Klasinc, L.; Wightman, R. M.; Kochi, J. K. (1984). "Electron transfer from aromatic hydrocarbons and their pi-complexes with metals. Comparison of the standard oxidation potentials and vertical ionization potentials". Journal of the American Chemical Society. 106 (14): 3968–3976. doi:10.1021/ja00326a014.
  7. ↑ Griesbaum, Karl; Behr, Arno; Biedenkapp, Dieter; Voges, Heinz-Werner; Garbe, Dorothea; Paetz, Christian; Collin, Gerd; Mayer, Dieter; Höke, Hartmut (2002). "Hydrocarbons". Ullmann's Encyclopedia of Industrial Chemistry . doi:10.1002/14356007.a13_227. ISBN   3527306730.
  8. ↑ Röhrscheid, F. (2012). "Carboxylic Acids, Aromatic". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a05_249. ISBN   978-3527306732.
  9. ↑ e.g. in Petr K. Sazonov, Vasyli A. Ivushkin, Galina A. Artamkina, and Irina P. Beletskaya (2003). "Metal carbonyl anions as model metal-centered nucleophiles in aromatic and vinylic substitution reactions". Arkivoc . 10: 323–334.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  10. ↑ 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)
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