Durene

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Durene
Skeletal formula of durene
Ball-and-stick model of the durene molecule
Names
Preferred IUPAC name
1,2,4,5-Tetramethylbenzene
Other names
Durol
Identifiers
3D model (
JSmol
)
ChEBI
ChemSpider
ECHA InfoCard
 100.002.242 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C10H14/c1-7-5-9(3)10(4)6-8(7)2/h5-6H,1-4H3 checkY
    Key: SQNZJJAZBFDUTD-UHFFFAOYSA-N checkY
  • 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).
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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.

Production

It is a component of coal tar and was first prepared from

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.

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]

References

  1. Zeitschrift für Chemie
    . 6: 161–162.
  2. ^
    doi:10.15227/orgsyn.010.0032
    ; Collected Volumes, vol. 2, p. 248.
  3. ISBN 978-3527306732
    .
  4. 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. doi:10.1021/ja00326a014
    .
  7. ISBN 3527306730
    .
  8. ISBN 978-3527306732
    .
  9. 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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