Movatterモバイル変換


[0]ホーム

URL:


Jump to content
WikipediaThe Free Encyclopedia
Search

Durene

From Wikipedia, the free encyclopedia
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 InfoCard100.002.242Edit 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 mass134.21816
Density0.868 g/cm3
Melting point79.2 °C (174.6 °F; 352.3 K)
Boiling point192 °C (378 °F; 465 K) at 760mmHg
−101.2·10−6 cm3/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Flammable
Flash point73.9 °C (165.0 °F; 347.0 K)
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Chemical compound

Durene, or1,2,4,5-tetramethylbenzene, is anorganic compound with the formula C6H2(CH3)4. It is a colourless solid with a sweet odor. The compound is classified as analkylbenzene. It is one of three isomers of tetramethylbenzene, the other two beingprehnitene (1,2,3,4-tetramethylbenzene) andisodurene (1,2,3,5-tetramethylbenzene). Durene has an unusually high melting point (79.2 °C), reflecting its high molecular symmetry.

Production

[edit]

It is a component of coal tar and was first prepared frompseudocumene in 1870.[1] It is produced bymethylation of other methylated benzene compounds such asp-xylene and pseudocumene.[2]

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

In industry, a mixture ofxylenes and trimethylbenzenes is alkylated withmethanol. 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 fromtoluene.[4]

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

Reactions and uses

[edit]

It is a relatively easily oxidized benzene derivative, with E1/2 of 2.03 V vs NHE.[6] Its nucleophilicity is comparable to that ofphenol.[7] It is readily halogenated on the ring for example. Nitration gives the dinitro derivative, a precursor toduroquinone. In industry, it is the precursor topyromellitic 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) andcross-linking agent foralkydresins.[8] It is also a suitable starting material for the synthesis ofhexamethylbenzene.[2]

With a simpleproton NMR spectrum comprising two signals due to the 2 aromatic hydrogens (2H) and four methyl groups (12H), durene is used as aninternal standard.[9]

Safety

[edit]

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

[edit]
  1. ^Jannasch, Paul; Fittig, Rudolph (1870)."Ueber das Tetramethylbenzol" [On tetramethylbenzene].Zeitschrift für Chemie.6:161–162.
  2. ^abSmith, Lee Irvin (1930)."Durene".Organic Syntheses.10: 32.doi:10.15227/orgsyn.010.0032;Collected Volumes, vol. 2, p. 248.
  3. ^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. Weinheim: Wiley-VCH.doi:10.1002/14356007.a13_227.ISBN 978-3-527-30673-2.
  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. inPetr K. Sazonov, Vasyli A. Ivushkin, Galina A. Artamkina, andIrina 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)
Saturated
aliphatic
hydrocarbons
Alkanes
CnH2n + 2
Linear alkanes
Branched alkanes
Cycloalkanes
Alkylcycloalkanes
Bicycloalkanes
Polycycloalkanes
Other
Unsaturated
aliphatic
hydrocarbons
Alkenes
CnH2n
Linear alkenes
Branched alkenes
Alkynes
CnH2n − 2
Linear alkynes
Branched alkynes
Cycloalkenes
Alkylcycloalkenes
Bicycloalkenes
Cycloalkynes
Dienes
Other
Aromatic
hydrocarbons
PAHs
Acenes
Other
Alkylbenzenes
C2-Benzenes
Xylenes
Other
C3-Benzenes
Trimethylbenzenes
Other
C4-Benzenes
Cymenes
Tetramethylbenzenes
Other
Other
Vinylbenzenes
Other
Other
Retrieved from "https://en.wikipedia.org/w/index.php?title=Durene&oldid=1279978776"
Categories:
Hidden categories:

[8]ページ先頭

©2009-2025 Movatter.jp