Durene

Durene: Durene

IUPAC name

1,2,4,5-tetramethylbenzene

Identifiers

CAS number 95-93-2^Y

PubChem 7269

ChemSpider 6999^Y

UNII 181426CFYB^Y

KEGG C14534^Y

ChEBI CHEBI:38978^Y

Jmol-3D images Image 1

SMILES

c1c(c(cc(c1C)C)C)C

InChI

InChI=1S/C10H14/c1-7-5-9(3)10(4)6-8(7)2/h5-6H,1-4H3^Y
Key: SQNZJJAZBFDUTD-UHFFFAOYSA-N^Y
InChI=1/C10H14/c1-7-5-9(3)10(4)6-8(7)2/h5-6H,1-4H3
Key: SQNZJJAZBFDUTD-UHFFFAOYAJ

Properties

Molecular formula C₁₀H₁₄

Molar mass 134.21816

Density 0.868g/cm3

Melting point
79.2 °C

Boiling point
192°C at 760mmHg

Hazards

Main hazards Flammable

Flash point 73.9°C

Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Infobox references

Durene, or 1,2,4,5-tetramethylbenzene, is an aromatic hydrocarbon used as a solvent. It is also an intermediate in the manufacture of pyromellitic acid, which is used for manufacturing curing agents, adhesives and coating materials. It is used in the manufacture of some raw materials for engineering plastics (polyimides) and cross-linking agent for alkyd resins.

1,2,4,5-Tetramethylbenzene has a simple proton NMR spectrum comprising two signals due to the 2 aromatic hydrogens (2H) and four methyl groups (12H). It is also readily soluble in chloroform. This compound is thus a useful internal standard.^[1]

Durene is a significant byproduct that is created in the process of gasoline synthesis from methanol. This is called the "MTG (Methanol To Gasoline) process". A network consisting of a few industrial plants in New Zealand, though currently (as of March 2011) not in operation because their method of gasoline synthesis is more expensive than "traditional" methods (i.e. drilling for oil), may be reopened if gasoline prices rise above a certain level. The MTG process these plants employed produces a significant quantity of durene; their gasoline had to go through a process to reduce the level of durene to an acceptable one when constituting their final product. This was done in order to comply with New Zealand laws on gasoline composition.^[2]

References

^ 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. http://www.arkat-usa.org/get-file/19535/.

^ Packer, John; Kooy, P.; Kirk, Dr. C.M.; Wrinkles, Claire. "The Production of Methanol and Gasoline". New Zealand Institute of Chemistry. http://nzic.org.nz/ChemProcesses/energy/7D.pdf.

Categories:
Hydrocarbon solvents
Alkylbenzenes

Durene


IUPAC name 1,2,4,5-tetramethylbenzene
Identifiers
CAS number	95-93-2^Y
PubChem	7269
ChemSpider	6999^Y
UNII	181426CFYB^Y
KEGG	C14534^Y
ChEBI	CHEBI:38978^Y
Jmol-3D images	Image 1
SMILES c1c(c(cc(c1C)C)C)C
InChI InChI=1S/C10H14/c1-7-5-9(3)10(4)6-8(7)2/h5-6H,1-4H3^Y Key: SQNZJJAZBFDUTD-UHFFFAOYSA-N^Y InChI=1/C10H14/c1-7-5-9(3)10(4)6-8(7)2/h5-6H,1-4H3 Key: SQNZJJAZBFDUTD-UHFFFAOYAJ
Properties
Molecular formula	C₁₀H₁₄
Molar mass	134.21816
Density	0.868g/cm3
Melting point	79.2 °C
Boiling point	192°C at 760mmHg
Hazards
Main hazards	Flammable
Flash point	73.9°C
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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Durène — Général Nom IUPAC 1,2,4,5 tétraméthylbenzène No CAS … Wikipédia en Français
Durene — Du rene, n. [L. durus hard; so called because solid at ordinary temperatures.] (Chem.) A colorless, crystalline, aromatic hydrocarbon, {C6H2(CH3)4}, off artificial production, with an odor like camphor. [1913 Webster] … The Collaborative International Dictionary of English
durene — durenas statusas T sritis chemija formulė C₆H₂(CH₃)₄ atitikmenys: angl. durene rus. дурол ryšiai: sinonimas – 1,2,4,5 tetrametilbenzenas … Chemijos terminų aiškinamasis žodynas
durene — du·rene … English syllables
durene — ˈd(y)u̇ˌrēn noun ( s) Etymology: International Scientific Vocabulary dur (from Latin durus hard) + ene : a colorless crystalline hydrocarbon C6H2(CH3)4 having an odor like camphor and oc … Useful english dictionary
C6H2CH34 — Durene Du rene, n. [L. durus hard; so called because solid at ordinary temperatures.] (Chem.) A colorless, crystalline, aromatic hydrocarbon, {C6H2(CH3)4}, off artificial production, with an odor like camphor. [1913 Webster] … The Collaborative International Dictionary of English
duryl — ˈd(y)u̇rə̇l noun ( s) Etymology: International Scientific Vocabulary durene + yl : a univalent radical C6H(CH3)4 derived from durene; 2,3,5,6 tetramethyl phenyl … Useful english dictionary
Durylic — Du*ryl ic, a. (Chem.) Pertaining to, allied to, or derived from, durene; as, durylic acid. [1913 Webster] … The Collaborative International Dictionary of English
Aromatic hydrocarbon — Arene redirects here. For other uses, see Arene (disambiguation). An aromatic hydrocarbon or arene[1] (or sometimes aryl hydrocarbon)[2] is a hydrocarbon with alternating double and single bonds between carbon atoms. The term aromatic was… … Wikipedia
Friedel-Crafts reaction — The Friedel Crafts reactions are a set of reactions developed by Charles Friedel and James Crafts in 1877. [Friedel, C.; Crafts, J. M. Compt. Rend. 1877, 84 , [http://gallica.bnf.fr/ark:/12148/bpt6k30410/f1386.table 1392]… … Wikipedia

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Durene

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