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Toluene

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Toluene
Toluene
General
Systematic name Toluene
Other names Methylbenzene
Phenylmethane
Toluol
Molecular formula C7H8
SMILES CC1=CC=CC=C1
Molar mass 92.14 g/mol
Appearance clear, colourless liquid
CAS number [108-88-3]
Hazards
MSDS Wikisource MSDS
Main Hazards Highly flammable
Flash point 7 C
R/S statement R: 11, 20
S: 16, 25, 29, 33
RTECS number XS5250000
Properties
Density and phase 0.8669 g/mL,
liquid at 20 C
Solubility in water 0.053 g/100 mL
(20-25 C)
Solubility in ethanol,
acetone, hexane,
dichloromethane
Fully miscible
Melting point -93 C (180 K)
Boiling point 110.6 C (383.8 K)
Viscosity 0.590 cP at 20 C
Dipole moment 0.36 D
Supplementary data page
Structure and
properties
n, εr, etc.
Thermodynamic data Phase behaviour
Solid, liquid, gas
Spectral data UV, IR, NMR, MS
Related compounds
Related
aromatic hydrocarbons
benzene
xylene
naphthalene
Related compounds Methylcyclohexane
Except where noted otherwise, data are given for
materials in their standard state (at 25°C, 100 kPa)
Infobox disclaimer and references

Toluene, also known as methylbenzene or phenylmethane is a clear water-insoluble liquid with the typical smell of paint thinners, reminiscent of the sweet smell of the related compound benzene. It is an aromatic hydrocarbon that is widely used as an industrial feedstock and as a solvent. Toluene is listed as a Table II precursor under the United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances[1] (http://www.incb.org/pdf/e/list/red.pdf).

Contents

History

The name toluene was derived from the older name toluol that refers to tolu balsam, an aromatic extract from the tropical American tree Myroxylon balsamum, from which it was first isolated. It was originally named by Jns Jakob Berzelius.

Chemical properties

Toluene reacts as a normal aromatic hydrocarbon towards electrophilic aromatic substitution. The methyl group makes it around 25 times more reactive than benzene in such reactions. It undergoes smooth sulfonation to give p-toluenesulfonic acid, and chlorination by Cl2 in the presence of FeCl3 to give ortho and para isomers of chlorotoluene. It undergoes nitration to give ortho and para nitrotoluene isomers, but if heated it can give dinitrotoluene and ultimately the explosive trinitrotoluene (TNT).

With other reagents the methyl side chain in toluene may react, undergoing oxidation. Potassium permanganate leads to benzoic acid, whereas chromyl chloride leads to benzaldehyde. Halogenation can be performed under free radical conditions, for example NBS leads gives benzyl bromide.

Hydrogenation of toluene to methylcyclohexane requires a high pressure of hydrogen to go to completion, because of the stability of the aromatic system.

Preparation

Toluene occurs naturally at low levels in crude oil and usually produced in the process of making gasoline via a catalytic reformer, in an ethylene cracker or making coke from coal. Final separation (either via distillation or solvent extraction) will take place in a BTX plant.

Uses

Toluene is used as an octane booster in fuel, as a solvent in paints, paint thinners, chemical reactions, rubber, printing, adhesives, lacquers, leather tanning, disinfectants, and to produce phenol and TNT. It is also used as a raw material for toluene diisocyanate, which is used in the manufacture of polyurethane foams.

Precautions

Inhaling of toluene fumes can be intoxicating, but in larger doses nausea-inducing. Chronic or frequent inhalation of toluene over long time periods leads to irreversible brain damage; lower levels can cause damage to teeth[4].

Suppliers/Manufacturers

  • Lancaster (http://www.lancastersynthesis.com/homecatsearch.htm) (now part of Alfa)
  • Fisher (https://www1.fishersci.com/index.jsp)
  • VWR (http://www.vwr.com/index.htm)
  • Alfa (http://www.alfa.com/alf/index.htm)
  • Aldrich (http://www.sigmaaldrich.com)
  • Aurora Fine Chemicals (http://www.aurora-feinchemie.com)

See also

  1. External solubility data (http://144.16.93.203/energy/HC270799/HDL/ENV/enven/vol364.htm)
  2. NIST WebBook (http://webbook.nist.gov/)

References

  1. B. S. Furnell et al., Vogel's Textbook of Practical Organic Chemistry, 5th edition, Longman/Wiley, New York, 1989.
  2. (a) L. G. Wade, Organic Chemistry, 5th ed., p. 871, Prentice Hall, Upper Saddle RIver, New Jersey, 2003.
  3. J. March, Advanced Organic Chemistry, 4th ed., p. 723, Wiley, New York, 1992.
  4. User:Walkerma has personally witnessed such injury.de:Toluol

es:Tolueno it:Toluene nl:Tolueen ja:トルエン pl:Toluen pt:Tolueno fi:Tolueeni zh:甲苯

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