Toluene

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Toluene, also known as Toluene
methylbenzene or
phenylmethane, is a clear,
water-insoluble liquid (/entry/File:Toluene_chemical_structure.png)

(/entry/Liquid) with the typical

smell of paint thinners, redolent (/entry/File:Toluene-potential-upside-down.png)

of the sweet smell of the related

General
compound benzene
(/entry/Benzene). It is an Systematic name methylbenzene
aromatic hydrocarbon that is
toluene
widely used as an industrial Other names phenylmethane
feedstock and as a solvent toluol
(/entry/Solvent).
Molecular formula (/entry/Chemical_formula) C7H8

History SMILES Cc1ccccc1

The name toluene was derived Molar mass (/entry/Molar_mass) 92.14 g/mol
from the older name toluol that
Appearance Clear colorless, liquid
refers to tolu balsam, an aromatic
extract from the tropical American CAS number [108-88-3]
tree Myroxylon balsamum, from
Properties
which it was first isolated. It was
originally named by Jns Jakob Density (/entry/Density) and phase 0.8669 g/cm, liquid
Berzelius
Solubility in water 0.053 g/100 mL (20-25C)

In ethanol (/entry/Ethanol),
acetone (/entry/Acetone), hexane, Fully miscible
dichloromethane

Melting point (/entry/Melting_point) 93 C (180 K)/(-135.4F)

Boiling point (/entry/Boiling_point) 110.6C (383.8 K)/ 231.08F

Critical temperature 320 C (593 K)/ 608F

Viscosity (/entry/Viscosity) 0.590 cP at 20C/ 68F

Dipole moment (/entry/Dipole#Molecular_dipoles) 0.36 D

Hazards

ScienceLab.com
MSDS (http://www.sciencelab.com/xMSDS-
Toluene-9927301)

Main hazards highly flammable

3
NFPA 704 2 0

(/entry/File:NFPA_704.svg)
 Flash point 4 C/ 39.2 F

R-phrases R11, R38, R48/20, R63, R65, R67

S-phrases S2, S36/37, S29, S46, S62

RTECS number XS5250000

Supplementary data page

n (/entry/Refractive_index), r
Structure & properties
(/entry/Dielectric_constant), etc.

Phase behaviour
Thermodynamic data
Solid, liquid, gas

UV, IR, NMR, MS

Spectral data
(/entry/Mass_spectrometry)

Related compounds

Related aromatic benzene (/entry/Benzene)

hydrocarbons (/p/index.php? xylene (/entry/Xylene)
title=Aromatic_hydrocarbon&action=edit&redlink=1) naphthalene (/entry/Naphthalene)

Related compounds methylcyclohexane

Except where noted otherwise, data are given for

materials in their standard state (at 25C, 100 kPa)

(/entry/J%C3%B6ns_Jakob_Berzelius).
Contents
1 History
Chemical properties
2 Chemical properties Toluene reacts as a normal aromatic hydrocarbon towards electrophilic aromatic
3 Preparation
substitution.[1][2][3] The methyl group makes it around 25 times more reactive than
4 Uses
benzene (/entry/Benzene) in such reactions. It undergoes smooth sulfonation to
5 Toxicology and metabolism
6 See also
give p-toluenesulfonic acid (/p/index.php?title=P-
7 Notes Toluenesulfonic_acid&action=edit&redlink=1), and chlorination by Cl2
8 References (/entry/Chlorine) in the presence of FeCl3 (/p/index.php?
9 External links title=Iron(III)_chloride&action=edit&redlink=1) to give ortho and para isomers
10 Credits (/entry/Isomer) of chlorotoluene. It undergoes nitration to give ortho and para
nitrotoluene isomers, but if heated it can give dinitrotoluene and ultimately the
explosive trinitrotoluene (/entry/Trinitrotoluene) (TNT).

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With other reagents the methyl side chain in toluene may react, undergoing
oxidation. Reaction with potassium permanganate leads to benzoic acid
(/entry/Benzoic_acid), whereas reaction with chromyl chloride leads to
benzaldehyde (tard reaction). Halogenation can be performed under free radical
(/entry/Free_radical) conditions. For example, N-bromosuccinimide
(/p/index.php?title=N-Bromosuccinimide&action=edit&redlink=1) (NBS) heated
with toluene in the presence of AIBN leads to benzyl bromide.

Catalytic hydrogenation of toluene to methylcyclohexane requires a high pressure of hydrogen (/entry/Hydrogen) to

go to completion, because of the stability of the aromatic system.

Preparation
Toluene occurs naturally at low levels in crude oil (/entry/Crude_oil) and is usually produced in the processes of
making gasoline (/entry/Gasoline) via a catalytic reformer, in an ethylene (/entry/Ethylene) cracker or making coke
from coal (/entry/Coal). Final separation (either via distillation (/entry/Distillation) or solvent extraction) takes place in
a BTX plant.

Uses
Toluene is a common solvent (/entry/Solvent), able to dissolve: paints (/entry/Paint), paint thinners, many chemical
reactants, rubber (/entry/Rubber), printing (/entry/Printing) ink, adhesives (/entry/Adhesive) (glues), lacquers, leather
tanners, and disinfectants. It can also be used as a fullerene (/entry/Fullerene) indicator, and is a raw material for
toluene diisocyanate (used in the manufacture of polyurethane foam) and TNT (/entry/Trinitrotoluene). Industrial uses
of toluene include dealkylation to benzene and disproportionation to a mixture of benzene and xylene (/entry/Xylene).
When oxidized it yields benzaldehyde and benzoic acid, two important intermediates in chemistry (/entry/Chemistry).
It is also used as a carbon source for making Multi-Wall Carbon Nanotubes. Toluene can be used to break open red
blood cells in order to extract hemoglobin (/entry/Hemoglobin) in biochemistry experiments.

Toluene can be used as an octane booster in gasoline (/entry/Gasoline) fuels used in internal combustion engines
(/entry/Internal_combustion_engine). Toluene at 84 percent by volume, fueled all the turbo Formula One teams in the
1980s.

Toxicology and metabolism

Inhalation of toluene fumes can be intoxicating, but in larger doses nausea-inducing. Toluene may enter the human
system not only through vapour inhalation from the liquid evaporation, but also following soil contamination events,
where human contact with soil, ingestion of contaminated groundwater or soil vapour off-gassing can occur.

The toxicity of toluene can be explained mostly by its metabolism. As toluene has very low water solubility, it cannot
exit the body via the normal routes (urine, feces, or sweat). It must be metabolized in order to be excreted. The
methyl group of toluene is more easily oxidized by cytochrome P450 than the benzene ring. Therefore, in the
metabolism of toluene, 95 percent is oxidized to become benzyl alcohol.[4] The toxic metabolites are created by the
remaining five percent that are oxidized to benzaldehyde and cresols.[5][6] Most of the reactive products are detoxified
by conjugation to glutathione but the remainder may severely damage cells.[7]

(/entry/File:Toluene_Metabolism_Scheme.png)
Toluene is mainly excreted as benzoic acid (/entry/Benzoic_acid) and hippuric acid, both formed by further metabolic
oxidation of benzyl alcohol.
 (/entry/File:Benzyl_Alcohol_Metabolism_Scheme.png)

See also
Benzene (/entry/Benzene)
Organic chemistry (/entry/Organic_chemistry)
Solvent (/entry/Solvent)

Notes
1. B. S. Furnell et al. Vogel's Textbook of Practical Organic Chemistry, 5th edition. Longman/Wiley, New York,
1989.
2. 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. Nakajima T, Wang R, Elovaara E, Gonzalez F, Gelboin H, Raunio H, Pelkonen O, Vainio H, Aoyama T (1997).
Toluene metabolism by cDNA-expressed human hepatic cytochrome P450. Biochem Pharmacol 53 (3): 271-7.
5. Chapman D, Moore T, Michener S, Powis G. Metabolism and covalent binding of [14C]toluene by human and rat
liver microsomal fractions and liver slices. Drug Metab Dispos 18 (6): 929-36.
6. Hanioka H, Hamamura M, Kakino K, Ogata H, Jinno H, Takahashi A, Nishimura T, Ando M (1995). Dog liver
microsomal P450 enzyme-mediated toluene biotransformation. Xenobiotica 25 (11): 1207-17.
7. van Doorn R, Leijdekkers C, Bos R, Brouns R, Henderson P (1981). Alcohol and sulphate intermediates in the
metabolism of toluene and xylenes to mercapturic acids. J Appl Toxicol 1 (4): 236-42.

References
March. J. Advanced Organic Chemistry, 4th ed. New York: Wiley, 1992. ISBN 978-0471601807
(http://www.amazon.com/dp/0471601802?tag=encyclopediap-
20&camp=14573&creative=327641&linkCode=as1&creativeASIN=0471601802&adid=0NQQZXQ96PDAJGB1J8XS)
McMurry, John. Organic Chemistry. 6th ed. Belmont, CA: Brooks/Cole, 2004. ISBN 0534420052
(http://www.amazon.com/dp/0534420052?tag=encyclopediap-
20&camp=14573&creative=327641&linkCode=as1&creativeASIN=0534420052&adid=0NQQZXQ96PDAJGB1J8XS)
Morrison, Robert T., and Robert N. Boyd. Organic Chemistry. 6th ed. Englewood Cliffs, NJ: Prentice Hall, 1992.
ISBN 0136436692 (http://www.amazon.com/dp/0136436692?tag=encyclopediap-
20&camp=14573&creative=327641&linkCode=as1&creativeASIN=0136436692&adid=0NQQZXQ96PDAJGB1J8XS)
Solomons, T.W. Graham, and Fryhle, Craig B. Organic Chemistry. 8th ed. Hoboken, NJ: John Wiley, 2004.
ISBN 0471417998 (http://www.amazon.com/dp/0471417998?tag=encyclopediap-
20&camp=14573&creative=327641&linkCode=as1&creativeASIN=0471417998&adid=0NQQZXQ96PDAJGB1J8XS)
Vogel, A.I. , A.R. Tatchell, B.S. Furnis, A.J. Hannaford, and P.W.G. Smith. Vogel's Textbook of Practical Organic
Chemistry 5th ed. Upper Saddle River, NJ: Prentice Hall, 1996. ISBN 978-0582462366
 (http://www.amazon.com/dp/0582462363?tag=encyclopediap-
20&camp=14573&creative=327641&linkCode=as1&creativeASIN=0582462363&adid=0NQQZXQ96PDAJGB1J8XS)
Wade, Leroy G. Organic Chemistry 5th ed. Upper Saddle River, NJ: Prentice Hall, 2003. ISBN 978-0130338327
(http://www.amazon.com/dp/013033832X?tag=encyclopediap-
20&camp=14573&creative=327641&linkCode=as1&creativeASIN=013033832X&adid=0NQQZXQ96PDAJGB1J8XS)

External links
All links retrieved December 10, 2015.

NIOSH Pocket Guide to Chemical Hazards: Toluene (http://www.cdc.gov/niosh/npg/npgd0619.html)

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