toulene

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Toluene/tluin/,formerly known as toluol/tlul/,is a clear,water-insoluble liquid with the typical

smell ofpaint thinners.It is a mono-substitutedbenzenederivative, i.e., one in which a single hydrogen

atom from a group of six atoms from the benzene molecule has been replaced by a univalent group, in

this caseCH3.As such, its IUPAC systematic name is methylbenzene.

It is anaromatic hydrocarbonthat is widely used as an industrialfeedstockand as asolvent.Like othersolvents, toluene is sometimes also used as aninhalantdrug for its intoxicating properties; however,

inhaling toluene has potential to cause severe neurological harm.[2][3]Toluene is an important organic

solvent, but is also capable of dissolving a number of notable inorganic chemicals such as sulfur,[4]iodine,

bromine, phosphorus, and other non-polar covalent substances.

Contents

[hide]

1 History

2 Physical properties 3 Chemical properties

4 Production

o 4.1 Laboratory preparation

5 Uses

o 5.1 Solvent

o 5.2 Fuel

o 5.3 Niche applications

6 Toxicology and metabolism 7 References

8 External links

History[edit]

The compound was first isolated in 1837 by aPolishchemistFilip Walterthrough a distillation ofpineoil

who named it retinaptha.[5]This name was replaced shortly after by the word toluenederived from the

older name toluol, which refers totolu balsam,an aromatic extract from the tropical Colombian

treeMyroxylon balsamum,from which it was also isolated later.[6]It was originally named byJns Jakob

Berzelius.

Physical properties[edit]The surface tension of toluene is 27.73 dyn/cm.

Chemical properties[edit]

Toluene reacts as a normalaromatic hydrocarbontowardselectrophilic aromatic

substitution.[7][8][9]Themethylgroup makes it around 25 times more reactive thanbenzenein such
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reactions. It undergoes smoothsulfonationto givep-toluenesulfonic acid,andchlorinationbyCl2in the

presence ofFeCl3to give ortho and paraisomersofchlorotoluene.

With otherreagentsthe methylside chainin toluene may react, undergoing oxidation. Reaction

withpotassium permanganateand diluted acid (e.g.,sulfuric acid)orpotassium permanganatewith

concentratedsulfuric acid,leads tobenzoic acid,whereas reaction withchromyl chlorideleads

tobenzaldehyde(tard reaction).Halogenationcan be performed underfree radicalconditions. For

example,N-bromosuccinimide(NBS) heated with toluene in the presence ofAIBNleads tobenzyl

bromide.Toluene can also be treated with elementalbrominein the presence of UV light (direct sunlight)

to yieldbenzyl bromide.Toluene may also be brominated by treating it with HBr and H2O2in the presence

of light.[10]

Catalytichydrogenationof toluene tomethylcyclohexanerequires a high pressure ofhydrogento go

to completion, because of the stability of the aromatic system. pKais approximately 45.

Production[edit]

Toluene occurs naturally at low levels incrude oiland is usually produced in the processes

ofgasolinevia acatalytic reformer,in anethylenecrackeror makingcokefromcoal.Final

separation, either viadistillationorsolvent extraction,takes place in one of the many available

processes for extraction of theBTXaromatics (benzene, toluene and xylene isomers).

Laboratory preparation[edit]

Toluene can be prepared industrially or in the laboratory by a variety of methods.

Frombenzene(FriedelCrafts reaction)

Although only of pedagogical interest, benzene reacts with methyl chloride in presence of anhydrous

aluminium chloride to form toluene. The formation follows an electrophilic substitution reaction

according to this stoichiometry:

C6H5H + CH3+ C6H5CH3+ HCl

Many catalysts can be used in place of AlCl3. Their order of reactivity is :AlCl3> SbCl3> SnCl4>

BF3> ZnCl2> HgCl2. The reaction is not very useful because toluene formed readily undergoes

further alkylation at a still-greater speed to produce polysubstituted products.

Frombromobenzene(Wurtz-Fittig reaction)

The Wurtz-Fittig reaction is the reaction of an aryl halide and alkyl halide in presence of sodium

metal to give substituted aromatic compounds. Whenbromobenzeneandmethyl bromidereact

with sodium metal in dry ether solution, toluene is obtained.[citation needed]

C6H5Br + CH3Br + 2Na C6H5CH3+ 2NaBr

From toluic acid (decarboxylation)

When sodium salt of toluic acid (o-,m-,p-)is heated withsoda lime,toluene is obtained.
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both two-stroke and four-stroke engines; however, due to the density of the

fuel and other factors, the fuel does not vaporize easily unless preheated to

70 degrees Celsius (Honda accomplished this in their Formula 1 cars by

routing the fuel lines through the muffler system to heat the fuel). Toluene

also poses similar problems as alcohol fuels, as it eats through standard

rubber fuel lines and has no lubricating properties, as standard gasolinedoes,[citation needed]which can break down fuel pumps and cause upper

cylinder bore wear.

In Australia, toluene has been found to have been illegally combined with

petrol in fuel outlets for sale as standard vehicular fuel. Toluene attracts no

fuel excise, while other fuels are taxed at over 40%, so fuel suppliers are

able to profit from substituting the cheaper toluene for petrol. This

substitution is likely to affect engine performance and result in additional

wear and tear. The extent of toluene substitution has not been

determined.[13][14]

Toluene is another in a group of fuels that have recently been used ascomponents forjet fuelsurrogate blends.[15]Toluene is used as ajet fuel

surrogatefor its content ofaromatic compounds.

Niche applications[edit]

Toluene has also been used as a coolant for its good heat transfer

capabilities in sodium cold traps used in nuclear reactor system loops.

Toluene had also been used in the process ofremoving the cocainefrom

coca leaves in the production of Coca-Cola syrup.[16]

Toxicology and metabolism[edit]

Main article:Toluene (toxicology)

Inhalation of toluene in low to moderate levels can cause tiredness,

confusion, weakness, drunken-type actions, memory loss, nausea, loss of

appetite, and hearing and color vision loss. These symptoms usually

disappear when exposure is stopped. Inhaling high levels of toluene in a

short time may cause light-headedness, nausea, or sleepiness. It can also

cause unconsciousness, and evendeath.[17][18]

Toluene is, however, much less toxic thanbenzene,and has, as a

consequence, largely replaced it as an aromatic solvent in chemical

preparation. For example, benzene is a known carcinogen, whereas

toluene has very little carcinogenic potential.[19]

Similar to many other solvents such as1,1,1-trichloroethaneand

somealkylbenzenes,toluene has been shown to act as anon-

competitiveNMDA receptor antagonistandGABAAreceptorpositive

allosteric modulator.[20]It is abused as aninhalantlikely on account of

theeuphoricanddissociativeeffects these actions produce.[20]Additionally,
http://en.wikipedia.org/wiki/Wikipedia:Citation_neededhttp://en.wikipedia.org/wiki/Wikipedia:Citation_neededhttp://en.wikipedia.org/wiki/Wikipedia:Citation_neededhttp://en.wikipedia.org/wiki/Wikipedia:Citation_neededhttp://en.wikipedia.org/wiki/Toluene#cite_note-13http://en.wikipedia.org/wiki/Toluene#cite_note-13http://en.wikipedia.org/wiki/Toluene#cite_note-13http://en.wikipedia.org/wiki/Jet_fuelhttp://en.wikipedia.org/wiki/Jet_fuelhttp://en.wikipedia.org/wiki/Jet_fuelhttp://en.wikipedia.org/wiki/Toluene#cite_note-15http://en.wikipedia.org/wiki/Toluene#cite_note-15http://en.wikipedia.org/wiki/Toluene#cite_note-15http://en.wikipedia.org/wiki/Jet_fuel_surrogatehttp://en.wikipedia.org/wiki/Jet_fuel_surrogatehttp://en.wikipedia.org/wiki/Jet_fuel_surrogatehttp://en.wikipedia.org/wiki/Aromatic_compoundshttp://en.wikipedia.org/wiki/Aromatic_compoundshttp://en.wikipedia.org/wiki/Aromatic_compoundshttp://en.wikipedia.org/w/index.php?title=Toluene&action=edit&section=9http://en.wikipedia.org/w/index.php?title=Toluene&action=edit&section=9http://en.wikipedia.org/w/index.php?title=Toluene&action=edit&section=9http://en.wikipedia.org/wiki/Coca-Cola_formulahttp://en.wikipedia.org/wiki/Coca-Cola_formulahttp://en.wikipedia.org/wiki/Coca-Cola_formulahttp://en.wikipedia.org/wiki/Toluene#cite_note-16http://en.wikipedia.org/wiki/Toluene#cite_note-16http://en.wikipedia.org/wiki/Toluene#cite_note-16http://en.wikipedia.org/w/index.php?title=Toluene&action=edit&section=10http://en.wikipedia.org/w/index.php?title=Toluene&action=edit&section=10http://en.wikipedia.org/w/index.php?title=Toluene&action=edit&section=10http://en.wikipedia.org/wiki/Toluene_(toxicology)http://en.wikipedia.org/wiki/Toluene_(toxicology)http://en.wikipedia.org/wiki/Toluene_(toxicology)http://en.wikipedia.org/wiki/Sudden_sniffing_deathhttp://en.wikipedia.org/wiki/Sudden_sniffing_deathhttp://en.wikipedia.org/wiki/Toluene#cite_note-17http://en.wikipedia.org/wiki/Toluene#cite_note-17http://en.wikipedia.org/wiki/Toluene#cite_note-17http://en.wikipedia.org/wiki/Benzenehttp://en.wikipedia.org/wiki/Benzenehttp://en.wikipedia.org/wiki/Benzenehttp://en.wikipedia.org/wiki/Toluene#cite_note-19http://en.wikipedia.org/wiki/Toluene#cite_note-19http://en.wikipedia.org/wiki/Toluene#cite_note-19http://en.wikipedia.org/wiki/1,1,1-trichloroethanehttp://en.wikipedia.org/wiki/1,1,1-trichloroethanehttp://en.wikipedia.org/wiki/1,1,1-trichloroethanehttp://en.wikipedia.org/wiki/Alkylhttp://en.wikipedia.org/wiki/Alkylhttp://en.wikipedia.org/wiki/Alkylhttp://en.wikipedia.org/wiki/Noncompetitive_inhibitionhttp://en.wikipedia.org/wiki/Noncompetitive_inhibitionhttp://en.wikipedia.org/wiki/Noncompetitive_inhibitionhttp://en.wikipedia.org/wiki/NMDA_receptor_antagonisthttp://en.wikipedia.org/wiki/NMDA_receptor_antagonisthttp://en.wikipedia.org/wiki/NMDA_receptor_antagonisthttp://en.wikipedia.org/wiki/GABAA_receptorhttp://en.wikipedia.org/wiki/GABAA_receptorhttp://en.wikipedia.org/wiki/GABAA_receptorhttp://en.wikipedia.org/wiki/GABAA_receptorhttp://en.wikipedia.org/wiki/Positive_allosteric_modulatorhttp://en.wikipedia.org/wiki/Positive_allosteric_modulatorhttp://en.wikipedia.org/wiki/Positive_allosteric_modulatorhttp://en.wikipedia.org/wiki/Toluene#cite_note-pmid19151967-20http://en.wikipedia.org/wiki/Toluene#cite_note-pmid19151967-20http://en.wikipedia.org/wiki/Toluene#cite_note-pmid19151967-20http://en.wikipedia.org/wiki/Inhalanthttp://en.wikipedia.org/wiki/Inhalanthttp://en.wikipedia.org/wiki/Inhalanthttp://en.wikipedia.org/wiki/Euphorianthttp://en.wikipedia.org/wiki/Euphorianthttp://en.wikipedia.org/wiki/Euphorianthttp://en.wikipedia.org/wiki/Dissociativehttp://en.wikipedia.org/wiki/Dissociativehttp://en.wikipedia.org/wiki/Dissociativehttp://en.wikipedia.org/wiki/Toluene#cite_note-pmid19151967-20http://en.wikipedia.org/wiki/Toluene#cite_note-pmid19151967-20http://en.wikipedia.org/wiki/Toluene#cite_note-pmid19151967-20http://en.wikipedia.org/wiki/Toluene#cite_note-pmid19151967-20http://en.wikipedia.org/wiki/Dissociativehttp://en.wikipedia.org/wiki/Euphorianthttp://en.wikipedia.org/wiki/Inhalanthttp://en.wikipedia.org/wiki/Toluene#cite_note-pmid19151967-20http://en.wikipedia.org/wiki/Positive_allosteric_modulatorhttp://en.wikipedia.org/wiki/Positive_allosteric_modulatorhttp://en.wikipedia.org/wiki/GABAA_receptorhttp://en.wikipedia.org/wiki/NMDA_receptor_antagonisthttp://en.wikipedia.org/wiki/Noncompetitive_inhibitionhttp://en.wikipedia.org/wiki/Noncompetitive_inhibitionhttp://en.wikipedia.org/wiki/Alkylhttp://en.wikipedia.org/wiki/Alkylhttp://en.wikipedia.org/wiki/1,1,1-trichloroethanehttp://en.wikipedia.org/wiki/Toluene#cite_note-19http://en.wikipedia.org/wiki/Benzenehttp://en.wikipedia.org/wiki/Toluene#cite_note-17http://en.wikipedia.org/wiki/Toluene#cite_note-17http://en.wikipedia.org/wiki/Sudden_sniffing_deathhttp://en.wikipedia.org/wiki/Toluene_(toxicology)http://en.wikipedia.org/w/index.php?title=Toluene&action=edit&section=10http://en.wikipedia.org/wiki/Toluene#cite_note-16http://en.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toluene has been shown to displayantidepressant-like effects in rodents in

theforced swim test(FST) and thetail suspension test(TST).[20]

vToluene/tluin/,formerly known as toluol/tlul/,is a clear,water-insoluble liquid with the

typical smell ofpaint thinners.It is a mono-substitutedbenzenederivative, i.e., one in which a single

hydrogen atom from a group of six atoms from the benzene molecule has been replaced by a univalent

group, in this caseCH3.As such, its IUPAC systematic name is methylbenzene.

It is anaromatic hydrocarbonthat is widely used as an industrialfeedstockand as asolvent.Like other

solvents, toluene is sometimes also used as aninhalantdrug for its intoxicating properties; however,




Contents

[hide]

1 History

2 Physical properties

3 Chemical properties

4 Production


5 Uses

o 5.1 Solvent

o 5.2 Fuel


6 Toxicology and metabolism

7 References

8 External links

History[edit]

The compound was first isolated in 1837 by aPolishchemistFilip Walterthrough a distillation ofpineoil

who named it retinaptha.[5]This name was replaced shortly after by the word toluenederived from the


treeMyroxylon balsamum,from which it was also isolated later.[6]

It was originally named byJns JakobBerzelius.

Physical properties[edit]

The surface tension of toluene is 27.73 dyn/cm.

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i/Tolu_balsamhttp://en.wikipedia.org/wiki/Tolu_balsamhttp://en.wikipedia.org/wiki/Tolu_balsamhttp://en.wikipedia.org/wiki/Myroxylonhttp://en.wikipedia.org/wiki/Myroxylonhttp://en.wikipedia.org/wiki/Myroxylonhttp://en.wikipedia.org/wiki/Toluene#cite_note-6http://en.wikipedia.org/wiki/Toluene#cite_note-6http://en.wikipedia.org/wiki/Toluene#cite_note-6http://en.wikipedia.org/wiki/J%C3%B6ns_Jakob_Berzeliushttp://en.wikipedia.org/wiki/J%C3%B6ns_Jakob_Berzeliushttp://en.wikipedia.org/wiki/J%C3%B6ns_Jakob_Berzeliushttp://en.wikipedia.org/wiki/J%C3%B6ns_Jakob_Berzeliushttp://en.wikipedia.org/w/index.php?title=Toluene&action=edit&section=2http://en.wikipedia.org/w/index.php?title=Toluene&action=edit&section=2http://en.wikipedia.org/w/index.php?title=Toluene&action=edit&section=2http://en.wikipedia.org/w/index.php?title=Toluene&action=edit&section=3http://en.wikipedia.org/w/index.php?title=Toluene&action=edit&section=3http://en.wikipedia.org/w/index.php?title=Toluene&action=edit&section=3http://en.wikipedia.org/w/index.php?title=Toluene&action=edit&section=3http://en.wikipedia.org/w/index.php?title=Toluene&action=edit&section=2http://en.wikipedia.org/wiki/J%C3%B6ns_Jakob_Berzeliushttp://en.wikipedia.org/wiki/J%C3%B6ns_Jakob_Berzeliushttp://en.wikipedia.org/wiki/Toluene#cite_note-6http://en.wikipedia.org/wiki/Myroxylonhttp://en.wikipedia.org/wiki/Tolu_balsamhttp://en.wikipedia.org/wiki/Toluene#cite_note-5http://en.wikipedia.org/wiki/Pinehttp://en.wikipedia.org/w/index.php?title=Filip_Walter&action=edit&redlink=1http://en.wikipedia.org/wiki/Poleshttp://en.wikipedia.org/w/index.php?title=Toluene&action=edit&section=1http://en.wikipedia.org/wiki/Toluene#External_linkshttp://en.wikipedia.org/wiki/Toluene#Referenceshttp://en.wikipedia.org/wiki/Toluene#Toxicology_and_metabolismhttp://en.wikipedia.org/wiki/Toluene#Niche_applicationshttp://en.wikipedia.org/wiki/Toluene#Fuelhttp://en.wikipedia.org/wiki/Toluene#Solventhttp://en.wikipedia.org/wiki/Toluene#Useshttp://en.wikipedia.org/wiki/Toluene#Laboratory_preparationhttp://en.wikipedia.org/wiki/Toluene#Productionhttp://en.wikipedia.org/wiki/Toluene#Chemical_propertieshttp://en.wikipedia.org/wiki/Toluene#Physical_propertieshttp://en.wikipedia.org/wiki/Toluene#Historyhttp://en.wikipedia.org/wiki/Toluenehttp://en.wikipedia.org/wiki/Toluene#cite_note-4http://en.wikipedia.org/wiki/Toluene#cite_note-2http://en.wikipedia.org/wiki/Toluene#cite_note-2http://en.wikipedia.org/wiki/Inhalanthttp://en.wikipedia.org/wiki/Solventhttp://en.wikipedia.org/wiki/Feedstockhttp://en.wikipedia.org/wiki/Aromatic_hydrocarbonhttp://en.wikipedia.org/wiki/Methyl_grouphttp://en.wikipedia.org/wiki/Benzenehttp://en.wikipedia.org/wiki/Paint_thinnerhttp://en.wikipedia.org/wiki/Water_(molecule)http://en.wikipedia.org/wiki/Help:IPA_for_Englishhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_Englishhttp://en.wikipedia.org/wiki/Help:IPA_for_Englishhttp://en.wikipedia.org/wiki/Help:IPA_for_Englishhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_Englishhttp://en.wikipedia.org/wiki/Help:IPA_for_Englishhttp://en.wikipedia.org/wiki/Toluene#cite_note-pmid19151967-20http://en.wikipedia.org/wiki/Tail_suspension_testhttp://en.wikipedia.org/wiki/Forced_swim_testhttp://en.wikipedia.org/wiki/Antidepressant

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presence ofFeCl3to give ortho and paraisomersofchlorotoluene.

With otherreagentsthe methylside chainin toluene may react, undergoing oxidation. Reaction







of light.[10]



Production[edit]





Laboratory preparation[edit]Toluene can be prepared industrially or in the laboratory by a variety of methods.






Many catalysts can be used in place of AlCl3. Their order of reactivity is :AlCl3> SbCl3> SnCl4>

BF3> ZnCl2> HgCl2. The reaction is not very useful because toluene formed readily undergoes






C6H5Br + CH3Br + 2Na C6H5CH3+ 2NaBr
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ikipedia.org/wiki/Catalytic_reforminghttp://en.wikipedia.org/wiki/Catalytic_reforminghttp://en.wikipedia.org/wiki/Ethylenehttp://en.wikipedia.org/wiki/Ethylenehttp://en.wikipedia.org/wiki/Cracking_(chemistry)http://en.wikipedia.org/wiki/Cracking_(chemistry)http://en.wikipedia.org/wiki/Cracking_(chemistry)http://en.wikipedia.org/wiki/Coke_(fuel)http://en.wikipedia.org/wiki/Coke_(fuel)http://en.wikipedia.org/wiki/Coke_(fuel)http://en.wikipedia.org/wiki/Coalhttp://en.wikipedia.org/wiki/Coalhttp://en.wikipedia.org/wiki/Coalhttp://en.wikipedia.org/wiki/Distillationhttp://en.wikipedia.org/wiki/Distillationhttp://en.wikipedia.org/wiki/Distillationhttp://en.wikipedia.org/wiki/Solvent_extractionhttp://en.wikipedia.org/wiki/Solvent_extractionhttp://en.wikipedia.org/wiki/Solvent_extractionhttp://en.wikipedia.org/wiki/BTX_(chemistry)http://en.wikipedia.org/wiki/BTX_(chemistry)http://en.wikipedia.org/wiki/BTX_(chemistry)http://en.wikipedia.org/w/index.php?title=Toluene&action=edit&section=5http://en.wikipedia.org/w/index.php?title=Toluene&action=edit&section=5http://en.wikipedia.org/w/index.php?title=Toluene&action=edit&section=5http://en.wikipedia.org/wiki/Benzenehttp://en.wikipedia.org/wiki/Benzenehttp://en.wikipedia.org/wiki/Benzenehttp://en.wikipedia.org/wiki/Friedel%E2%80%93Crafts_reactionhttp://en.wikipedia.org/wiki/Friedel%E2%80%93Crafts_reactionhttp://en.wikipedia.org/wiki/Friedel%E2%80%93Crafts_reactionhttp://en.wikipedia.org/wiki/Friedel%E2%80%93Crafts_reactionhttp://en.wikipedia.org/wiki/Friedel%E2%80%93Crafts_reactionhttp://en.wikipedia.org/wiki/Bromobenzenehttp://en.wikipedia.org/wiki/Bromobenzenehttp://en.wikipedia.org/wiki/Bromobenzenehttp://en.wikipedia.org/wiki/Wurtz-Fittig_reactionhttp://en.wikipedia.org/wiki/Wurtz-Fittig_reactionhttp://en.wikipedia.org/wiki/Wurtz-Fittig_reactionhttp://en.wikipedia.org/wiki/Bromobenzenehttp://en.wikipedia.org/wiki/Bromobenzenehttp://en.wikipedia.org/wiki/Bromobenzenehttp://en.wikipedia.org/wiki/Methyl_bromidehttp://en.wikipedia.org/wiki/Methyl_bromidehttp://en.wikipedia.org/wiki/Methyl_bromidehttp://en.wikipedia.org/wiki/Wikipedia:Citation_neededhttp://en.wikipedia.org/wiki/Wikipedia:Citation_neededhttp://en.wikipedia.org/wiki/Wikipedia:Citation_neededhttp://en.wikipedia.org/wiki/File:TolueneBromination2006.pnghttp://en.wikipedia.org/wiki/Wikipedia:Citation_neededhttp://en.wikipedia.org/wiki/Methyl_bromidehttp://en.wikipedia.org/wiki/Bromobenzenehttp://en.wikipedia.org/wiki/Wurtz-Fittig_reactionhttp://en.wikipedia.org/wiki/Bromobenzenehttp://en.wikipedia.org/wiki/Friedel%E2%80%93Crafts_reactionhttp://en.wikipedia.org/wiki/Benzenehttp://en.wikipedia.org/w/index.php?title=Toluene&action=edit&section=5http://en.wikipedia.org/wiki/BTX_(chemistry)http://en.wikipedia.org/wiki/Solvent_extractionhttp://en.wikipedia.org/wiki/Distillationhttp://en.wikipedia.org/wiki/Coalhttp://en.wikipedia.org/wiki/Coke_(fuel)http://en.wikipedia.org/wiki/Cracking_(chemistry)http://en.wikipedia.org/wiki/Ethylenehttp://en.wikipedia.org/wiki/Catalytic_reforminghttp://en.wikipedia.org/wiki/Gasolinehttp://en.wikipedia.org/wiki/Crude_oilhttp://en.wikipedia.org/w/index.php?title=Toluene&action=edit&section=4http://en.wikipedia.org/wiki/Hydrogenhttp://en.wikipedia.org/wiki/Methylcyclohexanehttp://en.wikipedia.org/wiki/Hydrogenationhttp://en.wikipedia.org/wiki/Toluene#cite_note-10http://en.wikipedia.org/wiki/Benzyl_bromidehttp://en.wikipedia.org/wiki/Brominehttp://en.wikipedia.org/wiki/Benzyl_bromidehttp://en.wikipedia.org/wiki/Benzyl_bromidehttp://en.wikipedia.org/wiki/Azobisisobutyronitrilehttp://en.wikipedia.org/wiki/N-Bromosuccinimidehttp://en.wikipedia.org/wiki/Free_radicalhttp://en.wikipedia.org/wiki/Halogenationhttp://en.wikipedia.org/wiki/%C3%89tard_reactionhttp://en.wikipedia.org/wiki/Benzaldehydehttp://en.wikipedia.org/wiki/Chromyl_chloridehttp://en.wikipedia.org/wiki/Benzoic_acidhttp://en.wikipedia.org/wiki/Sulfuric_acidhttp://en.wikipedia.org/wiki/Potassium_permanganatehttp://en.wikipedia.org/wiki/Sulfuric_acidhttp://en.wikipedia.org/wiki/Potassium_permanganatehttp://en.wikipedia.org/wiki/Side_chainhttp://en.wikipedia.org/wiki/Reagentshttp://en.wikipedia.org/wiki/Chlorotoluenehttp://en.wikipedia.org/wiki/Isomerhttp://en.wikipedia.org/wiki/Iron(III)_chloridehttp://en.wikipedia.org/wiki/Chlorinehttp://en.wikipedia.org/wiki/Halogenationhttp://en.wikipedia.org/wiki/P-Toluenesulfonic_acidhttp://en.wikipedia.org/wiki/Sulfonationhttp://en.wikipedia.org/wiki/Benzenehttp://en.wikipedia.org/wiki/Methylhttp://en.wikipedia.org/wiki/Toluene#cite_note-9http://en.wikipedia.org/wiki/Toluene#cite_note-7http://en.wikipedia.org/wiki/Toluene#cite_note-7http://en.wikipedia.org/wiki/Electrophilic_aromatic_substitutionhttp://en.wikipedia.org/wiki/Electrophilic_aromatic_substitutionhttp://en.wikipedia.org/wiki/Aromatic_hydrocarbon

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From toluic acid (decarboxylation)

When sodium salt of toluic acid (o-,m-,p-)is heated withsoda lime,toluene is obtained.

C6H4CH3COONa (sodium toluate) + NaOH C6H5CH3(toluene) + Na2CO3

Fromcresol

When cresol (o-, m-, p-) is distilled from zinc dust, toluene is obtained.

C6H4CH3OH (cresol) + Zn C6H5CH3(toluene) + ZnO

Fromtoluenesulfonic acid

When toluenesulfonic acid is treated with superheated steam or boiled with HCl,

toluene is obtained.

CH3C6H4SO3H (toluenesulfonic acid) + HOH (steam) C6H5CH3(toluene) + H2SO4(sulfuric

acid)

Fromtoluidine

Toluidine is first diazotized withsodium nitrite(NaNO2) and HCl at lowtemperature. Thediazoniumcompound thus obtained is heated with

alkalinestannous chloride(SnCl2). This reaction gives toluene.

Uses[edit]

Toluene is mainly used as a precursor to benzene. The process involves

hydrodealkylation:

C6H5CH3+ H2C6H6+ CH4

The second ranked application involves itsdisproportionationto a mixture

of benzene andxylene.When oxidized it yields benzaldehyde and benzoicacid, two important intermediates in chemistry.[11]

Solvent[edit]

Toluene is a commonsolvent,able to dissolvepaints,paint thinners,

silicone sealants,[12]manychemical

reactants,rubber,printingink,adhesives(glues),lacquers,leather tanners,

anddisinfectants.It can also be used as afullereneindicator, and is a raw

material fortoluene diisocyanate(used in the manufacture

ofpolyurethanefoam) andTNT.In addition, it is used as a solvent for

carbon nanotubes. It is also used as a cement for finepolystyrenekits(by

dissolving and then fusing surfaces) as it can be applied very precisely bybrush and contains none of the bulk of an adhesive. Toluene can be used

to break openred blood cellsin order to extracthemoglobinin biochemistry

experiments.

Fuel[edit]

Toluene can be used as anoctane boosteringasolinefuels used

ininternal combustion engines.Toluene at 86% by volume fueled all the
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g/wiki/Gasolinehttp://en.wikipedia.org/wiki/Gasolinehttp://en.wikipedia.org/wiki/Internal_combustion_enginehttp://en.wikipedia.org/wiki/Internal_combustion_enginehttp://en.wikipedia.org/wiki/Internal_combustion_enginehttp://en.wikipedia.org/wiki/Internal_combustion_enginehttp://en.wikipedia.org/wiki/Gasolinehttp://en.wikipedia.org/wiki/Octane_ratinghttp://en.wikipedia.org/w/index.php?title=Toluene&action=edit&section=8http://en.wikipedia.org/wiki/Hemoglobinhttp://en.wikipedia.org/wiki/Red_blood_cellshttp://en.wikipedia.org/wiki/Plastic_modelhttp://en.wikipedia.org/wiki/Polystyrenehttp://en.wikipedia.org/wiki/Trinitrotoluenehttp://en.wikipedia.org/wiki/Polyurethanehttp://en.wikipedia.org/wiki/Toluene_diisocyanatehttp://en.wikipedia.org/wiki/Fullerenehttp://en.wikipedia.org/wiki/Disinfectanthttp://en.wikipedia.org/wiki/Leather_tanninghttp://en.wikipedia.org/wiki/Lacquerhttp://en.wikipedia.org/wiki/Adhesivehttp://en.wikipedia.org/wiki/Printinghttp://en.wikipedia.org/wiki/Rubberhttp://en.wikipedia.org/wiki/Chemical_reactanthttp://en.wikipedia.org/wiki/Chemical_reactanthttp://en.wikipedia.org/wiki/Toluene#cite_note-12http://en.wikipedia.org/wiki/Painthttp://en.wikipedia.org/wiki/Solventhttp://en.wikipedia.org/w/index.php?title=Toluene&action=edit&section=7http://en.wikipedia.org/wiki/Toluene#cite_note-11http://en.wikipedia.org/wiki/Xylenehttp://en.wikipedia.org/wiki/Disproportionationhttp://en.wikipedia.org/w/index.php?title=Toluene&action=edit&section=6http://en.wikipedia.org/wiki/Stannous_chloridehttp://en.wikipedia.org/wiki/Diazoniumhttp://en.wikipedia.org/wiki/Sodium_nitritehttp://en.wikipedia.org/wiki/Toluidinehttp://en.wikipedia.org/wiki/Sulfuric_acidhttp://en.wikipedia.org/wiki/Sulfuric_acidhttp://en.wikipedia.org/wiki/Toluenesulfonic_acidhttp://en.wikipedia.org/wiki/Cresolhttp://en.wikipedia.org/wiki/Soda_limehttp://en.wikipedia.org/wiki/P-Toluic_acidhttp://en.wikipedia.org/wiki/M-Toluic_acidhttp://en.wikipedia.org/wiki/O-Toluic_acidhttp://en.wikipedia.org/wiki/Decarboxylation

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turbo Formula 1 teams in the 1980s, first pioneered by the Honda team.

The remaining 14% was a "filler" of n-heptane, to reduce the octane to

meet Formula 1 fuel restrictions. Toluene at 100% can be used as a fuel for

both two-stroke and four-stroke engines; however, due to the density of the

fuel and other factors, the fuel does not vaporize easily unless preheated to

70 degrees Celsius (Honda accomplished this in their Formula 1 cars byrouting the fuel lines through the muffler system to heat the fuel). Toluene

also poses similar problems as alcohol fuels, as it eats through standard

rubber fuel lines and has no lubricating properties, as standard gasoline

does,[citation needed]which can break down fuel pumps and cause upper

cylinder bore wear.

In Australia, toluene has been found to have been illegally combined with

petrol in fuel outlets for sale as standard vehicular fuel. Toluene attracts no

fuel excise, while other fuels are taxed at over 40%, so fuel suppliers are

able to profit from substituting the cheaper toluene for petrol. This

substitution is likely to affect engine performance and result in additionalwear and tear. The extent of toluene substitution has not been

determined.[13][14]

Toluene is another in a group of fuels that have recently been used as

components forjet fuelsurrogate blends.[15]Toluene is used as ajet fuel

surrogatefor its content ofaromatic compounds.

Niche applications[edit]

Toluene has also been used as a coolant for its good heat transfer

capabilities in sodium cold traps used in nuclear reactor system loops.

Toluene had also been used in the process ofremoving the cocainefromcoca leaves in the production of Coca-Cola syrup.[16]

Toxicology and metabolism[edit]

Main article:Toluene (toxicology)

Inhalation of toluene in low to moderate levels can cause tiredness,

confusion, weakness, drunken-type actions, memory loss, nausea, loss of

appetite, and hearing and color vision loss. These symptoms usually

disappear when exposure is stopped. Inhaling high levels of toluene in a

short time may cause light-headedness, nausea, or sleepiness. It can also

cause unconsciousness, and evendeath.[17][18]

Toluene is, however, much less toxic thanbenzene,and has, as a

consequence, largely replaced it as an aromatic solvent in chemical

preparation. For example, benzene is a known carcinogen, whereas

toluene has very little carcinogenic potential.[19]

Similar to many other solvents such as1,1,1-trichloroethaneand

somealkylbenzenes,toluene has been shown to act as anon-
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competitiveNMDA receptor antagonistandGABAAreceptorpositive

allosteric modulator.[20]It is abused as aninhalantlikely on account of

theeuphoricanddissociativeeffects these actions produce.[20]Additionally,

toluene has been shown to displayantidepressant-like effects in rodents in

theforced swim test(FST) and thetail suspension test(TST).[20]

Toluene/tluin/,formerly known as toluol/tlul/,is a clear,water-insoluble liquid with the typical

smell ofpaint thinners.It is a mono-substitutedbenzenederivative, i.e., one in which a single hydrogen

atom from a group of six atoms from the benzene molecule has been replaced by a univalent group, in

this caseCH3.As such, its IUPAC systematic name is methylbenzene.

It is anaromatic hydrocarbonthat is widely used as an industrialfeedstockand as asolvent.Like other

solvents, toluene is sometimes also used as aninhalantdrug for its intoxicating properties; however,




Contents

[hide]

1 History

2 Physical properties

3 Chemical properties

4 Production


5 Uses

o 5.1 Solvent

o 5.2 Fuel


6 Toxicology and metabolism

7 References

8 External links

History[edit]

The compound was first isolated in 1837 by aPolishchemistFilip Walterthrough a distillation ofpineoilwho named it retinaptha.[5]This name was replaced shortly after by the word toluenederived from the


treeMyroxylon balsamum,from which it was also isolated later.[6]It was originally named byJns Jakob

Berzelius.

Physical properties[edit]

The surface tension of toluene is 27.73 dyn/cm.
http://en.wikipedia.org/wiki/Noncompetitive_inhibitionhttp://en.wikipedia.org/wiki/NMDA_receptor_antagonisthttp://en.wikipedia.org/wiki/NMDA_receptor_antagonisthttp://en.wikipedia.org/wiki/NMDA_receptor_antagonisthttp://en.wikipedia.org/wiki/GABAA_receptorhttp://en.wikipedia.org/wiki/GABAA_receptorhttp://en.wikipedia.org/wiki/GABAA_receptorhttp://en.wikipedia.org/wiki/GABAA_receptorhttp://en.wikipedia.org/wiki/Positive_allosteric_modulatorhttp://en.wikipedia.org/wiki/Positive_allosteric_modulatorhttp://en.wikipedia.org/wiki/Positive_allosteric_modulatorhttp://en.wikipedia.org/wiki/Toluene#cite_note-pmid19151967-20http://en.wikipedia.org/wiki/Toluene#cite_note-pmid19151967-20http://en.wikipedia.org/wiki/Toluene#cite_note-pmid19151967-20http://en.wikipedia.org/wiki/Inhalanthttp://en.wikipedia.org/wiki/Inhalanthttp://en.wikipedia.org/wiki/Inhalanthttp://en.wikipedia.org/wiki/Euphorianthttp://en.wikipedia.org/wiki/Euphorianthttp://en.wikipedia.org/wiki/Euphorianthttp://en.wikipedia.org/wiki/Dissociativehttp://en.wikipedia.org/wiki/Dissociativehttp://en.wikipedia.org/wiki/Dissociativehttp://en.wikipedia.org/wiki/Toluene#cite_note-pmid19151967-20http://en.wikipedia.org/wiki/Toluene#cite_note-pmid19151967-20http://en.wikipedia.org/wiki/Toluene#cite_note-pmid19151967-20http://en.wikipedia.org/wiki/Antidepressanthttp://en.wikipedia.org/wiki/Antidepressanthttp://en.wikipedia.org/wiki/Antidepressanthttp://en.wikipedia.org/wiki/Forced_swim_testhttp://en.wikipedia.org/wiki/Forced_swim_testhttp://en.wikipedia.org/wiki/Forced_swim_testhttp://en.wikipedia.org/wiki/Tail_suspension_testhttp://en.wikipedia.org/wiki/Tail_suspension_testhttp://en.wikipedia.org/wiki/Tail_suspension_testhttp://en.wikipedia.org/wiki/Toluene#cite_note-pmid19151967-20http://en.wikipedia.org/wiki/Toluene#cite_note-pmid19151967-20http://en.wikipedia.org/wiki/Toluene#cite_note-pmid19151967-20http://en.wikipedia.org/wiki/Help:IPA_for_Englishhttp://en.wikipedia.org/wiki/Help:IPA_for_Englishhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_Englishhttp://en.wikipedia.org/wiki/Help:IPA_for_Englishhttp://en.wikipedia.org/wiki/Help:IPA_for_Englishhttp://en.wikipedia.org/wiki/Help:IPA_for_Englishhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_Englishhttp://en.wikipedia.org/wiki/Help:IPA_for_Englishhttp://en.wikipedia.org/wiki/Water_(molecule)http://en.wikipedia.org/wiki/Water_(molecule)http://en.wikipedia.org/wiki/Water_(molecule)http://en.wikipedia.org/wiki/Paint_thinnerhttp://en.wikipedia.org/wiki/Paint_thinnerhttp://en.wikipedia.org/wiki/Paint_thinnerhttp://en.wikipedia.org/wiki/Benzenehttp://en.wikipedia.org/wiki/Benzenehttp://en.wikipedia.org/wiki/Benzenehttp://en.wikipedia.org/wiki/Methyl_grouphttp://en.wikipedia.org/wiki/Methyl_grouphttp://en.wikipedia.org/wiki/Methyl_grouphttp://en.wikipedia.org/wiki/Methyl_grouphttp://en.wikipedia.org/wiki/Aromatic_hydrocarbonhttp://en.wikipedia.org/wiki/Aromatic_hydrocarbonhttp://en.wikipedia.org/wiki/Aromatic_hydrocarbonhttp://en.wikipedia.org/wiki/Feedstockhttp://en.wikipedia.org/wiki/Feedstockhttp://en.wikipedia.org/wiki/Feedstockhttp://en.wikipedia.org/wiki/Solventhttp://en.wikipedia.org/wiki/Solventhttp://en.wikipedia.org/wiki/Solventhttp://en.wikipedia.org/wiki/Inhalanthttp://en.wikipedia.org/wiki/Inhalanthttp://en.wikipedia.org/wiki/Inhalanthttp://en.wikipedia.org/wiki/Toluene#cite_note-2http://en.wikipedia.org/wiki/Toluene#cite_note-2http://en.wikipedia.org/wiki/Toluene#cite_note-2http://en.wikipedia.org/wiki/Toluene#cite_note-4http://en.wikipedia.org/wiki/Toluene#cite_note-4http://en.wikipedia.org/wiki/Toluene#cite_note-4http://en.wikipedia.org/wiki/Toluenehttp://en.wikipedia.org/wiki/Toluenehttp://en.wikipedia.org/wiki/Toluenehttp://en.wikipedia.org/wiki/Toluene#Historyhttp://en.wikipedia.org/wiki/Toluene#Historyhttp://en.wikipedia.org/wiki/Toluene#Physical_propertieshttp://en.wikipedia.org/wiki/Toluene#Physical_propertieshttp://en.wikipedia.org/wiki/Toluene#Chemical_propertieshttp://en.wikipedia.org/wiki/Toluene#Chemical_propertieshttp://en.wikipedia.org/wiki/Toluene#Productionhttp://en.wikipedia.org/wiki/Toluene#Productionhttp://en.wikipedia.org/wiki/Toluene#Laboratory_preparationhttp://en.wikipedia.org/wiki/Toluene#Laboratory_preparationhttp://en.wikipedia.org/wiki/Toluene#Useshttp://en.wikipedia.org/wiki/Toluene#Useshttp://en.wikipedia.org/wiki/Toluene#Solventhttp://en.wikipedia.org/wiki/Toluene#Solventhttp://en.wikipedia.org/wiki/Toluene#Fuelhttp://en.wikipedia.org/wiki/Toluene#Fuelhttp://en.wikipedia.org/wiki/Toluene#Niche_applicationshttp://en.wikipedia.org/wiki/Toluene#Niche_applicationshttp://en.wikipedia.org/wiki/Toluene#Toxicology_and_metabolismhttp://en.wikipedia.org/wiki/Toluene#Toxicology_and_metabolismhttp://en.wikipedia.org/wiki/Toluene#Referenceshttp://en.wikipedia.org/wiki/Toluene#Referenceshttp://en.wikipedia.org/wiki/Toluene#External_linkshttp://en.wikipedia.org/wiki/Toluene#External_linkshttp://en.wikipedia.org/w/index.php?title=Toluene&action=edit&section=1http://en.wikipedia.org/w/index.php?title=Toluene&action=edit&section=1http://en.wikipedia.org/w/index.php?title=Toluene&action=edit&section=1http://en.wikipedia.org/wiki/Poleshttp://en.wikipedia.org/wiki/Poleshttp://en.wikipedia.org/wiki/Poleshttp://en.wikipedia.org/w/index.php?title=Filip_Walter&action=edit&redlink=1http://en.wikipedia.org/w/index.php?title=Filip_Walter&action=edit&redlink=1http://en.wikipedia.org/w/index.php?title=Filip_Walter&action=edit&redlink=1http://en.wikipedia.org/wiki/Pinehttp://en.wikipedia.org/wiki/Pinehttp://en.wikipedia.org/wiki/Pinehttp://en.wikipedia.org/wiki/Toluene#cite_note-5http://en.wikipedia.org/wiki/Toluene#cite_note-5http://en.wikipedia.org/wiki/Toluene#cite_note-5http://en.wikipedia.org/wiki/Tolu_balsamhttp://en.wikipedia.org/wiki/Tolu_balsamhttp://en.wikipedia.org/wiki/Tolu_balsamhttp://en.wikipedia.org/wiki/Myroxylonhttp://en.wikipedia.org/wiki/Myroxylonhttp://en.wikipedia.org/wiki/Myroxylonhttp://en.wikipedia.org/wiki/Toluene#cite_note-6http://en.wikipedia.org/wiki/Toluene#cite_note-6http://en.wikipedia.org/wiki/Toluene#cite_note-6http://en.wikipedia.org/wiki/J%C3%B6ns_Jakob_Berzeliushttp://en.wikipedia.org/wiki/J%C3%B6ns_Jakob_Berzeliushttp://en.wikipedia.org/wiki/J%C3%B6ns_Jakob_Berzeliushttp://en.wikipedia.org/wiki/J%C3%B6ns_Jakob_Berzeliushttp://en.wikipedia.org/w/index.php?title=Toluene&action=edit&section=2http://en.wikipedia.org/w/index.php?title=Toluene&action=edit&section=2http://en.wikipedia.org/w/index.php?title=Toluene&action=edit&section=2http://en.wikipedia.org/w/index.php?title=Toluene&action=edit&section=2http://en.wikipedia.org/wiki/J%C3%B6ns_Jakob_Berzeliushttp://en.wikipedia.org/wiki/J%C3%B6ns_Jakob_Berzeliushttp://en.wikipedia.org/wiki/Toluene#cite_note-6http://en.wikipedia.org/wiki/Myroxylonhttp://en.wikipedia.org/wiki/Tolu_balsamhttp://en.wikipedia.org/wiki/Toluene#cite_note-5http://en.wikipedia.org/wiki/Pinehttp://en.wikipedia.org/w/index.php?title=Filip_Walter&action=edit&redlink=1http://en.wikipedia.org/wiki/Poleshttp://en.wikipedia.org/w/index.php?title=Toluene&action=edit&section=1http://en.wikipedia.org/wiki/Toluene#External_linkshttp://en.wikipedia.org/wiki/Toluene#Referenceshttp://en.wikipedia.org/wiki/Toluene#Toxicology_and_metabolismhttp://en.wikipedia.org/wiki/Toluene#Niche_applicationshttp://en.wikipedia.org/wiki/Toluene#Fuelhttp://en.wikipedia.org/wiki/Toluene#Solventhttp://en.wikipedia.org/wiki/Toluene#Useshttp://en.wikipedia.org/wiki/Toluene#Laboratory_preparationhttp://en.wikipedia.org/wiki/Toluene#Productionhttp://en.wikipedia.org/wiki/Toluene#Chemical_propertieshttp://en.wikipedia.org/wiki/Toluene#Physical_propertieshttp://en.wikipedia.org/wiki/Toluene#Historyhttp://en.wikipedia.org/wiki/Toluenehttp://en.wikipedia.org/wiki/Toluene#cite_note-4http://en.wikipedia.org/wiki/Toluene#cite_note-2http://en.wikipedia.org/wiki/Toluene#cite_note-2http://en.wikipedia.org/wiki/Inhalanthttp://en.wikipedia.org/wiki/Solventhttp://en.wikipedia.org/wiki/Feedstockhttp://en.wikipedia.org/wiki/Aromatic_hydrocarbonhttp://en.wikipedia.org/wiki/Methyl_grouphttp://en.wikipedia.org/wiki/Benzenehttp://en.wikipedia.org/wiki/Paint_thinnerhttp://en.wikipedia.org/wiki/Water_(molecule)http://en.wikipedia.org/wiki/Help:IPA_for_Englishhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_Englishhttp://en.wikipedia.org/wiki/Help:IPA_for_Englishhttp://en.wikipedia.org/wiki/Help:IPA_for_Englishhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_English#Keyhttp://en.wikipedia.org/wiki/Help:IPA_for_Englishhttp://en.wikipedia.org/wiki/Help:IPA_for_Englishhttp://en.wikipedia.org/wiki/Toluene#cite_note-pmid19151967-20http://en.wikipedia.org/wiki/Tail_suspension_testhttp://en.wikipedia.org/wiki/Forced_swim_testhttp://en.wikipedia.org/wiki/Antidepressanthttp://en.wikipedia.org/wiki/Toluene#cite_note-pmid19151967-20http://en.wikipedia.org/wiki/Dissociativehttp://en.wikipedia.org/wiki/Euphorianthttp://en.wikipedia.org/wiki/Inhalanthttp://en.wikipedia.org/wiki/Toluene#cite_note-pmid19151967-20http://en.wikipedia.org/wiki/Positive_allosteric_modulatorhttp://en.wikipedia.org/wiki/Positive_allosteric_modulatorhttp://en.wikipedia.org/wiki/GABAA_receptorhttp://en.wikipedia.org/wiki/NMDA_receptor_antagonisthttp://en.wikipedia.org/wiki/Noncompetitive_inhibition

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presence ofFeCl3to give ortho and paraisomersofchlorotoluene.With otherreagentsthe methylside chainin toluene may react, undergoing oxidation. Reaction







of light.[10]



Production[edit]





Laboratory preparation[edit]

Toluene can be prepared industrially or in the laboratory by a variety of methods.






Many catalysts can be used in place of AlCl3. Their order of reactivity is :AlCl3> SbCl3> SnCl4>BF3> ZnCl2> HgCl2. The reaction is not very useful because toluene formed readily undergoes





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toulene

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