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Toluene (), also known as toluol (), is a substituted aromatic hydrocarbon. It is a colorless, water-insoluble liquid with the smell associated with paint thinners. It is a mono-substituted benzene derivative, consisting of a methyl group (CH3) attached to a phenyl group. As such, its systematic IUPAC name is methylbenzene. Toluene is predominantly used as an industrial feedstock and a solvent.

Toluene
Names
Preferred IUPAC name
Toluene
Systematic IUPAC name
Methylbenzene
Other names
Phenyl methane
Toluol
Anisen
Identifiers
3D model (JSmol)
Abbreviations PhMe
MePh
BnH
Tol
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.003.297
KEGG
RTECS number
  • XS5250000
UNII
  • InChI=1S/C7H8/c1-7-5-3-2-4-6-7/h2-6H,1H3 Y
    Key: YXFVVABEGXRONW-UHFFFAOYSA-N Y
  • InChI=1/C7H8/c1-7-5-3-2-4-6-7/h2-6H,1H3
    Key: YXFVVABEGXRONW-UHFFFAOYAT
  • Cc1ccccc1
Properties
C7H8
Molar mass 92.141 g·mol−1
Appearance Colorless liquid
Odor sweet, pungent, benzene-like
Density 0.87 g/mL (20 °C)
Melting point −95 °C (−139 °F; 178 K)
Boiling point 111 °C (232 °F; 384 K)
0.52 g/L (20 °C)
log P 2.68
Vapor pressure 2.8 kPa (20 °C)
−66.11·10−6 cm3/mol
1.497 (20 °C)
Viscosity 0.590 cP (20 °C)
Structure
0.36 D
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
highly flammable
GHS labelling:
Danger
H225, H304, H315, H336, H361d, H373
P210, P240, P301+P310, P302+P352, P308+P313, P314, P403+P233
NFPA 704 (fire diamond)
2
3
0
Flash point 4 °C (39 °F; 277 K)
Explosive limits 1.1–7.1%
50 mL/m3, 190 mg/m3
Lethal dose or concentration (LD, LC):
>26700 ppm (rat, 1 h)
400 ppm (mouse, 24 h)
55,000 ppm (rabbit, 40 min)
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 200 ppm C 300 ppm 500 ppm (10-minute maximum peak)
REL (Recommended)
TWA 100 ppm (375 mg/m3) ST 150 ppm (560 mg/m3)
IDLH (Immediate danger)
500 ppm
Safety data sheet (SDS) SIRI.org
Related compounds
benzene
xylene
naphthalene
Related compounds
methylcyclohexane
Supplementary data page
Toluene (data page)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Nverify (what is YN ?)

As the solvent in some types of paint thinner, permanent markers, contact cement and certain types of glue, toluene is sometimes used as a recreational inhalant and has the potential of causing severe neurological harm.

Contents

The compound was first isolated in 1837 through a distillation of pine oil by the Polish chemist Filip Walter, who named it rétinnaphte. In 1841, French chemist Henri Étienne Sainte-Claire Deville isolated a hydrocarbon from balsam of Tolu (an aromatic extract from the tropical Colombian tree Myroxylon balsamum), which Deville recognized as similar to Walter's rétinnaphte and to benzene; hence he called the new hydrocarbon benzoène. In 1843, Jöns Jacob Berzelius recommended the name toluin. In 1850, French chemist Auguste Cahours isolated from a distillate of wood a hydrocarbon which he recognized as similar to Deville's benzoène and which Cahours named toluène.

Toluene reacts as a normal aromatic hydrocarbon in electrophilic aromatic substitution. Because the methyl group has greater electron-releasing properties than a hydrogen atom in the same position, toluene is more reactive than benzene toward electrophiles. It undergoes sulfonation to give p-toluenesulfonic acid, and chlorination by Cl2 in the presence of FeCl3 to give ortho and para isomers of chlorotoluene.

Importantly, the methyl side chain in toluene is susceptible to oxidation. Toluene reacts with potassium permanganate to yield benzoic acid, and with chromyl chloride to yield benzaldehyde (Étard reaction).

The C-H bonds of the methyl group in toluene are benzylic, which means that they are weaker than C-H bonds in simpler alkanes. Reflecting this weakness, the methyl group in toluene undergoes halogenation under free radical conditions. For example, when heated with N-bromosuccinimide (NBS) in the presence of AIBN, toluene converts to benzyl bromide. The same conversion can be effected with elemental bromine in the presence of UV light or even sunlight.

Toluene may also be brominated by treating it with HBr and H2O2 in the presence of light.

C6H5CH3 + Br2 → C6H5CH2Br + HBr
C6H5CH2Br + Br2 → C6H5CHBr2 + HBr

The methyl group in toluene undergoes deprotonation only with very strong bases, its pKa is estimated to be approximately 41. Complete hydrogenation of toluene gives methylcyclohexane. The reaction requires a high pressure of hydrogen and a catalyst.

Miscibility

A semiconductor grade toluene is miscible (soluble) with ethanol, benzene, diethyl ether, acetone, chloroform, glacial acetic acid and carbon disulfide. It's practically immiscible with water.

Toluene occurs naturally at low levels in crude oil and is a byproduct in the production of gasoline by a catalytic reformer or ethylene cracker. It is also a byproduct of the production of coke from coal. Final separation and purification is done by any of the distillation or solvent extraction processes used for BTX aromatics (benzene, toluene, and xylene isomers).

Other preparative routes

Toluene can be prepared by a variety of methods. For example, benzene reacts with methanol in presence of a solid acid to give toluene:

C 6 H 6 + CH 3 OH t o C 6 H 5 CH 3 + H 2 O {\displaystyle {\ce {C6H6 + CH3OH ->[t^o]C6H5CH3 + H2O}}}

Precursor to benzene and xylene

Toluene is mainly used as a precursor to benzene via hydrodealkylation:

C6H5CH3 + H2 → C6H6 + CH4

The second ranked application involves its disproportionation to a mixture of benzene and xylene.

Nitration

Nitration of toluene give mono-, di-, and trinitrotoluene, all of which are widely used. Dinitrotoluene is the precursor to toluene diisocyanate, which used in the manufacture of polyurethane foam. Trinitrotoluene is the explosive typically abbreviated TNT.

Oxidation

Benzoic acid and benzaldehyde are produced commercially by partial oxidation of toluene with oxygen. Typical catalysts include cobalt or manganese naphthenates.

Solvent

Toluene is a common solvent, e.g. for paints, paint thinners, silicone sealants, many chemical reactants, rubber, printing ink, adhesives (glues), lacquers, leather tanners, and disinfectants.

Fuel

Toluene can be used as an octane booster in gasoline fuels for internal combustion engines as well as jet fuel. Toluene at 86% by volume fuelled all the turbocharged engines in Formula One during the 1980s, first pioneered by the Honda team. The remaining 14% was a "filler" of n-heptane, to reduce the octane rating to meet Formula One 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 °C (158 °F). Honda solved this problem in their Formula One cars by routing the fuel lines through a heat exchanger, drawing energy from the water in the cooling system to heat the fuel.

In Australia in 2003, toluene was found to have been illegally combined with petrol in fuel outlets for sale as standard vehicular fuel. Toluene incurs no fuel excise tax, while other fuels are taxed at more than 40%, providing a greater profit margin for fuel suppliers. The extent of toluene substitution has not been determined.

Niche applications

In the laboratory, toluene is used as a solvent for carbon nanomaterials, including nanotubes and fullerenes, and it can also be used as a fullerene indicator. The color of the toluene solution of C60 is bright purple. Toluene is used as a cement for fine polystyrene kits (by dissolving and then fusing surfaces) as it can be applied very precisely by brush and contains none of the bulk of an adhesive. Toluene can be used to break open red blood cells in order to extract hemoglobin in biochemistry experiments. 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 of removing the cocaine from coca leaves in the production of Coca-Cola syrup.

Main article: Toluene (toxicology)

The environmental and toxicological effects of toluene have been extensively studied. Inhalation of toluene in low to moderate levels can cause tiredness, confusion, weakness, drunken-type actions, memory loss, nausea, loss of appetite, hearing loss, and colour vision loss. Some of these symptoms usually disappear when exposure is stopped. Inhaling high levels of toluene in a short time may cause light-headedness, nausea, or sleepiness, unconsciousness, and even death. Toluene is, however, much less toxic than benzene, and as a consequence, largely replaced it as an aromatic solvent in chemical preparation. The US Environmental Protection Agency (EPA) states that the carcinogenic potential of toluene cannot be evaluated due to insufficient information. In 2013, worldwide sales of toluene amounted to about 24.5 billion US-dollars.

Similar to many other solvents such as 1,1,1-trichloroethane and some alkylbenzenes, toluene has been shown to act as a non-competitive NMDA receptor antagonist and GABAA receptor positive allosteric modulator. Additionally, toluene has been shown to display antidepressant-like effects in rodents in the forced swim test (FST) and the tail suspension test (TST), likely due to its NMDA antagonist properties.

Toluene is sometimes used as a recreational inhalant ("glue sniffing"), likely on account of its euphoric and dissociative effects.

Toluene inhibits excitatory ion channels including the N-methyl-D-aspartate (NMDA) glutamate and nicotinic acetylcholine receptors (nAChRs) and potentiates the function of inhibitory ion channels such as the gamma-aminobutyric acid receptor type A, glycine, and serotonin receptors. In addition, toluene disrupts voltage-gated calcium channels and ATP-gated ion channels.

Recreational use

Toluene is used as an intoxicative inhalant in a manner unintended by manufacturers. People inhale toluene-containing products (e.g., paint thinner, contact cement, model glue, etc.) for its intoxicating effect. The possession and use of toluene and products containing it are regulated in many jurisdictions, for the supposed reason of preventing minors from obtaining these products for recreational drug purposes. As of 2007, 24 U.S. states had laws penalizing use, possession with intent to use, and/or distribution of such inhalants. In 2005 the European Union banned the general sale of products consisting of greater than 0.5% toluene.

Bioremediation

Several types of fungi including Cladophialophora, Exophiala, Leptodontidium (syn. Leptodontium), Pseudeurotium zonatum, and Cladosporium sphaerospermum, and certain species of bacteria can degrade toluene using it as a source of carbon and energy.

  1. Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 139. doi:10.1039/9781849733069-00130. ISBN 978-0-85404-182-4. Toluene and xylene are preferred IUPAC names, but are not freely substitutable; toluene is substitutable under certain conditions, but only for general nomenclature (see P-15.1.8 for a general substitution rules for retained names).
  2. Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  3. NIOSH Pocket Guide to Chemical Hazards. "#0619". National Institute for Occupational Safety and Health (NIOSH).
  4. "toluene_msds".
  5. "Toluene". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  6. "NFPA Chemicals". New Environment, Inc.
  7. "toluol". Dictionary.com Unabridged (Online). n.d.
  8. "toluene". The American Heritage Dictionary of the English Language (5th ed.). HarperCollins.
  9. McKeown NJ (Feb 1, 2015). Tarabar A (ed.). "Toluene Toxicity, Background, Pathophysiology, Epidemiology". WebMD Health Professional Network.{{cite journal}}:Cite journal requires |journal= ()
  10. Streicher HZ, Gabow PA, Moss AH, Kono D, Kaehny WD (June 1981). "Syndromes of toluene sniffing in adults". Annals of Internal Medicine. 94 (6): 758–62. doi:10.7326/0003-4819-94-6-758. PMID 7235417.
  11. Devathasan G, Low D, Teoh PC, Wan SH, Wong PK (February 1984). "Complications of chronic glue (toluene) abuse in adolescents". Australian and New Zealand Journal of Medicine. 14 (1): 39–43. doi:10.1111/j.1445-5994.1984.tb03583.x. PMID 6087782.
  12. See:
  13. See:
  14. Jacob Berzelius (1843) Jahres Berichte, 22 : 353-354..
  15. See:
  16. Vogel AS, Furniss BS, Hannaford AJ, Tatchell AR, Smith PW (1989). Vogel's Textbook of Practical Organic Chemistry (5th ed.). New York: Longman/Wiley.
  17. Wade LG (2003). Organic Chemistry (5th ed.). Upper Saddle River, New Jersey: Prentice Hall. p. 871.
  18. March J (1992). Advanced Organic Chemistry (4th ed.). New York: Wiley. p. 723.
  19. Podgoršek A, Stavber S, Zupan M, Iskra J (2006). "Free Radical Bromination by the H2O2–HBr System on water". Tetrahedron Letters. 47 (40): 7245–7247. doi:10.1016/j.tetlet.2006.07.109.
  20. Henry Hsieh, Roderic P. Quirk. Anionic Polymerization: Principles and Practical Applications. p. 41.
  21. "Toluene, Semiconductor Grade, 99% min, Thermo Scientific | Fisher Scientific". www.fishersci.com. Retrieved2022-04-26.
  22. Jörg F, Ulrich G, Simo TA (2005). "Toluene". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a27_147.pub2.
  23. Wade LG (2014). Organic Chemistry (Pearson new international ed.). Harlow: Pearson Education Limited. p. 985. ISBN 978-1-292-02165-2.
  24. "Dual cure, low-solvent silicone pressure sensitive adhesives - General Electric Company".
  25. Honda Formula One Turbo-charged V-6 1.5L Engine(PDF). SAE International Congress and Exposition. February 27 – March 3, 1989.
  26. "Scam on petrol sparks spot tests". Liberty Oil. Archived from the original on 3 March 2016.
  27. "The World Today Archive - Authorities yet to acknowledge petrol scam problem". Australian Broadcasting Corporation.
  28. Merory J (1968). Food Flavorings: Composition, Manufacture and Use (2nd ed.). Westport, CT: AVI Publishing Company, Inc..
  29. Hogan CM (2011), "Sulfur", in Jorgensen A, Cleveland CJ (eds.), Encyclopedia of Earth, Washington DC: National Council for Science and the Environment, retrieved26 October 2012, Sulfur is insoluble in water, but soluble in carbon disulfide, somewhat soluble in other non-polar organic solvents such as the aromatics benzene and toluene.
  30. Chang SJ, Chen CJ, Lien CH, Sung FC (August 2006). "Hearing loss in workers exposed to toluene and noise". Environmental Health Perspectives. 114 (8): 1283–6. doi:10.1289/ehp.8959. PMC1552019. PMID 16882540.
  31. Morata TC, Nylén P, Johnson AC, Dunn DE (1995). "Auditory and vestibular functions after single or combined exposure to toluene: a review". Archives of Toxicology. 69 (7): 431–43. doi:10.1007/s002040050196. PMID 8526738. S2CID 22919141.
  32. Kishi R, Eguchi T, Yuasa J, Katakura Y, Arata Y, Harabuchi I, et al. (January 2001). "Effects of low-level occupational exposure to styrene on color vision: dose relation with a urinary metabolite". Environmental Research. 85 (1): 25–30. Bibcode:2001ER.....85...25K. doi:10.1006/enrs.2000.4227. PMID 11161648.
  33. "Health Effects of Toluene", Canadian Centre for Occupational Health and Safety.
  34. "Toluene Toxicity Physiologic Effects" Archived 2016-10-12 at the Wayback Machine, Agency for Toxic Substances and Disease Registry.
  35. [1], EPA
  36. Ceresana. "Toluene – Study: Market, Analysis, Trends - Ceresana".
  37. Cruz SL, Soberanes-Chávez P, Páez-Martinez N, López-Rubalcava C (June 2009). "Toluene has antidepressant-like actions in two animal models used for the screening of antidepressant drugs". Psychopharmacology. 204 (2): 279–86. doi:10.1007/s00213-009-1462-2. PMID 19151967. S2CID 2235023.
  38. "Toluene".
  39. Spigel S (8 July 2009). "State Laws on Inhalant Use".
  40. "EU sets 0.1% limit on use of toluene, TCB". ICIS. Reed Business Information. 24 September 2005.
  41. Prenafeta-Boldu FX, Kuhn A, Luykx DM, Anke H, van Groenestijn JW, de Bont JA (April 2001). "Isolation and characterisation of fungi growing on volatile aromatic hydrocarbons as their sole carbon and energy source". Mycological Research. 105 (4): 477–484. doi:10.1017/S0953756201003719.
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Toluene Article Talk Language Watch Edit Toluene ˈ t ɒ l j u iː n also known as toluol ˈ t ɒ l j u ɒ l ɔː l oʊ l 7 8 is a substituted aromatic hydrocarbon It is a colorless water insoluble liquid with the smell associated with paint thinners It is a mono substituted benzene derivative consisting of a methyl group CH3 attached to a phenyl group As such its systematic IUPAC name is methylbenzene Toluene is predominantly used as an industrial feedstock and a solvent Toluene NamesPreferred IUPAC name Toluene 1 Systematic IUPAC name MethylbenzeneOther names Phenyl methane Toluol AnisenIdentifiersCAS Number 108 88 3 Y3D model JSmol Interactive imageAbbreviations PhMe MePh BnH TolChEBI CHEBI 17578 NChEMBL ChEMBL9113 YChemSpider 1108 YDrugBank DB01900 NECHA InfoCard 100 003 297IUPHAR BPS 5481KEGG C01455 YPubChem CID 1140RTECS number XS5250000UNII 3FPU23BG52 YCompTox Dashboard EPA DTXSID7021360InChI InChI 1S C7H8 c1 7 5 3 2 4 6 7 h2 6H 1H3 YKey YXFVVABEGXRONW UHFFFAOYSA N YInChI 1 C7H8 c1 7 5 3 2 4 6 7 h2 6H 1H3Key YXFVVABEGXRONW UHFFFAOYATSMILES Cc1ccccc1PropertiesChemical formula C 7H 8Molar mass 92 141 g mol 1Appearance Colorless liquid 2 Odor sweet pungent benzene like 3 Density 0 87 g mL 20 C 2 Melting point 95 C 139 F 178 K 2 Boiling point 111 C 232 F 384 K 2 Solubility in water 0 52 g L 20 C 2 log P 2 68 4 Vapor pressure 2 8 kPa 20 C 3 Magnetic susceptibility x 66 11 10 6 cm3 molRefractive index nD 1 497 20 C Viscosity 0 590 cP 20 C StructureDipole moment 0 36 DHazardsOccupational safety and health OHS OSH Main hazards highly flammableGHS labelling PictogramsSignal word DangerHazard statements H225 H304 H315 H336 H361d H373Precautionary statements P210 P240 P301 P310 P302 P352 P308 P313 P314 P403 P233NFPA 704 fire diamond 230Flash point 4 C 39 F 277 K 2 Explosive limits 1 1 7 1 3 Threshold limit value TLV 50 mL m3 190 mg m3Lethal dose or concentration LD LC LC50 median concentration gt 26700 ppm rat 1 h 400 ppm mouse 24 h 5 LCLo lowest published 55 000 ppm rabbit 40 min 5 NIOSH US health exposure limits PEL Permissible TWA 200 ppm C 300 ppm 500 ppm 10 minute maximum peak 3 REL Recommended TWA 100 ppm 375 mg m3 ST 150 ppm 560 mg m3 3 IDLH Immediate danger 500 ppm 3 Safety data sheet SDS SIRI orgRelated compoundsRelated aromatic hydrocarbons benzene xylene naphthaleneRelated compounds methylcyclohexaneSupplementary data pageToluene data page Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references As the solvent in some types of paint thinner permanent markers contact cement and certain types of glue toluene is sometimes used as a recreational inhalant 9 and has the potential of causing severe neurological harm 10 11 Contents 1 History 2 Chemical properties 2 1 Miscibility 3 Production 3 1 Other preparative routes 4 Uses 4 1 Precursor to benzene and xylene 4 2 Nitration 4 3 Oxidation 4 4 Solvent 4 5 Fuel 4 6 Niche applications 5 Toxicology and metabolism 5 1 Recreational use 5 2 Bioremediation 6 References 7 External linksHistory EditThe compound was first isolated in 1837 through a distillation of pine oil by the Polish chemist Filip Walter who named it retinnaphte 12 In 1841 French chemist Henri Etienne Sainte Claire Deville isolated a hydrocarbon from balsam of Tolu an aromatic extract from the tropical Colombian tree Myroxylon balsamum which Deville recognized as similar to Walter s retinnaphte and to benzene hence he called the new hydrocarbon benzoene 13 In 1843 Jons Jacob Berzelius recommended the name toluin 14 In 1850 French chemist Auguste Cahours isolated from a distillate of wood a hydrocarbon which he recognized as similar to Deville s benzoene and which Cahours named toluene 15 Chemical properties EditToluene reacts as a normal aromatic hydrocarbon in electrophilic aromatic substitution 16 17 18 Because the methyl group has greater electron releasing properties than a hydrogen atom in the same position toluene is more reactive than benzene toward electrophiles It undergoes sulfonation to give p toluenesulfonic acid and chlorination by Cl2 in the presence of FeCl3 to give ortho and para isomers of chlorotoluene Importantly the methyl side chain in toluene is susceptible to oxidation Toluene reacts with potassium permanganate to yield benzoic acid and with chromyl chloride to yield benzaldehyde Etard reaction The C H bonds of the methyl group in toluene are benzylic which means that they are weaker than C H bonds in simpler alkanes Reflecting this weakness the methyl group in toluene undergoes halogenation under free radical conditions For example when heated with N bromosuccinimide NBS in the presence of AIBN toluene converts to benzyl bromide The same conversion can be effected with elemental bromine in the presence of UV light or even sunlight Toluene may also be brominated by treating it with HBr and H2O2 in the presence of light 19 C6H5CH3 Br2 C6H5CH2Br HBr C6H5CH2Br Br2 C6H5CHBr2 HBr The methyl group in toluene undergoes deprotonation only with very strong bases its pKa is estimated to be approximately 41 20 Complete hydrogenation of toluene gives methylcyclohexane The reaction requires a high pressure of hydrogen and a catalyst Miscibility Edit A semiconductor grade toluene is miscible soluble with ethanol benzene diethyl ether acetone chloroform glacial acetic acid and carbon disulfide 21 It s practically immiscible with water 21 Production EditToluene occurs naturally at low levels in crude oil and is a byproduct in the production of gasoline by a catalytic reformer or ethylene cracker It is also a byproduct of the production of coke from coal Final separation and purification is done by any of the distillation or solvent extraction processes used for BTX aromatics benzene toluene and xylene isomers 22 Other preparative routes Edit Toluene can be prepared by a variety of methods For example benzene reacts with methanol in presence of a solid acid to give toluene 22 C 6 H 6 CH 3 OH t o C 6 H 5 CH 3 H 2 O displaystyle ce C6H6 CH3OH gt t o C6H5CH3 H2O Uses EditPrecursor to benzene and xylene Edit Toluene is mainly used as a precursor to benzene via hydrodealkylation C6H5CH3 H2 C6H6 CH4 The second ranked application involves its disproportionation to a mixture of benzene and xylene 22 Nitration Edit Nitration of toluene give mono di and trinitrotoluene all of which are widely used Dinitrotoluene is the precursor to toluene diisocyanate which used in the manufacture of polyurethane foam Trinitrotoluene is the explosive typically abbreviated TNT Oxidation Edit Benzoic acid and benzaldehyde are produced commercially by partial oxidation of toluene with oxygen Typical catalysts include cobalt or manganese naphthenates 23 Solvent Edit Toluene is a common solvent e g for paints paint thinners silicone sealants 24 many chemical reactants rubber printing ink adhesives glues lacquers leather tanners and disinfectants 22 Fuel Edit Toluene can be used as an octane booster in gasoline fuels for internal combustion engines as well as jet fuel Toluene at 86 by volume fuelled all the turbocharged engines in Formula One during the 1980s first pioneered by the Honda team The remaining 14 was a filler of n heptane to reduce the octane rating to meet Formula One 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 C 158 F Honda solved this problem in their Formula One cars by routing the fuel lines through a heat exchanger drawing energy from the water in the cooling system to heat the fuel 25 In Australia in 2003 toluene was found to have been illegally combined with petrol in fuel outlets for sale as standard vehicular fuel Toluene incurs no fuel excise tax while other fuels are taxed at more than 40 providing a greater profit margin for fuel suppliers The extent of toluene substitution has not been determined 26 27 Niche applications Edit In the laboratory toluene is used as a solvent for carbon nanomaterials including nanotubes and fullerenes and it can also be used as a fullerene indicator The color of the toluene solution of C60 is bright purple Toluene is used as a cement for fine polystyrene kits by dissolving and then fusing surfaces as it can be applied very precisely by brush and contains none of the bulk of an adhesive Toluene can be used to break open red blood cells in order to extract hemoglobin in biochemistry experiments 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 of removing the cocaine from coca leaves in the production of Coca Cola syrup 28 Toxicology and metabolism EditMain article Toluene toxicology The environmental and toxicological effects of toluene have been extensively studied 29 Inhalation of toluene in low to moderate levels can cause tiredness confusion weakness drunken type actions memory loss nausea loss of appetite hearing loss 30 31 and colour vision loss 32 Some of these symptoms usually disappear when exposure is stopped Inhaling high levels of toluene in a short time may cause light headedness nausea or sleepiness unconsciousness and even death 33 34 Toluene is however much less toxic than benzene and as a consequence largely replaced it as an aromatic solvent in chemical preparation The US Environmental Protection Agency EPA states that the carcinogenic potential of toluene cannot be evaluated due to insufficient information 35 In 2013 worldwide sales of toluene amounted to about 24 5 billion US dollars 36 Similar to many other solvents such as 1 1 1 trichloroethane and some alkylbenzenes toluene has been shown to act as a non competitive NMDA receptor antagonist and GABAA receptor positive allosteric modulator 37 Additionally toluene has been shown to display antidepressant like effects in rodents in the forced swim test FST and the tail suspension test TST 37 likely due to its NMDA antagonist properties Toluene is sometimes used as a recreational inhalant glue sniffing likely on account of its euphoric and dissociative effects 37 Toluene inhibits excitatory ion channels including the N methyl D aspartate NMDA glutamate and nicotinic acetylcholine receptors nAChRs and potentiates the function of inhibitory ion channels such as the gamma aminobutyric acid receptor type A glycine and serotonin receptors In addition toluene disrupts voltage gated calcium channels and ATP gated ion channels 38 Recreational use Edit Toluene is used as an intoxicative inhalant in a manner unintended by manufacturers People inhale toluene containing products e g paint thinner contact cement model glue etc for its intoxicating effect The possession and use of toluene and products containing it are regulated in many jurisdictions for the supposed reason of preventing minors from obtaining these products for recreational drug purposes As of 2007 24 U S states had laws penalizing use possession with intent to use and or distribution of such inhalants 39 In 2005 the European Union banned the general sale of products consisting of greater than 0 5 toluene 40 Bioremediation Edit Several types of fungi including Cladophialophora Exophiala Leptodontidium syn Leptodontium Pseudeurotium zonatum and Cladosporium sphaerospermum and certain species of bacteria can degrade toluene using it as a source of carbon and energy 41 References Edit Nomenclature of Organic Chemistry IUPAC Recommendations and Preferred Names 2013 Blue Book Cambridge The Royal Society of Chemistry 2014 p 139 doi 10 1039 9781849733069 00130 ISBN 978 0 85404 182 4 Toluene and xylene are preferred IUPAC names but are not freely substitutable toluene is substitutable under certain conditions but only for general nomenclature see P 15 1 8 for a general substitution rules for retained names a b c d e f Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health a b c d e f NIOSH Pocket Guide to Chemical Hazards 0619 National Institute for Occupational Safety and Health NIOSH toluene msds a b Toluene Immediately Dangerous to Life or Health Concentrations IDLH National Institute for Occupational Safety and Health NIOSH NFPA Chemicals New Environment Inc toluol Dictionary com Unabridged Online n d toluene The American Heritage Dictionary of the English Language 5th ed HarperCollins McKeown NJ Feb 1 2015 Tarabar A ed Toluene Toxicity Background Pathophysiology Epidemiology WebMD Health Professional Network a href wiki Template Cite journal title Template Cite journal cite journal a Cite journal requires journal help Streicher HZ Gabow PA Moss AH Kono D Kaehny WD June 1981 Syndromes of toluene sniffing in adults Annals of Internal Medicine 94 6 758 62 doi 10 7326 0003 4819 94 6 758 PMID 7235417 Devathasan G Low D Teoh PC Wan SH Wong PK February 1984 Complications of chronic glue toluene abuse in adolescents Australian and New Zealand Journal of Medicine 14 1 39 43 doi 10 1111 j 1445 5994 1984 tb03583 x PMID 6087782 See Pelletier and Walter 1837 Examen des produits provenant du traitement de la resine dans la fabrication du gaz pour l eclairage Examination of products arising from the treatment of resin during the production of illuminating gas Comptes rendus 4 898 899 Pelletier and Philippe Walter 1838 Examen des produits provenant du traitement de la resine dans la fabrication du gaz pour l eclairage Annales de Chimie et de Physique 2nd series 67 269 303 Toluene is named on pp 278 279 Nous designerons la substance qui nous occupe par le nom deretinnaphte qui rappelle son origine et ses proprietes physiques rhtinh nafta We will designate the substance that occupies us by the name of retinnaphte which recalls its origin and its physical properties rhtinh nafta resin naphtha See Deville 1841 Recherches sur les resines Etude du baume de Tolu Investigations of resins Study of Tolu balsam Comptes rendus 13 476 478 H Deville 1841 Recherches chimiques sur les resines Premier memoire Chemical investigations of resins first memoir Annales de Chimie et de Physique 3rd series 3 151 195 Deville names toluene on p 170 J ai adopte pour le corps qui m occupe dans ce moment le nom debenzoene qui rappelle dans les baumes dont il provient ce caractere presque generique qui est de contenir de l acide benzoique I ve adopted for this substance that occupies me at the moment the name benzoene which recalls in the balsams from which it comes that character which is contained in benzoic acid Wisniak J 2004 Henri Etienne Sainte Claire Deville A physician turned metallurgist Journal of Materials Engineering and Performance 13 2 117 118 Bibcode 2004JMEP 13 117W doi 10 1361 10599490418271 S2CID 95058552 Jacob Berzelius 1843 Jahres Berichte 22 353 354 See Cahours A 1850 Recherches sur les huiles legeres obtenues dans la distillation du bois Investigations of light oils obtained by the distillation of wood Comptes Rendus in French 30 319 323 320 Wisniak J October 2013 Auguste Andre Thomas Cahours Educacion Quimica 24 4 451 460 doi 10 1016 S0187 893X 13 72500 X Vogel AS Furniss BS Hannaford AJ Tatchell AR Smith PW 1989 Vogel s Textbook of Practical Organic Chemistry 5th ed New York Longman Wiley Wade LG 2003 Organic Chemistry 5th ed Upper Saddle River New Jersey Prentice Hall p 871 March J 1992 Advanced Organic Chemistry 4th ed New York Wiley p 723 Podgorsek A Stavber S Zupan M Iskra J 2006 Free Radical Bromination by the H2O2 HBr System on water Tetrahedron Letters 47 40 7245 7247 doi 10 1016 j tetlet 2006 07 109 Henry Hsieh Roderic P Quirk Anionic Polymerization Principles and Practical Applications p 41 a b Toluene Semiconductor Grade 99 min Thermo Scientific Fisher Scientific www fishersci com Retrieved 2022 04 26 a b c d Jorg F Ulrich G Simo TA 2005 Toluene Ullmann s Encyclopedia of Industrial Chemistry Weinheim Wiley VCH doi 10 1002 14356007 a27 147 pub2 Wade LG 2014 Organic Chemistry Pearson new international ed Harlow Pearson Education Limited p 985 ISBN 978 1 292 02165 2 Dual cure low solvent silicone pressure sensitive adhesives General Electric Company Honda Formula One Turbo charged V 6 1 5L Engine PDF SAE International Congress and Exposition February 27 March 3 1989 Scam on petrol sparks spot tests Liberty Oil Archived from the original on 3 March 2016 The World Today Archive Authorities yet to acknowledge petrol scam problem Australian Broadcasting Corporation Merory J 1968 Food Flavorings Composition Manufacture and Use 2nd ed Westport CT AVI Publishing Company Inc Hogan CM 2011 Sulfur in Jorgensen A Cleveland CJ eds Encyclopedia of Earth Washington DC National Council for Science and the Environment retrieved 26 October 2012 Sulfur is insoluble in water but soluble in carbon disulfide somewhat soluble in other non polar organic solvents such as the aromatics benzene and toluene Chang SJ Chen CJ Lien CH Sung FC August 2006 Hearing loss in workers exposed to toluene and noise Environmental Health Perspectives 114 8 1283 6 doi 10 1289 ehp 8959 PMC 1552019 PMID 16882540 Morata TC Nylen P Johnson AC Dunn DE 1995 Auditory and vestibular functions after single or combined exposure to toluene a review Archives of Toxicology 69 7 431 43 doi 10 1007 s002040050196 PMID 8526738 S2CID 22919141 Kishi R Eguchi T Yuasa J Katakura Y Arata Y Harabuchi I et al January 2001 Effects of low level occupational exposure to styrene on color vision dose relation with a urinary metabolite Environmental Research 85 1 25 30 Bibcode 2001ER 85 25K doi 10 1006 enrs 2000 4227 PMID 11161648 Health Effects of Toluene Canadian Centre for Occupational Health and Safety Toluene Toxicity Physiologic Effects Archived 2016 10 12 at the Wayback Machine Agency for Toxic Substances and Disease Registry 1 EPA Ceresana Toluene Study Market Analysis Trends Ceresana a b c Cruz SL Soberanes Chavez P Paez Martinez N Lopez Rubalcava C June 2009 Toluene has antidepressant like actions in two animal models used for the screening of antidepressant drugs Psychopharmacology 204 2 279 86 doi 10 1007 s00213 009 1462 2 PMID 19151967 S2CID 2235023 Toluene Spigel S 8 July 2009 State Laws on Inhalant Use EU sets 0 1 limit on use of toluene TCB ICIS Reed Business Information 24 September 2005 Prenafeta Boldu FX Kuhn A Luykx DM Anke H van Groenestijn JW de Bont JA April 2001 Isolation and characterisation of fungi growing on volatile aromatic hydrocarbons as their sole carbon and energy source Mycological Research 105 4 477 484 doi 10 1017 S0953756201003719 External links EditWikimedia Commons has media related to toluene Wikiquote has quotations related to Toluene ATSDR Case Studies in Environmental Medicine Toluene Toxicity U S Department of Health and Human Services public domain American Industrial Hygiene Association The Ear Poisons The Synergist November 2018 Toluene CDC NIOSH Workplace Safety and Health Topic DHHS OSHA NIOSH 2018 Preventing Hearing Loss Caused by Chemical Ototoxicity and Noise Exposure Safety and Health Information Bulletin SHIB Occupational Safety and Health Administration and the National Institute for Occupational Safety and Health SHIB 03 08 2018 DHHS NIOSH Publication No 2018 124 Retrieved from https en wikipedia org w index php title Toluene amp oldid 1088550153, wikipedia, wiki, book,

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