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Toluene
Toluene
General
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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, redolent 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. Like other solvents, toluene is also used as an inhalant drug for its intoxicating properties.[1][2]

HistoryEdit

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

Chemical propertiesEdit

Toluene reacts as a normal aromatic hydrocarbon towards electrophilic aromatic substitution.[3][4][5] 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. Reaction with potassium permanganate leads to benzoic acid, whereas reaction with chromyl chloride leads to benzaldehyde (Étard reaction). Halogenation can be performed under free radical conditions. For example, N-bromosuccinimide (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 to go to completion, because of the stability of the aromatic system. pKa is approximately 45.

ProductionEdit

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

UsesEdit

Toluene is a common solvent, able to dissolve paints, paint thinners, silicone sealants,[6] many chemical reactants, rubber, printing ink, adhesives (glues), lacquers, leather tanners, and disinfectants. It can also be used as a fullerene indicator, and is a raw material for toluene diisocyanate (used in the manufacture of polyurethane foam) and TNT. It is also 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.

Industrial uses of toluene include dealkylation to benzene, and the disproportionation to a mixture of benzene and xylene in the BTX process. When oxidized it yields benzaldehyde and benzoic acid, two important intermediates in 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 in biochemistry experiments.

Toluene can be used as an octane booster in gasoline fuels used in internal combustion engines. Toluene at 86% by volume fueled all the 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 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 gasoline does, which can break down fuel pumps and cause upper cylinder bore wear.

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 can be inhaled for its intoxicating effects. 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 can make you feel light-headed, dizzy, or sleepy. It can also cause unconsciousness, and even death. Toluene may negatively affect kidney function.[7]

Toluene has also been used in the process of removing the cocaine from coca leaves in the production of Coca-Cola syrup.[8]

Toxicology and metabolismEdit

Main article: Toluene (toxicology)

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% is oxidized to become benzyl alcohol.[9] The toxic metabolites are created by the remaining 5% that are oxidized to benzaldehyde and cresols.[10][11] Most of the reactive products are detoxified by conjugation to glutathione but the remainder may severely damage cells.[12]

Toluene is mainly excreted as benzoic acid and hippuric acid, both formed by further metabolic oxidation of benzyl alcohol.

See alsoEdit

FootnotesEdit

  1. Streicher HZ, Gabow PA, Moss AH, Kono D, Kaehny WD (1981). Syndromes of toluene sniffing in adults. Ann. Intern. Med. 94 (6): 758–62.
  2. Devathasan G, Low D, Teoh PC, Wan SH, Wong PK (1984). Complications of chronic glue (toluene) abuse in adolescents. Aust N Z J Med 14 (1): 39–43.
  3. B. S. Furnell et al., Vogel's Textbook of Practical Organic Chemistry, 5th edition, Longman/Wiley, New York, 1989
  4. L. G. Wade, Organic Chemistry, 5th ed., p. 871, Prentice Hall, Upper Saddle RIver, New Jersey, 2003
  5. J. March, Advanced Organic Chemistry, 4th ed., p. 723, Wiley, New York, 1992
  6. Dual cure, low-solvent silicone pressure sensitive adhesives - Patent 6387487
  7. http://www.atsdr.cdc.gov/tfacts56.html
  8. Merory, Joseph (1968). Food Flavorings: Composition, Manufacture and Use, 2nd, Westport, CT: AVI Publishing Company, Inc...
  9. 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.
  10. 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.
  11. 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.
  12. 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.

Further readingEdit

Key textsEdit

BooksEdit

  • Chen, H.-H., Wei, C.-T., & Chan, M.-H. (2004). Neonatal Toluene Exposure Alters Glutamate-Induced Calcium Signaling in Developing Cerebellar Granule Neurons. New York, NY: New York Academy of Sciences.

PapersEdit

  • Review of Toluene. Environmental Health Criteria 52. (1987). PsycCRITIQUES Vol 32 (1), Jan, 1987.
  • Balster, R. L., Wiley, J. L., Tokarz, M. E., & Knisely, J. S. (1992). Effects of ethanol and toluene on fixed-ratio performance in short sleep and long sleep mice: Drug and Alcohol Dependence Vol 31(1) Oct 1992, 65-75.
  • Bamat, N. A., Brunelli, S. A., Kron, M. M., Schulte, A. R., & Zimmerberg, B. (2005). Behavioral effects of toluene in rats selectively bred for infantile vocalization rate: Neurotoxicology and Teratology Vol 27(6) Nov-Dec 2005, 883-890.
  • Benignus, V. A., Bushnell, P. J., & Boyes, W. K. (2005). Toward Cost-Benefit Analysis of Acute Behavioral Effects of Toluene in Humans: Risk Analysis Vol 25(2) Apr 2005, 447-462.
  • Berenguer, P., Soulage, C., Fautrel, A., Pequignot, J.-M., & Abraini, J. H. (2004). Behavioral and neurochemical effects induced by subchronic combined exposure to toluene at 40 ppm and noise at 80 dB-A in rats: Physiology & Behavior Vol 81(3) May 2004, 527-534.
  • Berenguer, P., Soulage, C., Perrin, D., Pequignot, J.-M., & Abraini, J. H. (2003). Behavioral and neurochemical effects induced by subchronic exposure to 40 ppm toluene in rats: Pharmacology, Biochemistry and Behavior Vol 74(4) Mar 2003, 997-1003.
  • Beyer, C. E., Stafford, D., LeSage, M. G., Glowa, J. R., & Steketee, J. D. (2001). Repeated exposure to inhaled toluene induces behavioral and neurochemical cross-sensitization to cocaine in rats: Psychopharmacology Vol 154(2) Mar 2001, 198-204.
  • Boey, K. (1996). Psychological evaluation of brain function subsequent to exposure to a low level of toluene: Acta Psychologica Sinica Vol 28(2) 1996, 126-130.
  • Bowen, S. E. (2006). Increases in amphetamine-like discriminative stimulus effects of the abused inhalant toluene in mice: Psychopharmacology Vol 186(4) Jul 2006, 517-524.
  • Bowen, S. E. (2008). Time course of the ethanol-like discriminative stimulus effects of abused inhalants in mice: Pharmacology, Biochemistry and Behavior Vol 91(3) Nov 2008, 345-350.
  • Bowen, S. E., Batis, J. C., Mohammadi, M. H., & Hannigan, J. H. (2005). Abuse pattern of gestational toluene exposure and early postnatal development in rats: Neurotoxicology and Teratology Vol 27(1) Jan-Feb 2005, 105-116.
  • Bowen, S. E., Charlesworth, J. D., Tokarz, M. E., Wright, M. J., Jr., & Wiley, J. L. (2007). Decreased sensitivity in adolescent vs. adult rats to the locomotor activating effects of toluene: Neurotoxicology and Teratology Vol 29(6) Nov-Dec 2007, 599-606.
  • Bowen, S. E., & McDonald, P. (2009). Abuse pattern of toluene exposure alters mouse behavior in a waiting-for-reward operant task: Neurotoxicology and Teratology Vol 31(1) Jan-Feb 2009, 18-25.
  • Bowen, S. E., Mohammadi, M. H., Batis, J. C., & Hannigan, J. H. (2007). Gestational toluene exposure effects on spontaneous and amphetamine-induced locomotor behavior in rats: Neurotoxicology and Teratology Vol 29(2) Mar 2007, 236-246.
  • Bushnell, P. J., Kelly, K. L., & Crofton, K. M. (1994). Effects of toluene inhalation on detection of auditory signals in rats: Neurotoxicology and Teratology Vol 16(2) Mar-Apr 1994, 149-160.
  • Campagna, D., Stengel, B., Mergler, D., Limasset, J. C., Diebold, F., Michard, D., et al. (2001). Color vision and occupational toluene exposure: Neurotoxicology and Teratology Vol 23(5) Sep-Oct 2001, 473-480.
  • Campo, P., Waniusiow, D., Cossec, B., Lataye, R., Rieger, B., Cosnier, F., et al. (2008). Toluene-induced hearing loss in phenobarbital treated rats: Neurotoxicology and Teratology Vol 30(1) Jan-Feb 2008, 46-54.
  • Chan, M.-H., Chien, T.-H., Lee, P.-Y., & Chen, H.-H. (2004). Involvement of NO/cGMP pathway in toluene-induced locomotor hyperactivity in female rats: Psychopharmacology Vol 176(3-4) 2004, 435-439.
  • Chen, H.-H., & Lee, Y.-F. (2002). Neonatal toluene exposure selectively alters sensitivity to different chemoconvulsant drugs in juvenile rats: Pharmacology, Biochemistry and Behavior Vol 73(4) Nov 2002, 921-927.
  • Chen, H.-H., Lee, Y.-F., Chan, M.-H., & Lo, P.-S. (2004). The Role of N-Methyl-D-aspartate Receptors in Neurobehavioral Changes Induced by Toluene Exposure during Synaptogenesis. New York, NY: New York Academy of Sciences.
  • Chien, T.-H., Chan, M.-H., Tang, Y.-C., & Chen, H.-H. (2005). Toluene exposure during the brain growth spurt reduces behavioral responses to noncompetitive N-methyl-D-aspartate receptor antagonists in adult rats: Psychopharmacology Vol 182(4) Nov 2005, 468-474.
  • Cometto-Muniz, J. E., Cain, W. S., & Abraham, M. H. (2003). Dose-addition of individual odorants in the odor detection of binary mixtures: Behavioural Brain Research Vol 138(1) Jan 2003, 95-105.
  • Cruz, S. L., Gauthereau, M. Y., Camacho-Munoz, C., Lopez-Rubalcava, C., & Balster, R. L. (2003). Effects of inhaled toluene and 1,1,1-trichloroethane on seizures and death produced by N-methyl-{D}-aspartic acid in mice: Behavioural Brain Research Vol 140(1-2) Mar 2003, 195-202.
  • Damasceno, B. P., & de Capitani, E. M. (1994). Cerebellar atrophy related to chronic exposure to toluene: Arquivos de Neuro-Psiquiatria Vol 52(1) Mar 1994, 90-92.
  • Del Re, A. M., Dopico, A. M., & Woodward, J. J. (2006). Effects of the abused inhalant toluene on ethanol-sensitive potassium channels expressed in oocytes: Brain Research Vol 1087(1) May 2006, 75-82.
  • Del Re, A. M., & Woodward, J. J. (2005). Inhibition of gap junction currents by the abused solvent toluene: Drug and Alcohol Dependence Vol 78(2) May 2005, 221-224.
  • Filley, C. M., & Rosenberg, N. L. (1990). "Toluene dementia": Reply: Neurology Vol 40(8) Aug 1990, 1321.
  • Forkman, B. A., Ljungberg, T., Johnson, A. C., Nylen, P., & et al. (1991). Long-term effects of toluene inhalation on rat behavior: Neurotoxicology and Teratology Vol 13(5) Sep-Oct 1991, 475-481.
  • Fornazzari, L. (1990). The neurotoxicity of inhaled toluene: The Canadian Journal of Psychiatry / La Revue canadienne de psychiatrie Vol 35(8) Nov 1990, 723.
  • Funada, M., Sato, M., Makino, Y., & Wada, K. (2002). Evaluation of rewarding effect of toluene by the conditioned place preference procedure in mice: Brain Research Protocols Vol 10(1) Aug 2002, 47-54.
  • Gerasimov, M. R., Ferrieri, R. A., Schiffer, W. K., Logan, J., Gatley, S. J., Gifford, A. N., et al. (2002). Study of brain uptake and biodistribution of: Life Sciences Vol 70(23) Apr 2002, 2811-2828.
  • Gerasimov, M. R., Schiffer, W. K., Marstellar, D., Ferrieri, R., Alexoff, D., & Dewey, S. L. (2002). Toluene inhalation produces regionally specific changes in extracellular dopamine: Drug and Alcohol Dependence Vol 65(3) Feb 2002, 243-251.
  • Ghosh, T. K., Copeland, R. L., & Pradhan, S. N. (1990). Sensitivity of EEG in young rats to toluene exposure: Pharmacology, Biochemistry and Behavior Vol 36(4) Aug 1990, 779-785.
  • Gospe, S. M. (1990). Toluene dementia: Neurology Vol 40(8) Aug 1990, 1320-1321.
  • Gulsun, M., Uzun, O., & Doruk, A. (2006). Corpus Callosum Necrosis with Psychiatric Symptoms Resulting From Chronic Toluene Intoxication/Exposure: A Case Presentation: Bagimlik Dergisi Vol 7(1) Apr 2006, 44-48.
  • Hougaard, K. S., Andersen, M. B., Hansen, A. M., Hass, U., Werge, T., & Lund, S. P. (2005). Effects of prenatal exposure to chronic mild stress and toluene in rats: Neurotoxicology and Teratology Vol 27(1) Jan-Feb 2005, 153-167.
  • Hougaard, K. S., Hass, U., Lund, S. P., & Simonsen, L. (1999). Effects of prenatal exposure to toluene on postnatal development and behavior in rats: Neurotoxicology and Teratology Vol 21(3) May-Jun 1999, 241-250.
  • Ikeda, M., & Tsukagoshi, H. (1990). Encephalopathy due to toluene sniffing: Report of a case with magnetic resonance imaging: European Neurology Vol 30(6) Nov-Dec 1990, 347-349.
  • Jarosz, P. A., Fata, E., Bowen, S. E., Jen, K. L. C., & Coscina, D. V. (2008). Effects of abuse pattern of gestational toluene exposure on metabolism, feeding and body composition: Physiology & Behavior Vol 93(4-5) Mar 2008, 984-993.
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  • Johnson, A.-C. (1992). Auditory sensitivity in rats exposed to toluene and/or acetyl salicylic acid: Neuroreport: An International Journal for the Rapid Communication of Research in Neuroscience Vol 3(12) Dec 1992, 1141-1144.
  • Jones, H. E., & Balster, R. L. (1997). Neurobehavioral consequences of intermittent prenatal exposure to high concentrations of toluene: Neurotoxicology and Teratology Vol 19(4) Jul-Aug 1997, 305-313.
  • Katzelnick, D. J., Davar, G., & Scanlon, J. P. (1991). Reversibility of psychiatric symptoms in a chronic solvent abuser: A case report: Journal of Neuropsychiatry & Clinical Neurosciences Vol 3(3) Sum 1991, 319-321.
  • Kondo, H., Huang, J., Ichihara, G., Kamijima, M., & et al. (1995). Toluene induces behavioral activation without affecting striatal dopamine metabolism in the rat: Behavioral and microdialysis studies: Pharmacology, Biochemistry and Behavior Vol 51(1) May 1995, 97-101.
  • Lataye, R., & Campo, P. (1997). Combined effects of a simultaneous exposure to noise and toluene on hearing function: Neurotoxicology and Teratology Vol 19(5) Sep-Oct 1997, 373-382.
  • Lataye, R., Campo, P., & Loquet, G. (1999). Toluene ototoxicity in rats: Assessment of the frequency of hearing deficit by electrocochleography: Neurotoxicology and Teratology Vol 21(3) May-Jun 1999, 267-276.
  • Lataye, R., Campo, P., Pouyatos, B., Cossec, B., Blachere, V., & Morel, G. (2003). Solvent ototoxicity in the rat and guinea pig: Neurotoxicology and Teratology Vol 25(1) Jan-Feb 2003, 39-50.
  • Lee, D. E., Gerasimov, M. R., Schiffer, W. K., & Gifford, A. N. (2006). Concentration-dependent conditioned place preference to inhaled toluene vapors in rats: Drug and Alcohol Dependence Vol 85(1) Oct 2006, 87-90.
  • Lee, Y.-F., Lo, P.-S., Wang, Y.-J., Hu, A., & Chen, H.-H. (2005). Neonatal toluene exposure alters N-methyl-D-aspartate receptor subunit expression in the hippocampus and cerebellum in juvenile rats: Neuropharmacology Vol 48(2) Feb 2005, 195-203.
  • Lopez-Rubalcava, C., Hen, R., & Cruz, S. L. (2000). Anxiolytic-like actions of toluene in the burying behavior and plus-maze tests: Differences in sensitivity between 5-HT-sub(1B ) knockout and wild-type mice: Behavioural Brain Research Vol 115(1) Oct 2000, 85-94.
  • Lorenzana-Jimenez, M., & Salas, M. (1990). Behavioral effects of chronic toluene exposure in the developing rat: Neurotoxicology and Teratology Vol 12(4) Jul-Aug 1990, 353-357.
  • Matsumoto, T., Kosaka, K., Miyakawa, T., Kamijo, A., Endo, K., Yabana, T., et al. (2001). Clinical features of cigarette lighter fluid (butane gas) abusers: Seishin Igaku (Clinical Psychiatry) Vol 43(8) Aug 2001, 875-883.
  • Miyagawa, M., Honma, T., & Sato, M. (1995). Effects of subchronic exposure to toluene on working and reference memory in rats: Neurotoxicology and Teratology Vol 17(6) Nov-Dec 1995, 657-664.
  • Miyagi, Y., Shima, F., Ishido, K., Yasutake, T., & Kamikaseda, K. (1999). Tremor induced by toluene misuse successfully treated by a Vim thalamotomy: Journal of Neurology, Neurosurgery & Psychiatry Vol 66(6) Jun 1999, 794-796.
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Additional materialEdit

BooksEdit

PapersEdit

DissertationsEdit

  • Batis, J. C. (2007). Developmental profile of behavioral and pharmacological changes following repeated binge toluene administration. Dissertation Abstracts International: Section B: The Sciences and Engineering.
  • Dial, J. (1995). Toluene: Its effects on dietary self-selection in nonpregnant, pregnant, and lactating rats. Dissertation Abstracts International: Section B: The Sciences and Engineering.


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