Toluene

Toluene, also known as methylbenzene or phenylmethane, is a clear, inhalant drug for its intoxicating properties.^{[citation needed]}

History

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 properties

Toluene reacts as a normal trinitrotoluene (TNT).

With other reagents the methyl side chain in toluene may react, undergoing oxidation. Reaction with AIBN leads to benzyl bromide.

Catalytic hydrogen to go to completion, because of the stability of the aromatic system. pka is approximately 45.

Preparation

Toluene occurs naturally at low levels in crude oil and is usually produced in the processes of making gasoline via a distillation or solvent extraction) takes place in a BTX plant.

Uses

Toluene is a common 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.

Toxicology and metabolism

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).^{[citation needed]} It must be metabolized in order to be excreted. The methyl group of toluene is more easily oxidized by glutathione but the remainder may severely damage cells.^[7]

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

See also

• Organic chemistry
• Water pollution
• Isotoluenes are toluene isomers

References

1. ^ B. S. Furnell et al., Vogel's Textbook of Practical Organic Chemistry, 5th edition, Longman/Wiley, New York, 1989
2. ^ L. G. Wade, Organic Chemistry, 5th ed., p. 871, Prentice Hall, Upper Saddle RIver, New Jersey, 2003
3. ^ J. March, Advanced Organic Chemistry, 4th ed., p. 723, Wiley, New York, 1992
4. ^ Nakajima T, Wang R, Elovaara E, Gonzalez F, Gelboin H, Raunio H, Pelkonen O, Vainio H, Aoyama T (1997). "Toluene metabolism by cDNA-expressed human hepatic cytochrome P450". Biochem Pharmacol 53 (3): 271-7. PMID 9065730.
5. ^ Chapman D, Moore T, Michener S, Powis G. "Metabolism and covalent binding of [14C]toluene by human and rat liver microsomal fractions and liver slices". Drug Metab Dispos 18 (6): 929-36. PMID 1981539.
6. ^ Hanioka H, Hamamura M, Kakino K, Ogata H, Jinno H, Takahashi A, Nishimura T, Ando M (1995). "Dog liver microsomal P450 enzyme-mediated toluene biotransformation". Xenobiotica 25 (11): 1207-17. PMID 8592870.
7. ^ van Doorn R, Leijdekkers C, Bos R, Brouns R, Henderson P (1981). "Alcohol and sulphate intermediates in the metabolism of toluene and xylenes to mercapturic acids". J Appl Toxicol 1 (4): 236-42. PMID 6764216.