Toluene
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| Toluene | |
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| Other names | toluene phenylmethane toluol |
| Identifiers | |
| CAS number | |
| RTECS number | XS5250000 |
| SMILES | Cc1ccccc1 |
| Properties | |
| Molecular formula | C7H8 |
| Molar mass | 92.14 g/mol |
| Appearance | Clear colorless, liquid |
| Density | 0.8669 g/mL, liquid |
| Melting point |
−93 °C |
| Boiling point |
110.6 °C |
| Solubility in water | 0.053 g/100 mL (20-25°C) |
| Viscosity | 0.590 cP at 20°C |
| Structure | |
| Dipole moment | 0.36 D |
| Hazards | |
| MSDS | ScienceLab.com |
| Main hazards | highly flammable |
| NFPA 704 |
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| R-phrases | R11, R38, R48/20, R63, R65, R67 |
| S-phrases | (S2), S36/37, S29, S46, S62 |
| Flash point | 4 °C/ 39.2 °F |
| Related Compounds | |
| Related aromatic hydrocarbon | benzene xylene naphthalene |
| Related compounds | methylcyclohexane |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references | |
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Overview
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.
History
The name toluene was derived from the older name toluol that 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 aromatic hydrocarbon towards electrophilic aromatic substitution.[1][1][1] 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.
Preparation
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.
Uses
Toluene is a common solvent, able to dissolve: paints, paint thinners, 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. Industrial uses of toluene include dealkylation to benzene and disproportionation to a mixture of benzene and xylene. 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 84% by volume, fueled all the turbo Formula 1 teams in the 1980s.
Toxicology and metabolism
Inhalation of toluene fumes can be intoxicating, but in larger doses nausea-inducing. Toluene may enter the human system not only through vapour inhalation from the liquid evaporation, but also following soil contamination events, where human contact with soil, ingestion of contaminated groundwater or soil vapour off-gassing can occur.
The toxicity of toluene can be explained mostly by its metabolism. As toluene has very low water solubility, it cannot exit the body via the normal routes (urine, feces, or sweat).[citation needed] 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.[1] The toxic metabolites are created by the remaining 5% that are oxidized to benzaldehyde and cresols.[1][1] Most of the reactive products are detoxified by conjugation to glutathione but the remainder may severely damage cells.[1]
Toluene is mainly excreted as benzoic acid and hippuric acid, both formed by further metabolic oxidation of benzyl alcohol.
See also
- Organic chemistry
- Water pollution
- Isotoluenes are toluene isomers
References
External links
ca:Toluè cs:Toluen de:Toluoleo:Tolueno fa:تولوئن fr:Toluène ko:톨루엔 it:Toluene lv:Toluols lt:Toluenas mk:Толуен nl:Tolueen ja:トルエン no:Toluensk:Toluén fi:Tolueeni sv:Toluen ta:தொலுயீன் vi:Toluen
Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
