Toluene

The name Toluene (CAS NO.108-88-3) 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 J?ns Jakob Berzelius.

Community Right-To-Know List. Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

OSHA PEL: TWA 100 ppm; STEL 150 ppm
ACGIH TLV: TWA 50 ppm (skin); Not Classifiable as a Human Carcinogen; BEI: 1.6 g/g creatinine of hippuric acid in urine at end of shift; 0.05 mg/L toluene in venous blood prior to last shift of workweek; BEI: BEI: 0.05 mg/L toluene in venous blood prior to last shift of work ek; 0.5 mg/L o-cresol in urine at end of shift
DFG MAK: 50 ppm (190 mg/m³); BAT: 340 μg/dL in blood at end of shift
NIOSH REL: (Toluene) TWA 100 ppm; CL 200 ppm/10M
DOT Classification:  3; Label: Flammable Liquid

For occupational chemical analysis use NIOSH: Hydrocarbons, Aromatic, 1501; Hydrocarbons, Bp: 36–126°C, 1500.

Toluene, also called Methylbenzene, is a colorless, flammable liquid with a benzenelike odor. It is insoluble in water, but miscible with benzene, alcohol, ether and other organic solvents. Toluene was first isolated as aromatic extract from the tropical Colombian tree Myroxylon balsamum. In chemical, it is a mono-substituted benzene derivative commonly used as an industrial solvent for the manufacturing of paints, chemicals, pharmaceuticals, and rubber. And it is not only an important organic solvent, but also dissolving a number of notable inorganic chemicals such as sulfur.

Physical properties about Toluene are: (1)ACD/LogP: 2.72; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.72; (4)ACD/LogD (pH 7.4): 2.72; (5)ACD/BCF (pH 5.5): 68.71; (6)ACD/BCF (pH 7.4): 68.71; (7)ACD/KOC (pH 5.5): 718.68; (8)Index of Refraction: 1.5; (9)Molar Refractivity: 31.078 cm3; (10)Molar Volume: 105.709 cm³; (11)Polarizability: 12.32 10-24cm³; (12)Surface Tension: 28.8169994354248 dyne/cm; (13)Density: 0.872 g/cm³; (14)Flash Point: 10 °C; (15)Enthalpy of Vaporization: 33.48 kJ/mol; (16)Boiling Point: 110.602 °C at 760 mmHg; (17)Vapour Pressure: 27.7119998931885 mmHg at 25°C

Preparation of Toluene: Toluene can be produced by many methods.
1. It is derived from coal tar, and commercial grades usually contain small amounts of benzene as an impurity.

2. It can be obtained by benzene from Friedel–Crafts reaction. Benzene reacts with CH₃⁺ and AlCl₄^- which are got by CH₃Cl and AlCl₃ to form toluene. In this reaction, the AlCl³ is used as catalyst.
CH₃Cl + AlCl₃ → CH₃⁺ + AlCl₄^-
C₆H₅H + CH₃+ + AlCl₄^- → C₆H₅CH₃ + HCl + AlCl₃

3. It can be obtained by cresol from distillation with zinc dust.
C₆H₄CH₃OH (cresol) + Zn → C₆H₅CH₃ (toluene) + ZnO

4. It can be obtained by bromobenzene from Wurtz-Fittig reaction. When bromobenzene and methyl bromide react with sodium metal in dry ether solution, toluene is obtained.
C₆H₅Br + CH₃Br + 2Na → C₆H₅CH₃ + 2NaBr

5. It can be obtained by decarboxylation from toluic acid. Heat the sodium salt of toluic acid (o-, m-, p-) with soda lime, then toluene is synthesized.
C₆H₄CH₃COONa (sodium toluate) + NaOH → C₆H₅CH₃ (toluene) + Na₂CO₃

Uses of Toluene:
1. Toluene is not only widely used as organic solvent, but also used as raw material to synthetize pharmaceuticals, paints, resins, dyes, explosives, pesticides ansd so on. Moreover, it used as standard material for chromatography and analytical reagent.

2. Toluene is also used as raw material in production of benzene and many other chemical products. For example: it can react with tert-butyl hydroperoxide to get benzyl-tert-butyl peroxide. This reaction needs reagent RuIII-Montmorillonite K10 and solvent acetonitrile by heating. The reaction time is 4 hours. The yield is 60%.

3. It is used as leaching agent of plant components. Used in internal combustion engines, toluene can be used as an octane booster in gasoline fuels. And it has also been used as a coolant for its good heat transfer capabilities in sodium cold traps used in nuclear reactor system loops.

When you are using this chemical, please be cautious about it as the following: Toluene is toxic by inhalation, in contact with skin and if swallowed. And it also has danger of very serious irreversible effects. The vapours of toluene may cause drowsiness and dizziness. If you want to contact this product, you must wear suitable protective clothing and gloves. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) If swallowed, do not induce vomitting; seek medical advice immediately and show this container or label. So toluene should be sealed in the container and stored in the cool and dry place which must be away from oxidant.

You can still convert the following datas into molecular structure:
1.Smiles:c1(ccccc1)C
2.InChI:InChI=1S/C7H8/c1-7-5-3-2-4-6-7/h2-6H,1H3

The toxicity data is as follows: