Mesitylene

Colorless liquid with an aromatic odor oily

Liquid

0.86 g · cm -3

-45 ° C

165 ° C

2,69 hPa ( 20 ° C)

• Very poor in water ( 2.9 g · l-1 at 20 ° C)
• Soluble in ethanol and diethyl ether

1.49937 (20 ° C)

Attention

20 ml · m-3 and 100 mg · m-3

Template: Infobox chemical / molecular formula search available

Mesitylene (1,3,5- trimethylbenzene ) is substituted with three methyl groups, and thus an alkylbenzene and benzene, an aromatic hydrocarbon. It belongs with its isomers Hemellitol (1,2,3 -trimethylbenzene ) and pseudocumene (1,2,4- trimethylbenzene ) to the group of trimethyl benzenes and also to the group of C3 - benzenes.

History

Mesitylene was first produced in 1837 by the Irish chemist Robert Kane by acetone heated with concentrated sulfuric acid. He called the new substance " mesitylene ," because the German chemist Carl Reichenbach acetone " Mesit " had called (from the Greek μεσίτης, the mediator ); and Kane took the view that his reaction had drained Mesit, with a conversion to an alkene, the " mesitylene ." But Kane's determination of the chemical composition of mesitylene was not true. The correct empirical formula was found by August Wilhelm von Hofmann in 1849. In 1866 Adolf von Baeyer showed that the structure of the mesitylene coincides with that of 1,3,5- trimethylbenzene. The conclusive proof that mesitylene was identical with 1,3,5 - trimethylbenzene, was provided by Albert Ladenburg in 1874.

Occurrence and representation

It is found in petroleum and coal tar.

Mesitylene is obtained from acetone by distillation with sulfuric acid.

Properties

Mesitylene is a colorless liquid having a melting point of -45 ° C and a boiling point of 165 ° C. It has an oily aromatic odor and is highly flammable. In water it is insoluble; in benzene, ether and ethanol, it is readily soluble. The flash point is 44 ° C, the ignition temperature at 550 ° C. Above 44 ° C (flash point ) forms mesitylene with the explosive mixture in air. Inhalation and ingestion of lead to drowsiness, headache, cough, fatigue and sore throat. The substance irritates the skin ( it is caused by the material degreased), eyes and respiratory system. The vapors cause a narcotic effect to higher concentration.

Use and preparation

Mesitylene is used as a solvent for resin and rubber as well as for organic synthesis ( for example antioxidants).