What is methyl anthranilate used for?
|Brief description||colorless to brown liquid with an amine-like odor|
|Molar mass||93.13 g mol−1|
|density||1.02 g · cm−3 |
|Melting point||−6 ° C|
|boiling point||184 ° C|
40 Pa (20 ° C)
soluble in water: 34 g · l−1, easily soluble in ethanol, organic solvents
2 ml m−3 and 7.7 mg · m, respectively−3 
871 mg kg−1 (oral, rat)
|WGK||2 - hazardous to water|
|As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions.|
aniline [aniˈliːn] (from Arabic an-nil "Indigo plant") is a colorless, slightly oily liquid with a sweetish odor that turns slightly brownish in the air. It is a benzene ring with an amino group (–NH2) and thus an aromatic compound. When mixed with acids, it forms aniline salts. The basic effect of aniline is reduced by the mesomeric effect, as this leads to a lower electron density on the otherwise proton-absorbing NH2-Rest leads.
Aniline was first produced in 1826 by Otto Unverdorben by distilling lime from indigo - a blue dye. Hence it used to be under the name Blue oil known. Aniline has been used by the Badische Anilin- und Soda-Fabrik (BASF) since 1897 to synthesize the dye indigo, which was previously only obtained from vegetable raw materials (Heumann synthesis). Aniline had already been produced on a large scale before that, for example by Agfa (Aktien-Gesellschaft für Anilin-Fabrikation) from 1873 onwards. A well-known use of the dye was aniline leather. Aniline has also been used in printing technology, including flexographic printing was given the nickname aniline, which is still used today, because it was only through the aniline that a good print quality could be produced.
In technology, aniline is obtained by reducing nitrobenzene with iron in the presence of hydrochloric acid:
- Nitrobenzene, iron and water react to form aniline and iron (II, III) oxide.
It is then neutralized with quicklime (CaO) and the aniline is distilled off together with the water.
There are other processes, for example the ammonolysis of chlorobenzene or phenol:
In the chemical industry, it is primarily used as a raw material for the synthesis of colors and synthetic fibers, but also for the manufacture of rubber and medicines.
Toxicity of aniline
Aniline is a blood-altering poison that can trigger hemolysis and is suspected of causing cancer (carcinogenic). Since it can be absorbed through the skin, it is a contact poison.
- Karl Aloys Schenzinger: Aniline - novel of a dye. 1936, ASIN: B000W83G7E.
Safety data sheets
Safety data sheets from various manufacturers in alphabetical order for aniline:
Categories: Toxic Substance | Environmentally hazardous substance | Amine | Aromat
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