2,4-Diaminotoluene on:
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2,4-Diaminotoluene is an
organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. T ...
with the formula C6H3(NH2)2CH3. It is one isomer of six with this formula. It is a white solid although commercial samples are often yellow-tan.
Preparation
It is prepared byhydrogenation
Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to reduce or saturate organ ...
of 2,4-dinitrotoluene
2,4-Dinitrotoluene (DNT) or dinitro is an organic compound with the formula C7H6N2O4. This pale yellow crystalline solid is well known as a precursor to trinitrotoluene (TNT) but is mainly produced as a precursor to toluene diisocyanate.
Isomers ...
using a nickel catalyst. Commercial samples often contain up to 20% of the 2,6- isomer.Robert A. Smiley "Phenylene- and Toluenediamines" in ''Ullmann's Encyclopedia of Industrial Chemistry'', 2002, Wiley-VCH, Weinheim.
A laboratory method involves reduction of 2,4-dinitrotoluene with iron powder.
Use
It is mainly used as a precursor totoluene diisocyanate
Toluene diisocyanate (TDI) is an organic compound with the formula CH3C6H3(NCO)2. Two of the six possible isomers are commercially important: 2,4-TDI (CAS: 584-84-9) and 2,6-TDI (CAS: 91-08-7). 2,4-TDI is produced in the pure state, but TDI is oft ...
, a precursor to polyurethane
Polyurethane (; often abbreviated PUR and PU) refers to a class of polymers composed of organic units joined by carbamate (urethane) links. In contrast to other common polymers such as polyethylene and polystyrene, polyurethane is produced from ...
.
Its reaction with benzenediazonium chloride
Benzenediazonium tetrafluoroborate is an organic compound with the formula 6H5N2F4. It is a salt of a diazonium cation and tetrafluoroborate. It exists as a colourless solid that is soluble in polar solvents. It is the parent member of the ary ...
gives the cationic azo dye Basic Orange 1. Condensation of 2,4-diaminotoluene with acetaldehyde gives the acridine dye called Basic Yellow 9.Thomas Gessner and Udo Mayer "Triarylmethane and Diarylmethane Dyes" in Ullmann's Encyclopedia of Industrial Chemistry
''Ullmann's Encyclopedia of Industrial Chemistry'' is a major reference work related to industrial chemistry by Chemist Fritz Ullmann, first published in 1914, and exclusively in German as "Enzyklopädie der Technischen Chemie" until 1984.
Hist ...
2002, Wiley-VCH
Wiley-VCH is a German publisher owned by John Wiley & Sons. It was founded in 1921 as Verlag Chemie (meaning "Chemistry Press": VCH stands for ''Verlag Chemie'') by two German learned societies. Later, it was merged into the German Chemical Soci ...
, Weinheim.
References
{{DEFAULTSORT:Diaminotoluene, 2,4- Anilines Diamines Monomers Alkyl-substituted benzenes