O-Nitroaniliini

o-Nitroaniliini
Tunnisteet
IUPAC-nimi 2-nitroaniliini
CAS-numero 88-74-4
PubChem CID 6946
SMILES C1=CC=C(C(=C1)N)[N+](=O)[O-][1]
Ominaisuudet
Molekyylikaava C6H6N2O2
Moolimassa 138,128 g/mol
Sulamispiste 69,7 °C[2]
Kiehumispiste 284 °C[2]
Tiheys 1,442 g/cm3[2]
Liukoisuus veteen Veteen 0,126 g/100 ml (25 °C)[3] Liukenee myös orgaanisiin liuottimiin.[2]

o-Nitroaniliini eli 2-nitroaniliini (C6H6N2O2) on nitroryhmän sisältävä orgaaninen yhdiste ja aniliinin johdannainen. Yhdistettä käytetään orgaanisessa synteesissä valmistettaessa väriaineita ja muita kemikaaleja. o-Nitroaniliinista käytetään myös nimiä 2-nitroaminobentseeni ja 1-amino-2-nitrobentseeni. Kiinteänä aine on väriltään oranssia. o-Nitroaniliini on m-nitroaniliinin ja p-nitroaniliinin isomeeri.

Valmistus

o-Nitroaniliinia valmistetaan yleensä teollisesti o-kloorinitrobentseenin ammonolyysillä eli reaktiolla väkevän ammoniakkiliuoksen kanssa. Reaktio tapahtuu 4MPa:n paineessa ja lämpötila kohotetaan vähitellen 180 °C asti. Reaktio on hyvin eksoterminen ja liiallinen lämmitys voi johtaa hallitsemattomaan reaktioon.[4]

Yhdistettä voidaan valmistaa myös lähtemällä asetanilidista, jolloin muodostuu myös p-nitroaniliinia, tai 2-nitroaniliini-4-sulfonihaposta.[2]

Käyttö

Suurin osa o-nitroaniliinista käytetään o-fenyleenidiamiinin valmistukseen raudan tai vedyn avulla pelkistämällä. Ainetta käytetään myös atsovärien ja vat-väriaineiden sekä 2-aminoasetanilidin valmistamiseen.[2][4]

Lähteet

  1. o-Nitroaniline – Substance summary NCBI. Viitattu 7.3.2011.
  2. a b c d e f Raimo Alén: Kokoelma orgaanisia yhdisteitä, s. 554. Consalen Consulting, 2009. ISBN 978-952-92-5627-3
  3. O-Nitroaniliinin kansainvälinen kemikaalikortti
  4. a b Gerald Booth: Nitro Compounds, Aromatic, Ullmann's Encyclopedia of Industrial Chemistry, John Wiley & Sons, New York, 2002 Teoksen verkkoversio Viitattu 7.3.2011
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