Isoforoni

Isoforoni
Tunnisteet
IUPAC-nimi 3,5,5-trimetyylisykloheks-2-en-1-oni
CAS-numero 78-59-1
PubChem CID 6544
SMILES CC1=CC(=O)CC(C1)(C)C[1]
Ominaisuudet
Molekyylikaava C9H14O
Moolimassa 132,202 g/mol
Sulamispiste –8,1 °C[2]
Kiehumispiste 215,3 °C[2]
Tiheys 0,913 g/cm3[3]
Liukoisuus veteen Veteen 14,5 g/l (25 °C)[3]

Isoforoni (C9H14O) on rengasrakenteinen α,β-tyydyttymättömiin ketoneihin kuuluva orgaaninen yhdiste. Yhdistettä käytetään muun muassa liuottimena ja muiden orgaanisten yhdisteiden synteesien lähtöaineena.

Ominaisuudet

Isoforoni on huoneenlämpötilassa väritöntä tai hieman kellertävää nestettä. Sillä on piparmintun tai kamferinkaltainen haju. Isoforoni liukenee kohtalaisesti veteen ja liukenee hyvin moniin orgaanisiin liuottimiin kuten etanoliin, dietyylieetteriin, asetoniin, etyyliasetaattiin ja hiilivetyihin. Isoforonin reaktiot vat tyypillisiä tyydyttymättömille ketoneille.[3][2][4][5] Isoforoni on lievästi myrkyllistä. Yhdiste ärsyttää ihoa, silmiä ja hengitysteitä ja voi suurina pitoisuuksina olla huumaavaa.[2][6]

Valmistus ja käyttö

Isoforonia valmistetaan kondensoimalla asetoniä emäksisen katalyytin, esimerkiksi kaliumhydroksidin, läsnä ollessa noin 200 °C:n lämpötilassa. Reaktiossa välivaiheina muodostuu diasetonialkoholia ja mesityylioksidia. Mahdollisesti reaktioseokseen jäänyt reagoimaton asetoni ja sivutuotteet poistetaan ja hydrolysoidaan ja tuote puhdistetaan alipainetislauksella. [4][5]

Isoforoni ei haihdu kovin herkästi ja tämän ominaisuuden vuoksi sitä käytetään liuottimena painomusteissa, maaleissa ja lakoissa ja liuottamaan hartseja ja rasvoja. Isoforoni on myös monipuolinen synteettisen kemian lähtöaine. Siitä voidaan valmistaa isoforonidi-isosyanaattia, 3,5-ksylenolia, vitamiineja, väriaineita, lääkkeitä ja maatalouskemikaaleja.[3][2][4][5]

Lähteet

  1. ↑ Isophorone – Substance summary PubChem. NCBI. Viitattu 21.7.2018. (englanniksi)
  2. ↑ a b c d e Alén, Raimo: Kokoelma orgaanisia yhdisteitä: Ominaisuudet ja käyttökohteet, s. 281. Helsinki: Consalen Consulting, 2009. ISBN 978-952-92-5627-3
  3. ↑ a b c d Susan Budavari (päätoim.): Merck Index, s. 887. (12th Edition) Merck & Co., 1996. ISBN 0911910-12-3 (englanniksi)
  4. ↑ a b c Yng-Long Hwang & Thomas C. Bedard: Ketones, Kirk-Othmer Encyclopedia of Chemical Technology, John Wiley & Sons, New York, 2001. Viitattu 21.7.2018
  5. ↑ a b c Hardo Siegel & Manfred Eggersdorfer: Ketones, Ullmann’s Encyclopedia of Industrial Chemistry, John Wiley & Sons, New York, 2000. Viitattu 21.7.2018
  6. ↑ Isoforonin kansainvälinen kemikaalikortti Viitattu 21.7.2018

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