Syklododekanoni

Syklododekanoni
Tunnisteet
CAS-numero 830-13-7
PubChem CID 13246
SMILES C1CCCCCC(=O)CCCCC1[1]
Ominaisuudet
Molekyylikaava C12H22O
Moolimassa 182,296 g/mol
Sulamispiste 62,4 °C[2]
Kiehumispiste 274,8 °C[3]
Tiheys 0,9059 g/cm3[2]
Liukoisuus veteen 0,026 g/l (20 °C)[4]

Syklododekanoni (C12H22O) on syklisiin eli rengasrakenteisiin ketoneihin kuuluva orgaaninen yhdiste. Yhdistettä käytetään orgaanisen kemian synteeseissä muun muassa polymeerien ja hajusteiden valmistamiseen.

Ominaisuudet

Huoneenlämpötilassa syklododekanoni on valkoista vahamaista kiinteää ainetta. Yhdiste ei liukene veteen, mutta liukenee hyvin useisiin orgaanisiin liuottimiin. Syklododekanonin reaktiot ovat ketoneille tyypillisiä. Se muun muassa reagoi vetysyanidin kanssa muodostaen syanohydriinin, aldolikondensaatiolla, Wittig-reaktiolla ja hydroksyyliamiinin kanssa muodostaen syklododekanonioksiimin. Väkevän typpihapon avulla syklododekanoni voidaan hapettaa dodekaanidihapoksi.[3]

Valmistus ja käyttö

Syklododekanonin valmistuksen lähtöaine on syklododekaani. Syklododekaani hapetetaan ilman hapen avulla boorihapon toimiessa katalyyttinä syklododekanolin ja syklododekanonin seokseksi. Tämän seoksen sisältämä syklododekanoli hapetetaan syklododekanoniksi kuparin ja kromin seoksen toimiessa katalyyttinä.[3]

Syklododekanonia käytetään polymeeriteollisuuden raaka-aineiden kuten dodekaanidihapon ja laurolaktaamin valmistamiseen. Hydroksyyliamiini reagoi syklododekanonin kanssa muodostaen oksiimin, joka reagoi Beckmann-toisiintumisella laurolaktaamiksi. Yhdisteestä valmistetaan myös hajusteita kuten muskonia, syklopentadekanonia, pentadekanolidia ja hajusteiden synteesiin tarvittavia 2-bromisyklododekanonia ja 2,12-dibromisyklododekanonia.[3][5][6]

Lähteet

  1. ↑ Cyclododecanone – Substance summary PubChem. NCBI. Viitattu 4.11.2014.
  2. ↑ a b William M. Haynes, David R. Lide, Thomas J. Bruno: CRC Handbook of Chemistry and Physics, s. 3.132. (93rd Edition) CRC Press, 2012. ISBN 978-1439880494 Kirja Googlen teoshaussa (viitattu 4.11.2014). (englanniksi)
  3. ↑ a b c d Georg Oenbrink & Thomas Schiffer: Cyclododecanol, Cyclododecanone, and Laurolactam, Ullmann's Encyclopedia of Industrial Chemistry, John Wiley & Sons, New York, 2009. Viitattu 4.11.2014
  4. ↑ Cyclododecanone:Water solubility European Chemicals Agency. Viitattu 9.7.2024. (englanniksi)
  5. ↑ Jonathan Clayden, Nick Greeves, Stuart Warren: Organic Chemistry, s. 964. Oxford University Press, 2012. ISBN 978-0-19-927029-3 (englanniksi)
  6. ↑ Horst Surburg, Johannes Panten, Kurt Bauer: Common fragrance and flavor materials, s. 150. Wiley-VCH, 2006. ISBN 978-3-527-31315-0 Kirja Googlen teoshaussa (viitattu 4.11.2014). (englanniksi)

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