Ammonia → 2-Undecyl-2-oxazoline

HRID 1086418

Reaktionsgleichung

Reaktionsgleichung von HRID 1086418
[CH2:1]([C:12]#[N:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].N[CH2:15][CH2:16][OH:17].N>O.O.C([O-])(=O)C.[Cd+2].C([O-])(=O)C.C(O)CCC>[CH2:1]([C:12]1[O:17][CH2:16][CH2:15][N:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Komponenten

6

Edukt 3

HCID 222AmmoniaHCID 700EthanolamineHCID 17092Dodecanenitrile

Produkt 1

HCID 3470762-Undecyl-2-oxazolineAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6537495Cadmium acetate, dihydrateKatalysatorHCID 2631-ButanolLösungsmittel

Reaktionsbedingungen

Temperatur
125 °C

Versuchsvorschrift

The reaction was carried out under nitrogen atmosphere in a three neck flask equipped with a magnetic stirring bar, reflux condenser, addition funnel and thermometer. 50 ml of 1-butanol and 667 mg (2.5 mmoles) of cadmium acetate dihydrate was introduced and the catalyst was dissolved by slight warming. 18.13 g (100 mmoles) of undecyl cyanide was added and the solution was heated to 125° C. 7.33 g (120 mmoles) of 2-aminoethanol was then added dropwise controlling the evolution of ammonia. At the end of the reaction (ca. 48 hrs.) the solvent was removed under vacuo. The residue was treated with 100 ml of petroleum ether and filtered after keeping for several hours. The filtrate was washed with water, dried over anhydrous magnesium sulfate, concentrated and the residue was distilled 114° C./0.5 mm to give 19.83 g (88%) of 2-undecyl-2-oxazoline.

Aufarbeitung

  1. customequipped with a magnetic stirring bar
  2. temperaturereflux
  3. additioncondenser, addition funnel
  4. dissolutionthe catalyst was dissolved by slight warming
  5. customAt the end of the reaction (ca. 48 hrs.) the solvent
  6. customwas removed under vacuo
  7. additionThe residue was treated with 100 ml of petroleum ether
  8. filtrationfiltered
  9. waitafter keeping for several hours
  10. washThe filtrate was washed with water
  11. dry with materialdried over anhydrous magnesium sulfate
  12. concentrationconcentrated
  13. distillationthe residue was distilled 114° C./0.5 mm

Quellen und Nachweise

ORD-Eintrag
ord-fd788290069c4f7cb9cd5ed57b5a3c66
Quelldatensatz
uspto-grants-1991_07
Patentnummer
US05030629

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