Diisopropanolamine → 2,6-dimethyl-7a-undecyl-tetrahydro-2H-oxazolo[2,3-b]oxazole

HRID 2116744Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2116744
[CH3:1][CH:2]([OH:9])[CH2:3][NH:4][CH2:5][CH:6]([OH:8])[CH3:7].CO[Na].[C:13](OC)(=O)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>C([O-])(=O)C.[Zn+2].C([O-])(=O)C>[CH3:1][CH:2]1[O:9][C:24]2([CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH3:13])[O:8][CH:6]([CH3:7])[CH2:5][N:4]2[CH2:3]1

Komponenten

5

Edukt 3

HCID 8086Diisopropanolamine2×HCID 8139Methyl LaurateHCID 178418582HCID 178418582, Verbindung

Produkt 1

HCID 692034952,6-dimethyl-7a-undecyl-tetrahydro-2H-oxazolo[2,3-b]oxazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 11192Zinc AcetateKatalysator

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

In a first stage to a reactor, equipped with a distillation column, condenser, and graduated receiver, 199.8 g (1.5 mol) of diisopropanol amine (DIPA) and 7.5 g of CH3ONa (30% in methanol) were added and the batch heated to 75° C. 160.5 g (0.75 mol) of methyl laurate were added during 2 hours at 75° C. Temperature was gradually increased during 3 hours. Methanol has been removed at lower pressure 26,660 Pa) and at 120° C. and excess of DIPA has been removed at a pressure below 133 Pa and at 140° C. The so prepared amide looked as yellow fat (melting temperature of above 130° C). In a second stage 0.5 weight % of zinc acetate, based on the intermediate product after stage 1 were added and the batch was heated at 180° C. for 6 hours. Fraction distillation has been done at a pressure below 133 Pa. Three fractions were obtained: I) with boiling point <105° C.; amount above 5 weight %; mainly DIPA; II) with boiling point 105-145° C.; amount 50 weight %; amide acetal (purity 90%) and III) 45 weight %—distillation rest. The yield of amide acetal calculated on methyl laurate was 43%. Initial color and color stability during storage (on shelf) of an amide acetal prepared according to the invention and a comparative amide acetal prepared from nitriles have been evaluated. The amide acetal according to the invention shows a better initial color and better color stability than the amide acetal prepared from nitrites.

Aufarbeitung

  1. customIn a first stage to a reactor, equipped with a distillation column, condenser
  2. additionwere added
  3. temperatureTemperature was gradually increased during 3 hours
  4. customMethanol has been removed at lower pressure 26,660 Pa) and at 120° C.
  5. customexcess of DIPA has been removed at a pressure below 133 Pa and at 140° C
  6. customThe so prepared amide
  7. additionwere added
  8. temperaturethe batch was heated at 180° C. for 6 hours
  9. distillationFraction distillation
  10. customThree fractions were obtained
  11. distillationamide acetal (purity 90%) and III) 45 weight %—distillation rest
  12. customInitial color and color stability during storage (on shelf) of an amide acetal prepared

Quellen und Nachweise

ORD-Eintrag
ord-4e0326109ef0468eb11d23af43d74009
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07439354B2

Notizen zur Reaktion

Wird geladen…