Methane → Bis(2-Hydroxyethyl)Sebacate

HRID 328315

Reaktionsgleichung

Reaktionsgleichung von HRID 328315
[C:1]([OH:14])(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11].[CH2:15]1[O:17][CH2:16]1.C.[CH2:19]([C:23](C)=[O:24])C(C)C>>[OH:24][CH2:23][CH2:19][O:11][C:10](=[O:12])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([O:14][CH2:16][CH2:15][OH:17])=[O:13]

Komponenten

5

Edukt 4

HCID 297MethaneHCID 5192Sebacic AcidHCID 6354Ethylene OxideHCID 7909Methyl Isobutyl Ketone

Produkt 1

HCID 14094566Bis(2-Hydroxyethyl)SebacateAusbeute 44 %

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

Sebacic acid (50.5g, 0.25 mole), the catalyst of Example II (0.5g), and methyl isobutyl ketone (250 ml) were charged to the autoclave and heated to 150° C. Ethylene oxide (24.23g, 0.55 mole) was introduced from a nitrogen-pressurized cylinder to the autoclave. The temperature rose to 160° C and the pressure increased from 25 psi to 100 psi. After 60 minutes at 160° C, the pressure dropped to 88 psi and the system was vented. The light yellow green reaction mixture was mixed with carbon black, heated to boiling, and filtered through a sintered-glass funnel containing some Al2O3. Upon cooling to -30° C, the precipitated material was filtered, washed with cold hexane, dried in a vacuum desiccator for 48 hours and weighed (31.0g). The product was isolated in 44.0% yield and melted at 47° C. The infrared bands at 3350 cm-1 (OH), 2970 cm-1 (CH2) and 1730 cm-1 (C=O) were characteristic of the expected ester. Anal. Calcd. for C14H26O6 : C, 57.93; H, 8.97; O, 33.10, Found: C, 58.00; H, 9.02. Molecular weight by hydroxyl number. Theory: 290. Found: 289.

Aufarbeitung

  1. customrose to 160° C
  2. temperaturethe pressure increased from 25 psi to 100 psi
  3. additionthe pressure dropped to 88 psi
  4. temperatureheated
  5. filtrationfiltered through a sintered-glass funnel
  6. additioncontaining some Al2O3
  7. temperatureUpon cooling to -30° C
  8. filtrationthe precipitated material was filtered
  9. washwashed with cold hexane
  10. customdried in a vacuum desiccator for 48 hours
  11. customThe product was isolated in 44.0% yield and melted at 47° C

Quellen und Nachweise

ORD-Eintrag
ord-20e85d183a4340bda08dd08ec3e8aa8b
Quelldatensatz
uspto-grants-1977_04
Patentnummer
US04017429

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