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Hydrochloric Acid → Azelaic Acid

HRID 1769432
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1769432
[C:1]([OH:20])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]CC/C=C\C/C=C\CCCCC.[C:21]([OH:40])(=[O:39])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]C/C=C\CCCCCCCC.OO.Cl.[C:44]([OH:48])([CH3:47])(C)C>[O-][V]([O-])([O-])=O.[Na+].[Na+].[Na+]>[C:1]([OH:20])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[C:21]([OH:40])(=[O:39])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:47][C:44]([OH:48])=[O:19]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 6386tert-ButanolHCID 445639Oleic AcidHCID 5280450Linoleic Acid2×

Produkt 2

HCID 2266Azelaic AcidHCID 8892
Hexanoic Acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 61671Sodium orthovanadateKatalysator

Versuchsvorschrift

A mixture of linoleic acid (562.4 mg, 2 mmol) and oleic acid (565.7 mg, 2 mmol) was treated with sodium orthovanadate (18.9 mg, 0.1 mmol) and 30% w/v hydrogen peroxide (6 ml) in tertiary butanol (20 ml) in a manner analogous to that in Example 9. In this example, the pH of the reaction mixture was about 6 to 7 after the addition of catalyst. The pH was adjusted to about 2 to 3 with concentrated hydrochloric acid before heating was commenced. After heating, the resulting product was further processed and analyzed in a manner analogous to that in Example 1. The analytical results showed that essentially all of the linoleic acid had been cleaved to produce hexanoic acid and azelaic acid, whereas only 6% of the oleic acid was cleaved to produce pelargonic acid and azelaic acid.

Aufarbeitung

  1. additionafter the addition of catalyst
  2. temperaturebefore heating
  3. temperatureAfter heating
  4. customThe analytical results

Quellen und Nachweise

ORD-Eintrag
ord-1c2fecca1b2a479d9fafd320ef5ea175
Quelldatensatz
uspto-grants-1995_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05380931

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