Benzoic Acid → Benzoic acid, isodecyl ester

HRID 1869567

Reaktionsgleichung

Reaktionsgleichung von HRID 1869567
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:10](O)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18].[OH-].[K+].[OH-].[Na+]>CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-].[Ti+4].O>[C:1]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 243Benzoic AcidHCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 32898Isodecanol

Produkt 1

HCID 3078322Benzoic acid, isodecyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 21801Titanium tetrabutoxideKatalysatorHCID 962WaterLösungsmittel3×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A 4 liter distillation flask with top-mounted water separator and reflux condenser and also with a sampling port and thermometer was charged with 976 g of benzoic acid (8 mol), 1872 g (12 mol) of isodecanol (Exxal 10, ExxonMobil) and 0.59 g of butyl titanate (0.06% based on the amount of acid) and this initial charge was heated at boiling under a nitrogen atmosphere. The water of reaction produced during the esterification was taken off at regular intervals. When the acid number fell below 0.1 mg KOH/g, after about 3 hours, the excess alcohol was distilled off under reduced pressure through a 10 cm column with Raschig rings. Thereafter the mixture was cooled to 80° C. and transferred to a 4 liter reaction flask with dip tube, top-mounted dropping funnel and column, and attached to a Claisen bridge. It was then neutralized with 5% strength by weight aqueous sodium hydroxide solution (10-fold excess of alkali). The mixture was subsequently heated to 190° C. under reduced pressure (10 mbar). Then 8% by weight of fully demineralized water, based on the amount of crude ester employed, were added dropwise at constant temperature through the dropping funnel. After the water had been added the heating was shut off and cooling took place under reduced pressure. At room temperature, the ester was filtered off on a suction filter with filter paper and filter aid. Gas chromatography indicated a purity for the ester of 99.7%.

Aufarbeitung

  1. distillationA 4 liter distillation flask with top-mounted water separator
  2. temperaturereflux condenser
  3. additionthis initial charge
  4. temperaturewas heated
  5. customproduced during the esterification
  6. distillationthe excess alcohol was distilled off under reduced pressure through a 10 cm column with Raschig rings
  7. customtransferred to a 4 liter reaction flask with dip tube
  8. temperatureThe mixture was subsequently heated to 190° C. under reduced pressure (10 mbar)
  9. additionwere added dropwise at constant temperature through the dropping funnel
  10. temperaturecooling
  11. filtrationAt room temperature, the ester was filtered off on a suction
  12. filtrationfilter
  13. filtrationwith filter paper
  14. filtrationfilter aid

Quellen und Nachweise

ORD-Eintrag
ord-9d3e03c6b65642138840d0cd7b631ef0
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07638568B2

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