Benzoic Acid → Nonylbenzoate, branched and linear

HRID 2253416Notes

Reaction equation

HRID 2253416 reaction equation
[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][CH:16]([CH3:18])[CH3:17].CC(C(O)=O)C1C=CC(CC2C(=O)CCC2)=CC=1>CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-].[Ti+4]>[C:1]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 243Benzoic AcidHCID 3965LoxoprofenHCID 17072Isononanol

Product 1

HCID 53673956Nonylbenzoate, branched and linear

Reagents, catalysts & solvents 1

HCID 21801Titanium tetrabutoxideCatalyst

Procedure

976 g of benzoic acid (8 mol), 1728 g of isononanol from OXENO Olefinchemie GmbH (12 mol), and 0.59 g of butyl titanate (0.06%, based on the amount of acid) are weighed into a four liter distillation flask on top of which a water separator and reflux condenser have been attached, and which has a sampling port and thermometer, and are heated to boiling under nitrogen. The water of reaction produced during the esterification process was removed sequentially. Once the acid value fell below 0.1 mg KOH/g (after about 3 hours), the mixture was first cooled below 60° C., and a 20 cm multifill column was placed on the apparatus. The pressure was then reduced to 2 mbar, and excess alcohol was first distilled off (about 120° C.). After removal of an intermediate fraction at up to 140° C. it was possible to distill over the isononyl benzoate within a range of 142 to 147° C. (at 2 mbar) measured at the head of the column. Purity >99.7% was determined by gas chromatography.

Workup

  1. distillationare weighed into a four liter distillation flask on top of which a water separator
  2. temperaturereflux condenser
  3. temperatureare heated
  4. customThe water of reaction
  5. customproduced during the esterification process
  6. customwas removed sequentially
  7. custom(after about 3 hours)
  8. temperaturethe mixture was first cooled below 60° C.
  9. distillationwas first distilled off (about 120° C.)
  10. customAfter removal of an intermediate fraction at up to 140° C. it
  11. distillationto distill over the isononyl benzoate within a range of 142 to 147° C. (at 2 mbar)

Sources & evidence

ORD record
ord-a2f10b403ec040748e0e3c53ce6fa61b
Source dataset
uspto-grants-2008_01
Patent number
US07323588B2

Reaction notes

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