1-Octanol → Tetraoctyl pyromellitate

HRID 2068474Notes

Reaction equation

HRID 2068474 reaction equation
[C:1]([OH:18])(=[O:17])[C:2]1[C:3](=[CH:7][C:8](=[C:12]([CH:16]=1)[C:13]([OH:15])=[O:14])[C:9]([OH:11])=[O:10])[C:4]([OH:6])=[O:5].[CH2:19](O)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]>CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4].C1(C)C(C)=CC=CC=1>[CH2:19]([O:14][C:13](=[O:15])[C:12]1[C:8](=[CH:7][C:3](=[C:2]([CH:16]=1)[C:1]([O:18][CH2:9][CH2:8][CH2:7][CH2:3][CH2:2][CH2:16][CH2:12][CH3:13])=[O:17])[C:4]([O:6][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[O:5])[C:9]([O:11][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[O:10])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 2

HCID 9571-OctanolHCID 6961Pyromellitic Acid

Product 1

HCID 21895707Tetraoctyl pyromellitateYield 209%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 7237O-XyleneSolvent

Procedure

To a 2-liter four necked flask equipped with Dean Stark, 218 g of anhydrous pyromellitic acid, 650 g of n-octanol, 0.2 g of titanium tetraisopropoxide and 300 ml of xylene were added and reacted with agitation at 160 degrees C. for 4 hours under nitrogen stream while distilling water. Subsequently, washing by saturated saline and washing by 0.1 N aqueous sodium hydroxide were respectively conducted three times, followed by being dried by anhydrous magnesium sulfate. After magnesium sulfate was filtered, unreacted alcohol was distilled under diminished pressure to obtain 630 g of pyromellitic acid tetraoctyl ester as a residue. The obtained compound, regarded as Comparative 2-3, was similarly measured with respect to the properties.

Workup

  1. additionwere added
  2. customreacted with agitation at 160 degrees C
  3. distillationfor 4 hours under nitrogen stream while distilling water
  4. washSubsequently, washing by saturated saline
  5. washwashing by 0.1 N aqueous sodium hydroxide
  6. dry with materialby being dried by anhydrous magnesium sulfate
  7. filtrationAfter magnesium sulfate was filtered
  8. distillationunreacted alcohol was distilled under diminished pressure

Sources & evidence

ORD record
ord-099da2daed804ef08fe2d40c8e914b85
Source dataset
uspto-grants-2012_10
Patent number
US08299004B2

Reaction notes

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