1-Octanol → Tetraoctyl pyromellitate

HRID 405687

Reaction equation

HRID 405687 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>[C:9]([O:11][CH2:9][CH2:8][CH2:7][CH2:3][CH2:2][CH2:16][CH2:12][CH3:13])(=[O:10])[C:8]1[C:12](=[CH:16][C:2](=[C:3]([CH:7]=1)[C:4]([O:6][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[O:5])[C:1]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[O:17])[C:13]([O:15][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[O:14]

Participants

5

Reactant 2

HCID 9571-OctanolHCID 6961Pyromellitic Acid

Product 1

HCID 21895707Tetraoctyl pyromellitateYield 209%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 7237O-XyleneSolvent

Conditions

Temperature
160 °C

Procedure

To a 2-liter four necked flask equipped with Dean Stark apparatus, 218 g of anhydrous pyromellitic acid, 650 g of n-octanol, 0.2 g of titanium tetraisopropoxide and 300 cc of xylene were added and reacted with stirring at 160 degrees C. for 4 hours under nitrogen stream while distilling water. Subsequently, washing by saturated brine 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 reduced pressure to obtain 630 g of tetraoctyl pyromellitate. Tetraoctyl pyromellitate, regarded as Comparative Example 3, was similarly measured with respect to the properties.

Workup

  1. additionwere added
  2. customreacted
  3. distillationfor 4 hours under nitrogen stream while distilling water
  4. washSubsequently, washing by saturated brine
  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 reduced pressure

Sources & evidence

ORD record
ord-0c7ffbe529c247c1ac5f07b5d68037c1
Source dataset
uspto-grants-2014_06
Patent number
US08754019B2

Linked notes

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