Water → Bis(2-ethylhexyl) tetrabromophthalate

HRID 580657Notes

Reaction equation

HRID 580657 reaction equation
[Br:1][C:2]1[C:3]([Br:15])=[C:4]([Br:14])[C:5]([Br:13])=[C:6]2[C:11](=[O:12])[O:10][C:8](=[O:9])[C:7]=12.[CH2:16]([CH:18]([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:19]O)[CH3:17].[OH2:25]>CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[Br:13][C:5]1[C:4]([Br:14])=[C:3]([Br:15])[C:2]([Br:1])=[C:7]([C:8]([O:9][CH2:11][CH:6]([CH2:7][CH3:8])[CH2:5][CH2:4][CH2:3][CH3:2])=[O:25])[C:6]=1[C:11]([O:10][CH2:19][CH:18]([CH2:16][CH3:17])[CH2:21][CH2:22][CH2:23][CH3:24])=[O:12]

Participants

5

Reactant 3

HCID 962WaterHCID 77202-EthylhexanolHCID 12443Tetrabromophthalic anhydride

Product 1

HCID 117291Bis(2-ethylhexyl) tetrabromophthalate

Reagents, catalysts & solvents 1

HCID 11026Titanium isopropoxideCatalyst

Procedure

Tetrabromophthalic anhydride (1391.1 grams; 3.0 moles), 2-ethyl-1-hexanol (1171.8 grams; 9.0 moles) and titanium (IV) isopropoxide (7 ml.; 0.5 volume percent on tetrabromophthalic anhydride) were charged into a 3,000 ml. reaction flask maintained under a nitrogen atmosphere. The reaction flask was fitted with a mechanical stirrer. thermometer. nitrogen inlet tube, and a Dean-Stark water trap connected to a Friedrich condensor. The reaction mixture was heated with agitation at a temperature equal or less than about 200° C. for eight hours. The resulting product (2.497 grams) was an amber thick clear liquid having an acidity of 1.4 meq. per 100 grams.

Workup

  1. customreaction flask
  2. temperaturemaintained under a nitrogen atmosphere
  3. customThe reaction flask was fitted with a mechanical stirrer
  4. temperatureThe reaction mixture was heated with agitation at a temperature equal or less than about 200° C. for eight hours

Sources & evidence

ORD record
ord-e5ea6f147e794492a4e320ea48c16f24
Source dataset
uspto-grants-1988_06
Patent number
US04754053

Reaction notes

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