Bischlorophthalimide → Bisphenol A

HRID 1820948Notes

Reaction equation

HRID 1820948 reaction equation
[Na].[Na].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)([CH3:12])[CH3:11])=[CH:6][CH:5]=1.[Na].[Na].C1(O)C=CC(C2C=CC(O)=CC=2)=CC=1.ClC1C(Cl)=C2C(=O)NC(=O)C2=CC=1>C1C=CC(Cl)=C(Cl)C=1>[CH3:12][C:10]([C:7]1[CH:6]=[CH:5][C:4]([OH:3])=[CH:9][CH:8]=1)([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)[CH3:11]

Participants

5

Reactant 3

HCID 14948820BischlorophthalimideHCID 66941220disodium bisphenol-AHCID 670555084,4'-Biphenol disodium salt

Product 1

HCID 6623Bisphenol A

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent2×

Procedure

Bisphenol A disodium salt (4.6981 g, 17.2562 mmol), 4,4′-biphenol disodium salt (2.6479 g, 11.5042 mmol), and o-DCB (60 mL) were combined in a reaction vessel equipped with a mechanical stirrer, short path distillation head, receiver, and inert gas inlet and exit. o-DCB was distilled from the mixture until the distillate contained less than 10 ppm of water. Approximately 20 to 30 mL of o-DCB was removed in this drying step. Then, 15.3885 g (29.0716 mmol) of the bischlorophthalimide prepared from ODA and 98% 3ClPA, 2% 4ClPA, and 0.1334 g (0.5177 mmol) of 4-chloro-N-methyl phthalimide chain stopper were added quantitatively to the reaction vessel along with 10-20 mL of additional o-DCB. O-DCB was distilled from the mixture until a solids level of 25% was reached. Hexaethylguanidium chloride phase transfer catalyst (0.7 mole %) was then added and polymerization initiated. The product polyetherimide had a weight average molecular weight (Mw) of 60,282 grams per mole and a number average molecular weight (Mn) of 24,100 grams per mole.

Workup

  1. customequipped with a mechanical stirrer
  2. distillationshort path distillation head, receiver, and inert gas inlet and exit
  3. distillationo-DCB was distilled from the mixture until the distillate
  4. customApproximately 20 to 30 mL of o-DCB was removed in this drying step
  5. distillationO-DCB was distilled from the mixture until a solids level of 25%
  6. additionHexaethylguanidium chloride phase transfer catalyst (0.7 mole %) was then added
  7. custompolymerization

Sources & evidence

ORD record
ord-1d77988153b84e52b1ee3e92e70195d9
Source dataset
uspto-grants-2009_10
Patent number
US07605222B2

Reaction notes

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