Phosgene → bisphenol A 4,4'-dihydroxydiphenyl ether

HRID 30947

Reaction equation

HRID 30947 reaction equation
[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[C:3]([O:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[CH:2]=1.[OH:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([C:26]2[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=2)([CH3:25])[CH3:24])=[CH:19][CH:18]=1.[OH-].[Na+].C(C1C=CC(O)=CC=1)(C)(C)C.C(Cl)(Cl)=O.C(N1CCCCC1)C>O.C(Cl)Cl>[OH:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]([C:26]2[CH:27]=[CH:28][C:29]([OH:32])=[CH:30][CH:31]=2)([CH3:25])[CH3:24])=[CH:21][CH:22]=1.[CH:13]1[C:12]([OH:15])=[CH:11][CH:10]=[C:9]([O:8][C:3]2[CH:4]=[CH:5][C:6]([OH:7])=[CH:1][CH:2]=2)[CH:14]=1

Participants

9

Reactant 6

HCID 6371PhosgeneHCID 6623Bisphenol AHCID 73934-tert-ButylphenolHCID 13007N-EthylpiperidineHCID 14798Sodium Hydroxide2×HCID 160694,4'-Dihydroxydiphenyl ether

Product 1

HCID 131727054bisphenol A 4,4'-dihydroxydiphenyl ether

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

131 ml of methylene chloride are added to a solution, rendered inert with nitrogen, of 1.618 g (0.008 mol.) of 4,4′-dihydroxydiphenyl ether and 16.438 g (0.072 mol.) of bisphenol A as well as 7.04 g (0.176 mol.) of sodium hydroxide in 131 ml of water. In a one-step procedure, 0.36 g (0.0024 mol. or 3.0 mol. % relative to bisphenol) of p-tert.-butylphenol (BUP) are added as chain terminator. At a pH value of 14 and at room temperature, 11 ml (15.8 g, 0.16 mol.) of phosgene are added in the course of 10 minutes. In order to prevent the pH value from falling below 12, 25% sodium hydroxide solution was added during the phosgenation. When the phosgenation is complete, and after rinsing with nitrogen, 0.11 ml (0.0008 mol., 1 mol. % relative to bisphenol) of n-ethylpiperidine is added as catalyst, and stirring is then carried out for one hour. The aqueous phase is separated off, and the organic phase is acidified with phosphoric acid and washed with distilled water until neutral and free of salt. Precipitation of the polymer in methanol and drying yield 17.29 g of polycarbonate.

Workup

  1. additionwas added during the phosgenation
  2. additionis added as catalyst
  3. customThe aqueous phase is separated off
  4. washwashed with distilled water until neutral and free of salt
  5. customPrecipitation of the polymer in methanol
  6. dry with materialdrying yield 17.29 g of polycarbonate

Sources & evidence

ORD record
ord-50249aa91b5a4250b0f04858be17ae36
Source dataset
uspto-grants-2008_09
Patent number
US07425358B2

Linked notes

Loading…