Phosgene → 4,4'-Dihydroxydiphenyl ether 4,4'-dihydroxybiphenyl

HRID 30950

Reaction equation

HRID 30950 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]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=2)=[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>[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.[OH:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=2)=[CH:21][CH:22]=1

Participants

9

Reactant 6

HCID 6371PhosgeneHCID 71124,4'-DihydroxybiphenylHCID 73934-tert-ButylphenolHCID 13007N-EthylpiperidineHCID 14798Sodium Hydroxide2×HCID 160694,4'-Dihydroxydiphenyl ether

Product 1

HCID 1317270564,4'-Dihydroxydiphenyl ether 4,4'-dihydroxybiphenyl

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

220 ml of methylene chloride are added to a solution, rendered inert with nitrogen, of 8.088 g (0.04 mol.) of 4,4′-dihydroxydiphenyl ether and 1.826 g (0.01 mol.) of 4,4′-dihydroxybiphenyl (DOD) as well as 4.4 g (0.111 mol.) of sodium hydroxide in 220 ml of water. In a one-step procedure, 0.263 g (0.00175 mol. or 3.5 mol. % relative to bisphenol) of p-tert.-butylphenol (BUP) are added as chain terminator. At a pH value of 14 and at room temperature, 6.9 ml (9.88 g, 0.099 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, 0.07 ml (0.0005 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 8.55 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 8.55 g of polycarbonate

Sources & evidence

ORD record
ord-d9af9e4fee0240fb82ee0c0d7f8e14e9
Source dataset
uspto-grants-2008_09
Patent number
US07425358B2

Linked notes

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