Phosgene → bisphenol TMC 4,4'-dihydroxydiphenyl ether

HRID 30948

Reaction equation

HRID 30948 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.[CH3:16][CH:17]1[CH2:22][C:21]([C:30]2[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=2)([C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=2)[CH2:20][C:19]([CH3:38])([CH3:37])[CH2:18]1.[OH-].[Na+].C(C1C=CC(O)=CC=1)(C)(C)C.C(Cl)(Cl)=O.C(N1CCCCC1)C>O.C(Cl)Cl>[CH3:16][CH:17]1[CH2:22][C:21]([C:23]2[CH:24]=[CH:25][C:26]([OH:29])=[CH:27][CH:28]=2)([C:30]2[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=2)[CH2:20][C:19]([CH3:37])([CH3:38])[CH2:18]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 73934-tert-ButylphenolHCID 13007N-EthylpiperidineHCID 14798Sodium Hydroxide2×HCID 160694,4'-Dihydroxydiphenyl etherHCID 41340354,4'-(3,3,5-Trimethylcyclohexylidene)bis(phenol)

Product 1

HCID 131727055bisphenol TMC 4,4'-dihydroxydiphenyl ether

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

130 ml of methylene chloride are added to a solution, rendered inert with nitrogen, of 7.077 g (0.035 mol.) of 4,4′-dihydroxydiphenyl ether and 10.87 g (0.035 mol.) of bisphenol TMC as well as 6.16 g (0.154 mol.) of sodium hydroxide in 130 ml of water. In a one-step procedure, 0.368 g (0.0024 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, 9.7 ml (13.8 g, 0.14 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, 0.10 ml (0.0007 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 14.08 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 14.08 g of polycarbonate

Sources & evidence

ORD record
ord-7311ef6d8dd041a89e2326b3f0fb7878
Source dataset
uspto-grants-2008_09
Patent number
US07425358B2

Linked notes

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