Phosgene → bisphenol A 4,4'-dihydroxydiphenyl ether

HRID 30952

Reaction equation

HRID 30952 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)([CH3:10])[CH3:9])=[CH:4][CH:3]=1.[CH:18]1[C:23]([OH:24])=[CH:22][CH:21]=[C:20]([O:25][C:26]2[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=2)[CH:19]=1.[OH-].[Na+].C(C1C=CC(O)=CC=1)(C)(C)C.C(Cl)(Cl)=O.C(N1CCCCC1)C>O.C(Cl)Cl>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:11]2[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=2)([CH3:10])[CH3:9])=[CH:6][CH:7]=1.[CH:30]1[C:29]([OH:32])=[CH:28][CH:27]=[C:26]([O:25][C:20]2[CH:21]=[CH:22][C:23]([OH:24])=[CH:18][CH:19]=2)[CH:31]=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

31 litres of methylene chloride are added to a solution, rendered inert with nitrogen, of 3903.9 g (17.1 mol.) of bisphenol A, 182 g (0.9 mol.) of 4,4′-dihydroxydiphenyl ether and 1584 g (39.6 mol.) of sodium hydroxide in 31 litres of water. In a one-step procedure, 108.14 g (0.72 mol. or 4 mol. % relative to bisphenol A) of p-tert.-butylphenol (BUP) are added as chain terminator. At a pH value of 13.4 and at 21° C., 3560 g (36 mol.) of phosgene are added in the course of 1 hour and 20 minutes. In order to prevent the pH value from falling below 12.6, 25% sodium hydroxide solution was added during the phosgenation. When the phosgenation is complete, and after rinsing with nitrogen, 24.7 ml (0.18 mol., 1 mol. % relative to bisphenol A) of n-ethylpiperidine are 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. After replacing the solvent with chlorobenzene, the product is extruded at 290° C. using an evaporating extruder.

Workup

  1. additionwas added during the phosgenation
  2. additionare added as catalyst
  3. customThe aqueous phase is separated off
  4. washwashed with distilled water until neutral and free of salt
  5. customis extruded at 290° C.

Sources & evidence

ORD record
ord-bb40376617ed4778a10a74eb95eecb2b
Source dataset
uspto-grants-2008_09
Patent number
US07425358B2

Linked notes

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