bisphenol AF → 1,1'-(1,1,1,3,3,3-Hexafluoropropane-2,2-diyl)bis(4-chlorobenzene)

HRID 2164345Notes

Reaction equation

HRID 2164345 reaction equation
[Cl-:1].[Cl-:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[C:23]1[CH:28]=[CH:27][C:26]([C:29]([C:38]2[CH:43]=[CH:42][C:41](O)=[CH:40][CH:39]=2)([C:34]([F:37])([F:36])[F:35])[C:30]([F:33])([F:32])[F:31])=[CH:25][CH:24]=1>ClCCl>[Cl:1][C:23]1[CH:28]=[CH:27][C:26]([C:29]([C:38]2[CH:43]=[CH:42][C:41]([Cl:2])=[CH:40][CH:39]=2)([C:34]([F:37])([F:36])[F:35])[C:30]([F:33])([F:32])[F:31])=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 73864bisphenol AFHCID 13797396Triphenylphosphane dichloride

Product 1

HCID 220237961,1'-(1,1,1,3,3,3-Hexafluoropropane-2,2-diyl)bis(4-chlorobenzene)

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a slurry of triphenylphosphine dichloride (0.2 moles) in dichloromethane (250 ml) under argon is added 2,2-bis(4-hydroxyphenyl)hexafluoropropane (0.1 mole). The solvent is removed by distillation to form an essentially solid reaction mixture in the reaction vessel. The reaction vessel is heated in a molten metal bath to form a molten reaction mixture and the mixture agitated for approximately four hours before cooling to obtain a solid reaction product. The resulting solid is dissolved in dichloromethane and washed first with dilute sodium hydroxide and second with deionized water. The resulting organic fraction is collected and purified passing it through a silica gel chromatographic column using hexane as the eluting solvent. The hexane is removed from the eluate with a rotary evaporator to yield 2,2-bis(4-chlorophenyl)hexafluoropropane.

Workup

  1. customThe solvent is removed by distillation
  2. customto form
  3. customan essentially solid reaction mixture in the reaction vessel
  4. temperatureThe reaction vessel is heated in a molten metal bath
  5. customto form
  6. customa molten reaction mixture
  7. temperaturebefore cooling
  8. customto obtain
  9. customa solid reaction product
  10. washwashed first with dilute sodium hydroxide and second with deionized water
  11. customThe resulting organic fraction is collected
  12. custompurified
  13. customThe hexane is removed from the eluate with a rotary evaporator

Sources & evidence

ORD record
ord-8549fb1b5b3845cebdd8c04cb1bb0b84
Source dataset
uspto-grants-1985_03
Patent number
US04503254

Reaction notes

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