Phenol → Carbonic acid;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol

HRID 851313

Reaction equation

HRID 851313 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.C1([OH:24])C=CC=CC=1.[O:25]=[C:26]([O-:37])[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.[Na+].[OH-].[Na+].C(Cl)(Cl)=O>C(N(CC)CC)C.C(Cl)Cl.O>[CH3:10][C:8]([C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=1)([C:11]1[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=1)[CH3:9].[C:26]([OH:37])([OH:24])=[O:25]

Participants

9

Reactant 5

HCID 996Phenol2×HCID 6371Phosgene2×HCID 6623Bisphenol A3×HCID 14798Sodium Hydroxide2×HCID 23672301Sodium Gluconate

Product 1

HCID 159987Carbonic acid;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

A polymerization reactor was charged with 4.3 liters of water, 6.0 liters of methylene chloride, 2280 g. of bis(4-hydroxyphenol)propane-2,2 i.e., bisphenol-A also referred to herein as "BPA", 35 ml. of phenol also known as "hydroxy benzene", 10 g. of triethylamine, 3.4 g. of sodium gluconate, and 415 ml. of a 35% (w/w) of an aqueous sodium hydroxide solution. The admixture was equilibrated to form a substantially uniform agitated two-phase admixture by stirring for approximately 5 minutes while a pH of approximately 11.3 to 11.7 was attained. Phosgene was introduced from a calibrated flow meter at 63 g. per minute. By means of an automatic pH control a caustic 35% w/w aqueous sodium hydroxide solution was intermittently added to the reactor at a rate of 170 to 190 ml. per minute to maintain the reaction pH within the abovenoted pH range during the course of the reaction. After approximately 20-22 minutes phosgene flow was stopped, and the polymer reaction mixture was continuously agitated for an additional 2 minutes. The aqueous layer was sampled to determine residual "BPA" monomer which for control purposes was required to be less than 15 parts per million. The organic phase was separated and diluted with 4000 ml. of methylene chloride, washed twice with a dilute hydrochloric acid, (4000 ml. of a 2% w/v solution), and twice with 4000 ml. of deionized water. The resulting polymer solution was flash evaporated with steam and the resulting precipitate was collected and dried in nitrogen.

Workup

  1. customto form a substantially uniform agitated two-phase admixture
  2. temperatureper minute to maintain the reaction pH within the abovenoted pH
  3. customrange during the course of the reaction
  4. customthe polymer reaction mixture
  5. stirringwas continuously agitated for an additional 2 minutes
  6. aliquotThe aqueous layer was sampled
  7. customThe organic phase was separated
  8. additiondiluted with 4000 ml
  9. washof methylene chloride, washed twice with a dilute hydrochloric acid
  10. customevaporated with steam
  11. customthe resulting precipitate was collected
  12. customdried in nitrogen

Sources & evidence

ORD record
ord-94d3403c39f44c5ebfb75be9e6d3c74e
Source dataset
uspto-grants-1983_05
Patent number
US04384108

Linked notes

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