Phosgene → 4-[2-(4-Hydroxyphenyl)propan-2-yl]-2-methoxyphenol

HRID 888559Notes

Reaction equation

HRID 888559 reaction equation
[C:1]1([O:8][CH3:9])[C:2](=[CH:4][CH:5]=[CH:6][CH:7]=1)[OH:3].[CH3:10][C:11](C1C=CC(O)=CC=1)([C:13]1[CH:14]=[CH:15][C:16]([OH:19])=[CH:17][CH:18]=1)[CH3:12].CC(C1C=CC(O)=CC=1)(C1C=CC(O)=CC=1)C.C(C1C=CC(O)=CC=1)(C1C=CC=CC=1)(C)C.O=C([O-])[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.[Na+].C(Cl)(Cl)=O>C(N(CC)CC)C.O.C(Cl)Cl>[OH:19][C:16]1[CH:17]=[CH:18][C:13]([C:11]([C:6]2[CH:5]=[CH:4][C:2]([OH:3])=[C:1]([O:8][CH3:9])[CH:7]=2)([CH3:12])[CH3:10])=[CH:14][CH:15]=1

Participants

9

Reactant 5

HCID 6371PhosgeneHCID 6623Bisphenol AHCID 117424-CumylphenolHCID 23672301Sodium GluconateHCID 86642583HCID 86642583, compound

Product 1

HCID 235172484-[2-(4-Hydroxyphenyl)propan-2-yl]-2-methoxyphenol

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

Run 3—1% guaiacol BPA: Methylene chloride (23 L), water (8 L), BPA (4500 g, 19.8 mol), monomethoxyBPA (55 g of the above mixture), p-cumylphenol (135 g, 0.64 mol), triethylamine (40 ml) and sodium gluconate (10 g) was charged to a 75 L reactor equipped with mechanical agitation, condenser, and caustic scrubber vent system. Phosgene (2300 g, 23.2 mol) was added at a rate of 80 g/min to the reactor while 33 wt % caustic was added at a rate to maintain pH=10. The reactor contents were purged with nitrogen then transferred to another tank and centrifuged to remove the brine layer. The organic layer containing the polymer was washed on a centrifuge train with 1N HCl and then with deionized water until residual chloride levels were <5 ppm. The polymer was isolated by steam precipitation followed by drying under hot nitrogen. The final dried resin weighed 4.1 lbs, had Mw=27652 daltons and PDI=2.5 by GPC vs PC standard, <1 ppm TEA, 0.6 ppm chloride ion, <10 ppm residual free BPA, and <0.05 ppm Fe. The glass transition temperature was determined to be 153 C.

Workup

  1. customequipped with mechanical agitation, condenser, and caustic scrubber vent system
  2. additionwas added at a rate
  3. temperatureto maintain pH=10
  4. customThe reactor contents were purged with nitrogen
  5. customto remove the brine layer
  6. additionThe organic layer containing the polymer
  7. washwas washed on a centrifuge train with 1N HCl
  8. customThe polymer was isolated by steam precipitation
  9. customby drying under hot nitrogen

Sources & evidence

ORD record
ord-9cd320e369464a4198773a66d9bd6090
Source dataset
uspto-grants-2012_08
Patent number
US08247619B2

Reaction notes

Loading…