Phosgene → HCID 178439294, compound

HRID 1837282Notes

Reaction equation

HRID 1837282 reaction equation
[CH3:1][C:2]([C:11]1[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=1)([C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1)[CH3:3].C(C1C=CC(O)=CC=1)(C1C=CC=CC=1)(C)C.C(Cl)(Cl)=O.[OH-].[Na+].[SiH2:40]([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=1[OH:55])[O:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=1[OH:48].[C:56]1([O:66][CH3:67])[C:57](=[CH:59][CH:60]=[C:61]([CH:65]=1)[CH2:62][CH:63]=[CH2:64])[OH:58]>O.C(Cl)Cl.C(N(CC)CC)C>[CH3:3][C:2]([C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1)([C:11]1[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=1)[CH3:1].[SiH2:40]([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=1[OH:55])[O:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=1[OH:48].[C:56]1([O:66][CH3:67])[C:57](=[CH:59][CH:60]=[C:61]([CH:65]=1)[CH2:62][CH:63]=[CH2:64])[OH:58]

Participants

9

Reactant 5

HCID 6371Phosgene2×HCID 6623Bisphenol AHCID 117424-CumylphenolHCID 14798Sodium HydroxideHCID 178439295HCID 178439295, compound

Product 1

HCID 178439294HCID 178439294, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

A 500 mL Morton flask was charged with BPA (22.8 g, 100 mmol), p-cumylphenol (1.06 g, 5.0 mmol), methylene chloride (125 mL), distilled water (90 mL) and MTBAC (0.5 g of a 75 wt % solution in water). The pH was adjusted to about 10.5 with a solution of 50 percent by weight NaOH in water. Phosgene (7.8 g, 78 mmol) was added at 0.6 g/min maintaining the pH at about 10.5 by the addition of a solution of 50 percent by weight NaOH in water. The pH was allowed to drop to about 8.0 and additional phosgene (3.3 g) was added at 0.6 g/min while maintaining the pH at about 8.0. Eugenol siloxane bisphenol (p=9) (3.2 g, 3 mmol) was added and pH was raised to between about 9 and about 10. The reaction was stirred for 10 min. Triethylamine (125 microliters) was added and the reaction was stirred until no chloroformates were detected. Methylene chloride (25 mL) was added and the polymer solution was separated from the brine and washed once with 1N HCl and four times with distilled water. The polymer solution was precipitated into boiling water (750 mL) at high shear in a blender, washed with water (500 mL) and dried overnight at 110° C. under vacuum. The polymer, analyzed by 1H-NMR, showed complete incorporation of the eugenol siloxane bisphenol, had a Tg 122° C. and a weight average molecular weight (Mw) of 39,900. A film cast from this material was transparent. The product copolycarbonate was shown by 1H-NMR to have a random structure.

Workup

  1. distillationdistilled water (90 mL) and MTBAC (0.5 g of a 75 wt % solution in water)
  2. temperaturemaintaining the pH at about 10.5
  3. additionwas added at 0.6 g/min
  4. temperaturewhile maintaining the pH at about 8.0
  5. temperaturepH was raised to between about 9 and about 10
  6. customthe polymer solution was separated from the brine
  7. washwashed once with 1N HCl and four times with distilled water
  8. customThe polymer solution was precipitated
  9. washwashed with water (500 mL)
  10. customdried overnight at 110° C. under vacuum

Sources & evidence

ORD record
ord-8cd6a76855a14f59ad6319eba9c4caa1
Source dataset
uspto-grants-2004_08
Patent number
US06780956B2

Reaction notes

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