Phosgene → HCID 178439294, compound

HRID 1837285Notes

Reaction equation

HRID 1837285 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].[SiH2:18]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[OH:33])[O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[OH:26].[C:34]1([O:44][CH3:45])[C:35](=[CH:37][CH:38]=[C:39]([CH:43]=1)[CH2:40][CH:41]=[CH2:42])[OH:36].C(C1C=CC(O)=CC=1)(C1C=CC=CC=1)(C)C.C(Cl)(Cl)=O.[OH-].[Na+]>C(Cl)Cl>[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].[SiH2:18]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[OH:33])[O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[OH:26].[C:34]1([O:44][CH3:45])[C:35](=[CH:37][CH:38]=[C:39]([CH:43]=1)[CH2:40][CH:41]=[CH2:42])[OH:36]

Participants

7

Reactant 5

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

Product 1

HCID 178439294HCID 178439294, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 500 mL Morton flask was charged with BPA (22.8 g, 100 mmol), eugenol siloxane bisphenol (p=19) (3.2 g, 1.8 mmol), p-cumylphenol (0.85 g, 4.0 mmol, 4.0 mol %), methylene chloride (125 mL), distilled water (90 mL) and triethylamine (125 uL, 1 mol %). The pH was adjusted to 10.5 with 50 wt % NaOH. Phosgene (13.2 g, 132 mmol, 30 mol % excess) was added at 0.6 g/min maintaining the pH at 10.5 by the addition of the NaOH solution. Methylene chloride (25 mL) was added. 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) in a blender, washed with water (500 mL) and dried overnight at 110° C. under vacuum. The product polymer, analyzed by 1H-NMR, showed complete incorporation of the eugenol siloxane bisphenol (9.9 wt %). The product copolycarbonate had a Tg of 140° C. and a weight average molecular weight, Mw, of 57,600. The product copolycarbonate was shown by 1H-NMR to have a blocky structure.

Workup

  1. distillationdistilled water (90 mL) and triethylamine (125 uL, 1 mol %)
  2. temperaturemaintaining the pH at 10.5
  3. customThe polymer solution was separated from the brine
  4. washwashed once with 1N HCl and four times with distilled water
  5. customThe polymer solution was precipitated
  6. washwashed with water (500 mL)
  7. customdried overnight at 110° C. under vacuum

Sources & evidence

ORD record
ord-cea57a74bd7d4217ba415085336f6569
Source dataset
uspto-grants-2004_08
Patent number
US06780956B2

Reaction notes

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