Phosgene → HCID 178439294, compound

HRID 1837283Notes

Reaction equation

HRID 1837283 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.[SiH2:34]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=1[OH:49])[O:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[OH:42].[C:50]1([O:60][CH3:61])[C:51](=[CH:53][CH:54]=[C:55]([CH:59]=1)[CH2:56][CH:57]=[CH2:58])[OH:52].[OH-].[Na+].C(Cl)(Cl)=O>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].[SiH2:34]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=1[OH:49])[O:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[OH:42].[C:50]1([O:60][CH3:61])[C:51](=[CH:53][CH:54]=[C:55]([CH:59]=1)[CH2:56][CH:57]=[CH2:58])[OH:52]

Participants

9

Reactant 5

HCID 6371PhosgeneHCID 6623Bisphenol AHCID 117424-CumylphenolHCID 14798Sodium Hydroxide2×HCID 178439295HCID 178439295, compound

Product 1

HCID 178439294HCID 178439294, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent4×HCID 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), triethylamine (125 microliters) and eugenol siloxane bisphenol (3.2 g, 3 mmol) having a value of “p” of about 9. The pH was adjusted to about 10.5 with a solution of 50 percent by weight NaOH in water. Phosgene (13.2 g, 132 mmol) was added at 0.6 g/min while maintaining the pH at about 10.5 by the addition of a solution of 50 percent by weight NaOH in water. Methylene chloride (25 mL) was added and the organic phase was separated from the brine and washed once with 1 N HCl and four times with distilled water. The product polymer was isolated by the addition of the washed methylene chloride solution to boiling water (750 mL) at high shear. The flocculant powder was filtered, washed with distilled water (500 mL) and dried for 24 hr under vacuum at 110° C. The product silicone copolycarbonate had a Tg of 134° C. and a weight average molecular weight (Mw) of 40,700 as determined by gel permeation chromatography (gpc). 1H-NMR in CDCL3 solution revealed the complete incorporation of the eugenol siloxane bisphenol. The product copolycarbonate was further shown by 1H-NMR to have a blocky structure.

Workup

  1. temperaturewhile maintaining the pH at about 10.5
  2. customthe organic phase was separated from the brine
  3. washwashed once with 1 N HCl and four times with distilled water
  4. customThe product polymer was isolated by the addition of the washed methylene chloride solution
  5. filtrationThe flocculant powder was filtered
  6. washwashed with distilled water (500 mL)
  7. customdried for 24 hr under vacuum at 110° C

Sources & evidence

ORD record
ord-585e27bafc4845939c26a8fc04b5c5b8
Source dataset
uspto-grants-2004_08
Patent number
US06780956B2

Reaction notes

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