Phosgene → HCID 20025676, compound

HRID 511954Notes

Reaction equation

HRID 511954 reaction equation
C(Cl)(Cl)=O.C(N(CC)CC)C.[OH:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=2)([CH3:21])[CH3:20])=[CH:15][CH:14]=1.[C:29]([C:38]1C=CC(O)=C[CH:39]=1)([C:32]1C=CC=[CH:34][CH:33]=1)(C)C>O.C(Cl)Cl>[C:19]1([C:22]2[CH:23]=[CH:24][C:25]([OH:28])=[CH:26][CH:27]=2)([C:16]2[CH:15]=[CH:14][C:13]([OH:12])=[CH:18][CH:17]=2)[C:21]2[C:33](=[CH:32][CH:29]=[CH:38][CH:39]=2)[CH2:34][CH2:20]1

Participants

7

Reactant 4

HCID 6371PhosgeneHCID 6623Bisphenol AHCID 8471TriethylamineHCID 117424-Cumylphenol

Product 1

HCID 20025676HCID 20025676, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of 4,4′-(2,3-dihydro-1H-indene-1,1-diyl)diphenol (“IBP”) was prepared by dissolving 8.33 g (0.0275 moles) of IBP monomer (prepared according to Example 9) in 33% aqueous caustic (15 g) and water (30 ml). To a 2 L glass reactor equipped with a pH probe, condenser, agitator, phosgene inlet, and caustic scrubber was added methylene chloride (500 ml), deionized water (140 ml), triethylamine (0.17 ml, 0.0012 moles), bisphenol-A (7.67 g, 0.0337 moles), p-cumylphenol (0.39 g, 0.0018 moles), and IBP solution. The batch was phosgenated in excess at a rate of 2 grams per min for 4 minutes, maintaining the pH between 9 and 10 with concomitant caustic addition (33% w/w). At the completion of the phosgenation, the reactor was purged with nitrogen to remove excess phosgene and the reaction mixture extracted with dilute acid (1N HCl) and deionized water. The final product IBP-BPA Copolymer (PL-11-058) was isolated as a white powder by exposing the polymer solution (in methylene chloride) to hot water, evaporating the solvent and providing a white powder. Characterization data for the IBP-BPA Copolymer (PL-11-058) is provided in Table 1, shown below.

Workup

  1. dissolutionby dissolving
  2. customfor 4 minutes
  3. temperaturemaintaining the pH between 9 and 10
  4. additionwith concomitant caustic addition (33% w/w)
  5. customAt the completion of the phosgenation, the reactor was purged with nitrogen
  6. customto remove excess phosgene
  7. extractionthe reaction mixture extracted
  8. additionwith dilute acid (1N HCl)

Sources & evidence

ORD record
ord-282d504310ae4f029d42bf77b056d018
Source dataset
uspto-grants-2015_08
Patent number
US09102598B2

Reaction notes

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