Phosgene → Monoisobutyl phthalate

HRID 512083Notes

Reaction equation

HRID 512083 reaction equation
[CH3:1][CH:2]([CH2:4][O:5][C:6]([C:8]1[C:13]([C:14]([OH:16])=[O:15])=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:7])[CH3:3].C(Cl)(Cl)=O.[OH:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]([C:31]2[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=2)([CH3:30])[CH3:29])=[CH:24][CH:23]=1.C(N(CC)CC)C.C(C1C=CC(O)=CC=1)(C1C=CC=CC=1)(C)C>O.C(Cl)Cl>[CH3:3][CH:2]([CH2:4][O:5][C:6]([C:8]1[C:13]([C:14]([OH:16])=[O:15])=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:7])[CH3:1].[CH3:3][CH:2]([CH2:4][O:5][C:6]([C:8]1[C:13]([C:14]([OH:16])=[O:15])=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:7])[CH3:1].[CH3:30][C:28]([C:25]1[CH:24]=[CH:23][C:22]([OH:21])=[CH:27][CH:26]=1)([C:31]1[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=1)[CH3:29]

Participants

9

Reactant 5

HCID 6371PhosgeneHCID 6623Bisphenol AHCID 8471TriethylamineHCID 117424-CumylphenolHCID 92272Monoisobutyl phthalate2×

Product 2

HCID 92272Monoisobutyl phthalateHCID 131733273HCID 131733273, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of MIBP was prepared by dissolving (5.32 g, 0.0168 moles) MIBP monomer (prepared according to Example 7) in 33% aqueous caustic (7 g) and water (30 mL). To a 2 L glass reactor equipped with pH probe, condenser, agitator, phosgene inlet, and caustic scrubber was added methylene chloride (500 mL), deionized water (140 mL), bisphenol-A (4.68 g, 0.0205 moles), triethylamine (0.10 mL, 0.0007 moles), p-cumylphenol (0.24 g, 0.0011 moles), and MIBP solution. The batch was phosgenated in excess at a rate of 2 grams per min for 2 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. The reaction mixture extracted with dilute acid (1N HCl) and deionized water. The final product 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 MIBP-BPA Copolymer (PL-11-116) is provided in Table 1, shown below.

Workup

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

Sources & evidence

ORD record
ord-da01d1fafe7346f6a3cca18f30e02dd7
Source dataset
uspto-grants-2015_08
Patent number
US09102597B2

Reaction notes

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