Bisphenol A → Adipic Acid

HRID 1058537Notes

Reaction equation

HRID 1058537 reaction equation
C1C2C(=CC(C(OC)=O)=CC=2)C=CC=1C(OC)=O.[C:19]([O:29]C)(=[O:28])[CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26]C)=[O:25].[OH:31][C:32]1[CH:37]=[CH:36][C:35]([C:38]([C:41]2[CH:46]=[CH:45][C:44]([OH:47])=[CH:43][CH:42]=2)([CH3:40])[CH3:39])=[CH:34][CH:33]=1.O=[Sb]O[Sb]=O.P(OC)(OC)(OC)=O>C(O)CO.O.O.O.O.C([O-])(=O)C.[Mn+2].C([O-])(=O)C.CO>[C:19]([OH:29])(=[O:28])[CH2:20][CH2:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25].[OH:31][C:32]1[CH:33]=[CH:34][C:35]([C:38]([C:41]2[CH:42]=[CH:43][C:44]([OH:47])=[CH:45][CH:46]=2)([CH3:40])[CH3:39])=[CH:36][CH:37]=1

Participants

10

Reactant 5

HCID 6623Bisphenol AHCID 10541Trimethyl PhosphateHCID 12329Dimethyladipate2×HCID 27652Oxo(oxostibanyloxy)stibaneHCID 61225Dimethyl-2,6-naphthalenedicarboxylate2×

Product 2

HCID 196Adipic AcidHCID 6623Bisphenol A

Reagents, catalysts & solvents 3

HCID 93021Manganese acetate tetrahydrateCatalystHCID 174Ethylene GlycolSolventHCID 887MethanolSolvent

Procedure

Dimethyl 2,6-naphthalenedicarboxylate and dimethyl adipate were dispersed in ethylene glycol and an addition product of two ethylene oxides to bisphenol A (BPA•2EO). Then, 0.029 part of manganese acetate tetrahydrate, 0.028 parts of antimony trioxide and 0.1% of spherical silica particles having a mean particle size of 0.3 μm were added to 100 parts of the total of dimethyl 2,6-naphthalenedicarboxylate and dimethyl adipate, and heated with stirring to conduct the reaction. The temperature was elevated to 235° C. while removing methanol produced as a by-product. After the by-production of methanol was completed, 0.03 part of trimethyl phosphate was added thereto. Then, the pressure was reduced to 0.3 Torr while elevating the temperature to 285° C. to conduct the polymerization by changing the reaction time. Dyes described in JP-A-7-168309, compounds I-6 and I-24, were each further added to the solid matter in an amount of 54 ppm. The copolymerization composition ratios of adipic acid (AA) and BPA•2EO and the intrinsic viscosities of polyesters thus obtained are shown in Table I-1.

Workup

  1. temperatureheated
  2. customthe reaction
  3. customwas elevated to 235° C.
  4. customwhile removing methanol
  5. customproduced as a by-product
  6. customto 285° C.
  7. customthe polymerization
  8. additioneach further added to the solid matter in an amount of 54 ppm

Sources & evidence

ORD record
ord-762a449b262e47d0bda9c76022ad3f03
Source dataset
uspto-grants-2003_02
Patent number
US06518004B2

Reaction notes

Loading…