Bisphenol A → Sebacic Acid

HRID 1058538

Reaction equation

HRID 1058538 reaction equation
C1[C:10]2[C:5](=C[C:7]([C:11]([O:13]C)=[O:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:15]([O:17]C)=[O:16].C(OC)(=O)CCCCCCCCC(OC)=O.[OH:35][C:36]1[CH:41]=[CH:40][C:39]([C:42]([C:45]2[CH:50]=[CH:49][C:48]([OH:51])=[CH:47][CH:46]=2)([CH3:44])[CH3:43])=[CH:38][CH:37]=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:15]([OH:17])(=[O:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:10][CH2:9][CH2:8][CH2:7][C:11]([OH:13])=[O:12].[OH:35][C:36]1[CH:37]=[CH:38][C:39]([C:42]([C:45]2[CH:46]=[CH:47][C:48]([OH:51])=[CH:49][CH:50]=2)([CH3:44])[CH3:43])=[CH:40][CH:41]=1

Participants

10

Reactant 5

HCID 6623Bisphenol AHCID 7829Dimethyl sebacate2×HCID 10541Trimethyl PhosphateHCID 27652Oxo(oxostibanyloxy)stibaneHCID 61225Dimethyl-2,6-naphthalenedicarboxylate2×

Product 2

HCID 5192Sebacic AcidHCID 6623Bisphenol A

Reagents, catalysts & solvents 3

HCID 93021Manganese acetate tetrahydrateCatalystHCID 174Ethylene GlycolSolventHCID 887MethanolSolvent

Procedure

Dimethyl 2,6-naphthalenedicarboxylate and dimethyl sebacate were dispersed in ethylene glycol and an addition product of two ethylene oxides tobisphenol 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 sebacate, 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 sebacic acid (SA) and BPA•2EO and the intrinsic viscosities of polyesters thus obtained are shown in Table II-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-832781fb6f304d9ab43d6a66d2f9a938
Source dataset
uspto-grants-2003_02
Patent number
US06518004B2

Linked notes

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