Dimethyl isophthalate → 3,6-Dioxabicyclo(6.3.1)dodeca-1(12),8,10-triene-2,7-dione

HRID 1076943Notes

Reaction equation

HRID 1076943 reaction equation
[C:1]([O:13][CH3:14])(=[O:12])[C:2]1[CH:11]=[CH:10][CH:9]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH:3]=1.[Sb]#[Sb].OCCOC(=O)CCCCC(OCCO)=O>C([O-])(=O)C.[Mn+2].C([O-])(=O)C.C(O)CO>[C:5]1(=[O:6])[O:7][CH2:8][CH2:14][O:13][C:1](=[O:12])[C:2]2=[CH:11][CH:10]=[CH:9][C:4]1=[CH:3]2

Participants

6

Reactant 3

HCID 15088Dimethyl isophthalateHCID 2396732679-33-7HCID 74340Bis(2-hydroxyethyl) adipate

Product 1

HCID 817903,6-Dioxabicyclo(6.3.1)dodeca-1(12),8,10-triene-2,7-dione

Reagents, catalysts & solvents 2

HCID 12525Manganous AcetateCatalystHCID 174Ethylene GlycolSolvent

Procedure

Dimethyl isophthalate, 1.37 kg, and ethylene glycol, 0.92 kg, were charged into a reactor together with an ester exchange catalyst which was a mixture of 2.05 g manganese acetate and 1.35 g diantimony trixoide. The ester exchange reaction was carried out as described in Example 1, and 3.29 kg of bis(hydroxyethyl)adipate was added to the product thus obtained. The polymerization was carried out at 265°C. at 1 mm Hg pressure for 6 hours to provide a poly(ethylene isophthalate/adiphate) having a mol ratio of isophthalate to adipate of 33 to 67 and having an intrinsic viscosity of 0.56, as determined in a solvent mixture of 25 volume percent trifluoroacetic acid and 75 volume percent methylene chloride.

Workup

  1. additionwas added to the product
  2. customthus obtained

Sources & evidence

ORD record
ord-5121e02df81a4298aa201f3d53995026
Source dataset
uspto-grants-1976_05
Patent number
US03959200

Reaction notes

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