Terephthalic Acid → Bis(3-hydroxypropyl) terephthalate

HRID 635430Notes

Reaction equation

HRID 635430 reaction equation
[C:1]([OH:12])(=[O:11])[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[CH2:13]([OH:17])[CH2:14][CH2:15]O>>[OH:7][CH2:6][CH2:5][CH2:4][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([C:1]([O:12][CH2:15][CH2:14][CH2:13][OH:17])=[O:11])=[CH:3][CH:4]=1

Participants

3

Reactant 2

HCID 7489Terephthalic AcidHCID 104421,3-Propanediol

Product 1

HCID 9925756Bis(3-hydroxypropyl) terephthalate

Conditions

Temperature
245 °C

Procedure

50.6 kg of terephthalic acid (TPA) and 30.2 kg of 1,3-propanediol (PDO) were charged in an esterification vessel and stirred thoroughly at a stirring rate of 130 rpm in the presence of an esterification catalyst. Nitrogen was then introduced at a flow rate of 4 L/min, and the reaction pressure was maintained at 2 kg/cm2G. The internal temperature of the esterification vessel was increased to 245° C. During the esterification process, the byproducts water and 1,3-PDO were separated by using a separation tower such that 1,3-PDO was introduced to the esterification reaction system and that water was made to flow out from the top of the tower, which is then cooled and recovered. The total esterification reaction time was 3.5 hours. The esterified product BHPT was cooled and crushed, by which the saponification value can be determined, and the saponification value was then converted to have a calculated esterification conversion of 98.1%. The reaction conditions are summarized in Table 1.

Workup

  1. additionNitrogen was then introduced at a flow rate of 4 L/min
  2. customthe reaction pressure
  3. temperaturewas maintained at 2 kg/cm2G
  4. customDuring the esterification process, the byproducts water and 1,3-PDO were separated
  5. additionwas introduced to the esterification reaction system
  6. temperatureis then cooled
  7. customrecovered
  8. customThe total esterification reaction time
  9. temperatureThe esterified product BHPT was cooled
  10. customcrushed, by which the saponification value
  11. customThe reaction conditions

Sources & evidence

ORD record
ord-d91e6e59d1e54d358bbad42b0310c598
Source dataset
uspto-grants-2001_02
Patent number
US06187900B1

Reaction notes

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