2-Hydroxyethyl_terephthalic_acid

2-Hydroxyethyl terephthalic acid

2-Hydroxyethyl terephthalic acid

Chemical compound

2-Hydroxyethyl terephthalic acid is an organic compound with the formula HOC2H4O2CC6H4CO2H. It is the monoester of terephthalic acid and ethylene glycol. The compound is a precursor to poly(ethylene terephthalate) (PET), a polymer that is produced on a large scale industrially.[1] 2-Hydroxyethyl terephthalic acid is a colorless solid that is soluble in water and polar organic solvents. Near neutral pH, 2-hydroxyethyl terephthalic acid converts to 2-hydroxyethyl terephthalate, HOC2H4O2CC6H4CO2−.

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Occurrence and reactions

2-Hydroxyethyl terephthalic acid is an intermediate in both the formation and hydrolysis of PET. It is produced on a massive scale as the first intermediate in certain routes to PET. Specifically, it is produced in the course of the thermal condensation of terephthalic acid and ethylene glycol:

HOC2H4OH + HO2CC6H4CO2H → HOC2H4O2CC6H4CO2H + H2O

Further dehydration of 2-hydroxyethyl terephthalic acid gives PET.

It is also produced by the partial hydrolysis of PET, as catalyzed by the enzyme PETase:[2]

H[O2CC6H4CO2C2H4]nOH + (n−1) H2O → n HO2CC6H4CO2C2H4OH

References

  1. [1]
    Sheehan, Richard J. "Terephthalic Acid, Dimethyl Terephthalate, and Isophthalic Acid". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a26_193. ISBN 978-3527306732.
  2. [2]
    Yoshida, Shosuke; Hiraga, Kazumi; Takehana, Toshihiko; Taniguchi, Ikuo; Yamaji, Hironao; Maeda, Yasuhito; Toyohara, Kiyotsuna; Miyamoto, Kenji; Kimura, Yoshiharu (2016-03-11). "A bacterium that degrades and assimilates poly(ethylene terephthalate)". Science. 351 (6278): 1196–1199. Bibcode:2016Sci...351.1196Y. doi:10.1126/science.aad6359. ISSN 0036-8075. PMID 26965627. S2CID 31146235.
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