2-Hydroxyethyl terephthalic acid

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2-Hydroxyethyl terephthalic acid
2-hydroxyethyl terephthalic acid.svg
Names
Preferred IUPAC name
4-[(2-Hydroxyethoxy)carbonyl]benzoic acid
Other names
1,4-Benzenedicarboxylic acid, 1-(2-hydroxyethyl) ester
Identifiers
3D model (JSmol)
ChEBI
UNII
  • InChI=1S/C10H10O5/c11-5-6-15-10(14)8-3-1-7(2-4-8)9(12)13/h1-4,11H,5-6H2,(H,12,13)
    Key: BCBHDSLDGBIFIX-UHFFFAOYSA-N
  • C1=CC(=CC=C1C(=O)O)C(=O)OCCO
Properties
C10H10O5
Molar mass 210.185 g·mol−1
Appearance White solid
Melting point 183–186 °C (361–367 °F; 456–459 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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.

Occurrence and reactions[edit]

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 H2O → n HO2CC6H4CO2C2H4OH

References[edit]

  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.
  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.