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2-Hydroxyethyl terephthalic acid
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2-hydroxyethyl terephthalic acid.svg 92 4-[(2-Hydroxyethoxy)carbonyl]benzoic acid 1,4-Benzenedicarboxylic acid, 1-(2-hydroxyethyl) ester 1137-99-1 correct CAS 151881 875-651-4 C21450 correct FDA 8DN7KSY2WN 174073 131735 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) BCBHDSLDGBIFIX-UHFFFAOYSA-N C1=CC(=CC=C1C(=O)O)C(=O)OCCO 10 10 5 White solid 183-186 07 Warning 302 315 319 335 261 264 264+265 270 271 280 301+317 302+352 304+340 305+351+338 319 321 330 332+317 337+317 362+364 403+233 405 501
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.Richard J. Sheehan Terephthalic Acid, Dimethyl Terephthalate, and Isophthalic Acid 10.1002/14356007.a26_193 June 15, 2000No mention of 2-hydroxyethyl terepthtalic acid February 2025 2-Hydroxyethyl terephthalic acid is a colorless solid that is soluble in water and polar organic solvents.4-((2-Hydroxyethoxy)carbonyl)benzoic acid https://pubchem.ncbi.nlm.nih.gov/compound/174073 Near neutral pH, 2-hydroxyethyl terephthalic acid converts to 2-hydroxyethyl terephthalate, HOC2H4O2CC6H4CO2−.
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. It is substrate for the enzyme MHETase.Oda Kohei Wlodawer Alexander Development of Enzyme-Based Approaches for Recycling PET on an Industrial Scale Biochemistry 2024 10.1021/acs.biochem.3c00554 38285602
H[O2CC6H4CO2C2H4]nOH + (n−1) H2O → n HO2CC6H4CO2C2H4OH
References
Category:Hydroxyethyl compounds
Category:Terephthalate esters