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2-Hydroxyethyl terephthalic acid

2-Hydroxyethyl terephthalic acid is an organic compound with the formula HOC<sub>2</sub>H<sub>4</sub>O<sub>2</sub>CC<sub>6</sub>H<sub>4</sub>CO<sub>2</sub>H. 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. 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, HOC<sub>2</sub>H<sub>4</sub>O<sub>2</sub>CC<sub>6</sub>H<sub>4</sub>CO<sub>2</sub><sup>−</sup>.

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:

HOC<sub>2</sub>H<sub>4</sub>OH + HO<sub>2</sub>CC<sub>6</sub>H<sub>4</sub>CO<sub>2</sub>H → HOC<sub>2</sub>H<sub>4</sub>O<sub>2</sub>CC<sub>6</sub>H<sub>4</sub>CO<sub>2</sub>H + H<sub>2</sub>O

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.

H[O<sub>2</sub>CC<sub>6</sub>H<sub>4</sub>CO<sub>2</sub>C<sub>2</sub>H<sub>4</sub>]<sub>n</sub>OH + (n−1) H<sub>2</sub>O → n HO<sub>2</sub>CC<sub>6</sub>H<sub>4</sub>CO<sub>2</sub>C<sub>2</sub>H<sub>4</sub>OH

References