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2-Hydroxyethyl terephthalic acid
| Column 1 | Column 2 |
|---|---|
| Preferred IUPAC name | |
| 4-[(2-Hydroxyethoxy)carbonyl]benzoic acid | |
| Other names | |
| 1,4-Benzenedicarboxylic acid, 1-(2-hydroxyethyl) ester | |
| CAS Number | .mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}1137-99-1 Y |
| 3D model (JSmol) | Interactive image |
| ChEBI | CHEBI:131735 |
| ChemSpider | 151881 |
| EC Number | 875-651-4 |
| KEGG | C21450 |
| PubChem CID | 174073 |
| UNII | 8DN7KSY2WN Y |
| CompTox Dashboard (EPA) | DTXSID60622186 |
| InChI | |
| 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 | |
| SMILES | |
| C1=CC(=CC=C1C(=O)O)C(=O)OCCO | |
| Chemical formula | C10H10O5 |
| Molar mass | 210.185 g·mol−1 |
| Appearance | White solid |
| Melting point | 183–186 °C (361–367 °F; 456–459 K) |
| GHS labelling:[1] | |
| Pictograms | |
| Signal word | Warning |
| Hazard statements | H302, H315, H319, H335 |
| Precautionary statements | P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501 |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Infobox references | |
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. 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−.
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.
H[O2CC6H4CO2C2H4]nOH + (n−1) H2O → n HO2CC6H4CO2C2H4OH
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