Diphenolic acid
 | |
| Names | |
|---|---|
| IUPAC name
4,4-Bis(p-hydroxyphenyl)pentanoic acid | |
| Other names
4,4-Bis(4'-hydroxyphenyl)valeric acid 4-hydroxy-γ-(4-hydroxyphenyl)-γ-methylbenzenebutanoic acid | |
| Identifiers | |
126-00-1  | |
| 3D model (Jmol) | Interactive image |
| ChemSpider | 60518  |
| ECHA InfoCard | 100.004.331 |
| PubChem | 67174 |
| |
| |
| Properties | |
| C17H18O4 | |
| Molar mass | 286.33 g·mol−1 |
| Appearance | White to brown crystals |
| Melting point | 168 to 171 °C (334 to 340 °F; 441 to 444 K) |
| Boiling point | 507 °C (945 °F; 780 K) |
| Hazards | |
| Main hazards | Fire and explosion hazard with strong oxidisers Incompatible with bases |
| Safety data sheet | MSDS |
| Flash point | 274.5 °C (526.1 °F; 547.6 K) |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| verify (what is ?) | |
| Infobox references | |
Diphenolic acid is a carboxylic acid with molecular formula C17H18O4. Its IUPAC name is 4,4-bis(p-hydroxyphenyl)pentanoic acid, and it can be prepared by the condensation reaction of phenol with levulinic acid in the presence of hydrochloric acid. The equation for this synthesis is:
- 2 C6H5OH + CH3C(O)CH2CH2COOH → CH3C(p-C6H4OH)2CH2CH2COOH + H2O
Diphenolic acid is a solid at room temperature, melting at 168–171 °C and boiling at 507 °C. According to its MSDS, diphenolic acid is soluble in ethanol, isopropanol, acetone, acetic acid, and methyl ethyl ketone, but insoluble in benzene, carbon tetrachloride, and xylene.
Diphenolic acid may be a suitable replacement for bisphenol A as a plasticizer.[1]
Diphenolate esters have been used to synthesize epoxy resins as a replacement for the digylcidyl ether of bisphenol A.The digylcidyl ethers of n-alkyl diphenolate esters have similar thermomechanical properties to the digylcidyl ether of bisphenol A when cured, but the viscosity and glass transition temperature vary as a function of the ester length.[2] Diphenolate esters have also been used to synthesize polycarbonates with a potential for water solubility.[3]
References
- ↑ Diphenolic acid, National Toxicology Program
- ↑ Maiorana, A., Spinella, S., Gross, R.A., Biomacromolecules, 2015, doi 10.1021
- ↑ Ruifeng Zhang and J. A. Moore, Macromolecular Symposia,199 (Polycondensation 2002), 375-390 (2003)