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Preferred IUPAC name
4,4-Bis(4-hydroxyphenyl)pentanoic acid | |
Other names
4,4-Bis(4-hydroxyphenyl)valeric acid
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CAS Number
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3D model (JSmol)
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ChemSpider |
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ECHA InfoCard | 100.004.331 |
PubChem CID
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UNII |
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CompTox Dashboard (EPA)
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Properties | |
Chemical formula
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C17H18O4 |
Molar mass | 286.327 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 | |
Occupational safety and health (OHS/OSH): | |
Main hazards
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Fire and explosion hazard with strong oxidisers Incompatible with bases |
Flash point | 274.5 °C (526.1 °F; 547.6 K) |
Safety data sheet (SDS) | MSDS |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
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Diphenolic acid is a carboxylic acid with molecular formula C17H18O4. Its IUPAC name is 4,4-bis(4-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:
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 diglycidyl ether of bisphenol A.The diglycidyl ethers of n-alkyl diphenolate esters have similar thermomechanical properties to the diglycidyl 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]