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Diphenolic acid

Organic acid

Organic acid

Incompatible with bases

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: 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.

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. Diphenolate esters have also been used to synthesize polycarbonates with a potential for water solubility.

References

References

  1. [https://web.archive.org/web/20150907142419/http://ntp.niehs.nih.gov/ntp/htdocs/chem_background/exsumpdf/diphenolicacid_508.pdf Diphenolic acid], National Toxicology Program
  2. Maiorana, A., Spinella, S., Gross, R.A., Biomacromolecules, 2015, doi 10.1021 [http://pubs.acs.org/doi/abs/10.1021/acs.biomac.5b00014]
  3. Ruifeng Zhang and J. A. Moore, Macromolecular Symposia,199 (Polycondensation 2002), 375-390 (2003)
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4-hydroxyphenyl-compounds carboxylic-acids
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