Diphenolic acid

Diphenolic acid
Names
Preferred IUPAC name
4,4-Bis(4-hydroxyphenyl)pentanoic acid
Other names
4,4-Bis(4-hydroxyphenyl)valeric acid
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.004.331
UNII
  • InChI=1S/C17H18O4/c1-17(11-10-16(20)21,12-2-6-14(18)7-3-12)13-4-8-15(19)9-5-13/h2-9,18-19H,10-11H2,1H3,(H,20,21) ☒N
    Key: VKOUCJUTMGHNOR-UHFFFAOYSA-N ☒N
  • InChI=1/C17H18O4/c1-17(11-10-16(20)21,12-2-6-14(18)7-3-12)13-4-8-15(19)9-5-13/h2-9,18-19H,10-11H2,1H3,(H,20,21)
    Key: VKOUCJUTMGHNOR-UHFFFAOYAX
  • CC(CCC(=O)O)(C1=CC=C(C=C1)O)C2=CC=C(C=C2)O
Properties
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
 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

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.[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]

References

  1. ^ Diphenolic acid, National Toxicology Program
  2. ^ Maiorana, A., Spinella, S., Gross, R.A., Biomacromolecules, 2015, doi 10.1021 [1]
  3. ^ Ruifeng Zhang and J. A. Moore, Macromolecular Symposia,199 (Polycondensation 2002), 375-390 (2003)
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