Diphenolic acid

Diphenolic acid
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
CAS number	126-00-1
PubChem	67174
Jmol-3D images	Image 1
SMILES CC(CCC(=O)O)(C1=CC=C(C=C1)O)C2=CC=C(C=C2)O
Properties
Molecular formula	C17H18O4
Molar mass	286.32 g mol−1
Appearance	White to brown crystals
Melting point	168-171 °C, 441-444 K, 334-340 °F
Boiling point	507 °C, 780 K, 945 °F
Hazards
MSDS	MSDS
Main hazards	Fire and explosion hazard with strong oxidisers Incompatible with bases
Flash point	274.5 °C
Y acid (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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]

References

1. ^ Diphenolic acid, National Toxicology Program

External Links

• Material Safety Data Sheet for diphenolic acid