Organic acid
Diphenolic acid
Names
Preferred IUPAC name
4,4-Bis(4-hydroxyphenyl)pentanoic acid
Other names
4,4-Bis(4-hydroxyphenyl)valeric acid
Identifiers
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
C 17 H 18 O 4
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).
Chemical compound
Diphenolic acid is a carboxylic acid with molecular formula C17 H18 O4 . 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 C6 H5 OH + CH3 C(O)CH2 CH2 COOH → CH3 C(p -C6 H4 OH)2 CH2 CH2 COOH + H2 O
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
^ Diphenolic acid , National Toxicology Program
^ Maiorana, A., Spinella, S., Gross, R.A., Biomacromolecules, 2015, doi 10.1021 [1]
^ Ruifeng Zhang and J. A. Moore, Macromolecular Symposia,199 (Polycondensation 2002), 375-390 (2003)
External links