Diphenolic acid

Diphenolic acid
Names
	IUPAC name 4,4-Bis(4-hydroxyphenyl)pentanoic acid
	Other names 4,4-Bis(4-hydroxyphenyl)valeric acid
Identifiers
CAS Number	126-00-1 ;
3D model (JSmol)	Interactive image;
ChemSpider	60518 ;
ECHA InfoCard	100.004.331
PubChem CID	67174;
UNII	2SIZ2CO5L3 ;
CompTox Dashboard (EPA)	DTXSID0022436 ;
	InChI 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) Key: VKOUCJUTMGHNOR-UHFFFAOYSA-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;
	SMILES CC(CCC(=O)O)(C1=CC=C(C=C1)O)C2=CC=C(C=C2)O;
Properties
Chemical formula	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
Main hazards	Fire and explosion hazard with strong oxidisers; Incompatible with bases
Safety data sheet	MSDS
Flash point	274.5 °C (526.1 °F; 547.6 K)
	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

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

External links

Material Safety Data Sheet for diphenolic acid

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[1] Diphenolic acid, National Toxicology Program

[2] Maiorana, A., Spinella, S., Gross, R.A., Biomacromolecules, 2015, doi 10.1021

[3] Ruifeng Zhang and J. A. Moore, Macromolecular Symposia,199 (Polycondensation 2002), 375-390 (2003)