Diphenolic acid

Diphenolic acid Basic information
Product Name:Diphenolic acid
Synonyms:4,4-Bis(4-hydroxyphenyl)valeric acid,Diphenolic acid;3-d]pyriMidine;7-Trichloropyrido[2;2-dioxaborolan-2-yl)isoxazole;5-DiMethyl-4-(4;4-chloro-7-(4-Methoxybenzyl)-6;7-dihydro-5H-pyrrolo[2;2-dioxaborolan-2-yl)indole-1-carboxylate
CAS:126-00-1
MF:C17H18O4
MW:286.32
EINECS:204-763-2
Product Categories:Building Blocks;C13 to C42+;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Organic Building Blocks;bc0001
Mol File:126-00-1.mol
Diphenolic acid Structure
Diphenolic acid Chemical Properties
Melting point 167-170 °C(lit.)
Boiling point 388.69°C (rough estimate)
density 1.30
refractive index 1.5450 (estimate)
Fp 208°C
storage temp. Inert atmosphere,Room Temperature
solubility DMSO (Slightly), Methanol (Slightly)
form Solid
pka4.66±0.10(Predicted)
color White to Off-White
Merck 14,3312
BRN 1886361
InChIKeyVKOUCJUTMGHNOR-UHFFFAOYSA-N
LogP2.890 (est)
CAS DataBase Reference126-00-1(CAS DataBase Reference)
EPA Substance Registry SystemDiphenolic acid (126-00-1)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38-36
Safety Statements 26-37/39-36
WGK Germany 3
10
TSCA Yes
HS Code 29182900
MSDS Information
ProviderLanguage
SigmaAldrich English
ALFA English
Diphenolic acid Usage And Synthesis
Chemical PropertiesLight pink solid
UsesSince diphenolic acid is a close structural analog of bisphenol A, diphenolic acid has the potential to displace bisphenol A. A possible endocrine disruptor, bisphenol A is used in polymer applications such as for use in baby bottles, dental resins, and lacquers to coat food cans.
UsesDiphenolic Acid is a flux compound. Adhesives for semiconductor devices.
UsesDiphenolic acid (DPA) has been identified as a potential replacement for bisphenol A, which is one of the monomers for epoxy resins and polycarbonates. DPA also can Intermediate for surface coatings, lubricating oil additives, cosmetics, surfactants, plasticizers, textile chemicals.
DefinitionChEBI: Diphenolic acid is a bisphenol.
PreparationDiphenolic acid (DPA) can be made by the condensation reaction of levulinic acid with phenol in the presence of acid catalysts.
Synthesis of diphenolic acid from levulinic acid
Synthesis of diphenolic acid from levulinic acid

Industrial usesDiphenolic acid, the condensation product of levulinic acid and phenol, is useful in the preparation of the modified phenol formaldehyde resins, polyether resins and as monocarboxilic acid chain stopper in alkyd resin (Bader, 1960).
Purification MethodsWhen recrystallised from *C6H6, the crystals have 0.5 mol of *C6H6 (m 120-122o), and when recrystallised from toluene, the crystals have 0.5 mol of toluene. Purify the acid by recrystallisation from hot H2O. It is soluble in Me2CO, AcOH, EtOH, propan-2-ol, methyl ethyl ketone. It can also be recrystallised from AcOH, heptane/Et2O or Me2CO/*C6H6. It has max 225 and 279nm in EtOH. The methyl ester has m 87-89o (aqueous MeOH to give the trihydrate). [Bader & Kantowicz J Am Chem Soc 76 4465 1954, Beilstein 10 IV 1890.]
Diphenolic acid Preparation Products And Raw materials
Raw materialsLevulinic acid
Hydroxyphenyl 9,9-Bis(4-hydroxyphenyl)fluorene 4,4-BIS-(4-HYDROXY-3-NITROPHENYL)-VALERIC ACID 2-Ethylhexyl 2-(2,4-dichlorophenoxy)propionate Ethyl 2-(Chlorosulfonyl)acetate 4-Phenylbutyric acid 4,4'-Sulphonylbis(2,6-dibromophenol) Ascoric Acid Diphenolic acid TETRACHLORODIPHENOLIC ACID fatty acids/ oleic acid/ diphenolic acid/ ethylenediamine VALERIC ACID Tetrabromobisphenol A GAMMA,GAMMA-BIS(3,5-DICHLORO-4-HYDROXY-PHENYL)VALERIC ACID GAMMA,GAMMA-BIS(3,5-DIBROMO-4-HYDROXY-PHENYL)VALERIC ACID Isovaleric acid ETHYL GAMMA,GAMMA-BIS(4-HYDROXYPHENYL)VALERATE tert-Butyl acrylate

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