126-00-1 Usage
Description
Diphenolic acid (DPA) is a light pink solid that is a close structural analog of bisphenol A. It is the condensation product of levulinic acid and phenol, and has been identified as a potential replacement for bisphenol A, which is commonly used as a monomer for epoxy resins and polycarbonates.
Uses
Used in Plastics and Polymer Industry:
Diphenolic acid is used as a replacement for bisphenol A in the production of epoxy resins and polycarbonates. It offers a safer alternative to bisphenol A, which is a possible endocrine disruptor and is used in various applications such as baby bottles, dental resins, and lacquers to coat food cans.
Used in Surface Coatings Industry:
Diphenolic acid serves as an intermediate for surface coatings, providing a safer alternative to bisphenol A-based coatings.
Used in Lubricant Industry:
Diphenolic acid is used as a lubricating oil additive, enhancing the performance and longevity of lubricants.
Used in Cosmetics Industry:
Diphenolic acid is used in cosmetics as a safer alternative to bisphenol A, which is commonly used in personal care products.
Used in Surfactants Industry:
Diphenolic acid is used in the production of surfactants, which are essential in various cleaning and personal care products.
Used in Plasticizers Industry:
Diphenolic acid is used as a plasticizer, improving the flexibility and workability of plastics.
Used in Textile Industry:
Diphenolic acid is used in textile chemicals, enhancing the performance and durability of textiles.
Used in Semiconductor Industry:
Diphenolic acid is used as a flux compound in the production of adhesives for semiconductor devices.
Industrial Uses:
Diphenolic acid is useful in the preparation of modified phenol formaldehyde resins and polyether resins. It also serves as a monocarboxilic acid chain stopper in alkyd resins.
Preparation
Diphenolic 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
Purification Methods
When 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.]
Check Digit Verification of cas no
The CAS Registry Mumber 126-00-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 6 respectively; the second part has 2 digits, 0 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 126-00:
(5*1)+(4*2)+(3*6)+(2*0)+(1*0)=31
31 % 10 = 1
So 126-00-1 is a valid CAS Registry Number.
InChI:InChI=1/C17H14Br4O4/c1-17(3-2-14(22)23,8-4-10(18)15(24)11(19)5-8)9-6-12(20)16(25)13(21)7-9/h4-7,24-25H,2-3H2,1H3,(H,22,23)
126-00-1Relevant articles and documents
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Bader,Kontowicz
, p. 4465 (1954)
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Kinetics of phosphotungstic acid-catalyzed condensation of levulinic acid with phenol to diphenolic acid: Temperature-controlled regioselectivity
Evrard, Clint N.,Hossain, Md Anwar,Rahaman, Mohammad Shahinur,Sathitsuksanoh, Noppadon,Thompson, Lee M.,Tulaphol, Sarttrawut
, (2021/09/10)
Diphenolic acid (DPA) is a renewable compound to produce polycarbonates and epoxy resins. Diphenolic acid is produced by acid-catalyzed condensation of levulinic acid with phenol to form monophenolic acid. Subsequently, monophenolic acid undergoes condensation with phenol to form two DPA isomers, ortho-diphenolic acid (o,p′-DPA) and para-diphenolic acid (p,p′-DPA). Here we describe a kinetic analysis of solvent-free levulinic acid-phenol condensation catalyzed by phosphotungstic acid at temperatures between 70 and 140°C. The reaction appeared to be pseudo-first-order with respect to levulinic acid when the levulinic acid:phenol molar ratio was four or higher. We determined the kinetic parameters (reaction rate constants, pre-exponential factors, and activation energies) by fitting experimental results to simulated data. Although the activation energies of o,p′-DPA, and p,p′-DPA formation were higher than their corresponding reverse reactions, the kinetic analyses revealed that a steric effect controls the reaction products. Our findings demonstrated a simple temperature-controlled strategy to achieve a p,p′:o,p′ DPA molar ratio of 28.3 with 87% conversion and 98% selectivity to total DPA. This work provides a potential production route for p,p′-DPA from biomass.
Thiol-promoted catalytic synthesis of diphenolic acid with sulfonated hyperbranched poly(arylene oxindole)s
Van De Vyver, Stijn,Geboers, Jan,Helsen, Sasja,Yu, Feng,Thomas, Joice,Smet, Mario,Dehaen, Wim,Sels, Bert F.
scheme or table, p. 3497 - 3499 (2012/06/18)
Acid-catalyzed condensation of levulinic acid and phenol into high yields of diphenolic acid (>50%) is possible with a combination of sulfonated hyperbranched polymers and thiol promotors, either added as a physical mixture or bound to the polymer by ion-pairing.