126-00-1

Basic information

• Product Name: Diphenolic acid
• Synonyms: 4-Hydroxy-(4-hydroxyphenyl)benzenebutanoicacid;4-hydroxy-gamma-(4-hydroxyphenyl)-gamma-methyl-benzenebutanoicaci;4,4-BIS(4-HYDROXYPHENYL)-N-VALERIC ACID;4,4-BIS(4-HYDROXYPHENYL)PENTANOIC ACID;4,4-BIS(4-HYDROXYPHENYL)VALERIC ACID;4,4-BIS(P-HYDROXYPHENYL)PENTANOIC ACID;4,4'-BIS(P-HYDROXYPHENYL)VALERIC ACID;4,4-BIS(P-HYDROXYPHENYL)VALERIC ACID
• CAS NO: 126-00-1
• Molecular Formula: C₁₇H₁₈O₄
• Molecular Weight: 286.32
• EINECS: 204-763-2
• Product Categories: Building Blocks;C13 to C42+;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Organic Building Blocks
• Mol File: 126-00-1.mol
• Article Data: 7

Chemical Properties

• Melting Point: 167-170 °C(lit.)
• Boiling Point: 388.69°C (rough estimate)
• Flash Point: 208°C
• Appearance: Light brown particles
• Density: 1.30
• Vapor Pressure: 3.48E-11mmHg at 25°C
• Refractive Index: 1.5450 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 4.66±0.10(Predicted)
• Merck: 14,3312
• BRN: 1886361
• CAS DataBase Reference: Diphenolic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Diphenolic acid(126-00-1)
• EPA Substance Registry System: Diphenolic acid(126-00-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-36
• Safety Statements: 26-37/39-36
• WGK Germany: 3
• F: 10
• TSCA: Yes
• Hazardous Substances Data: 126-00-1(Hazardous Substances Data)

Usage

Chemical Properties

Light pink solid

Uses

Different sources of media describe the Uses of 126-00-1 differently. You can refer to the following data:
1. Diphenolic 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.
2. Diphenolic Acid is a flux compound. Adhesives for semiconductor devices.
3. Since 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.

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

Industrial uses

Diphenolic 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 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.]

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)

Synthetic route

levulinic acid (123-76-2) + phenol (108-95-2) → 4,4-bis(4-hydroxyphenyl)valeric acid (126-00-1)

Conditions	Yield
With sulfuric acid
With hydrogenchloride
With C16H28N4O6S2(2+)*2CF3O3S(1-); C16H28N4O6S2(2+)*2C3H7O3S2(1-) at 60℃; for 48h; Reagent/catalyst; Sealed tube; Inert atmosphere; Schlenk technique;	91 mol

4-hydroxy-γ-(4-hydroxyphenyl)-γ-methyl-benzenebutanoic acid methyl ester (7297-85-0) + methyl iodide (74-88-4) → 4,4-bis(4-hydroxyphenyl)valeric acid (126-00-1) + 4,4-bis(4'-methoxyphenyl)pentanoic acid (111161-78-5) + (4'-hydroxyphenyl)-4-(4''-methoxyphenyl)pentanoic acid

Conditions	Yield
With potassium hydroxide; cobalt(II) acetate; silver(l) oxide Product distribution; multistepreaction, degradative method for the determination of the degree of branching for hyperbranched macromolecules;

water (7732-18-5) + levulinic acid (123-76-2) + phenol (108-95-2) + mineral acid → 4,4-bis(4-hydroxyphenyl)valeric acid (126-00-1)

4-oxopentanoic acid ethyl ester (539-88-8) + phenol (108-95-2) → 4,4-bis(4-hydroxyphenyl)valeric acid (126-00-1)

Conditions	Yield
With sulfuric acid In water at 0 - 20℃; for 18h; Condensation;

levulinic acid (123-76-2) + phenol (108-95-2) → 4,4-bis(4-hydroxyphenyl)valeric acid (126-00-1) + C17H18O4 (1033556-25-0)

Conditions	Yield
With ethanethiol at 99.84℃; for 16h; Inert atmosphere;
With C16H28N4O6S2(2+)*2C3H7O3S2(1-) at 60℃; for 48h; Reagent/catalyst; Temperature; Time; Concentration; Sealed tube; Inert atmosphere; Schlenk technique; Overall yield = 75 mol;

4-oxopentanoic acid ethyl ester (539-88-8) + phenol (108-95-2) → 4,4-bis(4-hydroxyphenyl)valeric acid (126-00-1) + ethyl diphenolate (7297-86-1)

Conditions	Yield
With C16H28N4O6S2(2+)*2CF3O3S(1-); C16H28N4O6S2(2+)*2C3H7O3S2(1-) at 60℃; for 48h; Reagent/catalyst; Sealed tube; Inert atmosphere; Schlenk technique; Overall yield = 80 mol;	A 22 mol B 58 mol

levulinic acid methyl ester (624-45-3) + phenol (108-95-2) → 4,4-bis(4-hydroxyphenyl)valeric acid (126-00-1) + 4-hydroxy-γ-(4-hydroxyphenyl)-γ-methyl-benzenebutanoic acid methyl ester (7297-85-0)

Conditions	Yield
With C16H28N4O6S2(2+)*2CF3O3S(1-); C16H28N4O6S2(2+)*2C3H7O3S2(1-) at 60℃; for 48h; Sealed tube; Inert atmosphere; Schlenk technique; Overall yield = 79 mol;	A 22 mol B 57 mol

butyl levulinate (2052-15-5) + phenol (108-95-2) → 4,4-bis(4-hydroxyphenyl)valeric acid (126-00-1) + butyl diphenolate (7297-88-3)

Conditions	Yield
With C16H28N4O6S2(2+)*2CF3O3S(1-); C16H28N4O6S2(2+)*2C3H7O3S2(1-) at 60℃; for 48h; Sealed tube; Inert atmosphere; Schlenk technique; Overall yield = 81 mol;	A 16 mol B 65 mol

methanol (67-56-1) + 4,4-bis(4-hydroxyphenyl)valeric acid (126-00-1) → 4-hydroxy-γ-(4-hydroxyphenyl)-γ-methyl-benzenebutanoic acid methyl ester (7297-85-0)

Conditions	Yield
With sulfuric acid for 8h; Fischer-Speier Esterification; Reflux;	99%
With sulfuric acid for 3h; Esterification; Heating;	97%
for 2h; Reflux;	96%

methanol (67-56-1) + 4,4-bis(4-hydroxyphenyl)valeric acid (126-00-1) + trimethyl orthoformate (149-73-5) → 4-hydroxy-γ-(4-hydroxyphenyl)-γ-methyl-benzenebutanoic acid methyl ester (7297-85-0)

Conditions	Yield
With p-toluenesulfonic acid monohydrate for 16h; Reflux;	98%

4,4-bis(4-hydroxyphenyl)valeric acid (126-00-1) + trimethyl orthoformate (149-73-5) → 4-hydroxy-γ-(4-hydroxyphenyl)-γ-methyl-benzenebutanoic acid methyl ester (7297-85-0)

Conditions	Yield
With toluene-4-sulfonic acid In methanol for 16h; Reflux;	98%

formaldehyd (50-00-0) + 4,4-bis(4-hydroxyphenyl)valeric acid (126-00-1) + 1,3,5-triphenylhexahydro-1,3,5-triazine (91-78-1) → 4,4-bis[3-phenyl-3,4-dihydro-2H-1,3-benzoxazin-6-yl]pentanoic acid (918303-70-5)

Conditions	Yield
In toluene at 110℃; for 6h;	95%
In toluene at 110℃; for 6h;	94.8%

4,4-bis(4-hydroxyphenyl)valeric acid (126-00-1) + phosphazene base-P4-tert-butyl (111324-04-0) → C17H18O4*C22H63N13P4 (1370263-33-4)

Conditions	Yield
In tetrahydrofuran; hexane at 20℃; for 12h; Inert atmosphere;	95%

1-methyl-piperazine (109-01-3) + 4,4-bis(4-hydroxyphenyl)valeric acid (126-00-1) → N-methyl piperazine diphenolamide

Conditions	Yield
at 160 - 180℃; Inert atmosphere;	95%
at 80 - 180℃; Inert atmosphere;	85%

4,4-bis(4-hydroxyphenyl)valeric acid (126-00-1) + benzyl chloride (100-44-7) → benzyl 4,4-bis[4-(benzyloxy)phenyl]pentanoate (184866-14-6)

Conditions	Yield
With 18-crown-6 ether; potassium carbonate In acetone for 72h; Heating;	90%

ethanol (64-17-5) + 4,4-bis(4-hydroxyphenyl)valeric acid (126-00-1) → ethyl diphenolate (7297-86-1)

Conditions	Yield
With sulfuric acid for 16h; Fischer-Speier Esterification; Reflux;	85%
at 40℃; for 8h; Sealed tube; Inert atmosphere; Schlenk technique;	83 mol

4,4-bis(4-hydroxyphenyl)valeric acid (126-00-1) + 9-bromoethylanthracene (2417-77-8) → anthracen-9-ylmethyl-4,4-bis(4-hydroxyphenyl)pentanoate

Conditions	Yield
Stage #1: 4,4-bis(4-hydroxyphenyl)valeric acid With potassium hydrogencarbonate In N,N-dimethyl-formamide at 80℃; for 0.5h; Stage #2: 9-bromoethylanthracene In N,N-dimethyl-formamide at 80℃; for 2h;	84%

anthracenylmethyl chloride (24463-19-2) + 4,4-bis(4-hydroxyphenyl)valeric acid (126-00-1) → anthracen-9-ylmethyl-4,4-bis(4-hydroxyphenyl)pentanoate

Conditions	Yield
Stage #1: 4,4-bis(4-hydroxyphenyl)valeric acid With potassium hydrogencarbonate In N,N-dimethyl-formamide at 80℃; for 0.5h; Stage #2: anthracenylmethyl chloride In N,N-dimethyl-formamide at 80℃; for 5h;	84%

4,4-bis(4-hydroxyphenyl)valeric acid (126-00-1) + benzyl bromide (100-39-0) → benzyl 4,4-bis[4-(benzyloxy)phenyl]pentanoate (184866-14-6)

Conditions	Yield
With potassium carbonate; potassium iodide In acetone Reflux;	83.5%

4,4-bis(4-hydroxyphenyl)valeric acid (126-00-1) + (9H-fluoren-9-yl)methyl (S)-(2-amino-3-((3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propyl)(methyl)amino)-3-oxopropyl)carbamate → (9H-fluoren-9-yl)methyl (S)-(2-(4,4-bis(4-hydroxyphenyl)pentanamido)-3-((3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propyl)(methyl)amino)-3-oxopropyl)carbamate

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1h;	83%

2-bromoisobutyric acid bromide (20769-85-1) + 4,4-bis(4-hydroxyphenyl)valeric acid (126-00-1) → 4,4-bis-[4-(2-bromo-2-methyl-propionyloxy)-phenyl]-pentanoic acid

Conditions	Yield
With triethylamine In tetrahydrofuran for 48h;	82%

4,4-bis(4-hydroxyphenyl)valeric acid (126-00-1) + desipramine hydrochloride (58-28-6) → N-(3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propyl)-4,4-bis(4-hydroxyphenyl)-N-methylpentanamide

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1h;	82%

4,4-bis(4-hydroxyphenyl)valeric acid (126-00-1) + 4-(hydroxymethyl)-1-oxido-2,6,7-trioxa-1-phosphabicyclo [2.2.2] octane (5301-78-0) → C22H25O8P

Conditions	Yield
With toluene-4-sulfonic acid In acetonitrile at 70℃; for 24h; Inert atmosphere;	80.2%
With toluene-4-sulfonic acid In acetonitrile for 24h; Inert atmosphere; Reflux;	55%

4,4-bis(4-hydroxyphenyl)valeric acid (126-00-1) + ethyl 3-endo-3-hydroxy-8-azabicyclo[3.3.1]octane-8-carboxylate (30833-12-6) → N-ethoxycarbonyl diphenylglycol acetate

Conditions	Yield
Stage #1: 4,4-bis(4-hydroxyphenyl)valeric acid With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 30℃; for 2.5h; Stage #2: ethyl 3-endo-3-hydroxy-8-azabicyclo[3.3.1]octane-8-carboxylate With dmap In dichloromethane at 25 - 30℃; for 3.5h;	80%

4,4-bis(4-hydroxyphenyl)valeric acid (126-00-1) + tert-butyl alcohol (75-65-0) → tert-butyl 4,4-bis(4'-hydroxyphenyl)pentanoate (138721-52-5)

Conditions	Yield
Stage #1: 4,4-bis(4-hydroxyphenyl)valeric acid With trifluoroacetic anhydride In tetrahydrofuran at 5 - 20℃; for 2.5h; Stage #2: tert-butyl alcohol In tetrahydrofuran at 20℃; for 6h;	71.1%

tetrakis[bis(trimethylsilyl)methyl]digallane(4) (125370-09-4) + 4,4-bis(4-hydroxyphenyl)valeric acid (126-00-1) → Ga2(CH(SiMe3)2)2(4,4-bis(4-hydroxyphenyl)valerate)2 (1258211-74-3)

Conditions	Yield
In tetrahydrofuran digallium compd. and acid suspended in THF at room temp.; suspn. stirred at room temp. for 16 h; volatiles removed in vacuo; residue washed with n-pentane;	66%

4,4-bis(4-hydroxyphenyl)valeric acid (126-00-1) + 1,3-dibromo-propane (109-64-8) → 4,4-bis-(4-hydroxy-phenyl)-pentanoic acid 3-bromo-propyl ester (848599-31-5)

Conditions	Yield
Stage #1: 4,4-bis(4-hydroxyphenyl)valeric acid With potassium hydrogencarbonate In N,N-dimethyl-formamide at 80℃; for 0.5h; Stage #2: 1,3-dibromo-propane In N,N-dimethyl-formamide at 80℃; for 5h;	65%

3,4-dihydro-2H-pyran (110-87-2) + 4,4-bis(4-hydroxyphenyl)valeric acid (126-00-1) → 4,4-bis-[4-(tetrahydro-pyran-2-yloxy)-phenyl]-pentanoic acid

Conditions	Yield
With pyridinium p-toluenesulfonate	65%

methanol (67-56-1) + 4,4-bis(4-hydroxyphenyl)valeric acid (126-00-1) + 2-(chloromethyl)quinoline monohydrochloride (3747-74-8) → 4,4-bis(3-chloro-4-(2-quinolylmethoxy)phenyl)pentanoic acid methyl ester (189498-99-5) + 4-(3-chloro-4-(2-quinolylmethoxy)phenyl)-4-(3,5-dichloro-4-(2-quinolylmethoxy)phenyl)pentanoic acid methyl ester

Conditions	Yield
Stage #1: 4,4-bis(4-hydroxyphenyl)valeric acid With N-chloro-succinimide In 1,4-dioxane; chloroform for 5h; Chlorination; Heating; Stage #2: methanol With thionyl chloride at 20℃; for 16h; Esterification; Stage #3: 2-(chloromethyl)quinoline monohydrochloride With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 10h; Alkylation; Further stages.;	A 61% B 9%

Diethyl iminodiacetate (6290-05-7) + 4,4-bis(4-hydroxyphenyl)valeric acid (126-00-1) → {[4,4-bis-(4-hydroxyphenyl)-pentanoyl]-ethoxycarbonyl-methylamino}-acetic acid ethyl ester (625833-52-5)

Conditions	Yield
With 2-chloro-1-methyl-pyridinium iodide; triethylamine In 1,4-dioxane at 70℃; for 0.166667 - 0.333333h;	56%

4,4-bis(4-hydroxyphenyl)valeric acid (126-00-1) + (9H-fluoren-9-yl)methyl (2-((3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propyl)amino)ethyl)carbamate → (9H-fluoren-9-yl)methyl (2-(N-(3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propyl)-4,4-bis(4-hydroxyphenyl)pentanamido)ethyl)carbamate

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1h;	48%

4,4-bis(4-hydroxyphenyl)valeric acid (126-00-1) + 2-(3,4-bis((tert-butyldimethylsilyl)oxy)phenyl)ethan-1-amine (165749-18-8) → N-(3,4-bis((tert-butyldimethylsilyl)oxy)phenethyl)-4,4-bis(4-hydroxyphenyl)pentanamide

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In ethyl acetate at 20℃; for 3h; Inert atmosphere;	46%

4,4-bis(4-hydroxyphenyl)valeric acid (126-00-1) + 1,1'-carbonyldiimidazole (530-62-1) + dibenzylamine (103-49-1) → 4,4-Bis-(4-hydroxyphenyl)pentanoic acid dibenzylamide (188108-07-8)

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; water; ethyl acetate	40%

4,4-bis(4-hydroxyphenyl)valeric acid (126-00-1) + tert-butyldimethylsilyl chloride (18162-48-6) → C23H32O4Si (1219458-16-8)

Conditions	Yield
Stage #1: 4,4-bis(4-hydroxyphenyl)valeric acid; tert-butyldimethylsilyl chloride With 1H-imidazole In tetrahydrofuran for 12h; Reflux; Stage #2: With acetic acid In water at 20℃; for 2h;	40%

6-azido-2S-{[(9H-fluorenyl-9-ylmethoxy)carbonyl]amino}hexanoic acid (159610-89-6) + O-bis-(aminoethyl)ethylene glycol trityl resin + 4,4-bis(4-hydroxyphenyl)valeric acid (126-00-1) + N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)hex-5-ynamide (1623789-42-3) + Fmoc-Asp-O-t-Bu (129460-09-9, 134098-70-7) → N-[4,4-bis(4-hydroxyphenyl)pentanoyl]-β-aspartyl-β-aspartyl-N-{2-[2-(2-aminoethoxy)ethoxy]ethyl}-6-(4-{4-oxo-4-[(5-sulfamoyl-1,3,4-thiadiazol-2-yl)amino]butyl}-1H-1,2,3-triazol-1-yl)-L-norleucinamide

Conditions

Yield

Stage #1: 6-azido-2S-{[(9H-fluorenyl-9-ylmethoxy)carbonyl]amino}hexanoic acid; O-bis-(aminoethyl)ethylene glycol trityl resin With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 22℃; for 1.25h; trityl resin; Stage #2: With piperidine In N,N-dimethyl-formamide Stage #3: 4,4-bis(4-hydroxyphenyl)valeric acid; N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)hex-5-ynamide; Fmoc-Asp-O-t-Bu Further stages;

38%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + 4,4-bis(4-hydroxyphenyl)valeric acid (126-00-1) → 2,5-dioxopyrrolidin-1-yl-4,4-bis(4-hydroxyphenyl)pentanoate (1445510-01-9)

Conditions	Yield
With dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 22h;	36%
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 1h;	250 mg

4,4-bis(4-hydroxyphenyl)valeric acid (126-00-1) + Fmoc-Leu-OH (35661-60-0) + N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)hex-5-ynamide (1623789-42-3) + Boc-Lys(Fmoc)-OH (84624-27-1) + Fmoc-(tBu)Asp-OH (71989-14-5) + Fmoc-Asp-O-t-Bu (129460-09-9, 134098-70-7) + N-(9-fluorenylmethoxycarbonyl)-S-trityl-L-cysteine (103213-32-7) → C52H70N14O19S3

Conditions

Yield

Stage #1: N-(9-fluorenylmethoxycarbonyl)-S-trityl-L-cysteine With piperidine In N,N-dimethyl-formamide for 0.25h; Stage #2: Fmoc-(tBu)Asp-OH With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 0℃; for 1.25h; Stage #3: 4,4-bis(4-hydroxyphenyl)valeric acid; Fmoc-Leu-OH; N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)hex-5-ynamide; Boc-Lys(Fmoc)-OH; Fmoc-Asp-O-t-Bu Further stages;

22%

4,4-bis(4-hydroxyphenyl)valeric acid (126-00-1) + Fmoc-Leu-OH (35661-60-0) + 5-hexynoic amide (21233-94-3) + Fmoc-(tBu)Asp-OH (71989-14-5) + Fmoc-Asp-O-t-Bu (129460-09-9, 134098-70-7) + N-(9-fluorenylmethoxycarbonyl)-S-trityl-L-cysteine (103213-32-7) + Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine → NH2+-ValCit-MMAE

Conditions

Yield

Stage #1: N-(9-fluorenylmethoxycarbonyl)-S-trityl-L-cysteine With piperidine In N,N-dimethyl-formamide for 0.25h; Stage #2: Fmoc-(tBu)Asp-OH With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 0℃; for 1.25h; Stage #3: 4,4-bis(4-hydroxyphenyl)valeric acid; Fmoc-Leu-OH; 5-hexynoic amide; Fmoc-Asp-O-t-Bu; Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine Further stages;

11%

Upstream product

• 123-76-2 levulinic acid 
• 108-95-2 phenol 
• 7732-18-5 water 
• 7297-85-0 4-hydroxy-γ-(4-hydroxyphenyl)-γ-methyl-benzenebutanoic acid methyl ester 
• 74-88-4 methyl iodide 
• 2052-15-5 butyl levulinate 
• 624-45-3 levulinic acid methyl ester 
• 539-88-8 4-oxopentanoic acid ethyl ester 

Downstream Products

• 64523-93-9 4,4-Bis-(4-diphenoxymethoxy-phenyl)-pentanoic acid diphenoxymethyl ester 
• 7297-85-0 4-hydroxy-γ-(4-hydroxyphenyl)-γ-methyl-benzenebutanoic acid methyl ester 
• 848599-31-5 4,4-bis-(4-hydroxy-phenyl)-pentanoic acid 3-bromo-propyl ester 
• 25040-92-0 4,4'-(1-Methyl-4,4-diphenylbutylidene)bisphenol 
• 25051-19-8 4,4'-(4-Hydroxy-1-methyl-4,4-diphenylbutylidene)-bisphenol 
• 188108-09-0 4,4'-[4-[Bis(phenylmethyl)amino]-1-methylbutylidene]-bisphenol 
• 188108-07-8 4,4-Bis-(4-hydroxyphenyl)pentanoic acid dibenzylamide 
• 1397706-66-9 4,4'-(4,4'-(5-hydroxypentane-2,2-diyl)bis(4,1-phenylene))bis(oxy)dibenzaldehyde 
• 1397706-67-0 4,4'-bis(4-(4-formylphenoxy)phenyl)pentyl 2-bromopropanoate 
• 7297-86-1 ethyl diphenolate 
• 7297-88-3 butyl diphenolate 

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Mesoporous H3PW12O40-silica composite catalysts with controllable H3PW12O40 loadings (4.0–65.1%) were prepared by a direct sol–gel–hydrothermal technique in the presence of triblock poly(ethylene oxide)-poly(propylene oxide)-poly(ethylene oxide) copolymer. Powder X-ray diffraction (XRD) patte...detailed

Thermal stability of aromatic polyesters prepared from Diphenolic acid (cas 126-00-1) and its esters09/27/2019

The thermal performance of aromatic polyesters (poly(DPA–IPC), poly(MDP–IPC) and poly(EDP–IPC)) prepared from isophthaloyl chloride (IPC) with diphenolic acid (DPA) and its esters were studied with DSC and TG, and the decomposition mechanism of poly(DPA–IPC) were investigated using FTIR and ...detailed

Treatment of water contaminated with Diphenolic acid (cas 126-00-1) by gamma radiation in the presence of different compounds09/26/2019

The elimination of diphenolic acid (DPA) from contaminated water is an urgent challenge. The aim of this study was to investigate DPA degradation by gamma radiation, studying the influence of the dose rate, initial DPA concentration, solution pH, the presence of O2, and the presence of different...detailed

Diphenolic acid (cas 126-00-1) based biphosphate on the properties of polylactic acid: Synthesis, fire behavior and flame retardant mechanism09/25/2019

In an effort to impart fire protection properties to polylactic acid (PLA) utilizing renewable resources, diphenolic acid, a plant derived compound, was used to synthesize a biphosphate (hereinafter shortened as FR) that contains two types of phosphorus. The chemical structure of FR was confirme...detailed

Self-foaming Diphenolic acid (cas 126-00-1) benzoxazine09/09/2019

This work concerns the investigation of porous polybenzoxazines based on the non-toxic renewable diphenolic acid. The approach described relies on the in situ generation of foaming agent (CO2) during the thermal curing. For this purpose, the previously synthesized benzoxazine monomer from diphen...detailed

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Kinetics of phosphotungstic acid-catalyzed condensation of levulinic acid with phenol to diphenolic acid: Temperature-controlled regioselectivity

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

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.