BISPHENOL A DIGLYCIDYL ETHER RESIN

Base Information

• Chemical Name: BISPHENOL A DIGLYCIDYL ETHER RESIN
• CAS No.: 1675-54-3
• Deprecated CAS: 116161-20-7,170962-54-6,47424-12-4,85101-00-4,1018476-17-9,1226906-55-3,220756-60-5,64339-51-1,1253646-32-0,1416960-74-1,1608493-63-5,1645304-11-5,1826890-03-2,1826890-16-7,1886013-38-2,1889329-63-8,100629-69-4,104137-75-9,107461-90-5,110737-21-8,112603-15-3,115566-93-3,116469-81-9,118815-21-7,122157-02-2,122538-86-7,123584-39-4,125005-11-0,131151-70-7,132325-44-1,135668-53-0,137086-94-3,137545-84-7,137802-59-6,141093-30-3,145849-86-1,148092-60-8,150872-30-3,152059-80-8,161107-52-4,168759-37-3,171264-64-5,179530-03-1,181493-44-7,185702-25-4,26142-22-3,37217-54-2,37294-19-2,39378-82-0,39475-40-6,41178-38-5,51280-98-9,51374-21-1,51394-05-9,51910-45-3,52229-16-0,52350-20-6,52737-84-5,53637-50-6,55963-67-2,56690-61-0,56730-71-3,56832-64-5,58128-07-7,58615-59-1,58799-17-0,59979-12-3,59979-27-0,60202-18-8,60371-12-2,60825-75-4,61287-89-6,62362-68-9,62494-59-1,64083-68-7,64083-69-8,65098-97-7,66038-83-3,66198-86-5,66594-39-6,68190-11-4,72841-21-5,72847-21-3,73379-77-8,73612-85-8,75718-49-9,75831-43-5,78214-26-3,80702-62-1,81774-75-6,82496-74-0,83138-88-9,84069-58-9,84502-78-3,84617-15-2,85497-34-3,86168-14-1,86546-69-2,87004-20-4,87755-52-0,87912-89-8,9036-67-3,108058-29-3,108066-37-1,122897-17-0,128465-86-1,128513-55-3,129898-93-7,148569-29-3,161755-95-9,161936-32-9,166515-91-9,172451-28-4,193144-17-1,226910-00-5,243466-91-3,256338-94-0,303964-41-2,306971-27-7,441069-44-9,448927-08-0,495376-29-9,51425-98-0,532994-20-0,55774-85-1,56690-19-8,683815-99-8,74811-75-9,84135-55-7,852960-59-9,888316-32-3,898283-26-6,903885-45-0,99751-69-6,254448-95-8,908602-63-1,934479-37-5,934697-88-8,1000808-10-5,1009069-48-0,1020667-39-3,1200449-05-3,1207980-82-2,1227470-34-9,1259927-51-9,1268496-37-2,1310584-08-7,1311195-17-1,1400634-77-6,195459-69-9,295358-50-8,336790-36-4,39421-68-6,473553-29-6,82446-01-3,855526-28-2,87501-52-8,915090-50-5,1094621-90-5,117946-60-8,1204018-95-0,1233542-29-4,1254941-36-0,1262222-54-7,1315991-74-2,132893-71-1,1330081-80-5,1431940-00-9,1442645-03-5,1616883-17-0,1639783-41-7,1701460-40-3,174794-97-9,1803142-08-6,1818293-74-1,1860801-07-5,197592-26-0,2011755-07-8,2052302-38-0,209225-22-9,634603-84-2,77537-89-4,82513-45-9,898230-33-6,898230-35-8,905309-86-6,914982-96-0,945957-77-7,946123-74-6,1623062-02-1,2095665-24-8,2101185-81-1,2222994-56-9,2240175-31-7,918147-36-1,1231161-42-4,124759-84-8,1273321-32-6,1355342-16-3,141332-35-6,1486351-77-2,1663480-43-0,1803142-07-5,2234240-82-3,2304400-64-2,2311881-74-8,2311881-77-1,2374090-04-5,2411966-90-8,2412830-33-0,2490291-88-6,2590538-36-4,2601639-31-8,909776-77-8,945525-42-8,1219000-12-0,2704576-13-4,1018476-17-9,170962-54-6,220756-60-5,47424-12-4,64339-51-1,85101-00-4
• Molecular Formula: C21H24O4
• Molecular Weight: 340.419
• Hs Code.: 2910900090
• European Community (EC) Number: 216-823-5
• ICSC Number: 0151
• NSC Number: 5022
• UNII: F3XRM1NX4H
• DSSTox Substance ID: DTXSID6024624
• Nikkaji Number: J14.164J
• Wikipedia: Bisphenol_A_diglycidyl_ether
• Wikidata: Q2080808
• Metabolomics Workbench ID: 45716
• ChEMBL ID: CHEMBL258558
• Mol file: 1675-54-3.mol

Synonyms:Propane,2,2-bis[p-(2,3-epoxypropoxy)phenyl]- (6CI,8CI);2,2-Bis(4-glycidyloxyphenyl)propane;2,2-Bis(4-hydroxyphenyl)propane diglycidylether;2,2-Bis(p-glycidyloxyphenyl)propane;2,2-Bis(p-hydroxyphenyl)propane diglycidyl ether;2,2-Bis[4-(2,3-epoxypropyloxy)phenyl]propane;2,2-Di(4-glycidyloxyphenyl)propane;4,4'-Bis(2,3-epoxypropoxy)diphenyldimethylmethane;4,4'-Isopropylidenediphenoldiglycidyl ether;Bis(4-hydroxyphenyl)dimethylmethane diglycidyl ether;Bis(phenol) A diglycidal ether;Bisphenol Adiglycidyl ether;DGEBA;Diglycidylbisphenol A;Diomethanediglycidyl ether;NSC 5022;

Chemical Property of BISPHENOL A DIGLYCIDYL ETHER RESIN

Chemical Property:

• Appearance/Colour: colorless or yellowish brown liquid
• Vapor Pressure: 3.66E-09mmHg at 25°C
• Melting Point: 40-44 °C
• Refractive Index: 1.5735
• Boiling Point: 487 °C at 760 mmHg
• Flash Point: 148.5 °C
• PSA: 43.52000
• Density: 1.168 g/cm³
• LogP: 3.56770
• Storage Temp.: 2-8°C
• Solubility.: Soluble in DMSO (up to 30 mg/ml) or in Ethanol (up to 15 mg/ml)
• Water Solubility.: Soluble in 100% ethanol, dimethyl sulfoxide (100 mM), dimethyl formamide, chloroform, methanol, and ethanol (50 mM). Insoluble i
• XLogP3: 4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 340.16745924
• Heavy Atom Count: 25
• Complexity: 384

Purity/Quality:

99% ^*data from raw suppliers

Bisphenol?A diglycidyl ether ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/38-43
• Safety Statements: 28-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Plastics & Rubber -> Epoxy Resins
• Canonical SMILES: CC(C)(C1=CC=C(C=C1)OCC2CO2)C3=CC=C(C=C3)OCC4CO4
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Short Term Exposure: The substance is irritating to the eyes and skin. Exposure could cause lowering of consciousness.
• Effects of Long Term Exposure: Repeated or prolonged contact with skin may cause dermatitis. Repeated or prolonged contact may cause skin sensitization.
• Description: Most epoxy resins result from polymerization of bisphenol A diglycidyl ether (BADGE). Delayed hypersensitivity is caused by the low-molecular-weight monomer BADGE (MW 340 g/mol), the dimer having a much lower sensitization power. This allergen caused contact dermatitis in six workers in a plant producing printed circuits boards made of copper sheets and fiberglass fabric impregnated with a brominated epoxy resin. It can also be contained in adhesives. PPARγ is a ligand-activated transcription factor involved in the regulation of lipid homeostasis and may function as a master regulator of adipogenesis. Ligands for PPARγ include antidiabetic drugs of the thiazolidinedione structural class, 15-deoxy-Δ12,14-prostaglandin J2 , and NSAIDS. BADGE is a synthetic compound used in the production of polycarbonate and industrial plastics. BISPHENOL A DIGLYCIDYL ETHER RESIN was recently identified as an antagonist of PPARγ. BADGE binds to PPARγ with an apparent Kd of 100 μM and interferes with the ability of 3T3-L1 and 3T3-F442A cells to undergo hormone-mediated cell differentiation.
• Uses: Bisphenol A derivative. A PPARγ antagonist; exhibits estrogenic activity; An inhibitor of PPARγ and suppressor of TNFα. In the manufacture of epoxy resins and polycarbonates for food packaging. The uniqueness of D.E.R. 332 epoxy resin is reflected in its maximum epoxide equivalent weight of 178. Because of its high purity and lack of polymer factions, samples embedded using D.E.R. 322 have uniform performance, exceptionally low viscosity and color; and improved elevated temperature properties.

Technology Process of BISPHENOL A DIGLYCIDYL ETHER RESIN

There total 5 articles about BISPHENOL A DIGLYCIDYL ETHER RESIN which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

BPA (80-05-7) + epichlorohydrin (106-89-8,24969-06-0,13403-37-7) → diphenylolpropane diglycidyl ether (1675-54-3,25085-99-8,55774-85-1,91384-80-4)

Guidance literature:

With tetrabutylammomium bromide; potassium hydroxide; at 20 ℃; for 12h;

DOI:10.1021/jm1000584

Reference yield: 55.2%

bisphenol A diallyl ether (3739-67-1) → bisphenol A monoglycidyl ether (140896-80-6) + diphenylolpropane diglycidyl ether (1675-54-3,25085-99-8,55774-85-1,91384-80-4)

Guidance literature:

With tetramethyl ammoniumhydroxide; dihydrogen peroxide; acetonitrile; In methanol; water; at 30 ℃; for 4.5h; pH=11; Product distribution / selectivity;

Reference yield:

1-chloro-3-[4-[2-[4-(3-chloro-2-hydroxypropoxy)phenyl] propan-2-yl]phenoxy]propan-2-ol (4809-35-2) → racemic 1-chloro-3-(4-(2-(4-(oxiran-2-ylmethoxy)phenyl)propan-2-yl)phenoxy)propan-2-ol (13836-48-1) + C21H25ClO4 + C23H27ClO5 + C23H28O6 + C24H32O7 + 2-[4-(3-chloro-2-hydroxypropyloxy)phenyl]-2-[4-(2,3-dihydroxypropyloxy)phenyl]propane (227947-06-0) + C24H32O6 + diphenylolpropane diglycidyl ether (1675-54-3,25085-99-8,55774-85-1,91384-80-4) + 2-[4-(2,3-epoxypropanyloxy)phenyl]-2-[4-(2,3-dihydroxypropanyloxy)phenyl]propane (76002-91-0)

Guidance literature:

With sodium hydroxide; In 1-methoxy-2-propanol; water; at 25 - 52 ℃; for 2.5h;

upstream raw materials:

BPA

epichlorohydrin

1-chloro-3-[4-[2-[4-(3-chloro-2-hydroxypropoxy)phenyl] propan-2-yl]phenoxy]propan-2-ol

bisphenol A diallyl ether

Downstream raw materials:

2,2-bis-[4-(2,3-diacetoxy-propoxy)-phenyl]-propane

2,2'-bis(4-hydroxycyclohexyl)propane glycidyl ether

4,4'-(((propane-2,2-diylbis(4,1-phenylene))bis(oxy))bis(methylene))bis(1,3-dioxolan-2-one)

Refernces

Synthesis of bio-based epoxy monomers from natural allyl- and vinyl phenols and the estimation of their affinity to the estrogen receptor α by molecular docking

10.1039/c6nj00782a

This study investigates the creation of sustainable epoxy monomers as alternatives to the diglycidyl ether of bisphenol A (DGEBA). The researchers synthesized diepoxydized diphenyls from eugenol, 4-vinyl guaiacol, and canolol through glycidylation with epichlorohydrin followed by cross metathesis (CM) dimerization using the Grubbs II catalyst. The synthesized products and their hydrolysed forms were then assessed for their potential endocrine-disrupting activity by estimating their binding affinity to the estrogen receptor a (ERa) using molecular docking. The study found that the epoxy forms had a moderate affinity to the antagonistic conformation of ERa, six to forty times lower than bisphenol A (BPA), while their hydrolysed forms exhibited relatively weak affinity in both agonistic and antagonistic conformations. This suggests that the synthesized bio-based epoxy monomers could serve as safer alternatives to DGEBA, with reduced potential for endocrine disruption.

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