Bisphenol A dianhydride CAS No. 38103-06-9

Product Description

Bisphenol A dianhydride (BPADA) is an aromatic ether dianhydride widely used as a high-performance monomer in polyimide synthesis. Structurally, it features a Bisphenol A core linked via ether bonds to two phthalic anhydride groups, giving it the reactivity and rigidity needed for advanced polymer applications. Typically appearing as a white to off-white crystalline powder, BPADA is essential in producing thermoplastic polyimides—such as Ultem® resins—renowned for exceptional thermal stability (Tg often exceeding 200 °C), mechanical strength, and chemical resistance. These materials find critical use in aerospace, automotive, and electronics industries, including flexible circuits, insulating films, and high-temperature coatings and adhesives. Industrially, BPADA is prepared through etherification of Bisphenol A with 4-nitrophthalonitrile, followed by hydrolysis and dehydration to yield the dianhydride.

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Product Use & Characteristics

Physical and Chemical Properties

• Chemical Name: 2,2-Bis(4-(3,4-dicarboxyphenoxy)phenyl)propane dianhydride

• Other Names / Synonyms:

  • 4,4′-(4,4′-Isopropylidenediphenoxy)bis(phthalic anhydride)

  • 4,4′-(4,4′-Isopropylidenediphenoxy)bisphthalic dianhydride

  • 4,4′-Bisphenol A diphthalic anhydride

  • 4,4′-[4,4′-Isopropylidenedi(p-phenyleneoxy)]bis(phthalic anhydride)

  • BISDA, Bisphenol A dianhydride

• Molecular Formula: C₃₁H₂₀O₈

• Molecular Weight: 520.5 g/mol

• IUPAC Name: 5-[4-[2-[4-[(1,3-dioxo-2-benzofuran-5-yl)oxy]phenyl]propan-2-yl]phenoxy]-2-benzofuran-1,3-dione

• Appearance: White to off-white crystalline powder; solid at room temperature.

• Structure: Bisphenol A core connected via ether bonds to two phthalic anhydride groups.

• Key Functional Groups: Two cyclic anhydride groups (reactive sites for imidization reactions).

• Thermal Properties:

  • Polyimides derived from BPADA typically have glass transition temperatures (Tg) > 200 °C; Ultem® resins Tg ≈ 217 °C.

  • High thermal stability—polyimide films from BPADA can retain >80 wt% mass at 500 °C and form stable carbonaceous residue at 1000 °C.

• Solubility:

  • Insoluble in water and lower alcohols (methanol, ethanol).

  • Good solubility in aprotic polar solvents: NMP, DMF, DMSO, THF; also soluble in some low-boiling organic solvents such as acetone, dichloromethane, and ethyl acetate.

  • Solubility enhanced by structural features (ether linkages, isopropylidene group) that disrupt chain packing.

• Optical Properties: BPADA-based polyimides can have high optical transparency.

Uses

• Primary Application: Monomer in high-performance polyimide synthesis (thermoplastic and thermosetting types).

• End Products:

  • Thermoplastic Polyetherimides (PEIs) (e.g., Ultem® resins) — aerospace, automotive, and electronics.

  • Photosensitive Polyimides for microelectronics and advanced packaging.

  • High-temperature adhesives — BPADA-based precursors with phthalonitrile or other reactive end groups can achieve high lap shear strengths at elevated temperatures.

  • Epoxy resin curing agents.

  • Superhydrophobic aerogels.

  • Fuel cell membranes — due to chemical inertness and stability.

• Typical Applications:

  • Aerospace components (structural parts, composites, engine applications).

  • Electronics (flexible printed circuits, insulating films, dielectric layers in capacitors).

  • Automotive components requiring heat and chemical resistance.

  • Coatings, films, and protective layers with high temperature resistance.

Synthesis

• Conventional Route:

  1. Etherification: Bisphenol A reacts with 4-nitrophthalonitrile to produce a dinitrile intermediate.

  2. Hydrolysis: The dinitrile is hydrolyzed to yield a tetraacid.

  3. Dehydration: The tetraacid is cyclized to the dianhydride form.

• Alternative Route: Reaction of 4-chlorophthalic anhydride with bisphenol A via nucleophilic aromatic substitution.

• In Polyimide/PEI Film Production: BPADA reacts with diamines (e.g., m-phenylenediamine) to form poly(amic acid), followed by thermal imidization.

• Processing Innovations: Interfacial polymerization (IP) methodsallow formation of ultrathin films (200 nm–1 µm) with controlled morphology, improving scalability and reducing processing temperatures.

Storage and Transportation

• Storage Conditions:

  • Store in a cool, dry, well-ventilated area.

  • Keep container tightly closed to prevent moisture uptake (anhydrides hydrolyze to dicarboxylic acids in presence of water).

  • Avoid prolonged exposure to light and heat.

• Transportation:

  • Solid form; generally stable under recommended transport conditions.

  • Keep away from sources of moisture and incompatible materials (strong bases, strong oxidizers).

Safety Precautions

• Hazards:

  • Irritating to skin, eyes, and respiratory tract.

  • Dust may cause respiratory discomfort; high dust concentrations may aggravate pre-existing respiratory conditions.

• Handling Measures:

  • Use PPE: chemical-resistant gloves, protective goggles, and lab coat.

  • Ensure adequate local exhaust ventilation when handling powders.

  • Avoid breathing dust; use NIOSH-approved dust respirators if airborne concentrations are high.

• First Aid:

  • Skin/Eye Contact: Rinse immediately with plenty of water; seek medical attention if irritation persists.

  • Inhalation: Move to fresh air; seek medical attention if symptoms occur.

• Environmental Precautions: Avoid uncontrolled release into environment.

• Thermal Decomposition: Avoid temperatures above recommended processing limits without adequate ventilation; decomposition may release irritant fumes.

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