Description
Trimellitic anhydride acid chloride, also known as 4-Chloroformylphthalic anhydride or TMAC, is a trifunctional aromatic compound containing both an anhydride group and an acid chloride group attached to a benzene ring. This unique structure makes it a highly reactive and versatile chemical intermediate. The presence of two distinct reactive sites (the anhydride and the acid chloride) allows for selective reactions and the formation of complex polymeric structures and derivatives. It typically appears as a white to off-white or pale yellow crystalline solid and is a crucial raw material in the synthesis of various high-performance materials and specialty chemicals. Its reactivity requires careful handling, particularly regarding moisture, as it can readily hydrolyze.
Properties
Property Value Chemical Name Trimellitic anhydride acid chloride Synonyms 4-Chloroformylphthalic anhydride, TMAC, 1,3-Dioxo-1,3-dihydroisobenzofuran-5-carbonyl chloride CAS Number 1204-28-0 Molecular Formula C9H3ClO4 Molecular Weight 210.57 g/mol Appearance White to off-white or pale yellow crystalline powder/solid Purity ≥98% (typical, may vary by grade) Melting Point 68-71 °C (154-160 °F) (typical) Boiling Point 165-170 °C at 14 mmHg (approx. 280-285 °C at atmospheric pressure, may decompose); 120-124 °C (0.1 torr) Solubility Reacts with water and alcohols. Soluble in many organic solvents (e.g., chlorinated hydrocarbons, aromatic hydrocarbons, ethers, ketones), often with reaction. Stability Moisture sensitive; hydrolyzes in the presence of water. Stable under dry, inert conditions. Usage
Trimellitic anhydride acid chloride (TMAC) is primarily used as a highly reactive chemical intermediate and monomer in the synthesis of a wide range of materials. Its key applications include:
- High-Performance Polymers: TMAC is a crucial monomer for producing polyamide-imides (PAIs) and polyester-imides. These polymers exhibit excellent thermal stability, mechanical strength, and chemical resistance, making them suitable for demanding applications in aerospace, automotive, and electronics (e.g., wire enamels, coatings, films, and molded parts).
- Curing Agent for Epoxy Resins: It serves as an effective curing agent or hardener for epoxy resins, imparting high heat resistance and improved mechanical properties to the cured products. These are used in composites, adhesives, and coatings.
- Synthesis of Plasticizers: Used in the production of trimellitate ester plasticizers, which are valued for their permanence and performance at high temperatures in PVC and other polymers.
- Chemical Intermediate: TMAC is a versatile building block for synthesizing various specialty chemicals, including dyes, pigments, pharmaceuticals (less common), and other organic compounds where its trifunctional reactivity is beneficial.
- Adhesion Promoters: Derivatives of TMAC can be used as adhesion promoters in coatings and adhesives.
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