1,2,4,5-Cyclohexanetetracarboxylic acid dianhydride
[CAS# 2754-41-8]

Identification

• Classification: Chemical reagent >> Organic reagent >> Carboxylic anhydride
• Name: 1,2,4,5-Cyclohexanetetracarboxylic acid dianhydride
• Synonyms: 1,2,4,5-Cyclohexanetetracarboxylic dianhydride; HPMDA
• Molecular Formula: C₁₀H₈O₆
• Molecular Weight: 224.17
• CAS Registry Number: 2754-41-8
• EC Number: 691-475-9
• SMILES: C1C2C(CC3C1C(=O)OC3=O)C(=O)OC2=O

Properties

• Density: 1.567±0.1 g/cm³, Calc.^*
• Melting Point: 240 °C (Expl.)
• Index of Refraction: 1.556, Calc.^*
• Boiling Point: 517.5±50.0 °C (760 mmHg), Calc.^*
• Flash Point: 238.6±30.2 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

1,2,4,5-Cyclohexanetetracarboxylic acid dianhydride (CHTCA) is an important organic compound used in various chemical processes and materials science. This dianhydride is derived from 1,2,4,5-cyclohexanetetracarboxylic acid, a polyfunctional acid with significant applications in polymer chemistry and the production of advanced materials. The compound has a distinctive structure featuring a cyclohexane ring with four carboxylic acid groups, which, upon dehydration, form the dianhydride derivative.

The discovery of 1,2,4,5-cyclohexanetetracarboxylic acid dianhydride was part of ongoing efforts in the mid-20th century to develop polyfunctional organic compounds capable of forming high-performance polymers. Its synthesis is typically achieved by dehydration of the corresponding acid, often using a dehydrating agent like acetic anhydride. The unique reactivity of the dianhydride makes it a valuable intermediate in various chemical reactions, particularly in the preparation of polyimide and polyamide-imide polymers.

One of the major applications of 1,2,4,5-cyclohexanetetracarboxylic acid dianhydride is in the production of high-temperature-resistant polymers. It is often used as a monomer in the synthesis of polyimides, which are known for their excellent thermal stability, electrical insulating properties, and chemical resistance. These properties make polyimides suitable for use in aerospace, electronics, and automotive industries, where materials must withstand harsh operating conditions, including high temperatures and aggressive chemicals.

Another important application of CHTCA dianhydride is in the manufacture of polyamide-imide (PAI) polymers. PAI combines the features of both polyimides and polyamides, offering a balance of high strength, toughness, and temperature resistance. These polymers are used in applications such as bearings, bushings, and electrical insulation, where performance at elevated temperatures and under mechanical stress is critical.

In addition to its use in high-performance polymers, 1,2,4,5-cyclohexanetetracarboxylic acid dianhydride is also utilized in the production of specialty coatings and adhesives. These coatings, often applied to metal and composite materials, provide excellent adhesion, chemical resistance, and durability under extreme conditions.

The compound also plays a role in the development of advanced composite materials. By reacting with various epoxy resins or other polymer matrices, CHTCA dianhydride helps to improve the strength and heat resistance of composite materials, which are used extensively in the aerospace and automotive sectors.

In conclusion, 1,2,4,5-cyclohexanetetracarboxylic acid dianhydride is a versatile chemical compound with numerous applications in the production of high-performance polymers, coatings, adhesives, and composite materials. Its ability to form robust, heat-resistant materials makes it a key component in industries that require advanced materials with exceptional mechanical and thermal properties.

References

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