1,2,4-Benzenetricarboxylic anhydride
[CAS# 552-30-7]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Halogenation, sulfonation, nitration or nitration of carboxylic anhydrides
• Name: 1,2,4-Benzenetricarboxylic anhydride
• Synonyms: Benzene-1,2,4-tricarboxylic anhydride; Trimellitic anhydride
• Molecular Formula: C₉H₄O₅
• Molecular Weight: 192.13
• CAS Registry Number: 552-30-7
• EC Number: 209-008-0
• SMILES: C1=CC2=C(C=C1C(=O)O)C(=O)OC2=O

Properties

• Density: 1.54
• Melting point: 164-169 ºC
• Boiling point: 390 ºC
• Flash point: 227 ºC
• Water solubility: DECOMPOSES

Safety Data

• Hazard Symbols: GHS08;GHS05;GHS07 Danger
• Hazard Statements: H335-H318-H334-H317
• Precautionary Statements: P233-P260-P261-P264+P265-P271-P272-P280-P284-P302+P352-P304+P340-P305+P354+P338-P317-P319-P321-P333+P317-P342+P316-P362+P364-P403-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin sensitization	Skin Sens.	1	H317
Serious eye damage	Eye Dam.	1	H318
Respiratory sensitization	Resp. Sens.	1	H334
Specific target organ toxicity - single exposure	STOT SE	3	H335
Specific target organ toxicity - single exposure	STOT SE	3	H370
Acute toxicity	Acute Tox.	4	H332
Specific target organ toxicity - repeated exposure	STOT RE	1	H372
Specific target organ toxicity - single exposure	STOT SE	1	H370

Discovory and Applicatios

1,2,4-Benzenetricarboxylic anhydride, commonly known as trimellitic anhydride (TMA), is an important chemical compound with the formula C9H6O5. It appears as a white crystalline solid and is primarily used as an intermediate in the production of various chemicals and materials. The discovery of trimellitic anhydride can be traced back to the mid-20th century, as researchers sought to explore new compounds with useful chemical properties. TMA is derived from trimellitic acid, which itself is obtained through the oxidation of certain aromatic hydrocarbons, particularly toluene.

The synthesis of trimellitic anhydride typically involves the dehydration of trimellitic acid, a process that can be accomplished through heating or chemical methods. This anhydride form is significant in various chemical applications due to its reactivity and ability to form derivatives. Trimellitic anhydride has a structure that allows it to participate in a range of chemical reactions, making it a valuable compound in organic synthesis.

One of the primary applications of trimellitic anhydride is in the production of polyesters and polyimides. These polymers are essential in the manufacturing of high-performance materials, including coatings, adhesives, and electrical insulation. When reacted with various alcohols, TMA can be used to produce polyesters with enhanced thermal and mechanical properties. The incorporation of trimellitic anhydride into polymer matrices can significantly improve their flexibility and durability, making them suitable for demanding applications in industries such as automotive, aerospace, and electronics.

In addition to its role in polymer synthesis, trimellitic anhydride is utilized in the production of plasticizers. Plasticizers are additives that enhance the workability and flexibility of plastics. By incorporating trimellitic anhydride into plastic formulations, manufacturers can improve the performance characteristics of products like vinyl flooring, synthetic rubber, and various types of coatings. The ability of TMA to form stable esters with polyols contributes to the effectiveness of these plasticizers, enhancing the final product's usability in different environments.

Another notable application of trimellitic anhydride is in the formulation of surfactants and emulsifiers. TMA can be reacted with various amines and alcohols to create surfactants that are effective in stabilizing emulsions and foams. These surfactants are widely used in personal care products, household cleaners, and industrial applications, where they play a crucial role in enhancing product performance.

Trimellitic anhydride is also relevant in the field of medicine, particularly in drug delivery systems. Researchers are investigating its potential for use as a carrier for therapeutic agents, utilizing its ability to form biocompatible polymers that can encapsulate drugs and facilitate their controlled release. The development of such systems holds promise for improving the efficacy and safety of various pharmaceutical formulations.

While trimellitic anhydride has many beneficial applications, it is important to recognize that it can pose health risks. It is classified as a skin and respiratory sensitizer, and exposure may lead to allergic reactions in sensitive individuals. Therefore, proper safety measures should be implemented when handling this compound in industrial and laboratory settings, including the use of personal protective equipment and adequate ventilation.

In summary, 1,2,4-benzenetricarboxylic anhydride is a versatile chemical compound with a wide range of applications in polymer production, plasticizers, surfactants, and drug delivery systems. Its discovery has facilitated advancements in various industries, highlighting its significance as an important chemical intermediate. Ongoing research continues to explore new applications and formulations involving trimellitic anhydride, ensuring its relevance in modern chemical science.