Maleic anhydride
[CAS# 108-31-6]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Halogenation, sulfonation, nitration or nitration of carboxylic anhydrides
• Name: Maleic anhydride
• Synonyms: 2,5-Furandione; MA
• Molecular Formula: C₄H₂O₃
• Molecular Weight: 98.06
• CAS Registry Number: 108-31-6
• EC Number: 203-571-6
• SMILES: C1=CC(=O)OC1=O

Properties

• Density: 1.48
• Melting point: 52-55 ºC
• Boiling point: 200 ºC
• Flash point: 102 ºC
• Water solubility: 79 g/100 mL (25 ºC)

Safety Data

• Hazard Symbols: GHS07;GHS08;GHS05 Danger
• Hazard Statements: H302-H372
• Precautionary Statements: P233-P260-P261-P264-P264+P265-P270-P271-P272-P280-P284-P301+P317-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P354+P338-P316-P317-P319-P321-P330-P333+P317-P342+P316-P362+P364-P363-P403-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Respiratory sensitization	Resp. Sens.	1	H334
Skin corrosion	Skin Corr.	1B	H314
Skin sensitization	Skin Sens.	1	H317
Serious eye damage	Eye Dam.	1	H318
Specific target organ toxicity - repeated exposure	STOT RE	1	H372
Skin sensitization	Skin Sens.	1A	H317
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Skin sensitization	Skin Sens.	1B	H317
Specific target organ toxicity - single exposure	STOT SE	1	H370
Acute toxicity	Acute Tox.	3	H311
Acute toxicity	Acute Tox.	1	H330
Specific target organ toxicity - single exposure	STOT SE	2	H371
Flammable liquids	Flam. Liq.	3	H226
Acute toxicity	Acute Tox.	4	H312
Skin corrosion	Skin Corr.	1A	H314
Acute toxicity	Acute Tox.	4	H332
Eye irritation	Eye Irrit.	2	H319

• Transport Information: UN 2215

Discovory and Applicatios

Maleic anhydride is an important organic compound used extensively in the chemical industry, recognized for its versatile applications in polymer production, resins, and various chemical intermediates. It was first identified in the early 19th century through the oxidation of benzene and later became more significant with the advent of large-scale production methods. Maleic anhydride is a cyclic dicarboxylic anhydride, commonly synthesized by the oxidation of n-butane or benzene in modern industrial processes. Its discovery paved the way for a wide range of applications due to its reactive nature and functionality in organic synthesis.

The production of maleic anhydride is largely carried out through the catalytic oxidation of n-butane, a process that was developed in the mid-20th century as a more efficient method compared to older benzene oxidation techniques. This innovation allowed for the mass production of maleic anhydride and significantly lowered costs, making it widely available for various industries. The chemical is a white crystalline solid at room temperature and readily hydrolyzes in water to form maleic acid.

One of the primary applications of maleic anhydride is in the production of unsaturated polyester resins. These resins are created by reacting maleic anhydride with glycols, such as ethylene glycol, and are then cross-linked with styrene to produce durable and flexible materials. Unsaturated polyester resins are widely used in the construction, marine, and automotive industries for the manufacture of fiberglass-reinforced plastics, coatings, and adhesives. The high reactivity of maleic anhydride makes it a key component in these formulations, enabling the production of strong, lightweight composites that are resistant to corrosion and environmental degradation.

Another significant application of maleic anhydride is in the production of alkyd resins, which are widely used in paints and coatings. Alkyd resins are synthesized through the reaction of maleic anhydride with polyols and fatty acids, resulting in a versatile material that forms durable, glossy coatings with excellent adhesion properties. These resins are commonly used in architectural coatings, industrial finishes, and printing inks. The ability of maleic anhydride to improve the hardness, flexibility, and chemical resistance of alkyd resins makes it an essential raw material for the coatings industry.

In addition to its role in resin production, maleic anhydride is a precursor to a variety of chemical intermediates. It is used in the synthesis of fumaric acid, which is employed as a food additive, and tetrahydrofuran (THF), a solvent widely used in the polymer and pharmaceutical industries. Maleic anhydride also serves as a building block in the manufacture of agricultural chemicals, lubricating oil additives, and surfactants. The reactivity of maleic anhydride, particularly its ability to undergo Diels-Alder reactions, has made it a valuable tool in organic synthesis for the preparation of complex molecules.

Maleic anhydride has found specialized applications in the pharmaceutical industry as well. Its derivatives are used in the production of active pharmaceutical ingredients (APIs) and as intermediates in the synthesis of various drugs. Its versatility in forming bonds with different chemical structures allows for the development of novel therapeutic agents, particularly in anti-inflammatory and cardiovascular treatments.

Environmental considerations have led to advancements in the sustainable production of maleic anhydride. As concerns over the use of benzene, a known carcinogen, grew, the shift to n-butane as the primary feedstock for maleic anhydride production became a standard practice. This transition not only reduced environmental hazards but also improved the overall efficiency and safety of the production process. Furthermore, maleic anhydride’s use in producing biodegradable polymers aligns with the growing demand for environmentally friendly materials in packaging and consumer goods.

Safety precautions in handling maleic anhydride are essential due to its irritant nature, especially upon contact with skin, eyes, and respiratory systems. Adequate protective equipment and ventilation are required during its manufacturing and application processes to mitigate exposure risks.

References

1984. Effect of anionic polymeric hydrogels on spermatozoa motility. Biomaterials, 5(5).
DOI: 10.1016/0142-9612(84)90080-2

2024. Relationships between crosslinking behaviour and morphological development in PLA/ENR blends using maleic anhydride as a coupling and TPV agent. Journal of Polymer Research, 31(12).
DOI: 10.1007/s10965-024-04214-x

2024. Eco-Friendly Fillers for Polymer Composites: A Comprehensive Review 2000-2024. Proceedings of the International Conference on Eco-friendly Fibers and Polymeric Materials.
DOI: 10.1007/978-981-97-7071-7_56