Itaconic Acid, Methylene Succinic Acid, Methylidene Butanedioic Acid, Methylenesuccinic Acid, 97-65-4

ITACONIC ACID

Itaconic Acid / Methylene Succinic Acid / Methylidene Butane Dioic Acid / 2-Methylenesuccinic Acid
CAS Number: 97-65-4
EC Number: 202-599-6

1. PRODUCT IDENTIFICATION AND CHEMICAL IDENTITY

Itaconic acid is an unsaturated dicarboxylic acid with the chemical formula C₅H₆O₄. It is a white crystalline solid that is soluble in water and various organic solvents. As a bio-based chemical, itaconic acid is produced by fermentation of carbohydrates using microorganisms such as Aspergillus terreus. It is a sustainable alternative to petrochemical-based monomers and is considered a key building block for green chemistry. Itaconic acid contains two carboxyl groups and a reactive double bond, making it highly versatile for polymerization and derivatization reactions . It is used in the production of synthetic resins, plastics, textile fibers, adhesives, coatings, detergents, water treatment chemicals, and pharmaceuticals.

2. PHYSICAL AND CHEMICAL PROPERTIES

Itaconic acid is a white crystalline solid that decomposes upon heating at 162-164°C without melting. It is soluble in water (1 g/12 mL) and ethanol (1 g/5 mL) . The compound has two carboxyl groups and a reactive double bond (C=C) in its structure, which provides high reactivity and polymerization capability . Its bio-based origin makes it an environmentally friendly alternative to petrochemical-based monomers.

3. CHEMICAL PROPERTIES AND REACTIONS

Itaconic acid is an unsaturated dicarboxylic acid that undergoes the characteristic reactions of both carboxyl groups and the reactive double bond.

Polymerization:

Itaconic acid readily polymerizes with itself or with other monomers (acrylic acid, acrylamide, styrene, butadiene) to form homopolymers and copolymers. The double bond allows free-radical polymerization.

Esterification:

Itaconic acid reacts with alcohols to form mono- and diesters, which are used as plasticizers and intermediates.

Decarboxylation:

Itaconic acid can be decarboxylated to form itaconic anhydride or other derivatives.

Hydrogenation:

The double bond can be hydrogenated to form methylsuccinic acid.

Metal Complexation:

Itaconic acid forms complexes with metal ions, making it useful as a chelating agent and scale inhibitor .

4. PRODUCTION METHOD

Itaconic acid is produced industrially by fermentation of carbohydrates (sugars, molasses, starch) using the fungus Aspergillus terreus . The fermentation process is carried out under aerobic conditions at controlled temperature and pH. The itaconic acid is then recovered from the fermentation broth by precipitation, crystallization, and purification.

Fermentation Process:

1. Substrate Preparation: Carbohydrate sources (glucose, sucrose, molasses) are prepared with nutrients and mineral salts.

2. Fermentation: Aspergillus terreus is cultivated in fermenters under aerobic conditions at 30-35°C for 5-7 days.

3. Recovery: The fermentation broth is filtered to remove biomass, and itaconic acid is precipitated by adjusting pH.

4. Crystallization: The crude itaconic acid is crystallized and purified.

5. SPECIFICATIONS (INDUSTRIAL GRADE)

6. APPLICATIONS AND INDUSTRIAL USES

Itaconic acid is a versatile bio-based chemical with a wide range of applications across multiple industries .

6.1. Polymers and Resins (Most Important Application)

Itaconic acid is primarily used in polymer and resin applications. It is incorporated as a co-monomer in acrylic resins, SBR, unsaturated polyester resins, polyamides, and polyurethanes to enhance adhesion, flexibility, mechanical strength, and chemical resistance . Its bio-based nature makes it an ideal choice for sustainable polymer production.

6.2. Coatings and Paints

Itaconic acid is used in water-based coatings, low-VOC paints, and industrial coatings to improve adhesion, water resistance, and durability .

6.3. Adhesives and Dispersions

Itaconic acid is used in pressure-sensitive adhesives (PSA) as a co-monomer to improve tack and adhesion. It is also used as a stabilizer in SBR and acrylic latex dispersions .

6.4. Textile and Fiber Industry

Itaconic acid is used in textile finishing chemicals, fiber processing agents, and nonwoven binders to enhance durability, water resistance, and adhesion .

6.5. Detergents and Water Treatment

Itaconic acid is used in phosphate-free detergents as a chelating agent and dispersant. It is also used as a scale inhibitor and dispersant in water treatment systems .

6.6. Superabsorbent Polymers

Itaconic acid is used in superabsorbent polymers (SAP) for diapers, hygiene products, and agricultural applications to modify cross-linking structure and improve water absorption capacity.

6.7. Other Applications

7. TYPICAL FORMULATIONS AND USAGE RATES

Itaconic acid is typically used at concentrations of 1-5% in polymer applications, 0.5-2% in SAP formulations, and ppm levels in water treatment applications . The exact usage rate depends on the specific application and desired performance characteristics.

8. ADVANTAGES

Itaconic acid offers significant advantages as a bio-based, sustainable alternative to petrochemical-based monomers. It supports green chemistry, reduces VOC emissions, and improves product performance while being non-toxic and biodegradable .

9. INDUSTRY SUITABILITY TABLE

10. TEST METHODS

11. SAFETY AND TOXICOLOGY

Itaconic acid has very low toxicity (oral LD50 > 5,000 mg/kg in rats). It is non-irritating to skin and mildly irritating to eyes. It is not a skin sensitizer, not mutagenic, and not classified as carcinogenic. It is readily biodegradable and has low bioaccumulation potential .

12. FIRST AID MEASURES

13. SAFETY INFORMATION (GHS CLASSIFICATION)

Itaconic acid is not classified as a hazardous substance under GHS. However, fine powder may cause respiratory irritation.

Signal Word: WARNING

Hazard Statements (H-Codes):

Precautionary Statements (P-Codes):

14. STORAGE AND HANDLING

Itaconic acid should be stored below 25°C in cool, dry, well-ventilated areas, protected from moisture. It is slightly hygroscopic and should be protected from moisture. Containers should be kept tightly closed to prevent moisture absorption and contamination. It is incompatible with strong oxidizing agents, strong acids, and strong bases. Shelf life under proper storage conditions is typically 24-36 months.

15. OTHER NAMES AND DATABASE IDENTIFIERS

Database Identifiers:

16. SUMMARY AND CRITICAL WARNINGS

SUMMARY:

Itaconic acid (C₅H₆O₄, CAS 97-65-4) is a bio-based, unsaturated dicarboxylic acid produced by fermentation of carbohydrates using Aspergillus terreus . It appears as a white crystalline powder, is soluble in water and ethanol, and has a melting point of 162-164°C (decomposes). The molecular weight is 130.10 g/mol, and density is 1.63 g/cm³. It is used as a co-monomer in acrylic resins, SBR, unsaturated polyester resins, polyamides, and polyurethanes to improve adhesion, flexibility, chemical resistance, and water resistance. It is also used in coatings, adhesives, detergents, water treatment, superabsorbent polymers, textiles, and pharmaceuticals . It has very low toxicity, is non-irritating, and is readily biodegradable. It is stored below 25°C in cool, dry, well-ventilated areas, protected from moisture.

Key Properties:

Major Application Areas:

Key Safety Points:

• LOW TOXICITY: Oral LD50 > 5,000 mg/kg

• NON-IRRITANT: Non-irritating to skin; mild eye irritant

• BIO-BASED: Produced from renewable resources 

• READILY BIODEGRADABLE: Environmentally compatible 

• STORAGE: Below 25°C, cool, dry, tightly closed

• PPE RECOMMENDED: Dust mask, safety goggles, protective gloves (for handling powder)

Important Disclaimer: This Technical Data Sheet (TDS) is for informational purposes only. The information provided is based on available data and is believed to be accurate. However, the user is solely responsible for determining the suitability of the product for their specific application and for complying with all applicable regulations and safety requirements. For complete safety, handling, storage, and regulatory compliance information, always refer to the official Safety Data Sheet (SDS/MSDS) provided by the manufacturer/supplier. Users are responsible for testing the product in their own processes and applications. All local, national, and international regulations must be followed when working with itaconic acid.