Itaconic acid (C5H6O4) is a compound used in various industries. It is produced from renewable resources and has applications in polymers, adhesives, and pharmaceuticals due to its unique chemical properties.
| IUPAC Name | Methylidenebutanedioic acid |
| Molecular Formula | C5H6O4 |
| CAS Number | 97-65-4 |
| Synonyms | Methylenesuccinic acid; MSA; MIDA |
| InChI | InChI=1S/C5H6O4/c6-3(7)1-2-4(8)5(9)10/h1-2H2,(H,6,7)(H,8,9)(H,10) |
Itaconic Acid Properties
Itaconic Acid Formula
The chemical formula of itaconic acid is C5H6O4. It is composed of five carbon atoms, six hydrogen atoms, and four oxygen atoms. This formula represents the arrangement and types of atoms present in each molecule of itaconic acid.
Itaconic Acid Molar Mass
The molar mass of methylenesuccinic acid is calculated by summing up the atomic masses of all its constituent atoms. It is approximately 130.10 grams per mole. This value is useful in various calculations involving methylenesuccinic acid, such as determining the amount of substance in a given quantity.
Itaconic Acid Boiling Point
The boiling point of methylenesuccinic acid is the temperature at which it changes from a liquid to a gaseous state under standard atmospheric pressure. Itaconic acid has a boiling point of around 185 degrees Celsius. This property is important in industrial processes that require the conversion of methylenesuccinic acid from liquid to gas.
Itaconic Acid Melting Point
The melting point of methylenesuccinic acid is the temperature at which it changes from a solid to a liquid state. Itaconic acid has a melting point of approximately 168 degrees Celsius. This characteristic is crucial in applications where methylenesuccinic acid needs to be heated to a specific temperature for various purposes.
Itaconic Acid Density g/mL
The density of methylenesuccinic acid is a measure of its mass per unit volume. Itaconic acid has a density of around 1.62 grams per milliliter. This property is significant in determining the amount of methylenesuccinic acid present in a given volume, which aids in formulation and manufacturing processes.
Itaconic Acid Molecular Weight
The molecular weight of methylenesuccinic acid is the sum of the atomic weights of all the atoms in a molecule. Itaconic acid has a molecular weight of approximately 130.10 grams per mole. This value is utilized in various calculations involving methylenesuccinic acid, such as determining stoichiometry and molecular properties.
Itaconic Acid Structure
The structure of methylenesuccinic acid consists of a carboxylic acid group and a double bond between two carbon atoms. It has a linear molecular structure and belongs to the class of unsaturated dicarboxylic acids. The arrangement of atoms in the structure determines the chemical and physical properties of methylenesuccinic acid.
Itaconic Acid Solubility
Methylenesuccinic acid exhibits limited solubility in water, with a solubility of approximately 11 grams per liter at room temperature. It is more soluble in organic solvents such as ethanol and acetone. The solubility of methylenesuccinic acid impacts its applications, as it affects its ease of formulation and dissolution in various mediums.
| Appearance | White crystalline powder |
| Specific Gravity | 1.62 g/mL |
| Color | Colorless to pale yellow |
| Odor | Odorless |
| Molar Mass | 130.10 g/mol |
| Density | 1.62 g/mL |
| Melting Point | 168 °C |
| Boiling Point | 185 °C |
| Flash Point | Not applicable |
| Water Solubility | 11 g/L |
| Solubility | Soluble in organic solvents |
| Vapor Pressure | Not available |
| Vapor Density | Not available |
| pKa | 3.57 |
| pH | 1.0-2.0 |
Itaconic Acid Safety and Hazards
Methylenesuccinic acid poses certain safety hazards that should be taken into consideration. Direct contact with methylenesuccinic acid may cause skin and eye irritation, so it is advisable to wear protective gloves and eyewear when handling the substance. Ingestion or inhalation of methylenesuccinic acid can also be harmful and may result in respiratory and gastrointestinal discomfort. Itaconic acid should be stored in a cool, dry place away from incompatible materials. In case of accidental release or exposure, proper ventilation should be ensured, and contaminated areas should be promptly cleaned up. Following appropriate safety protocols and handling guidelines is crucial to minimize the risks associated with methylenesuccinic acid.
| Hazard Symbols | Xi (Irritant) |
| Safety Description | Avoid contact with eyes, skin, and clothing. Wear protective gloves and eyewear. Use in well-ventilated areas. |
| UN IDs | Not applicable |
| HS Code | 2917.19.9000 |
| Hazard Class | Not classified |
| Packing Group | Not classified |
| Toxicity | Moderately toxic |
Itaconic Acid Synthesis Methods
There are several synthesis methods for producing methylenesuccinic acid. One commonly used method is the fermentation process. It starts with the cultivation of microorganisms, such as Aspergillus terreus or Escherichia coli, which have the ability to produce methylenesuccinic acid. These microorganisms are grown in a suitable medium containing carbon sources like glucose or starch. During the fermentation, the microorganisms convert the carbon sources into methylenesuccinic acid through metabolic pathways.
Another method involves the catalytic oxidation of citric acid. In this process, citric acid is subjected to oxidation using a suitable catalyst, such as manganese or cobalt salts, under controlled conditions. The oxidation reaction leads to the formation of methylenesuccinic acid as one of the products.
Additionally, methylenesuccinic acid can be synthesized from maleic anhydride. Maleic anhydride undergoes a hydrolysis reaction in the presence of water or a suitable acid catalyst to produce methylenesuccinic acid. This method is often used in industrial settings due to the availability and relatively low cost of maleic anhydride.
These synthesis methods offer different approaches to obtain methylenesuccinic acid, allowing for flexibility in production depending on the specific requirements and scale. Each method has its own advantages and considerations in terms of yield, purity, and environmental impact, which are important factors to consider in choosing the appropriate synthesis route.
Itaconic Acid Uses
Methylenesuccinic acid finds applications in various industries due to its unique chemical properties. Here are some key uses of methylenesuccinic acid:
- Polymers: Itaconic acid is utilized as a monomer in the production of polymers such as polymethylenesuccinic acid and poly(methyl itaconate). These polymers have applications in water treatment, oil drilling, and as dispersants and thickeners in various industrial processes.
- Adhesives: Itaconic acid is used as a co-monomer in the production of adhesive formulations. It improves the adhesive properties and enhances the bonding strength in applications like wood adhesives, paperboard laminates, and textile coatings.
- Pharmaceuticals: Itaconic acid derivatives are employed in pharmaceutical formulations. They act as intermediates in the synthesis of active pharmaceutical ingredients (APIs) and exhibit bioactive properties, making them useful in drug development.
- Personal Care Products: Itaconic acid and its derivatives find use in the formulation of personal care products such as hair sprays, gels, and creams. They provide improved texture, film-forming properties, and rheological control in cosmetic formulations.
- Coatings and Paints: Methylenesuccinic acid is incorporated into coatings and paints to enhance their performance. It improves adhesion, durability, and water resistance, making it suitable for applications in automotive coatings, architectural paints, and protective coatings.
- Textiles: Methylenesuccinic acid is used in textile finishing processes to impart properties like wrinkle resistance, flame retardancy, and dye absorption. It enhances the performance of textile materials and provides desirable functional attributes.
- Agriculture: Methylenesuccinic acid is utilized in agriculture as a biodegradable and environmentally friendly ingredient in plant growth regulators and soil conditioners. It aids in improving crop yield, disease resistance, and nutrient absorption.
The diverse range of applications showcases the versatility and utility of methylenesuccinic acid in various industries, contributing to advancements in materials, pharmaceuticals, and agricultural practices.
Questions:
Q: What is the mechanism of free radical polymerization of itaconic acid?
A: Methylenesuccinic acid undergoes free radical polymerization, where the double bond in its structure acts as the reactive site for the initiation and propagation of polymer chains.
Q: What is the m/z value of itaconic acid?
A: The m/z value (mass-to-charge ratio) of methylenesuccinic acid is 130.1 g/mol, corresponding to its molecular weight.
Q: What is the weight of itaconic acid?
A: The weight of methylenesuccinic acid is approximately 130.1 grams per mole.
Q: What polymers can be obtained from itaconic acid through polycondensation and ring-opening metathesis polymerization?
A: Methylenesuccinic acid enables the production of renewable polymers by undergoing polycondensation and ring-opening metathesis polymerization. These processes result in the synthesis of biodegradable and sustainable polymer materials.