Introduction to Tridecanedioic Acid
Tridecanedioic acid, also known as Brassylic acid, is a saturated, dicarboxylic acid with the chemical formula C13H24O4. It features a chain of 13 carbon atoms with carboxyl groups (-COOH) at both ends. The compound is recognized by its CAS number 505-52-2 and has a variety of industrial applications due to its unique structure and chemical properties. This article provides an in-depth look at the chemical properties, production methods, and diverse uses of Brassylic acid, shedding light on its growing significance in both industrial and research contexts.
Chemical Properties of Tridecanedioic Acid
Molecular Structure and Composition
Tridecanedioic acid is a relatively simple organic molecule but offers a variety of reactivity options due to its two carboxyl groups. The molecular formula can be written as C13H24O4, where each carboxyl group (-COOH) can participate in different chemical reactions, such as esterification, reduction, or polymerization.
The compound’s chemical structure can be described as:
HOOC-(CH₂)₁₁-COOH
This structure classifies Brassylic acid as a long-chain dicarboxylic acid, with applications related to both fatty acids and dicarboxylic acid chemistry. It belongs to a class of aliphatic dicarboxylic acids, a family that includes other acids like azelaic acid (C9) and sebacic acid (C10).
Physical Properties
- Molecular Weight: 244.33 g/mol.
- Boiling Point: Approximately 380°C.
- Melting Point: 108°C to 112°C.
- Solubility: Brassylic acid is sparingly soluble in water but dissolves in organic solvents such as ethanol, acetone, and ether.
- Appearance: Typically, Brassylic acid is a white to off-white crystalline solid or powder.
Chemical Reactivity
- Acidity: The two carboxyl groups in the molecule are acidic, and their ability to donate protons (H⁺) makes them highly reactive in typical acid-base reactions. The pKa values of the two carboxyl groups fall between 4.5 and 5.0, indicating moderate acidity.
- Reduction: The carboxyl groups in Brassylic acid can undergo reduction reactions. Using reducing agents like lithium aluminum hydride (LiAlH₄), Brassylic acid can be converted to tridecanediol (a polyol), which finds applications in polyether and polyester resins.
- Esterification: One of the most significant chemical processes for Brassylic acid is esterification, where it reacts with alcohols to form esters. These esters, such as butyl tridecanedioate, are used as plasticizers in the polymer industry.
- Oxidation: Brassylic acid can be oxidized to produce shorter-chain acids or undergo various functional group transformations to produce novel products like ketones or aldehydes. Such transformations are valuable in chemical synthesis.
Thermal Stability
Brassylic acid has moderate thermal stability, as it can withstand typical industrial processing conditions but may decompose at higher temperatures (above 350°C), undergoing decarboxylation and breakdown of the alkyl chain.
Production Process of Tridecanedioic Acid
Raw Materials and Feedstocks
The primary feedstocks for the production of Brassylic acid are natural fatty acids. These fatty acids typically come from plant oils (e.g., palm oil, coconut oil) or animal fats. The long-chain fatty acids present in these materials (like tridecanoic acid or its precursor, tridecene) are subjected to various chemical processes to synthesize Brassylic acid.
Industrial Production Methods
- Oxidation of Long-Chain Fatty Acids: The production of Brassylic acid usually starts with a fatty acid that contains 13 carbon atoms. These fatty acids are oxidized using oxygen, air, or other oxidizing agents such as potassium permanganate. The oxidation process introduces two carboxyl groups to the fatty acid chain, converting it into tridecanedioic acid.
- Bio-based Routes: Bio-based methods are increasingly being studied for their potential to produce Brassylic acid sustainably. Microbial fermentation processes are one approach, where genetically engineered strains of microorganisms like Escherichia coli can be used to produce dicarboxylic acids, including Brassylic acid, from renewable feedstocks such as glucose or plant oils.
- Catalytic Hydrogenation and Cyclization: Catalytic hydrogenation or cyclization can be employed to modify the carbon chain or to introduce desired functional groups, further refining the properties of Brassylic acid.
- Purification: After synthesis, crude Brassylic acid must be purified to remove any impurities or by-products. This is usually done by recrystallization, where Brassylic acid is dissolved in a solvent, followed by crystallization under controlled conditions. Alternatively, distillation can be used to purify the compound under reduced pressure.
Challenges in Production
Despite its potential, the production of Brassylic acid remains relatively niche, and scalability continues to be a challenge. The yield from bio-based routes can be low, and conventional oxidation processes can be energy-intensive. Nonetheless, advancements in fermentation technology and process optimization are helping improve efficiency and reduce costs.
Applications of Tridecanedioic Acid
Brassylic acid has a wide range of applications across multiple industries. These applications are driven by its chemical properties, which make it suitable for use in the production of polymers, lubricants, plasticizers, and many other specialty chemicals.
1. Polymer Synthesis
One of the most significant applications of Brassylic acid is in the production of polyamides, a class of polymers known for their excellent mechanical properties, high thermal stability, and chemical resistance.
- Polyamide 13,10: This high-performance polymer is synthesized from Brassylic acid and diamines like 1,3-diaminopropane. Polyamide 13,10 is notable for its high melting point, stiffness, and resistance to wear and tear, making it ideal for automotive, aerospace, and industrial applications. The polymer is used in applications requiring durability, such as under-the-hood automotive components, bearings, and other friction-resistant materials.
- Aliphatic Polyamides: Brassylic acid is also used in the production of aliphatic polyamides, which are widely used in textiles and specialty fibers. These fibers are valued for their strength, elasticity, and resistance to degradation in harsh environments, making them ideal for use in military or technical textiles.
2. Plasticizers and Additives
Esters of Brassylic acid are employed as plasticizers in the polymer industry. Plasticizers are additives that increase the flexibility, processability, and workability of polymers like PVC (polyvinyl chloride) and polyurethane.
- Dioctyl Tridecanedioate (DOTD): This ester of Brassylic acid is commonly used as a plasticizer for PVC and polyvinyl acetate. The esterified form of Brassylic acid offers low volatility, excellent thermal stability, and low-temperature flexibility, making it particularly suitable for use in automotive parts, electrical cables, flooring, and medical devices.
- Bio-based Plasticizers: As part of the push for more sustainable chemical products, Brassylic acid-derived plasticizers are increasingly being considered as bio-based alternatives to traditional petroleum-derived plasticizers. These bio-based alternatives are biodegradable and have a reduced environmental footprint.
3. Lubricants and Greases
Tridecanedioic acid is used to create high-performance lubricants and greases. These products offer excellent thermal stability, oxidation resistance, and low volatility, making them ideal for industrial and automotive applications.
- High-Temperature Lubricants: Brassylic acid derivatives, such as its esters, are often used in lubricants designed for use in engines and other machinery operating at high temperatures. The lubricants reduce wear and friction, improving the lifespan of machinery while ensuring smooth operation in extreme conditions.
- Industrial Greases: The long-chain nature of Brassylic acid also allows it to function as a thickening agent in greases, contributing to their performance under heavy load conditions.
4. Cosmetics and Personal Care Products
Brassylic acid is increasingly being used in the cosmetic and personal care industry. The compound and its derivatives serve as surfactants, emulsifiers, and skin conditioning agents in various skincare products.
- Skin Care Products: Tridecanedioic acid’s mild acidic nature makes it a suitable ingredient in skin care formulations designed for sensitive skin. It acts as a moisturizer and pH adjuster in creams, lotions, and ointments. Its non-irritating properties help prevent skin reactions, making it ideal for use in facial cleansers, sunscreens, and anti-aging products.
- Surfactants and Cleansers: In addition to its use in skincare, Brassylic acid is used in the formulation of biodegradable surfactants, which are essential in shampoos, body washes, and facial cleansers. These surfactants help remove dirt and oil from the skin without disrupting its natural moisture barrier.
5. Food and Flavoring Agents (Continued)
Though less commonly used in food applications compared to other fatty acids, Brassylic acid and its esters have been explored as flavoring agents in certain niche markets. Their use in food products is generally focused on enhancing specific flavor profiles or providing a unique scent.
- Flavor Enhancement: The distinct “brassy” or “fatty” odor of Brassylic acid, derived from its long aliphatic chain, is sometimes used in savory or complex flavor systems. In low concentrations, its subtle and unique flavor characteristics can be beneficial in enhancing the flavor profile of certain processed foods, sauces, or dairy products.
- Flavor Modifiers: Brassylic acid esters are sometimes used to modify flavors in beverages and snacks, especially those in the fatty, umami, or “cheese-like” flavor categories. Its fatty and complex flavor notes can help in producing more nuanced or rounded flavor blends in processed foods, especially in plant-based food formulations that aim to mimic the taste and texture of traditional animal-derived products.
6. Pharmaceutical Applications
Tridecanedioic acid is gaining interest in the pharmaceutical industry, particularly as an intermediate for the synthesis of active pharmaceutical ingredients (APIs) and as a platform for drug delivery systems.
- Pharmaceutical Synthesis: The carboxyl groups in Brassylic acid make it a versatile intermediate for synthesizing pharmaceutical compounds, including esters and amides. Through selective esterification or amidation, derivatives of Brassylic acid can be utilized in the development of specialized drug formulations, particularly those requiring controlled release or unique solubility characteristics.
- Drug Delivery Systems: Brassylic acid’s ability to form stable salts or complexes with active compounds makes it an attractive candidate for drug delivery applications. For instance, it can be used to modify the solubility and release profiles of certain drugs, ensuring more efficient absorption and targeted delivery in the body. Research into the potential of Brassylic acid in nanoparticle or liposomal formulations is ongoing, as it may offer advantages in controlled drug release mechanisms.
- Biosynthesis and Medicinal Chemistry: The bio-based production of Brassylic acid provides a renewable and sustainable source of compounds for pharmaceutical synthesis. Its use in green chemistry processes aligns with the growing demand for environmentally friendly and bio-compatible materials in medicinal chemistry.
7. Research and Development in Green Chemistry
As sustainability and environmental concerns become more prominent, the use of Brassylic acid in green chemistry applications is a significant area of development. Researchers are exploring its potential as a building block for bio-based materials and chemicals.
- Biodegradable Polymers: One of the most exciting areas of research for Brassylic acid is its use in the production of biodegradable polymers. With increasing concerns about plastic waste and the environmental impact of petroleum-based plastics, bio-based polymers derived from renewable resources are gaining traction. Brassylic acid, as a dicarboxylic acid, can be polymerized with various alcohols or diamines to create biodegradable polyesters and polyamides. These bio-based materials could replace conventional plastics in applications such as packaging, textiles, and agricultural films.
- Sustainable Coatings and Adhesives: Brassylic acid is also being studied as a precursor for the synthesis of bio-based coatings and adhesives. These products, derived from renewable sources, would reduce the environmental impact of synthetic coatings and adhesives used in construction, automotive, and electronics industries. Bio-based coatings derived from Brassylic acid could offer advantages in terms of sustainability, biodegradability, and lower toxicity compared to their conventional counterparts.
- Bio-based Surfactants and Emulsifiers: Another potential application of Brassylic acid in green chemistry is in the production of surfactants and emulsifiers. These compounds are commonly used in detergents, cleaning agents, and personal care products. Bio-based surfactants, made from renewable raw materials like Brassylic acid, can help reduce reliance on petrochemical-based ingredients and improve the environmental footprint of these products. Brassylic acid-derived surfactants have the added benefit of being biodegradable, making them a more eco-friendly alternative to traditional surfactants.
Environmental Considerations and Sustainability
One of the key advantages of Brassylic acid is its potential to be produced from renewable resources, particularly through bio-based processes. The demand for bio-based chemicals is growing, driven by increasing awareness of the environmental and health risks associated with petrochemical-derived products.
- Carbon Footprint: Traditional methods of producing chemicals and polymers often rely on fossil fuels, contributing to greenhouse gas emissions and environmental degradation. However, bio-based production methods for Brassylic acid—whether through fermentation or other green chemistry approaches—offer the potential to significantly reduce the carbon footprint of these products. By sourcing raw materials from renewable plant-based feedstocks, the overall environmental impact can be minimized, aligning with global efforts to combat climate change and promote sustainability.
- Biodegradability: Another environmental benefit of Brassylic acid and its derivatives is their biodegradability. Unlike many petrochemical-based products, which persist in the environment and contribute to pollution, bio-based chemicals like Brassylic acid can break down naturally over time. This makes them more sustainable for use in consumer goods, packaging materials, and agricultural products, reducing the risk of long-term environmental damage.
- Circular Economy: As the world transitions to a circular economy—where waste is minimized, and resources are reused—chemicals like Brassylic acid, derived from renewable feedstocks, can play a critical role. By enabling the production of recyclable and biodegradable products, Brassylic acid aligns with the principles of circularity, where products can be recovered, recycled, and reused in closed-loop systems.
Future Prospects
Looking ahead, the demand for Brassylic acid is expected to increase as industries shift toward more sustainable, bio-based materials. Several factors will contribute to this growth:
- Increasing Demand for Bio-Based Polymers: With the growing global emphasis on reducing plastic waste and minimizing the environmental impact of synthetic materials, bio-based polymers derived from dicarboxylic acids like Brassylic acid are likely to see a surge in demand. The development of high-performance bio-based polyamides and polyesters using Brassylic acid could help replace traditional plastics in a variety of applications, from automotive parts to packaging.
- Advancements in Bio-Manufacturing: As fermentation and other bio-manufacturing techniques become more efficient and cost-effective, the production of Brassylic acid from renewable feedstocks will likely become more widespread. This could open up new markets for the chemical, making it more accessible and reducing reliance on petrochemical-based processes.
- Development of New Applications: The versatility of Brassylic acid’s chemical structure offers opportunities for continued innovation in various industries, including pharmaceuticals, food production, and advanced materials. As researchers explore new ways to use Brassylic acid in drug delivery, coatings, and even novel biodegradable materials, its range of applications is expected to broaden.
- Government Support and Regulation: Governments around the world are increasingly incentivizing the development and use of bio-based chemicals through subsidies, tax credits, and favorable regulations. This support will further accelerate the commercialization of Brassylic acid and other sustainable chemicals, fostering a transition toward greener manufacturing practices.
Conclusion
Tridecanedioic acid, or Brassylic acid, is an important chemical compound with a range of industrial and commercial applications. Its unique molecular structure, which features two carboxyl groups attached to a long aliphatic chain, makes it a versatile building block for polymers, plasticizers, lubricants, and bio-based chemicals. The compound’s ability to undergo various chemical reactions, including esterification, reduction, and polymerization, has led to its use in a diverse array of products across sectors such as automotive, cosmetics, pharmaceuticals, and food production.
As sustainability and environmental consciousness continue to shape industrial practices, Brassylic acid’s bio-based production methods and potential for use in biodegradable materials position it as a key player in the green chemistry movement. The compound’s role in developing sustainable alternatives to petroleum-based products highlights its growing importance in modern manufacturing.
Looking to the future, Brassylic acid will likely see expanded use across an increasing number of industries, driven by the global demand for bio-based, environmentally friendly products. Through continued innovation and improved production processes, this compound will play a central role in the development of a more sustainable and circular economy, benefiting both industry and the environment.