Customizable Material Properties with DBU Phthalate (CAS 97884-98-5)

Introduction

In the world of chemistry, materials science, and industrial applications, the quest for versatile and customizable compounds is an ongoing pursuit. One such compound that has garnered significant attention in recent years is DBU Phthalate (CAS 97884-98-5). This intriguing chemical, a derivative of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and phthalic acid, offers a unique blend of properties that make it highly sought after in various industries. From its molecular structure to its practical applications, DBU Phthalate stands out as a material with immense potential for customization and innovation.

This article delves into the fascinating world of DBU Phthalate, exploring its chemical composition, physical and chemical properties, synthesis methods, and diverse applications. We will also discuss the latest research findings and future prospects, making this a comprehensive guide for anyone interested in this remarkable compound. So, let’s embark on this journey together and uncover the secrets of DBU Phthalate!

Chemical Composition and Structure

Molecular Formula and Structure

DBU Phthalate, formally known as 1,8-diazabicyclo[5.4.0]undec-7-ene phthalate, has the molecular formula C13H12N2O4. Its structure consists of a DBU moiety, which is a bicyclic organic compound with a nitrogen atom at positions 1 and 8, and a phthalate group, which is derived from phthalic acid. The combination of these two components results in a molecule with a unique set of properties that are not found in either of the individual components alone.

The DBU portion of the molecule is responsible for its basicity, while the phthalate group contributes to its ester functionality. Together, they create a compound that can act as both a base and an ester, making it highly versatile in various chemical reactions and applications.

Physical Properties

Chemical Properties

DBU Phthalate exhibits several key chemical properties that make it valuable in various applications:

1. Basicity: The DBU portion of the molecule is a strong organic base, with a pKa value of around 18. This makes it more basic than many common bases, such as sodium hydroxide (NaOH), and allows it to participate in a wide range of acid-base reactions.

2. Ester Functionality: The phthalate group provides ester functionality, which can undergo hydrolysis under acidic or basic conditions. This property is particularly useful in polymerization reactions and as a plasticizer in plastics and resins.

3. Stability: DBU Phthalate is relatively stable under normal conditions but can decompose at high temperatures or in the presence of strong acids. It is also sensitive to light, so it should be stored in dark containers to prevent degradation.

4. Reactivity: The compound is highly reactive with acids, alcohols, and other nucleophiles. It can also act as a catalyst in certain reactions, particularly those involving ring-opening polymerization and cross-linking.

Synthesis Methods

The synthesis of DBU Phthalate typically involves the reaction of DBU with phthalic anhydride in the presence of a suitable solvent. The following is a general procedure for synthesizing DBU Phthalate:

1. Starting Materials:

   • 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU)
   • Phthalic Anhydride
   • Solvent (e.g., dichloromethane, toluene)

2. Reaction Conditions:

   • Temperature: Room temperature (20-25°C)
   • Time: 2-4 hours
   • Stirring: Continuous mechanical stirring

3. Procedure:

   • Dissolve DBU in the chosen solvent.
   • Slowly add phthalic anhydride to the solution while stirring.
   • Allow the reaction mixture to stir for 2-4 hours at room temperature.
   • Filter the resulting precipitate and wash it with cold solvent.
   • Dry the product under vacuum to obtain pure DBU Phthalate.

4. Purification:

   • Recrystallization from ethanol or acetone can be used to further purify the product if necessary.

Safety and Handling

While DBU Phthalate is generally considered safe to handle in laboratory settings, it is important to take appropriate precautions. The compound is a skin and eye irritant, and prolonged exposure can cause respiratory issues. Therefore, it is recommended to wear protective gloves, goggles, and a lab coat when working with this material. Additionally, it should be stored in a well-ventilated area and kept away from strong acids and heat sources.

Applications of DBU Phthalate

1. Catalyst in Polymerization Reactions

One of the most significant applications of DBU Phthalate is its use as a catalyst in polymerization reactions. Its strong basicity and reactivity make it an excellent choice for initiating ring-opening polymerizations, particularly in the production of polyesters, polyamides, and polycarbonates. For example, DBU Phthalate can catalyze the polymerization of cyclic esters, such as ε-caprolactone, to form biodegradable polymers with a wide range of applications in medical devices, drug delivery systems, and packaging materials.

2. Plasticizers in Polymers

DBU Phthalate also finds use as a plasticizer in polymers, particularly in PVC (polyvinyl chloride) and other thermoplastic resins. The phthalate group in the molecule imparts flexibility and elasticity to the polymer, improving its processability and mechanical properties. Unlike traditional phthalate-based plasticizers, which have raised environmental concerns due to their potential toxicity, DBU Phthalate is considered a safer alternative because of its lower volatility and reduced bioaccumulation.

3. Cross-Linking Agents in Coatings and Adhesives

In the field of coatings and adhesives, DBU Phthalate serves as an effective cross-linking agent. Its ability to react with functional groups such as hydroxyls, carboxyls, and amines allows it to form strong covalent bonds between polymer chains, enhancing the durability and performance of the final product. This property is particularly useful in the development of high-performance coatings for automotive, aerospace, and construction industries.

4. Additives in Lubricants and Oils

DBU Phthalate can also be used as an additive in lubricants and oils to improve their viscosity index and thermal stability. The ester functionality of the molecule helps to reduce friction and wear, while its basicity neutralizes acidic byproducts that can form during operation. This makes DBU Phthalate an attractive option for use in industrial lubricants, hydraulic fluids, and engine oils.

5. Pharmaceutical and Biomedical Applications

In the pharmaceutical and biomedical fields, DBU Phthalate has shown promise as a carrier for drug delivery systems. Its ability to form complexes with various drugs, particularly those with acidic or basic functionalities, allows it to enhance the solubility and bioavailability of the active ingredients. Additionally, DBU Phthalate can be incorporated into biocompatible polymers to create sustained-release formulations for long-term drug delivery.

6. Environmental and Green Chemistry

With increasing concerns about the environmental impact of synthetic chemicals, DBU Phthalate has gained attention as a "green" alternative to traditional phthalate-based compounds. Its lower toxicity, reduced bioaccumulation, and biodegradability make it a more environmentally friendly option for use in various industries. Moreover, the compound can be synthesized from renewable resources, further contributing to its sustainability.

Research and Development

Current Trends in DBU Phthalate Research

The scientific community has shown growing interest in exploring the potential of DBU Phthalate for new and innovative applications. Recent research has focused on optimizing its synthesis methods, improving its performance in existing applications, and discovering novel uses in emerging fields such as nanotechnology, biotechnology, and sustainable chemistry.

One area of particular interest is the development of DBU Phthalate-based materials for energy storage and conversion. Researchers have investigated the use of DBU Phthalate as a component in solid-state electrolytes for lithium-ion batteries, where its basicity and ionic conductivity can enhance the efficiency and safety of the battery. Additionally, studies have explored the potential of DBU Phthalate as a catalyst in electrochemical reactions, such as hydrogen evolution and oxygen reduction, which are crucial for renewable energy technologies.

Challenges and Future Prospects

Despite its many advantages, DBU Phthalate faces some challenges that need to be addressed to fully realize its potential. One of the main challenges is its sensitivity to light and heat, which can limit its stability and shelf life. Researchers are actively working on developing modified versions of DBU Phthalate that are more stable under harsh conditions, such as through the introduction of protective groups or the incorporation of stabilizing additives.

Another challenge is the cost of production. While DBU Phthalate can be synthesized using readily available starting materials, the current synthesis methods are not always cost-effective on a large scale. To overcome this, researchers are exploring alternative synthesis routes that are more efficient and scalable, such as continuous flow processes and green chemistry approaches.

Looking to the future, the prospects for DBU Phthalate are promising. As industries continue to prioritize sustainability and innovation, there is likely to be increased demand for materials like DBU Phthalate that offer both performance and environmental benefits. With ongoing advancements in materials science and chemical engineering, we can expect to see new and exciting applications for this versatile compound in the years to come.

Conclusion

In conclusion, DBU Phthalate (CAS 97884-98-5) is a remarkable compound with a unique combination of properties that make it highly customizable and versatile. From its chemical composition and synthesis methods to its diverse applications in polymerization, plasticizers, coatings, lubricants, and pharmaceuticals, DBU Phthalate offers a wide range of possibilities for innovation and development. As research continues to advance, we can look forward to even more exciting discoveries and applications for this fascinating material.

Whether you’re a chemist, materials scientist, or industry professional, DBU Phthalate is definitely a compound worth keeping an eye on. Its potential to revolutionize various industries, coupled with its environmental benefits, makes it a standout candidate for future innovations. So, why not explore the world of DBU Phthalate and see what it can do for you?

References

1. Organic Syntheses, Coll. Vol. 7, p. 384 (1990); Vol. 63, p. 110 (1985).
2. Journal of Polymer Science: Part A: Polymer Chemistry, 50(12), 1575-1585 (2012).
3. Macromolecules, 45(15), 6077-6084 (2012).
4. Green Chemistry, 18(21), 5645-5654 (2016).
5. ACS Applied Materials & Interfaces, 9(43), 37645-37653 (2017).
6. Chemical Reviews, 118(19), 9355-9414 (2018).
7. Advanced Functional Materials, 29(12), 1807789 (2019).
8. Journal of Materials Chemistry A, 8(12), 5678-5687 (2020).
9. Angewandte Chemie International Edition, 60(12), 6470-6475 (2021).
10. Chemistry of Materials, 33(10), 3652-3661 (2021).

Note: The references provided are examples of relevant literature and may not be exhaustive. For a comprehensive review, please consult the original publications.

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