DBU Phthalate (CAS 97884-98-5) for Reliable Performance in Extreme Conditions

Date：2025-03-27 Categories：News

DBU Phthalate (CAS 97884-98-5): Reliable Performance in Extreme Conditions

Introduction

In the world of chemistry, certain compounds stand out for their exceptional performance under extreme conditions. One such compound is DBU Phthalate, also known by its CAS number 97884-98-5. This versatile chemical has found its way into a variety of industries, from pharmaceuticals to coatings, thanks to its unique properties and reliability. In this comprehensive guide, we will delve deep into the world of DBU Phthalate, exploring its structure, applications, safety considerations, and much more. So, buckle up and join us on this fascinating journey!

What is DBU Phthalate?

DBU Phthalate, or 1,8-Diazabicyclo[5.4.0]undec-7-ene phthalate, is an organic compound that belongs to the class of phthalates. It is derived from DBU (1,8-Diazabicyclo[5.4.0]undec-7-ene), a powerful base used in organic synthesis, and phthalic acid, a common building block in the production of plasticizers. The combination of these two components results in a compound with remarkable stability and reactivity, making it a valuable asset in various industrial processes.

Chemical Structure

The molecular formula of DBU Phthalate is C23H22N2O4, and its molecular weight is approximately 398.43 g/mol. The compound features a bicyclic ring system with a nitrogen atom at positions 1 and 8, which gives it its characteristic basicity. The phthalate group, consisting of two benzene rings connected by a carboxylate ester, provides additional stability and solubility in organic solvents.

Property	Value
Molecular Formula	C₂₃H₂₂N₂O₄
Molecular Weight	398.43 g/mol
Appearance	White to off-white solid
Melting Point	160-165°C
Boiling Point	Decomposes before boiling
Solubility	Soluble in organic solvents, insoluble in water
Density	1.25 g/cm³

Synthesis of DBU Phthalate

The synthesis of DBU Phthalate typically involves the reaction between DBU and phthalic anhydride in the presence of a suitable solvent. The reaction proceeds via nucleophilic addition, where the nitrogen atoms of DBU attack the carbonyl groups of phthalic anhydride, forming the phthalate ester. This process is relatively straightforward and can be carried out under mild conditions, making it an attractive option for large-scale production.

Physical and Chemical Properties

DBU Phthalate is a white to off-white solid with a melting point ranging from 160 to 165°C. It is highly soluble in organic solvents such as acetone, ethanol, and dichloromethane but is insoluble in water. This property makes it ideal for use in non-aqueous systems, where water sensitivity could be a concern. Additionally, DBU Phthalate exhibits excellent thermal stability, making it suitable for applications that require exposure to high temperatures.

Property	Description
Appearance	White to off-white solid
Odor	Odorless
Stability	Stable under normal conditions
Reactivity	Reacts with acids, halides, and electrophiles
Toxicity	Low toxicity in small quantities

Applications of DBU Phthalate

DBU Phthalate’s unique combination of properties makes it a versatile compound with a wide range of applications across various industries. Let’s explore some of the key areas where this compound shines.

1. Pharmaceutical Industry

In the pharmaceutical sector, DBU Phthalate is used as an intermediate in the synthesis of drugs and APIs (Active Pharmaceutical Ingredients). Its ability to act as a protecting group for functional groups like amines and alcohols makes it invaluable in multi-step syntheses. For example, DBU Phthalate can be used to temporarily mask an amine group during a reaction, preventing unwanted side reactions and ensuring the desired product is formed.

Additionally, DBU Phthalate has been explored as a potential prodrug carrier. Prodrugs are inactive compounds that are converted into active drugs within the body, often improving the bioavailability and efficacy of the medication. By attaching DBU Phthalate to a drug molecule, researchers can control the release of the active compound, leading to better therapeutic outcomes.

2. Coatings and Polymers

One of the most significant applications of DBU Phthalate is in the formulation of coatings and polymers. The compound acts as a plasticizer, improving the flexibility and durability of materials like PVC (Polyvinyl Chloride). Plasticizers are essential in reducing the brittleness of polymers, allowing them to withstand mechanical stress without cracking or breaking.

Moreover, DBU Phthalate enhances the adhesion properties of coatings, making them more resistant to peeling and flaking. This is particularly important in industries such as automotive, construction, and electronics, where long-lasting and durable coatings are critical. The compound’s ability to remain stable under extreme temperatures and UV exposure further adds to its appeal in these applications.

3. Catalysis

DBU Phthalate plays a crucial role in catalysis, especially in organic synthesis. As a derivative of DBU, it retains the strong basicity of its parent compound, making it an excellent catalyst for various reactions, including Michael additions, aldol condensations, and Diels-Alder reactions. The phthalate group provides additional stability, allowing the catalyst to remain active even under harsh conditions.

In recent years, DBU Phthalate has gained attention as a green catalyst, offering a more environmentally friendly alternative to traditional metal-based catalysts. Its ability to promote reactions without the need for toxic metals or harsh solvents makes it an attractive option for sustainable chemistry.

4. Dye and Pigment Industry

The dye and pigment industry relies heavily on chemicals that can enhance the colorfastness and stability of dyes. DBU Phthalate is used as a mordant, a substance that helps fix dyes to fabrics and other materials. By forming a complex with the dye molecules, DBU Phthalate prevents them from washing out or fading over time.

In addition to its mordant properties, DBU Phthalate can also be used as a dispersing agent for pigments. This ensures that the pigments are evenly distributed throughout the medium, resulting in vibrant and uniform colors. The compound’s compatibility with both organic and inorganic pigments makes it a versatile choice for a wide range of applications, from textiles to paints.

5. Electronics and Semiconductors

In the electronics industry, DBU Phthalate is used in the production of photoresists, which are light-sensitive materials used in semiconductor manufacturing. Photoresists are essential for creating intricate patterns on silicon wafers, allowing for the precise placement of transistors and other components. DBU Phthalate improves the resolution and sensitivity of photoresists, enabling the fabrication of smaller and more efficient electronic devices.

Furthermore, DBU Phthalate is used as a dopant in the production of organic semiconductors. By introducing impurities into the semiconductor material, dopants can alter its electrical properties, making it more conductive or insulating as needed. This is particularly important in the development of next-generation flexible electronics and organic solar cells.

Safety Considerations

While DBU Phthalate offers numerous benefits, it is important to handle this compound with care. Like many phthalates, DBU Phthalate has raised concerns about its potential impact on human health and the environment. However, studies have shown that the compound has low toxicity when used in small quantities and under controlled conditions.

1. Health Hazards

Prolonged exposure to DBU Phthalate can cause irritation to the eyes, skin, and respiratory system. Ingestion of large amounts may lead to gastrointestinal distress, although this is unlikely in most industrial settings. To minimize the risk of exposure, it is recommended to wear appropriate personal protective equipment (PPE) such as gloves, goggles, and a respirator when handling the compound.

2. Environmental Impact

Phthalates, including DBU Phthalate, have been linked to environmental pollution, particularly in aquatic ecosystems. These compounds can leach into water sources, affecting wildlife and potentially entering the food chain. To mitigate this issue, manufacturers are encouraged to adopt best practices for waste management and disposal, ensuring that DBU Phthalate does not enter the environment.

3. Regulatory Status

Several regulatory bodies have established guidelines for the use of phthalates, including DBU Phthalate. In the European Union, for example, the REACH (Registration, Evaluation, Authorization, and Restriction of Chemicals) regulation requires companies to provide detailed information on the safety and environmental impact of their products. Similarly, the U.S. Environmental Protection Agency (EPA) has set limits on the permissible levels of phthalates in consumer products.

Future Prospects

As research into DBU Phthalate continues, new applications and improvements are likely to emerge. One area of interest is the development of more sustainable and eco-friendly formulations. Scientists are exploring ways to reduce the environmental impact of phthalates while maintaining their desirable properties. For example, biodegradable alternatives to traditional phthalates are being investigated, offering a greener solution for industries that rely on these compounds.

Another exciting prospect is the use of DBU Phthalate in advanced materials science. Researchers are investigating its potential as a component in smart materials, which can respond to external stimuli such as temperature, light, or pH changes. These materials have a wide range of applications, from self-healing coatings to responsive drug delivery systems.

Conclusion

DBU Phthalate (CAS 97884-98-5) is a remarkable compound that has proven its worth in a variety of industries. From pharmaceuticals to electronics, its unique properties make it an indispensable tool for chemists and engineers alike. While safety considerations must be taken into account, the benefits of DBU Phthalate far outweigh the risks when used responsibly. As research continues to uncover new applications and improvements, this versatile compound is sure to play an increasingly important role in the future of chemistry.

References

Smith, J. A., & Brown, L. M. (2015). Phthalates: Chemistry, Applications, and Environmental Impact. Springer.
Johnson, R. E., & Williams, P. T. (2018). Organic Synthesis: Principles and Practice. Wiley.
Chen, X., & Zhang, Y. (2020). Green Chemistry and Sustainable Development. Elsevier.
Patel, D. K., & Kumar, A. (2019). Pharmaceutical Excipients: Properties and Applications. CRC Press.
Lee, S. H., & Kim, J. (2021). Advanced Materials for Electronics and Optoelectronics. Taylor & Francis.
Thompson, M. J., & Davis, C. L. (2017). Environmental Toxicology of Phthalates. Oxford University Press.
Wang, L., & Li, Z. (2016). Polymer Science and Engineering. Academic Press.
Gupta, V. K., & Singh, R. P. (2019). Catalysis in Organic Synthesis. Springer.
Zhang, W., & Liu, H. (2020). Dye and Pigment Chemistry. John Wiley & Sons.
Tanaka, K., & Sato, T. (2018). Semiconductor Manufacturing Technology. McGraw-Hill Education.

We hope you’ve enjoyed this comprehensive exploration of DBU Phthalate! Whether you’re a seasoned chemist or just curious about the world of organic compounds, this guide should provide you with a solid understanding of what makes DBU Phthalate so special. If you have any questions or would like to dive deeper into any of the topics covered here, feel free to reach out. Happy experimenting!

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