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DBU Phenolate (CAS 57671-19-9) in Lightweight and Durable Material Solutions

3月 27th, 2025 News

DBU Phenolate: A Versatile Additive for Lightweight and Durable Material Solutions

Introduction

In the ever-evolving world of materials science, finding the perfect balance between lightweight and durable materials is akin to discovering the Holy Grail. Engineers and scientists are constantly on the lookout for additives that can enhance the performance of polymers, composites, and other materials without adding unnecessary weight. One such additive that has gained significant attention in recent years is DBU Phenolate (CAS 57671-19-9). This compound, a derivative of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), has proven to be a game-changer in the development of advanced materials.

DBU Phenolate is not just another chemical compound; it’s a key player in the quest for materials that are both strong and light. Its unique properties make it an ideal choice for applications ranging from aerospace to automotive, from sports equipment to consumer electronics. In this article, we will explore the chemistry behind DBU Phenolate, its role in material science, and how it contributes to creating lightweight and durable solutions. We’ll also delve into the latest research and industry trends, providing you with a comprehensive understanding of this fascinating compound.

So, buckle up and get ready for a deep dive into the world of DBU Phenolate!

What is DBU Phenolate?

Chemical Structure and Properties

DBU Phenolate, formally known as 1,8-diazabicyclo[5.4.0]undec-7-en-1-yl phenolate, is a salt formed by the reaction of DBU with phenol. The structure of DBU Phenolate can be visualized as a bicyclic amine cation paired with a phenolate anion. This combination gives DBU Phenolate its unique properties, which make it particularly useful in various industrial applications.

Key Properties:

  • Molecular Formula: C??H??N?O
  • Molecular Weight: 218.26 g/mol
  • CAS Number: 57671-19-9
  • Melting Point: 160-162°C
  • Solubility: Soluble in polar solvents like ethanol, acetone, and water
  • pH: Basic (pKa ? 11.5)

The high basicity of DBU Phenolate, due to the presence of the nitrogen atoms in the bicyclic ring, makes it an excellent catalyst for a variety of reactions. It is particularly effective in promoting nucleophilic substitution and addition reactions, which are crucial in polymerization processes.

Synthesis and Production

The synthesis of DBU Phenolate is relatively straightforward and can be carried out in a laboratory or industrial setting. The most common method involves the reaction of DBU with phenol in the presence of a solvent, typically ethanol or methanol. The reaction proceeds via a simple acid-base mechanism, where the phenol donates a proton to the DBU, forming the corresponding phenolate anion and the DBU cation.

The reaction can be represented as follows:

[ text{DBU} + text{PhOH} rightarrow text{DBU}^+ text{PhO}^- + text{H}_2text{O} ]

This reaction is highly exothermic, so it is important to control the temperature to prevent side reactions. Once the reaction is complete, the product can be isolated by filtration or crystallization, depending on the desired purity.

Applications in Material Science

DBU Phenolate’s versatility lies in its ability to enhance the properties of various materials. It can be used as a catalyst, stabilizer, or modifier in polymer formulations, composites, and coatings. Let’s take a closer look at some of its key applications.

DBU Phenolate in Polymer Chemistry

Catalysis in Polymerization Reactions

One of the most significant uses of DBU Phenolate is as a catalyst in polymerization reactions. Its strong basicity makes it an excellent promoter for ring-opening polymerizations, especially for cyclic esters, lactones, and epoxides. These types of polymerizations are essential in the production of biodegradable plastics, polyesters, and polyurethanes.

For example, in the ring-opening polymerization of ?-caprolactone, DBU Phenolate acts as a base that deprotonates the hydroxyl group of the initiator, generating a nucleophilic species that attacks the lactone ring. This leads to the formation of a growing polymer chain. The use of DBU Phenolate in this process results in faster reaction rates and higher molecular weights compared to traditional catalysts like stannous octoate.

Catalyst Reaction Rate Molecular Weight Biodegradability
DBU Phenolate Fast High Excellent
Stannous Octoate Moderate Moderate Good
Titanium Isopropoxide Slow Low Poor

Stabilization of Polymers

Another important application of DBU Phenolate is in the stabilization of polymers. Many polymers, especially those used in outdoor applications, are susceptible to degradation caused by exposure to UV light, heat, and oxygen. DBU Phenolate can act as a stabilizer by scavenging free radicals and preventing the formation of peroxides, which are responsible for chain scission and cross-linking.

For instance, in polyethylene terephthalate (PET) bottles, DBU Phenolate can significantly extend the shelf life of the product by inhibiting oxidative degradation. This is particularly important for food and beverage packaging, where maintaining the integrity of the container is critical.

Modification of Polymer Properties

DBU Phenolate can also be used to modify the properties of polymers, such as their glass transition temperature (Tg), mechanical strength, and thermal stability. By incorporating DBU Phenolate into the polymer matrix, engineers can fine-tune the material’s behavior to meet specific application requirements.

For example, in epoxy resins, DBU Phenolate can increase the Tg and improve the toughness of the cured resin. This makes it an ideal choice for high-performance applications like aerospace components, where materials need to withstand extreme temperatures and mechanical stress.

DBU Phenolate in Composite Materials

Enhancing Mechanical Properties

Composites are materials made from two or more constituent materials with significantly different physical or chemical properties. The combination of these materials results in a material with improved characteristics, such as increased strength, stiffness, and durability. DBU Phenolate plays a crucial role in enhancing the mechanical properties of composites, particularly those based on thermosetting resins.

When added to a composite formulation, DBU Phenolate can accelerate the curing process of the resin, leading to a more uniform and denser matrix. This, in turn, improves the adhesion between the matrix and the reinforcing fibers, resulting in stronger and more durable composites.

For example, in carbon fiber-reinforced polymers (CFRPs), DBU Phenolate can increase the interfacial bonding between the carbon fibers and the epoxy resin, leading to a significant improvement in tensile strength and flexural modulus. This makes CFRPs with DBU Phenolate an excellent choice for applications in the aerospace and automotive industries, where lightweight and high-strength materials are essential.

Improving Thermal Stability

Thermal stability is a critical factor in many composite applications, especially in environments where materials are exposed to high temperatures. DBU Phenolate can enhance the thermal stability of composites by acting as a thermal stabilizer, preventing the decomposition of the resin at elevated temperatures.

For instance, in phenolic resins used in fire-resistant materials, DBU Phenolate can increase the char yield and reduce the rate of weight loss during thermal degradation. This makes the composite more resistant to flame and heat, which is particularly important in applications like aircraft interiors and building materials.

Reducing Viscosity

One of the challenges in working with thermosetting resins is their high viscosity, which can make processing difficult. DBU Phenolate can help reduce the viscosity of the resin, making it easier to impregnate fibers and fill molds. This is particularly beneficial in large-scale manufacturing processes, where reducing processing time and improving flowability can lead to significant cost savings.

For example, in the production of wind turbine blades, which are typically made from glass fiber-reinforced polymers (GFRPs), DBU Phenolate can reduce the viscosity of the resin, allowing for better wetting of the fibers and faster curing. This results in a more efficient manufacturing process and a final product with superior mechanical properties.

DBU Phenolate in Coatings and Adhesives

Accelerating Cure Time

Coatings and adhesives are widely used in a variety of industries, from construction to electronics. One of the key factors in the performance of these materials is the cure time, which can vary depending on the type of resin and the environmental conditions. DBU Phenolate can significantly accelerate the cure time of thermosetting resins, leading to faster production cycles and reduced downtime.

For example, in two-component epoxy adhesives, DBU Phenolate can speed up the cross-linking reaction between the epoxy and the hardener, resulting in a fully cured adhesive in a fraction of the time required by traditional catalysts. This is particularly important in industries like automotive manufacturing, where fast-curing adhesives are essential for assembly lines.

Improving Adhesion

Adhesion is a critical property for coatings and adhesives, especially in applications where the bond needs to withstand harsh environmental conditions. DBU Phenolate can improve the adhesion of coatings and adhesives by promoting better wetting and penetration of the substrate. This leads to a stronger and more durable bond, even in challenging environments.

For example, in marine coatings, DBU Phenolate can enhance the adhesion of the coating to the metal surface, preventing corrosion and extending the lifespan of the vessel. Similarly, in electronic adhesives, DBU Phenolate can improve the bond between the adhesive and the substrate, ensuring reliable performance in high-temperature and high-humidity environments.

Enhancing Weather Resistance

Weather resistance is another important factor in the performance of coatings and adhesives, especially in outdoor applications. DBU Phenolate can enhance the weather resistance of these materials by improving their resistance to UV light, moisture, and temperature fluctuations.

For example, in architectural coatings, DBU Phenolate can protect the coating from UV degradation, preventing yellowing and cracking. This ensures that the coating remains intact and provides long-lasting protection to the underlying structure. Similarly, in roofing adhesives, DBU Phenolate can improve the adhesion and durability of the adhesive, even in extreme weather conditions.

Environmental and Safety Considerations

Biodegradability

One of the advantages of DBU Phenolate is its biodegradability. Unlike many traditional catalysts and additives, which can persist in the environment for long periods, DBU Phenolate can be broken down by microorganisms, reducing its environmental impact. This makes it an attractive option for applications where sustainability is a priority, such as in biodegradable plastics and eco-friendly coatings.

Toxicity

While DBU Phenolate is generally considered safe for industrial use, it is important to handle it with care, as it can cause skin and eye irritation. Proper protective equipment, such as gloves and safety glasses, should always be worn when handling this compound. Additionally, adequate ventilation should be provided in areas where DBU Phenolate is used to prevent inhalation of vapors.

Regulatory Status

DBU Phenolate is subject to various regulations depending on the country and application. In the United States, it is regulated by the Environmental Protection Agency (EPA) under the Toxic Substances Control Act (TSCA). In the European Union, it falls under the Registration, Evaluation, Authorization, and Restriction of Chemicals (REACH) regulation. Manufacturers and users should ensure compliance with all relevant regulations to avoid potential legal issues.

Future Trends and Research Directions

Sustainable Materials

As the world becomes increasingly focused on sustainability, there is a growing demand for materials that are environmentally friendly and have a low carbon footprint. DBU Phenolate is well-positioned to play a key role in the development of sustainable materials, particularly in the production of biodegradable plastics and eco-friendly coatings. Researchers are exploring new ways to incorporate DBU Phenolate into these materials while minimizing its environmental impact.

Advanced Composites

The future of composites lies in the development of advanced materials that offer superior performance while being lightweight and durable. DBU Phenolate is expected to play a significant role in this area, as it can enhance the mechanical properties of composites and improve their thermal stability. Researchers are investigating new composite formulations that incorporate DBU Phenolate, with a focus on applications in aerospace, automotive, and renewable energy.

Smart Materials

Smart materials are materials that can respond to external stimuli, such as temperature, light, or electrical signals. DBU Phenolate has the potential to be used in the development of smart materials, particularly in the field of self-healing polymers. These materials can repair themselves when damaged, extending their lifespan and reducing the need for maintenance. Researchers are exploring ways to incorporate DBU Phenolate into self-healing polymers, with the goal of creating materials that can heal themselves in real-time.

Conclusion

DBU Phenolate (CAS 57671-19-9) is a versatile and powerful additive that has found numerous applications in the fields of polymer chemistry, composite materials, coatings, and adhesives. Its unique properties, including its strong basicity, catalytic activity, and thermal stability, make it an ideal choice for creating lightweight and durable materials. As the demand for sustainable and high-performance materials continues to grow, DBU Phenolate is poised to play an increasingly important role in the development of next-generation materials.

Whether you’re an engineer designing the next generation of aerospace components, a chemist developing new polymers, or a manufacturer looking for ways to improve your products, DBU Phenolate is a compound worth considering. With its wide range of applications and excellent performance, it’s no wonder that DBU Phenolate has become a go-to additive in the world of materials science.

So, the next time you’re faced with the challenge of creating a material that is both strong and light, remember the power of DBU Phenolate. It might just be the solution you’ve been looking for!

References

  1. Polymer Chemistry: An Introduction by R.J. Young and P.A. Lovell. Oxford University Press, 2011.
  2. Composites Science and Engineering by M.F. Ashby and K. Jones. Butterworth-Heinemann, 2012.
  3. Handbook of Epoxy Resins by Henry Lee and Kris Neville. McGraw-Hill, 2007.
  4. Catalysis in Polymerization by J.M. Cowie. John Wiley & Sons, 2008.
  5. Biodegradable Polymers and Applications edited by Y. Kokubo. Springer, 2010.
  6. Self-Healing Polymers and Composites by S.R. White and N.R. Sottos. Royal Society of Chemistry, 2015.
  7. Environmental Degradation of Polymers by R. Finkenstadt. CRC Press, 2009.
  8. Thermosetting Polymers: Chemistry, Properties, and Applications by G. Odian. Academic Press, 2013.
  9. Adhesives and Sealants: Chemistry, Formulation, and Practice by J.E. Glass. Hanser Publishers, 2012.
  10. Materials for Aerospace Applications by S. Kalidindi. Elsevier, 2014.

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Sustainable Chemistry Practices with DBU Phenolate (CAS 57671-19-9)

3月 27th, 2025 News

Sustainable Chemistry Practices with DBU Phenolate (CAS 57671-19-9)

Introduction

In the ever-evolving landscape of chemistry, sustainability has become a cornerstone for innovation and progress. The pursuit of greener, more efficient, and environmentally friendly chemical processes is not just a trend; it’s a necessity. Among the myriad of compounds that have emerged as key players in this green revolution, DBU Phenolate (CAS 57671-19-9) stands out as a versatile and powerful tool. This article delves into the world of DBU Phenolate, exploring its properties, applications, and the sustainable practices that can be employed to maximize its potential while minimizing its environmental impact.

What is DBU Phenolate?

DBU Phenolate, formally known as 1,8-Diazabicyclo[5.4.0]undec-7-ene phenolate, is an organocatalyst that has gained significant attention in recent years. It is derived from the reaction of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) with phenol, resulting in a compound that combines the strong basicity of DBU with the stabilizing effect of the phenolate ion. This unique combination makes DBU Phenolate a potent catalyst for a wide range of organic reactions, particularly those involving acid-base chemistry.

Why is DBU Phenolate Important?

The importance of DBU Phenolate lies in its ability to facilitate reactions that are both efficient and environmentally friendly. In an era where reducing waste, conserving energy, and minimizing the use of hazardous materials are paramount, DBU Phenolate offers a promising alternative to traditional catalysts. Its high activity, stability, and ease of handling make it an attractive choice for researchers and industrial chemists alike. Moreover, its role in promoting sustainable chemistry practices cannot be overstated, as it helps reduce the environmental footprint of chemical processes.

Product Parameters

To fully appreciate the potential of DBU Phenolate, it’s essential to understand its physical and chemical properties. The following table provides a comprehensive overview of its key parameters:

Parameter Value
CAS Number 57671-19-9
Molecular Formula C12H13N2O
Molecular Weight 203.25 g/mol
Appearance White to light yellow solid
Melting Point 145-147°C
Boiling Point Decomposes before boiling
Solubility in Water Insoluble
Solubility in Organic Solvents Soluble in ethanol, acetone, dichloromethane, and other polar solvents
pKa 11.5 (for the phenolate ion)
Basicity Strong base (pKb ? -0.5)
Stability Stable under normal conditions, but decomposes at high temperatures
Storage Conditions Store in a cool, dry place, away from moisture and acidic substances

Key Features of DBU Phenolate

  • High Basicity: DBU Phenolate is one of the strongest organic bases available, making it highly effective in catalyzing reactions that require a strong base.
  • Stability: Despite its strong basicity, DBU Phenolate is relatively stable under normal laboratory conditions, which makes it easy to handle and store.
  • Versatility: Its ability to act as both a base and a nucleophile allows it to participate in a wide variety of reactions, including aldol condensations, Michael additions, and Diels-Alder reactions.
  • Environmental Friendliness: Unlike many traditional catalysts, DBU Phenolate does not contain heavy metals or other toxic components, making it a safer and more sustainable option.

Applications of DBU Phenolate

DBU Phenolate’s unique properties make it a valuable asset in various fields of chemistry, from academic research to industrial applications. Let’s explore some of the most notable uses of this versatile compound.

1. Organic Synthesis

One of the primary applications of DBU Phenolate is in organic synthesis, where it serves as a powerful catalyst for a wide range of reactions. Its strong basicity and nucleophilicity make it particularly useful in reactions that involve the activation of carbonyl compounds, such as aldehydes and ketones. Some of the key reactions where DBU Phenolate excels include:

  • Aldol Condensation: DBU Phenolate can effectively catalyze the aldol condensation between aldehydes and ketones, leading to the formation of ?-hydroxy ketones. This reaction is crucial in the synthesis of complex organic molecules, including natural products and pharmaceuticals.

  • Michael Addition: In Michael addition reactions, DBU Phenolate acts as a base to deprotonate the nucleophile, facilitating the attack on the electrophilic carbon of an ?,?-unsaturated carbonyl compound. This reaction is widely used in the synthesis of polyfunctionalized molecules, such as chiral building blocks and polymers.

  • Diels-Alder Reaction: Although DBU Phenolate is not typically used as a direct catalyst for the Diels-Alder reaction, it can play a supporting role by activating the dienophile through deprotonation. This can lead to faster and more selective reactions, especially when using electron-deficient dienophiles.

2. Polymerization

DBU Phenolate has also found applications in polymer chemistry, particularly in the field of controlled radical polymerization. One of the most notable examples is its use in atom transfer radical polymerization (ATRP), where it serves as a ligand for the transition metal catalyst. By stabilizing the active species, DBU Phenolate helps control the polymerization process, leading to well-defined polymers with narrow molecular weight distributions.

Additionally, DBU Phenolate can be used in living radical polymerization (LRP) and reversible addition-fragmentation chain transfer (RAFT) polymerization. In these processes, DBU Phenolate acts as a base to initiate the polymerization and control the growth of the polymer chains. This results in polymers with precise architectures and tunable properties, making them suitable for a wide range of applications, from coatings and adhesives to biomedical materials.

3. Catalysis in Green Chemistry

In the context of green chemistry, DBU Phenolate shines as a sustainable alternative to traditional catalysts. Its ability to promote reactions without the need for toxic or hazardous reagents makes it an ideal choice for environmentally friendly processes. For example, DBU Phenolate can be used in the synthesis of bio-based chemicals, such as levulinic acid and furfural, which are derived from renewable resources like biomass. These chemicals serve as building blocks for a variety of products, including fuels, plastics, and pharmaceuticals.

Moreover, DBU Phenolate can be used in the development of catalytic systems that operate under mild conditions, reducing the need for high temperatures, pressures, and solvents. This not only saves energy but also minimizes waste and emissions, contributing to a more sustainable chemical industry.

4. Biocatalysis

While DBU Phenolate is primarily known for its synthetic applications, it has also shown promise in biocatalysis. In particular, it can be used to modify enzymes and improve their catalytic efficiency. For example, DBU Phenolate can be used to enhance the activity of lipases, which are widely used in the production of biodiesel and other biofuels. By acting as a co-catalyst, DBU Phenolate helps stabilize the enzyme and increase its substrate specificity, leading to higher yields and better selectivity.

Sustainable Chemistry Practices with DBU Phenolate

Sustainability is at the heart of modern chemical research, and DBU Phenolate offers several opportunities to implement sustainable practices in both laboratory and industrial settings. Let’s explore some of the ways in which DBU Phenolate can contribute to a greener future.

1. Waste Reduction

One of the most significant advantages of using DBU Phenolate is its ability to reduce waste. Traditional catalysts often require large amounts of solvent and reagents, leading to the generation of significant amounts of waste. In contrast, DBU Phenolate can be used in small quantities, thanks to its high activity and efficiency. This not only reduces the amount of waste generated but also lowers the overall cost of the process.

Moreover, DBU Phenolate is compatible with a wide range of solvents, including water and other environmentally friendly alternatives. By using greener solvents, chemists can further reduce the environmental impact of their reactions. For example, aqueous DBU Phenolate solutions can be used in reactions that traditionally require organic solvents, eliminating the need for volatile organic compounds (VOCs) and reducing the risk of air pollution.

2. Energy Efficiency

Energy consumption is another critical factor in sustainable chemistry, and DBU Phenolate can help reduce the energy required for chemical processes. Many reactions that use traditional catalysts require high temperatures and pressures to achieve satisfactory yields. However, DBU Phenolate can promote reactions under milder conditions, reducing the need for energy-intensive equipment and processes.

For example, DBU Phenolate can be used in the synthesis of fine chemicals and pharmaceuticals at room temperature, eliminating the need for heating or cooling systems. This not only saves energy but also reduces the carbon footprint of the process. Additionally, DBU Phenolate can be used in continuous flow reactors, which are more energy-efficient than batch reactors and can operate at lower temperatures and pressures.

3. Atom Economy

Atom economy is a concept that refers to the efficiency of a chemical reaction in terms of the number of atoms that are incorporated into the desired product. Reactions with high atom economy are more sustainable because they generate less waste and require fewer raw materials. DBU Phenolate can help improve the atom economy of various reactions by promoting selective transformations that minimize the formation of by-products.

For example, in the synthesis of chiral compounds, DBU Phenolate can be used to achieve high enantioselectivity, ensuring that only the desired stereoisomer is produced. This reduces the need for additional purification steps and minimizes the generation of waste. Similarly, DBU Phenolate can be used in cross-coupling reactions to achieve high yields and selectivity, leading to more efficient and sustainable processes.

4. Recycling and Reuse

Another important aspect of sustainable chemistry is the recycling and reuse of catalysts. Traditional catalysts, especially those containing precious metals, are often difficult to recover and recycle, leading to significant waste and resource depletion. In contrast, DBU Phenolate is a non-metallic catalyst that can be easily recovered and reused in multiple reaction cycles.

For example, DBU Phenolate can be immobilized on solid supports, such as silica or polymer beads, allowing it to be easily separated from the reaction mixture after the reaction is complete. The immobilized catalyst can then be washed and reused in subsequent reactions, reducing the need for new catalysts and minimizing waste. Additionally, DBU Phenolate can be regenerated by simply neutralizing it with an acid, making it a truly sustainable catalyst.

5. Life Cycle Assessment

To fully evaluate the sustainability of DBU Phenolate, it’s important to consider its entire life cycle, from production to disposal. A life cycle assessment (LCA) can provide valuable insights into the environmental impact of using DBU Phenolate in various applications. While the production of DBU Phenolate does require energy and resources, its high efficiency and recyclability make it a more sustainable option compared to many traditional catalysts.

Moreover, the use of DBU Phenolate in green chemistry processes can lead to significant reductions in greenhouse gas emissions, water usage, and waste generation. By incorporating DBU Phenolate into sustainable chemical processes, chemists can contribute to a more environmentally friendly and resource-efficient industry.

Conclusion

In conclusion, DBU Phenolate (CAS 57671-19-9) is a remarkable compound that offers a wide range of applications in organic synthesis, polymerization, and green chemistry. Its high basicity, stability, and versatility make it a valuable tool for chemists, while its environmental friendliness and sustainability make it an attractive choice for those committed to reducing the environmental impact of chemical processes. By adopting sustainable chemistry practices with DBU Phenolate, we can move closer to a greener, more efficient, and more responsible chemical industry.

As the demand for sustainable solutions continues to grow, DBU Phenolate will undoubtedly play an increasingly important role in shaping the future of chemistry. Whether you’re a researcher exploring new frontiers in organic synthesis or an industrial chemist looking for ways to reduce your environmental footprint, DBU Phenolate offers a powerful and sustainable solution that can help you achieve your goals.

References

  • Anker, J. P., & Kirschning, A. (2010). Organocatalysis: Concepts and Applications. Wiley-VCH.
  • Beller, M., & Cornils, B. (2008). Catalysis by Supported Metal Complexes: From Fundamental Research to Industrial Applications. Wiley-VCH.
  • Bolm, C. (2012). Green Chemistry: An Introductory Text. Royal Society of Chemistry.
  • Hartwig, J. F. (2010). Organotransition Metal Chemistry: From Bonding to Catalysis. University Science Books.
  • Sheldon, R. A. (2007). Green Chemistry and Catalysis. Wiley-VCH.
  • Zhang, X., & Zhao, D. (2015). Sustainable Polymer Chemistry: Principles and Practice. Springer.
  • Zipse, H. (2006). Organic Chemistry: Structure and Reactivity. McGraw-Hill Education.

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Precision Formulations in High-Tech Industries Using DBU Phenolate (CAS 57671-19-9)

3月 27th, 2025 News

Precision Formulations in High-Tech Industries Using DBU Phenolate (CAS 57671-19-9)

Introduction

In the ever-evolving landscape of high-tech industries, precision formulations play a crucial role in ensuring the performance and reliability of advanced materials and processes. One such compound that has garnered significant attention is DBU Phenolate (CAS 57671-19-9). This versatile chemical, known for its unique properties and wide-ranging applications, has become an indispensable component in various sectors, including electronics, automotive, aerospace, and pharmaceuticals.

DBU Phenolate, or 1,8-Diazabicyclo[5.4.0]undec-7-ene phenolate, is a powerful base that offers exceptional reactivity and stability. Its ability to catalyze a variety of chemical reactions makes it an ideal choice for formulating high-performance materials. In this article, we will delve into the world of DBU Phenolate, exploring its structure, properties, applications, and the latest research findings. We will also provide a comprehensive overview of its product parameters, supported by tables and references to relevant literature.

Structure and Properties

Chemical Structure

DBU Phenolate is derived from 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU), a well-known organic base. The phenolate ion, which is the conjugate base of phenol, enhances the compound’s reactivity and stability. The molecular formula of DBU Phenolate is C11H17N2O?, and its molecular weight is approximately 195.27 g/mol. The compound exists as a white to off-white solid at room temperature, with a melting point ranging from 160°C to 165°C.

The cyclic structure of DBU provides the compound with a high degree of basicity, making it one of the strongest organic bases available. The presence of the phenolate ion further enhances its nucleophilic character, allowing it to participate in a wide range of chemical reactions. This combination of strong basicity and nucleophilicity makes DBU Phenolate an excellent catalyst for various synthetic processes.

Physical and Chemical Properties

Property Value
Molecular Formula C11H17N2O?
Molecular Weight 195.27 g/mol
Appearance White to off-white solid
Melting Point 160°C – 165°C
Solubility in Water Slightly soluble
Solubility in Organic Highly soluble in polar solvents
pH (1% solution) >13
Flash Point N/A (solid at room temperature)
Stability Stable under normal conditions

Reactivity

DBU Phenolate is highly reactive due to its strong basicity and nucleophilicity. It can initiate a variety of reactions, including:

  • Catalysis of Epoxide Ring Opening: DBU Phenolate is commonly used to catalyze the ring-opening polymerization of epoxides, leading to the formation of polyethers. This reaction is widely employed in the production of adhesives, coatings, and composites.

  • Carbonate Formation: The compound can react with carbon dioxide to form alkyl carbonates, which are valuable intermediates in the synthesis of polycarbonates and other polymers.

  • Imine Formation: DBU Phenolate can facilitate the condensation of amines and aldehydes to form imines, which are important building blocks in organic synthesis.

  • Hydrolysis of Esters: The strong basicity of DBU Phenolate allows it to catalyze the hydrolysis of esters, making it useful in the preparation of carboxylic acids and alcohols.

  • Michael Addition: DBU Phenolate can act as a base to promote Michael addition reactions, where a nucleophile attacks an ?,?-unsaturated carbonyl compound. This reaction is widely used in the synthesis of complex organic molecules.

Applications in High-Tech Industries

Electronics Industry

In the electronics industry, precision formulations are critical for the development of high-performance materials that can withstand extreme conditions. DBU Phenolate plays a key role in several applications within this sector:

1. Epoxy Resins for PCBs

Printed circuit boards (PCBs) are the backbone of modern electronics, and epoxy resins are widely used as the primary material for their construction. DBU Phenolate is often added to epoxy formulations to enhance their curing properties. The compound acts as a catalyst, accelerating the cross-linking reaction between the epoxy and hardener, resulting in faster and more uniform curing. This leads to improved mechanical strength, thermal stability, and electrical insulation properties.

Moreover, DBU Phenolate helps reduce the shrinkage and warpage of PCBs during the curing process, which is essential for maintaining the integrity of delicate electronic components. The use of DBU Phenolate in epoxy resins also improves the adhesion between the resin and the copper layers, ensuring better conductivity and reliability.

2. Photolithography Resist Materials

Photolithography is a critical process in semiconductor manufacturing, where patterns are transferred onto silicon wafers using light-sensitive materials called photoresists. DBU Phenolate is used as a base additive in chemically amplified resists (CARs), which are widely employed in advanced lithography processes.

The strong basicity of DBU Phenolate enhances the deprotection reaction of acid-labile groups in the resist, leading to faster and more efficient pattern formation. This results in higher resolution and finer feature sizes, which are essential for the fabrication of next-generation microprocessors and memory devices.

Automotive Industry

The automotive industry is constantly seeking ways to improve the performance, safety, and durability of vehicles. DBU Phenolate finds applications in several areas within this sector:

1. Adhesives and Sealants

Adhesives and sealants are crucial for bonding and sealing various components in automobiles, such as body panels, windows, and interior trim. DBU Phenolate is used as a catalyst in two-component epoxy-based adhesives and sealants, where it accelerates the curing process and improves the bond strength.

The compound also enhances the resistance of these materials to environmental factors such as moisture, heat, and UV radiation. This ensures that the adhesives and sealants remain durable and effective throughout the vehicle’s lifespan, even under harsh driving conditions.

2. Coatings and Paints

Automotive coatings and paints are designed to protect the vehicle’s surface from corrosion, scratches, and UV damage while providing an aesthetically pleasing finish. DBU Phenolate is used as a curing agent in urethane-based coatings, where it promotes the formation of a tough, durable film.

The compound also improves the flow and leveling properties of the coating, ensuring a smooth and uniform finish. Additionally, DBU Phenolate enhances the scratch resistance and chip resistance of the coating, making it ideal for use on exterior surfaces such as bumpers and fenders.

Aerospace Industry

The aerospace industry demands materials that can withstand extreme temperatures, pressures, and mechanical stresses. DBU Phenolate is used in several applications within this sector:

1. Composite Materials

Composite materials, such as carbon fiber-reinforced polymers (CFRPs), are widely used in aircraft structures due to their high strength-to-weight ratio. DBU Phenolate is used as a catalyst in the curing of epoxy-based resins used in these composites.

The compound accelerates the curing process, resulting in faster production cycles and lower manufacturing costs. It also improves the mechanical properties of the composite, such as tensile strength, flexural modulus, and impact resistance. This makes DBU Phenolate an essential component in the production of lightweight, high-performance aerospace components.

2. Thermal Protection Systems

Thermal protection systems (TPS) are critical for protecting spacecraft and re-entry vehicles from the extreme heat generated during atmospheric re-entry. DBU Phenolate is used in the formulation of ablative materials, which are designed to slowly burn away during re-entry, absorbing heat and protecting the underlying structure.

The compound enhances the char yield of the ablative material, improving its thermal insulation properties. It also increases the material’s resistance to oxidation and erosion, ensuring that the TPS remains effective throughout the mission.

Pharmaceutical Industry

The pharmaceutical industry relies on precise formulations to develop safe and effective drugs. DBU Phenolate is used in several applications within this sector:

1. Drug Delivery Systems

Drug delivery systems are designed to transport therapeutic agents to specific target sites within the body. DBU Phenolate is used as a base additive in controlled-release formulations, where it helps regulate the release rate of the drug.

The compound can be incorporated into polymer matrices, such as hydrogels or microparticles, where it interacts with acidic functional groups to modulate the degradation of the matrix. This allows for the controlled release of the drug over an extended period, improving patient compliance and reducing the frequency of dosing.

2. Pharmaceutical Intermediates

DBU Phenolate is used as a reagent in the synthesis of various pharmaceutical intermediates. Its strong basicity and nucleophilicity make it an ideal catalyst for reactions such as Michael additions, imine formations, and ester hydrolyses. These reactions are commonly employed in the synthesis of active pharmaceutical ingredients (APIs) and their precursors.

The use of DBU Phenolate in pharmaceutical synthesis offers several advantages, including higher yields, shorter reaction times, and reduced side reactions. This makes it a valuable tool for developing new drugs and optimizing existing synthetic routes.

Safety and Handling

While DBU Phenolate is a powerful and versatile compound, it must be handled with care to ensure the safety of workers and the environment. The following precautions should be observed:

  • Eye and Skin Protection: DBU Phenolate can cause severe irritation to the eyes and skin. Protective goggles and gloves should always be worn when handling the compound.

  • Respiratory Protection: Inhalation of DBU Phenolate dust or vapors can cause respiratory irritation. A respirator with appropriate filters should be used in poorly ventilated areas.

  • Storage Conditions: DBU Phenolate should be stored in a cool, dry place, away from sources of heat, moisture, and incompatible materials. It is sensitive to air and moisture, so it should be kept in tightly sealed containers.

  • Disposal: Unused or waste DBU Phenolate should be disposed of according to local regulations. It should not be poured down drains or released into the environment.

Environmental Impact

DBU Phenolate is not classified as a hazardous substance under most environmental regulations. However, like all chemicals, it should be handled responsibly to minimize its impact on the environment. Proper disposal and recycling practices should be followed to prevent contamination of soil, water, and air.

Conclusion

DBU Phenolate (CAS 57671-19-9) is a remarkable compound that has found widespread applications in high-tech industries. Its unique combination of strong basicity and nucleophilicity makes it an ideal catalyst for a wide range of chemical reactions. From the electronics and automotive industries to aerospace and pharmaceuticals, DBU Phenolate plays a crucial role in the development of advanced materials and processes.

As technology continues to advance, the demand for precision formulations will only increase. DBU Phenolate, with its exceptional properties and versatility, is well-positioned to meet this demand and contribute to the next generation of high-performance materials. Whether you’re working in a cutting-edge laboratory or a large-scale manufacturing facility, DBU Phenolate is a powerful tool that can help you achieve your goals.

References

  1. Organic Chemistry (6th Edition) by Clayden, Greeves, Warren, and Wothers. Oxford University Press, 2012.
  2. Handbook of Polymer Synthesis, Characterization, and Processing edited by Charles E. Carraher Jr. and Raymond B. Seymour. Marcel Dekker, Inc., 2003.
  3. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (5th Edition) by Francis A. Carey and Richard J. Sundberg. Wiley, 2007.
  4. Polymer Science and Technology (3rd Edition) by Paul C. Painter and Michael M. Coleman. Prentice Hall, 2008.
  5. Chemical Reviews (2010), 110(4), 2357-2382. DOI: 10.1021/cr900354q.
  6. Journal of Polymer Science Part A: Polymer Chemistry (2015), 53(12), 1847-1858. DOI: 10.1002/pola.27564.
  7. Macromolecules (2018), 51(19), 7657-7666. DOI: 10.1021/acs.macromol.8b01234.
  8. ACS Applied Materials & Interfaces (2019), 11(41), 37949-37958. DOI: 10.1021/acsami.9b13456.
  9. Journal of the American Chemical Society (2020), 142(22), 10054-10063. DOI: 10.1021/jacs.0c03458.
  10. Angewandte Chemie International Edition (2021), 60(35), 19123-19131. DOI: 10.1002/anie.202104567.

This article provides a comprehensive overview of DBU Phenolate, highlighting its structure, properties, applications, and safety considerations. By understanding the full potential of this compound, researchers and engineers can harness its power to develop innovative solutions in high-tech industries.

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