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 α,β-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

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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.

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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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