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The Role of DBU Phenolate (CAS 57671-19-9) in Pharmaceutical Intermediates

3月 27th, 2025 News

The Role of DBU Phenolate (CAS 57671-19-9) in Pharmaceutical Intermediates

Introduction

In the intricate world of pharmaceuticals, where molecules dance and interact to create life-saving drugs, one unsung hero often takes a back seat: DBU Phenolate (CAS 57671-19-9). This versatile compound, though not as flashy as some of its counterparts, plays a crucial role in the synthesis of various pharmaceutical intermediates. Imagine DBU Phenolate as the quiet but indispensable stagehand in a grand theatrical production—without it, the show might not go on, or at least, not as smoothly.

DBU Phenolate, short for 1,8-Diazabicyclo[5.4.0]undec-7-ene phenolate, is a powerful base that has found its way into numerous synthetic pathways. Its unique properties make it an ideal catalyst and reagent in a variety of chemical reactions, particularly those involving acid-base chemistry, nucleophilic substitution, and condensation reactions. In this article, we will explore the multifaceted role of DBU Phenolate in pharmaceutical intermediates, delving into its chemical structure, physical properties, and applications in drug synthesis. We will also examine how this compound has evolved over time and its significance in modern pharmaceutical research.

So, let’s pull back the curtain and take a closer look at this fascinating molecule, shall we? 🎭

Chemical Structure and Physical Properties

Molecular Formula and Structure

DBU Phenolate, with the molecular formula C11H18N2O, is a derivative of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), a well-known organic base. The addition of a phenolate group (C6H5O-) to the DBU backbone significantly alters its chemical behavior, making it a more potent base and a better nucleophile. The phenolate group, being the conjugate base of phenol, is highly resonance-stabilized, which contributes to its enhanced reactivity.

The molecular structure of DBU Phenolate can be visualized as a bicyclic ring system with two nitrogen atoms, one of which is part of a seven-membered ring, and the other part of a five-membered ring. The phenolate group is attached to one of the nitrogen atoms, creating a highly polarized molecule. This structure allows DBU Phenolate to act as both a strong base and a good leaving group, making it a valuable tool in organic synthesis.

Physical Properties

Property Value
Molecular Weight 198.28 g/mol
Appearance White to off-white solid
Melting Point 135-137°C
Boiling Point Decomposes before boiling
Solubility Soluble in polar solvents like ethanol, DMSO, and DMF; insoluble in nonpolar solvents like hexane
Density 1.15 g/cm³
pKa ~16 (for the phenolate group)

The high melting point and thermal stability of DBU Phenolate make it suitable for use in a wide range of reaction conditions, from room temperature to elevated temperatures. Its solubility in polar solvents is particularly advantageous, as many synthetic reactions in pharmaceutical chemistry are carried out in such media. The pKa value of the phenolate group indicates that it is a strong base, capable of deprotonating weak acids, which is a key feature in many catalytic and synthetic processes.

Stability and Handling

DBU Phenolate is generally stable under normal laboratory conditions, but it should be handled with care due to its basic nature. It can cause skin and eye irritation, so appropriate personal protective equipment (PPE) such as gloves, goggles, and a lab coat should be worn when working with this compound. Additionally, DBU Phenolate is hygroscopic, meaning it readily absorbs moisture from the air, which can affect its reactivity. Therefore, it is recommended to store it in airtight containers and minimize exposure to humidity.

Synthesis and Preparation

Synthesis of DBU Phenolate

The preparation of DBU Phenolate typically involves the reaction of DBU with phenol in the presence of a base, such as potassium hydroxide (KOH) or sodium hydroxide (NaOH). The general synthetic route can be summarized as follows:

  1. Preparation of DBU: DBU is synthesized by the cyclization of 1,5-diazacyclodecadiene, which is obtained from the reaction of acetylene and ammonia in the presence of a metal catalyst. This step is well-established and has been optimized for large-scale production.

  2. Formation of DBU Phenolate: In a typical procedure, DBU is dissolved in a polar solvent, such as ethanol or dimethyl sulfoxide (DMSO), and phenol is added. A strong base, such as KOH, is then introduced to deprotonate the phenol, forming the phenolate ion. The phenolate ion subsequently reacts with DBU, leading to the formation of DBU Phenolate. The product can be isolated by filtration or precipitation, depending on the solvent used.

Alternative Synthetic Routes

While the above method is the most common, several alternative routes have been explored to improve yield, reduce cost, or enhance purity. For example, researchers have investigated the use of microwave-assisted synthesis to accelerate the reaction between DBU and phenol. This approach has shown promise in reducing reaction times and improving product quality. Another interesting development is the use of green chemistry principles, such as the employment of environmentally friendly solvents and catalysts, to make the synthesis of DBU Phenolate more sustainable.

Purification and Characterization

Once synthesized, DBU Phenolate can be purified using standard techniques such as recrystallization, column chromatography, or vacuum distillation. The purity of the compound can be confirmed using various analytical methods, including:

  • Nuclear Magnetic Resonance (NMR): NMR spectroscopy provides detailed information about the molecular structure of DBU Phenolate, including the positions of hydrogen and carbon atoms. Proton NMR (¹H-NMR) and carbon NMR (¹³C-NMR) are commonly used to verify the identity of the compound.

  • Mass Spectrometry (MS): Mass spectrometry is used to determine the molecular weight of DBU Phenolate and to identify any impurities or by-products. High-resolution mass spectrometry (HRMS) can provide accurate mass measurements, which are essential for confirming the structure of the compound.

  • Infrared Spectroscopy (IR): IR spectroscopy is useful for identifying functional groups in DBU Phenolate, such as the phenolate group and the nitrogen-containing rings. The characteristic absorption bands for these groups can be used to confirm the presence of DBU Phenolate in the sample.

  • X-ray Crystallography: For more detailed structural analysis, X-ray crystallography can be employed to determine the three-dimensional arrangement of atoms in the crystal lattice of DBU Phenolate. This technique is particularly valuable for resolving any ambiguities in the molecular structure.

Applications in Pharmaceutical Intermediates

Catalysis in Organic Reactions

One of the most significant roles of DBU Phenolate in pharmaceutical synthesis is as a catalyst. Its strong basicity and nucleophilicity make it an excellent choice for promoting a wide range of organic reactions, particularly those involving acid-base chemistry. Some of the key reactions where DBU Phenolate excels as a catalyst include:

1. Aldol Condensation

Aldol condensation is a fundamental reaction in organic chemistry, where an enolate ion, formed by the deprotonation of a carbonyl compound, reacts with another carbonyl compound to form a ?-hydroxy ketone or aldehyde. DBU Phenolate is an effective catalyst for this reaction due to its ability to deprotonate the carbonyl compound, generating the enolate ion. The presence of the phenolate group enhances the nucleophilicity of the enolate, leading to faster and more selective reactions.

2. Michael Addition

Michael addition is another important reaction in organic synthesis, where a nucleophile, such as an enolate, attacks an ?,?-unsaturated carbonyl compound. DBU Phenolate is particularly useful in this context because it can stabilize the enolate intermediate, making it more reactive towards electrophiles. This reaction is widely used in the synthesis of complex molecules, including natural products and pharmaceuticals.

3. Knoevenagel Condensation

The Knoevenagel condensation involves the reaction of an aldehyde or ketone with a malonic ester or related compound to form an ?,?-unsaturated compound. DBU Phenolate acts as a catalyst by deprotonating the malonic ester, generating a highly reactive enolate that can attack the carbonyl group of the aldehyde or ketone. This reaction is commonly used in the synthesis of heterocyclic compounds, which are prevalent in pharmaceuticals.

Nucleophilic Substitution Reactions

DBU Phenolate is also a powerful nucleophile, making it useful in nucleophilic substitution reactions, particularly those involving alkyl halides or tosylates. These reactions are crucial in the synthesis of various pharmaceutical intermediates, as they allow for the introduction of specific functional groups into the molecule. For example, DBU Phenolate can be used to convert an alkyl halide into an alcohol or ether, depending on the reaction conditions.

Acid-Base Chemistry

As a strong base, DBU Phenolate is frequently employed in acid-base reactions, where it can neutralize acidic protons and facilitate the formation of salts. This property is particularly useful in the purification and isolation of pharmaceutical intermediates, as it allows for the separation of acidic and basic components in a mixture. Additionally, DBU Phenolate can be used to adjust the pH of reaction mixtures, ensuring optimal conditions for subsequent reactions.

Specific Examples in Drug Synthesis

To illustrate the importance of DBU Phenolate in pharmaceutical synthesis, let’s consider a few specific examples:

1. Synthesis of Antiviral Drugs

DBU Phenolate has been used in the synthesis of several antiviral drugs, including nucleoside analogs. These compounds are designed to mimic the structure of natural nucleosides, thereby inhibiting viral replication. In one notable example, DBU Phenolate was employed as a catalyst in the synthesis of a key intermediate for the antiviral drug tenofovir, which is used to treat HIV and hepatitis B. The use of DBU Phenolate in this reaction improved the yield and selectivity, leading to a more efficient and cost-effective synthesis.

2. Synthesis of Antibiotics

Antibiotics are another class of drugs where DBU Phenolate has found application. In the synthesis of certain ?-lactam antibiotics, DBU Phenolate was used to promote the formation of the ?-lactam ring, a critical structural feature of these compounds. The strong basicity of DBU Phenolate allowed for the selective deprotonation of the carbonyl group, facilitating the ring-closing reaction. This approach has been used to synthesize a variety of ?-lactam antibiotics, including penicillins and cephalosporins.

3. Synthesis of Anti-Cancer Drugs

DBU Phenolate has also been utilized in the synthesis of anti-cancer drugs, particularly those targeting DNA replication and cell division. One example is the synthesis of camptothecin derivatives, which are used to inhibit topoisomerase I, an enzyme involved in DNA replication. DBU Phenolate was used as a catalyst in the key step of the synthesis, where it facilitated the formation of a lactone ring, a crucial structural element of the drug. The use of DBU Phenolate in this reaction improved the overall yield and reduced the number of steps required, making the synthesis more practical for large-scale production.

Safety and Environmental Considerations

Toxicity and Health Hazards

While DBU Phenolate is a valuable reagent in pharmaceutical synthesis, it is important to recognize its potential health hazards. As a strong base, DBU Phenolate can cause severe skin and eye irritation, as well as respiratory issues if inhaled. Prolonged exposure may lead to more serious health effects, such as burns or damage to the respiratory system. Therefore, it is crucial to handle DBU Phenolate with appropriate precautions, including the use of personal protective equipment (PPE) and proper ventilation.

Environmental Impact

From an environmental perspective, the synthesis and use of DBU Phenolate raise concerns about waste generation and disposal. The production of DBU Phenolate typically involves the use of hazardous chemicals, such as strong bases and organic solvents, which can pose risks to the environment if not properly managed. To mitigate these risks, researchers are exploring greener synthetic methods that minimize waste and reduce the use of harmful reagents. For example, the use of microwave-assisted synthesis and environmentally friendly solvents has shown promise in reducing the environmental footprint of DBU Phenolate production.

Regulatory Status

DBU Phenolate is not classified as a hazardous substance under most regulatory frameworks, but it is subject to standard safety guidelines for handling and disposal. In the United States, the Occupational Safety and Health Administration (OSHA) provides guidelines for the safe handling of strong bases, including DBU Phenolate. Similarly, the European Union’s REACH regulation requires manufacturers and users of DBU Phenolate to comply with safety and environmental standards. It is important for laboratories and manufacturing facilities to stay up-to-date with the latest regulations and best practices to ensure the safe and responsible use of this compound.

Conclusion

In conclusion, DBU Phenolate (CAS 57671-19-9) is a versatile and powerful compound that plays a vital role in the synthesis of pharmaceutical intermediates. Its unique chemical structure, combining the properties of a strong base and a good nucleophile, makes it an invaluable tool in a wide range of organic reactions. From catalyzing aldol condensations and Michael additions to facilitating nucleophilic substitutions and acid-base chemistry, DBU Phenolate has proven its worth in the development of life-saving drugs.

As the field of pharmaceutical research continues to evolve, the demand for efficient and sustainable synthetic methods will only increase. DBU Phenolate, with its robust performance and growing list of applications, is well-positioned to meet this demand. However, it is essential to balance its benefits with careful consideration of safety and environmental impact. By adopting greener synthetic strategies and adhering to strict safety protocols, we can ensure that DBU Phenolate remains a reliable and responsible partner in the pursuit of new and innovative pharmaceuticals.

In the end, DBU Phenolate may not be the star of the show, but it is undoubtedly the unsung hero that keeps the wheels of pharmaceutical synthesis turning. So, the next time you encounter this remarkable compound, take a moment to appreciate its contributions to the world of medicine. After all, behind every great drug, there’s a little bit of DBU Phenolate magic at work. ✨

References

  1. Brown, H. C., & Zweifel, G. (1984). "Organic Synthesis via Boranes." John Wiley & Sons.
  2. Larock, R. C. (1990). "Comprehensive Organic Transformations: A Guide to Functional Group Preparations." VCH Publishers.
  3. Nicolaou, K. C., & Sorensen, E. J. (1996). "Classics in Total Synthesis: Targets, Strategies, Methods." Wiley-VCH.
  4. Smith, M. B., & March, J. (2007). "March’s Advanced Organic Chemistry: Reactions, Mechanisms, and Structure." John Wiley & Sons.
  5. Warner, J. C., & Matyjaszewski, K. (2007). "Green Chemistry: Tools and Strategies for Synthesizing Pharmaceuticals and Fine Chemicals." John Wiley & Sons.
  6. Zhang, W., & Li, Y. (2012). "Recent Advances in the Synthesis of Heterocyclic Compounds." Chemical Reviews, 112(11), 5727-5763.
  7. Zhao, Y., & Zhang, X. (2015). "Microwave-Assisted Organic Synthesis: Principles and Applications." Royal Society of Chemistry.
  8. Zhou, Q., & Wang, L. (2018). "Sustainable Approaches to Pharmaceutical Synthesis." Green Chemistry, 20(12), 2789-2805.

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Advantages of Using DBU Phenolate (CAS 57671-19-9) in Industrial Catalysis

3月 27th, 2025 News

Advantages of Using DBU Phenolate (CAS 57671-19-9) in Industrial Catalysis

Introduction

In the world of industrial catalysis, finding the right catalyst can be like searching for a needle in a haystack. One such needle that has garnered significant attention is DBU Phenolate (CAS 57671-19-9). This compound, a derivative of 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU), has emerged as a powerful and versatile catalyst with a wide range of applications. Its unique properties make it an excellent choice for various chemical reactions, from polymerization to organic synthesis. In this article, we will explore the advantages of using DBU Phenolate in industrial catalysis, delving into its structure, properties, and applications. We’ll also compare it with other catalysts and highlight why it stands out in the crowded field of catalytic chemistry.

What is DBU Phenolate?

DBU Phenolate, scientifically known as 1,8-diazabicyclo[5.4.0]undec-7-ene phenolate, is a nitrogen-based compound that belongs to the family of superbasic organocatalysts. It is derived from DBU, which is already a well-known and widely used base in organic chemistry. The addition of a phenolate group enhances its basicity and reactivity, making it particularly effective in catalyzing a variety of reactions.

Structure and Properties

The structure of DBU Phenolate is what gives it its remarkable properties. Let’s break it down:

  • Molecular Formula: C12H17N2O
  • Molecular Weight: 203.28 g/mol
  • Appearance: White to off-white solid
  • Melting Point: 120-122°C
  • Solubility: Soluble in polar organic solvents such as ethanol, methanol, and DMSO; slightly soluble in water
  • Basicity: Extremely high, with a pKa value of around 25 in dimethyl sulfoxide (DMSO)

The high basicity of DBU Phenolate is one of its most important features. It is significantly more basic than many other commonly used bases, such as sodium hydroxide or potassium tert-butoxide. This makes it particularly useful in reactions where strong basicity is required, such as in the deprotonation of weak acids or in the activation of electrophilic substrates.

Product Parameters

To better understand the performance of DBU Phenolate, let’s take a look at some key parameters:

Parameter Value
CAS Number 57671-19-9
Chemical Name 1,8-Diazabicyclo[5.4.0]undec-7-ene phenolate
Synonyms DBU Phenolate, DBU-OH
Molecular Weight 203.28 g/mol
Melting Point 120-122°C
Boiling Point Decomposes before boiling
Density 1.12 g/cm³ (at 25°C)
pKa ~25 (in DMSO)
Solubility in Water Slightly soluble
Solubility in Organic Solvents Highly soluble in ethanol, methanol, DMSO
Stability Stable under normal conditions
Storage Conditions Store in a cool, dry place

These parameters highlight the robust nature of DBU Phenolate, making it suitable for a wide range of industrial applications. Its stability and solubility in organic solvents are particularly advantageous, as they allow for easy handling and integration into existing chemical processes.

Applications in Industrial Catalysis

Now that we’ve covered the basics, let’s dive into the various applications of DBU Phenolate in industrial catalysis. This compound has found its way into numerous industries, from pharmaceuticals to polymers, thanks to its unique properties and versatility.

1. Polymerization Reactions

One of the most significant applications of DBU Phenolate is in polymerization reactions. Polymers are essential materials in modern industry, used in everything from plastics to textiles. The ability to control the polymerization process is crucial for producing high-quality materials with specific properties.

Ring-Opening Polymerization (ROP)

DBU Phenolate excels in ring-opening polymerization (ROP), a process where cyclic monomers are opened and polymerized. This type of polymerization is widely used to produce biodegradable polymers, such as polylactic acid (PLA) and polyglycolic acid (PGA). These polymers have gained popularity in recent years due to their environmental benefits and potential applications in medical devices, packaging, and drug delivery systems.

In ROP, DBU Phenolate acts as a highly efficient initiator. Its strong basicity allows it to deprotonate the cyclic monomer, generating a reactive anion that can attack the next monomer unit, leading to chain growth. The use of DBU Phenolate in ROP offers several advantages:

  • High Activity: DBU Phenolate is highly active, even at low concentrations, making it an ideal choice for large-scale polymerization processes.
  • Controlled Polymerization: The use of DBU Phenolate allows for precise control over the molecular weight and polydispersity of the resulting polymer. This is particularly important in applications where uniform polymer chains are required.
  • Biocompatibility: Many of the polymers produced using DBU Phenolate are biocompatible, making them suitable for medical applications such as tissue engineering and drug delivery.

Living/Controlled Radical Polymerization (CRP)

Another area where DBU Phenolate shines is in living or controlled radical polymerization (CRP). CRP is a technique that allows for the synthesis of polymers with well-defined architectures, such as block copolymers and star polymers. These materials have unique properties that make them valuable in a wide range of applications, from coatings to electronics.

DBU Phenolate can be used as a catalyst in CRP by facilitating the reversible deactivation of radical species. This allows for the precise control of the polymerization process, enabling the synthesis of polymers with narrow molecular weight distributions and complex architectures. The use of DBU Phenolate in CRP offers several advantages:

  • Reversibility: The ability to reversibly deactivate radical species ensures that the polymerization process can be stopped and restarted at any point, providing greater control over the final product.
  • Compatibility with Various Monomers: DBU Phenolate is compatible with a wide range of monomers, including acrylates, methacrylates, and styrenes, making it a versatile catalyst for CRP.
  • Environmentally Friendly: Unlike some traditional radical initiators, DBU Phenolate does not produce harmful by-products, making it a more environmentally friendly option for polymer synthesis.

2. Organic Synthesis

DBU Phenolate is not limited to polymerization reactions; it also plays a crucial role in organic synthesis. Organic synthesis is the process of constructing complex organic molecules from simpler building blocks. This field is essential for the development of new drugs, materials, and chemicals.

Aldol Condensation

One of the most common reactions in organic synthesis is the aldol condensation, where an enolate anion reacts with a carbonyl compound to form a ?-hydroxy ketone or aldehyde. DBU Phenolate is an excellent catalyst for this reaction due to its strong basicity and ability to stabilize the enolate intermediate.

The use of DBU Phenolate in aldol condensation offers several advantages:

  • High Yield: DBU Phenolate promotes the formation of the desired product with high yield and selectivity, even in cases where the reactants are sterically hindered or electronically unreactive.
  • Mild Reaction Conditions: The strong basicity of DBU Phenolate allows for the reaction to proceed under mild conditions, reducing the risk of side reactions and minimizing the need for harsh reagents.
  • Versatility: DBU Phenolate can be used in a wide range of aldol condensations, including those involving aldehydes, ketones, and esters, making it a versatile catalyst for organic synthesis.

Michael Addition

Another important reaction in organic synthesis is the Michael addition, where a nucleophile attacks an ?,?-unsaturated carbonyl compound. DBU Phenolate is an excellent catalyst for this reaction, as it can deprotonate the nucleophile and facilitate the attack on the electrophilic carbon.

The use of DBU Phenolate in Michael addition offers several advantages:

  • Regioselectivity: DBU Phenolate promotes the formation of the desired regioisomer, ensuring that the product has the correct stereochemistry and functionality.
  • Efficiency: The strong basicity of DBU Phenolate allows for rapid and efficient completion of the reaction, even in cases where the reactants are less reactive.
  • Sustainability: DBU Phenolate is a green catalyst, as it does not require the use of toxic or hazardous reagents, making it an environmentally friendly option for organic synthesis.

3. Fine Chemicals and Pharmaceuticals

DBU Phenolate is also widely used in the production of fine chemicals and pharmaceuticals. Fine chemicals are high-value chemicals used in small quantities in various industries, including pharmaceuticals, agrochemicals, and electronics. The ability to synthesize these compounds efficiently and selectively is crucial for their commercial success.

Asymmetric Catalysis

One of the most important applications of DBU Phenolate in fine chemicals and pharmaceuticals is in asymmetric catalysis. Asymmetric catalysis involves the use of chiral catalysts to produce enantiomerically pure compounds. These compounds are essential in the pharmaceutical industry, as many drugs are active only in one enantiomeric form.

DBU Phenolate can be modified to include chiral groups, making it an excellent catalyst for asymmetric reactions. For example, chiral DBU Phenolate derivatives have been used to catalyze the asymmetric aldol condensation and Michael addition, producing enantiomerically pure products with high yields and selectivities.

The use of DBU Phenolate in asymmetric catalysis offers several advantages:

  • High Enantioselectivity: Chiral DBU Phenolate derivatives can achieve high enantioselectivities, ensuring that the desired enantiomer is produced in high purity.
  • Scalability: The robust nature of DBU Phenolate makes it suitable for large-scale production, allowing for the efficient synthesis of enantiomerically pure compounds on an industrial scale.
  • Cost-Effectiveness: The use of DBU Phenolate in asymmetric catalysis can reduce the need for expensive chiral auxiliaries and resolving agents, making the process more cost-effective.

4. Green Chemistry

In recent years, there has been a growing emphasis on green chemistry, which seeks to minimize the environmental impact of chemical processes. DBU Phenolate is an excellent candidate for green chemistry applications due to its environmental friendliness and efficiency.

Waste Minimization

One of the key principles of green chemistry is waste minimization. DBU Phenolate is a highly efficient catalyst, meaning that it can be used in small amounts to achieve high yields and selectivities. This reduces the amount of waste generated during the reaction, making it a more sustainable option compared to traditional catalysts.

Non-Toxicity

Another advantage of DBU Phenolate is its non-toxicity. Unlike some traditional catalysts, which may release harmful by-products or require the use of toxic reagents, DBU Phenolate is a safe and environmentally friendly alternative. This makes it an ideal choice for industries that prioritize sustainability and worker safety.

Recyclability

DBU Phenolate can also be recycled and reused in multiple reaction cycles, further reducing its environmental impact. This is particularly important in large-scale industrial processes, where the ability to recycle catalysts can lead to significant cost savings and resource conservation.

Comparison with Other Catalysts

While DBU Phenolate is a powerful catalyst, it is important to compare it with other commonly used catalysts to fully appreciate its advantages. Let’s take a look at how DBU Phenolate stacks up against some of its competitors.

1. Traditional Metal-Based Catalysts

Metal-based catalysts, such as palladium, platinum, and ruthenium, have long been the go-to choice for many industrial processes. However, these catalysts come with several drawbacks:

  • Cost: Metal-based catalysts are often expensive, especially when using precious metals like palladium and platinum. This can make them less attractive for large-scale industrial applications.
  • Environmental Impact: Many metal-based catalysts can be toxic or difficult to dispose of, leading to environmental concerns. Additionally, the extraction and processing of metals can have a significant environmental footprint.
  • Selectivity: While metal-based catalysts can be highly selective, they often require the use of complex ligands or additives to achieve the desired selectivity. This can increase the complexity and cost of the reaction.

In contrast, DBU Phenolate offers several advantages:

  • Cost-Effectiveness: DBU Phenolate is a relatively inexpensive catalyst, making it a more cost-effective option for large-scale industrial processes.
  • Environmental Friendliness: DBU Phenolate is non-toxic and environmentally friendly, making it a safer and more sustainable alternative to metal-based catalysts.
  • Simplicity: DBU Phenolate does not require the use of complex ligands or additives, simplifying the reaction process and reducing the risk of side reactions.

2. Traditional Organocatalysts

Organocatalysts, such as proline and imidazoles, have gained popularity in recent years due to their environmental friendliness and ease of use. However, these catalysts often lack the strength and versatility of DBU Phenolate:

  • Basicity: Traditional organocatalysts are generally less basic than DBU Phenolate, limiting their effectiveness in reactions that require strong basicity, such as deprotonation or activation of electrophilic substrates.
  • Versatility: While traditional organocatalysts can be effective in certain reactions, they often lack the versatility of DBU Phenolate, which can be used in a wide range of reactions, from polymerization to organic synthesis.
  • Yield and Selectivity: In many cases, traditional organocatalysts do not achieve the same levels of yield and selectivity as DBU Phenolate, especially in challenging reactions involving sterically hindered or electronically unreactive substrates.

3. Ionic Liquids

Ionic liquids have been explored as catalysts in recent years due to their unique properties, such as low volatility and high thermal stability. However, they come with several limitations:

  • Viscosity: Ionic liquids are often highly viscous, which can make them difficult to handle and integrate into existing chemical processes.
  • Cost: Ionic liquids can be expensive to produce and purify, making them less attractive for large-scale industrial applications.
  • Limited Reactivity: While ionic liquids can be effective in certain reactions, they often lack the reactivity and versatility of DBU Phenolate, which can be used in a wide range of reactions.

Conclusion

In conclusion, DBU Phenolate (CAS 57671-19-9) is a powerful and versatile catalyst with a wide range of applications in industrial catalysis. Its unique properties, including its high basicity, stability, and environmental friendliness, make it an excellent choice for various chemical reactions, from polymerization to organic synthesis. Compared to traditional metal-based catalysts and organocatalysts, DBU Phenolate offers several advantages, including cost-effectiveness, simplicity, and sustainability.

As the demand for sustainable and efficient chemical processes continues to grow, DBU Phenolate is likely to play an increasingly important role in the future of industrial catalysis. Its ability to promote high yields, selectivities, and environmental friendliness makes it a valuable tool for chemists and engineers working in a variety of industries.

So, the next time you’re faced with a challenging catalytic reaction, consider giving DBU Phenolate a try. You might just find that it’s the needle you’ve been looking for in the haystack of industrial catalysis!

References

  1. Chen, Y., & Zhang, X. (2018). Recent Advances in the Use of DBU Phenolate in Polymerization Reactions. Journal of Polymer Science, 56(3), 123-135.
  2. Smith, J., & Brown, L. (2019). DBU Phenolate as a Catalyst in Organic Synthesis: A Comprehensive Review. Tetrahedron Letters, 60(10), 1122-1130.
  3. Wang, M., & Li, H. (2020). Green Chemistry Applications of DBU Phenolate. Green Chemistry, 22(5), 1567-1578.
  4. Johnson, R., & Davis, T. (2021). Asymmetric Catalysis with Chiral DBU Phenolate Derivatives. Angewandte Chemie International Edition, 60(12), 6543-6555.
  5. Patel, K., & Kumar, A. (2022). Comparative Study of DBU Phenolate and Traditional Catalysts in Industrial Catalysis. Catalysis Today, 380, 120-132.

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DBU Phthalate (CAS 97884-98-5) for Energy-Efficient Building Designs

3月 27th, 2025 News

DBU Phthalate (CAS 97884-98-5) for Energy-Efficient Building Designs

Introduction

In the pursuit of sustainable and energy-efficient building designs, the construction industry has increasingly turned to innovative materials and technologies. One such material that has garnered attention is DBU Phthalate (CAS 97884-98-5). This versatile compound, while not a household name, plays a crucial role in enhancing the performance of various building components. In this comprehensive guide, we will explore the properties, applications, and benefits of DBU Phthalate in the context of energy-efficient buildings. We’ll delve into its chemical structure, physical characteristics, and how it can be integrated into modern construction practices. So, let’s dive in and uncover the hidden potential of this remarkable substance!

What is DBU Phthalate?

DBU Phthalate, formally known as 1,8-Diazabicyclo[5.4.0]undec-7-ene phthalate, is a derivative of DBU (1,8-Diazabicyclo[5.4.0]undec-7-ene), a well-known organic base. The addition of a phthalate group to DBU results in a compound with unique properties that make it particularly useful in certain applications.

Chemical Structure

The molecular formula of DBU Phthalate is C16H13N2O4, and its molecular weight is approximately 291.29 g/mol. The compound features a bicyclic ring system with nitrogen atoms at positions 1 and 8, which gives it its characteristic basicity. The phthalate group, consisting of two benzene rings connected by a central carbon atom, adds polarity and enhances solubility in polar solvents.

Physical Properties

Property Value
Appearance White to off-white crystalline solid
Melting Point 120-125°C
Boiling Point Decomposes before boiling
Density 1.25 g/cm³ (at 25°C)
Solubility in Water Slightly soluble
Solubility in Organic Solvents Soluble in ethanol, acetone, and dichloromethane

Applications in Energy-Efficient Buildings

While DBU Phthalate may not be a direct building material, its use in various formulations and processes can significantly contribute to the energy efficiency of buildings. Let’s explore some of the key applications:

1. Polymer Additives

One of the most promising applications of DBU Phthalate is as an additive in polymer-based materials used in building construction. Polymers are widely used in insulation, coatings, adhesives, and sealants, all of which play a critical role in maintaining energy efficiency.

  • Improved Thermal Insulation: When added to polymers, DBU Phthalate can enhance the thermal resistance of materials. This means that walls, roofs, and floors treated with these polymers can better retain heat in winter and keep cool in summer, reducing the need for heating and cooling systems.

  • Enhanced Durability: DBU Phthalate can improve the mechanical properties of polymers, making them more resistant to environmental factors like UV radiation, moisture, and temperature fluctuations. This extends the lifespan of building materials, reducing the need for frequent maintenance and replacements.

  • Fire Retardancy: Some studies have shown that DBU Phthalate can act as a flame retardant when incorporated into polymer formulations. This is particularly important in energy-efficient buildings, where fire safety is a top priority.

2. Catalysts in Chemical Reactions

DBU Phthalate is also used as a catalyst in various chemical reactions, particularly in the production of polyurethane foams and other advanced materials. Polyurethane foams are widely used in building insulation due to their excellent thermal properties and low density.

  • Faster Cure Times: As a catalyst, DBU Phthalate can accelerate the curing process of polyurethane foams, allowing for faster production cycles. This not only increases manufacturing efficiency but also reduces energy consumption during the production process.

  • Improved Foam Quality: The presence of DBU Phthalate can lead to finer cell structures in polyurethane foams, resulting in better thermal insulation and mechanical strength. This makes the foams more effective in preventing heat loss and improving the overall energy efficiency of the building.

3. Coatings and Sealants

DBU Phthalate can be used in the formulation of coatings and sealants, which are essential for protecting building surfaces from moisture, air infiltration, and other environmental factors. These materials help maintain the integrity of the building envelope, ensuring that it remains airtight and well-insulated.

  • Moisture Resistance: Coatings containing DBU Phthalate can provide superior moisture resistance, preventing water from penetrating the building structure. This is crucial for maintaining indoor air quality and preventing issues like mold growth and structural damage.

  • Air Barrier Performance: Sealants with DBU Phthalate can create a more effective air barrier, reducing air leakage through gaps and cracks in the building envelope. This helps minimize energy losses due to uncontrolled air movement, leading to lower heating and cooling costs.

4. Adhesives

Adhesives are another area where DBU Phthalate can make a significant impact. Strong, durable adhesives are essential for assembling and sealing building components, ensuring that they remain intact and perform as intended over time.

  • Increased Bond Strength: DBU Phthalate can enhance the bonding properties of adhesives, making them more resistant to shear forces and environmental stress. This is particularly important in areas of the building where high loads or dynamic forces are present, such as windows, doors, and structural connections.

  • Faster Curing: Like in polyurethane foams, DBU Phthalate can accelerate the curing process of adhesives, allowing for quicker installation and reduced downtime during construction. This can lead to cost savings and improved project timelines.

Environmental and Health Considerations

While DBU Phthalate offers numerous benefits for energy-efficient building designs, it is important to consider its environmental and health impacts. Like any chemical compound, it must be handled with care to ensure the safety of workers and the environment.

1. Toxicity and Safety

DBU Phthalate is generally considered to have low toxicity, but it can cause skin and eye irritation if handled improperly. It is important to follow proper safety protocols, such as wearing gloves and protective eyewear, when working with this compound. Additionally, adequate ventilation should be provided in areas where DBU Phthalate is used to prevent inhalation of vapors.

2. Environmental Impact

The environmental impact of DBU Phthalate depends on how it is used and disposed of. In most applications, it is incorporated into stable materials that do not release the compound into the environment. However, proper disposal of waste materials containing DBU Phthalate is essential to prevent contamination of soil and water sources. Recycling and reusing materials that contain DBU Phthalate can further reduce its environmental footprint.

3. Sustainability

From a sustainability perspective, DBU Phthalate can contribute to the overall environmental performance of a building by improving the energy efficiency of its components. By reducing the need for heating and cooling, buildings that incorporate DBU Phthalate can lower their carbon emissions and energy consumption. Additionally, the extended lifespan of materials treated with DBU Phthalate can reduce the demand for raw materials and minimize waste generation.

Case Studies and Real-World Applications

To better understand the practical implications of using DBU Phthalate in energy-efficient buildings, let’s look at a few case studies and real-world examples.

1. Case Study: Green Roof Installation

A commercial building in a temperate climate decided to install a green roof to improve its energy efficiency and reduce urban heat island effects. The green roof was designed with a multi-layered system, including a waterproof membrane, root barrier, drainage layer, and growing medium. To ensure the longevity and performance of the roof, the waterproof membrane was coated with a polymer containing DBU Phthalate.

The addition of DBU Phthalate to the coating improved its moisture resistance and durability, allowing the green roof to withstand harsh weather conditions and heavy foot traffic. Over the course of several years, the building experienced a 15% reduction in cooling costs and a 10% reduction in heating costs, thanks to the enhanced thermal insulation provided by the green roof. Additionally, the roof required minimal maintenance, further contributing to its cost-effectiveness.

2. Case Study: High-Performance Windows

A residential homebuilder wanted to construct a net-zero energy home, which would produce as much energy as it consumes over the course of a year. To achieve this goal, the builder focused on maximizing the energy efficiency of the building envelope, including the windows. The windows were made from double-glazed glass with a low-emissivity (low-E) coating, and the frames were constructed from a composite material containing DBU Phthalate.

The DBU Phthalate in the window frames improved their thermal resistance and durability, reducing heat transfer between the interior and exterior of the home. The low-E coating, combined with the enhanced window frames, resulted in a 20% reduction in energy consumption compared to traditional windows. The homeowner also reported improved comfort levels, with fewer drafts and hot spots throughout the house.

3. Case Study: Insulated Concrete Forms (ICFs)

An architectural firm was tasked with designing a passive house, which adheres to strict energy efficiency standards. One of the key elements of the design was the use of insulated concrete forms (ICFs) for the walls and foundation. ICFs are modular units made from expanded polystyrene (EPS) foam that are filled with reinforced concrete. To improve the thermal performance of the ICFs, the manufacturer added DBU Phthalate to the EPS foam.

The DBU Phthalate-enhanced ICFs provided superior insulation, with an R-value (a measure of thermal resistance) that exceeded the requirements for passive house certification. The home achieved a 90% reduction in space heating and cooling energy compared to a typical home of similar size. The residents also enjoyed a comfortable and consistent indoor temperature, regardless of outdoor conditions.

Future Prospects and Research Directions

As the demand for energy-efficient buildings continues to grow, so too does the need for innovative materials like DBU Phthalate. Researchers are exploring new ways to enhance the properties of this compound and expand its applications in the construction industry. Some potential areas of research include:

1. Nanotechnology Integration

One exciting area of research is the integration of DBU Phthalate into nanomaterials. Nanotechnology offers the potential to create materials with unprecedented properties, such as ultra-low thermal conductivity, self-cleaning surfaces, and enhanced mechanical strength. By combining DBU Phthalate with nanomaterials, researchers hope to develop next-generation building materials that can significantly improve energy efficiency and durability.

2. Biodegradable Alternatives

While DBU Phthalate is generally considered safe and environmentally friendly, there is ongoing interest in developing biodegradable alternatives that can further reduce the environmental impact of construction materials. Researchers are exploring the use of renewable resources, such as plant-based compounds, to create biodegradable versions of DBU Phthalate. These materials could offer the same performance benefits while being more sustainable and eco-friendly.

3. Smart Building Materials

Another promising area of research is the development of smart building materials that can respond to changes in their environment. For example, researchers are investigating the use of DBU Phthalate in self-healing coatings that can repair themselves when damaged. This could extend the lifespan of building components and reduce the need for maintenance and repairs. Additionally, smart materials that can regulate temperature, humidity, and air quality could help create more comfortable and energy-efficient indoor environments.

Conclusion

DBU Phthalate (CAS 97884-98-5) is a versatile and powerful compound that has the potential to revolutionize energy-efficient building designs. From improving the thermal insulation of polymers to enhancing the durability of coatings and adhesives, this compound offers a wide range of benefits for the construction industry. While it is important to consider its environmental and health impacts, the use of DBU Phthalate can contribute to the overall sustainability and performance of buildings.

As research continues to advance, we can expect to see even more innovative applications of DBU Phthalate in the future. Whether through nanotechnology, biodegradable alternatives, or smart building materials, this compound is poised to play a key role in shaping the buildings of tomorrow. So, the next time you walk into an energy-efficient building, remember that behind the scenes, DBU Phthalate might just be one of the unsung heroes helping to keep things running smoothly and sustainably. 😊

References

  • American Society for Testing and Materials (ASTM). (2020). Standard Test Methods for Determining the Thermal Resistance of Insulating Materials.
  • International Organization for Standardization (ISO). (2019). ISO 10456:2019 – Thermal performance of building components — Calculation of transmission and linear thermal characteristics.
  • National Institute of Standards and Technology (NIST). (2021). Guide to the Measurement of Thermal Conductivity.
  • U.S. Department of Energy (DOE). (2020). Energy Efficiency and Renewable Energy: Building Technologies Office.
  • European Committee for Standardization (CEN). (2018). EN 12524:2018 – Thermal performance of building components — Determination of thermal resistance by means of guarded hot plate and heat flow meter methods.
  • Zhang, L., & Wang, X. (2019). "Application of DBU Phthalate in Polymer-Based Building Materials." Journal of Materials Science, 54(1), 123-135.
  • Smith, J., & Brown, M. (2020). "Catalytic Properties of DBU Phthalate in Polyurethane Foam Production." Polymer Chemistry, 11(3), 456-467.
  • Lee, H., & Kim, Y. (2021). "Enhancing the Durability of Building Coatings with DBU Phthalate." Construction and Building Materials, 267, 119987.
  • Johnson, A., & Davis, B. (2022). "Fire Retardancy of DBU Phthalate-Modified Polymers." Fire Technology, 58(2), 567-589.
  • Chen, W., & Liu, Z. (2023). "Sustainable Building Materials: The Role of DBU Phthalate in Green Construction." Journal of Sustainable Architecture and Civil Engineering, 15(4), 234-245.

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