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Cost-Effective Solutions with DBU Benzyl Chloride Ammonium Salt in Industrial Processes

3月 27th, 2025 News

Cost-Effective Solutions with DBU Benzyl Chloride Ammonium Salt in Industrial Processes

Introduction

In the world of industrial chemistry, finding cost-effective and efficient solutions is akin to discovering a hidden treasure. One such gem that has garnered significant attention in recent years is DBU Benzyl Chloride Ammonium Salt (DBUBCAS). This versatile compound, often referred to as a "chemical chameleon," has found its way into a variety of industrial applications, from catalysis to material synthesis. Its unique properties make it an indispensable tool for chemists and engineers alike, offering a balance between performance and economy.

But what exactly is DBUBCAS, and why is it so special? Let’s dive into the world of this remarkable chemical and explore how it can revolutionize industrial processes, all while keeping costs in check. Along the way, we’ll take a closer look at its structure, properties, and applications, backed by data from both domestic and international literature. So, buckle up and get ready for a journey through the fascinating world of DBUBCAS!

What is DBU Benzyl Chloride Ammonium Salt?

Chemical Structure and Properties

DBU Benzyl Chloride Ammonium Salt, or DBUBCAS, is a quaternary ammonium salt derived from 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and benzyl chloride. The molecular formula of DBUBCAS is C12H16N3Cl, and its molecular weight is approximately 243.72 g/mol. The compound is a white crystalline solid at room temperature, with a melting point ranging from 160°C to 165°C. It is highly soluble in water and polar organic solvents, making it easy to handle and integrate into various industrial processes.

One of the most striking features of DBUBCAS is its pKa value, which is around 11.0. This high pKa indicates that DBUBCAS is a strong base, capable of deprotonating weak acids and facilitating a wide range of reactions. Additionally, its quaternary ammonium structure imparts excellent stability, ensuring that the compound remains active even under harsh conditions. This combination of basicity and stability makes DBUBCAS a powerful tool in many chemical transformations.

Synthesis and Production

The synthesis of DBUBCAS is relatively straightforward, involving the reaction of DBU with benzyl chloride in the presence of a solvent. The process can be summarized as follows:

  1. Preparation of DBU: DBU is synthesized from cyclohexadiene and ammonia in a multi-step process. This step is well-documented in the literature and is widely used in the production of various heterocyclic compounds.

  2. Quaternization Reaction: Once DBU is prepared, it reacts with benzyl chloride to form the quaternary ammonium salt. This reaction is typically carried out in a polar solvent, such as methanol or ethanol, at elevated temperatures (around 60°C). The reaction proceeds via a nucleophilic substitution mechanism, where the nitrogen atom of DBU attacks the electrophilic carbon of benzyl chloride, leading to the formation of the quaternary ammonium ion.

  3. Purification: After the reaction is complete, the product is purified by filtration and recrystallization. The final product, DBUBCAS, is obtained as a white crystalline solid with high purity (typically >98%).

This simple and scalable synthesis method has made DBUBCAS an attractive choice for industrial applications, particularly in industries where cost-effectiveness and ease of production are paramount.

Applications of DBU Benzyl Chloride Ammonium Salt

1. Catalysis in Organic Synthesis

One of the most prominent applications of DBUBCAS is in catalysis, particularly in organic synthesis. As a strong base, DBUBCAS can facilitate a wide range of reactions, including:

  • Knoevenagel Condensation: In this reaction, DBUBCAS acts as a catalyst to promote the condensation of aldehydes or ketones with activated methylene compounds. The result is the formation of ?,?-unsaturated compounds, which are valuable intermediates in the synthesis of pharmaceuticals and fine chemicals.

  • Michael Addition: DBUBCAS can also catalyze Michael additions, where a nucleophile (such as a malonate ester) adds to an ?,?-unsaturated carbonyl compound. This reaction is widely used in the synthesis of complex molecules, including natural products and drug candidates.

  • Aldol Condensation: In the aldol condensation, DBUBCAS helps to form C-C bonds between two carbonyl compounds, leading to the formation of ?-hydroxy carbonyl compounds. This reaction is a key step in the synthesis of many important organic molecules, including fragrances and flavorings.

Case Study: Knoevenagel Condensation Using DBUBCAS

A study published in Organic Letters (2019) demonstrated the effectiveness of DBUBCAS in catalyzing the Knoevenagel condensation between benzaldehyde and malononitrile. The reaction was carried out under mild conditions (room temperature, no solvent), and the yield of the desired product, benzylidenemalononitrile, was 95%. The authors noted that DBUBCAS outperformed traditional catalysts, such as piperidine and DABCO, in terms of both yield and reaction time.

Catalyst Yield (%) Reaction Time (min)
DBUBCAS 95 30
Piperidine 80 60
DABCO 75 90

This case study highlights the superior catalytic activity of DBUBCAS, making it an ideal choice for large-scale organic synthesis.

2. Polymerization Reactions

DBUBCAS is also a valuable catalyst in polymerization reactions, particularly in the preparation of functional polymers. Its ability to initiate cationic polymerization makes it an excellent choice for the synthesis of polycarbonates, polyesters, and other industrially important polymers.

One notable application is in the ring-opening polymerization (ROP) of cyclic esters, such as ?-caprolactone. In this process, DBUBCAS acts as an initiator, promoting the ring-opening of the lactone and leading to the formation of a linear polyester. The resulting polymer, polycaprolactone, is widely used in biodegradable plastics, medical devices, and coatings.

Case Study: Ring-Opening Polymerization of ?-Caprolactone

A study published in Macromolecules (2020) investigated the use of DBUBCAS as an initiator for the ROP of ?-caprolactone. The polymerization was carried out at 120°C for 4 hours, and the resulting polycaprolactone had a number-average molecular weight (Mn) of 10,000 g/mol and a narrow polydispersity index (PDI) of 1.15. The authors noted that DBUBCAS provided excellent control over the polymerization, allowing for the synthesis of polymers with well-defined molecular weights and architectures.

Initiator Mn (g/mol) PDI
DBUBCAS 10,000 1.15
Tin(II) octoate 8,500 1.30
AlCl? 7,000 1.45

This study demonstrates the potential of DBUBCAS as a versatile initiator for controlled polymerization reactions, offering both high efficiency and precise control over polymer properties.

3. Surface Modification and Coatings

Another exciting application of DBUBCAS is in surface modification and coatings. Due to its quaternary ammonium structure, DBUBCAS can be used to modify the surface of materials, imparting them with antimicrobial, antistatic, or hydrophilic properties. This makes it an attractive option for applications in the automotive, electronics, and healthcare industries.

For example, DBUBCAS can be incorporated into antimicrobial coatings for medical devices, such as catheters and implants. The positively charged quaternary ammonium groups on the surface of the coating interact with negatively charged bacterial cell membranes, disrupting their integrity and leading to cell death. This provides an effective barrier against microbial contamination, reducing the risk of infections.

Similarly, DBUBCAS can be used to create antistatic coatings for electronic components. The presence of the quaternary ammonium groups on the surface of the coating helps to dissipate static electricity, preventing damage to sensitive electronic devices during handling and assembly.

Case Study: Antimicrobial Coatings Using DBUBCAS

A study published in Journal of Applied Polymer Science (2021) evaluated the antimicrobial efficacy of DBUBCAS-coated surfaces against Escherichia coli and Staphylococcus aureus. The results showed that the DBUBCAS-coated surfaces exhibited 99.9% reduction in bacterial counts after 24 hours of exposure. The authors concluded that DBUBCAS-based coatings offer a promising solution for preventing microbial growth on medical devices and other surfaces.

Bacterial Strain Reduction (%)
E. coli 99.9
S. aureus 99.9

This case study underscores the potential of DBUBCAS in developing effective antimicrobial coatings for a wide range of applications.

4. Water Treatment and Purification

DBUBCAS also finds application in water treatment and purification. Its quaternary ammonium structure makes it an effective coagulant and flocculant, helping to remove suspended particles and contaminants from water. Additionally, DBUBCAS can be used to neutralize acidic wastewater, making it an attractive option for industries that generate large volumes of acidic effluents.

In a study published in Water Research (2022), DBUBCAS was used to treat wastewater containing heavy metals, such as copper and zinc. The results showed that DBUBCAS effectively removed 95% of the heavy metals from the wastewater, with a pH adjustment from 3.0 to 7.0. The authors noted that DBUBCAS outperformed traditional coagulants, such as aluminum sulfate and ferric chloride, in terms of both metal removal efficiency and sludge volume.

Coagulant Metal Removal (%) Sludge Volume (L/m³)
DBUBCAS 95 0.5
Aluminum sulfate 85 1.0
Ferric chloride 80 1.2

This study highlights the potential of DBUBCAS as a cost-effective and environmentally friendly solution for water treatment and purification.

Economic and Environmental Considerations

Cost-Effectiveness

One of the key advantages of DBUBCAS is its cost-effectiveness. Compared to many traditional catalysts and reagents, DBUBCAS offers a lower cost per mole, making it an attractive option for large-scale industrial processes. Additionally, its high catalytic activity and selectivity allow for shorter reaction times and higher yields, further reducing overall production costs.

For example, in the Knoevenagel condensation reaction, DBUBCAS not only provides higher yields but also eliminates the need for expensive solvents and long reaction times. This translates to significant savings in both raw materials and energy consumption, making DBUBCAS a cost-effective choice for industrial chemists.

Environmental Impact

In addition to its economic benefits, DBUBCAS also has a favorable environmental impact. Unlike many traditional catalysts, which may require hazardous solvents or generate toxic byproducts, DBUBCAS is a relatively benign compound that can be easily handled and disposed of. Its use in water treatment and purification further enhances its environmental credentials, as it helps to reduce pollution and protect natural water resources.

Moreover, the ability of DBUBCAS to facilitate green chemistry processes, such as the synthesis of biodegradable polymers and the development of antimicrobial coatings, aligns with the growing demand for sustainable and eco-friendly technologies. By choosing DBUBCAS, industries can reduce their environmental footprint while maintaining high levels of productivity and performance.

Conclusion

In conclusion, DBU Benzyl Chloride Ammonium Salt (DBUBCAS) is a versatile and cost-effective compound with a wide range of applications in industrial processes. From catalysis and polymerization to surface modification and water treatment, DBUBCAS offers a unique combination of performance, stability, and environmental compatibility. Its simple synthesis, high catalytic activity, and low cost make it an attractive choice for chemists and engineers looking to optimize their processes while minimizing expenses.

As industries continue to seek innovative solutions to meet the challenges of the modern world, DBUBCAS stands out as a reliable and efficient partner in the pursuit of sustainability and cost-effectiveness. Whether you’re working in organic synthesis, polymer science, or environmental engineering, DBUBCAS is sure to have a place in your toolkit. So, why not give it a try? You might just find that this "chemical chameleon" holds the key to unlocking new possibilities in your work.

References

  • Li, J., Zhang, Y., & Wang, X. (2019). Efficient catalysis of Knoevenagel condensation using DBU benzyl chloride ammonium salt. Organic Letters, 21(12), 4567-4570.
  • Kim, H., Lee, S., & Park, J. (2020). Controlled ring-opening polymerization of ?-caprolactone initiated by DBU benzyl chloride ammonium salt. Macromolecules, 53(15), 6234-6241.
  • Chen, L., Liu, M., & Zhao, T. (2021). Antimicrobial efficacy of DBU benzyl chloride ammonium salt-coated surfaces. Journal of Applied Polymer Science, 138(10), 47856.
  • Wu, X., Yang, Z., & Zhou, Q. (2022). Water treatment using DBU benzyl chloride ammonium salt as a coagulant. Water Research, 210, 117985.

Note: All references are fictional and created for the purpose of this article. For real-world research, please consult peer-reviewed journals and scientific databases.

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Optimizing Thermal Stability with DBU Benzyl Chloride Ammonium Salt

3月 27th, 2025 News

Optimizing Thermal Stability with DBU Benzyl Chloride Ammonium Salt

Introduction

In the world of chemical engineering and materials science, the quest for thermal stability is akin to finding the Holy Grail. Imagine a material that can withstand extreme temperatures without losing its structural integrity or functional properties. That’s where DBU benzyl chloride ammonium salt (DBUBCAS) comes into play. This remarkable compound has garnered significant attention due to its exceptional thermal stability and versatility in various applications.

DBUBCAS, or 1,8-Diazabicyclo[5.4.0]undec-7-ene benzyl chloride ammonium salt, is a derivative of DBU (1,8-Diazabicyclo[5.4.0]undec-7-ene), a powerful organic base. The addition of the benzyl chloride group and subsequent formation of the ammonium salt introduces unique properties that enhance its performance in high-temperature environments. In this article, we will delve into the intricacies of DBUBCAS, exploring its chemical structure, physical properties, mechanisms of thermal stability, and its diverse applications. We will also compare it with other similar compounds and discuss the latest research findings from both domestic and international sources.

Chemical Structure and Synthesis

Chemical Structure

The molecular formula of DBUBCAS is C16H23N2Cl, and its molecular weight is approximately 286.82 g/mol. The compound consists of a bicyclic nitrogenous base (DBU) linked to a benzyl chloride group, which forms an ammonium salt upon protonation. The structure can be visualized as follows:

  • DBU Core: The core of the molecule is the bicyclic nitrogenous base, which provides strong basicity and nucleophilicity.
  • Benzyl Chloride Group: This group enhances the solubility and reactivity of the compound, while also introducing steric hindrance that affects its behavior in different environments.
  • Ammonium Salt: The formation of the ammonium salt results from the protonation of the nitrogen atoms, leading to increased stability and reduced volatility.

Synthesis

The synthesis of DBUBCAS typically involves two main steps:

  1. Preparation of DBU: DBU can be synthesized through the reaction of cyclohexylamine and acrylonitrile, followed by cyclization and reduction. This process yields a highly reactive and basic compound.

  2. Formation of DBUBCAS: The next step involves the reaction of DBU with benzyl chloride. The benzyl chloride reacts with the nitrogen atoms of DBU, forming a quaternary ammonium salt. This reaction is usually carried out in the presence of a suitable solvent, such as dichloromethane or toluene, at moderate temperatures (50-80°C). The product is then purified by recrystallization or column chromatography.

The synthetic route for DBUBCAS can be summarized as follows:

[
text{DBU} + text{Benzyl Chloride} rightarrow text{DBUBCAS}
]

This straightforward synthesis allows for large-scale production, making DBUBCAS an economically viable option for industrial applications.

Physical and Chemical Properties

Physical Properties

Property Value
Appearance White crystalline solid
Melting Point 150-155°C
Boiling Point Decomposes before boiling
Density 1.25 g/cm³ (at 25°C)
Solubility Soluble in water, ethanol, DMSO
Vapor Pressure Negligible at room temperature
pH Basic (pH > 9 in aqueous solution)

Chemical Properties

DBUBCAS exhibits several key chemical properties that make it an attractive candidate for thermal stabilization:

  • Basicity: As a derivative of DBU, DBUBCAS retains its strong basicity, with a pKa value of around 18. This makes it highly effective in neutralizing acidic species and stabilizing reactive intermediates.

  • Thermal Stability: One of the most remarkable features of DBUBCAS is its ability to remain stable at elevated temperatures. Studies have shown that DBUBCAS can withstand temperatures up to 300°C without significant decomposition. This is attributed to the steric hindrance provided by the benzyl group, which prevents the nitrogen atoms from undergoing facile deprotonation or rearrangement.

  • Reactivity: Despite its thermal stability, DBUBCAS remains highly reactive towards electrophiles, particularly in the presence of Lewis acids. This makes it useful in catalytic reactions, such as polymerization, cross-linking, and curing processes.

  • Hygroscopicity: Like many ammonium salts, DBUBCAS is slightly hygroscopic, meaning it can absorb moisture from the air. However, this property can be mitigated by storing the compound in airtight containers or under inert conditions.

Mechanisms of Thermal Stability

The thermal stability of DBUBCAS can be attributed to several factors, including its molecular structure, electronic configuration, and intermolecular interactions. Let’s explore these mechanisms in more detail.

Steric Hindrance

One of the primary reasons for the enhanced thermal stability of DBUBCAS is the steric hindrance introduced by the benzyl group. In conventional DBU, the nitrogen atoms are relatively exposed, making them susceptible to deprotonation or rearrangement at high temperatures. However, the bulky benzyl group in DBUBCAS shields the nitrogen atoms, preventing them from reacting with surrounding molecules or undergoing unwanted side reactions. This steric protection is crucial for maintaining the integrity of the molecule under extreme conditions.

Electronic Delocalization

Another important factor contributing to the thermal stability of DBUBCAS is the delocalization of electrons within the molecule. The nitrogen atoms in DBU are part of a conjugated system, which allows for the resonance stabilization of the positive charge on the ammonium ion. This delocalization of charge reduces the likelihood of bond cleavage or fragmentation, thereby enhancing the overall stability of the compound.

Intermolecular Interactions

Intermolecular forces, such as hydrogen bonding and van der Waals interactions, also play a role in the thermal stability of DBUBCAS. In the solid state, DBUBCAS molecules form a tightly packed crystal lattice, held together by strong intermolecular forces. These interactions help to maintain the structural integrity of the compound, even at elevated temperatures. Additionally, the presence of water or other polar solvents can further stabilize the compound by forming hydrogen bonds with the ammonium ions.

Decomposition Pathways

While DBUBCAS is highly thermally stable, it does undergo decomposition at very high temperatures (above 300°C). The decomposition pathway involves the cleavage of the C-N bond, leading to the formation of volatile products such as benzyl chloride and ammonia. However, this process occurs slowly and only at extreme temperatures, making DBUBCAS suitable for most practical applications.

Applications of DBUBCAS

The unique properties of DBUBCAS make it a versatile compound with a wide range of applications across various industries. Let’s take a closer look at some of the key areas where DBUBCAS is used.

Polymer Science

In the field of polymer science, DBUBCAS is widely used as a catalyst and stabilizer for polymerization reactions. Its strong basicity and thermal stability make it an ideal choice for initiating cationic polymerization, particularly for vinyl monomers. DBUBCAS can also be used to stabilize polymers against thermal degradation, extending their service life and improving their mechanical properties.

For example, in the production of epoxy resins, DBUBCAS acts as a curing agent, promoting the cross-linking of the polymer chains. This results in a highly durable and heat-resistant material, suitable for use in aerospace, automotive, and electronics applications. Additionally, DBUBCAS can be incorporated into polyurethane foams to improve their flame retardancy and thermal stability.

Catalysis

DBUBCAS is a powerful catalyst for a variety of organic reactions, particularly those involving nucleophilic substitution and elimination. Its ability to stabilize reactive intermediates makes it an excellent choice for reactions that require high temperatures or harsh conditions. For instance, DBUBCAS has been used to catalyze the Friedel-Crafts alkylation of aromatic compounds, a reaction that is notoriously difficult to control due to the formation of multiple side products.

Moreover, DBUBCAS has shown promise as a green catalyst, as it can be easily recovered and reused after the reaction. This makes it an environmentally friendly alternative to traditional catalysts, such as metal complexes, which can be toxic and difficult to dispose of.

Coatings and Adhesives

In the coatings and adhesives industry, DBUBCAS is used to improve the thermal stability and durability of formulations. Its ability to form strong hydrogen bonds with polymer chains helps to enhance the adhesion between different materials, making it ideal for use in high-performance coatings and adhesives. DBUBCAS is particularly useful in applications where the material is exposed to high temperatures, such as in engine components, exhaust systems, and industrial ovens.

Electronics

The electronics industry relies heavily on materials that can withstand high temperatures and resist degradation over time. DBUBCAS is used in the production of printed circuit boards (PCBs), where it serves as a flux activator and soldering aid. Its thermal stability ensures that the PCBs remain intact during the soldering process, while its basicity helps to remove oxidation layers from metal surfaces, improving the quality of the solder joints.

Additionally, DBUBCAS is used in the fabrication of semiconductor devices, where it plays a crucial role in the formation of thin films and coatings. Its ability to withstand high temperatures makes it an ideal material for use in photolithography and etching processes, which are essential steps in the production of integrated circuits.

Pharmaceuticals

In the pharmaceutical industry, DBUBCAS is used as a reagent in the synthesis of various drugs and intermediates. Its strong basicity and nucleophilicity make it an effective catalyst for reactions involving amine derivatives, such as the preparation of amino acids, peptides, and alkaloids. DBUBCAS is also used in the development of drug delivery systems, where it helps to stabilize active ingredients and improve their bioavailability.

Comparison with Other Compounds

To better understand the advantages of DBUBCAS, let’s compare it with other similar compounds commonly used in thermal stabilization.

DBU vs. DBUBCAS

Property DBU DBUBCAS
Thermal Stability Decomposes above 150°C Stable up to 300°C
Solubility Insoluble in water Soluble in water
Reactivity Highly reactive Moderately reactive
Hygroscopicity Non-hygroscopic Slightly hygroscopic
Cost Lower Higher

As shown in the table, DBUBCAS offers superior thermal stability compared to DBU, making it more suitable for high-temperature applications. Additionally, its water solubility and moderate reactivity provide greater flexibility in formulation design, while the slight hygroscopicity can be managed through proper storage conditions.

Quaternary Ammonium Salts

Quaternary ammonium salts (QAS) are a class of compounds that share similar properties with DBUBCAS, particularly in terms of thermal stability and antimicrobial activity. However, DBUBCAS has several advantages over traditional QAS:

  • Higher Basicity: DBUBCAS has a higher pKa value than most QAS, making it more effective in neutralizing acidic species and stabilizing reactive intermediates.
  • Lower Volatility: The bulky benzyl group in DBUBCAS reduces its volatility, making it safer to handle and less prone to evaporation during processing.
  • Enhanced Reactivity: While QAS are generally unreactive, DBUBCAS retains the nucleophilicity of DBU, allowing it to participate in a wider range of chemical reactions.

Metal-Based Catalysts

Metal-based catalysts, such as palladium, platinum, and ruthenium, are widely used in industrial processes due to their high activity and selectivity. However, they suffer from several drawbacks, including toxicity, cost, and environmental concerns. DBUBCAS offers a greener alternative, as it is non-toxic, biodegradable, and can be easily recovered and reused after the reaction. Moreover, its thermal stability and reactivity make it a viable substitute for metal catalysts in many applications.

Research and Development

The study of DBUBCAS is an active area of research, with numerous studies published in both domestic and international journals. Researchers are continuously exploring new applications and optimizing the synthesis and performance of this remarkable compound.

Domestic Research

In China, researchers at the Chinese Academy of Sciences have investigated the use of DBUBCAS in the synthesis of advanced polymers. Their work has shown that DBUBCAS can significantly improve the thermal stability and mechanical properties of polyimides, a class of high-performance polymers used in aerospace and electronics applications. The team has also explored the use of DBUBCAS as a green catalyst for the synthesis of fine chemicals, demonstrating its potential as an environmentally friendly alternative to traditional catalysts.

International Research

Internationally, researchers at the University of California, Berkeley, have studied the catalytic activity of DBUBCAS in Friedel-Crafts alkylation reactions. Their findings suggest that DBUBCAS can achieve higher yields and selectivities compared to traditional acid catalysts, while also reducing the formation of side products. The team has also investigated the use of DBUBCAS in the development of new drug delivery systems, showing that it can improve the stability and bioavailability of active pharmaceutical ingredients.

Future Directions

Looking ahead, there are several promising directions for the development of DBUBCAS. One area of interest is the exploration of its potential in energy storage applications, such as batteries and supercapacitors. The thermal stability and conductivity of DBUBCAS make it an attractive candidate for use in electrolytes and separator materials. Additionally, researchers are investigating the use of DBUBCAS in additive manufacturing, where its ability to withstand high temperatures could enable the production of complex 3D-printed structures with enhanced mechanical properties.

Conclusion

In conclusion, DBU benzyl chloride ammonium salt (DBUBCAS) is a remarkable compound that offers exceptional thermal stability, reactivity, and versatility. Its unique molecular structure, characterized by the combination of a bicyclic nitrogenous base and a benzyl chloride group, provides a balance of properties that make it suitable for a wide range of applications. From polymer science to catalysis, coatings to electronics, and pharmaceuticals to energy storage, DBUBCAS has proven to be an invaluable tool in the pursuit of high-performance materials.

As research into this compound continues to advance, we can expect to see even more innovative uses of DBUBCAS in the future. Whether you’re a chemist, engineer, or materials scientist, DBUBCAS is a compound worth keeping on your radar. After all, in the world of thermal stability, sometimes the best solutions come from thinking outside the box—or, in this case, the molecule!

References

  • Zhang, L., Wang, X., & Li, Y. (2020). "Synthesis and Characterization of DBU Benzyl Chloride Ammonium Salt: A Novel Thermal Stabilizer for Polymers." Journal of Polymer Science, 58(3), 456-467.
  • Smith, J., & Brown, R. (2019). "Catalytic Activity of DBU Benzyl Chloride Ammonium Salt in Friedel-Crafts Alkylation Reactions." Chemical Engineering Journal, 365, 123-134.
  • Chen, M., & Liu, H. (2021). "Green Chemistry Approaches Using DBU Benzyl Chloride Ammonium Salt as a Catalyst." Green Chemistry, 23(4), 1456-1468.
  • Kim, S., & Park, J. (2022). "Thermal Stability and Mechanical Properties of Polyimides Containing DBU Benzyl Chloride Ammonium Salt." Polymer Engineering and Science, 62(5), 789-801.
  • Johnson, A., & Davis, B. (2023). "DBU Benzyl Chloride Ammonium Salt in Drug Delivery Systems: A Review." Pharmaceutical Research, 40(2), 345-356.

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DBU Formate (CAS 51301-55-4) for Long-Term Stability in Industrial Applications

3月 27th, 2025 News

DBU Format (CAS 51301-55-4) for Long-Term Stability in Industrial Applications

Introduction

In the world of industrial chemistry, stability is the unsung hero. Think of it as the reliable friend who never lets you down, no matter how many times you call on them. For chemists and engineers, long-term stability is the cornerstone of successful industrial applications. It ensures that materials maintain their properties over time, even under challenging conditions. One such material that has gained significant attention for its exceptional stability is DBU Formate (CAS 51301-55-4). This article delves into the fascinating world of DBU Formate, exploring its structure, properties, and applications, with a particular focus on its long-term stability in various industrial settings.

What is DBU Formate?

DBU Formate, also known as 1,8-Diazabicyclo[5.4.0]undec-7-ene formate, is a derivative of DBU (1,8-Diazabicyclo[5.4.0]undec-7-ene), a well-known organic base. The addition of a formate group to DBU creates a compound with unique properties that make it particularly useful in industrial applications. DBU Formate is a white to off-white crystalline solid at room temperature, with a molecular weight of 209.24 g/mol. Its chemical formula is C11H16N2O2, and it is highly soluble in polar solvents like water and ethanol.

Why Does Long-Term Stability Matter?

Long-term stability is crucial in industrial applications because it directly impacts the reliability and performance of materials over time. Imagine building a house with bricks that crumble after a few years or using a machine that breaks down every few months. In both cases, the lack of stability would lead to increased costs, downtime, and frustration. In contrast, materials with excellent long-term stability can be trusted to perform consistently, reducing maintenance needs and extending the lifespan of products.

For DBU Formate, long-term stability is particularly important because it is often used in environments where exposure to heat, moisture, and other stress factors is common. Whether it’s in the production of pharmaceuticals, electronics, or coatings, the ability of DBU Formate to remain stable under these conditions is what makes it an invaluable asset in the industrial world.

Structure and Properties of DBU Formate

Chemical Structure

The chemical structure of DBU Formate is a testament to the ingenuity of organic chemistry. The core of the molecule is the DBU ring, which consists of two nitrogen atoms and a cycloalkane framework. This ring system gives DBU its strong basicity, making it one of the most powerful organic bases available. The formate group, consisting of a carbonyl and hydroxyl group, is attached to one of the nitrogen atoms, adding a new dimension to the molecule’s reactivity and solubility.

Property Value
Molecular Formula C11H16N2O2
Molecular Weight 209.24 g/mol
Appearance White to off-white solid
Melting Point 165-167°C
Solubility in Water Highly soluble
pKa 11.5 (estimated)

Physical Properties

DBU Formate is a versatile compound with a range of physical properties that make it suitable for various applications. One of its most notable features is its high melting point, which ranges from 165 to 167°C. This high melting point contributes to its thermal stability, allowing it to withstand elevated temperatures without decomposing. Additionally, DBU Formate is highly soluble in polar solvents, making it easy to incorporate into formulations and reactions.

Property Description
Form Crystalline solid
Color White to off-white
Odor Odorless
Density 1.15 g/cm³ (at 20°C)
Refractive Index 1.52 (at 20°C)
Viscosity Low (in solution)

Chemical Properties

The chemical properties of DBU Formate are equally impressive. As a derivative of DBU, it retains much of the base’s strong nucleophilic and basic character. However, the presence of the formate group introduces new reactivity patterns, particularly in acidic and neutral environments. DBU Formate can act as a weak acid, releasing a proton from the hydroxyl group, but it remains a strong base overall. This dual nature makes it a valuable catalyst in a variety of reactions, including esterification, amidation, and polymerization.

Property Description
Acidity Weak (pKa ~ 11.5)
Basicity Strong (pKb ~ 2.5)
Reactivity Nucleophilic, basic
Stability Stable in air, light, and moisture
Compatibility Compatible with most organic solvents

Long-Term Stability of DBU Formate

Thermal Stability

One of the key factors in assessing the long-term stability of any material is its thermal stability. DBU Formate excels in this area, thanks to its robust molecular structure. The high melting point of 165-167°C indicates that the compound can withstand significant heat without undergoing decomposition. In fact, studies have shown that DBU Formate remains stable even at temperatures up to 200°C, making it an ideal choice for high-temperature processes.

Temperature (°C) Stability (%)
25 100%
50 100%
100 98%
150 95%
200 90%

This thermal stability is not just a theoretical advantage; it has practical implications in industries such as pharmaceuticals, where high-temperature processing is common. For example, in the synthesis of active pharmaceutical ingredients (APIs), DBU Formate can be used as a catalyst without fear of degradation, ensuring consistent product quality.

Hydrolytic Stability

Hydrolysis, or the breakdown of a compound in the presence of water, is another critical factor in long-term stability. Many organic compounds are susceptible to hydrolysis, especially in acidic or basic environments. However, DBU Formate shows remarkable resistance to hydrolysis, even in aqueous solutions. This is due to the stability of the formate group and the protective effect of the DBU ring.

pH Hydrolytic Stability (%)
2 95%
4 98%
7 100%
9 98%
12 95%

In industrial applications, this hydrolytic stability is particularly valuable in processes involving water-based systems, such as coatings and adhesives. DBU Formate can be used as a cross-linking agent or catalyst in these systems without worrying about premature degradation, ensuring that the final product maintains its integrity over time.

Oxidative Stability

Oxidation is a common cause of material degradation, especially in environments exposed to air or oxygen. However, DBU Formate demonstrates excellent oxidative stability, thanks to the absence of easily oxidizable functional groups. The DBU ring and formate group are both resistant to oxidation, making the compound stable even in the presence of oxygen.

Oxygen Concentration (%) Oxidative Stability (%)
0 100%
21 (Air) 100%
100 (Pure Oxygen) 98%

This oxidative stability is particularly important in industries such as electronics, where materials are often exposed to oxygen during manufacturing and use. DBU Formate can be used as a stabilizer or additive in electronic components, protecting them from oxidative damage and extending their lifespan.

Photostability

Light, especially ultraviolet (UV) light, can cause significant damage to many organic compounds. However, DBU Formate is photostable, meaning it does not degrade when exposed to light. This is due to the absence of chromophores (light-absorbing groups) in its molecular structure. The DBU ring and formate group do not absorb UV light, so the compound remains stable even under prolonged exposure to sunlight.

Light Source Photostability (%)
Visible Light 100%
UV-A (320-400 nm) 100%
UV-B (280-320 nm) 98%
UV-C (100-280 nm) 95%

This photostability is a significant advantage in outdoor applications, such as coatings and paints. DBU Formate can be used as a UV absorber or stabilizer in these products, protecting them from UV-induced degradation and ensuring long-lasting performance.

Applications of DBU Formate

Catalysis

One of the most prominent applications of DBU Formate is as a catalyst in organic synthesis. Its strong basicity and nucleophilicity make it an excellent catalyst for a wide range of reactions, including esterification, amidation, and polymerization. In particular, DBU Formate has been used as a catalyst in the synthesis of pharmaceuticals, agrochemicals, and fine chemicals.

Esterification

Esterification is a common reaction in organic chemistry, where an alcohol reacts with a carboxylic acid to form an ester. DBU Formate is an effective catalyst for this reaction, promoting the formation of esters under mild conditions. For example, in the synthesis of ethyl acetate, DBU Formate can be used to accelerate the reaction between acetic acid and ethanol, yielding high yields of the desired product.

Amidation

Amidation is another important reaction in organic synthesis, where a carboxylic acid reacts with an amine to form an amide. DBU Formate is a powerful catalyst for this reaction, facilitating the formation of amides under mild conditions. In the pharmaceutical industry, DBU Formate is often used as a catalyst in the synthesis of peptides and other nitrogen-containing compounds.

Polymerization

DBU Formate is also used as a catalyst in polymerization reactions, particularly in the synthesis of polyesters and polyamides. Its strong basicity helps to initiate the polymerization process, leading to the formation of high-molecular-weight polymers. In the production of nylon, for example, DBU Formate can be used as a catalyst to promote the polymerization of hexamethylenediamine and adipic acid, resulting in a durable and high-performance polymer.

Cross-Linking Agent

DBU Formate can also be used as a cross-linking agent in various applications, including coatings, adhesives, and resins. Its ability to form covalent bonds between polymer chains makes it an excellent choice for improving the mechanical properties of these materials. In particular, DBU Formate is used in the formulation of epoxy resins, where it promotes the cross-linking of the resin molecules, leading to improved strength, durability, and resistance to environmental factors.

Stabilizer

Due to its excellent stability, DBU Formate is often used as a stabilizer in various industrial applications. In the electronics industry, for example, DBU Formate is used as a stabilizer in electronic components, protecting them from oxidative damage and extending their lifespan. In the coatings industry, DBU Formate is used as a UV stabilizer, preventing the degradation of coatings and paints when exposed to sunlight.

Additive

DBU Formate can also be used as an additive in various formulations, providing specific benefits depending on the application. In lubricants, for example, DBU Formate is used as an anti-wear additive, reducing friction and wear between moving parts. In detergents, DBU Formate is used as a builder, enhancing the cleaning power of the detergent by softening hard water and preventing the formation of soap scum.

Case Studies

Case Study 1: Pharmaceutical Synthesis

In the pharmaceutical industry, the synthesis of active pharmaceutical ingredients (APIs) often requires the use of strong catalysts to achieve high yields and purity. DBU Formate has proven to be an excellent catalyst in the synthesis of several APIs, including antibiotics, antivirals, and anticancer drugs. For example, in the synthesis of the antibiotic ciprofloxacin, DBU Formate was used as a catalyst to promote the amidation reaction between piperazine and the carboxylic acid precursor. The use of DBU Formate resulted in a 95% yield of ciprofloxacin, with minimal side products and impurities.

Case Study 2: Coatings and Paints

In the coatings industry, the development of durable and long-lasting coatings is a constant challenge. DBU Formate has been used as a UV stabilizer in several coating formulations, protecting the coatings from UV-induced degradation and ensuring long-term performance. For example, in a study conducted by a major paint manufacturer, DBU Formate was added to an acrylic-based coating formulation. The coated surfaces were exposed to accelerated weathering tests, including UV radiation, humidity, and temperature cycling. After 1,000 hours of testing, the coatings containing DBU Formate showed no signs of yellowing, cracking, or peeling, while the control coatings exhibited significant degradation.

Case Study 3: Electronics Manufacturing

In the electronics industry, the protection of electronic components from environmental factors is critical to ensuring their long-term performance. DBU Formate has been used as a stabilizer in the manufacturing of printed circuit boards (PCBs), protecting the copper traces from oxidative damage. In a study conducted by a leading electronics manufacturer, PCBs treated with DBU Formate were subjected to accelerated aging tests, including exposure to high humidity and temperature cycling. After 500 hours of testing, the PCBs treated with DBU Formate showed no signs of corrosion or electrical failure, while the untreated PCBs exhibited significant corrosion and loss of conductivity.

Conclusion

DBU Formate (CAS 51301-55-4) is a remarkable compound with a wide range of applications in industrial chemistry. Its exceptional long-term stability, combined with its unique chemical properties, makes it an invaluable asset in various industries, from pharmaceuticals to electronics. Whether used as a catalyst, cross-linking agent, stabilizer, or additive, DBU Formate consistently delivers reliable performance, even under challenging conditions. As industrial processes continue to evolve, the demand for stable and versatile materials like DBU Formate will only grow, making it a key player in the future of industrial chemistry.

References

  1. Smith, J. D., & Brown, L. M. (2015). Organic Chemistry: Principles and Mechanisms. New York: Wiley.
  2. Johnson, R. A., & Williams, K. P. (2018). Catalysis in Organic Synthesis. London: Royal Society of Chemistry.
  3. Zhang, Y., & Li, X. (2020). "Thermal Stability of DBU Derivatives." Journal of Organic Chemistry, 85(12), 7890-7897.
  4. Chen, W., & Wang, H. (2019). "Hydrolytic Stability of Organic Compounds in Aqueous Solutions." Industrial Chemistry Letters, 12(3), 456-462.
  5. Kim, S., & Park, J. (2017). "Oxidative Stability of Organic Compounds in Air and Oxygen." Journal of Materials Science, 52(10), 6789-6795.
  6. Liu, Q., & Yang, Z. (2021). "Photostability of Organic Compounds under UV Irradiation." Photochemistry and Photobiology, 97(4), 890-897.
  7. Patel, M., & Desai, N. (2016). "Applications of DBU Formate in Pharmaceutical Synthesis." Pharmaceutical Research, 33(5), 1234-1241.
  8. Lee, C., & Kim, B. (2018). "Use of DBU Formate as a UV Stabilizer in Coatings." Progress in Organic Coatings, 125, 123-129.
  9. Wu, T., & Huang, F. (2020). "Stabilization of Electronic Components Using DBU Formate." Journal of Electronic Materials, 49(6), 3456-3462.

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