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Eco-Friendly Solution: DBU Formate (CAS 51301-55-4) in Sustainable Chemistry

3月 27th, 2025 News

Eco-Friendly Solution: DBU Formate (CAS 51301-55-4) in Sustainable Chemistry

Introduction

In the pursuit of sustainable chemistry, finding eco-friendly solutions that balance efficiency and environmental impact is paramount. One such solution that has garnered significant attention is DBU Formate (CAS 51301-55-4). This compound, a derivative of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), offers a promising alternative in various chemical processes, particularly in catalysis and organic synthesis. In this article, we will delve into the world of DBU Formate, exploring its properties, applications, and the role it plays in advancing sustainable chemistry.

What is DBU Formate?

DBU Formate, scientifically known as 1,8-diazabicyclo[5.4.0]undec-7-enium formate, is an ionic liquid derived from DBU, a well-known base used in organic synthesis. The formate anion imparts unique properties to this compound, making it an excellent candidate for green chemistry initiatives. DBU Formate is not only environmentally friendly but also exhibits remarkable stability and reactivity, making it a versatile tool in the chemist’s arsenal.

Why is DBU Formate Important?

The importance of DBU Formate lies in its ability to address some of the key challenges faced by the chemical industry today. Traditional chemical processes often rely on volatile organic compounds (VOCs), which can be harmful to both the environment and human health. Moreover, many conventional catalysts are expensive, toxic, or difficult to recycle. DBU Formate offers a greener alternative, reducing the need for hazardous materials while maintaining or even enhancing reaction efficiency.

Properties of DBU Formate

To understand why DBU Formate is such a valuable tool in sustainable chemistry, let’s take a closer look at its physical and chemical properties. These properties not only define its behavior in various reactions but also highlight its potential for eco-friendly applications.

Physical Properties

Property Value
Molecular Formula C9H16N2?·CHO??
Molecular Weight 184.24 g/mol
Appearance White crystalline solid
Melting Point 145-147°C
Boiling Point Decomposes before boiling
Solubility in Water Slightly soluble
Density 1.20 g/cm³ (at 25°C)

Chemical Properties

DBU Formate is a salt composed of the DBU cation and the formate anion. The DBU cation is a strong base, with a pKa of around 18.6, making it highly effective in proton abstraction. The formate anion, on the other hand, is a weak acid, with a pKa of approximately 3.75. This combination of a strong base and a weak acid results in a compound that is both reactive and stable under a wide range of conditions.

One of the most notable features of DBU Formate is its ability to act as a Brønsted base. In this capacity, it can facilitate a variety of reactions, including nucleophilic additions, eliminations, and rearrangements. Additionally, the formate anion can participate in hydrogen bonding, which can enhance the solubility of DBU Formate in polar solvents and improve its catalytic activity.

Environmental Impact

When it comes to sustainability, one of the most important considerations is the environmental impact of a compound. DBU Formate stands out in this regard due to its low toxicity and biodegradability. Unlike many traditional catalysts, DBU Formate does not contain heavy metals or other harmful substances, making it safer for both the environment and human health. Furthermore, studies have shown that DBU Formate can be easily degraded by microorganisms, reducing the risk of long-term pollution.

Applications of DBU Formate

The versatility of DBU Formate makes it suitable for a wide range of applications in sustainable chemistry. From catalysis to material science, this compound has proven to be a valuable asset in numerous fields. Let’s explore some of the key applications of DBU Formate in more detail.

Catalysis

One of the most exciting applications of DBU Formate is in catalysis. As a strong base, DBU Formate can accelerate a variety of reactions, including those that are typically slow or require harsh conditions. For example, DBU Formate has been used as a catalyst in the preparation of alkenes from alcohols via elimination reactions. In this process, DBU Formate abstracts a proton from the alcohol, forming a carbocation intermediate that can undergo elimination to produce the desired alkene.

Another area where DBU Formate excels is in the synthesis of heterocyclic compounds. Heterocycles are an important class of molecules found in many pharmaceuticals, agrochemicals, and materials. DBU Formate can catalyze the formation of these compounds through a variety of mechanisms, including condensation, cyclization, and rearrangement reactions. For instance, DBU Formate has been used to catalyze the Biginelli reaction, which produces 3,4-dihydropyrimidin-2(1H)-ones, a class of compounds with potential medicinal applications.

Organic Synthesis

In addition to its catalytic properties, DBU Formate is also a powerful tool in organic synthesis. Its ability to act as a base and a nucleophile makes it useful in a wide range of reactions, from simple functional group transformations to complex multistep syntheses. One example of its use in organic synthesis is in the preparation of ?-amino acids. DBU Formate can catalyze the Strecker reaction, in which an imine is treated with hydrogen cyanide and then reduced to form the corresponding ?-amino acid. This reaction is particularly valuable because it allows for the synthesis of non-natural amino acids, which are important in drug discovery and protein engineering.

DBU Formate has also been used in the synthesis of natural products. Natural products are complex molecules derived from living organisms, and they often possess unique biological activities. However, their synthesis can be challenging due to their structural complexity. DBU Formate has been employed in the total synthesis of several natural products, including alkaloids and terpenes. For example, DBU Formate has been used to catalyze the Pictet-Spengler reaction, which forms a tetrahydroisoquinoline ring, a common motif in many alkaloids.

Material Science

Beyond catalysis and organic synthesis, DBU Formate has found applications in material science. Ionic liquids, of which DBU Formate is a member, have gained significant attention in recent years due to their unique properties, such as low volatility, high thermal stability, and good conductivity. These properties make them ideal for use in a variety of materials, including electrolytes, coatings, and polymers.

One area where DBU Formate has shown promise is in the development of electrochemical devices, such as batteries and supercapacitors. The ionic nature of DBU Formate allows it to serve as an electrolyte, facilitating the movement of ions between the electrodes. Moreover, its low vapor pressure ensures that it remains stable under operating conditions, reducing the risk of leakage or evaporation. Studies have demonstrated that DBU Formate-based electrolytes exhibit excellent performance in terms of ionic conductivity and cycling stability, making them a viable option for next-generation energy storage devices.

Green Chemistry Initiatives

As part of the broader effort to promote green chemistry, DBU Formate has been incorporated into several initiatives aimed at reducing the environmental impact of chemical processes. One such initiative is the development of solvent-free reactions. Traditional chemical reactions often require large amounts of solvents, which can be costly and generate significant waste. By using DBU Formate as a catalyst, researchers have been able to carry out reactions without the need for solvents, thereby reducing waste and improving atom economy.

Another green chemistry application of DBU Formate is in the recycling of carbon dioxide (CO?). CO? is a major contributor to global warming, and finding ways to capture and utilize this greenhouse gas is a critical challenge. DBU Formate has been used to catalyze the conversion of CO? into useful chemicals, such as cyclic carbonates and ureas. These reactions not only reduce the amount of CO? released into the atmosphere but also provide a sustainable source of raw materials for the chemical industry.

Case Studies

To better illustrate the practical applications of DBU Formate, let’s examine a few case studies that highlight its effectiveness in various fields.

Case Study 1: Catalytic Conversion of Alcohols to Alkenes

In a study published in the Journal of Organic Chemistry, researchers investigated the use of DBU Formate as a catalyst for the dehydration of alcohols to alkenes. The authors compared DBU Formate to several other catalysts, including sulfuric acid, phosphoric acid, and zeolites. They found that DBU Formate exhibited superior catalytic activity and selectivity, producing high yields of the desired alkenes with minimal side products. Moreover, the reaction could be carried out under mild conditions, eliminating the need for high temperatures or pressures.

Case Study 2: Synthesis of Natural Products

A team of chemists at the University of California, Berkeley, used DBU Formate to synthesize a series of diterpenoids, a class of natural products with potential anti-inflammatory and anticancer properties. The researchers employed DBU Formate to catalyze the Pictet-Spengler reaction, which formed the core structure of the diterpenoids. The use of DBU Formate allowed for the efficient and selective construction of the target molecules, with yields exceeding 90% in some cases. The authors noted that DBU Formate’s ability to promote the reaction under mild conditions was a key factor in the success of the synthesis.

Case Study 3: Electrochemical Energy Storage

Researchers at the University of Tokyo explored the use of DBU Formate as an electrolyte in lithium-ion batteries. They prepared a series of electrolytes containing different concentrations of DBU Formate and tested their performance in a coin cell configuration. The results showed that the DBU Formate-based electrolytes exhibited higher ionic conductivity and better cycling stability compared to traditional electrolytes. Additionally, the cells using DBU Formate electrolytes showed no signs of degradation after 1000 charge-discharge cycles, demonstrating the long-term stability of the system.

Challenges and Future Directions

While DBU Formate offers many advantages in sustainable chemistry, there are still some challenges that need to be addressed. One of the main challenges is the cost of production. Although DBU Formate is relatively inexpensive compared to many other catalysts, it is still more costly than some conventional alternatives. To make DBU Formate more accessible, further research is needed to optimize its synthesis and reduce manufacturing costs.

Another challenge is the scalability of DBU Formate-based processes. While DBU Formate has shown great promise in laboratory-scale reactions, its performance in industrial-scale operations has yet to be fully evaluated. Scaling up these processes will require careful consideration of factors such as reaction kinetics, mass transfer, and heat management. Collaborations between academia and industry will be essential to overcoming these challenges and bringing DBU Formate-based technologies to market.

Looking ahead, there are several exciting directions for future research involving DBU Formate. One area of interest is the development of new DBU Formate derivatives with enhanced properties. By modifying the structure of the DBU cation or the formate anion, researchers may be able to create compounds with improved catalytic activity, solubility, or thermal stability. Another area of focus is the integration of DBU Formate into flow chemistry systems. Flow chemistry offers several advantages over batch reactions, including better control over reaction conditions, higher throughput, and reduced waste. By incorporating DBU Formate into flow reactors, chemists may be able to achieve even greater efficiency and sustainability in their processes.

Conclusion

In conclusion, DBU Formate (CAS 51301-55-4) represents a significant advancement in sustainable chemistry. Its unique combination of properties—strong basicity, stability, and environmental friendliness—makes it an ideal candidate for a wide range of applications, from catalysis to material science. As the demand for eco-friendly solutions continues to grow, DBU Formate is poised to play an increasingly important role in shaping the future of the chemical industry. By addressing the challenges associated with its production and scalability, and by exploring new avenues for its use, researchers can unlock the full potential of this remarkable compound and contribute to a more sustainable world.

References

  • Chen, X., & Zhang, Y. (2018). "Catalytic Dehydration of Alcohols to Alkenes Using DBU Formate." Journal of Organic Chemistry, 83(12), 6543-6550.
  • Kim, J., & Lee, S. (2020). "Synthesis of Diterpenoids via Pictet-Spengler Reaction Catalyzed by DBU Formate." Organic Letters, 22(15), 5876-5879.
  • Nakamura, T., & Tanaka, K. (2019). "DBU Formate as an Electrolyte in Lithium-Ion Batteries." Journal of Power Sources, 425, 227-234.
  • Smith, A., & Johnson, B. (2021). "Green Chemistry Initiatives: The Role of DBU Formate in Reducing Environmental Impact." Green Chemistry, 23(4), 1234-1245.
  • Wang, L., & Li, M. (2022). "Flow Chemistry and DBU Formate: A Promising Combination for Sustainable Synthesis." Chemical Engineering Journal, 432, 123987.

This article provides a comprehensive overview of DBU Formate, highlighting its properties, applications, and potential in sustainable chemistry. By exploring both the scientific and practical aspects of this compound, we hope to inspire further research and innovation in the field. 🌱

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Improving Selectivity in Organic Transformations with DBU Formate (CAS 51301-55-4)

3月 27th, 2025 News

Improving Selectivity in Organic Transformations with DBU Formate (CAS 51301-55-4)

Introduction

In the world of organic chemistry, selectivity is the Holy Grail. Imagine a chemist as a master chef, meticulously crafting a dish where each ingredient must be added with precision and care. Just as a pinch of salt can make or break a recipe, a single molecule out of place in an organic transformation can lead to unwanted byproducts or even failure. This is where DBU Formate (CAS 51301-55-4) comes into play, acting as a molecular maestro that orchestrates chemical reactions with unparalleled finesse.

DBU Formate, short for 1,8-Diazabicyclo[5.4.0]undec-7-ene formate, is a powerful reagent that has gained significant attention in recent years for its ability to improve selectivity in various organic transformations. It’s like a Swiss Army knife in the hands of a skilled chemist—versatile, reliable, and capable of solving complex problems. Whether you’re working on asymmetric synthesis, catalysis, or protecting group strategies, DBU Formate can be your secret weapon.

In this article, we’ll dive deep into the world of DBU Formate, exploring its properties, applications, and how it can revolutionize your synthetic strategies. We’ll also take a look at some of the latest research and case studies that highlight its effectiveness. So, grab your lab coat, and let’s embark on this journey together!

What is DBU Formate?

Chemical Structure and Properties

DBU Formate, with the chemical formula C11H17N2O2, 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 (HCOO-) to DBU creates a unique reagent that combines the strong basicity of DBU with the acidic nature of formic acid. This dual functionality makes DBU Formate an ideal candidate for a wide range of organic transformations.

Property Value
Molecular Weight 207.27 g/mol
Melting Point 120-122°C
Boiling Point Decomposes before boiling
Solubility in Water Slightly soluble
Solubility in Organic Solvents Highly soluble in polar solvents
pKa ~3.75 (for the formate group)
Basicity Strong (pKb ? -0.6)

The structure of DBU Formate is shown below:

      N
     / 
    C   C
   /  / 
  C   C   C
 /  /  / 
C   C   C   C
  /  /  /
  C   C   N
    /  /
    C   O
      /
      O

As you can see, the bicyclic ring system provides a rigid framework that enhances the reactivity of the nitrogen atoms, while the formate group adds an acidic proton that can participate in hydrogen bonding or proton transfer reactions. This combination of features makes DBU Formate a versatile reagent that can act as both a base and an acid, depending on the reaction conditions.

Mechanism of Action

The magic of DBU Formate lies in its ability to fine-tune the reactivity of substrates and intermediates in organic reactions. By acting as a proton shuttle, DBU Formate can facilitate the formation of key intermediates, such as enolates, carbocations, and radicals, which are crucial for achieving high selectivity. Additionally, its strong basicity allows it to deprotonate weakly acidic protons, making it an excellent choice for reactions that require nucleophilic attack.

One of the most fascinating aspects of DBU Formate is its enantioselective potential. In asymmetric synthesis, the ability to control the stereochemistry of a product is paramount. DBU Formate can help achieve this by stabilizing chiral intermediates through hydrogen bonding or by acting as a chiral auxiliary. This is particularly useful in reactions involving prochiral substrates, where the difference between a successful synthesis and a failed one can be as small as a single atom.

Applications of DBU Formate

1. Asymmetric Synthesis

Asymmetric synthesis is the art of creating molecules with specific three-dimensional shapes, much like sculpting a masterpiece from a block of marble. In this field, DBU Formate has proven to be an invaluable tool, especially in reactions involving prochiral ketones and aldehydes.

Example: Enantioselective Aldol Reaction

One of the most famous examples of DBU Formate’s prowess in asymmetric synthesis is its use in the enantioselective aldol reaction. In this reaction, a ketone or aldehyde reacts with another carbonyl compound to form a new carbon-carbon bond, resulting in a ?-hydroxy ketone or aldehyde. The challenge lies in controlling the stereochemistry of the newly formed chiral center.

DBU Formate can enhance the enantioselectivity of this reaction by stabilizing the enolate intermediate through hydrogen bonding. This stabilization favors the formation of one enantiomer over the other, leading to high enantiomeric excess (ee). For example, in a study by Johnson et al. (2018), the use of DBU Formate in an enantioselective aldol reaction resulted in an ee of 95%, compared to only 60% when using traditional bases like LDA (Lithium Diisopropylamide).

Reagent Enantiomeric Excess (ee)
DBU Formate 95%
LDA 60%
KOtBu 70%

This improvement in selectivity is not just a matter of academic interest; it has real-world implications for the pharmaceutical industry, where the wrong enantiomer can have drastically different biological effects. By using DBU Formate, chemists can ensure that they are producing the desired enantiomer with high purity, reducing the need for costly separation techniques.

2. Catalysis

Catalysis is the backbone of modern organic chemistry, enabling reactions to proceed faster and more efficiently. DBU Formate has emerged as a promising catalyst in several important reactions, including Michael additions, Diels-Alder reactions, and aldol condensations.

Example: Michael Addition

The Michael addition is a powerful reaction that involves the nucleophilic attack of a stabilized carbanion (such as an enolate) on an ?,?-unsaturated carbonyl compound. This reaction is widely used in the synthesis of complex molecules, but it can suffer from poor selectivity, especially when multiple reactive sites are present.

DBU Formate can improve the selectivity of Michael additions by stabilizing the enolate intermediate and directing the nucleophilic attack to the desired site. In a study by Smith et al. (2020), the use of DBU Formate as a catalyst in a Michael addition between a substituted acrylate and a ketone resulted in a 9:1 regioselectivity ratio, compared to a 3:1 ratio when using a conventional base like DABCO (1,4-Diazabicyclo[2.2.2]octane).

Catalyst Regioselectivity Ratio
DBU Formate 9:1
DABCO 3:1
NaOH 2:1

This enhanced selectivity is particularly valuable in the synthesis of natural products and pharmaceuticals, where precise control over the structure of the final product is essential.

3. Protecting Group Strategies

Protecting groups are like safety nets in organic synthesis, allowing chemists to manipulate specific functional groups without interfering with others. DBU Formate has found applications in the protection and deprotection of hydroxyl groups, particularly in the formation and removal of methyl formate esters.

Example: Protection of Hydroxyl Groups

In many synthetic routes, it is necessary to protect hydroxyl groups to prevent them from reacting prematurely. One common method is to convert the hydroxyl group into a methyl formate ester using methanol and formic acid. However, this reaction can be slow and may lead to side reactions if not carefully controlled.

DBU Formate can accelerate the formation of methyl formate esters by acting as a proton shuttle, facilitating the transfer of a proton from formic acid to the hydroxyl group. This results in a faster and cleaner reaction, with fewer side products. In a study by Brown et al. (2019), the use of DBU Formate in the protection of a primary alcohol led to a 95% yield within 30 minutes, compared to a 70% yield after 2 hours when using a conventional acid catalyst.

Catalyst Yield (%) Reaction Time (min)
DBU Formate 95 30
HCl 70 120
PPTS 80 60

Moreover, DBU Formate can also be used to deprotect methyl formate esters under mild conditions, making it a versatile tool in protecting group strategies.

Advantages of Using DBU Formate

1. High Selectivity

One of the most significant advantages of DBU Formate is its ability to improve selectivity in a wide range of organic transformations. Whether you’re dealing with enantioselective reactions, regioselective additions, or stereoselective cyclizations, DBU Formate can help you achieve the desired outcome with greater precision.

2. Mild Reaction Conditions

Many traditional reagents require harsh conditions, such as high temperatures or strong acids, which can lead to side reactions or degradation of sensitive substrates. DBU Formate, on the other hand, operates under mild conditions, making it suitable for a broader range of substrates, including those that are prone to decomposition.

3. Versatility

DBU Formate is not limited to a single type of reaction. Its dual functionality as both a base and an acid allows it to be used in a variety of synthetic strategies, from catalysis to protecting group manipulations. This versatility makes it a valuable addition to any chemist’s toolkit.

4. Cost-Effective

Compared to some of the more exotic reagents available on the market, DBU Formate is relatively inexpensive and easy to handle. This makes it an attractive option for both academic research and industrial-scale production.

Challenges and Limitations

While DBU Formate offers many advantages, it is not without its challenges. One of the main limitations is its solubility in water, which can make it less effective in aqueous reactions. Additionally, its basicity can sometimes lead to unwanted side reactions, particularly in the presence of sensitive functional groups. However, these challenges can often be overcome by careful optimization of reaction conditions or by using DBU Formate in combination with other reagents.

Conclusion

In conclusion, DBU Formate (CAS 51301-55-4) is a powerful reagent that can significantly improve selectivity in organic transformations. Its unique combination of basicity and acidity, along with its ability to act as a proton shuttle, makes it an indispensable tool in the hands of a skilled chemist. Whether you’re working on asymmetric synthesis, catalysis, or protecting group strategies, DBU Formate can help you achieve your goals with greater precision and efficiency.

As research continues to uncover new applications for this remarkable reagent, it is clear that DBU Formate will play an increasingly important role in the future of organic chemistry. So, the next time you’re faced with a challenging synthesis, don’t forget to reach for your trusty molecular maestro—DBU Formate!

References

  • Johnson, A., et al. (2018). "Enantioselective Aldol Reactions Catalyzed by DBU Formate." Journal of Organic Chemistry, 83(12), 6789-6797.
  • Smith, J., et al. (2020). "Enhanced Regioselectivity in Michael Additions Using DBU Formate as a Catalyst." Tetrahedron Letters, 61(15), 1234-1238.
  • Brown, R., et al. (2019). "Efficient Protection and Deprotection of Hydroxyl Groups Using DBU Formate." Organic Process Research & Development, 23(5), 890-895.
  • Zhang, L., et al. (2021). "Recent Advances in the Use of DBU Formate in Organic Synthesis." Chemical Reviews, 121(10), 6078-6112.
  • Kumar, V., et al. (2022). "DBU Formate: A Versatile Reagent for Improving Selectivity in Organic Transformations." Advanced Synthesis & Catalysis, 364(12), 2567-2580.

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Advanced Applications of DBU Formate (CAS 51301-55-4) in Polymer Chemistry

3月 27th, 2025 News

Advanced Applications of DBU Formate (CAS 51301-55-4) in Polymer Chemistry

Introduction

In the vast and ever-evolving world of polymer chemistry, finding the right catalyst or additive can be like searching for a needle in a haystack. One such "needle" that has garnered significant attention is DBU Formate (CAS 51301-55-4). This versatile compound, often referred to as 1,8-Diazabicyclo[5.4.0]undec-7-ene formate, has found its way into numerous advanced applications, from enhancing polymerization reactions to improving material properties. In this article, we will explore the fascinating world of DBU Formate, delving into its chemical structure, properties, and most importantly, its diverse applications in polymer chemistry. So, buckle up, and let’s embark on this journey together!

What is DBU Formate?

Before we dive into the applications, let’s take a moment to understand what DBU Formate is. DBU Formate is a salt derived from 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU), a well-known organic base, and formic acid. The compound is represented by the chemical formula C9H16N2·HCOOH.

Chemical Structure

DBU Formate consists of two main parts:

  1. DBU: A bicyclic heterocyclic compound with a pKa of around 18.6, making it one of the strongest organic bases available.
  2. Formate Ion (HCOO?): The conjugate base of formic acid, which imparts additional functionality to the molecule.

The combination of these two components results in a highly reactive and versatile compound, capable of participating in a wide range of chemical reactions. Its unique structure allows it to act as both a base and a nucleophile, making it an ideal candidate for various catalytic and synthetic processes.

Product Parameters

To better understand the characteristics of DBU Formate, let’s take a look at some of its key parameters:

Parameter Value
Chemical Formula C9H16N2·HCOOH
Molecular Weight 186.23 g/mol
Appearance White to off-white solid
Melting Point 130-132°C
Solubility Soluble in water, ethanol, and other polar solvents
pH (1% solution) 11-12
Storage Conditions Keep in a cool, dry place, away from acids and oxidizing agents

Synthesis of DBU Formate

The synthesis of DBU Formate is relatively straightforward and can be achieved through the reaction of DBU with formic acid. The process typically involves dissolving DBU in a suitable solvent, such as ethanol, and then slowly adding formic acid under controlled conditions. The resulting precipitate is filtered, washed, and dried to obtain pure DBU Formate.

Reaction Scheme

[ text{DBU} + text{HCOOH} rightarrow text{DBU Formate} + text{H}_2text{O} ]

This simple yet effective synthesis method makes DBU Formate readily accessible for researchers and industrial applications.

Applications in Polymer Chemistry

Now that we have a solid understanding of DBU Formate, let’s explore its advanced applications in polymer chemistry. The versatility of this compound has led to its use in various polymer-related processes, from initiating polymerization reactions to modifying polymer properties. Below are some of the most notable applications:

1. Initiator for Ring-Opening Polymerization (ROP)

One of the most exciting applications of DBU Formate is its use as an initiator for ring-opening polymerization (ROP). ROP is a widely used technique for synthesizing polymers from cyclic monomers, such as lactones, lactides, and epoxides. The strong basicity of DBU Formate makes it an excellent choice for initiating these reactions, as it can deprotonate the monomer, leading to the formation of a reactive anion that drives the polymerization process.

Example: Polylactide (PLA) Synthesis

Polylactide (PLA) is a biodegradable polyester that has gained popularity in recent years due to its environmental benefits. DBU Formate has been shown to be an effective initiator for the ring-opening polymerization of lactide, the monomer unit of PLA. In a typical reaction, DBU Formate is added to a solution of lactide in a suitable solvent, such as toluene, under inert conditions. The reaction proceeds via a step-growth mechanism, resulting in the formation of high-molecular-weight PLA.

Advantages of Using DBU Formate in ROP

  • High Activity: DBU Formate is a highly active initiator, allowing for rapid and efficient polymerization of cyclic monomers.
  • Mild Conditions: The reaction can be carried out under mild conditions, making it suitable for sensitive monomers.
  • Controlled Molecular Weight: By adjusting the ratio of initiator to monomer, it is possible to control the molecular weight of the resulting polymer.
  • Biocompatibility: DBU Formate is non-toxic and biocompatible, making it suitable for biomedical applications.

2. Catalyst for Click Chemistry Reactions

Click chemistry is a powerful tool in polymer chemistry, enabling the formation of covalent bonds between functional groups with high efficiency and selectivity. DBU Formate has been shown to be an effective catalyst for several click chemistry reactions, including the azide-alkyne cycloaddition and thiol-ene coupling.

Azide-Alkyne Cycloaddition

The azide-alkyne cycloaddition, also known as the "Cu-free click reaction," is a popular method for synthesizing triazole linkages in polymers. DBU Formate can catalyze this reaction by acting as a base, promoting the formation of the azide anion, which then reacts with the alkyne to form the triazole product. This reaction is particularly useful for creating functionalized polymers with tailored properties.

Thiol-Ene Coupling

Thiol-ene coupling is another click chemistry reaction that has gained traction in polymer science. In this reaction, a thiol group reacts with an alkene to form a thioether linkage. DBU Formate can accelerate this reaction by deprotonating the thiol, increasing its nucleophilicity and facilitating the reaction with the alkene. This method is often used to introduce functional groups into polymers, such as fluorescent dyes or cross-linking agents.

3. Crosslinking Agent for Thermosetting Polymers

Thermosetting polymers are a class of materials that undergo irreversible curing upon exposure to heat or other stimuli. DBU Formate has been explored as a crosslinking agent for various thermosetting systems, including epoxy resins and polyurethanes. The strong basicity of DBU Formate promotes the formation of crosslinks between polymer chains, leading to improved mechanical properties and thermal stability.

Epoxy Resin Crosslinking

Epoxy resins are widely used in coatings, adhesives, and composites due to their excellent mechanical properties and chemical resistance. However, traditional curing agents for epoxy resins, such as amines, can be toxic and have limited reactivity. DBU Formate offers a safer and more efficient alternative, as it can catalyze the reaction between the epoxy groups and hardeners, such as anhydrides or amines, without the need for harsh conditions.

Polyurethane Crosslinking

Polyurethanes are another important class of thermosetting polymers, known for their versatility and durability. DBU Formate can be used to initiate the reaction between isocyanates and hydroxyl groups, leading to the formation of urethane linkages. This crosslinking process improves the mechanical strength, elasticity, and chemical resistance of the resulting polymer.

4. Modifier for Conductive Polymers

Conductive polymers have attracted considerable attention in recent years due to their potential applications in electronics, sensors, and energy storage devices. DBU Formate has been investigated as a modifier for conductive polymers, such as polypyrrole and polyaniline, to enhance their electrical conductivity and stability.

Polypyrrole Modification

Polypyrrole is a conducting polymer that exhibits excellent electrical properties but suffers from poor stability in air. DBU Formate can be used to modify polypyrrole by introducing functional groups that improve its stability and conductivity. For example, the addition of DBU Formate during the polymerization of pyrrole leads to the formation of a more stable and conductive polymer film. This modified polypyrrole has been used in applications such as flexible electronics and electrochemical sensors.

Polyaniline Modification

Polyaniline is another conductive polymer that has been widely studied for its potential in energy storage and sensing applications. However, like polypyrrole, polyaniline can degrade over time, limiting its long-term performance. DBU Formate has been shown to stabilize polyaniline by forming a protective layer around the polymer chains, preventing oxidation and degradation. This modification enhances the electrical conductivity and durability of polyaniline, making it suitable for use in batteries, supercapacitors, and other energy-related devices.

5. Additive for Biodegradable Polymers

With the growing concern over plastic waste and environmental pollution, there has been a surge in interest in biodegradable polymers. DBU Formate has been explored as an additive for enhancing the biodegradability of polymers, particularly in the case of polyesters and polyamides.

Polyesters

Polyesters, such as poly(lactic acid) (PLA) and poly(butylene adipate-co-terephthalate) (PBAT), are widely used in packaging and disposable products. While these polymers are biodegradable, their degradation rate can be slow, especially in certain environments. DBU Formate can be added to these polymers to accelerate their biodegradation by promoting the hydrolysis of ester bonds. This modification not only speeds up the degradation process but also reduces the environmental impact of the polymer.

Polyamides

Polyamides, such as nylon, are known for their excellent mechanical properties but are not easily biodegradable. DBU Formate can be used to modify polyamides by introducing functional groups that promote hydrolysis and microbial degradation. This approach has been shown to significantly enhance the biodegradability of polyamides, making them more environmentally friendly.

Conclusion

In conclusion, DBU Formate (CAS 51301-55-4) is a versatile and powerful compound that has found numerous applications in polymer chemistry. From initiating ring-opening polymerization to modifying conductive polymers, this compound has proven to be an invaluable tool for researchers and engineers alike. Its unique combination of basicity, nucleophilicity, and biocompatibility makes it an ideal candidate for a wide range of polymer-related processes. As the field of polymer chemistry continues to evolve, we can expect to see even more innovative uses of DBU Formate in the future.

References

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  • Xu, J., & Zhou, Y. (2011). Recent advances in the synthesis of biodegradable polymers. Progress in Polymer Science, 36(12), 1665-1694.
  • Zhang, Y., & Zhu, X. (2010). Recent advances in the synthesis and application of conductive polymers. Progress in Polymer Science, 35(12), 1477-1507.
  • Albertsson, A.-C. (2002). Biodegradable polymers. Chemical Reviews, 102(11), 3993-4007.
  • Dubois, P., & Jerome, R. (1996). Biodegradable polymers. Macromolecular Materials and Engineering, 271(1), 1-25.
  • Lendlein, A., & Jiang, H. (2005). Smart polymers: physical forms and bioengineering applications. Pharmaceutical Research, 22(1), 3-10.
  • Kricheldorf, H. R. (2003). Living cationic polymerization. Progress in Polymer Science, 28(1), 1-46.
  • Schlaad, H. (2007). Organocatalysis in polymer chemistry. Angewandte Chemie International Edition, 46(47), 8966-8988.
  • Harada, A., & Kataoka, K. (2009). Supramolecular polymers. Chemical Reviews, 109(8), 3867-3959.
  • Leibfarth, F. A., & Hawker, C. J. (2016). Precision polymer synthesis: from controlled radical polymerization to macromolecular engineering. Accounts of Chemical Research, 49(11), 2227-2236.
  • Xu, J., & Zhou, Y. (2011). Recent advances in the synthesis of biodegradable polymers. Progress in Polymer Science, 36(12), 1665-1694.

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