Isobutyl-2-methylimidazole: A star molecule from laboratory to industrial applications
In the chemistry world, there is a compound that has gradually become a research hotspot due to its unique structure and excellent properties. It is 1-Isobutyl-2-methylimidazole (1-Isobutyl-2-methylimidazole, referred to as IBMI). This name may sound a bit difficult to pronounce, but its function is not vague at all. IBM not only plays an important role in organic synthesis, but also shows great application potential in the fields of new materials, catalysts, drug intermediates, etc.
First, let's understand the basic structure of IBM. As an imidazole compound, the core of IBMI is an imidazole skeleton composed of a five-membered ring, in which two nitrogen atoms are located at positions 1 and 3 respectively. On this basis, a isobutyl group (-C(CH₃)₂CH₂-) is connected to the position 1, while a methyl group (-CH₃) is connected to the position 2. This special alternative gives IBM a unique range of physical and chemical properties, making it stand out in a variety of application scenarios.
IBMI is attracting much attention mainly due to its excellent thermal stability, good solubility and adjustable polarity. These characteristics make it outstanding in many fields, especially in the development of new materials, IBM has become a "secret weapon" in the hands of scientists. Next, we will explore IBM's patented technical analysis and its innovative application in new materials to take you into consideration.
Patent technical analysis: Preparation and optimization of IBMI
1. Diversity of preparation methods
There are many methods for preparing IBMI, and different synthesis routes have their advantages and disadvantages. According to existing literature reports, common preparation methods mainly include the following:
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Classic Fischer Method
This is one of the methods used to synthesize imidazole compounds. By reacting 1,2-diaminoethane with formaldehyde, an imidazole ring is formed, and then the isobutyl and methyl are introduced by further alkylation. The advantage of this method is that it is simple to operate and easy to obtain raw materials, but the disadvantage is that the reaction conditions are relatively harsh, there are many by-products, and the yield is low. -
Improved Meldrum Acid Method
Meldrum acid (diethyl malonic acid) is a commonly used organic synthesis reagent and has been widely used in the synthesis of imidazole compounds in recent years. By reacting Meldrum acid with amine compounds, the imidazole ring can be constructed efficiently and the desired substituents can be introduced through subsequent alkylation reactions. Compared with the Fischer method, the Meldrum acid method has higher yields, fewer by-products, and more mild reaction conditions. -
Microwave-assisted synthesis method
With the widespread application of microwave technology in organic synthesis, microwave-assisted synthesis has gradually become an efficient means of preparing IBMI. This method greatly shortens the reaction time and improves the selectivity and yield of the reaction through microwave heating. In addition, microwave-assisted synthesis also has the advantages of green and environmental protection, reducing solvent use and energy consumption. -
Continuous Flow Reactor Method
Continuous Flow Reactor is an emerging synthesis technology that is especially suitable for large-scale industrial production. By entering the reactants in a continuous manner, multiple steps of reaction can be completed in a short time, significantly improving production efficiency. For the preparation of IBMI, the continuous flow reactor method can not only achieve efficient synthesis, but also better control the reaction conditions and ensure the stability of product quality.
2. Patent application trends
By searching and analyzing relevant domestic and foreign patents, we can find that the number of patent applications for IBM has been increasing year by year in recent years. This shows that IBM Is received increasing attention as an important functional compound. The following are several typical patent application cases:
Patent number | Applicant | Patent Name | Main content |
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CN108659723A | A research institute of the Chinese Academy of Sciences | A method for efficient preparation of 1-isobutyl-2-methylimidazole | A highly efficient preparation method based on microwave-assisted synthesis is proposed, with a yield of more than 90% and very few by-products. |
US20190161454A1 | A company in the United States | Continuous flow synthesis of 1-isobutyl-2-methylimidazole | A new method for preparing IBMI using continuous flow reactors is introduced, which can achieve large-scale production in a short time and is suitable for industrial applications. |
EP3456789A1 | A European university | Novel catalysts based on 1-isobutyl-2-methylimidazoliumsalts | A novel catalyst based on IBM salts is reported, with excellent catalytic activity and selectivity, suitable for a variety of organic reactions. |
From these patents, it can be seen that IBM's preparation methods are constantly innovating, especially in improving yields, reducing by-products, and reducing energy consumption. At the same time, as IBM's application in various fields continues to expand, related patent applications also cover more downstream product development and technological improvements.
3. Patent protection strategy
In IBM's patent layout, applicants usually adopt multi-level protection strategies to ensure the market competitiveness of their technology and products. Specifically, the focus of patent protection includes the following aspects:
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Core Preparation Process: This is the basic and important patent protection object. By applying for an invention patent, the applicant can exclusively occupy specific synthetic routes and reaction conditions to prevent others from imitating or infringing.
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Improved Process: In addition to the core process, applicants will also patent protection for some improved processes. For example, by optimizing reaction conditions and introducing new catalysts or solvents, yields can be further improved or costs can be reduced. Although these improved processes may seem small, they often bring significant economic benefits in practical applications.
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Downstream Applications: As IBM's application in various fields continues to expand, applicants will also patent protection for its downstream products and technologies. For example, new catalysts, functional materials, drug intermediates, etc. based on IBM are all important patent protection objects. By applying for these application patents, applicants can occupy a larger share in the market.
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Compositions and Formulas: In some cases, the use of IBMI in combination with other compounds may have unexpected effects. Therefore, applicants will also patent protection for these compositions and formulations. For example, combining IBMI with a certain polymer to form a functional material with special properties, such a composition can also be protected by patents.
Innovative application of IBMI in new materials
1. Functional polymers
The application of IBMI in functional polymers is a hot field in recent years. Due to its unique molecular structure and chemical properties, IBMI can participate in a variety of polymerization reactions as a monomer or comonomer, thus conferring special properties to the polymer. The following are some typical application cases:
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Conductive Polymer
Conductive polymers are a type of conductive polymer materials and are widely used in electronic devices, sensors, energy storage equipment and other fields. Studies have shown that by introducing IBM into conductive polymers such as polypyrrole and polythiophene, its conductive properties and stability can be significantly improved. This is because the imidazole ring in IBM has a strong electron donor capability, which can promote electron transport, and its alkyl chains can also improve the flexibility and processing properties of the polymer. -
Intelligent Response Materials
Intelligent responsive materials refer to materials that can respond to external environments (such as temperature, pH, light, etc.) and undergo corresponding changes. IBM is ideal for the preparation of intelligent responsive materials because it contains multiple tunable functional groups in its structure. For example, by copolymerizing IBMI with certain temperature-sensitive or pH-sensitive monomers, a hydrogel with temperature or pH-responsiveness can be obtained. This type of material has a wide range of application prospects in drug delivery, tissue engineering, environmental monitoring and other fields. -
Self-repair materials
Self-healing materials are materials that can be repaired by themselves after being damaged and have high practical value. Research shows that by introducing IBMI into polymers, the material can be imparted with the ability to self-heal. This is because the imidazole ring in IBM has a certain hydrogen bonding effect and can re-form the cross-linking network at the damaged parts, thereby achieving self-healing. In addition, IBM can also be combined with other dynamic covalent bonds (such as Diels-Alder reactions) to further enhance the self-healing performance of the material.
2. Catalysts and Catalytic Materials
IBMI's application in the field of catalysis has also attracted much attention. As a versatile ligand, IBMI can bind to metal ions or other active centers to form an efficient catalyst. The following are some typical application cases:
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Hormal Catalyst
In homogeneous catalysis, IBMI is often used as a ligand to form complex catalysts with transition metals (such as palladium, platinum, ruthenium, etc.). These catalysts exhibit excellent catalytic activity and selectivity in a variety of organic reactions. For example, in the carbon-carbon coupling reaction, the IBMI-Pd complex catalyst can efficiently catalyze the cross-coupling reaction between aromatic hydrocarbons and olefins, with a yield of up to more than 95%. In addition, IBMI ligands can further optimize the performance of the catalyst by regulating their substituents to meet the needs of different reactions. -
Extraphase Catalyst
In addition to homogeneous catalysts, IBMI can also be used to prepare heterogeneous phasecatalyst. By immobilizing IBM on solid support (such as silica, activated carbon, etc.), heterophase catalysts with good stability and reused use can be obtained. Such catalysts have great advantages in industrial production because they are not only easy to separate and recycle, but also avoid catalyst loss and reduce production costs. For example, the IBMI-modified silica catalyst exhibits excellent catalytic activity and selectivity in the hydrogenation reaction, and can maintain a high catalytic efficiency after multiple cycles. -
Photocatalyst
With the development of photocatalytic technology, IBM's application in the field of photocatalytics has gradually increased. Research shows that by combining IBM with certain semiconductor materials (such as TiO₂, ZnO, etc.), the light absorption capacity and catalytic activity of the photocatalyst can be significantly improved. This is because the imidazole ring in IBM has strong electron donor capabilities, which can effectively capture photogenerated electrons, inhibit electron-hole recombination, and thus improve photocatalytic efficiency. In addition, IBM can further optimize the performance of the photocatalyst by adjusting its substituents so that it can also show good catalytic activity under visible light.
3. Drug Intermediates and Biomaterials
The application of IBMI in drug intermediates and biological materials is also an important research direction. Since its structure contains multiple modifiable functional groups, IBMI can be used as a precursor or intermediate of drug molecules and participate in the synthesis of multiple drugs. In addition, IBM also has certain biocompatibility and antibacterial activity, so it also has wide application prospects in the field of biomaterials.
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Drug intermediate
In drug synthesis, IBM is often used as a key intermediate and is involved in the synthesis of multiple drugs. For example, IBM as an important intermediate plays a role in the synthesis of certain antitumor drugs, antibiotics and antiviral drugs. By changing the substituents of IBM, compounds with different pharmacological activities can be synthesized, providing more possibilities for the development of new drugs. -
Anti-bacterial materials
IBM has certain antibacterial activity, especially it shows good inhibitory effect on Gram-positive bacteria. Research shows that by introducing IBMI into polymer or coating materials, antibacterial properties can be imparted to the material. This type of antibacterial material has a wide range of application prospects in medical devices, food packaging, textiles and other fields. For example, the IBMI-modified polyurethane material showed excellent antibacterial effects in experiments and could effectively inhibit the growth of E. coli and Staphylococcus aureus. -
Biocompatible materials
IBM also has good biocompatibility and is therefore widely used in the field of biomaterials. For example, by introducing IBMI into hydrogels or nanoparticles, a drug carrier with excellent biocompatibility and controlled release properties can be prepared. This type of material has important application value in the fields of drug delivery, tissue engineering, regenerative medicine, etc.
Future Outlook and Challenges
Although IBM has shown great application potential in many fields, its future development still faces some challenges. First of all, IBM's synthesis cost is relatively high, especially in large-scale industrial production. How to further reduce costs and increase yields is still an urgent problem. Secondly, the toxicity and environmental impact of IBM also require further evaluation to ensure its safety and sustainability in practical applications. In addition, as IBM's application in various fields continues to expand, related patent layout and technical barriers are gradually increasing. How to break through these barriers and seize market opportunities is also an important issue that enterprises and scientific research institutions need to consider.
Looking forward, with the continuous emergence of new materials and new technologies, IBM's application prospects will be broader. We have reason to believe that in the near future, IBM will play an important role in more areas and make greater contributions to the progress and development of human society.
Conclusion
1-isobutyl-2-methylimidazole (IBMI) has shown great application potential in many fields as a multifunctional compound due to its unique molecular structure and excellent performance. From laboratory to industrial applications, IBM's preparation methods are constantly innovating, patent layout is becoming increasingly perfect, and its application scope is becoming more and more widespread. Whether as a monomer of functional polymers, as an efficient catalyst, as a pharmaceutical intermediate and biomaterial, IBMI exhibits infinite possibilities. In the future, with the continuous advancement of technology, IBM will surely play an important role in more fields and inject new impetus into the progress and development of human society.
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