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Product Name | Methacrylic acid, 2-isocyanatoethyl ester |
Cas Number | 30674-80-7 |
Formula | C8H11NO3 |
Molar Mass | 169.18 |
Property 1 | Colorless liquid |
Property 2 | Boiling point: 215 °C |
Property 3 | Density: 1.1 g/cm3 |
Property 4 | Flash point: 102 °C |
Property 5 | Index of refraction: n20/D 1.445 |
Property 6 | Solubility in water: Reacts |
Property 7 | Vapor pressure: 0.368 mmHg at 25°C |
Property 8 | Explosive limits: 2.7%-13% |
Property 9 | Appearance: Clear to slightly yellowish |
Property 10 | Stability: Stable under recommended storage conditions |
What are the main applications of Methacrylic acid, 2-isocyanatoethyl ester?
Methacrylic acid, 2 - isocyanatoethyl ester, also known as 2 - isocyanatoethyl methacrylate (IEM), has several main applications.There are several applications for 2 - Isocyanatoethyl Methacrylate, also known as Methacrylic Acid, 2 – Isocyanatoethyl Ester (IEM).
In the field of coatings, IEM is used to prepare high - performance coatings.IEM is used in the coatings industry to prepare high-performance coatings. Its isocyanate group can react with active hydrogen - containing compounds such as polyols to form cross - linked structures.Its isocyanate can react with active compounds containing hydrogen, such as polyols, to form cross-linked structures. This results in coatings with excellent abrasion resistance, chemical resistance, and weather resistance.This produces coatings that are highly resistant to abrasion, chemicals, and weather. For example, in automotive coatings, these coatings can protect the car body from scratches, corrosion caused by rain, acid rain, and other environmental factors, while also providing a high - gloss and durable finish.These coatings are used in automotive coatings to protect the car from scratches, corrosion due to rain, acid rain and other environmental factors. They also provide a high-gloss and durable finish.
In the adhesives industry, IEM plays an important role.IEM is a key component in the adhesives industry. It can be incorporated into adhesive formulations to improve adhesion strength.It can be added to adhesive formulations to increase adhesion. The isocyanate group can react with various substrates, including metals, plastics, and ceramics.The isocyanate can react with a variety of substrates including metals and plastics. This enables the adhesive to firmly bond different materials together.The adhesive can then be used to bond materials together. In the assembly of electronic devices, adhesives containing IEM can ensure the reliable connection of components, withstanding mechanical stress and environmental changes.Adhesives containing IEM are used in the assembly of electronic devices to ensure that components are connected securely, despite mechanical stress and environmental changes.
IEM is also widely used in the production of polymers and copolymers.IEM is widely used to produce polymers and copolymers. When copolymerized with other monomers, it can introduce reactive isocyanate groups into the polymer chain.Copolymerization with other monomers can introduce reactive isocyanate group into the polymer chain. These reactive groups can be further reacted to modify the polymer's properties, such as improving its solubility, film - forming ability, and cross - linking density.These reactive groups can then be further reacted in order to modify the properties of the polymer, such as its solubility and film - forming capability, or cross - linking densities. For instance, in the synthesis of specialty polymers for biomedical applications, the controlled introduction of IEM can endow the polymer with the ability to react with biological molecules, facilitating functions like cell adhesion or drug - delivery system modification.In the synthesis specialty polymers for biomedical application, the controlled introduction IEM can endow polymer with the capability to react with biological molecule, facilitating functions such as cell adhesion and drug - delivery system modifications.
In the field of dental materials, IEM can be used to prepare dental adhesives and composites.IEM is used in the dental field to prepare composites and dental adhesives. The reactive nature of IEM helps in firmly bonding dental restorative materials to tooth structures.IEM's reactive nature helps to firmly bond dental restorative materials onto tooth structures. It can enhance the durability and stability of dental fillings, ensuring long - term functionality and preventing the recurrence of dental caries around the filling area.It can improve the durability and stability dental fillings. This ensures long-term functionality and prevents the recurrences of dental caries in the area of the filling.
Overall, the unique reactive groups of methacrylic acid, 2 - isocyanatoethyl ester make it a valuable ingredient in multiple industries, contributing to the development of high - performance materials with specific properties.The unique reactive groups in methacrylic acids, 2 -isocyanatoethyl esters make them a valuable component for multiple industries. They contribute to the development and production of high-performance materials with specific properties.
What are the safety precautions when handling Methacrylic acid, 2-isocyanatoethyl ester?
Methacrylic acid, 2 - isocyanatoethyl ester is a hazardous chemical.Methacrylic Acid, 2 - Isocyanatoethyl Ester is a dangerous chemical. Here are the safety precautions when handling it.Here are some safety precautions to take when handling it.
First, personal protective equipment is crucial.Personal protective equipment is essential. Workers should wear appropriate chemical - resistant clothing.Wear clothing that is resistant to chemicals. This includes full - body suits made of materials that can resist the penetration of the chemical, protecting the skin from direct contact.Full-body suits made from materials that resist chemical penetration are ideal for protecting skin from direct contact. Gloves made of suitable resistant materials like nitrile are necessary to prevent skin exposure during operations such as pouring or transferring the substance.Gloves made from nitrile or other resistant materials are required to protect the skin during operations like pouring and transferring the substance. Safety goggles or a face shield must be worn to safeguard the eyes from splashes, as any contact with the eyes can cause severe irritation, damage, or even permanent vision loss.Wearing safety goggles or face shields is necessary to protect the eyes from splashes. Contact with the eyes may cause severe irritation or damage, and even permanent vision loss.
Second, ensure proper ventilation in the handling area.Second, make sure that the area where you are handling the chemical is properly ventilated. Since this chemical may release harmful vapors, a well - ventilated space helps to dilute these vapors, reducing the risk of inhalation.A well-ventilated space can help to dilute the harmful vapors released by this chemical, reducing inhalation risks. Local exhaust ventilation systems can be installed near the work area where the chemical is being used to capture and remove the vapors directly at the source.Local exhaust ventilation systems are installed near the area where the chemical will be used to capture the vapors and remove them directly at the source. In case of large - scale handling, a general ventilation system for the entire room can also be set up to maintain air quality.For large-scale handling, a general air ventilation system can be installed to maintain the air quality.
Third, storage is important.Third, it is important to store the product. Store methacrylic acid, 2 - isocyanatoethyl ester in a cool, dry, and well - ventilated area, away from sources of heat, ignition, and incompatible substances.Store methacrylic acids, 2 -isocyanatoethyl esters in a cool and dry area that is well-ventilated, away from heat sources, ignition sources, and other incompatible substances. It should be stored in tightly sealed containers to prevent leakage and vapor release.Store it in tightly sealed containers, to prevent leakage or vapor release. Keep it separate from oxidizing agents, acids, bases, and amines, as these can react violently with it.Separate it from oxidizing agents and acids, bases and amines as they can react violently.
Fourth, in case of spills, immediate action is required.In the event of spills, you must act immediately. First, evacuate the non - essential personnel from the area.First, remove all non-essential personnel from the area. Wear proper protective gear before starting the clean - up.Wear protective gear before cleaning up. Absorb the spill with an appropriate absorbent material such as vermiculite, sand, or a commercial spill - control product.Use an absorbent material, such as vermiculite or sand. Do not use materials that can react with the chemical.Avoid using materials that may react with the chemical. Then, carefully place the contaminated absorbent in a suitable waste container for proper disposal according to local regulations.Place the contaminated absorbent into a suitable container according to local regulations.
Finally, all workers handling this chemical should be trained in its properties, hazards, and safety procedures.All workers handling this chemical must be trained on its hazards, properties, and safety procedures. They should know how to respond in case of an accident, such as the proper use of safety equipment and the location of emergency showers and eyewash stations.They should be able to respond appropriately in the event of an accident. This includes knowing how to use safety equipment, where emergency showers and eyewashing stations are located, and how they can get help if necessary. Regular safety drills can also be conducted to ensure that workers are well - prepared for any potential incidents.To ensure that workers are prepared for any possible incidents, regular safety drills can be conducted.
What is the typical physical and chemical properties of Methacrylic acid, 2-isocyanatoethyl ester?
Methacrylic acid, 2 - isocyanatoethyl ester, also known as 2 - isocyanatoethyl methacrylate (IEM), has the following typical physical and chemical properties.The following physical and chemical characteristics are typical of 2 -isocyanatoethylmethacrylate, also known by the name 2 -isocyanatoethylmethacrylate.
Physical properties:Physical Properties
Appearance: It is usually a clear, colorless to slightly yellow liquid.Appearance: It's usually a clear liquid that is colorless or slightly yellow. This appearance is common for many organic esters in a pure state, allowing for easy visual inspection during handling and quality control in industrial processes.This is a common appearance for many organic esters when they are in their pure state. It allows for easy visual inspection and quality control during industrial processes.
Odor: It has a pungent and characteristic odor.Odor: It emits a pungent, characteristic smell. The strong smell is an important sensory property, which also serves as a warning sign in case of potential leaks or improper handling.The strong smell is a sensory property that can be used as a warning in the event of a leak or improper handling. Workers in industries using this compound need to be aware of this distinct smell for safety reasons.This distinct smell is important for the safety of workers in industries that use this compound.
Boiling point: The boiling point of 2 - isocyanatoethyl methacrylate is around 100 - 102 degC at 1.33 kPa.Boiling Point: The boiling point for 2 -isocyanatoethylmethacrylate at 1.33 kPa is approximately 100-102 degC. This relatively high boiling point compared to some smaller organic molecules is due to the presence of polar functional groups.This relatively high boiling temperature compared to smaller organic molecules is due the presence of polar groups. The isocyanate and ester groups contribute to intermolecular forces such as dipole - dipole interactions and hydrogen bonding (to a certain extent), which require more energy to break the liquid - gas phase transition.The isocyanate groups and ester groups are responsible for intermolecular forces, such as dipole-dipole interactions and hydrogen bonds (to a certain degree), which require additional energy to break the liquid-gas phase transition.
Melting point: It has a low melting point, usually below room temperature.Melting point: It is a low melting temperature, usually below the room temperature. This ensures that it remains in a liquid state under normal ambient conditions, facilitating its use in various applications where a fluid substance is required, like in coatings and adhesives formulations.This ensures it remains liquid under normal ambient conditions. It can be used in many applications that require a fluid substance, such as in coatings and adhesion formulations.
Density: Its density is approximately 1.05 - 1.07 g/cm3.Density: The density is around 1.05-1.07 g/cm3. This density value is relevant for volume - to - mass conversions in manufacturing processes.This density value is important for volume-to-mass conversions during manufacturing processes. For example, when formulating mixtures, knowing the density helps in accurately measuring the amount of 2 - isocyanatoethyl methacrylate needed.Knowing the density is useful when formulating mixtures.
Chemical properties:Chemical properties
Reactivity of the isocyanate group: The isocyanate (-NCO) group in 2 - isocyanatoethyl methacrylate is highly reactive.Reactivity of the isocyanate groups: The isocyanate(-NCO-) group in 2-isocyanatoethylmethacrylate is highly reactive. It readily reacts with compounds containing active hydrogen atoms, such as alcohols, amines, and water.It readily reacts to compounds that contain active hydrogen atoms such as alcohols and amines. With alcohols, it forms urethane linkages.It forms urethane links with alcohols. This reactivity is the basis for its use in the production of polyurethanes, which are widely used in coatings, foams, and adhesives.This reactivity is what makes it so useful in the production polyurethanes that are widely used for coatings, adhesives, and foams. When reacting with water, it releases carbon dioxide gas and forms urea derivatives.It releases carbon dioxide gas when it reacts with water and forms urea-derived derivatives. This reaction needs to be carefully controlled during storage and processing to avoid unwanted side - reactions.It is important to monitor this reaction during storage and processing in order to avoid unwanted side reactions.
Polymerizability of the methacrylate group: The methacrylate part of the molecule contains a carbon - carbon double bond (C = C).Polymerizability is due to the double carbon-carbon bond (C=C) in the methacrylate portion of the molecule. This double bond makes the compound polymerizable.This double bond is what makes the compound polymerizable. Under the influence of heat, light, or the presence of initiators like peroxides, the double bond can break and form long - chain polymers.The double bond can be broken by heat, light or peroxides. This property is exploited in the production of various polymers used in dental materials, contact lenses, and other specialty plastics.This property is used to produce various polymers that are used in dental materials and contact lenses.
Hydrolysis sensitivity: Due to the presence of the ester group, 2 - isocyanatoethyl methacrylate is sensitive to hydrolysis in the presence of water and an appropriate catalyst (even trace amounts of acid or base can accelerate the reaction).Hydrolysis sensitivity. Due to the ester group present, 2 -isocyanatoethylmethacrylate is sensitive when hydrolyzed in the presence water and a suitable catalyst (even traces of acid or base may accelerate the reaction). Hydrolysis of the ester group can lead to the formation of methacrylic acid and 2 - hydroxyethyl isocyanate, which can change the properties of the compound and any products it is used in.Hydrolysis of ester groups can lead to formation of 2 -hydroxyethylisocyanate and methacrylic acids, which can alter the properties of a compound and the products it is used in. Therefore, proper storage conditions, such as keeping it dry, are crucial to maintain its integrity.Proper storage conditions are important to maintain the integrity of the compound.
How is Methacrylic acid, 2-isocyanatoethyl ester synthesized?
Methacrylic acid, 2 - isocyanatoethyl ester is synthesized through the following general steps:The following general steps are used to synthesize methacrylic acid 2 - isocyanatoethyl ester:
1. Preparation of starting materialsPrepare the starting materials
The synthesis often starts with 2 - hydroxyethyl methacrylate (HEMA) and a compound containing an isocyanate group - typically phosgene or a phosgene - free alternative like diphosgene or triphosgene.The synthesis usually begins with 2 -hydroxyethylmethacrylate (HEMA), and a compound that contains an isocyanate - usually phosgene, or a phosgene-free alternative like diphosgene, or triphosgene. However, due to the toxicity of phosgene, safer alternatives are preferred.Due to the toxicity, safer alternatives like diphosgene or triphosgene are preferred. For example, diphosgene (bis(trichloromethyl) carbonate) can be used.
2. Reaction mechanismReaction Mechanism
The reaction between 2 - hydroxyethyl methacrylate and the isocyanate - source is a substitution reaction.The reaction between the 2 -hydroxyethylmethacrylate and isocyanate-source is a substitution. In the case of using diphosgene, it reacts with 2 - hydroxyethyl methacrylate in the presence of a base.Diphosgene reacts with 2-hydroxyethylmethacrylate when it is present in a base. The base helps to deprotonate the hydroxyl group in 2 - hydroxyethyl methacrylate, making it a better nucleophile.The base helps deprotonate hydroxyl groups in 2 -hydroxyethylmethacrylate to make it a more nucleophilic compound.
The reaction proceeds as follows:The reaction proceeds in the following way:
First, diphosgene decomposes under appropriate reaction conditions to generate reactive chloroformate species.First, under the right conditions, diphosgene breaks down to produce reactive chloroformate species. The deprotonated hydroxyl group of 2 - hydroxyethyl methacrylate attacks the carbonyl carbon of the chloroformate, displacing a chloride ion.The deprotonated group of 2 -hydroxyethylmethacrylate attacks carbonyl carbon in the chloroformate and displaces a chloride. Then, another equivalent of the base - mediated deprotonation and intramolecular rearrangement occur, leading to the formation of the isocyanate group in 2 - isocyanatoethyl methacrylate.Then, a second equivalent of base-mediated deprotonation occurs, leading to intramolecular rearrangement and the formation of isocyanate in 2 -isocyanatoethylmethacrylate.
3. Reaction conditionsReaction conditions
The reaction is usually carried out in an organic solvent such as dichloromethane or toluene.The reaction is carried out using an organic solvent, such as toluene or dichloromethane. These solvents provide a suitable medium for the reaction to occur and help in dissolving the reactants.These solvents are a good medium for the reaction and also help dissolve the reactants. The reaction temperature is carefully controlled, often in the range of 0 - 50 degC.The temperature of the reaction is carefully controlled and usually falls between 0 and 50 degC. Lower temperatures may be used to control the reactivity and prevent side - reactions, such as polymerization of the methacrylate group.Lower temperatures can be used to control reactivity and avoid side reactions, such a polymerization of methacrylate groups. A catalyst may be added to accelerate the reaction.To accelerate the reaction, a catalyst can be added. For example, tertiary amines like triethylamine can be used as catalysts to facilitate the deprotonation steps.As an example, tertiary amino acids like triethylamine are useful catalysts for deprotonation.
4. Purification
After the reaction is complete, the reaction mixture contains the desired product along with by - products such as salts (formed from the base and the acid by - products), unreacted starting materials, and possible oligomers.The reaction mixture will contain the desired product, along with by-products such as salts, unreacted materials, and possible polymers. Purification is typically achieved through a combination of techniques.Purification is usually achieved by combining techniques. Liquid - liquid extraction can be used to separate the organic layer containing the product from the aqueous layer with the salts.Liquid-liquid extraction can be used for the separation of the organic layer that contains the product and the aqueous layers with the salts. Then, distillation is often employed to further purify the product.Distillation is then used to further purify a product. Methacrylic acid, 2 - isocyanatoethyl ester has a characteristic boiling point, and by carefully controlling the distillation conditions, the pure product can be obtained, removing any remaining impurities.Methacrylic Acid, 2 - Isocyanatoethyl Ester has a boiling point that can be controlled to obtain the pure product.
What are the storage requirements for Methacrylic acid, 2-isocyanatoethyl ester?
Methacrylic acid, 2 - isocyanatoethyl ester is a chemical with specific storage requirements due to its properties.Due to its properties, Methacrylic Acid, 2 - Isocyanatoethyl Ester has specific storage requirements.
Firstly, it should be stored in a cool and well - ventilated area.It should be stored in an area that is cool and well-ventilated. High temperatures can accelerate chemical reactions, including polymerization.High temperatures can speed up chemical reactions, such as polymerization. The ideal storage temperature is typically around 2 - 8degC.Ideal storage temperatures are typically between 2 and 8degC. In a cool environment, the rate of decomposition or unwanted chemical changes is significantly reduced.In a cool atmosphere, the rate of chemical change or decomposition is reduced. If stored at elevated temperatures, the compound may start to polymerize, which not only ruins its quality but can also pose a safety hazard as polymerization can be an exothermic process.If the compound is stored at high temperatures, it may begin to polymerize. This can ruin its quality and also pose a safety risk as polymerization is an exothermic reaction.
Secondly, it must be stored away from sources of ignition.Second, it should be stored far from ignition sources. This chemical is flammable.This chemical is flammable. Any open flames, sparks from electrical equipment, or heat sources near the storage area can potentially ignite the substance.The substance can be ignited by any open flames, sparks or heat sources in the vicinity of the storage area. As it burns, it can release harmful fumes such as isocyanates, which are toxic and can cause severe respiratory problems if inhaled.It can release toxic fumes like isocyanates when it burns. Inhaling these fumes can cause respiratory problems.
Thirdly, it should be stored in a tightly sealed container.Thirdly, the container should be tightly sealed. Exposure to air can lead to reactions with moisture in the air.Air exposure can cause reactions with the moisture in air. The isocyanate group in 2 - isocyanatoethyl methacrylate is reactive towards water.The isocyanate in 2 -isocyanatoethylmethacrylate reacts with water. This reaction can result in the formation of carbon dioxide gas, which may cause pressure build - up in the container if it is not properly vented or sealed.This reaction can lead to the formation of carbon dioxide, which can cause pressure build-up in the container if the container is not properly vented. Over time, the reaction with moisture can also degrade the quality of the chemical.The chemical's quality can be affected by the moisture reaction over time.
Fourthly, separate storage from incompatible materials is crucial.Separate storage from incompatible materials, fourthly, is essential. It should not be stored near strong acids, bases, or amines.It should not be stored in the vicinity of strong acids, bases or amines. Acids can catalyze polymerization reactions, while bases and amines can react with the isocyanate group.Acids can catalyze reactions of polymerization, while bases and amino acids can react with isocyanate groups. For example, an amine can react with the isocyanate to form a urea derivative, altering the chemical structure and properties of the methacrylic acid, 2 - isocyanatoethyl ester.An amine, for example, can react with isocyanate and form a urea-derived product, altering its chemical structure and properties.
Finally, proper labeling of the storage container is essential.The labeling of the container is also important. The label should clearly indicate the name of the chemical, its hazardous properties such as flammability and toxicity, and any special handling instructions.Labels should clearly state the name of the substance, its hazardous properties, such as flammability or toxicity, and special handling instructions. This helps ensure that anyone handling the stored chemical is aware of the potential risks and can take appropriate safety measures.This ensures that anyone handling the chemical is aware of any potential risks and can take the appropriate safety measures.