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2-(hydroxymethyl)acrylic Acid Ethyl Ester


Properties
Product Name 2-(Hydroxymethyl)acrylic acid ethyl ester
Cas Number 110-49-6
Formula C6H10O3
Molar Mass 130.14 g/mol
Density 1.057 g/cm³
Boiling Point 160-163 °C
Melting Point -39 °C
Flash Point 52 °C
Vapor Pressure 5.3 mmHg at 25 °C
Refractive Index 1.418
Solubility Soluble in water
Stability Stable under recommended storage conditions
Flammability Flammable
FAQ

What is the chemical structure of 2-(Hydroxymethyl)acrylic acid ethyl ester?

2 - (Hydroxymethyl)acrylic acid ethyl ester is an organic compound with an interesting chemical structure.
Let's break down its structure based on its name.Let's deconstruct its structure using its name. First, we start with the acrylic acid ethyl ester part.We will start with the acrylic ethyl ester. Acrylic acid has the structure of a carboxylic acid with a double bond in the molecule.Acrylic acid is a carboxylic with a double-bond structure. When it forms an ethyl ester, the -OH group of the carboxylic acid reacts with the -OH group of ethanol in an esterification reaction.In an esterification process, the OH group of the carboxylic acids reacts with the group OH of ethanol to form an ethyl ester. The result is that the -OH of the carboxylic acid is replaced by -O - CH2 - CH3.The carboxylic acid's -OH is replaced by a -O-CH2 -CH3 group. So, the basic structure of acrylic acid ethyl ester has a double - bonded carbon - carbon (C = C) group, a carbonyl group (C = O) adjacent to an oxygen atom which is part of the ester linkage, and an ethyl group (-CH2 - CH3) attached to this oxygen.The basic structure of acrylic ethyl esters has a double-bonded carbon-carbon (C=C) group, an adjacent carbonyl (C=O) group to an oxygen atom that is part of the ester bond, and an attached ethyl (-CH2 -- CH3) group.

Now, let's consider the 2 - (hydroxymethyl) part.Let's now look at the 2 - (hydroxymethyl). The "2 -" indicates that the substitution occurs at the second carbon atom of the acrylic acid - based structure.The "2 –" indicates that the substitution takes place at the second carbon of the acrylic acid-based structure. The hydroxymethyl group (-CH2 - OH) is attached to this second carbon atom.This second carbon atom is attached with the hydroxymethyl group (CH2 OH).

In terms of its overall formula, if we represent the structure more formally, the main chain contains a carbon - carbon double bond (C = C).If we formalize the structure, the main chain has a double carbon-carbon bond (C =C). One of the carbon atoms of the double bond is attached to the carbonyl - oxygen - ethyl group (C = O - O - CH2 - CH3), and the other carbon atom of the double bond has a hydroxymethyl group (-CH2 - OH) attached to it.One of the carbons in the double bonds is attached to a carbonyl-oxygen-ethyl group. (C = O-O-CH2-CH3) The other carbon atom has an hydroxymethyl group attached.

In summary, 2 - (Hydroxymethyl)acrylic acid ethyl ester has a structure that combines an acrylic acid - derived ethyl ester framework with a hydroxymethyl substitution at the second carbon atom of the acrylic acid backbone. This structure gives the compound unique chemical and physical properties.This structure gives this compound unique chemical properties. The double bond can participate in polymerization reactions, which is useful in the synthesis of various polymers.The double bond is useful for polymerization reactions. The hydroxymethyl group can also be involved in further chemical reactions such as esterification or etherification, enabling the compound to be used as a building block in the synthesis of more complex organic molecules.The hydroxymethyl group is also involved in other chemical reactions, such as esterification and etherification. This allows the compound to be used in the synthesis more complex organic molecules. The ester group contributes to the compound's solubility and reactivity patterns, making it suitable for applications in areas like coatings, adhesives, and polymer chemistry.The ester group is responsible for the compound's reactivity and solubility, making it a good choice for coatings, adhesives and polymer chemistry.

What are the main applications of 2-(Hydroxymethyl)acrylic acid ethyl ester?

2 - (Hydroxymethyl)acrylic acid ethyl ester, also known as hydroxyethyl methacrylate (HEMA), has several important applications.
One of the major areas of application is in the field of coatings.Coatings are one of the most important areas of application. It can be used to formulate high - performance coatings.It can be used to create high-performance coatings. In industrial coatings, HEMA - containing polymers can provide good adhesion to various substrates, such as metals, plastics, and wood.HEMA-containing polymers are used in industrial coatings to provide good adhesion on various substrates such as metals and plastics. These coatings offer excellent abrasion resistance, chemical resistance, and weather resistance.These coatings are resistant to abrasion, chemicals, and weather. For example, in automotive coatings, the addition of HEMA can enhance the durability and appearance of the paint finish, protecting the vehicle body from environmental damage like UV radiation, moisture, and chemical contaminants.HEMA, for example, can be added to automotive coatings to improve the durability and appearance. It also protects the vehicle body against environmental damage such as UV radiation, moisture and chemical contaminants.

In the realm of adhesives, HEMA is a valuable component.HEMA is an important component in the world of adhesives. It can be incorporated into adhesive formulations to improve adhesion strength and flexibility.It can be added to adhesive formulations to increase adhesion strength and elasticity. In pressure - sensitive adhesives, HEMA helps in achieving a good balance between tack (the initial stickiness) and peel strength.HEMA is used in pressure-sensitive adhesives to achieve a good balance between initial stickiness (tack) and peel strength. This makes these adhesives suitable for applications like label - making, where the label needs to adhere firmly to the surface but also be removable without leaving residue.These adhesives are ideal for applications such as label-making, where labels need to adhere strongly to the surface while also being removable without leaving residue.

HEMA is also crucial in the production of dental materials.HEMA is also essential in the production dental materials. It is used in dental composites, which are widely used for tooth restoration.It is widely used in dental composites for tooth restoration. Dental composites containing HEMA have properties that mimic natural teeth, such as good esthetics, mechanical strength, and biocompatibility.HEMA-based dental composites have properties that mimic the natural teeth. These include good esthetics and mechanical strength. They are also biocompatible. HEMA - based polymers can bond well to the tooth structure, ensuring long - lasting restorations.HEMA-based polymers bond well with the tooth structure and ensure long-lasting restorations. Additionally, in dental cements, HEMA helps in providing good adhesion to dental substrates, enabling the secure fixation of dental appliances.HEMA is also used in dental cements to provide good adhesion. This allows for the secure fixing of dental appliances.

Another significant application is in the manufacture of contact lenses.Contact lenses are another important application. HEMA is a key monomer in the production of hydrophilic contact lenses.HEMA is an important monomer for the production of hydrophilic lenses. The hydroxyl group in HEMA allows the polymer to absorb water, making the contact lenses comfortable to wear as they can maintain a moist surface on the eye.The hydroxyl group of HEMA allows for the polymer to absorb moisture, which makes the contact lenses more comfortable to wear because they can maintain a wet surface on the eyes. The resulting lenses also have good oxygen permeability, which is essential for the health of the cornea.The lenses have good oxygen permeability which is important for the health and well-being of the cornea.

In the field of plastics and polymers, HEMA can be used as a cross - linking agent or a modifier.HEMA is used in the field of polymers and plastics as a cross-linking agent or modifier. When added to polymers, it can increase the polymer's mechanical strength, hardness, and chemical stability.HEMA can be added to polymers to increase their mechanical strength, hardness and chemical stability. For instance, in the production of acrylic polymers, HEMA can be copolymerized to introduce additional functionality, enhancing the overall performance of the plastic product.HEMA, for example, can be copolymerized in the production process of acrylic polymers to add functionality and improve the overall performance.

What are the physical and chemical properties of 2-(Hydroxymethyl)acrylic acid ethyl ester?

2 - (Hydroxymethyl)acrylic acid ethyl ester, also known as Ethyl 2 - (hydroxymethyl)acrylate.
Physical Properties

Appearance
It is usually a colorless to slightly yellow liquid.It is usually a colorless or slightly yellow liquid. This appearance is typical for many organic esters with relatively simple molecular structures and the presence of a hydroxyl and ester functional groups.This is a common appearance for many organic esters, which have relatively simple molecular structure and a presence of hydroxyl and ester functional groups. The lack of extensive conjugation or complex chromophores in its structure contributes to its relatively light color.Its relatively light color is due to the lack of complex chromophores or extensive conjugation in its structure.

Boiling Point
The boiling point of 2 - (hydroxymethyl)acrylic acid ethyl ester is influenced by the intermolecular forces present. The hydroxyl group can participate in hydrogen bonding, while the ester group contributes to dipole - dipole interactions.The hydroxyl can participate in hydrogen bonds, while the ester contributes to dipole-dipole interactions. These forces require a certain amount of energy to overcome for the liquid to vaporize.To overcome these forces, a certain amount energy is required to cause the liquid to vaporize. Typically, it has a boiling point in the range where the balance between these intermolecular forces and the thermal energy is reached, allowing the transition from the liquid to the gas phase.It has a boiling temperature in the range of energy required to balance these intermolecular interactions and thermal energy, allowing it to transition from liquid into gas phase.

Melting Point
The melting point is related to how the molecules are arranged in the solid state.The melting point is determined by the arrangement of the molecules in the solid state. The presence of the hydroxyl group can lead to some degree of ordered packing through hydrogen - bonding networks.The presence of hydroxyl groups can lead to a degree of ordered packing via hydrogen-bonding networks. However, the relatively small size and flexibility of the molecule may prevent extremely high - ordered packing, resulting in a melting point that is not overly high, enabling it to exist as a liquid at or near room temperature under normal conditions.The relatively small size and flexibility may prevent extremely high-ordered packing, resulting a melting temperature that is not too high.

Solubility
It is soluble in many organic solvents.It is soluble with many organic solvents. The ester group and the hydroxyl group both contribute to its solubility behavior.Its solubility is influenced by both the ester and hydroxyl groups. The ester group is lipophilic, allowing it to interact with non - polar solvents through van der Waals forces.The ester group interacts with non-polar solvents via van der Waals forces because it is lipophilic. The hydroxyl group can form hydrogen bonds with polar solvents, such as alcohols.The hydroxyl group is able to form hydrogen bonds with alcohols and other polar solvents. It also has some solubility in water due to the hydrogen - bonding ability of the hydroxyl group, although its solubility in water is limited because of the relatively large non - polar ethyl ester part of the molecule.The hydroxyl group can form hydrogen bonds with polar solvents, such as alcohols.

Chemical Properties

Reactivity of the Double BondDouble Bond Reactivity
The most reactive part of the molecule is the carbon - carbon double bond.The double carbon bond is the most reactive part of a molecule. It can undergo addition reactions, such as polymerization.It can undergo polymerization and other addition reactions. In the presence of initiators, the double bond can break, and monomers of 2 - (hydroxymethyl)acrylic acid ethyl ester can link together to form polymers. This property is widely used in the synthesis of various polymers, for example, in the production of coatings, adhesives, and resins.This property is used to synthesize various polymers. For example, it can be used in the production or adhesives and resins. The double bond can also react with electrophiles in electrophilic addition reactions, adding other functional groups to the molecule.In electrophilic additions, the double bond can react with electrophiles to add other functional groups.

Reactivity of the Hydroxyl GroupReactivity of Hydroxyl Group
The hydroxyl group can participate in esterification reactions.The hydroxyl group is a participant in esterification reactions. It can react with carboxylic acids or acid anhydrides to form new esters.It can react to form new esters with carboxylic acid or acid anhydrides. This can be used to modify the properties of the molecule, for example, to introduce different functional groups or to change the solubility and reactivity of the compound.This can be used for modifying the properties of a molecule. For example, it can be used to introduce different functional group or to change the solubility or reactivity of a compound. Additionally, the hydroxyl group can be deprotonated in the presence of strong bases, making the molecule more reactive in certain substitution reactions.In addition, the hydroxyl groups can be deprotonated when strong bases are present, increasing the reactivity of the molecule in certain substitution reactions.

Reactivity of the Ester GroupReactivity of Ester Group
The ester group can undergo hydrolysis reactions.The ester group is susceptible to hydrolysis reactions. In acidic or basic conditions, the ester bond can be cleaved.The ester bond can be broken in acidic or basic conditions. In acidic hydrolysis, the ester reacts with water to form the corresponding carboxylic acid and alcohol.In acidic hydrolysis the ester reacts to water and forms the carboxylic acid. In basic hydrolysis (saponification), the ester reacts with a base to form the carboxylate salt and alcohol.In basic hydrolysis, the ester reacts to a base in order to form alcohol and carboxylate salt. These reactions are important in the degradation and modification of the molecule in various chemical processes.These reactions are crucial in the degradation and modification the molecule during various chemical processes.

How is 2-(Hydroxymethyl)acrylic acid ethyl ester synthesized?

2 - (Hydroxymethyl)acrylic acid ethyl ester can be synthesized through the following general approach.
One common method is based on the reaction of acrolein with formaldehyde and ethanol.One common method relies on the reaction between acrolein and formaldehyde. In the first step, acrolein reacts with formaldehyde in the presence of a catalyst.In the first stage, acrolein is reacted with formaldehyde and ethanol in the presence a catalyst. This reaction is typically a condensation reaction.This reaction is usually a condensation reaction. The carbon - carbon double bond in acrolein and the carbonyl group of formaldehyde can react under appropriate reaction conditions.Under the right conditions, the carbon-carbon double bond of acrolein can react with formaldehyde's carbonyl group. A base - catalyzed reaction is often employed.Often, a base-catalyzed process is used. Bases such as sodium hydroxide or potassium hydroxide can be used.You can use bases such as potassium hydroxide or sodium hydroxide. These bases help to initiate the reaction by deprotonating the reactants to form reactive intermediates.These bases can help initiate the reaction by deprotonating reactants to produce reactive intermediates. The reaction between acrolein and formaldehyde leads to the formation of an intermediate compound containing both the carbon - carbon double bond from acrolein and a hydroxymethyl group introduced from formaldehyde.The reaction between formaldehyde and acrolein leads to an intermediate compound that contains both the carbon-carbon double bond from formaldehyde and the hydroxymethyl group from acrolein.

After the formation of the intermediate containing the hydroxymethyl group, the next step is to react this intermediate with ethanol.The next step is to react the intermediate with ethanol. This reaction is an esterification reaction.Esterification is the name of this reaction. An acid catalyst is usually required for this esterification process.This esterification reaction usually requires an acid catalyst. Sulfuric acid or p - toluenesulfonic acid can be used as catalysts.As catalysts, sulfuric acid or p-toluenesulfonic acids can be used. The acid catalyst protonates the carboxylic acid group (or the intermediate functional group) of the compound formed from acrolein and formaldehyde, making it more reactive towards the nucleophilic attack by ethanol.The acid catalyst protonates carboxylic acid groups (or intermediate functional groups) of the compound made from acrolein & formaldehyde. This makes it more reactive to the nucleophilic attack of ethanol. The ethanol molecule attacks the protonated intermediate, and through a series of reaction steps, including the elimination of a water molecule, the 2 - (Hydroxymethyl)acrylic acid ethyl ester is formed.

The reaction conditions need to be carefully controlled.The reaction conditions must be carefully controlled. For the reaction between acrolein and formaldehyde, the reaction temperature is usually in the range of 20 - 60 degrees Celsius, and the reaction time can vary from several hours to overnight depending on the catalyst used and the reactant concentrations.The temperature of the reaction between formaldehyde and acrolein is usually between 20 and 60 degrees Celsius. The reaction time can range from several hours to over night depending on the concentrations of the reactants and the catalyst. For the esterification step with ethanol, the temperature is often higher, typically around 80 - 120 degrees Celsius, to facilitate the formation of the ester bond.The esterification with ethanol is usually carried out at a higher temperature, typically between 80 and 120 degrees Celsius. This helps to form the ester bond. After the reaction is completed, the product can be purified through methods such as distillation, extraction, or column chromatography to obtain pure 2 - (Hydroxymethyl)acrylic acid ethyl ester.

What are the safety precautions when handling 2-(Hydroxymethyl)acrylic acid ethyl ester?

2 - (Hydroxymethyl)acrylic acid ethyl ester is a chemical compound that requires certain safety precautions during handling.
First, personal protective equipment is essential.Wearing appropriate chemical-resistant gloves is essential. Wear appropriate chemical - resistant gloves, preferably made of materials like nitrile or neoprene.Wear gloves that are resistant to chemicals, preferably made from nitrile or Neoprene. These gloves can prevent the chemical from coming into contact with the skin, as skin contact may cause irritation, redness, and potential long - term damage.These gloves will prevent the chemical from contacting the skin. Skin contact can cause irritation, redness and long-term damage. Also, wear safety goggles or a face shield to protect the eyes.Wear safety goggles, or a face shield, to protect your eyes. In case of any splashes, the eyes are extremely vulnerable, and even a small amount of this chemical in the eyes can lead to severe pain, irritation, and possible vision impairment.Eyes are very vulnerable in case of splashes. Even a small amount can cause severe pain, irritation and vision impairment.

Ventilation is crucial.Ventilation is essential. Handle the compound in a well - ventilated area, preferably under a fume hood.Handle the compound in an area that is well-ventilated, preferably under a fumehood. This chemical may release vapors that can be harmful if inhaled.Inhalation of vapors from this chemical can be harmful. Inhalation can cause respiratory tract irritation, coughing, and shortness of breath.Inhalation of this chemical can cause irritation to the respiratory tract, coughing and shortness in breath. A fume hood effectively removes these vapors, reducing the risk of inhalation exposure.A fume hood removes these vapors effectively, reducing the risk for inhalation.

When storing 2 - (Hydroxymethyl)acrylic acid ethyl ester, keep it in a cool, dry place away from sources of ignition. This chemical is flammable, so any open flames, sparks, or hot surfaces should be avoided.This chemical is flammable. Avoid open flames, sparks or hot surfaces. Store it in a container made of a compatible material, such as glass or certain types of plastics that can withstand the chemical's properties without reacting.Store it in a container that is compatible with the chemical, such as a glass container or certain types plastics.

In case of spills, take immediate action.Take immediate action in the event of spills. First, evacuate the area to prevent others from being exposed.To prevent exposure to others, first evacuate the area. Then, use appropriate absorbent materials like sand or vermiculite to soak up the spill.Use absorbent materials such as sand or Vermiculite to absorb the spill. Avoid using materials that may react with the chemical.Avoid materials that could react with the chemical. After cleaning up the spill, properly dispose of the absorbent material according to local regulations.After cleaning the spill, dispose of the absorbent materials according to local regulations.

If there is skin contact, immediately wash the affected area with plenty of soap and water for at least 15 minutes.If the chemical gets into your eyes, rinse them thoroughly with clean water for at least 15 min. If the chemical gets into the eyes, rinse them thoroughly with clean water for at least 15 minutes and seek immediate medical attention.If the chemical gets in the eyes, rinse the eyes thoroughly with clean water and seek immediate medical care. In case of inhalation, move to fresh air immediately and, if symptoms persist, seek medical help.In the event of inhalation, get to fresh air as soon as possible. If symptoms persist, consult a doctor.