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Product Name | 3,3-Dimethylacrylic acid methyl ester |
Cas Number | 924-50-5 |
Formula | C6H10O2 |
Molar Mass | 114.14 |
Boiling Point | 130-132 °C |
Density | 0.91 g/cm³ |
Refractive Index | 1.405 |
Flash Point | 28 °C |
Appearance | Colorless liquid |
Odor | Characteristic |
Solubility | Slightly soluble in water |
Vapor Pressure | 5.5 mmHg at 25 °C |
Stability | Stable under recommended storage conditions |
Autoignition Temperature | 400 °C |
Viscosity | Not available |
What is the chemical structure of 3,3-Dimethylacrylic acid methyl ester?
3,3 - Dimethylacrylic acid methyl ester is an organic compound.Dimethylacrylic Acid methyl Ester is a compound. Let's break down its chemical structure step by step.Let's break it down step by step.
First, consider the acrylic acid part.Consider first the acrylic acid. Acrylic acid has the structure CH2=CH - COOH.Acrylic acid is composed of the structure CH2=CH-COOH. It contains a carbon - carbon double bond (C = C) and a carboxylic acid functional group (-COOH).It contains a double carbon-carbon bond (C = C), and a carboxylic group (-COOH).
In 3,3 - Dimethylacrylic acid, two methyl groups (-CH3) are attached to the third carbon atom of the acrylic acid structure.Two methyl groups (CH3) are attached to carbon 3 of the acrylic acid. So the structure of 3,3 - Dimethylacrylic acid is (CH3)2C=CH - COOH.The structure of 3,3-Dimethylacrylic Acid is (CH3)2C=CH-COOH.
When it forms the methyl ester, the -OH group of the carboxylic acid reacts with methanol (CH3OH) in an esterification reaction.Esterification occurs when the -OH group from the carboxylic acids reacts with the methanol (CH3OH). In this process, the -OH of the carboxylic acid is replaced by the -OCH3 group from methanol.This process replaces the -OH group of the carboxylic acids with the -OCH3 from methanol.
So, the chemical structure of 3,3 - Dimethylacrylic acid methyl ester has a carbon - carbon double bond at the start of the chain.The chemical structure of 3,3-Dimethylacrylic Acid methyl Ester begins with a double carbon-carbon bond. Connected to the second carbon atom of this chain is a carbon atom with two methyl groups attached.A carbon atom with two attached methyl groups is connected to the second carbon of this chain. And at the end of the chain, there is a carbonyl group (C = O) which is then connected to an -OCH3 group.At the end of the chain is a carbonyl (C = O) group which is connected to an OCH3 group. In a more descriptive way, the molecule can be written as (CH3)2C=CH - COOCH3.The molecule can also be written (CH3)2C=CH-COOCH3.
The carbon - carbon double bond gives the compound the potential for addition reactions, such as reacting with halogens, hydrogen, or other reagents that can break the double bond and add new atoms or groups to the molecule.The double bond between carbon and carbon gives the compound the ability to undergo addition reactions. For example, it can react with halogens or hydrogens which can break the double bonds, adding new atoms or groupings to the molecule. The ester functional group (-COOCH3) has its own set of chemical properties.The ester functional groups (-COOCH3) have their own chemical properties. Esters can undergo hydrolysis reactions in the presence of acids or bases to break back into the carboxylic acid and the alcohol from which they were formed.Esters can undergo hydrolysis in the presence acid or base to break back into carboxylic acids and alcohols from which they were originally formed. In the case of 3,3 - Dimethylacrylic acid methyl ester, hydrolysis would yield 3,3 - Dimethylacrylic acid and methanol.In the case 3,3-Dimethylacrylic Acid methyl ester hydrolysis would result in 3,3-Dimethylacrylic Acid and methanol. Overall, the combination of the double bond and the ester group in 3,3 - Dimethylacrylic acid methyl ester endows it with a unique set of chemical reactivity and physical properties that are important in various chemical applications, including in the synthesis of polymers and other organic compounds.Overall, the combination between the double bond and ester group in 3,3- Dimethylacrylic Acid methyl ester gives it a unique set chemical reactivity, and physical properties, which are important for various chemical applications.
What are the main applications of 3,3-Dimethylacrylic acid methyl ester?
3,3 - Dimethylacrylic acid methyl ester has several important applications.The dimethylacrylic acid methyl ester has many important applications.
In the field of polymer synthesis, it serves as a valuable monomer.It is a valuable monomer in the field of polymer syntheses. When polymerized, the resulting polymers can possess unique properties.The polymers that result from polymerization can have unique properties. For example, the methyl ester group and the dimethyl substitution on the acrylic acid backbone can influence the polymer's solubility, hardness, and weather resistance.The methyl ester and dimethyl substitutions on the acrylic acid backbone, for example, can influence the polymer’s solubility and weather resistance. These polymers can be used in the production of coatings.These polymers are used to produce coatings. Coatings made from polymers containing 3,3 - Dimethylacrylic acid methyl ester monomers may have enhanced abrasion resistance, which is beneficial for protecting surfaces of various materials such as metals, woods, and plastics.Coatings made of polymers containing 3,3-Dimethylacrylic acid monomers can have improved abrasion resistance. This is beneficial for protecting surfaces such as metals and woods. They can also improve the adhesion of the coating to the substrate, ensuring long - lasting protection.They can also improve adhesion, which ensures long-lasting protection.
In the area of adhesive manufacturing, this compound plays a significant role.This compound is important in the adhesive manufacturing industry. The properties of 3,3 - Dimethylacrylic acid methyl ester contribute to the development of high - performance adhesives.The properties of 3,3-Dimethylacrylic Acid methyl Ester contribute to the creation of high-performance adhesives. The acrylic - based polymers formed from it can provide strong bonding capabilities.Acrylic - based plastics can be formed from this acid. They have strong bonding abilities. These adhesives are useful in a wide range of industries, including automotive, electronics, and packaging.These adhesives can be used in many industries, such as automotive, electronics, packaging, and more. In the automotive industry, they can be used to bond interior components, like plastic trims, due to their good adhesion and durability.Due to their high adhesion and durability, they are used in the automotive industry to bond interior trims like plastic trims. In electronics, they are suitable for bonding circuit boards and small components because of their ability to withstand different environmental conditions.They are ideal for bonding small components and circuit boards in electronics due to their ability to withstand various environmental conditions.
It is also involved in the synthesis of specialty chemicals.It is also used in the production of specialty chemicals. Through various chemical reactions, 3,3 - Dimethylacrylic acid methyl ester can be transformed into other complex molecules.Through different chemical reactions, 3,3-Dimethylacrylic Acid methyl ester is transformed into complex molecules. For instance, it can be used in the preparation of certain pharmaceutical intermediates.It can be used to prepare certain pharmaceutical intermediates, for example. The specific structure of this ester can be modified to create molecules with specific biological activities.This ester's structure can be altered to create molecules that have specific biological properties. Additionally, in the fragrance and flavor industry, derivatives of 3,3 - Dimethylacrylic acid methyl ester can be synthesized to produce unique scents or flavors.In the fragrance and flavor industries, derivatives of 3,3-Dimethylacrylic acid, methyl ester, can be synthesized in order to produce unique scents or tastes. The chemical reactivity of the ester group allows for the creation of new compounds with desired olfactory or gustatory properties.The ester group's chemical reactivity allows for the creation new compounds with desired olfactory and gustatory properties. Overall, 3,3 - Dimethylacrylic acid methyl ester is a versatile compound with applications that span multiple industries, contributing to the development of various high - quality products.Overall, 3,3- Dimethylacrylic Acid methyl Ester is a versatile chemical compound that has applications in multiple industries. It contributes to the development of high-quality products.
How is 3,3-Dimethylacrylic acid methyl ester synthesized?
3,3 - Dimethylacrylic acid methyl ester can be synthesized through the following general approaches:The following general approaches can be used to synthesize 3,3-dimethylacrylic acid methyl esters:
1. Esterification of 3,3 - Dimethylacrylic Acid with MethanolEsterification of 3,3-Dimethylacrylic Acid with Methanol
The most straightforward method is the direct esterification reaction.Direct esterification is the easiest method. First, obtain 3,3 - dimethylacrylic acid.To begin, you will need to obtain 3,3-dimethylacrylic acid. This acid can react with methanol in the presence of a catalyst.This acid can be used to react with methanol when a catalyst is present. Commonly used catalysts for such esterification reactions are sulfuric acid or p - toluenesulfonic acid.Catalysts are commonly used for these esterification reactions, such as sulfuric acid or the p-toluenesulfonic acids.
The reaction is set up in a suitable reaction vessel.The reaction is carried out in a reaction vessel. For example, a round - bottom flask equipped with a reflux condenser can be used.You can use a flask with a round bottom and a reflux condenser, for example. The appropriate amounts of 3,3 - dimethylacrylic acid and methanol are mixed in the flask.In the flask, mix the 3,3-dimethylacrylic acid with methanol in the appropriate amounts. If sulfuric acid is chosen as the catalyst, a small amount of concentrated sulfuric acid is carefully added.If sulfuric is the catalyst of choice, a small quantity of concentrated sulfuric is added. The mixture is then heated under reflux.The mixture is heated under reflux. The heat provides the energy needed to drive the reaction forward.The heat is what drives the reaction. During the reaction, water is formed as a by - product.Water is formed during the reaction. To shift the equilibrium towards the formation of the ester, methods such as removing water from the reaction system can be employed.Methods such as removing the water from the system can be used to shift the equilibrium in favor of the ester. One way to do this is by using a Dean - Stark apparatus, which allows the continuous separation of water from the reaction mixture.This can be achieved by using the Dean-Stark apparatus which allows for the continuous separation water from the reaction mix.
2. From Precursors via Multiple StepsFrom Precursors by Multiple Steps
Another route might involve starting from precursors that can be transformed into the desired ester in a series of reactions.A second route would be to start with precursors which can be transformed in the desired ester through a series reactions. For instance, one could start with an appropriate aldehyde or ketone.One could, for example, start with a suitable aldehyde. Through a sequence of reactions like aldol condensation and subsequent modifications.Through a series of reactions such as aldol condensation, and subsequent modifications.
If starting from an aldehyde, an aldol - type reaction could be carried out to build up the carbon - carbon double - bond structure.Starting with an aldehyde a reaction of the type aldol could be performed to build up a double-bond structure between carbon and carbon. After forming the unsaturated acid intermediate through oxidation steps, methylation can be achieved to form the methyl ester.After forming an unsaturated intermediate through oxidation, methylation is possible to form a methyl ester. This multi - step approach might require more careful reaction control and purification at each step.This multi-step approach may require more careful reaction monitoring and purification at every step. But it can be useful when the starting materials are more readily available or when the direct esterification approach faces challenges.It can be used when the starting materials available are easier to obtain or when the direct esterification approach is difficult.
For example, if starting from isobutyraldehyde, an aldol - like reaction with another carbonyl - containing compound could be used to form an intermediate with the correct carbon - chain structure.If starting with isobutyraldehyde you could use an aldol-like reaction with another compound containing carbonyl to form an intermediate that has the correct carbon-chain structure. Oxidation of the intermediate alcohol or aldehyde group to a carboxylic acid, followed by esterification with methanol, would lead to the formation of 3,3 - dimethylacrylic acid methyl ester.The esterification of methanol with the carboxylic acid formed by oxidation of the intermediate aldehyde or alcohol group would result in the 3,3 - dimethylacrylic methyl ester.
Purification of the synthesized 3,3 - dimethylacrylic acid methyl ester is typically required.Purification is usually required for the synthesized 3,3-dimethylacrylic acid. This can be done through techniques such as distillation, taking advantage of the different boiling points of the ester and any unreacted starting materials or by - products.Distillation techniques, which take advantage of the different boiling point of the ester as well as any unreacted starter materials or by-products, can be used to achieve this. Chromatographic methods like column chromatography can also be used for more precise purification if needed.If needed, chromatographic methods such as column chromatography may be used to achieve a more precise purification.
What are the physical and chemical properties of 3,3-Dimethylacrylic acid methyl ester?
3,3 - Dimethylacrylic acid methyl ester, also known as methyl 3,3 - dimethylacrylate, has the following physical and chemical properties:The physical and chemical properties of methyl 3,3-dimethylacrylate, also known by the name methyl 3,3-dimethylacrylate, are as follows:
Physical properties:Physical Properties
Appearance: It is typically a colorless to slightly yellow liquid.Appearance: This liquid is usually colorless or slightly yellow. This appearance is common for many esters in the organic chemistry realm.This is a common appearance for many esters used in organic chemistry. The relatively light color is due to its simple molecular structure without highly conjugated or complex chromophoric groups.The light color is a result of its simple molecular composition, which lacks highly conjugated or complicated chromophoric group.
Boiling point: It has a boiling point in the range of around 138 - 140 degC.Boiling point : Its boiling point is between 138 and 140 degrees Celsius. This boiling point is influenced by the size of the molecule and the intermolecular forces present.This boiling point depends on the size of a molecule and intermolecular forces. The ester functional group contributes to dipole - dipole interactions, and the overall molecular size determines the strength of London dispersion forces.The ester functional groups contribute to dipole-dipole interactions and the overall molecule size determines the strength London dispersion forces. These forces need to be overcome for the liquid to vaporize.These forces must be overcome in order for the liquid vapor to occur.
Melting point: The melting point of 3,3 - dimethylacrylic acid methyl ester is relatively low, usually below room temperature.Melting point: The melting temperature of 3,3-dimethylacrylic acid is usually below room temperatures. This is because the molecules are not arranged in a highly ordered, rigid structure in the solid state due to the branching of the dimethyl groups, which disrupts close - packing.This is due to the fact that the molecules are not arranged into a highly-ordered, rigid structure when in the solid state, as a result of the branching dimethyl groups.
Density: It has a density of approximately 0.9 g/cm3.Density: Its density is approximately 0.9g/cm3. The density is related to the mass of the molecule and the volume it occupies in the liquid state.The density is a function of the mass and volume of the molecule in liquid form. The combination of carbon, hydrogen, and oxygen atoms in the molecule gives it this characteristic density value.The combination of oxygen, hydrogen, and carbon atoms within the molecule determines its characteristic density.
Solubility: It is sparingly soluble in water.It is sparingly water soluble. The ester group contains polar C = O and C - O - C bonds, but the non - polar alkyl groups (the dimethyl - substituted propyl part) dominate the molecule's solubility behavior.The ester group contains C = O and C-O-C bonds, but it is the non-polar alkyl groups that dominate the solubility of the molecule (the dimethyl-substituted propyl portion). As a result, it has a limited ability to interact with polar water molecules through hydrogen bonding.It is therefore limited in its ability to interact with water molecules that are polar through hydrogen bonds. However, it is soluble in many organic solvents such as ethanol, diethyl ether, and chloroform.It is soluble in ethanol, chloroform, and diethylether. These organic solvents have similar non - polar or weakly polar characteristics, allowing for favorable intermolecular interactions through London dispersion forces and dipole - dipole interactions.These organic solvents are non-polar or weakly-polar, allowing for favorable interactions between molecules through London dispersion and dipole-dipole interactions.
Chemical properties:Chemical properties
Reactivity of the double bond: The most reactive part of 3,3 - dimethylacrylic acid methyl ester is the carbon - carbon double bond.Carbon-carbon double bond is the most reactive part of the 3,3-dimethylacrylic acid methyl ester. It can undergo addition reactions.It can undergo addition reaction. For example, it can react with halogens (such as bromine in an addition reaction to form a dibromo - derivative).It can, for example, react with halogens to form dibromo-derivatives (such bromine in addition reactions). In the presence of a suitable catalyst, it can also participate in polymerization reactions.It can also be used in polymerization reactions when a suitable catalyser is present. The double bond can open up, allowing monomers to link together to form polymers.The double bond can be opened, allowing monomers and polymers to link. This property makes it useful in the synthesis of various polymers and copolymers.This property makes it useful for the synthesis of polymers and copolymers.
Hydrolysis of the ester group: The ester group in 3,3 - dimethylacrylic acid methyl ester can be hydrolyzed.The ester group of 3,3-dimethylacrylic acid can be hydrolyzed. In the presence of an acid or a base, the ester bond can be cleaved.The ester bond may be cleaved in the presence of an base or acid. Under acidic conditions, a carboxylic acid (3,3 - dimethylacrylic acid) and an alcohol (methanol) are formed in a reversible reaction.In a reversible reaction, under acidic conditions, a carboxylic (dimethylacrylic acid, 3,3-) and alcohol (methanol), are formed. In basic hydrolysis, the carboxylate salt of 3,3 - dimethylacrylic acid and methanol are produced.In basic hydrolysis the carboxylate of 3,3-dimethylacrylic acid is produced. This hydrolysis reaction is important in the chemical modification and degradation of the compound.This hydrolysis reaction plays a crucial role in the chemical modification and degradation.
Reaction with nucleophiles: The carbonyl carbon in the ester group is electrophilic due to the electron - withdrawing nature of the oxygen atoms.The electron-withdrawing nature of oxygen atoms makes the carbonyl carbon in ester groups electrophilic. Nucleophiles such as amines can react with the ester to form amides.Nucleophiles, such as amines, can react with esters to form amides. This reactivity allows for the synthesis of more complex organic compounds with different functional groups.This reactivity allows the synthesis of organic compounds with more complex functional groups.
What safety precautions should be taken when handling 3,3-Dimethylacrylic acid methyl ester?
When handling 3,3 - Dimethylacrylic acid methyl ester, several important safety precautions should be observed.When handling 3,3-Dimethylacrylic acid, methyl ester you should observe several safety precautions.
First, personal protective equipment (PPE) is crucial.Personal protective equipment is essential. Wear appropriate chemical - resistant gloves, such as those made of nitrile or neoprene.Wear gloves that are resistant to chemicals, such as those made from nitrile or Neoprene. These gloves can prevent skin contact, which could lead to skin irritation, allergic reactions, or potential absorption of the chemical through the skin.These gloves can protect the skin from contact with chemicals, which may cause skin irritation, allergic reactions or absorption through the skin. A lab coat or other protective clothing should be worn to cover the body and minimize the risk of chemical spills on the skin or clothing.Wearing a lab coat or other protective clothing will cover the body, reducing the risk of chemical spills. Additionally, safety goggles or a face shield should be used to protect the eyes from splashes.Safety goggles or face shields can also be used to protect eyes from splashes. The ester could cause severe eye damage if it comes into contact with the eyes.If the ester comes into contact with your eyes, it can cause serious eye damage.
Ventilation is another key aspect.Ventilation is also important. Work with 3,3 - Dimethylacrylic acid methyl ester in a well - ventilated area, preferably under a fume hood.Work with 3,3-Dimethylacrylic Acid methyl Ester in an area that is well-ventilated, preferably under a hood. This chemical may give off vapors that can be irritating to the respiratory system.This chemical can emit vapors which can irritate the respiratory system. Inadequate ventilation can lead to the build - up of these vapors, increasing the risk of inhalation.Inadequate ventilation may lead to a build-up of these vapors and increase the risk of inhalation. Inhalation may cause symptoms such as coughing, shortness of breath, and irritation of the nose and throat.Inhalation can cause symptoms like coughing, shortness in breath, and irritation to the nose and throat.
Storage of 3,3 - Dimethylacrylic acid methyl ester also requires attention.The storage of 3,3-Dimethylacrylic Acid methyl Ester is also important. Store it in a cool, dry place away from heat sources and open flames.Store it in a dry, cool place away from heat and open flames. This compound is flammable, so keeping it away from ignition sources is essential to prevent fires or explosions.To prevent fires and explosions, it is important to keep this compound away from ignition sources. It should be stored in a tightly - sealed container to prevent vapor leakage.Store it in a tightly-sealed container to prevent vapor leaking. Additionally, ensure that the storage area is clearly labeled with the nature of the chemical and appropriate hazard warnings.Also, make sure that the storage area has a label clearly stating the type of chemical and any appropriate warnings.
When handling the substance, avoid generating dust or mists.Avoid generating dust and mists when handling the substance. This can be achieved by using proper pouring and transfer techniques.Pouring and transferring the material in the correct manner can achieve this. For example, when transferring the ester from one container to another, do it slowly and carefully to prevent splashing and aerosol formation.When transferring the ester between containers, pour it slowly and carefully in order to avoid splashing or aerosol formation.
In case of a spill, immediate action is necessary.Immediate action is required in the event of a spill. First, evacuate the area if the spill is large enough to pose a significant inhalation or fire risk.If the spill is large and poses a fire or inhalation risk, you should evacuate the area. For small spills, absorb the liquid with an appropriate absorbent material, such as vermiculite or sand.If the spill is small, absorb it with an absorbent material such as vermiculite, sand, or other suitable absorbent materials. Dispose of the contaminated absorbent according to local regulations.Dispose of contaminated absorbents according to local regulations. Wash the affected area thoroughly with water.Wash the affected area with water. If the chemical comes into contact with the skin or eyes, immediately rinse with large amounts of water for at least 15 minutes and seek medical attention.If the chemical gets into the eyes or skin, rinse immediately with large amounts water for at least fifteen minutes and seek medical assistance.