Chem Explorers

Unlocking the Power of Acryloyl Chloride: Versatile Applications in Chemical Industry

Acryloyl Chloride: Properties and UsesChemical compounds have their unique properties, and acryloyl chloride is no exception. It is a colorless liquid with a pungent odor.

In this article, we will discuss the chemical and physical properties of acryloyl chloride, its molecular formula, and identification facts, along with synonyms and chemical structures.

Acryloyl Chloride Definition

Acryloyl chloride is an organic compound that belongs to the family of acyl halides, which are compounds containing a carbonyl group attached to a halogen atom. Its molecular formula is C3H3ClO, with a molecular weight of 106.51g/mol.

Acryloyl Chloride Identification Facts

Acryloyl chloride has a Chemical Abstract Service (CAS) number of 814-68-6, a PubChem compound number of 10408, a ChemSpider ID number of 9972, and an European Community (EC) number of 212-082-2. These numbers help to identify the compound by its chemical structure and properties.

Acryloyl Chloride Molecular Formula

The molecular formula for acryloyl chloride is C3H3ClO. The compound contains a carbonyl group (C=O) and a chloride group (-Cl) attached to the second carbon atom of an ethene molecule (CH2=CH-).

Acryloyl Chloride Synonyms

Acryloyl chloride has several synonyms, including 2-propenoyl chloride, prop-2-enoyl chloride, and acrylic acid chloride. These synonyms make it easier to find information on the compound by using different search terms.

Chemical Structure

The chemical structure of acryloyl chloride shows the carbonyl and chloride groups connected to the C=C double bond. The presence of a double bond in the structure makes acryloyl chloride more reactive than other acyl halides.

The structure also determines the compound’s physical and chemical properties.

Uses of Acryloyl Chloride

Acryloyl chloride finds numerous applications in the chemical industry. It is an essential compound in the production of polymers, such as acrylic resins and polyurethanes.

It is also used to produce agrochemicals, pharmaceuticals, and surfactants.

Acrylic Resins

Acrylic resins find widespread use in the production of coatings, adhesives, and paint. The addition of acryloyl chloride to acrylic resins imparts the desired properties to the final product.

The properties of acrylic resins depend on the molecular weight and functionality of acryloyl chloride. A higher molecular weight leads to a higher viscosity of resins, while increasing the functionality of acryloyl chloride increases the crosslinking density, resulting in a stronger resin.

Polyurethanes

Polyurethanes are polymers containing urethane linkages (-NH-C(O)-O-) in their molecular structure. They find extensive use in the production of foams, fibers, and coatings.

Acryloyl chloride acts as a crosslinker in the production of polyurethanes, providing mechanical strength and chemical resistance to the final product.

Agrochemicals

Acryloyl chloride is used to produce several agrochemicals, such as herbicides, insecticides, and fungicides. It is used to attach functional groups that enhance the biological activity of the final product.

Pharmaceuticals

Acryloyl chloride is used in the production of several pharmaceuticals, such as analgesics and anti-inflammatory drugs. It is used to modify the chemical structure of bioactive compounds to enhance their potency and selectivity.

Surfactants

Surfactants are compounds that lower the surface tension between two liquids or between a liquid and a solid. Acryloyl chloride is used to produce surfactants with specific properties, such as hydrophobicity and amphiphilicity.

Conclusion

Acryloyl chloride is a versatile compound used in the production of various chemicals, including acrylic resins, polyurethanes, agrochemicals, pharmaceuticals, and surfactants. Its unique chemical structure contributes to its properties, enabling it to impart desired traits to products.

Understanding the various aspects of acryloyl chloride is essential for the efficient production of these chemicals.

Acryloyl Chloride Preparation in Laboratory

Acryloyl chloride is prepared in the laboratory by reacting acrylic acid with thionyl chloride. The reaction takes place at room temperature, and the product is obtained after distillation.

The reaction follows the following equation:

CH2=CHCOOH + SOCl2 CH2=CHC(O)Cl + SO2 + HCl

In the laboratory, precautions must be taken while handling acryloyl chloride as it is a highly reactive and toxic substance. It is advisable to use protective gloves, goggles, and clothing to avoid skin and eye contact.

Inhibitor

In laboratory preparation, an inhibitor is used to control the reaction rate of acryloyl chloride. An alkylated aromatic amine, such as N,N-dimethylaniline, is commonly used as an inhibitor.

These inhibitors undergo an electrophilic substitution reaction with acryloyl chloride, forming nonreactive cationic intermediates that prevent further reaction with the reactants.

Acryloyl Chloride Properties

Physical Properties

Acryloyl chloride is a colorless and volatile liquid with a pungent odor. Its melting point is -88C, while its boiling point is 75C.

The compound has a density of 1.13g/cm and a refractive index of 1.438. Acryloyl chloride is soluble in polar solvents, such as water, alcohols, and ether, but insoluble in nonpolar solvents, such as benzene and carbon tetrachloride.

Chemical Properties

Acryloyl chloride is a highly reactive compound due to its double bond between the two carbon atoms in the molecule. The reactive groups of acryloyl chloride are the carbonyl and chloride groups.

The compound undergoes various chemical reactions, including nucleophilic addition, substitution, and polymerization. Acryloyl chloride reacts with primary and secondary amines to form stable amides, and with primary and secondary alcohols to form esters.

It undergoes a nucleophilic substitution reaction with water to form acrylic acid and hydrogen chloride.

Acryloyl chloride undergoes a free radical polymerization reaction with various monomers, such as styrene, methyl methacrylate, and vinyl acetate, to produce polymers with desired properties.

Thermodynamic Properties

The thermodynamic properties of acryloyl chloride are significant in understanding its behavior under different conditions. The standard enthalpy of formation of acryloyl chloride is -104.9kJ/mol, while its standard enthalpy of vaporization is 28.4kJ/mol.

The standard entropy of the compound is 259.0 J/Kmol.

The Gibbs free energy of formation of acryloyl chloride is -48.6 kJ/mol at standard temperature and pressure.

It indicates that the formation of acryloyl chloride is spontaneous, and the product is more stable than the reactants.

Furthermore, the thermodynamic properties of acryloyl chloride determine its reactivity and stability in different environments.

For instance, the compound is more stable in the presence of strong bases than strong acids, making it suitable for reactions with amines.

Conclusion

Acryloyl chloride is a key compound used in various chemical industries, including coatings, adhesives, pharmaceuticals, and surfactants. Understanding the properties, preparation, and reactivity of acryloyl chloride is essential in efficient production and utilization of the compound.

The use of an inhibitor in laboratory preparation and thermodynamic properties is a crucial aspect in controlling the reaction rate and understanding the stability of the compound.

Acryloyl Chloride Uses

Acryloyl chloride is a multifaceted compound that finds a variety of uses in the chemical industry. Some applications of acryloyl chloride include the manufacture of acrylate, cross-metathesis substrates, and new polymers.

Manufacture of Acrylate

Acryloyl chloride is commonly used in the production of acrylate, which is an essential component in the production of paints, coatings, and adhesives. The reaction between acryloyl chloride and an alcohol, such as ethanol, results in the formation of the corresponding acrylate ester.

The reaction formula is as follows:

CH2=CHC(O)Cl + ROH CH2=CHC(O)OR + HCl

Acrylate compounds find use in the modification of polymers, improving their hardness, stiffness, and adhesion properties.

Substrate for Cross-Metathesis

Acryloyl chloride is used as a substrate for cross-metathesis reactions, which involve the exchange of alkene functional groups between two molecules. The reaction yields a new molecule with different properties than the reactants.

Acryloyl chloride can undergo cross-metathesis with various substrates, including alkenes, alkynes, and other acrylates. The resulting products are used as intermediates in the production of surfactants, lubricants, and medicinal compounds.

Manufacturing New Polymers

Acryloyl chloride is used to manufacture new polymers by introducing the acryloyl group into the polymer chain. The resulting polymers can have different properties, including thermal stability, mechanical strength, and adhesion to different substrates.

The crosslinking of polymers with acryloyl chloride is an essential process in the production of coatings, adhesives, and composites.

Acryloyl Chloride MSDS

Acryloyl chloride is a toxic and highly reactive compound that requires proper handling and storage. The Material Safety Data Sheet (MSDS) provides essential information on the physical, chemical, and safety properties of the compound.

Inflammability

Acryloyl chloride is a flammable liquid that can ignite when exposed to heat, flame, and oxidizing agents. It can also react violently with water, releasing toxic hydrogen chloride gas.

The MSDS provides guidelines on how to handle and store acryloyl chloride in a safe manner.

Toxicity

Acryloyl chloride is highly toxic and can cause skin and eye irritation upon contact. The compound can also cause respiratory irritation and can be fatal if ingested.

The MSDS outlines the safety precautions to be taken by workers when dealing with acryloyl chloride and guidelines to prevent accidental exposure.

Transportation

Transportation of acryloyl chloride is subject to strict safety regulations due to its toxic and flammable nature. The MSDS provides information on the proper shipping and storage guidelines for acryloyl chloride and its compatibility with other materials.

Personal Safety

The MSDS provides essential guidelines to ensure personal safety while working with acryloyl chloride. This includes the provision of personal protective equipment, such as gloves, face shields, and protective clothing.

It also includes measures to be taken when dealing with spills, leaks, and other emergency situations.

First Aid

The MSDS outlines the first aid measures to be taken in case of accidental exposure to acryloyl chloride. This includes guidelines on how to handle skin and eye contact, inhalation, and ingestion.

Storage Instructions

Acryloyl chloride requires proper storage conditions to minimize the risk of fire and exposure to workers. The MSDS provides instructions on the storage guidelines, including the temperature range, storage containers, and compatibility with other materials.

Conclusion

Acryloyl chloride finds use in several applications, including the manufacture of acrylate, cross-metathesis substrates, and new polymers. However, acryloyl chloride is a highly reactive and toxic compound that requires proper handling, storage, and safety precautions.

The MSDS provides essential information on the physical, chemical, and safety properties of acryloyl chloride, which is crucial in ensuring safe handling and transportation of the compound.

Acryloyl Chloride Organic Synthesis

Acryloyl chloride finds wide application in organic synthesis, principally for the introduction of acrylic moieties into a molecule.of an acrylic moiety into a molecule confers unique properties, such as thermal stability, UV-resistance, and hydrophobicity. Acryloyl chloride can react with an extensive range of functional groups under mild conditions, making it an attractive choice for organic synthesis.

The organic compounds obtained from acryloyl chloride can be used in coatings, adhesives, and pharmaceuticals, among others.

Acrylic Moieties

Acrylic moieties are widely used in organic synthesis, and their applications in coatings, adhesives, and polymer chemistry are well-known. The incorporation of acrylic moieties into a molecule improves its reactivity, thermal and electrochemical stability, and solvent resistance.

Acryloyl chloride readily introduces acrylic moieties into a molecule by reaction with compounds having active hydrogen, such as amines, alcohols, and carboxylic acids.

Acryloyl Chloride Reactions

Acryloyl chloride undergoes various chemical reactions that allow for modification of the molecule and introduction of acrylic moieties. Some common reactions of acryloyl chloride are;

Reaction with Water

Acryloyl chloride reacts with water to form acrylic acid and hydrogen chloride. This reaction is highly exothermic and must be carried out with caution.

The reaction is as follows,

CH2=CHC(O)Cl + H2O CH2=CHCOOH + HCl

Anhydride Formation

Acryloyl chloride reacts with carboxylic acids to form anhydrides. The reaction is stereochemically less demanding than other anhydride-forming reactions and occurs under mild conditions.

The reaction is as follows,

RC(O)OH + CH2=CHC(O)Cl RC(O)O(CH2=CHCO)R + HCl

Ester and Amide Formation

Acryloyl chloride reacts with amines, alcohols, and carboxylic acids to form esters and amides. The reaction with amines and alcohols results in the formation of amides and esters, respectively, while reaction with carboxylic acids results in formation of anhydrides.

The reaction follows the following equation,

CH2=CHC(O)Cl + 2ROH CH2=CHC(O)OR + HCl + H2O

The resulting compounds find use as intermediates in the production of adhesives, coatings, and surfactants.

Conclusion

Acryloyl chloride finds extensive use in organic synthesis, and its ability to introduce acrylic moieties into a molecule is vital for the synthesis of new chemicals. The introduction of acrylic moieties gives the molecule unique properties, such as thermal stability, UV-resistance, and hydrophobicity.

Acryloyl chloride undergoes various chemical reactions, such as reaction with water, formation of anhydrides, esters and amides, among others, providing an extensive toolkit for modifying the molecule and introducing desired functional groups. Understanding acryloyl chloride’s reactivity and ability to introduce acrylic moieties is essential in the design of new chemicals with specific properties.

In conclusion, acryloyl chloride is a versatile compound with applications in various industries. Its ability to introduce acrylic moieties provides unique properties such as thermal stability and hydrophobicity.

Through organic synthesis, acryloyl chloride allows for the modification of molecules and the production of new chemicals for coatings, adhesives, and pharmaceuticals. Its reactivity with water, carboxylic acids, amines, and alcohols opens up possibilities for the formation of anhydrides, esters, and amides.

Understanding acryloyl chloride’s role in organic synthesis is crucial for developing innovative materials and compounds. Overall, acryloyl chloride plays a vital role in the chemical industry, driving advancements in various applications.

FAQs:

1. What is the significance of acryloyl chloride in organic synthesis?

Acryloyl chloride allows for the introduction of acrylic moieties, which impart unique properties to molecules, making it important for synthesizing materials with specific characteristics. 2.

How does acryloyl chloride react with water? Acryloyl chloride reacts with water to form acrylic acid and hydrogen chloride, which is a highly exothermic reaction.

3. What reactions can acryloyl chloride undergo with carboxylic acids?

Acryloyl chloride can react with carboxylic acids to form anhydrides, which play a crucial role in the development of adhesives, coatings, and surfactants. 4.

How does acryloyl chloride contribute to the production of esters and amides? Acryloyl chloride reacts with amines and alcohols to form amides and esters, respectively, offering a way to create new compounds with tailored properties.

5. What are the applications of acrylic moieties in the chemical industry?

Acrylic moieties are widely used in coatings, adhesives, and polymer chemistry, providing improved reactivity, stability, and resistance to solvents and environmental factors.

Popular Posts