March 4, 2024
Allyl Chloride and Vinyl Chloride

Difference Between Allyl Chloride and Vinyl Chloride

Welcome to this comprehensive guide where we will explore the fascinating topic of the difference between allyl chloride and vinyl chloride. Both elements belong to a class of organic compounds called chloroalkenes. Despite their similar-sounding names, they have distinct chemical properties and applications. At our workshop, we will investigate the characteristics, applications, and variants of these compounds to provide a fuller picture of their distinct abilities.

Importance and applications of both compounds

Allyl chloride and vinyl chloride are two important compounds that find wide-ranging applications in various industries. Allyl chloride, with the molecular formula C3H5Cl, is a colorless to pale yellow liquid with a pungent odor. One of its primary applications is as an intermediate in creating allyl compounds – compounds used in synthesizing polymers, resins, and plastics. Allyl chloride is also employed in the manufacturing of pharmaceuticals, dyes, and pesticides.

Its reactivity and ability to undergo various chemical reactions make it a valuable compound in organic synthesis. Furthermore, allyl chloride serves as a precursor for allyl alcohol, an essential building block for the production of allyl esters and various specialty chemicals. Vinyl chloride, represented by the molecular formula C2H3Cl, is a colorless gas with a slightly sweet odor. PVC plastic, one of the most widely utilized plastics, is one prominent use for polyvinyl chloride (PVC).

PVC is utilized in construction materials, pipes, window frames, cables, flooring, and various consumer products. Vinyl Chloride is Used in the Manufacturing of Copolymers and Vinyl Resins That Are Utilized in Coatings, Adhesives, Textiles, and Textile Coating Applications. Vinyl chloride is also a starting material for the production of vinyl-based monomers, such as vinyl acetate and vinylidene chloride, which further expand its utility in various industries.

Both allyl chloride and vinyl chloride play crucial roles in the production of essential materials and chemicals. Their applications extend to diverse industries, including construction, automotive, packaging, pharmaceuticals, and textiles, contributing to the advancement and innovation of numerous products we encounter in our daily lives.

Definition of Allyl Chloride and Vinyl Chloride

Allyl Chloride: Allyl Chloride, commonly referred to as 3-chloropropene is an organic compound with the formula C3H5Cl. It is a colorless to pale yellow liquid with a pungent odor. Allyl Chloride belongs to the organochlorine compound family and can be identified by two carbon bonds bonded together and an attached chlorine atom, both present. It is highly reactive and serves as a versatile building block for the synthesis of various allyl compounds, resins, polymers, and specialty chemicals. Allyl chloride finds applications in industries such as plastics, pharmaceuticals, dyes, and pesticides.

Vinyl Chloride: vinyl chloride (VCH3) is an organic chemical with the formula C2H3Cl and has long been considered an ideal material for vinyl monomers (VCMs). It is a colorless gas with a slightly sweet odor. Vinyl chloride is characterized by the presence of a double bond between carbon and chlorine atoms. PVC resins are integral ingredients in the production of popular plastic applications like polyvinyl chloride (PVC), making this substance invaluable to industrial producers and end-use applications alike. PVC is utilized in construction materials, pipes, window frames, cables, flooring, and consumer products. Vinyl Chloride Can Also Be Used to Produce Copolymers, Vinyl Resins, and Monomers for Use in Textiles, Coatings, and Adhesives, Among Other Areas of Application.

What is Allyl Chloride?

Allyl Chloride (often referred to as 3-chloropropene) is an organic chemical with the chemical formula C3H5Cl. It is a colorless to pale yellow liquid with a pungent odor. The structure of allyl chloride consists of a propane molecule (C3H6) with one of the hydrogen atoms replaced by a chlorine atom (Cl). An alkyl Halide can be formed when hydrogen atoms are exchanged for chlorine atoms to create an alkyl Halide compound.

Allyl chloride is highly reactive due to the double bond formed from two carbon atoms within its structure. This reactivity makes it a valuable compound in organic synthesis. Chemical Intermediate for Making Allelyl Compounds Like Alcohol, Esters, and Allylamines Used In Polymers Resin Dye Pharmaceutical Plastic Pesticides and More

Allyl chloride itself has some applications. Guar gum and resins, and cellulose. It serves as a solvent. It also finds limited use as a reagent in organic reactions, such as in the synthesis of allyl sulfides and allyl ethers.

Difference Between Allyl Chloride and Vinyl Chloride | Compare the Difference Between Similar Terms

Keep in mind that allyl chloride should always be considered hazardous material. It is highly flammable and can react violently with strong oxidizing agents and reducing agents. Chemical exposures that contain lead are potentially toxic if inhaled, absorbed through skin absorption, or consumed directly; excessive doses could have serious health repercussions. Therefore, proper safety precautions and handling guidelines must be followed when working with allyl chloride.

Physical Properties

Allyl chloride possesses certain physical properties that define its behavior and characteristics.

Here are the key physical properties of allyl chloride:

1. State: Allyl chloride is a liquid at room temperature and atmospheric pressure. It exists as a colorless to pale yellow liquid.

2. Odor: Allyl chloride has a pungent and irritating odor. It is often described as having a strong, garlic-like smell.

3. Density: The density of allyl chloride is approximately 0.94 grams per cubic centimeter (g/cm³) at 25°C. This value indicates that allyl chloride is less dense than water.

4. Melting Point: Allyl chloride has a relatively low melting point of -136.7°C (-214.1°F). This temperature is below the freezing point of water, indicating that allyl chloride remains a liquid under typical ambient conditions.

5. Boiling Point: Allyl chloride has a boiling point of 44.1°C (111.4°F). This low boiling point means that allyl chloride readily vaporizes at relatively low temperatures.

6. Solubility: Allyl chloride is sparingly soluble in water, with a solubility of approximately 0.9 grams per 100 milliliters of water at 25°C. Organic Solvents Like Acetone, Ethanol, and Chloroform Dissolve It Easily.

7. Vapor Pressure: Allyl chloride has a relatively high vapor pressure at room temperature. This indicates that it can readily evaporate and form vapors in the air.

These physical properties of allyl chloride are important to consider when handling and working with the compound, as they affect its storage, transportation, and use in various industrial applications.

Odor and Appearance

Allyl chloride is characterized by its distinct odor and appearance.

Here are details about its odor and appearance:

1. Odor: Allyl chloride has a pungent and irritating odor. It is often described as having a strong, garlic-like smell. The odor can be quite noticeable even at low concentrations, making it easily detectable.

2. Appearance: Allyl chloride is a colorless to pale yellow liquid. Physically, liquid at ambient temperatures and pressure are similar to its state at ambient conditions. The liquid form allows for ease of handling and application in various industrial processes.

The combination of the pungent odor and the liquid appearance of allyl chloride are important characteristics to be aware of when working with this compound. Strong Odors Indicate the Presence of Chemicals That Pose a Potential Danger. Precautionary Steps Must Be Taken to Avoid Inhaling Toxic Fumes From These Sources and Inhalation May Become Hazardous Over Time. The liquid form makes it essential to handle and store allyl chloride appropriately, following safety guidelines and regulations.

What is Vinyl Chloride?

Vinyl chloride, also known as chloroethene or vinyl chloride monomer (VCM), is an organic compound with the chemical formula C2H3Cl. It is a colorless gas with a slightly sweet odor. The structure of vinyl chloride consists of a vinyl group (CH2=CH-) with a chlorine atom (Cl) attached to one of the carbon atoms.

Vinyl chloride (VC) is a widely utilized plastic material worldwide and its production accounts for roughly 30% of world plastic production. PVC is a versatile material with a range of applications in various industries. PVC plastic has long been utilized by construction industries as window frames, pipe flooring, roofing material, and roofing tiles. PVC also finds widespread usage in automobile parts production as well as electrical cables medical devices as well as toys vinyl records packaging materials etc.

The polymerization of vinyl chloride molecules forms the PVC polymer, which possesses desirable properties such as durability, chemical resistance, and flame retardancy. These properties make PVC suitable for diverse applications. Additionally, vinyl chloride can be copolymerized with other monomers to produce vinyl-based resins and copolymers with specific properties tailored for various industries.

Vinyl chloride - Wikipedia

Vinyl chloride’s use in industry can be essential, yet it must always be remembered that it’s a highly hazardous chemical substance. Breathing in Large Doses Has Been Shown to Cause Cancerous Growths; Its Inhalation Has Also Been Linked to Adverse Health Impacts; Thus Appropriate Precautions and Regulations Must Be in Place to Guarantee Safe Handling, Storage, and Disposal in Industrial Settings.

Production Methods

Allyl Chloride Production Methods: There are several industrial methods for the production of allyl chloride.

Two commonly used methods are:

1. Direct Chlorination: Allyl chloride is produced by directly chlorinating propylene (C3H6) with chlorine gas (Cl2) in the presence of a catalyst, typically a copper-based catalyst. The reaction takes place at elevated temperatures and is carried out in the gas phase. The chemical equation for this reaction is:

C3H6 + Cl2 → C3H5Cl + HCl

The resulting allyl chloride is then separated and purified from the reaction mixture.

2. Oxychlorination: This process involves the oxychlorination of propylene to produce allyl chloride. Propylene is reacted with chlorine gas and oxygen (or air) in the presence of a catalyst, usually a copper or copper chloride-based catalyst. The reaction takes place at moderate temperatures and is typically carried out in a fixed-bed reactor.

The chemical equation for the main reaction involved is:

C3H6 + 3 Cl2 + 3/2 O2 → C3H5Cl + 3 HCl

The allyl chloride formed is separated and purified through distillation or other separation techniques.

Vinyl Chloride Production Methods: The primary industrial method for the production of vinyl chloride is the process called the “ethylene-based” method.

The major steps involved in this method are:

1. Ethylene Chlorination: Ethylene gas (C2H4) is chlorinated with chlorine gas (Cl2) in the presence of a catalyst, often a ferric chloride (FeCl3) or cupric chloride (CuCl2) catalyst. The reaction takes place at elevated temperatures and is typically carried out in a fluidized-bed reactor.

The chemical equation for this reaction is:

C2H4 + Cl2 → C2H3Cl + HCl

Dichloroethane, Produced Through This Process, Consists of Both 1,2-Dichloroethane and 1,1-Dichloroethane Components.

2. Dehydrochlorination: The dichloroethane produced in the previous step is then subjected to dehydrochlorination. At high temperatures, dichloroethane must be heated under certain circumstances in the presence of catalysts like an iron- or copper-based catalyst to be converted. The reaction eliminates a molecule of hydrogen chloride (HCl) to form vinyl chloride.

The chemical equation for this reaction is:

C2H4Cl2 → C2H3Cl + HCl

The vinyl chloride is then separated and purified from the reaction mixture through various distillation and purification processes.

These production methods are industrially employed to manufacture allyl chloride and vinyl chloride on a large scale. Be mindful that specific procedures will differ based on the manufacturing company and plant configuration used.

Industrial synthesis of vinyl chloride

The industrial synthesis of vinyl chloride, also known as VCM (vinyl chloride monomer), predominantly involves an ethylene-based process.

The key steps in the industrial synthesis of vinyl chloride are as follows:

1. Ethylene Chlorination: The process begins with the chlorination of ethylene (C2H4) using chlorine gas (Cl2). This reaction is typically carried out in a fluidized-bed reactor or a fixed-bed reactor. A catalyst, often based on iron or copper compounds, is employed to facilitate the reaction. Chlorination Reactions Result in Dichloroethane (C2H4Cl2) Which is Comprised of 1,2-Dichloroethane and 1,1-Dichloroethane Combined.

C2H4 + Cl2 → C2H4Cl2

2. Oxychlorination: The next step involves the conversion of the dichloroethane produced in the previous step to vinyl chloride through oxychlorination. Oxychlorination is a process that uses oxygen (O2) or air as an oxidizing agent along with hydrogen chloride (HCl) and the presence of a copper-based catalyst, commonly cupric chloride (CuCl2), in a fluidized-bed reactor. The reaction results in the selective chlorination and dehydrochlorination of dichloroethane, leading to the formation of vinyl chloride.

C2H4Cl2 + O2 + HCl → C2H3Cl + H2O + Cl2

3. Separation and Purification: After the oxychlorination step, the reaction mixture contains various components, including unreacted ethylene, chlorine, water, hydrogen chloride, and vinyl chloride. Distillation and other methods of purification are used to separate and extract vinyl chloride from its mix. Distillation is used to separate vinyl chloride from the byproducts, including unreacted gases and other impurities.

4. Further Treatment: The final product, vinyl chloride, undergoes further processing to remove any remaining impurities and stabilize it for storage and transportation. Polymerization inhibitors may be added to prevent premature polymerization of vinyl chloride during storage.

The production of vinyl chloride requires special equipment, extensive monitoring of process parameters, and stringent safety regulations due to its dangerous and potentially flammable ingredients.

Difference Between Allyl Chloride and Vinyl Chloride

Allyl chloride and vinyl chloride are two distinct compounds that differ in their chemical structures and properties.

Here are the key differences between allyl chloride and vinyl chloride:

Chemical Structure:
• Allyl Chloride (C3H5Cl): Allyl chloride consists of a propane molecule (C3H6) with one of the hydrogen atoms replaced by a chlorine atom (Cl). It contains a double bond between two carbon atoms and is characterized by the presence of the allyl group (-CH2CH=CH2) in its structure.

• Vinyl Chloride (C2H3Cl): Vinyl chloride consists of a vinyl group (CH2=CH-) with a chlorine atom (Cl) attached to one of the carbon atoms. It contains a single carbon-carbon bond and a double bond between carbon and chlorine atoms.

Physical Properties:
• Physical State: Allyl chloride is a colorless to pale yellow liquid at room temperature, while vinyl chloride is a colorless gas.
• Odor: Allyl chloride has a pungent odor, often described as garlic-like. Vinyl chloride has a slightly sweet odor.

Applications:
• Allyl Chloride: Allyl chloride serves as an intermediate in the production of various allyl compounds, resins, polymers, and specialty chemicals. Dye, pharmaceutical, plastics, and pesticide industries all rely heavily on it.

• Vinyl Chloride: Vinyl Chloride Is Primarily Used in the Production of Polyvinyl Chloride (PVC), a Widely Used Plastic. PVC finds applications in construction materials, pipes, window frames, cables, flooring, and consumer products.

Reactivity:
• Allyl Chloride: Allyl chloride is highly reactive due to the presence of a double bond between carbon atoms. It undergoes various chemical reactions and is used in organic synthesis.

• Vinyl Chloride: Vinyl chloride is relatively stable and does not undergo significant chemical reactions under normal conditions. However, it can undergo polymerization to form a polyvinyl chloride (PVC) with suitable initiators and conditions.

Toxicity and Safety:
• Allyl Chloride: Allyl chloride is considered a hazardous substance. LPG can be highly flammable and react violently with certain substances. Furthermore, its toxic nature poses serious health hazards if inhaled through breathing or swallowed directly.

• Vinyl Chloride: Vinyl chloride is considered a carcinogen and poses health hazards. Substantial Exposure to Vinyl Chloride May Pose Significant Health Hazards, Including Damage to the Lungs, Liver, and Nervous Systems.

 

Allyl chloride and vinyl chloride differ in their chemical structures, physical states, odor, applications, reactivity, and toxicity. While allyl chloride is utilized as an intermediate in various chemical syntheses, vinyl chloride is primarily used in the production of PVC plastic. Both compounds require careful handling and adherence to safety guidelines due to their hazardous nature.

Comparison Chart

Here’s a comparison chart highlighting the key differences between allyl chloride and vinyl chloride:

Allyl Chloride Vinyl Chloride
Chemical Formula C3H5Cl C2H3Cl
Chemical Structure Propene with a chlorine atom Vinyl group with a chlorine atom
Physical State Liquid Gas
Odor Pungent Slightly sweet
Reactivity Highly reactive Relatively stable
Applications Intermediate in chemical synthesis, production of resins, polymers, specialty chemicals Primary precursor for polyvinyl chloride (PVC) production, construction materials, consumer products
Toxicity Toxic and hazardous Carcinogenic and hazardous
Flammability Highly flammable Flammable
Health Effects Can cause severe health effects if inhaled, absorbed, or ingested Carcinogenic, can cause liver, lung, and nervous system damage
Physical State Liquid Gas
Handling and Safety Requires proper handling, storage, and safety precautions Requires proper handling, storage, and safety precautions
Polymerization Can be used for polymerization reactions Can polymerize to form polyvinyl chloride (PVC) under suitable conditions
Industrial Production Direct chlorination or oxychlorination of propylene Ethylene chlorination followed by oxychlorination

This chart provides a concise overview of the main differences between allyl chloride and vinyl chloride in terms of their chemical structure, physical properties, reactivity, applications, toxicity, and industrial production methods.

Conclusion

Allyl chloride and vinyl chloride are two distinct chloroalkene compounds that possess unique properties and applications. While allyl chloride is a highly reactive liquid used as an intermediate in organic synthesis and polymer production, vinyl chloride is a stable gas primarily employed in the manufacturing of PVC and other chemicals. Understanding the differences between these compounds is crucial for their safe handling and effective utilization in various industries.