Epichlorohydrin (C3H5ClO) is a chemical compound used in the production of epoxy resins, synthetic rubber, and other industrial applications. It is known for its strong odor and potential health hazards.
| IUPAC name | (chloromethyl)oxirane |
| Molecular formula | C3H5ClO |
| CAS number | 106-89-8 |
| Synonyms | Glycidyl chloride, Chloropropylene oxide, 1-Chloro-2,3-epoxypropane, alpha-epichlorohydrin |
| InChI | InChI=1S/C3H5ClO/c4-1-3-2-5-3/h3H,1-2H2 |
Epichlorohydrin Properties
Epichlorohydrin Formula
The formula for epichlorohydrin is C3H5ClO. It consists of three carbon atoms, five hydrogen atoms, one chlorine atom, and one oxygen atom. The formula represents the composition of the compound and is used to identify its chemical structure.
Epichlorohydrin Molar Mass
The molar mass of glycidyl chloride is calculated by adding up the atomic masses of its constituent elements. For glycidyl chloride, the molar mass is approximately 92.5 grams per mole. Molar mass is an important parameter in chemical calculations and determines the amount of substance present in a given sample.
Epichlorohydrin Boiling Point
The boiling point of glycidyl chloride is around 117-119 degrees Celsius. It refers to the temperature at which the liquid form of the compound changes into a gas at atmospheric pressure. The boiling point is a key characteristic used to identify and handle the compound during various industrial processes.
Epichlorohydrin Melting Point
The melting point of glycidyl chloride is about -57 degrees Celsius. It denotes the temperature at which the solid form of the compound transitions into a liquid. The melting point is crucial for determining the physical state of glycidyl chloride under different conditions.
Epichlorohydrin Density g/mL
The density of glycidyl chloride is approximately 1.18 grams per milliliter. Density represents the mass of a substance per unit volume and is used to determine its compactness or concentration. The density of glycidyl chloride provides insights into its physical behavior and handling requirements.
Epichlorohydrin Molecular Weight
The molecular weight of glycidyl chloride is around 92.5 grams per mole. It is the sum of the atomic weights of all the atoms present in one molecule of the compound. The molecular weight is utilized in various chemical calculations, such as determining the amount of substance in a given sample.
Epichlorohydrin Structure
The structure of glycidyl chloride consists of a three-membered ring with an oxygen atom and two carbon atoms. One of the carbon atoms is bonded to a chlorine atom, while the other carbon atom is connected to a hydrogen atom and forms a chain with additional carbon atoms. The structure is crucial in understanding the compound’s reactivity and behavior.
Epichlorohydrin Solubility
Glycidyl chloride is soluble in various organic solvents, such as acetone, ethyl acetate, and chloroform. However, it is sparingly soluble in water. Solubility refers to the ability of a substance to dissolve in a particular solvent. The solubility of glycidyl chloride impacts its applications and how it interacts with other substances in different environments.
| Appearance | Clear, colorless liquid |
| Specific Gravity | 1.180 – 1.183 g/mL at 25°C |
| Color | Colorless |
| Odor | Strong, pungent |
| Molar Mass | 92.52 g/mol |
| Density | 1.180 – 1.183 g/mL at 25°C |
| Melting Point | -57°C |
| Boiling Point | 117-119°C |
| Flash Point | 31.7°C |
| Water Solubility | Miscible |
| Solubility | Soluble in organic solvents |
| Vapour Pressure | 12.2 mmHg at 25°C |
| Vapour Density | 3.2 (air = 1) |
| pKa | 13.7 |
| pH | Approximately 6-7 |
Epichlorohydrin Safety and Hazards
Glycidyl chloride poses potential safety hazards and should be handled with caution. It is classified as a hazardous substance due to its irritant and corrosive properties. Direct contact with the compound can cause skin and eye irritation. Inhalation of its vapors may lead to respiratory irritation and damage. Glycidyl chloride has a strong, pungent odor, which serves as a warning sign. Prolonged or repeated exposure to glycidyl chloride has been associated with adverse health effects, including respiratory and gastrointestinal issues, as well as potential reproductive and developmental effects. Adequate ventilation, protective clothing, and equipment should be used when working with glycidyl chloride to minimize exposure and ensure safety.
| Hazard Symbols | Corrosive, Health Hazard |
| Safety Description | – Causes severe skin burns and eye damage – May cause respiratory irritation – Harmful if swallowed or inhaled – Toxic to aquatic life with long-lasting effects |
| UN IDs | UN 2023 |
| HS Code | 2910.90.00 |
| Hazard Class | Class 8 – Corrosive Substances |
| Packing Group | PG II |
| Toxicity | Toxic and corrosive |
Epichlorohydrin Synthesis Methods
Various methods can synthesize glycidyl chloride. One common method involves chlorinating allyl chloride, where chlorine gas reacts with allyl chloride in the presence of a catalyst like iron or aluminum chloride. The reaction yields glycidyl chloride as the major product.
Another method entails reacting glycerol with hydrochloric acid and sodium hypochlorite. Glycerol undergoes a series of reactions, including chlorination and dehydrochlorination, to produce glycidyl chloride.
In the synthesis of glycidyl chloride, one can epoxidize allyl alcohol. This reaction employs hydrogen peroxide and an acid catalyst such as sulfuric acid or p-toluenesulfonic acid. The epoxidation of allyl alcohol forms the desired product, glycidyl chloride.
Additionally, the oxidation of chloropropene can yield glycidyl chloride. To achieve this, one can oxidize chloropropene using an oxidizing agent like hydrogen peroxide or air with the presence of a catalyst such as iron or copper salts.
These synthesis methods offer different routes to produce glycidyl chloride, allowing for flexibility in industrial applications. It is crucial to note that handling hazardous materials and adhering to safety protocols are necessary to ensure the well-being of workers and the environment.
Epichlorohydrin Uses
Glycidyl chloride finds application in various industries due to its versatile properties. Here are some common uses of glycidyl chloride:
- Epoxy Resins: Glycidyl chloride plays a crucial role as a raw material in producing epoxy resins, which find widespread use in coatings, adhesives, composites, and electrical insulation materials.
- Synthetic Rubber: Glycidyl chloride functions as a monomer in manufacturing synthetic rubber, such as glycidyl chloride rubber (ECO), which demonstrates excellent oil and fuel resistance, making it suitable for automotive seals and hoses.
- Water Treatment: Glycidyl chloride finds application in synthesizing cationic flocculants, vital for water treatment processes, assisting in removing suspended solids and contaminants from water.
- Pharmaceuticals: Glycidyl chloride serves as an intermediate in the pharmaceutical industry, particularly in the synthesis of certain drugs like glycerol-based compounds and antibiotics.
- Paper Industry: The paper industry utilizes glycidyl chloride as a wet-strength agent to enhance the strength and durability of paper, enabling its use in moisture-resistant applications.
- Textile Chemicals: Glycidyl chloride contributes to the production of textile auxiliaries and dye intermediates, imparting desirable properties such as softness, color fastness, and wrinkle resistance.
- Solvent Extraction: Glycidyl chloride acts as a solvent in various extraction processes, specifically for separating natural products and chemicals from raw materials.
- Adhesives and Sealants: Glycidyl chloride serves as a component in formulating adhesives and sealants, offering robust bonding strength and resistance to chemicals and moisture.
Glycidyl chloride’s wide range of applications highlights its significance in various industries, contributing to the development of products and materials that enhance our daily lives.
Questions:
Q: Is epichlorohydrin in Pukka tea bags?
A: Glycidyl chloride is not used in the manufacturing process of Pukka tea bags.
Q: How to wash epichlorohydrin in glycidyl ether reaction?
A: Washing the reaction mixture with an appropriate solvent, such as water or an aqueous solution, helps remove residual glycidyl chloride from the glycidyl ether.
Q: Is there epichlorohydrin in every Lipton tea bag?
A: The presence of glycidyl chloride in Lipton tea bags is unlikely as it is not a common ingredient used in tea bag manufacturing.
Q: How to rotovap epichlorohydrin?
A: Glycidyl chloride can be removed by rotary evaporation (rotovap) under reduced pressure and elevated temperature to facilitate its evaporation.
Q: What brand of tea bags are treated with epichlorohydrin?
A: The specific brand of tea bags treated with glycidyl chloride is not mentioned or known, as it is not a common practice in the tea industry.
Q: How to make epichlorohydrin from allyl chloride?
A: Glycidyl chloride can be produced from allyl chloride by chlorination using chlorine gas and a suitable catalyst, such as iron or aluminum chloride.
Q: Which of the following synthetic routes is used in industry to provide epichlorohydrin?
A: One common industrial method to produce glycidyl chloride is the chlorination of allyl chloride.
Q: What polymers are made using epichlorohydrin?
A: Glycidyl chloride is used in the production of polymers such as epoxy resins and glycidyl chloride rubber (ECO).
Q: How to wash epichlorohydrin in glycidyl ether?
A: Washing the glycidyl ether with an appropriate solvent, such as water or an aqueous solution, can help remove any residual glycidyl chloride.