and Background
Acetanilide is an organic compound that has been widely used since its synthesis in 1853 by Charles Gerhardt. Initially, it was marketed as a fever-reducing drug under the name of Antifebrin, but later it was discovered that it had significant toxic side effects.
Today, it is mainly used in the synthesis of various chemicals and pharmaceuticals. In this article, we will discuss the identification and properties of acetanilide, its chemical formula and structure, and its various applications.
History and Uses
The discovery of acetanilide was a turning point in the development of organic chemistry. Gerhardt synthesized it by reacting aniline with acetic anhydride and used it as an intermediate in the production of several dyes.
However, it was Heinrich Hlasiwetz who first recognized its medicinal properties and marketed it under the name Antifebrin. In the early 20th century, it was replaced by safer alternatives, such as aspirin and paracetamol.
Today, acetanilide is used mainly as an intermediate in the synthesis of various compounds. It is used in the manufacturing of sulfa drugs, dyes, and rubber chemicals.
It is also used in organic chemistry as a reagent and catalyst in the production of many pharmaceuticals, including analgesics, antipyretics, and anti-inflammatory drugs.
Acetanilide Identification
Chemical Identification
Acetanilide has a chemical formula of C8H9NO and a molecular weight of 135.17 g/mol. It has a CAS number of 103-84-4, a ChemSpider ID of 8900, a UNII number of 4F9R1J8B87, an EC-number of 203-150-7, and a KEGG ID of D03723.
Its chemical structure consists of a benzene ring attached to a carbonyl group and an amino group.
Chemical Formula and Structure
The chemical formula of acetanilide indicates that it contains eight carbon atoms, nine hydrogen atoms, one nitrogen atom, and one oxygen atom. The positions of these atoms can be represented using a structural formula.
The structural formula of acetanilide shows that it has a benzene ring attached to a carbonyl group (-CO-) and an amino group (-NH2). The benzene ring is represented by a hexagon with alternating double bonds and is commonly referred to as the phenyl group (-C6H5).
Applications
Acetanilide has many applications in the chemical and pharmaceutical industries. One of its primary uses is as an intermediate in the synthesis of various chemicals.
It is used in the production of sulfur dyes, which are used in the textile industry. It is also used in the production of rubber chemicals, which are used in the manufacturing of tires, hoses, and other rubber products.
In the pharmaceutical industry, acetanilide is used mainly as a precursor for the synthesis of various analgesics, antipyretics, and anti-inflammatory drugs. For example, acetaminophen (a common pain reliever) is synthesized by reacting acetanilide with acetic anhydride and then treating the product with hydrochloric acid.
The final product is then purified to obtain pure acetaminophen.
Conclusion
In conclusion, acetanilide is an organic compound that has played a significant role in the development of organic chemistry. Although its use as a fever-reducing drug was discontinued due to its toxicity, it is still widely used in the chemical and pharmaceutical industries.
Its chemical formula and structure have allowed it to be used as an intermediate in the synthesis of various compounds. Its applications include the production of dyes, rubber chemicals, and various pharmaceuticals such as analgesics, antipyretics, and anti-inflammatory drugs.
Preparation of Acetanilide
Acetanilide can be synthesized through the chemical reaction between aniline and acetic anhydride. The process involves the addition of acetic anhydride to the aniline molecule, which then forms a compound that subsequently undergoes hydrolysis to form acetanilide.
The synthesis method begins by adding a mixture of aniline and acetic anhydride to a round bottom flask. The solution is then continuously stirred and heated to 60 to 70C for a few hours.
During the reaction, the solution becomes dark in color and may exude a pungent odor. The next step involves cooling the solution using cold water.
Once the solution is chilled, it is then decanted into a Buchner funnel, and the solid acetanilide is collected by filtration. The collected solid should then be purified through a recrystallization process, using a suitable solvent such as hot water or ethanol, before being dried.
In introductory Organic Chemistry lab classes, acetanilide synthesis is an essential experiment in which students learn how to carry out a basic purification process through recrystallization. The experiment allows students to understand the theoretical principles of condensation reactions and hydrolysis.
Additionally, the experiment provides insights into the fundamental concepts of chemical reactions, such as the generation of energy, entropy, and Gibbs free energy.
Physical and Chemical Properties
Appearance, Odor, and Solubility
Acetanilide has a white crystalline appearance and is odorless. It is relatively soluble in water at low temperatures, with a solubility of around 1-1.5 g/L at 20C.
The solubility of acetanilide increases at higher temperatures, with a solubility of around 20 g/L at 98C. It is also soluble in ethanol, methanol, ethyl ether, and chloroform.
Molecular Weight, Melting and Boiling Points, Density, and Vapor Pressure
The molecular weight of Acetanilide is 135.17 g/mol. It has a melting point of 113 to 115C and a boiling point of 304C.
Acetanilide has a density of 1.219 g/cm at 20C and a vapor pressure of approximately 0.0001 mmHg at 20C. The physical and chemical properties of acetanilide are essential in understanding the behavior and properties of the compound.
The solid-state properties of acetanilide, such as its high melting point and solubility nature, make it an ideal chemical for the synthesis of various medicines and pharmaceutical products. Its density implies that it has low volatility and is relatively stable, which enhances its suitability in chemical reactions.
In conclusion, acetanilide is an organic compound with proven reliability and versatility. It is synthesized through the reaction of aniline and acetic anhydride and mainly used in the chemical and pharmaceutical industries.
Understanding the synthesis process and the physical and chemical properties of acetanilide is crucial in designing and producing chemical products for industry applications. In academic settings, its synthesis and purification processes are commonly taught in introductory organic chemistry laboratory classes, providing fundamental knowledge and practical experience to aspiring chemists.
Uses of Acetanilide:
Industrial
Applications
Acetanilide has a variety of industrial applications and is frequently used as an inhibitor and/or stabilizer in chemical reactions. It has a propensity to suppress dangerous chemical chain reactions and can consequently be utilized as an anti-blocking or anti-caking agent in the production of plastics and resins.
Acetanilide is also used extensively as an intermediate in the manufacturing of numerous chemical substances, such as rubber accelerators, dyes, and pigments. As a sulfa pharmaceutical precursor, it is additionally utilized in the production of sulfa drugs that are used in the treatment of bacterial infections.
Pharmaceutical Uses and Development
Acetanilide has been used in medicine as a fever reducer (under the trade name Antifebrin). However, it was discovered to be linked with hemoglobin damage, and hence, it was replaced with safer medications, such as aspirin and paracetamol.
Moreover, the primary modern use of acetanilide is as a precursor in the production of various pharmaceutical products. It is utilized in the synthesis of analgesics such as phenacetin, propacetamol, and other derivatives.
It is also used as a precursor for the synthesis of paracetamol, which is a common over-the-counter pain reliever that is a less toxic alternative to aspirin. Acetanilide has properties that make it highly desirable as a raw material for pharmaceuticals.
Thus, it is an essential component of the pharmaceutical industry, contributing to its continued growth by generating new medicines designed to improve the quality of human life. Bromination and Nitration of Acetanilide:
Bromination of Acetanilide:
The Bromination of Acetanilide is a substitution reaction that replaces a hydrogen atom in the benzene ring with a bromine atom.
This reaction can be carried out using several reagents such as bromine, potassium bromate, and hydrogen bromide. The reaction between Acetanilide with bromine produces a mono-substituted product, 4-bromoacetanilide.
In this reaction, the bromine atom acts as an electrophile, which attacks the benzene ring and forms a bromonium ion intermediate. The bromonium ion intermediate is then attacked by the Acetanilide molecule, which results in the formation of the mono-substituted product.
The chemical equation for the bromination of Acetanilide is as follows:
C8H9NO + Br2 C8H8BrNO + HBr
Nitration of Acetanilide:
The nitration of Acetanilide is also an electrophilic aromatic substitution reaction that replaces a hydrogen atom on the benzene ring with a nitro group (-NO2). In this reaction, Acetanilide acts as a Lewis base and reacts with a nitronium ion (NO2+) that is generated through the reaction between Nitric Acid and Sulfuric Acid.
The chemical equation for the nitration of Acetanilide is as follows:
C8H9NO + HNO3 C8H8N2O3 + H2O
In conclusion, The Bromination and Nitration of Acetanilide are significant chemical reactions. The bromination reaction introduces a substituent into the benzene ring, while the nitration reaction introduces a nitro group (-NO2) into the ring.
These reactions demonstrate the diverse synthetic uses of Acetanilide in organic chemistry. Furthermore, Acetanilide exhibits a wide variety of industrial and pharmaceutical applications, making it an essential chemical in various sectors.
Acetanilide Material Safety Data Sheet (MSDS):
Toxicology and Hazards:
Acetanilide can have harmful effects on both human health and the environment. It is important to take necessary precautions when handling and working with acetanilide.
Potential health hazards include:
– Skin Contact: Acetanilide is harmful if it comes into contact with skin. It can cause skin irritation, dermatitis, and chemical burns.
– Eye Contact: Acetanilide can cause severe eye irritation and damage. – Respiratory Tract: Inhalation of acetanilide can cause irritation to the nose, throat, and lungs.
Exposure to high levels of acetanilide vapor can lead to respiratory distress, bronchitis, and pneumonia. – Ingestion: Acetanilide can cause gastrointestinal distress, nausea, vomiting, and diarrhea.
Ingestion of large amounts can lead to blood abnormalities, including methemoglobinemia, which is a condition that causes a decrease in the ability of the blood to carry oxygen. First Aid Measures and Personal Safety:
In case of exposure to acetanilide, it is important to take necessary first aid measures and practice personal safety.
– Eye Contact: If acetanilide contacts the eyes, immediately flush them with water for at least 15 minutes. Seek immediate medical attention.
– Skin Contact: If acetanilide contacts the skin, immediately remove contaminated clothing and wash skin thoroughly with soap and water. Seek medical attention if necessary.
– Inhalation: When exposed to acetanilide, immediately remove the person to fresh air. If breathing is difficult, administer oxygen, and seek medical attention.
– Ingestion: If acetanilide is ingested, DO NOT INDUCE VOMITING. Give the affected person plenty of water to drink and seek medical attention immediately.
It is important to ensure personal protection measures while working with acetanilide. When handling acetanilide, use gloves, protective clothing, safety goggles, and a respiratory mask to prevent skin contact, inhalation of vapors, and eye contact.
Storage and Disposal:
Acetanilide should be stored in a cool, dry, well-ventilated area, away from heat, sparks, and flames. The container should be tightly closed and labeled with the name of the substance and its hazardous properties.
It should not be stored near oxidizing agents or other chemicals that may react with or decompose acetanilide. Acetanilide should be disposed of in accordance with local, state, and federal regulations.
The waste material should be labeled and stored in an appropriate container. Disposal may be through incineration or chemical waste disposal facilities.
Acetanilide Availability:
Acetanilide is readily available in the market and can be found in most chemical supply stores and online stores. The price of acetanilide varies depending on the quantity and quality of the product.
Online stores like Amazon offer acetanilide at reasonable prices, providing easy access to the product. In conclusion, Acetanilide has toxic properties that can have harmful effects on human health and the environment.
It is important to handle and work with acetanilide with proper caution and personal protective equipment. When handling, storing, and disposing of acetanilide, all necessary safety measures must be strictly adhered to.
Acetanilide is widely available in the market, and one can easily purchase it from online stores at reasonable prices. In conclusion, acetanilide is a versatile compound with various industrial and pharmaceutical uses.
Its synthesis and properties make it valuable as an intermediate in the production of chemicals and as a precursor for the synthesis of analgesics and antipyretics. However, it is important to handle acetanilide with caution due to its potential health hazards.
It is crucial to follow proper safety protocols, such as wearing protective gear and ensuring proper storage and disposal. Acetanilide is readily available in the market, and online platforms offer convenient access at reasonable prices.
Overall, understanding the uses, properties, and safety precautions associated with acetanilide is essential for those working in the chemical and pharmaceutical industries.
FAQs:
1.
What are the uses of acetanilide? Acetanilide is used as an inhibitor, stabilizer, and intermediate in various industrial applications, including the production of dyes, rubber chemicals, and sulfa drugs.
It is also a precursor for the synthesis of analgesics and antipyretics. 2.
What are the hazards associated with acetanilide? Acetanilide can cause skin and eye irritation, respiratory issues, and blood abnormalities.
High levels of exposure can lead to severe health problems, such as methemoglobinemia. 3.
How can I ensure personal safety while working with acetanilide? It is important to wear gloves, protective clothing, safety goggles, and a respiratory mask to prevent skin contact, inhalation of vapors, and eye contact.
Follow proper first aid measures and seek medical attention if necessary. 4.
How should acetanilide be stored and disposed of? Acetanilide should be stored in a cool, dry, well-ventilated area, away from heat and oxidizing agents.
It should be disposed of in accordance with local regulations, labeled and stored in appropriate containers, and may be incinerated or sent to a chemical waste disposal facility. 5.
Where can I purchase acetanilide? Acetanilide is available in chemical supply stores and online platforms like Amazon, where it can be purchased at reasonable prices.