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Last updated date: 23rd Apr 2024
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What is Chlorobenzene?

Chlorobenzene is a compound that has a chemical formula of C6H5Cl. This liquid is flammable and is also known as a common solvent. Chlorobenzene is commonly used to manufacture chemicals. The main use of this compound is done to produce commodities that include herbicides, rubber, and any other dyestuffs. It is also used as a solvent in various industrial applications and laboratories. It is nitrated to produce a mixture that includes 2-nitrochlorobenzene and 4-nitrochlorobenzene on a huge scale. Then, the mononitro chlorobenzenes are turned into 2-nitrophenol and other elements of chloride. Sometimes, many industries convert Aniline to chlorobenzene to use it as an agent for all the alkenes produced.

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How to Convert Aniline to Chlorobenzene?

The process to convert Aniline to chlorobenzene is quite challenging. You will have to use NaNO2/HCl to convert Aniline to benzene diazonium chloride. It then converts to chlorobenzene as the presence of CuCl affects the entire reaction. This type of reaction is called Sandmeyer Reaction.

The Formula For the Reaction is as follows:

C6​H5​NH2NaNO2​/ HCl​C6H5​N2​ClCu2​Cl2​​C6​H5​C

The entire process is completed in two steps. The temperature at which the reaction occurs stands at 0 degrees to 5 degrees centigrade.

When it comes to Sandmeyer Reaction, there are many types of reactions. You can react with benzene diazonium chloride with other solvents, including CuCI, CuCN, and many more. It forms chlorobenzene, benzonitrile, and many more.

How Can You Convert Benzene to Chlorobenzene?

The process of benzene to chlorobenzene conversion is pretty simple. You will first have to react to Benzene with Chlorine. However, you will have to ensure that a catalyst can replace the Hydrogen atoms with chlorine atoms. The room temperature is suitable for this type of reaction. You can take aluminium, chlorine, and iron in the form of catalysts. 

However, it is not advised to take iron as a catalyst because, during the reaction, the particles get permanently altered. Iron has the ability to react with chlorine and form FeCl3 (Iron Chloride).

Also, you can take iron chloride in the form of a catalyst and make it behave like Aluminium Chloride (ALCL3). Then, chlorobenzene is formed when this type of reaction comes in contact with aluminium chloride.

The Process to Convert Chlorobenzene to Aniline

To convert Chlorobenzene to Aniline, you can prepare it commercially with the help of a catalyst, Nitrobenzene. You can also use ammonia on the produced chlorobenzene. All you have to do is reduce Nitrobenzene by carrying out a reaction in aqueous acid with the help of iron borings. As Aniline is considered a weak base, it tends to form salts when you dilute it in mineral acid.

How Can You Convert Chlorobenzene to Benzene?

You can convert chlorobenzene to benzene in three different steps altogether. You can start the reaction by reacting HNO3 with H2SO4 that will form Nitrobenzene. Then, you can reduce it by forming a reaction of Nitrobenzene and Sn+HCL, Fe+HCL, or H2/Pd to produce Aniline. After the reaction is completed, you can then add NaNO2+HCL to the reaction that will form benzene Diazonium Chloride. After that, you can react with Sandmeyer’s Reaction (CuCl) or Gatterman Reaction (Cu Powder). This will form Chlorobenzene.

How Can You Obtain Mono Chlorobenzene?

When you dissolve or suspend Aniline with cold aqueous mineral acid and treatment with sodium nitrite, then a diazonium salt comes into existence. This salt has to be treated with cuprous bromide to form mono chlorobenzene. 

When you substitute chlorine at any given spot, then you will see that six carbons remain constant. Therefore, only one possible benzene is formed. 

How Can You Prepare Chlorobenzene From Aniline?

You can prepare chlorobenzene from Aniline with the help of Sandmeyer Reaction. You can fit the reaction with diphenyl and extract it from chlorobenzene.

Here is a Step-By-Step Process to Prepare Chlorobenzene From Aniline:

Step 1: Sandmeyer Reaction: It is a chemical reaction that you can use to synthesize the aryl halides from the diazonium salts by using agents of copper salts and catalysts. 

Step 2: You can follow a two-step reaction that includes converting benzene diazonium chloride by utilizing the Sodium Nitrate solutions and aqueous hydrochloric acid. Then, you can react to the benzene diazonium with cuprous chloride to form chlorobenzene.

FAQs on Chlorobenzene

1. When Did the Production For Chlorobenzene Start?

Ans: The production for Chlorobenzene started back in 1951. It is manufactured by the process of chlorination of benzene with the help of Lewis acid that includes ferric chloride, aluminium chloride, and sulphur dichloride. The catalyst helps in enhancing the chlorine’s electrophilicity. As chlorine is considered to be a negative atom, C6H4Cl exhibits decreased chances of susceptibility and fast

There are also industrial uses of chlorobenzene. The reaction is done continuously to minimize dichlorobenzene formation. This helps in controlling the reaction and making the process of chlorination seamless and smoother. Chlorobenzene is also produced from Aniline with the help of benzene diazonium chloride. This entire process is called the Sandmeyer reaction.

2. What are the Uses of Chlorobenzene?

Ans: There are many uses of Chlorobenzene. It is a high-profile application that is produced for pesticide DDT via chloral reaction. It is otherwise known as trichloroacetaldehyde when sulphuric acid reacts with it.

The main use of this chemical is in producing commodities that include herbicides, rubber, as well as dyestuffs. Manufacturers also utilize it in manufacturing adhesives, paint removers, dyes, drugs, as well as paints.

In the construction industry, it is also utilized in manufacturing polyurethane insulation. It is produced by diisocyanate. 

3. What is the Impact of Chlorobenzene on the Environment?

Ans: It can evaporate when it comes in contact with air. Chlorobenzene dissolved to some extent when it was exposed to water. Many industries release chlorobenzene into the air. It also has the ability to evaporate when it is mixed with water or soil. Once it is in the air, it breaks down into other chemicals. As it is in the form of a liquid state, it doesn’t react well with the soil. It rather makes its path into the ground and can reach underwater. Many plants or animals cannot store chlorobenzene.