Acetyl chloride

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Acetyl chloride

Acetyl chloride is an acid chloride (also known as an acyl chloride) derived from acetic acid

Acetic acid

Acetic acid, CH3COOH, also known as ethanoic acid, is an organic acid which gives vinegar its sour taste and pungent smell. Pure, water-free acetic acid is a colourless liquid that absorbs water from the environment , and freezes at 16.7 Celsius to a colourless crystalline solid....
. It has the formula CH₃COCl and it belongs to the class of organic compound

Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
s called acyl halide

Acyl halide

An acyl halide is a chemical compound derived from an oxoacid by replacing a hydroxyl group with a halide group.If the acid is a carboxylic acid, the compound contains a ?COX functional group, which consists of a carbonyl group singly bonded to a halogen atom....
s. At room temperature and pressure, it is a clear colorless liquid

Liquid

Liquid is one of the principal states of matter. A liquid is a fluid that has the particles loose and can freely form a distinct surface at the boundaries of its bulk material....
. Acetyl chloride does not exist in nature, because contact with water

Water (molecule)

File:Blue-water-pool.jpgWater is the most abundant molecule on Earth's surface, constituting about 70% of the Earth's surface in liquid, solid, and gaseous states....
would hydrolyze it into acetic acid and hydrogen chloride

Hydrogen chloride

The Chemical compound hydrogen chloride has the chemical formula HydrogenChlorine. At room temperature, it is a colorless gas, which forms white fumes of hydrochloric acid upon contact with atmospheric humidity....
. In fact, if handled in open air it gives off white smoke

Smoke

File:Bling-Bling Skywriting David Shankbone.jpgSmoke is the collection of airborne solid and liquid particulates and gases emitted when a material undergoes combustion or pyrolysis, together with the quantity of air that is entrainment or otherwise mixed into the mass....
owing to the hydrolysis from the moisture in the air.

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Synthesis

Like other acyl chloride

Acyl chloride

In organic chemistry, an acyl chloride is an organic compound which is a reactive derivative of a carboxylic acid. As part of its molecular structure, an acyl chloride has the reactive functional group -Carbonyl-Chlorine and has the general formula RCOCl, where R is an organic radical group....
s, acetyl chloride is synthesized

Chemical synthesis

In chemistry, chemical synthesis is purposeful execution of chemical reactions in order to get a product , or several products. This happens by physics and chemical manipulations usually involving one or more reactions....
by the reaction of acetic acid

Acetic acid

Thionyl chloride

Thionyl chloride is an inorganic compound with the chemical formula SulfurOxygenChlorine2. It is a reactive chemical reagent used in chlorination chemical reaction....
(O=SCl₂) under liberation of sulfur dioxide

Sulfur dioxide

Sulfur dioxide is the chemical compound with the formula SO2. It is produced by volcanoes and in various industrial processes. Since coal and petroleum often contain sulfur compounds, their combustion generates sulfur dioxide....
(SO₂).

CH₃COO-H + O=SCl₂ ? CH₃COCl + SO₂ + H-Cl

Hydrogen chloride

It may also be synthesized from the catalytic carbonylation

Carbonylation

Carbonylation refers to Chemical_reactions that introduce carbon monoxide into Organic_compound and inorganic compound substrates. Carbon monoxide is abundantly available and conveniently reactive, so it is widely used as a reactant in industrial chemistry....
of methyl chloride.

Uses

It is a reagent for acetylation

Acetylation

Acetylation describes a reaction that introduces an acetyl functional group into an organic compound. Deacetylation is the removal of the acetyl group....
in the synthesis

Synthesis

The term synthesis is used in many fields, usually to mean a process which combines together two or more pre-existing elements resulting in the formation of something new....
or derivatization of chemical compound

Chemical compound

A chemical compound is a Chemical substance consisting of two or more different chemical element Chemical bond together in a fixed mass ratio that can be split into simpler substances....
s. Examples of acetylation reactions include acylation

Acylation

In chemistry, acylation is the process of adding an acyl group to a compound. The compound providing the acyl group is called the acylating agent....
processes such as esterification

Esterification

Esterification is the general name for a chemical reaction in which two reactants form an ester as the product . Esters are common in organic chemistry and biological materials, and often have a characteristic pleasant, fruity odor....
(see below) and the Friedel-Crafts reaction

Friedel-Crafts reaction

The Friedel-Crafts reactions are a set of organic reaction developed by Charles Friedel and James Crafts in 1877. There are two main types of Friedel-Crafts reactions: alkylation reactions and acylation reactions....
).

CH₃COCl + HO-CH₂-CH₃

Ethanol

Ethanol, also called ethyl alcohol, pure alcohol, grain alcohol, or drinking alcohol, is a volatility , flammable, colorless liquid....
? CH₃-COO-CH₂-CH₃

Ethyl acetate

Ethyl acetate is the organic compound with the formula CH3COOCH2CH3. This colorless liquid has a characteristic sweet smell like certain glues or nail polish removers, in which it is used....
+ H-Cl

Hydrogen chloride

Frequently such acylations are carried out in the presence of a base such as pyridine

Pyridine

Pyridine is a simple and important heterocyclic aromatic organic compound with the formula CarbonHydrogenNitrogen. This colorless liquid with a distinctive fish-like odor is structurally related to benzene, wherein one CH group in the six-membered ring is replaced by a nitrogen atom....
, triethylamine

Triethylamine

Triethylamine is the chemical compound with the chemical formula N3, commonly abbreviated ethyl group3N or TEA. It is a commonly encountered in organic synthesis probably because it is the simplest symmetrically trisubstituted amine, i.e....
, or DMAP

4-Dimethylaminopyridine

4-Dimethylaminopyridine is a nucleophilic derivative of pyridine with the chemical formula 2NC5H4N. This colourless solid is a useful nucleophilic catalyst for a variety of reactions such as esterifications with anhydrides, the Baylis-Hillman reaction, hydrosilylations, tritylation, the Steglich rearrangemen...
, which as catalysts help to promote the reaction and as base

Base (chemistry)

In chemistry, a base is most commonly thought of as an aqueous substance that can accept protons. A base is also often referred to as an alkali if OH- ions are involved....
s neutralize

Neutralization

In chemistry, neutralization is a chemical reaction in which an acid and a base or alkali react to produce salt and water.During the process, hydrogen ions H+ from the acid or a hydronium H3O+ and hydroxide ions OH- or oxide ions O2- from the base react together to form a water mo...
the resulting HCl. Such reactions will often proceed via ketene

Ketene

A ketene is an organic compound of the form R2C=C=O. Hermann Staudinger pioneered the research of ketenes. Ketene also refers to ethenone, the specific compound of this class in which both Rs are hydrogen....
.

Acetylation is the introduction of an acetyl

Acetyl

In organic chemistry, acetyl , is a functional group, the acyl of acetic acid, with chemical formula -CarbonOxygenCarbonHydrogen3. It is sometimes abbreviated as Ac ....
group via acylation

Acylation

In chemistry, acylation is the process of adding an acyl group to a compound. The compound providing the acyl group is called the acylating agent....
using a reactant such as acetyl chloride or acetic anhydride

Acetic anhydride

Acetic anhydride is the chemical compound with the chemical formula 2O. Commonly abbreviated Acetyl2O, it is one of the simplest acid anhydrides and is a widely used reagent in organic synthesis....
. An acetyl group is an acyl

Acyl

An acyl group is a functional group derived by the removal of one or more hydroxyl groups from an oxoacid.. In organic chemistry, the acyl group is usually derived from a carboxylic acid of the form RCarbon Oxygen hydroxyl....
group having the formula

-C(=O)-CH₃

For further information on the types of chemical reactions compounds such as acetyl chloride can undergo, see acyl halide

Acyl halide

Acetyl chloride

Synthesis

Uses

External links