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ACETYL CHLORIDE

CAS NUMBER: 75-36-5

EC NUMBER: 200-865-6

MOLECULAR FORMULA: CH3COCl

MOLECULAR WEUGHT: 78.50

 

 

Acetyl chloride is an acyl chloride derived from acetic acid. 
Acetyl chloride belongs to the class of organic compounds called acyl halides. 

Acetyl chloride is a colorless, corrosive, volatile liquid. 
Acetyl chlorides formula is commonly abbreviated to AcCl.

Acetyl chloride appears as a colorless, fuming liquid with a pungent odor. 
Density 9.2 lb / gal. 

Flash point 40°F. 
Vapor, which is heavier than air, irritates the eyes and mucous membranes. Corrosive to metals and tissue.

Acetyl chloride (CH3COCl) is an acyl chloride derived from acetic acid. 
Acetyl chloride belongs to the class of organic compounds called acyl halides. 

Acetyl chloride is a colorless, corrosive, volatile liquid. 
Acetyl chlorides formula is commonly abbreviated to AcCl.

Acetyl chloride is produced in the laboratory by the reaction of acetic acid with chlorodehydrating agents such as PCl3, PCl5, SO2Cl2, phosgene, or SOCl2. 
Acetyl chloride is an acid chloride reagent used for acetylation in organic synthesis reactions such as esterification and the Friedel-Crafts reaction. 

Acetyl chloride has been reported that Acetyl chloride can be used as a fluorescence histochemical in combination with formaldehyde to identify tryptophyl-peptide-containing endocrine cells of the hypophysis. 
Furthermore, gaseous Acetyl chloride can be used in Fourier-transform infrared emission spectroscopy at 248nm, which can detect fragments of HCl, CO, and CH2 in the presence of Ar or O2. 

Alternate studies suggest that Acetyl chloride can be used as a derivatizing agent for determining high molecular weight alcohols in fish oil.
Acetyl chloride is a colorless pungent fuming liquid CH3COCl made by chlorination of acetic acid or its derivatives (as by distilling a mixture of acetic acid and phosphorus trichloride) and used chiefly in preparing acetyl derivatives.

Also known as ethanoyl chloride, acetyl chloride is an "acid chloride" derived from acetic acid. 
Acetyl chloride does not exist in nature, because upon contact with water it hydrolizes into acetic acid and hydrogen chloride. 

Acetyl chloride is used in acylation processes such as esterification and the Friedel-Crafts Reaction.
Acetyl chloride is a radical formed from an organic acid by removal of a hydroxyl group. 
 
Acetyl chloride halide is one of a large group of organic substances containing the halocarbonyl group, have the general formula RCO·X, where X is a halogen atom (fluorine, chlorine, bromine, iodine, and astatine) and R may be aliphatic, alicyclic, aromatic, and H etc. 
In substitutive chemical nomenclature, their names are formed by adding '-oyl' as a suffix to the name of the parent compound; ethanoyl chloride, CH3COCl, is an example. 

The terms acyl and aroyl halides refer to aliphatic or aromatic derivatives, respectively. 
Acetyl chloride halides are made by replacing the -OH group in carboxylic acids by halogen using halogenating agents. 

They react readily with water, alcohols, and amines and are widely used in organic synthetic process whereby the acyl group is incorporated into the target molecules by substitution of addition-elimination sequence called acylation reaction.  
Acetyl chloride reaction involves substitution by an electron donor (nucleophile) at the electrophilic carbonyl group (C=O). 

Common nucleophiles in the acylation reaction are aliphatic and aromatic alcohols, both of which give rise to esters and amines (RNH2) which give amides. 
The carboxylic acid (X = OH) itself can function as an acylating agent when it is protonated by a strong acid catalyst as in the direct esterification of an alcohol. 

Two common acylation agents, with the general formula RCOX, are acid halides (X = halogen atom) and anhydrides (X = OCOR). 
Schotten-Baumann reaction is an Acetyl chloride reaction that uses an acid chloride in the presence of dilute alkali to acylate the hydroxyl and amino group of organic compounds. 

There are also other Acetyl chloride agents. 
Acetyl chlorides are used as very reactive intermediates to prepare carboxylic acid derivatives including anhydrides, esters and amides because of the two strong electron withdrawing chlorine and oxygen on the carbonyl compound, and positive charge carbon accordingly. 

Acetyl chloride is easy for a weak nucleophile to attack the carbon. 
Acid chlorides are also reactive with Gilman reagents to prepare large molecules from smal ones by replacing the halides with an organic group. 

Acetyl Chloride is a clear, corrosive and fuming liquid; melting point of -112 C, boiling point of 51-52 C, refractive Index of 1.3890. 
Acetyl chloride undergoes violently hydrolysis in presence of atmospheric moisture. 

Acetyl chloride is soluble in ether, acetone, and acetic acid. 
Acetyl chloride is prepared by reacting acetic acid with a halogenating agent such as phosphorus(III or V) chloride or sulphur dichloride oxide. 

Acetyl chloride is widely used as an acetylating agent in the synthesis of fine chemicals, agrochemicals and pharmaceuticals. 
The hydrogen atoms replace oxygen atoms in alcohols or nitrogen atoms in amines, which protects amine groups during amino acid synthesis. 

Acetyl chloride is also used as an intermediate for dyes. 
Acetyl chloride is also used to determine water in organic liquids.

Acetic chloride is a colourless to light yellow liquid with a pungent and choking odour. 
Acetic chloride is highly flammable and reacts violently with DMSO, water, lower alcohols, and amines. 

Along with air, acetic chloride may form an explosive mixture. 
Acetyl chloride is incompatible with water, alcohols, amines, strong bases, strong oxidising agents, and most common metals. 

On decomposition when heated, acetic chloride produces carbon monoxide, carbon dioxide, hydrogen chloride, and phosgene.
A colorless, fuming liquid with a pungent odor. 

Vapor, which is heavier than air, irritates the eyes and mucous membranes. 
Corrosive to metals and tissue.

Acetyl chloride can be prepared by chlorination of acetic anhydride in several different ways, by reaction of methyl chloride with carbon monoxide in the presence of catalysts, by reaction ofketene with HCI, or by partial hydrolysis of 1, 1, l-trichloroethane, Acetyl chloride hydrolyzes in the presence of water to give acetic acid. 
Acetyl chloride reacts with ammonia and amines to give acetamides. 

Reaction with alcohols gives the corresponding acetate esters. 
Acetyl chloride will add across unsaturated bonds in the presence ofsuitable catalysts to give halogenated ketones.

 

 

USES OF ACETYL CHLORIDE:


Acetyl chloride is used for acetylation reactions, i.e., the introduction of an acetyl group. 
Acetyl is an acyl 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. 
Two major classes of acetylations include esterification and the Friedel-Crafts reaction.

Acetyl chloride is a reagent for the preparation of esters and amides of acetic acid, used in the derivatization of alcohols and amines. 
One class of acetylation reactions are esterification.

Acetyl Chloride is a very useful synthetic intermediate. 
Acetyl chloride is a derivative of acetic acid, a weak acid, used as a reagent in numerous industrial processes. 

Acetyl chloride is a chemical for acetylation in the synthesis or derivatization of organic compounds.
Acetyl Chloride is a very useful synthetic intermediate. 

Acetyl chloride is a derivative of acetic acid, a weak acid, used as a reagent in numerous industrial processes. 
Acetyl chloride is a chemical for acetylation in the synthesis or derivatization of organic compounds.

Acetyl chloride is a kind of acetylating agent, being used as raw materials for pesticides and medicine, or the intermediates for the manufacturing of water treatment agent ethylidene diphosphate.
Acetyl chloride can be used for the analysis of reagents as well as used for the preparation of acetyl derivatives and dyes

Acetyl chloride can be used for organic synthesis, dyes and pharmaceutical industries
Acetyl chloride can be used as the raw materials of pesticides and pharmaceutical as well as the intermediate for the manufacture of water treatment agent ethylene diphosphate. 

Moreover, Acetyl chloride can also be used for the manufacture of new electroplating complexing agent. 
Acetyl chloride is an important acetylating agent with the acylation capability being stronger than acetic anhydride. 

Acetyl chloride is widely used in organic synthesis and dyes. 
Acetyl chloride is also the catalyst for the carboxylic acid to have chlorination reaction as well as being used for hydroxyl and amino quantitative analysis.
Acetyl chloride can be used as raw material for organic synthesis, used in the production of pesticides, pharmaceuticals, new electroplating complexing agent, the catalyst for carboxylic acid to have chlorination, acetylation agent, and other kinds of fine organic synthesis intermediates.

 

 

APPLICATION OF ACETYL CHLORIDE:


Acetyl chloride for synthesis. CAS 75-36-5, molar mass 78.49 g/mol.
Acetyl chloride is the most commonly used acetylating agent with reaction with alcohol and phenol generating acetate ether. 

Acetyl chlorides reaction with ammonia can generate acetamide with its interaction with primary amine and secondary amine to generate N-substituted acetamide.
Acetyl chloride can be used for the manufacturing of pharmaceutical industry, pesticide manufacturing, acetyl derivatives and dyes. 

Acetyl chloride can be used as the reagents for the determination of phosphorus, cholesterol, water content contained in organic solvents, nitroso, hydroxyl and tetraethyl lead.
Acetyl chloride is the most important acyl halide and can be manufactured through the reaction between glacial acetic acid and thionyl chloride or phosphorus trichloride and phosphorus pentachloride.

 

 

PROPERTIES OF ACETYL CHLORIDE:


Acetyl chloride appears as colorless fuming liquid with a strong odor and eye irritation effect. 
The relative density of 1.1051 (20 ° C), the melting point of-112 ° C, the boiling point of 51-52 ° C and the flash point is 4.4 ° C (closed dish). 

In the wet air, Acetyl chloride can slowly undergo decomposition and give white smoke. 
When coming across water, Acetyl chloride can be violently hydrolyzed into acetic acid and hydrogen chloride, and thus should be sealed for storage. 

Acetyl chloride is miscible with benzene, acetone, chloroform, ether, glacial acetic acid and petroleum ether. 
Liquid is heavier than water with the vapor being heavier than air. 

Acetyl chloride can have metathesis reaction with many compounds. 
Acetyl chloride can bind to the thiol group in the protein, and therefore being toxic to humans. 

Acetyl chloride is an important kind of acetylation agents with its acylation capability being stronger than acetic anhydride. 
Acetyl chloride is widely used in organic synthesis, being also the catalyst for the chlorination of carboxylic acids. 

Acetyl chloride appears as colorless transparent liquid smoke with irritating smell. 
Acetyl chloride is miscible with ether, acetic acid and benzene.

 

 

PHYSICAL AND CHEMICAL SPECIFICATIONS OF ACETYL CHLORIDE:


-Formula: CH3COCl / C2ClH3O

-Molecular mass: 78.5

-Boiling point: 51°C

-Melting point: -112°C

-Relative density (water = 1): 1.11

-Solubility in water: reaction

-Vapour pressure, kPa at 20°C: 32

-Relative vapour density (air = 1): 2.7

-Flash point: 5°C c.c.

-Auto-ignition temperature: 390°C

-Explosive limits, vol% in air: 7.3-19

-Octanol/water partition coefficient as log Pow: -0.47  

 

 

PHYSICAL PROPERTIES OF ACETYL CHLORIDE:


-Boiling point:    52 °C (1013 hPa)

-Density: 1.10 g/cm3 (20 °C)

-Explosion limit: 7.3 - 19 %(V)

-Flash point: 5 °C

-Ignition temperature: 390 °C DIN 51794

-Melting Point:    -112 °C

-Vapor pressure: 320 hPa (20 °C)

 

 

PRODUCTION METHOD OF ACETYL CHLORIDE:

Industrial, acetyl chloride can be manufactured through the reaction between ethylene with hydrogen chloride, or the reaction between sodium acetate, sulfur dioxide and chlorine. 
The laboratory can apply acetic acid, sodium acetate or acetic anhydride to have reaction with a variety of chlorination agents. 
For example, Acetyl chloride can be obtained through the reaction between acetic anhydride with chlorosulfonic acid (or hydrogen chloride, carbon tetrachloride, phosgene); or obtained through the reaction between glacial acetic acid and benzoyl chloride.

 

 

OCCURENCE OF ACETYL CHLORIDE:

Acetyl chloride is not expected to exist in nature, because contact with water would hydrolyze it into acetic acid and hydrogen chloride. 
In fact, if handled in open air Acetyl chloride releases white "smoke" resulting from hydrolysis due to the moisture in the air. 
The smoke is actually small droplets of hydrochloric acid and acetic acid formed by hydrolysis.

 

 

STABILITY OF ACETYL CHLORIDE:

Stable under recommended storage conditions.

 

 

STORAGE OF ACETYL CHLORIDE:


-Acetic chloride should be stored in a segregated and approved area, away from incompatibles such as oxidizing agents, alkalis and moisture. 

-The container of acetic chloride should be kept in a cool, well-ventilated area, tightly sealed until ready for use. 

-Fireproof. 

-Store in an area without drain or sewer access. 

-Separated from incompatible materials. 

-Dry. 

-Well closed. 

 

 

SYNONYM:

75-36-5
Ethanoyl chloride
Acetic chloride
Acetylchloride
Acetic acid chloride
CH3COCl
RCRA waste number U006
UNII-QD15RNO45K
CH3-CO-Cl
MFCD00000719
QD15RNO45K
Acetyl chloride, 98%
Acetyl chloride, 99+%
Acetic acid, chloride
Acetyl chloride, 99%, ACS reagent
Acetyl chloride, reagent grade, 98%
CCRIS 4568

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