Manufacturing of

Acetyl Chloride

MIRKA

Presented by:
ER. Chandan Jain
29 january ‘14
 Introduction
Molecular formula- CH3COCl

3-D Structure

2-D structure

Acetyl chloride is also known:-

IUPAC Name- Ethanoyl chloride
Common name- Acyl chloride
 HISTORICAL PROFILE
 The Acetyl chloride was described in 1850 directly from Acetic
acid has been accomplished by the various chlorinating agent,
but the parcentage yield of acetyl chloride was never found
satisfactory, owing to the difficulty in recovering the last traces
of acetyl chloride from the effluent gases product as well as to
the tendency towards further chlorinating in these old process.

 Afterword Acetyl chloride was prepared by distilling a mixture

of anhydrous sodium (C2H3O2Na), and phosphorous
oxychloride (POCl3)
 Application
Traditional Application:-

 Used in manufacturing of dyestuffs and

pharmaceuticals.

 Household uses include toilet, metal and drain cleaners.

 Industrial uses include metal refining, plumbing,

bleaching, engraving, plating, photography, disinfection,
munitions, fertilizer manufacture

 Used as a prime for artificial nails

 Current applications:-

 Acetyl chloride is an efficient acetylating agent for alcohols and

amines to produce the corresponding esters and amides.
.
 Acetyl chloride is used in the synthesis of dyes and
pharmaceutical chemicals.

 Acetyl chloride is also used in acylation of benzene to make

acetophenone.
 Properties
Physical Properties:-
Molecular Formula CH3COCl

Molecular Weight 78.50

Boiling Point 51.5°C

Density 1.104 g/ml, liquid

Melting point -112 °C, 161 K, 170 F

Solubility in water Rapidly hydrolysis

Appearance colorless liquid

Color/form Colorless Fuming liquid

Critical temperature 475 deg F = 246° C = 519 K

Critical pressure 845 psia = 57.5 atm = 5.83 MN/sq m

Flash point 4°C

Autoagination 390°C

Specific gravity 1.104

Contd….
 Chemical properties:-
Contd…..
 It is a chemical for acetylation in the synthesis or derivatization
of organic compounds Examples of acetylation reactions
include acylation processes such as esterification (see below)
and the Friedel-Crafts reaction.

CH3COCl + HO-CH2-CH3 → CH3-COO-CH2-CH3 + H-Cl

Economic Scenario
Acetyl chloride is mostly manufactured as Captive product.

Thus, little is known about the market of acetyl chloride.

The total U.S. market = 500 MT annually in 1994.

3 Grade of Acetyl chloride:-

 Puriss. p.a., ≥99.0%
 Reagent grade, 98%
 Reagent grade, 98%

The price of Acetyl chloride varies according to there respective

grade
Contd…
 Acetyl chloride has price in Indian Market =9,901.10
Rupee/liters (>99%pure) [5]

 The total manufacturing capacity in India = 12000 TPA

( Year 2010)

 The total consumption in India = 24000 TPA (Year

2010)

 The total gap in supply and demand = 12000 TPA

(Year 2010)
Manufacturers
 A.B. Enterprises Mumbai

 Jai Ganesh Chemicals Navi Mumbai

 Sahyadri Organic Industries Sangli

 Transpek Industry Limited, Vadodara

Criteria for plant capacity selection
 After having a look at world, as well as, Indian economic
scenario of Acetyl chloride we have analyzed and found a lag of
12,000 TPA between demand and supply of the same, in India.

 Therefore, targeting Indian market only, it is decided to come up

with a plant having capacity of
12,000TPA .
Manufacturing Processes
 Acyl chlorides are generally prepared in the same manner
as alkyl chlorides, by replacing the corresponding hydroxy
substituents with chlorides. Thus, carboxylic acids are treated
with thionyl chloride (SOCl2), phosphorus trichloride (PCl3),
or phosphorus pentachloride (PCl5):

 RCOOH + SOCl2 → RCOCl + SO2 + HCl

 3 RCOOH + PCl3 → 3 RCOCl + H3PO3

 RCOOH + PCl5 → RCOCl + POCl3 + HCl

 Contd…..
 The usual method involves the reaction of acetic acid with
standard inorganic chlorodehydrating agents, such as by
using PCl3 PCl5, SO2Cl2, or SOCl2. However, this usually gives
acetyl chloride which is contaminated by phosphorus or sulfur
impurities, which may interfere with the organic reactions.

 It is produced by the reaction of hydrogenchloride with acetic

anhydrid

(CH3CO)2O + HCl → CH3COCl + CH3CO2H

 Selected process flow diagram
NaOH(10%aq) Vent to atmosphere
Water Vacuum pump
Acetyl chloride
Effluent
Ab
Mono chloroacetic so
Mono chloro- rb Acetic acid
acid,storage
er
acetic acid
`

reactor-2

SO2+HCl

SCl2 +Cl2 Surge

drum
Mono chloro-acetic acid
storage
 Process Description
 For cyclic operation, these reactions may be considered as accurring
in two chambers which will be donominated in Chlorination chamber
reaction 2nd will proceeding

 Anhydrization and halohydragenation chamber reaction 3rd and 4th

will proceed

 When chloroacetic acid (b.p189°C), it reacts with chlorine in the

presence of sulpur chloride at temp. 60°C, and produce an almost
quantitative yield of chloroacetyl chloride (b.p 105°C), is brought into
reaction with one mole of glacial acetic acid (b.p 118°C) there is
produced a one mole of the mixed anhydride-monochloracetic-acetic
anhydride (b.p 170°C).
Main reactions:-

 Cl.CH2CO.OH+SCl2+Cl2 2Cl.CH2.CO.Cl+2HCl+SO2

 Cl.CH2.CO.Cl+HO.CO.CH3 ClCH2CO.O.COCH3+HCl

 ClCH2CO.O.CO.CH3+HCl ClCH2.COOH+CH3COCl
Contd….

 And the production of mixed anhydride in reaction 3rd with the

one mole hydrogen chloride is like wise produced so that
immediately there is a augurated in reaction 4th . the condition of
equilibrium it depend on hydrogen chloride , actually operate to
promote the formation of the volatile acetyl chloride and the
creation of residual mass of chloroacetic acid this hydrogen
chloride will further used in reaction 4th

 In reactor 2nd , reaction 3rd between chloroacetyl chloride and

glacial acetic acid and it use to give the yield of about 80-85%.
And further the desirable product can be separated by distillation
 Reference
1. http://www.gfschemicals.com/statics/productdetails/
acetyl_chloride_5307.html
2. http://www.alfa.com/en/gp100w.pgm?dsstk=43262
3. http://www.chemspider.com/Chemical-Structure.6127.html
4. http://www.chemindustry.com/apps/search
5. http://www.sigmaaldrich.com/catalog/search?interface=CAS
%20No.&term=75-36-
5&lang=en&region=IN&focus=product&N=220003048+2198
53147+219853286&mode=partialmax
THANK

YOU