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Experiment # 2:

Preparation of
Acetaldehyde

Date: 05-10-10

Muhammad Usman

(2008-chem-02-B)

Unit process lab


Department of Chemical Engineering, UET Lahore
1. Ethanol:

Harmful:
Pure Ethanol will irritate the skin and eyes. Nausea, vomiting and intoxication
are symptoms of ingestion. Long term use by ingestion can result in serious liver
damage. Death from Ethyl alcohol consumption is possible when blood alcohol
level reaches 0.4%.
A blood level of 0.5% or more is commonly fatal. Levels of even less than 0.1%
can cause intoxication, with unconsciousness often occurring at 0.3–0.4%

Highly flammable:
It has a flash point of 13 oC. It can readily catch fire. So care should be taken
while handling it because its combustion products include Acetaldehyde which
is a strongly carcinogenic substance. However, ethanol itself is not cancer
causing.

Properties of Ethanol:

IUPAC Name Ethanol


Absolute alcohol
Drinking alcohol
Ethyl alcohol
Other names
Ethyl hydrate
Grain alcohol
Hydroxy-Ethane

Appearance Colorless liquid

Unit process lab


Department of Chemical Engineering, UET Lahore
Structure

Molecular formula C2H6O


Molar mass 46.07 g mol-1
Density 0.789 g cm-3
Melting point -114.3 oC
Boiling point 78.4 oC
Solubility in water Miscible
Acidity (Pka) 15.9
Flash point 13 oC
Auto-ignition temperature 422 oC

Sodium Di-chromate:

Oxidant:
Sodium di-chromate is a strong oxidizing agent. It will readily oxidize
anything that will come into contact with it. Precautionary measures are
necessary while handling it.

Corrosive:
It is a strongly corrosive compound as it readily oxidizes anything.

Dangerous to Environment:
It is a Hexa-valent chromium ion so is considered hazardous. It can
contaminate potable water as it is of carcinogenic properties.

Unit process lab


Department of Chemical Engineering, UET Lahore
Very toxic:
If swallowed, this compound can even cause death because it is very toxic
compound. It is carcinogenic in nature. Potable water should especially be
treated which may contain Hexa-valent chromium compounds.

Harmful:
It is a very harmful substance. Its contact with skin should be avoided.

Properties of sodium di-chromate:

IUPAC name Sodium dichromate


Other names Chromic acid, (H2Cr2O7), disodium salt

Structure

Molecular formula Na2Cr2O7


261.97 gmol-1 (anhydrous)
Molar mass
298.00 gmol-1(di-hydrate)

Appearance

Density 2.52 g cm-3


Melting point 356.7 oC
Boiling point 400 oC decomposes
Solubility in water 730 g/ l (25 oC)

Unit process lab


Department of Chemical Engineering, UET Lahore
Sulphuric acid:

Corrosive:
It is a strongly corrosive compound as it readily oxidizes anything.

Dangerous to Environment:
Although sulfuric acid is non-flammable, contact with metals in the event of a
spillage can lead to the liberation of hydrogen gas. The dispersal of acid aerosols
and gaseous sulfur dioxide is an additional hazard of fires involving sulfuric acid.

Very toxic:
Sulfuric acid is not considered toxic besides its obvious corrosive hazard, and the
main occupational risks are skin contact leading to burns and the inhalation of
aerosols. Exposure to aerosols at high concentrations leads to immediate and
severe irritation of the eyes, respiratory tract and mucous membranes.

Properties of sulfuric acid:

IUPAC name Sulfuric acid


Other names Oil of vitriol

Structure

Unit process lab


Department of Chemical Engineering, UET Lahore
Molecular formula H2SO4
Molar mass 98.06 g/gmol

Appearance

Density 1.84 g/cm3 (liquid)


Melting point 10 oC
Boiling point 337 oC
Solubility in water Miscible
Acidity (Pka) -3
Viscosity 26.7 cP (20 oC)
Flash point Non- flammable

Water:
It is a non-hazardous compound.

Environmentally safe:
Water is an essential part of life. Life cannot be sustained without water.
Food & eatables contain some amount of water in them. It is a non-
hazardous compound.

Water
IUPAC name
Oxidane
Hydrogen oxide
Dihydrogen monoxide
Hydrogen monoxide
Other names
Hydroxylic acid
Hydrogen hydroxide
R-718

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Department of Chemical Engineering, UET Lahore
Oxygen dihydride
Oxygen hydride
Oxane

Structure

Molecular formula H2O


Molar mass 18.0152833 gmol-1

Appearance

1000 kg m-3 (liquid)


Density 917 kg m-3 (solid)

Melting point 0 oC
Boiling point 99.98 oC
Acidity (Pka) 15.74
Basicity (Pkb) 15.74
Viscosity 0.001 Pa.S (20 oC)

Unit process lab


Department of Chemical Engineering, UET Lahore
Preparation of Acetaldehyde

Chemicals required:
1) Ethanol 2) Sodium di-chromate
3) Concentrated H2SO4 4) Water

Chemical reaction:

[O] -[H2O]
CH3CH2OH CH3CH (OH)3 CH3CHO

Apparatus Required:
Bolt head flask Dropping funnel
Knee tube Water condenser
Adopter Conical flask beaker
Stirrer

Procedure:
1. Place 50 ml water in Bolt head flask & add slowly with shaking 17 ml of concentrated H2SO4.
Finally add some fragments of porcelain.
2. Dissolve 50 g of Na-Dichromate in 50 ml of water in a beaker. Add 40 ml of Ethanol & then
place the well stirred mixture in the dropping funnel.
3. Arrange the apparatus & check that rapid stream of cold water is passing through the condenser
& adopter dips into a conical flask which is surrounded by cold/ice water. Now heat the dilute
acid in flask until it starts boiling gently.
4. Then remove the flame & run Di-Chromate solution slowly. A vigorous reaction occurs & a
mixture of Acetaldehyde & H2O containing a little Acetic acid begins to distill over.
5. The reaction mixture becomes green due to the reduction of Di-Chromate. The addition of Di-
Chromate solution should take 20 minutes.

Unit process lab


Department of Chemical Engineering, UET Lahore
Uses of Acetaldehyde:
1. Acetaldehyde is used in the manufacture of pentaerythritol, per acetic acid, pyridines,
paraldehyde, acetic acid, acetic anhydride, 2-ethylhexanol, aldol, chloral, 1,3-butylene glycol,
trimethylolpropane, butanol, perfumes, aniline dyes, plastics and synthetic rubber.
2. It is used in silvering mirrors and in hardening gelatin fibers.
3. It is also used as a chemical intermediate and synthetic flavoring substance and adjuvant

Industrial production of Acetaldehyde:


Industrially acetaldehyde is produced via following process.

Raw materials:
Raw materials used are following.

a. Air (provide oxygen for oxidation)


b. Ethanol (C2H5OH)

Air, with the help of a compressor is introduced into the mixing chamber via a sparger that distributes it
very finely into the column. Ethanol is added in liquid form.

Catalyst:
Silver catalyst is used for dehydrogenation of ethanol in order to convert it to acetaldehyde. By nature Ag
catalysts are dehydrogenative in nature.

The catalyst is in the form of silver gauze.

Preheating:
Steam is used as a heating medium to increase the ethanol-air mixture temperature to nearly 150 oC. At
this temperature both the reactants will be in vapor phase.

Steam point:
Here steam is introduced into the mixture to provide heat blast in order to maintain the heat contents of
mixture.

Super heater:
Here the temperature of the stream is raised to a value of 600-650 oC.

Unit process lab


Department of Chemical Engineering, UET Lahore
Reactor vessel:
There are two parts of the reaction vessel.

1. Reactor:
In upper part of reaction vessel chemical reaction takes place in the presence of silver catalyst and
reactants change into the products along with the formation of side products.
2. Boiler:
Lower part of the reaction column is called the boiler unit. Here the heat of the reaction mixture is
exchanged with water that is converted in steam by taking the heat from mixture and a result
lowering its temperature.

Cooling water heat Exchanger:


A cooling water heat exchanger is used to reduce further the temperature of the stream.

Absorption tower:
Product stream including acetaldehyde along with other un-reacted, unwanted side products is introduced
into absorption column from the bottom & water is showered from the top of the column. Acetaldehyde is
absorbed into the water along with ethanol while other materials that are usually in the form of gases
leave away from he column and are called tail gases.

Distillation tower:
In distillation tower ethanol and acetaldehyde are separated on the basis of difference in their volatility.
Acetaldehyde is collected at the bottom where ethanol at the top from where it is again recycled back.

References:
1. Unit processes in organic synthesis by P.H. Groggins

5th edition, page 518-519

2. Shrives chemical process industries by George T. Austin


2nd edition, page 946-947
3. Wikipedia
http://en.wikipedia.org/wiki/acetaldehyde/

Unit process lab


Department of Chemical Engineering, UET Lahore