Chapter 6:

Fatty Alcohols
By : Muhammad Imran Ismail
Faculty of Chemical Engineering,
UiTM Caw. Johor, Pasir Gudang Campus

Lecture 6.1 CHE 321 OLEOCHEMICAL TECHNOLOGY

 Syllabus Content
 WEEK CH  CHAPTER/CONTENT

1 1.0 Overview on development of oleochemical industries.

2-3 2.0 Oleochemical technology in Malaysia

4-5 3.0 Raw material feedstock for the oleochemical industries. 

6-7 4.0 Fatty acids.

8-9 5.0 Fatty Esters.

10-11 6.0 Fatty alcohols.

Latest technology available in oleochemical industries and future
12-13 7.0 challenges.

14 8.0 Plant visit to palm oil refinery.

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 Chapter 5: Fatty Alcohols

5.1 Production of fatty alcohols and its derivatives.

5.2 Flow chart

5.3 Uses and application of fatty alcohols.

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 LEARNING
OUTCOMES
The student should be able to:

• Define fatty alcohols.

• Describe the production processes of fatty alcohols

and its derivatives.

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The composition of
fatty alcohols
 Fatty Alcohols
• Term : Fatty alcohols (or long-chain alcohols) are usually
high-molecular-weight, straight-chain primary alcohols,
but can also range from as few as 4-6 carbons to as many
as 22-26, derived from natural fats and oils. The precise
chain length varies with the source.

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Flowchart & Production of
fatty esters
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 Production of fatty alcohols
1. Direct hydrogenation of fats and oils

2. Catalytic hydrogenation of
fatty acids and methyl esters from fats 
& oils • not commercially
• loss of glycerine
• higher consumption of H2
• increased use of catalyst

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 Catalytic hydrogenation of
fatty acids and methyl esters
Method 1: through Fatty acids (FA) Method 2: through Methyl esters (FAME)

1. Corrosion resistant required 1. Corrosion resistant not required

2. Higher reaction T causes lower yield
and damaged of catalyst by FA
3. High pressure required
4. Direct hydrogenation of FA not used in a
large commercial scale
2. Lower reaction temperature and
pressure
3. Acid-resistant catalyst not required
 High-Pressure Hydrogenation Processes

Methyl esters
Reaction Temp: 250–300⁰C
Cat: Copper Cat: Zinc
chromite chromite
Pressure:
25,000–30,000 kPa
Saturated Fatty Unsaturated Fatty
Alcohol Alcohol Equipment: Tubular
column

Hydrogenation – two methods

Depends on
• Fixed bed process catalyst type
used
• Suspension process
 High Pressure Hydrogenation Using Fixed-bed Process

Fixed bed=catalyst fixed as ‘bed’

and supported on carrier Hydrogen
(recycle)
Reaction
Temp: 200–
300⁰C

Heater
Methyl ester
Heater
Pressure:
20,000–
30,000 
kPa Separator
Resident
time:
5 min

Fatty alcohol
(separate
from
Excess methanol)
hydrogen
 High Pressure Hydrogenation Using Fixed-bed Process

The operating conditions are comparatively mild

- (fatty alcohol produced does not require further processing)

Overall yield is 99% (hydrocarbons and unreacted ester < 1%)

Catalyst consumption is claimed to be < 0.3%

 High Pressure Hydrogenation
Using Suspension Process
• Preheated fatty acid feed, recirculated fatty alcohol with the slurried catalyst & hydrogen gas are fed continuously (reaction is
carried out at approximately 30,000 kPa and 280⁰C)
• Heat of the product mixture leaving the reactor is recovered by the recirculating hydrogen gas through the heat exchanger
(Two-stage cooling–expansion system).
• Gas phase (excess H2 gas, some low boiling alcohols & reaction water) is separated from the liquid alcohols in the hot
separator.
• Gas mixture cooled further in the cold separator, where the low boiling alcohols and reaction water are condensed and
separated excess hydrogen gas is recycled into the system.
• Liquid alcohols from the hot separator are pumped into a flash drum where the dissolved hydrogen is released and recycled
with the make up hydrogen.
• Catalyst is separated from the crude fatty alcohol using a centrifugal separator, part of the catalyst is replaced with fresh
catalyst to maintain the activity.
• Clear phase portion from the centrifugal separator is passed through a polishing filter to remove all traces of suspended solids
• The resulting crude alcohol undergoes further distillation to remove hydrocarbons and may undergo fractionation if desired.
 High Pressure Hydrogenation
Using Suspension Process
Lurgi method
• Simultaneously
(a) esterification of the fatty acid with the fatty alcohol
(b) hydrogenation of the ester
~ to form 2 mol of fatty alcohol in the same reactor

Reduce damaging
Esterification is rapid effect of fatty acid on
catalyst

Fatty Alcohols = 250 *

(Volume of Fatty Acid) Feed is diluted
 Suspension Hydrogenation of Fatty Acids (Lurgi-Process)

H2 gas
some low boiling alcohols H2 gas
Hydrogen water

Reactor

Hot Separation
Cold Sep
aration
H2 gas
30000kPa
280⁰C
Liquid alcohol
Dissolved H2
Catalyst
Fatty Acid

Recirculated fatty alcohol some low boiling alcohols

with slurried catalyst water
 Suspension Process Versus Fixed Bed Process
Suspension Process
- Requires additional equipment
(separation of catalyst, distillation of the crude
fatty alcohol, rework of unreacted methyl ester)
- Lower yield
- Higher catalyst consumption (0.4% - 0.7%)
- Quality of fatty alcohol can be brought up to
same level by further distillation
- Constant hydrogenation activity (continuous
replacement of the catalyst)
Fixed Bed Process
- Requires higher capital cost
(larger reaction vessels, gas recirculation pump,
pipe work due to higher volume of hydrogen gas
used)
- Higher yield
- Lower catalyst consumption (0.2 %- 0.3%)
- Higher quality of fatty alcohol (lower hydrocarbon
content and lower saponification values)
- Gradual decrease in the hydrogenation activity due
to catalyst poisons (sulfur, phosphorus or chlorine)
 Fractionation of Fatty Alcohols
Crude fatty alcohol resulting from the various hydrogenation  processes
 undergo fractionation to produce different cuts of  alcohol.
Application of Fatty Alcohols
 Ethylene Fatty Alcohol Emulsifier for waxes
Fatty
oxide/ Polyglycol Ether and ointment bases
Alcohol
Propylene (Nonionic Surfactant)
oxide

SO3/ Fatty Alcohol Laundry detergent,

Fatty foaming agent in
chlorosulfoni Sulfates (Anionic
Alcohol toothpastes,
c acid/ Surfactants)
sulfuric acid.

Ethylenoxide then
Fatty Fatty Alcohol Ether Liquid shampoo,
with sulfuric
Alcohol Sulfates (Anionic bath preparation
trioxide/
Surfactants
chlorosulfonic acid
 Lubricants during the
polymer processing, raw
materials for waxes and
Fatty Fatty Wax creams.
Alcohol acids Esters

Fatty Arcylic acid/

Esters Precursor of
Alcohol Methacrylic acid
polymethacrylates

Adipic acid/ Acelaic

Fatty
acid/ Sebacic acid/
Alcohol Esters Plasticizers for PVC
Trimellitic acid/
Citric acid
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 TRAIN YOUR BRAIN
1. Define Fatty Alcohol.

2. Using a process flow diagram, show a production process of fatty alcohol from fats and
oils.

3. Provide chemical structure of hydrogenation of FAME. List two(2) products produced.

4. Reaction of fatty acid with hydrogen produced fatty alcohol and water. Show a chemical
reaction of the production process.

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 TRAIN YOUR BRAIN
Based on your understanding, suggest suitable methods of fatty alcohol production
with suitable explanations.

With an aid of diagram, Explain in details Fixed Bed Process.

With an aid of diagram, Explain in details Lurgi Process.

Differentiate between hydrogenation process using fixed bed versus suspension.

List uses of alcohol based on the given derivatives:

Fatty Alcohol Polyglycol Ether (Nonionic Surfactant)

Fatty Alcohol Sulfates (Anionic Surfactants)

Fatty Alcohol Ether Sulfates (Anionic Surfactants

Wax Esters

Esters

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 Next Class Activities
This is group activities on Wednesday which be held at Lab. You need to produce a bar
soap/liquid soap and packed it nicely. Make sure all FKK’s lecturers get the soap and send sweet
words to appreciate their teaching. Don’t forget to write your code subject and lecturers name.

Answer this questions and submit y group.

• Name the process of soap formation.
• List two(2) reactants used to produced soap.
• With an aid of chemical formula, describe the soap formation process.
• Describe the process of soap formation process. List material used.
• Depending of the nature of the alkali used, soap have distinct properties. Give two examples
of alkali which produce hard and soft soap.
• Explain the cleaning process using soap.

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