customers What do Croda make Sheeps wool Rapeseed oil Wheat Fish Moisturisers Omega 3 capsules Polymer additives Shampoo A B C D 1 2 3 4 Fish oil and Croda Crude Fish oil Product ID: 933131
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Slide1
Slide2Markets We Serve
Slide3Croda’s
customers
Slide4What do Croda make?
Sheep’s wool
Rapeseed oil
Wheat
Fish
Moisturisers
Omega 3 capsules
Polymer additives
Shampoo
A
B
C
D
1
2
3
4
Slide5Fish oil and Croda
Crude Fish oil
Product
Extraction of fish oil from fish
Fish
Slide6Card sort activity
In front of you are some cards with steps that take you from the raw material (fish) to crude fish oil (coloured product)
Can you work out the correct order of the process…?NB: “Bleaching” in this context refers to a process that lightens the colour of the mixture (not standard kitchen bleach!)
5 minutes
Slide7Card sort answers
Waste
material from fishing industry
Breaks raw material into
smaller pieces
(increases surface area for subsequent steps)
Breaks down further and
releases more oil
Separates
oil phase (containing the fish oil) from an aqueous phase
Removes solids
Material at this stage can be
slightly acidic
Improves
colour
& is also used to remove impurities (such as arsenic and heavy metals)
Semi-refined “crude” fish oil
(
intermediate product
)
1
2
3
4
8
7
6
5
Slide8Fish Oil and Omega-3
Crude fish oil is a mixture of many different saturated and unsaturated fats bonded together as triglycerides
Saturated no C=C double bonds
Mono-unsaturated one C=C double bond
Polyunsaturated
multiple C=C double bonds
Slide9Unsaturated VS Saturated
Double Bond
Single Bond
Unsaturated
Saturated
Slide10Fish Oil and Omega-3
Crude fish oil is a mixture of many different saturated and unsaturated fats bonded together as triglycerides
Saturated fats are generally bad for healthOmega-3 oils are large poly-unsaturated fats which have lots of health benefits including:
Brain Function
Eye Health
Heart Health
Slide11Glycerol
Glycerol is a naturally occurring molecule (Propane 1,2,3-Triol)
It is also referred to as glycerine and is used as a sweetenerFigure: Structure of Glycerol
Slide12Molecular modelling kits
You have some molecular modelling kits in front of you
Various different atoms and bond possibilities can be made, an example is shown below:
Make glycerol
Hint: it has three hydroxyl groups (OH)
Hydrogen
Carbon
Oxygen
Single bond
Double bond
5 minutes
Activity
Slide13Glycerol
5 minutes
Activity
Slide14Fatty acids
Many different kinds with different chemical structures and properties
Present in naturally occurring fats and oils Long hydrocarbon chainHydrophobic – water hatingOily or fatty partCarboxylic acid functional group
Hydrophilic – water loving
Constitutes “acid” part
Surfactant structure – when it contains both hydrophobic and hydrophilic it is called
amphiphilic
hydrophilic
hydrophobic/lipophilic
Slide15Common examples
Systematic name
Trivial name
Shorthand designation
Simple saturated
butanoic
butyric
C4:0
hexanoic
caproic
C6:0
dodecanoic
lauric
C12:0
hexadecanoic
palmitic
C16:0
octadecanoic
stearic
C18:0
Mono-unsaturated
hexadecenoic
palmitoleic
C16:1
octadecenoic
oleic
C18:1
docosenoic
erucic
C22:1
Poly-u
nsaturated
6,9,12-octadecatrienoic
gamma-linolenic
9,12,15-octadecatrienoic
alpha-linolenic
5,8,11,14,17-eicosapentaenoic
EPA
4,7,10,13,16,19-docosahexaenoic
DHA
Slide16Molecular modelling kits
You have some molecular modelling kits in front of you
Various different atoms and bond possibilities
Make a C6:0 fatty acid (IUPAC name:
hexanoic
acid)
Hydrogen
Carbon
Oxygen
Single bond
Double bond
5 minutes
Activity
Slide17Hexanoic Acid
5 minutes
Activity
Slide18Shorthand lipid numbers
Shorthand system
Different from the IUPAC system but often used in industry and related academic fieldsFormat is - CX:
Y
(
omega-Z
) - where
X
,
Y, Z are numbersProcess to assign X, Y
, and Z Count number of carbon atoms including carboxylic acid carbon = X
Count number of double bonds = YCount number of carbon atoms from the omega carbon to the start of the first double bond = ZWhat is the lipid number of the below fatty acid?
Slide19C
22
: 6 (ω- 3 )
Shorthand system
Different from the IUPAC system but often used in industry and related academic fields
Format is C
X
:
Y
(ω-Z)
X = total number of carbon atoms in the moleculeY = number of double bondsZ = distance from
omega (ω) carbon to closest double bondShorthand lipid numbers
C
_
: _ (ω-
_ )
C
22: _ (
ω- _ )C
22: 6 (ω- _ )
Slide20Systematic name
Trivial name
Shorthand designation
butanoic
butyric
C4:0
hexanoic
caproic
C6:0
dodecanoic
lauric
C12:0
hexadecanoic
palmitic
C16:0
octadecanoic
stearic
C18:0
cis-9-hexadecenoic
palmitoleic
C16:1(
ω
-7)
cis-9-octadecenoic
oleic
C18:1(
ω
-9)
cis-13-docosenoic
erucic
C22:1(
ω
-9)
6,9,12-octadecatrienoic
gamma-linolenic
C18:3(
ω
-6)
9,12,15-octadecatrienoic
alpha-linolenic
C18:3(
ω
-3)
5,8,11,14,17-eicosapentaenoic
EPA
C20:5(
ω
-3)
4,7,10,13,16,19-docosahexaenoic
DHA
C22:6(
ω
-3)
Common examples
Slide21Take the
hexanoic
acid previously built and make it into an unsaturated fatty acid and giveLipid number CX:Y(
ω
-
Z
)
IUPAC name
Hint: will be ____
enoic
acid as we have make a molecule with alkene and carboxylic acid functional groups
Molecular modelling
5 minutes
Activity
Slide22Hexenoic Acid
5 minutes
Activity
Slide23What is a triglyceride?
“Glyceride” = derived from the structure of glycerol
“Tri” = three
R = hydrocarbon chains – connected to the glycerol by an ester bond
glycerol
triglyceride
Slide24Join two other groups
Make a triglyceride from the
the fatty acid chain using one glycerol moleculeConsider what atoms you have leftover when the triglyceride is formed – what might they make?Molecular modelling
5 minutes
Activity
Slide25Triglyceride
5 minutes
Activity
Slide26Esterification is any reaction that produces an ester bond – acid + alcohol is a classic example
Water is also produced – hence this is known as a “condensation” reaction
Esterification
Glycerol
(alcohol)
Fatty acid
Triglyceride (ester groups)
Water
+
+
Slide27Naturally occurring triglycerides are a mixture of different fatty acid chains bonded to glycerol
Palmitic
– saturatedOleic – mono-unsaturatedLinolenic – poly-unsaturated
What is a triglyceride?
Slide28Fish oil is a complex mix of different fatty acids esterified with glycerol
Omega-3 fatty acids are poly-unsaturated fatty acids with unsaturation three bonds away from the “
omega” carbonEPA – 5,8,11,14,17 eicosapentaenoic acidDHA – 4,7,10,13,16,19 docosahexaenoic acid
Triglycerides in fish oil
Slide29Fish oil and
Croda
Crude Fish oil
Product
Fish
Slide30Croda Leek Process
Break
triglyceride into ethyl esters of individual fatty acidsTake this ethyl ester mixture and
enrich
in omega-3 fatty acid esters (EPA/DHA)
Recombine
omega-3 fatty acid esters with glycerol to make triglycerides with a high concentration of EPA and DHA
Slide31This process is conventionally done at 80
o
C and reach an equilibrium, limiting the amount of product we get.
How can we make this process more energy efficient?
How can we increase the yield of fatty acid esters?
Transesterification – Break the Triglyceride
5 minutes
Activity
Slide32Transesterification
How could we make this process more energy efficient?
How could we increase the yield of fatty acid esters?
Catalyst!
Use excess alcohol to drive equilibrium by Le
Chateliers
principle
Slide33As obtained the product is a mixture of fatty acid esters
We want a product with a high concentration of omega-3 fatty acid esters (EPA/DHA)
How could we accomplish this?You have some cards in front of you with fatty acids and their key physical properties. In groups discuss how you would separate them to increase the concentration of EPA and DHACard sort activity
15 minutes
Activity
Slide34Can you separate based on boiling point?
What effect does pressure have on boiling point? E.g. can lowering the pressure lower the boiling point – a lower boiling point is safer for manufacturing
Do you need more than one distillation step? A two step distillation could make separation easier.
Card sort activity - Hints
Activity
15 minutes
Slide35Card Sort Answers
Activity
Slide36Can you separate based on boiling point?
What effect does pressure have on boiling point? E.g. can lowering the pressure lower the boiling point – a lower boiling point is safer for manufacturing
We separate at 230ºC at 20 mBar in Stage 1 Distillation. In this case we keep the residues – those above 230ºC and discard the distillatesDo you need more than one distillation step? A two step distillation could make separation easier.
Card sort activity
Activity
Slide37After distillation at 230ºC
Activity
Slide38Can you separate based on boiling point?
What effect does pressure have on boiling point? E.g. can lowering the pressure lower the boiling point – a lower boiling point is safer for manufacturing
We separate at 230ºC at 20 mBar
in Stage 1 Distillation. In this case we keep the residues – those above 230ºC and discard the distillates
Do you need more than one distillation step? A two step distillation could make separation easier.
We distil again at 265ºC at 20
mBar
and keep the distillate cut (below 265ºC) and discard the residue (above 265ºC)
Card sort activity
Activity
Slide39Distillation at 265ºC
Activity
Slide40Distillation is the separation of liquids based on different boiling points
You should have as the final group
C
22
H
38
O
2
(Linolenic)
C
24
H
46
O2 (Erucic)C22H34O2 (EPA)C24H38
O2 (DPA)C24H36O2 (DHA)
Activity
Distillation – Enriching DHA & EPA
*DPA -
Docospentaenoate
Slide41Omega-3 enriched ethyl ester
Product
Omega 3’s
Fish oil
Omega 3’s
Gas Chromatography – GC
Before Distillation
After Distillation
Slide42HEAT
Feed
Cooling water
HEAT
Residue
Distillate
Cool
Low boiling smaller oils
High boiling larger oils
Deep Vacuum
Molecular Distillation
The reason we use thin film evaporation is the oils can degrade if held at high temperature for a long time.
The process by which they degrade is called
oxidation
Slide43Glycerolysis
– Recombination after Distillation
This process is conventionally done at 230
o
C and reach and reach an equilibrium, limiting the amount of product we get.
How can we make this process more energy efficient?
How can we increase the yield of triglycerides?
5 minutes
Activity
Slide44Glycerolysis
How can we make this process more energy efficient?
How can we increase the yield of triglycerides?
Aiming for 50-60% triglyceride in final product
Catalyst!
Distil off ethanol to drive equilibrium
Activity
Slide45Kahoot
quiz
Use you phone, tablet, laptop
Log onto
kahoot.it
Enter the number
code
which will be displayed on the screen
Click
here
to access
Activity
Slide46You are employed by Croda as a business development team. One of your objectives for this year is to increase the sales of
Croda’s
enriched omega three fish oils by 25 %. How will you achieve this? You could try one of the following: New marketing campaign Lower cost of manufacture (a barrier for some customers) New product ideas / formats (moving away from capsules) Alternative sources of EPA/DHA
Activity
20 minutes
Activity
Slide47Activity
Spend the first 5 minutes brainstorming ideas
Explore your chosen topic, the opportunities & how you are going to achieve your target as a team
Pitch your idea back to the group (you’ll only have 3 minutes!)
Slide48Objective
: Increase the sales of
Croda’s enriched omega three oils by 25 % Considerations:Who is your customer?What is the market need?How will you manufacture the product?
Cost vs. Benefit?
Activity
20 minutes
Slide49Questions & Feedback
THANK YOU