Markets We Serve Croda’s - PowerPoint Presentation

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Markets We Serve

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Croda’s

customers

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What 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

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Fish oil and Croda

Crude Fish oil

Product

Extraction of fish oil from fish

Fish

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Card 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

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Card 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

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Fish 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

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Unsaturated VS Saturated

Double Bond

Single Bond

Unsaturated

Saturated

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Fish 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

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Glycerol

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

Slide12

Molecular 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

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Glycerol

5 minutes

Activity

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Fatty 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

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Common 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

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Molecular 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

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Hexanoic Acid

5 minutes

Activity

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Shorthand 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?

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C

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- _ )

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Systematic 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

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Take 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

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Hexenoic Acid

5 minutes

Activity

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What 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

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Join 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

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Triglyceride

5 minutes

Activity

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Esterification 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

+

+

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Naturally occurring triglycerides are a mixture of different fatty acid chains bonded to glycerol

Palmitic

– saturatedOleic – mono-unsaturatedLinolenic – poly-unsaturated

What is a triglyceride?

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Fish 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

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Fish oil and

Croda

Crude Fish oil

Product

Fish

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Croda 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

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This 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

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Transesterification

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

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As 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

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Can 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

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Card Sort Answers

Activity

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Can 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

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After distillation at 230ºC

Activity

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Can 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

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Distillation at 265ºC

Activity

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Distillation 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

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Omega-3 enriched ethyl ester

Product

Omega 3’s

Fish oil

Omega 3’s

Gas Chromatography – GC

Before Distillation

After Distillation

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HEAT

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

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Glycerolysis

– 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

Slide44

Glycerolysis

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

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Kahoot

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

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You 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

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Activity

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!)

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Objective

: 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

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Questions & Feedback

THANK YOU