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© 2014 Biotage 1
Designed polymers for purification of flavor oils IFEAT Conference 2014 Rome, September 23, 2014 Ecevit Yilmaz, PhD Global Product Manager – Industrial Resins MIP Technologies AB – a subsidiary of Biotage AB [email protected]
© 2014 Biotage 2
» The company
» Separation techniques
» Chromatography, adsorbents and selective separations
» Case study: selective pesticide removal from lemon oil
» Summary
Overview of the presentation
© 2014 Biotage 3
About Biotage and MIP Technologies
© 2014 Biotage 4
Where we are
Charlotte Lund
Cardiff
Shanghai
Tokyo
Legend Sales office
Production and R&D
Uppsala Corporate headquarter
Nearly 300 employees – ca 500 M SEK turnover
© 2014 Biotage 5
» Founded in 2000, Lund Sweden
» Acquired by Biotage AB in 2010
» Total of 12 chemists (9 PhD)
» R&D team to develop novel adsorbents
» Full analytical lab to test and QC
» Pilot plant to scale-up and manufacture
MIP Technologies Experts in polymeric adsorbents
» Activities:
» Polymeric adsorbents
» Development of new adsorbents and applications
» Problem solving service for customers:
» High success rate (~ 75 %) in conducted projects
» Worked with many of top 100 companies
» ~ 15 years in the business
© 2014 Biotage 6
» The company
» Separation techniques
» Chromatography, Adsorbents and Selective separations
» Case study: Selective pesticide removal from lemon oil
» Summary
Overview of the presentation
© 2014 Biotage 7
» Separations/Purifications basically have 2 goals:
» 1) to remove unwanted substances
» Example: remove toxic or allergenic from complex mixtures
» 2) to recover a desired substance
» Example: extract a valuable compound from a mixture
» Selectivity is the ability to distinguish one molecule from other molecules
» Target compound
» Other compounds etc
» Adsorbent = Polymer = Resin
Separations and purifications
© 2014 Biotage 8
» Distillation
» By volatility
Separation techniques A few generic examples
» Membranes /Filtration
» By permeability
© 2014 Biotage 9
Separation techniques
» Liquid/Liquid Extraction
» By solubility
» Precipitation / Re-crystallisation
» By solubility
© 2014 Biotage 10
» The company
» Separation techniques
» Chromatography, Adsorbents and Selective separations
» Case study: Selective pesticide removal from lemon oil
» Summary
Overview of the presentation
© 2014 Biotage 11
Chromatography By reversible surface interactions
Colu
mn
1 2
Typical adsorbent properties
Particle size ~ 100 µm
Pore size ~ 100 Å
Pore volume ~ 0.5 ml/g
Surface area ~ 500 m2/g
Cross-linking ~ 50 %
Ligand density ~ 0.5 mmol/g
10 mm
Adsorbent
© 2014 Biotage 12
Adsorbent surface landscape
Imprinted
+ + +
+ +
Reversed Phase Ionic/Polar Affinity
Selectivity
+
-
Designed
O
Non-selective materials (hydrophobic, ionic/polar): wide-spread general use. For difficult separations, selective materials are needed: Affinity, imprinted adsorbents, designed adsorbents...
In general: non-selective materials are cheap, selective materials cost more Most affinity materials are fragile (biological molecules as ligands)
© 2014 Biotage 13
» Resolution of difficult-to-separate compounds
» Selective removal of unwanted contaminants
» Targeted recovery or enrichment of valuable compounds
» Cumbersome purifications with many or large columns
Potential of selective adsorbents
» Replacing distillation or liquid-liquid extraction
» Energy consumption, purity, contaminants…
» Avoiding undesired chemicals e.g. salts,
flammable organic solvents or toxic chemicals
» Green chemistry…
© 2014 Biotage 14
» The company
» Separation techniques
» Chromatography, Adsorbents and Selective separations
» Case study: Selective pesticide removal from lemon oil
» Summary
Overview of the presentation
© 2014 Biotage 15
Important ingredient in
» Food industry
» Drinks industry
» Fragrances
» Etc…
Citrus flavor oils
Extracted from the peel
Flavor oils may be contaminated with agricultural residues
© 2014 Biotage 16
Pesticides in lemon oil
• Toxic: similar to nerve agents (e.g. sarin) • Many pesticides have a thiophosphoester moiety • Present at ppm levels
© 2014 Biotage 17
» Distillation and other standard unit operations cannot always remove the pesticides well
» Pesticides and lemon oil constituents are chemically similar (e.g. vapor pressure)
» Heat may influence aroma / taste profile
» Standard adsorbents do not exhibit sufficient selectivity
Development of a selective adsorbent to remove pesticides without affecting key aroma molecules
Selective pesticide removal
© 2014 Biotage 18
Adsorbent library
2500 candidates
Screen
Hit Adsorbent
How to find the best adsorbent?
Application Note
• ------
• ------
Method opt.
Extraction Method
Material opt.
© 2014 Biotage 19
Adsorbent surface chemistries
B
OH
OH
NH
NHO
R
OH
O
N
Acidic/ Anionic
Basic/ Cationic
Neutral/ hydrophilic
Neutral/ hydrophobic
S
O
O
OH S
O
O
OH
N
O
N+
Cl-
OH
NH2
O
N
HN
N
O
N
N
NH2
Adsorbents have combinations of chemistries…
© 2014 Biotage 20
Outcome of a screening example Using the MIP Tech adsorbent library
0.0
10.0
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110.0E
A0
01
EA
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Phase
% B
ou
nd
© 2014 Biotage 21
» Material morphology
» Pore size
» Surface area
» Pore volume
» Bead size
» Rigidity
Adsorbent design & optimisation
Surface chemistry
Interaction design
Ligand density
Binding site design
+
-
O
© 2014 Biotage 22
Optimised designed adsorbent Pesticide clean-up in one step
Citrus oil containing pesticides
RENSA™ 101 column
© 2014 Biotage 23
Selective pesticide removal
Selective extraction of pesticides without extracting vital matrix components
GC-MS scan
© 2014 Biotage 24
Unaffected color, flavor and aroma
The cleaned-up lemon oil passed all sensory tests with no impact on the oil quality
© 2014 Biotage 25
» The company
» Separation techniques
» Chromatography, Adsorbents and Selective separations
» Case study: Selective pesticide removal from lemon oil
» Summary
Overview of the presentation
© 2014 Biotage 26
» Pressure from regulation will force raw material producers and users to evaluate new technologies
» New agricultural residues or other contaminants
» New knowledge about problematic natural constituents
» Separation techniques have pros and cons
» Distillation is versatile & established but energy demanding
» Old techniques may be expensive and less efficient
» Many techniques do not deliver sufficient selectivity
» Choosing the right adsorbent + method may be a challenge
» Novel adsorbents could improve or lead to new quality of essential oils and economics of processing
Summary
