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• Minafin Group Structure• Pennakem’s Value Chain• Pennkem’s Offering:
– Green solvents • 2-MeTHF
– Green specialty chemicals– Forward integration in furan derivatives
Minakem SAS (F)R&D; Pilot;
Small scale manufacturingCGMP; FDA Inspected
Minakem Leuna GmbH (D)R&D; Pilot,
Medium scale manufacturingCGMP; FDA inspected
Minakem Dunkirk (F)API's
Large scale manufacturingCGMP; FDA Inspected
Pennakem ChinaFurfural producer
Large scale manufacturing
Pennakem (MemphisUSA)R&D; Pilot
Medium/large scale manufacturingISO certified
Minasolve SAS (F)Shared infrastructure
Minafin SARLHolding
MINAKEM MINASOLVE
Minakem LeunaGmbH
Complexity(# of steps & regulatory capability)
Max. Volume
Minakem SAS
10’s MT 100’s MT 1000’s MT
Pennakem LLC
Minakem Dunkirk
SAS
Workshop
AssemblyLine
R&D; Pilot; Small Scale
• Minafin group is a highly diversified group:• Geographically
– Global footprint (Europe, USA)• Across molecule complexities
– Basic advanced intermediates actives• Across client industry focus
– Pharmaceutical, cosmetics & food, industrials, agrochem• Across scale
– From laboratory to pilot to large scale• Across regulatory
– From ISO to CGMP• Minafin Group is an end to end manufacturing outsourcing partner
for the global chemical industry
• Minafin Hldg. structure• Pennakem’s Value Chain• Pennkem’s Offering:
– Green solvents • 2-MeTHF
– Green specialty chemicals– Forward integration in furan derivatives
O
HOH
HH
OHH
OH H
OH
H
AcidSugar Cane
Corn cobs
Pentoses Furfural
PharmaChem
Rubber
AgChem
FineChem
Food &Cosmetics
- 3H2O OCHO
• Minafin Hldg. structure• Pennakem’s Value Chain• Pennkem’s Offering:
– Green solvents • 2-MeTHF
– Green specialty chemicals– Forward integration in furan derivatives
Furfural
Specialty Chemicals
Green Solvents
Advanced FuranIntermediates
CustomManufacturing
Fit?
Opportunisticbusiness
O CHO
Furfural
furan tetrahydrofuran
O O
methyltetrahydrofuran
O CH3
furfuryl alcohol tetrahydrofurfuryl alcohol
O CH2OH OCH2OH
O CH3O CH3
O CH3O CH3
O CH3O CH3O CH3
O CH3O CH3O CH3
O CH3O CH3O CH3
O CH3
• Adapted from “Moving Towards Greener Solvents In Pharmaceutical Manufacturing” ; Peter Dunn (Pfizer), Richard Henderson (GSK), Ingrid Merlgesberg (Schering-Plough) & Andrew Wells (Astra-Zeneca)
• Website: www.acs.org/gcipharmaroundtable
2-MeTHF Is Better Than THF
Reduced costs Improved process
Green product& process
Comparable/better safety
Purchasing R&D/Manufacturing
Safety Environmental
Long term price stability
MeTHF versus THF Improves Processes
• Advantages from chemical properties– Increased reaction yields– Increased stereo and regio selectivity
• Regioselectivity• Diastereoselectivity • Enantioselectivity
– Less impurities due to higher stability than THF
• Advantages from physical properties
Improved Process: Chemical Properties
• MeTHF better yields and more versatile than THF!
1. Mg/Cu • Regioselective from 1,2 &1,4 additions• Enantio, diastereoselective reactions
2. Lithiation 3. Hydride based reduction4. Organopalladium coupling5. Organozinc chemistry6. Biphasic reactions (DCM replacement)
B. Comanita; D. Aycock, Industrie Pharma Magazine, No.17, 2005, 54-56D. Aycock, Org. Process Res. Dev. 2007,11,156-159
• MeTHF is the solution to THF’s shortcomings:
1. MeTHF is not miscible with water• Eliminates second solvent or saline solution• Less solvent
2. Clean phase separation with no emulsions & rag layers3. Extracts better solids and/or polar products4. Higher solubility of extract
• Reduced number of extraction steps• Less solvent
5. Easy to dry (forms azeotrope like toluene)6. Easy to recycle and reuse
Improved Process: physical properties
Pennakem LLC & Chemetall GmbH
New Marketing Agreement2-MeTHF
Informex 2010
Furfural
Specialty Chemicals
Green Solvents
Advanced FuranIntermediates
CustomManufacturing
Fit?
Opportunisticbusiness
Furfural
Specialty Chemicals
Green Solvents
Advanced FuranIntermediates
CustomManufacturing
Fit?
Opportunisticbusiness
Furan Derivatives
maleic anhydride adduct
furfural
O CHO
Diels Alder
OO
O
O
3-bromofuran
O
Br
methylpropionylfuran
OCH3 CH3
O
5-methyl-2-ethy-3-hydroxypyridine
N
OH
CH3CH3
Acylation
RearrangementsBromination
