minafin group structure • pennakem’s value chain • …pennakem.com/news/pennakem presentation...

• 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