Minafin Group Structure Pennakem s Value Chain Pennkem s Offering:
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2 Minafin Group Structure Pennakem s Value Chain Pennkem s ffering: Green solvents 2-MeTHF Green specialty chemicals Forward integration in furan derivatives
3 Minafin SARL Holding Minakem SAS (F) R&D; Pilot; Small scale manufacturing CGMP; FDA Inspected Minakem Leuna GmbH (D) R&D; Pilot, Medium scale manufacturing CGMP; FDA inspected Minakem Dunkirk (F) API's Large scale manufacturing CGMP; FDA Inspected MINAKEM Pennakem (MemphisUSA) R&D; Pilot Medium/large scale manufacturing IS certified Pennakem China Furfural producer Large scale manufacturing Minasolve SAS (F) Shared infrastructure MINASLVE
4 Complexity (# of steps & regulatory capability) Workshop Minakem SAS Minakem Leuna GmbH Minakem Dunkirk SAS Assembly Line Pennakem LLC R&D; Pilot; Small Scale 10 s MT 100 s MT 1000 s MT Max. Volume
5 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 IS to CGMP Minafin Group is an end to end manufacturing outsourcing partner for the global chemical industry
6 Minafin Hldg. structure Pennakem s Value Chain Pennkem s ffering: Green solvents 2-MeTHF Green specialty chemicals Forward integration in furan derivatives
7 PharmaChem Rubber AgChem Sugar Cane H H H H H H Acid H H -3H 2 CH H H Pentoses Furfural FineChem Corn cobs Food & Cosmetics
8 Minafin Hldg. structure Pennakem s Value Chain Pennkem s ffering: Green solvents 2-MeTHF Green specialty chemicals Forward integration in furan derivatives
9 Furfural pportunistic business Green Solvents Specialty Chemicals Fit? Advanced Furan Intermediates Custom Manufacturing
10 furan tetrahydrofuran Furfural CH CH 3 methyltetrahydrofuran CH 2 H CH 2 H furfuryl alcohol tetrahydrofurfuryl alcohol
11 CH 3 CH 3 CH CH 3 3 CH CH 3 3 CH 3
12 CH 3 Adapted from Moving Towards Greener Solvents In Pharmaceutical Manufacturing ; Peter Dunn (Pfizer), Richard Henderson (GSK), Ingrid Merlgesberg (Schering-Plough) & Andrew Wells (Astra-Zeneca) Website:
13 2-MeTHF Is Better Than THF Purchasing R&D/Manufacturing Reduced costs Long term price stability Comparable/better safety Improved process Green product & process Safety Environmental
14 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
15 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 reduction 4. rganopalladium coupling 5. rganozinc chemistry 6. Biphasic reactions (DCM replacement) B. Comanita; D. Aycock, Industrie Pharma Magazine, No.17, 2005, D. Aycock, rg. Process Res. Dev. 2007,11,
16 Improved Process: physical properties 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 layers 3. Extracts better solids and/or polar products 4. 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
17 Pennakem LLC & Chemetall GmbH New Marketing Agreement 2-MeTHF Informex 2010
18 Furfural pportunistic business Green Solvents Specialty Chemicals Fit? Advanced Furan Intermediates Custom Manufacturing
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20 Furfural pportunistic business Green Solvents Specialty Chemicals Fit? Advanced Furan Intermediates Custom Manufacturing
21 Furan Derivatives H 3 C CH 3 methylpropionylfuran maleic anhydride adduct Acylation Diels Alder CH Rearrangements H furfural Bromination Br H 3 C N 5-methyl-2-ethy-3- hydroxypyridine CH 3 3-bromofuran
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