Gfs chemicals   organic capabilities 2010
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  • Many reactions are Palladium or Copper catalyzed.
  • Many reactions are Palladium or Copper catalyzed.
  • Terminal Alkynes, Internal Alkynes, Alkynols, Amines (Ammonia to bromo alkane)
  • Alkylate across diphenylmethane (diphenylalkanes), Birch reductions, trans-olefins (Cis done through palladium catalysis), alkylation of nitriles
  • Terminal alkynes – Bromoalkane & Na/Li acetylide, Terminal alkynes & ethylene oxide (3-yn-1-ol), Na/Li acetylide & Bromochloroalkane, Acetylene & epichlorohydrin to make 2-en-4-yn-1-ols, dibromoalkane & acetylene SLA gives alpha-omega diynes.
  • Aldehydes(Triethylorthoformate), Ketones(from amide), Esters(chloroformate coupling, alcohols (ethlyene oxide for 3-yn-1-ols)
  • Symmetric and asymmetric diynes. Alkynyl grignards (displacement of alkane with acetylene), organometallic diyn (lithium) for further addition
  • Scores of heterocycles can be made using acetylenes. See detailed technical acetylenic presentation for more info.
  • Alkyl lithium and alkyl Magnesium halides. Chain lengthening of alkanes. Addition to aryl ring, alkynyl grignards for addition, Blocked alcohol addition
  • Dimethylformamide + alkyl lithium or Alkyl MgX (adds across carbonyl, hydrolysis splits out dimethylamine) or Triethylorthoformate + alkyl lithium or Alkyl MgX – displace two ethyl group through reaction and hydrolysis, paraformaldehyde and addition across carbonyl by alkyl lithium or grignard, michael addition for ene one (unsaturated ketone), substituded phenyl addition
  • Aldehydes, Ketones, Esters, alcohols (ethlyene oxide for 3-yn-1-ols)
  • Many reactions are Palladium or Copper catalyzed.

Transcript

  • 1. ISO 9001:2008 Certified U.S. Based Manufacturing Since 1928
  • 2. www.GFSChemicals.com Leaders in Small Molecule Building Blocks Shipping/Receiving Columbus, OH Manufacturing Complex
  • 3. Why Source from GFS?
    • Manufacturer, since 1928
      • ISO certified; non-cGMP
    • Depth and diversity of core product lines
    • Support for Research -> Commercial volumes
    • Support for custom specifications and products
    www.GFSChemicals.com Leaders in Small Molecule Building Blocks
  • 4. Equipment Capabilities and Scale (Organic Division)
    • Kilo Lab Scale
      • Glassware up to 72 L scale
      • Distillation support up to 50L scale
        • Short path
          • Bench Strip
          • Rotary Evaporators
        • Long path
          • 18” to 48” packed columns
          • Stainless, Hastelloy, Ceramic packing
    www.GFSChemicals.com Leaders in Small Molecule Building Blocks
    • Pilot Scale
      • 10 gal – 100 gal glass lined steel
      • 10 gal – 200 gal Stainless
      • Distillation Support
        • Rotary Evaporator
        • 30 gal – 50 gal glass lined steel distillation pots
          • 4’ to 12’ columns
          • Glass & stainless packing
  • 5. Equipment Capabilities and Scale (Organic Division)
    • Plant Scale
      • 350-500 gal Hastelloy
      • 100-1000 gal Glass
      • 200-1000 gal Stainless
      • Distillation support
        • Short path
          • 50 gal-500 gal glass lined
        • Long path
          • 4’ to 16’ column
          • Stainless, Hastelloy, Glass packing
      • Solids Handling
        • Hastelloy and Stainless centrifugation
    www.GFSChemicals.com Leaders in Small Molecule Building Blocks
    • Plant Scale Supports
      • Vacuum capabilities to < 10 Torr
      • Pressure handled to < 100 psi
      • Reaction conditions controlled from -40 o C to +140 o C
      • Distillation conditions controlled from 20 o C to 250 o C
      • Scrubbing supports for acid/base, ammonia and sulfide
      • Nitrogen used as inerting atmosphere
  • 6. Core Organic Technologies
    • Reactions in Liquid Ammonia
    • Acetylene Reactions
    • Alkyne Chemistry
    • Organometallic Chemistry (Mg, Li, Na)
    • Halogen Chemistry (Cl, Br, I)
    • Heteroaromatic Compounds
    www.GFSChemicals.com Leaders in Small Molecule Building Blocks
  • 7.
    • RC CH RC CR '
    • RC CCCOH RNH 2
    Liquid Ammonia www.GFSChemicals.com Leaders in Small Molecule Building Blocks NH 3
  • 8. Liquid Ammonia
    • CC n
    • Z
    • n=2 to 7
    • R
    • CCCN
    • R
    www.GFSChemicals.com Leaders in Small Molecule Building Blocks NH 3
  • 9. Acetylene Reactions
    • HC CR HC CC 2 OH HC CC n Cl
    • HC CC n C CH RC CC CCOH
    www.GFSChemicals.com Leaders in Small Molecule Building Blocks HC CH
  • 10. Alkyne Chemistry
    • RC CCHO RC CC(O)R 1
    • RC CCO 2 R 1
    • RC CCO 2 H
    • RC CCOH RC CC 2 OH
    www.GFSChemicals.com Leaders in Small Molecule Building Blocks RC CH
  • 11. Alkyne Chemistry
    • RC CC CR RC CC CR’
    • RC CC n X RC CC n C CC m X
    www.GFSChemicals.com Leaders in Small Molecule Building Blocks RC CH
  • 12. Alkyne Chemistry www.GFSChemicals.com Leaders in Small Molecule Building Blocks RC CH Benzofurans Indoles Isocoumarins Isoquinolines Pyrimidines Furopyridines
  • 13. Organometallics (Mg, Li, Na)
    • R R’ Ar R
    • (Ar)
    • RC CR’ R(CH2) n OTHP
    www.GFSChemicals.com Leaders in Small Molecule Building Blocks RMgX RLi
  • 14. Organometallics (Mg, Li, Na)
    • RCHO RCCOH
    • Z
    • E O R’
    • R’ CC CR
    www.GFSChemicals.com Leaders in Small Molecule Building Blocks RMgX RLi
  • 15. Halogen Chemistry (Cl, Br, I)
    • RCC CCBr CH 3
    • CH 3 CCH 2 I
    • CH 3
    • I
    • Br(CH 2 )Cl
    www.GFSChemicals.com Leaders in Small Molecule Building Blocks Cl, Br, I
  • 16. Heteroaromatic Chemistry
    • Phenanthrolines
    • Quinolines
    • Bipyridines
    • Terpyridines
    • Pyrimidines
    www.GFSChemicals.com Leaders in Small Molecule Building Blocks Pyridines Phenylenediamines Acetylenes
  • 17. Core Organic Synthetic Methods Performed at GFS
    • Acetylene Chemistry
    • Halogenation
    • Dehydrohalogenation
    • Alkylation(NH 3 )
    • Sonogashira Reactions
    • Kumada Couplings
    • Cadiot-Chodkiewicz
    • Suzuki Coupling
    • Trans Reductions(NH 3 )
    • Diels-Alder Synthesis
    • Ethynylation
    • Barbier Reaction
    • Skraup Synthesis
    • Birch Reduction
    • Heck Reaction
    • Grignard/Alkyl Lithium Synthesis
    • Finklestein Reaction
    • Phase Transfer
    www.GFSChemicals.com Leaders in Small Molecule Building Blocks
  • 18. Reagents Handled Routinely at GFS in > 100 kg Quantities
    • Acetylene
    • Ammonia,liq.
    • Alkyllithium
    • Carbon disulfide
    • Chloroformates
    • Chlorosulfonic acid
    • Epichlorohydrin
    • Ethylene oxide
    • Bromine
    • Lithium amide
    • Lithium metal
    • Magnesium
    • Sodium amide
    • Sodium hydride
    • Sodium metal
    • Trialkylsilanes
    • Iodine
    • Hydrogen Chloride
    www.GFSChemicals.com Leaders in Small Molecule Building Blocks