SACHEM Inc'

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SACHEM Inc. Ionic Liquid Solvents
Willy Wilson Manager, Technical Service SACHEM,
Inc.
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SACHEM Ionic Liquids

• Rosemary Hoffman, Marketing Manager
• Dr. Roger Moulton, Tech. Development Mgr.
• Willy Wilson, Technical Service Manager

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Ionic Liquids
Ionic Liquids Salts that are liquid at ambient
temperatures -New Class of Solvents -Cation and
anion can be tailored to specific application -No
Vapor Pressure (no VOCs) -Non-flammable -Unique
Properties -Enable Opportunities
for new or improved processes
Separations, Reuse and Recycle
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Ionic Liquids are Salts with Asymmetric Organic
Cations
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Research Projects Involving Ionic Liquids are
Increasing
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Three Classes of Ionic Liquids

• Lewis Acidic catalytic
• contain AlCl3, ZnCl2, InCl3, FeCl3, CuCl2, etc
• Hydrophobic
• most common is 1-butyl-3-methylimidazolium
  hexafluorophosphate (BMIM PF6)
• water immiscible
• can be polar or non polar
• Hydrophilic
• water soluble

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Polarity of Ionic Liquids Span the Range of
Conventional Solvents

• Test uses Reichardts Dye spectrum to measure
  solvent polarity
• Values normalized to water 1.0 and hexane 0.0

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Viscosity of Ionic Liquids is Higher Than Most
Solvents
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Ionic Liquids in Liq/Liq Extraction
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Ionic liquids
Examples of reactions in Ionic Liquids u Diels-A
lder cycloadditions u Friedel-Crafts
u Esterifications u Hydroformylation u Hydrodimer
ation u N or O alkylation u Oxidations u Reductio
ns u Hydrogenations u Heck coupling reactions
C-C bond forming u Suzuki Cross-Coupling u Copper
catalyzed C-C/C-O bond formation u Enzymatic
reactions
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Lipase Activity in Ionic Liquids
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Heck Reaction in Ionic Liquid Media
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Heck Reaction in 3-phase Reaction Mixture

• Top layer is alkane
• brings in substrate
• carries away product
• Bottom layer is catalyst in Ionic Liquid
• Middle layer is water
• washes out inorganic byproducts

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Sachems Family of Next Generation Ionic Liquids

• Terrasail
• hydrophobic
• nonfluorinated
• miscible with hydrocarbons
• Marisail
• hydrophilic
• low halide content
• Catasail
• acidic/catalytic
• less corrosive and less expensive than
  traditional catalytic ionic liquids
• 1-Butyl-3-methylimidazolium PF6 (BMIM PF6)

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Reuse and Recycle

• Reuse Phase separation, extraction of products,
  distillation, etc
• Recycle/Regeneration possible
• Sachem has active program and patented toolbox
  for recycle of quaternary ammonium compounds

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Why Sachem?

• Chemical Science company specializing in
• High purity onium salts and hydroxides
• Commercial volumes
• Finding system solutions
• Markets
• Electronics
• Life Sciences
• Polymers and Catalysts
• Petrochemical

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Sachems Ionic Liquids Program

• Samples available in all classes
• TerrasailTM, MarisailTM, CatasailTM
• Sachem is continuing development on recycle
• Large scale production capability
• IL expertise