Ionic Liquid
Presented by :Xin
Huang
Green Chemistry
Presentation
Developmen
t
Outline
Definition
Conclusion
Examples
Ionic liquid in synthesis
Advantage
Applications
What are Ionic Liquids
Common Definition
■ Ionic Liquids (ILs) is the generic term for a class of materials, consisting
entirely of ions and being liquid below 100°C.
■ If they are liquid at room temperature, we call them room temperature
ionic liquids (RTILs).
Typical Cation and Anion
Typical IL Cations
* [PF6]-
for moisture stable, water immiscible IL
* [BF4]-
for moisture stable, but water miscible IL
* [AlCl4
-
] (or other Lewis acids) decomposes in water
Discovery and History
■ * The description of a low melting point salt -
1914
■Ethyl ammonium nitrate
■ * The first room temperature ionic liquid -1951
■N-ethylpyridinium bromide- aluminium chloride melt
■ * The most stable and conductive salts -
1982
■1,3-dialkylimidazolium salts
■ * The hydrophobic ionic liquids -
1992
■1-ethyl-3-methylimidazolium tetrafluoroborate
Paul Walden
Advantage
■Easy separation
■Very low vapor pressure
■Non-flammable substance
■High thermally stable
■High mechanically stable
■Electrochemically stable
■Low toxicity
■Non-volatility
Application
Comparison of organic solvents with ionic
liquids
Plechkova, N. V.; Seddon K. R. Chem. Soc. Rev. 2008, 37, 123–150
Ionic Liquids in Organic
Synthesis
■ Catalytic
■ Hydrogenetions
■ Hydroformylations
■ Heck reactions
■ Suzuki coupling
■ Stille Coupling
Friedel–Crafts
Alkoxycarbonylation
Olefin dimerization
Diels-Alder
Oxidations
Diels-Alder reaction
Heck Reaction
Wittig reaction
Suzuki-Miyaura coupling
reaction
Stille reaction
Friedel-Crafts reaction
Hydrogenation
Fluorination
12 principles of Green
Chemistry
■ 1. Waste Prevention
■ 2. Atom Economy
■ 3. Less Hazardous Chemical Process
■ 4. Designing Safer Chemicals
■ 5. Safer Solvents and Auxiliaries
■ 6. Energy Efficiency
■ 7. Renewable Feedstocks
■ 8. Reduce Derivatives
■ 9. Catalysis
■ 10. Design for Degradation
■ 11. Real-time Analysis for Pollution Prevention
■ 12. Safer Chemistry for Accident Prevention
Journal of Fluorine Chemistry
A novel pyrrolidinium ionic liquid with 1,1,2,2
tetrafluoro 2 (1,1,2,2-tetrafluoroethoxy)
ethanesulfonate anion as a recyclable reaction
medium and efficient catalyst for Friedel–Crafts
alkylations of indoles with nitroalkenes
Jin-Hong Lin, Cheng-Pan Zhang, Zhi-Qiang Zhu, Qing-Yun Chen, Ji-
Chang Xiao *
Preparation of pyrrolidinium
salts
Reaction
Flow chart
AlCl3
Green Aspects
■ The yeild for preparing Ionic liquid is as high 99%. (Principle
2)
■ Seperation of Ionic liquid is easy , just by filtration.
■ Reaction condition is mild .(Principle 12)
■ No byproducts in the preparation .(Principle 8)
Green Aspects
■ The high concentration of highly acidic species that can be
immobilized in ionic liquids and that leads to a highly reactive
catalytic phase allowing for fast reactions under mild conditions. In
fact, acidic ionic liquids catalyze all reactions that are
conventionally catalyzed by AlCl3, but without suffering the
disadvantage of the low solubility of AlCl3 in many solvents.
(Principle #3,5,9)
■ The liquid nature of the catalytic phase eliminates the heat and
mass transfer problems frequently encountered with
heterogeneous Friedel–Crafts-catalysts and make the reaction get
high yield .(Principle 2)
■ The miscibility gap of most ionic liquids with alkylated aromatics
allows for product isolation by simple decantation.(Principle #1,7)
Green Aspects
■Ionic liquid also act as solvent in this
reaction ,it prevents the waste of solvent.
(Principle 1)
Ionic liquid can be used directly for the next
run after removing the solvent. Principle 7
Conclusion
■ Ionic liquids ,as the new materials of multifunction , are
widely used in various of fields.
■ Environmently-friendly reaction process have vigorously
been studied from the standpoint of green chemistry and
based on the properities of easy separation , low toxicity ,
selective miscibility , ILS play an important role in organic
synthesis as the green alternative solvent.
■ Withe the development of multifunctional ILS , we can
expect IlS would apply in more fields .
ionic liquid presentation for green chemistry.pptx

ionic liquid presentation for green chemistry.pptx

  • 1.
    Ionic Liquid Presented by:Xin Huang Green Chemistry Presentation
  • 2.
  • 3.
  • 4.
  • 5.
    Common Definition ■ IonicLiquids (ILs) is the generic term for a class of materials, consisting entirely of ions and being liquid below 100°C. ■ If they are liquid at room temperature, we call them room temperature ionic liquids (RTILs).
  • 6.
    Typical Cation andAnion Typical IL Cations * [PF6]- for moisture stable, water immiscible IL * [BF4]- for moisture stable, but water miscible IL * [AlCl4 - ] (or other Lewis acids) decomposes in water
  • 7.
    Discovery and History ■* The description of a low melting point salt - 1914 ■Ethyl ammonium nitrate ■ * The first room temperature ionic liquid -1951 ■N-ethylpyridinium bromide- aluminium chloride melt ■ * The most stable and conductive salts - 1982 ■1,3-dialkylimidazolium salts ■ * The hydrophobic ionic liquids - 1992 ■1-ethyl-3-methylimidazolium tetrafluoroborate Paul Walden
  • 8.
    Advantage ■Easy separation ■Very lowvapor pressure ■Non-flammable substance ■High thermally stable ■High mechanically stable ■Electrochemically stable ■Low toxicity ■Non-volatility
  • 9.
  • 10.
    Comparison of organicsolvents with ionic liquids Plechkova, N. V.; Seddon K. R. Chem. Soc. Rev. 2008, 37, 123–150
  • 11.
    Ionic Liquids inOrganic Synthesis ■ Catalytic ■ Hydrogenetions ■ Hydroformylations ■ Heck reactions ■ Suzuki coupling ■ Stille Coupling Friedel–Crafts Alkoxycarbonylation Olefin dimerization Diels-Alder Oxidations
  • 12.
  • 13.
  • 14.
  • 15.
  • 16.
  • 17.
  • 18.
  • 19.
  • 20.
    12 principles ofGreen Chemistry ■ 1. Waste Prevention ■ 2. Atom Economy ■ 3. Less Hazardous Chemical Process ■ 4. Designing Safer Chemicals ■ 5. Safer Solvents and Auxiliaries ■ 6. Energy Efficiency ■ 7. Renewable Feedstocks ■ 8. Reduce Derivatives ■ 9. Catalysis ■ 10. Design for Degradation ■ 11. Real-time Analysis for Pollution Prevention ■ 12. Safer Chemistry for Accident Prevention
  • 21.
    Journal of FluorineChemistry A novel pyrrolidinium ionic liquid with 1,1,2,2 tetrafluoro 2 (1,1,2,2-tetrafluoroethoxy) ethanesulfonate anion as a recyclable reaction medium and efficient catalyst for Friedel–Crafts alkylations of indoles with nitroalkenes Jin-Hong Lin, Cheng-Pan Zhang, Zhi-Qiang Zhu, Qing-Yun Chen, Ji- Chang Xiao *
  • 22.
  • 23.
  • 24.
  • 25.
    Green Aspects ■ Theyeild for preparing Ionic liquid is as high 99%. (Principle 2) ■ Seperation of Ionic liquid is easy , just by filtration. ■ Reaction condition is mild .(Principle 12) ■ No byproducts in the preparation .(Principle 8)
  • 26.
    Green Aspects ■ Thehigh concentration of highly acidic species that can be immobilized in ionic liquids and that leads to a highly reactive catalytic phase allowing for fast reactions under mild conditions. In fact, acidic ionic liquids catalyze all reactions that are conventionally catalyzed by AlCl3, but without suffering the disadvantage of the low solubility of AlCl3 in many solvents. (Principle #3,5,9) ■ The liquid nature of the catalytic phase eliminates the heat and mass transfer problems frequently encountered with heterogeneous Friedel–Crafts-catalysts and make the reaction get high yield .(Principle 2) ■ The miscibility gap of most ionic liquids with alkylated aromatics allows for product isolation by simple decantation.(Principle #1,7)
  • 27.
    Green Aspects ■Ionic liquidalso act as solvent in this reaction ,it prevents the waste of solvent. (Principle 1) Ionic liquid can be used directly for the next run after removing the solvent. Principle 7
  • 28.
    Conclusion ■ Ionic liquids,as the new materials of multifunction , are widely used in various of fields. ■ Environmently-friendly reaction process have vigorously been studied from the standpoint of green chemistry and based on the properities of easy separation , low toxicity , selective miscibility , ILS play an important role in organic synthesis as the green alternative solvent. ■ Withe the development of multifunctional ILS , we can expect IlS would apply in more fields .