1. Green Chemistry Presentation
Ionic Liquid
Presented by :Xin Huang

2. Development

3. Ionic liquid in synthesis
Outline
Definition
Advantage
Applications
Ionic liquid in synthesis
Examples
Conclusion

4. What are Ionic Liquids

5. 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).

6. 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

7. Discovery and History Paul Walden
* The description of a low melting point salt
Ethyl ammonium nitrate
* The first room temperature ionic liquid
N-ethylpyridinium bromide- aluminium chloride melt
* The most stable and conductive salts
1,3-dialkylimidazolium salts
* The hydrophobic ionic liquids
1-ethyl-3-methylimidazolium tetrafluoroborate

8. Advantage Easy separation Very low vapor pressure
Non-flammable substance
High thermally stable
High mechanically stable
Electrochemically stable
Low toxicity
Non-volatility

9. Application

10. Comparison of organic solvents with ionic liquids
Plechkova, N. V.; Seddon K. R. Chem. Soc. Rev. 2008, 37, 123–150

11. Ionic Liquids in Organic Synthesis
Friedel–Crafts
Alkoxycarbonylation
Olefin dimerization
Diels-Alder
Oxidations
Catalytic
Hydrogenetions
Hydroformylations
Heck reactions
Suzuki coupling
Stille Coupling

12. Diels-Alder reaction

13. Heck Reaction

14. Wittig reaction

15. Suzuki-Miyaura coupling reaction

16. Stille reaction

17. Friedel-Crafts reaction

18. Hydrogenation

19. Fluorination

20. 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

21. 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 *

22. Preparation of pyrrolidinium salts

23. Reaction

24. Flow chart
AlCl3

25. 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)

26. 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)

27. 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

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 .

29. Thank you