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Isfahan University of Technology Department of Chemistry

Isfahan University of Technology Department of Chemistry Continuous Synthesis of Diethyl Ether from Sub and Supercritical Ethanol in the Presence of Homogeneous Catalysts By : H. Rastegari Supervisor : Prof. H. S. Ghaziaskar Advisor : Prof. M. Yalpani. Contents Introduction.

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Isfahan University of Technology Department of Chemistry

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  1. Isfahan University of TechnologyDepartment of Chemistry Continuous Synthesis ofDiethyl Ether from Sub and Supercritical Ethanol in thePresence of Homogeneous Catalysts By : H. Rastegari Supervisor : Prof. H. S. Ghaziaskar Advisor : Prof. M. Yalpani

  2. Contents • Introduction Supercritical Fluid Definition • Supercritical Fluid Properties • Supercritical Fluids Classification • Supercritical Fluid Selection for Chemical Reactions • Supercritical Ethanol Properties • Supercritical Ethanol Applications 1

  3. Experimental Section • Instrumentation • Diethyl Ether Determination • Diethyl Ether Identification • Effective Parameters on The Reaction • Conclusion • Providence 2

  4. Supercritical Fluid Definition 3

  5. Supercritical Fluid Properties 4

  6. Supercritical Fluids Classification • Non-associating Fluids • Associating Fluids 5

  7. Supercritical Fluid Selection for Chemical Reactions • Critical Temperature and Pressure • Solvent Strength • Corrosion • Toxicity Supercritical Ethanol 6

  8. Supercritical Ethanol Properties Critical Temperature and Pressure 7

  9. Density 8

  10. Viscosity 9

  11. Diffusion Coefficient 10

  12. Dielectric Constant 11

  13. Hydrogen Bonding 12

  14. 13

  15. 14

  16. Kamlet-Taft Solvent Parameters: • Polarity / Polarizability (π ∗) • Hydrogen-Bond Donating Acidity (α) • Hydrogen-Bond Accepting Basicity (β) Polarity 15

  17. Polarity / Polarizability (π ∗) 16

  18. Hydrogen-Bond Donating Acidity (α) 17

  19. Hydrogen-Bond Accepting Basicity (β) 18

  20. Supercritical Ethanol Applications • Biodiesel Production • Chemical Reaction • Extraction • Micro and Nano Particle Formation • Drying 19

  21. Experimental Section 20

  22. Instrumentation 21

  23. Diethyl Ether Determination Carrier Gas: Nitrogen ( %99.999) Column Type: Capillary (HP-5) Injector Temperature : 230 oC Detector Temperature : 250 oC Temperature Program : Column Primary Temperature : 40 oC Column Hold Time at 40 oC : 2 min Temperature Increasing Rate: 30 oC/min Final Temperature : 250 oC Hold Time at 250 oC : 5 min 22

  24. Diethyl Ether Ethanol 23

  25. 24

  26. Diethyl Ether Identification 25

  27. Effective Parameters on The Reaction: Temperature Flow Rate Catalyst Concentration Pressure Catalyst Type 26

  28. Temperatureand Flow Rate Effect • Catalyst : PTSA 2(%w/v) • Pressure : 80 bar • Temperature : (100-300) oC • Flow Rate : (0.1-0.7) mL/min 27

  29. Ethanol Conversion 28

  30. Diethyl Ether Selectivity 29

  31. Diethyl Ether Yield 30

  32. 31

  33. Catalyst Concentration Effect Temperature : 200 oC Flow Rate : 0.1 mL/min Pressure : 80 bar PTSA Concentration : 2-4 (%w/v) 32

  34. Pressure Effect Temperature : 200 oC Flow Rate : 0.1 mL/min PTSA Concentration : 2 (%w/v) Pressure : (60-80) bar 33

  35. Catalyst Type Temperature : 200 oC Flow Rate : 0.1 mL/min Pressure : 80 bar Catalyst Concentration : 2 (%w/v) 34

  36. Conclusion • Synthesis of Diethyl Ether in Sub and Supercritical Ethanol inThe Presence of Para Toluene Sulfonic Acid and Sulfuric Acid. • Maximum Yield with Para Toluene Sulfonic Acid: %60 • Maximum Yield with Sulfuric Acid: %75 35

  37. Providence • Synthesis of Other Alkyl Ethers • Diethyl Ether Synthesis in The Presence of Heterogeneous Catalysts • Diethyl Ether Separation from Ethanol 36

  38. Thanks for Your Attention

  39. Page 5 dG = ( u2-u1) dn u = (dG/ dn)T,P

  40. Page 6 the transition-state theory rate constant : or One could also develop an alternate expression for the transition-state theory rate constant that employs fugacity coefficients rather than activity coefficients. This alternate form of the rate constant is convenient to use whenan accurate analytical equation of state is available for the fluid phase.

  41. Page 8

  42. Page 25 Swine Manure Bio-oil T = 240-360 oC and P= 34.47 MPas and Purge with N2 30 gr waste + 120 gr ethanol Solid + Bio-oil +Liquid Bio-oil + Liquid Bio-oil Filter Distillation at 60 oC

  43. Page 25 Depolymerization of PET T= 543 – 573 K and P= 0.1 – 15 MPas These products were produced by the methanolysis ethanolysis or hydrolysis of the ester bond between TPA and EG.

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