Production of hydrogen peroxide in liquid CO2. 2. Catalytic hydrogenation of CO2-philic anthraquinones

Industrial and Engineering Chemistry Research

Volumn 38, Issue 7, 1999, Pages 2833-2841

  Hâncu, Dan ^a   Beckman, Eric J ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON DIOXIDE; CATALYSTS; DIFFUSION; HYDROGEN; HYDROGENATION; KETONES; LIQUIDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; PALLADIUM; RATE CONSTANTS; REACTION KINETICS;

CATALYTIC HYDROGENATION; EFFECTIVE DIFFUSIVITIES; FUNCTIONALIZED ANTHRAQUINONES;

HYDROGEN PEROXIDE;

ANTHRAQUINONE DERIVATIVE; CARBON DIOXIDE; HYDROGEN; HYDROGEN PEROXIDE; LEAD;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CONTROLLED STUDY; HYDROGENATION; OXIDATION;

EID: 0344242070     PISSN: 08885885     EISSN: None     Source Type: Journal    
DOI: 10.1021/ie9807396     Document Type: Article

References (49)

1. Subramaniam, B.; McHugh, M. A. Reactions in Supercritical Fluids-A review. Ind. Eng. Chem. Process Des. Dev. 1986, 25, 1.
2. Tiltscher, H.; Hofmann, H. Trends in High-Pressure Chemical Reaction Engineering. Chem. Eng. Sci. 1987, 42, 959.
3. Savage, P. E.; Gopalan, S.; Mizan, T. I.; Martino, C. J.; Brock, E. E. Reactions at Supercritical Conditions: Applications and Fundamentals. AIChE J. 1995, 41, 1723.
4. (a) Baiker, A. Supercritical Fluids in Heterogeneous Catalysis. Chem. Rev. 1999, 99, 453.
5. (b) Jessop, P. G.; Ikariya, T.; Noyori, R. Homogeneous Catalysis in Supercritical Fluids. Chem. Rev. 1999, 99, 475.
6. (c) Savage, P. E. Organic Chemical Reactions in Supercritical Water. Chem. Rev. 1999, 99, 603.
7. 2. Chem. Eng. Sci. 1997, 52, 4163.
8. 2: Kinetic Measurements in a Gradientless Internal-Recycle Reactor. Ind. 'Eng. Chem. Res. 1997, 36, 2626.
9. Hitzler, M. G.; Poliakoff, M. Continuous Hydrogenation of Organic Compounds in Supercritical Fluids. Chem. Commun. 1997, 1667.
10. Yokota, K.; Fujimoto, K. Supercritical-Phase FischerTropsch Synthesis Reaction: 2. The Effective Diffusion of Reactant and Products in Supercritcal-Phase Reaction. Ind. Eng. Chem. Res. 1991, 30, 95.
11. (a) Tiltscher, H.; Wolf, H.; Schelchshorn, J. A Mild and Effective Method for the Reactivation or Maintenance of Activity of Heterogeneous Catalysts. Angew. Chem., Int. Ed. Engl. 1981, 20, 892.
12. (b) Subramaniam, B.; McCoy, B. J. Catalyst Activity Maintenance or Decay: A Model for Formation and Desorption of Coke. Ind. Eng. Chem. Res. 1994, 33, 504.
13. 2 System at Temperatures from 220 to 290 K and Pressures to 172 MPa. Chem. Eng. Sci. 1981, 36, 993.
14. Valderrama, J. D.; Cortes, F. H.; Ibrahim, A. A.; Celiker, H. Literature Survey on Solubility of Hydrogen in Liquid Solvents. Chem. Eng. Technol. 1992, 64, 750.
15. Mills, P. L.; Ramachandran, P. A.; Chaudari, R. V. Multiphase Reaction Engineering for Fine Chemicals and Pharmaceuticals. Rev. Chem. Eng. 1992; 8, 1.
16. (a) Burk, M. J.; Feng, S.; Gross, M. F.; Tumas, W. Asymmetric Catalytic Hydrogénation Reactions in Supercritical Carbon Dioxide. J. Am. Chem. Soc. 1995, 117, 8277.
17. (b) Jessop, P. G.; Ikariya, T.; Noyori, R. Selectivity for Hydrogenation or Hydroformylation of Olefins by Hydridopentacarbonylmanganese(I) in Supercritical Carbon Dioxide. Organometallics 1995, 14, 1510.
18. (c) Palo, D. R.; Erkey, C. Homogeneous Catalytic Hydroformylation of 1-octene in Supercritical Carbon Dioxide Using a Novel Rhodium Catalyst with Fluorinated Arylphosphine Ligands. Ind. Eng. Chem. Res. 1998, 37, 4203.
19. (d) Jessop, P. G.; Hsiao, Y.; Ikariya, T.; Noyori, R. Homogeneous Catalysis in Supercritical Fluids: Hydrogénation of Supercritical Carbon Dioxide to Formic Acid, Alkyl Formates, and Formamides. J. Am. Chem. Soc. 1996, 118, 344.
20. Hess, W. T. Hydrogen Peroxide. In Kirk-Othmer Encyclopedia of Chemical Technology, 4th ed.; Kroschwitz, I., Howe-Grant, M., Eds.; John Wiley & Sons: New York, 1995; Vol. 13, p 961.
21. Guenter, T. E. Hydrogen Peroxide. In Encyclopedia of Chemical Processing and Design; McKetta, J. J., Cunningham, W. A., Eds.; Marcel Dekker: New York, 1988; Vol. 27, p 27.
22. Powell, R. Hydrogen Peroxide; Noyes: Park Ridge, NJ, 1968.
23. Berglin, T.; Schöön, N. H. Kinetic and Mass Transfer Aspects of the Hydrogenation Stage of the Anthraquinone Process for Hydrogen Peroxide Production. Ind. Eng. Chem. Process Des. Dev. 1981, 20, 615.
24. Kirdin, K. K.; Franchuk, V. I.; Balabin, I Y.; Agafonova, M. I. Mathematical Model of Liquid Phase Hydrogenation of Anthraquinones. Sov. Chem. Ind. 1970, 9, 5.
25. (a) Drelinkiewicz, A. Kinetics and Mechanism of the Hydrogénation of 2-Ethyl-9,10-Anthraquinone in Liquid Phase. I. Introductory Study. Bull. Pol. Acad. Sci., Chem. 1991, 39, 63.
26. (b) Drelinkiewicz, A. Kinetics and Mechanism of the Hydrogenation of 2-Ethyl-9,10-Anthraquinone in Liquid Phase. II. The Effect of the Catalyst Concentration, Grain Size and Temperature. Bull. Pol. Acad. Sec., Chem. 1991, 39, 113.
27. Drelinkiewicz, A. Kinetics and Mechanism of the Hydrogenation of 2-Ethyl-9,10-Anthraquinone in Liquid Phase. III. Catalyst Deactivation by Hydrogénation Product and Thiophene. Bull. Pol. Acad. Sci., Chem. 1991, 39, 129.
28. Drelinkiewicz, A. Kinetics and Mechanism of the Hydrogénation of 2-Ethyl-9,10-Anthraquinone in Liquid Phase. IV. The Influence of Water Additives on the Rate of Hydrogénation. Bull. Pol. Acad. Sci., Chem. 1991, 39, 139.
29. Santacesaria, E.; Wilkinson, P.; Babini, P.; Carra, S. Hydrogenation of 2-Ethyltetrahydroanthraquinone in the Presence of Palladium Catalyst. Ind. Eng. Chem. Res. 1988, 27, 780.
30. Santacesaria, E.; Di Serio, M.; Velloti, R.; Leone, U. Kinetics, Mass Transfer, and Palladium Catalyst Deactivation in the Hydrogenation Step of the Hydrogen Peroxide Synthesis via Anthraquinone. Ind. Eng. Chem. Res. 1994, 33, 277.
31. 2-Miscible Anthraquinones. Ind. Eng. Chem. Res., in press.
32. Lide, D. R.; Kehiaian, H. V. CRC Handbock of Thermophysical and Thermochemical Data; CRC Press: Boca Raton, FL, 1994; pp 69-71.
33. 2-Soluble Chelating Agents for Removal of Metals. Ind. Eng. Chem. Res. 1996, 35, 3644.
34. 2-Soluble Chelating Agents. 2. Effect of Chelate Structure and Process Parameters on Extraction Efficienty. Ind. Eng. Chem. Res. 1997, 36, 2368.
35. Hamanque, K.; Nakayama, T.; Sasaki, H.; Ikenaga, K.; Ibuki, K. Solvent Effects on the Formation and Decay of Ionic Intermediates for the Photoreduction of Anthraquinone by Triethylamine in Ethanol, Toluene, and Acetonitrile at Room Temperature. Bull. Chem. Soc. Jpn. 1992, 65, 3141.
36. Breslin, D. T.; Schuster, G. B. Anthraquinone Photonucleases: Mechanisms for GG-Selective and Nonselective Cleavage of Double-Stranded DNA. J. Am. Chem. Soc. 1996, 118, 2311.
37. Ramachandran, P. A.; Chaudhari, R. V. Three-Phase Catalytic Reactors; Gordon and Breach, Science Publishers: New York, 1983.
38. Sano, Y.; Yamaguchi, N.; Adachi, T. Mass Transfer Coefficients for Suspended Particles in Agitated Vessels and Bubble Columns. J. Chem. Eng. Jpn. 1974, 7, 255.
39. Kamat, S. V.; Iwaskewycz, B.; Beckman, E. J.; Russell, A. J. Biocatalytic Synthesis of Acrylates in Supercritical Fluids: Tuning Enzyme Activity by Changing Pressure. Proc. Natl. Acad. Sci. U.SA. 1993, 32, 2940.
40. Minder, B.; Mallat, T.; Pickel, K. H.; Steiner, K; Baiker, A. Enantioselective Hydrogenation of Ethyl Pyruvate in Supercritical Fluids. Catal. Lett. 1995, 34, 1.
41. 2 over Palladium on Various Supports. J. Catal. 1985, 95, 567.
42. 2 over Supported Palladium. J. Catal. 1986, 98, 166.
43. Clarke, A.; Cloydlangston, J.; Thomas, W. J. An Experimental Investigation of a Copper Catalyst for the Liquid-Phase Hydrogenation of Olefins. Trans. Inst. Chem. Eng. 1977, 55, 93.
44. Akgerman, A.; Erkey, C.; Orejuela, M. Limiting Diffusion Coefficients of Heavy Molecular Weight Organic Contaminants in Supercritical Carbon Dioxide. Ind. Eng. Chem. Res. 1996, 35, 911.
45. Suva, C. M.; Macedo, E. A. Diffusion Coefficients of Ethers in Supercritical Carbon Dioxide. Ind. Eng. Chem. Res. 1998, 37, 1490.
46. Satterfield, C. N. Mass Transfer in Heterogeneous Catalysis; The Massachusetts Institute of Technology: Cambridge, MA, 1977.
47. 2 Catalyst in the Liquid Phase. J. Mol. Catal. 1992, 75, 321.
48. 2. J. Mol. Catal A 1995, 101, 61.
49. Santacesaria, E.; Di Serio, M.; Velloti, R.; Leone, U. Hydrogenation of the Aromatic Rings of 2-Ethylanthraquinone on Palladium Catalyst. J. Mol. Catal. 1994, 94, 37.