Continuous hydrogenation reactions in a tube reactor packed with Pd/C

Chemical Communications

Volumn , Issue 1, 2005, Pages 40-42

  Yoswathananont, Nungruethai ^a   Nitta, Kohei ^a   Nishiuchi, Yumi ^a   Sato, Masaaki ^a  

^a Osaka Prefecture University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; PALLADIUM;

ARTICLE; ATMOSPHERIC PRESSURE; CATALYST; CHEMICAL REACTION; CONTINUOUS FLOW REACTOR; DERIVATIZATION; DIFFUSION; FLOW KINETICS; FLUORINATION; GAS FLOW; HYDROGENATION; TUBE;

EID: 12744273350     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b410014j     Document Type: Article

References (23)

1. G. W. Kabalka and R. S. Verma, in Comprehensive Organic Synthesis, Eds. B. M. Trost and I. Fleming, Pergamon Press, Oxford, 1991, vol. 8, p. 363; P. L. Mills and R. V. Chaudhari, Catal. Today, 1997, 37, 367.
2. G. W. Kabalka and R. S. Verma, in Comprehensive Organic Synthesis, Eds. B. M. Trost and I. Fleming, Pergamon Press, Oxford, 1991, vol. 8, p. 363; P. L. Mills and R. V. Chaudhari, Catal. Today, 1997, 37, 367.
3. H. J. R. Löwenthal and E. Zass, A Guide for the Perplexed Organic Experimentalist, John Wiley, Salzburg, 1990; H. U. Blaser, H. Steiner and M. Studer, in Transition Metals for Organic Synthesis, M. Beller and C. Bolm, Eds., Wiley-VCH, Weinheim, 1998, vol. 2, p. 87.
4. H. J. R. Löwenthal and E. Zass, A Guide for the Perplexed Organic Experimentalist, John Wiley, Salzburg, 1990; H. U. Blaser, H. Steiner and M. Studer, in Transition Metals for Organic Synthesis, M. Beller and C. Bolm, Eds., Wiley-VCH, Weinheim, 1998, vol. 2, p. 87.
5. W. Ehrfeld, V. Hessel and H. Löwe, Microreactors: New Technology for Modern Chemistry, Wiley-VCH, Weinheim, 2000; W. Ehrfeld, V. Hessel and H. Lehr, Microsyst. Technol. Chem. Life Sci., 1998, 233; K. F. Jensen, Chem. Eng. Sci., 2001, 56, 293; P. D. I. Fletcher, S. J. Haswell, E. Pombo-Villar, B. H. Warrington, P. Watts, S. Y. F. Wong and X. Zhang, Tetrahedron, 2002, 58, 4735.
6. W. Ehrfeld, V. Hessel and H. Löwe, Microreactors: New Technology for Modern Chemistry, Wiley-VCH, Weinheim, 2000; W. Ehrfeld, V. Hessel and H. Lehr, Microsyst. Technol. Chem. Life Sci., 1998, 233; K. F. Jensen, Chem. Eng. Sci., 2001, 56, 293; P. D. I. Fletcher, S. J. Haswell, E. Pombo-Villar, B. H. Warrington, P. Watts, S. Y. F. Wong and X. Zhang, Tetrahedron, 2002, 58, 4735.
7. W. Ehrfeld, V. Hessel and H. Löwe, Microreactors: New Technology for Modern Chemistry, Wiley-VCH, Weinheim, 2000; W. Ehrfeld, V. Hessel and H. Lehr, Microsyst. Technol. Chem. Life Sci., 1998, 233; K. F. Jensen, Chem. Eng. Sci., 2001, 56, 293; P. D. I. Fletcher, S. J. Haswell, E. Pombo-Villar, B. H. Warrington, P. Watts, S. Y. F. Wong and X. Zhang, Tetrahedron, 2002, 58, 4735.
8. W. Ehrfeld, V. Hessel and H. Löwe, Microreactors: New Technology for Modern Chemistry, Wiley-VCH, Weinheim, 2000; W. Ehrfeld, V. Hessel and H. Lehr, Microsyst. Technol. Chem. Life Sci., 1998, 233; K. F. Jensen, Chem. Eng. Sci., 2001, 56, 293; P. D. I. Fletcher, S. J. Haswell, E. Pombo-Villar, B. H. Warrington, P. Watts, S. Y. F. Wong and X. Zhang, Tetrahedron, 2002, 58, 4735.
9. R. D. Chambers and R. C. H. Spink, Chem. Commun., 1999, 883; K. Jähnisch, M. Baerns, V. Hessel, W. Ehrfeld, V. Haverkamp, H. Löwe, C. Wille and A. Guber, J. Fluorine Chem., 2000, 105, 117.
10. R. D. Chambers and R. C. H. Spink, Chem. Commun., 1999, 883; K. Jähnisch, M. Baerns, V. Hessel, W. Ehrfeld, V. Haverkamp, H. Löwe, C. Wille and A. Guber, J. Fluorine Chem., 2000, 105, 117.
11. The Pd/C catalyst was purchased from N.E.CHEMCAT Co. (AER type).
12. The molar ratio of the dissolved hydrogen in the solution (at atmospheric pressure) to the product was approximately 1:50.
13. C. de Bellefon, N. Tanchoux, S. Caravieilhes, P. Grenouillet and V. Hessel, Angew. Chem., Int. Ed, 2000, 39, 3442; C. de Bellefon, R. Abdallah, T. Lamouille, S. Caravieilhes and P. Grenouillet, Chimia, 2002, 56, 621.
14. C. de Bellefon, N. Tanchoux, S. Caravieilhes, P. Grenouillet and V. Hessel, Angew. Chem., Int. Ed, 2000, 39, 3442; C. de Bellefon, R. Abdallah, T. Lamouille, S. Caravieilhes and P. Grenouillet, Chimia, 2002, 56, 621.
15. G. Wießmeier and D. Hönicke, Ind. Eng. Chem. Res., 1996, 35, 4412; G. Wießmeier and D. Hönicke, J. Micromech. Microeng., 1996, 6, 285.
16. G. Wießmeier and D. Hönicke, Ind. Eng. Chem. Res., 1996, 35, 4412; G. Wießmeier and D. Hönicke, J. Micromech. Microeng., 1996, 6, 285.
17. M. W. Losey, R. J. Jackman, S. L. Firebaugh, M. A. Schmidt and K. F. Jensen, J. Microelectromech. Syst., 2002, 11, 709; J. Kobayashi, Y. Mori, K. Okamoto, R. Akiyama, M. Ueno, T. Kitamori and S. Kobayashi, Science, 2004, 304, 1305.
18. M. W. Losey, R. J. Jackman, S. L. Firebaugh, M. A. Schmidt and K. F. Jensen, J. Microelectromech. Syst., 2002, 11, 709; J. Kobayashi, Y. Mori, K. Okamoto, R. Akiyama, M. Ueno, T. Kitamori and S. Kobayashi, Science, 2004, 304, 1305.
19. For reviews on the contamination of secondary amine in the catalytic hydrogenation of nitrites, see: P. Rylander, in Catalytic Hydrogenation in Organic Syntheses, Academic Press, New York, 1979, Ch 8; M. Freifelder, in Catalytic Hydrogenation in Organic Synthesis. Procedure and Commentary, Wiley-Interscience, New York, 1978, Ch 6; H. Greenfield, Ind. Eng. Chem., Prod Res. Dev., 1976, 15, 156.
20. For reviews on the contamination of secondary amine in the catalytic hydrogenation of nitrites, see: P. Rylander, in Catalytic Hydrogenation in Organic Syntheses, Academic Press, New York, 1979, Ch 8; M. Freifelder, in Catalytic Hydrogenation in Organic Synthesis, Procedure and Commentary, Wiley-Interscience, New York, 1978, Ch 6; H. Greenfield, Ind. Eng. Chem., Prod Res. Dev., 1976, 15, 156.
21. For reviews on the contamination of secondary amine in the catalytic hydrogenation of nitrites, see: P. Rylander, in Catalytic Hydrogenation in Organic Syntheses, Academic Press, New York, 1979, Ch 8; M. Freifelder, in Catalytic Hydrogenation in Organic Synthesis. Procedure and Commentary, Wiley-Interscience, New York, 1978, Ch 6; H. Greenfield, Ind. Eng. Chem., Prod Res. Dev., 1976, 15, 156.
22. Toluene derivative can be produced by the hydrogenolysis of benzylamine in the hydrogenation reaction of benzonitrile using palladium-loaded pyridyl catalyst at 100 °C and 2.9 MPa; M. B. Dines, L. Beach, P. J. DiGiacomo, M. Viejo, K. P. Callahan and C. Mesa, US Patent 4384 981, 1983.
23. Toluene derivative can be produced by the hydrogenolysis of benzylamine in the hydrogenation reaction of benzonitrile using palladium-loaded pyridyl catalyst at 100 °C and 2.9 MPa; M. B. Dines, L. Beach, P. J. DiGiacomo, M. Viejo, K. P. Callahan and C. Mesa, US Patent 4384 981, 1983.