On the quantitative recycling of Raney–Nickel catalysts on a lab-scale

Green Chemistry

Volumn 9, Issue 11, 2007, Pages 1163-1165

  Czaplik, Waldemar M ^a   Neudörfl, Jörg M ^a   von Wangelin, Axel Jacobi ^a  

^a UNIVERSITY OF COLOGNE   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 35648970527     PISSN: 14639262     EISSN: 14639270     Source Type: Journal    
DOI: 10.1039/b708057c     Document Type: Article

References (26)

1. For reviews and monographs on catalyst recovery strategies, see: Thematic Issue: Recoverable Catalysts and Reagents; J. A. Gladysz Ed.; Chem. Rev. 2002, 102, No. 10.
2. C. C. Tzschucke C. Markert W. Bannwarth S. Roller A. Hebel R. Haag Angew. Chem., Int. Ed. 2002 41 3964-4000.
3. D. J. Cole-Hamilton Science 2003 299 1702-1706.
4. Catalyst Separation, Recovery and Recycling: Chemistry and Process Design, ed. D. J. Cole-Hamilton and R. P. Tooze, Springer, 2006.
5. For selected examples of magnetically recoverable catalysts, see: A. Hu G. T. Yee W. Lin J. Am. Chem. Soc. 2005 127 12486-12487.
6. C. M. White K. L. Jensen P. C. Rohar J. P. Tamilia L. J. Shaw R. F. Hickey Energy Fuels 1996 10 1067-1073.
7. W. Teunissen A. A. Bol J. W. Geus Catal. Today 1999 48 329-336.
8. T. Osawa, in Modern Organonickel Chemistry, ed. Y. Tamaru, Wiley-VCH, Weinheim, 2005, p. 273.
9. M. S. Wainwright, in Handbook of Heterogeneous Catalysis, ed. G. Ertl, H. Knözinger and J. Weitkamp, VCH, Poitiers, 1997, p. 64.
10. M.-A. Flyvholm G. D. Nielsen A. Andersen Z. Lebens. Unters. Forsch. 1984 179 427-431.
11. Handbook on the Toxicology of Metals, ed. L. Friberg, G. F. Nordberg and V. B. Vouk, Elsevier, Amsterdam, 1986.
12. M. N. Hughes Comprehensive Coord. Chem. 1987 6 643-648.
13. M. C. Cann and M. E. Connelly, Real-World Cases in Green Chemistry, ACS, Washington, 2000, p. 19.
14. K. Weissermel and H.-J. Arpe, Industrial Organic Chemistry, Wiley-VCH, Weinheim, 1997, p. 345.
15. D. Lucet T. Le Gall C. Mioskowski Angew. Chem., Int. Ed. 1998 19 2580-2627.
16. C. Metallinos F. B. Barrett J. L. Chaytor M. E. A. Heska Org. Lett. 2004 6 3641-3644.
17. W.-B. Wang S.-M. Lu P. Y. Yang X.-W. Han Y.-G. Zhou J. Am. Chem. Soc. 2003 125 10536-10537.
18. I. F. Eckhard R. Fielden L. A. Summers Aust. J. Chem. 1975 28 1149-1151.
19. Preparation of Raney-Nickel: R. Mozingo Org. Synth. 1962 3 181-183.
20. Commercially available Raney–Nickel from Acros Organics.
21. See ESI D. Buchecker P. A. Marnot J. P. Sauvage Tetrahedron Lett. 1982 23 5291-5294.
22. For the synthesis of substituted phenanthrolines via side chain functionalization of neocuproine, see: W. M. Czaplik, J. Lex and A. Jacobi von Wangelin, manuscript in preparation.
23. Representative procedure: A 50 mL Parr® high pressure reactor was charged with [1,10]-phenanthroline (150 mg, 0.833 mmol) and abs. ethanol (6 mL). A Teflon-coated magnetic stir bar covered with Raney-Nickel (5 mg, 0.083 mmol, 10 mol%) was added, and the reactor was pressurized with hydrogen (20 bar). The reaction was stirred at 100 °C (appr. 25 bar). After 16 h, the reactor was cooled to rt and slowly depressurized. The catalyst-covered stir bar was retrieved with a pair of tweezers, washed with ethanol (2 × 1 mL), and the solution passed through a Celite pad (3 cm). The filtrate was concentrated in an oil pump vacuum to give octahydrophenanthroline 1 in 99% yield (155 mg, 0.825 mmol). The compound undergoes slow aerobic decomposition to the imine and thus was stored under argon at −20 °C. The stir bar was stored in ethanol for up to 7 days and used for a new reaction without further manipulation.
24. See also ESI The unit cell contains meso and rac isomers and exhibits some disorder in 2- and 3-positions of R, R-2 and meso-2. From structural refinement, a statistical 3/1 (rac/meso) mixture in the crystal can be deducted.
25. −3.
26. S. Goto, J. Velder, S. El Sheikh, Y. Sakamoto, M. Mitani, S. Elmas, A. Adler, A. Becker, J.-M. Neudörfl and H.-G. Schmalz, manuscript in preparation.