Removal of heavy metals from organic reaction mixtures: Preparation and application of functionalized resins

Organic Process Research and Development

Volumn 13, Issue 6, 2009, Pages 1068-1079

  Barbaras, Damien ^a,c   Brozio, Jörg ^a   Johannsen, Ib ^b   Allmendinger, Thomas ^a  

^a NOVARTIS PHARMA AG   (Switzerland)

^b UNIVERSITY OF SOUTHERN DENMARK   (Denmark)

^c ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 72449146233     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op900102a     Document Type: Article

References (44)

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9. The sometimes low solubility of aromatic compounds makes this approach inefficient. For a recent successful alternative approach based on the reslurry of the metal-contaminated compound in the presence of soluble scavengers, see: Flahive, E. J.; Ewanicki, B. L.; Sach, N. W.; O'Neill-Slawecki, S. A.; Stankovic, N. S.; Yu, S.; Guinness, S. M.; Dunn, J. Org. Process. Res. Dev. 2008, 12, 637-645.
10. For details, see the experimental section.
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16. (b) See entries for "Deloxan" at http://www.finechemicals.de.
17. Matrix innovation: http://www.matrix-innovation.com; other companies now offer similar kits, see: http://www.silicycle.com; http://www. reaxa.com; http://www.jmcatalysts.com/pharma/index.asp (Smopex); http://www.phosphonics. com; http://www.polymerlabs.com.
18. Rohm & Haas: http://www.amberlyst.com/literature/us/IRC748.pdf.
19. For the preparation of PS-TMT, see: Ishihara, K.; Nakayama, M.; Kurihara, H.; Haraguchi, H. Chem. Lett. 2000, 10, 1218-1219.
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29. For details, see the Experimental Section.
30. This was described in a patent to be an efficient scavenger, see reference 11.
31. Kaden, T. University of Basel, personal communication.
32. E the less efficient is the resin.
33. Rohm & Haas did not disclose the details for Amberlite GT73 which is now replaced by the commercial Amberlite GT74.
34. 2-SH) proved to be efficient in certain other cases tested by Markus Bänziger (personal communication).
35. One target of catalyst optimization is, of course, to increase the turnover number and thus to decrease the amount of precious metal needed.
36. 4 solution. For details, see reference 19.
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38. See Table 15; 30 CHF/g compared to 1 CHF/g (Sigma-Aldrich prices for 25 and 250 mL quantities, respectively).
39. Similar resins are now commercially available: Isolute Si-TMT by Biotage (http://www.biotage.com) and SiliaBond DMT by Silicycle (http://www.silicycle. com) which could be enumerated in our system as S3e.
40. For cost reasons, reuse of the resin needs to be considered; during regeneration the precious metal may be recovered as well.
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42. Naphthalene-1-carboxylic acid, sulfuric acid, benzene-sulfonic acid, and naphthalene-2-sulfonic acid were used.
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