ReactIR flow cell: A new analytical tool for continuous flow chemical processing

Organic Process Research and Development

Volumn 14, Issue 2, 2010, Pages 393-404

  Carter, Catherine F ^a   Lange, Heiko ^a   Ley, Steven V ^a   Baxendale, Ian R ^a   Wittkamp, Brian ^b   Goode, Jon G ^c   Gaunt, Nigel L ^c  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b Mettler Toledo AutoChem   (United States)

^c Mettler Toledo Ltd   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77950124624     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op900305v     Document Type: Article

References (70)

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21. Of special interest in this respect are, for example: azide sources (see ref 19), ozone (see ref 5a), diazomethane (Martin, L. J.; Ley, S. V. University of Cambridge, UK. Unpublished work, 2009), fluoride sources (see ref 10)
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25. (d) Sedelmeier, J.; Ley, S. V.; Lange, H.; Baxendale, I. R. Eur. J. Org. Chem. 2009, 4412-4420.
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27. (f) Smith, C. J.; Iglesias-Sigüenza, F. J.; Baxendale, I. R.; Ley, S. V. Org. Biomol. Chem. 2007, 5, 1562-1568.
28. (g) Vickerstaffe, E.; Villard, A.-L.; Ladlow, M.; Ley, S. V. Synlett 2007, 1251-1254.
29. (h) Baxendale, I. R.; Deeley, J.; Griffiths-Jones, C. M.; Ley, S. V.; Saaby, S.; Tranmer, G. K. Chem. Commun. 2006, 2566-2568.
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31. Selected publications on inline IR spectroscopy and closely related topics: (a) Hübner, S.; Bentrup, U.; Budde, U.; Lovis, K.; Dietrich, T.; Freitag, A.; Küpper, L.; Jähnisch, K. Org. Process Res. Dev. 2009, 13, 952-960.
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44. An ATR technology based IR flow cell specially tailored for analyzing aqueous solutions is available from Bruker Optik GmbH Rudolf-Plank-Strasse 27, 76275 Ettlingen, Germany. Website: www.brukeroptics.com
45. (a) The ReactIR 45m and the reaction analysis software iC IR 4.0 are available from Mettler-Toledo AutoChem, 7075 Samuel Morse Drive, Columbia, Maryland, U.S.A. Webinars are available detailing the use of these two previously launched parts of the analytical tool described in here; website: www.mt.com
46. (b) The IR flow cell can be easily replaced by the conventional fibre-optic probe arm as necessary (and Vice Versa). This exchange needs to be accompanied by selecting the probe-specific preadjustments within the software rather than the IR flow cell-specific set of preadjustments.
47. (a) Carter, C. F.; Baxendale, I. R.; O'Brien, M.; Pavey, J. B. J.; Ley, S. V. Org. Biomol. Chem. 2009, 7, 4594-4597.
48. (b) Carter, C. F.; Baxendale, I. R.; Pavey, J. B. J.; Ley, S. V. Org. Biomol. Chem. 2009, 7, in press.
49. Vapourtec R2+ and R4 units are available from Vapourtec Ltd., Place Farm, Ingham, Suffolk IP31 1NQ, UK. Website: www.vapourtec.co.uk.
50. (a) Baumann, M.; Baxendale, I. R.; Martin, L. J.; Ley, S. V. Tetrahedron 2009, 65, 6611-6625.
51. (b) Bluck, G. W.; Ley, S. V. University of Cambridge, UK. Unpublished work, 2009.
52. (c) Baumann, M.; Baxendale, I. R.; Ley, S. V. Synlett 2008, 2111-2114.
53. We are currently awaiting a number of third-generation IR flow cells. These include a diamond-based flow cell with improved optics, a silicon-based flow cell, a double-headed IR flow cell, and a flow cell with 10 μL head volume. These cells will be thoroughly tested in due course. The results will be compared to the results obtained with the prototype.
54. The H-Cube and the H-Cube Midi are available from Thales Nano, Inc.,Gázgyaru.1-3,Budapest,HungryH-1031.Website: www.thalesnano.com.
55. (a) Moon, M. S.; Lee, S. H.; Cheong, C. S. Bull. Korean Chem. Soc. 2001, 22, 1167-1168.
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57. Review: Marshall, J. A. J. Org. Chem. 2007, 72, 8153-8166.
58. Sakai, D. S.; Lange, H.; Ley, S. V. University of Cambridge, UK. Unpublished work, 2009.
59. The Flow Start microfluidic reactor is available from Future Chemistry Holding BV, Toernooiveld 100, 6525 EC Nijmegen, The Netherlands. Website: www.futurechemistry.com.
60. Baumann, M.; Baxendale, I. R.; Ley, S. V.; Nikbin, N.; Smith, C. D.; Tierney, J. P. Org. Biomol. Chem. 2008, 6, 1577-1586.
61. Smith C. J.; Nikbin, N.; Smith, C. D.; Ley, S. V.; Baxendale, I. R. Org. Biomol. Chem. 2010, 8. Manuscript in preparation.
62. Issues could potentially arise when the diamond-based ATR IR flow cell is used for monitoring azide chemistry, as some azide species are not compatible with the gold seal that is currently employed. However, we did not see any damage of that gold seal while operating the system for azide monitoring as described. We assume that the low concentrations of aggressive azide species were beneficial in this case. Alternative types of seals are available upon request if necessary.
63. For azide detection down to concentrations of 0.005 M using ferric(III) chloride solution, see: (a) Reference 15 in: Kopach, M. E.; Murray, M. M.; Braden, T. M.; Kobierski, M. E.; Williams, O. L. Org. Process Res. Dev. 2009, 13, 152-160.
64. (b) Feigl, F.; Anger, V.; Oesper, R. E. Spots in Inorganic Analysis, 6th ed.; Elsevier Publishing Company: Amsterdam, London, NY, 1972.
65. An NE-1000 single-syringe pump was used which is available from New Era Pump System, Inc., 2517 Bayview Ave., Wantagh, New York 11793-4305, U.S.A. Website: www.syringepump.com.
66. Kumarn, S.; Hoffmann, T. J.; Ley, S. V. University of Cambridge, UK. Unpublished work, 2009.
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69. For the destruction of azides using ceric ammonium nitrate solution, see: Armour, M.-A. Hazardous Laboratory Chemicals Disposal Guide, 3rd ed.; CRC Press LLC: Boca Raton, Florida, U.S.A., 2003; p 461.
70. Prepared according to Deeley, J.; Bertram, A.; Pattenden, G. Org. Biomol. Chem. 2008, 6, 1994-2010.