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Synlett 2012; 23(9): 1402-1406
DOI: 10.1055/s-0031-1290963
DOI: 10.1055/s-0031-1290963
letter
Continuous-Flow Processing of Gaseous Ammonia Using a Teflon AF-2400 Tube-in-Tube Reactor: Synthesis of Thioureas and In-Line Titrations
Authors
Further Information
Publication History
Received: 24 February 2012
Accepted after revision: 23 March 2012
Publication Date:
08 May 2012 (online)
Abstract
A simple tube-in-tube reactor based on the gas-permeable membrane Teflon AF-2400 was used in the continuous flow reaction of gaseous ammonia with isothiocyanates and one isocyanate. A colourimetric in-line titration technique is also reported as a simple method to quantify the amount of ammonia taken up by the solvent in the system.
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References
-
For some reviews in this area, see:
- 1a Wegner J, Ceylan S, Kirschning A. Adv. Synth. Catal. 2012; 354: 17
- 1b Baumann M, Baxendale IR, Ley SV. Mol. Divers. 2011; 15: 613
- 1c Wiles C, Watts P. Chem. Commun. 2011; 47: 6512
- 1d Hartman RL, McMullen JP, Jensen KF. Angew. Chem. Int. Ed. 2011; 50: 7502
Reference Ris Wihthout Link
- 1e Webb D, Jamison TF. Chem. Sci. 2010; 1: 675
Reference Ris Wihthout Link
- 1f Razzaq T, Kappe CO. Chem.–Asian J. 2010; 5: 1274
- 1g Yoshida JI. Chem. Rec. 2010; 10: 332
- 1h Hessel V. Chem. Eng. Technol. 2009; 32: 1655
Reference Ris Wihthout Link
- 1i Mak XY, Laurino P, Seeberger PH. Beilstein J. Org. Chem. 2009; 5: No. 19
- 1j O’Brien M, Denton R, Ley SV. Synthesis 2011; 1157
- 2a O’Brien M, Baxendale IR, Ley SV. Org. Lett. 2010; 12: 1596
- 2b Petersen T, Polyzos A, O’Brien M, Ulven T, Baxendale IR, Ley SV. ChemSusChem 2012; 5: 274
- 2c O’Brien M, Taylor N, Polyzos A, Baxendale IR, Ley SV. Chem. Sci. 2011; 2: 1250
- 2d Polyzos A, O’Brien M, Petersen T, Baxendale IR, Ley SV. Angew. Chem. Int. Ed. 2011; 50: 1190
- 2e Koos P, Gross U, Polyzos A, O’Brien M, Baxendale IR, Ley SV. Org. Biomol. Chem. 2011; 9: 6903
- 2f Bourne SL, Koos P, O’Brien M, Martin B, Schenkel B, Baxendale IR, Ley SV. Synlett 2011; 2643
- 2g Kasinathan S, Bourne SL, Tolstoy P, Koos P, O’Brien M, Bates RW, Baxendale IR, Ley SV. Synlett 2011; 2648
- 3a Kobayashi J, Mori Y, Okamoto K, Akiyama R, Ueno M, Kitamori T, Kobayashi S. Science 2004; 304: 1305
- 3b Fukuyama T, Rahman T, Kamata N, Ryu I. Beilstein J. Org. Chem. 2009; 5: No. 34
- 3c Irfan M, Glasnov TN, Kappe CO. Org. Lett. 2011; 13: 984
- 3d Chambers RD, Fox MA, Sandford G, Trmcic J, Goeta A. J. Fluor. Chem. 2007; 128: 29
- 3e Hubner S, Bentrup U, Budde U, Lovis K, Dietrich T, Freitag A, Kupper L, Jahnisch K. Org. Process Res. Dev. 2009; 13: 952
- 3f Wada Y, Schmidt MA, Jensen KF. Ind. Eng. Chem. Res. 2006; 45: 8036
- 3g Murphy ER, Martinelli JR, Zaborenko N, Buchwald SL, Jensen KF. Angew. Chem. Int. Ed. 2007; 46: 1734
- 3h Hamano M, Nagy KD, Jensen KF. Chem. Commun. 2012; 48: 2086
- 3i Miller PW, Jennings LE, deMello AJ, Gee AD, Long NJ, Vilar R. Adv. Synth. Catal. 2009; 351: 3260
- 3j Abdallah R, Meille V, Shaw J, Wenn D, de Bellefon C. Chem. Commun. 2004; 372
- 3k Han X, Bourne RA, Poliakoff M, George MW. Chem. Sci. 2011; 2: 1059
- 3l Csajagi C, Borcsek B, Niesz K, Kovacs I, Szekelyhidi Z, Bajko Z, Urge L, Darvas F. Org. Lett. 2008; 10: 1589
- 3m Saaby S, Knudsen KR, Ladlow M, Ley SV. Chem. Commun. 2005; 2909
- 4a Resnick PR, Buck WH In Fluoropolymers II . Hougham GG, Cassidy PE, Johns K, Davidson T. Kluwer Academic; New York: 1999: 25
- 4b Resnick PR. US Patent US3978030, 1976
- 4c Nemser SM, Roman IC. US Patent US5051114, 1991
- 4d Polyakov A, Yampolskii Y. Desalination 2006; 200: 20
- 5a Park CP, Kim D.-P. J. Am. Chem. Soc. 2010; 132: 10102
- 5b Maurya RA, Park CP, Kim D.-P. Beilstein J. Org. Chem. 2011; 7: 1158
- 5c Park CP, Maurya RA, Lee JH, Kim D.-P. Lab Chip 2011; 11: 1941
- 5d Maurya RA, Park CP, Lee JH, Kim D.-P. Angew. Chem. Int. Ed. 2011; 50: 5952
- 6 Mercadante MA, Leadbeater NE. Org. Biomol. Chem. 2011; 9: 6575
-
For early work on the application of in-line titration for analytical purposes, see:
- 7a Nicholson MM. Anal. Chem. 1961; 33: 1328
- 7b Blaedel WJ, Laessig RH. Anal. Chem. 1964; 36: 1617
- 8a Dolman SJ, Nyrop JL, Kuethe JT. J. Org. Chem. 2011; 76: 993
- 8b Koos P, Browne DL, Ley SV. Green Process. Synth. 2012; 1: 11
-
For examples of some recent papers, see:
- 9a Noël T, Naber JR, Hartman RL, McMillan JP, Jensen KF, Buchwald SL. Chem. Sci. 2011; 2: 287
- 9b Browne DL, Deadman BJ, Ashe R, Baxendale IR, Ley SV. Org. Process Res. Dev. 2011; 15: 693
- 9c Browne DL, Baumann M, Harji BH, Baxendale IR, Ley SV. Org. Lett. 2011; 13: 3312
- 9d Browne DL, Baxendale IR, Ley SV. Tetrahedron 2011; 67: 10296
- 9e Rasheed M, Wirth T. Angew. Chem. Int. Ed. 2011; 50: 357
- 9f Nieuwland PJ, Segers R, Koch K, van Floris JC. M, Rutjes PJ. J. Org. Process Res. Dev. 2011; 15: 783
- 9g Dalinger D, Lehmann JD, Moseley JD, Kappe CO. Org. Process Res. Dev. 2011; 15: 841
- 9h Opalka SM, Longstreet AB, McQuade DT. Beilstein J. Org. Chem. 2011; 7: 1671
- 9i Rueping M, Bootwicha T, Baars H, Sugiono E. Beilstein J. Org. Chem. 2011; 7: 1680
- 9j Baumann M, Baxendale IR, Kirschning A, Ley SV, Wagner J. Heterocycles 2011; 2: 1297
- 9k Hodgkinson JT, Galloway WR. J. D, Saraf S, Baxendale IR, Ley SV, Ladlow M, Welch M, Spring DR. Org. Biomol. Chem. 2011; 9: 57
- 9l Smith CJ, Smith CD, Nikbin N, Ley SV, Baxendale IR. Org. Biomol. Chem. 2011; 9: 1927
- 9m Smith CJ, Nikbin N, Ley SV, Lange H, Baxendale IR. Org. Biomol. Chem. 2011; 9: 1938
- 9n Gutierrez AC, Jamison TF. J. Flow Chem. 2011; 1: 24
- 9o Pagano N, Herath A, Cosford ND. P. J. Flow Chem. 2011; 1: 28
- 9p Parrott AJ, Bourne RA, Akien GR, Irvine DJ, Poliakoff M. Angew. Chem. Int. Ed. 2011; 50: 3788