Authors:
Ana Cukalovic SynBioC Research Group, Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, B-9000, Coupure Links 653, Gent, Belgium

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Jean-Christophe M. Monbaliu SynBioC Research Group, Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, B-9000, Coupure Links 653, Gent, Belgium

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Geraldine J. Heynderickx Laboratory for Chemical Technology, Department of Chemical Engineering, Faculty of Engineering and Architecture, Ghent University, B-9000, Krijgslaan 281-S5, Gent, Belgium

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Christian V. Stevens SynBioC Research Group, Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, B-9000, Coupure Links 653, Gent, Belgium

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The Kiliani reaction, i.e. the elongation of the carbon chain by means of cyanide addition to the carbonyl group of carbohydrate derivatives, is studied on lower C3-, C4- and C6-ketoses under continuous flow conditions. Depending on the process parameters, the corresponding cyanohydrins or α-hydroxycarboxylic acids are obtained. A simple on-line purification of the effluent is studied using cation exchange resins. Reactions provide high yields and selectivity within short residence times, emphasizing the assets of the continuous flow process versus the batch process.

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  • 5. Wiles, C ; Watts., P. Micro Reaction Technology in Organic Synthesis; CRC Press Taylor & Francis: Boca Raton, FL 2011; pp xxii+432.

  • 6. (a) Acke, D.R.J. Evaluation of Microreactor Technology for Multicomponent Reactions. Ph.D. thesis, Faculty of Bioscience Engineering, Ghent University, Ghent, 2007; (b) Acke, D.R.J.; Orru, R.V.A.; Stevens, C.V. QSAR Comb. Sci. 2006, 25, 474–483; (c) Acke, D.R.J.; Stevens, C.V. Green Chem. 2007, 9, 386–390; (d) Acke, D.R.J.; Stevens, C.V.; Roman, B.I. Org. Process Res. Dev. 2008, 12, 921–928; (e) Heugebaert, T.S.A.; Roman, B.I.; De Blieck, A.; Stevens, C.V. Tetrahedron Lett. 2010, 51, 4189–4191.

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  • 7. (a) Monbaliu, J.C.M.R.; Cukalovic, A.; Marchand-Brynaert, J.; Stevens, C.V. Tetrahedron Lett. 2010, 51, 58305833; (b) Monbaliu, J.C.M.R.; Winter, M.; Chevalier, B.; Schmidt, F.; Jiang, Y.; Hoogendoorn, R.; Kousemaker, M.A.; Stevens, C.V. Bioresource Technol. 2011, 102, 9304–9307.

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  • 8. Schwalbe, T.; Golbig K. et al. Eur. Pat. Appl. EP 1123734, 2001. Chem. Abstr. 2001, 135, 154468b.

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  • 11. Serianni, A.S.; Nunez, H.A.; Barker, R. 1980 J.Org. Chem. 45 33293341.

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Journal of Flow Chemistry
Language English
Size A4
Year of
Foundation
2011
Volumes
per Year
1
Issues
per Year
4
Founder Áramlásos Kémiai Tudományos Társaság
Founder's
Address
H-1031 Budapest, Hungary Záhony utca 7.
Publisher Akadémiai Kiadó
Springer Nature Switzerland AG
Publisher's
Address
H-1117 Budapest, Hungary 1516 Budapest, PO Box 245.
CH-6330 Cham, Switzerland Gewerbestrasse 11
Responsible
Publisher
Chief Executive Officer, Akadémiai Kiadó
ISSN 2062-249X (Print)
ISSN 2063-0212 (Online)