Continuous production of 1-methyl-1-cyclopenten-3-one using a micro module combined with tubular mixers

Jaehoon Choe; Hyosun Lee; Young-Jun Kim; Sang Mi Lee; Kwang Ho Song

Journal of Industrial and Engineering Chemistry, Vol.14, No.1, 66-70, January, 2008

DOI10.1016/j.jiec.2007.09.003 Export Citation

Continuous production of 1-methyl-1-cyclopenten-3-one using a micro module combined with tubular mixers

Jaehoon Choe, Hyosun Lee¹, Young-Jun Kim², Sang Mi Lee², and Kwang Ho Song^{2, †}

LG Chem Research Park, Daejeon 305-380, Korea
¹Department of Chemistry, Kyungpook National University, Daegu 702-701, Korea
²Department of Chemical & Biological Engineering, Korea University, Seoul 136-713, Korea

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A high pressure microreaction system was applied to synthesize 1-methyl-1-cyclopenten-3-one. Design of experiment was used to identify the most dominant factors and the interactions from the microreaction system of an intramolecular aldol condensation reaction of 2,6-hexanedione. The response surface methodology coupled with Box-Behnken design was applied to obtain the optimum process conditions. The feed flow rates or residence time were identified as significant variables of this microreaction system. 1-methyl-1-cyclopenten-3-one was isolated in 60% yield after purification with 99.9% purity within the optimum operation ranges determined by design of experiment method. (c) 2007 The Korean Society of Industrial and Engineering Chemistry. Published by Elsevier B.V. All rights reserved.

Keywords:micro module;tubular mixer;microreaction;endothermic;DOE

[References]

Cho ES, Won YC, Lee SY, Lee BY, Shin DM, Chung YK, Inorg. Chim. Acta., 357, 2301 (2004)
Lee H, Hong S, Park Y, Jeong B, Nam D, Jung YH, Jung MY, Song KH, J. Organomet. Chem., 689, 3402 (2004)
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Straus DS, Glass CK, Med. Res. Rev., 21, 185 (2001)
Mikolajczyk M, Mikina M, Zurawinski R, Pure Appl. Chem., 71, 473 (1999)
Rodriquez Rivero M, Alonso I, Carretero JC, Chem. Eur. J., 10, 5443 (2004)
Dauben WG, Kowalczyk BA, Tetrahedron Lett., 31, 635 (1990)
Smith AB, Branca SJ, Toder BH, Tetrahedron Lett., 16, 4225 (1975)
Guthrie JP, Guo JN, J. Am. Chem. Soc., 118(46), 11472 (1996)
Guida A, Lhouty MH, Tichit D, Figueras F, Geneste P, Appl. Catal. A: Gen., 164(1-2), 251 (1997)
Watts P, Wiles C, Chem. Commun., 443 (2007)
Wiles C, Watts P, Haswell SJ, Pombo-Villar E, Lab. Chip, 1, 100 (2001)

[Referenced By]

[Related Articles]

[1] Cho ES, Won YC, Lee SY, Lee BY, Shin DM, Chung YK, Inorg. Chim. Acta., 357, 2301 (2004)

[2] Lee H, Hong S, Park Y, Jeong B, Nam D, Jung YH, Jung MY, Song KH, J. Organomet. Chem., 689, 3402 (2004)

[3] Yamamoto M, Seki K, Onuki M, JP Patent 2001176551 A2 (2001)

[4] Yamamoto M, Seki K, Onuki M, JP Patent 2,001,176,550 A2 (2001)

[5] Lanz M, Novak P, J. Power Sources, 102(1-2), 277 (2001)

[6] Straus DS, Glass CK, Med. Res. Rev., 21, 185 (2001)

[7] Mikolajczyk M, Mikina M, Zurawinski R, Pure Appl. Chem., 71, 473 (1999)

[8] Rodriquez Rivero M, Alonso I, Carretero JC, Chem. Eur. J., 10, 5443 (2004)

[9] Dauben WG, Kowalczyk BA, Tetrahedron Lett., 31, 635 (1990)

[10] Smith AB, Branca SJ, Toder BH, Tetrahedron Lett., 16, 4225 (1975)

[11] Guthrie JP, Guo JN, J. Am. Chem. Soc., 118(46), 11472 (1996)

[12] Guida A, Lhouty MH, Tichit D, Figueras F, Geneste P, Appl. Catal. A: Gen., 164(1-2), 251 (1997)

[13] Watts P, Wiles C, Chem. Commun., 443 (2007)

[14] Wiles C, Watts P, Haswell SJ, Pombo-Villar E, Lab. Chip, 1, 100 (2001)