Factors influencing the formation of 2-hydroxy-6-naphthoic acid from carboxylation of naphthol

So-Jin Ahn; Yong-Kul Lee

Journal of Industrial and Engineering Chemistry, Vol.19, No.6, 2060-2063, November, 2013

DOI10.1016/j.jiec.2013.03.016 Export Citation

Factors influencing the formation of 2-hydroxy-6-naphthoic acid from carboxylation of naphthol

So-Jin Ahn, and Yong-Kul Lee^†

Laboratory of Advanced Catalysis for Energy and Environment, Department of Chemical Engineering, Dankook University, 126 Jukjeondong, Yongin 448-701, South Korea

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The synthesis of 2-hydroxy-6-naphthoic acid (2,6-HNA) from carboxylation of alkali-naphthoxide was studied with varying alkali cation types and reaction conditions such as reactant concentration, reaction time, temperature, and pressure. The product selectivity was strongly affected by the types of alkali cation, reaction time, and temperature, while the product yield was governed by reaction pressure. The maximum HNA yield, 28.6%, was achieved with 2,6-HNA selectivity of 81.6% at 6 atm of CO2, 543 K, and 6 h of reaction. The addition of K2CO3 led to further increase in the productivity of 2,6-HNA via suppression of the decarboxylation of HNA.

Keywords:2-Naphthol;2-Hydroxy-6-naphthoic acid;Carboxylation;Kolbe-Schmitt

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[1] Dott DJ, Ziegler KJ, Owens VP, Glennon JD, Graham AE, Holtmes JD, Green Chemistry., 7, 105 (2005)

[2] Wang Y, Li Q, Gong XF, Zhao XL, Zhang Y, Advances in Materials Research., 634-638, 2044 (2013)

[3] Song Y, Zhang C, Li J, Advances in Materials Research., 602-604, 1391 (2013)

[4] Gao EJ, Zhu MC, Liu L, Zhang WZ, Sun YG, Journal of Structural Chemistry., 52, 1040 (2011)

[5] Kolbe H, Annalen der Chemie und Pharmacie., 113, 126 (1860)

[6] Schmitt R, Journal fu¨ r Praktische Chemie., 21, 397 (1885)

[7] Ueno R, Sakota K, JP 195599/81 (1981)

[8] Ueno R, Masada Y, JP 86-176254 (1986)

[9] Hautzel V, Main FA, Rittner S, Walldorf M, US 5312974 (1994)

[10] Markovic Z, Markovic S, Durovic I, Monatshefte fur Chemie., 139, 329 (2008)

[11] Markovic Z, Markovic S, Begovic N, Journal of Chemical Information and Modeling., 46, 1957 (2006)

[12] Kosugi Y, Imaoka Y, Gotoh F, Rahim MA, Matsui Y, Sakanishi K, Organic & Biomolecular Chemistry., 1, 817 (2003)

[13] Iijima T, Yamaguchi T, Appl. Catal. A: Gen., 345(1), 12 (2008)

[14] Iijima T, Yamaguchi T, Tetrahedron Letters., 48, 5309 (2007)

[15] Iijima T, Iwase T, Yamaguchi T, Journal of the Japan Petroleum Institute., 49, 206 (2006)

[16] Iijima T, Takagi D, Yamaguchi T, Journal of the Japan Petroleum Institute., 1, 65 (2008)

[17] Pugach J, Borough M, Derussy DT, US 5075496 (1991)

[18] Rahim MA, Matsui Y, Kosugi Y, Bulletin of the Chemical Society of Japan., 55, 3029 (1933)

[19] Fujita S, Bhanage BM, Ikushima Y, Arai M, Green Chemistry., 3, 87 (2001)

[20] Wang H, Lu B, Cai QH, Wu F, Shan YK, Chinese Chemistry Letters., 6, 1267 (2005)

[21] Fang SN, Fujimoto K, Appl. Catal. A: Gen., 142(1), L1 (1996)