Influence of Chain Length of Tertiary Amines on Extractability and Chemical Interactions in Reactive Extraction of Succinic Acid

Yeon Ki Hong; Won Hi Hong

Korean Journal of Chemical Engineering, Vol.21, No.2, 488-493, March, 2004

Yeon Ki Hong, and Won Hi Hong^{1, †}

Department of Chemical Engineering, Chungju National University, 123 Geomdan-ri, Iryu-myeon, Chungju, Chungbuk 380-702, Korea
¹Department of Chemical and Biomolecular Engineering, Korea Advanced Institute of Science and Technology (KAIST), 373-1 Guseong-dong, Yuseong-gu, Daejeon 305-701, Korea

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Reactive extraction of succinic acid from aqueous solutions with various tertiary amines dissolved in 1-octanol and in n-heptane has been studied as a function of the chain length of the tertiary amine. In the tertiary amine extractants in 1-octanol, the extractabilities of tertiary amines were proportional to their chain length. But, in n-heptane, the extractabilities of tertiary amines decreased with their chain length. In order to analyze chemical interactions involved in the complexation of succinic acid with amine extractants in 1-octanol and n-heptane, infrared (IR) spectroscopy was used. From IR spectroscopy, it was found that the difference of extractability in 1-octanol and in n-heptane was mainly due to the different degree of intramolecular hydrogen bonding of succinic acid with the polarity of diluents. And the possible stoichiometry of acid-amine-diluent complex was predicted as (1,1), (2,1), (1,1,1).

Keywords:Succinic Acid;Chain Length of Amine;Intramolecular Hydrogen Bond;Polarity

[References]

Barrow GM, Yerger EA, J. Am. Chem. Soc., 76, 5211 (1954)
Bizek V, Horacek J, Rericha R, Kousova M, Ind. Eng. Chem. Res., 31, 1554 (1992)
Bressler E, Braun S, J. Chem. Technol. Biotechnol., 74(9), 891 (1999)
Gottschalk G, "Bacterial Metabolism," Springer-Verlag, NY (1986)
Grinstead RR, "Base Strengths of Amines in Liquid-Liquid Extraction Systems," Solv. Extr. Chem. (ISEC 67), North-Holland, Amsterdam, 426 (1967)
Han DH, Hong WH, Korean J. Chem. Eng., 15(3), 324 (1998)
Han DH, Hong YK, Hong WH, Hong WH, Korean J. Chem. Eng., 17(5), 528 (2000)
Hong YK, Han DH, Hong WH, Korean J. Chem. Eng., 19(1), 83 (2002)
Hong YK, Hong WH, Bioprocess Eng., 22, 477 (2000)
Hong YK, Hong WH, Chang HN, Biotechnol. Lett., 22(10), 871 (2000)
Kertes AS, King CJ, Biotechnol. Bioeng., 28, 269 (1986)
Kim BS, Hong YK, Hong WH, Korean J. Chem. Eng., 19(4), 669 (2002)
Ricker NL, Michaels JN, King CJ, J. Sep. Proc. Technol., 1, 36 (1979)
Rieux A, Rumeau M, Tremillon B, Bull. Soc. Chim. Fr., 1053 (1964)
San-Martin M, Pazos C, Coca J, J. Chem. Technol. Biotechnol., 54, 1 (1992)
Tamada JA, "Extraction of Carboxylic Acids by Amine Extractants," Ph.D. Thesis, Univ. of California at Berkeley (1989)
Tamada JA, Kang CJ, Ind. Eng. Chem. Res., 29, 1327 (1990)
Tung LA, King CJ, Ind. Eng. Chem. Res., 33(12), 3217 (1994)
Weast RC, "CRC Handbook of Chemistry and Physics," 79th ed., CRC Press, Florida (1998)
Yang ST, White SA, Hsu ST, Ind. Eng. Chem. Res., 30, 1335 (1991)
Zeikus JG, Jain MK, Elankovan P, Appl. Microbiol. Biotechnol., 51(5), 545 (1999)
Ziegenfuss H, Maurer G, Fluid Phase Equilib., 102(2), 211 (1994)

[Referenced By]

[Related Articles]

[1] Barrow GM, Yerger EA, J. Am. Chem. Soc., 76, 5211 (1954)

[2] Bizek V, Horacek J, Rericha R, Kousova M, Ind. Eng. Chem. Res., 31, 1554 (1992)

[3] Bressler E, Braun S, J. Chem. Technol. Biotechnol., 74(9), 891 (1999)

[4] Gottschalk G, "Bacterial Metabolism," Springer-Verlag, NY (1986)

[5] Grinstead RR, "Base Strengths of Amines in Liquid-Liquid Extraction Systems," Solv. Extr. Chem. (ISEC 67), North-Holland, Amsterdam, 426 (1967)

[6] Han DH, Hong WH, Korean J. Chem. Eng., 15(3), 324 (1998)

[7] Han DH, Hong YK, Hong WH, Hong WH, Korean J. Chem. Eng., 17(5), 528 (2000)

[8] Hong YK, Han DH, Hong WH, Korean J. Chem. Eng., 19(1), 83 (2002)

[9] Hong YK, Hong WH, Bioprocess Eng., 22, 477 (2000)

[10] Hong YK, Hong WH, Chang HN, Biotechnol. Lett., 22(10), 871 (2000)

[11] Kertes AS, King CJ, Biotechnol. Bioeng., 28, 269 (1986)

[12] Kim BS, Hong YK, Hong WH, Korean J. Chem. Eng., 19(4), 669 (2002)

[13] Ricker NL, Michaels JN, King CJ, J. Sep. Proc. Technol., 1, 36 (1979)

[14] Rieux A, Rumeau M, Tremillon B, Bull. Soc. Chim. Fr., 1053 (1964)

[15] San-Martin M, Pazos C, Coca J, J. Chem. Technol. Biotechnol., 54, 1 (1992)

[16] Tamada JA, "Extraction of Carboxylic Acids by Amine Extractants," Ph.D. Thesis, Univ. of California at Berkeley (1989)

[17] Tamada JA, Kang CJ, Ind. Eng. Chem. Res., 29, 1327 (1990)

[18] Tung LA, King CJ, Ind. Eng. Chem. Res., 33(12), 3217 (1994)

[19] Weast RC, "CRC Handbook of Chemistry and Physics," 79th ed., CRC Press, Florida (1998)

[20] Yang ST, White SA, Hsu ST, Ind. Eng. Chem. Res., 30, 1335 (1991)

[21] Zeikus JG, Jain MK, Elankovan P, Appl. Microbiol. Biotechnol., 51(5), 545 (1999)

[22] Ziegenfuss H, Maurer G, Fluid Phase Equilib., 102(2), 211 (1994)