Shake Flask법을 이용한 1-Octanol/Water 분배계수 측정

한선덕; 박수진; 박소진

HWAHAK KONGHAK, Vol.35, No.1, 96-101, February, 1997

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Shake Flask법을 이용한 1-Octanol/Water 분배계수 측정

Determination of 1-Octanol/Water Partition Coefficients by Using Shake Flask Method

한선덕, 박수진, 박소진

초록

화학무릴의 운명과 생체에 대한 평가에 유용하게 이용되는 1-octanol/water 분배계수(K_ow)를 shake flask(SF)법으로 측정하기 위하여, 먼저 tert-butanol을 모델로 포화용액제조와 분배평형에 필요한 교반시간을 정립하고, n-alcohol(C₁-C₇)에 대해 K_ow를 측정하여 문헌치와 비교하였다. 비교편차가 평균 5% 미만으로 본 실험방법의 정확성과 재현성을 확인할 수 있었으므로, 이 방법으로 염소화합물과 방향족화합물의 K_ow를 측정하였다. 이들의 K_ow는 모든 화합물에서 몰부피에 따라 선형적으로 증가하는 경향을 보였으며, K_ow와 water에 대한 포화용해도사이의 관계를 1차 선형식으로 표현할 수 있었다.

The 1-octanol/water partition coefficient(K_ow) is used to estimate the chemical’s fate and the behavior of chemicals against the organization. We want to determine the K_ow by using shake flask(SF) method. Firstly we established the requiring time for preparing of saturated solution and for partitioning equilibrium in the SF method with tert-butanol. The accuracy and reproducibility of this SF method was reliable since the average deviation was less than 5% between measured K_ow values of alcohols(C₁-C₇) and the reported values. The K_ow for some chlorinated and aromatic compounds were measured. The K_ow of these organic chemicals were linearly proportional to their molar volumes and the relationship of K_ow and water solubilities can be expressed by a first order linear equation.

Keywords:K_ow SF Method;Solubility;Chlorinated Compound;Aromatic compound

[References]

Mackay D, "Multimedia Environmental Models; The Fugacity Approach," Lewis Pub. Inc. (1991)
Wasik SP, Miller MM, Tewari Y, May W, Devoe H, Zoller W, "Residue Reviews 85," Springer-Verlag, New York, Inc. (1983)
Imboden DM, Gschwend PM, "Environmental Organic Chemistry," John Wiley & Sons (1993)
Burkhard PL, Andren AW, Armstrong DE, Environ. Sci. Technol., 19, 500 (1985)
Suzuki T, J. Computer-Aided Molecular Design, 5, 149 (1991)
Kamlet M, Doherty RM, Carr PW, Mackay D, Abraham M, Taft RW, Environ. Sci. Technol., 22, 5 (1988)
Nirmalakhandan NN, Speece RE, Environ. Sci. Technol., 22, 11 (1989)
Dearden JC, Bresnen GM, Quant. Struc. Act. Relat., 7, 133 (1988)
Fendinger N, Glotfelty D, Freeman H, Environ. Sci. Technol., 23, 12 (1989)
Bidleman T, Anal. Chem., 56, 2490 (1984)
Brooke D, Dobbs AJ, Williams N, Ecotoxicology Environ. Safty, 11, 251 (1986)
Mandava NB, Ito Y, "Countercurrent Chromatography," Marcel Dekker Inc., New York (1988)
Alrore C, Tsai R, Carotti A, Benedetti PG, J. Pharm. Pharmacol., 43, 191 (1991)
Racanatini M, Quant. Struc. Act. Relat., 6, 12 (1987)
Mackay D, Shiu WY, Sutherland RP, Environ. Sci. Technol., 13, 333 (1979)
Leo A, Hansch C, Elkins D, Chem. Rev., 71, 6 (1971)
Chiou CT, Schmedding DW, Environ. Sci. Technol., 16, 1 (1982)
Sangster J, J. Phys. Chem. Ref. Data, 18, 3 (1989)
Fujita T, Iwasa J, Hansch C, J. Am. Chem. Soc., 86, 5175 (1964)
Arce A, J. Chem. Eng. Data, 38, 336 (1993)
Riddick JA, Bunger EB, "Organic Solvents Physical Properties and Methods of Purification," Wiley-Interscience, New York, 4th ed. (1986)
Pettenati C, Alessi P, Fermeglia M, Kikie I, Thermochim. Acta, 162, 203 (1990)
Dean JA, "Handbook of Organic Chemistry," Donelly & Sons, Co. (1987)
Garg SK, J. Chem. Eng. Data, 38, 227 (1993)
Cobos JC, J. Chem. Eng. Data, 37, 535 (1992)
Arlaguppl MI, J. Chem. Eng. Data, 37, 298 (1992)

[Referenced By]

[1] Mackay D, "Multimedia Environmental Models; The Fugacity Approach," Lewis Pub. Inc. (1991)

[2] Wasik SP, Miller MM, Tewari Y, May W, Devoe H, Zoller W, "Residue Reviews 85," Springer-Verlag, New York, Inc. (1983)

[3] Imboden DM, Gschwend PM, "Environmental Organic Chemistry," John Wiley & Sons (1993)

[4] Burkhard PL, Andren AW, Armstrong DE, Environ. Sci. Technol., 19, 500 (1985)

[5] Suzuki T, J. Computer-Aided Molecular Design, 5, 149 (1991)

[6] Kamlet M, Doherty RM, Carr PW, Mackay D, Abraham M, Taft RW, Environ. Sci. Technol., 22, 5 (1988)

[7] Nirmalakhandan NN, Speece RE, Environ. Sci. Technol., 22, 11 (1989)

[8] Dearden JC, Bresnen GM, Quant. Struc. Act. Relat., 7, 133 (1988)

[9] Fendinger N, Glotfelty D, Freeman H, Environ. Sci. Technol., 23, 12 (1989)

[10] Bidleman T, Anal. Chem., 56, 2490 (1984)

[11] Brooke D, Dobbs AJ, Williams N, Ecotoxicology Environ. Safty, 11, 251 (1986)

[12] Mandava NB, Ito Y, "Countercurrent Chromatography," Marcel Dekker Inc., New York (1988)

[13] Alrore C, Tsai R, Carotti A, Benedetti PG, J. Pharm. Pharmacol., 43, 191 (1991)

[14] Racanatini M, Quant. Struc. Act. Relat., 6, 12 (1987)

[15] Mackay D, Shiu WY, Sutherland RP, Environ. Sci. Technol., 13, 333 (1979)

[16] Leo A, Hansch C, Elkins D, Chem. Rev., 71, 6 (1971)

[17] Chiou CT, Schmedding DW, Environ. Sci. Technol., 16, 1 (1982)

[18] Sangster J, J. Phys. Chem. Ref. Data, 18, 3 (1989)

[19] Fujita T, Iwasa J, Hansch C, J. Am. Chem. Soc., 86, 5175 (1964)

[20] Arce A, J. Chem. Eng. Data, 38, 336 (1993)

[21] Riddick JA, Bunger EB, "Organic Solvents Physical Properties and Methods of Purification," Wiley-Interscience, New York, 4th ed. (1986)

[22] Pettenati C, Alessi P, Fermeglia M, Kikie I, Thermochim. Acta, 162, 203 (1990)

[23] Dean JA, "Handbook of Organic Chemistry," Donelly & Sons, Co. (1987)

[24] Garg SK, J. Chem. Eng. Data, 38, 227 (1993)

[25] Cobos JC, J. Chem. Eng. Data, 37, 535 (1992)

[26] Arlaguppl MI, J. Chem. Eng. Data, 37, 298 (1992)