Methoxy Polyoxyethylene Dodecanoate의 합성

강윤석; 노승호; 최성옥; 남기대

Journal of the Korean Industrial and Engineering Chemistry, Vol.9, No.5, 749-753, October, 1998

Export Citation

Methoxy Polyoxyethylene Dodecanoate의 합성

Synthesis of Methoxy Polyoxyethlene Dodecaniates

강윤석, 노승호, 최성옥, 남기대

초록

고급지방산 메틸에스테르의 일종인 dodecanoic acid methyl ester (DME)에 금속 산화물인 고체촉매 (W-7)를 이용하여 고온, 고압하에서 ethyleneoxide (EO)를 5, 7, 9, 및 12 몰씩 부가반응시켜 얻은 비이온성 계면활성제인 methoxy polyoxy ethylene dodecanoate (MPD)류 4종을 높은 수율 (93∼97%)로 합성하여 얻었다. DME는 구조적으로 활성수소가 없어서 일반적인 산, 알칼리 촉매에서는 반응이 어렵고 활성고체촉매를 사용해야 EO의 단위 몰수를 부가 시킬 수 있었다. 최종 생성물에 대한 것을 IR, HPLC 및 ¹H NMR를 이용하여 각각의 화합물에 대한 구조를 확인하였다. 이 결과 EO의 부가 몰수는 5.2, 7.1, 9.2 및 12.1 몰이었고, 각 몰의 평균 EO 분포는 polyoxyethylene alkyl ether (AE)처럼 정규분포 곡선을 나타내었다.

Methoxy polyoxyethylene dodecanoates, kinds of nonionic surfactants, could be obtained from addition of ethylene oxide (5, 7, 9, and 12mol) with fatty acid methyl ester utilizing solid catalyst, metal oxide. Because ethylene oxide (EO) couldn't react directly in acid or alkali catalyst with dodecanoic acid methyl ester (DME) that had no active hydrogen, the reaction to add EO was carried out using active solid catalyst. By using IR, HPLC and ¹H NMR analysis, structural confirmation of methyl polyoxy ethylene dodecanate showed high yield ranging from 93 to 97%. EO unit mol number of reacted products was 5.2, 7.1, 9.2 and 12.1 mol respectively. Also, EO adduct distrobution of ethoxylated methyl laurate (MPD) had normal distribution curve like polyoxyethylene alkyl ether (AE).

Keywords:Nonionic Surfactant;Methoxy PDE Alkaniate;Ethoxylation;Metal Oxide

[References]

Raymond AM, Pro. the 4th World Surfactants Congress, CESIO Press, 1, 24 (1996)
남기대, "계면활성제(2): 공업적응용," 수서원, 311 (1994)
Lim JC, J. Korean Ind. Eng. Chem., 8(3), 473 (1997)
Gilbert PA, Pro. the 4th World Surfactants Congress, CESIO Press, 1, 57 (1996)
Miller CA, Neogi P, "Interfacial Phenomena: Equilibrium and Dynamic Effects," Marcel Dekker, New York (1985)
남기대, 정노희, 권석기, "유기공업화학," 보성각, 141 (1997)
Hill EF, Wilson GR, Steinle EC, Ind. Eng. Chem., 46(9), 1917 (1954)
Hansley VL, Ind. Eng. Chem., 39, 55 (1947)
Kastens ML, Peddicord H, Ind. Eng. Chem., 41, 438 (1949)
Hama I, Okamoto T, Yomada K, J. Am. Oil Chem. Soc., 74, 19 (1997)
Bruce L, Wharry D, U.S. Patent, 4,775,653 (1988)
Fujimori Y, Uyuchi N, U.S. Patent, 5,374,750 (1994)
Weerasooriya, Cynthia U, Lin J, U.S. Patent, 5,220,046 (1993)
Weerasooriya, Cynthia U, Lin J, U.S. Patent, 5,386,045 (1995)
Hama I, Nakamura H, Nakano H, J. Am. Oil Chem. Soc., 4, 486 (1993)
Boyd DR, Marle ER, J. Chem. Soc., 105, 2117 (1974)
Schechter L, Wyntra J, Ind. Eng. Chem., 48, 86 (1956)
Madsen EH, J. Chem. Soc., 103, 966 (1973)
Richards TW, Rowe AW, J. Am. Chem. Soc., 44, 684 (1922)

[Referenced By]

[1] Raymond AM, Pro. the 4th World Surfactants Congress, CESIO Press, 1, 24 (1996)

[2] 남기대, "계면활성제(2): 공업적응용," 수서원, 311 (1994)

[3] Lim JC, J. Korean Ind. Eng. Chem., 8(3), 473 (1997)

[4] Gilbert PA, Pro. the 4th World Surfactants Congress, CESIO Press, 1, 57 (1996)

[5] Miller CA, Neogi P, "Interfacial Phenomena: Equilibrium and Dynamic Effects," Marcel Dekker, New York (1985)

[6] 남기대, 정노희, 권석기, "유기공업화학," 보성각, 141 (1997)

[7] Hill EF, Wilson GR, Steinle EC, Ind. Eng. Chem., 46(9), 1917 (1954)

[8] Hansley VL, Ind. Eng. Chem., 39, 55 (1947)

[9] Kastens ML, Peddicord H, Ind. Eng. Chem., 41, 438 (1949)

[10] Hama I, Okamoto T, Yomada K, J. Am. Oil Chem. Soc., 74, 19 (1997)

[11] Bruce L, Wharry D, U.S. Patent, 4,775,653 (1988)

[12] Fujimori Y, Uyuchi N, U.S. Patent, 5,374,750 (1994)

[13] Weerasooriya, Cynthia U, Lin J, U.S. Patent, 5,220,046 (1993)

[14] Weerasooriya, Cynthia U, Lin J, U.S. Patent, 5,386,045 (1995)

[15] Hama I, Nakamura H, Nakano H, J. Am. Oil Chem. Soc., 4, 486 (1993)

[16] Boyd DR, Marle ER, J. Chem. Soc., 105, 2117 (1974)

[17] Schechter L, Wyntra J, Ind. Eng. Chem., 48, 86 (1956)

[18] Madsen EH, J. Chem. Soc., 103, 966 (1973)

[19] Richards TW, Rowe AW, J. Am. Chem. Soc., 44, 684 (1922)