European Journal of Chemistry

Novelties of solid-liquid phase transfer catalyzed synthesis of benzyl diethyl phosphate from the sodium salt of diethyl phosphate



Main Article Content

Na Ge
Yumin Zhang
Dongmin Shi
Qiang Gu
Xuefeng Zhu
Zhiyong Ding

Abstract

Solid-liquid phase transfer catalysis coupled with mixed solvents, which could be recycled, as a green chemistry procedure, was applied to the synthesis of phosphate from the sodium salt of diethyl phosphate. The benzyl diethyl phosphate was synthesized in good yield via one-pot method from the reaction of the industrial by-product sodium salt of diethyl phosphate with benzyl chloride in solid-liquid phase transfer catalysis and toluene-water mixed solvents. The effects of catalyst structure, the amounts of catalyst, the raw material molar ratio, water loading, and reaction temperature on the conversion of the reaction were investigated. The structure of the benzyl diethyl phosphate generated was confirmed by Elemental Analysis, IR, 1H NMR and GC/MS.

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(1)
Ge, N.; Zhang, Y.; Shi, D.; Gu, Q.; Zhu, X.; Ding, Z. Novelties of Solid-Liquid Phase Transfer Catalyzed Synthesis of Benzyl Diethyl Phosphate from the Sodium Salt of Diethyl Phosphate. Eur. J. Chem. 2011, 2, 269-271.

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Author Biography

Qiang Gu, College of Chemistry, Jilin University, Changchun, 130012, China


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References

[1]. Macquarrie, D. J.; Nazih, R.; Sebti, S. Green Chem. 2002, 4, 56-59.
doi:10.1039/b109015c

[2]. Fraile, J. M.; García, J. I.; Mayoral, J. A.; Sebti, S.; Tahir, R. Green Chem. 2001, 3, 271-274.
doi:10.1039/b104201g

[3]. Silverberg, L. J.; Dillon, J. L.; Vemishetti, P. Tetrahedron Lett. 1996, 37, 771-774.
doi:10.1016/0040-4039(95)02294-5

[4]. Jones, S.; Smanmoo, C. Tetrahedron Lett. 2004, 45, 1585-1588.
doi:10.1016/j.tetlet.2004.01.003

[5]. Bache, C. A.; Lisk, D. J. Anal. Chem. 1965, 37, 1477-1480.
doi:10.1021/ac60231a008
PMid:5828144

[6]. Brown, D. M. Advances in Organic Chemistry, Interscience Publishers, Inc., New York, 1963, Vol. 3, 89-90.

[7]. Slotin, L. A. Synthesis 1977, 737-752.
doi:10.1055/s-1977-24556

[8]. Cherbuliez, E.; Kosolapoff, G. M. L.; Eds, M. In Organic Phosphorus Chemistry, Wiley-Interscience, New York, 1973, Vol. 6, Ch 15.

[9]. Cadogan, J. I. G. Organophosphorus Reagents in Organic Synthesis, Academic Press, Inc, London, 1979.

[10]. McLaughlin, M. Org. Lett. 2005, 7, 4875-4878.
doi:10.1021/ol0517271
PMid:16235911

[11]. Kofink, C. C.; Knochel, P. Org. Lett. 2006, 8, 4121-4124.
doi:10.1021/ol0616790
PMid:16928089

[12]. Kenner, G. W.; Mather, J. J. Chem. Soc. 1956, 3524-3531.

[13]. Nitta, Y.; Arakawa, Y. Chem. Pharm. Bull. 1986, 34, 3121-3129.

[14]. Givens, R. S.; Matuszewski, B.; Athey, P. S.; Stoner, R. M. J. Am. Chem. Soc. 1990, 112, 6016-6021.
doi:10.1021/ja00172a016

[15]. Zwierzak, A.; Kluba, M. Tetrahedron 1971, 27, 3163-3170.
doi:10.1016/S0040-4020(01)98109-8

[16]. Zwierzak, A. Synthesis 1976, 5, 305-306.
doi:10.1055/s-1976-24022

[17]. Yadav, G. D.; Bisht, P. M. J. Mol. Catal. A: Chem. 2005, 236, 54-64.
doi:10.1016/j.molcata.2005.04.003

[18]. Yang, H. M.; Wu, P. I. Appl. Catal. A 2001, 209, 17-26.
doi:10.1016/S0926-860X(00)00739-0

[19]. Yang, H. M.; Liu, H.-C. Appl. Catal. A 2004, 258, 25-31.
doi:10.1016/j.apcata.2003.08.002

[20]. Yadav, G. D.; Ceasar, J. L. J. Mol. Catal. A. Chem. 2006, 260, 202-209
doi:10.1016/j.molcata.2006.06.052

[21]. Yadav, G. D.; Paranjape, P. M. J. Fluorine Chem. 2005, 126, 289-295.
doi:10.1016/j.jfluchem.2004.10.005

[22]. Yadav, G. D.; Subramanian, S. J. Mol. Catal. A. Chem. 2004, 209, 75-82.
doi:10.1016/j.molcata.2003.09.003

[23]. Yadav, G. D.; Jadhav, Y. B. Langmuir 2002, 18, 5995-6002.
doi:10.1021/la0255727

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Daqing New Century Fine Chemicals Co., Ltd., China
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