European Journal of Chemistry 2011, 2(2), 269-271. doi:10.5155/eurjchem.2.2.269-271.261

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


Na Ge (1) , Yumin Zhang (2) , Dongmin Shi (3) , Qiang Gu (4,*) , Xuefeng Zhu (5) , Zhiyong Ding (6)

(1) College of Chemistry, Jilin University, Changchun, 130012, China
(2) College of Chemistry, Jilin University, Changchun, 130012, China
(3) College of Chemistry, Jilin University, Changchun, 130012, China
(4) College of Chemistry, Jilin University, Changchun, 130012, China
(5) Daqing New Century Fine Chemicals Co. Ltd., Daqing, Heilongjiang Province, 163511, China
(6) Daqing New Century Fine Chemicals Co. Ltd., Daqing, Heilongjiang Province, 163511, China
(*) Corresponding Author

Received: 24 Aug 2010, Accepted: 08 Dec 2010, Published: 30 Jun 2011

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.

2_2_269_271_800


Keywords


Benzyl diethyl phosphate; Sodium salt of diethyl phosphate; Solid-liquid phase transfer catalysis; Nucleophilic substitution; Organic phosphate; Mechanism

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DOI: 10.5155/eurjchem.2.2.269-271.261

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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


How to cite


Ge, N.; Zhang, Y.; Shi, D.; Gu, Q.; Zhu, X.; Ding, Z. Eur. J. Chem. 2011, 2(2), 269-271. doi:10.5155/eurjchem.2.2.269-271.261
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(2), 269-271. doi:10.5155/eurjchem.2.2.269-271.261
Ge, N., Zhang, Y., Shi, D., Gu, Q., Zhu, X., & Ding, Z. (2011). Novelties of solid-liquid phase transfer catalyzed synthesis of benzyl diethyl phosphate from the sodium salt of diethyl phosphate. European Journal of Chemistry, 2(2), 269-271. doi:10.5155/eurjchem.2.2.269-271.261
Ge, Na, Yumin Zhang, Dongmin Shi, Qiang Gu, Xuefeng Zhu, & Zhiyong Ding. "Novelties of solid-liquid phase transfer catalyzed synthesis of benzyl diethyl phosphate from the sodium salt of diethyl phosphate." European Journal of Chemistry [Online], 2.2 (2011): 269-271. Web. 19 Sep. 2019
Ge, Na, Zhang, Yumin, Shi, Dongmin, Gu, Qiang, Zhu, Xuefeng, AND Ding, Zhiyong. "Novelties of solid-liquid phase transfer catalyzed synthesis of benzyl diethyl phosphate from the sodium salt of diethyl phosphate" European Journal of Chemistry [Online], Volume 2 Number 2 (30 June 2011)

DOI Link: https://doi.org/10.5155/eurjchem.2.2.269-271.261

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