European Journal of Chemistry 2011, 2(2), 269-271 | doi: https://doi.org/10.5155/eurjchem.2.2.269-271.261 | Get rights and content






  OPEN ACCESS | PEER-REVIEWED | SHORT COMMUNICATION | DOWNLOAD PDF | VIEW FULL-TEXT PDF | TOTAL VIEWS

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 | Revised: 24 Feb 2011 | Accepted: 08 Dec 2010 | Published: 30 Jun 2011 | Issue Date: June 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

Full Text:

PDF /    /


DOI: 10.5155/eurjchem.2.2.269-271.261

Links for Article


| | | | |

| | | | | | |

Related Articles




Article Metrics

This Abstract was viewed 734 times | PDF Article downloaded 314 times

Funding information


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

Citations

/


[1]. Varathan Selvaraj, Pachaiyappan Abimannan, Venugopal Rajendran
Ultrasound assisted arylation of benzyl alcohol with 4-nitrochlorobenzene under a new multi-site phase-transfer catalyst in solid–liquid condition
Ultrasonics Sonochemistry  21(5), 1805, 2014
DOI: 10.1016/j.ultsonch.2014.04.010
/


[2]. Hung-Ming Yang, Wei-Ming Chu
Esterification of sodium 4-hydroxybenzoate by ultrasound-assisted solid–liquid phase-transfer catalysis using dual-site phase-transfer catalyst
Ultrasonics Sonochemistry  21(1), 395, 2014
DOI: 10.1016/j.ultsonch.2013.08.004
/


[3]. Kang Zhang, Xiaohua Zhang, Yan Li, Xinxin Wang, Qing Cao, Li’e Jin
Synthesis, characteristics and evaluation of antioxidant activity of [1-(tannin-ether)-ethyl]stearate
Journal of Food Science and Technology  54(11), 3483, 2017
DOI: 10.1007/s13197-017-2805-3
/


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

Supporting information


The Supplementary Material for this article can be found online at: Supplementary files

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. 21 Feb. 2020
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

| | | | |

| | | | | |

Save to Zotero Save to Mendeley



European Journal of Chemistry 2011, 2(2), 269-271 | doi: https://doi.org/10.5155/eurjchem.2.2.269-271.261 | Get rights and content

Refbacks

  • There are currently no refbacks.




Copyright (c)




© Copyright 2019  Atlanta Publishing House LLC All Right Reserved.

The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.

Copyright 2019 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 4614 Lavista road, Tucker, GA, 30084, USA. Registered in USA.

hatay escort hatay escort corlu escort corum escort burgaz escort giresun escort aydin escort ordu escort erzincan escort hatay escort sivas escort rize escort edirne escort aksaray escort kibris escort isparta escort erzurum escort tekirdag escort usak escort urfa escort kastamonu escort kibris escort manisa escort giresun escort urfa escort nevsehir escort sivas escort yalova escort ordu escort hatay escort yalova escort amasya escort kayseri escort ordu escort maras escort canakkale escort yalova escort balikesir escort manisa escort urfa escort mugla escort trabzon escort bolu escort corlu escort diyarbakir escort isparta escort kutahya escort elazig escort erzurum escort sakarya escort afyon escort kutahya escort konya escort agri escort cesme escort sinop escort sivas escort konya escort kibris escort adapazari escort luleburgaz escort adana escort kibris escort rize escort sakarya escort alanya escort isparta escort burdur escort konya escort bitlis escort canakkale escort sivas escort amasya escort mus escort aydin escort van escort yalova escort kastamonu escort mardin escort bolu escort afyon escort sakarya escort isparta escort tokat escort trakya escort bayburt escort urfa escort mardin escort