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Synthesis 2012; 44(16): 2515-2518
DOI: 10.1055/s-0031-1290823
practical synthetic procedures
© Georg Thieme Verlag Stuttgart · New York

Convenient Preparation of Long-Chain Dialkyl Phosphates: Synthesis of Dialkyl Phosphates

R. Alan Aitken*
a   EaStCHEM School of Chemistry, University of St Andrews, North Haugh, St Andrews, Fife KY16 9ST, UK
,
Chris J. Collett
a   EaStCHEM School of Chemistry, University of St Andrews, North Haugh, St Andrews, Fife KY16 9ST, UK
b   SynOil Energy Services, 2000, 300 - 5th Ave SW, Calgary, AB, T2P 3C4, Canada, Fax: +44(1334)463808   Email: raa@st-and.ac.uk
,
Shaun T. E. Mesher
b   SynOil Energy Services, 2000, 300 - 5th Ave SW, Calgary, AB, T2P 3C4, Canada, Fax: +44(1334)463808   Email: raa@st-and.ac.uk
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Further Information

Publication History

Received: 07 February 2012

Accepted after revision: 02 March 2012

Publication Date:
17 April 2012 (online)

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Abstract

Reaction of phosphorus oxychloride with a primary alcohol (1.8 equiv) and triethylamine (1.8 equiv) in toluene, followed by filtration and treatment with steam, gives dialkyl phosphates in good yield and essentially free from trialkyl phosphate contamination.

Key words

dialkyl phosphates - esterification - hydrolysis - hydraulic fracturing - enhanced oil recovery
 

  • References

  • 1 Smith KW, Persinski LJ. US Patent 5417287, 1995 ; Chem. Abstr. 1995, 123, 87963
  • 2 Mesher ST, Collett C. PCT Int. Appl. WO 2010/022496, 2010 ; Chem. Abstr. 2010, 152, 339215
  • 3 Huddleston DA. US Patent 5110485, 1992 ; Chem. Abstr. 1992, 117, 154297
  • 4 Woodstock WH. US Patent 2402703, 1946 ; Chem. Abstr. 1946, 40, 27725
  • 5 Mesher ST. E. US Patent 6039865, 2000 ; US Patent Appl. 2003/0024855, 2003; Chem. Abstr. 2000, 132, 210047
    • 6a Lukocs B, Mesher S, Wilson TP, Garza T, Mueller W, Zamora F, Gatlin LW. Canadian Patent 2552657, 2006 , US Patent Appl. 2007/0173413; Chem. Abstr. 2007, 147, 192514
    • 6b Funkhouser GP. US Patent 7066262, 2006 ; Chem. Abstr. 2006, 144, 256872
  • 7 Quaedflieg PJ. L. M, Timmers CM, van der Marel GA, Kuyl-Yeheskiely E, van Boom JH. Synthesis 1993; 627
    Thieme Connect
  • 8 Wu P.-L, Chen J.-H, Huang D.-S. J. Chin. Chem. Soc. 1999; 46: 967 ; Chem. Abstr. 2000, 132, 166275
    Search in Google Scholar
  • 9 Kunitake T, Okahata Y. Bull. Chem. Soc. Jpn. 1978; 51: 1877
    CrossrefSearch in Google Scholar
  • 10 Dewa T, Asai T, Nango M, Oku N. US Patent 0094020, 2010 ; Chem. Abstr. 2010, 152, 453842
  • 11 Grosse-Ruyken H, Uhlig K. J. Prakt. Chem. 1962; 18: 287
    CrossrefSearch in Google Scholar
  • 12 Petrov KA, Nifant’ev EE, Lysenko TN. Zh. Obshch. Khim. 1961; 31: 1709 ; Chem. Abstr. 1961, 55, 124269
    Search in Google Scholar
  • 13 Bailer JC. Inorg. Synth. 1953; 4: 61
    Search in Google Scholar
  • 14 Acharya J, Gupta AK, Shakya PD, Kaushik MP. Tetrahedron Lett. 2005; 46: 5293
    CrossrefSearch in Google Scholar
  • 15 Gupta HK, Mazumder A, Garg P, Gutch PK, Dubey DK. Tetrahedron Lett. 2008; 49: 6704
    CrossrefSearch in Google Scholar
  • 16 Nehmsmann LJ III, Nunn LG. Jr, Schenck LM. US Patent 3277217, 1966 ; Chem. Abstr. 1965, 62, 90779
  • 17 Cox JR. Jr, Westheimer FH. J. Am. Chem. Soc. 1958; 80: 5441
    CrossrefSearch in Google Scholar
  • 18 Chachaty C, Korb J.-P. J. Phys. Chem. 1988; 92: 2834
    CrossrefSearch in Google Scholar
  • 19 Arad-Yellin R, Zangen M, Gottlieb H, Warshawsky A. J. Chem. Soc., Dalton Trans. 1990; 2081
  • 20 Wagenaar A, Rupert LA. M, Engberts JB. F. N, Hoekstra D. J. Org. Chem. 1989; 54: 2638
    CrossrefSearch in Google Scholar
  • 21 Okahata Y, Seki T. J. Am. Chem. Soc. 1984; 106: 8065
    CrossrefSearch in Google Scholar