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Synlett 2024; 35(05): 598-602
DOI: 10.1055/s-0042-1751532
letter

Investigation of Factors Affecting the Rate of High-Boiling-Point Solvent Removal Using a Rotary Evaporator

Yinzhe Chen
a   Department of Chemistry, Xi’an-Jiaotong Liverpool University, Suzhou, Jiangsu Province, 215123, P. R. of China
c   Institute of Systems, Molecular and Integrative Biology, University of Liverpool, Liverpool L69 7BE, UK
,
Weiding Wang
a   Department of Chemistry, Xi’an-Jiaotong Liverpool University, Suzhou, Jiangsu Province, 215123, P. R. of China
b   Department of Chemistry, University of Liverpool, Liverpool L69 7ZD, UK
,
Qian Zhang  ∗
a   Department of Chemistry, Xi’an-Jiaotong Liverpool University, Suzhou, Jiangsu Province, 215123, P. R. of China
b   Department of Chemistry, University of Liverpool, Liverpool L69 7ZD, UK
› Author AffiliationsThis work was supported by the Research Development Fund (RDF-20-02-30) and by PGRS2112027 of Xi’an Jiaotong-Liverpool University.
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Abstract

Factors that might affect the removal time of high-boiling-point solvents with a rotary evaporator were examined. Considering several essential factors, the optimized conditions for removing a high-boiling-point solvent are suggested. The results and discussion from this work can serve as a reference for current and future organic chemists. Finally, two examples of fast and successful dehydration reactions are given to demonstrate that the rotary evaporator can be used to conduct organic syntheses.

Key words

high-boiling solvents - dehydration - organic solvents - solvent removal - rotary evaporator

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0042-1751532.
  • Supporting Information


Publication History

Received: 11 October 2023

Accepted after revision: 01 November 2023

Article published online:
26 January 2024

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  • References and Notes

    • 1a Dick FD. Occup. Environ. Med. 2006; 63: 221
      CrossrefPubMed
    • 1b Physical Chemistry of Organic Solvent Systems . Covington AK, Dickinson T. Plenum Press; London: 1973
      Google Scholar
  • 2 Ullmann’s Encyclopedia of Industrial Chemistry, Vol. 17. Elvers B. Wiley; Chichester: 1991. DOI: DOI: 10.1002/14356007
    CrossrefGoogle Scholar
  • 3 Grodowska K, Parczewski A. Acta Pol. Pharm. 2010; 67: 1
  • 4 Martinez RM, Rosado C, Velasco MV. R, Lannes SC. S, Baby AR. Int. J. Cosmet. Sci. 2019; 41: 109
    CrossrefPubMed
  • 5 Petrelli G, Siepi G, Miligi L, Vineis P. Scand. J. Work, Environ. Health 1993; 63
    CrossrefPubMed
  • 6 Warrag SE, Peters CJ, Kroon MC. Curr. Opin. Green Sustainable Chem. 2017; 5: 55
    Crossref
    • 7a Welton T, Reichardt C. Solvents and Solvent Effects in Organic Chemistry, 4th ed. Wiley-VCH; Weinheim: 2011
      Google Scholar
    • 7b Solvent Extraction Principles and Practice, 2nd ed. Rydberg J, Cox M, Musikas C, Choppin GR. Marcel Dekker; New York: 2004
      Google Scholar
  • 8 Barwick VJ. Trends Anal. Chem. 1997; 16: 293
    Crossref
    • 9a Craig LC, Gregory JD, Hausmann W. Anal. Chem. 1950; 22: 1462
      Crossref
    • 9b Jensen WB. J. Chem. Educ. 2008; 85: 1481
      Crossref
    • 10a Kumta P, Gallet D, Waghray A, Blomgren G, Setter M. J. Power Sources 1998; 72: 91
      Crossref
    • 10b Mkawi E, Ibrahim K, Ali MK. M, Saron KM. A, Farrukh MA, Allam NK. Mater. Lett. 2014; 125: 195
      Crossref
    • 10c Zhong R, Peng L, Iacobescu RI, Pontikes Y, Shu R, Ma L, Sels BF. ChemCatChem 2017; 9: 65
      Crossref
    • 10d Wang S, Zhang L, Chen W, Jin H, Zhang Y, Wu L, Shao H, Fang Z, He X, Zheng S, Cao CY, Wong HM, Li Q. Mater. Sci. Eng., C 2020; 115: 111141
      CrossrefPubMed
  • 11 Clark CA, Lee DS, Pickering SJ, Poliakoff M, George MW. Org. Process Res. Dev. 2016; 20: 1792
    Crossref
  • 12 Constable DJ, Jimenez-Gonzalez C, Henderson RK. Org. Process Res. Dev. 2007; 11: 133
    Crossref
  • 13 Prat D, Hayler J, Wells A. Green Chem. 2014; 16: 4546
    Crossref
    • 14a Nagata Y, Takeda R, Suginome M. ACS Cent. Sci. 2019; 5: 1235
      CrossrefPubMed
    • 14b Peplow M. Chem. Eng. News 2019; 97: 8
  • 15 Thomas J. Trends Anal. Chem. 1995; 14: 186
    • 16a Silbergeld EK, Mandrioli D, Cranor CF. Annu. Rev. Public Health 2015; 36: 175
      CrossrefPubMed
    • 16b Wang Y, Shen N. Renewable Sustainable Energy Rev. 2016; 62: 758
      Crossref
    • 17a Loupy A. Top. Curr. Chem. 1999; 206: 153
      Crossref
    • 17b Martins MA. P, Frizzo CP, Moreira DN, Buriol L, Machado P. Chem. Rev. 2009; 109: 4140
      CrossrefPubMed
    • 18a Tanaka K, Toda F. Chem. Rev. 2000; 100: 1025
      CrossrefPubMed
    • 18b Yoshizawa K, Toyota S, Toda F. Tetrahedron Lett. 2001; 42: 7983
      Crossref
    • 18c Yusubov MS, Wirth T. Org. Lett. 2005; 7: 519
      CrossrefPubMed
    • 19a Candito DA, Dobrovolsky D, Lautens M. J. Am. Chem. Soc. 2012; 134: 15572
      CrossrefPubMed
    • 19b Kovács S, Csincsi AI, Nagy TZ, Boros S, Timári G, Novák Z. Org. Lett. 2012; 14: 2022
      CrossrefPubMed
    • 19c Reddy RS, Lagishetti C, Kiran IC, You H, He Y. Org. Lett. 2016; 18: 3818
      CrossrefPubMed
    • 19d You H, Vegi SR, Lagishetti C, Chen S, Reddy RS, Yang X, Guo J, Wang C, He Y. J. Org. Chem 2018; 83: 4119
      CrossrefPubMed
    • 19e Yoshioka E, Kakigi K, Miyoshi S, Kawasaki Y, Miyabe H. J. Org. Chem 2020; 85: 13544
      CrossrefPubMed
  • 20 Kolesnichenko IV, Goloverda GZ, Kolesnichenko VL. Org. Process Res. Dev. 2019; 24: 25
    CrossrefPubMed
    • 21a Li C.-J, Chen L. Chem. Soc. Rev. 2006; 35: 68
      CrossrefPubMed
    • 21b Simon M.-O, Li C.-J. Chem. Soc. Rev. 2012; 41: 1415
      CrossrefPubMed
    • 21c Gawande MB, Bonifacio VD. B, Luque R, Branco PS, Varma RS. Chem. Soc. Rev. 2013; 42: 5522
      CrossrefPubMed
  • 22 Alsohaimi IH, Wabaidur SM, Kumar M, Khan MA, Alothman ZA, Abdalla MA. Chem. Eng. J. (Amsterdam, Neth.) 2015; 270: 9
  • 23 El-Faham A, Albericio F. Chem. Rev. 2011; 111: 6557
    CrossrefPubMed
  • 24 Le Bras J, Muzart J. Chem. Rev. 2011; 111: 1170
    CrossrefPubMed
  • 25 Dean E, Stark D. Ind. Eng. Chem. 1920; 12: 486
    Crossref
  • 26 ACS Division of Organic Chemistry; Common Solvents Used in Organic Chemistry: Table of Properties; American Chemical Society: Washington, DC: 2022 (accessed Nov 27, 2023); https://organicchemistrydata.org/solvents/.
  • 27 Suslick KS. In 1997 IEEE Ultrasonics Symposium Proceedings. An International Symposium . Schneider SC, Levy M, McAvoy BR. IEEE; Piscataway: 1997. DOI: DOI: 10.1109/ULTSYM.1997.663076
    CrossrefGoogle Scholar
  • 28 The appropriately sized round-bottomed flask was charged with the substrates and catalyst. For the reaction in the rotavap, the temperature of the water bath was fixed at 70 °C, the temperature of the coolant-circulation system was fixed at 0 ℃, and the rotation speed was set to 100 rpm. The pressure was maintained at 20 mbar by the vacuum system during the reaction. For the reaction at ambient pressure, the mixture was heated and refluxed in a 500 mL round-bottomed flask.
  • 29 Chiba T, Kurokawa H. US 2013101934, 2013
    PubMed
  • 30 The substrates and catalyst were added to a 500 mL round-bottomed flask, which was then attached to a rotavap. The temperature of the water bath was fixed at 70 ℃, the temperature of the coolant-circulation system was fixed at 0 ℃, and the rotation speed was set to 100 rpm. The crude product was obtained after quenching the reaction with sat. aq NaHCO3, extraction, and evaporation of the solvent.
  • 31 Wang S, Rodríguez-Escrich C, Fan X, Pericàs MA. Tetrahedron 2018; 74: 3943
    Crossref