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Synlett 2024; 35(05): 598-602
DOI: 10.1055/s-0042-1751532
DOI: 10.1055/s-0042-1751532
letter
Investigation of Factors Affecting the Rate of High-Boiling-Point Solvent Removal Using a Rotary Evaporator
This work was supported by the Research Development Fund (RDF-20-02-30) and by PGRS2112027 of Xi’an Jiaotong-Liverpool University.
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 evaporatorSupporting 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
- 1b Physical Chemistry of Organic Solvent Systems . Covington AK, Dickinson T. Plenum Press; London: 1973
- 2 Ullmann’s Encyclopedia of Industrial Chemistry, Vol. 17. Elvers B. Wiley; Chichester: 1991. DOI:
- 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
- 5 Petrelli G, Siepi G, Miligi L, Vineis P. Scand. J. Work, Environ. Health 1993; 63
- 6 Warrag SE, Peters CJ, Kroon MC. Curr. Opin. Green Sustainable Chem. 2017; 5: 55
- 7a Welton T, Reichardt C. Solvents and Solvent Effects in Organic Chemistry, 4th ed. Wiley-VCH; Weinheim: 2011
- 7b Solvent Extraction Principles and Practice, 2nd ed. Rydberg J, Cox M, Musikas C, Choppin GR. Marcel Dekker; New York: 2004
- 8 Barwick VJ. Trends Anal. Chem. 1997; 16: 293
- 9a Craig LC, Gregory JD, Hausmann W. Anal. Chem. 1950; 22: 1462
- 9b Jensen WB. J. Chem. Educ. 2008; 85: 1481
- 10a Kumta P, Gallet D, Waghray A, Blomgren G, Setter M. J. Power Sources 1998; 72: 91
- 10b Mkawi E, Ibrahim K, Ali MK. M, Saron KM. A, Farrukh MA, Allam NK. Mater. Lett. 2014; 125: 195
- 10c Zhong R, Peng L, Iacobescu RI, Pontikes Y, Shu R, Ma L, Sels BF. ChemCatChem 2017; 9: 65
- 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
- 11 Clark CA, Lee DS, Pickering SJ, Poliakoff M, George MW. Org. Process Res. Dev. 2016; 20: 1792
- 12 Constable DJ, Jimenez-Gonzalez C, Henderson RK. Org. Process Res. Dev. 2007; 11: 133
- 13 Prat D, Hayler J, Wells A. Green Chem. 2014; 16: 4546
- 14a Nagata Y, Takeda R, Suginome M. ACS Cent. Sci. 2019; 5: 1235
- 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
- 16b Wang Y, Shen N. Renewable Sustainable Energy Rev. 2016; 62: 758
- 17a Loupy A. Top. Curr. Chem. 1999; 206: 153
- 17b Martins MA. P, Frizzo CP, Moreira DN, Buriol L, Machado P. Chem. Rev. 2009; 109: 4140
- 18a Tanaka K, Toda F. Chem. Rev. 2000; 100: 1025
- 18b Yoshizawa K, Toyota S, Toda F. Tetrahedron Lett. 2001; 42: 7983
- 18c Yusubov MS, Wirth T. Org. Lett. 2005; 7: 519
- 19a Candito DA, Dobrovolsky D, Lautens M. J. Am. Chem. Soc. 2012; 134: 15572
- 19b Kovács S, Csincsi AI, Nagy TZ, Boros S, Timári G, Novák Z. Org. Lett. 2012; 14: 2022
- 19c Reddy RS, Lagishetti C, Kiran IC, You H, He Y. Org. Lett. 2016; 18: 3818
- 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
- 19e Yoshioka E, Kakigi K, Miyoshi S, Kawasaki Y, Miyabe H. J. Org. Chem 2020; 85: 13544
- 20 Kolesnichenko IV, Goloverda GZ, Kolesnichenko VL. Org. Process Res. Dev. 2019; 24: 25
- 21a Li C.-J, Chen L. Chem. Soc. Rev. 2006; 35: 68
- 21b Simon M.-O, Li C.-J. Chem. Soc. Rev. 2012; 41: 1415
- 21c Gawande MB, Bonifacio VD. B, Luque R, Branco PS, Varma RS. Chem. Soc. Rev. 2013; 42: 5522
- 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
- 24 Le Bras J, Muzart J. Chem. Rev. 2011; 111: 1170
- 25 Dean E, Stark D. Ind. Eng. Chem. 1920; 12: 486
- 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:
- 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
- 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