Abstract
Researchers are forced to find alternative bio-based sources to produce fine chemicals due to the growing consumption and depletion of fossil resources. Methylsuccinic acid esters represent an exciting group of substances that could find potential in several areas of the chemical industry, such as polymers' production or a replacement of phthalates in plasticizers. Density, viscosity, and saturated vapor pressure are the fundamental properties for process simulations relating to the production of these compounds. 4 methylsuccinic acid esters with the commercial potential were studied in this paper—dimethyl methylsuccinate, diethyl methylsuccinate, di-n-propyl methylsuccinate, and di-n-butyl methylsuccinate. The presented data were experimentally determined, compared to the previously published data, if possible, and subsequently fitted by a relevant model for each property in Aspen Plus simulation software. The conformity between the experimental and calculated data were determined by values of average absolute deviation. The basic knowledge about these physical–chemical properties will be helpful in future process simulations and development in producing these esters.
Similar content being viewed by others
Abbreviations
- IA:
-
Itaconic acid
- MSA:
-
Methylsuccinic acid
- PBMS:
-
Poly(butylene-2-methyl succinate)
- DMMS:
-
Dimethyl methylsuccinate
- DEMS:
-
Diethyl methylsuccinate
- DPMS:
-
Di-n-propyl methylsuccinate
- DBMS:
-
Di-n-butyl methylsuccinate
- MAD:
-
Mean absolute deviation
- AAD:
-
Average absolute deviation
References
T. Werpy, G. Petersen, Top Value Added Chemicals from Biomass (the Pacific Northwest National Library and the National Renewable Energy Laboratory, 2004) https://www.nrel.gov/docs/fy04osti/35523.pdf. Accessed 23 Jan 2021
B. Cornils, P. Lappe, Ullmann’s Encyclopedia of Industrial Chemistry (Wiley, Weinhein, 2014)
J.T. Trotta, A. Watts, A.R. Wong, A.M. LaPointe, M.A. Hillmyer, B.P. Fors, ACS Sustain. Chem. Eng. 7, 2691 (2019)
B.C. Saha, G.J. Kennedy, N. Qureshi, M.J. Bowman, Biotechnol. Prog. 33, 1059 (2017)
J.C. De Carvalho, A.I. Magalhaes Jr., Soccol. C. R. Chim. Oggi 36, 56 (2018)
T. Klement, J. Buechs, Bioresour. Technol. 135, 422 (2013)
A. Kuenz, Y. Gallenmueller, T. Willke, K.-D. Vorlop, Appl. Microbiol. Biotechnol. 96, 1209 (2012)
W.E. Levinson, C.P. Kurtzman, T.M. Kuo, Enzyme Microb. Technol. 39, 824 (2006)
N. Maassen, M. Panakova, N. Wierckx, E. Geiser, M. Zimmermann, M. Boelker, U. Klinner, L.M. Blank, Eng. Life Sci. 14, 129 (2014)
X. Huang, X. Lu, Y. Li, X. Li, J.-J. Li, Microb. Cell Fact. 13, 119 (2014)
Y. Liu, G. Liu, J. Zhang, V. Balan, J. Bao, Biomass Convers. Biorefin. 10, 463 (2020)
F.J. Holzhäuser, J. Artz, S. Palkovits, D. Kreyenschulte, J. Büchs, R. Palkovits, Green Chem. 19, 2390 (2017)
R. Luque, J.H. Clark, Catal. Commun. 11, 928 (2010)
D. Mijolovic, Z. J. Szarka, J. Heimann, S. Garnier, DE102011080722 (2012)
L. Wu, M. Mascal, T.J. Farmer, S.P. Arnaud, M.-A. WongChang, ChemSusChem 10, 166 (2017)
T. Xie, C. Gao, C. Wang, S.E. Shen, Y. Wu, Polym.-Plast. Technol. Eng. 53, 465 (2014)
J. Han, J. Shi, Z. Xie, J. Xu, B. Guo, Materials 12, 1507 (2019)
H. Richard, B. Muller, WO2012119861 (2012)
J. Trejbal, M. Zapletal, A. Obuchov, T. Sommer, Int. J. Thermophys. 43, 51 (2022)
G. H. Jeffery, A. I. Vogel, J. Chem. Soc. 658 (1948)
J.W. Brühl, R. Braunschweig, J. Prakt. Chem. 47, 274 (1893)
P.A. Meerburg, Recl. Trav. Chim. Pays-Bas 18, 367 (1899)
W. Ipatiew, G. Rasuwajew, Ber. Dtsch. Chem. Ges. 59, 2031 (1926)
W.H. Perkin, J. Chem. Soc. Trans. 45, 421 (1884)
N.A. Preobrazhenskii, M.E. Maurit, G.I. Bazilevskaya, G.V. Smirnova, M.M. El’manovich, A.I. Valakhanovich, E. Persiyanova, Zh. Obshch, Khim. 30, 2250 (1960)
K.V. Auwers, B. Ottens, Ber. Dtsch. Chem. Ges. 57, 437 (1924)
G. Natta, P. Pino, E. Mantica, Gazz. Chim. Ital. 80, 680 (1950)
R. Rossi, P. Diversi, G. Ingrosso, Gazz. Chim. Ital. 98, 1391 (1968)
M. S. Adjangba, Bull. Soc. Chim. Fr. 1942 (1963)
F. Echalier, O. Constant, J. Bolte, J. Org. Chem. 58, 2747 (1993)
Y. Murakami, Y. Hisaeda, T. Ozaki, T. Tashiro, T. Ono, Y. Tani, Y. Matsuda, Bull. Chem. Soc. Jpn. 60, 311 (1987)
M. Qudrat-i-Khuda, S.K. Ghosh, J. Indian Chem. Soc. 17, 19 (1940)
B. Wojcik, H. Adkins, J. Am. Chem. Soc. 56, 2424 (1934)
Author information
Authors and Affiliations
Contributions
The manuscript was written through the contribution of Martin Zapletal, Jiří Pokorný, Jiří Trejbal, and Tomáš Sommer.
Corresponding author
Ethics declarations
Conflict of interest
The authors declare no competing financial interests. All authors have approved the final version of the manuscript.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Supplementary Information
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Zapletal, M., Pokorný, J., Trejbal, J. et al. Experimental Determination and Correlation of Density, Viscosity, and Saturated Vapor Pressure Data of Various Methylsuccinic Acid Esters. Int J Thermophys 43, 120 (2022). https://doi.org/10.1007/s10765-022-03047-4
Received:
Accepted:
Published:
DOI: https://doi.org/10.1007/s10765-022-03047-4