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Investigation of propylene carbonate synthesis regularities by the interaction of propylene glycol with carbamide

https://doi.org/10.32362/2410-6593-2019-15-1-55-61

Abstract

Objectives. Cyclic carbonates are important products of organic synthesis, which are widely used as solvents, catalysts, and reagents for the production of various compounds (in particular, urethane-containing polymers) by the non-isocyanate method. The process of carbamide alcoholysis with polybasic alcohols is a promising method for the synthesis of cyclic carbonates. The purpose of this study is to determine the reaction conditions for the interaction of propylene glycol with carbamide in the presence of zinc acetate as a catalyst.

Methods. We conducted experiments to study the synthesis of propylene carbonate in a batch laboratory apparatus. Moreover, we analyzed the starting reagents and final products using gas–liquid chromatography.

Results. We studied the synthesis of propylene carbonate by carbamide alcoholysis with propylene glycol in the presence of a catalyst (zinc acetate) by varying the following parameters: initial molar ratio of propylene glycol/carbamide = (0.5–5):1, synthesis temperature 130–190°С, reagent residence time in the reactor 0.5–4 h, and the catalyst amount in the reaction mixture 0–1.5 wt %.

Conclusions. We determined the technological parameters of propylene carbonate synthesis in a batch reactor. Moreover, we showed that the process allowed the production of propylene carbonate with a sufficiently high yield of 80%—at the initial molar ratio of propylene glycol/ carbamide = 3:1, temperature 170°C, and residence time 2 h.

About the Authors

A. V. Sulimov
Nizhny Novgorod State Technical University n.a. R.E. Alekseev
Russian Federation

Aleksandr V. Sulimov, Dr. of Sci. (Engineering), Professor, Department of Chemical and Food Technologies. Scopus Author ID 56497239500, ResearcherID K-5437-2015

49, Gaidara ul., Dzerzhinsk, Nizhny Novgorod oblast, 606000



A. V. Ovcharova
Nizhny Novgorod State Technical University n.a. R.E. Alekseev
Russian Federation

Anna V. Ovcharova, Cand. of Sci. (Chemistry), Associate Professor, Department of Chemical and Food Technologies. Scopus Author ID 55263080200

49, Gaidara ul., Dzerzhinsk, Nizhny Novgorod oblast, 606000



G. M. Kravchenko
Nizhny Novgorod State Technical University n.a. R.E. Alekseev
Russian Federation

Grigory M. Kravchenko, Master Student, Department of Chemical and Food Technologies.

49, Gaidara ul., Dzerzhinsk, Nizhny Novgorod oblast, 606000



Yu. K. Sulimova
Nizhny Novgorod State Technical University n.a. R.E. Alekseev
Russian Federation

Yulia K. Sulimova, Master Student, Department of Chemical and Food Technologies.

49, Gaidara ul., Dzerzhinsk, Nizhny Novgorod oblast, 606000



References

1. Shaikh A.G., Sivaram S. Organic Carbonates. Chem. Rev. 1996;96(3):951-976. https://doi.org/10.1021/cr950067i

2. Debotton N., Dahan A. Applications of Polymers as Pharmaceutical Excipients in Solid Oral Dosage Forms. Med. Res. Rev. 2017;37(1):52-97. https://doi.org/10.1002/med.21403

3. Zhou J., Dongfang W., Zhang B., Guo Y. Synthesis of propylene carbonate from urea and 1,2-propylene glycol over metal carbonates. Chem. Ind. Chem. Eng. Q. 2011;17(3):323-331. https://doi.org/10.2298/CICEQ101123018Z

4. Suib S.L. (Ed.) New and Future Developments in Catalysis. Elsevier: Amsterdam; 2013. 478 p. ISBN 978-0-444-53882-6

5. Darensbourg D.J., Holtcamp M.W. Catalysts for the reactions of epoxides and carbon dioxide. Coord. Chemi. Rev. 1996;153:155-174. https://doi.org/10.1016/0010-8545(95)01232-X

6. Shukla K., Srivastava V.C. Synthesis of organic carbonates from alcoholysis of urea: A review. Catal. Rev. 2017;59(1)1-43. https://doi.org/10.1080/01614940.2016.1263088

7. Aresta M., Dibenedetto A. Utilisation of CO<sub>2</sub> as a chemical feedstock: opportunities and challenges. Dalton Transactions. 2007;28:2975-2992. https://doi.org/10.1039/B700658F

8. Mikkelsen M., Jorgensen M., Krebs F.C. The teraton challenge. A review of fixation and transformation of carbon dioxide. Energ. Environ. Sci. 2010;3(1)43-81. https://doi.org/10.1039/B912904A

9. Dasari M.A., Kiatsimku P.-P., Sutterlin W.R., Suppes G.J. Low-pressure hydrogenolysis of glycerol to propylene glycol. Appl. Catal. A-G. 2005;281(1):225-231. https://doi.org/10.1016/j.apcata.2004.11.033

10. Maris E.P., Davis R.J. Hydrogenolysis of glycerol over carbon-supported Ru and Pt catalysts. J. Catal. 2007;249(2):328-337. https://doi.org/10.1016/j.jcat.2007.05.008

11. Xiu Z.-L., Zeng A.-P. Present state and perspective of downstream processing of biologically produced 1,3-propanediol and 2,3-butanediol. Appl. Microbiol. Biotechnol. 2008;78(6):917-926. https://doi.org/10.1007/s00253-008-1387-4

12. Sulimov A.V., Ovcharova A.V., Ovcharov A.A., Ryabova T.A., Kravchenko G.M., Lysanov S.A. Synthesizing cyclic carbonates from olefin oxides and carbon dioxide. I: Catalysis with ionic liquids. Catalysis in Industry. 2016;8(4):300-309. https://doi.org/10.1134/s2070050416040103

13. Decortes A., Castilla A.M., Kleij A.W. SalenComplex-Mediated Formation of Cyclic Carbonates by Cycloaddition of CO<sub>2</sub> to Epoxides. Angew. Chem. Int. Ed. 2010;49(51):9822-9837. https://doi.org/10.1002/anie.201002087

14. Sheng, X., Guo H., Qin Y., Wang X., Wang F. A novel metalloporphyrin-based conjugated microporous polymer for capture and conversion of CO<sub>2</sub> . RSC Advances. 2015;5(40):31664-31669. https://doi.org/10.1039/C4RA16675B

15. Li Q., Zhao N., Wei W., Sun Y. Catalytic performance of metal oxides for the synthesis of propylene carbonate from urea and 1,2-propanediol. J. Mol. Catal. A-Chem. 2007;270(1):44-49. https://doi.org/10.1016/j.molcata.2007.01.018

16. Zhao X., Sun N., Wang S., Li F. Synthesis of Propylene Carbonate from Carbon Dioxide and 1,2-Propylene Glycol over Zinc Acetate Catalyst. Ind. Eng. Chem. Res. 2008;47(5):1365-1369. https://doi.org/10.1021/ie070789n

17. Gurvich L.V., Veyts I.V., Medvedev V.A. Thermodynamic properties of individual substances. Vol. 1, part 1. New York, United States: 1989. 551 p.


Supplementary files

1. Possible routes for the synthesis of propylene carbonate.
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2. This is to certify that the paper titled Investigation of propylene carbonate synthesis regularitiesby the interaction of propylene glycol with carbamide commissioned to Enago by Aleksandr V. Sulimov, Anna V. Ovcharova, Grigory M. Kravchenko, Yulia K. Sulimova has been edited for English language and spelling by Enago, an editing brand of Crimson Interactive Inc.
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The synthesis of propylene carbonate from propylene glycol and carbamide (urea) is described herein. The synthetic yield depended on the initial ratio of the reactants, temperature, time, and concentration of the catalyst. Zinc acetate was used as the reaction catalyst.

Review

For citations:


Sulimov A.V., Ovcharova A.V., Kravchenko G.M., Sulimova Yu.K. Investigation of propylene carbonate synthesis regularities by the interaction of propylene glycol with carbamide. Fine Chemical Technologies. 2020;15(1):55-61. https://doi.org/10.32362/2410-6593-2019-15-1-55-61

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ISSN 2410-6593 (Print)
ISSN 2686-7575 (Online)