Novel eco-efficient reactive distillation process for dimethyl carbonate production by indirect alcoholysis of urea

Iulian Patrașcu, Costin S. Bîldea, Anton A. Kiss

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PDF(3382 KB)
Front. Chem. Sci. Eng. ›› 2022, Vol. 16 ›› Issue (2) : 316-331. DOI: 10.1007/s11705-021-2047-9
RESEARCH ARTICLE
RESEARCH ARTICLE

Novel eco-efficient reactive distillation process for dimethyl carbonate production by indirect alcoholysis of urea

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Abstract

Dimethyl carbonate is an eco-friendly essential chemical that can be sustainably produced from CO2, which is available from carbon capture activities or can even be captured from the air. The rapid increase in dimethyl carbonate demand is driven by the fast growth of polycarbonates, solvent, pharmaceutical, and lithium-ion battery industries. Dimethyl carbonate can be produced from CO2 through various chemical pathways, but the most convenient route reported is the indirect alcoholysis of urea. Previous research used techniques such as heat integration and reactive distillation to reduce the energy use and costs, but the use of an excess of methanol in the trans-esterification step led to an energy intensive extractive distillation required to break the dimethyl carbonate-methanol azeotrope. This work shows that the production of dimethyl carbonate by indirect alcoholysis of urea can be improved by using an excess of propylene carbonate (instead of an excess of methanol), a neat feat that we showed it requires only 2.64 kW·h·kg–1 dimethyl carbonate in a reaction-separation-recycle process, and a reactive distillation column that effectively replaces two conventional distillation columns and the reactor for dimethyl carbonate synthesis. Therefore, less equipment is required, the methanol-dimethyl carbonate azeotrope does not need to be recycled, and the overall savings are higher. Moreover, we propose the use of a reactive distillation column in a heat integrated process to obtain high purity dimethyl carbonate (>99.8 wt-%). The energy requirement is reduced by heat integration to just 1.25 kW·h·kg–1 dimethyl carbonate, which is about 52% lower than the reaction-separation-recycle process. To benefit from the energy savings, the dynamics and control of the process are provided for ±10% changes in the nominal rate of 32 ktpy dimethyl carbonate, and for uncertainties in reaction kinetics.

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Keywords

dimethyl carbonate / reactive distillation / process design / plantwide control

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Iulian Patrașcu, Costin S. Bîldea, Anton A. Kiss. Novel eco-efficient reactive distillation process for dimethyl carbonate production by indirect alcoholysis of urea. Front. Chem. Sci. Eng., 2022, 16(2): 316‒331 https://doi.org/10.1007/s11705-021-2047-9

References

[1]
Tundo P, Selva M. The chemistry of dimethyl carbonate. Accounts of Chemical Research, 2002, 35(9): 706–716
CrossRef Google scholar
[2]
Santos B A V, Silva V M T M, Loureiro M J, Rodrigues A E. Review for the direct synthesis of dimethyl carbonate. ChemBioEng Reviews, 2014, 1(5): 214–229
CrossRef Google scholar
[3]
Huang Z, Li J, Wang L, Jiang H, Qiu T. Novel procedure for the synthesis of dimethyl carbonate by reactive distillation. Industrial & Engineering Chemistry Research, 2014, 53(8): 3321–3328
CrossRef Google scholar
[4]
Kongpanna P, Pavarajarn V, Gani R, Assabumrungrat S. Techno-economic evaluation of different CO2-based processes for dimethyl carbonate production. Chemical Engineering Research & Design, 2015, 93: 496–510
CrossRef Google scholar
[5]
Matsuzaki T, Nakamura A. Dimethyl carbonate synthesis and other oxidative reactions using alkyl nitrites. Catalysis Surveys from Japan, 1997, 1(1): 77–88
CrossRef Google scholar
[6]
Sánchez A, Gil L M, Martín M. Sustainable DMC production from CO2 and renewable ammonia and methanol. Journal of CO2 Utilization, 2019, 33: 521–531
[7]
Shi L, Wang D J, Wong D S H, Huang K. Novel process design of synthesizing propylene carbonate for dimethyl carbonate production by indirect alcoholysis of urea. Industrial & Engineering Chemistry Research, 2017, 56(40): 11531–11544
CrossRef Google scholar
[8]
Patrașcu I, Bîldea C S, Kiss A A. Novel eco-efficient process for dimethyl carbonate production by indirect alcoholysis of urea. Chemical Engineering Research & Design, 2020, 160: 486–498
CrossRef Google scholar
[9]
Pacheco M A, Marshall C L. Review of dimethyl carbonate (DMC) manufacture and its characteristics as a fuel additive. Energy & Fuels, 1997, 11(1): 2–29
CrossRef Google scholar
[10]
Tan H Z, Wang Z Q, Xu Z N, Sun J, Xu Y P, Chen Q S, Chen Y, Guo G C. Review on the synthesis of dimethyl carbonate. Catalysis Today, 2018, 316: 2–12
CrossRef Google scholar
[11]
Kuenen H J, Mengers H J, Nijmeijer D C, van der Ham A G J, Kiss A A. Techno-economic evaluation of the direct conversion of CO2 to dimethyl carbonate using catalytic membrane reactors. Computers & Chemical Engineering, 2016, 86: 136–147
CrossRef Google scholar
[12]
Hsu K Y, Hsiao Y C, Chien I L. Design and control of dimethyl carbonate-methanol separation via extractive distillation in the dimethyl carbonate reactive-distillation process. Industrial & Engineering Chemistry Research, 2010, 49(2): 735–749
CrossRef Google scholar
[13]
Wang S J, Yu C C, Huang H P. Plant-wide design and control of DMC synthesis process via reactive distillation and thermally coupled extractive distillation. Computers & Chemical Engineering, 2010, 34(3): 361–373
CrossRef Google scholar
[14]
Li Q, Zhang S, Ding B, Cao L, Liu P, Jiang Z, Wang B. Isobaric vapor liquid equilibrium for methanol+ dimethyl carbonate+ trifluoromethanesulfonate-based ionic liquids at 101.3 kPa. Industrial & Engineering Chemistry Chemical & Engineering Data Series, 2014, 59: 3488–3494
[15]
Matsuda H, Takahara H, Fujino S, Constantinescu D, Kurihara K, Tochigi K, Ochi K, Gmehling J. Isothermal vapor-liquid equilibria at 383.15–413.15 K for the binary system methanol+ DMC and the pressure dependency of the azeotropic point. Fluid Phase Equilibria, 2019, 492: 101–109
CrossRef Google scholar
[16]
Luo H P, Zhou J H, Xiao W D, Zhu K H J. Isobaric vapor-liquid equilibria of binary mixtures containing DMC under atmospheric pressure. Journal of Chemical & Engineering Data, 2001, 46(4): 842–845
CrossRef Google scholar
[17]
Mathuni T, Kim J I, Park S J J. Phase equilibrium and physical properties for the purification of propylene carbonate (PC) and y-butyrolactone (GBL). Journal of Chemical & Engineering Data, 2011, 56(1): 89–96
CrossRef Google scholar
[18]
Pyrlik A, Hoelderich W, Müller K, Arlt W, Strautmann J, Kruse D. Dimethyl carbonate via transesterification of propylene carbonate with methanol over ion exchange resign. Applied Catalysis, 2012, B125: 486–491
CrossRef Google scholar
[19]
Holtbruegge J, Leimbrink M, Lutze P, Górak A. Synthesis of dimethyl carbonate and propylene glycol by transesterification of propylene carbonate with methanol: catalyst screening, chemical equilibrium and reaction kinetics. Chemical Engineering Science, 2013, 104: 347–360
CrossRef Google scholar
[20]
Dimian A C. Integrated Design and Simulation of Chemical Processes. Amsterdam: Elsevier, 2003
[21]
Luyben W L. Principles and Case Studies of Simultaneous Design. Hoboken: Wiley, 2011
[22]
Kiss A A. Advanced Distillation Technologies. Chichester: Wiley, 2013
[23]
Alibaba. Dimethyl carbonate (CAS 616-38-6), Alibaba website, 2020
[24]
IndexMundi. Urea monthly price—US dollars per metric ton, IndexMundi website, 2020
[25]
Methanex. Methanex posts regional contract methanol prices for North America, Europe and Asia, Methanex website, 2020
[26]
Schwartz J, Beloff B, Beaver E. Use sustainability metrics to guide decision-making. Chemical Engineering Progress, 2002, 98(7): 58–63

Acknowledgements

The financial support of the European Commission through the European Regional Development Fund and of the Romanian state budget, under the grant agreement POC P-37-449 (acronym ASPiRE) is gratefully acknowledged. AAK gratefully acknowledges the Royal Society Wolfson Research Merit Award (Grant No. WM170003).

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