Computational Study of Catalytic Urethane Formation

Waleed, Hadeer Q.; Csécsi, Marcell; Hadjadj, Rachid; Thangaraj, Ravikumar; Pecsmány, Dániel; Owen, Michael; Szőri, Milán; Fejes, Zsolt; Viskolcz, Béla; Fiser, Béla

doi:10.3390/polym14010008

Open AccessArticle

Computational Study of Catalytic Urethane Formation

by

Hadeer Q. Waleed

¹

,

Marcell Csécsi

¹,

Rachid Hadjadj

¹,

Ravikumar Thangaraj

¹,

Dániel Pecsmány

^1,2,

Michael Owen

^1,2,

Milán Szőri

¹

,

Zsolt Fejes

¹

,

Béla Viskolcz

¹

and

Béla Fiser

^1,2,3,*

¹

Institute of Chemistry, University of Miskolc, 3515 Miskolc, Hungary

²

Higher Education and Industrial Cooperation Centre, University of Miskolc, 3515 Miskolc, Hungary

³

Ferenc Rákóczi II, Transcarpathian Hungarian College of Higher Education, 90200 Berehove, Transcarpathia, Ukraine

^*

Author to whom correspondence should be addressed.

Polymers 2022, 14(1), 8; https://doi.org/10.3390/polym14010008

Submission received: 29 November 2021 / Revised: 13 December 2021 / Accepted: 16 December 2021 / Published: 21 December 2021

(This article belongs to the Special Issue Functional Polyurethanes II)

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Abstract

Polyurethanes (PUs) are widely used in different applications, and thus various synthetic procedures including one or more catalysts are applied to prepare them. For PU foams, the most important catalysts are nitrogen-containing compounds. Therefore, in this work, the catalytic effect of eight different nitrogen-containing catalysts on urethane formation will be examined. The reactions of phenyl isocyanate (PhNCO) and methanol without and in the presence of catalysts have been studied and discussed using the G3MP2BHandHLYP composite method. The solvent effects have also been considered by applying the SMD implicit solvent model. A general urethane formation mechanism has been proposed without and in the presence of the studied catalysts. The proton affinities (PA) were also examined. The barrier height of the reaction significantly decreased (∆E₀ > 100 kJ/mol) in the presence of the studied catalysts, which proves the important effect they have on urethane formation. The achieved results can be applied in catalyst design and development in the near future.

Keywords: catalysts; urethane formation; catalyst-free; DFT; proton affinities; composite method

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MDPI and ACS Style

Waleed, H.Q.; Csécsi, M.; Hadjadj, R.; Thangaraj, R.; Pecsmány, D.; Owen, M.; Szőri, M.; Fejes, Z.; Viskolcz, B.; Fiser, B. Computational Study of Catalytic Urethane Formation. Polymers 2022, 14, 8. https://doi.org/10.3390/polym14010008

AMA Style

Waleed HQ, Csécsi M, Hadjadj R, Thangaraj R, Pecsmány D, Owen M, Szőri M, Fejes Z, Viskolcz B, Fiser B. Computational Study of Catalytic Urethane Formation. Polymers. 2022; 14(1):8. https://doi.org/10.3390/polym14010008

Chicago/Turabian Style

Waleed, Hadeer Q., Marcell Csécsi, Rachid Hadjadj, Ravikumar Thangaraj, Dániel Pecsmány, Michael Owen, Milán Szőri, Zsolt Fejes, Béla Viskolcz, and Béla Fiser. 2022. "Computational Study of Catalytic Urethane Formation" Polymers 14, no. 1: 8. https://doi.org/10.3390/polym14010008

APA Style

Waleed, H. Q., Csécsi, M., Hadjadj, R., Thangaraj, R., Pecsmány, D., Owen, M., Szőri, M., Fejes, Z., Viskolcz, B., & Fiser, B. (2022). Computational Study of Catalytic Urethane Formation. Polymers, 14(1), 8. https://doi.org/10.3390/polym14010008

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Computational Study of Catalytic Urethane Formation

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