A Theoretical Study on the Phosgenation of 2,4-Toluenediamine (2,4-TDA)
Industrially relevant phosgenation mechanisms of 2,4-toluenediamine (2,4-TDA) were investigated using G3MP2B3 model chemistry. Six reaction pathways had been explored, which resulted in the formation of toluene diisocyanate (2,4-TDI) including different scenarios of the ‘phosgenations first’ and ‘co...
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| Format: | Article |
| Language: | English |
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MDPI AG
2022-05-01
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| Series: | Polymers |
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| Online Access: | https://www.mdpi.com/2073-4360/14/11/2254 |
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| author | Ravikumar Thangaraj Tamás Horváth R. Zsanett Boros Béla Viskolcz Milán Szőri |
| author_facet | Ravikumar Thangaraj Tamás Horváth R. Zsanett Boros Béla Viskolcz Milán Szőri |
| author_sort | Ravikumar Thangaraj |
| collection | DOAJ |
| description | Industrially relevant phosgenation mechanisms of 2,4-toluenediamine (2,4-TDA) were investigated using G3MP2B3 model chemistry. Six reaction pathways had been explored, which resulted in the formation of toluene diisocyanate (2,4-TDI) including different scenarios of the ‘phosgenations first’ and ‘consecutive phosgenations’ mechanisms in both gas and condensed phases. Two possible ‘phosgenations first’ mechanisms show superior to the others in terms of energy, regardless of which phases are considered. Due to the o-dichlorobenzene (ODCB) solvation, the reaction barriers are dramatically reduced compared to the gas-phase reaction mechanism and the solvent effect can be described by linear relationship. Standard enthalpy of formation value was also recommended for 2,4-TDA (59.3 kJ/mol) and 2,4-TDI (−94.1 kJ/mol), as well as for the gas-phase intermediates (IM). |
| first_indexed | 2024-03-10T00:57:10Z |
| format | Article |
| id | doaj.art-dd3cc0799167412099fb5f1efef02a14 |
| institution | Directory Open Access Journal |
| issn | 2073-4360 |
| language | English |
| last_indexed | 2024-03-10T00:57:10Z |
| publishDate | 2022-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Polymers |
| spelling | doaj.art-dd3cc0799167412099fb5f1efef02a142023-11-23T14:42:06ZengMDPI AGPolymers2073-43602022-05-011411225410.3390/polym14112254A Theoretical Study on the Phosgenation of 2,4-Toluenediamine (2,4-TDA)Ravikumar Thangaraj0Tamás Horváth1R. Zsanett Boros2Béla Viskolcz3Milán Szőri4Institute of Chemistry, University of Miskolc, Miskolc-Egyetemváros A/2, H-3515 Miskolc, HungaryInstitute of Chemistry, University of Miskolc, Miskolc-Egyetemváros A/2, H-3515 Miskolc, HungaryBorsodChem Zrt, Bolyai tér 1., H-3700 Kazincbarcika, HungaryInstitute of Chemistry, University of Miskolc, Miskolc-Egyetemváros A/2, H-3515 Miskolc, HungaryInstitute of Chemistry, University of Miskolc, Miskolc-Egyetemváros A/2, H-3515 Miskolc, HungaryIndustrially relevant phosgenation mechanisms of 2,4-toluenediamine (2,4-TDA) were investigated using G3MP2B3 model chemistry. Six reaction pathways had been explored, which resulted in the formation of toluene diisocyanate (2,4-TDI) including different scenarios of the ‘phosgenations first’ and ‘consecutive phosgenations’ mechanisms in both gas and condensed phases. Two possible ‘phosgenations first’ mechanisms show superior to the others in terms of energy, regardless of which phases are considered. Due to the o-dichlorobenzene (ODCB) solvation, the reaction barriers are dramatically reduced compared to the gas-phase reaction mechanism and the solvent effect can be described by linear relationship. Standard enthalpy of formation value was also recommended for 2,4-TDA (59.3 kJ/mol) and 2,4-TDI (−94.1 kJ/mol), as well as for the gas-phase intermediates (IM).https://www.mdpi.com/2073-4360/14/11/2254phosgenationtoluenediaminetoluene diisocyanateG3MP2B3carbamic chloride |
| spellingShingle | Ravikumar Thangaraj Tamás Horváth R. Zsanett Boros Béla Viskolcz Milán Szőri A Theoretical Study on the Phosgenation of 2,4-Toluenediamine (2,4-TDA) Polymers phosgenation toluenediamine toluene diisocyanate G3MP2B3 carbamic chloride |
| title | A Theoretical Study on the Phosgenation of 2,4-Toluenediamine (2,4-TDA) |
| title_full | A Theoretical Study on the Phosgenation of 2,4-Toluenediamine (2,4-TDA) |
| title_fullStr | A Theoretical Study on the Phosgenation of 2,4-Toluenediamine (2,4-TDA) |
| title_full_unstemmed | A Theoretical Study on the Phosgenation of 2,4-Toluenediamine (2,4-TDA) |
| title_short | A Theoretical Study on the Phosgenation of 2,4-Toluenediamine (2,4-TDA) |
| title_sort | theoretical study on the phosgenation of 2 4 toluenediamine 2 4 tda |
| topic | phosgenation toluenediamine toluene diisocyanate G3MP2B3 carbamic chloride |
| url | https://www.mdpi.com/2073-4360/14/11/2254 |
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