Investigations of catalysis of urethane formation using organotin dicarboxylate
The reaction mechanism of the urethane formation for both aliphatic and aromatic isocyanates in the presence of organotin dicarboxylate as a catalyst is investigated theoretically and experimentally. Modelling on a dispersion corrected DFT level of theory (B3LYP-D3) shows that an alkoxide complex is...
| Main Authors: | , , |
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| Format: | Article |
| Language: | English |
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Elsevier
2020-05-01
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| Series: | Heliyon |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S240584402030918X |
| _version_ | 1819111188905066496 |
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| author | Ransi Devendra Neil R. Edmonds Tilo Söhnel |
| author_facet | Ransi Devendra Neil R. Edmonds Tilo Söhnel |
| author_sort | Ransi Devendra |
| collection | DOAJ |
| description | The reaction mechanism of the urethane formation for both aliphatic and aromatic isocyanates in the presence of organotin dicarboxylate as a catalyst is investigated theoretically and experimentally. Modelling on a dispersion corrected DFT level of theory (B3LYP-D3) shows that an alkoxide complex is formed between organotin dicarboxylate and alcohol. This complex is the dominant catalyst for the urethane formation reaction. In this study, the interaction between the alkoxide complex and isocyanate through N-coordination is considered. By using thermochemical data, it is possible to show that aliphatic isocyanates can be more sensitive to the carboxylic ligand content of the organotin compound as a catalyst in urethane formation in non-polar solvents compared to aromatic isocyanates. The interactions of carboxylic acid, which is formed as an intermediate in the catalysis process, with isocyanate and the effects on the catalytic process are also discussed. |
| first_indexed | 2024-12-22T03:53:39Z |
| format | Article |
| id | doaj.art-da91303e25454b55a2afb4ee1f51d0e2 |
| institution | Directory Open Access Journal |
| issn | 2405-8440 |
| language | English |
| last_indexed | 2024-12-22T03:53:39Z |
| publishDate | 2020-05-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Heliyon |
| spelling | doaj.art-da91303e25454b55a2afb4ee1f51d0e22022-12-21T18:39:56ZengElsevierHeliyon2405-84402020-05-0165e04074Investigations of catalysis of urethane formation using organotin dicarboxylateRansi Devendra0Neil R. Edmonds1Tilo Söhnel2School of Chemical Sciences, University of Auckland, Private Bag 92019, Auckland, New Zealand; Uroxsys Ltd., P.O. Box 58333, Botany, Auckland, New ZealandSchool of Chemical Sciences, University of Auckland, Private Bag 92019, Auckland, New Zealand; Department of Mechanical Engineering & Centre of Advanced, Composite Materials, University of Auckland, Private Bag 92019, Auckland, New ZealandSchool of Chemical Sciences, University of Auckland, Private Bag 92019, Auckland, New Zealand; MacDiarmid Institute of Advanced Materials and Nanotechnology, Victoria University of Wellington, P.O. Box 600, Wellington, New Zealand; Corresponding author.The reaction mechanism of the urethane formation for both aliphatic and aromatic isocyanates in the presence of organotin dicarboxylate as a catalyst is investigated theoretically and experimentally. Modelling on a dispersion corrected DFT level of theory (B3LYP-D3) shows that an alkoxide complex is formed between organotin dicarboxylate and alcohol. This complex is the dominant catalyst for the urethane formation reaction. In this study, the interaction between the alkoxide complex and isocyanate through N-coordination is considered. By using thermochemical data, it is possible to show that aliphatic isocyanates can be more sensitive to the carboxylic ligand content of the organotin compound as a catalyst in urethane formation in non-polar solvents compared to aromatic isocyanates. The interactions of carboxylic acid, which is formed as an intermediate in the catalysis process, with isocyanate and the effects on the catalytic process are also discussed.http://www.sciencedirect.com/science/article/pii/S240584402030918XInorganic chemistryOrganic chemistryOrganotin dicarboxylateComputationalUrethaneCatalysis |
| spellingShingle | Ransi Devendra Neil R. Edmonds Tilo Söhnel Investigations of catalysis of urethane formation using organotin dicarboxylate Heliyon Inorganic chemistry Organic chemistry Organotin dicarboxylate Computational Urethane Catalysis |
| title | Investigations of catalysis of urethane formation using organotin dicarboxylate |
| title_full | Investigations of catalysis of urethane formation using organotin dicarboxylate |
| title_fullStr | Investigations of catalysis of urethane formation using organotin dicarboxylate |
| title_full_unstemmed | Investigations of catalysis of urethane formation using organotin dicarboxylate |
| title_short | Investigations of catalysis of urethane formation using organotin dicarboxylate |
| title_sort | investigations of catalysis of urethane formation using organotin dicarboxylate |
| topic | Inorganic chemistry Organic chemistry Organotin dicarboxylate Computational Urethane Catalysis |
| url | http://www.sciencedirect.com/science/article/pii/S240584402030918X |
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