Highly efficient isocyanate-free microwave-assisted synthesis of [6]-oligourea

Handle URI:
http://hdl.handle.net/10754/598503
Title:
Highly efficient isocyanate-free microwave-assisted synthesis of [6]-oligourea
Authors:
Qaroush, Abdussalam K.; Al-Hamayda, Asmaa S.; Khashman, Yasmeen K.; Vagin, Sergei I.; Troll, Carsten; Rieger, Bernhard
Abstract:
A new eco-friendly, isocyanate-free, energy-saving method for the production of [6]-oligourea, utilizing a green carbonylating agent, viz. propylene carbonate, is reported. It comprises an organocatalyzed, microwave-assisted, solvent-free synthesis. Two modes of microwave-assisted synthesis, viz. dynamic and fixed energy modes, were applied. Upon optimization, the dynamic mode gave 79% yields of [6]-oligourea. On the other hand, almost quantitative yields were obtained using the fixed mode, within 20 min, at 10 W and with the same catalyst loading. Combination of both organocatalysis and microwave energy input appears to be a key issue for the efficiency of the reaction, with the fixed energy mode being best suited. It should be noted that all data reported are reproducible (due to the homogeneous microwave technology used by CEM Discover S-Class of microwave reactors). To the best of our knowledge, this is the best eco-friendly synthetic approach for the preparation of the title oligomers. It paves the way for using more of the biorenewable and sustainable chemicals as a feedstock for the production of polyureas. The oligomer produced was analyzed by EA, ATR-FTIR, XRD, 1H and 13CNMR. Furthermore, thermal properties of the resulting [6]-oligourea were analyzed using TGA and DSC. © The Royal Society of Chemistry 2013.
Citation:
Qaroush AK, Al-Hamayda AS, Khashman YK, Vagin SI, Troll C, et al. (2013) Highly efficient isocyanate-free microwave-assisted synthesis of [6]-oligourea. Catalysis Science & Technology 3: 2221. Available: http://dx.doi.org/10.1039/c3cy00117b.
Publisher:
Royal Society of Chemistry (RSC)
Journal:
Catalysis Science & Technology
KAUST Grant Number:
UK-C0020/KSA-C0069
Issue Date:
2013
DOI:
10.1039/c3cy00117b
Type:
Article
ISSN:
2044-4753; 2044-4761
Sponsors:
A. K. Q. is grateful to King Abdullah University for Science and Technology, KAUST for the financial support of the scholarship of his PhD for the project UK-C0020/KSA-C0069. In addition, we thank Dr Wolfgang Eisenreich and Dr Timo Anselment for their help with the NMR experiments.
Appears in Collections:
Publications Acknowledging KAUST Support

Full metadata record

DC FieldValue Language
dc.contributor.authorQaroush, Abdussalam K.en
dc.contributor.authorAl-Hamayda, Asmaa S.en
dc.contributor.authorKhashman, Yasmeen K.en
dc.contributor.authorVagin, Sergei I.en
dc.contributor.authorTroll, Carstenen
dc.contributor.authorRieger, Bernharden
dc.date.accessioned2016-02-25T13:31:09Zen
dc.date.available2016-02-25T13:31:09Zen
dc.date.issued2013en
dc.identifier.citationQaroush AK, Al-Hamayda AS, Khashman YK, Vagin SI, Troll C, et al. (2013) Highly efficient isocyanate-free microwave-assisted synthesis of [6]-oligourea. Catalysis Science & Technology 3: 2221. Available: http://dx.doi.org/10.1039/c3cy00117b.en
dc.identifier.issn2044-4753en
dc.identifier.issn2044-4761en
dc.identifier.doi10.1039/c3cy00117ben
dc.identifier.urihttp://hdl.handle.net/10754/598503en
dc.description.abstractA new eco-friendly, isocyanate-free, energy-saving method for the production of [6]-oligourea, utilizing a green carbonylating agent, viz. propylene carbonate, is reported. It comprises an organocatalyzed, microwave-assisted, solvent-free synthesis. Two modes of microwave-assisted synthesis, viz. dynamic and fixed energy modes, were applied. Upon optimization, the dynamic mode gave 79% yields of [6]-oligourea. On the other hand, almost quantitative yields were obtained using the fixed mode, within 20 min, at 10 W and with the same catalyst loading. Combination of both organocatalysis and microwave energy input appears to be a key issue for the efficiency of the reaction, with the fixed energy mode being best suited. It should be noted that all data reported are reproducible (due to the homogeneous microwave technology used by CEM Discover S-Class of microwave reactors). To the best of our knowledge, this is the best eco-friendly synthetic approach for the preparation of the title oligomers. It paves the way for using more of the biorenewable and sustainable chemicals as a feedstock for the production of polyureas. The oligomer produced was analyzed by EA, ATR-FTIR, XRD, 1H and 13CNMR. Furthermore, thermal properties of the resulting [6]-oligourea were analyzed using TGA and DSC. © The Royal Society of Chemistry 2013.en
dc.description.sponsorshipA. K. Q. is grateful to King Abdullah University for Science and Technology, KAUST for the financial support of the scholarship of his PhD for the project UK-C0020/KSA-C0069. In addition, we thank Dr Wolfgang Eisenreich and Dr Timo Anselment for their help with the NMR experiments.en
dc.publisherRoyal Society of Chemistry (RSC)en
dc.titleHighly efficient isocyanate-free microwave-assisted synthesis of [6]-oligoureaen
dc.typeArticleen
dc.identifier.journalCatalysis Science & Technologyen
dc.contributor.institutionTechnische Universitat Munchen, Munich, Germanyen
dc.contributor.institutionGerman Jordanian University, Amman, Jordanen
kaust.grant.numberUK-C0020/KSA-C0069en
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