Synthesis of industrially relevant carbamates towards isocyanates using carbon dioxide and organotin(IV) alkoxides
Abstract A straightforward phosgene-free synthesis of aromatic isocyanates and diisocyanates is disclosed. Theoretical investigations suggested that the insertion of carbon dioxide (CO2) by dialkyltin(IV) dialkoxides could be used to convert aromatic amines into aromatic mono- and dicarbamates. Here...
Gespeichert in:
| Hauptverfasser: | , , , , , , |
|---|---|
| Dokumenttyp: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
20 June 2016
|
| In: |
ChemSusChem
Year: 2016, Jahrgang: 9, Heft: 13, Pages: 1586-1590 |
| ISSN: | 1864-564X |
| DOI: | 10.1002/cssc.201600580 |
| Online-Zugang: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1002/cssc.201600580 Verlag, lizenzpflichtig, Volltext: https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/cssc.201600580 
|
| Verfasserangaben: | Nicolas Germain, Imke Müller, Matthias Hanauer, Rocco A. Paciello, Robert Baumann, Oliver Trapp, and Thomas Schaub |
MARC
| LEADER | 00000caa a2200000 c 4500 | ||
|---|---|---|---|
| 001 | 1699328706 | ||
| 003 | DE-627 | ||
| 005 | 20230515145703.0 | ||
| 007 | cr uuu---uuuuu | ||
| 008 | 200603s2016 xx |||||o 00| ||eng c | ||
| 024 | 7 | |a 10.1002/cssc.201600580 |2 doi | |
| 035 | |a (DE-627)1699328706 | ||
| 035 | |a (DE-599)KXP1699328706 | ||
| 035 | |a (OCoLC)1341328227 | ||
| 040 | |a DE-627 |b ger |c DE-627 |e rda | ||
| 041 | |a eng | ||
| 084 | |a 30 |2 sdnb | ||
| 100 | 1 | |a Germain, Nicolas |e VerfasserIn |0 (DE-588)1160449481 |0 (DE-627)1023619210 |0 (DE-576)505001586 |4 aut | |
| 245 | 1 | 0 | |a Synthesis of industrially relevant carbamates towards isocyanates using carbon dioxide and organotin(IV) alkoxides |c Nicolas Germain, Imke Müller, Matthias Hanauer, Rocco A. Paciello, Robert Baumann, Oliver Trapp, and Thomas Schaub |
| 264 | 1 | |c 20 June 2016 | |
| 300 | |a 5 | ||
| 336 | |a Text |b txt |2 rdacontent | ||
| 337 | |a Computermedien |b c |2 rdamedia | ||
| 338 | |a Online-Ressource |b cr |2 rdacarrier | ||
| 500 | |a Gesehen am 03.06.2020 | ||
| 520 | |a Abstract A straightforward phosgene-free synthesis of aromatic isocyanates and diisocyanates is disclosed. Theoretical investigations suggested that the insertion of carbon dioxide (CO2) by dialkyltin(IV) dialkoxides could be used to convert aromatic amines into aromatic mono- and dicarbamates. Here we show, that methyl phenylcarbamate (MPC) from aniline using organotin(IV) dimethoxide and CO2 can be formed in high yield of up to 92?%, experimentally corroborating the predictions of density functional theory (DFT) calculations. MPC was then separated from the tin oxide residues and converted into phenyl isocyanate. Furthermore, organotin(IV) alkoxides could be regenerated from the tin oxide residues and reused, paving the way for a continuous industrial process. Extension of the scope to the synthesis of diurethanes from toluene 2,4-diamine and 4,4?-methylenedianiline could potentially allow the efficient production of industrially relevant diisocyanates. | ||
| 650 | 4 | |a carbamates | |
| 650 | 4 | |a carbon dioxide | |
| 650 | 4 | |a isocyanates | |
| 650 | 4 | |a polymers | |
| 650 | 4 | |a tin | |
| 700 | 1 | |a Müller, Imke Britta |e VerfasserIn |0 (DE-588)1289275556 |0 (DE-627)1845289714 |4 aut | |
| 700 | 1 | |a Hanauer, Matthias |d 1985- |e VerfasserIn |0 (DE-588)1034341979 |0 (DE-627)745238351 |0 (DE-576)381960897 |4 aut | |
| 700 | 1 | |a Paciello, Rocco |e VerfasserIn |0 (DE-588)1144886066 |0 (DE-627)1005027323 |0 (DE-576)495499897 |4 aut | |
| 700 | 1 | |a Baumann, Robert |e VerfasserIn |4 aut | |
| 700 | 1 | |a Trapp, Oliver |d 1973- |e VerfasserIn |0 (DE-588)123258634 |0 (DE-627)70623071X |0 (DE-576)184366003 |4 aut | |
| 700 | 1 | |a Schaub, Thomas |d 1980- |e VerfasserIn |0 (DE-588)132888343 |0 (DE-627)690969082 |0 (DE-576)299482499 |4 aut | |
| 773 | 0 | 8 | |i Enthalten in |t ChemSusChem |d Weinheim : Wiley-VCH, 2008 |g 9(2016), 13, Seite 1586-1590 |h Online-Ressource |w (DE-627)559078358 |w (DE-600)2411405-4 |w (DE-576)277981522 |x 1864-564X |7 nnas |a Synthesis of industrially relevant carbamates towards isocyanates using carbon dioxide and organotin(IV) alkoxides |
| 773 | 1 | 8 | |g volume:9 |g year:2016 |g number:13 |g pages:1586-1590 |g extent:5 |a Synthesis of industrially relevant carbamates towards isocyanates using carbon dioxide and organotin(IV) alkoxides |
| 856 | 4 | 0 | |u https://doi.org/10.1002/cssc.201600580 |x Verlag |x Resolving-System |z lizenzpflichtig |3 Volltext |
| 856 | 4 | 0 | |u https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/cssc.201600580 |x Verlag |z lizenzpflichtig |3 Volltext |
| 951 | |a AR | ||
| 992 | |a 20200603 | ||
| 993 | |a Article | ||
| 994 | |a 2016 | ||
| 998 | |g 132888343 |a Schaub, Thomas |m 132888343:Schaub, Thomas |p 7 |y j | ||
| 998 | |g 123258634 |a Trapp, Oliver |m 123258634:Trapp, Oliver |d 120000 |d 120100 |e 120000PT123258634 |e 120100PT123258634 |k 0/120000/ |k 1/120000/120100/ |p 6 | ||
| 998 | |g 1144886066 |a Paciello, Rocco A. |m 1144886066:Paciello, Rocco A. |d 120000 |d 120100 |e 120000PP1144886066 |e 120100PP1144886066 |k 0/120000/ |k 1/120000/120100/ |p 4 | ||
| 998 | |g 1034341979 |a Hanauer, Matthias |m 1034341979:Hanauer, Matthias |d 120000 |d 120100 |e 120000PH1034341979 |e 120100PH1034341979 |k 0/120000/ |k 1/120000/120100/ |p 3 | ||
| 998 | |g 1289275556 |a Müller, Imke Britta |m 1289275556:Müller, Imke Britta |d 120000 |d 120100 |e 120000PM1289275556 |e 120100PM1289275556 |k 0/120000/ |k 1/120000/120100/ |p 2 | ||
| 998 | |g 1160449481 |a Germain, Nicolas |m 1160449481:Germain, Nicolas |d 120000 |d 120100 |e 120000PG1160449481 |e 120100PG1160449481 |k 0/120000/ |k 1/120000/120100/ |p 1 |x j | ||
| 999 | |a KXP-PPN1699328706 |e 3681841705 | ||
| BIB | |a Y | ||
| SER | |a journal | ||
| JSO | |a {"note":["Gesehen am 03.06.2020"],"type":{"bibl":"article-journal","media":"Online-Ressource"},"recId":"1699328706","language":["eng"],"title":[{"title":"Synthesis of industrially relevant carbamates towards isocyanates using carbon dioxide and organotin(IV) alkoxides","title_sort":"Synthesis of industrially relevant carbamates towards isocyanates using carbon dioxide and organotin(IV) alkoxides"}],"person":[{"display":"Germain, Nicolas","roleDisplay":"VerfasserIn","role":"aut","family":"Germain","given":"Nicolas"},{"family":"Müller","given":"Imke Britta","roleDisplay":"VerfasserIn","display":"Müller, Imke Britta","role":"aut"},{"given":"Matthias","family":"Hanauer","role":"aut","roleDisplay":"VerfasserIn","display":"Hanauer, Matthias"},{"given":"Rocco","family":"Paciello","role":"aut","roleDisplay":"VerfasserIn","display":"Paciello, Rocco"},{"given":"Robert","family":"Baumann","role":"aut","display":"Baumann, Robert","roleDisplay":"VerfasserIn"},{"given":"Oliver","family":"Trapp","role":"aut","display":"Trapp, Oliver","roleDisplay":"VerfasserIn"},{"family":"Schaub","given":"Thomas","roleDisplay":"VerfasserIn","display":"Schaub, Thomas","role":"aut"}],"physDesc":[{"extent":"5 S."}],"relHost":[{"id":{"zdb":["2411405-4"],"doi":["10.1002/(ISSN)1864-564X"],"eki":["559078358"],"issn":["1864-564X"]},"origin":[{"publisher":"Wiley-VCH","dateIssuedDisp":"[2008]-","publisherPlace":"Weinheim"}],"physDesc":[{"extent":"Online-Ressource"}],"title":[{"title":"ChemSusChem","subtitle":"chemistry, sustainability, energy, materials","title_sort":"ChemSusChem"}],"recId":"559078358","language":["eng"],"note":["Gesehen am 5. November 2022"],"disp":"Synthesis of industrially relevant carbamates towards isocyanates using carbon dioxide and organotin(IV) alkoxidesChemSusChem","type":{"bibl":"periodical","media":"Online-Ressource"},"part":{"volume":"9","text":"9(2016), 13, Seite 1586-1590","extent":"5","year":"2016","issue":"13","pages":"1586-1590"},"titleAlt":[{"title":"Chem sus chem"}],"pubHistory":["1.2008 -"]}],"origin":[{"dateIssuedKey":"2016","dateIssuedDisp":"20 June 2016"}],"id":{"doi":["10.1002/cssc.201600580"],"eki":["1699328706"]},"name":{"displayForm":["Nicolas Germain, Imke Müller, Matthias Hanauer, Rocco A. Paciello, Robert Baumann, Oliver Trapp, and Thomas Schaub"]}} | ||
| SRT | |a GERMAINNICSYNTHESISO2020 | ||