Industrial Upscaling of DOPO-Based Phosphonamidates and Phosphonates Derivatives Using Cl2 Gas as a Chlorinating Agent
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Autor:innen
Salmeia, Khalifah A.
Baumgartner, Georg
Jovic, Milijana
Zich, Thomas
Gaan, Sabyasachi
Autor:in (Körperschaft)
Publikationsdatum
10/2018
Typ der Arbeit
Studiengang
Typ
01A - Beitrag in wissenschaftlicher Zeitschrift
Herausgeber:innen
Herausgeber:in (Körperschaft)
Betreuer:in
Übergeordnetes Werk
Organic Process Research & Development
Themenheft
DOI der Originalpublikation
Link
Reihe / Serie
Reihennummer
Jahrgang / Band
22
Ausgabe / Nummer
11
Seiten / Dauer
1570-1577
Patentnummer
Verlag / Herausgebende Institution
American Chemical Society
Verlagsort / Veranstaltungsort
Auflage
Version
Programmiersprache
Abtretungsempfänger:in
Praxispartner:in/Auftraggeber:in
Zusammenfassung
Herein, we report the industrial synthesis procedure of phosphonamidate and phosphonate derivatives via an efficient and simple chlorination of 9,10-dihydro-9-oxa-10-phosphaphenanthren-10-oxide (DOPO) with Cl2 gas. The key step in the synthesis is the conversion of the P–H bond to P–Cl of DOPO by flowing Cl2 gas into a solution of DOPO in dichloromethane, affording the key intermediate 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-chloride (DOPO-Cl) compound which is industrially not available. DOPO-Cl was isolated, characterized, and used for this synthesis of DOPO-based phosphonamidates and phosphonates in relatively high yield by reaction with the corresponding amines and alcohols, respectively. The experimental results show that the chlorination reaction occurs in equimolar ratios of Cl2 gas to DOPO compound. Subsequently, the procedure developed in laboratory scale was industrially applied for synthesis of the 6,6′-(ethane-1,2-diylbis(azanediyl))bis(dibenzo[c,e][1,2]oxaphosphinine-6-oxide) (EDA-DOPO) compound and 6-((1-oxido-2,6,7-trioxa-1-phosphabicyclo[2.2.2]octan-4-yl)methoxy)dibenzo[c,e][1,2]oxaphosphinine-6-oxide (DOPO-PEPA). All synthetic compounds thus obtainedwere characterized and found to be identical to the authentic laboratory scale products.
Schlagwörter
chlorination reaction, Cl2 Gas, DOPO-Cl, industrial upscalling, phosphonamidates, phosphonates
Fachgebiet (DDC)
Veranstaltung
Startdatum der Ausstellung
Enddatum der Ausstellung
Startdatum der Konferenz
Enddatum der Konferenz
Datum der letzten Prüfung
ISBN
ISSN
1083-6160
1520-586X
1520-586X
Sprache
Englisch
Während FHNW Zugehörigkeit erstellt
Ja
Publikationsstatus
Veröffentlicht
Begutachtung
Peer-Review der ganzen Publikation
Open Access-Status
Lizenz
Zitation
SALMEIA, Khalifah A., Georg BAUMGARTNER, Milijana JOVIC, Angelo GÖSSI, Wolfgang RIEDL, Thomas ZICH und Sabyasachi GAAN, 2018. Industrial Upscaling of DOPO-Based Phosphonamidates and Phosphonates Derivatives Using Cl2 Gas as a Chlorinating Agent. Organic Process Research & Development. Oktober 2018. Bd. 22, Nr. 11, S. 1570–1577. DOI 10.1021/acs.oprd.8b00295. Verfügbar unter: http://hdl.handle.net/11654/27317