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Industrial Upscaling of DOPO-Based Phosphonamidates and Phosphonates Derivatives Using Cl2 Gas as a Chlorinating Agent

Datum
10.2018
Autorin/Autor
Salmeia, Khalifah A.
Baumgartner, Georg
Jovic, Milijana
Gössi, Angelo
Riedl, Wolfgang
Zich, Thomas
Gaan, Sabyasachi
Metadata
Zur Langanzeige
Type
01 - Zeitschriftenartikel, Journalartikel oder Magazin
Primary target group
Science
Created while belonging to FHNW?
Yes
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.
URI
http://hdl.handle.net/11654/27317

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