Phosphoryl Compounds

Timperley, Christopher M.; Renard, Pierre; Gomez, Catherine

doi:10.1016/b978-0-08-098212-0.00004-2

Cited by 4 publications

(4 citation statements)

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“…License: CC BY 4.0 route). [11] In this context, we aimed to develop a direct esterification reaction of 1 to establish a new methodology for the production of phosphate triesters (Fig. 1a, this work).…”

Section: ]mentioning

confidence: 99%

“…[9] Hence, phosphorus recovery and recycling are crucial in terms of not only resource risk avoidance but also achieving a sustainable global environment. [1, 3,10,11] To address this issue, technologies to recover phosphorus sources from various wastes, such as sewage sludge ash, steel slag, manure and biowaste, have been developed, enabling the production of phosphate salts as fertilizer from recovered phosphoric acid (H3PO4, 1). […”

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confidence: 99%

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Chemical upcycling of phosphoric acid recovered from sewage waste

Naganawa,

Sakamoto,

Fujita

et al. 2023

Preprint

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Global concerns surrounding the depletion and strategic importance of phosphorus resources have heightened the demand for the recovery and recycling efforts. However, the phosphorus compound obtained from waste exists primarily as chemically inert phosphoric acid or its salts, and the direct conversion into high-value chemicals has remained largely elusive. Our objective was to develop an innovative technology that bypasses the use of white phosphorus and enables the direct esterification of phosphoric acid, leading to the production of phosphate triesters widely utilized across versatile applications. Tetraalkyl orthosilicates emerged as highly effective reagents for the direct triple esterification of 85% phosphoric acid, as well as the esterification of organophosphinic and phosphonic acids. Through both experimental and theoretical investigations, we have elucidated a novel mechanism governing the reaction, wherein tetraalkyl orthosilicate not only serves as an alkyl transfer reagent but also facilitates the formation of multimolecular aggregates as a reaction template, assisting the proton shuttle process. By optimizing the recovery method of phosphoric acid from sewage sludge ash, we successfully achieved the direct esterification of the recovered phosphoric acid with tetraalkyl orthosilicate, thus pioneering a groundbreaking upcycling pathway from sewage waste to valuable phosphorus chemicals.

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Section: ]mentioning

confidence: 99%

mentioning

confidence: 99%

Chemical upcycling of phosphoric acid recovered from sewage waste

Naganawa,

Sakamoto,

Fujita

et al. 2023

Preprint

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“…This concept is now recognized as one of the most important and urgent challenges within the international framework. 1, [3][4][5][6][7][8][9][10] The industrial route to produce phosphorus-containing chemicals generally begins from the production of white phosphorus (P4) via the energy-intensive reduction of phosphate rock as a nonrenewable natural resource using large amounts of electrical power, approximately 12.5 to 14 MWh per ton of P4 (Figure 1a). 3,7,11,12 Owing to this method, there have been repeated instances in the past, such as a global price spike of phosphorus resources, that have also raised concerns about the sustainability of P4 production.…”

Section: Introductionmentioning

confidence: 99%

“…16 In particular, flame retardants possessing phosphate triester structures are normally synthesized in large quantities (360,000 tons in 2020) 5 via alcoholysis of POCl3 prepared from P4 (Figure 1a, conventional route). 6 In this context, we focused on the chemical recycling of sewage waste by a direct molecular transformation of 1 to provide phosphate triesters (Figure 1a, this work). 17 The bottleneck in developing a direct molecular transformation for 1 lies in the high chemical and thermodynamic stability of 1 as a strong acid.…”

Section: Introductionmentioning

confidence: 99%

Chemical Recycling of Phosphoric Acid Recovered from Sewage Waste via Direct Esterification with Organosilicate

Naganawa,

Sakamoto,

Fujita

et al. 2024

Preprint

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Global concerns regarding the depletion and strategic importance of phosphorus resources have increased demand for the recovery and recycling. However, waste-derived phosphorus compounds, primarily as chemically inert phosphoric acid or its salts, present a challenge to their direct conversion into high-value chemicals. We aimed to develop an innovative technology that bypasses the use of white phosphorus and enables direct esterification of phosphoric acid to produce widely applicable phosphate triesters. Tetraalkyl orthosilicates emerged as highly effective reagents for the direct triple esterification of 85% phosphoric acid, as well as the esterification of organophosphinic and phosphonic acids. Furthermore, we achieved direct esterification of recovered phosphoric acid with tetraalkyl orthosilicate, thus pioneering a recycling pathway from sewage waste to valuable phosphorus chemicals. Experimental and theoretical investigations revealed a novel mechanism, wherein tetraalkyl orthosilicates facilitate multimolecular aggregation to achieve alkyl transfer from tetraalkylorthosilicate to phosphoric acid via multiple proton shuttling.

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Ethyl ester and silyl ester of imidodiphosphate: An alternative route to access phosphorus‐nitrogen‐phosphorus bonds via Staudinger reaction

Low

Levalois-Grützmacher

2018

Heteroatom Chemistry

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We present herein an alternative synthesis route to obtain tetraethyl imidodiphosphate (EtO) 2 P(O)NH(O)P(OEt) 2 (3) and its silylester derivative tetrakis(trimethylsilyl) imidodiphosphate (Me 3 SiO) 2 P(O)NH(O)P(OSiMe 3 ) 2 (4) involving a phosphorazidate intermediate (1) and the Staudinger reaction. Compared to previous methods, this synthesis route is simpler, more atom efficient, and energetically inexpensive.Moreover, the final compounds are obtained with larger yield and higher purity.

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Phosphoryl Compounds

Cited by 4 publications

References 341 publications

Chemical upcycling of phosphoric acid recovered from sewage waste

Chemical upcycling of phosphoric acid recovered from sewage waste

Chemical Recycling of Phosphoric Acid Recovered from Sewage Waste via Direct Esterification with Organosilicate

Ethyl ester and silyl ester of imidodiphosphate: An alternative route to access phosphorus‐nitrogen‐phosphorus bonds via Staudinger reaction

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