Catalytic Synthesis of Phosphorus-Containing Extractant: Tributyl Phosphate

Bishimbaeva, G. K.; Nalibaeva, A. M.; Polimbetova, G. S.; Borangazieva, A. K.; Ibraimova, Zh. U.; Zhanabaeva, A. K.

doi:10.1134/s1070427219040104

Cited by 3 publications

(4 citation statements)

References 6 publications

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“…In 2019, Borangazieva found that the combination of excess Cu(acac) 2 or Cu(C 3 H 7 CO 2 ) 2 (1.5 equiv.) and oxygen produced ( n ‐BuO) 2 P(O)H in 87% yield (Scheme 1c) [17] . Using stoichiometric transition metal or explosive organo‐peroxide is not without drawbacks, from the inevitable loss of atom economy to the safety of experimental operation.…”

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confidence: 99%

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Direct Synthesis of Dialkylphosphites from White Phosphorus

et al. 2022

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Dialkyl phosphites (DAPIs), traditionally prepared from hazardous and corrosive PCl3, are the fundamental reactive starting materials used in organophosphorus chemistry. Here, a KBr‐mediated synthesis of DAPIs involving P4, alcohols and water is presented. With the use of silica gel as the catalyst, oxone as the safe oxidant, industrially important (EtO)2P(O)H, (i‐PrO)2P(O)H and (MeO)2P(O)H are prepared in 70–90% yields. Furthermore, rare metal extractant bis(2‐ethylhexyl) phosphate (D2EHPA) is obtained in 73% yield. The reaction is characterized by a complete conversion of white phosphorus. Moreover, this method can be easily adapted to large‐scale preparation.

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Section: Figurementioning

confidence: 99%

“…and oxygen produced (n-BuO) 2 P(O)H in 87% yield (Scheme 1c). [17] Using stoichiometric transition metal or explosive organo-peroxide is not without drawbacks, from the inevitable loss of atom economy to the safety of experimental operation. In order to address this problem, using cheap inorganic catalyst and green oxidant may be a good choice.…”

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confidence: 99%

Direct Synthesis of Dialkylphosphites from White Phosphorus

et al. 2022

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“…A selective and operationally simple method to access industrially important DAPIs from P 4 is of vital interest, as it would avoid the use of Cl 2 and PCl 3 and allow simple inorganic phosphorus as the starting feedstock. In this context, the Abdreimova group tried transition-metal-catalyzed phosphorylation of alcohols with P 4 , but large amounts of oxidants such as benzoyl peroxide and NaNO 2 were needed (Scheme c). , The combination of excess transition metals and O 2 was also effective in the synthesis of DAPIs (Scheme c) . Notwithstanding the progress, these transformations require stoichiometric transition metals or external chemical oxidants, leading to negative environmental impacts.…”

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confidence: 99%

“…21,22 The combination of excess transition metals and O 2 was also effective in the synthesis of DAPIs (Scheme 1c). 23 Notwithstanding the progress, these transformations require stoichiometric transition metals or external chemical oxidants, leading to negative environmental impacts. We recently reported a silica−KBr-mediated phosphorylation reaction of alcohols enabled by oxone as an oxidant (Scheme 1c), 24 but this method has inefficiencies for certain alcohol-containing reductive groups and unsaturated bonds, likely due to the strong oxidation condition.…”

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Ternary Photoredox/Nickel/Halide Catalysis for the Phosphorylation of Alcohols with White Phosphorus

et al. 2023

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Dialkyl phosphites (DAPIs) are important precursors in the formation of phosphorus−carbon and phosphorus− heteroatom bonds with significant industrial applications. Traditional PCl 3 -based procedures suffer from high waste production and toxic reaction conditions. The direct conversion of white phosphorus (P 4 ) to DAPIs can circumvent these issues by avoiding the use of Cl 2 and PCl 3 . We present a waste-free, environmentally friendly approach for synthesizing DAPIs using P 4 and alcohols, leveraging a combination of photoredox catalyst, nickel catalyst, and halide anion. This photocatalytic method enables the efficient coupling of various alcohols. Advantageously, this method is also suitable for the synthesis of trialkyl phosphates and triaryl phosphorotrithioates.

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Recent progress on the functionalization of white phosphorus in China

Huangfu,

Wang,

Chen

et al. 2024

National Science Review

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Direct synthesis of organophosphorus compounds from white phosphorus represents a significant but challenging subject, especially in the context of ongoing efforts to comprehensively improve phosphorus-derived chemical industry driven by sustainability and safety concerns. China is the world's largest producer of white phosphorus, creating a significant demand for the green transformation of this crucial feedstock. This review provides an overview of advancements in white phosphorus activation by Chinese research teams, organized by the direct construction of P−C/N/O/S/M bonds from white phosphorus. Additionally, we offer some insights into prospective directions for the activation and transformation of white phosphorus in the future. This review paper aims to attract more researchers to engage in this area, stimulating follow-up exploration and fostering enduring advances.

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Catalytic Synthesis of Phosphorus-Containing Extractant: Tributyl Phosphate

Cited by 3 publications

References 6 publications

Direct Synthesis of Dialkylphosphites from White Phosphorus

Direct Synthesis of Dialkylphosphites from White Phosphorus

Ternary Photoredox/Nickel/Halide Catalysis for the Phosphorylation of Alcohols with White Phosphorus

Recent progress on the functionalization of white phosphorus in China

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