A simple technology for phosphorus recovery using acid-treated concrete sludge

Okano, Kenji; Yamamoto, Yasuhisa; Takano, Hiroyuki; Aketo, Tsuyoshi; Honda, Kohsuke; Ohtake, Hisao

doi:10.1016/j.seppur.2016.03.054

Cited by 16 publications

(6 citation statements)

References 12 publications

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“…(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-Heptadecafluorodecyl)diphenylphosphine oxide (2′): white solid, 5.27 g, 58%; mp 123.3− 124.1 °C; 1 H NMR (400 MHz, CDCl 3 ) δ 7.78−7.73 (m, 4H), 7.60−Table 4. Synthesis of Various Alkenes from Fluorous Phosphine 2, Alkyl Bromides 3, and Aldehydes 9 aa Reaction conditions: (i) 2 (0.09−0.19 mmol) b , 3 (1.2 equiv), CH 3 CN (0.6 mL), 60 °C, 3 h. (ii) 9 (1.0 equiv), i Pr 2 NEt (2.0 equiv), 60 °C, 6 h.bThe scale of 2: 0.12 mmol (entry 1), 0.16 mmol (entry 2), 0.09 mmol (entry 3), 0.15 mmol (entry 4), 0.13 mmol (entry 5), 0.13 mmol (entry 6), 0.12 mmol (entry 7), 0.16 mmol (entry 8), and 0.19 mmol (entry 9) c Determined by 1 H NMR spectroscopy.…”

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Phosphorus-Recycling Wittig Reaction: Design and Facile Synthesis of a Fluorous Phosphine and Its Reusable Process in the Wittig Reaction

et al. 2020

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This study shows that phosphorus sources can be recycled using the appropriate fluorous phosphine in the Wittig reaction. The designed fluorous phosphine, which has an ethylene spacer between its phosphorus atom and the perfluoroalkyl group, was synthesized from air-stable phosphine reagents. The synthesized phosphine can be used for the Wittig reaction process to obtain various alkenes in adequate yields and stereoselectivity. The concomitantly formed fluorous phosphine oxide was extracted from the reaction mixture using a fluorous biphasic system. The fluorous phosphine was regenerated by reducing the fluorous phosphine oxide with diisobutylaluminum hydride. Finally, a series of gram scale phosphorus recycling processes were performed, which included the Wittig reaction, separation, reduction, and reuse.

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“…Benzyl(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)diphenylphosphonium bromide (7b): light yellow solid, 79.0 mg, 98%; mp 153.5−154.1 °C; 1 H NMR (400 MHz, CDCl 3 ) δ 7.97−7.92…”

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Phosphorus-Recycling Wittig Reaction: Design and Facile Synthesis of a Fluorous Phosphine and Its Reusable Process in the Wittig Reaction

et al. 2020

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“…Phosphorus plays an important role in living organisms as it is one of the main components of cell structure [ 1 ]. Usually, phosphorus exists in three species (orthophosphate, polyphosphate, and organic phosphorus) in solution.…”

Section: Introductionmentioning

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Thermodynamics Analysis and Removal of P in a P-(M)-H2O System

et al. 2021

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In order to efficiently remove phosphorus, thermodynamic equilibrium diagrams of the P-H2O system and P-M-H2O system (M stands for Fe, Al, Ca, Mg) were analyzed by software from Visual MINTEQ to identify the existence of phosphorus ions and metal ions as pH ranged from 1 to 14. The results showed that the phosphorus ions existed in the form of H3PO4, H2PO4−, HPO42−, and PO43−. Among them, H2PO4− and HPO42− were the main species in the acidic medium (99% at pH = 5) and alkaline medium (97.9% at pH = 10). In the P-Fe-H2O system ((P) = 0.01 mol/L, (Fe3+) = 0.01 mol/L), H2PO4− was transformed to FeHPO4+ at pH = 0–7 due to the existence of Fe3+ and then transformed to HPO42− at pH > 6 as the Fe3+ was mostly precipitated. In the P-Ca-H2O system ((P) = 0.01 mol/L, (Ca2+) = 0.015 mol/L), the main species in the acidic medium was CaH2PO4+ and HPO42−, and then transformed to CaPO4− at pH > 7. In the P-Mg-H2O system ((P) = 0.01 mol/L, (Mg2+) = 0.015 mol/L), the main species in the acidic medium was H2PO4− and then transformed to MgHPO4 at pH = 5–10, and finally transformed to MgPO4− as pH increased. The verification experiments (precipitation experiments) with single metal ions confirmed that the theoretical analysis could be used to guide the actual experiments.

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“…For example, concrete sludge (CS) is an alkaline waste slurry containing CSHs as a major component. CS is abundantly available at construction sites where more concrete materials are generated than required (Okano et al 2016b). Conventionally, CS has been disposed of as a landfill material after solid–liquid separation followed by neutralization with a strong acid (Tsunashima et al 2012).…”

Section: Introductionmentioning

confidence: 99%

“…Previously, we have shown that a substitute for chemically synthesized A-CSHs could be obtained simply by soaking CS in hydrochloric acid solution for a short period of time (Okano et al 2016b). Like chemically synthesized A-CSHs, the acid-treated CS could serve as a bifunctional adsorption–aggregation agent for P i .…”

Section: Introductionmentioning

confidence: 99%

Simple technology for recycling phosphate from wastewater to farmland in rural areas

Ohtake

Okano

Kunisada³

et al. 2017

Ambio

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A simple technology for phosphate (Pi) recovery has been developed using a bifunctional adsorption–aggregation agent. The bifunctional agent was prepared by soaking calcium silicates in hydrochloric acid solution. Importantly, recyclable calcium silicates were available almost free of charge from the cement industry and also from the steel industry. The acid treatment was essential not only for enhancing the ability of calcium silicates to remove Pi from aqueous solution but also for enabling the high settleability of removed Pi. On-site experiments using a mobile plant showed that approximately 80% Pi could be recovered from anaerobic sludge digestion liquor at a wastewater treatment plant. This technology has the potential to offer a simple, compact service for recycling Pi from wastewater to farmland in rural areas.

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A simple technology for phosphorus recovery using acid-treated concrete sludge

Cited by 16 publications

References 12 publications

Phosphorus-Recycling Wittig Reaction: Design and Facile Synthesis of a Fluorous Phosphine and Its Reusable Process in the Wittig Reaction

Phosphorus-Recycling Wittig Reaction: Design and Facile Synthesis of a Fluorous Phosphine and Its Reusable Process in the Wittig Reaction

Thermodynamics Analysis and Removal of P in a P-(M)-H2O System

Simple technology for recycling phosphate from wastewater to farmland in rural areas

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