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FUEL PROCESSING TECHNOLOGY · 2015 · IF 3.352

Separation of toluene from toluene/alkane mixtures with phosphonium salt based deep eutectic solvents

Yucui Hou,Zhongyi Li,Shuhang Ren,Weize Wu

In this work, separation of aromatic hydrocarbons from aromatic/aliphatic mixtures by deep eutectic solvents (DESs) at room temperature was developed. It was found that DES formed by levulinic acid as hydrogen bond donor and tetrabutylphosphonium bromide (TBPB) as hydrogen bond acceptor could efficiently separate aromatic hydrocarbons from aromatic/aliphatic mixtures. Levulinic acid/TBPB mole ratio, DES/toluene mole ratio, toluene mole fraction , and extraction temperature had an influence on the selectivity and extraction rate of toluene. The extraction could be performed at optimal conditions of 6:1   mol ratio of levulinic acid to TBPB and 6.4:1   mol ratio of DES to toluene at room temperature. Toluene in DES could be recovered by distillation of toluene at 100   °C under reduced pressure and DES was reused four times without obvious decrease in weight, selectivity and extraction rate. The work may provide an environmentally friendly method to separate aromatic/aliphatic mixtures, which avoids using a large number of toxic organic solvents.

CAS / MDL: 67-48-1
研究领域: 化学工程 · 环境科学
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LANGMUIR · 2011 · IF 4.269

Synergistic Antibacterial Brilliant Blue/Reduced Graphene Oxide/Quaternary Phosphonium Salt Composite with Excellent Water Solubility and Specific Targeting Capability

Xiang Cai,Shaozao Tan,Minsong Lin,Agui Xie,Wenjie Mai,Xiuju Zhang,Zhidan Lin,Ting Wu,Yingliang Liu

A water-soluble brilliant blue/reduced graphene oxide/tetradecyltriphenylphosphonium bromide composite (BB-rGO-TTP) was prepared by using noncovalent brilliant blue-functionalized reduced graphene oxide (BB-rGO) as the tetradecyltriphenylphosphonium bromide (TTP) carrier. Antibacterial performance of this novel composite was investigated for both Gram-positive and Gram-negative bacteria. The results showed that the novel BB-rGO-TTP, combing the advantages of graphene and TTP, displayed excellent synergistic antibacterial activity, specific targeting capability, water solubility, and mild cytotoxicity, suggesting the great potential application as sprayable graphene-based antibacterial solutions.

研究领域: 材料科学 · 微生物学
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FOOD CHEMISTRY · 2024 · IF 8.5

Preparation of citric acid cross-linked chitosan quaternary phosphonium/polyvinyl alcohol composite film and its application in strawberry preservation

Wangkun Lai,Lin Wang,Yu Pang,Meihua Xin,Mingchun Li,Lulu Shi,Yangfan Mao

Chitosan quaternary phosphine salts (NPCS) were synthesized with enhanced antimicrobial properties using a two-step method. Composite films (CNSP) were prepared by incorporating NPCS and polyvinyl alcohol (PVA) as the base material, citric acid as the crosslinker and functional additive, exhibiting antibacterial and UV-blocking properties. The composite film showed a maximum tensile strength of 20.4 MPa, an elongation at break of 677%, and a UV light barrier transmittance of 70%. Application of these composite membranes in preserving strawberries demonstrated effectiveness in maintaining freshness by preventing water loss, inhibiting microbial growth , and extending shelf life. In addition, the composite film demonstrated biosafety. These results indicate that CNSP composite films holds significant promise for safe and sustainable food packaging applications.

CAS / MDL: 9002-18-0 8013-01-2
研究领域: 食品科学 · 材料科学 · 生物技术
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POLYMER BULLETIN · 2014 ·Vol. 71 ·期 10 ·2543-2557 · IF 1.491

Quaternary phosphonium modified epoxidized natural rubber: effect of reaction time, reaction mechanism, thermal property and antimicrobial activity

Li Chun,Liu Yuan,Cao Ping,He Jia,Lin Zhongshi,Ao Ningjian,Chu Bin

Herein we endow epoxidized natural rubber with antimicrobial activity by chemical modification. The rubber is firstly ring-opened by bromoacetic acid and then modified by antimicrobial group quaternary phosphonium salt. Using the hydrogen nuclear magnetic resonance spectroscopy ( 1 H NMR) and the ICP atomic emission spectrometry (ICP-AES), the degree of epoxidation, the convert ratio of epoxy groups, and the phosphorus content of the products are measured, and then the effects of reaction time on the structure of products are investigated. The possible reaction mechanism and side reactions in ring-opening procedure are discussed through the comparison of data with different reaction time, and the ring-expansion reaction is supposed to be dominated in the side reactions. The thermal properties of modified rubbers and the structural factors behind are also investigated using differential scanning calorimeter and thermogravimetric analyzer. Antimicrobial activities of modified rubbers with different ring-opening reaction time toward Escherichia coli are studied, and the activity may increase with the content of quaternary phosphonium salt groups. This research may have the benefit for optimizing the structure of chemically modified antimicrobial rubbers.

CAS / MDL: 79-08-3 603-35-0
研究领域: 材料科学 · 化学工程 · 生物医学
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Advanced Optical Materials · 2023 ·Vol. 11 ·期 17 ·2300328 · IF 9

A New Class of Donor-π-Acceptor Phosphonium Salt Exhibiting Intriguing Thermally Activated Delayed Fluorescence

Jun-Hua Wei,Jian-Bin Luo,Zi-Lin He,Zhi-Zhong Zhang,Dai-Bin Kuang

Thermally activated delayed fluorescence (TADF) behaviors in metal halide perovskite and perovskite derivatives are rarely reported due to the absence of suitable TADF molecules that can serve as the A-site cations. Herein, a series of novel donor- π -acceptor type of molecules are developed by adopting substituted phosphine and phosphonium as the electron donor and acceptor linked by the polarized π -spacer. The prepared ((diphenylphosphaneyl)phenyl)diphenylphosphonium-X (BzDPP-X, X = counterions: Cl − , Br − , I − , NO 3 − , CH 3 COO − etc.) salts show bright emission in the visible range with TADF characteristics due to the strong intramolecular charge transfer (ICT). Benefiting from the spatially separated highest occupied molecular orbital and lowest unoccupied molecular orbital, small singlet-triplet energy splitting (Δ E ST ) is obtained, facilitating the reverse intersystem crossing process. It turns out that the emission of BzDPP-X is dependent on the counter anions, and the counterions help to stabilize the ICT state. Intriguingly, the emission can be tuned by integrating metal-halide units into the above phosphonium salt. Remarkably, the zinc-based halide exhibits a higher photoluminescence quantum yield (36.2%) than the pure benzyl(2-(diphenylphosphaneyl)phenyl)diphenylphosphonium bromide (26.9%). This work exemplifies an easy design concept and a facile synthetic method toward ionic luminescent materials.

研究领域: 材料科学 · 化学
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Molecular Catalysis · 2025 · IF 4.9

Efficient bifunctional urea–phosphonium halide catalysts for the cycloaddition of CO2 to epoxides

Bo Liu,Xin Zou,Zhenjiang Li,Ping Chen,Shengxin Chen,Xin Yuan,Yongzhu Hu,Yanqi Shi,Ziqi Liu,Kai Guo

The cycloaddition of CO 2 to epoxides (CCE) reaction is one of the few chemical processes viable commercially in the valorization of CO 2 . A bifunctional urea–phosphonium halide with both electrophilic and nucleophilic centers was proposed as an effective catalyst for CCE reactions here. The urea–phosphonium halides with different urea substituents and halide anions were simply synthesized and systematically evaluated in CCE reactions. It was found that the H-bond donicity of the urea N–Hs, the nucleophilicity of the halide anion, and the affinity between the urea and halide anions jointly affected the catalytic activity of the urea–phosphonium halide in CCE reactions. The H-bonding strength between the N–Hs and nucleophilic anions was disclosed via NMR titrations. The catalyst featuring a 3,5-bis(trifluoromethyl)phenyl-substituted urea structure and an iodide anion was selected as the optimal structure, which promoted the cycloaddition of styrene oxide with excellent conversion (92 %) and selectivity (99 %) in 6 h under mild conditions (1 mol% catalyst loading, 100 °C, 0.1 MPa CO 2 ). Furthermore, the bifunctional catalyst performed exceptional recyclability, exhibiting no discernible decline in catalytic activity over five consecutive reaction cycles. The structure−performance relationship of the urea–phosphonium halides and a wide range of substrates applicability provided valuable insights for the optimization of the existing catalysts or the further design of new effective organocatalysts.

CAS / MDL: 4848-43-5
研究领域: 有机化学 · 催化化学 · 绿色化学 · 二氧化碳利用 · 分子催化 · 功能材料化学
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INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES · 2024 · IF 7.7

Novel antibacterial pullulan derivatives modified with quaternary phosphonium salts for infected wound treatments

Wenzhuang Cui,Yujie Liu,Ying Yue,Jun Wang,Xianhua Meng,Zhizhou Yang,Chu Gong,Jun-Li Yang

The development of novel antibacterial agents is urgently needed to tackle bacterial infection, the major global issue menacing human health. Among them, polymeric quaternary phosphonium salts are worth noticing owing to their strong antibacterial activities and other merits including low bacterial drug resistance. Herein, pullulan modified with quaternary phosphonium salts (PQP) was synthesized using esterification reactions of pullulan and (5-carboxypentyl)triphenylphosphonium bromide (CPTPPB) mediated by N,N′‑carbonyldiimidazole (CDI), and was evaluated as novel antibacterial agents for treating wound infection for the first time. The chemical structures, chemical bonding, elemental compositions, crystalline properties and thermostability of PQP were systematically investigated. PQP exhibited in vitro antibacterial activities against Staphylococcus aureus ( S. aureus ) and Escherichia coli ( E. coli ), which were unveiled by the spread plate method and possibly resulted from the damage of bacterial cell walls/membranes mediated by electrostatic and hydrophobic interactions according to preliminary mechanism studies. Weak cytotoxicity and excellent hemocompatibility of PQP at the effective bactericidal concentration were observed. Moreover, in the infected wound model of mice, PQP was capable of disinfecting the wound and accelerating the healing. We opine PQP in this work is promising for antibacterial applications and will inspire the synthesis of novel antibacterial agents derived from natural polymers.

研究领域: 药学 · 材料科学 · 生物医学工程 · 微生物学
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CHEMOSPHERE · 2017 · IF 4.208

Advanced oxidation removal of hypophosphite by O3/H2O2 combined with sequential Fe(II) catalytic process

Zilong Zhao,Wenyi Dong,Hongjie Wang,Guanhan Chen,Wei Wang,Zekun Liu,Yaguang Gao,Beili Zhou

Elimination of hypophosphite (HP) was studied as an example of nickel plating effluents treatment by O 3 /H 2 O 2 and sequential Fe(II) catalytic oxidation process. Performance assessment performed with artificial HP solution by varying initial pH and employing various oxidation processes clearly showed that the O 3 /H 2 O 2 ─Fe(II) two-step oxidation process possessed the highest removal efficiency when operating under the same conditions. The effects of O 3 dosing, H 2 O 2 concentration, Fe(II) addition and Fe(II) feeding time on the removal efficiency of HP were further evaluated in terms of apparent kinetic rate constant. Under improved conditions (initial HP concentration of 50 mg L −1 , 75 mg L −1 O 3 , 1 mL L −1 H 2 O 2 , 150 mg L −1 Fe(II) and pH 7.0), standard discharge (<0.5 mg L −1 in China) could be achieved, and the Fe(II) feeding time was found to be the limiting factor for the evolution of apparent kinetic rate constant in the second stage. Characterization studies showed that neutralization process after oxidation treatment favored the improvement of phosphorus removal due to the formation of more metal hydroxides. Moreover, as a comparison with lab-scale Fenton approach, the O 3 /H 2 O 2 ─Fe(II) oxidation process had more competitive advantages with respect to applicable pH range, removal efficiency, sludge production as well as economic costs.

研究领域: 环境工程 · 废水处理 · 化学工程
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CHEMICAL ENGINEERING JOURNAL · 2024 · IF 13.3

Quaternary phosphonium strong based anion exchangers for the selective adsorption of nitrate

Yingpeng Gu,Yue Sun

Nitrate (NO 3 − ) has become a global issue in the field of water treatment due to its extensive distribution in the natural waterbody and industrial process. Quaternary ammonium (R 4 N + ) strong based anion exchangers are still the main product used for NO 3 − remediation. However, the quaternary phosphonium groups (R 4 P + ) with stronger polarization and anionic affinity have not been adequately studied. This work employed triphenylphosphine (PPh 3 ) and tributylphosphine (TBP) to quaternize chloromethylated macroporous polystyrene resin (PS-Cl), and prepared novel strong anion exchangers (PS-PPh 3 and PS-TBP) for the selective adsorption of NO 3 − . These exchangers exhibited good adsorption performance for NO 3 − in the broad-spectrum pH range of 2.0–11.0. The adsorption capacities of PS-PPh 3 and PS-TBP fitted by Langmuir isotherm were approximately 20.14 and 25.53 mg NO 3 − -N/g, respectively. The adsorption processes of these exchangers could be fitted using pseudo-second-order (PSO) kinetic curves. Both selectivity experiments and density functional theory (DFT) indicated the superior NO 3 − selectivity of quaternary phosphonium exchangers, and demonstrated that the effect of charge distribution density of the exchanger on NO 3 − selectivity was greater than that of steric hindrance and hydrophobicity, which emphasized the importance of enhancing anionic affinity of functional group at low charge density. After five cycles of adsorption–desorption cycles with NaCl desorption solution, these two exchangers still maintained above 90 % of adsorption capacities for NO 3 − . The column experiment and benefit assessment also indicated that quaternary phosphonium exchangers had the good application value and potential to become a substitute for quaternary ammonium anion exchangers when facing extremely complex water matrix.

CAS / MDL: 64-17-5 78-87-5 67-64-1
研究领域: 环境科学 · 水处理 · 化学工程 · 材料科学
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INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES · 2023 · IF 8.2

Effect of the structure of chitosan quaternary phosphonium salt and chitosan quaternary ammonium salt on the antibacterial and antibiofilm activity

Lin Wang,Meihua Xin,Mingchun Li,Wenfeng Liu,Yangfan Mao

N -(4- N′, N′, N′ -trimethylphosphonium chloride) benzoyl chitosan (TMPCS), N -(4- N′, N′, N′ -triphenylphosphonium chloride) benzoyl chitosan (TPPCS), and N- (4- N′, N′, N′ -trimethylmethanaminium chloride) benzoyl chitosan (TMACS) were synthesized. The structures of the products were characterized by Fourier transform infrared spectroscopy, Nuclear magnetic resonance spectroscopy and ultraviolet-visible spectroscopy. Their antibacterial activities against Escherichia coli ( E. coli ) and Staphylococcus aureus ( S. aureus ) were investigated in vitro using the antibacterial rate, minimal inhibitory concentration (MIC) and minimum bactericidal concentration (MBC), the antibiofilm activity was investigated by crystal violet assay. The antibacterial assessment revealed that the chitosan quaternary phosphonium salts of similar structure had superior antibacterial activity than chitosan quaternary ammonium salt. The antibacterial rate of CS, TMPCS, TPPCS and TMACS against E. coli at 0.5 mg/mL was 10.4 %, 42.0 %, 58.5 % and 21.6 % respectively. At the same concentration, the antibacterial rate of TMPCS, TPPCS and TMACS against S.aureus was all up to 100 %. The biofilm inhibition rate of CS, TMPCS, TPPCS and TMACS at a half of MIC against E.coli was 28.4 %, 33.9 %, 56.6 % and 57.6 % respectively, and against S.aureus was 30.8 %, 53.8 %, 62.2 % and 58.5 % respectively. The biofilm removal rate of CS, TMPCS, TPPCS, TMACS against E.coli at 2.5 mg/mL was 20.6 %, 46.4 %, 48.9 % and 41.6 % respectively, and against S.aureus at 2.5 mg/mL was 41.5 %, 60.4 %, 69.9 % and 59.01 % respectively.

CAS / MDL: 548-62-9 594-09-2
研究领域: 材料科学 · 生物技术 · 微生物学
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