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JOURNAL OF MOLECULAR LIQUIDS · 2019 · IF 4.561

Synthesis, physicochemical and antimicrobial properties of cardanol-derived quaternary ammonium compounds (QACs) with heterocyclic polar head

Jingyi Ma,Na Liu,Mengen Huang,Limin Wang,Jianwei Han,Hui Qian,Fei Che

As new biomass derived raw material, cardanol has attracted the attention of numerous academic and industrial groups due to its renewability and unique structural features. In this work, seven cardanol-derived quaternary ammonium compounds (QACs) were synthetized with their physicochemical properties and antimicrobial ability evaluated. The surface tension was measured in aqueous medium by the platinum ring method, 2b has the optimal surface activities, which is considerably better than commercialized QAC product cetyltrimethylammonium bromide . Both broth dilution method and agar dilution method were used to obtain the MIC and MBC values of the targeted QACs. 1a , 1b , 2b inhibit the tested bacterial at a concentration of 32 μg/mL. Scanning electron microscopy (SEM) results intuitively showed that the QACs could interact with the bacterial cell membrane, for disrupting the integrity of the membrane. Meanwhile, it was found that the antimicrobial activity depended not only on the alkyl chain length, but also on the CMC value. To sum, seven cardanol-derived QACs were synthetized easily, which showed excellent surface activities and antimicrobial activity, as a promising alternative to the existing fossil fuel derived cationic surfactants and antiseptics.

CAS / MDL: 106-89-8
研究领域: 化学 · 生物学 · 材料科学
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Fundamental Research · 2026 · IF 7

Chain-Length Engineered QACs-Perchlorate Co-Assembly: A Floc-Enhanced Ultrafiltration Strategy for Selective and Efficient Perchlorate Removal

Jian Ao,Lingjun Bu,Yangtao Wu,Jingyi Zhu,Shiqing Zhou

Strategies for selective perchlorate (ClO 4 − ) removal from industrial wastewater remain critical but insufficiently explored, as existing technologies prioritize idealized performance metrics over scalability and cost-effectiveness. Herein, a counterintuitive phenomenon is reported that specific-chain-length QACs (C12-C16) can initiate selective ClO 4 − co-assembly into 0.2-0.3 μm flocs starting at sub-CMC concentrations. Thus, we propose a QACs-assisted ultrafiltration (UF) process to treat ClO 4 − wastewater. Our experimental results show that QACs-assisted UF achieves up to ∼99% ClO 4 − removal for specific industrial wastewater, with only ∼10% decline in flux and resist interference from 10-fold excess competing anions. Through state-of-the-art characterizations and meticulous theoretical calculations, we reveal that ClO 4 − triggers interaction transition from repulsion to attraction between QACs with C12-C16 alkyl chains via synergistic van der Waals, hydrophobic, and electrostatic effects, enabling QACs−ClO 4 − co-assembly and spontaneous floc formation. Furthermore, we demonstrate that QACs with C12, C14, and C16 alkyl chains bind ClO 4 − with high K d of 1.4 × 10 4 , 3.4 × 10 4 , and 7.6 × 10 4 M -1 , and ΔG of -23.60, -25.86, and -27.86 kJ/mol, respectively. Overall, QAC-assisted UF provides a low-pressure, interference-tolerant route to achieve near-complete ClO 4 − removal in real industrial wastewater.

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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2015 · IF 2.912

Analysis of Trace Quaternary Ammonium Compounds (QACs) in Vegetables Using Ultrasonic-Assisted Extraction and Gas Chromatography–Mass Spectrometry

Lei Xiang,Xiong-Ke Wang,Yan-Wen Li,Xian-Pei Huang,Xiao-Lian Wu,Hai-Ming Zhao,Hui Li,Quan-Ying Cai,Ce-Hui Mo

A reliable, sensitive, and cost-effective method was developed for determining three quaternary ammonium compounds (QACs) including dodecyltrimethylammonium chloride, cetyltrimethylammonium chloride, and didodecyldimethylammonium chloride in various vegetables using ultrasonic-assisted extraction and gas chromatography–mass spectrometry. The variety and acidity of extraction solvents, extraction times, and cleanup efficiency of sorbents were estimated to obtain an optimized procedure for extraction of the QACs in nine vegetable matrices. Excellent linearities (R2 > 0.992) were obtained for the analytes in the nine matrices. The limits of detection and quantitation were 0.7–6.0 and 2.3–20.0 μg/kg (dry weight, dw) in various matrices, respectively. The recoveries in the nine matrices ranged from 70.5% to 108.0% with relative standard deviations below 18.0%. The developed method was applied to determine the QACs in 27 vegetable samples collected from Guangzhou in southern China, showing very high detection frequency with a concentration of 23–180 μg/kg (dw).

CAS / MDL: 112-00-5
研究领域: 食品科学 · 分析化学
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JOURNAL OF HAZARDOUS MATERIALS · 2022 · IF 14.224

Insights into the impact of quaternary ammonium disinfectant on sewage sludge anaerobic digestion: Dose-response, performance variation, and potential mechanisms

Wan Yang,Chen Cai,Rui Wang,Xiaohu Dai

Wide commercial applications of antimicrobial quaternary ammonium compounds (QACs) inevitably lead to the release into wastewater and enrichment in sewage sludge . This study evaluated the impacts of levels and structures of QACs on sewage sludge properties, microbial community , and methane production during anaerobic digestion . Methane production was stimulated or not affected at low QACs concentrations, but significantly inhibited at high QACs concentrations. Compared with benzyl and alkyltrimethyl QACs, dialkyl QACs showed least toxicity on digestion performance. Meanwhile, microbial community analysis indicated that shifts in bacterial communities mainly depended on QACs doses, but the archaeal communities were affected by both QACs doses and types. The dominant methanogenic pathway shifted from acetotrophic/methylotrophic methanogens to mixotrophic methanogens by low levels of benzyl and alkyltrimethyl QACs but not dialkyl QACs, and further to hydrogenotrophic methanogens at high QACs concentration. Mechanism exploration revealed that the presence of QACs promoted sludge solubilization by the integrated effects of cell lysis, electric neutralization, and hydrophobicity improvement, but inhibited methanogenesis due to the accumulation of volatile fatty acids and susceptibility of methanogens to QACs. These findings provided a reference for potential impacts of different QACs on sludge biological treatment, which had implications for the use and selection of QACs disinfectants.

研究领域: 环境工程 · 微生物学 · 废物管理
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Journal of Environmental Sciences · 2022 · IF 6.796

Toxicity of the disinfectant benzalkonium chloride (C14) towards cyanobacterium Microcystis results from its impact on the photosynthetic apparatus and cell metabolism

Yunlu Jia,Yi Huang,Jin Ma,Shangwei Zhang,Jin Liu,Tianli Li,Lirong Song

Quaternary ammonium compounds (QACs) are commonly used in a variety of consumer and commercial products, typically as a component of disinfectants. During the COVID-19 pandemic, QACs became one of the primary agents utilized to inactivate the SARS-CoV-2 virus on surfaces. However, the ecotoxicological effects of QACs upon aquatic organisms have not been fully assessed. In this study, we examined the effects of a widely used QAC (benzalkonium chloride-C 14 , BAC-14) on two toxigenic Microcystis strains and one non-toxigenic freshwater Microcystis strain and carried out an analysis focused on primary, adaptive and compensatory stress responses at apical (growth and photosynthesis) and metabolic levels. This analysis revealed that the two toxic Microcystis strains were more tolerant than the non-toxic strain, with 96 hr-EC 50 values of 0.70, 0.76, and 0.38 mg/L BAC-14 for toxigenic M. aeruginosa FACHB-905, toxigenic M. aeruginosa FACHB-469, and non-toxigenic M. wesenbergii FACHB-908, respectively. The photosynthetic activities of the Microcystis , assessed via F v /F m values, were significantly suppressed under 0.4 mg/L BAC-14. Furthermore, this analysis revealed that BAC-14 altered 14, 12, and 8 metabolic pathways in M. aeruginosa FACHB-905, M. aeruginosa FACHB-469, and M. wesenbergii FACHB-908, respectively. It is noteworthy that BAC-14 enhanced the level of extracellular microcystin production in the toxigenic Microcystis strains , although cell growth was not significantly affected. Collectively, these data show that BAC-14 disrupted the physiological and metabolic status of Microcystis cells and stimulated the production and release of microcystin, which could result in damage to aquatic systems.

研究领域: 生态毒理学 · 水生微生物学 · 环境科学 · 藻类学 · 毒理学
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CHEMOSPHERE · 2023 · IF 8.8

Metagenomic insights into the effects of benzyl dodecyl dimethyl ammonium bromide (BDAB) shock on bacteria-driven nitrogen removal in a moving-bed biofilm reactor (MBBR)

Jing Wang,Ling Li,Baihui Chi,Jiajia Shan,Xianliang Yi,Yang Liu,Hao Zhou

The use of disinfectants made from quaternary ammonium compounds (QACs) has greatly increased since the outbreak of SARS-CoV-2. However, the effect of QACs on wastewater treatment performance is still unclear. In this study, a commonly used QAC, i.e., benzyl dodecyl dimethyl ammonium bromide (BDAB), was added to a moving-bed biofilm reactor (MBBR) to investigate BDAB's effect on nutrient removal. When the BDAB concentration was increased to 50 mg L −1 , the ammonia removal efficiency (ARE) greatly decreased, as did the nitrate production rate constants (NPR). This inhibition was partly recovered by decreasing the BDAB concentration to 30 mg L −1 . Metagenomic sequencing revealed the functional genera present during different stages of the control (Rc) and BDAB-added reactors (Re). The enriched genera ( Rudaea , Nitrosospira , Sphingomonas , and Rhodanobacter ) in Rc mainly related to the nitrogen metabolism , while the enriched genera in Re was BDAB-concentration dependent. Functional genes analysis suggested that a lack of ammonia oxidase-encoding genes ( amo ABC) may have caused a decrease in ARE in Re, while the efflux pump-encoding genes emr E, mdf A, and opr M and a gene encoding BAC oxygenase ( oxy BAC) were responsible for BDAB resistance. The increase in the total abundance of antibiotic resistance genes (ARGs) in Re revealed a potential risk arising from BDAB. Overall, this study revealed the potential effect and ecological risks of BDAB introduction in WWTPs .

CAS / MDL: 75-05-8
研究领域: 环境科学 · 微生物学 · 污水处理 · 宏基因组学
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