Theoretical support for the enhancement of infrared spectrum signals by derivatization of phthalic acid esters using a pharmacophore model

Qiu, Youli; Jiang, Long; Yu, Li

doi:10.1080/00387010.2018.1442353

Cited by 17 publications

(4 citation statements)

References 36 publications

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“…Phthalic acid esters (PAEs), commonly known as phthalates, are widely used as plasticizers in plastic industries [ 14 ], with up to 90% of the plasticizers used in China alone [ 15 ]. Although plasticizers improve the strength and flexibility of plastic products significantly [ 16 ], the addition of several plasticizers increases the flammability of plastic polymers, which eventually restricts applicability [ 17 ].…”

Section: Introductionmentioning

confidence: 99%

“…In summary, plastics and its main additive PAEs are consistent in exhibiting several adverse effects in the environment and eco-system that include flammability, biotoxicity, and enrichment. On the other hand, the application of many flame retardant additives and their byproducts cause serious health hazards and environmental issues, which limit their industrial application [ 14 , 24 ]. Due to the same reason, development of low toxic and eco-friendly flame retardant technologies has become a very important research direction.…”

Section: Introductionmentioning

confidence: 99%

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A Modified 3D-QSAR Model Based on Ideal Point Method and Its Application in the Molecular Modification of Plasticizers with Flame Retardancy and Eco-Friendliness

Zhang

Zhao

2020

Polymers

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The addition of plasticizers makes plastics flammable, and thus, poses a potential risk to the environment. In previous researches, plasticizers with flame retardancy had been synthesized, but their eco-friendliness had not been tested or described. Thus, in this paper, eco-friendliness plasticizers with flame retardancy were designed based on phthalic acid esters (PAEs), which are known as common plasticizers and major plastic additives. For a comprehensive analysis, such as flammability, biotoxicity, and enrichment effects, 17 PAEs’ comprehensive evaluation values were calculated based on the ideal point method. Further, a multi-effect three-dimensional quantitative structure-activity relationship (3D-QSAR) model of PAEs’ flammability, biotoxicity and enrichment effects was constructed. Thus, 18 dimethyl phthalate (DMP) derivatives and 20 diallyl phthalate (DAP) derivatives were designed based on three-dimensional contour maps. Through evaluation of eco-friendliness and flammability, six eco-friendly PAE derivatives with flame retardancy were screened out. Based on contour maps analysis, it was confirmed that the introduction of large groups and hydrophobic groups was beneficial to the simultaneous improvement of PAEs’ comprehensive effects, and multiple effects. In addition, the group properties were correlated significantly with improved degrees of the comprehensive effects of corresponding PAE derivatives, confirming the feasibility of the comprehensive evaluation method and modified scheme.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

A Modified 3D-QSAR Model Based on Ideal Point Method and Its Application in the Molecular Modification of Plasticizers with Flame Retardancy and Eco-Friendliness

Zhang

Zhao

2020

Polymers

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“…LogKow is related to the hydrophobicity of compounds, ranging from 1.60 (DMP) to 8.71 (DEHP). The alkyl chain length represents the average of two alkyl chains, with DMP having the most petite chain length (1), followed by DEP (2), DIBP (4), DnBP (4), BBP (5.5), and DEHP (8). The logKow and alkyl chain length of the five PAEs increase while their solubility in water decreases, which is related to the increase in molecular weight.…”

Section: Correlation Analysismentioning

confidence: 99%

“…During the process of plastic film production, plastic films were often supplemented as plasticizers to enhance their chemical stability, flexibility, transparency, and other properties of plastic films [5,6]. Studies have indicated that PAEs can constitute up to 80 wt% of the plasticizers used in China [7,8]. Residual plastic films in the soils could also release pollutants, such as PAEs, into the soils [9].…”

Section: Introductionmentioning

confidence: 99%

Accumulation and Transport of Phthalic Acid Esters in the Soil-Plant System of Agricultural Fields with Different Years of Film Mulching

Zhang,

Li,

et al. 2023

Sustainability

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In this study, we investigated the accumulation and transport patterns of phthalate ester (PAEs) compounds in the soil-plant system of maize and cabbage fields under different film mulching years. The total content of five PAEs in the maize fields soil ranged from 156.19 to 566.1 μg kg−1 with film mulching for 0–20 years. The total content of five PAEs in the cabbage field soils ranged from 252.48 to 559.07 μg kg−1 with film mulching for 0–30 years. The PAEs content in cabbage and maize field soils was lower than the environmental quality standards for soil (GB 15618-2008). With the increase in film mulching years, both maize and cabbage soil PAEs contents increased significantly (p < 0.05), while among the five PAEs, the contents of di-n-butyl phthalate (DnBP) and di(2-ethylhexyl) phthalate (DEHP) increased the most significantly, and the content of DEHP in the soils was the highest. The DEHP content in soils planted with maize ranges from 134.03 to 406.79 μg kg−1 with the film mulching for 20 years; while in soil planted with cabbage, it ranges from 229.35 to 405.2 μg kg−1 with the film mulching for 30 years. The DEHP content in all of the soils has not exceed the limit value established by the USEPA in U.S. Five PAEs were detected in maize seeds and cabbage leaves, among which the DEHP content exceeded the maximum residue limit set by the National Food Safety Standard (GB 9685-2016) for DEHP in food after more than 10 years of mulching. The bioaccumulation and translocation factors in cabbage showed a significant positive correlation with the film mulching years. However, the bioaccumulation factor and translocation factor in maize have weak correlations with the film mulching years, possibly due to the lower PAEs content in the deep soil layers where maize roots are distributed. Our research revealed a significant association between the presence and distribution of PAEs in crops and mulching years. These novel discoveries provide fundamental information for controlling PAEs pollution in agricultural environments.

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Investigation of the Potential Environmental Risks of Phthalate Derivatives Designed To Be Environmentally Friendly

Zhang

Sun

Hou

et al. 2020

Enviro Toxic and Chemistry

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Phthalate derivatives with low estrogenic activity, high infrared spectrum signals, high Raman characteristic vibration spectrum, high fluorescence intensity, and high ultraviolet sensitivity were selected as precursors from our previous studies, so that the changes in their toxicity and estrogenic activity during biological metabolism, ozone oxidation, photocatalytic degradation, photodegradation, and microbial degradation could be studied.The transformation pathways of these derivatives were simulated, and the reaction energy barriers were calculated. To determine the potential environmental risks of these phthalate derivatives, the pharmacophore models of biotoxicity and estrogen activity of phthalates were used to predict the biotoxicity and estrogen activity of the transformed products. The results showed an increase in the biotoxicity and estrogen activity of the biometabolites, ozonation products, photocatalytic degradation products, and microbial degradation products; the only products that did not follow this trend were the photodegradation products. Notably, the pathways that produced more potentially toxic compounds were the less favorable paths. Our results indicate that the transformation products of the designed environmentally friendly phthalate derivatives potentially pose environmental risks. To avoid such risks, the environmental transformation pathway of these derivatives should be simulated to screen for environmentally friendly phthalate molecules. Environ Toxicol Chem 2020;39:1138–1148. © 2020 SETAC

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Theoretical support for the enhancement of infrared spectrum signals by derivatization of phthalic acid esters using a pharmacophore model

Cited by 17 publications

References 36 publications

A Modified 3D-QSAR Model Based on Ideal Point Method and Its Application in the Molecular Modification of Plasticizers with Flame Retardancy and Eco-Friendliness

A Modified 3D-QSAR Model Based on Ideal Point Method and Its Application in the Molecular Modification of Plasticizers with Flame Retardancy and Eco-Friendliness

Accumulation and Transport of Phthalic Acid Esters in the Soil-Plant System of Agricultural Fields with Different Years of Film Mulching

Investigation of the Potential Environmental Risks of Phthalate Derivatives Designed To Be Environmentally Friendly

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