JOURNAL OF CHEMICAL AND ENGINEERING DATA
·
2013
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IF 2.004
Binwei Shen,Qinbo Wang,Yufang Wang,Xiang Ye,Fuqiong Lei,Xing Gong
The solubilities of adipic acid in acetic acid + water mixtures at (303.2 to 333.2) K and acetic acid + cyclohexane mixtures at (303.2 to 343.2) K are measured. The measured solubility of adipic acid in acetic acid + cyclohexane mixtures with the mass fraction of acetic acid in the solvent mixtures at (0.1 to 1.0) decreases with increasing mass fraction of cyclohexane at constant temperature. However, for the solubility of adipic acid in acetic acid + water with the mass fraction of acetic acid in the solvent mixtures at (0 to 1.0), acetic acid with a mass fraction of 50 % has the best dissolving capacity for adipic acid at constant temperature. The experimental data was correlated by the nonrandom two-liquid (NRTL) activity coefficient model, and the values of the solubilities calculated using the model showed good agreement with the experimental observations.
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ACS Sustainable Chemistry & Engineering
·
2026
·
IF 7.3
Ying Liang,Xianping Liao,Yingshuai Jia,Shiming Guan,Wanling Zhang,Wenbiao Zhang,Yuying Meng,Yi Tang,Qingsheng Gao
Electrooxidation offers a sustainable alternative by utilizing renewable energy to convert biomass-derived cyclohexanol (CHA) to adipic acid (AA), a key industrial chemical for nylon-66 and polyurethane production. While bimetallic Ni-based catalysts enhance the conversion, the role of secondary metals in modulating Ni active-site reconstruction during operation remains unclear, limiting performance optimization. Here, we demonstrate that Cr-doping promoted the dynamic reconstruction of Ni(OH)2 nanosheets to form NiOOH with abundant Ni3+ and oxygen vacancies (OVs), significantly boosting AA electrosynthesis. In situ characterizations reveal that Cr-doping accelerates OH– adsorption and promotes NiOOH formation, while subsequent Cr3+ leaching generates OVs, thus, resolving the long-standing dilemma between stabilizing high-valence Ni and maintaining abundant defects. The optimized catalyst achieves 78.1% AA yield and 85.4% Faradaic efficiency at 1.45 V vs RHE, outperforming undoped Ni(OH)2 and prior systems. Mechanistic studies identify surface Ni3+ and OVs-stabilized *OOH species as the keys for CHA dehydrogenation and cyclohexanone oxidation, respectively. Moreover, a membrane electrode assembly electrolyzer was designed for the efficient coproduction of AA (0.078 mmol h–1 cm–2) and H2 (42.9 mL h–1 cm–2) at a current density of 100 mA cm–2, demonstrating the scalability. This work clarifies the in situ reconstruction of bimetallic sites and provides a design strategy for the efficient electrosynthesis.
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高影响因子
CATALYSIS LETTERS
·
2020
·Vol. 151
·期 2
·338-343
·
IF 2.482
Shi Hexian,Zhang Linfeng,Wu Yudong,Yu Rui,Peng Yang,Wang Yantao,Li Teng,Yang Weiran
Abstract Glucose and its derivatives are valuable and sustainable carbon sources that can be converted into varieties of value-added chemicals. In this study, d -glucaric acid was selectively converted to 3-iodoadipic acid (3-IAA) by hydrodeoxygenation in HI-Rh/C-H 2 system. During this process, HI was a reducing reagent, which can be regenerated in situ by metal catalyzed hydrogenation. The reaction pathway was proposed based on the intermediates identification. Under the optimal conditions, 67.2% yield of 3-IAA was obtained at 130 ℃ for 4 h. As a platform molecule, 3-IAA can be further converted to varieties of building block efficiently, such as adipic acid (AA) and 3-hydroxyadipic acid (3-HAA). Graphic Abstract
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高影响因子
FLUID PHASE EQUILIBRIA
·
2016
·
IF 1.846
Xiaoxiao Sheng,Qinbo Wang,Zhenhua Xiong,Chuxiong Chen
The solubilities of adipic acid in cyclohexanone + cyclohexanol mixtures at (303.15–349.45) K, in cyclohexane + cyclohexanol mixtures at (304.15–339.45) K, and in cyclohexane + cyclohexanone mixtures at (304.85–342.45) K were determined at atmospheric pressure by the dynamic method. Experimental results show that when solvent composition remains constant, solubilities of adipic acid in the studied binary mixed solvents increase monotonically with temperature increasing, and when temperature remains constant, solubilities of adipic acid decrease monotonically with the increasing mass fraction of cyclohexane in cyclohexane + cyclohexanol and cyclohexane + cyclohexanone mixture. However, the measured solubility firstly increases monotonically with the increasing mass fraction of cyclohexanone in cyclohexanone + cyclohexanol mixtures and then reaches the maximum solubility at the mass fraction of cyclohexanone at 0.4. When the mass fraction of cyclohexanone was bigger than 0.40, the solubility of adipic acid decreased with the increasing mass fraction of cyclohexanone. There exists a maximum-solubility effect. Further, both the NRTL equation and the Apelblat equation were used to correlate the experimentally determined solubilities. A fairly good agreement was obtained between the correlated solubilities with the experimental observations. Thermodynamic quantities of dissolution were calculated by the Clark and Glew equation, including dissolution enthalpy, entropy, Gibbs energy and isobaric heat capacity for adicip acid in cyclohexane + cyclohexanol, cyclohexane + cyclohexanone, and cyclohexanone + cyclohexanol solvent mixtures .
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ORGANIC PROCESS RESEARCH & DEVELOPMENT
·
2024
·
IF 3.1
Jimi Su,Lei Ni,Zhen Cheng,Nan Chen,Peiqing Hao,Dongyan Yang,Yong Pan
Adipic acid green synthesis is hazardous due to its highly exothermic nature and thermal instability of the raw material, hydrogen peroxide (H2O2). In this work, an effective chemical method was proposed to inhibit the potential risk of reaction runaway based on a comprehensive study. Reaction species, including reactive intermediates, radicals were identified to establish the radical chain mechanism by various monitoring techniques, such as electron paramagnetic resonance (EPR). Meanwhile, the standard molar reaction enthalpies of each step were determined by theoretical calculations. Combined with the process hazard evaluation and reaction mechanism, the exothermic mechanism was proposed, indicating the heat release was mainly concentrated during the former stage (73 °C stage) of the reaction. Thus, a series of runaway inhibition experiments using radical inhibitor, 2,2,6,6-tetramethylpiperidine oxide (TEMPO) were conducted under different conditions. The results showed that the addition of TEMPO could reduce the maximum temperature, heat release, and maximum exothermic rate of the reaction. The addition of the radical inhibitor could quench all the radicals and terminate the reaction. Thus, the reaction runaway could be inhibited effectively.
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Journal of Environmental Chemical Engineering
·
2026
·Vol. 14
·期 2
·121436
·
IF 7.2
Lei Ni,Yuanyuan Li,Qichao Wang,Juncheng Jiang,Zhiquan Chen,Luping Gu,Na Li,Dongxiao Zhang
The green synthesis of adipic acid is prone to thermal runaway because of unstable peroxide bonds and high exothermicity. In this work, phase change microcapsules (PCMs) were employed as inhibitors to mitigate the potential hazard of uncontrolled thermal behaviour at the source of the reaction. Two PCMs—octadecane/MF (melamine–formaldehyde) and paraffin/MF—were synthesised and characterised systematically. Moreover, the inhibition performance of the phase change capsules under different operating conditions was studied through calorimetric reactions combined with the differential variance (DIV) criterion. The addition of 6.74 wt% octadecane/MF PCMs at the 73 °C reaction stage optimally suppressed thermal runaway, resulting in a maximum reduction in DIV to 0.071, a decrease in heat release of 52.6 kJ and a reduction in the maximum temperature of 19.8 °C. Adding 4.04 wt% paraffin/MF PCMs resulted in a maximum reduction in DIV to 0.087, a decrease in heat release of 28.9 kJ and a reduction in the maximum temperature of 18.7 °C. The results demonstrated that the introduction of phase change microcapsules significantly suppressed the risk of thermal runaway during adipic acid synthesis. In particular, the inhibitory performance of the n-octadecane/MF microcapsules was positively correlated with the dosage within the scope of this study.
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Sustainability
·
2023
·Vol. 15
·期 8
·6530
·
IF 3.9
Yinshan Liu,Lei Ni,Hang Yao,Jimi Su,Zhen Cheng
The synthesis of adipic acid, which is formed by the reaction of cyclohexene oxidized by hydrogen peroxide (H2O2), is hazardous because of the highly exothermic nature of this reaction and H2O2decomposition. The objective of this comprehensive study was to investigate and illustrate the effects of sulfuric acid (H2SO4) and H2O2stabilizer (EDTA) on the thermal hazard of H2O2decomposition and the green synthesis of adipic acid, which also provided a reference to reduce the risk of the reactions. Various calorimetry techniques were carried out to characterize the exothermic behavior of the reactions. An HPLC device was used to characterize the yield of adipic acid and the conversion rate of the raw materials, cyclohexene and H2O2. Meanwhile, density functional theory calculations were performed to understand the reaction mechanism and the associated energies of H2O2decomposition catalyzed by sodium tungstate dihydrate (Na2WO4·2H2O). Finally, combined with the calorimetry results, the risk of the adipic acid synthesis reaction was assessed using the intrinsic control index method (ITHI). The results show that the addition of H2SO4and EDTA can reduce the exothermic heat of the H2O2decomposition reaction and the green synthesis reaction of adipic acid. The yield of adipic acid was also increased. The hazard level of stage A was IV, and to remove more reaction heat, it was recommended to enhance the reflux cooling of stage A. The hazard level of stage B was I, which was very low and no further measures could be taken.Keywords:adipic acid;hydrogen peroxide decomposition reaction;hydrogen peroxide stabilizer;thermal hazard assessment
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MACROMOLECULES
·
2022
·
IF 6.057
Yu-Pei Tian,Tianyu Wu,Xiaoyu Meng,Hai-Mu Ye
Thermodynamic features of extended-chain crystals (ECCs) are the basis for determining crystallization driving force of polymers. However, accurate determination of melting points (Tm0) and enthalpy of fusion (ΔHm0) of ECCs is still a challenge due to the lack of corresponding physically fabricated structures, especially for a copolymer whose ECC has not been prepared or reported yet. Herein, we choose poly(butylene succinate) (PBS) and its random copolymers with adipic acid (PBSA) as model polymers and successfully fabricate their ECCs through a preparation pathway by forming inclusion complexes with urea. Consequently, the values of Tm0 and ΔHm0 have been directly determined, which are quite different from those extrapolated in previous literature. The Tm0 and ΔHm0 of PBS are respectively identified as 136 °C and 133.5 J/g. With the increase of cocrystallized butylene adipate (BA) units in the lattice, the as-measured Tm0 of the ECC declines more significantly than the extrapolated value by the Hoffman–Weeks equation based on a mismatched crystalline structure. The ΔHm0 of PBSA displays an almost linear downward dependence on BA composition, explicitly revealing a defect Gibbs free energy of 0.7 kJ/mol for the cocrystallization of BA units in PBS lattices. Our work sheds light on the accurate determination of properties of polymer ECCs and is essential to expand the understanding of ECCs from homopolymers to copolymers.
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JOURNAL OF CHEMICAL AND ENGINEERING DATA
·
2021
·
IF 2.694
Yangyi Huang,Lin Zhang,Mengqi Yan,Qinan Huang,Yuning Zhang,Yanqun Ren,Weiping Luo
In this research, the solubilities of adipic acid in sec-butyl alcohol (SBA), isobutyl alcohol (IBA), and n-octyl alcohol (NOA); glutaric acid in n-propyl alcohol, isopropyl alcohol, n-butyl alcohol, SBA, IBA, tert-butyl alcohol (TBA), and NOA; and succinic acid in SBA, IBA, TBA, and NOA were determined by the dynamic laser method from 302.65 to 352.95 K at atmospheric pressure (101.3 kPa). Furthermore, the solubilities of three dibasic acids in straight-chain alcohols of different lengths and alcohol isomers were compared. Meanwhile, X-ray diffraction was used to detect the change of the crystal form before and after dissolution. Additionally, the experimental data were correlated by two models (Apelblat model and the modified nonrandom two liquid activity coefficient model), showing that the model matched well with the experimental data. The most accurate model is selected for every system after calculating the Akaike information criterion of each model.
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JOURNAL OF ORGANIC CHEMISTRY
·
2023
·
IF 3.6
Tianyuan Zhang,Jiawu Zhang,Akihiro Mori,Taku Morii,Keisuke Kuramochi,Hirofumi Maekawa
A novel tactic to synthesize unsymmetrical 3-aryladipic acid esters has been developed via magnesium-promoted reductive coupling of ethyl cinnamates with methyl acrylate. In the present methodology, 3-aryladipic acid derivatives were prepared with good functional group tolerance and a wide substrate scope under very mild reaction conditions in good yields. The application of this reaction to dienic acid esters led to the successful control of the reaction to give 5-aryl-oct-3-enedioic acid esters with high regioselectivity.
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PubMed
高影响因子
Journal of Environmental Chemical Engineering
·
2021
·
IF 5.909
Guangrong Liu,Mingxin Chen,Xin Jin,Chuangfu Song,Feifei He,Qiang Huang
In this work, 12-tungstophosphoric acid-TiO 2 composite (PTA-TiO 2 ) catalysts were fabricated by a simple method of impregnation-heat treatment. PTA-TiO 2 composites were characterized by XRD , XPS, TG/DSC, FTIR , UV−vis diffuse reflectance spectra and N 2 adsorption–desorption measurements. The results showed that the heat treatment temperature (200–500 °C) significantly affected the composition and structure of the composite. The higher calcination temperature could destroy the Keggin structure of PTA. The PTA-TiO 2 catalyzed oxidation of cyclohexene by H 2 O 2 to adipic acid demonstrated that the Keggin structure of PTA was critical to the catalytic activity of PTA-TiO 2 . Furthermore, under the photo-thermal catalytic condition, the reaction system showed higher cyclohexene conversion and adipic acid yield. A synergistic effect between the photo- and thermal approach was noticed in the PTA-TiO 2 catalyst prepared at 200 °C (PTA-TiO 2 (200)). Based on the experimental data, a thermocatalysis-dominated but photocatalysis-promoted mechanism was proposed to explain the improvement in catalytic efficiency. The catalyzed oxidation of cyclohexene with photo-thermal synergy enables utilization of sunlight and offers a novel perspective for the manufacture of adipic acid.
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JOURNAL OF MOLECULAR LIQUIDS
·
2019
·
IF 4.561
Sile Shi,Mengqi Yan,Bao Tao,Weiping Luo
In this study, the solid-liquid equilibrium (SLE) data of succinic acid (SA) and glutaric acid (GA) and adipic acid (AA) in N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMAC), dimethyl sulfoxide (DMSO), 1-Methyl-2-pyrrolidinone (NMP) and sulfolane were determined by using the method of dynamic laser at atmospheric pressure. The experimental SLE data indicates that within the temperature range studied (286.25–358.75 K), the solubilities of SA, GA and AA in above five solvents is proportional to the temperature. Meanwhile, three thermodynamic models (Apelblat model, λh model, the modified nonrandom two liquid (NRTL) activity coefficient model) were used to correlate the experimental data, the results show that the correlated data is generally consistent with the experimental data. The result of Akaike Information Criterion (AIC) analysis filter out the best model for every system. In addition, the thermodynamic functions (dissolution enthalpy, entropy, Gibbs energy) were obtained from the SLE data by calculating the van't Hoff equation.
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