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Highly crystalline core dominated the catalytic performance of carbon dot for cyclohexane to adipic acid reaction

Nano Research 2022年第8期15卷 7662-7669页

作者： Xiao Wang Wenyi Bian Tianyang Zhang Yajie Zhao Mingwang Shao Haiping Lin Yang Liu Hui Huang Zhenhui Kang Institute of Functional Nano&Soft Materials(FUNSOM) Jiangsu Key Laboratory for Carbon-Based Functional Materials&DevicesSoochow UniversitySuzhou 215123China Macao Institute of Materials Science and Engineering(MIMSE) MUST-SUDA Joint Research Center for Advanced Functional MaterialsMacao University of Science and TechnologyTaipa 999078MacaoChina School of Physics and Information Technology Shaanxi Normal UniversityXi’an 710062China

Carbon dots(CDs)have uniquely structural,physicochemical and photochemical properties,suggesting a promising platform for catalysis applications.The in-depth understanding of the structure-activity relationship in the CDs-based catalyst system needs to know the effect of the crystalline core on their catalytic performance.The efficient catalytic oxidation of cyclohexane is an urgent challenge in current chemical industry,in which,adipic acid(AA)plays an important role in industry for synthesis of nylon6 and nylon-66.Here,we fabricated the pristine CDs by electrochemical etching graphite rod method and derived CDs with high crystalline core(CD-600,CD-800,and CD-1100)through a thermal treatment method in tube furnace.Furthermore,these CDs performed an outstanding catalytic performance for one-step synthesis of AA from cyclohexane.With the help of machine learning(ML),the deep correlations between features(structures of CDs,catalytic conditions)and catalytic performances were investigated by XGBoost(XGB)model.Then under the optimization and prediction of XGB,it was found that high crystalline core preceded the other features and CD-1100 could get the best conversion of 30.696%and selectivity to AA of 92.52%at reaction conditions of 130℃,1.5 MPa,and 10 h.This work pioneered the application of ML in industrial issues and demonstrated a comprehensive understanding on CDs as catalyst to realize one-step synthesis of AA.

关键词： adipic acid carbon dots machine learning catalytic performances crystalline core

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Kinetic study for the oxidation of cyclohexanol and cyclohexanone with nitric acid to adipic acid

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Chinese Journal of Chemical Engineering 2021年第1期34卷 183-189页

作者： Detao Pan Guangxiao Li Yuanhai Su Huilong Wei Zhenghong Luo Department of Chemical Engineering School of Chemistry and Chemical EngineeringState Key Laboratory of Metal Matrix CompositesShanghai Jiao Tong UniversityShanghai 200240China

The adipic acid is an important intermediate in the production of nylon,polyurethane and polye ster resin s.The industrial approach for preparing adipic acid is through the liquid catalytic oxidation of KA oil with nitric acid.In this work,a comprehensive model is developed for this reaction based on the kinetic study conducted in a continuous flow tubular reactor.The kinetic model fits well with the experimental results across the experimental conditions,and the average relative error between the calculated and experimental values is 5.7%.Results show that there was an induction period at the early stage of reaction.Moreover,it is found that at temperature range of 328-358 K,the formation rate of adipic acid strongly dependents on the temperature and nitric acid concentration.The developed model is used to predict the yield of adipic acid at 359-368 K.The work in this study could provide much knowledge for industrial tubular reactor design.

关键词： adipic acid Nitric acid Tubular reactor Kinetic model

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Highly dispersed metal incorporated hexagonal mesoporous silicates for catalytic cyclohexanone oxidation to adipic acid

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Chinese Journal of Chemical Engineering 2020年第10期28卷 2542-2548页

作者： Wenjuan Yan Wenxiang Zhang Qi Xia Shuaishuai Wang Shuxia Zhang Jian Shen Xin Jin State Key Laboratory of Heavy Oil Processing Center for Chemical Engineering Experimental TeachingChina University of PetroleumQingdao 266580China College of Environment and Resources Xiangtan UniversityXiangtan 411105China

adipic acid is a dicarboxylic acid of great industrial importance,mainly used in the production of nylon-6,6 and polyurethane.The use of nitric acid as an oxidant in the industrial production of adipic acid poses significant carbon footprint to the environment.Clean adipic acid synthesis methods using a heterogeneous catalyst with H2O2 as oxidant and water as solvent have potential advantages of low catalyst cost,easy synthesis and recovery,cleanness and environmental protection.In this work,hexagonal mesoporous silicate materials were synthesized by a sol–gel method and evaluated for cyclohexanol/cyclohexanone oxidation to adipic acid.The physical and chemical properties of Fe-HMS were characterized by XRD,HR-TEM,BET and UV–Vis.The experimental results showed that Fe-HMS materials show pore sizes ranging from 2–3 nm.W-and Mo-based polyoxometalates were also evaluated and compared to the Fe-based HMS catalysts.To improve the adipic acid yield,the influence of the transition metal as well as the effect of metal loading,reaction temperature and catalyst amount on the catalytic performances of Fe-HMS have been investigated in details.When Si/Fe atomic ratio=100,Fe-HMS catalyst shows the highest activity,with a cyclohexanone conversion of 92.3%and adipic acid selectivity of 29.4%.The reaction pathway of cyclohexanone oxidation was further proposed based on experimental data.

关键词： Oxidation adipic acid Hexagonal mesoporous silicates hydrogen peroxide

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Scenario analysis on abating industrial process greenhouse gas emissions from adipic acid production in China

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Petroleum Science 2020年第4期17卷 1171-1179页

作者： Qing Tong Han-Yi Lin Xu-Ying Qin Run-Sheng Yan Yue-Feng Guo Xin-Yang Wei Institute of Nuclear and New Energy Technology Tsinghua UniversityBeijing 100084China School of Energy Power and Mechanical EngineeringNorth China Electric Power UniversityBeijing 102206China Environmental Protection Research Institute of Light Industry Beijing 100089China State Key Laboratory of Virtual Reality and Suzhou Institute of Beihang University Suzhou 215200China Department of Accounting and Finance School of BusinessMacao University of Science and TechnologyMacao 999078China

adipic acid is an important petrochemical product,and its production process emits a high concentration of greenhouse gas N_2 O.This paper aims to provide quantitative references for relevant authorities to formulate greenhouse gas control roadmaps.The forecasting method of this paper is consistent with the published national inventory in terms of caliber.Based on the N_2 O abatement technical parameters of adipic acid and the production trend,this paper combines the scenario analysis and provides a measurement of comprehensive N_2 O abatement effect of the entire industry in China.Four future scenarios are assumed.The baseline scenario(BAUS) is a frozen scenario.Three emission abatement scenarios(ANAS,SNAS,and ENAS) are assumed under different strength of abatement driving parameters.The results show that China's adipic acid production process can achieve increasingly significant N_2 O emission abatement effects.Compared to the baseline scenario,by 2030,the N_2 O emission abatements of the three emission abatement scenarios can reach 207-399 kt and the emission abatement ratios can reach 32.5%-62.6%.By 2050,the N_2 O emission abatements for the three emission abatement scenarios can reach 387-540 kt and the emission abatement ratios can reach 71.4%-99.6%.

关键词： Scenario analysis Industrial process greenhouse gas emissions adipic acid N2O emission abatement China

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Studies on QSAR of metalloporphyrin catalysts in the oxidation of cyclohexane to adipic acid

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Frontiers of Chemical Science and Engineering 2007年第2期1卷 155-161页

作者： CHEN Yixia SHE Yuanbin XU Jing LI Yan Institute of Green Chemistry and Fine Chemicals and Department of Chemistry and Chemical Engineering College of Environmental and Energy EngineeringBeijing University of TechnologyBeijing 100022China

The catalysis of chloridized metalloporphyrins in the oxidation of cyclohexane to adipic acid was systemati-cally investigated.The turnover numbers(TON)data of 19 catalysts were obtained experimentally under optimal reac-tion conditions,and 2.4x106 TON for T(o-Cl)PP-MnIIICl catalyst at 2.0x10–6 mol/L of dosage was reached under the conditions of dioxygen pressure of 2.5 MPa at 150°C for 4 h.This was the best result reported for this reaction up to now.The QSAR models for each concerned metallopor-phyrin were established,where the catalytic activity was significantly correlated with the ELUMO(the energy level of the lowest unoccupied molecule orbit)and LM-N(the bond length between metal-nitrogen atoms).Using the QSAR models,four new metalloporphyrins with substituted nitro group were designed,and their catalytic activities were predicted.The experimental TON data of newly designed porphyrins were in good agreement with the predicted ones,and the square of their correlation coefficient was more than 0.958.The above results demonstrated that the proposed structure-activity relationship model could be applied to design some new metalloporphyrin catalysts,and to predict their catalytic activity in cyclohexane oxidation.

关键词： metalloporphyrin catalyst quantitative structure-activity relationship(QSAR)model cyclohexane oxidation adipic acid

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Production of adipic acid by the native-occurring pathway in Thermobifida fusca B6

Production of adipic acid by the native-occurring pathway in...

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中国生物工程学会第六次全国会员代表大会暨第九届学术年会

作者：邓禹毛银江南大学粮食发酵工艺与技术国家工程实验室 The Key Laboratory of Industrial Biotechnology Ministry of EducationJiangnan University National Engineering Laboratory for Cereal Fermentation Technology (NELCF) Jiangnan University

Aims:To identify the native-occurring adipate pathway in a previously engineered Thermobifida fusca B6 strain and optimize the adipic acid production of this strain on glucose and corncob.Methods and Results:The native-occurring adipate pathway in T.fusca B6 was identified to be the reverse adipate degradation pathway,including 5 steps:β-ketothiolase(Tfu875),3-hydroxyacyl-CoA dehydrogenase(Tfu399),3-hydroxyadipyl-CoA dehydrogenase(Tfu067),5-Carboxy-2-pentenoyl-CoA reductase(Tfu647) and succinyl-CoA synthetase(Tfu576,Tfu577).The cell lysates of T.fusca wild-type strain with the addition of the Tfu647 protein produced trace adipic acid,while no adipic acid was produced in the absence of this protein.The above results prove that the low expression of Tfu647 in the WT strain was the reason why it didn’t produce any adipic acid.We then demonstrated that in T.fusca B6,the maximal titer of adipic acid on 50 g/L glucose was 2.23 g/L with 0.045 g/g-glucose yield and 0.22 g/L adipic acid was produced from 19.38 g/L milled corncob.Conclusions:The reverse adipate degradation pathway was found to be responsible for the adipate synthesis in T.fusca B6 and Tfu647 was the regulatory node on this pathway.Significance and Impact of Study:T.fusca B6 was the first reported microorganism using its native-occurring pathway to accumulate adipic acid.It had the highest reported yield and titer of adipic acid so far.

关键词： adipic acid T.fusca B6 reverse adipate degradation pathway 5-Carboxy-2-pentenoyl-CoA reductase corncob

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环己酮绿色氧化合成己二酸质谱分析

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分析测试学报 2004年第Z1期23卷 126-128页

作者：张敏胡岚雷蓓樊永惠杨彩宁西安近代化学研究所陕西西安710065

　　己二酸是合成尼龙-66的主要原料,同时在低温润滑油、合成纤维、油漆、聚亚胺酯树脂及食品添加剂的制备等方面也有重要用途,目前己二酸的世界年产量估计已达220万吨.工业上己二酸的生产是以环己烷经两步氧化合成,第一步为环己烷在金... 详细信息

　　己二酸是合成尼龙-66的主要原料,同时在低温润滑油、合成纤维、油漆、聚亚胺酯树脂及食品添加剂的制备等方面也有重要用途,目前己二酸的世界年产量估计已达220万吨.工业上己二酸的生产是以环己烷经两步氧化合成,第一步为环己烷在金属离子催化下用氧气氧化为环己醇、环己酮,第二步用浓HNO3氧化环己醇、环己酮制得己二酸.……

关键词： GC- MS (EI, CI) Hydrogen peroxide Clear catalytic oxidation Cyclohexanone adipic acid

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Comparative Heat Transfer Data for Solid-Liquid Phase Change of D-Mannitol and adipic acid

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Energy and Power Engineering 2022年第11期14卷 680-704页

作者： Ulyana Horbatyuk Ana Magalhães Victor Ferreira Carlos Pinho CEFT DEMEC Faculty of Engineering University of Porto Porto Portugal

The goal of this work was to measure the heat transfer rates from thermofluid, Therminol 66, to two phase change materials, D-mannitol and adipic acid. It concerns the determination of heat transfer coefficients for the design of a concentrated solar energy plant requiring PCM thermal energy storage and is part of a wider set of experiments, where several PCMs were tested. An experimental installation was used with a cylindrical vessel with three tubes disposed almost horizontally (5°inclination), containing the phase change material, around which the thermal fluid flowed almost perpendicular to the tubes. The experimental installation allowed to recreate heating and cooling cycles. In order to evaluate the influence of the flow on the rate at which the heating and cooling processes took place, tests were performed at different thermofluid mass flow rates, concluding that there is no great influence, since the thermal resistance inside the tubes is much higher than on the outside. D-mannitol and adipic acid, present different phase change temperatures, 164°C for D-mannitol and 152°C for adipic acid. The average heat transfer coefficient, during the phase change process, was of 340 W/(m2K) for D-mannitol and 1320 W/(m2K) for adipic acid.

关键词： adipic acid D-Mannitol Heat Transfer Coefficient Phase Change Materials

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Production of adipic acid by the native-occurring pathway in Thermobifida fusca B6

Production of adipic acid by the native-occurring pathway in...

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2015年中国化工学会年会

作者：邓禹江南大学

＜正＞Aims:To identify the native-occurring adipate pathway in a previously engineered Thermobifida fusca B6 strain and optimize the adipic acid production of this strain on glucose and corncob.Methods and Results:The native-occurring adipate pathway in T.fusca B6 was identified to be the reverse adipate degradation pathway,including 5 steps:

关键词： adipic acid reverse adipate degradation pathway

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Catalytic synthesis of adipic acid with H4SiW6Mo6O40/SiO2

Catalytic synthesis of adipic acid with H4SiW6Mo6O40/SiO2

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2012 China Functional Materials Technology and Industry Forum

作者： Bao-lan LV Hui-fang JIANG Shui-jin YANG College of Chemistry and Environmental Engineering Hubei Normal University

Using aqueous hydrogen peroxide solution(30wt%) as oxidant,potassium bisulfate(KHS04) as acid ligand,adipic acid was synthesized with cyclohexanone as raw material and HSiWMoO/SiO as catalyst.The factors influencing the synthesis were discussed and the best reaction conditions were found out.Experimental results showed that HSiWMoO/SiO is an excellent catalyst.The optimal conditions are:n(cyclohexanone).n(HO)=1:4.0,catalyst dosage is 0.4g,mass of acidic ligands is 0.1g,and the reaction time is 4 h,the yield of adipic acid can reach 93.7%.

关键词： adipic acid H4SiW6Mo6O40/SiO2 Catalysis

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