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1. Brønsted acidic Heteropolyanion-Based ionic Liquid:A highly efficient Reaction-induced Self-separation catalyst for Baeyer-Villiger reaction

Author:
Xiangshan Li; Shihao Liu; Yao Chen; Guangxu Zhang
Source:
Tetrahedron letters 2022 pp. 154042
ISSN:
0040-4039
Subject:
acidity; catalysts; catalytic activity; cations; cyclohexanones; ionic liquids; liquids; models; reaction kinetics; synergism; thermal stability; tungsten
Abstract:
... A novel Brønsted acidic heteropolyanion-based ionic liquid (IL) ([MIMPS]₃PW₁₂O₄₀) was synthesized and employed to catalyze the Baeyer-Villiger (BV) reaction to produce ε-Caprolactone (ε-CL). Noteblely, the prepared IL catalyst exhibited higher catalytic activity compared to solid acid catalysts duo to its behavior of reaction-induced self-separation. It meaned that the IL catalyst could switch fro ...
DOI:
10.1016/j.tetlet.2022.154042

2. Cometabolic biodegradation system employed subculturing photosynthetic bacteria: A new degradation pathway of 4-chlorophenol in hypersaline wastewater

Author:
Liang Wang; Zhongce Hu; Mian Hu; Jun Zhao; Peijie Zhou; Yongjie Zhang; Xin Zheng; Yifeng Zhang; Zhong-Ting Hu; Zhiyan Pan
Source:
Bioresource technology 2022 v.361 pp. 127670
ISSN:
0960-8524
Subject:
4-chlorophenol; Bacteroidetes; Firmicutes; biodegradation; carbon; cyclohexanones; hypersalinity; microbial communities; photosynthesis; pollutants; sodium acetate; technology; toxicity; wastewater
Abstract:
... 4-chlorophenol (4-CP) as a toxic persistent pollutant is quite difficult treatment by using traditional biological processes. Herein, photosynthetic bacteria (PSB) driven cometabolic biodegradation system associated with exogeneous carbon sources (e.g., sodium acetate) has been demonstrated as an effective microbial technique. The biodegradation rate (rᵢ) can be at 0.041 d⁻¹ with degradation effic ...
DOI:
10.1016/j.biortech.2022.127670

3. Comparison of mesoporous fractal characteristics of silica-supported organocatalysts derived from bipyridine-proline and resultant effects on the catalytic asymmetric aldol performances

Author:
Guangpeng Xu; Liujie Bing; Bingying Jia; Shiyang Bai; Jihong Sun
Source:
RSC advances 2022 v.12 no.17 pp. 10800-10814
ISSN:
2046-2069
Subject:
cyclohexanones; ligands; organocatalysts; porous media; silica; stereoselectivity
Abstract:
... Three kinds of the bipyridine-proline chiral ligands as highly active species were successfully introduced on Zn-modified mesoporous silica nanomaterials (BMMs, MCM-41, and SBA-15) via the covalent attachment and coordination methods. Their microstructural features and physicochemical properties were extensively characterized via XRD patterns, SEM/TEM images, TGA profiles, FT-IR and UV-Vis spectra ...
DOI:
10.1039/d2ra00971d

4. Concise Enantioselective Total Synthesis of Daphenylline Enabled by an Intramolecular Oxidative Dearomatization

Author:
Meng-Yue Cao; Bin-Jie Ma; Qing-Xiu Gu; Bei Fu; Hai-Hua Lu
Source:
Journal of the American Chemical Society 2022 v.144 no.13 pp. 5750-5755
ISSN:
1520-5126
Subject:
Daphniphyllum; amination; aromatization; cyclization reactions; cyclohexanones; enantioselectivity; hydrogenation; triterpenoids
Abstract:
... Daphenylline is a structurally unique member of the triterpenoid Daphniphyllum natural alkaloids, which exhibit intriguing biological activities. Six total syntheses have been reported, five of which utilize aromatization approaches. Herein, we report a concise protecting-group-free total synthesis by means of a novel intramolecular oxidative dearomatization reaction, which concurrently generates ...
DOI:
10.1021/jacs.2c01674

5. Conformation Selectivity and Disharmony of the Lattice Constant Depending on the Guest Size in Clathrate Hydrates

Author:
Yusuke Jin; Masato Kida; Jiro Nagao
Source:
Journal of physical chemistry 2022 v.126 no.1 pp. 58-65
ISSN:
1932-7455
Subject:
X-ray diffraction; cages; cyclohexanones; energy; hydrogen; hydrogen bonding; molecular conformation
Abstract:
... This study reports the guest molecular conformation selectivity of a clathrate hydrate and lattice shrunk by hydrogen bonds between the guest and host water frameworks. Cyclohexanol (CHnol) exhibited two conformations (equatorial and axial structures) with small energy differences. The Rietveld refinement results of the powder X-ray diffraction profiles of two structure II (sII) hydrates enclosing ...
DOI:
10.1021/acs.jpcc.1c09140

6. Copper(I)-Catalyzed Synthesis of Unsymmetrical All-Carbon Bis-Quaternary Centers at the Opposing α-Carbons of Cyclohexanones

Author:
Joshua A. Malone; Satish Chandra Philkhana; Jacob R. Stepherson; Fatimat O. Badmus; Frank R. Fronczek; Rendy Kartika
Source:
Organic letters 2022 v.24 no.26 pp. 4810-4815
ISSN:
1523-7052
Subject:
Lewis bases; chemical reactions; cyclohexanones; diastereoselectivity; indoles; regioselectivity; stereochemistry
Abstract:
... We describe a new synthetic reaction that generates all-carbon bis-quaternary centers at the opposing side of α-carbons in cyclohexanone with four different substituents in a controlled manner. Catalyzed by Cu(MeCN)₄BF₄ salt, this chemistry is proposed to proceed via an intermediacy of unsymmetrical O-allyl oxyallyl cations, which undergo a sequence of regioselective nucleophilic addition with sub ...
DOI:
10.1021/acs.orglett.2c01890

7. Correlating Lewis acid activity to extra-framework aluminum species in zeolite Y introduced by Ion-exchange

Author:
Syeda R. Batool; Vitaly L. Sushkevich; Jeroen A. van Bokhoven
Source:
Journal of catalysis 2022 v.408 pp. 24-35
ISSN:
0021-9517
Subject:
Fourier transform infrared spectroscopy; Lewis acids; X-ray diffraction; acidity; aluminum; carbon monoxide; catalytic activity; cyclohexanones; ion exchange; isopropyl alcohol; nitrogen; pyridines; zeolites
Abstract:
... Lewis acidity was introduced into zeolite Y (Si/Al = 30) by a facile ion-exchange of aluminum cations followed by calcination. X-ray diffraction and nitrogen physisorption suggest that the zeolitic framework is retained after these treatments. With an increase in the total extra-framework aluminum in the modified zeolites, there was a pronounced increase in the number of Lewis acid sites, as illus ...
DOI:
10.1016/j.jcat.2022.02.010

8. Electrochemical Cross-Dehydrogenative Aromatization Protocol for the Synthesis of Aromatic Amines

Author:
Shao-Kun Tao; Shan-Yong Chen; Mei-Lin Feng; Jia-Qi Xu; Mao-Lin Yuan; Hai-Yan Fu; Rui-Xiang Li; Hua Chen; Xue-Li Zheng; Xiao-Qi Yu
Source:
Organic letters 2022 v.24 no.4 pp. 1011-1016
ISSN:
1523-7052
Subject:
aromatization; cyclohexanones; electrochemistry; heterocyclic compounds
Abstract:
... The introduction of amines onto aromatics without metal catalysts and chemical oxidants is synthetically challenging. Herein, we report the first example of an electrochemical cross-dehydrogenative aromatization (ECDA) reaction of saturated cyclohexanones and amines to construct anilines without additional metal catalysts and chemical oxidants. This reaction exhibits a broad scope of cyclohexanone ...
DOI:
10.1021/acs.orglett.1c04129

9. Electrochemical Strategy for the Simultaneous Production of Cyclohexanone and Benzoquinone by the Reaction of Phenol and Water

Author:
Ruizhi Wu; Qinglei Meng; Jiang Yan; Huizhen Liu; Qinggong Zhu; Lirong Zheng; Jing Zhang; Buxing Han
Source:
Journal of the American Chemical Society 2022 v.144 no.4 pp. 1556-1571
ISSN:
1520-5126
Subject:
absorption; alloy nanoparticles; anodes; benzoquinones; carbon; cathodes; cyclohexanones; durability; electrochemistry; oxidation; phenol
Abstract:
... Cyclohexanone and benzoquinone are important chemicals in chemical and manufacturing industries. The simultaneous production of cyclohexanone and benzoquinone by the reaction of phenol and water is an ideal route for the economical production of the two chemicals. In principle, this can be achieved in an electrochemical reaction system that couples the cathodic reduction of phenol to cyclohexanone ...
DOI:
10.1021/jacs.1c09021

10. Enhanced flow electrochemistry for cyclohexane Conversion: From simulation to application

Author:
Yujun Zhang; Hao Tian; Zhaowei Cui; Zhen Yin; Hongsen Hui; Hong Wang; Lei Zhang; Hongchang Pei; Zhenhuan Li; Bhekie B. Mamba; Jianxin Li
Source:
Journal of catalysis 2022 v.410 pp. 84-92
ISSN:
0021-9517
Subject:
catalytic activity; cyclohexanones; density functional theory; electric field; electrochemistry; electrodes; oils; oxidation; prediction
Abstract:
... To further improve the capability of flow electrochemistry, the multistage plug-flow electrochemical membrane reactor (PF-ECMR) with membrane electrode was developed for enhancing the oxidation of cyclohexane (CHA) to produce KA oil (mixture of cyclohexanol and cyclohexanone). The catalytic results demonstrated that the CHA conversion and the selectivity to KA oil were up to 95.6% and > 99%, which ...
DOI:
10.1016/j.jcat.2022.04.008

11. Environmentally Benign Blue Emissive Films from Host-Dopant Interaction of PLA–Bischalcone Combination with High UV Endurance

Author:
Ammembal Jaya Pai; Balladka Kunhanna Sarojini; Kishori Ramachandra Harshitha; Armand Soldera
Source:
Journal of polymers and the environment 2022 v.30 no.1 pp. 373-384
ISSN:
1566-2543
Subject:
absorption; anthracenes; bioplastics; crystal structure; cyclohexanones; environment; molecular dynamics; photoluminescence; spectroscopy; ultraviolet radiation
Abstract:
... This work reports the fabrication of blue luminescent bioplastic PLA films on doping with 4-chloro and 4-fluoro substituted bisarylidene cyclohexanone derivatives A and B. The successful doping of A and B to host matrix was evidenced by spectroscopic and analytical methods. The appearance of an absorption band at 1665 cm⁻¹ owing to the conjugated alkene stretching frequency for bischalcones approv ...
DOI:
10.1007/s10924-021-02196-1

12. Experimental and Theoretical Studies of Ultrafine Pd-Based Biochar Catalyst for Dehydrogenation of Formic Acid and Application of In Situ Hydrogenation

Author:
Liangyu Zou; Qi Liu; Daoyun Zhu; Yangqiang Huang; Yu Mao; Xiao Luo; Zhiwu Liang
Source:
ACS applied materials & interfaces 2022 v.14 no.15 pp. 17282-17295
ISSN:
1944-8252
Subject:
ambient temperature; ammonium oxalate; biochar; carbon; carboxymethylcellulose; cyclohexanones; dehydrogenation; density functional theory; formic acid; hydrogen; hydrogenation; nanocatalysts; palladium; phenol; phosphoric acid; sodium bicarbonate
Abstract:
... In this work, a novel “foaming” strategy uses sodium bicarbonate (NaHCO₃) and ammonium oxalate ((NH₄)₂C₂O₄) as the foaming agent, turning biomass-derived carboxymethyl cellulose (CMC) into N-doped porous carbon. Highly active palladium nanoparticles (Pd NPs) immobilized on nitrogen-doped porous carbon (Pd@MC(2)-P) are produced through a phosphate-mediation approach. The phosphoric acid (H₃PO₄) bec ...
DOI:
10.1021/acsami.2c00343

13. Extraction of thorium (IV) ions from aqueous sulfate media by amino bromo phenyl diazenyl pyrazolo pyrimidinyl cyclohexanone

Author:
Ghada M. Hussein
Source:
International journal of environmental analytical chemistry 2022 v.102 no.2 pp. 528-545
ISSN:
1029-0397
Subject:
Fourier transform infrared spectroscopy; ammonia; analytical chemistry; cyclohexanones; ligands; nuclear magnetic resonance spectroscopy; pH; sand; solvents; sulfates; thorium
Abstract:
... In the present study, 2-(2-Amino-3-((4-bromophenyl) diazenyl)pyrazolo [1,5-a]pyrimidin-7-yl) cyclohexanone (PPC) as an organic ligand was evaluated in the liquid-liquid (water-chloroform) extraction to extract Th (IV) from thorium sulphate solution. The characterisation of the ligand was carried out using elemental analysis, fourier-transform infrared spectroscopy (FTIR), nuclear magnetic resonanc ...
DOI:
10.1080/03067319.2020.1724982

14. Facile C–H bond activation on a transient gallium imide

Author:
Aishabibi Kassymbek; Denis Spasyuk; Anton Dmitrienko; Melanie Pilkington; Georgii I. Nikonov
Source:
Chemical communications 2022 v.58 no.49 pp. 6946-6949
ISSN:
1364-548X
Subject:
X-ray diffraction; amides; azides; carbon-hydrogen bond activation; cyclohexanones; ethyl acetate; gallium; pyridines
Abstract:
... Reaction of NacNacGa with azide N₃SiMe₃ results in the generation of a transient imide NacNacGa(NSiMe₃) that can cleave unactivated sp³ C–H and sp² C–H bonds of different substrates, affording gallium amides. Pyridine, cyclohexanone, ethyl acetate, DMSO, and triethylphosphine oxide were activated in this process producing corresponding gallium amides. All new compounds were characterised by multi ...
DOI:
10.1039/d2cc01857h

15. Flower colour and essential oil compositions, antibacterial activities in Lagerstroemia indica L.

Author:
Qiang Wei; Rui-jie Liu
Source:
Natural product research 2022 v.36 no.8 pp. 2145-2148
ISSN:
1478-6427
Subject:
Escherichia coli; Lagerstroemia indica; cyclohexanones; essential oils; flower color; flowers; research; xylene
Abstract:
... Compositions of volatile oil from Lagerstroemia indica L. were reported for the first time. Out of 114 components where 58, 63, 67 and 61 compounds were identified from the white, pink, mauve, carmine flower with yields of 0.92%, 1.15%, 1.12% and 1.08%, respectively. Main compounds of white flower were 2-methyl-cyclopentanone (9.41%), m-xylene (7.53%) while the pink, carmine flower contained octac ...
DOI:
10.1080/14786419.2020.1843034

16. Formal Synthesis of Arboridinine Enabled by a Double-Mannich Reaction

Author:
Jinghua Wu; Yubing Pang; Huanfeng Jiang; Zhiqiang Ma
Source:
Journal of organic chemistry 2022 v.87 no.12 pp. 8223-8228
ISSN:
1520-6904
Subject:
cyclohexanones; journals; organic chemistry
Abstract:
... A formal synthesis of arboridinine has been achieved. In this synthesis, a double-Mannich reaction of the complex multisubstituted cyclohexanone was used to form the core skeleton of arboridinine. ...
DOI:
10.1021/acs.joc.2c00602

17. GC–MS profiling, phytochemical and biological investigation of aerial parts of Leucophyllum frutescens (Berl.) I.M. Johnst (Cenizo)

Author:
Imtiaz Ahmad; Saeed Ahmed; Esra Küpeli Akkol; Huma Rao; Muhammad Nadeem Shahzad; Umar Shaukat; Abdul Basit; Maryam Fatima
Source:
South African journal of botany 2022 v.148 pp. 200-209
ISSN:
0254-6299
Subject:
Leucophyllum; antioxidants; cataract; cyclohexanones; cytotoxicity; drugs; dysentery; furans; liver; oleic acid; palmitic acid; phytochemicals; squalene; stearic acid; traditional medicine; urease; Mexico
Abstract:
... Leucophyllum frutescens (Berl.) I.M. Johnst has been used as a crude drug for treating various respiratory ailments, dysentery, cataract and liver disorders in the folk medicine systems by the inhabitants of America and Mexico. The Phytochemical and biological investigation was established by spectrophotometrically and chemical profiling was performed by GC–MS analysis. The chemical profiling by G ...
DOI:
10.1016/j.sajb.2022.04.038

18. Green solvent extraction and properties characterization of Poly(3-hydroxybutyrate-co-3-hydroxyvalerate) biosynthesized by mixed microbial consortia fed fermented dairy manure

Author:
Maryam Abbasi; Erik R. Coats; Armando G. McDonald
Source:
Bioresource technology reports 2022 v.18 pp. 101065
ISSN:
2589-014X
Subject:
biosynthesis; carbonates; cyclohexanones; dairy manure; ethanol; fermentation; molecular weight; rheological properties; solid phase extraction; solvents
Abstract:
... The aims of this study were to assess the large-scale extraction and recovery of poly(3-hydroxybutyrate-co-3-hydroxyvalerate) (PHBV) biosynthesized by mixed microbial consortia (MMC) that was fed fermented dairy manure at the pilot level using green solvents (ethanol, cyclohexanone (CYC), and dimethyl carbonate (DMC)). The reflux extraction procedure with CYC for 3 h at 130 °C and DMC for 4 h at 9 ...
DOI:
10.1016/j.biteb.2022.101065

19. Guaiacol hydrotreating with in-situ generated hydrogen over ni/modified zeolite supports

Author:
Lingyu Tai; Roya Hamidi; Benedetta de Caprariis; Martina Damizia; Laura Paglia; Marco Scarsella; Ramin Karimzadeh; Paolo De Filippis
Source:
Renewable energy 2022 v.182 pp. 647-658
ISSN:
0960-1481
Subject:
active sites; alkali treatment; benzene; catalysts; catalytic activity; cyclohexanones; guaiacol; hydrogen; mass transfer; oxidation; phenol; renewable energy sources; zeolites; zinc oxide
Abstract:
... Catalytic hydrotreating of guaiacol as a model compound was investigated using bifunctional catalysts constituted of Ni supported on chemically modified zeolites with increased mesoporosity. In the reaction conditions, the hydrogen required for the process was generated in situ by the Zn–H₂O redox system, which represents a promising green alternative to the use of gaseous hydrogen. The guaiacol h ...
DOI:
10.1016/j.renene.2021.10.048

20. Hierarchical Pd@PC-COFs as Efficient Catalysts for Phenol Hydrogenation

Author:
Xinhui Shen; Jiuxuan Zhang; Hong Jiang; Yan Du; Rizhi Chen
Source:
Industrial & engineering chemistry process design and development 2022 v.61 no.13 pp. 4534-4545
ISSN:
1520-5045
Subject:
catalysts; catalytic activity; crystal structure; cyclohexanones; hydrogenation; mass transfer; nylon; phenol; process design; surface area
Abstract:
... One-step hydrogenation of phenol is a green approach to produce cyclohexanone, an important intermediate for the synthesis of nylon. The design and fabrication of high-performance catalysts still present a great challenge. Herein, a series of triazinyl covalent organic frameworks (PC-COFs) were prepared by adjusting the synthesis time using a solvothermal method, and then, Pd@PC-COF catalysts were ...
DOI:
10.1021/acs.iecr.1c05009

21. Highly selective hydrogenation of phenol to cyclohexanone over a Pd-loaded N-doped carbon catalyst derived from chitosan

Author:
Qiong Wu; Lu Wang; Baozheng Zhao; Lang Huang; Shitao Yu; Arthur J. Ragauskas
Source:
Journal of colloid and interface science 2022 v.605 pp. 82-90
ISSN:
0021-9797
Subject:
Lewis acids; carbon; catalysts; catalytic activity; chitosan; cyclohexanones; hydrogenation; hydrothermal carbonization; nitrogen; phenol
Abstract:
... A highly stable Pd-loaded N-doped carbon catalyst (ACNₚd) for phenol hydrogenation was prepared from chitosan by hydrothermal carbonization. ACNₚd does not require a reduction step before catalytic use due to the Pd in the as-prepared catalyst mainly exists in the form of Pd⁰ (80%). The carbon support involves N-containing groups such as pyridinic nitrogen and pyrrolic nitrogen, which could provid ...
DOI:
10.1016/j.jcis.2021.07.077

22. Hydrophobized hollow TS-1 zeolite as pickering interfacial catalyst for selective oxidation reactions

Author:
Guojun Lv; Tao Wang; Yan Chen; Jiangzhang Wang; Xuyang Zou; Jun Lu; Fumin Wang; Xubin Zhang; Yi Zhai
Source:
Colloids and surfaces 2022 v.633 pp. 127842
ISSN:
0927-7757
Subject:
Fourier transform infrared spectroscopy; X-ray diffraction; catalysts; catalytic activity; cyclohexanones; cyclohexenes; emulsifiers; epoxidation reactions; nitrogen; oxidation; transmission electron microscopy; ultraviolet-visible spectroscopy; wettability; zeolites
Abstract:
... Design of catalyst particles bearing excellent diffusion performance and suitable surface wettability is of great importance to the successful application of Pickering interfacial catalysis. In this study, selective oxidation reactions over hydrophobized hollow TS-1 zeolite were applied as probe reactions to investigate the influence of catalyst diffusion performance closely related to mesopore si ...
DOI:
10.1016/j.colsurfa.2021.127842

23. Identification and functional characterization of three iridoid synthases in Gardenia jasminoides

Author:
Chong Xu; Peng Ye; Qingwen Wu; Shuangcheng Liang; Wuke Wei; Jinfen Yang; Weiwen Chen; Ruoting Zhan; Dongming Ma
Source:
Planta 2022 v.255 no.3 pp. 58
ISSN:
0032-0935
Subject:
Catharanthus roseus; Gardenia jasminoides; biochemical pathways; biosynthesis; catalytic activity; cyclohexanones; genomics; health promotion; introns; iridoid glycosides; monoterpenoids; progesterone; transcriptomics
Abstract:
... MAIN CONCLUSION: The discovery of three iridoid synthases (GjISY, GjISY2 and GjISY4) from Gardenia jasminoides and their functional characterization increase the understanding of iridoid scaffold/iridoid glycoside biosynthesis in iridoid-producing plants. Iridoids are a class of noncanonical monoterpenes that are found naturally in the plant kingdom mostly as glycosides. Over 40 iridoid glycosides ...
DOI:
10.1007/s00425-022-03824-3

24. Importance of Species Heterogeneity in Supported Metal Catalysts

Author:
Jie Zhang; Meng Wang; Zirui Gao; Xuetao Qin; Yao Xu; Zhaohua Wang; Wu Zhou; Ding Ma
Source:
Journal of the American Chemical Society 2022 v.144 no.11 pp. 5108-5115
ISSN:
1520-5126
Subject:
catalysts; catalytic activity; cyclohexanones; dehydrogenation; hydrogen; phenol; quantitative analysis; rhodium; transportation
Abstract:
... The structural heterogeneity of surface metal species, which is represented by the distribution in size, morphology, and local coordination environment of the active metal component, is almost inevitable in practical supported metal catalysts. This is often regarded as a major hindrance to the full utilization of metal loading and the high mass-specific catalytic activity. In this work, by quantit ...
DOI:
10.1021/jacs.2c00202

25. Light-Irradiated Thermal Energy-Promoted Selective Phenol Hydrogenation on Cellulose-Supported Palladium Catalyst with Green Hydrogen

Author:
Peijing Guo; Shaoyu Yuan; Chenyang Yu; Zhangyi Xiong; Yushan Yang; Jianlong Du; Yaguang Li; Yongjun Gao
Source:
ACS sustainable chemistry & engineering 2022 v.10 no.28 pp. 9205-9215
ISSN:
2168-0485
Subject:
adsorption; catalysts; catalytic activity; cellulose; cyclohexanones; electrolysis; glucose; green chemistry; hydrogen; hydrogenation; irradiation; palladium; phenol; thermal energy; xenon
Abstract:
... The energy and environmental crises urge us to develop a green and sustainable catalytic strategy to achieve chemical transformation. Thus, light-irradiated thermal energy, green hydrogen generated from water electrolysis, and natural cellulose were combined into a catalytic system for phenol hydrogenation to cyclohexanone in this article. The cellulose containing abundant hydroxyl groups improves ...
DOI:
10.1021/acssuschemeng.2c02391

26. Liquid-Phase Amination of Phenol to Aniline over the Pd/MgO Catalyst without External Hydrogen Addition

Author:
Xiaoying Liu; Weikun Chen; Jinglin Zou; Linmin Ye; Youzhu Yuan
Source:
ACS sustainable chemistry & engineering 2022 v.10 no.21 pp. 6988-6998
ISSN:
2168-0485
Subject:
amination; ammonia; aniline; catalysts; cyclohexanones; green chemistry; hydrogen; hydrogenation; phenol; secondary amines; stoichiometry
Abstract:
... The amination of phenol to aniline is a sustainable method to replace the traditional synthesis of primary aniline by nitrobenzene–hydrogenation and halobenzene–amination. Under a hydrogen atmosphere, the supported Pd catalyst exhibits significant activity in phenol amination with various amines, but the selectivity to primary aniline is poor. Here, we showed that the phenol amination to aniline c ...
DOI:
10.1021/acssuschemeng.2c00273

27. Mechanistic Insight Into the Application of Alumina-Supported Pd Catalysts for the Hydrogenation of Nitrobenzene to Aniline

Author:
Clément G. A. Morisse; Annelouise M. McCullagh; James W. Campbell; Chris Mitchell; Robert H. Carr; David Lennon
Source:
Industrial & engineering chemistry process design and development 2022 v.61 no.30 pp. 10712-10722
ISSN:
1520-5045
Subject:
aniline; byproducts; catalysts; cyclohexanones; desorption; heat recovery; hydrogen; hydrogenation; infrared spectroscopy; nitrobenzenes; process design; temperature; vapors
Abstract:
... Two Pd/γ-Al₂O₃ catalysts are examined for the vapor phase hydrogenation of nitrobenzene over the temperature range of 60–200 °C. A 1 wt % catalyst is selected as a reference material that is diluted with γ-alumina to produce a 0.3 wt % sample, which is representative of a metal loading linked to a candidate industrial specification aniline synthesis catalyst. Cyclohexanone oxime is identified as a ...
DOI:
10.1021/acs.iecr.2c01134

28. Metabolism of key atmospheric volatile organic compounds by the marine heterotrophic bacterium Pelagibacter HTCC1062 (SAR11)

Author:
Eric R. Moore; Alec J. Weaver; Edward W. Davis; Stephen J. Giovannoni; Kimberly H. Halsey
Source:
Environmental microbiology 2022 v.24 no.1 pp. 212-222
ISSN:
1462-2912
Subject:
Bacillariophyceae; acetone; aquatic bacteria; atmospheric chemistry; biochemical pathways; biosynthesis; coculture; cyclohexanones; fosmidomycin; genome; isoprene; phytoplankton; seawater
Abstract:
... Plants and phytoplankton are natural sources of the volatile organic compounds (VOCs) acetone and isoprene, which are reactive and can alter atmospheric chemistry. In earlier research we reported that, when co‐cultured with a diatom, the marine bacterium Pelagibacter (strain HTCC1062; ‘SAR11 clade’) reduced the concentration of compounds tentatively identified as acetone and isoprene. In this stud ...
DOI:
10.1111/1462-2920.15837

29. Metal- and Solvent-Free Synthesis of Tetrahydrobenzo[c]carbazolones through NaI-Catalyzed Formal [4 + 2] Annulation

Author:
Fang Fang; Haolin Zheng; Guojiang Mao; Shanping Chen; Guo-Jun Deng
Source:
Journal of organic chemistry 2022 v.87 no.9 pp. 6052-6063
ISSN:
1520-6904
Subject:
alkenes; alkynes; carbazoles; cyclohexanones; organic chemistry
Abstract:
... A novel strategy for the preparation of functional carbazoles through NaI-catalyzed formal [4 + 2] annulation of 2-(indol-3-yl)cyclohexanones and alkynes/alkenes has been developed. The present approach started from easily available raw materials and provided a variety of tetrahydrobenzo[c]carbazolones in satisfactory yields under metal- and solvent-free conditions. Furthermore, the products could ...
DOI:
10.1021/acs.joc.2c00315

30. Mg-stabilized subnanometer Rh particles in zeolite Beta as highly efficient catalysts for selective hydrogenation

Author:
Hongwei Zhang; Lixiang Zhong; Ismail Bin Samsudin; Kazu Okumura; Hui-Ru Tan; Shuzhou Li; Stephan Jaenicke; Gaik-Khuan Chuah
Source:
Journal of catalysis 2022 v.405 pp. 489-498
ISSN:
0021-9517
Subject:
catalytic activity; cyclohexanones; electrostatic interactions; hydrogenation; nylon; phenol; zeolites
Abstract:
... Nanoparticles are of interest in heterogeneous catalysis because of their excellent activity associated with atoms in a low coordination environment. However, their high reactivity becomes a drawback where selectivity is desired, compounded by their propensity towards agglomeration. Here, we show that stable subnanometric Rh particles can be prepared in a Mg-doped zeolite Beta based on the electro ...
DOI:
10.1016/j.jcat.2021.11.026

31. A Mild Two-Step Synthesis of Structurally Valuable Indole-Fused Derivatives

Author:
Shanping Chen; Yi Xia; Shikai Jin; Hanwen Lei; Kuiyi You; Guo-Jun Deng
Source:
Journal of organic chemistry 2022 v.87 no.5 pp. 3212-3222
ISSN:
1520-6904
Subject:
cyclohexanones; indoles; organic chemistry; phenothiazine
Abstract:
... A mild two-step synthetic approach for the preparation of structurally valuable indolo[3′,2′:4,5]pyrrolo[3,2,1-kl]phenothiazines has been developed. In this work, cyclohexanone was used as the key bridge to connect the indole and phenothiazine frameworks to construct a structurally valuable indole-fused derivative. The present protocol achieved the cascade construction of multiple C–hetero bonds, ...
DOI:
10.1021/acs.joc.1c02927

32. Multi-functionalized carbon aerogels derived from chitosan

Author:
Lu Wang; Qiong Wu; Baozheng Zhao; Zelin Li; Yuehong Zhang; Lang Huang; Shitao Yu
Source:
Journal of colloid and interface science 2022 v.605 pp. 790-802
ISSN:
0021-9797
Subject:
Lewis acids; acetone; active sites; aerogels; ascorbic acid; capacitance; carbon; carbonization; catalysts; chitosan; cyclohexanones; electrochemical capacitors; electrodes; energy density; fluorescence; glycine (amino acid); hydrogenation; ionic liquids; nitrogen; phenol; quantum dots; temperature; vapors; water solubility
Abstract:
... Carbon aerogels are prepared by a thermal treating-freeze drying approach from chitosan, with glycine hydrochloride ionic liquid (IL) acting as solvent and nitrogen source. Different post-treatments such as ball milling and high temperature carbonization are employed to functionalize the obtained carbon aerogels with tuned properties, making it promising candidates as fluorescence material (NACs-Q ...
DOI:
10.1016/j.jcis.2021.07.132

33. Nanometer-thick defective graphene films decorated with oriented ruthenium nanoparticles. Higher activity of 101 vs 002 plane for silane-alcohol coupling and hydrogen transfer reduction

Author:
Aicha Anouar; Rubén Ramírez Grau; Nadia Katir; Antonio Franconetti; Abdelkrim El Kadib; Ana Primo; Hermenegildo García
Source:
Journal of catalysis 2022 v.407 pp. 342-352
ISSN:
0021-9517
Subject:
adsorption; alginates; ammonium; catalytic activity; cyclohexanones; dehydrogenation; graphene; hydrogen; particle size; pyrolysis; ruthenium; silanes
Abstract:
... Pyrolysis of ammonium alginate films containing Ru(NH₃)₆Cl₃ leads to the formation of Ru nanoparticles (NPs) supported on defective graphene films. The procedure allows controlling the preferential facet orientation of small Ru NPs (5–20 nm), either 002 when the pyrolysis is carried out under Ar atmosphere or the 002 and 101 planes for pyrolysis in the presence of H₂. Ru is a metal difficult to pr ...
DOI:
10.1016/j.jcat.2022.02.007

34. Optimizing the Local Chemical Environment on a Bifunctional Helical Peptide Scaffold Enables Enhanced Enantioselectivity and Cooperative Catalysis

Author:
Adam X. Wayment; Mariur Rodriguez Moreno; Carter J. Jones; Gabriel J. Smith; Parker Jarman; Nayeli J. Garcia Morin; Morgan J. Coombs; Jacob A. Parkman; Connor D. Barlow; Stacy Allington Smith; Scott R. Burt; David J. Michaelis
Source:
Organic letters 2022 v.24 no.16 pp. 2983-2988
ISSN:
1523-7052
Subject:
catalysts; catalytic activity; circular dichroism spectroscopy; cyclohexanones; enamines; enantioselectivity; molecular dynamics; nuclear magnetic resonance spectroscopy; peptides; thiourea
Abstract:
... We describe a proof-of-concept study in which peptide-bound enamine and thiourea catalysts are used to facilitate the conjugate addition of cyclohexanone to nitroolefins. Our bifunctional peptide scaffold is modified to optimize the local environment around both catalysts to enhance both reactivity and enantioselectivity, affording selectivities of ≤95% ee. Circular dichroism, nuclear magnetic res ...
DOI:
10.1021/acs.orglett.2c00857

35. Organocatalyzed Beckmann Rearrangement of Cyclohexanone Oxime by Trifluoroacetic Anhydride in Microreactors

Author:
Chencan Du; Yubin Wang; Jian Deng; Guangsheng Luo
Source:
Industrial & engineering chemistry process design and development 2022 v.61 no.25 pp. 8714-8723
ISSN:
1520-5045
Subject:
Fourier transform infrared spectroscopy; activation energy; anhydrides; caprolactam; cyclohexanones; enthalpy; kinetics; process design; reaction mechanisms; temperature
Abstract:
... The kinetics of the Beckmann rearrangement of cyclohexanone oxime (CHO) catalyzed by trifluoroacetic anhydride (TFAA) and trifluoroacetic acid (TFA) is proposed in this work. The effects of experimental parameters on the reaction rate are studied in microreactors, including CHO concentration, TFAA concentration, temperature, and caprolactam (CPL) concentration. The reaction is verified as first-or ...
DOI:
10.1021/acs.iecr.2c01078

36. Oxygen affinity of transition metal cations: A coherent descriptor elucidating catalytic oxygenate transformations

Author:
Huixiang Li; Peifang Yan; Bo-Qing Xu; Z. Conrad Zhang
Source:
Journal of catalysis 2022 v.412 pp. 21-29
ISSN:
0021-9517
Subject:
absorbance; acidity; catalytic activity; chlorides; cyclohexanones; dissociation; ethyl ether; ethylene glycol; glucose; isomerization; metal ions; oxygen; spectroscopy
Abstract:
... This work reports a complementary descriptor to acidity for metal cations - oxygen affinity, to scale the interaction strength of metal cations with oxygenate groups. A method for measuring oxygen affinity is developed in alkyl methylimidazolium chloride solvents using in-situ far infrared (FIR) spectroscopy. The relative oxygen affinity values of metal cations in metal chlorides with model compou ...
DOI:
10.1016/j.jcat.2022.05.015

37. Palladium (Pd⁰) Loading-Controlled Catalytic Activity and Selectivity for Chlorophenol Hydrodechlorination and Hydrosaturation

Author:
Yi-Hao Luo; Yuhang Cai; Xiangxing Long; Dandan Zhou; Chen Zhou; Bruce E. Rittmann
Source:
Environmental science & technology 2022 v.56 no.7 pp. 4447-4456
ISSN:
1520-5851
Subject:
catalytic activity; chlorophenols; cyclohexanones; dechlorination; energy; environmental science; hydrogenation; palladium; phenol
Abstract:
... Reductive catalysis by zero-valent palladium nanoparticles (Pd⁰NPs) has emerged as an efficient strategy for promoting the detoxification of chlorophenols (CPs) via hydrogenation. Most studies achieved hydrodechlorination of CP to phenol for detoxification, but it requires considerably high energy input and harsh conditions to further hydrosaturate phenol to cyclohexanone (CHN) as the most desired ...
DOI:
10.1021/acs.est.1c08347

38. Phase inversion of hydrophobized hollow TS-1 stabilized Pickering emulsions with addition of lipophilic Span 80

Author:
Guojun Lv; Yan Chen; Xuyang Zou; Jiangzhang Wang; Tao Wang; Xubin Zhang; Fumin Wang
Source:
Colloids and surfaces 2022 v.645 pp. 128939
ISSN:
0927-7757
Subject:
cyclohexanones; emulsifiers; emulsions; lipophilicity; oils; zeolites
Abstract:
... There are few reports concentrated on the interactions between lipophilic surfactants and hydrophobized hollow TS-1 zeolite particles in the stabilization of emulsions. In this study, hydrophobized hollow TS-1 zeolite particles were synthesized and applied as emulsifier to stabilize the W/O Pickering emulsions employing cyclohexanone and water, and the influence of addition of lipophilic Span 80 o ...
DOI:
10.1016/j.colsurfa.2022.128939

39. Photo-thermo catalytic selective oxidation of cyclohexane by In-situ prepared nonstoichiometric Molybdenum oxide and Silver-palladium alloy composite

Author:
Xiaoyu Wang; Xuyang Feng; Jincheng Liu; Zhilin Huang; Shuang Zong; Linlin Liu; Jiarong Liu; Yanxiong Fang
Source:
Journal of colloid and interface science 2022 v.607 pp. 954-966
ISSN:
0021-9797
Subject:
air; alcohols; alloy nanoparticles; alloys; catalysts; catalytic activity; chemical industry; crystal structure; cyclohexanones; hot water treatment; molybdenum; nanowires; oils; oxidation; polyvinylpyrrolidone; temperature
Abstract:
... The highly selective oxidation of cyclohexane to cyclohexanone and cyclohexanol (KA oil) is one of the most challenging issues in the chemical industry. However, the difficulty in attaining high selectivity and high conversion rate in parallel for the existing catalysts limits its practical application. In this paper, a novel photo-thermo synergistic catalyst was reported for the aerobic oxidation ...
DOI:
10.1016/j.jcis.2021.09.058

40. Poly(ionic liquid)s hollow spheres nanoreactor for enhanced cyclohexane catalytic oxidation

Author:
Shengxin Chen; Yingwei Li; Zicheng Wang; Ying Jin; Ruixia Liu; Xingang Li
Source:
Journal of catalysis 2022 v.411 pp. 135-148
ISSN:
0021-9517
Subject:
activation energy; adipic acid; catalysts; catalytic activity; cyclohexanones; ionic liquids; oxidation; reaction kinetics; theoretical models
Abstract:
... Hollow structure nanoreactors take advantage of catalyst loading and enhanced activity by shell construction. In this work, functionalized poly(ionic liquid)s (PILs) with hollow spherical structures were synthesized by polymerization- and quaternization-based approaches. These hollow structure PILs (HPILs) could be controllable designed from IL monomer easily, giving HPILs various properties. In t ...
DOI:
10.1016/j.jcat.2022.05.012

41. Reductive amination of cyclohexanol/cyclohexanone to cyclohexylamine using SBA-15 supported copper catalysts

Author:
Sateesh Kumar Beepala; Harisekhar Mitta; Hussain Sk; Putrakumar Balla; V.R Chary Komandur
Source:
Journal of the Indian Chemical Society 2022 v.99 no.6 pp. 100451
ISSN:
0019-4522
Subject:
acidity; amination; catalysts; catalytic activity; copper; cupric oxide; cyclohexanones; particle size; porosity; porous media; surface area; vapors
Abstract:
... Amination of cyclohexanol was investigated in vapour phase over copper catalysts supported on mesoporous SBA-15. The different products identified during reductive amination of cyclohexanol reaction were cyclohexanone, cyclohexylamine, along with small amounts of N-Cyclohexylidinecyclohexylamine and dicyclohexylamine. Among several catalysts tested for the reductive amination, 5% Cu supported on S ...
DOI:
10.1016/j.jics.2022.100451

42. Reusable Deep Eutectic Solvents for Clean ε-Caprolactam Synthesis under Mild Conditions

Author:
Shiqin Sun; Shiwei Liu; Fengli Yu; Jian Zhang; Weiguo Xing; Shitao Yu
Source:
ACS sustainable chemistry & engineering 2022 v.10 no.4 pp. 1675-1688
ISSN:
2168-0485
Subject:
Gibbs free energy; acidity; activation energy; catalysts; catalytic activity; choline chloride; cyclohexanones; green chemistry; hydrogen; hydrogen bonding; solvents; thermal stability
Abstract:
... A deep eutectic solvent (DES) with adjustable Brønsted acidity was prepared easily by choline chloride (ChCl) and trifluoromethanesulfonic acid (TfOH). The obtained DES [ChCl][TfOH]₃ exhibited great stability and excellent catalytic performance in the Beckmann rearrangement reaction as solvent and catalyst. High cyclohexanone oxime (CHO) conversion (100%) and ε-caprolactam selectivity (98.8%) were ...
DOI:
10.1021/acssuschemeng.1c07613

43. Solvent-Free Production of ε-Caprolactone from Oxidation of Cyclohexanone Catalyzed by Nitrogen-Doped Carbon Nanotubes

Author:
Zhihui Cai; Duo Liu; Jiangnan Huang; Jianning Feng; Hongjuan Wang; Guangxing Yang; Feng Peng; Yonghai Cao; Hao Yu
Source:
Industrial & engineering chemistry process design and development 2022 v.61 no.5 pp. 2037-2044
ISSN:
1520-5045
Subject:
autoxidation; benzaldehyde; carbon nanotubes; catalysts; catalytic activity; cyclohexanones; graphene; nitrogen; oxidants; oxygen; plastics; process design; pyridines; raw materials
Abstract:
... As an important raw material for the synthesis of polycaprolactone, a significant alternative for the nondegradable plastic, ε-caprolactone (ε-CL) monomer is typically produced through the Baeyer–Villiger oxidation of cyclohexanone (Cy═O). In this work, a solvent-free, highly efficient, and nonmetallic catalytic system was developed to produce the ε-CL monomer with dioxygen as the oxidant and benz ...
DOI:
10.1021/acs.iecr.1c04407

44. Study on the mechanism of anaerobic fluidized bed microbial fuel cell for coal chemical wastewater treatment

Author:
Yanjie Niu; Xinmin Liu; Lingyun Wang; Qingjie Guo; Jianjun Wu
Source:
Bioprocess and biosystems engineering 2022 v.45 no.3 pp. 481-492
ISSN:
1615-7591
Subject:
Aeromonas; Pseudomonas; acetic acid; activated sludge; adsorption; bioprocessing; coal; computer software; cyclohexanones; diffusivity; energy; fluidized beds; heat; microbial communities; microbial fuel cells; molecular dynamics; organic matter; phenol; porous media; power generation; wastewater; wastewater treatment
Abstract:
... The coal chemical wastewater (CCW) was treated by anaerobic fluidized bed microbial fuel cell (AFB-MFC) with macroporous adsorptive resin (MAR) as fluidized particle. Isosteric heat calculation and molecular dynamics simulation (MDS) have been performed to study the interaction between organics of CCW and MAR. The isosteric heat of MAR to m-cresol was the largest at 65.4961 kJ/mol, followed by phe ...
DOI:
10.1007/s00449-021-02672-x

45. Supported l-tryptophan on Fe₃O₄@SiO₂ as an efficient and magnetically separable catalyst for one-pot construction of spiro[indene-2,2′-naphthalene]-4′-carbonitrile derivatives

Author:
Aref Ghasemi-Ghahsareh; Javad Safaei-Ghomi; Hourieh Sadat Oboudatian
Source:
RSC advances 2022 v.12 no.3 pp. 1319-1330
ISSN:
2046-2069
Subject:
cyclohexanones; magnetic materials; magnetism; nanocatalysts; tryptophan
Abstract:
... In this work, l-tryptophan functionalized silica-coated magnetic nanoparticles were readily prepared and evaluated as a recyclable magnetic nanocatalyst for the synthesis of spiro[indene-2,2′-naphthalene]-4′-carbonitrile derivatives through the one-pot four-component reaction of malononitrile, cyclohexanone, aromatic aldehydes, and 1,3-indandione. This novel magnetic nanocatalyst was confirmed to ...
DOI:
10.1039/d1ra07654j

46. Synthesis of Cyclohexanones by a Tandem Photocatalyzed Annulation

Author:
Anna V. Bay; Emelia J. Farnam; Karl A. Scheidt
Source:
Journal of the American Chemical Society 2022 v.144 no.16 pp. 7030-7037
ISSN:
1520-5126
Subject:
carbenes; cycloaddition reactions; cyclohexanones; heterocyclic compounds; photocatalysis; redox reactions
Abstract:
... The rapid synthesis of cyclic scaffolds is of high importance to the chemistry community. Strategies for the convergent synthesis of substituted carbocycles and heterocycles remain underexplored despite the plethora of applications that these cyclic motifs have in the pharmaceutical and materials industries. Reported herein is a tandem carbene and photoredox-catalyzed process for the convergent sy ...
DOI:
10.1021/jacs.1c13105

47. Synthesis of renewable diesel and jet fuel range alkanes using 2-methylfuran and cyclohexanone

Author:
Shaoying Sun; Xing Zhang; Yanqing Li; Xianzhao Shao; Jianwei Ji; Junhai Liu; Wei Wang; Zhizhou Li; Xiaohui Ji
Source:
RSC advances 2022 v.12 no.20 pp. 12932-12937
ISSN:
2046-2069
Subject:
alkylation; aviation; bisphenol A; catalysts; catalytic activity; cyclohexanones; kerosene; titration
Abstract:
... New solid acid catalysts were prepared by bisphenol A, paraformaldehyde and chlorosulfonic acid, and applied to hydroxylalkylation/alkylation (HAA) of 2-methylfuran (2-MF) and cyclohexanone. After optimizing the reaction conditions, the conversion of 2-MF reached 99% and the yield of 5,5′-(cyclohexane-1,1-diyl)bis(2-methylfuran) acquired 98%. The activity and catalytic efficiency were higher than ...
DOI:
10.1039/d2ra01987f

48. Activated Carbon Supported Non-noble Bimetallic Ni-Based Catalysts for Nitrocyclohexane Hydrogenation to Cyclohexanone Oxime under Mild Conditions

Author:
Fangbo Yao; Sihua Liu; Haishuai Cui; Yang Lv; Yuchen Zhang; Pingle Liu; Fang Hao; Wei Xiong; He’an Luo
Source:
ACS sustainable chemistry & engineering 2021 v.9 no.8 pp. 3300-3315
ISSN:
2168-0485
Subject:
activated carbon; adsorption; catalysts; catalytic activity; cyclohexanones; density functional theory; energy; green chemistry; hydrogen; hydrogenation; nickel oxide; temperature
Abstract:
... Activated carbon supported bimetallic Ni-based catalysts were prepared and applied in the selective hydrogenation of nitrocyclohexane (NCH) to cyclohexanone oxime (CHO). The characterization results show that the introduction of the metal promoter can inhibit Ni nanoparticle agglomeration and sintering. Among these bimetallic catalysts, the Cu-Ni/AC catalyst shows the best catalytic performance. T ...
DOI:
10.1021/acssuschemeng.0c09168

49. Activated charcoal-mediated synthesis of chalcones catalyzed by NaOH in water

Author:
Kiyoshi Tanemura; Taoufik Rohand
Source:
Tetrahedron letters 2021 v.71 pp. 152918
ISSN:
0040-4039
Subject:
acetophenones; activated carbon; benzaldehyde; chalcones; cyclohexanones
Abstract:
... A variety of chalcones were synthesized in good yields by the activated charcoal-mediated aldol reactions between benzaldehydes and acetophenones catalyzed by NaOH in water. 2,6-Bis((E)-benzylidene)cyclohexan-1-ones were prepared by the aldol reactions between benzaldehydes and cyclohexanone. Activated charcoal could be recycled five times without the significant decrease of yields. ...
DOI:
10.1016/j.tetlet.2021.152918

50. Assembly of Silicalite-1 Crystals Like Toy Lego Bricks into One-, Two-, and Three-Dimensional Architectures for Enhancing Its Adsorptive Separation and Catalytic Performances

Author:
Shiying Li; Hu Shi; Sen Wang; Zhikai Li; Pengfei Wang; Xingchen Liu; Yanhong Quan; Mei Dong; Jianguo Wang; Weibin Fan
Source:
ACS applied materials & interfaces 2021 v.13 no.48 pp. 58085-58095
ISSN:
1944-8252
Subject:
1-propanol; adsorption; benzaldehyde; butanol; catalytic activity; composite polymers; cyclohexanones; energy; ethanol; gels; nanocrystallites; nanosheets; spectroscopy; zeolites
Abstract:
... Many researchers have contributed to the assembly of zeolitic nanosheets and nanocrystallites into three-dimensional (3D) networks as it can remarkably improve the catalytic and/or adsorptive performances of zeolites. However, the applications of these synthesized materials are seriously limited because of low hydrothermal stability. A highly interesting strategy, but a great challenge, is the ali ...
DOI:
10.1021/acsami.1c15226