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Science China Chemistry 2024年第7期67卷 2282-2291页

作者： Meichen Jiao Chunmin Jia Hao Xu Peng Wu Xian-Ming Zhang School of Chemistry&Material Science Shanxi Normal UniversityTaiyuan 030006China Shanghai Key Laboratory of Green Chemistry and Chemical Processes School of Chemistry and Molecular EngineeringEast China Normal UniversityShanghai 200062China School of Chemistry Taiyuan University of TechnologyTaiyuan 030024China

Ge-containing Lewis acidic zeolites are typically synthesized using a conventional hydrothermal strategy from amorphous silica sources,through a long time-and energy-consuming approach limiting their wide *** study reports a rapid synthesis strategy for a series of IWV aluminogermanosilicate zeolites(T-x-Al)with a wide range of Si/Ge molar ratios(5–15)by interzeolite transformation of dealuminated FAU(DA-FAU).Notably,Ge-rich IWV could be obtained with crystallization time as short as one day by the equimolecular Si/Ge ratio *** effect of synthetic parameters was investigated and the obtained T-x-Al samples were characterized by XRD,SEM,EDS,ICP,^(29)Si and^(27)Al MAS NMR,FTIR,and N_(2)physisorption *** with a previously reported IWV germanosilicate(H-3),T-x-Al displayed a better catalytic activity in baeyer-villiger(BV)oxidation,attributed to the presence of the active framework Ge sites with the assistance of the extraframework Al *** cyclic catalysis tests revealed that the presence of framework Al species contributed to the stability of the ***,T-x-Al,with 14-membered ring(MR)supercages,outperformed the typical 12-MR Sn-beta catalyst in the BV oxidation of large ketone-like 2-admantanone,indicating a promising potential application in the macromolecular catalytic process.

关键词： Ge-rich IWV interzeolite transformation Al assistance baeyer-villiger oxidation

baeyer-villiger oxidation of cyclic ketones utilizing potassium peroxydisulfate(K_2S_2O_8) or sodium perborate(NaBO_3) in acidic media

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Chinese Chemical Letters 2009年第12期20卷 1400-1404页

作者： S.Zarrabi N.O.Mahmoodi K.Tabatabaeian M.A.Zanjanchi Department of Chemistry Faculty of ScienceUniversity of GuilanRashtP.O.Box 1914Iran

The efficient, green, facile, mild and straightforward conversion procedure for the oxidation of cyclic ketones to lactones at room temperature utilizing potassium peroxydisulfate （K2S2O8） in acidic media is satisfactory to high yields without using traditional chlorinated solvents is reported. This oxidative reagent is cheap and friendly environmental procedure for industrial purposes than use of organic peracids.

关键词： baeyer-villiger oxidation Cyclic ketones Potassium peroxydisulfate (K2S208) Acidic media Sodium perborate (NaBO3)

baeyer-villiger oxidation of Cyclic Ketones Catalyzed by Amino Acid Ionic Liquids

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Chemical Research in Chinese Universities 2020年第5期36卷 865-869页

作者： YU Fengli CHI Yujie GAO Chong CHEN Ruirui XIE Congxia YU Shitao State Key Laboratory Base of Eco-chemical Engineehng College of Chemistry and Molecular EngineeringQingdao University of Science and TechnologyQingdao 266042P.R.China College of Chemical Engineering Qingdao University of Science and TechnologyQingdao 266042P.R.China

A series of amino-acid-based ionic liquids was synthesized via one-step protonation of the corresponding L-amiiio acid by utilizing an array of proton *** catalytic activity of the amino-acid-based ionic liquids for the baeyer-villiger oxidation of cyclic ketones was investigated using cyclopentanone as a model ***-based ionic liquid[ProH]CF3SO3 was shown to exliibit thebest catalytic *** reaction condition was optimized to give the following reagent ratio of h(cyclopentanone):n(catalyst):w(H2O2)=1:0.06:4,60℃and 6 *** the optimum conditions,the conversion of cyclopentanone was 96.57%and the selectivity forδ-valerolactone was 73.01%.The catalytic activity was shown to be constant after 4 cycles.A simple treatment was allowed for the recover and the reuse of[ProH]*** successful utilization of[ProH]CF3SO3 to catalyze a host of cyclic ketones via baeyer-villiger oxidation clearly demonstrated the capacity of[ProH]CF3S03 to tolerate variation in the substrate.

关键词： Amino acid ionic liquid baeyer-villiger oxidation Cyclic ketone Lactone

baeyer-villiger oxidation of ketones with hydrogen peroxide catalyzed by Sn-aniline complex

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Chinese Chemical Letters 2007年第1期18卷 4-6页

作者： Qing Hua Zhang Shou Feng Wang Zi Qiang Lei Key Laboratory of Polymer Materials of Gansu Province College of Chemistry and Chemical Engineering Northwest Normal University Lanzhou 730070 China

Sn-aniline complex was prepared by a simple procedure. Cyclic and acyclic ketones were oxidized into lactones or esters with very high selectivity and yield with 30% hydrogen peroxide in the presence of Sn-aniline com... 详细信息

关键词： baeyer-villiger oxidation Sn-aniline complex Ketone oxidation Hydrogen peroxide

Aureobasidium subglaciale F134 is a bifunctional whole-cell biocatalyst for baeyer-villiger oxidation or selective carbonyl reduction controllable by temperature

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Chinese Journal of Chemical Engineering 2020年第12期28卷 3044-3051页

作者： Liqun Shen Ran Cang Guang Yang Anqi Zeng He Huang Zhigang Zhang School of Pharmaceutical Sciences Nanjing Tech UniversityNanjing 211816China State Key Laboratory of Materials-Oriented Chemical Engineering Nanjing Tech UniversityNanjing 211816China

The microbial production of either ester/lactones or enantio-enriched alcohols through baeyer-villiger oxidation or stereoselective reduction of ketones,respectively,is possible by using whole cells of *** F134 as a bifunctional *** chemoselective pattern of acetophenone biotransformation catalyzed by these cells can be regulated through reaction temperature,directing the reaction either towards oxidation or reduction *** baeyer–villiger oxidation activity of *** F134 whole cells is particularly dependent on reaction *** was transformed efficiently to phenol via the primary baeyer–villiger product phenyl acetate at 20℃ after 48 h with 100% *** contrast,at 35℃,enantio-enriched(S)-1-phenylethanol was obtained as the sole product with 64% conversion and 89% *** addition,*** F134 cells also catalyze the selective reduction of various structurally different aldehydes and ketones to alcohols with 40% to 100% yield,indicating broad substrate spectrum and good enantioselectivity in relevant *** study provides a bifunctional biocatalyst systemthat can be used in baeyer–villiger oxidation aswell as in asymmetric carbonyl reduction,setting the stage for future work concerning the identification and isolation of the respective enzymes.

关键词： Biocatalysis Whole cells baeyer-villiger oxidation Aureobasidium subglaciale Carbonyl reduction

Study on the Mechanisms for baeyer-villiger oxidation of Cyclohexanone with Hydrogen Peroxide in Different Systems

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China Petroleum Processing & Petrochemical Technology 2012年第2期14卷 7-17页

作者： Xia Changjiu Lin Min Zhu Bin Shu Xingtian State Key Laboratory of Catalytic Material and Reaction Engineering Research Institute of Petroleum ProcessingSINOPECBeijing 100083

The green and effective baeyer-villiger oxidation reaction of cyclohexanone for preparing e-caprolactone is of particular importance in the synthesis of new polymer materials. We have discussed here several mechanism types of baeyer-villiger oxidation of cyclohexanone with H2O2 in different reaction systems. Five main types have been addressed, i. e.：（1） the non-catalyzed reaction type, where the C=O of ketones is activated by H＋, which is electrolytically dissociated from H202 and H20, to improve the capability of C=O group for accepting the electron pairs; （2） the thermally activated radical reaction type, where the Criegee intermediate is produced via two steps of radical reaction with -OH attack, with much more hydroxyl radicals being excited in the presence of TS-1 zeolite; （3） the Bronsted acid catalysis reaction type, where both O-O moiety and C=O group could be activated by BriSnsted acid; （4） the solid Lewis acid catalyzed C=O of the substrate activation reaction type through enhancing the donor-acceptor interaction between the antibonding π＊c-o orbital of cyclohexanone and HOMO of Sn-containing zeolites; and （5） the solid Lewis acid catalyzed H202 to form Me-OOH oxidative species by converting the highest occupied molecular orbital （HOMO） of Ti-OOH into a singly occupied molecular orbital （SOMO）, making the O--O group highly electrophilic to attack the C--O of cyclohexanone during the baeyer-villiger oxidation process. In the end, we have also compared the different mechanisms and put forward our opinions on the development direction of catalytic materials aiming at eco-friendly baeyer-villiger oxidation of cyclohexanone in the years to come.

关键词： reaction mechanism baeyer-villiger oxidation Lewis acid Br'6nsted acid thermally activated radical hydrogen peroxide

One-pot baeyer-villiger oxidation of cyclohexanone with in situ generated hydrogen peroxide over Sn-Beta zeolites

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Green Chemical Engineering 2021年第3期2卷 294-300页

作者： Jianwei Luo Haoran Yuan Hui Liu Jingbo Li Yu Wang Yong Wang Jia Yao Haoran Li Department of Chemistry ZJU-NHU United R&D CenterZhejiang UniversityHangzhou310027China State Key Laboratory of Chemical Engineering College of Chemical and Biological EngineeringZhejiang UniversityHangzhou310027China Zhejiang NHU Company Ltd. Xinchang312500China

ε-Caprolactone is traditionally produced through baeyer-villiger oxidation of cyclohexanone oxidized by peracids in industry,which inevitably results in large discard acid and environmental *** this end,a green route toε-caprolactone was developed by coupling the direct generation of hydrogen peroxide from aerobic oxidation of benzhydrol catalyzed by NHPI and baeyer-villiger oxidation of cyclohexanone with the in situ hydrogen peroxide over Sn-Beta zeolites in one *** oxygen was employed as the terminal oxidant,and the effects of several reaction factors were *** with one-step process,the one-pot two-step method noticeably improved the selectivity ofε-*** the amount of in situ hydrogen peroxide was 0.72 equivalent,the selectivity ofε-caprolactone was obtained 94.8%with 39.2%conversion of cyclohexanone,and the efficiency of H_(2)O_(2) was up to 51.5%.As compared to the commercial 30 wt%aqueous H_(2)O_(2) added directly,in situ H_(2)O_(2) dramatically improved the selectivity ofε-caprolactone and had higher ***,the catalyst could be easily separated from the reaction solution and reused several times without the remarkable loss of activity.

关键词： baeyer-villiger oxidation ε-Caprolactone Sn-Beta Hydrogen peroxide Molecular oxygen

Synthesis of Submicrometer-sized Sn-MCM-41 Particles and Their Catalytic Performance in baeyer-ViUiger oxidation

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Chemical Research in Chinese Universities 2015年第1期31卷 138-143页

作者： CHEN Na JIANG Yanqiu CHENG Wenjing LIN Kaifeng XU Xianzhu State Key Laboratory of Urban Water Resource and Environment Harbin Institute of Technology Harbin 150090 P. R. China Academy of Fundamental and Interdisciplinary Sciences Harbin Institute of Technology Harbin 150080 P. R. China

Submicrometer-sized tin-containing MCM-41 particles with a size of several hundred nanometers（Sn-MCM-41/SMPs） were rapidly prepared with tin chloride as tin source and tetraethyl orthosilicate as silicon source via a dilute solution route in sodium hydroxide medium at room temperature. The characterization results show the highly ordered hexagonal mesopores and tetrahedral Sn species in Sn-MCM-41/SMPs. The material proved to be active and selective for baeyer-villiger oxidation of adamantanone with aqueous H2O2. Notably, Sn-MCM-41/ SMPs displayed a higher initial reaction rate and turnover number（TON） than common micrometer-sized Sn-MCM-41 large particles（Sn-MCM-41/LPs）, mainly attributed to the accelerated diffusion of the reactants and enhanced accessibility to the catalytic Sn species via shorter mesopore channels in Sn-MCM-41/SMPs. Furthermore, Sn-MCM-41/SMPs could be reused without the loss of activity after five runs, indicating that Sn active sites in the submicrometer-sized particles are remarkably stable. The study shows that decreasing particle size of Sn-MCM-41 in submicrometer scale is an effective way to achieve catalysts for baeyer-villiger oxidations with improved catalytic performance.

关键词： Sn-MCM-41 Submicrometer-sized particle Shorter mesopore channel baeyer-villiger oxidation

One-pot Synthesis of 6-Hydroxyhexanoic Acid from Cyclohexanone Catalyzed by Dealuminated HBEA Zeolite with Aqueous 30% H_2O_2 Solution

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China Petroleum Processing & Petrochemical Technology 2018年第3期20卷 1-6页

作者： Xia Changjiu Yang Yongjia Zhao Yi Lin Min Zhu Bin Peng Xinxin Dai Zhenyu Luo Yibin Shu Xingtian State Key Laboratory of Catalytic Materials and Reaction Engineering Research Institute of Petroleum Processing SINOPEC

The one-pot synthesis of 6-hydroxyhexanoic acid from cyclohexanone via the integrated baeyer-villiger oxida-tion and ring opening reaction catalyzed by dealuminated HBEA zeolite has been developed. Under optimized conditions,the cyclohexanone conversion and 6-hydroxyhexanoic acid selectivity are over 95%, respectively. The excellent catalyticperformance is attributed to the activation of carbonyl group of cyclohexanone and the fast hydrolysis and ring opening ofs-caprolactone by both Lewis acid and Br0nsted acid sites under aqueous conditions.

关键词： baeyer-villiger oxidation cyclohexaxlone 6-hydroxyhexanoic acid zeolite hydrolysis

A Short and Stereoselective Synthesis of the (-)-(5R,6S)-6-Acetoxy-hexadecane-5-olide

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Chinese Chemical Letters 2004年第10期15卷 1177-1178页

作者： BinSUN LiZengPENG XueSongCHEN YuLinLI YingLI StateKeyLaboratoryofAppliedOrganicChemistry InstituteofOrganicChemistryLanzhouUniversityLanzhou730000 LunanPharmaceuticalCo.Ltd. Linyi276003

R, 6S)-6-Acetoxyhexadecan-5-olide 1, a natural mosquito attractant pheromone, was synthesized from readily available aldehyde 2 and cyclopentanone 3 using L-proline-catalyzed asymmetric aldol reaction as the key step.

关键词： Acetoxyhexadecan-5-olide baeyer-villiger oxidation aldol reaction L-proline.