6931-54-0Relevant academic research and scientific papers
Catalytic epoxidation of β-pinene with aqueous hydrogen peroxide
Fomenko,Bakhvalov,Kollegov,Salakhutdinov
, p. 1675 - 1679 (2017)
Epoxidation of β-pinene with 35–38% aqueous hydrogen peroxide in a new catalytic system containing manganese sulfate, salicylic acid, sodium bicarbonate and polar solvent (DMF, acetonitrile, methanol) is described. The method of quantitavive determination of β-pinene and its epoxide is developed.
Diamine-Decorated Graphene Oxide with Immobilized Gold Nanoparticles of Small Size for Alkenes Epoxidation with H2O2
Zheng, Weiguo,Hu, Haining,Chen, Yaju,Tan, Rong,Yin, Donghong
, p. 3328 - 3337 (2019)
Abstract: Diamine-decorated graphene oxide (NH2-GO) is successfully synthesized by covalently intercalated ethanediamines into the flat planes and edge of the GO sheet. The diamines could be act as buffer layer, thereby avoiding the stacking of graphene sheets, and offer abundant metal-chelating sites to subsequently obtain well-dispersed metal nanoparticles of small size. After the in situ reduction and deposition of AuNPs, it was found that the Au particle size of Au0.9%@NH2-GO estimated to be around 2–5?nm. The as-prepared GO-supported small AuNPs exhibited good catalytic performance for the heterogeneous epoxidation of alkenes with H2O2 under mild conditions. Notably, they presented good expansibility for either bulky or less bulky alkenes in this reaction, owing to the facilitated efficiency of mass transfer of substrates and products resulted from the supporting effect of intercalated diamines and high surface area of GO. Moreover, these heterogeneous catalysts could be readily recovered and recycled for five times with the remained activity and selectivity. Graphic Abstract: Gold nanoparticles of small size immobilized on the diamine-decorated graphene oxide has been developed, which employed as an efficient, universal and reusable catalyst for the epoxidation of alkenes using H2O2 as an oxidant.[Figure not available: see fulltext.].
A highly efficient method of epoxidation of olefins with hydrogen peroxide catalyzed by changeable hexadentate 8-quinolinolato manganese(III) complexes
Zhong, Sheng,Tan, Yueming,Fu, Zaihui,Xie, Qingji,Xie, Fang,Zhou, Xiaoping,Ye, Zhengpei,Peng, Guosheng,Yin, Dulin
, p. 154 - 158 (2008)
Novel hexadentate binding 8-quinolinolato manganese(III) complexes were proposed and conveniently synthesized for the epoxidation of olefins with aqueous hydrogen peroxide in water-acetone media with ammonium acetate and acetic acid as additives. The catalytic efficiencies of the suggested catalysts were found to be obviously superior to the traditional tetradentate salen-MnIIICl, due to their special hexadentate binding structures that could be easily converted to the corresponding pentadentate with pendant hydroxyl groups by opening an axial Mn{single bond}O bond in the reaction media, as supported by UV-vis spectra, in situ cyclic voltammetry, and quartz crystal microbalance characterizations.
A recyclable cobalt(iii)-ammonia complex catalyst for catalytic epoxidation of olefins with air as the oxidant
Wang, Chenlong,Zhan, Hongju,Lu, Xinhuan,Jing, Run,Zhang, Haifu,Yang, Lu,Li, Xixi,Yue, Fanfan,Zhou, Dan,Xia, Qinghua
, p. 2147 - 2156 (2021/02/06)
[Co(NH3)6]Cl3and other ammonia complexes with different external anions or metal ions were synthesized to catalyze the epoxidation of α-pinene. The synthesized complexes were characterized using XRD, SEM, TGA, FTIR and UV spectra. With air as the oxidant, [Co(NH3)6]Cl3exhibited excellent catalytic activity for the epoxidation of α-pinene among the prepared complexes. The conversion of α-pinene reached 97.4%, with 98.3% selectivity of epoxide when using a small amount of cumene hydroperoxide (CHP) as the initiator. The results revealed that a single Co(iii) system can also catalyze the epoxidation process in the absence of Co(ii), even showing better catalytic performance than single Co(ii). Recycling experiments showed that there was no significant drop in activity after 10 cycles, demonstrating that it is a stable and efficient heterogeneous catalyst for the epoxidation of α-pinene. The excellent recycling performance may be attributed to the stability of the coordination complex itself.
Method for synthesizing epoxy pinane from pinene
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Paragraph 0036-0037, (2021/04/07)
The invention relates to a method for synthesizing epoxy pinane from pinene. The method comprises the following steps: 1) fully mixing pinene, a solvent and an auxiliary agent; 2) dropwise adding hydrogen peroxide and acetic anhydride into the mixed solution obtained in the step 1) at a certain temperature for reaction; and 3) after the reaction is finished, washing the material, recovering the solvent under reduced pressure, and rectifying under reduced pressure to obtain the product epoxy pinane. The method provided by the invention has the advantages of high conversion rate, good selectivity, mild reaction conditions, simple operation and the like, and the method has high economic applicability and is suitable for industrial production.
Easy Epoxidation of Monoterpenes from Common Starting Materials
Benitez, Ricardo B.,Bermudez, John H.,Franco, Jaime M.,Rojas, Giovanni
, p. 1086 - 1092 (2020/10/14)
Epoxidation of monoterpenes, α-pinene, β-pinene, limonene, α-terpinene, and (R)-carvone was carried out by the in situ production of a peroxyacid rather than direct addition of such an expensive and difficult to handle chemical. Previous reports showed use of metal catalysts with high yields, while methodologies without catalysts at high temperature showed yields lower than 30%. The authors report a methodology that produces peroxyacetic acid in situ yielding up to 75% pure epoxide at room temperature avoiding the use of catalysts. The products were analyzed by gas chromatography mass spectrometry (GC-MS), and structures were characterized by 1H and 13C nuclear magnetic resonance (NMR).
Fast-synthesis and catalytic property of heterogeneous Co-MOF catalysts for the epoxidation of α-pinene with air
Zhang, Haifu,He, Jie,Lu, Xinhuan,Yang, Lu,Wang, Chenlong,Yue, Fanfan,Zhou, Dan,Xia, Qinghua
, p. 17413 - 17421 (2020/11/02)
In the past decades, many methods have been developed for synthesizing MOFs, including solvothermal synthesis, mechanical synthesis, electrochemical synthesis, and microwave synthesis. Based on the existing research, a method is proposed for synthesizing Co-MOF by rapidly rotating hydrothermal crystallization, which largely shortens the crystallization time of Co-MOF. When the rotation speed was 150 rpm, only 2 h of crystallization time was needed to synthesize Co-MOF-150-2 with high crystallinity and stability. The optimal Co-MOF-150-2 manifested remarkable activity and selectivity for the epoxidation of α-pinene under mild conditions. The catalytic conversion of α-pinene reached the highest over the Co-MOF-150-2 catalyst, in which the conversion of α-pinene was 99.5% and the yield of 2,3-epoxypinane was 95.7%. The Co-MOF materials synthesized by the rotary method also had excellent stability and highly catalytic activity in recycling experiments. This journal is
Selective Allylic Oxidation of Terpenic Olefins Using Co-Ag Supported on SiO2 as a Novel, Efficient, and Recyclable Catalyst
Aberkouks, Abderrazak,Mekkaoui, Ayoub Abdelkader,Ait Ali, Mustapha,El Firdoussi, Larbi,El Houssame, Soufiane
, (2020/02/15)
Co-Ag supported on the SiO2 catalyst was synthesized by the sol-gel method and characterized using XRD, FT-IR, TG-DTG, BET, CV, and SEM/EDX analysis. The catalytic performance of the resulting catalyst was examined by the oxidation of mono and sesquiterpenic olefins using hydrogen peroxide and tert-butyl peroxide as oxidant agents. Various parameters such as catalyst amount, temperature, and solvents have been studied. The Co-Ag supported on the SiO2 catalyst showed a high activity, selectivity, and recyclability for the selected oxidation reaction.
Cobalt imine–pyridine–carbonyl complex functionalized metal–organic frameworks as catalysts for alkene epoxidation
Qin, Yutian,Wang, Bowei,Li, Jiayi,Wu, Xingchun,Chen, Ligong
, p. 595 - 602 (2019/05/04)
Aerobic epoxidation of alkene is a green and economical route to produce epoxides. For such reaction, transition metal complexes exhibit favorable catalytic activity. In this work, NH2-MIL-101, a stable metal–organic framework (MOF) material with large surface area and high pore volume, was functionalized with pyridine-2,6-dicarbaldehyde and Co(NO3)2, to realize the immobilization of Co(II) via imine–pyridine–carbonyl (N,N,O) tridentate ligands bonding to MOF skeleton. The modified materials were applied as heterogeneous catalysts for the aerobic epoxidation of cyclohexene at ambient temperature, and multiple factors were studied to explore their influences on catalytic effects. Under the optimal reaction conditions, satisfactory substrate conversion and epoxide selectivity were reached. In addition, this catalytic system is suitable for a variety of alkene substrates. Furthermore, recycle experiments and infrared spectroscopy characterization illustrated that the coordination surroundings of Co are altering smoothly during the reaction process, thus having?an impact on the performance of catalyst.
Kinetics of the Aqueous Phase Reactions of Atmospherically Relevant Monoterpene Epoxides
Cortés, DIego A.,Elrod, Matthew J.
, p. 9297 - 9305 (2017/12/18)
Laboratory and field measurements have demonstrated that an isoprene-derived epoxide intermediate (IEPOX) is the origin of a wide range of chemical species found in ambient secondary organic aerosol (SOA). In order to explore the potential relevance of a similar mechanism for the formation of monoterpene-derived SOA, nuclear magnetic resonance techniques were used to study kinetics and reaction products of the aqueous-phase reactions of several monoterpene epoxides: β-pinene oxide, limonene oxide, and limonene dioxide. The present results, combined with a previous study of α-pinene oxide, indicate that all of these epoxides will react more quickly than IEPOX with aqueous atmospheric particles, even under low-acidity conditions. As for α-pinene oxide, the observed products can be mainly rationalized with a hydrolysis mechanism, and no long-lived organosulfate or nitrate species nor species that retain the β-pinene bicyclic carbon backbone are observed. As bicyclic ring-retaining organosulfate and nitrate species have been previously observed in monoterpene-derived SOA, it appears that monoterpene-derived epoxides may not be as versatile as IEPOX in producing a range of SOA species, and other mechanisms are needed to rationalize organosulfate and nitrate formation.
