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CATALYSIS LETTERS · 2021 ·Vol. 152 ·期 1 ·162-171 · IF 3.186

Magnesium Pyrophosphate-Catalyzed Epoxidation of 1-Octene with Aqueous Hydrogen Peroxide

Yang Xingyu,Li Xu,Dong Jinxiang

The epoxidation of terminal olefins (e.g., 1-octene) presents an enormous challenge owing to their electron-deficient nature, whereas the vicinal diols that are derived from epoxides are highly desirable as fine chemicals. We report the facile preparation of magnesium pyrophosphate via the thermal decomposition of commercially available newberyite and the first use of magnesium pyrophosphate as a solid catalyst for terminal olefin epoxidation. The as-synthesized magnesium pyrophosphate was characterized by XRD, FTIR, SEM–EDS, and CO 2 -TPD techniques. The CO 2 -TPD results proved that the medium base was dominant in magnesium pyrophosphate. Magnesium pyrophosphate exhibited an effective catalytic activity in the liquid-phase epoxidation of 1-octene with a 94.2% selectivity of epoxide using aqueous hydrogen peroxide as oxidant in the presence of acetonitrile solvent. The influences of various reaction parameters, including solvent, temperature, H 2 O 2 to 1-octene molar ratio, amount of magnesium pyrophosphate, reaction time, and solvent amount were investigated. According to the reaction mechanism, the perhydroxyl ion that originated from H 2 O 2 heterocracking formed in the presence of magnesium pyrophosphate and reacted with acetonitrile to generate active intermediate peroxycarboximidic acid. The epoxide and amide formed when active oxygen was transferred from peroxycarboximidic acid to the olefin. Therefore, magnesium pyrophosphate was an appropriate catalyst for 1-octene epoxidation. Graphic Abstract

CAS / MDL: 75-05-8 111-66-0
研究领域: 化学 · 催化化学
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NEW JOURNAL OF CHEMISTRY · 2022 ·Vol. 46 ·期 8 ·3901-3908 · IF 3.925

Hydroisomerization of 1-octene utilizing hierarchical SAPO-11-supported Ni catalysts: effect of the alkyl chain length of the mesoporogen

Zhiping Chen,Li Liu,Faxiang Shi,Wenwu Zhou,Zhiyuan Yang,Anning Zhou

A series of hierarchical SAPO-11 molecular sieves synthesized by adding mesoporogens with different alkyl chain lengths were prepared. The synthesized hierarchical SAPO-11s were characterized by XRD, SEM, N2 adsorption–desorption, TEM, NH3-TPD and Py-IR. The results showed that the physicochemical properties of the hierarchical SAPO-11s change with the increase of the alkyl chain length, and the hierarchical SAPO-11 molecular sieve synthesized with DTAB has the largest external surface area and pore volume, and the most medium and strong B acid sites. Furthermore, the 1-octene hydroisomerization reaction on Ni catalysts supported on hierarchical SAPO-11 was investigated and the experimental results showed that the alkyl chain length of the mesoporogen has an obvious influence on the hydroisomerization selectivity. The hierarchical Ni/SAPO-11 catalyst synthesized using DTAB has the highest selectivity of C8 isomers and the lowest cracking selectivity. These results indicate that DTAB is the most suitable mesoporogen for the synthesis of hierarchical SAPO-11 molecular sieves for 1-octene hydroisomerization.

研究领域: 催化化学 · 材料科学
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Catalysis Science & Technology · 2019 ·Vol. 9 ·期 24 ·7034-7044 · IF 5.726

Insight into the impact of Al distribution on the catalytic performance of 1-octene aromatization over ZSM-5 zeolite

Liwei Zhang,Huaike Zhang,Zhiqiang Chen,Qiang Ning,Suyao Liu,Jie Ren,Xiaodong Wen,Yong-Wang Li

To correlate the relationship between the Al distribution and the catalytic performance of long-chain olefin aromatization, several ZSM-5 zeolites with different Al locations and proximities were prepared via adjusting the hydrothermal synthesis conditions. Characterization by XRD, SEM and N2-adsorption indicated that all the as-prepared ZSM-5 zeolites exhibited high crystallinities, uniform morphologies and open channels. However, a great difference in the framework Al (AlF) positions was observed by 27Al MAS NMR and UV-vis-DRS of Co(II) ions, thus leading to the distinct acidity of various zeolites as determined by NH3-TPD and Py-IR. In 1-octene aromatization reaction, ZSM-5 catalysts exhibited significantly different catalytic performances and reaction pathways, which were closely related to the types and locations of the AlF atoms. The ZSM-5 zeolite catalyst with the most abundant single Al sites exhibited the lowest aromatics selectivity, while Al pairs in the framework were more favorable to the formation of aromatics. Moreover, the product distribution revealed that the Al pairs in the channel intersections of the ZSM-5 zeolite were responsible for the improved selectivity to heavy aromatics due to the fewer space restrictions; however, the Al pairs in the sinusoidal and straight channels with severe size restrictions suppressed the generation of bigger aromatics on the Al sites. This result provided a new potential method for precisely tailoring the catalytic selectivity in olefin conversion and upgrading the Fischer–Tropsch oil.

CAS / MDL: 71-43-2 111-66-0
研究领域: 催化化学 · 材料科学
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FARADAY DISCUSSIONS · 2016 ·Vol. 190 ·219-230 · IF 3.544

Immobilization of a rhodium catalyst using a diphosphine-functionalized ionic liquid in RTIL for the efficient and recyclable biphasic hydroformylation of 1-octene

Yong-Qi Li,Huan Liu,Peng Wang,Da Yang,Xiao-Li Zhao,Ye Liu

A highly efficient and stable Rh–P catalytic system in the RTIL of [PEmim]BF4 was developed for the biphasic hydroformylation of 1-octene by using the diphosphine-functionalized ionic liquid (FIL) of 2. While 2-Rh(acac)(CO)2 was immobilized in [PEmim]BF4 (solvent), a typical biphasic catalysis was fulfilled with advantages of facile separation and recycling ability – 9 runs without any loss of activity. It was found that not only the acquired π-acceptor character of 2, but also the synergetic role of the piperidyl group in [PEmim]BF4 as an N-containing donor, cooperatively contributed to the efficient hydroformylation due to the facilitated formation and stability of the Rh-H active species (ν 2045 cm−1). This was supported by the in situ high-pressure FT-IR spectral analysis.

研究领域: 化学工程 · 催化科学
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JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL · 2013 · IF 3.187

An ionic phosphine-ligated rhodium(III) complex as the efficient and recyclable catalyst for biphasic hydroformylation of 1-octene

Sheng-Jie Chen,Yong-Yong Wang,Wei-Min Yao,Xiao-Li Zhao,Giang VO-Thanh,Ye Liu

A novel ionic complex with insensitivity to moisture and air, bis-[1-butyl-2-diphenylphosphanyl-3-methylimidazolium]tetrachloridorhodium(III) hexafluorophosphate ( 1A ), has been synthesized and fully characterized. The single-crystal X-ray diffraction analysis shows that 1A is composed of the Rh(III)-complex cation and the counter-anion of PF 6 − . The complex cation has highly symmetrical Rh III -centered octahedron geometry with four Cl atoms in the equatorial plane and two imidazolium-substituted phosphine ligands in the axial position. The catalytic performance of 1A , which could be tailored by the ligands and the solvents, was investigated toward the biphasic hydroformylation of 1-octene. It was found that the presence of the hemilabile hybrid P,N-ligand of 3 (1-(2′-piperid-1′-yl-ethyl)-2-diphenylphosphino-3-methylimidazolium hexafluorophosphate), as a kind of ligand-functionalized ionic liquids (ILs), could dramatically spur the catalytic activity of 1A . The use of the RTIL of [PEmim]BF 4 (1-(2′-piperid-1′-yl-ethyl)-3-methylimidazolium tetrafluoroborate) as the solvent not only fulfilled the efficient biphasic hydroformylation of 1-octene, but also guaranteed the successful recovery and recycling of the ionic compositions of 1A and 3 .

研究领域: 化学 · 催化反应
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DALTON TRANSACTIONS · 2023 ·Vol. 52 ·期 39 ·13955-13961 · IF 4

Enhancing stability via confining Rh–P species in ZIF-8 for hydroformylation of 1-octene

Xiaorui Yan,Lele Chen,Haisheng Wei,Tiantian Liu,Kairui Li,Jing Li

The stability of Rh-based heterogeneous catalysts is a key issue in the hydroformylation of olefins. Confinement of active Rh species has been considered an effective strategy to achieve stable catalysts. In this work, a phosphine ligand was successfully confined in ZIF-8 material and coordinated with Rh metal by a reduction procedure to develop an efficient and stable Rh-based catalyst for hydroformylation of 1-octene. The results indicate that the catalyst reduced at 300 °C under H2 atmosphere exhibits better stability than that with NaBH4 as reductant and undoped P catalyst. Various characterization studies demonstrate that the superior performance is due to the strong interaction between Rh metal and P, which inhibits the leaching of active Rh species. This work reveals an effective strategy for the synthesis of highly stable catalysts for use in the hydroformylation reaction.

CAS / MDL: 693-98-1 111-66-0
研究领域: 催化 · 化学工程 · 材料科学
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JOURNAL OF CHEMICAL THERMODYNAMICS · 2025 · IF 2.2

Liquid−liquid equilibrium for ternary systems of 1-Octene +2-Hexanone + ionic liquid: Phase equilibrium measurement and correlation

Xianming Zhang,Yanping Li,Yongli Wu,Yunfei Wang,Panpan Yan,Zhilei Zheng,Hongyu Peng,Yuexin Chu

Liquid–liquid equilibrium (LLE) for the binary systems of 1-octene +1-ethyl-3-methylimidazolium acetate ([EMIM][Ac]), 1-octene +1-butyl-3-methylimidazolium acetate ([BMIM][Ac]), 1-octene +1-butyl-3-methylimidazolium tetrafluoroborate ([BMIM][BF 4 ]), 2-hexanone + [EMIM][Ac], and 2-hexanone + [BMIM][Ac], and the ternary systems of 1-octene +2-hexanone + [EMIM][Ac], 1-octene +2-hexanone + [BMIM][Ac], and 1-octene +2-hexanone + [BMIM][BF 4 ] were measured at 298.15 K, 303.15 K and 313.15 K under 101.3 kPa. The solute distribution coefficient ( D ) and selectivity ( S ) were calculated to investigate the efficiencies of [EMIM][Ac], [BMIM][Ac], and [BMIM][BF 4 ] as solvents. Moreover, the temperature dependencies of D and S were investigated in this study. NRTL and UNIQUAC models were applied to correlate the experimental LLE data.

研究领域: 化学工程 · 物理化学
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JOURNAL OF CATALYSIS · 2017 · IF 6.844

A novel route to synthesize SAPO-11 molecular sieves with a high external surface area in the presence of ethylene glycol and supercritical carbon dioxide for 1-octene hydroisomerization to dimethylhexanes

Chenglong Wen,Shanlei Han,Jundong Xu,Yu Fan

The article proposes a novel and eco-friendly method for synthesizing SAPO-11 in ethylene glycol (EG) and supercritical carbon dioxide (ScCO 2 ). The method incorporates ScCO 2 into EG to decrease the solubility of SAPO-11 precursors in EG and thereby forms a highly supersaturated solution of SAPO-11 precursors. The as-synthesized SAPO-11 possesses smaller particles, a larger external surface area, and a larger number of acid sites than the SAPO-11 synthesized in EG and the SAPO-11 synthesized in water and ScCO 2 , respectively. These advantages of the as-synthesized SAPO-11 endow the corresponding catalyst with superior dibranched isomer selectivity and low cracking selectivity during 1-octene hydro isomerization.

研究领域: 化学工程 · 催化材料
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Food Bioscience · 2025 · IF 5.9

Enhancement of 1-octen-3-ol in Lentinus edodes Maillard peptides through exogenous linoleic acid and its synergistic effect with l-cysteine

Mengli Wang,Xinjing Li,Foxin Zhang,Heping Cui,Khizar Hayat,Xiaoming Zhang,Chi-Tang Ho

Extra-added l- cysteine effectively inhibited the browning of Maillard peptides (MPs) derived from Lentinus edodes . Meanwhile, an unsaturated fatty acid (UFA) was introduced to increase the content of 1-octen-3-ol (mushroom alcohol) to enhance the mushroom aroma of the MPs. Among the three UFAs tested, linoleic acid (LA) exhibited the strongest promoting effect on 1-octen-3-ol, resulting in a 1-octen-3-ol content of 74.57 ± 1.48 μg/L in MPs. When LA was co-heated with l- cysteine and/or xylose, a synergistic effect was observed between LA and l- cysteine, leading to the highest 1-octen-3-ol content of 211.29 ± 3.62 μg/L in LA- l- cysteine-xylose system. The enzymatic hydrolysate of commercial safflower seed oil was further used as an alternative source of LA to fortify the typical mushroom flavor. The incorporation of 25 % safflower seed oil hydrolysate was recommended to enhance the 1-octen-3-ol production (133.09 ± 8.74 μg/L) in MPs. These findings provide new ideas for enhancing the mushroom aroma, offering potential applications in flavor design and food processing.

CAS / MDL: 3391-86-4 3777-69-3
研究领域: 食品科学 · 生物化学
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Polymers · 2024 ·Vol. 16 ·期 4 ·526 · IF 4.7

The Effect of Feeding Sequence on the Structure and Properties of the Ethylene/1-Octene Copolymer in the Semi-Continuous Polymerization Reaction System

Qiqi He,Ruijun Zhang,Yuexin Hu,Junhua Li,Hongbo Yu,Yong Zheng,Jianhua Qian

The performance of ethylene/1-octene copolymer primarily depends on the microstructure of the polymer chain. This study employed a new method to control the inter-distribution of hexyl chain branches directly on the backbone of the ethylene/1-octene copolymer. Three ethylene/1-octene copolymers with different inter-distributions of hexyl chain branches were synthesized using [Me2Si(C5Me4) (NtBu)] TiCl2(Ti–CGC) by different feeding sequences in the semi-continuous polymerization reaction system. The three copolymers were named according to the feeding sequence of the materials: ethylene/1-octene/Ti–CGC (EOC), 1-octene/Ti–CGC/ethylene (OCE), and ethylene/Ti–CGC/1-octene (ECO), respectively. The structure and properties of the copolymers were characterized using HT-GPC,13C-NMR, DSC, WAXD, DMA, MI, and Uniaxial Tension Test. The results showed that the feeding sequence greatly affected the comonomer distribution of the molecular chains, molecular weight, molecular weight distribution, and chemical composition of the copolymers, consequently influencing their thermal performance and mechanical properties. Thus, it is probable that one could obtain an ethylene/1-octene copolymer with designed properties by controlling the feeding sequence during the ethylene/1-octene semi-continuous copolymerization process.

研究领域: 材料科学 · 高分子化学
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INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH · 2018 · IF 3.141

Insight into Copolymerization of Methyl (Meth)Acrylate and 1-Octene with Aluminum Trichloride

Changfa Xiao,Yuyan Yu,Long Jiang,Yi Dan

Aluminum trichloride (AlCl3) catalyzed copolymerization of polar monomers, including both methyl methacrylate (MMA) and methyl acrylate (MA), with nonpolar 1-octene is investigated. The copolymerization of MMA and 1-octene produces copolymers with acceptable productivity in the present of AlCl3, but no alternating copolymer can be obtained even in a 1-octene rich condition (n(1-octene)/n(MMA) = 6.14/1). However, AlCl3-catalyzed copolymerization of MA and 1-octene unveils that MA is more feasible than MMA to copolymerize with 1-octene for the formation of alternating copolymer. An alternating copolymer of MA and 1-octene can be obtained even at MA-rich conditions (n(1-octene)/n(MA) = 0.58/1). Meanwhile, temperature shows a significant impact on the copolymerization behaviors. Performing AlCl3-catalyzed copolymerization of MA and 1-octene at lower temperature leads to an increase in the molecular weight and the incorporation of MA into the backbone of the copolymer, probably due to low temperature-enhanced complexation between AlCl3 and the ester functionality.

CAS / MDL: 7446-70-0
研究领域: 高分子化学 · 催化化学
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POSTHARVEST BIOLOGY AND TECHNOLOGY · 2025 · IF 6.8

Unravelling the inhibition mechanism of 1-octene-3-ol combined with 3-heptene-2-one on Aspergillus flavus and its application in the preservation of wolfberries

Lijun Ling,Rongxiu Mo,Wenyue Zhang,Yijuan Jiang,Fanjin Kong,Lijun Feng,Yao Li,Rui Yue,Yongpeng Zhou

The antifungal activity of six microbial-derived volatile organic compounds (VOCs) [ 3-hepten-2-one (Hep), cis-3-octen-1-ol, 3-methylvalerate, isovalerate, 1-octen-3-ol (Oct), and 2-methylbutyrate] against Aspergillus flavus was investigated by determining the minimum inhibitory concentration (MIC) and the fractional inhibitory concentration index (FICI). The results demonstrated that all 15 binary combinations of the VOCs presented additive effects against A. flavus . Among them, the combination of Hep and Oct, refers to C OH , with concentrations of 2 μL L −1 and 2.5 μL L −1 , respectively, displayed the most potent antifungal effect with the lowest concentration, in contrast to the individual MIC of Hep or Oct, which were reduced to 1/8 and 1/2. C OH can induce membrane lipid peroxidation, enhance cell membrane permeability, and cause leakage of nucleic acids and proteins within the cell, and 1-octen-3-ol might play a leading role. Finally, applying C OH at a concentration of 1/2 MIC Oct + 1/4 MIC Hep could effectively restrain the spread of A. flavus on wolfberries and exhibit excellent preservation effects. This study validates the antifungal effect of C OH and may serve as a natural alternative to antimicrobial agents for post-harvest agricultural products.

研究领域: 食品科学 · 微生物学 · 植物保护
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