34475-76-8Relevant academic research and scientific papers
On the Thermal Cycloisomerization of 1-Vinylnaphthalene to Acenaphthene. A Mechanistic D-Labeling Study
Zimmermann, Gerhard,Ondruschka, Bernd,Nuechter, Matthias,Kopinke, Frank-Dieter,Remmler, Matthias
, p. 415 - 420 (1994)
Unlabeled 1-vinylnaphthalene (1) as well as positionally D-labeled 1 have been prepared and subjected to gas phase pyrolysis at low partial pressures of the educt compounds in nitrogen.At 700 deg C, 1 rearranges exclusively to acenaphthene (2).Under the conditions applied a significant H-D-exchange in the 1-vinylnaphthalene as well as in the formed acenaphthene takes place.The results obtained in this way and those resulting from pyrolysis in hydrogen (instead of nitrogen) show that despite the very high degree of dilution the high selectivity of cycloisomerization from 1 to 2 is firstly controlled by H-atom driven radical chain processes, in which the cyclization of the 2-naphthylethylradical dominates the reaction course.
Preparation of a new solid acid and its catalytic performance in di(1-naphthyl)methane hydrocracking
Zhao, Meixia,Wei, Xianyong,Zong, Zhimin
, p. 1324 - 1330 (2016)
A new solid acid was prepared by trifluoromethanesulfonic acid (TFMSA) impregnation into an acid-treated attapulgite (ATA). Di(1-naphthyl)methane (DNM) hydrocracking was used as the probe reaction to evaluate the catalytic performance of TFMSA/ATA for cleaving Car–Calk bridged bonds in coals. The results show that DNM was specifically hydrocracked to naphthalene and 1-methylnaphthalene over TFMSA/ATA in methanol in the absence of gaseous hydrogen. In particular, TFMSA/ATA was demonstrated to be stable after four cycles with slight loss in catalytic activity. Furthermore, a proposed H+ transfer mechanism successfully interprets the TFMSA/ATA-catalyzed hydrocracking reaction of DNM.
Shape Selective Catalysis by ZSM-5 in Disproportionation of 2-Methylnaphthalene
Matsuda, Takeshi,Yogo, Katsunori,Mogi, Yashuhiro,Kikuchi, Eiichi
, p. 1085 - 1088 (1990)
Disproportionation of methylnaphthalene (MN) was carried out on ZSM-5 catalysts.The external acid sites were eliminated by dealumination with (NH4)2SiF6.The dealuminated ZSM-5 gave 2,6- and 2,7-dimethylnaphthalene (DMN) from disproportionation of 2-methylnaphthalene (MN), due to its shape selective property.
A new solid acid for specifically cleaving the CarC alk bond in di(1-naphthyl)methane
Yue, Xiao-Ming,Wei, Xian-Yong,Sun, Bing,Wang, Ying-Hua,Zong, Zhi-Min,Fan, Xing,Liu, Zi-Wu
, p. 79 - 84 (2012)
Three catalysts were prepared by impregnating the same volume of pentachloroantimony (PCA), trimethylsilyl trifluoromethanesulfonate (TMSTFMS), or isometric PCA and TMSTFMA into an activated carbon (AC). Di(1-naphthyl) methane (DNM) was used as a coal-related model compound to evaluate their catalytic activity. The results show that CarCalk bond in DNM can be specifically cleaved over each catalyst to afford naphthalene and 1-methylnaphthalene under pressurized hydrogen at temperatures up to 300 °C, but as a new solid acid (NSA), PCA-TMSTFMS/AC is significantly more active for DNM hydrocracking than the other two catalysts. FTIR and SEM analyses reveal the strong interactions among PCA, TMSTFMS, and the AC in the NSA. NH 3-TPD analysis suggests that the NSA should exhibit appreciably stronger acidity than the other two catalysts. The strong interactions may result in the appreciably stronger acidity of the NSA than that of the other two catalysts and thereby facilitate DNM hydrocracking. It is presumed that H 2 was heterolytically cleaved to immobile H- and mobile H+. The addition of mobile H+ to ipso-position of DNM should be crucial step for DNM hydrocracking.
SHAPE SELECTIVE DISPROPORTIONATION OF METHYLNAPHTHALENE ON ZSM-5 CATALYST
Kikuchi, Eiichi,Mogi, Yasuhiro,Matsuda, Takeshi
, p. 909 - 919 (1992)
The conversion of 2-methylnaphthalene (2-MN) was studied at atmospheric pressure in a flow-type fixed bed reactor using H-Y, H-beta, H-mordenite, H-ZSM-5, H-ZSM-11 and H-ZSM-48 as catalysts.H-Y and H-beta exhibited high activities for disproportionation and isomerization of 2-MN.H-Mordenite and zeolites having medium size pores were active for the conversion of 2-MN which was mainly isomerized to 1-MN.The low disproportionation activities of these zeolites resulted from their shape selective properties.Disproportionation of 2-MN on the zeolite catalysts gave 2,6- and 2,7-dimethylnaphthalenes (DMN) in higher proportions than the thermodynamically attainable level.H-ZSM-5 was the most selective catalyst to produce these DMN isomers among the zeolite catalysts tested, although 2,7-DMN was formed in a higher proportion than 2,6-DMN.On H-mordenite catalyst, 2,6-DMN was more selectively formed than 2,7-DMN.The selectivity for 2,6-DMN against 2,7-DMN increased with increasing SiO2/Al2O3 ratio of H-mordenite.It is suggested that the composition of DMN isomers produced by disproportionation of 2-MN depends on the acid strength as well as on the shape selective properties of zeolites used.
Synthesis of renewable alkylated naphthalenes with benzaldehyde and angelica lactone
Cong, Yu,Li, Guangyi,Li, Ning,Wang, Aiqin,Wang, Ran,Wang, Xiaodong,Xu, Jilei,Zhang, Tao
supporting information, p. 5474 - 5480 (2021/08/16)
Herein, we report a new route for the synthesis of renewable alkylated naphthalenes (ANs) with benzaldehyde and angelica lactone, two platform compounds that can be derived from lignocellulose.
Catalytic Methylation of Aromatic Hydrocarbons using CO2/H2 over Re/TiO2 and H-MOR Catalysts
Hakim Siddiki, S. M. A.,Kamakura, Haruka,Maeno, Zen,Matsushita, Koichi,Poly, Sharmin S.,Shimizu, Ken-ichi,Ting, Kah Wei,Toyao, Takashi
, (2020/03/11)
A combined catalyst comprising TiO2-supported Re (Re(1)/TiO2; Re=1 wt%) and H-MOR (SiO2/Al2O3=90) was found to promote the methylation of benzene using CO2 and H2. This catalytic system exhibited high performance with regard to the synthesis of methylated benzenes and gave high yields of total methylated products (up to 52 % benzene-based yield and 42 % CO2-based yield) under the reaction conditions employed in this study (pCO2=1 MPa; pH2=5 MPa; T=250 °C; t=20 h) in a batch reactor. Catalyst screening demonstrated that a combination of Re(1)/TiO2 and H-MOR (SiO2/Al2O3=90) exhibited superior performance compared to other combinations of supported metal catalysts and zeolites in terms of both yield and selectivity for methylated benzenes.
Generation of Organozinc Reagents by Nickel Diazadiene Complex Catalyzed Zinc Insertion into Aryl Sulfonates
Klein, Philippe,Lechner, Vivien Denise,Schimmel, Tanja,Hintermann, Lukas
, p. 176 - 180 (2019/12/11)
The generation of arylzinc reagents (ArZnX) by direct insertion of zinc into the C?X bond of ArX electrophiles has typically been restricted to iodides and bromides. The insertions of zinc dust into the C?O bonds of various aryl sulfonates (tosylates, mesylates, triflates, sulfamates), or into the C?X bonds of other moderate electrophiles (X=Cl, SMe) are catalyzed by a simple NiCl2–1,4-diazadiene catalyst system, in which 1,4-diazadiene (DAD) stands for diacetyl diimines, phenanthroline, bipyridine and related ligands. Catalytic zincation in DMF or NMP solution at room temperature now provides arylzinc sulfonates, which undergo typical catalytic cross-coupling or electrophilic substitution reactions.
Catalytic Carboxylation of Heteroaromatic Compounds: Double and Single Carboxylation with CO 2
Mita, Tsuyoshi,Masutani, Hiroki,Ishii, Sho,Sato, Yoshihiro
supporting information, p. 841 - 845 (2019/04/25)
In the presence of PdCl 2 [P(n -Bu) 3 ] 2 (10 mol%) and ZnEt 2, 2-furyl and 2-pyrrolylmethyl acetate were carboxylated with CO 2 (1 atm), affording doubly carboxylated products in good yields. In this dearomative transformation, α,?-dicarboxylic acids were obtained selectively, in contrast to our previous report in which α,γ-dicarboxylic acids were selectively produced from 2-indolylmethyl acetates. In contrast, 5-thiazolylmethyl acetate and naphthylmethyl acetates predominantly underwent single carboxylation.
Synthesis of mesoporous ZSM-5 zeolites and catalytic cracking of ethanol and oleic acid into light olefins
Zhao, Tingting,Li, Fuwei,Yu, Hongchang,Ding, Shilei,Li, Zhixia,Huang, Xinyuan,Li, Xiang,Wei, Xiaohan,Wang, Zhenlin,Lin, Hongfei
, p. 101 - 110 (2019/02/24)
Conversion of biomass-derived chemicals into light olefins is a promising method to maintain sustainable development of light olefin industry. In this study, three mesoporous ZSM-5 zeolites (MZSM-5-A, MZSM-5-B and MZSM-5-C) with major pore diameter about 4.8 nm, 16 nm and 22 nm were synthesized using a hydrothermal method by utilizing different templates. The catalytic activity of catalysts was studied by catalytic cracking of ethanol and oleic acid. The influence of reaction temperature on conversion and product selectivity was investigated. The characterization of ZSM-5 samples showed that the orders of the external surface area and mesopore volume were MZSM-5-C > MZSM-5-B > MZSM-5-A > conventional HZSM-5. In ethanol to light olefin reaction, MZSM-5-C achieved the highest light olefin yield (318.3 mL g?1) and ethylene selectivity (42.3%) at 400 °C. In oleic acid to light olefin reaction, MZSM-5-B achieved a complete conversion of oleic acid at 500 °C, and obtained the highest light olefin selectivity (38.1%) at 550 °C. The difference may be relevant to the size and chemical structure of feedstock molecular as well as the acidity of catalysts. Regardless of ethanol or oleic acid as feedstock, introduction of mesopore in zeolites significantly enhanced the light olefin yield and selectivity.
