1,2,3,4-tetrahydro-4,6-dimethyldibenzo[b,d]thiophene | 89816-78-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 1,2,3,4-tetrahydro-4,6-dimethyldibenzo[b,d]thiophene
• 英文别名: 1,2,3,4-tetrahydro-4,6-dimethyldibenzothiophene；4,6-dimethyl-1,2,3,4-tetrahydrodibenzothiophene；tetrahydro-4,6-dimethyldibenzothiophene；4,6-dimethyltetrahydrodibenzothiophene；4,6-tetrahydrodimethyldibenzothiophene；4,6-dimethyldibenzothiophene；4,6-Dimethyl-1,2,3,4-tetrahydrodibenzo[b,d]thiophene
• CAS: 89816-78-4
• 化学式: C₁₄H₁₆S
• 分子量: 216.347
• InChiKey: RIGZTSXZDJDRHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,2,3,4-tetrahydro-4,6-dimethyldibenzo[b,d]thiophene 在 哌啶 、 tungsten phosphide 、 氢气 作用下， 以 萘烷 为溶剂， 240.0 ℃ 、4.0 MPa 条件下， 生成 4,6-dimethylhexahydrodibenzothiophene
  参考文献：
  名称：

  Hydrodesulfurization of dibenzothiophene, 4,6-dimethyldibenzothiophene, and their hydrogenated intermediates over bulk tungsten phosphide

  摘要：

  The kinetics of the hydrodesulfurization (HDS) of dibenzothiophene (DBT), 4,6-dimethyldibenzothiophene (4,6-DMDBT), and their hydrogenated intermediates over bulk tungsten phosphide (WP) was studied. WP possessed high hydrogenation/dehydrogenation activity but was highly sensitive to piperidine inhibition. 4,6-DMDBT reacted faster than DBT, and both DBT and 4,6-DMDBT reacted mainly through the hydrogenation pathway. The methyl groups suppressed the direct desulfurization of 4,6-DMDBT but significantly promoted the hydrogenation of 4,6-DMDBT and the dehydrogenation of 1,2,3,4-tetrahydro-4,6-dimethyldibenzothiophene (TH-4,6-DMDBT) and 1,2,3,4,4a,9b-hexahydro-4,6-dimethyldibenzothiophene, but decreased the rate of hydrogenation of TH-4,6-DMDBT. Piperidine inhibited the HDS of 4,6-DMDBT much more strongly than that of DBT. Substantial dehydrogenation of TH-4,6-DMDBT to 4,6-DMDBT and two of its isomers occurred. The formation of these 4,6-DMDBT isomers in the dehydrogenation of TH-4,6-DMDBT and the hydrocracking of 1-methyl-4-(3-methylcyclohexyl)-benzene, as well as the formation of cyclopentylphenylmethane and (cyclopentylmethyl)cydohexane, is ascribed to the metallic character of WP. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jcat.2015.07.019
• 作为产物：
  描述：

  3-甲基环己酮 在 溴 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 7.5h， 生成 1,2,3,4-tetrahydro-4,6-dimethyldibenzo[b,d]thiophene
  参考文献：
  名称：

  通过Tilak环合法合成4,6-二甲基二苯并噻吩和1,2,3,4-四氢-4,6-二甲基二苯并噻吩

  摘要：

  1,2,3,4-四氢-4,6-二甲基二苯并噻吩的制备方法是将2-溴-3-3-甲基环己酮与2-甲基苯硫醇偶合，然后借助多磷酸对产物进行环化处理。1,2,3,4-四氢-4,6-二甲基二苯并噻吩和4,6-二甲基二苯并噻吩的混合物是通过将2-溴-3-甲基环己基-2-烯-1-酮与2-甲基苯硫酚偶联并环化而制得的产品借助多磷酸。通过溴化Me 3 Al到Cu-催化的2-Bromocyclohex-2-en-1-one和2-bromo-3-3-methylcyclohex-2-en-1-one中共轭合成Me 3 Al来合成2-Bromo-3-甲基环己酮。消除了3-methylcyclohex-2-en-1-one。1,2,3,4,4a，9b-六氢-4,6-二甲基二苯并噻吩是通过用Zn和CF 3 COOH还原1,2,3,4-四氢-4,6-二甲基二苯并噻吩制备的。

  DOI：

  10.1002/hlca.201100191

文献信息

• Hydroconversion of Thiophene Derivatives over Dispersed Ni–Mo Sulfide Catalysts
  作者：A. V. Vutolkina、D. F. Makhmutov、A. V. Zanina、A. L. Maximov、D. S. Kopitsin、A. P. Glotov、S. V. Egazar’yants、E. A. Karakhanov

  DOI：10.1134/s0965544118140141

  日期：2018.12

  catalysts and yields of the products are explored. It is shown that, in the СО/H2О system, the highest conversion of benzothiophene and dibenzothiophene is attained at a temperature of 380°С, a СО pressure of 5 MPa, and a СО/H2О molar ratio of 2. The introduction of alkyl substituents into a dibenzothiophene molecule causes a reduction in the rate of reaction that predominantly occurs via the hydrogenation

  摘要不支持的Ni-Mo系硫化物催化剂的活性进行了研究在苯并噻吩和二苯并噻吩的温度范围340-380°С的加氢转化和以增加的ħ 2压力和СО/ H 2 О系统。通过TEM研究了油溶性前体（六羰基钼，环烷酸镍）的原位高温分解形成的分散催化剂的结构。的СО/ H影响2进行了探索О摩尔比，在系统中的水的质量含量，并且在催化剂和产物的收率的活性CO压力。它被示出的是，在СО/ H 2 О系统，苯并噻吩和二苯并噻吩的最高转化率达到380℃С，5MPa的压力СО的温度，和一个СО/ H2摩尔比为2。将烷基取代基引入二苯并噻吩分子中会导致反应速率降低，而反应速率的降低主要是通过芳香环的氢化而发生的。在H在氢化催化剂活性2压力和СО/ H 2 О系统是相当的。
• Desulfurization of diesel fuel with nickel boride in situ generated in an ionic liquid
  作者：Chenhua Shu、Tonghua Sun、Qingbin Guo、Jinping Jia、Ziyang Lou

  DOI：10.1039/c4gc00695j

  日期：——

  In order to improve the desulfurization efficiency, an ionic liquid (IL) was used as the solvent for the desulfurization of diesel fuel with nickel boride. The nickel boride prepared in IL–H2O showed high specific surface area. The desulfurization efficiency of model organosulfur compounds in this work was higher than that in the previous studies. The desulfurization reactivity of model organosulfur compounds followed the order of BT (DBT) > 3-MBT > 4,6-DMDBT. Furthermore, the products of model organosulfur compounds after desulfurization were analyzed by GC/MS and their corresponding reaction routes were proposed. The effectiveness of nickel salts followed the order of NiCl2 (Ni(OAc)2) > NiSO4 > Ni(NO3)2. The desulfurization efficiency of model diesel fuels reached 90.6% under the conditions of B/S molar ratio = 9, Ni(OAc)2/S molar ratio = 3, oil/IL volume ratio = 3, water content in IL = 5%, and reaction time = 50 min. ILs maintained their original structures after regeneration. Finally, the desulfurization of real diesel fuel was carried out and a desulfurization efficiency of 88.6% was obtained in 50 min.

  为了提高脱硫效率，使用离子液体（IL）作为硼化镍对柴油进行脱硫的溶剂。在 IL-H2O 中制备的硼化镍显示出较高的比表面积。与之前的研究相比，本研究中模型有机硫化合物的脱硫效率更高。模型有机硫化合物的脱硫反应性依次为 BT (DBT) > 3-MBT > 4,6-DMDBT。此外，还利用 GC/MS 分析了模型有机硫化合物脱硫后的产物，并提出了相应的反应路线。镍盐的有效性顺序为 NiCl2 (Ni(OAc)2) > NiSO4 > Ni(NO3)2。在 B/S 摩尔比 = 9、Ni(OAc)2/S 摩尔比 = 3、油/IL 体积比 = 3、IL 中水含量 = 5%、反应时间 = 50 分钟的条件下，模型柴油的脱硫效率达到 90.6%。IL 在再生后保持了原有结构。最后，对实际柴油进行了脱硫处理，在 50 分钟内脱硫效率达到 88.6%。
• Effect of the amount of citric acid used in the preparation of NiMo/SBA-15 catalysts on their performance in HDS of dibenzothiophene-type compounds
  作者：Miguel Ángel Calderón-Magdaleno、Juan Arturo Mendoza-Nieto、Tatiana E. Klimova

  DOI：10.1016/j.cattod.2013.06.002

  日期：2014.3

  addition of different amounts of citric acid (CA) in the impregnation solutions. The aim of this study was to inquire into the effect of the amount of citric acid on the activity and selectivity of the NiMo/SBA-15 catalysts in deep hydrodesulfurization (HDS). Catalysts were prepared by coimpregnation of Ni and Mo species from acidic aqueous solutions containing citric acid without further adjusting the solution's

  在当前的工作中，在浸渍溶液中添加不同量的柠檬酸（CA）制备了负载在SBA-15上的NiMo催化剂。这项研究的目的是调查柠檬酸的量对NiMo / SBA-15催化剂在深度加氢脱硫（HDS）中的活性和选择性的影响。通过从含柠檬酸的酸性水溶液中共浸渍Ni和Mo物质来制备催化剂，而无需进一步调节溶液的pH值。催化剂制备中使用的柠檬酸的量在CA：Mo摩尔比0.5至2.0之间变化。另外，在没有柠檬酸的情况下制备了参考NiMo / SBA-15催化剂。浸渍后，将催化剂干燥（100°C，6 h）并煅烧（500°C，4 h）。制备的催化剂的特征在于氮的物理吸附作用，小角度和粉末X射线衍射（XRD），紫外可见漫反射光谱（DRS），程序升温还原（TPR），高分辨率透射电子显微镜（HRTEM）并在二苯并噻吩（DBT）和在间歇反应器中在300°C下进行4，h，4-二甲基二苯并噻吩（4,6-DMDBT）8小时。XRD
• Mo and NiMo catalysts supported on SBA-15 modified by grafted ZrO2 species: Synthesis, characterization and evaluation in 4,6-dimethyldibenzothiophene hydrodesulfurization
  作者：O GUTIERREZ、D VALENCIA、G FUENTES、T KLIMOVA

  DOI：10.1016/j.jcat.2007.04.014

  日期：2007.7.25

  respective Mo and NiMo catalysts were prepared to study the effect of zirconia loading on the characteristics of Ni and Mo species and their catalytic activity in 4,6-dimethyldibenzothiophene hydrodesulfurization (HDS). ZrO-containing SBA-15 solids with different metal loadings (up to 23 wt% of ZrO) were prepared by chemical grafting at room temperature. Supports and catalysts were characterized by

  制备了一系列含ZrO介孔SBA-15载体及其各自的Mo和NiMo催化剂，研究了氧化锆负载对Ni和Mo物种特征及其在4,6-二甲基二苯并噻吩加氢脱硫（HDS）中的催化活性的影响。在室温下通过化学接枝制备了具有不同金属负载量（ZrO 高达 23 wt%）的含 ZrO 的 SBA-15 固体。通过 N 物理吸附、XRD、UV-vis DRS、TPR、化学分析和 HRTEM 对载体和催化剂进行了表征。将氧化锆掺入 SBA-15 载体可为沉积的钼物质提供更好的分散性，从而增加 MoS2 相的有效表面。负载在 SBA-15 材料上的 Mo 和 NiMo 催化剂显示，载体中负载氧化锆后，4,6-二甲基二苯并噻吩 HDS 的催化活性有所增加。未促进的 Mo 催化剂在 4,6-DMDBT 的氢化中间体（即四氢和六氢二甲基二苯并噻吩）的形成中具有活性；然而，他们无法通过形成脱硫产品来实现从这些中间体中有效脱硫。
• Ultradeep hydrodesulfurization of fuel over superior NiMoS phases constructed by a novel Ni(MoS₄)₂(C₁₃H₃₀N)₂ precursor
  作者：Jundong Xu、Chenglong Wen、Shuisen He、Yu Fan

  DOI：10.1039/d0cy01177k

  日期：——

  bromide-dispersed Ni–Mo sulfide (DTMA-NiMo) as a precursor for preparing an efficient NiMoS/γ-Al2O3 hydrodesulfurization (HDS) catalyst. The as-synthesized DTMA-NiMo is a sulfide containing both long-chain quaternary ammonium and Ni–Mo–S elements. The proposed method not only significantly improves the dispersion of Mo species but also greatly promotes the incorporation of Ni into MoS2 slabs, leading

  本文介绍新癸基三甲基溴化铵分散的NiMo硫化物（DTMA-的NiMo）作为用于制备高效NiMoS /γ-Al系的前体2 ö 3加氢脱硫（HDS）催化剂。合成后的DTMA-NiMo是一种既含有长链季铵盐又含有Ni-Mo-S元素的硫化物。所提出的方法不仅显着改善了Mo物种的分散，而且极大地促进了Ni掺入MoS 2平板中，从而导致NiMoS相的数量增加。其结果是，基于DTMA-的NiMo-NiMoS /γ-Al系2个ö 3催化剂显示出高得多的对4,6-二甲基（4,6-DMDBT）和流化催化裂化（FCC）柴油比NiMoS的HDS活性/ γ-铝2通过共浸渍和四丙基溴化铵（TPAB）辅助方法制备的O 3催化剂。这种新颖的策略为无需硫化处理的便捷且低成本的高级NiMoS相制备提供了启示。