1,7-二异丙基萘 | 94133-80-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1,7-二异丙基萘
• 中文别名: 二乙基5-(甘氨酰氨基)-2-羟基-4,6-二甲基苯-1,3-二羧酸酯
• 英文名称: 1,7-diisopropylnaphthalene
• 英文别名: 1,7-DIPN；1,7-di(propan-2-yl)naphthalene
• CAS: 94133-80-9
• 化学式: C₁₆H₂₀
• 分子量: 212.335
• InChiKey: XNSUVOOWWSAQMZ-UHFFFAOYSA-N

物化性质

• 沸点：
  305.8±12.0 °C(Predicted)
• 密度：
  0.949±0.06 g/cm3(Predicted)
• 物理描述：
  Liquid
• 保留指数：
  1667

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  2,3-二甲基-2-环戊烯酮 在 磷酸 作用下， 反应 3.0h， 生成 1,2,3,4-四甲基萘 、 卡达萘 、 1,7-二异丙基萘 、 1,4,5,8-四甲基萘
  参考文献：
  名称：

  聚（3-羟基丁酸酯）催化重整为可再生烃油的反应路线†

  摘要：

  聚（3-羟基丁酸酯）或PHB是微生物的能量存储材料，可以重整为富含芳族化合物的烃油。这项工作研究了从PHB到关键中间体和最终碳氢化合物的主要反应路线。在中等温度（200–230°C）下催化磷酸的主要顺序反应包括：（1）PHB分解为巴豆酸，主要的单体中间体，（2）巴豆酸脱氧，以及（3）组合脱氧分子。PHB中的氧气以CO 2和H 2的形式除去在步骤（2）中的O，涉及巴豆酸的脱羧和酮化。主要的芳族化合物是在阶段（3）中由丙烯和2,3-二甲基-2-环戊烯-1-酮作为两个关键中间体形成的，前者来自脱羧作用，后者来自巴豆酸的酮化作用。反应路线表明，反应中磷酸和水的浓度在很大程度上影响芳烃的形成，可用于控制烃油的组成。

  DOI：

  10.1039/c5ra03195h

文献信息

• Isopropylation of naphthalene by isopropanol over conventional and Zn- and Fe-modified USY zeolites
  作者：Marimuthu Banu、Young Hye Lee、Ganesan Magesh、Jae Sung Lee

  DOI：10.1039/c3cy00691c

  日期：——

  Catalytic performances of USY, MOR, and BEA zeolites were compared for the isopropylation of naphthalene by isopropyl alcohol in a high-pressure, fixed-bed reactor. The USY catalyst showed a high conversion of 86% and good stability but a low 2,6-/2,7-DIPN shape selectivity ratio of 0.94. In contrast, over the MOR catalyst, 2,6-DIPN was selectively synthesized with a high 2,6-/2,7-DIPN ratio of 1.75, but low naphthalene conversions and fast deactivation of the catalyst were observed. The USY catalyst was modified by Zn and Fe using the wet impregnation method to enhance the selectivity for 2,6-DIPN. The highest conversion (~95%) and selectivity for 2,6-DIPN (~20%) were achieved with 4% Zn/USY catalyst. It appeared that small metal oxide islands formed in the USY pores to decrease the effective pore size and thus render it mildly shape-selective. Zn loading also decreased the number of strong acid sites responsible for coke formation and increased the number of weak acid sites. The high conversion and stability of Zn-modified catalysts were ascribed to the presence of a suitable admixture of weak and strong acid sites with less coke deposition. The Fe-modified USY catalysts were less effective because the modification increased the number of the strong acid sites.

  比较了 USY、MOR 和 BEA 沸石在高压固定床反应器中用异丙醇对萘进行异丙基化反应的催化性能。USY 催化剂的转化率高达 86%，稳定性良好，但 2,6-/2,7-二硝基萘的形状选择性较低，仅为 0.94。相反，在 MOR 催化剂上，2,6-DIPN 被选择性合成，2,6-/2,7-DIPN 比率高达 1.75，但萘转化率低，催化剂失活快。采用湿浸渍法对 USY 催化剂进行了锌和铁改性，以提高 2,6-DIPN 的选择性。在使用 4% Zn/USY 催化剂时，2,6-DIPN 的转化率（约 95%）和选择性（约 20%）最高。USY 孔中似乎形成了小的金属氧化物岛，从而减小了有效孔径，使其具有轻微的形状选择性。此外，锌的添加还减少了导致焦炭形成的强酸位点的数量，增加了弱酸位点的数量。Zn 改性催化剂的高转化率和稳定性可归因于弱酸和强酸位点的适当混合以及较少的焦炭沉积。铁改性 USY 催化剂的效果较差，因为改性增加了强酸位点的数量。
• The Alkylation of Naphthalene over One-Dimensional Fourteen-Membered Ring Zeolites. The Influence of Zeolite Structure and Alkylating Agent on the Selectivity for Dialkylnaphthalenes
  作者：Yoshihiro Sugi、Hiroyoshi Maekawa、Hiroaki Naiki、Kenichi Komura、Yoshihiro Kubota

  DOI：10.1246/bcsj.81.1166

  日期：2008.9.15

  The alkylation, i.e., isopropylation, s-butylation, and t-butylation, of naphthalene (NP) was examined over one-dimensional fourteen-membered (14-MR) zeolites: CIT-5 (CFI), UTD-1 (DON), and SSZ-53 (SFH), and compared to the results over H-mordenite (MOR) to elucidate how zeolite structure and alkylating agent play roles in the shape-selective catalysis. The β,β-selectivities (for β,β-dialkylnaphthalene (2,6- and 2,7-dialkylnaphthalenes, β,β-DAN)) and the 2,6-selectivities (for 2,6-DAN) were varied with the types of zeolite and of alkylating agent. MOR gave high β,β-selectivities in the all alkylations in the range of 150–300 °C. However, the 14-MR zeolites, CFI, DON, and SFH, gave much lower β,β-selectivities in the isopropylation: bulky and less stable α,β- and α,α-diisopropylnaphthalenes (α,β-DIPN: 1,3-, 1,5-, and 1,7-DIPN); α,α-DIPN (1,4- and 1,5-DIPN) were predominantly obtained under kinetic control at low temperatures, and stable and less bulky β,β-DIPN were formed under thermodynamic control at high temperatures. The β,β-selectivities were higher than 95% over CFI in the s-butylation, and increased from 50–60% at 150 °C to 75% at 300 °C over DON and SFH, respectively. They were almost 100% in the t-butylation over all zeolites. The alkylation over MOR occurred with high 2,6-selectivities in the range of 150–250 °C: 60% for the isopropylation, 80% for the s-butylation, and 95% for the t-butylation. CFI, DON, and SFH gave the 2,6-selectivities in the range of 5–30% in the isopropylation, 65%, 55%, and 50%, respectively, in the s-butylation, and higher than 80% in the t-butylation. These different features are explained by the discrimination of the least bulky DAN isomers from the other isomers by steric restriction with the zeolite channels at the transition states: β,β-DAN from the DAN isomers, and 2,6-DAN from β,β-DAN. The bulkiness of alkylating agent also enhances the discrimination of the isomers, particularly, between 2,6- and 2,7-DAN. The β,β- and 2,6-selectivities are synergistically governed by the zeolite channel and the bulkiness of alkylating agents.

  研究了萘 (NP) 在一维十四元胞（14-MR）沸石上的烷基化，即异丙基化、叔丁基化和叔丁基化：CIT-5（CFI）、UTD-1（DON）和 SSZ-53（SFH），并与 H-莫来石（MOR）上的结果进行了比较，以阐明沸石结构和烷基化剂如何在形状选择催化中发挥作用。β,β-选择性（对 β,β-二烷基萘（2,6- 和 2,7-二烷基萘，β,β-DAN））和 2,6-选择性（对 2,6-DAN）随沸石类型和烷化剂的不同而变化。在 150-300 °C 范围内，MOR 在所有烷基化反应中都具有较高的β,β-选择性。然而，14-MR 沸石、CFI、DON 和 SFH 在异丙基化反应中的 β、β-选择性要低得多：体积大且不太稳定的 α、β- 和 α、α-二异丙基萘（α、β-DIPN：α,β-二异丙基萘（α,β-DIPN：1,3-、1,5- 和 1,7-DIPN）；α,α-二异丙基萘（1,4- 和 1,5-DIPN）主要是在低温下通过动力学控制获得的，而稳定且体积较小的 β,β-二异丙基萘则是在高温下通过热力学控制形成的。在 s 丁基化反应中，相对于 CFI 的 β,β-选择性高于 95%，相对于 DON 和 SFH 的 β,β-选择性分别从 150 ℃ 时的 50-60% 增加到 300 ℃ 时的 75%。在所有沸石上的 t-丁基化过程中，烷基化率几乎达到 100%。在 150-250 °C的范围内，在 MOR 上发生的烷基化具有很高的 2,6-选择性：异丙基化为 60%，s-丁基化为 80%，t-丁基化为 95%。CFI、DON 和 SFH 在异丙基化反应中的 2,6 选择性为 5-30%，在 s-丁基化反应中分别为 65%、55% 和 50%，而在 t-丁基化反应中则高于 80%。这些不同特征的原因是，在过渡状态下，沸石通道的立体限制将体积最小的 DAN 异构体与其他异构体区分开来：β,β-DAN 与 DAN 异构体区分开来，2,6-DAN 与 β,β-DAN 区分开来。烷基化剂的体积也提高了异构体的鉴别能力，特别是 2,6- 和 2,7-DAN 之间的鉴别能力。沸石通道和烷基化剂的体积对 β、β- 和 2,6-选择性具有协同作用。
• The Isopropylation of Naphthalene over USY Zeolite with FAU Topology. The Selectivities of the Products
  作者：Yoshihiro Sugi、Stalin Joseph、Kavitha Ramadass、Sathish Clastinrusselraj Indirathankam、Selvarajan Premkumar、Venkata D B C Dasireddy、Jae-Hun Yang、Ala'a H Al-Muhtaseb、Qing Liu、Yoshihiro Kubota、Kenichi Komura、Ajayan Vinu

  DOI：10.1246/bcsj.20200340

  日期：2021.2.15

  The isopropylation of naphthalene (NP) over USY zeolite (FAU06, SiO2/Al2O3 = 6) gave all possible eight diisopropylnaphthalene (DIPN) isomers: β,β- (2,6- and 2,7-), α,β- (1,3-, 1,6-, and 1,7-), and...

  萘 (NP) 在 USY 沸石 (FAU06, SiO2/Al2O3 = 6) 上的异丙基化得到所有可能的八种二异丙基萘 (DIPN) 异构体：β,β- (2,6- 和 2,7-), α,β- ( 1,3-、1,6- 和 1,7-) 和...
• Shape-selective synthesis of 2,6-diisopropylnaphthalene over H-mordenite catalyst
  作者：Atsuhiko Katayama、Makoto Toba、Genki Takeuchi、Fujio Mizukami、Shu-ichi Niwa、Shuichi Mitamura

  DOI：10.1039/c39910000039

  日期：——

  2,6-Diisopropylnaphthalene is selectively produced in the liquid phase alkylation of naphthalene with propene or propan-2-ol over H-mordenite catalyst.

  萘与丙烯或 2-丙醇在 H-莫代森催化剂上进行液相烷基化反应时，可选择性地生成 2,6-二异丙基萘。
• Shape-selective diisopropylation of naphthalene in H-Mordenite: Myth or reality?
  作者：Christophe Bouvier、Wim Buijs、Jorge Gascon、Freek Kapteijn、Bogdan C. Gagea、Pierre A. Jacobs、Johan A. Martens

  DOI：10.1016/j.jcat.2009.12.005

  日期：2010.3

  Selective diisopropylation of naphthalene to 2,6-diisopropylnaphthalene is a challenging goal in sustainable catalysis. Ultrastable Y and H-Mordenite zeolites are the best catalysts reported in the literature with respect to 2,6-diisopropylnaphthalene selectivity. It is generally accepted that in the case of H-Mordenite, shape-selectivity is responsible for the observed 2,6-diisopropylnaphthalene selectivity, while on Ultrastable Y-zeolite, the observed selectivity reflects the internal thermodynamic equilibrium of positional isomers. Revisiting both the experimental and the computational work in this field now leads to the conclusion that shape-selectivity of whatever kind can be ruled out in the case of H-Mordenite. H-Mordenite catalysts produce usually a kinetically controlled mixture of diisopropylnaphthalene isomers which can shift to the direction of a thermodynamical distribution at high reaction temperatures or over more active catalysts. (C) 2009 Elsevier Inc. All rights reserved.