1,3-二(异丙基)萘 | 57122-16-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1,3-二(异丙基)萘
• 英文名称: 1,3-di-i-propylnaphthalene
• 英文别名: 1,3-diisopropylnaphthalene；1,3-DIPN；1,3-bis(isopropyl)naphthalene；1,3-di(propan-2-yl)naphthalene
• CAS: 57122-16-4
• 化学式: C₁₆H₂₀
• 分子量: 212.335
• InChiKey: JDBFIFNXALGSOF-UHFFFAOYSA-N

物化性质

• 沸点：
  298.8±10.0 °C(Predicted)
• 密度：
  0.949±0.06 g/cm3(Predicted)
• 保留指数：
  1662

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 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

安全信息

• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  1,3-二(异丙基)萘 生成 1,3-naphthalenedicarboxylic acid
  参考文献：
  名称：

  KAGEHYAMA, KEHNDZI;YAMADA, TEHRUAKI

  摘要：

  DOI：
• 作为产物：
  描述：

  2,6-二异丙基萘 在 H-USY (CBV₇₆₀) zeolite 作用下， 以 环己烷 为溶剂， 反应 24.0h， 生成 2-异丙基萘 、 异丙基萘 、 2,7-双全酮立构乙酸乙酯 、 1,3-二(异丙基)萘
  参考文献：
  名称：

  Shape-selective diisopropylation of naphthalene in H-Mordenite: Myth or reality?

  摘要：

  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.

  DOI：

  10.1016/j.jcat.2009.12.005

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。
• Zeolite Pore Entrance Effect on Shape Selectivity in Naphthalene Isopropylation
  作者：R Brzozowski

  DOI：10.1006/jcat.2002.3702

  日期：2002.9.10

  obtained over zeolites than over amorphous aluminosilicate catalysts. The explanation of such results was proposed to be a specific shape-selectivity effect of alkylation reaction occurring in the entrances to the pores of zeolite. This type of shape selectivity can be very significant and conceal other shape-selectivity effects such as β-selectivity of reactions occurring inside the pores. Results available

  在各种大孔沸石以及无定形硅铝酸盐催化剂上研究了丙烯与丙烯的萘烷基化。在不同温度下比较了异丙基萘和二异丙基萘的异构分布。令人惊讶地，在沸石上获得的产物比在无定形铝硅酸盐催化剂上观察到的产物中观察到更高的单烷基化α-选择性和更高的二异丙基化中的大体积异构体浓度。提出这种结果的解释是在沸石孔的入口处发生的烷基化反应的特定形状选择性作用。这种类型的形状选择性可能非常显着，并掩盖了其他形状选择性效果，例如在孔内发生的反应的β选择性。从文献中得出的结果，
• Disproportionation of isopropylnaphthalene on zeolite catalysts
  作者：R Brzozowski

  DOI：10.1016/s0021-9517(03)00237-9

  日期：2003.11.15

  Disproportionation of isopropylnaphthalene (IPN) was tested over H-mordenite, HY, H-beta zeolites and over amorphous aluminosilicate in the range of 150–300 °C. High β,β-selectivity in diisopropylnaphthalene (DIPN) product obtained over zeolites was observed. However, the 2,6-DIPN/2,7-DIPN mole ratio was dependent on the pore structure of the applied zeolite and on the temperature. Over H-mordenites

  在150-300°C的温度范围内，在H-丝光沸石，HY，H-β沸石和无定形硅铝酸盐上测试了异丙基萘（IPN）的歧化作用。高β，β观察到在沸石上获得的二异丙基萘（DIPN）产物的选择性。然而，2，6-DIPN / 2，7-DIPN的摩尔比取决于所施加的沸石的孔结构和温度。最优选的异构体是H-丝光沸石，而不是H-丝光沸石，而HY和H-β沸石则更倾向于使用2,7-DIPN。在DIPN产物中占主导地位的异构体中的这种歧化可以通过歧化的双分子机理来解释。由于沸石的孔结构，导致2，7-DIPN（HY和H-β）或更线性的弯曲过渡态络合物是优选的，从而导致2，6-DIPN（H-丝光沸石）。在高温下，单分子歧化机理（脱烷基重烷基化）占主导地位，并且（与副反应同时）掩盖了形状选择性效应。结果是2,6-DIPN / 2，
• 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...