4,4'-di-s-butylbiphenyl | 16236-41-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4,4'-di-s-butylbiphenyl
• 英文别名: 4,4'-Di-sec-butyl-biphenyl；4,4'-Di-sec.-butyl-diphenyl；4,4'-Di-sek.-butylbiphenyl；1,1'-Biphenyl, 4,4'-bis(1-methylpropyl)-；1-butan-2-yl-4-(4-butan-2-ylphenyl)benzene
• CAS: 16236-41-2
• 化学式: C₂₀H₂₆
• 分子量: 266.426
• InChiKey: GBWGKFFUMJXHST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  alkaline earth salt of/the/ methylsulfuric acid 在 铜 作用下， 生成 4,4'-di-s-butylbiphenyl
  参考文献：
  名称：

  Boedtker, Bulletin de la Societe Chimique de France, 1929, vol. <4> 45, p. 648

  摘要：

  DOI：

文献信息

• The Alkylation of Biphenyl over Fourteen-Membered Ring Zeolites. The Influence of Zeolite Structure and Alkylating Agent on the Selectivity for 4,4′-Dialkylbiphenyl
  作者：Yoshihiro Sugi、Hiroyoshi Maekawa、Shafeek Abdul Rashid Mulla、Akira Ito、Chikayo Naitoh、Kazunori Nakagawa、Kenichi Komura、Yoshihiro Kubota、Jong-Ho Kim、Gon Seo

  DOI：10.1246/bcsj.80.1418

  日期：——

  Alkylation, i.e. isopropylation, s-butylation, and t-butylation, of biphenyl (BP) was examined over fourteen-membered ring (14-MR) zeolites, CIT-5, UTD-1, and SSZ-53, in order to elucidate the relationships between structure of zeolites and bulkiness of alkylating agents on the shape-selective catalysis. CIT-5 zeolite (CFI) yielded 4,4′-diisopropylbiphenyl (4,4′-DIPB) in the level of 50–60% in the isopropylation in the range of 150–300 °C. 2,2′-, 2,3′-, and 2,4′-DIPB (2,x′-DIPB) isomers were obtained as the predominant DIPB isomers at lower temperatures, and the formation of 3,4′- and 3,3′-DIPB isomers increased with an increase in the temperature. However, the selectivities were in the level of 10–15% for UTD-1 (DON) and SSZ-53 (SFH) zeolites in the range of 150–350 °C. The s-butylation with 1-butene gave results similar to the isopropylation, although the selectivities for 4,4′-di-s-butylbiphenyl (4,4′-DSBB) were higher than those for 4,4′-DIPB at 250 °C: 80–85% for CFI, 40–50% for DON, and 30–40% for SFH. High selectivity for 4,4′-di-t-butylbiphenyl (4,4′-DTBB) was observed in the t-butylation at 250 °C: 95% for CFI, 90% for DON, and 80% for SFH. These differences are due to the spatial difference in their channels, and also due to bulkiness of alkylating agents, propene, 1-butene, and 2-methylpropene. The selectivity for 4,4′-dialkylbiphenyl (4,4′-DABP) was governed by the exclusion of the bulky DABP isomers at the transition state by steric restriction in the zeolite channels.

  研究了联苯（BP）在十四元环（14-MR）沸石（CIT-5、UTD-1 和 SSZ-53）上的烷基化反应，即异丙基化、正丁基化和叔丁基化，以阐明沸石结构和烷化剂体积对形状选择性催化的关系。CIT-5 沸石（CFI）在 150-300 ℃范围内进行异丙基化时，4,4′-二异丙基联苯（4,4′-DIPB）的产率为 50-60%。在较低温度下，2,2′-、2,3′- 和 2,4′-DIPB （2,x′-DIPB）异构体是主要的 DIPB 异构体，而随着温度的升高，3,4′- 和 3,3′-DIPB 异构体的生成量增加。不过，在 150-350 °C 的范围内，UTD-1（DON）和 SSZ-53（SFH）沸石的选择性在 10-15% 之间。用 1-丁烯进行 s-丁基化反应的结果与异丙基化反应相似，但在 250 ℃ 时，4,4′-二-s-丁基联苯（4,4′-DSBB）的选择性高于 4,4′-DIPB：CFI为80-85%，DON为40-50%，SFH为30-40%。在 250 ℃ 的 t 丁基化反应中，4,4′-二叔丁基联苯（4,4′-DTBB）具有较高的选择性：CFI为 95%，DON 为 90%，SFH 为 80%。这些差异是由于它们通道的空间差异以及烷基化剂丙烯、1-丁烯和 2-甲基丙烯的体积差异造成的。对 4,4′-二烷基联苯（4,4′-DABP）的选择性取决于沸石通道中的立体限制对过渡态笨重的 DABP 异构体的排斥。
• Shape-Selective Alkylation of Biphenyl over H-[Al]-SSZ-24 Zeolites with AFI Topology
  作者：Akira Ito、Hiroyoshi Maekawa、Hiroaki Kawagoe、Kenichi Komura、Yoshihiro Kubota、Yoshihiro Sugi

  DOI：10.1246/bcsj.80.215

  日期：2007.1

  H-[Al]-SSZ-24 zeolites with AFI topology were synthesized through the alumination of [B]-SSZ-24 zeolites, and applied for the alkylation of biphenyl (BP). H-[Al]-SSZ-24 zeolites have high activity for the isopropylation. The shape-selective formation of 4,4′-diisopropylbiphenyl (4,4′-DIPB) occurred at moderate temperature; however, the selectivity for 4,4′-DIPB decreased with an increase in the reaction temperature. Isomerization of 4,4′-DIPB occurred at higher temperatures over internal and external acid sites when there are enough acid sites inside the channels. The channels can discriminate 4,4′-DIPB from the other DIPB isomers in their transition states; however, they can not prevent the isomerization of 4,4′-DIPB at higher temperatures. The selectivity for the least bulky 4,4′-dialkylbiphenyl increased with the bulkiness of alkylating agents in the order: isopropylation < s-butylation < t-butylation. These results strongly support the shape-selective formation of the least bulky products inside the channels of H-[Al]-SSZ-24 zeolites.

  通过矾化[B]-SSZ-24沸石合成了具有 AFI 拓扑结构的 H-[Al]-SSZ-24 沸石，并将其应用于联苯（BP）的烷基化反应。H-[Al]-SSZ-24沸石具有较高的异丙基化活性。在中等温度下，4,4′-二异丙基联苯（4,4′-DIPB）的形成具有形状选择性；然而，4,4′-DIPB 的选择性随着反应温度的升高而降低。当通道内有足够的酸性位点时，4,4′-DIPB 在较高温度下通过内部和外部酸性位点发生异构化。通道可以区分处于过渡态的 4,4′-DIPB 和其他 DIPB 异构体，但不能阻止 4,4′-DIPB 在较高温度下发生异构化。对体积最小的 4,4′-二烷基联苯的选择性随着烷基化剂体积的增加而增加，其顺序为：异丙基化 < s-丁基化 < t-丁基化。这些结果有力地支持了在 H-[Al]-SSZ-24 沸石通道内形成最不笨重产物的形状选择性。
• Boedtker, Bulletin de la Societe Chimique de France, 1929, vol. <4> 45, p. 648
  作者：Boedtker

  DOI：——

  日期：——