5,5'-(oxybis(methylene))bis(5-ethyl-1,3-dioxan-2-one) | 84056-46-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: 5,5'-(oxybis(methylene))bis(5-ethyl-1,3-dioxan-2-one)
• 英文别名: di(trimethylolpropane) carbonate；5-Ethyl-5-[(5-ethyl-2-oxo-1,3-dioxan-5-yl)methoxymethyl]-1,3-dioxan-2-one
• CAS: 84056-46-2
• 化学式: C₁₄H₂₂O₇
• 分子量: 302.324
• InChiKey: YQNMLIKYIJPPOP-UHFFFAOYSA-N

物化性质

• 沸点：
  493.7±10.0 °C(Predicted)
• 密度：
  1.153±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5,5'-(oxybis(methylene))bis(5-ethyl-1,3-dioxan-2-one) 生成 3,3’-[氧基双亚甲基]双[3-乙基]氧杂环丁烷
  参考文献：
  名称：

  研究“踢起”的氧杂环丁烷在光引发的阳离子聚合中的反应性

  摘要：

  某些烷基取代的环氧化物通过基本上完全减少或消除诱导期来促进氧杂环丁烷单体的光引发阳离子开环聚合的能力已被我们称为“起步”。在本通讯中，量化了几个模型“由脚踢启动”的氧杂环丁烷体系的光聚合速率，并将其与类似的双环脂族环氧单体3,4-环氧环己基甲基3'，4'-环氧环己烷羧酸酯（ERL）进行了比较。已经发现，“启动”系统进行光致聚合的速率至少比ERL快两倍。这些结果表明，在许多应用中，“快速启动”的氧杂环丁烷可以代替ERL，而在这些应用中，高速紫外诱导的交联光聚合反应得以进行。©2014 Wiley Periodicals，Inc. J. Polym。科学，A部分：Polym。化学2015年，53，586-593

  DOI：

  10.1002/pola.27479
• 作为产物：
  描述：

  、 氯甲酸乙酯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以74%的产率得到5,5'-(oxybis(methylene))bis(5-ethyl-1,3-dioxan-2-one)
  参考文献：
  名称：

  Biodegradable cross-linked poly(trimethylene carbonate) networks for implant applications: Synthesis and properties

  摘要：

  In order to avoid the deformation of poly(trimethylene carbonate) (PTMC) in vivo applications, bis(cyclic carbonate) was synthesized and used as cross-linker to prepare PTMC based biodegradable networks via ring-opening polymerization of TMC and/or CL with stannous octanoate as catalyst. The effect of the cross-linking on the resulted networks was studied. The results showed that the crosslinker had high reactivity and efficiency to form stable polymeric networks with high gel percentage, high decomposition temperature and good mechanical properties. These obtained networks were amorphous and elastic, and the glass transition temperatures were below physiological temperature (37 degrees C), which were expected to be rubbery for in vivo applications. The properties of the networks could be predictably controlled and tailed by varying the polymer composition and cross-linker amount in feed. The crosslinked PTMC based networks showed a potential biomedical application of loading drugs for implanted devices. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2013.03.059

文献信息

• Chlorine-Free Synthesis of Organic Alkyl Carbonates and Five- and Six-Membered Cyclic Carbonates
  作者：Sang-Hyun Pyo、Rajni Hatti-Kaul

  DOI：10.1002/adsc.201500654

  日期：2016.3.3

  report presents a new, one‐pot, facile, selective and green method for methoxycarbonylation of alcohols and synthesis of five‐ and six‐membered cyclic carbonates from corresponding alcohols with dimethyl carbonate (DMC) in the presence of molecular sieves without any additional solvent and catalyst. Syntheses of bifunctional structures comprising a six‐membered cyclic carbonate with allyl ether and methacrylate

  该报告提出了一种新的，简单易用，选择性，绿色的醇甲氧基羰基化方法，以及在没有任何其他溶剂的情况下，在分子筛存在下由相应的醇与碳酸二甲酯（DMC）合成五元和六元环状碳酸酯的方法。和催化剂。还实现了分别包含六元环状碳酸酯和烯丙基醚和甲基丙烯酸酯基团的六官能环状碳酸酯在不同聚合模式下的合成，并且在扩大工艺规模时显示出可重复性。
• [EN] METHOD FOR PRODUCING CYCLIC CARBONATES<br/>[FR] PROCÉDÉ POUR PRODUIRE DES CARBONATES CYCLIQUES
  申请人：HATTI-KAUL RAJNI

  公开号：WO2012158107A1

  公开（公告）日：2012-11-22

  Linear or cyclic carbonates as potential monomers for isocyanate-free polyurethanes and polycarbonates were prepared from polyols and dialkylcarbonatesor diphenyl carbonates. This invention was developed to produce linear or cyclic carbonates with or without using catalysts. Polyol compounds were reacted with carbonates such as dimethylcarbonate and diethylcarbonate to produce thecorresponding linear and/or cyclic carbonate.

  线性或环状碳酸酯作为异氰酸酯自由聚氨酯和聚碳酸酯的潜在单体，是由多元醇和二烷基碳酸酯或二苯碳酸酯制备的。这项发明旨在生产带有或不带有催化剂的线性或环状碳酸酯。多元醇化合物与碳酸酯（如二甲基碳酸酯和二乙基碳酸酯）反应，以产生相应的线性和/或环状碳酸酯。
• Reworkable Polyhydroxyurethane Films with Reversible Acetal Networks Obtained from Multifunctional Six-Membered Cyclic Carbonates
  作者：Hiroyuki Matsukizono、Takeshi Endo

  DOI：10.1021/jacs.7b11824

  日期：2018.1.24

  Multifunctional 6-membered cyclic carbonates (6-CCs) comprising acetal structures have been synthesized via phosgene-free routes and utilized for the fabrication of reworkable networked poly(acetal-hydroxyurethane) (PAHU) films. Dibenzoyl-protected di(trimethylolpropane) (DTMP) reacts with multifunctional aldehydes derived from nonexpensive alcohols to afford protected multifunctional DTMPs. After

  包含缩醛结构的多功能 6 元环状碳酸酯 (6-CC) 已通过无光气路线合成，并用于制造可再加工的网络聚（缩醛-羟基氨基甲酸酯）（PAHU）薄膜。二苯甲酰基保护的二(三羟甲基丙烷) (DTMP) 与衍生自廉价醇的多功能醛反应，得到受保护的多功能 DTMP。去保护后，多功能 DTMP 可以与碳酸二苯酯反应，有效地形成多功能 6-CC。6-CCs 和二胺的加聚在 DMF 中有效地进行，得到具有良好透明度和柔韧性的网络 PAHU 薄膜。这些薄膜具有基于酸催化的缩醛键可逆性的可再加工性。特别是，
• [EN] DYNAMIC POLYMER WITH HYBRID CROSS-LINKED NETWORK AND APPLICATION THEREOF<br/>[FR] POLYMÈRE DYNAMIQUE À RÉSEAU RÉTICULÉ HYBRIDE, ET APPLICATION ASSOCIÉE<br/>[ZH] 具有杂化交联网络的动态聚合物及其应用
  申请人：WENG QIUMEI

  公开号：WO2018028365A1

  公开（公告）日：2018-02-15

  具有杂化交联网络结构的动态聚合物，其中包含共价键交联和超分子氢键交联；其中，共价键交联由结合性可交换共价键实现，超分子氢键交联由聚合物链骨架的侧基和/或侧链上的氢键基团以及可选的链骨架上的氢键基团实现。该聚合物融合了超分子动态特性和类玻璃的动态共价特性；超分子氢键赋予材料刺激响应性、耗能性和自修复性；结合性可交换共价键则一方面既赋予共价交联聚合物的结构稳定性和机械强度，又由于其动态可逆性，使得聚合物具有自修复性、可回收性、可重复加工性等。所述具有杂化交联网络结构的动态聚合物可广泛应用于减震缓冲材料、抗冲击防护材料、自修复材料、韧性材料、密封件等。
• Mechanically Activated, Catalyst-Free Polyhydroxyurethane Vitrimers
  作者：David J. Fortman、Jacob P. Brutman、Christopher J. Cramer、Marc A. Hillmyer、William R. Dichtel

  DOI：10.1021/jacs.5b08084

  日期：2015.11.11

  Vitrimers are polymer networks whose cross-links undergo associative exchange processes at elevated temperature, usually in the presence of an embedded catalyst. This design feature enables the reshaping of materials with mechanical properties similar to thermoset resins. Here we report a new class of vitrimers consisting of polyhydroxyurethanes (PHUs) derived from six-membered cyclic carbonates and amines. PHU networks relax stress and may be reprocessed at elevated temperature and pressure in the absence of an external catalyst. The as-synthesized networks exhibit tensile properties comparable to those of leading thermosets and recover ca. 75% of their as-synthesized values following reprocessing. Stress relaxation occurs through an associative process involving nudeophilic addition of free hydroxyl groups to the carbamate linkages and exhibits an Arrhenius activation energy of 111 +/- 10 kJ/mol, which is lower than that observed for molecular model compounds (148 +/- 7 kJ/mol). These findings suggest that transcarbamoylation is activated by mechanical stress, which we attribute, on the basis of DFT calculations, to the twisting of N lone pairs out of conjugation with the carbonyl pi orbitals. PHU vitrimers are a promising new class of repairable networks because of their outstanding mechanical properties, avoidance of toxic isocyanate monomers, and catalyst-free repair processes.