octadec-9-enoic acid propane-1,2,3-triyl ester | 69466-36-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: octadec-9-enoic acid propane-1,2,3-triyl ester
• 英文别名: triolein；9-octadecenoic acid, 1,2,3-propanetriyl ester；2,3-Di(octadec-9-enoyloxy)propyl octadec-9-enoate
• CAS: 69466-36-0
• 化学式: C₅₇H₁₀₄O₆
• 分子量: 885.449
• InChiKey: PHYFQTYBJUILEZ-UHFFFAOYSA-N

物化性质

• 物理描述：
  Liquid
• 颜色/状态：
  Colorless to yellowish, oily liquid
• 气味：
  Odorless
• 味道：
  Tasteless
• 沸点：
  237 °C at 18 atm
• 熔点：
  -4 °C
• 溶解度：
  Insoluble in water
• 密度：
  0.915 at 15 °C/4 °C
• 蒸汽压力：
  1.15X10-9 mm Hg at 25 °C (est)
• 燃烧热：
  Enthalpy of Combustion of liquid at standard conditions = -35099.6 kJ/mol
• 表面张力：
  0.035829 N/m (est)
• 折光率：
  Index of refraction: 1.4676 at 20 °C/D; 1.4561 at 60 °C/D

计算性质

• 辛醇/水分配系数(LogP)：
  22.4
• 重原子数：
  63
• 可旋转键数：
  53
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  octadec-9-enoic acid propane-1,2,3-triyl ester 在 甲基二乙氧基硅烷 、 zinc diacetate 、 甲醇 、 potassium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以86%的产率得到油醇
  参考文献：
  名称：

  锌催化的醇对酯的化学选择性还原

  摘要：

  经济型酒精！已经开发出使用廉价的乙酸锌和硅烷将酯一般和化学选择性催化还原成醇的方法。不需要保护和脱保护步骤，操作简便和高官能团耐受性使该方法对有机合成特别有吸引力。

  DOI：

  10.1002/chem.201100800
• 作为产物：
  描述：

  1,2,3-三溴丙烷 、 sodium Oleate 生成 octadec-9-enoic acid propane-1,2,3-triyl ester
  参考文献：
  名称：

  Guth, 1903, vol. 44, p. 92

  摘要：

  DOI：

文献信息

• Amide/Iminium Zwitterionic Catalysts for (Trans)esterification: Application in Biodiesel Synthesis
  作者：Ying-Pong Lam、Xinyan Wang、Fei Tan、Wing-Hin Ng、Ying-Lung Steve Tse、Ying-Yeung Yeung

  DOI：10.1021/acscatal.9b01959

  日期：2019.9.6

  organocatalysts based on an amide anion/iminium cation charge pair has been developed. The zwitterions are easily prepared by reacting aziridines with aminopyridines. They are catalytically applicable to transesterifications and dehydrative esterifications. Mechanistic studies reveal that the amide anion and iminium cation work synergistically in activating the reaction partners, with the iminium cationic

  已经开发了一类基于酰胺阴离子/亚胺阳离子电荷对的两性离子有机催化剂。两性离子易于通过使氮丙啶与氨基吡啶反应来制备。它们催化地适用于酯交换和脱水酯化。机理研究表明，酰胺阴离子和亚胺阳离子在活化反应伙伴方面具有协同作用，亚胺阳离子部分通过非经典氢键与羰基底物相互作用。该反应可在温和条件下用于大规模合成生物柴油。
• 1,2,3-Trimethoxypropane and Glycerol Ethers as Bio-Sourced Solvents from Glycerol. Synthesis by Solvent-Free Phase-Transfer Catalysis and Utilization as an Alternative Solvent in Chemical Transformations
  作者：Marc Sutter、Wissam Dayoub、Estelle Métay、Yann Raoul、Marc Lemaire

  DOI：10.1002/cctc.201300458

  日期：2013.10

  phase‐transfer catalyst with no additional solvent. No heating was required, and the synthesis was easily performed under atmospheric pressure on a 150 g scale. For the preparation of 2, the conversion of glycerol was complete and the selectivity for the expected glycerol trimethylether was above 95 %. This product was utilized as a solvent in organic reactions such as transesterifications between glycerol

  1,2,3-三甲氧基丙烷（2），1-烷氧基-2,3-二甲氧基丙烷和1-芳氧基-2,3-二甲氧基丙烷在固相转移催化中得到了良好的收率和选择性。无机碱和铵盐作为相转移催化剂，无需其他溶剂。不需要加热，并且容易在大气压下以150g规模进行合成。准备2，甘油的转化完成，并且预期的甘油三甲醚的选择性高于95％。该产品在有机反应中用作溶剂，例如甘油和植物油之间的酯交换反应，有机金属反应（格氏和巴比尔型反应），碳-碳偶联反应（Suzuki，Sonogashira，Heck）以及在脱氢反应中的醚化反应中烷基化。溶剂显示出有趣的聚合物增溶性能。
• NOVEL METHOD FOR PREPARING POLYOLS AND PRODUCTS OBTAINED
  申请人：Cramail Henri

  公开号：US20130005937A1

  公开（公告）日：2013-01-03

  The present invention relates to a method for preparing polyols of formula (I″) R′ 1 being H or an alkyl group, R″ being especially an alkyl group, A 1 , being an alkylene radical and R 3 , are being especially a group -A 2 -O—Y′, A 2 being an alkylene radical and Y′ being especially H, said method especially comprising a step of epoxidation of a compound of formula R″ 1 being H or an alkyl group, A 1 being defined as above in formula (I″) and R 4 being especially a group -A 2 -O—Y 1 ′, A 2 being defined as above in formula (I″) and Y′ 1 being especially H, in order to obtain a compound of formula A 1 being defined as above, R′″ 1 being H or an alkyl group and R 5 being especially a group of formula -A 2 -O—Y 2 ′, A 2 being as defined above in formula (I″) and Y′ 2 being especially H,

  该发明涉及一种制备式(I″)的聚醇的方法，其中R′1为H或烷基，R″尤其为烷基，A1为亚烷基基团，R3尤其为一个-A2-O—Y′基团，A2为亚烷基基团，Y′尤其为H，所述方法尤其包括一步骤，即将式R″1为H或烷基，A1如上述在式(I″)中定义，R4尤其为一个-A2-O—Y1′基团，A2如上述在式(I″)中定义，Y′1尤其为H的化合物环氧化，以获得式A1如上述定义，R′″1为H或烷基，R5尤其为一个-A2-O—Y2′基团，A2如上述在式(I″)中定义，Y′2尤其为H的化合物。
• Hydrogenation of carboxylic acids with a homogeneous cobalt catalyst
  作者：Ties J. Korstanje、Jarl Ivar van der Vlugt、Cornelis J. Elsevier、Bas de Bruin

  DOI：10.1126/science.aaa8938

  日期：2015.10.16

  Making alcohols via hydrogen addition to C=O bonds is among the most widely applied reactions in chemistry. The transformation has also garnered renewed interest for generating commodity chemicals from biomass. Korstanje et al. now show that a cobalt compound can catalyze hydrogenation of the C=O bonds in carboxylic acids. These constitute a particularly challenging substrate class, given the propensity of many other catalysts to degrade under acidic conditions. The cobalt catalyst tolerates a versatile substrate range, and the Earth abundance of the metal bodes well for long-term utility.

  Science , this issue p. 298

  将酸转化为醇的直接途径 通过向C=O键添加氢制备醇是化学中最广泛应用的反应之一。这种转化也引起了人们对利用生物质生成商品化学品的新兴兴趣。Korstanje等人现在展示了一种钴化合物可以催化羧酸中C=O键的加氢反应。鉴于许多其他催化剂在酸性条件下容易降解，这些羧酸构成了一类特别具有挑战性的底物。钴催化剂能容忍多种底物范围，并且金属的地球丰度为其长期实用性打下了良好基础。 《科学》，本期第298页。
• Living carbocationic polymerization of a vinyl ether monomer derived from soybean oil, 2-(vinyloxy)ethyl soyate
  作者：Andrey Chernykh、Samim Alam、Anurad Jayasooriya、James Bahr、Bret J. Chisholm

  DOI：10.1039/c3gc40605a

  日期：——

  A novel vinyl ether monomer was produced from soybean oil by base-catalyzed transesterification of 2-(vinyloxy)ethanol with soybean oil. The cationic polymerization of this monomer, which is being referred to as 2-(vinyloxy)ethyl soyate (2-VOES), was investigated using a polymerization system involving a difunctional cationogen, ethylaluminum sesquichloride as the coinitiator, toluene as the solvent, and a polymerization temperature of 0 °C. With this polymerization system, the polymerization was first order with respect to monomer and molecular weight increased linearly with monomer conversion. Further, the molecular weight distribution of the polymers obtained were below 1.2. The addition of fresh monomer to a polymerization that had reach approximately 90 percent monomer conversion resulted in a further increase in molecular weight without an increase in molecular weight distribution. These results indicate that the polymerization was a living polymerization, which will enable well-defined polymer architectures, such as triblock copolymers, to be produced in the future.

  一种新颖的乙烯基醚单体通过碱催化的转酯化反应，从大豆油中得到，该反应是将2-(乙烯氧基)乙醇与大豆油进行反应。对这种单体的阳离子聚合进行了研究，该单体称为2-(乙烯氧基)乙基大豆酸酯（2-VOES），聚合系统使用了二官能团阳离子引发剂、作为共同引发剂的三氯化铝乙基、氯化铝胺和溶剂乙苯，聚合温度为0°C。在该聚合系统中，聚合反应对单体的一阶反应，并且分子量随着单体转化率线性增加。此外，所得到聚合物的分子量分布低于1.2。当向聚合反应中加入新鲜单体时，该聚合反应已达到约90%的单体转化率，结果导致分子量的进一步增加，而分子量分布没有增加。这些结果表明，聚合反应是一种活性聚合反应，这将在未来实现良好定义的聚合物结构，如三嵌段共聚物。