Methyl 10-chloro-9-methoxy-octadecanoate | 872803-71-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Methyl 10-chloro-9-methoxy-octadecanoate
• 英文别名: methyl 10-chloro-9-methoxyoctadecanoate
• CAS: 872803-71-9
• 化学式: C₂₀H₃₉ClO₃
• 分子量: 362.981
• InChiKey: GSYSBKXYHQLVAW-UHFFFAOYSA-N

物化性质

• 沸点：
  424.3±25.0 °C(Predicted)
• 密度：
  0.953±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  24
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  甲醇 、 油酸甲酯 在 calcium hypochlorite 、 硫酸 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 10-氯-9-羟基十八烷酸甲酯 、 9-氯-10-羟基十八烷酸甲酯 、 Methyl 10-chloro-9-methoxy-octadecanoate 、 Methyl 9-chloro-10-methoxy-octadecanoate
  参考文献：
  名称：

  氯代烷氧基和油酸甲酯的烷氧基衍生物的合成

  摘要：

  AbstractVegetable oil based lubricants typically have improved lubricity and biodegradability over their mineral oil based counterparts. However, vegetable oil lubricants often fail to meet the performance standards of mineral based oils with respect to cold temperature and resistance to oxidation. Olefins are an oxidatively weak point for vegetable based compounds. Removal of the olefin in a vegetable based lubricant through functionalization may increase resistance to oxidation. If the added functionality also causes branching of the alkyl chain, cold temperature properties may be improved. Any chemical modifications considered must be scalable and cost‐effective to be useful in a commercial application. In this study, methyl oleate was functionalized into a chloro alkoxy derivative. Sodium hypochlorite (household bleach) and calcium hypochlorite were both used to generate hypochlorous acid in situ. Hypochlorous acid and a series of alcohols (methanol, ethanol, and butanol) were reacted with methyl oleate to make chloro alkoxy compounds in 29.8–77.9 % yields. In an effort to make a branched saturated ether we removed the chlorine moiety of the chloro alkoxy compounds. Dehalogenation was achieved under basic conditions over a Pd/C catalyst in 2‐propanol. Reaction times increased substantially as the size of the adjacent alkoxy group increased. The reaction rate could be improved by heating the reactions above 100 °C in a pressure reactor. Increased reaction temperature also resulted in an increase in ketone side products from the competing elimination reactions. Saturated ether yields were 4.1–43.2 %.

  DOI：

  10.1007/s11746-013-2224-1

文献信息

• Synthesis of Chloro Alkoxy and Alkoxy Derivatives of Methyl Oleate
  作者：Benjamin A. Lowery、Brad Andersh、Terry A. Isbell

  DOI：10.1007/s11746-013-2224-1

  日期：2013.6

  AbstractVegetable oil based lubricants typically have improved lubricity and biodegradability over their mineral oil based counterparts. However, vegetable oil lubricants often fail to meet the performance standards of mineral based oils with respect to cold temperature and resistance to oxidation. Olefins are an oxidatively weak point for vegetable based compounds. Removal of the olefin in a vegetable based lubricant through functionalization may increase resistance to oxidation. If the added functionality also causes branching of the alkyl chain, cold temperature properties may be improved. Any chemical modifications considered must be scalable and cost‐effective to be useful in a commercial application. In this study, methyl oleate was functionalized into a chloro alkoxy derivative. Sodium hypochlorite (household bleach) and calcium hypochlorite were both used to generate hypochlorous acid in situ. Hypochlorous acid and a series of alcohols (methanol, ethanol, and butanol) were reacted with methyl oleate to make chloro alkoxy compounds in 29.8–77.9 % yields. In an effort to make a branched saturated ether we removed the chlorine moiety of the chloro alkoxy compounds. Dehalogenation was achieved under basic conditions over a Pd/C catalyst in 2‐propanol. Reaction times increased substantially as the size of the adjacent alkoxy group increased. The reaction rate could be improved by heating the reactions above 100 °C in a pressure reactor. Increased reaction temperature also resulted in an increase in ketone side products from the competing elimination reactions. Saturated ether yields were 4.1–43.2 %.