(10E)-10-十八碳烯酸 | 5684-82-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: (10E)-10-十八碳烯酸
• 英文名称: trans-10-octadecenoic acid
• 英文别名: 10-octacosenoic acid；trans-octadec-10-enoic acid；10(E)-octadecenoic acid；gadoleic acid；isooleic acid；octadec-10t-enoic acid；(E)-octadec-10-enoic acid
• CAS: 5684-82-2
• 化学式: C₁₈H₃₄O₂
• 分子量: 282.467
• InChiKey: QXJSBBXBKPUZAA-CMDGGOBGSA-N

物化性质

• 熔点：
  51 - 53°C
• 溶解度：
  氯仿（微溶）、己烷（微溶）
• 物理描述：
  Liquid; OtherSolid; OtherSolid, Liquid

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  20
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (10E)-10-十八碳烯酸 在 硫酸 作用下， 生成 4-羟基十八烷酸
  参考文献：
  名称：

  Shukow; Schestakow, Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1908, vol. 40, p. 832

  摘要：

  DOI：
• 作为产物：
  描述：

  (Z,Z)-9,12-十八烷二烯酸二聚物 在 镍 作用下， 生成 (10E)-10-十八碳烯酸
  参考文献：
  名称：

  Displacement of the double bonds during hydrogenation of unsaturated fatty acid methyl esters

  摘要：

  摘要 研究了几种不饱和脂肪酸甲酯在 180°C 下使用镍-基瑟古尔催化剂进行氢化时的双键位移。通过分配色谱法对二羧酸（反应产物在醋酸溶液中用 KMnO4 氧化得到）进行分析，可以对所形成的位置异构体进行可靠的半定量测定。双键发生了双向迁移，但在所有情况下，与酯基相反方向的迁移都非常明显。起始原料中双键的位置和构型（顺式或反式）在这方面显然并不重要。因此，众所周知，脂肪酸酯氢化产生的产物要复杂得多。这一点对于氢化脂肪油在食品工业中的应用尤为重要。

  DOI：

  10.1007/bf02634998

文献信息

• FUNCTIONALIZED MONOMERS AND POLYMERS
  申请人：DiBiase Stephen Augustine

  公开号：US20120245063A1

  公开（公告）日：2012-09-27

  This invention relates to a composition, comprising: an unsaturated functionalized monomer of from about 5 to about 30 carbon atoms, which is: (a) polymerized to form a functionalized polymer; (b) copolymerized with a comonomer to form a functionalized copolymer; or (c) reacted with an enophilic reagent to form a polyfunctionalized monomer. The polyfunctionalized monomer may be polymerized to form a polyfunctionalized polymer which may be further reacted with one or more additional reagents. The invention relates to lubricants, functional fluids, fuels, dispersants, detergents and polymeric resins.

  这项发明涉及一种组合物，包括：一个由约5至约30个碳原子的不饱和官能化单体组成，该单体：(a)聚合形成官能化聚合物；(b)与共聚单体共聚形成官能化共聚物；或(c)与亲亚烯试剂反应形成多官能单体。多官能单体可以聚合形成多官能聚合物，该聚合物可以进一步与一个或多个额外试剂反应。该发明涉及润滑剂、功能流体、燃料、分散剂、清洁剂和聚合树脂。
• NickelButadiene Catalytic System for the Cross-Coupling of Bromoalkanoic Acids with Alkyl Grignard Reagents: A Practical and Versatile Method for Preparing Fatty Acids
  作者：Takanori Iwasaki、Kiyokazu Higashikawa、Vutukuri P. Reddy、Willbe W. S. Ho、Yukari Fujimoto、Koichi Fukase、Jun Terao、Hitoshi Kuniyasu、Nobuaki Kambe

  DOI：10.1002/chem.201204222

  日期：2013.2.25

  The knights who say Ni: A practical and convenient synthetic route to fatty acids involves the Ni‐catalyzed alkylalkyl cross‐coupling of bromoalkanoic acids and alkyl Grignard reagents in the presence of 1,3‐butadiene as an additive (see scheme).

  说Ni的骑士们：一种实用且方便的合成脂肪酸途径涉及在1,3-丁二烯作为添加剂的情况下，Ni催化的溴链烷酸与烷基Grignard试剂的烷基烷基交叉偶联（参见方案）。
• Esters with antimicrobial, bioresistant and fungal resistant properties
  申请人：Daly Thomas

  公开号：US20050287094A1

  公开（公告）日：2005-12-29

  A bromine/nitro moiety linked into the backbone of an ester or other compound over a wide range of occurrence rates provides antimicrobial, bio-resistant and fungal resistant properties for metal working fluids (MWF)s, coatings, plastics, and medical devices. The moiety can be have the bromo and nitro groups linked to the same or different carbon atoms. The present invention also relates to urethanes, urea, amides, imides, carbonates, ethers, siloxanes, and many other types of linkages essential to MWF bases.

  溴/硝基团连接到酯类或其他化合物的骨架中，在广泛的出现率范围内，为金属加工液（MWF）、涂料、塑料和医疗器械提供抗菌、抗生物降解和抗真菌性能。该基团可将溴基和硝基连接到相同或不同的碳原子上。本发明还涉及对MWF基础至关重要的脲酮、脲、酰胺、亚酰胺、碳酸酯、醚、硅氧烷等许多其他类型的连接。
• Catalytic hydrogenation of linoleic acid on nickel, copper, and palladium
  作者：Yoshie Kitayama、Masahiro Muraoka、Megumi Takahashi、Tatsuya Kodama、Hirofumi Itoh、Eriko Takahashi、Mutsuo Okamura

  DOI：10.1007/bf02525461

  日期：1996.10

  The catalytic activity and selectivity for hydrogenation of linoleic acid were studied on Ni, Cu, and Pd catalysts. A detailed analysis of the reaction product was performed by a gas‐liquid chromatograph, equipped with a capillary column, and Fourier transform‐infrared spectroscopy. Geometrical and positional isomerization of linoleic acid occurred during hydrogenation, and many kinds of linoleic acid isomers (trans‐9,trans‐12; trans‐8,cis‐12 orcis‐9,trans‐13; cis‐9,trans‐12; trans‐9,cis‐12 andcis‐9,cis‐12 18∶2) were contained in the reaction products. The monoenoic acids in the partial hydrogenation products contained eight kinds of isomers and showed different isomer distributions on Ni, Cu, and Pd catalysts, respectively. The positional isomers of monoenoic acid were produced by double‐bond migration during hydrogenation. On Ni and Pd catalysts, the yield ofcis‐12 andtrans‐12 monoenoic acids was larger than that ofcis‐9 andtrans‐9 monoenoic acids. On the contrary, the yield ofcis‐9 andtrans‐9 monoenoic acids was larger than that ofcis‐12 andtrans‐12 monoenoic acids on Cu catalyst. From these results, it is concluded that the double bond closer to the methyl group (Δ12) and that to the carboxyl group (Δ9) show different reactivity for hydrogenation on Ni, Cu, and Pd catalysts. Monoenoic acid formation was more selective on Cu catalyst than on Ni and Pd catalysts.

  摘要 研究了 Ni、Cu 和 Pd 催化剂对亚油酸加氢反应的催化活性和选择性。利用配备毛细管色谱柱的气液相色谱仪和傅立叶变换红外光谱对反应产物进行了详细分析。氢化过程中亚油酸发生了几何和位置异构化，反应产物中含有多种亚油酸异构体（反式-9,反式-12；反式-8,顺式-12 或顺式-9,反式-13；顺式-9,反式-12；反式-9,顺式-12 和顺式-9,顺式-12 18∶2）。部分加氢产物中的单烯酸含有八种异构体，在镍、铜和钯催化剂上分别呈现出不同的异构体分布。单烯酸的位置异构体是在氢化过程中通过双键迁移产生的。在 Ni 和 Pd 催化剂上，顺式-12 和反式-12 单烯酸的产率大于顺式-9 和反式-9 单烯酸。相反，在铜催化剂上，顺-9 和反-9 单烯酸的产率大于顺-12 和反-12 单烯酸的产率。从这些结果可以得出结论，在镍、铜和钯催化剂上，与甲基（Δ12）较接近的双键和与羧基（Δ9）较接近的双键在氢化过程中表现出不同的反应活性。在铜催化剂上形成单烯酸比在镍和钯催化剂上更具选择性。
• Isomerization during hydrogenation. III. Linoleic acid
  作者：Robert R. Allen、Arthur A. Kiess

  DOI：10.1007/bf02665110

  日期：1956.8

  The isomerization that takes place during the catalytic hydrogenation of linoleic acid and methyl linoleate producescis andtrans 9, 10, 11, and 12 monoenes. The double bond at the 12 position appears to hydrogenate slightly faster than that in the 9 position. More octadecenoic acids with double bonds at the 10 or 11 positions are produced during a selective (high temperature, low pressure) hydrogenation than during a non‐selective process.

  Although the degree of selectivity of the hydrogenation is determined by the amount of isomerization of the original pentadiene system to a conjugated diene, only part of the methylene‐interrupted diene goes through this type of isomerization even during a highly selective hydrogenation.

  The half hydrogenation‐dehydrogenation reaction mechanism is applied to explain the simultaneous positional and geometrical isomerizations.

  摘要亚油酸和亚油酸甲酯在催化氢化过程中发生异构化，生成顺式和反式 9、10、11 和 12 单烯。位于 12 位的双键似乎比位于 9 位的双键氢化速度稍快。在选择性（高温、低压）氢化过程中，10 或 11 位双键的十八烯酸的生成量要多于非选择性过程。虽然氢化的选择性程度取决于原始戊二烯体系向共轭二烯异构化的程度，但即使在高选择性氢化过程中，也只有部分亚甲基间断二烯经过这种异构化。