methyl formylstearate | 52414-68-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl formylstearate
• 英文别名: Methyl-9-formyl-stearat；Methyl 9-formylstearate；methyl 9-formyloctadecanoate
• CAS: 52414-68-3
• 化学式: C₂₀H₃₈O₃
• 分子量: 326.52
• InChiKey: GOLWMOKZQHJLDP-UHFFFAOYSA-N

物化性质

• 沸点：
  407.5±28.0 °C(Predicted)
• 密度：
  0.907±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  23
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  油酸甲酯 、 一氧化碳 在 (acetylacetonato)dicarbonylrhodium (l) 、 tris[(R)-2’-(benzyloxy)-1,1’-binaphthyl-2-yl]phosphite 、 氢气 作用下， 以 甲苯 为溶剂， 60.0 ℃ 、2.5 MPa 条件下， 反应 24.0h， 生成 methyl formylstearate 、 methyl formylstearate
  参考文献：
  名称：

  用于位阻烷基烯烃加氢甲酰化的高效 Rh(I)/三联萘单亚磷酸酯催化剂

  摘要：

  摘要 使用在 2'-联萘位置（OMe、OBn、OCHPh 2 和 OAdamantyl）含有不同醚取代基的铑 (I)/三联萘单亚磷酸酯催化剂有效地进行了高度取代的烷基烯烃的加氢甲酰化。对非 3-烯酸甲酯的加氢甲酰化进行的系统动力学研究表明，配体的 OR 基团对铑催化剂的性能有显着影响，Rh(I)/tris[2'-benzyloxy-1, 1'-联萘-2-基]亚磷酸酯催化体系 (Rh(I)/ L2 -OBn) 对醛类化合物具有最高的化学选择性，对 C-5 甲酰基产物具有最高的区域选择性。该催化体系进一步应用于天然产物的负载CC双键的加氢甲酰化，即油酸甲酯、(-)-异胡薄荷醇苄基醚和17β-acetoxyandrost-4-ene，

  DOI：

  10.1016/j.molcata.2016.02.016

文献信息

• A bulky phosphite-modified rhodium catalyst for the hydroformylation of unsaturated fatty acid esters
  作者：Koen F. Muilwijk、Paul C. J. Kamer、Piet W. N. M. van Leeuwen

  DOI：10.1007/s11746-997-0127-8

  日期：1997.3

  AbstractA series of hydroformylation experiments was performed with a high‐grade and a technical‐grade‐derived methyl oleate (MO) and a rhodium catalyst modified by the bulky tris(2‐tert‐butyl‐4‐methylphenyl)phosphite. In the hydroformylation of pure methyl oleate, relatively high turnover numbers were obtained (400–500 mol/mol/h) under mild conditions (molar ratio MO/Rh=910, 80–100°C and 20 bar; CO/H2=1:1, solvent toluene), leading to about 95% conversion in 3 h. Fast isomerization occurs under these conditions to produce the trans oleate. Trans oleate reacts more slowly than cis oleate. At temperatures below 50°C, isomerization does not occur. The use of technical‐grade methyl oleate, containing 14% 9,12 diene, methyl linoleate (ML), results in lower reaction rates because dienes form stable π‐allylic intermediates, which slowly undergo hydroformylation. More severe conditions were applied to obtain higher rates. The rate varied from 50 to 400 mol/mol/h, depending on conditions (molar ratio MO/Rh=910, T=50–120°C, P = 50–80 bar; CO/H2=1:1–1:6, solvent, toluene). Several isomers of ML were formed during the reaction. Subsequent hydroformylation of these isomers results in a complicated mixture of products. The product mixture consists predominantly of methyl formylstearate, methyl formyloleate, methyl diformylstearate, and some yet unidentified side products. A comparison of the classic triphenylphosphine‐modified catalyst and the bulky phosphite‐modified catalyst has shown that the latter is several times more active.
• SEPARATION OF NATURAL OIL-DERIVED ALDEHYDES OR HYDROXY METHYL ESTERS USING PROCESS CHROMATOGRAPHY
  申请人：Feist Shawn D.

  公开号：US20100331559A1

  公开（公告）日：2010-12-30

  Use process chromatographic apparatus and process (for example, SMB chromatographic separation) to effect removal of at least a portion of components that contain neither a hydroxy moiety nor an aldehyde moiety from a feedstream that includes such components as well as components that contain one or more of a hydroxy moiety and an aldehyde moiety.
• [EN] SEPARATION OF NATURAL OIL-DERIVED ALDEHYDES OR HYDROXY METHYL ESTERS USING PROCESS CHROMATOGRAPHY<br/>[FR] SÉPARATION D'ALDÉHYDES NATURELS DÉRIVÉS DU PÉTROLE OU D'HYDROXYMÉTHYLESTERS À L'AIDE D'UNE CHROMATOGRAPHIE INDUSTRIELLE
  申请人：DOW GLOBAL TECHNOLOGIES INC

  公开号：WO2009105351A1

  公开（公告）日：2009-08-27

  Use process chromatographic apparatus and process (for example, SMB chromatographic separation) to effect removal of at least a portion of components that contain neither a hydroxy moiety nor an aldehyde moiety from a feedstream that includes such components as well as components that contain one or more of a hydroxy moiety and an aldehyde moiety.
• Highly efficient Rh(I)/tris-binaphthyl monophosphite catalysts for hydroformylation of sterically hindered alkyl olefins
  作者：Gonçalo N. Costa、Rui M.B. Carrilho、Lucas D. Dias、Júlio C. Viana、Gilberto L.B. Aquino、Marta Pineiro、Mariette M. Pereira

  DOI：10.1016/j.molcata.2016.02.016

  日期：2016.5

  Abstract The hydroformylation of highly substituted alkyl olefins was efficiently performed, with use of rhodium(I)/tris-binaphthyl monophosphite catalysts, containing different ether substituents at the 2′-binaphthyl position (OMe, OBn, OCHPh 2 and OAdamantyl). A systematic kinetic study, carried out for hydroformylation of methyl non-3-enoate, has shown a significant influence of the ligand’s OR group

  摘要 使用在 2'-联萘位置（OMe、OBn、OCHPh 2 和 OAdamantyl）含有不同醚取代基的铑 (I)/三联萘单亚磷酸酯催化剂有效地进行了高度取代的烷基烯烃的加氢甲酰化。对非 3-烯酸甲酯的加氢甲酰化进行的系统动力学研究表明，配体的 OR 基团对铑催化剂的性能有显着影响，Rh(I)/tris[2'-benzyloxy-1, 1'-联萘-2-基]亚磷酸酯催化体系 (Rh(I)/ L2 -OBn) 对醛类化合物具有最高的化学选择性，对 C-5 甲酰基产物具有最高的区域选择性。该催化体系进一步应用于天然产物的负载CC双键的加氢甲酰化，即油酸甲酯、(-)-异胡薄荷醇苄基醚和17β-acetoxyandrost-4-ene，