4,4′-(ethane-1,1′-diyl)bis(3-methylphenol) | 108843-03-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4,4′-(ethane-1,1′-diyl)bis(3-methylphenol)
• 英文别名: 3,3'-dimethyl-4,4'-ethylidene-di-phenol；1,1-Bis-(4-hydroxy-2-methyl-phenyl)-aethan；3,3'-Dimethyl-4,4'-aethyliden-di-phenol；4-[1-(4-Hydroxy-2-methylphenyl)ethyl]-3-methylphenol
• CAS: 108843-03-4
• 化学式: C₁₆H₁₈O₂
• 分子量: 242.318
• InChiKey: QEPTUZJHFVCCNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cyanogen bromide 、 4,4′-(ethane-1,1′-diyl)bis(3-methylphenol) 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以79.6%的产率得到4,4′-(ethane-1,1′-diyl)bis(1-cyanato-3-methylbenzene)
  参考文献：
  名称：

  Effects of o-Methoxy Groups on the Properties and Thermal Stability of Renewable High-Temperature Cyanate Ester Resins

  摘要：

  Renewable phenols derived from biomass sources often contain methoxy groups that alter the properties of derivative polymers. To evaluate the impact of o-methoxy groups on the performance characteristics of cyanate ester resins, three bisphenols derived from the renewable phenol creosol were deoxygenated by conversion to ditriflates followed by palladium-catalyzed elimination and hydrolysis of the methoxy groups. The deoxygenated bisphenols were then converted to the following cyanate ester resins: bis(4-cyanato-2-methylphenyl)methane (16), 4,4'-(ethane-1,1'-diy1)bis-(1-cyanato-3-methylbenzene) (17), and 4,4'-(propane-1,1'-diy1)bis(1-cyanato-3-methylbenzene) (18). The physical properties, cure chemistry, and thermal stability of these resins were evaluated and compared to those of cyanate esters derived from the oxygenated bisphenols. 16 and 18 had melting points 37 and >95 degrees C lower, respectively, than the oxygenated versions, while 17 had a melting point 14 degrees C higher. The T-g's of thermosets generated from the deoxygenated resins ranged from 267 to 283 degrees C, up to 30 degrees C higher than the oxygenated resins, while the onset of thermal degradation was 50-80 degrees C higher. The deoxygenated resins also exhibited water uptakes up to 43% lower and wet T(g)s up to 37 degrees C higher than the oxygenated resins. TGA-FTIR of thermoset networks derived from 16-18 revealed a different decomposition mechanism compared to the oxygenated resins. Instead of a low-temperature pathway that resulted in the evolution of phenolic compounds, 16-18 had significantly higher char yields and decomposed via evolution of small molecules including isocyanic acid, CH4, CO2, and NH3.

  DOI：

  10.1021/acs.macromol.5b00496
• 作为产物：
  描述：

  5,5′-(ethane-1,1-diyl)bis(2-methoxy-4-methylphenol) 在 吡啶 、 1,1'-双(二苯基膦)二茂铁 、 甲酸 、 palladium diacetate 、 三溴化硼 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.33h， 生成 4,4′-(ethane-1,1′-diyl)bis(3-methylphenol)
  参考文献：
  名称：

  Effects of o-Methoxy Groups on the Properties and Thermal Stability of Renewable High-Temperature Cyanate Ester Resins

  摘要：

  Renewable phenols derived from biomass sources often contain methoxy groups that alter the properties of derivative polymers. To evaluate the impact of o-methoxy groups on the performance characteristics of cyanate ester resins, three bisphenols derived from the renewable phenol creosol were deoxygenated by conversion to ditriflates followed by palladium-catalyzed elimination and hydrolysis of the methoxy groups. The deoxygenated bisphenols were then converted to the following cyanate ester resins: bis(4-cyanato-2-methylphenyl)methane (16), 4,4'-(ethane-1,1'-diy1)bis-(1-cyanato-3-methylbenzene) (17), and 4,4'-(propane-1,1'-diy1)bis(1-cyanato-3-methylbenzene) (18). The physical properties, cure chemistry, and thermal stability of these resins were evaluated and compared to those of cyanate esters derived from the oxygenated bisphenols. 16 and 18 had melting points 37 and >95 degrees C lower, respectively, than the oxygenated versions, while 17 had a melting point 14 degrees C higher. The T-g's of thermosets generated from the deoxygenated resins ranged from 267 to 283 degrees C, up to 30 degrees C higher than the oxygenated resins, while the onset of thermal degradation was 50-80 degrees C higher. The deoxygenated resins also exhibited water uptakes up to 43% lower and wet T(g)s up to 37 degrees C higher than the oxygenated resins. TGA-FTIR of thermoset networks derived from 16-18 revealed a different decomposition mechanism compared to the oxygenated resins. Instead of a low-temperature pathway that resulted in the evolution of phenolic compounds, 16-18 had significantly higher char yields and decomposed via evolution of small molecules including isocyanic acid, CH4, CO2, and NH3.

  DOI：

  10.1021/acs.macromol.5b00496

文献信息

• THE CONDENSATION OF CERTAIN PHENOLS WITH SOME ALIPHATIC ALDEHYDES¹
  作者：Wilton C. Harden、E. Emmet Reid

  DOI：10.1021/ja01350a027

  日期：1932.11
• US4943665A
  申请人：——

  公开号：US4943665A

  公开（公告）日：1990-07-24
• US5021528A
  申请人：——

  公开号：US5021528A

  公开（公告）日：1991-06-04
• [EN] CURING AGENTS FOR EPOXY RESINS<br/>[FR] AGENTS DE POLYMÉRISATION POUR RÉSINES ÉPOXY
  申请人：DESIGNER MOLECULES INC

  公开号：WO2011116050A2

  公开（公告）日：2011-09-22

  The present invention relates to curatives for epoxy resins, and compositions (e.g. adhesives) containing such resins cured using the same methods of preparation and uses therefor. More specifically, the present invention relates to hybrid curatives for epoxy resins comprising both aromatic amine, phenol and/or phenyl ester moieties. A further aspect of the current invention relates to new imidazole catalysts that possess a combination of excellent cure latency as well as low cure temperature onset.
• Effects of <i>o</i>-Methoxy Groups on the Properties and Thermal Stability of Renewable High-Temperature Cyanate Ester Resins
  作者：Benjamin G. Harvey、Andrew J. Guenthner、William W. Lai、Heather A. Meylemans、Matthew C. Davis、Lee R. Cambrea、Josiah T. Reams、Kevin R. Lamison

  DOI：10.1021/acs.macromol.5b00496

  日期：2015.5.26

  Renewable phenols derived from biomass sources often contain methoxy groups that alter the properties of derivative polymers. To evaluate the impact of o-methoxy groups on the performance characteristics of cyanate ester resins, three bisphenols derived from the renewable phenol creosol were deoxygenated by conversion to ditriflates followed by palladium-catalyzed elimination and hydrolysis of the methoxy groups. The deoxygenated bisphenols were then converted to the following cyanate ester resins: bis(4-cyanato-2-methylphenyl)methane (16), 4,4'-(ethane-1,1'-diy1)bis-(1-cyanato-3-methylbenzene) (17), and 4,4'-(propane-1,1'-diy1)bis(1-cyanato-3-methylbenzene) (18). The physical properties, cure chemistry, and thermal stability of these resins were evaluated and compared to those of cyanate esters derived from the oxygenated bisphenols. 16 and 18 had melting points 37 and >95 degrees C lower, respectively, than the oxygenated versions, while 17 had a melting point 14 degrees C higher. The T-g's of thermosets generated from the deoxygenated resins ranged from 267 to 283 degrees C, up to 30 degrees C higher than the oxygenated resins, while the onset of thermal degradation was 50-80 degrees C higher. The deoxygenated resins also exhibited water uptakes up to 43% lower and wet T(g)s up to 37 degrees C higher than the oxygenated resins. TGA-FTIR of thermoset networks derived from 16-18 revealed a different decomposition mechanism compared to the oxygenated resins. Instead of a low-temperature pathway that resulted in the evolution of phenolic compounds, 16-18 had significantly higher char yields and decomposed via evolution of small molecules including isocyanic acid, CH4, CO2, and NH3.