1-[2-(2-乙氧基乙氧基)乙氧基]-1,2,2-三氟乙烯 | 197356-84-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 中文名称: 1-[2-(2-乙氧基乙氧基)乙氧基]-1,2,2-三氟乙烯
• 英文名称: 1-[2-(2-ethoxyethoxy)ethoxy]-1,2,2-trifluoroethene
• 英文别名: Ethene, [2-(2-ethoxyethoxy)ethoxy]trifluoro-
• CAS: 197356-84-6
• 化学式: C₈H₁₃F₃O₃
• 分子量: 214.185
• InChiKey: PUJCFSQVLRTYOQ-UHFFFAOYSA-N

物化性质

• 沸点：
  195.4±40.0 °C(Predicted)
• 密度：
  1.131±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  sodium;hydride 、 乙二醇二甲醚 、 2-(2-叔-丁氧基乙氧基)乙醇 、 、 、 1-[2-(2-乙氧基乙氧基)乙氧基]-1,2,2-三氟乙烯 在 18-冠醚-6 sodium salts 、 crude product 、 potassium carbonate 作用下， 以 正戊烷 为溶剂， 5.0~65.0 ℃ 、2.67 kPa 条件下， 反应 2.75h， 以14.1 g (63% yield) of the desired product, 1-[2-(2-ethoxyethoxy)ethoxy]-1,2,2-trifluoroethene, was isolated at a boiling point of 26-27° C. (pressure 0.15 mmHg, >99% purity by GC)的产率得到1-[2-(2-t-butoxyethoxy)ethoxy]-1,2,2-trifluoroethene
  参考文献：
  名称：

  NEW FLUOROMONOMERS AND METHODS OF PRODUCTION, AND NEW FLUOROPOLYMERS PRODUCED THEREFROM

  摘要：

  本发明提供了具有通用结构的新型氟单体：CF2═CF（OCH2CH2）nOR，其中n为整数，R为功能基团，并提供了制备同样的方法。本发明还提供了一种新的合成氟单体的方法。本发明还涉及由任何一种或组合的新氟单体制备的新氟聚合物，其具有通用结构：—[—CF2CF{(OCH2CH2)nOR}—]m—，其中n为整数，m为整数，R代表未取代或惰性取代的烃基团。该方法还涉及由新氟单体单独、新氟单体和现有氟单体或新氟单体和现有碳氢化合物或功能化碳氢单体制备的新共聚物或三聚物。

  公开号：

  US20030040591A1
• 作为产物：
  描述：

  trimethylsilyl 2-[2-(2-ethoxyethoxy)ethoxy]-2,3,3,3-tetrafluoropropionate 反应 1.0h， 以63%的产率得到1-[2-(2-乙氧基乙氧基)乙氧基]-1,2,2-三氟乙烯
  参考文献：
  名称：

  Synthesis of Trifluorovinyl Ethers Incorporating Functionalized Hydrocarbon Ether Groups:  Insight into the Mechanism of Trifluorovinyl Ether Formation from Trimethylsilyl 2-Alkoxy-2,3,3,3-tetrafluoropropionates

  摘要：

  Novel trifluorovinyl ethers (TFVEs, ROCF=CF2), where R is an oligoether, were synthesized from the corresponding sodium alkoxide and hexafluoropropene oxide. The sodium alkoxide ring opened hexafluoropropene oxide at the more highly substituted carbon (C2) to give the 2-alkoxy-2,3,3,3-tetrafluoropropionic acid ester incorporating 2 equiv of the alcohol, ROCF(CFB)CO2R. Hydrolysis of the ester and reaction of the resulting sodium 2-alkoxy-2,3,3,3-tetrafluoropropionate with chlorotrimethylsilane gave the trimethylsilyl 2-alkoxy-2,3,3,3-tetrafluoropropionate, ROCF(CF3)CO2-Si(CH3)(3). Gas phase vacuum thermolysis of the trimethylsilyl ester at 140-150 degrees C gave the corresponding TFVEs in 55-63% yields. Thus, 1-[2-(ethoxyethoxy)ethoxy]-1,2,2-trifluoroethene and 1-[2-(2-tert-butoxyethoxy)ethoxy]-1,2,2-trifluoroethene were synthesized from 2-(2-ethoxyethoxy)ethanol and 2-(2-tert-butoxyethoxy)ethanol, respectively. Interestingly, thermolysis of sodium or potassium 2-alkoxy-2,3,3,3-tetrafluoropropionates resulted in negligible to low yields of TFVEs.(1) For example, thermolysis of sodium 2-[2-(ethoxyethoxy)ethoxy]-2,3,3,3-tetrafluoropropionate gave a trifluoroacetate ester, 2-(2-ethoxyethoxy)ethyl trifluoroacetate. Variable temperature F-19 NMR spectroscopy of trimethylsilyl 2-[2-(ethoxyethoxy)ethoxy]-2,3,3,3-tetrafluoropropionate suggests that an equilibrium exists between two structural conformations of these trimethylsilyl esters: one in which there is an intramolecular ''interaction'' of silicon with fluorine and one in which there is no silicon-fluorine interaction. This interaction may affect the outcome of the trimethylsilyl ester thermolysis.

  DOI：

  10.1021/jo971319d

文献信息

• New fluoromonomers and methods of production, and new fluoropolymers produced therefrom
  申请人：——

  公开号：US20030109653A1

  公开（公告）日：2003-06-12

  The present invention provides new fluoromonomers having the generic structure: CF 2 ═CF(OCH 2 CH 2 ) n OR where n is an integer and R is a functional group and methods for producing same. A new method of synthesizing the fluoromonomers is provided. The present invention also relates to new fluoropolymers prepared from any one or combination of the new fluoromonomers and having the generic structure: —[—CF 2 CF{(OCH 2 CH 2 ) n OR}—] m — where n is an integer, m is an integer and R represents an unsubstituted or inertly substituted hydrocarbyl group. The method also relates to new copolymers or terpolymers prepared from the new fluoromonomers alone, the new fluoromonomers and existing fluoromonomers or the new fluoromonomers and existing hydrocarbon or functionalized hydrocarbon monomers.

  本发明提供了具有通用结构的新氟单体：CF2CF(OCH2CH2)nOR，其中n是整数，R是一个功能基团，以及制备它们的方法。提供了一种合成氟单体的新方法。本发明还涉及从任何一种或多种新氟单体制备的新氟聚合物，其具有通用结构：—[—CF2CF(OCH2CH2)nOR]m—其中n为整数，m为整数，R代表未取代或惰性取代的烃基团。该方法还涉及仅从新氟单体、新氟单体和现有氟单体或新氟单体和现有碳氢化合物或官能化碳氢单体制备的新共聚物或三元共聚物。
• Fluoromonomers and method of production, and new fluoropolymers produced therefrom
  申请人：——

  公开号：US06531558B1

  公开（公告）日：2003-03-11

  The present invention provides new fluoromonomers having the generic structure: CF2═CF(OCH2CH2)nOR where n is an integer and R is a functional group and methods for producing same. A new method of synthesizing the fluoromonomers is provided. The present invention also relates to new fluoropolymers prepared from any one or combination of the new fluoromonomers and having the generic structure: —[—CF2CF{(OCH2CH2)nOR}—]m— where n is an integer, m is an integer and R represents an unsubstituted or inertly substituted hydrocarbyl group. The method also relates to new copolymers or terpolymers prepared from the new fluoromonomers alone, the new fluoromonomers and existing fluoromonomers or the new fluoromonomers and existing hydrocarbon or functionalized hydrocarbon monomers.

  本发明提供了具有通用结构的新的氟单体：CF2═CF（OCH2CH2）nOR，其中n为整数，R为功能基团，以及制备它们的方法。本发明提供了一种合成氟单体的新方法。本发明还涉及从任何一种或多种新的氟单体制备的具有通用结构的新氟聚合物：—[—CF2CF{(OCH2CH2)nOR}—]m—，其中n为整数，m为整数，R代表未取代或惰性取代的烃基团。该方法还涉及仅使用新的氟单体，新的氟单体和现有的氟单体或新的氢碳或功能化氢碳单体制备的新共聚物或三元聚物。
• US6531558B1
  申请人：——

  公开号：US6531558B1

  公开（公告）日：2003-03-11
• Synthesis of Trifluorovinyl Ethers Incorporating Functionalized Hydrocarbon Ether Groups:  Insight into the Mechanism of Trifluorovinyl Ether Formation from Trimethylsilyl 2-Alkoxy-2,3,3,3-tetrafluoropropionates
  作者：Robert D. Lousenberg、Molly S. Shoichet

  DOI：10.1021/jo971319d

  日期：1997.10.1

  Novel trifluorovinyl ethers (TFVEs, ROCF=CF2), where R is an oligoether, were synthesized from the corresponding sodium alkoxide and hexafluoropropene oxide. The sodium alkoxide ring opened hexafluoropropene oxide at the more highly substituted carbon (C2) to give the 2-alkoxy-2,3,3,3-tetrafluoropropionic acid ester incorporating 2 equiv of the alcohol, ROCF(CFB)CO2R. Hydrolysis of the ester and reaction of the resulting sodium 2-alkoxy-2,3,3,3-tetrafluoropropionate with chlorotrimethylsilane gave the trimethylsilyl 2-alkoxy-2,3,3,3-tetrafluoropropionate, ROCF(CF3)CO2-Si(CH3)(3). Gas phase vacuum thermolysis of the trimethylsilyl ester at 140-150 degrees C gave the corresponding TFVEs in 55-63% yields. Thus, 1-[2-(ethoxyethoxy)ethoxy]-1,2,2-trifluoroethene and 1-[2-(2-tert-butoxyethoxy)ethoxy]-1,2,2-trifluoroethene were synthesized from 2-(2-ethoxyethoxy)ethanol and 2-(2-tert-butoxyethoxy)ethanol, respectively. Interestingly, thermolysis of sodium or potassium 2-alkoxy-2,3,3,3-tetrafluoropropionates resulted in negligible to low yields of TFVEs.(1) For example, thermolysis of sodium 2-[2-(ethoxyethoxy)ethoxy]-2,3,3,3-tetrafluoropropionate gave a trifluoroacetate ester, 2-(2-ethoxyethoxy)ethyl trifluoroacetate. Variable temperature F-19 NMR spectroscopy of trimethylsilyl 2-[2-(ethoxyethoxy)ethoxy]-2,3,3,3-tetrafluoropropionate suggests that an equilibrium exists between two structural conformations of these trimethylsilyl esters: one in which there is an intramolecular ''interaction'' of silicon with fluorine and one in which there is no silicon-fluorine interaction. This interaction may affect the outcome of the trimethylsilyl ester thermolysis.
• NEW FLUOROMONOMERS AND METHODS OF PRODUCTION, AND NEW FLUOROPOLYMERS PRODUCED THEREFROM
  申请人：——

  公开号：US20030040591A1

  公开（公告）日：2003-02-27

  The present invention provides new fluoromonomers having the generic structure: CF 2 ═CF(OCH 2 CH 2 ) n OR where n is an integer and R is a functional group and methods for producing same. A new method of synthesizing the fluoromonomers is provided. The present invention also relates to new fluoropolymers prepared from any one or combination of the new fluoromonomers and having the generic structure: —[—CF 2 CF{(OCH 2 CH 2 ) n OR}—] m — where n is an integer, m is an integer and R represents an unsubstituted or inertly substituted hydrocarbyl group.The method also relates to new copolymers or terpolymers prepared from the new fluoromonomers alone, the new fluoromonomers and existing fluoromonomers or the new fluoromonomers and existing hydrocarbon or functionalized hydrocarbon monomers.

  本发明提供了具有通用结构的新型氟单体：CF2═CF（OCH2CH2）nOR，其中n为整数，R为功能基团，并提供了制备同样的方法。本发明还提供了一种新的合成氟单体的方法。本发明还涉及由任何一种或组合的新氟单体制备的新氟聚合物，其具有通用结构：—[—CF2CF{(OCH2CH2)nOR}—]m—，其中n为整数，m为整数，R代表未取代或惰性取代的烃基团。该方法还涉及由新氟单体单独、新氟单体和现有氟单体或新氟单体和现有碳氢化合物或功能化碳氢单体制备的新共聚物或三聚物。