全氟异丁烯 | 382-21-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 全氟异丁烯
• 中文别名: 八氟异丁烯
• 英文名称: Perfluoroisobutylen
• 英文别名: octafluoroisobutene；Perfluoroisobutylene；1,1,3,3,3-pentafluoro-2-(trifluoromethyl)prop-1-ene
• CAS: 382-21-8
• 化学式: C₄F₈
• 分子量: 200.031
• InChiKey: DAFIBNSJXIGBQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  8

ADMET

代谢

PFIB的化学性质通过使用电子顺磁共振自旋捕捉技术进行研究，并得出结论，这种高度亲电性的化学品可能会经历电子转移，从而导致多种高度反应性的中间体。PFIB对亲核试剂具有反应性，能够产生取代和加成自由基副产物。PFIB几乎与所有已知的亲核试剂反应。

Chemistry of PFIB /was studied/ by using electron paramagnetic resonance spin-trapping techniques and concluded that this highly electrophilic chemical likely undergoes electron transfer that leads to several highly reactive intermediates. PFIB is reactive towards nucleophilic reagents to yield substitution and addition radical byproducts. PFIB reacts with almost all known nucleophiles.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 毒性总结

识别和使用：全氟异丁烯是一种无色气体，可溶于水。它可能被用作潜在的化学战剂；半导体制造和合成聚合材料的蚀刻材料。人类暴露和毒性：一旦失去控制，空气中这种气体的有害浓度会很快达到。该物质可以通过吸入进入人体。该物质刺激呼吸道。吸入暴露可能导致严重的肺水肿症状，伴有喘息、呼吸困难、咳痰和皮肤发蓝。起初可能出现咳嗽和胸痛。然而，严重的肺水肿症状可能会延迟几小时，然后迅速恶化。过度暴露可能导致死亡。这种化学物质是人类皮肤、眼睛和粘膜的刺激物。人类急性暴露会导致结膜、喉咙和肺部的明显刺激。职业暴露于全氟异丁烯是有限的，但可能在生产或使用它或其聚合物，聚四氟乙烯（PTFE，特氟龙）的工作场所通过吸入发生。动物研究：在一项急性研究中，大鼠暴露于0.25 ppm的全氟异丁烯4小时。在暴露期间，一些动物出现过度换气，其中6只动物中有3只在暴露后3小时出现呼吸困难。还记录了一些动物出现充血、打喷嚏、呼吸困难和轻度反应性。大鼠通过吸入暴露于这种化学物质，无论是0.24还是0.49 ppm，持续4小时，都显示出条件反射的改变，伴有血液中谷氨酸草酸乙酸转移酶和谷氨酸丙酮酸转移酶活性的增加。肺中出现水肿。在大鼠急性暴露于78 ppm的全氟异丁烯1.5分钟后，对大鼠肺的组织病理学进行了研究。暴露5分钟内观察到支气管和肺泡周围肺泡的变化，表现为纤毛结构的改变、吞噬作用的增加和电子透明度，偶尔伴有I型肺泡上皮细胞的囊泡形成。还看到了细胞间泄漏和肺泡空间的最小积液。肺水肿逐渐发展，在暴露后2-3小时在组织学上可见，死亡发生在7小时后。在暴露后24小时处死的大鼠显示出广泛的肺水肿和肺泡间质由淋巴-单核细胞和巨噬细胞浸润的证据。

IDENTIFICATION AND USE: Perfluoroisobutylene is a colorless gas which is soluble in water. It may be used as a potential chemical warfare agent; etching material for semiconductor fabrication and synthesis of polymeric materials. HUMAN EXPOSURE AND TOXICITY: A harmful concentration of this gas in the air will be reached very quickly on loss of containment. The substance can be absorbed into the body by inhalation. The substance irritates the respiratory tract. Inhalation exposure may cause severe symptoms of pulmonary edema with wheezing, difficulty in breathing, coughing up sputum and bluish discoloration of the skin. Coughing and chest pain may occur initially. However, severe symptoms of pulmonary edema may be delayed for several hours and then become rapidly worse. Overexposure may cause death. This chemical is a human skin, eye, and mucous membrane irritant. Human acute exposures causes marked irritation of conjunctivae, throat, and lungs. Occupational exposure to perfluoroisobutylene is limited but may occur through inhalation at workplaces where it or the polymer, polytetrafluoroethylene (PTFE, Teflon) is produced or used. ANIMAL STUDIES: In an acute study, rats were exposed to perfluoroisobutylene at 0.25 ppm for 4 hours. During exposure, some animals showed hyperpnea, while three of six animals had dyspnea for 3 hours postexposure. Hyperemia, sneezing, dyspnea, and mild responsiveness were also documented in some animals. Rats exposed by inhalation to this chemicalat either 0.24 or 0.49 ppm for 4 hours showed changes in conditioned reflexes, accompanied by an increase in the activity of glutamicoxaloacetic and glutamicpyruvic transaminases in the blood serum. Edema was seen in the lungs. The histopathology of rat lung has been studied after an acute exposure to perfluoroisobutylene at a concentration of 78 ppm for 1.5 minutes. Within 5 minutes of exposure changes to bronchioles and peribronchial alveoli were observed which took the form of alterations to cilial structure, increased pinocytosis and electron lucency, with occasional vesicle formation of type I alveolar epithelial cells. Intercellular leakage with minimal fluid accumulation in the alveolar spaces was also seen. Gradual development of pulmonary edema followed and was visible histologically 2-3 hr post exposure with deaths occurring from 7 hr onwards. Animals sacrificed at 24 hr post exposure showed evidence of widespread pulmonary edema and alveolar interstitial infiltration by lympho-mononuclear cells and macrophages.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 暴露途径

这种物质可以通过吸入被身体吸收。

The substance can be absorbed into the body by inhalation.

来源:ILO-WHO International Chemical Safety Cards (ICSCs)

毒理性

• 吸入症状

喉咙痛。咳嗽。恶心。头痛。虚弱。气短。呼吸困难。症状可能会延迟出现。

Sore throat. Cough. Nausea. Headache. Weakness. Shortness of breath. Laboured breathing. Symptoms may be delayed.

来源:ILO-WHO International Chemical Safety Cards (ICSCs)

毒理性

• 副作用

有害性肺炎 - 由于吸入金属烟雾或有毒气体和蒸气引起的肺部炎症。

Toxic Pneumonitis - Inflammation of the lungs induced by inhalation of metal fumes or toxic gases and vapors.

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

毒理性

• 毒性数据

LC50 (大鼠) = 0.5 ppm/6小时

LC50 (rat) = 0.5 ppm/6hr

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

反应信息

• 作为反应物：
  描述：

  全氟异丁烯 在 氢气 作用下， 50.0 ℃ 、100.0 kPa 条件下， 反应 10.0h， 生成 2-(二氟甲基)-1,1,1,3,3,3-六氟丙烷
  参考文献：
  名称：

  气相连续制备3,3,3-三氟-2-(三氟甲基)-1-丙烯的方法

  摘要：

  本发明公开了一种气相连续制备3,3,3‑三氟‑2‑(三氟甲基)‑1‑丙烯的方法，以八氟异丁烯为原料通过加氢‑脱氟化氢‑加氢‑脱氟化氢四步气相连续反应，得到3,3,3‑三氟‑2‑(三氟甲基)‑1‑丙烯。本发明的加氢催化剂、脱氟化氢催化剂均具有活性高、使用寿命长的特点；并通过气相独立循环工艺，将反应不完全的物料进行独立循环，可以使初始原料几乎完全地转化3,3,3‑三氟‑2‑(三氟甲基)‑1‑丙烯，最终从工艺体系中高效率、气相连续循环地采出的是产品3,3,3‑三氟‑2‑(三氟甲基)‑1‑丙烯，从而不产生液废和废气，实现绿色生产。

  公开号：

  CN112794787A
• 作为产物：
  描述：

  2,2-difluoro-3,3-bis(trifluoromethyl)thiirane 在 五氟化锑 作用下， 反应 0.33h， 以52%的产率得到全氟异丁烯
  参考文献：
  名称：

  Dehydrohalogenation of fluorinated sulfenyl chlorides. synthesis and properties of perfluoroisobutylene sulfide

  摘要：

  DOI：

  10.1007/bf00954716
• 作为试剂：
  描述：

  methyl-thiophosphonic acid O-isopropyl ester 在 全氟异丁烯 、 potassium acetate 作用下， 以 溶剂黄146 为溶剂， 生成 沙林
  参考文献：
  名称：

  Reactions of fluoro olefins Communication 18. Addition of acid phosphono- and phosphoro-thioic esters to perfluoro olefins

  摘要：

  DOI：

  10.1007/bf00848907

文献信息

• PYROLYSIS PROCESS
  申请人：Noelke Joseph Charles

  公开号：US20050137430A1

  公开（公告）日：2005-06-23

  The present invention relates to the pyrolysis of hydrochlorofluorocarbons to form fluoromonomers such as tetrafluoroethylene, the pyrolysis being carried out in a reaction zone lined with nickel and mechanically supported by a jacket of other corrosion resistant metal, the nickel lining providing an improved yield of valuable reaction products.

  本发明涉及氢氯氟烃的热解，以形成四氟乙烯等氟单体，热解是在镍衬里的反应区内进行的，并且通过其他耐腐蚀金属的夹套进行机械支撑，镍衬提供了更高产值的有价值的反应产物。
• 以六氟丙烯为起始原料合成氟代异丁烯的方法
  申请人：北京宇极科技发展有限公司

  公开号：CN112794788A

  公开（公告）日：2021-05-14

  本发明公开了一种以六氟丙烯为起始原料合成氟代异丁烯的方法，包括以下步骤：（1）气相加成反应：在嵌段催化剂存在下，六氟丙烯与氟代甲烷CHFXY(X,Y=F或H)发生气相加成得到(CF3)2CFCHXY，（2）脱氟化氢反应：在脱氟化氢催化剂存在下，( )2CFCHXY为原料发生脱氟化氢反应，得到( )2C=CXY。本发明中的嵌段催化剂、脱氟化氢催化剂均具有活性高、使用寿命长的特点，可用于高效率、气相连续循环地生产氟代异丁烯。
• Synthesis of 3,3,3-trifluoroethyl isocyanate, carbamate and ureas. Anticancer activity evaluation of N-(3,3,3-trifluoroethyl)-N′-substituted ureas
  作者：Elena L. Luzina、Anatoliy V. Popov

  DOI：10.1016/j.jfluchem.2015.06.005

  日期：2015.8

  isocyanate from perfluoroisobutene (PFIB). Isocyanate was used for synthesis of carbamates and ureas. A series of trifluoroethyl-substituted ureas has been tested in the National Cancer Institute (NCI, Bethesda, USA) by the NCI-60 DTP Human Tumor Cell Line Screening Program at a single high dose (10−5 M). The moderate anticancer activity was shown against some types of cancer on the individual human cell

  描述了一种由全氟异丁烯（PFIB）生产3,3,3-三氟乙基异氰酸酯的新方法。异氰酸酯用于合成氨基甲酸酯和脲。美国国家癌症研究所（NCI，Bethesda，USA）已通过NCI-60 DTP人肿瘤细胞系筛选计划以单一高剂量（10 -5  M）测试了一系列三氟乙基取代的脲。在白血病，非小细胞肺癌和肾癌的单个人细胞系上显示出对某些类型癌症的中等抗癌活性。
• Novel reactions of perfluoro-2-(trifluoromethyl)-propene
  作者：S. Munavalli、E.O. Lewis、A.J. Muller、D.I. Rossman、D.K. Rohrbaugh、C.P. Ferguson

  DOI：10.1016/s0022-1139(00)80569-2

  日期：1993.8

  hydrocarbon counterpart, perfluoro-2-(trifluoromethyl)propene is a highly reactive compound. It participates in both heterolytic and homolytic reactions. It readily reacts with nucleophiles and sluggishly with electrophiles. It reacts as well with common organic solvents, such as dimethylformamide, ethanol and others. In this communication, we describe its reactions with trifluoromethylthiocopper, sulfur

  与它的烃对应物不同，全氟-2-（三氟甲基）丙烯是高反应性化合物。它参与了杂溶和均溶反应。它容易与亲核试剂反应，而与亲电子试剂反应缓慢。它也可以与常见的有机溶剂（例如二甲基甲酰胺，乙醇等）反应。在本文中，我们描述了其与三氟甲基硫代铜，三氧化硫和三丁基氰化锡的反应，各种产物的形成机理及其质谱数据。
• Perfluoroalkyl derivatives of nitrogen. Part XXV. The reactions of tristrifluoromethylhydroxylamine and mercuric bistrifluoromethylamide with unsaturated systems
  作者：R. N. Haszeldine、A. E. Tipping

  DOI：10.1039/j39670001241

  日期：——

  obutane), and lower yields of other products including perfluoro-(1,2-bisdimethylaminocyclobutane), perfluoro-(2,2′-dimethoxybicyclobutyl), and perfluoro-(2-dimethylamino-2′-methoxybicyclobutyl). Reaction with perfluorobut-2-ene is more complex. Perfluoro-2-azapropene gives low yields of the two isomeric 1:1 adducts perfluoro-(2,3-dimethyl-5-oxa-2,3-diazahexane) and perfluoro-(3,5-dimethyl-2-oxa-3

  三氟甲基羟胺在辐照下与全氟环丁烯反应，生成全氟-（1-二甲基氨基-2-甲氧基环丁烷）1：1加合物，并降低其他产物的收率，包括全氟-（1,2-双二甲基氨基环丁烷），全氟-（2,2 '-二甲氧基双环丁基）和全氟-（2-二甲基氨基-2'-甲氧基双环丁基）。与全氟丁-2-烯的反应更为复杂。全氟-2-氮杂丙烯使全氟-（2,3-二甲基-5-氧杂-2,3-二氮杂己烷）和全氟-（3,5-二甲基-2-氧杂-3）的两种异构体1：1加合物的收率低，5-重氮己烷）。

表征谱图