七氟丙烷 | 431-89-0

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氟化物
• 中文名称: 七氟丙烷
• 中文别名: 氢氟碳227EA；1,1,1,2,3,3,3-七氟代丙烷；阿帕氟烷；1,1,1,2,3,3,3-七氟丙烷；2H-七氟丙烷
• 英文名称: 1,1,1,2,3,3,3-Heptafluoropropane
• 英文别名: R-227ea
• CAS: 431-89-0
• 化学式: C₃HF₇
• mdl: MFCD00043834
• 分子量: 170.03
• InChiKey: YFMFNYKEUDLDTL-UHFFFAOYSA-N

物化性质

• 稳定性/保质期：
  稳定，在强氧化剂和碱金属存在下不相容。

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  7

ADMET

代谢

研究了七氟丙烷（HFA-227）作为气溶胶推进剂在大鼠体内的生物转化，以及在鼠和人类肝脏微体中的情况。在暴露于5000 ppm HFA-227 6小时的大鼠尿液中，通过19F-NMR鉴定出极微量的六氟乙酰三水合物作为HFA-227的代谢物。暴露动物尿液样本（暴露结束后0-48小时）中的氟化物浓度与非暴露大鼠样本中的浓度没有显著差异。在鼠和人类肝脏微体中，只有在用吡啶处理的大鼠肝脏微体和八个人类肝脏微体样本中的两个（表现出最高的细胞色素P4502E1活性）中检测到了HFA-227转化为氟化物和六氟乙酰三水合物的极低水平。由于一些醛类物质可能会与蛋白质共价结合，而氟化蛋白加合物的形成与氟烷诱导的免疫介导性肝炎有关，因此也研究了六氟乙酰三水合物与蛋白质的结合。当研究六氟乙酰三水合物与人类血清白蛋白的结合时，与乙基三氟乙酰化剂S-乙基三氟乙酸盐相比，它在氟化物NMR实验中只产生了非常小的共振。此外，六氟乙酰三水合物与N-乙酰-L-赖氨酸反应没有形成含氟产物，在大鼠体内六氟乙酰三水合物也没有被代谢为含氟代谢物或无机氟化物。在人类肝脏微体的比较研究中表明，氟烷的一种代谢物可能会与蛋白质共价结合；相比之下，HFA-227的代谢和共价结合无法得到证实。总之，这些数据表明HFA-227以非常低的速率转化为六氟乙酰三水合物，但即使应用非常敏感的方法，也无法证明六氟乙酰三水合物与蛋白质的不可逆结合，根据所获得的结果组合来看，这种情况被认为是不太可能的。

The biotransformation of the aerosol propellant 1,1,1,2,3,3,3-heptafluoropropane (HFA-227) was investigated in rats in vivo and in rat and human liver microsomes. In the urine of rats exposed to 5000 ppm HFA-227 for 6 hr, very small amounts of hexafluoroacetone trihydrate were identified as an HFA-227 metabolite by 19F-NMR. Fluoride concentrations in the urine samples (0-48 hr after the end of the exposure) from exposed animals were not significantly different from those found in samples from nonexposed rats. In rat and human liver microsomes, fluoride and hexafluoroacetone trihydrate formation from HFA-227 was detected in very low levels only in liver microsomes from pyridine-treated rats and in two of eight human liver microsome samples, which exhibited the highest cytochrome P4502E1 activities. Because some aldehydes may covalently bind to proteins and the formation of fluorinated protein adducts has been implicated in immune-mediated hepatitis induced by halothane, the binding of hexafluoroacetone trihydrate to proteins was also investigated. Hexafluoroacetone trihydrate also gave only a very small resonance in fluorine NMR experiments when binding to human serum albumin was studied in comparison with the acylating agent S-ethyltrifluoroacetate. Moreover, no fluorine-containing products were formed by the reaction of hexafluoroacetone trihydrate with N alpha-acetyl-L-lysine, and hexafluoroacetone trihydrate was not metabolized to fluorine-containing metabolites or inorganic fluoride in rats. Comparative studies in human liver microsomes demonstrated that a halothane metabolite may covalently bind to proteins; in contrast, metabolism and covalent binding of HFA-227 could not be demonstrated. In summary, these data indicate that HFA-227 is biotransformed at very low rates to hexafluoroacetone trihydrate but irreversible binding of hexafluoroacetone trihydrate cannot be demonstrated, even with the application of very sensitive methods, and is considered unlikely, based on the combination of the results obtained.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 毒性总结

识别与用途：1,1,1,2,3,3,3-七氟丙烷（HFC 227）是一种无色气体。它用作制冷剂、高温热泵、空调系统；作为灭火剂；以及用于药物气雾剂和定量吸入器。人类暴露与毒性：健康志愿者暴露于高达8000 ppm HFC 227的暴露水平并未对脉搏、血压、心电图或肺功能产生任何不利影响。动物研究：将HFC 227释放到兔子的眼睛中并未引起任何刺激迹象。暴露于HFC 227可以在浓度为100,000 ppm（10%体积比）及更高时，在狗身上诱导出对外源性肾上腺素挑战的心脏敏感化。大鼠和小鼠单次吸入暴露于300,000和500,000 ppm时没有发生死亡。从100,000 ppm观察到中枢神经系统抑制的迹象。当大鼠和小鼠每天吸入1小时，连续2年暴露于0、60,000、120,000和240,000 ppm的浓度时，与对照组相比并未观察到良性或恶性肿瘤发病率的增加。在几项关于雄性和雌性大鼠的生育研究中，动物每天暴露于HFC 227浓度高达150,000 ppm，1到6小时，在生育和妊娠指数上并未观察到有毒理学意义的效应。高达150,000 ppm的HFC 227浓度在大鼠或兔子中没有胚胎毒性或胎儿毒性效应。类似的浓度对暴露大鼠后代的发展和行为没有显著影响。HFC 227在小鼠骨髓微核试验中呈阴性。HFC 227在测试的最高浓度下有毒，但在S. typhimurium中无致突变性。在小鼠淋巴瘤试验中未观察到毒性或致突变性。

IDENTIFICATION AND USE: 1,1,1,2,3,3,3-Heptafluoropropane (HFC 227) is a colorless gas. It is used in refrigerants, high temperature heat pumps, air-conditioning systems; as a fire suppressant; and for pharmaceutical aerosols and metered-dose inhalers. HUMAN EXPOSURE AND TOXICITY: Exposure of healthy volunteers to exposure levels up to 8000 ppm HFC 227 did not result in any adverse effects on pulse, blood pressure, electrocardiogram, or lung function. ANIMAL STUDIES: HFC 227 released into the eyes of rabbits did not induce any sign of irritation. Exposure to HFC 227 can induce cardiac sensitization in dogs at concentrations from 100,000 ppm (10% v/v) and higher after an exogenous epinephrine challenge. No deaths occurred when rats and mice were exposed by inhalation once to 300,000 and 500,000 ppm respectively. Signs of CNS depression were observed from 100,000 ppm. When rats and mice were exposed by inhalation to concentrations of 0, 60,000, 120,000 and 240,000 ppm for 2 years at a regimen of 1 hour per day, no increased incidence of benign or malignant neoplasms were observed when compared to controls. In several fertility studies in male and female rats in which animals were exposed for 1 to 6 hours per day to HFC 227 concentrations up to 150,000 ppm, no effects of toxicological significance were observed when measured on the fertility and pregnancy index. Concentrations of up to 150,000 ppm HFC 227 had no embryotoxic nor fetotoxic effects in rats or rabbits. Similar concentrations had no significant effect on the development and behavior of the offspring of exposed rats. HFC 227 was negative in the mouse bone marrow micronucleus test. HFC 227 was toxic at the highest concentrations tested but not mutagenic in S. typhimurium. Neither toxicity nor mutagenicity was observed in the mouse lymphoma assay.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 副作用

神经毒素 - 急性溶剂综合征

Neurotoxin - Acute solvent syndrome

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

毒理性

• 毒性数据

大鼠经口LD50 > 10355290 毫克/千克

LC (rat) > 1,035,529 ppm/4h

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

毒理性

• 解毒与急救

立即急救：确保已经进行了充分的中毒物清洗。如果患者停止呼吸，开始人工呼吸，最好使用需求阀复苏器、袋阀面罩装置或口袋面罩，按训练操作。如有必要，进行心肺复苏。立即用缓慢流动的水冲洗受污染的眼睛。不要催吐。如果发生呕吐，让患者前倾或置于左侧（如果可能，头部向下）以保持呼吸道畅通，防止吸入性肺炎。保持患者安静，维持正常体温。寻求医疗帮助。/氯氟烃（CFCs）及相关化合物/

Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Chlorinated fluorocarbons (CFCs) and related compounds/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

基本治疗：建立专利气道（如需要，使用口咽或鼻咽气道）。必要时进行抽吸。观察呼吸不足的迹象，并在需要时辅助通气。通过非循环呼吸面罩以10至15升/分钟的速度给予氧气。尽量减少体力活动并提供安静的环境。监测肺水肿，并在必要时进行治疗……。预见并治疗癫痫发作……。对于眼睛污染，立即用水冲洗眼睛。在运输过程中用0.9%的生理盐水（NS）持续冲洗每只眼睛……。不要使用催吐剂。如果患者能够吞咽、有强烈的呕吐反射且不流口水，则用温水冲洗口腔，并给予5毫升/千克，最多200毫升的水进行稀释。给予活性炭……。使用快速复温技术治疗冻伤……。/氯氟烃（CFCs）及相关化合物/

Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations as needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Minimize physical activity and provide a quiet atmosphere. Monitor for pulmonary edema and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. Rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . Treat frostbite with rapid rewarming techniques ... . /Chlorinated fluorocarbons (CFCs) and related compounds/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

口服吸收迅速，但不如肺吸收完全。皮肤吸收微不足道，除非患者有皮肤破损（例如烧伤、溃疡、严重鱼鳞病）。增加的代谢率也可能导致更多的吸入吸收。吸入后很快达到血药峰值，但口服给药后1到2小时才出现。这些化学物质分布到血流丰富的组织（例如大脑、心脏、肝脏、肾脏）然后到脂肪组织，通常在那里找到最高的化学浓度。卤代烃在肝脏通过细胞色素P-450氧化代谢。可能发生部分谷胱甘肽结合。卤代溶剂可以通过肺部不变地排出。由于长期暴露或肝功能不全，消除半衰期可能会增加。长期暴露允许更多的化学物质储存在脂肪组织中，这作为持续释放的来源。/卤代烃 - 卤代溶剂/

Oral absorption is rapid but less complete than pulmonary absorption. Skin absorption is insignificant, except in patients with skin breakdown (e.g., burns, ulcers, severe ichthyosis). Increased metabolic rate can lead to greater inhalational absorption as well. Peak blood levels occur soon after inhalation but occur in 1 to 2 hours after oral administration. The chemicals distribute to tissues with high blood flow (e.g., brain, heart, liver, kidney) and then to adipose tissue, where the highest chemical concentrations are typically found. Halogenated hydrocarbons are metabolized in the liver by cytochrome P-450 oxidation. Partial glutathione conjugation may occur. Halogenated solvents can be excreted unchanged through the lungs. Elimination half-lives can be increased because of either prolonged exposure or hepatic dysfunction. Prolonged exposure allows more chemical to be stored in the adipose tissue, which serves as a source of continued release. /Halogenated Hydrocarbons - Halogenated Solvents/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

HFC 134a（1,1,1,2-四氟乙烷）和HFC 227（1,1,1,2,3,3,3-七氟丙烷）的安全性和药代动力学在两项单独的双盲研究中进行了评估。每种HFC（氢氟烃）都以气态形式通过全身暴露给八名（四名男性和四名女性）健康志愿者。志愿者每周一次暴露1小时，首先接触空气，然后是递增浓度的HFC（1000、2000、4000和8000 ppm），其间穿插第二次空气暴露和两次CFC 12（二氯二氟甲烷）暴露（1000和4000 ppm）。HFC 134a、HFC 227和CFC 12的血药浓度迅速增加，并与暴露浓度相关，虽然不是严格成比例，并接近稳态。最大血药浓度（C(max)）在男性中往往高于女性；在HFC 227研究中，对于每种HFC 227和CFC 12暴露水平，男性的最大血药浓度统计学上显著（P < 0.05）高于女性。在HFC 227研究中，对于CFC 12和HFC 227，在每种暴露水平下，t(1/2)alpha（α消除半衰期）都很短（< 9分钟），且在男性中往往比女性低。对于CFC 12，平均t(1/2)beta（β消除半衰期）范围从23到43分钟，对于HFC 227，平均范围是19-92分钟。HFC 227的值在女性中往往低于男性。对于CFC 12和HFC 227，平均驻留时间（MRT）在男性中统计学上显著低于女性（P < 0.05），且与暴露浓度无关。对于CFC 12，MRT在男性和女性中分别是37和45分钟，对于HFC 227，MRT分别是36和42分钟...

... The safety and pharmacokinetics of HFC 134a (1,1,1,2-tetrafluoroethane) and HFC 227 (1,1,1,2,3,3, 3-heptafluoropropane) were assessed in two separate double-blind studies. Each HFC (hydrofluorocarbon) was administered via whole-body exposure as a vapor to eight (four male and four female) healthy volunteers. Volunteers were exposed, once weekly for 1 hr, first to air and then to ascending concentrations of HFC (1000, 2000, 4000, and 8000 ppm), interspersed with a second air exposure and two CFC 12 (dichlorodifluoromethane) exposures (1000 and 4000 ppm). HFC 134a, HFC 227, and CFC 12 blood concentrations increased rapidly and in an exposure-concentration-dependent manner, although not strictly proportionally, and approached steady state. Maximum blood concentrations (C(max)) tended to be higher in males than females; in the HFC 227 study, these were statistically significantly (P < 0. 05) higher in males for each HFC 227 and CFC 12 exposure level. ... In the HFC 227 study, t(1/2)alpha (alpha elimination half-life) for both CFC 12 and HFC 227, at each exposure level, was short (< 9 min) and tended to be lower in males than females. For CFC 12 mean t(1/2)beta (beta elimination half-life) ranged from 23 to 43 min and for HFC 227 the mean range was 19-92 min. The values tended to be lower for females than males for HFC 227. For both CFC 12 and HFC 227, mean residence time (MRT) was statistically significantly lower (P < 0.05) in males than females and independent of exposure concentration. For CFC 12, MRT was a mean of 37 and 45 min for males and females, respectively, and for HFC 227 MRT was a mean of 36 and 42 min, respectively...

来源:Hazardous Substances Data Bank (HSDB)

制备方法与用途

制备方法： 属于洁净气体灭火剂，主要用于扑灭A类、B类和C类等各种火灾。

用途简介： 暂无详细介绍。

用途： 由于其灭火效能高、毒性低，并且对大气臭氧层没有破坏性，不对使用现场造成污染，七氟丙烷被认为是哈龙1301的理想替代品。它已被美国国家防火协会列入NFPA2001灭火用品标准。此外，七氟丙烷还被用作制冷剂和医用喷射剂。

反应信息

• 作为反应物：
  描述：

  七氟丙烷 在 铁粉 作用下， 反应 4.0h， 以16%的产率得到1,1,3,3,3-五氟-1-丙烯
  参考文献：
  名称：

  PREPARATION OF SELECTED FLUOROOLEFINS

  摘要：

  公开号：

  EP1175380B1
• 作为产物：
  描述：

  六氟丙烯 在 四丁基氟化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以70%的产率得到七氟丙烷
  参考文献：
  名称：

  Fluorine chemistry. Part 2. Synthesis and characterization of 2H-heptafluoropropane (HFC-227ea)

  摘要：

  已经开发出一种简便的方法，用于合成和表征挥发性1,1,1,2,3,3,3-七氟丙烷（HFC-227ea），它是一种潜在的非臭氧破坏氢氟烃替代品，可替代Halon 1301（CF₃Br）。该方法涉及使用从无水四丁基氟化铵分解产生的离子双氟化物，在位生成的离子双氟化物对六氟丙烯进行氢氟化反应。该试剂是氢氟酸的一个很好的等效物，可以使用普通的玻璃器皿。关键词：2H-七氟丙烷，氢氟烃，六氟丙烯，四丁基氟化铵，氢氟化反应。

  DOI：

  10.1139/v04-111
• 作为试剂：
  描述：

  1-溴-3,5-二甲氧基苯 、 苯硼酸 在 potassium phosphate 、 四(三苯基膦)钯 、 三叔丁基膦 作用下， 以 七氟丙烷 、 乙醇 、 1,1,1,3,3-五氟丁烷 为溶剂， 反应 24.0h， 以99%的产率得到1,3-二甲氧基-5-苯基苯
  参考文献：
  名称：

  在环境温度下 Solkane365/227/乙醇混合物中的 Suzuki-Miyaura 交叉偶联反应

  摘要：

  一种环境友好的溶剂系统，Solkane365/227/乙醇混合物，被开发用于芳基硼酸和芳基卤化物的 Suzuki-Miyaura 交叉偶联反应。该反应非常普遍，对各种芳基、杂芳基和氟芳基硼酸或卤化物的产率都非常好。有趣的是，该系统还允许合成多芳基化合物。

  DOI：

  10.1002/ejoc.201101783

文献信息

• 一种新型Friedel-Crafts反应方法及其催化剂
  申请人：福建永晶科技股份有限公司

  公开号：CN110776406B

  公开（公告）日：2022-11-04

  本发明涉及通过称为Friedel‑Crafts的反应分别制备或合成酰化或烷基化芳基化合物，例如酰化或烷基化苯的新方法，以及用于该方法的新催化剂。本发明特别涉及用于合成所述酰化或烷基化化合物Friedel‑Crafts反应的新的环保方法。
• An Experimental and Modelling Study of Ignition Delays in Shock-Heated Ethane-Oxygen-Argon Mixtures Inhibited by 2H-Heptafluoropropane
  作者：K. Ikeda、J.C. Mackie

  DOI：10.1524/zpch.2001.215.8.997

  日期：2001.1.1

  Ignition delay times have been measured behind reflected shock waves in ethane-oxygen-argon mixtures at temperatures between 1150 and 1500 K and pre-ignition pressures between 10 and 14 atm. Delay times have been measured both by pressure rise and OH absorption at 307 nm. Kinetic modelling of the ignition delays has been made using the GRIMech 3.0 mechanism which with addition of several reactions involving HO

  点火延迟时间已在反射激波后的乙烷-氧气-氩混合物中测量，在1150至1500K的温度和10至14大气压的预点火压力下。延迟时间已通过压力升高和307纳米处OH吸收来测量。使用GRIMech 3.0机制进行了点火延迟的动力学建模，其中包括涉及HO的几个反应。
• Unimolecular Rate Constant and Threshold Energy for the HF Elimination from Chemically Activated CF₃CHFCF₃
  作者：Juliana R. Duncan、Michael S. Roach、Brooke Sibila Stiles、Bert E. Holmes

  DOI：10.1021/jp100195e

  日期：2010.7.8

  of CF3CHF and CF3 radicals at room temperature generated chemically activated CF3CHFCF3 molecules with 95 ± 3 kcal/mol of internal energy that decompose by loss of HF, initially attached to adjacent carbons, with an experimental unimolecular rate constant of (4.5 ± 1.1) × 102 s−1. Density functional theory was used to model the unimolecular rate constant for HF elimination, kHF, to determine a threshold

  CF 3 CHF和CF 3自由基在室温下的结合产生了化学活化的CF 3 CHFCF 3分子，其内部能量为95±3 kcal / mol，由于HF的损失而分解，最初附着在相邻的碳上，实验的单分子速率常数为（4.5±1.1）×10 2 s -1。使用密度泛函理论对消除HF的单分子速率常数k HF进行建模，以确定75±2 kcal / mol的阈值能量。
• Preparation of 1-X-2, 2-Difluoroethenylxenon(II) Tetrafluoroborates [CF2=CXXe][BF4]
  作者：Hermann-Josef Frohn、Vadim V. Bardin

  DOI：10.1002/zaac.200300224

  日期：2003.12

  [CF2=CXBF3] and their transformation into the boranes CF2=CXBF2 by fluoride abstraction in PFP is reported. Die Darstellung von 1-X-2, 2-Difluorethenylxenon(II)-tetrafluoroboraten [CF2=CXXe][BF4] Der neue Typ von Alkenylxenon(II)salzen [CF2=CXXe] [BF4] (X = H, Cl, CF3) wurde durch Reaktion der entsprechenden Alkenyldifluorborane CF2=CXBF2 mit XeF2 in 1, 1, 1, 3, 3-Pentafluorpropan (PFP) bei —60 °C erhalten

  通过将相应的烯基二氟硼烷 CF2 = CXBF2 与 XeF2 在 1, 1, 1, 3, 3-五氟丙烷中反应制备新型烯基氙 (II) 盐 [CF2 = CXXe] [BF4] (X = H, Cl, CF3) (PFP) 在-60°C。烯基氙(II)盐通过多核NMR光谱表征。讨论了 C-1 上的取代基 X 对烯基氙 (II) 盐稳定性的影响。此外，还报道了烯基三氟硼酸钾 K [CF2 = CXBF3] 的制备以及通过 PFP 中的氟化物提取将它们转化为硼烷 CF2 = CXBF2。1-X-2, 2-二氟乙烯基二烯酮(II)四氟硼酸盐的制备[CF2=CXXe][BF4]新型烯基二烯酮(II)盐类[CF2=CXXe][BF4](X=H,Cl,CF3)通过相应的烯基二氟硼烷 CF2 = CXBF2 与 XeF2 在 1、1、1、3、3-五氟丙烷（PFP）在-60°C下获得。烯基氙(II)盐通过多核NMR光谱表征。讨论了碳
• Synthesis of methyl polyfluoroalkyl sulphides and polyfluoroalkane-sulphonic acids
  作者：R. N. Haszeldine、B. Hewitson、B. Higginbottom、R. B. Rigby、A. E. Tipping

  DOI：10.1039/c39720000249

  日期：——

  Methyl polyfluoroalkyl sulphides, synthesised by two novel routes: (i) photochemical reaction of a polyfluoroiodoalkane with dimethyl sulphide or dimethyl disulphide and (ii) reaction of a polyfluoroiodoalkane with sodium methanethiolate in the presence of dimethyl disulphide, are useful precursors of polyfluoroalkane-sulphonic acids.

  通过两种新途径合成的甲基多氟烷基硫化物：（i）多氟碘代烷与二甲基硫醚或二甲基二硫化物的光化学反应，和（ii）多氟碘代烷与甲烷硫醇钠在二甲基二硫化物存在下的反应是多氟链烷磺酸的有用前体。

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