异丁烯 | 115-11-7

• 物质功能分类: 有机原料 - 烃类化合物及其衍生物 - 无环烃
• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 中文名称: 异丁烯
• 中文别名: 2-甲基丙烯；1,1-二甲基乙烯；2-甲基-1-丙烯
• 英文名称: isobutene
• 英文别名: isobutylen；isobutylene；2-methylpropene；2-methylprop-1-ene
• CAS: 115-11-7
• 化学式: C₄H₈
• mdl: MFCD00008898
• 分子量: 56.1075
• InChiKey: VQTUBCCKSQIDNK-UHFFFAOYSA-N

物化性质

• 熔点：
  −140 °C
• 沸点：
  −6.9 °C(lit.)
• 密度：
  0.5879
• 蒸气密度：
  2 (vs air)
• 闪点：
  -80 °C
• LogP：
  2.35 at 20℃
• 物理描述：
  Isobutylene is a colorless gas with a faint petroleum-like odor. For transportation it may be stenched. It is shipped as a liquefied gas under its own vapor pressure. Contact with the liquid can cause frostbite. It is easily ignited. Its vapors are heavier than air and a flame can flash back to the source of leak very easily. The leak can either be a liquid or vapor leak. It can asphyxiate by the displacement of air. Under prolonged exposure to fire or heat the containers may rupture violently and rocket. It is used in the production of isooctane, a high octane aviation gasoline.
• 颜色/状态：
  Colorless gas
• 气味：
  Coal gas odor
• 溶解度：
  In water, 263 mg/L at 25 °C
• 蒸汽密度：
  1.9 (NTP, 1992) (Relative to Air)
• 蒸汽压力：
  2,308 mm Hg at 25 °C
• 亨利常数：
  Henry's Law constant = 0.218 atm cu-m/mol at 25 °C
• 大气OH速率常数：
  5.14e-11 cm3/molecule*sec
• 稳定性/保质期：
  1. 稳定性^[28]：稳定。 2. 禁配物^[29]：强氧化剂、强酸、卤代烃、卤素。 3. 应避免的条件^[30]：受热。 4. 聚合危害^[31]：可能发生聚合。
• 自燃温度：
  869 °F (465 °C)
• 分解：
  Hazardous decomposition products formed under fire conditions: Carbon oxides
• 折光率：
  Index of refraction: 1.3926 at 25 °C
• 保留指数：
  384 ;392 ;391 ;391 ;390 ;390 ;380 ;390 ;385 ;370 ;384 ;390 ;383 ;384.2 ;384.9 ;387 ;388 ;388 ;386 ;383 ;390 ;400

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  4
• 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：
  0

ADMET

代谢

大鼠（Sprague Dawley）和小鼠（B6C3F1）对异丁烯（2-甲基丙烯）的代谢遵循米氏动力学（Michaelis-Menten）。最大代谢消除速率分别为大鼠340 umol/kg/hr和小鼠560 umol/kg/hr。达到Vmax/2的大气浓度分别为大鼠1200 ppm和小鼠1800 ppm。在稳态下，大气浓度低于约500 ppm时，异丁烯的代谢速率与其浓度成正比。1,1-二甲基环氧乙烷在大鼠代谢异丁烯过程中形成作为主要的活性中间体，并且可以在动物的呼出气体中检测到。在异丁烯代谢饱和的条件下，封闭暴露系统中的1,1-二甲基环氧乙烷浓度仅约为乙烯氧化物观察到的浓度的1/15，约为乙烯或1,3-丁二烯代谢中间体1,2-环氧-3-丁烯观察到的浓度的1/100。

Metabolism of isobutene (2-methylpropene) in rats (Sprague Dawley) and mice (B6C3F1) follows kinetics according to Michaelis-Menten. The maximal metabolic elimination rates are 340 umol/kg/hr for rats and 560 umol/kg/hr for mice. The atmospheric concentration at which Vmax/2 is reached is 1200 ppm for rats and 1800 ppm for mice. At steady state, below atmospheric concentrations of about 500 ppm the rate of metabolism of isobutene is direct proportional to its concentration. 1,1-Dimethyloxirane is formed as a primary reactive intermediate during metabolism of isobutene in rats and can be detected in the exhaled air of the animals. Under conditions of saturation of isobutene metabolism the concentration of 1,1-dimethyloxirane in the atmosphere of a closed exposure system is only about 1/15 of that observed for ethene oxide and about 1/100 of that observed for 1,2-epoxy-3-butene as intermediates in the metabolism of ethene or 1,3-butadiene.

来源:Hazardous Substances Data Bank (HSDB)

代谢

研究了2-甲基丙烯的生物转化，2-甲基丙烯是一种在工业中广泛使用的气态烯烃。在体外实验中，使用了大鼠、小鼠和人类的肝脏组织。种间比较显示，初级环氧代谢物水平在人类肝脏匀浆中最低，其次是大鼠和小鼠。然而，在人类肝脏样本中观察到了显著的个体间差异。在分析的16个样本中，只有2个样本含有可测量的环氧量，而在其他样本中仅能检测到痕迹量。已经证实大鼠肝脏细胞色素P450 2E1参与了2-甲基丙烯活化为其环氧代谢物2-甲基-1,2-环氧丙烷的过程。与啮齿动物相比，人类肝脏样本的混合功能氧化酶系统的能力较低。关于环氧解毒酶，人类肝脏组织中观察到高微体环氧水解酶活性，大鼠肝脏中为中等活性，而小鼠肝脏中测得的活性较低。这些发现与三种研究中动物肝脏组织体外测得的环氧水平呈负相关。可以得出结论，就2-甲基丙烯的体外代谢而言，无论是小鼠还是大鼠，都不能很好地代表人类的情况。尽管涉及相同的生物转化途径，但环氧水平的显著定量差异被观察到。结果表明，人类肝脏组织在体外接触初级代谢物2-甲基-1,2-环氧丙烷的浓度比啮齿动物肝脏要低。

The biotransformation of 2-methylpropene, a gaseous alkene widely used in industry, was investigated in vitro in liver tissue of rats, mice, and humans. Interspecies comparison revealed that the lowest levels of the primary epoxide metabolite were detected in incubations of 2-methylpropene with human liver homogenate, followed by rat and mouse, respectively. Among the human liver samples, however, important interindividual variations were observed. Out of the 16 samples analyzed, only 2 contained measurable epoxide amounts, while in the other samples only traces were detectable. The involvement of rat liver cytochrome P450 2E1 in the activation of 2-methylpropene to its epoxide 2-methyl-1,2-epoxypropane has been established. The lower capacity of the mixed function oxidase system in human liver samples compared to rodents is confirmed. Concerning epoxide detoxifying enzymes, a high microsomal epoxide hydrolase activity was observed in human liver tissue and an intermediate in rat liver, while a low activity was measured in mouse liver. These findings were inversely correlated with the epoxide levels measured in vitro in liver tissue of the three species studied. It can be concluded that, as far as the in vitro metabolism of 2-methylpropene is concerned, neither mouse nor rat represents a good model for the human situation. Although, the same biotransformation pathways are involved, marked quantitative differences in epoxide levels were observed. The results indicate that human liver tissue is exposed in vitro to smaller concentrations of the primary metabolite 2-methyl-1,2-epoxypropane than rodent liver.

来源:Hazardous Substances Data Bank (HSDB)

代谢

年龄和性别对2-甲基丙烯在体外生物转化的影响进行了研究，2-甲基丙烯是一种被代谢为2-甲基-1,2-环氧丙烷的烯烃。研究了不同年龄的布朗挪威大鼠雄性和雌性中环氧丙烷浓度和环氧丙烷代谢酶活性的变化。与年轻动物相比，衰老大鼠的肝脏组织暴露于较小的2-甲基-1,2-环氧丙烷浓度，尽管在衰老过程中的变化相对较小。随着年龄的增长，发现雄性谷胱甘肽S-转移酶和细胞质环氧水解酶活性女性化，以及最年长雌性大鼠的微粒体环氧水解酶活性显著下降和细胞色素p450含量的增加。

The effect of age and gender on the in vitro biotransformation of 2-methylpropene, an alkene metabolized to 2-methyl-1,2-epoxypropane, was studied. The epoxide concentration and the epoxide metabolizing enzymatic activities were investigated in male and female Brown Norway rats of different ages. Liver tissue of senescent rats was exposed to smaller 2-methyl-1,2-epoxypropane concentrations than that of young animals, although changes during ageing were rather modest. With advancing age a feminization of male glutathione S-transferase and cytosolic epoxide hydrolase activities was found, as well as a significant decline of the female microsomal epoxide hydrolase activity and an increase of the cytochrome p450 content in the oldest female rats.

来源:Hazardous Substances Data Bank (HSDB)

代谢

作为长期毒性研究计划的一个辅助，进行了研究以确定暴露浓度对F344/N大鼠吸收和代谢异丁烯的影响。将11至15周龄的雄性F344/N大鼠暴露于0、40、400或4000 ppm异丁烯2小时，并使用顶空分析方法对异丁烯的血药水平进行了时间过程评估。异丁烯的血药水平在40至400 ppm的暴露浓度之间呈线性关系，但在最高浓度下呈超线性增长，这表明大鼠代谢异丁烯的能力已被超出。在0、2、40、400或4000 ppm [(14)C]异丁烯暴露长达6小时的大鼠中研究了总摄取量、排泄模式和代谢转化。吸入的异丁烯的吸收率约为8%，直到40 ppm异丁烯，但在更高浓度下降低。每ppm.hr暴露代谢的异丁烯量在40 ppm以下也是线性的，但在更高浓度下降低。在400 ppm以下的暴露浓度下，超过90%的异丁烯被代谢，但暴露于大约4000 ppm异丁烯导致大约20%的吸收剂量以未代谢的异丁烯形式呼出。两种尿代谢物被鉴定为异丁烯二醇和2-羟基异丁酸。另外两种尿代谢物暂时被鉴定为异丁烯二醇的硫酸结合物。根据这些研究，在40 ppm异丁烯的暴露下，预计在慢性毒性研究中会有线性剂量-反应关系...

... As an aid to planning long-term toxicity studies, research was conducted to determine the effect of exposure concentrations on the absorption and metabolism of isobutene in F344/N rats. Male F344/N rats (11-15 weeks of age) were exposed for 2 hr to 0, 40, 400, or 4000 ppm isobutene, and a time-course evaluation of blood levels of isobutene was performed using headspace analysis methods. Blood levels of isobutene were linearly related to exposure concentrations between 40 and 400 ppm but increased in a supralinear fashion at the highest concentration, suggesting that the capacity of the rats to metabolize isobutene had been exceeded. Total uptake, excretion patterns, and metabolic conversions were studied in rats exposed for up to 6 hr to 0, 2, 40, 400, or 4000 ppm [(14)C]isobutene. Absorption of the inhaled isobutene was approximately 8% up to 40 ppm isobutene, but decreased at the higher concentrations. The amount of isobutene metabolized per ppm.hr of exposure was also linear up to 40 ppm but decreased at higher concentrations. Over 90% of the absorbed isobutene was metabolized at exposure concentrations up to 400 ppm, but the exposure to approximately 4000 ppm isobutene resulted in approximately 20% of the absorbed dose exhaled as the unmetabolized isobutene. Two urinary metabolites were identified as isobutenediol and 2-hydroxyisobutyric acid. Two other urinary metabolites were tentatively identified as sulfate conjugates of isobutenediol. Based on these studies, linear dose-response relationships would be expected in chronic toxicity studies for exposures up to 40 ppm isobutene ...

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 毒性总结

识别和使用：异丁烯是一种易于液化的气体。它用于生产二异丁烯、三聚物、丁基橡胶和其他聚合物。它还用于生产食品、包装、食品补充剂和塑料的抗氧化剂。人体研究：异丁烯在高浓度下会导致中枢神经系统抑制。中枢神经系统抑制的程度与大脑浓度之间存在线性关系。在用人淋巴细胞进行的体外微核试验中，异丁烯没有表现出致突变性。动物研究：异丁烯在30%的浓度下对小鼠没有中枢神经系统抑制作用，在40%的浓度下7到8分钟内产生兴奋和中枢神经系统抑制，在50%的浓度下2到2.25分钟内立即产生中枢神经系统抑制，或者在60到70%的浓度下50到60秒内产生。通过吸入异丁烯暴露2年，导致小鼠鼻部病变（包括嗅上皮的透明变性）的发病率和/或严重程度增加，以及雄性和雌性小鼠呼吸上皮的透明变性。在雄性和雌性小鼠每天6小时，每周5天，持续105周，暴露于500、2000或8000 ppm的异丁烯中，没有发现异丁烯具有致癌活性的证据。基于甲状腺滤泡细胞癌发病率增加，有证据表明异丁烯对雄性大鼠具有致癌活性。在Escherichia coli、Ames Salmonella typhimurium试验和修改后的沙门氏菌试验中，无论是否加入代谢活化系统，异丁烯的致突变性测试均为阴性。在通过吸入异丁烯处理14周的雄性和雌性小鼠的外周血液中，没有观察到微核红细胞频率的增加。

IDENTIFICATION AND USE: Isobutylene is an easily liquefied gas. It is used to produce diisobutylene, trimers, butyl rubber, and other polymers. It is also used to produce antioxidants for foods, packaging, food supplements, and for plastics. HUMAN STUDIES: Isobutene causes CNS depression at higher concentrations. There is a linear relationship between the degree of CNS depression and the cerebral concentrations. Isobutylene was not mutagenic when tested in the in vitro micronucleus test using human lymphocytes. ANIMAL STUDIES: Isobutene, at 30%, produces no CNS depression in mice, and excitement and CNS depression in 7 to 8 min at 40%, but immediate CNS depression in 2-2.25 min at 50%, or in 50-60 sec at 60 to 70%. Exposure to isobutene by inhalation for 2 years resulted in increased incidences and/or severities of nasal lesions including hyaline degeneration of the olfactory epithelium in mice and hyaline degeneration of the respiratory epithelium in male and female mice. There was no evidence of carcinogenic activity of isobutylene in male or female mice exposed to 500, 2,000, or 8,000 ppm 6 hours per day, 5 days per week, for 105 weeks. There was some evidence of carcinogenic activity of isobutene in male rats based on an increased incidence of follicular cell carcinoma of the thyroid gland. It was negative when tested for mutagenicity in Escherichia coli, the Ames Salmonella typhimurium assay, and a modified Salmonella assay, with and without metabolic activation. No increase in the frequency of micronucleated erythrocytes was seen in peripheral blood of male or female mice treated with isobutylene by inhalation for 14 weeks.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

A4：不能归类为人类致癌物。

A4: Not classifiable as a human carcinogen.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 暴露途径

该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

晕眩。嗜睡。乏力。恶心。昏迷。呕吐。

Dizziness. Drowsiness. Lethargy. Nausea. Unconsciousness. Vomiting.

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

毒理性

• 皮肤症状

接触液体时：冻伤。

ON CONTACT WITH LIQUID: FROSTBITE.

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

吸收、分配和排泄

在大鼠和小鼠的代谢研究中，吸入的异丁烯在大脑和实质性器官的水平相似，但在脂肪组织中的水平显著高于大脑、肝脏、肾脏或脾脏。据推测，异丁烯的主要排泄途径是通过肺呼出。

In metabolic studies on rats and mice, inhaled isobutene levels in the brain and parenchymatous organs were similar, but the level in the fatty tissue was significantly higher than in the brain, liver, kidneys, or spleen. It is assumed that the major route of excretion of isobutene is by pulmonary exhalation.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 危险等级：
  2.1
• 危险品标志：
  F+
• 安全说明：
  S16,S33,S9
• 危险类别码：
  R12
• WGK Germany：
  -
• 海关编码：
  2901233000
• 危险品运输编号：
  UN 1055 2.1
• 危险类别：
  2.1
• RTECS号：
  UD0890000
• 包装等级：
  O52
• 储存条件：
  储存注意事项： - 储存于阴凉、通风的易燃气体专用库房。 - 远离火种、热源，库温不宜超过30℃。 - 应与氧化剂分开存放，切忌混储。 - 使用防爆型照明和通风设施。 - 禁止使用易产生火花的机械设备和工具。 - 储区应备有泄漏应急处理设备。

SDS

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