Cyclopenta-1,3-Diene 环戊二烯

CAS 542-92-7 MFCD00542927

化学结构图

542-92-7
SMILES: C1=CCC=C1

化学属性

Mol. Weight66.11
Mol. FormulaC5H6
Solubility不溶于水,溶于乙醇、乙醚、苯等多数有机溶剂。
Density0.805000

别名和识别编码

Synonym 1,3-cyclopentadiene Cyclopentadiene Pentole Pyropentylene R-Pentine cyclopenta-1,3-diene cyclopentadiene 环戊二烯
EC Number208-835-4
CAS Number542-92-7
Chemical NameCyclopenta-1,3-Diene
Wiswesser Line NotationL5 AHJ
LabNetwork Molecule IDLN01813665
Chemical Name Translation环戊二烯
PubChem Substance ID7612
InChIInChI=1S/C5H6/c1-2-4-5-3-1/h1-4H,5H2
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分类

  • {Chemicalbook} 农药中间体: 杀虫剂中间体: 其他杀虫剂
  • {uni_hamburg} no charge; carbocycle; alicycle; 5ring; 1fragment

相关文献及参考

  • Short: II/14a Title: Molecular Constants: Diamagnetic Molecules Author: Demaison, J.; Dubrulle, A.; Hüttner, W.; Tiemann, E. Editor: Hellwege, K.-H.; Hellwege, A.M. Source: Landolt-Börnstein, New Series Volume: II/14a Page: 1-788 Year: 1982 Keyword: organic compounds; molecular constants; spectroscopy; microwave spectroscopy ISBN: 3-540-11365-7 ISBN: 978-3-540-11365-2 Internet Resource: DOI:10.1007/b19966 RefComment: 196 figs., XI
  • Short: II/19b Title: Molecular Constants: Rotational, Centrifugal Distortion and Related Constants of Diamagnetic Asymmetric Top Molecules Author: Demaison, J.; Hüttner, W.; Vogt, J.; Wlodarczak, G. Editor: Hüttner, W. Source: Landolt-Börnstein, New Series Volume: II/19b Year: 1992 Keyword: organic compounds; molecular constants; spectroscopy; microwave spectroscopy ISBN: 3-540-54578-6 ISBN: 978-3-540-54578-1 Internet Resource: DOI:10.1007/b44334 RefComment: XI, 488 pages. Abstract: Volume II/19 Molecular Constants mostly from Microwave, Molecular Beam and Sub-Doppler Laser Spectroscopy is a supplement to the earlier volumes II/4, II/6, and II/14. The slight change in the title reflects current trends in the applications of spectroscopic methods. Together, the four volumes collect all the critically evaluated data published up to 1989/90 on constants of free molecules obtained by classical and modern spectroscopy. Volume II/19 is divided into four parts to record the growing number of investigations, especially in the microwave and millimeter wave regions, where modern techniques like Fourier Transform Microwave Spectroscopy have made new objects of interest such as molecular complexes and clusters accessible to study. Subvolume II/19b contains corresponding data on diamagnetic asymmetric top molecules.
  • Short: II/25D Title: Structure Data of Free Polyatomic Molecules: Molecules Containing Five or More Carbon Atoms Author: Graner, G.; Hirota, E.; Iijima, T.; Kuchitsu, K.; Ramsay, D.A.; Vogt, J.;

安全信息

UN Number 1993
Warnings 危化品目录(2015)
RTECSGY1000000
TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 200 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   TPKVAL Toksikologiya Novykh Promyshlennykh Khimicheskikh Veshchestv.
   Toxicology of New Industrial Chemical Substances.  For English translation,
   see TNICS*.  (Izdatel'stvo Meditsina, Moscow, USSR)  No.1-    1961-
   Volume(issue)/page/year: 9,27,1967

TYPE OF TEST            : LC50 - Lethal concentration, 50 percent kill
ROUTE OF EXPOSURE       : Inhalation
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 14 gm/m3
TOXIC EFFECTS :
   Behavioral - excitement
   Behavioral - muscle contraction or spasticity
   Behavioral - aggression
REFERENCE :
   GTPZAB Gigiena Truda i Professional'nye Zabolevaniya.  Labor Hygiene and
   Occupational Diseases. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR)
   V.1-36, 1957-1992. For publisher information, see MTPEEI
   Volume(issue)/page/year: 9(12),13,1965

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 800 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   TPKVAL Toksikologiya Novykh Promyshlennykh Khimicheskikh Veshchestv.
   Toxicology of New Industrial Chemical Substances.  For English translation,
   see TNICS*.  (Izdatel'stvo Meditsina, Moscow, USSR)  No.1-    1961-
   Volume(issue)/page/year: 9,27,1967

TYPE OF TEST            : LC50 - Lethal concentration, 50 percent kill
ROUTE OF EXPOSURE       : Inhalation
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 39 gm/m3
TOXIC EFFECTS :
   Behavioral - excitement
   Behavioral - muscle contraction or spasticity
   Behavio

Hazard statements
  • H226 Flammable liquid and vapour 易燃液体和蒸气
  • H228 Flammable solid 易燃固体
  • H301 Toxic if swallowed 吞食有毒
  • H302 Harmful if swallowed 吞食有害
  • H312 Harmful in contact with skin 皮肤接触有害
  • H315 Causes skin irritation 会刺激皮肤
  • H319 Causes serious eye irritation 严重刺激眼睛
  • H332 Harmful if inhaled 吸入有害
  • H335 May cause respiratory irritation 可能导致呼吸道刺激
  • H411 Toxictoaquaticlifewithlonglastingeffects 对水生生物有毒性并具有长期影响。
Precautionary statements
  • P210 Keep away from heat/sparks/open flames/hot surfaces. — No smoking. 远离热源/火花/明火/热的表面。——禁止吸烟。
  • P233 Keep container tightly closed. ?保持容器密闭。
  • P240 Ground/bond container and receiving equipment. 与地面接触/连接集装箱和接受设备。
  • P241 Use explosion-proof electrical/ventilating/lighting/…/equipment. 使用防爆电气/通风/照明/ .../设备。
  • P242 Use only non-sparking tools. 只能使用无火花工具。
  • P243 Take precautionary measures against static discharge. 采取预防措施,防止静电放电。
  • P260 Do not breathe dust/fume/gas/mist/vapours/spray. 不要吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P270 Do not eat, drink or smoke when using this product. 使用本产品时不要吃东西,喝水或吸烟。
  • P271 Use only outdoors or in a well-ventilated area.? 只能在室外或通风良好的地方使用。
  • P273 Avoid release to the environment. 避免释放到环境中。
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
  • P301+P310
  • P301+P312
  • P302+P352
  • P303+P361+P353
  • P304+P312
  • P304+P340
  • P305+P351+P338
  • P312 Call a POISON CENTER or doctor/physician if you feel unwell. 如果你感觉不适,呼叫解毒中心或医生/医师。
  • P314 Get medical advice/attention if you feel unwell. 获取医疗咨询/就医,如果你觉得不舒服
  • P321 Specific treatment (see … on this label). 具体治疗(见本标签上的)。
  • P322 Specific measures (see …on this label). 具体治疗(见本标签上的)。
  • P330 Rinse mouth. 漱口
  • P332+P313
  • P337+P313
  • P361 Remove/Take off immediately all contaminated clothing. 立即去除/脱掉所有被污染的衣服。
  • P362 Take off contaminated clothing and wash before reuse. 脱掉污染的衣服,清洗后方可重新使用
  • P363 Wash contaminated clothing before reuse. 被污染的衣服洗净后方可重新使用。
  • P370+P378
  • P391 Collect spillage. Hazardous to the aquatic environment 收集对水环境有危害的泄漏物。
  • P403+P233
  • P403+P235
  • P405 Store locked up. 上锁保管。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
Restrict 危险品

其他信息

  • 稳定性:Stable at room temperature. Incompatible with oxidizing agents, acids and a wide variety of other compounds. May form peroxides in storage. May undergo spontaneous polymerisation. Decomposes on heating. Highly flammable. Mixtures with air are explosive.
  • 生产方法:其制备方法是由煤焦油苯前馏分分离得到较纯的环戊二烯二聚体,经高温裂解和分馏得到环戊二烯单体。 将环戊二烯二聚体加入用载热油循环加热的二聚体裂解釜中,当釜温达到165℃时,二聚体热解明显加快,通过直接与热解釜连接的填料塔进行分馏。环戊二烯从塔顶蒸出,控制冷却水量,收集塔顶温度在39~43℃的馏分即为所需产物,环戊二烯收率为58%左右。此过程为间歇法中温裂解。若改为连续管道高温裂解,则反应收率可达90%以上。
  • MOL 文件:542-92-7.mol
  • HazardClass:3.2
  • 用途:主要用于石油树脂和合成橡胶。以环戊二烯为第三单体合成乙丙橡胶。环戊二烯性质活泼,作为有机合成工业的原料已显得起来越重要。主要利用途经如下。1.环戊二烯聚合反应的应用 环戊二烯能聚合成双环戊二烯、三环戊二烯、四或五环戊二烯等聚合物,其中以双环戊二烯用途最大。它是多种合成橡胶和乙丙橡胶(EpDM)的第三单体。环戊二烯和双环戊二烯热聚合,可制得石油树脂,用于增粘剂、增塑剂、涂料、防腐剂和油墨等。2.环戊二烯加成反应的应用 环戊二烯选择加氢制环戊烯是工业生产环戊烯的主要方法。3.双烯加成反应的应用 环戊二烯极易与烯烃进行Diels-Alder双烯加成反应,通常生成双环[2.2.1]庚烯衍生物。通过双烯加成可将环戊二烯转化生成许多有用的衍生物。如环戊二烯与乙烯加成生成降冰片烯;与丁二烯反应生成5-乙烯基-2-降冰片烯(VNB),再转位生成5-乙叉-2-降冰片稀(ENB);与间戊二烯反应生成5-丙烯基-2-降冰片烯(PNB);与顺丁烯二酸酐反应生成双环[2.2.1]庚-5-烯-2,3-二羧酸酐(降冰片二酸酐)。此外,环戊二烯分别与丙烯、丙烯腈、异戊二烯经Diels-Alder反应制得5-甲基-2-降冰片烯、5-氰基-2-降冰片烯、5-或6-甲基四氢茚等都是合成树脂的单体。4.卤化反应的利用 卤素和卤氢酸能迅速地加到环戊二烯的不饱和双键上而生成许多衍生物,如六氯环戊二烯有很大的工业价值,是合成农药艾氏剂、狄氏剂、氯丹、硫丹、遍地克、草完降、灭蚊灵、碳氯灵、七氯等农药原料。5.缩合反应的作用 环戊二烯中的亚甲基非常活泼,能够与各种醛、酮等进行缩合生成大量的衍生物。丙酮和环戊二烯反应生成的二甲基甲叉茂能与丁二烯共聚制备橡胶。6.氧化反应的应用工业上利用环戊二烯或含环戊二烯的混合物气相催化氧化制取马来酸酐。7.合成异氰酸酯类化合物 环戊二烯与丙烯腈加成生成2-氰基降冰片烯,再经羧基合成等反应制得二异氰酸酯化合物。它们都是聚氨酯塑料的原料。8.合成多元醇化合物 双环戊二烯经羧基合成得到二醛,再加氢即可制得二元醇。它可在聚氨酯生产上行到应用,如用作增塑剂。与甲苯二异氰酸酯、己二酸反应,则可制得热塑性聚氨酯塑料。六氯环戊二烯与二乙酰基环戊烯加成反应后制成的多元醇,再与4,4'二异氰酸酯二苯基甲烷反应生成耐冲击热稳定性能优异的聚合物。9.合成檀香醇 由环戊二烯作原料可制取β-檀香醇。此外,环戊二烯与溴代巴豆酸作原料经一系列反应也可制取β-檀香醇。β-檀香醇是一种香气优雅、留香持久的名贵香料之一。10.合成大比重高能烃类燃料 由于双环戊二烯和环戊二烯的密度高,燃烧时产生很高的热值,这种性能使之成为优良的高能燃料。
  • 外观性质:无色液体,有类似萜烯气味。
  • PackingGroup:III

系列性分类


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