环戊二烯

环戊二烯用途

1.环戊二烯在农药上用于合成杀虫剂氯丹、硫丹的中间体四氯环戊烷，也可用于生产杀虫剂吡虫啉的中间体，此外，它主要用于树脂工业，合成橡胶等。

2.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。

3.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。

4.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。

5.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。

6.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。

7.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。

8.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。

9.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。

10.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。

11.用作有机合成中间体，及用于制造农药杀虫剂氯丹等。

环戊二烯名称

[ CAS 号 ]:
542-92-7

[ 中文名 ]:
环戊二烯

[ 英文名 ]:
Cyclopentadiene

[英文别名 ]:

cyclopentadienalpotassium
1,3-cyclopentadiene
Cyclopenta-1,3-diene
Potassium,2,4-cyclopentadien-1-yl
Cyclopentadienylpotassium
1,3-Cyclopentadiene,potassium complex
cyclopentanediene
cyclopentadienyl
POTASSIUM CYCLOPENTADIENIDE
EINECS 208-835-4

环戊二烯物理化学性质

[ 密度 ]:
0.9±0.1 g/cm3

[ 沸点 ]:
41.5±0.0 °C at 760 mmHg

[ 熔点 ]:
-97.2ºC

[ 分子式 ]:
C₅H₆

[ 分子量 ]:
66.101

[ 闪点 ]:
-32.2±13.0 °C

[ 精确质量 ]:
66.046951

[ LogP ]:
1.79

[ 外观性状 ]:
无色液体

[ 蒸汽压 ]:
418.5±0.0 mmHg at 25°C

[ 折射率 ]:
1.503

[ 储存条件 ]:
库房通风低温干燥,与氧化剂、酸类分开存放,不宜久储,以防聚合

[ 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.

环戊二烯MSDS

详细MSDS(安全技术说明书)

环戊二烯毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: GY1000000

CHEMICAL NAME :: 1,3-Cyclopentadiene

CAS REGISTRY NUMBER :: 542-92-7

LAST UPDATED :: 199712

DATA ITEMS CITED :: 31

MOLECULAR FORMULA :: C5-H6

MOLECULAR WEIGHT :: 66.11

WISWESSER LINE NOTATION :: L5 AHJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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 - rat

DOSE/DURATION :: 39 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 - 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 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TCLo - Lowest published toxic concentration

ROUTE OF EXPOSURE :: Inhalation

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 350 mg/m3/4H/26W-I

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 *** REVIEWS *** ACGIH TLV-TWA 203 mg/m3 (75 ppm) DTLVS* The Threshold Limit Values (TLVs) and Biological Exposure Indices (BEIs) booklet issues by American Conference of Governmental Industrial Hygienists (ACGIH), Cincinnati, OH, 1996 Volume(issue)/page/year: TLV/BEI,1997 *** U.S. STANDARDS AND REGULATIONS *** MSHA STANDARD-air:TWA 75 ppm (200 mg/m3) DTLVS* The Threshold Limit Values (TLVs) and Biological Exposure Indices (BEIs) booklet issues by American Conference of Governmental Industrial Hygienists (ACGIH), Cincinnati, OH, 1996 Volume(issue)/page/year: 3,66,1971 OSHA PEL (Gen Indu):8H TWA 75 ppm (200 mg/m3) CFRGBR Code of Federal Regulations. (U.S. Government Printing Office, Supt. of Documents, Washington, DC 20402) Volume(issue)/page/year: 29,1910.1000,1994 OSHA PEL (Construc):8H TWA 75 ppm (200 mg/m3) CFRGBR Code of Federal Regulations. (U.S. Government Printing Office, Supt. of Documents, Washington, DC 20402) Volume(issue)/page/year: 29,1926.55,1994 OSHA PEL (Shipyard):8H TWA 75 ppm (200 mg/m3) CFRGBR Code of Federal Regulations. (U.S. Government Printing Office, Supt. of Documents, Washington, DC 20402) Volume(issue)/page/year: 29,1915.1000,1993 OSHA PEL (Fed Cont):8H TWA 75 ppm (200 mg/m3) CFRGBR Code of Federal Regulations. (U.S. Government Printing Office, Supt. of Documents, Washington, DC 20402) Volume(issue)/page/year: 41,50-204.50,1994 *** OCCUPATIONAL EXPOSURE LIMITS *** OEL-AUSTRALIA:TWA 75 ppm (200 mg/m3) JAN 1993 OEL-AUSTRIA:TWA 75 ppm (200 mg/m3) JAN 1993 OEL-BELGIUM:TWA 75 ppm (203 mg/m3) JAN 1993 OEL-DENMARK:TWA 75 ppm (200 mg/m3) JAN 1993 OEL-FINLAND:TWA 75 ppm (200 mg/m3);STEL 115 ppm (310 mg/m3) JAN 1993 OEL-FRANCE:TWA 75 ppm (200 mg/m3) JAN 1993 OEL-GERMANY:TWA 75 ppm (200 mg/m3) JAN 1993 OEL-HUNGARY:TWA 20 mg/m3;STEL 40 mg/m3 JAN 1993 OEL-THE NETHERLANDS:TWA 75 ppm (200 mg/m3) JAN 1993 OEL-THE PHILIPPINES:TWA 75 ppm (200 mg/m3) JAN 1993 OEL-RUSSIA:STEL 5 mg/m3 JAN 1993 OEL-SWITZERLAND:TWA 75 ppm (200 mg/m3) JAN 1993 OEL IN BULGARIA, COLOMBIA, JORDAN, KOREA check ACGIH TLV OEL IN NEW ZEALAND, SINGAPORE, VIETNAM check ACGIH TLV *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH RECOMMENDED EXPOSURE LEVEL (REL) : NIOSH REL TO CYCLOPENTADIENE-air:10H TWA 75 ppm REFERENCE : NIOSH* National Institute for Occupational Safety and Health, U.S. Dept. of Health, Education, and Welfare, Reports and Memoranda. Volume(issue)/page/year: DHHS #92-100,1992 NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 20065 No. of Facilities: 3138 (estimated) No. of Industries: 19 No. of Occupations: 26 No. of Employees: 18381 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 20065 No. of Facilities: 3 (estimated) No. of Industries: 1 No. of Occupations: 3 No. of Employees: 51 (estimated)

环戊二烯安全信息

[ 危险品运输编码 ]:
UN 1993

[ 包装等级 ]:
III

[ 危险类别 ]:
3.2

环戊二烯合成路线

详细合成路线

环戊二烯上下游产品

环戊二烯上游产品

环戊二烯下游产品

环戊二烯制备

1.工业上环戊二烯主要来源于煤炼焦过程所得粗苯中的苯前馏分，以及烃类裂解制乙烯时副产的C5馏分。在裂解C5馏分中，环戊二烯含约10-15%，是环戊二烯的主要来源；轻苯精炼加工中所得的苯前馏分内含环戊二烯约30%，利用环戊二烯易受热二聚的特性，首先在100-130℃温度下加热混合馏分，使环戊二烯二聚成双环戊二烯，经蒸馏得到粗双环戊二烯。再经高温解聚反应得高纯度的环戊二烯。合成法制备环戊二烯有以下方法。（1）以环戊烯或环戊烷为原料，用活性氧铝（84%）、氧化铬（14%）、氧化钾2%为催化剂，于600℃、2.7-3.3kPa下脱氢而得。（2）由1,4-戊二烯脱氢环化制环戊二烯；（3）由1,3-戊二烯脱氢、环化制环戊二烯。

2.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。