双乙烯酮

双乙烯酮用途

【用途一】
作为有机合成试剂,用于制备农药、染料、颜料中间体=、乙酰乙酰苯胺（AAA）及吡唑酮（PMP）衍生物。
【用途二】
用作染料、颜料、农药、医药及有机合成中间体
【用途三】
双乙烯酮是农药、医药的重要中间体，可以制备杀菌剂拌种灵、禾穗胺、萎锈灵、恶霉灵、二甲嘧酚、乙嘧酚，杀虫剂久效磷、磷胺、蝇毒磷、胺丙畏、嘧啶氧磷、百治磷、二嗪磷、杀线威、抗蚜威、乐果、氧乐果，除草剂甲草胺、乙草胺、丁草胺、喹禾灵、毒草胺、莎稗磷等。
【用途四】
双烯酮的反应能力很强，可衍生多种产品，是精细化学品染料、医药、农药、食品和饲料添加剂、助剂等的原料。双烯酮和二乙胺反应得到的乙酰乙酰二乙胺是有机磷杀虫剂磷胺的中间体；而与一甲胺反应得到的乙酰乙酰甲胺则是久效磷的中间体。双烯酮与氨反应生成乙酰乙酰胺，用于合成染料中间体1-（4-氯苯基）-3-甲基-5-吡唑酮、1-（4-磺酸基苯基）-3-甲基-5-吡唑酮；双烯酮与乙醇反应生成乙酰乙酸乙酯，用于合成染料中间体1-苯基-3-甲基-5-吡唑酮、1-（2，5-二氯-4-磺酸基苯基）-3-甲基-5-吡唑酮等。由这些中间体可制得染料永固黄G、酸性媒介枣红BN、中性橙RL、中性棕5RL、中性深棕BRL、酸性嫩黄G、弱酸嫩黄G、酸性嫩黄2G、活性嫩黄K-6G、活性嫩黄M-5G、活性嫩黄X-6G、中性桃红BL等。1-苯基-3-甲基-5-吡唑酮及其衍生物更多用于解热镇痛药安替比林、氨基比林、安乃近等的生产。双烯酮还可用于氨基酸的合成。双烯酮和邻硝基苯胺、乙醇胺为原料，可制得饲料添加剂喹乙醇（快育灵）。双烯酮用于合成多种杂环化合物，例如合成吡咯衍生物、异噁唑衍生物、吡唑酮衍生物、嘧啶衍生物、噻唑衍生物、喹啉类化合物、香豆素类化合物、呋喃衍生物；双烯酮还可以与一系列化合物反应，生成吡喃酮、吡啶酮、二氧六环、噁嗪及黄酮类化合物等。

双乙烯酮名称

[ CAS 号 ]:
674-82-8

[ 中文名 ]:
双乙烯酮

[ 英文名 ]:
Diketene

[中文别名 ]:

[英文别名 ]:

ACETYLKETENE
4-Methylidenoxetan-2-on
Acety ketene
Diketene(DK)
4-Methyleneoxetan-2-one
Ketene dimer
4-methylideneoxetan-2-one
EINECS 211-617-1
But-1-ene-1,3-dione
Ketenedimere

双乙烯酮物理化学性质

[ 密度 ]:
1.1±0.1 g/cm3

[ 沸点 ]:
127.4±0.0 °C at 760 mmHg

[ 熔点 ]:
-7.5°C

[ 分子式 ]:
C₄H₄O₂

[ 分子量 ]:
84.073

[ 闪点 ]:
34.4±0.0 °C

[ 精确质量 ]:
84.021126

[ PSA ]:
26.30000

[ LogP ]:
0.27

[ 外观性状 ]:
无色液体

[ 蒸汽密度 ]:
2.9 (vs air)

[ 蒸汽压 ]:
11.1±0.2 mmHg at 25°C

[ 折射率 ]:
1.450

[ 储存条件 ]:
库房通风低温干燥,与氧化剂(硝铵)、食品添加剂分开存放

双乙烯酮MSDS

详细MSDS(安全技术说明书)

双乙烯酮毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: RQ8225000

CHEMICAL NAME :: 2-Oxetanone, 4-methylene-

CAS REGISTRY NUMBER :: 674-82-8

BEILSTEIN REFERENCE NO. :: 0104541

LAST UPDATED :: 199710

DATA ITEMS CITED :: 15

MOLECULAR FORMULA :: C4-H4-O2

MOLECULAR WEIGHT :: 84.08

WISWESSER LINE NOTATION :: T4VOY DHJ CU1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: Standard Draize test

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

REFERENCE :: 85JCAE "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986 Volume(issue)/page/year: -,301,1986

TYPE OF TEST :: Open irritation test

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

REFERENCE :: UCDS** Union Carbide Data Sheet. (Union Carbide Corp., 39 Old Ridgebury Rd., Danbury, CT 06817) Volume(issue)/page/year: 2/20/1963

TYPE OF TEST :: Standard Draize test

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

REFERENCE :: IHFCAY Industrial Hygiene Foundation of America, Chemical and Toxicological Series, Bulletin. (Pittsburgh, PA) 1947-69. Volume(issue)/page/year: 6,1,1967

TYPE OF TEST :: Standard Draize test

ROUTE OF EXPOSURE :: Administration into the eye

SPECIES OBSERVED :: Rodent - rabbit

REFERENCE :: 85JCAE "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986 Volume(issue)/page/year: -,301,1986

TYPE OF TEST :: Standard Draize test

ROUTE OF EXPOSURE :: Administration into the eye

SPECIES OBSERVED :: Rodent - rabbit

REFERENCE :: UCDS** Union Carbide Data Sheet. (Union Carbide Corp., 39 Old Ridgebury Rd., Danbury, CT 06817) Volume(issue)/page/year: 2/20/1963

TYPE OF TEST :: Standard Draize test

ROUTE OF EXPOSURE :: Administration into the eye

SPECIES OBSERVED :: Rodent - rabbit

REFERENCE :: IHFCAY Industrial Hygiene Foundation of America, Chemical and Toxicological Series, Bulletin. (Pittsburgh, PA) 1947-69. Volume(issue)/page/year: 6,1,1967 ** ACUTE TOXICITY DATA **

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 560 uL/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 28,313,1974

TYPE OF TEST :: LCLo - Lowest published lethal concentration

ROUTE OF EXPOSURE :: Inhalation

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 20000 ppm/1H

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: IHFCAY Industrial Hygiene Foundation of America, Chemical and Toxicological Series, Bulletin. (Pittsburgh, PA) 1947-69. Volume(issue)/page/year: 6,1,1967

TYPE OF TEST :: LDLo - Lowest published lethal dose

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 :: KODAK* Kodak Company Reports. (343 State St., Rochester, NY 14650) Volume(issue)/page/year: 21MAY1971

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 2830 uL/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 28,313,1974

TYPE OF TEST :: LC50 - Lethal concentration, 50 percent kill

ROUTE OF EXPOSURE :: Inhalation

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 3 gm/m3/2H

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85JCAE "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986 Volume(issue)/page/year: -,301,1986

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 10 mL/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: KODAK* Kodak Company Reports. (343 State St., Rochester, NY 14650) Volume(issue)/page/year: 21MAY1971 *** OCCUPATIONAL EXPOSURE LIMITS *** OEL-RUSSIA:STEL 1 mg/m3 JAN 1993

双乙烯酮安全信息

[ 符号 ]:

GHS02, GHS06

[ 信号词 ]:
Danger

[ 危害声明 ]:
H226-H302-H331

[ 警示性声明 ]:
P261-P301 + P312 + P330-P304 + P340 + P312-P403 + P233-P403 + P235

[ 个人防护装备 ]:
Eyeshields;Faceshields;full-face respirator (US);Gloves;multi-purpose combination respirator cartridge (US);type ABEK (EN14387) respirator filter

[ 危害码 (欧洲) ]:
Xn:Harmful

[ 风险声明 (欧洲) ]:
R10;R20

[ 安全声明 (欧洲) ]:
S3-S36/37-S33-S24/25-S23-S16

[ 危险品运输编码 ]:
UN 2929 6.1/PG 2

[ WGK德国 ]:
2

[ RTECS号 ]:
RQ8225000

[ 包装等级 ]:
I

[ 危险类别 ]:
6.1(a)

双乙烯酮上下游产品

双乙烯酮上游产品

双乙烯酮下游产品

双乙烯酮制备

1.工业上乙酸制取双烯酮，也可用丙酮、乙酐、乙酸酯为原料进行热分解。丙酮热分解法可用于小规模生产，这种方法由于副产甲烷，得到的乙烯酮气体的纯度低，同时要除去残留的丙酮也比较困难。冰醋酸在磷酸三乙酯存在下，于750-780℃裂解得乙烯酮，再于8-10℃聚合生成双乙烯酮。

2.将三只洗气瓶串连，分别置于千冰一丙酮冷阱中，在第二、第三只洗气瓶中各加入150毫升无水丙酮。通入乙烯酮气体(注)，直至通入量达到2摩尔，约需4一4.5小时。在乙烯酮通入1.5小时后，倒出第一只冷阱中的干冰一乙酮，在乙烯酮通入结束2小时后，倒出第二只冷阱中的干冰一丙酮，再过6小时后，倒出第三只瓶中的干冰一丙酮。在实验开始24小时后，让体系达到室温。合并洗气瓶中的液体进行分馏。先除去丙酮，收集67-69℃/92mm的馏份为产品，重42-46克(50一55%)。

双乙烯酮文献

Chemical reactivity and biological activity of diketene.

Chem. Res. Toxicol. 21(10) , 1964-9, (2008)

The alkylating potential of diketene (4-methylene-2-oxetanone), the basic unit of many derivatives of pesticides, chemicals, pharmaceuticals, and dyestuffs, was investigated kinetically. The nucleophi...

Novel approach to 1,5-benzodiazepine-2-ones containing peptoid backbone via one-pot diketene-based Ugi-4CR.

J. Comb. Chem. 12(4) , 497-502, (2010)

An efficient and simple route for preparation of substituted 1,5-benzodiazepine-2-one containing peptoid backbone is presented. The classical Ugi reaction is considerably extended by application of o-...

One-pot multicomponent synthesis of 1-aryl-5-methyl-N-R2-1H-1,2,3-triazole-4-carboxamides: an easy procedure for combinatorial chemistry.

J. Comb. Chem. 11(3) , 481-5, (2009)

A convenient synthetic protocol was elaborated for creation of combinatorial libraries of 1-(R(1)-phenyl)-5-methyl-N-R(2)-1H-1,2,3-triazole-4-carboxamides. As starting materials, commercially availabl...

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