Diketene 二乙烯酮

CAS 674-82-8 MFCD00005173

化学结构图

674-82-8
SMILES: C=C1CC(=O)O1

化学属性

Mol. FormulaC4H4O2
Mol. Weight84.08
Refractive indexn20/D 1.439(lit.)
Boiling Point69-70 °C/100 mmHg(lit.)
Density1.09 g/mL at 25 °C(lit.)
Autoignition Point590 °F
Vapor Density2.9 (vs air)
Vapor Pressure7.9 mmHg ( 20 °C)
Flash Point34 ºF
Melting Point-7.5 ºC
Solubility溶于水、多数有机溶剂。

别名和识别编码

Chemical NameDiketene
Beilstein Registry Number0104541
CAS Number674-82-8
PubChem Substance ID12661
EC Number211-617-1
MDL NumberMFCD00005173
Synonym 2-Oxetanone, 4-methylene- 3-Buteno-beta-lactone 3-Butenoic acid, 3-hydroxy-, beta-lactone 3-Butenoic acid, 3-hydroxy-, ß-lactone 3-Butenoic acid, 3-hydroxy-, β-lactone 3-buteno-beta-lactone 3-hydroxy-3-butenoicacibeta-lactone 3-羟基丁烯酸-β-内酯 4-METHYLENE-2-OXETANONE 4-Methylen-2-oxetanon 4-Methylen-2-oxethanon 4-Methylene-2-oxetanone 4-Methylene-2-oxetanone; Diketene; But-3-en-3-olide 4-Methyleneoxetan-2-one 4-methylen-oxetan-2-one 4-methylene-2-oxetanon 4-methylene-2-oxetanone 4-亚甲基-2-氧杂环丁烷酮 ACETYLKETENE Acety ketene But-3-en-3-olide DIKETENE Diketen Diketene Diketene(DK) Dikitene dike
Alfabeta NameDIKETENE
Chemical Name Translation二乙烯酮
Wiswesser Line NotationT4VOY DHJ CU1
LabNetwork Molecule IDLN01308229
InChIInChI=1S/C4H4O2/c1-3-2-4(5)6-3/h1-2H2
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分类

  • {uni_hamburg} no charge; oxygen heterocycle; alicycle; 4ring; ester; lactone; 1fragment
  • {Chemicalbook} 农药中间体: 杀菌剂中间体: 其他类杀菌剂
  • Building Blocks, Carbonyl Compounds, Chemical Synthesis, Lactones, Organic Building Blocks
  • {SNA} Building Blocks, Carbonyl Compounds, Chemical Synthesis, Lactones, Organic Building Blocks

相关文献及参考

  • 1. Aldrichimica Acta 27 , 39, (1994)
  • Merck 14 ,10341
  • Beil. 17 ,V,9,115
  • Fieser 1 ,264 / Fieser 5 ,225 / Fieser 6 ,202 / Fieser 14 ,142
  • Corp MSDS 1 (1), 1301:C / FT-IR 2 (1), 1172:B / FT-NMR 1 (1), 1124:C / RegBook 1 (1), 803:C / Sax 6 , 1679 / Structure Index 1 , 125:B:5
  • Short: II/27C Title: Diamagnetic Susceptibility and Magnetic Anisotropy of Organic Compounds Author: Kumar, Mahendra; Gupta, Rajni Editor: Gupta, Radha Raman Source: Landolt-Börnstein, New Series Volume: II/27C Year: 2008 Keyword: diamagnetic susceptibility; magnetic anisotropy; organic compounds ISBN: 978-3-540-44734-4 (print) ISBN: 978-3-540-44736-8 (online) Internet Resource: doi:10.1007/978-3-540-44736-8 RefComment: VIII, 204 p., Hardcover RefComment: Written for: Scientists and researchers in the fields of physics, chemistry, materials science RefComment: Supplement and Revised Editon to II/16 Abstract: The volume II/27 has been divided into three subvolumes according to the classes of compounds: Subvolume A: Diamagnetic susceptibility and magnetic anisotropy of inorganic and organometallic compounds; Subvolume B: Diamagnetic susceptibility of organic compounds (Part 1); Subvolume C: Diamagnetic susceptibility and magnetic anisotropy of organic compounds (Part 2). The data presented in this volume are based on the literature survey of the chemical abstracts up to 2005.
  • Short: II/6 Title: Molecular Constants from Microwave, Molecular Beam, and Electron Spin Resonance Spectroscopy Author: Demaison, J.; Hüttner, W.; Starck, B.; Buck, I.; Tischer, R.; Winnewisser, M. Editor: Hellwege, K.-H.; Hellwege, A.M. Source: Landolt-Börnstein, New Series Volume: II/6 Year: 1974 Keyword: organic compounds; molecular constants; spectroscopy; microwave spectroscopy ISBN: 3-540-05977-6 ISBN: 978-3-540-05977-6 Internet Resource: DOI:10.1007/b19951 RefComme

安全信息

GHS Symbol
WGK Germany1
Hazard Codes Xn
Hazard statements
  • H226 Flammable liquid and vapour 易燃液体和蒸气
  • H301 Toxic if swallowed 吞食有毒
  • H302 Harmful if swallowed 吞食有害
  • H315 Causes skin irritation 会刺激皮肤
  • H318 Causes serious eye damage 严重伤害眼睛
  • H330 Fatal if inhaled 吸入致命
  • H331 Toxic if inhaled 吸入中毒
  • H332 Harmful if inhaled 吸入有害
  • H335 May cause respiratory irritation 可能导致呼吸道刺激
Personal Protective Equipment Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
RTECSRQ8225000
Signal word Warning
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。
  • P264+P265
  • 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。
  • 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。
  • P281 Use personal protective equipment as required. 使用所需的个人防护装备。
  • P284 Wear respiratory protection.? 佩戴呼吸保护装置。
  • P301+P310
  • P301+P312
  • P301+P316
  • P301+P317
  • P302+P352
  • P303+P361+P353
  • P304+P312
  • P304+P340
  • P305+P351+P338
  • P305+P354+P338
  • P308+P316
  • P309+P311
  • P310 Immediately call a POISON CENTER or doctor/physician. 立即呼救解毒中心或医生/医师。
  • P311 Call a POISON CENTER or doctor/physician. 呼叫解毒中心或医生/医师。
  • 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。
  • P316
  • P317
  • P319
  • P320 Specific treatment is urgent (see … on this label). 紧急具体治疗(见本标签上的)。
  • P321 Specific treatment (see … on this label). 具体治疗(见本标签上的)。
  • P330 Rinse mouth. 漱口
  • P332+P313
  • P332+P317
  • 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
  • P362+P364
  • P370+P378
  • 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.....
Safety Statements
  • S3 Keep in a cool place 保存在阴凉处;
  • S16 Keep away from sources of ignition - No smoking 远离火源,禁止吸烟;
  • S33 Take precautionary measures against static discharges 对静电采取预防措施;
  • S23 Do not breathe gas/fumes/vapour/spray (appropriate wording to be specified by the manufacturer) 不要吸入气体/烟雾/蒸汽/喷雾;
  • S36/37 Wear suitable protective clothing and gloves 穿戴适当的防护服和手套;
  • S24/25 Avoid contact with skin and eyes 避免皮肤和眼睛接触;
Risk Statements
  • R10 Flammable 易燃
  • R20 Harmful by inhalation 吸入有害
  • R40 Limited evidence of a carcinogenic effect 有限证据表明其致癌作用
UN Number 2521 UN 2929 6.1/PG 2
Warnings 危化品目录(2015) TOXIC BY INHALATION, FLAMMABLE
Packing GroupI
Hazard Class6.1(a)
Storage condition 2-8°C
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            : 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

TYPE OF TEST            : LCLo - Lowest published lethal concentration
ROUTE OF EXPOSURE       : Inhalation
SPECIES OBSERVED        : Rodent -

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            : 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

Restrict 危险品

其他信息

  • 刺激数据:皮肤-兔子 20 毫克/24小时 中度;眼睛-兔子 0.05 毫克/24小时 重度
  • 常规方法:本品易燃,应贮于铝制或搪玻璃容器中,低温(0~5℃)存放。运输中不得与火、无机酸及水接触,严禁撞击,以防爆炸。按易燃化学品规定贮运。
  • MOL 文件:674-82-8.mol
  • 蒸气压:7.9 mm Hg ( 20 °C)
  • 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
  • 下游产品:乙酐 --> 乙酰乙酸乙酯 --> 氯乙酰氯 --> 依达拉奉 --> 乙酰乙酸甲酯 --> N-乙酰乙酰苯胺 --> 山梨酸 --> 颜料红 122 --> 精喹禾灵 --> 脱氢乙酸 --> 丁酸酐 --> alpa-乙酰基-gama-丁酯 --> 安赛蜜 --> 咪草烟 --> 4-氯乙酰乙酸乙酯 --> 安塞蜜 --> 邻甲氧基-N-乙酰乙酰苯胺 --> 奥拉多司 --> 乙酰乙酸叔丁酯 --> N,N-二乙基乙酰乙酰胺 --> 马尼地平 --> 盐酸阿米替林 --> 2-氨基-4-甲基-5-甲酰苯胺噻唑 --> N-甲基乙酰基乙酰胺 --> 乙酰乙酸异丁酯 --> 2'-氯-N-乙酰乙酰苯胺 --> 磷胺 --> 1,3-丁二酮胺 --> 2'-甲基乙酰乙酰苯胺 --> 乙酰乙酸正丁酯 --> 芸苔素内酯 --> 庚二酮 --> N-乙酰基-N-(4-氯-2-硝基苯基)乙酰胺 --> 1-(2,5-二氯-4-磺酸苯基)-3-甲基-5-吡唑酮 --> 乙酰乙酸犍牛儿酯 --> 双乙酰乙酰-3,3'-二甲基联苯胺 --> 乙酰基乙酰对甲氧基苯胺
  • 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。
  • 用途二:用作染料、颜料、
  • 外观性质:无色液体,有刺激气味。
  • 毒性分级:中毒
  • 方法一:其制备方法是在催化剂磷酸三乙酯的存在下,使乙酸在700℃左右热裂解,脱水生成乙烯酮,净化的乙烯酮气体在吸收塔内二聚化生成双乙烯酮。若温度过高,已生成的双乙烯酮会发生高聚生成多聚乙烯酮,同时在乙酸热裂解过程中必须加入阻聚剂氨气以免乙烯酮分解。其工艺是乙酸经气化器(在约40 kPa下)气化,在乙酸蒸气中加入乙酸投料量的0.3%的磷酸三乙酯,然后经预热器加热至反应温度,迅速通过裂解
  • 灭火剂:水、泡沫、砂土。
  • 图谱信息:二乙烯酮(67
  • 用途一:作为有机合成试剂,用于制备农药、
  • 蒸气密度:2.9 (vs air)
  • 方法二: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。
  • 储运特性:库房通风低温干燥; 与氧化剂(硝铵)、食品添加剂分开存放

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