化工社化工社化学信息打印报告 · 仅供科研参考
丁烯酮
丁烯酮 · DX铜 · 亚甲基丙酮 · 甲基乙烯酮 · 甲基乙烯基酮 · 甲基乙烯基甲酮 · 3-丁烯-2酮 · 3-丁烯-2-酮
标识与物理属性
| CAS No. | 78-94-4 |
|---|---|
| 分子式 | C4H6O |
| 平均分子量 | 70.09 g/mol |
| 单同位素质量 | 70.04186481 g/mol |
| SMILES | C=CC(C)=O |
| InChIKey | FUSUHKVFWTUUBE-UHFFFAOYSA-N |
| PubChem CID | 6570 |
| ChEMBL | CHEMBL1600824 |
| ChEBI | CHEBI:48058 |
| EC No. | 201-160-6 |
| DTXSID | DTXSID3025671 |
| 中文名 | 丁烯酮 |
化学与物理性质
| XLogP | 0.5 |
|---|---|
| 极性表面积 | 17.1 |
| 氢键供体 | 0 |
| 氢键受体 | 1 |
| 可旋转键 | 1 |
| 重原子 | 5 |
| 形式电荷 | 0 |
| 复杂度 | 54.7 |
| 物质类别 | Toxic Gases & Vapors -> Other Toxic Gases & VaporsFlammable agents - 3rd degree |
| 脂质 | Fatty Acyls [FA] -> Oxygenated hydrocarbons [FA12] |
| SpringerMaterials Properties | Schoenflies notation |
| LogP（油水分配系数） | 0.117 (estimated) |
| 气味 | Pungent odorOdor concn (low) = 0.5720 mg/cu m. Odor concn (high) = 0.5720 mg/cu m.at 100.00%. sweet |
| 密度 | 0.8407 to 0.8636 at 68 to 77 °F (EPA, 1998)0.8636 at 20 °C/4 °C0.8407 at 25 °C/4 °CSaturated vapor density = 0.01714 lb/cu ft at 70 °FRelative density (water = 1): 0.860.86 @ 20°C0.864 g/mL at 25 °C(lit.) |
| Viscosity | 0.807 Cp at 70 °F |
| Color/Form | Colorless liquid |
| 溶解性 | greater than or equal to 100 mg/mL at 72 °F (NTP, 1992)Easily sol in methanol, ethanol, ether, acetone, glacial acetic acidslightly sol in hydrocarbons.Slightly soluble in carbon tetrachloridesoluble in benzeneSolubility in water: goodChloroform (Sparingly), Methanol (Slightly)MISCIBLE |
| 闪点 | 20 °F (EPA, 1998)20 °F (-7 °C) (Closed cup)30 °F (open cup)-7 °C c.c. |
| 沸点 | 179 °F at 760 mmHg (EPA, 1998)81.4 °CForms binary azeotrope with waterBP: 75 °C at 760 mm Hg (12% water) ... polymerizes on standing.81 °C81.4 °C @760 [mm Hg]80 °C |
| 熔点 | 20 °F (EPA, 1998)FP: 20 °F = -7 °C = 266 deg K-7°C |
| 蒸气密度 | 1.3 (vs air) |
| 蒸气压 | 310 mm Hg ( 55 °C) |
| 折射率 | n20/D 1.411(lit.) |
| 储存条件 | 2-8°C |
| 形态 | Liquid |
| 颜色 | Clear colorless to pale yellow, may discolor to brown on storage |
| 比重 | 0.864 |
| 爆炸极限 | 15.64% |
| Merck | 14,6134 |
| BRN | 506021 |
| 亨利常数 | 4.0×10-1 mol/(m3Pa) at 25℃, Burkholder et al. (2019) |
| 稳定性 | Stable. Incompatible with strong bases, strong oxidizing agents, strong reducing agents. Heat and light sensitive. May undergo autopolymerization. Highly flammable. Refrigerate. |
| InChI | 1S/C4H6O/c1-3-4(2)5/h3H,1H2,2H3 |
| InChIKey | FUSUHKVFWTUUBE-UHFFFAOYSA-N |
| SMILES | O=C(C)C=C |
| LogP（油水分配系数） | 0.142 (est) |
| CAS 数据库 | 78-94-4(CAS DataBase Reference) |
| NIST化学物质信息 | Methyl vinyl ketone(78-94-4) |
| EPA化学物质信息 | Methyl vinyl ketone (78-94-4) |
化学性质
具有刺激性臭的无色液体。 易溶于水、甲醇、乙醇、乙醚、丙酮和冰醋酸，微溶于烃类。
安全与法规
| GHS 分类 | DangerH225 (99.4%): Highly Flammable liquid and vapor [Danger Flammable liquids]P210, P233, P240, P241, P242, P243, P260, P261, P262, P264, P264+P265, P270, P271, P272, P273, P280, P284, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P320, P321, P330, P333+P317, P361+P364, P362+P364, P363, P370+P378, P391, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 154 reports by companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H225: Highly Flammable liquid and vapor [Danger Flammable liquids] |
|---|---|
| Hazards Identification | Toxic/poison by inhalation (TIH/PIH) |
| 法规信息 | Chemical: 3-Buten-2-oneStatus: Active Update: 20-10-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/10900Methyl vinyl ketone: HSNO Approval: HSR003027 Approved with controlsThe New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.) |
| 运输标签（DOT） | Poison Inhalation Hazard Flammable Liquid Corrosive |
| 火灾危害 | Vapors form flammable mixtures with air, and may travel a considerable distance to a source of ignition and flash back. Polymerization may take place in containers, possibly with violent rupture of containers. Upon exposure to heat or flame, it emits toxic and irritating fumes. Container may explode in heat of fire. Vapor explosion and poison hazard indoors, outdoors, or in sewers. Polymerizes on standing. Hazardous polymerization may occur. Avoid heat or sunlight. (EPA, 1998)· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.Highly flammable. Vapour/air mixtures are explosive. |
| 火灾可能性 | Dangerous fire hazard when exposed to hest, flame, or oxidizers.... Flammable liquid ... |
| 健康危害 | This material is readily absorbed through the skin, causing general poisoning, similar to other ketonesinhalation has central nervous system depressant effects. It is irritating to mucous membranes and respiratory tract and to the skinit is a lachrymator and can cause eye injury. (EPA, 1998)· TOXICmay be fatal if inhaled, ingested or absorbed through skin. |
| 危害概述 | TLV Basis is upper respiratory damage and leukopeniaNo human studies availableSufficient data were not available to assign Skin, DSEN, RSEN or carcinogenicity notations. [ACGIH] Highly toxic[Quick CPC] A lachrymatorCan cause liver injury (animal studies)Potential for pulmonary edema after heavy inhalation exposure[HSDB] Causes lachrymationMay cause skin sensitization[ICSC] Liquid causes second or third degree burns on short contact[CHRIS] May polymerize exothermically if heated, exposed to sunlight, or contaminated[CAMEO] Danger of skin sensitization[MAK] A severe skin irritant (1% solution)Causes acute pulmonary edema, emphysema, and other liver changes in inhalation lethal-concentration studies of ratsCauses impaired liver function tests in repeated-dose inhalation studies of rats[RTECS] Methyl vinyl ketone, stabilized (UN1251) has warning of explosive polymerization[ERG 2016]The major hazards encountered in the use and handling of methyl vinyl ketone stem from its toxicologic properties and flammability. Toxic by all routes (ie, inhalation, ingestion, and dermal contact), exposure to this colorless, pungent-smelling liquid may occur from its use as an alkylating agent, as an intermediate in the synthesis of steroids and vitamin A, and as a precursor in the production of plastics and polymers for packaging materials. Effects from exposure may include contact burns to the skin and eyes, tachycardia, nausea, shortness of breath, headache, dizziness, fainting, coma and death. In activities or situations where over-exposure is possible, wear a self-contained breathing apparatus with full face piece, and full chemical protective clothing specifically recommended by the shipper or producer, including rubber gloves, and boots, and bands around the arms and legs to prevent any skin contact. If contact should occur. immediately flush affected skin or eyes with running water for at least 15 minutes, and remove contaminated clothing and shoes at the site. Methyl vinyl ketone may be easily ignited by heat, sparks, or flame (flash point: 30 °F, open cup) in a wide range of concentrations (flammable limits - lower: 2.1%, upper: 15.6%). Its heavier than air vapor may travel to a source of ignition and flash back, or result in the build-up of explosive concentrations in enclosed spaces such as sewers. Also, containers may explode in the heat of a fire. Fires involving methyl vinyl ketone may be extinguished with dry chemical, CO2, Halon, water spray, alcohol or standard foam, water spray or fog (solid streams of water may be ineffective). Since methyl vinyl ketone fires may produce toxic fumes, when tank cars and trucks are involved, isolate the area for 1/2 mile in all directions. Fight fire from as far distance as possible, and dike fire control water. Methyl vinyl ketone should be stored in cool, well ventilated areas, away from direct sunlight, sources of ignition and shipped via air, rail, road, and water in containers bearing the label, "Flammable liquid". Small spills of methyl vinyl ketone may be taken up with sand or other noncombustible absorbent and placed into containers for later disposal. Before implementing land disposal of waste methyl vinyl ketone, consult with environmental regulatory agencies for guidance. |
| 运输编号与指南（DOT） | 1251 131P |
| 反应性基团 | Ketones |
| 联合国分类 | UN Hazard Class: 6.1UN Subsidiary Risks: 3 and 8UN Pack Group: I |
| Reactivity Alerts | Highly Flammable |
| Reactivity Profile | METHYL VINYL KETONE is incompatible with strong oxidizers and strong bases. It polymerizes spontaneously upon exposure to heat or sunlight. This polymerization may cause violent ruptures in containers. (NTP, 1992). |
| 消防 | Use water to keep fire-exposed containers cool. Keep unnecessary people awayisolate hazard area and deny entry. Stay upwindkeep out of low areas. Wear positive pressure breathing apparatus and special protective clothing. Isolate for 1/2 mile in all directions if tank car or truck is involved in fire.Use water spray, powder, alcohol-resistant foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water. |
| 急救措施 | Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer for medical attention.Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rinse mouth. Do NOT induce vomiting. Give one or two glasses of water to drink. Refer for medical attention . |
| 泄漏应急措施 | · CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. |
| 急救 | Warning: This material is readily absorbed through the skin, causing general poisoning similar to other ketones.General First Aid: |
| 安全储存 | Fireproof. Cool. Keep in the dark. Separated from strong reducing agents, strong oxidants and strong bases. Store only if stabilized. |
| Firefighting Hazards | ... The inhibited monomer may ... polymerize if heated sufficiently (by exposure to fire) and lead to rupture of the containing vessel.Vapors are heavier than air and may travel to a source of ignition and flash back. Closed containers may rupture violently when heated. Reacts violently with a broad range of materials under fire conditions. Combustion may produce irritants and toxic gases.... Vapors are uninhibited and may form polymers and block the vents ... A harmful contamination of the air can be reached very quickly on evaporation of this substance at 20 °C. |
| 暴露控制与个人防护 | · Wear positive pressure self-contained breathing apparatus (SCBA).TIH (Toxic Inhalation Hazard) - Term used to describe gases and volatile liquids that are toxic when inhaled. Some are TIH materials themselves, e.g., chlorine, and some release TIH gases when spilled in water, e.g., chlorosilanes. [ERG 2016]. |
| 灭火程序 | Use dry chemical, "alcohol resistant" foam, carbon dioxide, or water spray. Water may be ineffective. Use water spray to keep fire-exposed containers cool. fight fire from protected location or maximum possible distance. Approach fire from upwind to avoid hazardous vapors and toxic decomp products.If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, dry chemical or carbon dioxide. /Methyl vinyl ketone, stabilized/Evaculation: If fire becomes uncontrollable or container is exposed to direct flame consider evacuation of one-half (1/2) mile radius. /Methyl vinyl ketone, stabilized/ |
| 储存条件 | 3-Buten-2-one can only be stored in stabilized form at room temperature.Store in a cool, dry, well-ventilated location. Store away from heat, oxidizing materials, and sunlight. Separate from alkalies, reducing agents. Outside or detached storage is preferred.Fireproof ... Keep in the dark ... Store only if stabilized. |
| 清理方法 | Environmental considerations: air spill: Apply water spray or mist to knock down vapors. /Methyl vinyl ketone, stabilized/Environmental considerations: water spill: Use natural barriers or oil spill control booms to limit spill travel. Remove trapped material with suction hoses. /Methyl vinyl ketone, stabilized/Environmental considerations: land spill: Dig a pit, pond, lagoon, holding are to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents. /Methyl vinyl ketone, stabilized/Eliminate all ignition sources. Stop or control the leak, if this can be done without indue risk. Use water spray to cool and disperse vapors, protect personnel, and dilute spills to form nonflammable mixtures. Control runoff and isolate discharged material for proper disposal.Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent and remove to safe place. Personal protection: chemical protection suit including self-contained breathing apparatus. |
| 非火灾泄漏应对 | Excerpt from ERG Guide 131 [Flammable Liquids - Toxicpolymerization hazard]: |
| 处置方法 | SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations. |
| 体内负荷 | In a pilot study of pollutants in the milk of women living in 4 urban industrial areas in the USA, methyl vinyl ketone was detected in 1 of 8 samples(1). |
| 相互作用 | An added stabilizer or inhibitor can influence the toxicological properties of this substance, consult an expert. |
| 生态毒性数值 | EC50Species: Pseudokirchneriella subcapitata (Green algae)Conditions: freshwaterstaticConcentration: 120 ug/L (95% confidence limit: 0 to 610 ug/L) for 96 hrEffect: population, biomass /active ingredient/Species: Tetrahymena pyriformis (ciliated protozoan)Conditions: not specifiedConcentration: 2.17 mg/L/40 hrEffects: cell-multiplication inhibitionSpecies: Selenastrum capricornutum (algae))Concentration: 0.13 mg/L/96 hrEffects: biomass |
| 环境归趋 | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 3.8(SRC), determined from a structure estimation method(2), indicates that methyl vinyl ketone is expected to have very high mobility in soil(SRC). Volatilization of methyl vinyl ketone from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 4.65X10-5 atm-cu m/mole(3). Methyl vinyl ketone is expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 152 mm(4). A 0% theoretical BOD in 5 days using an acclimated sewage inoculum(5,6) suggests that biodegradation may not be an important environmental fate process in soil(SRC).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 3.8(SRC), determined from a structure estimation method(2), indicates that methyl vinyl ketone is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 4.65X10-5 atm-cu m/mole(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 18 hours and 8.1 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 3.2(SRC), from an estimated log Kow of 0.41(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). A 0% theoretical BOD in 5 days using an acclimated sewage inoculum(8,9) suggests that biodegradation may not be an important environmental fate process in water(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), methyl vinyl ketone, which has an estimated vapor pressure of 152 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase methyl vinyl ketone is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC)the half-life for this reaction in air is estimated to be 20 hours(SRC), calculated from its rate constant of 1.88X10-11 cu cm/molecule-sec at 25 °C(3). The rate constant for the vapor-phase reaction of methyl vinyl ketone with ozone has been estimated as 4.7X10-16 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(4). This corresponds to an atmospheric half-life of about 2.4 days at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(5). The rate constant for the vapor-phase reaction of methyl vinyl ketone with nitrate has been estimated as 1.62X10-14 cu cm/molecule-sec at 25 °C(6). This corresponds to an atmospheric half-life of about 2.1 days at an atmospheric concentration of 2.4X10+8 nitrate molecules per cu cm(7). |
| 食品调查数值 | Methyl vinyl ketone has been identified, not quantified, in chicken and pork(1). |
| 不良影响 | Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation. |
| 暴露途径 | The substance can be absorbed into the body by inhalation, through the skin and by ingestion. |
| Milk Concentrations | ENVIRONMENTAL: In a pilot study of pollutants in the milk of women living in 4 urban industrial areas in the USA, methyl vinyl ketone was detected in 1 of 8 samples(1). |
| 生态毒性摘录 | /AQUATIC SPECIES/ A 24 hr germination test with the mold Cladosporium cladosporioides with methyl vinyl ketone showed an almost complete, yet reversible, suppression of spore germination as of 0.2 mg/L./AQUATIC SPECIES/ ... 24 hr and 48 hr EC0 /no effect/ values of 0.25 mg/L and 0.125 mg/L, respectively, were found with respect to the swimming inability of Daphnia magna. |
| Plant Concentrations | Methyl vinyl ketone has been identified in the volatile emissions from southern red oak(1), aspen(2) and European oak(2) trees. |
| Signs and Symptoms | Burning sensation. Cough. Sore throat. Shortness of breath. Laboured breathing. Headache. Dizziness. Tremor. Symptoms may be delayed.MAY BE ABSORBED! Redness. Pain. Skin burns. Further see Inhalation.Watering of the eyes. Redness. Pain. Severe deep burns.Burning sensation. Abdominal pain. Shock or collapse. Further see Inhalation. |
| Ongoing Test Status | The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=78-94-4] |
| CERCLA 应报告数量 | Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Methyl vinyl ketone is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 10 lbs. |
| F | 8-10-19-23 |
| 水危害等级（WGK） | 3 |
| TSCA 清单状态 | TSCA listed |
| RTECS 号 | EM9800000 |
| 包装类别 | I |
| 危险类别 | 6.1Acute Tox. 1 DermalAcute Tox. 1 InhalationAcute Tox. 2 OralAquatic Acute 1Aquatic Chronic 1Eye Dam. 1Flam. Liq. 2Skin Corr. 1BSkin Sens. 1 |
| 储存类别 | 3 - Flammable liquids |
| 安全说明（S） | 16-26-28-36/37/39-45-60-61-38 |
| 海关编码 | 29141990 |
| 自燃温度 | 491°C |
| 危险品标志 | F,T+,N |
| 危险类别码（R） | 11-26/27/28-34-43-50/53-26/28-68-40 |
| 毒害物质数据 | 78-94-4(Hazardous Substances Data) |
| 运输编号（UN） | UN 1251 |
急性毒性
口服- 大鼠 LD50:30 毫克/ 公斤; 口服- 小鼠 LD50: 33 毫克/ 公斤
职业标准
STEL 0.1 毫克/ 立方米
可燃性危险特性
遇明火、高温、氧化剂易燃; 高热放出有毒刺激烟雾
储运特性
库房通风低温干燥; 与氧化剂、酸类分开存放
灭火剂
干粉、干石粉、二氧化碳、泡沫
用途与应用
用途
用作聚合反应单体制取阴离子树脂，还可用作烷基化剂和合成甾族化合物及维生素A的中间体
用途
该品具有很强的反应能力，用作聚合物的单体，制取阴离子树脂、胶片乳化剂；还用作烷基化剂和合成甾族化合物及维生素A等的中间体。
制备与合成方法
生产方法
由丙酮与甲醛缩合得到乙酰乙醇，再在草酸存在下脱水而制得甲基乙烯酮。甲醛溶液与丙酮按1:30混合进入管道反应器（温度51-53℃），控制流量，保持反应停留时间3-4min，将反应液移至盛有柠檬-丙酮的反应罐中，回流10min，回收丙酮，蒸尽水分后，加草酸进行脱水，再加少量氢醌，常压蒸馏，得甲基乙烯酮与水的共沸液。用精盐盐析，分层，将有机层加氯化钙脱水，加氢至精馏，收集80-83℃馏分，即为甲基乙烯酮，收率42%。此外，也可采用汞、银、铜等的硫酸盐作催化剂、由乙烯基乙炔经水合而得到甲基乙烯酮。