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HCID 6570作成日：2026年10月27日

メチルビニルケトン

メチルビニルケトン · 1-ブテン-3-オン · 3-ブテン-2-オン · メチルエテニルケトン · エテニルメチルケトン · ビニルメチルケトン · メチルビニルケトン ビニル ケトン · MVK

https://huagongshe.com/ja/chemical/6570

メチルビニルケトン の分子構造式

識別子と物理属性

CAS No.78-94-4
分子式C4H6O
平均分子量70.09 g/mol
単同位体質量70.04186481 g/mol
SMILESC=CC(C)=O
InChIKeyFUSUHKVFWTUUBE-UHFFFAOYSA-N
PubChem CID6570
ChEMBLCHEMBL1600824
ChEBICHEBI:48058
EC No.201-160-6
DTXSIDDTXSID3025671
現地名メチルビニルケトン

化学・物理的性質

XLogP0.5
極性表面積17.1
水素結合供与体数0
水素結合受容体数1
回転可能結合数1
重原子数5
形式電荷0
複雑度54.7
物質分類Toxic Gases & Vapors -> Other Toxic Gases & VaporsFlammable agents - 3rd degree
脂質Fatty Acyls [FA] -> Oxygenated hydrocarbons [FA12]
SpringerMaterials PropertiesSchoenflies notation
LogP（分配係数）0.117 (estimated)
臭いPungent odorOdor concn (low) = 0.5720 mg/cu m. Odor concn (high) = 0.5720 mg/cu m.100.00?%で。甘い
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.)
Viscosity0.807 Cp at 70 °F
Color/FormColorless liquid
溶解度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: goodクロロホルム（少量）、メタノール（少量）混和性
引火点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
融点20 °F (EPA, 1998)FP: 20 °F = -7 °C = 266 deg K-7°C
蒸気密度1.3 (vs air)
蒸気圧310 mm Hg ( 55 °C)
屈折率n20/D 1.411(lit.)
貯蔵条件2-8°C
外観・状態液体
色無色透明～淡黄色透明、保管により茶色に変色することがあります
比重0.864
爆発限界15.64%
Merck14,6134
BRN506021
ヘンリー定数4.0×10-1 mol/(m3Pa) at 25℃, Burkholder et al. (2019)
安定性安定。 強塩基、強酸化剤、強還元剤とは相容れない。 熱と光に敏感。 自己凝集が起こることがあります。 とても燃えやすい。 要冷蔵保管です。
InChI1S/C4H6O/c1-3-4(2)5/h3H,1H2,2H3
InChIKeyFUSUHKVFWTUUBE-UHFFFAOYSA-N
SMILESO=C(C)C=C
LogP（分配係数）0.142 (est)
CAS データベース78-94-4(CAS DataBase Reference)
NISTの化学物質情報Methyl vinyl ketone(78-94-4)
EPAの化学物質情報Methyl vinyl ketone (78-94-4)

安全性と法規制

GHS 分類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 IdentificationToxic/poison by inhalation (TIH/PIH)
規制情報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.)
輸送ラベル（DOT）Poison Inhalation Hazard Flammable Liquid Corrosive
火災危険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.
火災の可能性Dangerous fire hazard when exposed to hest, flame, or oxidizers.... Flammable liquid ...
健康有害性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 skin

用途

解説

不飽和ケトン，CH2＝CHCOCH3．ビニルアセチレンと水との付加反応で合成される．

用途

アルキル化剤、合成樹脂原料、ステロイド、レチノールの合成原料 (化学工業日報社)

説明

Methyl vinyl ketone (MVK) is a stable, highly flammable, heatand light-sensitive, and colourless liquid. It is incompatible with strong bases, strong oxidising agents, and strong reducing agents and undergoes autopolymerisation. MVK is a reactive organic compound classified as an enone. It is a colourless to yellow, flammable, highly toxic liquid with a pungent odour. It is easily soluble in water, methanol, ethanol, and acetic acid. It can act as an alkylating agent. Its alkylating ability is both the source of its high toxicity and the feature that makes it a useful intermediate in organic synthesis. It polymerises spontaneously and is used in the manufacture of plastic polymers. It is also an intermediate in the synthesis of steroids and vitamin A.

使用

Alkylating agent; commercial starting material for plastics; as intermediate in the synthesis of steroids and vitamin A.

一般的な説明

A clear colorless liquid with a pungent odor. Flash point 20 °F. May polymerize with the release of heat under exposure to heat or contamination. Less dense than water. Highly toxic by inhalation. Causes burns to skin, eyes and mucous membranes.

使用用途

メチルビニルケトンは、工業的に多くの用途を持つ汎用性の高い化学中間体です。一般的には、樹脂や塗料、の製造に使用されます。また、溶剤、香料、他の有機化合物の合成のための出発物質としても使用されます。 1. 樹脂・塗料 メチルビニルケトンには、他のモノマーと架橋しポリマーを形成する能力があるため、樹脂やコーティング剤の製造によく用いられます。塗料などに含まれるアクリル樹脂やビニル樹脂を生産する際、メチルビニルケトンはコモノマーとして添加され、ポリマーに高い接着性、耐薬品性、耐候性を与えます。 2. 粘着剤 メチルビニルケトンはエポキシ接着剤の製造において、反応性希釈剤としても使用されています。反応性希釈剤とは、エポキシ樹脂の性能を損なわずに粘度を下げるために用いられる希釈剤です。メチルビニルケトンの添加によって、接着剤の柔軟性や接着性が向上します。

製法・合成法

製造方法

メチルビニルケトンは、イソブチレンの酸化、3級ブチルアルコールの脱水、3-ペンタノンの脱水素など、さまざまな方法で合成することができます。このうち、工業的な製造方法としては、銅や銀の触媒を用いてイソプロピルアルコールを脱水素する方法が最も一般的です。 この合成法は気相で行われます。250～400℃の温度で気体にしたイソプロピルアルコールを銅触媒あるいは銀触媒の入った反応器に供給することで、イソプロピルアルコールの脱水素化が起こり、メチルビニルケトンと水素ガスが副生されます。 反応終了後、蒸留などの分離手段により、メチルビニルケトンと副生成物、および未反応のイソプロピルアルコールを分離することが可能です。

純化方法

It forms an 85% azeotrope with water. After drying with K2CO3 and CaCl2 (with cooling), the ketone is distilled at low pressures. [Beilstein 1 IV 3444.]

it is a lachrymator and can cause eye injury. (EPA, 1998)
· TOXIC
may be fatal if inhaled, ingested or absorbed through skin.
有害性の概要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.
輸送番号・ガイド（DOT）1251 131P
反応性グループKetones
UN 分類UN Hazard Class: 6.1UN Subsidiary Risks: 3 and 8UN Pack Group: I
Reactivity AlertsHighly Flammable
Reactivity ProfileMETHYL 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).
消火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.
応急処置措置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 .
漏出応急措置· 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.
応急処置Warning: This material is readily absorbed through the skin, causing general poisoning similar to other ketones.General First Aid:
安全保管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.
暴露管理・個人防護· 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].
消火手順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/
保管条件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.
清掃方法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.
非火災時の漏出対応Excerpt from ERG Guide 131 [Flammable Liquids - Toxicpolymerization hazard]:
処分方法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.
体内負荷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.
生態毒性値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
環境中動態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).
食品調査値Methyl vinyl ketone has been identified, not quantified, in chicken and pork(1).
有害作用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.
暴露経路The substance can be absorbed into the body by inhalation, through the skin and by ingestion.
Milk ConcentrationsENVIRONMENTAL: 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).
生態毒性抜粋/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 ConcentrationsMethyl vinyl ketone has been identified in the volatile emissions from southern red oak(1), aspen(2) and European oak(2) trees.
Signs and SymptomsBurning 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 StatusThe 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 報告数量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.
F8-10-19-23
水環境危害等級（WGK）3
TSCA 収載状態TSCA listed
RTECS 番号EM9800000
輸送番号（UN）UN 1251
税関コード29141990
危険文句（R）11-26/27/28-34-43-50/53-26/28-68-40
危険表示F,T+,N
安全措置（S）16-26-28-36/37/39-45-60-61-38
危険等級6.1Acute Tox. 1 DermalAcute Tox. 1 InhalationAcute Tox. 2 OralAquatic Acute 1Aquatic Chronic 1Eye Dam. 1Flam. Liq. 2Skin Corr. 1BSkin Sens. 1
包装等級I
自然発火温度491°C
貯蔵分類3 - Flammable liquids
有害物質データ78-94-4(Hazardous Substances Data)