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シクロブタン
テトラメチレン · シクロブタン · Tetramethylene · Cyclobutan · Cyclobutane
識別子と物理属性
| CAS No. | 287-23-0 |
|---|---|
| 分子式 | C4H8 |
| 平均分子量 | 56.11 g/mol |
| 単同位体質量 | 56.06260026 g/mol |
| SMILES | C1CCC1 |
| InChIKey | PMPVIKIVABFJJI-UHFFFAOYSA-N |
| PubChem CID | 9250 |
| ChEBI | CHEBI:30377 |
| EC No. | 206-014-5 |
| DTXSID | DTXSID2059772 |
| 現地名 | シクロブタン |
化学・物理的性質
| XLogP | 2.5 |
|---|---|
| 極性表面積 | 0 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 0 |
| 回転可能結合数 | 0 |
| 重原子数 | 4 |
| 形式電荷 | 0 |
| 複雑度 | 8 |
| 物質分類 | Toxic Gases & Vapors -> Simple AsphyxiantsFlammable agents - 4th degree |
| SpringerMaterials Properties | Coriolis coupling |
| 密度 | 0.7038 AT 0 °C0.7125 @ 5 °Cd0 0.7038d-5 0.7185 |
| Color/Form | Colorless gas |
| 溶解度 | INSOL IN WATERFREELY SOL IN ALCOHOL, ACETONESol in ethanol, ether, and acetone |
| 引火点 | BELOW 50 °F Closed Cup |
| 沸点 | 13.08 °C @ 741 MM HGbp741 13.08° |
| Decomposition | When heated to decomposition it emits acrid smoke and fumes. |
| 融点 | -80 °C-80° |
| 蒸気密度 | 1.93 (AIR= 1) |
| 蒸気圧 | 1.18X10+3 mm Hg @ 25 °C |
| 屈折率 | INDEX OF REFRACTION: 1.3625 @ 290 °C/DnD0 1.37520 |
| ヘンリー定数 | 1.3×10-6 mol/(m3Pa) at 25℃, Hayer et al. (2022) |
| EPAの化学物質情報 | Cyclobutane (287-23-0) |
化学的特性
Cyclobutane is a colorless, flammable, explosive gas.
安全性と法規制
| GHS 分類 | DangerH220 (100%): Extremely flammable gas [Danger Flammable gases]P203, P210, P222, P280, P377, P381, P403, and P410+P403 (click each P-code to see the statement)Aggregated GHS information provided per 71 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 規制情報 | The 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） | Flammable Gas |
| 火災危険 | Excerpt from ERG Guide 115 [Gases - Flammable (Including Refrigerated Liquids)]:· EXTREMELY FLAMMABLE. |
| 火災の可能性 | VERY DANGEROUS, WHEN EXPOSED TO HEAT OR FLAMECAN REACT WITH OXIDIZING MATERIALS. |
| 健康有害性 | Excerpt from ERG Guide 115 [Gases - Flammable (Including Refrigerated Liquids)]:· Vapors may cause dizziness or asphyxiation without warning, especially when in closed or confined areas. |
| 有害性の概要 | Fire hazard[Hawley] In confined space spill, may displace air and act as simple asphyxiant[HSDB] Evaporating liquid can cause frostbiteMay cause asphyxiation without warning[CAMEO] May cause difficulty breathing and suffocationEvaporating liquid can cause frostbite[MSDSonline] See n-Butane. |
| 輸送番号・ガイド（DOT） | 2601 115 |
| 反応性グループ | Hydrocarbons, Aliphatic Saturated |
| Reactivity Alerts | Highly Flammable |
| Reactivity Profile | CYCLOBUTANE may be incompatible with strong oxidizing agents like nitric acid. Charring may occur followed by ignition of unreacted material and other nearby combustibles. In other settings, mostly unreactive. Not affected by aqueous solutions of acids, alkalis, most oxidizing agents, and most reducing agents. |
| DOT Emergency Guidelines | /GUIDE 115: GASES - FLAMMABLE (Including Refrigerated Liquids)/ Fire or Explosion: EXTREMELY FLAMMABLE. Will be easily ignited by heat, sparks or flames. Will form explosive mixtures with air. Vapors from liquefied gas are initially heavier than air and spread along ground. CAUTION: Hydrogen (UN1049), Deuterium (UN1957), Hydrogen, refrigerated liquid (UN1966) and Methane (UN1971) are lighter than air and will rise. Hydrogen and Deuterium fires are difficult to detect since they burn with an invisible flame. Use an alternate method of detection (thermal camera, broom handle, etc.) Vapors may travel to source of ignition and flash back. Cylinders exposed to fire may vent and release flammable gas through pressure relief devices. Containers may explode when heated. Ruptured cylinders may rocket./GUIDE 115: GASES - FLAMMABLE (Including Refrigerated Liquids)/ Health: Vapors may cause dizziness or asphyxiation without warning. Some may be irritating if inhaled at high concentrations. Contact with gas or liquefied gas may cause burns, severe injury and/or frostbite. Fire may produce irritating and/or toxic gases./GUIDE 115: GASES - FLAMMABLE (Including Refrigerated Liquids)/ Public Safety: CALL Emergency Response Telephone Number on Shipping Paper first. If Shipping Paper not available or no answer, refer to appropriate telephone number listed on the inside back cover. As an immediate precautionary measure, isolate spill or leak area for at least 100 meters (330 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Many gases are heavier than air and will spread along ground and collect in low or confined areas (sewers, basements, tanks). Keep out of low areas./GUIDE 115: GASES - FLAMMABLE (Including Refrigerated Liquids)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. Always wear thermal protective clothing when handling refrigerated/cryogenic liquids.For more DOT Emergency Guidelines (Complete) data for CYCLOBUTANE (8 total), please visit the HSDB record page. |
| DOT Hazard Classification | CyclobutaneUN2601Div 2.1 Flammable gas (49 eCFR § 173.115) |
| 消火 | Excerpt from ERG Guide 115 [Gases - Flammable (Including Refrigerated Liquids)]: |
| 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 | Excerpt from ERG Guide 115 [Gases - Flammable (Including Refrigerated Liquids)]:General First Aid: |
| 暴露管理・個人防護 | · Wear positive pressure self-contained breathing apparatus (SCBA). |
| 消火手順 | STOP FLOW OF GASCARBON DIOXIDE, DRY CHEMICAL, OR WATER SPRAY. |
| 非火災時の漏出対応 | Excerpt from ERG Guide 115 [Gases - Flammable (Including Refrigerated Liquids)]: |
| 処分方法 | SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices. |
| Isolation and Evacuation | Excerpt from ERG Guide 115 [Gases - Flammable (Including Refrigerated Liquids)]:Immediate precautionary measure |
| Threshold Limit Values (TLV) | 1000.0 [ppm] |
| Personal Protective Equipment (PPE) | Excerpt from ERG Guide 115 [Gases - Flammable (Including Refrigerated Liquids)]: |
| Emergency Response Planning Guidelines | · DO NOT EXTINGUISH A LEAKING GAS FIRE UNLESS LEAK CAN BE STOPPED. |
| 環境中動態 | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 49(SRC), determined from a structure estimation method(2), indicates that cyclobutane is expected to have very high mobility in soil(SRC). Volatilization of cyclobutane from moist soil surfaces is expected to be important(SRC) given an estimated Henry's Law constant of 0.14 atm-cu m/mole(3). The potential for volatilization of cyclobutane from dry soil surfaces may exist(SRC) based on a vapor pressure of 1.18X10+3 mm Hg(4). Activated sludge tests suggest that biodegradation of cyclobutane is expected to be slow in soil(5).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 49(SRC), determined from a structure estimation method(2), indicates that cyclobutane is not expected to adsorb to suspended solids and sediment in water(SRC). Cyclobutane is expected to volatilize from water surfaces(3,SRC) based on an estimated Henry's Law constant of 0.14 atm-cu m/mole(4). Estimated volatilization half-lives for a model river and model lake are 2 hrs and 3 days, respectively(3,SRC). According to a classification scheme(5), an estimated BCF of 10(3,SRC), from an estimated log Kow(2,SRC), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Cyclobutane is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(3). Activated sludge tests suggest that biodegradation of cyclobutane is expected to be slow in water(6).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), cyclobutane, which has a vapor pressure of 1.18X10+3 mm Hg at 25 °C(2,SRC), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase cyclobutane 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 10 days(3,SRC). Cyclobutane is not expected to undergo direct photolysis due to the lack of absorption in the environmental spectrum(4). |
| 有害作用 | Neurotoxin - Acute solvent syndrome |
| Effluent Concentrations | Cyclobutane was found to be an emission from commercial natural gas, but not from gasoline or vehicle exhausts(1). |
| Soil Adsorption/Mobility | Using a structure estimation method based on molecular connectivity indices(1), the Koc for cyclobutane can be estimated to be about 49(SRC). According to a classification scheme(2), this estimated Koc value suggests that cyclobutane is expected to have very high mobility in soil(SRC). |
| Human Toxicity Excerpts | MAY BE SIMPLE ASPHYXIANT. |
| Artificial Pollution Sources | Cyclobutane's production and use in organic synthesis(1) may result in its release to the environment through various waste streams(SRC). |
| Environmental Biodegradation | When incubated with either adapted or nonadapted activated sludge, cyclobutane underwent <25% of the theoretical BOD in 24 hrs(1). Pure culture studies showed various isolated species of bacteria were unable to utilize cyclobutane as the sole carbon source in soil(2). |
| Environmental Bioconcentration | An estimated BCF of 10 was calculated for cyclobutane(1,SRC), using an estimated log Kow of 2.19(1,SRC) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low. |
| Volatilization from Water/Soil | The Henry's Law constant for cyclobutane is estimated as 0.14 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that cyclobutane is expected to volatilize rapidly from water surfaces(2,SRC). Based on this Henry's Law constant, the estimated volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec) is approximately 2 hours(2,SRC). The estimated volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec) is approximately 3 days(2,SRC). Cyclobutane's Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur(SRC). The potential for volatilization of cyclobutane from dry soil surfaces may exist(SRC) based on a vapor pressure of 1.18X10+3 mm Hg(3). |
| Environmental Abiotic Degradation | The rate constant for the vapor-phase reaction of cyclobutane with photochemically-produced hydroxyl radicals of 1.20X10-12 cu cm/molecule-sec at 25 °C(1) corresponds to an atmospheric half-life of about 10 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(2,SRC). Cyclobutane is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(3) nor to directly photolyze due to the lack of absorption in the environmental spectrum. |
| Probable Routes of Human Exposure | INDUSTRIALLY...NOT EXPECTED TO BE HEALTH HAZARD.Occupational exposure to cyclobutane may occur through inhalation and dermal contact with this compound at workplaces where cyclobutane is produced or used. (SRC) |
| Environmental Water Concentrations | SURFACE WATER: Cyclobutane was detected in 1 of 8 Rhine River water samples, 1989, at a concn of 0.027 ug/l(1). |
| TSCA 収載状態 | TSCA listed |
| 輸送番号（UN） | UN 2601 |
| 危険等級 | 2.1 |
| 有害物質データ | 287-23-0(Hazardous Substances Data) |
用途
解説
C4H8(56.11)．臭化シクロブチルマグネシウムとブチルアルコールとの反応で得られる．シクロブタンカルボン酸の熱分解でも生成する．"無色の気体．融点－80 ℃，沸点12 ℃．d04 0.7038．ニッケル触媒の存在下，200 ℃ で還元するとブタンになる．4個の炭素原子は同一平面上になく，折れまがった構造をとる．[CAS 287-23-0]森北出版「化学辞典（第2版）
一般的な説明
Gas that condenses to a liquid at 55°F. Density of liquid 0.7 g / cm3. Insoluble in water. Soluble in alcohol, acetone and ether. Under prolonged exposure to fire or intense heat the containers may rupture violently and rocket.
製法・合成法
調製方法
Cyclobutane is produced from cyclobutene and reutilized in catalytic cracking processes.
純化方法
This easily liquefiable gas is dried over Na at melting ice temperature for 4days and distilled at low temperature through a Podbielniak (p 10) precision still. A dry sample has been prepared by passage through P2O5 and distilled repeatedly until all fractions had similar vapour pressures at 0o. [Cansson & Wat J Org Chem 14 31 1949, Heisig J Am Chem Soc 63 1698 1941, Stodola & Heisig Org Synth Coll Vol III 213 1955.]