化工社化工社 化学情報印刷レポート · 研究参考用
ブチルエーテル
ブチルエーテル · ジ-n-ブチルエーテル · 1,1'-オキシビスブタン · n-ブチルエーテル · 1-ブトキシブタン · ジブチルエーテル · 1,1'-オキシビス[ブタン] · 酸化ブチル
識別子と物理属性
| CAS No. | 142-96-1 |
|---|---|
| 分子式 | C8H18O |
| 平均分子量 | 130.23 g/mol |
| 単同位体質量 | 130.1357652 g/mol |
| SMILES | CCCCOCCCC |
| InChIKey | DURPTKYDGMDSBL-UHFFFAOYSA-N |
| PubChem CID | 8909 |
| ChEMBL | CHEMBL48132 |
| EC No. | 205-575-3 |
| DTXSID | DTXSID1022007 |
| 現地名 | ブチルエーテル |
化学・物理的性質
| XLogP | 3.2 |
|---|---|
| 極性表面積 | 9.2 |
| 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 | 6 |
| 重原子数 | 9 |
| 形式電荷 | 0 |
| 複雑度 | 37.8 |
| 物質分類 | Flammable agents - 3rd degree |
| Solvents | Solvents -> Ethers (<C12) |
| SpringerMaterials Properties | Activity |
| LogP（分配係数） | log Kow= 3.21 |
| 臭い | Mild, ethereal odor穏やかな、エーテルのような。 |
| 密度 | 0.767 at 68 °F (USCG, 1999) - Less dense than waterwill float0.7684 at 20 °C/4 °C% In saturated air: 0.9 at 25 °C, 760 mm Hgdensity of saturated air: 1.1 at 25 °C, 760 mm hg (air= 1)Density (at 20 °C): 0.8 g/cm³Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.00.7689 @25 °C0.764 g/mL at 25 °C (lit.) |
| Viscosity | 0.0069 poise (20 °C)0.86 mm²/s at 20 °C |
| Color/Form | Colorless liquid |
| 溶解度 | less than 1 mg/mL at 72.5 °F (NTP, 1992)Miscible with benzene and most org solventsSol in all prop in alc, ethervery sol in acetoneMiscible with oxygenated solventsIn water, 300 mg/L at 25 °CSolubility in water, g/100ml:H2O: 20℃で可溶0.113g/L0.03g/100mL(20℃) |
| 引火点 | 77 °F (NTP, 1992)37 °C (CLOSED CUP)25 °C c.c. |
| 沸点 | 288 °F at 760 mmHg (NTP, 1992)140.8 °C142 °C142 °C @760 [mm Hg]142-143 °C (lit.) |
| Decomposition | When heated to decomposition it emits acrid smoke and fumes. |
| 融点 | -98 °C (lit.) |
| 蒸気密度 | 4.48 (vs air) |
| 蒸気圧 | 4.8 mm Hg ( 20 °C) |
| 屈折率 | n20/D 1.399(lit.) |
| 貯蔵条件 | Store at <= 20°C. |
| 外観・状態 | 液体 |
| 色 | 無色透明 |
| pH | 5.2 (0.2g/l, H2O, 20℃) |
| 爆発限界 | 0.9-8.5%(V) |
| 比熱容量 | Cp(liquid): 2.14 J/(g·K), at 25℃ |
| Merck | 14,1569 |
| BRN | 1732752 |
| ヘンリー定数 | 2.1×10-3 mol/(m3Pa) at 25℃, Brockbank (2013) |
| 誘電率 | 3.1(25℃) |
| 安定性 | 安定。可燃性。保管中に過酸化物が形成される場合があります。強力な酸化剤とは相容れない。 |
| InChI | 1S/C8H18O/c1-3-5-7-9-8-6-4-2/h3-8H2,1-2H3 |
| InChIKey | DURPTKYDGMDSBL-UHFFFAOYSA-N |
| SMILES | CCCCOCCCC |
| LogP（分配係数） | 3.35 |
| 表面張力 | 23.049mN/m at 293.15K |
| CAS データベース | 142-96-1(CAS DataBase Reference) |
| NISTの化学物質情報 | n-Butyl ether(142-96-1) |
| EPAの化学物質情報 | Butyl ether (142-96-1) |
安全性と法規制
| GHS 分類 | WarningH226: Flammable liquid and vapor [Warning Flammable liquids]P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P271, P273, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)H226 (99.9%): Flammable liquid and vapor [Warning Flammable liquids] |
|---|---|
| 規制情報 | Chemical: Butane, 1,1'-oxybis-Butane, 1,1'-oxybis- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Butane, 1,1'-oxybis- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 16-11-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/11808Butane, 1,1'-oxybis-: HSNO Approval: HSR001076 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） | Flammable Liquid |
| 火災危険 | Behavior in Fire: Vapor is heavier than air and may travel a considerable distance to a source of ignition and flash back. (USCG, 1999)Flammable. Above 25 °C explosive vapour/air mixtures may be formed. |
| 火災の可能性 | ONLY ELECTRICAL EQUIPMENT OF EXPLOSION-PROOF TYPE (GROUP C CLASSIFICATION) IS PERMITTED TO BE OPERATED IN ETHER AREAS. ETHER SHOULD NOT BE STORED NEAR POWERFUL OXIDIZERS OR IN AREAS OF HIGH FIRE HAZARD. /ETHERS/ |
| 健康有害性 | Inhalation causes irritation of nose and throat. Liquid irritates eyes and may irritate skin on prolonged contact. Ingestion causes irritation of mouth and stomach. (USCG, 1999) |
| 有害性の概要 | May form explosive peroxides[Hawley] A skin, eye, and respiratory tract irritantMay have effects on CNS and liverDefats the skin[ICSC] A skin and eye irritant[eChemPortal: ERMA] An irritantEffects in high-dose animal studies include general anesthesia and fatty liver degeneration[MSDSonline] |
| 反応性グループ | Ethers |
| EC 分類 | Symbol: XiR: 10-36/37/38-52/53S: (2)-61 |
| UN 分類 | UN Hazard Class: 3UN Pack Group: III |
| Reactivity Alerts | Highly Flammable |
| Reactivity Profile | Ethers, such as N-BUTYL ETHER can act as bases. They form salts with strong acids and addition complexes with Lewis acids. The complex between diethyl ether and boron trifluoride is an example. Ethers may react violently with strong oxidizing agents. In other reactions, which typically involve the breaking of the carbon-oxygen bond, ethers are relatively inert. |
| Chemical Dangers | The substance can form explosive peroxides , especially in anhydrous form. Reacts violently with nitrogen trichloride and strong oxidants. Reacts with strong acids. |
| 消火 | Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:Use foam, powder, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water. |
| 応急処置措置 | Fresh air, rest. Refer for medical attention.First rinse with plenty of water for at least 15 minutes, then remove contaminated clothes and rinse again.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. Refer for medical attention . |
| 応急処置 | EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. |
| 安全保管 | Fireproof. Provision to contain effluent from fire extinguishing. Separated from incompatible materials. See Chemical Dangers. Cool. Keep in the dark. Store only if stabilized. Store in an area without drain or sewer access. |
| 消火手順 | Use dry chemical, foam, carbon dioxide or water spray. Water may be ineffective. Use water spray to keep fire-exposed containers cool.Eliminate all ignition sources. Stop or control the leak, if this can be done without undue risk. Use appropriate foam to blanket release and suppress vapors. Absorb in noncombustible material for proper disposal.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 spread fire. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use foam, dry chemical, or carbon dioxide. |
| 保管条件 | /DUE TO FIRE HAZARD, ETHERS/ ... SHOULD BE KEPT COOL & CONTAINERS ELECTRICALLY GROUNDED TO AVOID SPARKS ... . /ETHERS/Store in a cool, dry, well-ventilated location. Store away from heat, oxidizing materials, sunlight, and acids. |
| 清掃方法 | Evacuate and restrict persons not wearing protective equipment from area of spill or leak until cleanup is complete. Remove all ignition sources. Establish forced ventilation to keep levels below explosive limit. Absorb liquids in vermiculite, dry sand, earth, peat, carbon, or similar material and deposit in sealed containers. It may be necessary to contain and dispose of this chemical as a hazardous waste. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Contact your Department of Environmental Protection or your regional office of the federal EPA for specific recommendations. If employees are required to clean up spills, they must be properly trained and equipped. OSHA 1910.120(q) may be applicable.Environmental considerations-land spill: Dig a pit, pond, lagoon, holding area 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.Environmental considerations-water spill: Use natural barriers or oil spill control booms to limit spill travel. Remove trapped material with suction hoses.Environmental considerations-air spill: Apply water spray or mist to knock down vapors. |
| 非火災時の漏出対応 | Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: |
| 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.IncinerationThe following wastewater treatment technologies have been investigated for butyl ether: Concentration process: Activated carbon.Used ether containers, which are suspected of containing ether crystals or solids, are especially hazardous and may require bomb-squad assistance for their disposal. /Short alkyl-chain ethers/This compound should be susceptible to removal from waste water by air stripping. /Bis(2-chloroethyl)ether/ |
| 漏出処分 | Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Cover the spilled material with foam. Collect leaking liquid in sealable containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. |
| Preventive Measures | SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.TO PREVENT EXPOSURE OF WORKERS TO HARMFUL CONCN OF SOLVENT VAPOR, MOST EFFECTIVE MEASURE IS ENCLOSURE OF PROCESS. LOCAL EXHAUST VENTILATION SHOULD BE INSTALLED ON ENCLOSURE ... /IF/ THIS IS NOT PRACTICABLE OPERATIONS MAY BE CONDUCTED UNDER HOOD FITTED WITH EXHAUST VENTILATION ... . /SOLVENTS INDUST/... COMMON /ETHERS/ ... ARE EASILY IGNITED & HAVE LOW FLASH POINTS. IT IS NECESSARY TO CONTROL SMOKING, OPEN FLAMES OR HOT PLATES IN AREAS WHERE LOW MOL WT ETHERS ARE APT TO REACH 1% CONCN OR MORE IN AIR. /ETHERS/If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard. Use water spray to knock-down vapors.Personnel protection: Avoid breathing vapors. Keep upwind. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. |
| Isolation and Evacuation | Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: |
| 生態毒性値 | LC50 Cyprinodon variegatus (Sheepshead minnows, juvenile 14-28 days old) above 430 ppm/24, 48, 72 and 96 hr, seawater at 25-31 °C, static bioassayLC50 Pimephales promelas (fathead minnow) 32.5 mg/L 96 hr flow-through bioassay, wt 0.12 g, water hardness 45.5 mg/L CaCO3, temp: 25 + or - 1 °C, pH 7.5, dissolved oxygen greater than 60% of saturationLC50 Pimephales promelas (fathead minnow) 52 mg/L for 96 hr /Conditions of bioassay not speicifed/EC50Species: Daphnia magna (Water flea)Conditions: freshwater, static, pH 8.0Concentration: 150 mg/L for 24 hrEffect: behavior, equilibriumFor more Ecotoxicity Values (Complete) data for DIBUTYL ETHER (6 total), please visit the HSDB record page. |
| 環境中動態 | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 51(SRC), determined from a structure estimation method(2), indicates that dibutyl ether is expected to have high mobility in soil(SRC). Volatilization of dibutyl ether from moist soil surfaces may be important(SRC) given a Henry's Law constant of 6.0X10-3 atm-cu m/mole(3). Volatilization of dibutyl ether from dry soil surfaces is expected(SRC) based upon an extrapolated vapor pressure of 6.0 mm Hg at 25 °C(4). Biodegradation of dibutyl ether in soil is expected to be a slow process(SRC), based upon its slow biodegradation in aqueous screening studies(5,6).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 51(SRC), determined from a structure estimation method(2), indicates that dibutyl ether is not expected to adsorb to suspended solids and sediment in water(SRC). Dibutyl ether is expected to volatilize from water surfaces(3) based on a Henry's Law constant of 6.0X10-3 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 3.5 hours and 4.6 days, respectively(SRC). According to a classification scheme(5), BCFs ranging from 30 to 114 measured in carp(6), suggest that bioconcentration in aquatic organisms is moderate to high(SRC). Biodegradation of dibutyl ether in water is expected to be a slow process(SRC), based upon its slow biodegradation in aqueous screening studies(6,7).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dibutyl ether, which has an extrapolated vapor pressure of 6.0 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase dibutyl ether 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 13 hours(SRC) calculated from its rate constant of 2.88X10-11 cu cm/molecule-sec at 25 °C(3). Direct photolysis is not expected to be an important removal process since aliphatic ethers do not absorb light in the environmental spectrum(4). |
| 有害作用 | Neurotoxin - Acute solvent syndrome |
| 暴露経路 | The substance can be absorbed into the body by inhalation of its vapour. |
| Signs and Symptoms | Cough. Sore throat.Dry skin.Redness. Pain.Burning sensation. Nausea. Sore throat. |
| Effluent Concentrations | Dibutyl ether has been detected in 1 out of 63 samples of industrial effluents collected from a wide variety of industries across the U.S. at a concn of <10 ug/L (dates not reported)(1). Dibutyl ether was tentatively identified, but not quantified, in an advanced waste treatment concentrate from Lake Tahoe, CA, sampled in Oct 1974(2). Dibutyl ether was detected at concn of 5.6 and 0.2 ug/L in 2 of 7 sites sampled in Feb 1979 for standing water and impoundments which were discharged into Wilson Creek from a hazardous waste dump site called "Valley of the Drums" in Bullitt County, KY(3). |
| ICSC Environmental Data | The substance is harmful to aquatic organisms. It is strongly advised not to let the chemical enter into the environment. The substance may cause long-term effects in the aquatic environment. Bioaccumulation of this chemical may occur along the food chain, for example in fish. |
| Soil Adsorption/Mobility | Using a structure estimation method based on molecular connectivity indices(1), the Koc for dibutyl ether can be estimated to be 51(SRC). According to a classification scheme(2), this estimated Koc value suggests that dibutyl ether is expected to have high mobility in soil(SRC). |
| Human Toxicity Excerpts | /SIGNS AND SYMPTOMS/ ... humans exposed to 100 ppm of dibutyl ether estimated it satisfactory for 8 hr exposures. At 200 ppm for 15 min the vapors produced a sensation of irritation to the eyes and nose, although at 300 ppm the odor was not objectionable to the majority of subjects./SIGNS AND SYMPTOMS/ Dibutyl ether, although not highly toxic orally, seems to have a greater toxicity by inhalation than the lower ethers of the series. It is also more irritating to the skin. |
| Artificial Pollution Sources | Dibutyl ether's production and use as an extracting agent and solvent(1) may result in its release to the environment through various waste streams(SRC). |
| Environmental Biodegradation | AEROBIC: Dibutyl ether achieved 16% of its theoretical BOD in screening tests which utilized acclimated mixed microbial cultures over a 5 day incubation period(1). Many ethers are known to be resistant to biodegradation(2). Dibutyl ether at 100 mg/L reached 3 to 4% of its theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/L and the Japanese MITI test(3).ANAEROBIC: 0% loss of dibutyl ether was observed in landfill leachate impacted aquifer slurries amended with sulfate or nitrate after 244 and 85 days incubation, respectively(1). Dibutyl ether was not biodegraded in aquifer slurries prepared from the methanogenic portion of a shallow anoxic aquifer polluted by municipal landfill leachate(2). |
| Environmental Bioconcentration | BCFs of 47 to 83 and 30 to 114 were measured for carp exposed to 200 and 20 ug/L of dibutyl ether over the course of a 6 week incubation period(1). According to a classification scheme(2), these BCFs suggest bioconcentration in aquatic organisms is moderate to high, provided the compound is not metabolized by the organism(SRC). |
| 水環境危害等級（WGK） | 2 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | EK5425000 |
| 輸送番号（UN） | UN 1149 (DIBUTYL ETHERS) |
| 毒性 | LD50 orally in rats: 7.4 g/kg (Smyth) |
| 税関コード | 29091990 |
| 危険文句（R） | 10-36/37/38-52/53 |
| 化審法 | (2)-363 |
| 消防法 | 危険物第4類第二石油類(非水溶性) |
| 危険表示 | Xi |
| hazard_note | Irritant |
| 安全措置（S） | 61-24/25 |
| 危険等級 | 3Aquatic Chronic 3Eye Irrit. 2Flam. Liq. 3Skin Irrit. 2STOT SE 3 |
| 包装等級 | III |
| 自然発火温度 | 365 °F |
| 貯蔵分類 | 3 - Flammable liquids |
| 有害物質データ | 142-96-1(Hazardous Substances Data) |
用途
用途
有機合成反応用溶媒、抽出溶媒
用途
有機合成反応用溶剤、有機酸
説明
Butyl ether (dibutyl ether) is a colorless, stable liquid, with a mild ether-like odor. It is immiscible with water, with a specific gravity of 0.8, which is lighter than water. Butyl ether is a moderate fire risk and will form explosive peroxides on aging. Flammable range is 1.5%–7.6% in air, with a boiling point of 286°F (141°C) and a flash point of 77°F (25°C). Ignition temperature is 382°F (194°C), and the vapor density is 4.5, which is heavier than air. In addition to flammability, butyl ether is toxic on prolonged inhalation. The four-digit UN identification number is 1149. The NFPA 704 designation is health 2, flammability 3, and reactivity 1. The primary use is as a solvent.
使用
Di-n-butyl ether is used as a solvent for Grignard, Witting and alkyl lithium reactions. It is also used as a solvent for oils and fats and some natural and synthetic resins. It is considered as a replacement for terathydofuran in organic synthesis due to its less water and peroxide and high boiling point. In the pharmaceutical industry, it is used in the manufacturing process of active pharmaceutical ingredient such as procarbazine and cefaclor. In addition to this, it is used as an important solvent for the application of the coating.
一般的な説明
Di-n-butyl ether is a clear colorless liquid with an ethereal odor. Flash point below 141°F. Less dense than water and insoluble in water. Vapors heavier than air. Irritates the eyes, nose, throat, and respiratory tract.
製法・合成法
純化方法
Peroxides (detected by the liberation of iodine from weakly acid HCl solutions of 2% KI) can be removed by shaking 1L of ether with 5-10mL of a solution comprising of 6.0g of ferrous sulfate and 6mL conc H2SO4 and 110mL of water, with aqueous Na2SO3, or with acidified NaI, water, then aqueous Na2S2O3. After washing with dilute NaOH, KOH, or Na2CO3, then water, the ether is dried with CaCl2 and distilled. It can be further dried by distillation from CaH2 or Na (after drying with P2O5), and stored in the dark with Na or NaH. The ether can also be purified by treating with CS2 and NaOH, expelling the excess sulfide by heating. The ether is then washed with water, dried with NaOH and distilled [Kusama & Koike J Chem Soc Jpn, Pure Chem Sect 72 229 1951]. Other purification procedures include passage through an activated alumina column to remove peroxides, or through a column of silica gel, and distillation after adding about 3% (v/v) of a 1M solution of MeMgI in n-butyl ether. [Beilstein 1 IV 1520.]