化工社化工社 化学情報印刷レポート · 研究参考用
tert-ブタノール
tert-ブタノール · t-ブチルアルコール · tert-ブチルアルコール · 1,1-ジメチル-エタノール · 1,1-ジメチルエタノール · 1,1,1-トリメチルメチルアルコール · t-ブタノール · 2-メチル-2-プロパノール
識別子と物理属性
| CAS No. | 75-65-0 |
|---|---|
| 分子式 | C4H10O |
| 平均分子量 | 74.12 g/mol |
| 単同位体質量 | 74.07316494 g/mol |
| SMILES | CC(C)(C)O |
| InChIKey | DKGAVHZHDRPRBM-UHFFFAOYSA-N |
| PubChem CID | 6386 |
| ChEMBL | CHEMBL16502 |
| ChEBI | CHEBI:45895 |
| EC No. | 200-889-7 |
| DTXSID | DTXSID8020204 |
| 現地名 | tert-ブタノール |
化学・物理的性質
| XLogP | 0.5 |
|---|---|
| 極性表面積 | 20.2 |
| 水素結合供与体数 | 1 |
| 水素結合受容体数 | 1 |
| 回転可能結合数 | 0 |
| 重原子数 | 5 |
| 形式電荷 | 0 |
| 複雑度 | 25.1 |
| 物質分類 | Flammable agents - 3rd degreeVolatile Organic Compound (VOC) |
| 医薬品 | Pharmaceuticals -> Listed in ZINC15 |
| Solvents | Solvents -> Alcohols (<C12) |
| 化粧品 | Cosmetics ingredient -> FragranceOther (Specify)Preservative/StabilizerSolventCosmetic ingredients (t-Butyl Alcohol) -> CIR (Cosmetic Ingredient Review)Denaturant |
| SpringerMaterials Properties | Schoenflies notation |
| 香料 | Fragrance Ingredient (2-Methyl-2-propanol) -> IFRA transparency List |
| 農薬 | Pesticide -> EPA IRIS |
| LogP（分配係数） | log Kow = 0.350.34 |
| 臭い | Camphor-like odor特性樟脳のような刺激的な。 |
| 密度 | 0.78 at 78.8 °F (USCG, 1999) - Less dense than waterwill float0.7886 g/cu cm at 20 °CRelative density (water = 1): 0.80.781 @25 °C0.79 (Solid)0.775 g/mL at 25 °C (lit.) |
| 香味料 | EU Flavoring substances |
| Color/Form | A colorless liquid, which forms rhombic crystals melting at 25 to 25.5 °CColorless liquid or rhombic prisms or platesColorless liquid or solid (above 77 °F) [Note: Often used in aqueous solutions]. |
| 融点 | 23-26 °C (lit.) |
| 沸点 | 83 °C (lit.) |
| 蒸気密度 | 2.55 (vs air) |
| 蒸気圧 | 31 mm Hg ( 20 °C) |
| 屈折率 | n20/D 1.399(lit.) |
| 引火点 | 95 °F |
| 貯蔵条件 | Store at +5°C to +30°C. |
| 溶解度 | 水: 混和性溶ける |
| pKa（酸解離定数） | 19(at 25℃) |
| 外観・状態 | 融解後の液体 |
| 色 | APHA: ≤20 |
| pH | 7 (20°C) |
| 臭気閾値 | 4.5ppm |
| 爆発限界 | 2.3-8.0%(V) |
| 比熱容量 | Cp(liquid): 2.95 J/(g·K)Cp(gas): 1.53 J/(g·K), at 25℃ |
| Merck | 14,1542 |
| JECFA Number | 85 |
| BRN | 906698 |
| ヘンリー定数 | 1.22 at 25 °C (static headspace-GC, Merk and Riederer, 1997) |
| 誘電率 | 7.8(19℃) |
| 安定性 | 安定。非常に可燃性です。強力な酸化剤、銅、銅合金、アルカリ金属、アルミニウムとは相容れない。 |
| 化粧品成分の機能 | 溶媒香料変性剤 |
| InChI | 1S/C4H10O/c1-4(2,3)5/h5H,1-3H3 |
| InChIKey | DKGAVHZHDRPRBM-UHFFFAOYSA-N |
| SMILES | CC(C)(C)O |
| LogP（分配係数） | 0.350 |
| 表面張力 | 20.3mN/m at 298.15K |
| CAS データベース | 75-65-0(CAS DataBase Reference) |
| NISTの化学物質情報 | Ethanol, 1,1-dimethyl-(75-65-0) |
| EPAの化学物質情報 | tert-Butanol (75-65-0) |
化学的特性
ブタノールは化学式がC4H9OHで表される一価のアルコールですこの化合物は工業的にも自然界にも存在し特に溶剤や化学合成の基礎原料として重要な役割を果たしていますブタノールには異性体が四種類存在しそれぞれが異なる物理的および化学的性質を持っていますこれらの異性体にはnブタノールイソブタノールsecブタノールtertブタノールが含まれます
安全性と法規制
| GHS 分類 | DangerH225: Highly Flammable liquid and vapor [Danger Flammable liquids]P210, P233, P240, P241, P242, P243, P261, P264+P265, P271, P280, P303+P361+P353, P304+P340, P305+P351+P338, P317, P319, P337+P317, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)This chemical does not meet GHS hazard criteria for < 0.1% (1 of 3040) of reports.H225 (> 99.9%): Highly Flammable liquid and vapor [Danger Flammable liquids] |
|---|---|
| 規制情報 | Chemical: 2-Propanol, 2-methyl-Hazard Traits - CarcinogenicityCommission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)2-Propanol, 2-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propanol, 2-methyl- 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: 09-08-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/141122-Propanol, 2-methyl-: HSNO Approval: HSR001099 Approved with controls |
| その他の安全情報 | IMAP assessments - 2-Propanol, 2-methyl-: Human health tier II assessment |
| 輸送ラベル（DOT） | Flammable Liquid |
| 火災危険 | This chemical is flammable. (NTP, 1992)Highly flammable. Vapour/air mixtures are explosive. Heating will cause rise in pressure with risk of bursting. |
| 火災の可能性 | Highly flammable liquid and vapor. |
| 健康有害性 | Vapor is narcotic in action and irritating to respiratory passages. Liquid is irritating to skin and eyes. (USCG, 1999) |
| 有害性の概要 | Animals in feeding studies develop alcohol intoxication[ACGIH] A skin, eye, and respiratory tract irritantInhalation of high concentrations can cause CNS depression[ICSC] |
| 輸送番号・ガイド（DOT） | 1120 129 |
| FDA 要件 | Defoaming agents used in coatings. The defoaming agents described in this section may be safely used as components of articles intended for use in producing, manufacturing, packing, processing, preparing, treating, packaging, transporting, or holding food, subject to the provisions of this section. tert-Butyl alcohol is included on this list. |
| 反応性グループ | Alcohols and Polyols |
| EC 分類 | Symbol: F, XnR: 11-20-36/37S: (2)-9-16-46 |
| UN 分類 | UN Hazard Class: 3UN Pack Group: II |
| 消火 | Fire Extinguishing Agents Not to Be Used: Water may be ineffective on fireUse water spray, alcohol-resistant 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.Remove contaminated clothes. Rinse skin with plenty of water or shower.First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rinse mouth. Give one or two glasses of water to drink. 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.(General first aid procedures) |
| 安全保管 | Fireproof. Separated from strong oxidants and strong acids. |
| Firefighting Hazards | Flashback along vapor trail may occur. |
| 暴露管理・個人防護 | 20.0 [ppm] |
| 消火手順 | Flash back possible over considerable distance.Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.Wear self contained breathing apparatus for fire fighting if necessary.In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.Use water spray to cool unopened containers.Flammable in the presence of a source of ignition when the temperature is above the flash point. Keep away from heat/sparks/open flame/hot surface. No smoking. |
| 保管条件 | Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage. |
| 清掃方法 | Personal precautions: Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low areas. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Methods and materials for containment and cleaning up: Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and place in container for disposal according to local regulations. |
| 非火災時の漏出対応 | SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Seal the absorbent paper, as well as any of your clothing which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Wash any surfaces you may have contaminated with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. |
| 処分方法 | SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.1. Absorbing in vermiculite, dry sand, earth or similar material & disposing in secured sanitary landfill. 2. Atomizing in suitable combustion chamber./t-Butyl alcohol/ is a waste chemical stream constituent which may be subjected to ultimate disposal by controlled incineration. /Butanols, from table/Incineration & landfill: Incinerate waste by atomizing into a suitable combustion chamber. Bury absorbed waste in an approved landfill. |
| 漏出処分 | Remove all ignition sources. Evacuate danger area! Consult an expert! Personal protection: self-contained breathing apparatus. Ventilation. Collect leaking liquid in sealable containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Wash away remainder with plenty of water. |
| 体内負荷 | t-Butyl alcohol was identified, not quantified, in mother's milk(1,2). Results of blood analysis were reported for t-butyl alcohol from the 15 participants in the third National Health and Nutrition Examination Survey (NHANES III) and 18 Fairbanks, AK workers exposed to gasoline fumes and/or combustion products of gasoline(3). t-Butyl alcohol blood levels in the NHANES III study were 0.4-6.0 ug/L with a mean of 1.9 ug/LFairbanks post-shift workers blood levels were 1.6-76.5 ug/L with a mean of 23.1 ug/L(3). Twelve road-tanker truck drivers that worked various depot routes in Finland had t-butyl alcohol levels in urine of 173 to 1293 nmol/L (mean 461 nmol/L), immediately after the shift16 hours later the mean concentration was 322 nmol/L(4).t-Butyl alcohol levels in blood and urine samples from tank-lorry drivers from Helsinki, Finland were reported(1).[Table#88] |
| Cancer Sites | Endocrine |
| 相互作用 | Tertiary butyl alcohol and trichloroacetic acid are known to be contaminants in drinking water. In order to evaluate the interactive toxicity of t-butyl alcohol with trichloroacetic acid, young male Wistar rats were dosed through water at a dose level of t-butyl alcohol (TBA)-0.5% (v/v), trichloroacetic acid (TCA)-25 ppm and a combined dose of TBA + TCA (0.5% v/v TBA-25 ppm TCA) for a period of 10 weeks ad libitum and were maintained on normal diet. The control animals received plain water and normal diet. The liver and kidney histology was undertaken to see whether subtoxic administration of TBA and TCA individually as well as combined administration for a period of 10 weeks would bring about any histological alterations. It was observed that TBA, TCA and TBA + TCA caused histological alterations in the liver such as centrilobular necrosis, vacuolation in hepatocytes and loss of hepatic architecture. TBA and TBA + TCA caused periportal proliferation and lymphocytic infiltration. Hypertrophy of hepatocytes in the periportal area was a characteristic feature in the liver of TCA treated rats. Moreover, in the histology of the kidney, in the three treated groups, degeneration of renal tubules, with syncitial arrangements of the nucleus of renal tubular epithelial cells was evident. In addition to this, degeneration of the basement membrane of the Bowmans capsule, diffused glomeruli and vacuolation of glomeruli was also evident in the three treated rat kidneys. Renal tubular proliferation in certain areas was also evident in certain areas of the kidney in TCA treated rats. The results indicate that, TBA and TCA do bring about alterations in histology of liver and kidney, but on combined administration, do not show enhanced toxicity in the form of increased hepatic and renal injury. |
| 標的器官 | UrinaryEyes, skin, respiratory system, central nervous system |
| 生態毒性値 | LD100Species: Semolitus atromaculatus (creek chub) 6000 mg/L for 24 hr in Detroit river water /Conditions of bioassay not specified/LC50Species: Poecilia reticulata (guppy) 3550 ppm for 7 days /Conditions of bioassay not specified/Species: Xenopus laevis (African Clawed Frog) age 3-4 wkConditions: freshwater, static, 20 °CConcentration: 2450000 ug/L for 48 hr /formulated product/EC50Species: Daphnia magna (Water Flea)Conditions: freshwater, staticEffect: equilibriumConcentration: 5050000 ug/L for 24 hr /formulated product/For more Ecotoxicity Values (Complete) data for T-BUTYL ALCOHOL (6 total), please visit the HSDB record page. |
| 環境中動態 | TERRESTRIAL FATE: Based on a classification scheme(1), a Koc value of 37(2-3), indicates that t-butyl alcohol is expected to have very high mobility in soil(SRC). Volatilization of t-butyl alcohol from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 9.05X10-6 atm-cu m/mole(4). t-Butyl alcohol is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 40.7 mm Hg at 25 °C(5). The half-life of t-butyl alcohol under anoxic conditions in a non-amended soil was about 200 days, but the half-lives in the same soil amended with nitrate and sulfate nutrients were 100 and 50 days, respectively(6). Biodegradation of t-butyl alcohol in unamended soils collected at different depths had rates of <0.01 to 0.15 mg/L/day/gram dry soil(7).Degradation rates have been reported to be 4.01X10-8, 4.46X10-8 and 3.26X10-7/s for t-butyl alcohol(1). Primary persistence in soil, water and air are reported as 148, 160 and 64.6 days, respectively. Secondary persistence in soil, water and air are reported as 134, 156 and 123 days, respectively. Joint persistence with its parent compound methyl-t-butyl ether in soil, water and air are reported as 87.9, 105 and 81.5 days, respectively(1).AQUATIC FATE: Based on a classification scheme(1), a reported Koc value of 37(2-3), indicates that t-butyl alcohol is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(4) based upon a Henry's Law constant of 9.05X10-6 atm-cu m/mole(5). Using this Henry's Law constant and an estimation method(4), volatilization half-lives for a model river and model lake are 3.6 and 29 days, respectively(SRC). According to a classification scheme(6), a BCF of <5 in carp(7), suggests for bioconcentration in aquatic organisms is low(SRC). t-Butyl alcohol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(4). The biodegradation half-life of t-butyl alcohol was reported to range from about 28 to 180 days in aerobic water and 100 to 500 days in anaerobic water(8).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), t-butyl alcohol, which has a vapor pressure of 40.7 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase t-butyl alcohol 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 14 days(SRC), calculated from its rate constant of 1.12X10-12 cu cm/molecule-sec at 25 °C(3). t-Butyl alcohol does not contain chromophores that absorb at wavelengths >290 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC). |
| 食品調査値 | t-Butyl alcohol was identified, not quantified, in beer(1) and chickpeas(2). |
| 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 and by ingestion.inhalation, ingestion, skin and/or eye contact |
| Milk Concentrations | t-Butyl alcohol was identified, but not quantified, in mother's milk(1,2). |
| 毒性の概要 | Safe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.org |
| Signs and Symptoms | Dizziness. Drowsiness. Nausea. Headache. Vomiting.Redness.Redness. Pain.See Inhalation.irritation eyes, skin, nose, throatdrowsiness, narcosis |
| TSCA 要件 | Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329. Effective date: 1/26/94Reporting date: 3/28/94.Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. t-Butyl alcohol is included on this list. Effective date: 1/26/94Sunset date: 6/30/98. |
| FIFRA 要件 | As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their continued use. Under this pesticide reregistration program, EPA examines newer health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether the use of the pesticide does not pose unreasonable risk in accordance to newer saftey standards, such as those described in the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern than those on List C, and with List C containing pesticides of greater concern than those on List D. Butyl alcohol is found on List D. Case No: 4003Pesticide type: insecticide, fungicide, herbicide, antimicrobialCase Status: RED Approved 3/95OPP has made a decision that some/all uses of the pesticide are eligible for reregistration, as reflected in a Reregistration Eligibility Decision (RED) document .Active ingredient (AI): butyl alcoholAI Status: The active ingredient is no longer contained in any registered products. Thus, we characterize it as "cancelled.". |
| 大気基準 | This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. t-Butyl alcohol is produced, as an intermediate or a final product, by process units covered under this subpart. |
| 州飲料水ガイドライン | (CA) CALIFORNIA 12 ug/L(MA) MASSACHUSETTS 120 ug/L(NH) NEW HAMPSHIRE 40 ug/L(NJ) NEW JERSEY 100 ug/L |
| 職業暴露区分（OEB） | A |
| 職業暴露限界（OEL） | TWA: 100 ppm (300 mg/m3), STEL: 150 ppm (450 mg/m3) |
| 水環境危害等級（WGK） | 1 |
| 生命健康即時危険濃度 | 1,600 ppm |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | EO1925000 |
| 輸送番号（UN） | UN 1120 3/PG 3 |
| 毒性 | LD50 orally in rats: 3.5 g/kg (Schaffarzick, Brown) |
| 税関コード | 29051410 |
| 危険文句（R） | 11-20-39/23/24/25-23/24/25-36/37 |
| 化審法 | (2)-3049 |
| 安衛法 | 57,57-2 |
| 消防法 | 危険物第4類第一石油類(水溶性) |
| 危険表示 | Xn,F,T |
| 安全措置（S） | 9-16-45-36/37-7-46-26 |
| 危険等級 | 3Acute Tox. 4 InhalationEye Irrit. 2Flam. Liq. 2STOT SE 3 |
| 包装等級 | II |
| 自然発火温度 | 896 °F |
| 環境リスク評価 | 2-メチルプロパン-2-オール(75-65-0) |
| 貯蔵分類 | 3 - Flammable liquids |
| 有害物質データ | 75-65-0(Hazardous Substances Data) |
用途
用途
ブタノールは多様な用途で使用されており溶剤燃料の添加物化学合成の中間体などがあります具体的には塗料やインクプラスチックの製造過程で溶剤として利用されることが多いですまたブタノールはガソリンのオクタン価を向上させる添加物としても用いられ燃料の性能を高めるのに貢献していますさらにアセトンやブタンジオールなどの化学物質の生産においても重要な原料となっています
使用
tert-Butanol can be used as a solvent (e.g., for paints, lacquers, and varnishes); as a denaturant for ethanol and several other alcohols; as an octane booster in gasoline; as a dehydrating agent; as a chemical intermediate in the manufacturing of methyl methacrylate; and in the manufacturing of flotation agents, fruit essences, and perfumes.
一般的な説明
Colorless oily liquid with a sharp alcohol odor. Floats and mixes with water. Produces irritating vapor. Freezing point is 78°F.
製法・合成法
調製方法
tert-Butanol is produced as a by-product from the isobutane oxidation process for manufacturing propylene oxide. It is also produced by the acidcatalyzed hydration of isobutylene, a process no longer used in the United States.
純化方法
tert-Butanol is synthesised commercially by the hydration of 2-methylpropene in dilute H2SO4. Dry it with CaO, K2CO3, CaSO4 or MgSO4, filter and fractionally distil it. Dry further by refluxing with, and distilling from, either magnesium activated with iodine, or small amounts of calcium, sodium or potassium, under nitrogen. Passage through a column of type 4A molecular sieve is another effective method of drying; as well as refluxing with tert-butyl phthalate or succinate. (For method see Ethanol.) Other methods include refluxing with excess aluminium tert-butylate, or standing with CaH2, and distilling as needed. Further purification is achieved by fractional crystallisation by partial freezing, taking care to exclude moisture. tert-Butyl alcohol samples containing much water can be dried by adding *benzene, so that the water distils off as a tertiary azeotrope, b 67.3o. Traces of isobutylene have been removed from dry tert-butyl alcohol by bubbling dry pre-purified nitrogen through for several hours at 40-50o before using. It forms azeotropic mixtures with a large number of compounds. It has also been purified by distillation from CaH2 into Linde 4A molecular sieves which had been activated at 350o for 24hours [Jaeger et al. J Am Chem Soc 101 717 1979]. [Beilstein 1 IV 1609.] Rapid purification: Dry tert-butanol over CaH2 (5% w/v), distil and store it over 3A molecular sieves.