化工社化工社 化学情報印刷レポート · 研究参考用
2,3-ブタンジオール
2,3-ブタンジオール (ステレオ異性体混合物) · プソイドブチレングリコール · ジメチレングリコール · ジメチルエチレングリコール · ψ-ブチレングリコール · 1,2-ジメチル-1,2-エタンジオール · β,γ-ブチレングリコール · 2,3-ブチレングリコール
識別子と物理属性
| CAS No. | 35007-63-7 |
|---|---|
| 分子式 | C4H10O2 |
| 平均分子量 | 90.12 g/mol |
| 単同位体質量 | 90.06807956 g/mol |
| SMILES | CC(O)C(C)O |
| InChIKey | OWBTYPJTUOEWEK-UHFFFAOYSA-N |
| PubChem CID | 262 |
| ChEMBL | CHEMBL2312529 |
| ChEBI | CHEBI:62064 |
| EC No. | 208-173-6 |
| DTXSID | DTXSID8041321 |
| 現地名 | 2,3-ブタンジオール |
化学・物理的性質
| XLogP | -0.9 |
|---|---|
| 極性表面積 | 40.5 |
| 水素結合供与体数 | 2 |
| 水素結合受容体数 | 2 |
| 回転可能結合数 | 1 |
| 重原子数 | 6 |
| 形式電荷 | 0 |
| 複雑度 | 30 |
| LogP（分配係数） | log Kow = -0.92 |
| 臭い | Odorlessジプロピレングリコール中0.10%。フルーティーでクリーミーなバターのような |
| 味 | Sweet taste |
| 密度 | 1.045 at 20 °C/20 °C1.002 g/mL at 20 °C (lit.) |
| Viscosity | 0.121 sq m/sec at 25 °C |
| Color/Form | Nearly colorless, crystalline solid or liquid |
| 溶解度 | In water, miscible at 20 °CMiscible with waterEasily soluble in low molecular mass alcohols and ketones.Soluble in alcohol, ether1000 mg/mL at 20 °Cクロロホルム、メタノール溶ける |
| 引火点 | 85 °C85 °C (185 °F) - closed cup185 °F - open cup |
| 沸点 | BP: 182 °C at 1 atm182.00 °C. @ 760.00 mm Hg183-184 °C (lit.) |
| Decomposition | Hazardous decomposition products formed under fire conditions - Carbon oxides.When heated to decomposition it emits acrid smoke and fumes. |
| 融点 | 19 °C25 °C25 °C (lit.) |
| 蒸気密度 | 3.1 (Air = 1) |
| 蒸気圧 | <1 hPa (20 °C) |
| 屈折率 | n20/D 1.433(lit.) |
| 貯蔵条件 | Store below +30°C. |
| pKa（酸解離定数） | 14.67±0.20(Predicted) |
| 外観・状態 | 粘性液体 |
| 色 | 無色～淡黄色 |
| pH | 7 (H2O, 20℃)Aqueous solution |
| 爆発限界 | 3.1-11.4%(V) |
| においのタイプ | クリーミーな |
| 比熱容量 | Cp(liquid): 2.36 J/(g·K), at 25℃ |
| Merck | 14,1568 |
| BRN | 969165 |
| ヘンリー定数 | 1.1×103 mol/(m3Pa) at 25℃, Burkholder et al. (2019) |
| 安定性 | 安定。可燃性。強力な酸化剤、酸無水物、酸塩化物、クロロホルメート、還元剤とは相容れない。 |
| 化粧品成分の機能 | 保湿剤溶媒スキンコンディショニング香料 |
| InChI | 1S/C4H10O2/c1-3(5)4(2)6/h3-6H,1-2H3 |
| InChIKey | OWBTYPJTUOEWEK-UHFFFAOYSA-N |
| SMILES | CC(O)C(C)O |
| LogP（分配係数） | -0.92 at 25℃ |
| CAS データベース | 513-85-9(CAS DataBase Reference) |
| NISTの化学物質情報 | 2,3-Butanediol(513-85-9) |
| EPAの化学物質情報 | 2,3-Butanediol (513-85-9) |
化学的特性
viscous colourless liquid, or colourless to white solid
化学性质
脱水することでブタジエンに変換される
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 94.5% (208 of 220) of all reports.Not ClassifiedReported as not meeting GHS hazard criteria by 208 of 220 companies (only 5.5% companies provided GHS information). For more detailed information, please visit ECHA C&L website.Aggregated GHS information provided per 220 reports by companies from 3 notifications to the ECHA C&L Inventory.Reported as not meeting GHS hazard criteria per 208 of 220 reports by companies.There are 2 notifications provided by 12 of 220 reports by companies with hazard statement code(s).Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.WarningH227: Combustible liquid [Warning Flammable liquids]P210, P280, P370+P378, P403, and P501 (click each P-code to see the statement) |
|---|---|
| 規制情報 | Chemical: 2,3-ButanediolCommission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)Status: Active Update: 15-08-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/100602,3-Butylene glycol: Does not have an individual approval but may be used under an appropriate group standard |
| その他の安全情報 | Evaluation - Chemicals that are unlikely to require further regulation to manage risks to environment |
| 火災の可能性 | Flammable when exposed to heat or flame. |
| 有害性の概要 | Emergency treatment: Glycols[HSDB] Intraperitoneal dose of 3920 mg/kg was lowest dose to produce ataxia in rats[RTECS] May cause irritation[MSDSonline] |
| EPA Safer Chemical | Chemical: 2,3-ButanediolGreen circle - The chemical has been verified to be of low concern based on experimental and modeled data. |
| NFPA Hazard Classification | 1 - Materials that, under emergency conditions, can cause significant irritation.1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.0 - Materials that in themselves are normally stable, even under fire conditions. |
| Hazard Classes and Categories | Not Classified |
| Hazardous Reactivities and Incompatibilities | Incompatible materials: Acid chlorides, acid anhydrides, oxidizing agents, chloroformates, reducing agents, zinc.Incompatible with oxidizing materials. |
| 消火手順 | Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.Use water spray to cool unopened containers.To fight fire, use alcohol foam, carbon dioxide, dry chemical. |
| 保管条件 | Keep container tightly closed in a dry and well-ventilated place. Hygroscopic. |
| 清掃方法 | ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Avoid breathing vapors, mist or gas. Remove all sources of ignition. 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. Keep in suitable, closed containers for disposal. |
| 処分方法 | SRP: 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 air, soil or watereffects on animal, aquatic and plant lifeand conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.Product: This combustible material may be burned in a chemical incinerator equipped with an afterburner and scrubber. Offer surplus and non-recyclable solutions to a licensed disposal companyContaminated packaging: Dispose of as unused product. |
| Preventive Measures | ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Avoid breathing vapors, mist or gas. Remove all sources of ignition. 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.Precautions for safe handling: Avoid inhalation of vapor or mist. Keep away from sources of ignition - No smoking. Take measures to prevent the build up of electrostatic charge.Appropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. |
| Personal Protective Equipment (PPE) | Eye/face protection: Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).Skin protection: Handle with gloves.Body Protection: Impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with multipurpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU). |
| 相互作用 | Erythrocytes were stored at 4 degrees C in solutions of phosphate-buffered saline containing 2,3-butanediol and 4% (w/w) trehalose, sucrose, sorbitol, or mannitol. The 2,3-butanediol contained 96.7% (w/w) racemic mixture of the levo and dextro isomers and only 3.1% (w/w) of the meso isomer (2,3-butanediol 97% dl). The concentrations of 2,3-butanediol were 30 and 35% (w/w). A solution of 30% 2,3-butanediol showed relatively low toxicity. Hemolysis was only 2% after 5 hr, but increased to 6% after 21 hr and reached 60% after 46 hr. Adding 4% (w/w) of one of the above compounds drastically decreased the toxicity. The two most efficient were the sugars trehalose and sucrose. With 30% 2,3-butanediol and 4% of any of the four compounds, hemolysis was about 0.6% after 2 days of storage. Furthermore, with trehalose or sucrose, hemolysis remained below 3% for 1 month. With sorbitol or mannitol, hemolysis slowly increased to 2% after 7 days and then increased rapidly. Even with 35% 2,3-butanediol, solutions containing trehalose or sucrose showed low toxicity. Hemolysis was also measured after redilution to buffered solution without 2,3-butanediol and without the additive, to mimic perfusion of organs with cryoprotectants and washing. Minima of hemolysis were observed after a few days of storage. The present solutions also have high glass-forming tendencies. They could be of great interest for organ vitrification.... A 16 hr pretreatment with either 2-butanone (2.1 mL/kg, orally) or 2,3-butanediol (2.12 mL/kg, orally) markedly enhanced the hepatotoxic response to CCl4 (0.1 mL/kg, ip), as measured by serum glutamic pyruvic transaminase activity and hepatic triglyceride content. In vivo, limited formation of 3-hydroxy-2-butanone occurred after this dose of 2,3-butanediol. |
| 環境中動態 | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that 2,3-butanediol is expected to have very high mobility in soil(SRC). Volatilization of 2,3-butanediol from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.9X10-8 atm-cu m/mole(SRC), based upon its vapor pressure, 0.24 mm Hg(3), and assigned value for water solubility of 1X10+6 mg/L (miscible)(4). 2,3-Butanediol is not expected to volatilize from dry soil surfaces(SRC) based upon a its vapor pressure(3). Using anaerobic test conditions, 75-100% biodegradation was reported(5), suggesting that biodegradation may be an important enviornmental fate process in soil under anoxic conditions(src).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that 2,3-butanediol is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.9X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 0.18 mm Hg(4), and assigned value for water solubility of 1X10+6 mg/L (miscible)(5). 2,3-Butanediol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). According to a classification scheme(6), an estimated BCF of 3(SRC), from its log Kow of -0.92(7) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low. Using anaerobic test conditions, 75-100% biodegradation was reported(8), suggesting that biodegradation may be an important enviornmental fate process in soil and water under anoxic conditions.ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2,3-butanediol, which has a vapor pressure of 0.24 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2,3-butanediol 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 16 hours(SRC), calculated from its reported rate constant of 2.36X10-11 cu cm/molecule-sec at 25 °C(3). 2,3-Butanediol 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 | 2,3-Butanediol is a volatile constituent of sweet corn with concentrations >5,000 ppb in canned cream, canned kernel, and frozen kernel and >3,000 ppb in fresh kernel corn(1). 2,3-Butanediol and meso-2,3-butanediol were detected as volatile constituents of microwave oven-produced popcorn with concentrations of 800 ppb and 1200 ppb, respectively(2). It was detected as a volatile constituent in two different brands of rice cakes with concentrations of 62 ppb and 38 ppb(3). 2,3-Butanediol was detected among volatile components in two of three samples of commercial fermented soybean curds with concentrations of 244.3 ppb and 333.5 ppb(4) and was detected among volatile components of whole and ground grains (sorghum)(5). 2,3-Butanediol was detected as a volatile constituent in rotten mussels collected from the Oarai coast in Ibaraki, Japan on July 31, 1985 with a concentration of 14.2 ppm(6).2,3-Butanediol was detected in muskmelon (Cucumis melo cv Athena) fruit at 0.47 ppm, it was not detected in muskmelon essence, samples were collected in Florida(1). 2,3-Butanediol was detected in pink guava fruit (Psidium guajava L), it was not detected in guava essence, samples were collected in Florida(2). Balsamic vinegars, aged 0-25 years, collected from Modena and Reggio Emilia, Italy, contained 2,3-butanediol at 110-1561 mg/kg(3). The concentration of 2,3-butanediol in white wines from Muscat Lefko (Vitis vinifera) grapes from the Islands of Samos was reported as 130-2986 mg/L(4). 2,3-Butanediol was detected in red wines (Cabernet Sauvignon, Campbell Early, Shiraz, Cabernet Sauvignon/Merlot) from France, Korea, Australia and California(5). In wine samples collected from Basilicata and Campania, Italy, 2,3-butanediol was detected at 385.1-725.4 and 297.9-479.5 mg/L, respectively(6). 2,3-Butanediol was identified, not qualified, in Manchego-type cheese from Madrid, Spain(7). |
| 有害作用 | Neurotoxin - Acute solvent syndrome |
| 毒性の概要 | The Panel also concluded that the available data are insufficient to make a determination that ... 2,3-Butanediol ... is safe under the intended conditions of use in cosmetic formulations.The available data are insufficient to support safetyIDENTIFICATION AND USE: 2,3-Butanediol is nearly colorless, crystalline solid or liquid. 2,3-Butanediol is used as a crosslinking agent for naphthalene-1,5-diisocyanate in the production of specific hard-rubber products. Derivatives of 2,3-butanediol are important as intermediates in the pharmaceutical industry. 2,3-Butanediols have some interest as humectants and in the synthesis of polymers and plasticizers. HUMAN STUDIES: For erythrocytes a solution of 30% 2,3-butanediol showed relatively low toxicity. Hemolysis was only 2% after 5 hr, but increased to 6% after 21 hr and reached 60% after 46 hr. ANIMAL STUDIES: Effects of 2,3-butanediol on the central nervous system (CNS) were investigated by using the analysis of EEG (electroencephalogram) spectral powers recorded at the frontal cortex in rats. It was found that 2,3-butanediol treatment led to increase in EEG spectral powers by oral and intravenous administrations at relatively low doses. From these findings it can be concluded that 2,3-butanediol has a potent CNS depressant effect. 2,3-Butanediol was not embryotoxic when examined in cultured 10-day rat embryo. 2,3-Butanediol has a negative regulatory effect on rats innate immunity response. |
| Plant Concentrations | 2,3-Butanediol is found in the fruit of sweet pepper plants (Capsicum annuumSolanaceae)(1). |
| Ongoing Test Status | EPA has released the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays/[USEPAICSS Dashboard ApplicationAvailable from, as of July 27, 2017: http://actor.epa.gov/dashboard/] |
| Effluent Concentrations | 2,3-Butanediol was qualitatively identified as a component of garden waste volatiles collected from headspace gas in three waste collection trucks in Denmark(1). An unspecified isomer of butanediol was qualitatively identified as a volatile component at 1 of 5 hazardous waste sites(2). 2,3-Butanediol was detected in 3 of 7 samples of scrape tire pyrolysis at 5, 64 and 250 mg/kg scrap tire(3). |
| Soil Adsorption/Mobility | Using a structure estimation method based on molecular connectivity indices(1), the Koc of 2,3-butanediol can be estimated to be 1(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2,3-butanediol is expected to have very high mobility in soil(SRC). |
| Natural Pollution Sources | 2,3-Butanediol is a volatile constituent of sweet corn(1), fermented soybean curds(2), whole and ground grains(3), and rotten mussels(4). 2,3-Butanediol is produced in the fermentation of many fruits and grains(5). 2,3-Butanediol is found in the fruit of sweet pepper plants (Capsicum annuum)(6). |
| Human Toxicity Excerpts | /ALTERNATIVE and IN VITRO TESTS/ Erythrocytes were stored at 4 degrees C in solutions of phosphate-buffered saline containing 2,3-butanediol and 4% (w/w) trehalose, sucrose, sorbitol, or mannitol. The 2,3-butanediol contained 96.7% (w/w) racemic mixture of the levo and dextro isomers and only 3.1% (w/w) of the meso isomer (2,3-butanediol 97% dl). The concentrations of 2,3-butanediol were 30 and 35% (w/w). A solution of 30% 2,3-butanediol showed relatively low toxicity. Hemolysis was only 2% after 5 hr, but increased to 6% after 21 hr and reached 60% after 46 hr. Adding 4% (w/w) of one of the above compounds drastically decreased the toxicity. The two most efficient were the sugars trehalose and sucrose. With 30% 2,3-butanediol and 4% of any of the four compounds, hemolysis was about 0.6% after 2 days of storage. Furthermore, with trehalose or sucrose, hemolysis remained below 3% for 1 month. With sorbitol or mannitol, hemolysis slowly increased to 2% after 7 days and then increased rapidly. Even with 35% 2,3-butanediol, solutions containing trehalose or sucrose showed low toxicity. Hemolysis was also measured after redilution to buffered solution without 2,3-butanediol and without the additive, to mimic perfusion of organs with cryoprotectants and washing. Minima of hemolysis were observed after a few days of storage. The present solutions also have high glass-forming tendencies. They could be of great interest for organ vitrification. |
| Artificial Pollution Sources | 2,3-Butanediol's production and use as a solvent for dyes, in resins, as an intermediate, and as a blending agent(1) may result in its release to the environment through various waste streams(SRC). |
| 水環境危害等級（WGK） | 1 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | EK0532000 |
| 毒性 | LD50 orally in Rabbit: > 5000 mg/kg |
| 税関コード | 29053980 |
| 化審法 | (2)-235 |
| 消防法 | 危-4-3-III |
| 安全措置（S） | 24/25 |
| 自然発火温度 | 395 °C DIN 51794 |
| 貯蔵分類 | 10 - Combustible liquids |
| 有害物質データ | 513-85-9(Hazardous Substances Data) |
用途
用途
凍結防止剤としてエチレングリコールの代用として、またタバコ、織物、接着剤の湿潤剤または軟化剤として用いられるが、重要な用途は脱水によりブタジエンを合成することである。
説明
2,3-Butanediol(23BD) is the organic compound with the formula (CH3CHOH). It is classified as a vic-diol (glycol). It exists as three stereoisomers, a chiral pair and the meso isomer. All are colorless liquids. Applications include precursors to various plastics and pesticides.2,3-Butanediol is a commodity chemical usually produced from oil. It can be used as a precursor in the manufacture of a range of chemical products, including the solvents methyl ethyl ketone (MEK), gamma-butyrolactone (GBL), and 1,3-butadiene.
使用
2,3-Butanediol (2,3-BD) is a promising bulk chemical with a potentially wide range of applications e.g., in the manufacture of printing inks, perfumes, synthetic rubber, fumigants, antifreeze agents, fuel additives, foodstuffs and pharmaceuticals. Its high heating value and ability to increase the octane number of fuels make 2,3-BD a promising drop-in fuel. It can also be converted to methyl-ethyl ketone (MEK), which is considered an effective liquid fuel additive. After combination with MEK and hydrogenation reaction, 2,3-BD can be converted to octane, which is used to produce high-quality aviation fuel.
一般的な説明
2,3-Butanediol is a chiral compound which is extensively utilized in chemical feedstocks and liquid fuels.
製法・合成法
製造方法
2,3-Butanediol is prepared by hydrolysis of 2,3-epoxybutane:(CH3CH)2O + H2O → CH3(CHOH)2CH3
合成方法
アセトインを経由した発酵法
純化方法
Recrystallise it from isopropyl ether at low temperature. [Beilstein 1 IV 2524.]