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4-甲基-2-戊醇
甲异醇 · 仲己醇 · 2-己醇 · 甲基戊醇 · 1-乙基丁醇 · 甲基吲哚甲酸 · 四甲基二戊醇 · 甲基異丁基甲醇
标识与物理属性
| CAS No. | 108-11-2 |
|---|---|
| 分子式 | C6H14O |
| 平均分子量 | 102.17 g/mol |
| 单同位素质量 | 102.10446507 g/mol |
| SMILES | CC(C)CC(C)O |
| InChIKey | WVYWICLMDOOCFB-UHFFFAOYSA-N |
| PubChem CID | 7910 |
| ChEMBL | CHEMBL448896 |
| EC No. | 203-551-7 |
| DTXSID | DTXSID2026781 |
| 中文名 | 4-甲基-2-戊醇 |
化学与物理性质
| XLogP | 1.7 |
|---|---|
| 极性表面积 | 20.2 |
| 氢键供体 | 1 |
| 氢键受体 | 1 |
| 可旋转键 | 2 |
| 重原子 | 7 |
| 形式电荷 | 0 |
| 复杂度 | 41.4 |
| 物质类别 | Flammable agents - 2nd degreeVolatile Organic Compound (VOC) |
| Solvents | Solvents -> Alcohols (<C12) |
| 香料 | Fragrance Ingredient (4-Methyl-2-pentanol) -> IFRA transparency List |
| LogP（油水分配系数） | log Kow= 1.43 |
| 气味 | Mild odor.Sharpmild and nonresidual. |
| 密度 | 0.807 at 68 °F (USCG, 1999) - Less dense than waterwill float0.8075 @ 20 °C/4 °C% IN SATURATED AIR: 0.46 @ 20 °CDENSITY OF SATURATED AIR: 1.01 (AIR= 1)Relative density (water = 1): 0.820.810.802 g/mL at 25 °C(lit.) |
| 食用香料 | EU Flavoring substances |
| Color/Form | COLORLESS LIQColorless liquid. |
| 溶解性 | 2 % (NIOSH, 2024)SOL IN ALC & ETHER.MISCIBLE WITH MOST COMMON ORG SOLVENTS.Water solubility of 1.64X10+4 mg/kg (experimental).Solubility in water, g/100ml: 22%16.4g/l2 g/100 mL |
| 闪点 | 106 °F (USCG, 1999)105 °F105 °F (OPEN CUP)41 °C107 °F |
| 沸点 | 269.2 °F at 760 mmHg (USCG, 1999)133 °C @ 760 MM HG132 °C271 °F134-135 °C(lit.) |
| 熔点 | less than -130 °F (USCG, 1999)-90 °C |
| 蒸气密度 | 3.5 (vs air) |
| 蒸气压 | 3.7 mm Hg ( 20 °C) |
| 折射率 | n20/D 1.415(lit.) |
| 储存条件 | Store below +30°C. |
| 形态 | Liquid |
| pKa（酸度系数） | 15.31±0.20(Predicted) |
| 颜色 | Clear colorless |
| 香型 | pungent |
| 爆炸极限 | 1-5.5%(V) |
| 比热容 | Cp(liquid): 2.67 J/(g·K), at 25℃ |
| BRN | 1098268 |
| 亨利常数 | 2.2×10-1 mol/(m3Pa) at 25℃, Brockbank (2013) |
| 暴露限值 | ACGIH:TLV-TWA 20 ppmTLV-STEL 40 ppmOSHA:PEL-TWA 25 ppm (100 mg/m3)NIOSH:REL-TWA 25 ppmREL-STEL 40 ppm |
| 稳定性 | Stable. Flammable. Incompatible with oxidizing agents, acids, acid chlorides. |
| 化妆品成分功效 | PERFUMING |
| InChI | 1S/C6H14O/c1-5(2)4-6(3)7/h5-7H,4H2,1-3H3 |
| InChIKey | WVYWICLMDOOCFB-UHFFFAOYSA-N |
| SMILES | CC(C)CC(C)O |
| LogP（油水分配系数） | 1.57 at 20℃ |
| CAS 数据库 | 108-11-2(CAS DataBase Reference) |
| NIST化学物质信息 | 2-Pentanol, 4-methyl-(108-11-2) |
| EPA化学物质信息 | 4-Methyl-2-pentanol (108-11-2) |
化学性质
无色稳定液体。熔点-90℃，凝固点-90℃，沸点132℃，相对密度0.8083（20/20℃），折射率1.4112，闪点40.6℃，蒸气压（20℃）0.373kPa，粘度5.2mPa·s。在低于-90℃时固化为玻璃体。蒸气与空气形成爆炸性混合物，爆炸极限1%-5.5%。能与多种有机溶剂混溶，微溶于水，20℃时在水中的溶解为1.9%。
安全与法规
| GHS 分类 | WarningH226: Flammable liquid and vapor [Warning Flammable liquids]P210, P233, P240, P241, P242, P243, P261, P271, P280, P303+P361+P353, P304+P340, P319, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]P210, P233, P240, P241, P242, P243, P261, P264+P265, P271, P280, P303+P361+P353, P304+P340, P305+P351+P338, P319, P337+P317, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement) |
|---|---|
| 法规信息 | Chemical: 2-Pentanol, 4-methyl-Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)2-Pentanol, 4-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Pentanol, 4-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: 03-04-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/161892-Pentanol, 4-methyl-: HSNO Approval: HSR001193 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.) |
| 其他安全信息 | IMAP assessments - 2-Pentanol, 4-methyl-: Environment tier I assessment |
| 运输标签（DOT） | Flammable Liquid |
| 火灾危害 | Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.Flammable. Above 41 °C explosive vapour/air mixtures may be formed. |
| 火灾可能性 | MODERATE FIRE RISK. |
| 健康危害 | Vapor irritates eyes and nosemay cause anesthesia. Prolonged contact with liquid causes irritation and cracking of skinalso irritates eyes. (USCG, 1999)· May cause toxic effects if inhaled or absorbed through skin. |
| 危害概述 | In acute animal studies, high concentrations induce narcosis and anesthesia. [ACGIH] Inhalation of high concentrations can cause CNS depressionA skin, eye, and respiratory tract irritant[ICSC] |
| 运输编号与指南（DOT） | 2053 129 |
| 反应性基团 | Alcohols and Polyols |
| 欧共体分类 | Symbol: XiR: 10-37S: (2)-24/25 |
| 联合国分类 | UN Hazard Class: 3UN Pack Group: III |
| OSHA Standards | Permissible Exposure Limit: Table Z-1 8-hr Time-Weighted Avg: 25 ppm (100 mg/cu m). Skin Designation.Vacated 1989 OSHA PEL TWA 25 ppm (100 mg/cu m)STEL 40 ppm (165 mg/cu m), skin designation, is still enforced in some states. |
| 消防 | Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:Use water spray, powder, alcohol-resistant foam, carbon dioxide. |
| 急救措施 | Fresh air, rest. 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. Rest. Refer for medical attention . |
| 泄漏应急措施 | · 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. |
| 急救 | Excerpt from NIOSH Pocket Guide for Methyl isobutyl carbinol:General First Aid:(General first aid procedures) |
| 安全储存 | Fireproof if in building. Separated from strong oxidants. Cool. |
| 暴露控制与个人防护 | · Wear positive pressure self-contained breathing apparatus (SCBA).20.0 [ppm] |
| 灭火程序 | ALCOHOL FOAM. |
| 非火灾泄漏应对 | Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]: |
| 泄漏处置 | Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Ventilation. Collect leaking liquid in sealable containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Do NOT wash away into sewer. |
| Preventive Measures | The worker should immediately wash the skin when it becomes contaminated.Work clothing that becomes wet or significantly contaminated should be removed and replaced.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. |
| Isolation and Evacuation | Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:Immediate precautionary measure |
| Eye Prevention | Wear safety goggles. |
| 靶器官 | Eyes, skin, central nervous system |
| 生态毒性数值 | LD50 Goldfish 360 mg/l/24 hr (modified ASTM D 1345) |
| 环境归趋 | TERRESTRIAL FATE: If 4-methyl-2-pentanol is released to soil, it will be expected to exhibit high to very high mobility in soil(1,SRC) based upon estimated Koc of 143 and 21 estimated from log Kow(2) and water solubility(3), respectively, using a recommended regression equations(4,SRC). It may, therefore, leach through soil(SRC). It will not hydrolyze in moist soil(4), but it may be subject to volatilization from near surface soil based upon estimated rates for its volatilization from water(4-6). It may be subject to biodegradation in soil based upon the rapid biodegradation observed in laboratory aqueous screening tests using sewage and activated sludge inoculum(7,8).AQUATIC FATE: If 4-methyl-2-pentanol is released to water, it will not be expected to adsorb to sediment and suspended particulate matter or to bioconcentrate in aquatic organisms based upon estimated Koc and BCF, respectively, estimated(2,SRC) from the measured log Kow (1) and water solubility(3). It will not be expected to hydrolyze(2) or directly photolyze(4,SRC). It may be subject to biodegradation in natural waters based upon the rapid biodegradation observed in laboratory aqueous screening tests using sewage and activated sludge inoculum(5,6). It will be subject to volatilization from surface waters based upon half-lives of 23 hr for volatilization from a model river one meter deep flowing 1 m/sec with a wind velocity of 3 m/sec(2,SRC) and 10.6 days for volatilization from a model pond(7,SRC), respectively, estimated using a measured Henry's Law constant(8).ATMOSPHERIC FATE: If 4-methyl-2-pentanol is released to the atmosphere, it can be expected to exist mainly in the vapor-phase in the ambient atmosphere(1,SRC) based upon an experimental vapor pressure of 5.3 mm Hg at 25 °C(2,SRC). The measured rate constant for vapor-phase reaction with photochemically produced hydroxyl radicals of 7.1X10-12 cu cm/molecule-sec at 25 °C(3) corresponds to an atmospheric half-life of 2.3 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(SRC). 4-Methyl-2-pentanol has been rated a moderately reactive (Class III) compound(4) with respect to ozone formation as observed in smog chamber tests(5). 4-Methyl-2-pentanol will not be expected to directly photolyze in the atmosphere(6,SRC). |
| 食品调查数值 | 4-Methyl-2-pentanol was qualitatively detected in the mixture of volatiles from mountain Beaufort cheese(1). |
| 不良影响 | Neurotoxin - Acute solvent syndrome |
| 暴露途径 | The substance can be absorbed into the body by inhalation of its vapour and through the skin.inhalation, skin absorption, ingestion, skin and/or eye contact |
| Signs and Symptoms | Cough. Sore throat. Unconsciousness.Dry skin. Redness. Pain.irritation eyes, skinheadache, drowsinessdermatitisIn Animals: narcosis |
| Effluent Concentrations | 4-Methyl-2-pentanol was detected at a concn of 136 ppb in a sample of influent water from an unspecified municipal wastewater treatment plant(1). It was not indicated whether the compound was detected in final effluent from the plant(1). It was detected at a concn of 45 ppb in effluent samples taken from the Los Angeles County wastewater treatment plant discharge, Palos Verdes, CA between Nov 1980 and Aug 1981(2). A concn of 140 ppm was found in samples of leachate or samples of groundwater plume taken at an unspecified industrial landfill at an unspecified time(3). 4-Methyl-2-pentanol was qualitatively detected in 4 of 16 samples of concentrate derived from large volume (>400 gallons) samples of advanced treatment concentrate from 4 of 6 cities (Lake Tahoe, CA, Oct 1974Pomona, CA, 1975Orange County, CA, Feb 1976Blue Plains, Washington, DC, May 1975)(4). |
| Soil Adsorption/Mobility | Based upon an experimental log Kow of 1.43(1), a Koc of 143 has been estimated using a recommended regression equation(2). Based upon an experimental water solubility of 1.64X10+4 mg/kg(3), a Koc of 21 has been estimated using a recommended regression equation(2). Based upon these estimated Koc, 4-methyl-2-pentanol will be expected to exhibit high to very high mobility in soil(4). 4-Methyl-2-pentanol, therefore, may leach through soil to groundwater if it does not volatilize or biodegrade first(SRC). |
| Natural Pollution Sources | 4-Methyl-2-pentanol was qualitatively detected in the mixture of volatiles from mountain Beaufort cheese(1) which indicates that the compound may be formed naturally(SRC). |
| Atmospheric Concentrations | 4-Methyl-2-pentanol was qualitatively detected in ambient air samples taken Nov 20, 1979 at the BFI Landfill in New Jersey(1). It was detected in ambient air during an air pollution peak at concn ranging from 0.9 to 7.0 ppbdate and location not specified(2). |
| Human Toxicity Excerpts | THE LIQ MAY BE VERY SLIGHTLY IRRITATING TO SKIN & IS SLIGHTLY TOXIC WHEN INGESTED.... EYE IRRITATION WAS PRODUCED @ 50 PPM, ALTHOUGH ODOR WAS NOT OBJECTIONABLE @ THIS LEVEL. |
| 大气标准 | 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. Methyl isobutyl carbinol is produced, as an intermediate or final product, by process units covered under this subpart. |
| 水危害等级（WGK） | 1 |
| TSCA 清单状态 | TSCA listed |
| 毒性 | LD50 orally in Rabbit: 2590 mg/kg LD50 dermal Rabbit 2884 mg/kg |
| RTECS 号 | SA7350000 |
| 包装类别 | III |
| 危险类别 | 3Eye Irrit. 2Flam. Liq. 3STOT SE 3 |
| 储存类别 | 3 - Flammable liquids |
| 安全说明（S） | 24/25-26 |
| 海关编码 | 29051900 |
| 自燃温度 | 305 °C |
| 危险品标志 | Xi |
| 危险类别码（R） | 10-37-36/37/38 |
| 毒害物质数据 | 108-11-2(Hazardous Substances Data) |
| 职业暴露等级（OEB） | A |
| 职业暴露限值（OEL） | TWA: 25 ppm (100 mg/m3), STEL: 40 ppm (165 mg/m3) [skin] |
| 运输编号（UN） | UN 2053 |
| 立即危及生命和健康浓度 | 400 ppm |
急性毒性
口服-大鼠 LD50: 2590 毫克/公斤; 腹腔-小鼠 LD50: 812 毫克/公斤
职业标准
TLV-TWA 100 毫克/立方米; STEL 160 毫克/立方米
爆炸物危险特性
蒸气与空气混合可爆
可燃性危险特性
易燃; 火场释放辛辣刺激烟雾
储运特性
库房通风低温干燥; 与氧化剂分开储运
灭火剂
干粉, 二氧化碳, 1211, 泡沫
用途与应用
用途
4-甲基-2-戊醇是优良的中沸点溶剂。主要用作染料、石油、橡胶、树脂、石蜡、硝基纤维素和乙基纤维素等的溶剂，用作硝化纤维素漆的惰性溶剂，可增加涂料的光泽和平整性，改进泛红性能；在润滑油添加剂制造中用作溶剂等。用于有机合成的原料，矿物浮选洗剂，如萃取硅和硫酸铜矿；还可用于刹车液。
制备与合成方法
生产方法
先由丙酮在碱性催化剂存在下，加压缩合转化成二丙酮醇（见11360）。使用的催化剂为氢氧化钙或氢氧化钡。当催化剂粒子很小、表面积很大时，这一液相接触反应接近于均相反应。反应过程放出热量，低温下平衡转化率大。因此，原料丙酮要预冷，反应在0-10℃下操作。然后，二丙酮醇脱水生成异丙叉丙酮。过程获得的二两样酮醇，一般含量为10-15%，采用常压蒸馏浓缩至80%，同时分离和回收未转化的丙酮。在硝酸、硼酸或苯磺酸等酸性催化剂存在下，加热至100-200℃，二丙酮醇脱水生成异丙叉丙酮，转化率为80-85%。但二丙酮醇能受热分解成丙酮，因此脱水产物需回收基中的丙酮。最后上步反应是异丙叉两样酮加氢生成4-甲基-2-戊醇。实际上，如果以镍或铜为催化剂，气相加氢在常压下进行的条件比较温和时，则得到较多的部分加氢产物甲基异丁基甲酮。当温度控制为170-210℃，氢与异丙叉丙酮的摩尔配比加大时，则较多获得完全加氢产物甲基异丁基甲醇。而一般情况下得到的是两者混合物，精馏分离时采用减压蒸馏系统。也可以甲基-异丁基（甲）酮经镍催化加氢制成，经精馏塔分馏，得成品。