4-甲基-2-戊酮 | 108-10-1

• 物质功能分类: 有机原料 - 酮类化合物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-甲基-2-戊酮
• 中文别名: 甲基异丁基酮；异己酮；六碳酮；甲基异丁基甲酮；甲基异丁酮；MIBK
• 英文名称: 4-methyl-2-pentanone
• 英文别名: methyl isobutyl ketone；4-methylpentan-2-one；MIBK；isobutyl methyl ketone
• CAS: 108-10-1
• 化学式: C₆H₁₂O
• 分子量: 100.161
• InChiKey: NTIZESTWPVYFNL-UHFFFAOYSA-N

物化性质

• 熔点：
  -80 °C (lit.)
• 沸点：
  117-118 °C
• 密度：
  0.801 g/mL at 25 °C (lit.)
• 蒸气密度：
  3.5 (vs air)
• 闪点：
  56 °F
• 溶解度：
  水：可溶20g/L
• 最大波长(λmax)：
  λ: 335 nm Amax: 1.00λ: 340 nm Amax: 0.50λ: 360 nm Amax: 0.15λ: 380 nm Amax: 0.02λ: 400 nm Amax: 0.01
• 介电常数：
  13.0（Ambient）
• 暴露限值：
  TLV-TWA 205 mg/m3 (50 ppm); STEL 300 mg/m3 (75 ppm) (ACGIH); IDLH 3000 ppm (NIOSH).
• LogP：
  1.3-1.9 at 20℃
• 物理描述：
  Methyl isobutyl ketone appears as a clear colorless liquid with a pleasant odor. Flash point 73°F. Less dense than water. Vapors heavier than air.
• 颜色/状态：
  Liquid
• 气味：
  Pleasant odor
• 蒸汽密度：
  3.45 (NTP, 1992) (Relative to Air)
• 蒸汽压力：
  19.9 mm Hg at 25 °C
• 大气OH速率常数：
  1.41e-11 cm3/molecule*sec
• 稳定性/保质期：
  1. 能与乙醇、乙醚、苯等大多数有机溶剂和动植物油相混溶，是硝酸纤维素、聚氯乙烯、聚乙酸乙烯酯、聚苯乙烯、环氧树脂、天然及合成橡胶、DDT、2,4-D以及许多有机物的优良溶剂。能配制成低黏度溶液，防止凝胶化。 2. 化学性质：分子中羰基及邻接的氢原子具有较强的化学反应性，与丁酮相似。例如，在强氧化剂如铬酸的作用下，会生成乙酸、异丁酸、异戊酸、二氧化碳和水；在催化加氢作用下，则可得到4-甲基-2-戊醇。与亚硫酸氢钠形成加成产物。在碱性催化剂存在的情况下，与其他羰基化合物发生缩合反应。还能与肼缩合生成腙，并与乙酸乙酯进行Claisen缩合反应。 3. 稳定性：稳定。 4. 禁配物：强氧化剂、强还原剂和强碱。 5. 聚合危害：不会发生聚合。
• 自燃温度：
  840 °F (448 °C)
• 燃烧热：
  -10,400 Btu/lb = -5,800 cal/g = -242X10+5 J/kg (est)
• 汽化热：
  40.61 kJ/mol at 25 °C
• 表面张力：
  23.6 dynes/cm = 0.0236 N/m at 20.0 °C
• 电离电位：
  9.30 eV
• 气味阈值：
  0.10 ppm
• 折光率：
  Index of refraction: 1.3962 at 20 °C/D
• 相对蒸发率：
  1.6 (Butyl acetate = 1)
• 保留指数：
  729.5;716;723;719;721.2;724;728;719.78;720.12;720.65;721.7;722.94;720;721;722;723;730;726;724;727;753;721;698;721;722;713;720;725;720;722.1;720;715.83;723;715.8;726;721;720.1;722.2;732;723;726;720;720;723;724;725;720;730;722.7

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

ADMET

代谢

甲基异丁基酮（MIBK）最近被发现能够增强胆汁淤积，这种胆汁淤积是由胆红素-锰（Mn-BR）或锰（Mn）在大鼠体内诱导的。在本研究中，我们调查了MIBK的两个主要代谢物4-甲基-2-戊醇（4MPOL）和4-羟甲基异丁基酮（4-OHMIBK）对这些胆汁淤积模型的影响。剂量从1.88到15 mmol/kg的4MPOL或4-OHMIBK在给予胆汁淤积的Mn-BR组合前18小时一次性给药。当4MPOL的剂量为3.75 mmol/kg及更高时，增强了锰-胆红素组合的胆汁淤积效果。另一方面，小于15 mmol/kg的4-OHMIBK剂量并未增强Mn-BR引起的胆汁淤积。连续预处理3天会导致对Mn-BR或单独Mn引起的胆汁淤积挑战的响应增加。重复给药的4MPOL在Mn-BR胆汁淤积模型中是一个更好的增强剂。然而，在单独使用Mn的情况下，4-OHMIBK证明更为有效。4MPOL和4-OHMIBK本身并没有胆汁淤积的特性，因为在胆汁淤积挑战前测量的胆汁流量并没有减少，在某些情况下甚至显著高于车辆预处理动物。这些结果表明，MIBK的代谢物能够增强肝毒性的胆汁淤积形式。/4-甲基-2-戊醇和4-羟甲基异丁基酮（代谢物）/

Methyl isobutyl ketone (MIBK) has recently been shown to potentiate the cholestasis induced by manganese-bilirubin (Mn-BR) or manganese (Mn) in rats. In this study, we investigated the effect of 4-methyl-2-pentanol (4MPOL) and 4-hydroxymethyl isobutyl ketone (4-OHMIBK), two major metabolites of MIBK, on these models of cholestasis. Dosages varying from 1.88 to 15 mmol/kg 4MPOL or 4-OHMIBK were administered once, 18 hr prior to the administration of a cholestatic Mn-BR combination. The cholestatic effect of the manganese-bilirubin combination was enhanced with dosages of 4MPOL of 3.75 mmol/kg and larger. On the other hand, dosages smaller than 15 mmol/kg of 4-OHMIBK did not potentiate the Mn-BR cholestasis. Daily pretreatment for 3 days resulted in an increased response to the cholestatic challenges of either Mn-BR or Mn alone. 4MPOL administered repetitively was a better potentiator than 4-OHMIBK with the Mn-BR model of cholestasis. However, with Mn alone, 4-OHMIBK proved to be more effective. 4MPOL and 4-OHMIBK per se were devoid of cholestatic properties, since the bile flow measured prior to the cholestatic challenge was not decreased and in some cases was significantly greater than that of vehicle-pretreated animals. These results show that MIBK metabolites can potentiate the cholestatic form of hepatotoxicity. /4-methyl-2-pentanol and 4-hydroxymethyl isobutyl ketone (metabolites)/

来源:Hazardous Substances Data Bank (HSDB)

代谢

研究了雄性Sprague-Dawley大鼠口服单次给予5 mmol/kg体重MIBK（以玉米油为溶剂，相当于501 mg/kg体重）的吸收和代谢。口服暴露后，MIBK迅速吸收进入系统循环，平均最大血浆浓度（Cmax）为0.644 mmol/L，发生在给药后0.25小时（达到最大血浆浓度的时间，tmax）。给药后9小时，MIBK在血浆中的水平非常低（0.006 mmol/L）。在整个研究过程中，甲基异丁基甲醇（MIBC）的血浆水平也非常低（<0.012 mmol/L）。血液中的主要物质是4-羟甲基-4-甲基-2-戊酮（根据化学名称简称为HMP）[即双丙酮醇（DAA）]，其Cmax为2.03 mmol/L，发生在9小时，并在给药后12小时仍可检测到。12小时样本中未检测到MIBK和MIBC。除了HMP和MIBK，血液中未检测到其他化合物。MIBK、MIBC和HMP的12小时血浆浓度-时间曲线下面积（AUC0-12 h）分别为0.089、3.558和17,436 mmol/L/小时。HMP和MIBK分别占总AUC的79%和20%。MIBK和HMP的血浆消除半衰期（t1/2）分别为2.529小时和4.831小时。根据本研究的结果，大鼠口服暴露后MIBK迅速吸收进入血液，并且迅速且广泛地代谢为HMP（给药后3小时血液中的主要代谢物）。

The absorption and metabolism of MIBK was studied in male Sprague-Dawley rats orally administered a single dose of 5 mmol/kg body weight of MIBK in corn oil, equivalent to 501 mg/kg body weight, by gavage. MIBK was rapidly absorbed into the systemic circulation following oral exposure, with a mean maximum plasma concentration (Cmax) of 0.644 mmol/L occurring at 0.25 hours [(time to maximum plasma concentration (tmax)] post-administration. MIBK was detected at very low levels (0.006 mmol/L) at 9 hours post-administration. The plasma levels of methyl isobutyl carbinol (MIBC) were very low (<0.012 mmol/L) all over the study. The major material in the blood was 4-hydroxymethyl-4-methyl-2-pentanone (referred to as HMP based on the chemical name) [i.e., diacetone alcohol (DAA], with a Cmax of 2.03 mmol/L at 9 hours and remained detectable at 12 hours post-dosing. Neither MIBK nor MIBC were detectable in 12-hour samples. No compounds other than HMP and MIBK were detected in the blood. The 12-hour area under the plasma concentration time curve (AUC0-12 h) for MIBK, MIBC and HMP were 0.089, 3.558 and 17, 436 mmol/L/hour, respectively. HMP and MIBK represented 79% and 20% of the total AUC, respectively. The plasma elimination half-life (t1/2) of MIBK and HMP were 2.529 and 4.831 hours, respectively. Based on the results of this study, MIBK is rapidly absorbed into the blood in rats following oral exposure and is rapidly and extensively metabolized to HMP (the major metabolite in blood after 3 hours).

来源:Hazardous Substances Data Bank (HSDB)

代谢

甲基异丁基甲醇（MIBC）是一种氧化溶剂，代谢成为甲基异丁基酮（MIBK），然后转化为4-羟基甲基-4-甲基-2-戊酮（HMP）。在大鼠单次口服5毫摩尔/千克剂量的MIBC或MIBK后，测定了血浆中MIBC、MIBK和HMP的水平，时间长达12小时。在两种情况下，血浆中的主要物质是HMP，在给药后9小时，曲线下面积（AUC）和C(max)相似。在MIBK或MIBC给药后，MIBK的血浆水平和AUC也是相当的。MIBC的AUC仅占MIBC给药后血液中总物质的约6%，在MIBK给药后则微不足道。在使用的分析条件下，血浆中未检测到其他代谢物。通过比较MIBK和HMP的AUC总和，MIBC代谢为MIBK的程度至少为73%。

Methyl isobutyl carbinol (MIBC) is an oxygenated solvent that is metabolized to methylisobutyl ketone (MIBK) and then to 4-hydroxymethyl-4-methyl-2-pentanone (HMP). Plasma levels of MIBC, MIBK and HMP were determined up to 12 hr after a single oral 5 mmol/kg dose of MIBC or MIBK to male rats. The major material in the plasma in both cases was HMP, with similar areas-under-the-curve (AUC) and C(max) at 9 hr after dosing. MIBK plasma levels and AUC were also comparable after MIBK or MIBC administration. MIBC AUC was only about 6% of the total material in the blood after MIBC, and insignificant after MIBK administration. No other metabolites were detected in the plasma under the analytical conditions used. The extent of metabolism of MIBC to MIBK, by comparing combined AUCs for MIBK and HMP, was at least 73%. ...

来源:Hazardous Substances Data Bank (HSDB)

代谢

丁酮（MnBK）及其同分异构体甲基异丁酮（MiBK）在小鼠体内的代谢命运进行了研究。在给药后不同时间间隔测量了血液和大脑中两种酮及其代谢物的浓度。MiBK的主要代谢物是4-甲基-2-戊醇（4-MPOL）和4-羟基-4-甲基-2-戊酮（HMP）。... 给予4-甲基-2-戊醇后，MiBK和HMP出现。给予HMP并未导致MiBK或4-MPOL的出现。...

The metabolic fate of methyl n-butyl ketone (MnBK) and its isomer methyl isobutyl ketone (MiBK) was studied in mice. The concentrations of both ketones and their metabolites in blood and brain were measured at different time intervals after their administration. The principal metabolites of ... MiBK were 4-methyl-2-pentanol (4-MPOL) and 4-hydroxy-4 methyl-2-pentanone (HMP). .... The administration of 4-methyl-2-pentanol resulted in the appearance of MiBK and HMP. The administration of HMP did not result in the appearance of MiBK or 4-MPOL. ....

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 毒性总结

甲基异丁基酮（MIBK）是一种无色液体。它被用作树胶、树脂、硝化纤维素、油漆、清漆和喷漆的溶剂。它还用作擦洗酒精的变性剂，在制造甲基戊醇和干洗制剂中使用。它还广泛应用于橡胶化学品，用于生产轮胎。在人类研究中，中毒的症状和体征包括：眼睛、皮肤和呼吸道的刺激，以及中枢神经系统抑制。暴露于高浓度可能会出现胃肠道疼痛和肝脏毒性。在每天暴露于高达2050毫克/立方米（500 ppm）MIBK约20-30分钟和328毫克/立方米（80 ppm）大部分工作时间的工作者中，超过一半的19名工人抱怨感到虚弱、食欲不振、头痛、眼睛刺激、胃痛、恶心、呕吐和喉咙痛。一些工人出现失眠、嗜睡、胃灼热、肠痛和一些不稳。四名工人的肝脏略有增大，六人出现非特异性结肠炎。长时间或重复的皮肤接触可能会导致皮肤干燥和脱屑。意外吸入液态MIBK可导致化学性肺炎。在动物研究中，MIBK对完整兔皮没有引起皮肤刺激。豚鼠暴露于1000、16800、28000 ppm MIBK。1000 ppm的水平对动物的眼睛和鼻子几乎没有或没有刺激。豚鼠在暴露的前6小时内表现出呼吸速率下降，归因于低级别中枢神经系统抑制。16800 ppm的水平立即引起眼睛和鼻子的刺激症状，随后是流涎、流泪、共济失调和死亡。在暴露6小时内，10只动物中有9只死亡。使用的最高浓度（28000 ppm）在45分钟内杀死了50%的动物。只有少数豚鼠在暴露60分钟后存活下来。观察到脂肪肝和大脑、肺和脾的充血。暴露于25 ppm MIBK的大鼠在压力杆反应上显示出最小的统计增加，但暴露于20-40 ppm的狒狒的鉴别行为没有受损。在皮肤暴露于300-600毫克/千克/天MIBK的大鼠中，4个月内观察到皮肤、大脑、肝脏、肾上腺、脾脏和睾丸的形态学变化，呈剂量和时间依赖性。体温下降，氧气消耗增加。在一项大鼠的两代吸入研究中评估了MIBK的生殖毒性。在F1和F2中、高暴露组雄性和雌性幼崽出生后14天，唯一报告的影响是显著降低体重；然而，在出生后7天和21天，幼崽的体重与对照组没有差异。在任何生殖或发育终点，包括F0和亲代F1生殖器官的解剖学变化方面，没有观察到其他与暴露相关的变化。MIBK的遗传毒性试验包括沙门氏菌/微粒体（Ames）试验、L5178Y/TK +/-小鼠淋巴瘤试验、BALB/3T3细胞转化试验、非计划DNA合成试验和微核试验。在L5178Y/TK +/-小鼠淋巴瘤试验中，在测试的最高细胞毒性浓度下仅观察到边缘反应，BALB/3T3细胞转化试验缺乏可重复性，以及Ames试验、非计划DNA合成和微核试验的明确阴性结果，这表明MIBK在哺乳动物系统中不太可能是遗传毒性的。生态毒性研究：水生无脊椎动物对MIBK毒性的敏感性低于鱼类。MIBK的毒性也在绿藻Scenedesmus quadricauda中进行了测量，其8天毒性阈值为725毫克/升，在更敏感的蓝藻（蓝绿藻）Microcystis aeruginosa中，毒性阈值为136毫克/升。

IDENTIFICATION AND USE: Methyl isobutyl ketone (MIBK) is a colorless liquid. It is used as a solvent for gums, resins, nitrocellulose, paints, varnishes, and lacquers. It is also used as denaturant for rubbing alcohol, in the manufacture of methyl amyl alcohol, and in dry-cleaning preparations. It is also widely used in rubber chemicals for the production of tyres. HUMAN STUDIES: Symptoms and signs of poisoning include: irritation of the eyes, skin, and respiratory tract, as well as CNS depression. Gastrointestinal pain and hepatic toxicity may occur with exposure to high concentrations. In workers exposed to up to 2050 mg MIBK/cu m (500 ppm) for 20-30 min per day and to 328 mg/cu m (80 ppm) for much of the remainder of the working day, over half of the 19 workers complained of weakness, loss of appetite, headache, eye irritation, stomach ache, nausea, vomiting, and sore throat. A few of the workers experienced insomnia, somnolence, heartburn, intestinal pain, and some unsteadiness. Four workers had slightly enlarged livers and six had a nonspecific colitis. Prolonged or repeated skin contact may cause drying and flaking of the skin. Accidental aspiration of liquid MIBK can cause chemical pneumonitis. ANIMAL STUDIES: MIBK elicited no dermal irritation to intact rabbit skin. Guinea pigs were exposed to 1000, 16,800, 28,000 ppm MIBK. The 1000 ppm level caused little or no irritation of eyes and nose of the animals. Guinea pigs showed a decreased respiratory rate during the first 6 hr of exposure attributed to a low grade CNS depression. The 16,800 ppm level caused immediate signs of eye and nose irritation followed by salivation, lacrimation, ataxia, and death. Nine of 10 animals died within 6 hr of exposure. The highest concentration used (28,000 ppm) killed 50 percent of the animals within 45 min. Only a few guinea pigs survived 60 min of exposure. Fatty livers and congestion of the brain, lungs and spleen were noted. Rats exposed to 25 ppm MIBK showed a minimal statistical increase in pressor lever response, but the discriminatory behavior of baboons was not impaired by exposures of 20-40 ppm. In rats exposed dermally to 300-600 mg MIBK/kg per day for 4 months, dose- and time-dependent morphological changes were observed in the skin, brain, liver, adrenals, spleen, and testis. Body temperature decreased and oxygen consumption increased. Reproductive toxicity of MIBK was evaluated in a two-generation inhalation study in rats. The only effect reported in offspring was significantly depressed body weights on day 14 postpartum in F1 and F2 male and female pups in mid- and high-exposure groups; however, pup body weights were not different from those of controls on days 7 and 21 post-partum. No other exposure-related changes were observed in any reproductive or developmental endpoint in either generation, including an absence of anatomical changes in F0 and parental F1 reproductive organs. Genotoxicity assays of MIBK included the Salmonella/microsome (Ames) assay, L5178Y/TK+/- mouse lymphoma assay, BALB/3T3 cell transformation assay, unscheduled DNA synthesis assay, and micronucleus assay. The presence of a marginal response only at the highest cytotoxic concentration tested in the L5178Y/TK+/- mouse lymphoma assay, the lack of reproducibility in the BALB/3T3 cell transformation assay, and clearly negative results in the Ames assay, unscheduled DNA synthesis and micronucleus assays, suggest that MIBK is unlikely to be genotoxic in mammalian systems. ECOTOXICITY STUDIES: Aquatic invertebrates are less sensitive than fish to the toxicity of MIBK. The toxicity of MIBK was also measured in the green alga Scenedesmus quadricauda, in which the 8-day threshold for toxicity was 725 mg/L, and in the relatively more sensitive cyanobacterium (blue-green alga) Microcystis aeruginosa, in which the toxicity threshold was 136 mg/L.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

人类癌症：工作组没有可用的数据。实验动物癌症：有充分的证据表明甲基异丁基酮对实验动物具有致癌性。总体评估：甲基异丁基酮可能对人类致癌（2B组）。

Cancer in humans: No data were available to the Working Group. Cancer in experimental animals: There is sufficient evidence in experimental animals for the carcinogenicity of methyl isobutyl ketone. Overall evaluation: Methyl isobutyl ketone is possibly carcinogenic to humans (Group 2B).

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

A3; 已确认的动物致癌物，对人类的相关性未知。

A3; Confirmed animal carcinogen with unknown relevance to humans.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌物分类

国际癌症研究机构致癌物：甲基异丁基甲酮

IARC Carcinogenic Agent:Methyl isobutyl ketone

来源:International Agency for Research on Cancer (IARC)

毒理性

• 致癌物分类

国际癌症研究机构（IARC）致癌物分类：2B组：可能对人类致癌

IARC Carcinogenic Classes:Group 2B: Possibly carcinogenic to humans

来源:International Agency for Research on Cancer (IARC)

吸收、分配和排泄

甲基异丁基酮（MIBK）是一种在许多产品和工艺中使用的溶剂，可能以蒸汽的形式存在于工作场所的空气中。美国政府工业卫生学家会议（ACGIH）对MIBK的阈限值-时间加权平均（TLV-TWA）和阈限值-短期暴露限值（TLV-STEL）分别为50和75 ppm。这些工作场所空气浓度限制是为了保护工人免受刺激、神经衰弱症状以及对肝脏和肾脏可能的不良影响。最近有人提议修订ACGIH限值，将当前的TLV-TWA降至30 ppm。本文预测了在不同暴露情景（每天8、12和24小时，连续7天）下，人类反复暴露于当前ACGIH TLV-TWA 50 ppm的MIBK的动力学和积累情况。模型的动力学参数来源于已发表的单一2小时吸入48.9 ppm MIBK的人体时间过程血液MIBK数据。该模型正确模拟了单次暴露实验数据，血液浓度在1小时内迅速上升至1.06 ug/mL，并在4小时暴露期内达到大于或等于99%的稳态血液水平。预测MIBK在终止暴露后会被迅速从血液中消除，在暴露后0.5小时和2小时分别达到0.53 ug/mL和0.13 ug/mL。在暴露结束后4小时内，预计血液浓度将降至稳态浓度的1%以下。基于这些结果，可以得出结论，在当前TLV-TWA浓度50 ppm下，由于反复吸入暴露导致MIBK在工人体内积累的情况不太可能发生。

Methyl isobutyl ketone (MIBK) is a solvent used in numerous products and processes and may be present in the air of the workplace as a vapor. The American Conference of Governmental Industrial Hygienists (ACGIH) threshold limit value-time-weighted average (TLV-TWA) and TLV-short term exposure limit (TLV-STEL) for MIBK are 50 and 75 ppm, respectively. These workplace air concentration limits were set to protect workers from irritation, neurasthenic symptoms and possible adverse effects to their livers and kidneys. A recent revision of the ACGIH limit value has been proposed, to reduce the current TLV-TWA to 30 ppm. This article predicts the kinetics and accumulation of MIBK in humans exposed repeatedly in various exposure scenarios (8, 12, and 24 hr/day for 7 days) to the current ACGIH TLV-TWA of 50 ppm. The kinetic parameters of the model were derived from published human time-course blood MIBK data from a single 2 hr inhalation exposure to 48.9 ppm MIBK. The model correctly simulated single exposure experimental data with a rapid rise in blood concentration to 1.06 ug/mL within 1 hr and approached >or=99% steady-state blood level in 4 hr of exposure. MIBK was predicted to be rapidly eliminated from blood after terminating the exposure, reaching 0.53 ug/mL and 0.13 ug/mL within 0.5 and 2 hr post-exposure, respectively. Within 4h after the termination of exposure, blood concentration would be expected to <1% of the steady-state concentration. On the basis of these results, it is concluded that accumulation of MIBK in workers due to repeated inhalation exposure is not likely to occur at the current TLV-TWA concentration of 50 ppm.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

甲基异丁基酮在人类母体血液样本中被报告，这些样本是在分娩后立即收集的，表明该化合物有可能进入脐带并穿过胎盘。

Methyl isobutyl ketone /was reported/ in human maternal blood samples collected immediately after delivery, indicating the potential for the compound to enter the umbilical cord and cross the placenta.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

甲基异丁基酮在两名喷漆工人接触多种有机溶剂后死亡的脑、肝、肺、玻璃体液、肾脏和血液中被检测到。一名工人死于坠落，另一名工人在9小时后死于脑水肿。报告的组织浓度（毫克/100克）为：案例1 - 脑，0.25；肝，0.49；肺，0.43；玻璃体液，0.52；肾脏，0.24；股骨血液，0.14；案例2 - 脑，0.06；肝，0.22；肺，0.11；玻璃体液，0.02；肾脏，0.08；心脏血液，0.04。

Methyl isobutyl ketone was detected in the brain, liver, lung, vitreous fluid, kidney, and blood in two workers who died after exposure to several organic solvents during spray painting. One died from a fall and the other died of cerebral edema 9 hours later. Tissue concentrations (mg/100 g) were reported to be: case 1 - brain, 0.25; liver, 0.49; lung, 0.43; vitreous fluid, 0.52; kidney, 0.24; and femoral blood, 0.14; and case 2 - brain, 0.06; liver, 0.22; lung, 0.11; vitreous fluid, 0.02; kidney, 0.08; and heart blood, 0.04.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

98名男性和女性志愿者在一个环境室里暴露于100 ppm（410 mg/立方米）甲基异丁基酮4小时。在暴露2小时后达到了甲基异丁基酮的稳态血浓度。暴露后90分钟收集的血样和呼吸样本表明，大部分吸收的化合物已经被排出体外。

Human volunteers (98 men and women) were exposed to 100 ppm (410 mg/cu m) methyl isobutyl ketone for 4 hours in an environmental chamber. Steady-state blood concentrations of methyl isobutyl ketone were attained after 2 hours of exposure. Blood and breath samples collected 90 minutes after exposure indicated that most of the absorbed compound had been eliminated from the body.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 职业暴露等级：
  A
• 职业暴露限值：
  TWA: 50 ppm (205 mg/m3), STEL: 75 ppm (300 mg/m3)
• TSCA：
  Yes
• 危险等级：
  3
• 立即威胁生命和健康浓度：
  500 ppm
• 危险品标志：
  F
• 安全说明：
  S16,S29,S36/37,S45,S7,S9
• 危险类别码：
  R66,R36/37,R11,R20
• WGK Germany：
  1
• 海关编码：
  2914130000
• 危险品运输编号：
  UN 1245 3/PG 2
• 危险类别：
  3
• RTECS号：
  SA9275000
• 包装等级：
  II
• 危险标志：
  GHS02,GHS07
• 危险性描述：
  H225,H319,H332,H335
• 危险性防范说明：
  P210,P261,P305 + P351 + P338
• 储存条件：
  储存注意事项： - 储存在阴凉、通风的库房中。 - 远离火种、热源，库温不宜超过37℃。 - 保持容器密封。 - 应与氧化剂、还原剂、碱类分开存放，切忌混储。 - 使用防爆型照明和通风设施。 - 禁止使用易产生火花的机械设备和工具。 - 储区应配备泄漏应急处理设备和合适的收容材料。

SDS

第一部分：化学品名称

制备方法与用途

简介

4-甲基-2-戊酮（甲基异丁基甲酮）是一种广泛应用于化工、制药的溶剂，还可用于核裂变产物的分离回收及科研试验。市场上销售的产品含量通常不超过99%，其中含有少量醇、酸性物质和水等杂质。

这种化合物被用作硝化棉、漆和某些聚合物及树脂的溶剂，同时也是合成2-(1-羟基-3-甲基丁炔)- 1h -茚-1,3(2H)二酮的重要原料。

含量分析

按“乙醛(03401)”中的含量分析法测定。取样量为1.2 g，反应时间改为60 min。每毫升0.5 mol/L硫酸相当于含有4-甲基-2-戊酮（C6H12O）50.08 mg。

毒性

急性毒性：大鼠口服LD50: 2080毫克/公斤；小鼠口服LD50: 2671毫克/公斤。皮肤刺激：兔子500毫克/24小时轻度；眼睛刺激：兔子500毫克/24小时轻度。

使用限量

• FEMA(mg/kg)：软饮料、冷饮、糖果和焙烤食品中限用6.3 mg/kg。
• 适度为限（FDA §172.515，2000）。

化学性质

这是一种具有樟脑气味的无色透明液体，熔点-80℃，沸点117～118℃，密度1.3960，相对密度0.801。沸点为87.9℃时含水量24.3%，酮含量75.7%。几乎不溶于水但可与水形成共沸物，能与酚、醛、醚、苯等有机溶剂混溶。有毒性，蒸气刺激眼睛和呼吸道。

用途

4-甲基-2-戊酮又称甲基异丁基酮，是杀鼠剂“鼠完”的中间体；用于医药、染料中间体中；用作硝化纤维素、树脂、树胶等的溶剂；合成2-(1-羟基-3-甲基丁炔)- 1h -茚-1,3(2H)二酮。

生产方法

该化合物可以通过以下几种方式制备：

• 异丙醇法：在常压下，温度180～220℃通过铝铜催化剂使异丙醇脱氢成丙酮，再与异丙醇缩合脱水而得。
• 丙酮法：将丙酮加热，在常压下与氢氧化钠催化剂反应得到双丙醇酮。在磷酸催化下进行脱水反应生成异丙烯丙酮，并在铜催化剂存在下催化加氢，温度170～200℃制得产品。

分类

• 类别：易燃液体
• 毒性分级：中毒
• 急性毒性：
  • 大鼠口服LD50: 2080毫克/公斤
  • 小鼠口服LD50: 2671毫克/公斤

安全特性

• 与空气混合可爆。
• 明火、受热或氧化剂下可燃；燃烧排放刺激烟雾。

储运及灭火方法

库房通风低温干燥，轻装轻卸，并与其他氧化剂和酸类分开存放。灭火剂包括雾状水、泡沫、二氧化碳和1211灭火剂。

• 职业标准：
  • TLV-TWA：50 PPM (205毫克/立方米)
  • STEL：75 PPM (300毫克/立方米)

反应信息

• 作为反应物：
  描述：

  4-甲基-2-戊酮 在 Montmorillonite 、 (-)N-dodecyl-N-methyl ephedrinium borohydride 作用下， 以 苯 为溶剂， 反应 6.0h， 以92%的产率得到4-甲基-2-戊醇
  参考文献：
  名称：

  蒙脱土负载的（-）N-十二烷基-N-甲基麻黄硼氢化物：一种有效的还原剂

  摘要：

  粘土负载的试剂在相转移条件下有效地还原了酮。羰基的两倍活化-一种是通过粘土上的路易斯酸位点活化，另一种是通过麻黄碱部分的β-羟基活化，确保了简便的离析-在还原某些环状酮方面保持了相当的立体选择性。在某些前手性酮的情况下，观察到不对称诱导为1–9.7％。

  DOI：

  10.1016/s0040-4039(00)92057-4
• 作为产物：
  描述：

  4-甲基-2-戊醇 在 iron(III) chloride hexahydrate 、 氧气 、 silica gel 、 2,2,6,6-四甲基哌啶氧化物 作用下， 以 甲苯 为溶剂， 80.0 ℃ 、500.01 kPa 条件下， 反应 90.08h， 以90%的产率得到4-甲基-2-戊酮
  参考文献：
  名称：

  硅胶存在下六水合氯化铁/ TEMPO催化的醇的选择性好氧氧化

  摘要：

  在硅胶存在下，使用分子印迹技术完成了FeCl 3 •6H 2 O / 2,2,6,6-四甲基哌啶N-氧基（TEMPO）催化的醇氧化为相应的醛和酮的环保，高效过程氧气或空气作为终端氧化剂。缺电子的苯甲醇被平滑氧化为相应的醛，分离产率高达99％。发现硅胶不仅可以提高催化反应速率，而且可以提高产物的选择性。FeCl 3 •6H 2的高性能硅胶存在下的O / TEMPO催化剂体系可能归因于表面硅烷醇基团。紫外可见光谱分析表明，Fe（III）-TEMPO配合物可作为本催化体系中的活性中间物质。提出了催化系统的合理机理。版权所有©2012 John Wiley＆Sons，Ltd.

  DOI：

  10.1002/aoc.1862
• 作为试剂：
  描述：

  4-methoxybenzhydryl chloride 、 alkaline earth salt of/the/ methylsulfuric acid 在 三正丁胺 、 4-甲基-2-戊酮 作用下， 生成 4-(4-methoxy-benzhydryloxy)-1-methyl-piperidine
  参考文献：
  名称：

  Process for preparing benzhydryl ethers

  摘要：

  公开号：

  US02751388A1

文献信息

• Separate Sets of Mutations Enhance Activity and Substrate Scope of Amine Dehydrogenase
  作者：Robert D. Franklin、Conner J. Mount、Bettina R. Bommarius、Andreas S. Bommarius

  DOI：10.1002/cctc.201902364

  日期：2020.5.7

  average of 2.5‐fold higher activity toward aliphatic ketones and an 8.0 °C increase in melting temperature. L‐AmDH‐TV did not show significant changes in relative activity for different substrates. In contrast, L39A, L39G, A112G, and T133G in varied combinations added to L‐AmDH‐TV changed the shape of the substrate binding pocket. L‐AmDH‐TV was not active on ketones larger than 2‐hexanone. L39A and L39G

  将突变引入衍生自嗜热脂肪芽孢杆菌的亮氨酸胺脱氢酶（L‐AmDH）亮氨酸脱氢酶（LeuDH）的目的是提高活性和扩大底物接受度。包括D32A，F101S和C290V在内的三重变体（L‐AmDH‐TV）对脂族酮的活性平均提高了2.5倍，熔融温度提高了8.0°C。L‐AmDH‐TV在不同底物的相对活性方面未显示出显着变化。相反，添加到L‐AmDH‐TV中的L39A，L39G，A112G和T133G的各种组合改变了底物结合袋的形状。L-AmDH-TV在大于2-己酮的酮上不起作用。L39A和L39G可以激活高达2-癸酮的直链酮，并与A112G结合起来可以活化更长的支链酮，包括5-甲基-2-辛酮。
• Novel processes for the preparation of adenosine compounds and intermediates thereto
  申请人：——

  公开号：US20030069423A1

  公开（公告）日：2003-04-10

  Novel processes for the preparation of adenosine compounds and intermediates thereto. The adenosine compounds prepared by the present processes may be useful as cardiovascular agents, more particularly as antihypertensive and anti-ischemic agents, as cardioprotective agents which ameliorate ischemic injury or myocardial infarct size consequent to myocardial ischemia, and as an antilipolytic agents which reduce plasma lipid levels, serum triglyceride levels, and plasma cholesterol levels. The present processes may offer improved yields, purity, ease of preparation and/or isolation of intermediates and final product, and more industrially useful reaction conditions and workability.

  新型的制备腺苷化合物及其中间体的方法。通过本方法制备的腺苷化合物可能作为心血管药物有用，更具体地作为降压和抗缺血药物，作为改善缺血性损伤或心肌梗死大小的心脏保护剂，以及作为降脂剂，可降低血浆脂质水平、血清甘油三酯水平和血浆胆固醇水平。本方法可能提供改善产率、纯度、制备和/或中间体和最终产品的分离的便利性，以及更具工业应用的反应条件和可操作性。
• SUBSTITUTED ARYL AND HETEROARYL CARBOXYLIC ACID HYDRAZIDES OR SALTS THEREOF AND USE THEREOF TO INCREASE STRESS TOLERANCE IN PLANTS
  申请人：BAYER CROPSCIENCE AKTIENGESELLSCHAFT

  公开号：US20180206495A1

  公开（公告）日：2018-07-26

  Substituted aryl- and heteroarylcarbonyl hydrazides The invention relates to substituted aryl- and heteroarylcarbonyl hydrazides of the general formula (I) or salts thereof where the radicals of the formula (I) are each as defined in the description for enhancing stress tolerance in plants to abiotic stress, and for enhancing plant growth and/or for increasing plant yield.

  该发明涉及通式（I）的取代芳基和杂芳基羰基肼或其盐，其中通式（I）的基团如描述中所定义，用于增强植物对非生物胁迫的耐受性，促进植物生长和/或增加植物产量。
• HERBICIDAL AND FUNGICIDAL 5-OXY-SUBSTITUTED 3-PHENYLISOXAZOLINE-5-CARBOXAMIDES AND 5-OXY-SUBSTITUTED 3-PHENYLISOXAZOLINE-5-THIOAMIDES
  申请人：BAYER CROPSCIENCE AG

  公开号：US20150245616A1

  公开（公告）日：2015-09-03

  Herbicidally and fungicidally active 5-oxy-substituted 3-phenylisoxazoline-5-carboxamides and 5-oxy-substituted 3-phenylisoxazoline-5-thioamides of the formula (I) are described. In this formula (I), X, X 2 to X 6 , R 1 to R 4 are radicals such as hydrogen, halogen and organic radicals such as substituted alkyl. A is a bond or a divalent unit. Y is a chalcogen.

  具有除草和杀菌活性的5-氧代取代的3-苯基异噁唑啉-5-羧酰胺和5-氧代取代的3-苯基异噁唑啉-5-硫酰胺的化合物如下式（I）所述。 在这个式子（I）中，X，X2至X6，R1至R4是氢、卤素和有机基团，如取代烷基等。A是一个键或二价基团。Y是硫族元素。
• [EN] SUBSTITUTED QUINAZOLINES AS FUNGICIDES<br/>[FR] QUINAZOLINES SUBSTITUÉES, UTILISÉES EN TANT QUE FONGICIDES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2010136475A1

  公开（公告）日：2010-12-02

  The present invention relates to a compound of formula (I) wherein wherein the substituents have the definitions as defined in claim 1or a salt or a N-oxide thereof, their use and methods for the control and/or prevention of microbial infection, particularly fungal infection, in plants and to processes for the preparation of these compounds.

  本发明涉及一种具有如下式（I）的化合物，其中取代基具有权利要求1中定义的定义，或其盐或N-氧化物，它们的用途以及用于控制和/或预防植物中微生物感染，特别是真菌感染的方法，以及制备这些化合物的方法。

表征谱图