甲苯 | 108-88-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 甲苯
• 中文别名: 甲苯（易制毒）；苯基甲烷；无水甲苯；甲基苯
• 英文名称: toluene
• 英文别名: methylbenzene；PhMe
• CAS: 108-88-3
• 化学式: C₇H₈
• 分子量: 92.1405
• InChiKey: YXFVVABEGXRONW-UHFFFAOYSA-N

物化性质

• 稳定性/保质期：
  1. 在强氧化剂如高锰酸钾、重铬酸钾、硝酸的作用下，甲苯会被氧化成苯甲酸。在催化剂存在下，使用空气或氧气也可以实现这一转化。在硫酸的存在下，于40℃以下用二氧化锰进行氧化反应会生成苯甲醛。当镍或铂作为催化剂时，在还原条件下可得到甲基环己烷。采用三氯化铝或三氯化铁作催化剂，甲苯与卤素反应会生成邻位和对位的卤代甲苯。加热并光照下，甲苯与卤素发生反应，则会产生苄基卤；与硝酸作用则生成邻位和对位的硝基甲苯。若用混酸（硫酸+硝酸）进行硝化反应可得到2,4-二硝基甲苯；进一步硝化会生成2,4,6-三硝基甲苯，即TNT。此外，在浓硫酸或发烟硫酸的作用下，甲苯会发生磺化反应形成邻位和对位的甲基苯磺酸。在三氯化铝或三氟化硼催化作用下，甲苯可以与卤代烃、烯烃、醇进行烷基化反应生成多种烷基甲苯混合物。而通过甲醛和盐酸的作用，甲苯会发生氯甲基化反应生成邻位或对位的甲基苄基氯。 2. 稳定性：甲苯性质稳定。 3. 禁配物：强氧化剂、酸类、卤素等。 4. 聚合危害：不会发生聚合。

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

ADMET

代谢

甲苯被很好地代谢，但有一部分未改变地被呼出。肝脏的P450酶催化甲苯的代谢，主要生成苯甲醇和较少量的甲酚。苯甲醇通过醇脱氢酶和醛脱氢酶（ALDH）转化为苯甲酸，苯甲酸主要与甘氨酸结合，并以马尿酸的形式随尿液排出体外。

Toluene is well metabolized, but a portion is exhaled unchanged. Hepatic P450s catalyze metabolism of toluene primarily to benzyl alcohol and lesser amounts of cresols. Benzyl alcohol is converted by ADH and aldehyde dehydrogenase (ALDH) to benzoic acid, which is primarily conjugated with glycine and eliminated in the urine as hippuric acid.

来源:Hazardous Substances Data Bank (HSDB)

代谢

甲苯被代谢成苯甲酸，随后通过肝脏细胞色素P-450催化的甘氨酸结合反应形成马尿酸。大约75%到80%被吸收的甲苯被代谢成苯甲酸，其中62%到72%以马尿酸的形式通过人类的尿液排出。随着吸收的甲苯量增加，葡萄糖醛酸结合的相对重要性也随之增加。相对少量的o-甲酚（0.12%-0.43%）和p-甲酚出现在尿液中，它们以葡萄糖醛酸和硫酸盐衍生物的形式存在。被吸收的甲苯中不到2%通过粪便排出。

Toluene is metabolized to benzoic acid, followed by hepatic cytochrome P-450 catalyzed glycine conjugation to form hippuric acid. Approximately 75% to 80% of the absorbed toluene is metabolized to benzoic acid, and 62% to 72% is eliminated by humans in the urine as hippuric acid. As the amount of absorbed toluene is increased, the relative importance of the glucuronide conjugated increased. Relatively small amounts appear in urine as the o-cresol (0.12%-0.43%) and p-cresol where they occur as glucuronide and sulfate derivatives. Less than 2% of the absorbed toluene is eliminated in feces.

来源:Hazardous Substances Data Bank (HSDB)

代谢

在大鼠中，大约0.5%-1.1%的剂量会转化为邻甲酚和对甲酚，并以葡萄糖醛酸苷和硫酸盐结合物的形式排出体外。

In rats, approx 0.5%-1.1% of the dose is converted to o-cresol and p-cresol and is excreted as glucuronide and sulfate conjugates.

来源:Hazardous Substances Data Bank (HSDB)

代谢

在哺乳动物物种中，酸性代谢物与甘氨酸结合形成马尿酸和苯乙酸。在人类中，苯乙酸代谢物也与谷氨酰胺结合形成苯乙酰谷氨酰胺。

In mammalian species, acidic metabolites are conjugated with glycine to form hippuric acid and phenylacetic acid. In humans, the phenylacetic acid metabolite is also conjugated with glutamine to form phenacetylglutamine.

来源:Hazardous Substances Data Bank (HSDB)

代谢

甲苯已知的人类代谢物包括对甲基酚、邻甲酚和苯甲醇。

Toluene has known human metabolites that include 4-Methylphenol, o-Cresol, and Benzyl alcohol.

来源:NORMAN Suspect List Exchange

毒理性

• 毒性总结

识别和使用：甲苯是一种无色液体。目前在美国没有注册用于当前的农药使用，但批准的农药用途可能会定期更改，因此必须咨询联邦、州和地方当局以获取当前批准的用途。甲苯是汽油、油漆、墨水、硝基漆、油漆稀释剂、粘合剂、指甲油、清洁剂和橡胶的成分。BTX（苯、甲苯和二甲苯的混合物）被添加到汽油中以提高辛烷值。甲苯用于生产苯、三硝基甲苯（TNT）、尼龙、塑料和聚氨酯。它也用于生产滥用药物。甲苯是溶剂滥用者的最爱，他们故意吸入高浓度的甲苯以达到兴奋效果。人类暴露和毒性：在100 ppm（377 mg/m³）甲苯的空气水平下暴露6.5小时后，眼睛和上呼吸道出现刺激，并且在500 mg/m³时出现流泪。志愿者在100 ppm（377 mg/m³）甲苯中每天暴露6小时，连续四天，出现头痛、眩晕和醉酒感的主观抱怨。在750 mg/m³下暴露8小时的受试者出现疲劳、肌肉无力、混乱、协调能力受损、瞳孔扩大和调节障碍；在大约3000 mg/m³时，观察到严重疲劳、明显恶心、精神混乱、显著不协调和步态蹒跚以及瞳孔光反射受到强烈影响。在高水平暴露后，肌肉疲劳、神经质和失眠持续了几天。重度意外暴露会导致昏迷。对暴露于甲苯的妇女的研究表明，月经紊乱，主要与异常出血有关。在一项对两名遭受甲苯中毒的成年白人男性的案例研究中，注意到了心律失常。反应似乎在个体间高度可变。一个人在1890 ppm以下甲苯中暴露2小时表现出快速心跳（窦性心动过速），而第二个人在3小时暴露后表现出缓慢心跳（心动过缓）。在五名慢性滥用含甲苯涂料的孕妇中观察到了严重的肾小管酸中毒。一名27岁的男性在五年广泛的胶水吸嗅过程中发展为大脑和脑干萎缩。他还发展为双侧视神经萎缩伴失明和严重感音神经性听力损失。CYP2E1是一种多功能的I期药物代谢酶，负责大多数挥发性有机化合物的生物转化，包括甲苯。人类甲苯暴露增加了CYP2E1 mRNA并改变了其在白细胞中的活性。一项对1978年至1983年间在职业数据库中监测的芬兰人的研究表明，平均血浓度为0.18 mg/L的甲苯暴露个体的癌症风险没有增加。对意大利34名凹版印刷工人的外周血淋巴细胞进行的染色体研究显示与对照组相比没有变化。几个病例系列表明，怀孕期间通过嗅吸高暴露于甲苯会诱导一种与胎儿酒精综合征非常相似的综合征，包括出生前后生长不足、小头畸形和发育迟缓，典型的颅面特征包括小颌、小睑裂和耳部异常。动物研究：为了评估急性反复吸入甲苯（15或30分钟；约5000 ppm）对青春期（1个月）、年轻成年（2-3个月）、成年（5-6个月）和老年（10-12个月）大鼠在运动、探索、平衡、步态和神经功能任务上的影响，研究了大鼠。在所有年龄组中，急性甲苯吸入后运动和神经功能均受损。然而，只有从运动功能缺陷中恢复所需的时间在不同年龄组之间有所不同，青春期和年轻成年大鼠需要明显比老年大鼠更长的恢复时间。当0.25、0.5或2.0 mL甲苯应用于豚鼠总表面积的0.7%时，没有动物死亡，但体重增长减少。雄性大鼠每天吸入1400至2000 ppm甲苯8小时，仅3天就出现了可逆的高频听力损失。雄性大鼠皮下注射50和500 mg/kg，每天一次，连续10天，导致精子计数降低和血清睾酮减少。在大鼠怀孕的第2周（8-15天）或第3周（14-20天）皮下注射1.3 g/kg甲苯，并评估其畸形、骨骼发育、大脑和肝脏的宫内生长、出生后生长和行为效应。唯一由甲苯引起的改变是低出生体重，发现于怀孕第三周给药的大鼠中。兔在怀孕的第6天至第15天每天24小时暴露于1000 mg/m³（265 ppm）时，自然流产增加。小鼠在怀孕的第6天至第15天每天24小时暴露于1000 mg/m³（265 ppm）和大鼠在怀孕的第7天至第15天暴露于2400 mg/m³（636 ppm）时，出现生长和骨骼迟缓。小鼠在怀孕的第6天至第13天每天24小时暴露于133 ppm甲苯和大鼠在怀孕的第

IDENTIFICATION AND USE: Toluene is a colorless liquid. It is not registered for current pesticide use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses. Toluene is a component of gasoline, paints, inks, lacquers, paint thinners, adhesives, fingernail polish, cleaning agents, and rubber. BTX (a mixture of benzene, toluene, and xylene) is added to gasoline to improve octane ratings. Toluene is used to produce benzene, trinitrotoluene (TNT), nylon, plastics, and polyurethanes. It is also used in production of drugs of abuse. Toluene is a favorite of solvent abusers, who intentionally inhale high concentrations to achieve a euphoric effect. HUMAN EXPOSURE AND TOXICITY: Eye and upper airway irritation occurred after a 6.5 hr exposure to an air level of 100 ppm (377 mg/cu m) toluene, and lacrymation was seen at 500 mg/cu m. Volunteers exposed to 100 ppm (377 mg/cu m) toluene for 6 hr/day for four days suffered from subjective complaints of headache, dizziness and a sensation of intoxication. In subjects exposed to 750 mg/cu m for 8 hr, fatigue, muscular weakness, confusion, impaired coordination, enlarged pupils and accommodation disturbances were experienced; at about 3000 mg/cu m, severe fatigue, pronounced nausea, mental confusion, considerable incoordination with staggering gait and strongly affected pupillary light reflexes were observed. After exposure at the high level, muscular fatigue, nervousness and insomnia lasted for several days. Heavy accidental exposure leads to coma. Studies of women exposed to toluene have shown menstrual disturbances, principally associated with abnormal bleeding. n a case study of two adult white males who suffered from toluene intoxication cardiac arrhythmias were noted. Response seemed to be highly variable among individuals. One person exposed for 2 hr to less than 1890 ppm toluene exhibited a rapid heartbeat (sinus tachycardia), while the second person, exposed for 3 hr, exhibited a slow heartbeat (bradycardia). Severe renal tubular acidosis was observed in five pregnant women who were chronic abusers of paints containing toluene. A 27-year-old male developed cerebral and cerebellar atrophy over a period of five years of extensive glue sniffing. He also developed bilateral optic atrophy with blindness and severe sensorineural hearing loss. CYP2E1 is a versatile phase I drug-metabolizing enzyme responsible for the biotransformation of most volatile organic compounds, including toluene. Human toluene exposure increases CYP2E1 mRNA and modifies its activity in leucocytes. A study of Finnish individuals monitored in an occupational database during the years 1978 to 1983 showed that there was no increase in cancer risk with individuals exposed to toluene with average blood levels of 0.18 mg/L. Chromosome studies on peripheral blood lymphocytes of 34 rotogravure workers in Italy showed no changes when compared with the control group. Several case series have demonstrated that high exposure to toluene through sniffing during pregnancy induces a syndrome that closely resembles the fetal alcohol syndrome, with pre- and postnatal growth deficiency, microcephaly and developmental delay, typical craniofacial features including micrognathia, small palpebral fissures, and ear anomalies. ANIMAL STUDIES: Rats were studied to assess the effects of acute binge-like toluene inhalations (15 or 30 min; ~5,000 ppm) on tasks that examine locomotion, exploration, balance, gait, and neurological functioning for adolescent (1 month), young adult (2-3 months), adult (5-6 months), and older adult (10-12 months) rats. Both motor and neurological functions were impaired following acute toluene inhalation at all ages. However, only the duration to recover from deficits in motor functions differed among age groups, with adolescent and young adult rats requiring notably longer recovery times than older rats. When 0.25, 0.5, or 2.0 mL toluene were applied to 0.7% of the total body surface of guinea pigs, none of the animals died, but reduced body-weight gain occurred. Inhalation of 1400 to 2000 ppm toluene by male rats, 8 hours/day for as little as 3 days resulted in reversible, high-frequency hearing loss. Subcutaneous injection of 50 and 500 mg/kg once a day for 10 days caused decreased sperm counts and serum testosterone in male rats. Rats were dosed with 1.3 g/kg toluene subcutaneously during either week 2 (8-15 days) or week 3 (14-20 days) of pregnancy and evaluated for malformations, development of the skeleton, prenatal growth of the brain and liver, postnatal growth, and behavioral effects. The only toluene-induced change was low birth weight and was found in the rats dosed in the third week of pregnancy. Rabbits exposed 24 hours/day at 1000 mg/cu m (265 ppm) from day 6 to 15 of pregnancy showed increased spontaneous abortions. Mice exposed 24 hours/day at 1000 mg/cu m (265 ppm) on days 6 to 15 of pregnancy and rats exposed to 2400 mg/cu m (636 ppm) on days 7 to 15 of pregnancy showed growth and skeletal retardation. Mice exposed 24 hours/day at 133 ppm toluene on days 6 to 13 of pregnancy and rats exposed 24 hours/day at 399 ppm on days 1 to 8 of pregnancy and on days 9 to 14 of pregnancy showed fetal growth retardation and an increase in skeletal anomalies. There was maternal mortality in these groups. Mice exposed 6 hours/day at 100 ppm toluene during days 1 to 17 of pregnancy showed no significant differences in number of implantation sites, number of fetuses, or mean fetal body weight when compared with control. When toluene was applied to shaved interscapular skin of male mice 3 times per week for 4 weeks, followed by a secondary treatment of 3 times per week for up to 112 weeks, no tumors were observed. Groups of 60 male and female mice that were exposed 6.5 hours/day, 5 days/week for 2 years via inhalation at inhaled 0, 120, 600, or 1200 ppm toluene showed no biologically relevant increases for any non-neoplastic or neoplastic tissue changes. When groups of 60 rats of each sex were exposed via inhalation 6.5 hours/day, 5 days/week for 2 years to atmospheres containing 0, 600, or 1200 ppm toluene, nephropathy occurred in nearly all of the rats. The olfactory and respiratory epithelia showed signs of degeneration with nasal inflammation and metaplasia of the olfactory epithelium (principally in the females). No treatment-related neoplasms occurred in the male rats. and the few scattered tumors found in the females were considered not associated with toluene inhalation. Toluene did not induce gene mutations in Salmonella typhimiurium strain TA98, TA100, TA1535, or TA1537 with or without exogenous metabolic activation. In the mouse lymphoma assay, toluene gave an equivocal response with and without exogenous metabolic activation. Toluene did not induce sister chromatid exchanges or chromosomal aberrations in Chinese hamster ovary cells in the presence or absence of exogenous metabolic activation. ECOTOXICITY STUDIES: The toluene contamination significantly reduced the mass of the cell wall material in the alfalfa roots. Furthermore, the toluene pollution can change the alfalfa root cell wall properties by reducing the cell wall functional groups. These functional groups are probably related to the proteins and polysaccharides in the cell wall.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 毒性总结

甲苯是一种胆碱酯酶或乙酰胆碱酯酶（AChE）抑制剂。胆碱酯酶抑制剂（或“抗胆碱酯酶”）抑制乙酰胆碱酯酶的作用。由于其基本功能，干扰乙酰胆碱酯酶作用的化学物质是强大的神经毒素，在低剂量时会导致过度流涎和眼泪，随后是肌肉痉挛，最终导致死亡。神经气体和许多用于杀虫剂的物质已被证明通过结合乙酰胆碱酯酶活性位点的丝氨酸，完全抑制该酶。乙酰胆碱酯酶分解神经递质乙酰胆碱，该神经递质在神经和肌肉接合处释放，以便让肌肉或器官放松。乙酰胆碱酯酶抑制的结果是乙酰胆碱积累并继续发挥作用，使得任何神经冲动不断传递，肌肉收缩不会停止。最常见的乙酰胆碱酯酶抑制剂之一是基于磷的化合物，它们被设计成与酶的活性位点结合。结构要求是一个带有两个亲脂性基团的磷原子，一个离去基团（如卤素或硫氰酸盐）以及一个末端的氧。

Toluene is a cholinesterase or acetylcholinesterase (AChE) inhibitor. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. Because of its essential function, chemicals that interfere with the action of acetylcholinesterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses, followed by muscle spasms and ultimately death. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop. Among the most common acetylcholinesterase inhibitors are phosphorus-based compounds, which are designed to bind to the active site of the enzyme. The structural requirements are a phosphorus atom bearing two lipophilic groups, a leaving group (such as a halide or thiocyanate), and a terminal oxygen.

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌性证据

评估：在人类中，对于甲苯的致癌性证据不足。有证据表明，在实验动物中甲苯缺乏致癌性。总体评估：甲苯的致癌性对人体不可分类（第3组）。

Evaluation: There is inadequate evidence for the carcinogenicity of toluene in humans. There is evidence suggesting lack of carcinogenicity of toluene in experimental animals. Overall evaluation: Toluene is not classifiable as to its carcinogenicity to humans (Group 3).

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

根据美国环保局2005年的致癌物风险评估指南，由于对长期接触甲苯的人体研究结论不确定，甲苯在足够的老鼠和小鼠终身吸入癌症生物测试中并未表现出致癌性，且在终身大鼠口服生物测试中，仅在高剂量水平500毫克/千克/天时报告了乳腺癌症和白血病的发病率增加，而在800毫克/千克/天剂量水平下并未报告，因此缺乏评估甲苯致癌潜力的足够信息。

Under the Guidelines for Carcinogen Risk Assessment (U.S. EPA, 2005), there is inadequate information to assess the carcinogenic potential of toluene because studies of humans chronically exposed to toluene are inconclusive, toluene was not carcinogenic in adequate inhalation cancer bioassays of rats and mice exposed for life, and increased incidences of mammary cancer and leukemia were reported in a lifetime rat oral bioassay at a dose level of 500 mg/kg-day but not at 800 mg/kg-day.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

A4；不可归类为人类致癌物。

A4; Not classifiable as a human carcinogen.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

在37名凹版印刷工人中，发现工作周（5天）内接触甲苯的时间加权浓度（范围8-416 mg/m³，中位数75）与皮下脂肪组织中甲苯浓度（范围1.1-20.7 mg/kg，中位数3.8）之间存在密切相关性（rs = 0.78）。在接触停止后，对11名受试者进行了甲苯消除情况的跟踪研究。静脉血中甲苯浓度呈非线性下降，消除曲线至少包含三个指数组分。前两个组分的估计半衰期中位数分别为9分钟和2小时。第三个组分，其半衰期中位数为90小时，反映了脂肪组织中甲苯浓度的下降，脂肪组织中甲苯的半衰期中位数为79小时（范围44-178）。研究表明，在外源暴露结束后很长时间内，脂肪组织储库中仍会持续内源性地暴露于甲苯。观察结果还表明，周一早晨的血中甲苯浓度可以作为前一周暴露情况的指标。

In a group of 37 rotogravure printers a close correlation (rs = 0.78) was found between the time weighted toluene exposure during a five day working week (range 8-416 mg/cu m, median 75) and the concentration of toluene in subcutaneous adipose tissue (range 1.1-20.7 mg/kg, median 3.8). After exposure ceased, the elimination of toluene was followed up in 11 subjects. The toluene concentration in venous blood decreased non-linearly and the elimination curves contained at least three exponential components. The first two had median estimated half times of nine minutes and two hours respectively. The third component, with a median half time of 90 hours, reflected the decline in adipose tissue, which had a median half time of 79 hours (range 44-178). The study showed protracted endogenous toluene exposure from adipose tissue depots long after the end of exogenous exposure. The observations also suggest that the blood toluene concentrations on Monday mornings might be used as an index of the exposure in the previous week.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

关于甲苯口腔吸收的研究有限，但已经证实单次口服暴露后几乎100%被吸收。在一项研究中，志愿者通过胃管接受2毫克/分钟的甲苯输注，持续3小时（约5毫克/千克），通过监测呼出气体中的甲苯和尿液中的甲苯代谢物来测量甲苯的吸收，发现甲苯被完全吸收。另一项研究报告称，大鼠单次灌胃剂量的放射性标记甲苯中有超过99%通过尿液或呼出气体排出，这表明暴露剂量几乎被完全吸收。

Studies quantifying oral absorption of toluene are limited but have demonstrated nearly 100% absorption following a single oral exposure. In volunteers exposed to an infusion of 2 mg toluene/minute for 3 hours (~5 mg/kg) via a gastric tube, absorption of toluene, measured by monitoring exhaled air for toluene and urine for toluene metabolites, was found to be complete. /Another study/ reported that greater than 99% of a single gavage dose of radiolabeled toluene in rats was eliminated in the urine or expired air, indicating near-total absorption of the exposure dose.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

甲苯通过人体皮肤吸收速度较慢，吸收率范围在14到23毫克/平方厘米-小时。

Toluene is absorbed through human skin slowly, with absorption rates ranging from 14 to 23 mg/sq cm-hour.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

在人和动物的研究中已经表明，体内的大部分甲苯通过尿液排出，主要是以代谢物的形式。

Studies in both humans and animals have shown that the majority of toluene in the body is eliminated in the urine, mainly as metabolites.

来源:Hazardous Substances Data Bank (HSDB)

制备方法与用途

制备方法

1. 煤焦化副产的粗苯馏分中含甲苯15-20%，曾经是甲苯主要来源，生产每吨焦炭可回收甲苯1.1-1.3kg。从20世纪50年代开始，世界甲苯的主要来源已由煤焦化副产转变为催化重整和烃类裂解；到1982年，石油甲苯的产量已占总产量的96%以上。催化重整油中含芳烃50-60%，其中甲苯含量可达40-45%；裂解汽油中的芳烃含量为70%（质量）左右，其中15-20%是甲苯。

2. 炼焦副产的甲苯主要通过蒸馏和精制获得。先经过初步蒸馏分离出粗甲苯，再进行进一步纯化处理，包括脱硫、脱水等步骤。

3. 另一种方法是在甲苯中慢慢加入98%的硫酸，混匀并使噻吩反应完全后静置0.5小时，分出下层酸液。当硫酸试验合格时即表示酸洗结束；然后用蒸馏水充分洗涤至硫化合物含量合格，并用水洗至酸碱度合格，最后通过无水氯化钙脱水，进行最终的精馏处理以获得纯甲苯。

用途简介

甲苯是芳香族碳氢化合物的一员，其性质与苯相似。在工业中常被用作有机溶剂及有毒性苯的替代品，并作为许多化工产品的原料，包括但不限于制造炸药、农药、苯甲酸、染料和合成树脂等。此外，它还是一种重要的汽油组分。

用途

1. 广泛用于有机溶剂、合成医药、涂料、树脂、染料及炸药和农药的原料；也可作为色谱分析的标准物质和试剂。

2. 甲苯用作生产苯和其他化工产品的原料。它在油漆、清漆、粘合剂及油墨制造等领域的应用非常广泛，还可用于萃取及脱脂过程，以及化学合成中的溶剂；此外，还可以用来提高汽油的辛烷值，并作为涂料和硝酸纤维素的溶剂。

3. 甲苯还用作植物成分浸出剂、溶剂，以及高辛烷值汽油添加剂。它也可用于清洗剂，同时被广泛应用于染料和香料合成等领域。

4. 在工业上，甲苯可用来制造炸药，并作为许多农药和医药中间体的原料。其蒸汽与空气混合能形成爆炸性物质，在制造梯思梯炸药方面有重要作用。

5. 作为分析试剂时，它可用作溶剂、萃取分离剂及色谱分析试剂；也可以用作清洗剂以及在有机合成中制备苯甲酸和其他化合物。此外，甲苯还用于调配汽油组成，并作为生产甲苯衍生物、炸药和染料中间体的主要原料之一。

反应信息

• 作为反应物：
  描述：

  甲苯 在 ammonium sulfide 、 硝酸 作用下， 生成 对氨基苯甲酸
  参考文献：
  名称：

  Fischer,G., Justus Liebigs Annalen der Chemie, 1863, vol. 127, p. 145

  摘要：

  DOI：
• 作为产物：
  描述：

  (benzyloxy)benzene 在 氢气 作用下， 249.84 ℃ 、4.0 MPa 条件下， 反应 0.5h， 生成 甲苯
  参考文献：
  名称：

  苄基苯基醚在水相和非极性相中的催化裂解机理

  摘要：

  探索了使用镍基和沸石基催化剂在液相中裂解苄基苯基醚（BPE）中的醚键的催化途径。在不存在催化剂的情况下，通过水解在水中选择性裂解C-O键，形成苯酚和苯甲醇作为中间体，然后进行烷基化。通过在523 K下水的离解提供催化反应的水合氢离子。添加HZSM-5后，相对于质子浓度，水解和烷基化速率显着提高。在Ni / SiO 2存在下，选择性氢解作用主要用于裂解C脂族-O键。在双功能Ni / HZSM-5的催化下，氢解反应是主要途径，而不是水解（次要途径）。在非极性十一烷中，非催化热解路线占主导地位。在Ni / SiO 2存在下十一烷中BPE的氢解作用似乎是主要的反应途径或Ni / HZSM-5，几乎完全抑制了自由基反应。密度泛函理论（DFT）的计算有力地支持了BPE在水相和非极性相中提出的C-O键断裂机理。这些计算表明，BPE首先被质子化，随后在水相中水解。DFT计算表明，在非极性溶剂中的自由基反应

  DOI：

  10.1016/j.jcat.2013.10.024
• 作为试剂：
  描述：

  硫代异氰酸苯酯 在 乙醇 、 甲苯 、 苯 作用下， 生成 1,4-diphenyl-5-thio-1,2,4-triazolidin-3-one
  参考文献：
  名称：

  Marckwald, Chemische Berichte, 1892, vol. 25, p. 3106,3107

  摘要：

  DOI：

文献信息

• Iron-catalyzed thioesterification of methylarenes with thiols in water
  作者：Liang Wang、Jing Cao、Qun Chen、Ming-yang He

  DOI：10.1016/j.tetlet.2014.10.155

  日期：2014.12

  An iron-catalyzed coupling reaction of methylarenes with thiols leading to thioesters has been developed. The reactions were carried out in water with tert-butyl hydroperoxide (TBHP) as the oxidant and polyoxyethanyl α-tocopheryl sebacate (PTS) as the surfactant. The reaction medium is compatible with a series of functional groups and can be reused.

  已经开发了铁催化的甲基芳烃与硫醇的偶联反应，从而生成硫酯。反应在水中以氢过氧化叔丁基（TBHP）为氧化剂，以聚环氧乙烷基α-生育酚癸二酸酯（PTS）为表面活性剂进行。反应介质与一系列官能团相容，可以重复使用。
• Facile Approach for C(sp3)–H Bond Thioetherification of Isochroman
  作者：Chun Cai、Jie Feng、Guoping Lu、Meifang Lv

  DOI：10.1055/s-0034-1380125

  日期：——

  An unprecedented C–S formation protocol via the direct oxidative C(sp 3 )–H bond thioesterification of isochroman under metal-free conditions was developed. A series of isochroman derivatives could be afforded efficiently by the green, simple, and atom-economical method.

  通过在无金属条件下异色满的直接氧化 C(sp 3 )-H 键硫酯化，开发了一种前所未有的 C-S 形成方案。通过绿色、简单和原子经济的方法可以有效地提供一系列异色满衍生物。
• Copper-Catalyzed Protodecarboxylation of Aromatic Carboxylic Acids
  作者：Lukas J. Gooßen、Werner R. Thiel、Nuria Rodríguez、Christophe Linder、Bettina Melzer

  DOI：10.1002/adsc.200700223

  日期：2007.10.8

  A catalyst generated from copper(I) oxide and 4,7-diphenyl-1,10-phenanthroline for the first time allows the catalytic protodecarboxylation even of deactivated aromatic carboxylic acids, giving rise to the corresponding arenes. Based on DFT calculations, a reaction pathway is proposed that accurately reflects the experimental results, such as the observed reactivity order of the substrates.

  首次由氧化铜（I）和4,7-二苯基-1,10-菲咯啉生成的催化剂甚至可以使失活的芳族羧酸进行催化原脱羧，从而生成相应的芳烃。基于DFT计算，提出了一种反应路径，可以准确反映实验结果，例如观察到的底物反应顺序。
• Metal-Free Intermolecular Oxidative C–N Bond Formation via Tandem C–H and N–H Bond Functionalization
  作者：Abhishek A. Kantak、Shathaverdhan Potavathri、Rose A. Barham、Kaitlyn M. Romano、Brenton DeBoef

  DOI：10.1021/ja2087085

  日期：2011.12.14

  development of a novel intermolecular oxidative amination reaction, a synthetic transformation that involves the simultaneous functionalization of both a N-H and C-H bond, is described. The process, which is mediated by an I(III) oxidant and contains no metal catalysts, provides a rapid and green method for synthesizing protected anilines from simple arenes and phthalimide. Mechanistic investigations

  描述了一种新型分子间氧化胺化反应的发展，这是一种合成转化，涉及同时对 NH 和 CH 键进行功能化。该过程由 I(III) 氧化剂介导，不含金属催化剂，为从简单的芳烃和邻苯二甲酰亚胺合成受保护的苯胺提供了一种快速、绿色的方法。机理研究表明，该反应是通过邻苯二甲酰亚胺对芳族自由基阳离子的亲核攻击进行的，这与已报道的其他 I(III) 胺化反应的亲电芳族胺化相反。证明了这种新反应在合成各种取代苯胺衍生物中的应用。
• Homogeneous Catalytic Hydrogenation of Amides to Amines
  作者：Jacorien Coetzee、Deborah L. Dodds、Jürgen Klankermayer、Sandra Brosinski、Walter Leitner、Alexandra M. Z. Slawin、David J. Cole-Hamilton

  DOI：10.1002/chem.201204270

  日期：2013.8.12

  Hydrogenation of amides in the presence of [Ru(acac)3] (acacH=2,4‐pentanedione), triphos [1,1,1‐tris‐ (diphenylphosphinomethyl)ethane] and methanesulfonic acid (MSA) produces secondary and tertiary amines with selectivities as high as 93 % provided that there is at least one aromatic ring on N. The system is also active for the synthesis of primary amines. In an attempt to probe the role of MSA and

  在[Ru（acac）3 ]（acacH = 2,4-戊二酮），三[[1,1,1-三（二苯基膦甲基）乙烷]]和甲磺酸（MSA）的存在下进行酰胺加氢生成仲胺和叔胺如果在N上至少有一个芳环，则其选择性高达93％。该系统对伯胺的合成也具有活性。为了探索MSA的作用和反应机理，已经从[Ru（acac）3 ]，三醇和MSA或[RuX（OAc）（triphos）]的反应中制备了一系列甲磺酸钠络合物。 （X = H或OAc）或[RuH 2（CO）（triphos ）]与MSA。晶体学表征复合物包括：[茹（OAC-κ 1 O）2（H 2O）（triphos）]，[Ru（OAc‐κ 2 O，O'）（CH 3 SO 3 ‐κ 1 O）（triphos ）]，[Ru（CH 3 SO 3‐ κ 1 O）2（H 2 O）（三膦）]和[孺2（μ-CH 3 SO 3）3（三磷酸）2 ] [CH 3 SO 3 ]，而其他复合物，例如[茹（OAC-κ

表征谱图