化工社化工社 化学情報印刷レポート · 研究参考用
ニトロメタン
ニトロメタン · ニトロメタン (55%メタノール溶液, 約8.7mol/L) · ニトロメタン [吸光分析用] · ニトロメタン, 0.1 mg/mL in MeOH · ニトロカルボール · ニトロメタン標準液 · CH3NO2 · MeNO2
識別子と物理属性
| CAS No. | 23717-53-5 |
|---|---|
| 分子式 | CH3NO2 |
| 平均分子量 | 61.04 g/mol |
| 単同位体質量 | 61.01637834 g/mol |
| SMILES | C[N+](=O)[O-] |
| InChIKey | LYGJENNIWJXYER-UHFFFAOYSA-N |
| PubChem CID | 6375 |
| ChEMBL | CHEMBL276924 |
| ChEBI | CHEBI:77701 |
| EC No. | 200-876-6 |
| DTXSID | DTXSID2020977 |
| 現地名 | ニトロメタン |
化学・物理的性質
| XLogP | 0.1 |
|---|---|
| 極性表面積 | 45.8 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 2 |
| 回転可能結合数 | 0 |
| 重原子数 | 4 |
| 形式電荷 | 0 |
| 複雑度 | 27.5 |
| 物質分類 | Nitrogen Compounds -> Nitros, AliphaticCarcinogens |
| 化粧品 | Anticorrosive |
| pH | pH of 0.01M aqueous solution = 6.126.4 (0.6g/l, H2O, 20℃) |
| SpringerMaterials Properties | Schoenflies notation |
| LogP（分配係数） | low Kow = -0.350.08 |
| 臭い | Moderately strong, somewhat disagreeable odor不快なフルーティーな匂い |
| 密度 | 1.139 at 68 °F (USCG, 1999) - Denser than waterwill sink1.1371 g/cu cm at 20 °CBulk density = 9.5 lb/galRelative density (water = 1): 1.141.38 @ 20°C1.127 g/mL at 25 °C (lit.) |
| Viscosity | 0.614 cP at 25 °C |
| Color/Form | Colorless liquidOily liquid |
| 溶解度 | greater than or equal to 100 mg/mL at 68 °F (NTP, 1992)Solubility of water in nitromethane: 2.1% at 25 °CIn water, 1.11X10+5 mg/L at 25 °CSoluble in ethanol, ethyl ether, acetone, carbon tetrachloride, and alkali10%105g/リットル9.5g/100mL(20℃) |
| 引火点 | 95 °F (NTP, 1992)95-96 °F95 °F (35 °C) (Closed Cup)36 °C (97 °F) (Closed cup)35 °C c.c. |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| 融点 | -29 °C (lit.) |
| 沸点 | 101.2 °C (lit.) |
| 蒸気密度 | 2.1 (vs air) |
| 蒸気圧 | 27.3 mm Hg ( 20 °C) |
| 屈折率 | n20/D 1.382(lit.) |
| 貯蔵条件 | Flammables area |
| pKa（酸解離定数） | 10.2(at 25℃) |
| 外観・状態 | 液体 |
| 色 | APHA: ≤10 |
| 爆発限界 | 7.3-63.0%(V) |
| 比熱容量 | Cp(liquid): 1.75 J/(g·K)Cp(gas): 0.91 J/(g·K), at 25℃ |
| Merck | 14,6611 |
| BRN | 1698205 |
| ヘンリー定数 | 2.24 at 20.00 °C, 3.61 at 30.00 °C, 5.40 at 40.00 °C, 7.97 at 50.00 °C (inert gas stripping, Bene and Dohnal, 1999) |
| 誘電率 | 22.7(Ambient) |
| 主な用途 | 食品および飲料 |
| 化粧品成分の機能 | 防錆剤 |
| InChI | 1S/CH3NO2/c1-2(3)4/h1H3 |
| InChIKey | LYGJENNIWJXYER-UHFFFAOYSA-N |
| SMILES | C[N+]([O-])=O |
| 表面張力 | 36.8mN/m at 20°C |
| CAS データベース | 75-52-5(CAS DataBase Reference) |
| NISTの化学物質情報 | Methane, nitro-(75-52-5) |
| EPAの化学物質情報 | Nitromethane (75-52-5) |
化学的特性
Nitromethane is a highly flammable and explosive colorless liquid with a strong, disagreeable odor. Nitromethane is not explosive, but is used as industrial chemical for various purposes. Nitromethane can explode only in big quantity and in strong confinement. In combination with some further components, nitromethane is the important part of very strong, cap sensitive explosives. Therefore, nitromethane is an easy accessible precursor for preparation of strong home-made explosives.Nitromethane is used as a stabilizer of halogenated organic solvents, rocket and racing fuel and a chemical intermediate. It is also used as a solvent for cyanoacrylate adhesives, polymers and waxes. It serves as a Michael donor, adding to alfa,beta-unsaturated carbonyl compounds through 1,4-addition in the Michael reaction. It acts as a solvent used for extractions, reaction medium and as a cleaning solvent. Further, it is used in the manufacture of pharmaceuticals, explosives, fibers and coatings.
安全性と法規制
| GHS 分類 | WarningH226: Flammable liquid and vapor [Warning Flammable liquids]P210, P233, P240, P241, P242, P243, P264, P270, P280, P301+P317, P303+P361+P353, P330, P370+P378, P403+P235, and P501 (click each P-code to see the statement)H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]P203, P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P317, P303+P361+P353, P304+P340, P317, P318, P330, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement) |
|---|---|
| 規制情報 | Chemical: Methane, nitro-Hazard Traits - CarcinogenicityMethane, nitro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Methane, nitro- 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: 22-11-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/11417Methane, nitro-: HSNO Approval: HSR001206 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.) |
| その他の安全情報 | IMAP assessments - Methane, nitro-: Human health tier II assessment |
| 輸送ラベル（DOT） | Flammable Liquid |
| 火災危険 | Behavior in Fire: Containers may explode (USCG, 1999)· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.Flammable. Gives off irritating or toxic fumes (or gases) in a fire. Vapour/air mixtures are explosive. Risk of fire and explosion on contact with incompatible substances. See Chemical Dangers. |
| 火災の可能性 | A very dangerous fire hazard when exposed to heat, oxidizers or flame. |
| 健康有害性 | Liquid may dry out skin and cause irritation. (USCG, 1999)· May cause toxic effects if inhaled or absorbed through skin. |
| 有害性の概要 | The lethal oral dose in humans is between 0.5 and 5 g/kg. Nitromethane can cause respiratory irritation, narcosis, and possibly liver injury. Animals in subchronic inhalation studies suffer thyroid injury. [ACGIH] Not irritating to the skinCan detonate under conditions of normal temperature and pressure[CHEMINFO] A skin, eye, and respiratory tract irritantMay cause CNS depressionMay cause effects on the liver, kidneys, and peripheral nervous system after repeated exposuresWill turn shock-sensitive if contaminated with acids, bases, metal oxides, hydrocarbons and other combustible materials. [ICSC] |
| 輸送番号・ガイド（DOT） | 1261 129 |
| 反応性グループ | Nitro, Nitroso, Nitrate, and Nitrite Compounds, Organic |
| EC 分類 | Symbol: XnR: 5-10-22S: (2)-41 |
| UN 分類 | UN Hazard Class: 3UN Pack Group: II |
| Special Reports | Matthews rdestimated permissible levels, ambient concentrations, and adverse effects of the nitrogenous products of combustion: the cyanides, nitroolefins, and nitroparaffinsJ combust toxicol 7 (aug): 157 (1980). Review with 51 references includes estimate of maximum permissible levels.Toxicology & Carcinogenesis Studies of Nitromethane in F344/N Rats and B6C3F1 Mice (Inhalation Studies). Technical Report Series No. 461 (1997) NIH Publication No. 97-3377 U.S. Department of Health and Human Services, National Toxicology Program, National Institute of Environmental Health Sciences, Research Triangle Park, NC 27709European Chemicals BureauIUCLID Dataset, Nitromethane (75-52-5) (2000 CD-ROM edition).[Available from, as of July 15,2005: http://esis.jrc.ec.europa.eu/] |
| 消火 | Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:Use water spray, powder, alcohol-resistant foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water. Combat fire from a sheltered position. |
| 応急処置措置 | Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer for medical attention.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.Refer for medical attention . |
| 漏出応急措置 | · 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. |
| 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:(General first aid procedures) |
| 安全保管 | Fireproof. Separated from incompatible materials. See Chemical Dangers. |
| Firefighting Hazards | Special hazards arising from the substance or mixture: Carbon oxides, nitrogen oxides (NOx). |
| 暴露管理・個人防護 | · Wear positive pressure self-contained breathing apparatus (SCBA). |
| 消火手順 | Fire Fighting Procedures: Explosive decomposition may occur under fire conditions. Fight fires from protected location or maximum possible distance. Use water spray, dry chemical, foam, or carbon dioxide. Use water spray to keep fire-exposed containers cool.If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, or carbon dioxide.Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.Advice for firefighters Wear self contained breathing apparatus for fire fighting if necessary.Use water spray to cool unopened containers. |
| 保管条件 | Storage Recommendations: Store in a cool, dry, well-ventilated location. Separate from amines, acids, bases, oxidizing materials, and metal oxides. Outside or detached storage is preferred.Conditions for safe storage, including any incompatibilities: 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. Hygroscopic. Store under inert gas. |
| 清掃方法 | Remove all ignition sources. establish forced ventilation to keep levels below explosive limit. Absorb liquids in vermiculite, dry sand, earth, peat, carbon, or a similar material and deposit in sealed containers. Follow by washing surfaces well first with alcohol, then with soap and water.Spill or Leak Procedures: Eliminate all ignition sources. Stop or control the leak, if this can be done without undue risk. Use water spray to cool and disperse vapors and protect personnel.Accidental Release Measures: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Beware of vapours accumulating to form explosive concentrations. Vapours can accumulate in low areas. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. 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 | Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]: |
| 処分方法 | SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. 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 soil or watereffects on animal and plant lifeand conformance with environmental and public health regulations.Incineration. Large quantities of material may require nitrogen oxide removal by catalytic or scrubbing processes.Waste treatment methods. Product: Burn in a chemical incinerator equipped with an afterburner and scrubber but exert extra care in igniting as this material is highly flammable. Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Contaminated packaging: Dispose of as unused product.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. |
| 体内負荷 | Nitromethane was detected, but not quantified in 1 of 12 human milk samples from four US urban areas(1). Nitromethane was detected (unspecified concentration) in a breast milk sample collected in Jersey City, NJ(2). |
| 相互作用 | A patient who ingested a methanol/nitromethane mixture (model airplane fuel) showed an apparent plasma creatinine concentration of 8.0 mmol/L by the Jaff'e reaction when the actual creatinine concentration, as measured by a specific enzymatic method, was 0.09 mmol/L. This effect was due to nitromethane in the plasma. Interference by nitromethane with the determination of creatinine by reaction with alkaline picrate (the Jaff'e reaction) has not previously been reported. When nitromethane was added to plasma, the apparent creatinine measured was linearly related to the amount of nitromethane added. Comparison of spectral changes occurring during creatinine/picrate and nitromethane/picrate reactions show substantial similarity, suggeting a similar structure for the products. Although the findings are of interest for both their toxicological and analytical implications, the main interest lies with their suggestion of a model system for future investigation of the Jaff'e reaction. |
| 標的器官 | Eyes, skin, central nervous system, liver |
| 生態毒性値 | LC50Species: Pimephales promelas (Fathead minnow)Conditions: staticConcentration: <278 mg/L for 96 hrSpecies: Brachydanio rerio (Zebrafish)Concentration: 460 mg/L for 48 hr |
| 環境中動態 | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that nitromethane is expected to have very high mobility in soil(SRC). Volatilization of nitromethane from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 2.86X10-5 atm-cu m/mole(3). Nitromethane is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 35.8 mm Hg(4). Nitromethane was readily degradable in a solid surface photomineralization test with 4.4% mineralization to CO2 in 17 hr(5)therefore, direct photolysis is expected to occur on soil surfaces exposed to sunlight(SRC). Utilizing a soil microcosm test, 5.1 and 2.3% conversion to CO2 in aerobic and anerobic soil, respectively, after 35 days(6) indicates that biodegradation may be important environmental fate process in soil(SRC).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that nitromethane is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 2.86X10-5 atm-cu m/mole(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 27 hours and 10 days, respectively(SRC). According to a classification scheme(5), a BCF of 1.4 measured for fish (Golden ide)(6) suggests the potential for bioconcentration in aquatic organisms is low(SRC). Direct photolysis in water exposed to sunlight is expected to occur(SRC) based on an observed photodegradation of 64.8% in 24 hours(7). Hydrolysis is not expected to occur in water(7). Biodegradation studies utilizing aqueous media give conflicting results(6,7).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), nitromethane, which has a vapor pressure of 35.8 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase nitromethane 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 123 days(SRC), calculated from its rate constant of 1.30X10-13 cu cm/molecule-sec at 25 °C(3). Nitromethane is expected to undergo direct photolysis in the atmosphere based on 83% degradation within 24 hours, and a half-life of 4.3 hours measured during tests for photodegradation(4,5). |
| 食品調査値 | Nitromethane has been detected at unspecified concentrations in stored food exudate(1). |
| 有害作用 | Neurotoxin - Sensorimotor |
| 暴露経路 | The substance can be absorbed into the body by inhalation and by ingestion.inhalation, ingestion, skin and/or eye contact |
| Milk Concentrations | ENVIRONMENTAL: Nitromethane was detected, but not quantified in 1 of 12 human milk samples from four US urban areas(1). Nitromethane was detected (unspecified concentration) in a breast milk sample collected in Jersey City, NJ(2). |
| 毒性の概要 | IDENTIFICATION AND USE: Nitromethane is a colorless oily liquid. It is used as solvent for cellulosic compounds, polymers, waxes, fatschemical synthesismodel rocket fuelgasoline additive. HUMAN EXPOSURE AND TOXICITY: Symptoms of inhalation include cough, drowsiness, headache, nausea, sore throat, unconsciousness, and vomiting. Allergic contact hand dermatitis was documented in 4 coworkers who similarly handled an adhesive solvent containing nitromethane. All 4 cases were confirmed by patch testing and resolved after allergen avoidance. One case of human poisoning has been reported. In that case, a handyman was exposed to high concentrations of nitrocellulose and nitromethane resulting in a 67% conversion of his hemoglobin to methemoglobin and sulfhemoglobin. Treatment with hyperbaric oxygen, transfusion, peritoneal dialysis and then 6 sessions of hemodialysis resulted in recovery. Nitromethane is confirmed animal carcinogen with unknown relevance to humans. ANIMAL STUDIES: The most common signs of toxicity in acute animal studies were central nervous system (CNS) depression and slight irritation of the respiratory tract. Histopathologic changes were mainly in the liver and kidneys with the liver showing the most prominent injury, ie subcapsular damage, focal necrosis, fatty infiltration, congestion, and edema. The sulfhemoglobinemia and methemoglobinemia formation activities of similar drugs were studied in mice after administration of one or three ip doses. After administration of a single dose, nitromethane did not produce methemoglobinemia. Nitromethane produced sulfhemoglobinemia only after administration of three consecutive doses. Under the conditions of 2 yr inhalation studies conducted by NTP, there was no evidence of carcinogenic activity of nitromethane in male rats. There was clear evidence of carcinogenic activity of nitromethane in female rats based on increased incidences of mammary gland fibroadenomas and carcinomas. There was clear evidence of carcinogenic activity of nitromethane in male mice based on increased incidences of harderian gland adenomas and carcinomas. There was clear evidence of carcinogenic activity in female mice, based on increased incidences of liver neoplasms (primarily adenomas) and harderian gland adenomas and carcinomas. Increased incidences of alveolar/bronchiolar adenomas and carcinomas in male and female mice exposed to nitromethane were also considered to be related to chemical administration. Reproductive effects were investigated in female rats. No differences were found between treated and control rats in percentages of successful matings, litter size, pup mortality, birth weight, or maternal behavior. Pups were tested at 2.5 months of age in a maze-learning apparatusthe offspring of treated rats showed impaired maze learning when compared to controls. In another developmental study male rats had decreased caudal, epididymal, and testicular weights and decreased sperm counts. There was a dose-response decrease in epididymal sperm motility. Female mice showed a dose-related increase in the average estrous cycle length. Nitromethane was not mutagenic in Salmonella typhimurium strains TA 98 and TA 100 with and without activation. Nitromethane was further tested for mutagenicity of using the Salmonella assay, Drosophila melanogaster and an in vivo micronucleus test. Nitromethane was inactive in each of the three mutagenic test systems. |
| 生態毒性抜粋 | /PLANTS/ Tested for phytotoxicity in wheat, alfalfa, soybean, tobacco, corn, white oak and scotch pine. Max dose was 25 mg/cu m. Minimum or no injury observed on any of plants. |
| Signs and Symptoms | Cough. Drowsiness. Headache. Nausea. Sore throat. Unconsciousness. Vomiting.Dry skin. Redness.See Inhalation.dermatitisIn Animals: irritation eyes, respiratory systemconvulsions, narcosisliver damage |
| TSCA 要件 | 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. Nitromethane is included on this list. Effective date: 4/13/89Sunset date: 12/19/95. |
| 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. Nitromethane is produced, as an intermediate or a final product, by process units covered under this subpart. |
| DHS Chemicals of Interest (COI) | NitromethaneA Commercial Grade400Explosive/Improvised Explosive Device Precursor material that, if stolen or diverted, can be converted into weapons using simple chemistry, equipment, or techniques. |
| F | 3-10 |
| 水環境危害等級（WGK） | 2 |
| 生命健康即時危険濃度 | 750 ppm |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | PA9800000 |
| 輸送番号（UN） | UN 1261 |
| 毒性 | LC (in air) in guinea pigs: 1000 ppmLD50 orally in mice: 1.44 g/kg (Weatherby) |
| PRTR法 | 第一種指定化学物質 |
| 税関コード | 29042090 |
| 危険文句（R） | 5-10-22 |
| 化審法 | (2)-191 優先評価化学物質 |
| 安衛法 | 有機則 第二種有機溶剤等 |
| 消防法 | 危険物第5類 |
| 危険表示 | Xn,F,Xi |
| hazard_note | Irritant/Flammable |
| 安全措置（S） | 41 |
| 危険等級 | 3Acute Tox. 4 InhalationAcute Tox. 4 OralCarc. 2Flam. Liq. 3Repr. 2 |
| 包装等級 | II |
| 自然発火温度 | 784 °F |
| 環境リスク評価 | ニトロメタン(75-52-5) |
| 貯蔵分類 | 4.1A - Other explosive hazardous materials |
| 有害物質データ | 75-52-5(Hazardous Substances Data) |
用途
解説
ニトロメタン，無色の液体．融点－29 ℃，沸点101.2 ℃，46.6 ℃(13.3 kPa)，27.5 ℃(5.3 kPa)．d254 1.1322．n22D 1.3806．水に難溶，エタノール，エーテル，ジメチルホルムアミドに可溶．水溶液は酸性を呈する．ニトロン酸としてアルカリ金属と塩をつくり，爆発性の固体となる．溶剤，ロケット燃料，界面活性剤，医薬品原料などに用いられる．有毒である．
用途
溶剤、界面活性剤、医薬中間体(原料)
用途
有機合成(和光試薬時報Vol.66 No.1,p.27(1998))。
説明
Nitromethane (75-52-5) is an explosive material that was originally manufactured for various applications including mining, construction, demolition, law enforcement, and military uses. However, due to threats of terrorism and increased attention to accident prevention, regulations concerning the transportation, storage, use, and transfer relating to explosives have steadily increased over the last few years and manufacturing limited.
使用
Most of the nitromethane produced in the United States (85% to 90%) is used in the synthesis of nitromethane derivatives used as pharmaceuticals, agricultural soil fumigants, and industrial antimicrobials (Markofsky 1991, Angus 2001). Nitromethane also is used as a fuel or fuel additive with methanol in racing cars, boats, and model engines. It formerly was used in the explosives industry as a component in a binary explosive formulation with ammonium nitrate and in shaped charges, and it was used as a chemical stabilizer to prevent decomposition of various halogenated hydrocarbons (NTP 1997, IARC 2000, Angus 2001).
一般的な説明
A colorless oily liquid. Flash point 95°F. May violently decompose if intensely heated when contaminated. Denser than water and slightly soluble in water. Hence sinks in water. Vapors are heavier than air. Moderately toxic. Produces toxic oxides of nitrogen during combustion.
製法・合成法
調製方法
Nitromethane was first prepared in 1872 by Kolbe, and is produced commercially by high-temperature vapour-phase nitration of propane. The process, which uses nitric acid as the nitrating agent, is based on a free-radical reaction in which the active species is the NO2 radical (Markofsky, 1991; Angus Chemical Co., 1998).Nitromethane and the other important nitroparaffins are synthesized commercially by the vapor-phase nitration of propane (Baker and Bollmeier 1978). At temperatures of 370-450°C and pressures of 8-12 atmospheres, nitromethane, nitroethane and 1- and 2-nitropropane are formed and then separated by distillation.