N-Methylaniline
| Aniline | |
| Names | |
|---|---|
| Other names
N-Monomethylaniline
Anilinomethane N-phenylmethylamine Monomethylaniline N-methylaminobenzene Methylbenzeneamine N-Methyl-phenylamine (methylamino) benzene |
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| Identifiers | |
100-61-8  |
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| ChEBI | CHEBI:15733 |
| ChemSpider | 7234 |
| EC Number | 249-927-4 |
| Jmol 3D model | Interactive image |
| KEGG | C02299 |
| PubChem | 7515 |
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| Properties | |
| C7H9N | |
| Molar mass | 107.16 g·mol−1 |
| Appearance | Yellow to light-brown liquid[1] |
| Odor | weak, ammonia-like[1] |
| Density | 0.99 g/mL |
| Melting point | −57 °C (−71 °F; 216 K) |
| Boiling point | 194 to 196 °C (381 to 385 °F; 467 to 469 K) |
| Insoluble | |
| Vapor pressure | 0.3 mmHg (20 °C)[1] |
| Vapor pressure | {{{value}}} |
| Related compounds | |
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Related aromatic amines
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Aniline Dimethylaniline |
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Related compounds
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Toluidines |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |
N-Methylaniline (NMA) is an aniline derivative. It is an organic compound with the chemical formula C6H5NH(CH3). The substance exists as a colorless or slightly yellow viscous liquid and turns brown when exposed to air. The chemical is insoluble in water. It is used as a latent and coupling solvent and is also used as an intermediate for dyes, agrochemicals and other organic products manufacturing. NMA is toxic and exposure can cause damage to the central nervous system and can also cause liver and kidney failure.[2]
Contents
Use as a fuel additive
N-Methylaniline is a principal component of MMA (monomethylaniline), a non-traditional antiknock agent used by some as a cheap method to increase the octane number of gasoline petrol. It is usually added to gasoline in concentrations around 1.3% mass. However, its use can result in gum formation, drastically shortened induction period, and sharply increased seal swell. High gum levels cause increased carbon deposits in engine parts. Shorter induction times can cause gasoline stability to decline and antiknock. The swelling of seal rings may cause oil leaks in engines. The addition of NMA to gasoline could also cause heavier copper strip corrosion, which can lead to engine corrosion. NMA also contains nitrogen, which when combusted forms harmful nitrogen oxides (NoX). Gasoline blends with greater than 5% concentration of NMA can cause sediment to form in the engine combustion chambers, which can cause failure of engine anti-knock sensors, according to one study.[3]
Policies on blending NMA in gasoline
China
China has banned the use of most chemical gasoline additives, including NMA, in gasoline standard directive GB17930-2013[4] dated Dec. 18 2013, which states that “Additives used in gasoline for motor vehicles should not contain recognised harmful substances and should be used by following up with the recommended safe dosage. Chemicals, such as methylal, aniline-type compounds, halogens and those containing phosphorus and silicon, etc. should not intentionally be added in gasoline.”[3]
United States
NMA is not in the U.S. Environmental Protection Agency’s (EPA) List of Registered Gasoline Additives. Under section 211 of the U.S. Clean Air Act, all fuel additive products must be registered with the EPA before these products are sold in the United States.[3]
Europe
NMA is not in the list of recommended oxygenates in European Union (EU) petrol standards. Referring to EU EN 228:2012 and Directive 2009/30/EC, Automotive Fuels of Unleaded Petrol—Requirements and Test Methods, NMA is not in the list of recommended oxygenates, and its use is restricted by the European emission standards, Euro 5/6 standards (2209/2014): Regulation 715/2007.[3]
Worldwide Fuel Charter
NMA is not in the list of recommended oxygenates under category 4 of the Worldwide Fuel Charter published by the European Automobile Manufacturers Association (ACEA), which refers to emission standards for unleaded gasoline for “markets with advanced requirements for emission control.”[5]
See also
References
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External links
- (English) MSDS sheet for N-methylaniline (pdf)
