N-Methylaniline

N-Methylaniline
Names
	Preferred IUPAC name N-Methylaniline
	Other names N-methylbenzenamine; N-Monomethylaniline; Anilinomethane; N-phenylmethylamine; Monomethylaniline; N-methylaminobenzene; Methylbenzeneamine; N-Methyl-phenylamine; (methylamino) benzene
Identifiers
CAS Number	100-61-8 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:15733;
ChemSpider	7234;
ECHA InfoCard	100.002.610
EC Number	249-927-4;
KEGG	C02299;
PubChem CID	7515;
RTECS number	BY4550000;
UNII	TH45GK410O ;
UN number	2294
CompTox Dashboard (EPA)	DTXSID9021841 ;
	InChI InChI=1S/C7H9N/c1-8-7-5-3-2-4-6-7/h2-6,8H,1H3 Key: AFBPFSWMIHJQDM-UHFFFAOYSA-N;
	SMILES CNC1=CC=CC=C1;
Properties
Chemical formula	C7H9N
Molar mass	107.156 g·mol−1
Appearance	colorless liquid
Odor	weak, ammonia-like
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)
Solubility in water	Insoluble
Vapor pressure	0.3 mmHg (20 °C)
Magnetic susceptibility (χ)	-82.74·10−6 cm3/mol
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H311, H331, H373, H410
Precautionary statements	P260, P261, P264, P270, P271, P273, P280, P301+P310, P302+P352, P304+P340, P311, P312, P314, P321, P322, P330, P361, P363, P391, P403+P233, P405, P501
Flash point	79 °C; 175 °F; 353 K
	Lethal dose or concentration (LD, LC):
LDLo (lowest published)	280 mg/kg (rabbit, oral); 1200 mg/kg (guinea pig, oral)
	NIOSH (US health exposure limits):
PEL (Permissible)	TWA 2 ppm (9 mg/m3) [skin]
REL (Recommended)	TWA 0.5 ppm (2 mg/m3) [skin]
IDLH (Immediate danger)	100 ppm
Related compounds
Related aromatic amines	Aniline; Dimethylaniline
Related compounds	Toluidines
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

N-Methylaniline (NMA) is an aniline derivative. It is an organic compound with the chemical formula C₆H₅NH(CH₃). The substance is a colorless viscous liquid, Samples turn 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.^[3]

Use as a fuel additive

N-Methylaniline is a principal component of NMA (monomethylaniline), a non-traditional antiknock agent increasingly used by petroleum refiners and fuel distributors around the world to increase the octane number of gasoline petrol. It is usually added to gasoline in concentration of around 1.3% volume to avoid high gum levels that can cause increased carbon deposits in engine parts ^{[citation needed]}. Higher concentrations are permitted by most regulatory agencies if a detergent and a fuel combustion modifier are added to the component to keep gum formation from happening. NMA blended in those concentrations to gasoline / petrol is not more toxic than the hundreds of chemicals that compose this fuel.

Policies on blending NMA in gasoline

Tank railcar carrying N-methylaniline in Astana, Kazakhstan

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.”^[5]

United States

N-Methylaniline as is (neat) does not appear on the U.S. Environmental Protection Agency’s (EPA) List of Registered Gasoline Additives. However, registration can be obtained at higher concentration which maximum authorized dosage depends on a suitable detergent and an effective fuel combustion modifier added to this component.

Fuel additives in the United States are regulated under section 211 of the Clean Air Act (as amended in January 1995). The Environmental Protection Agency (EPA) requires the registration of all fuel additives which are commercially distributed for use in highway motor vehicles in the United States, and may require testing and ban harmful additives. The EPA also regularly reviews the health and net economic benefits of Clean Air Act policies. The act also requires deposit control additives (DCAs) be added to all gasolines. This type of additive is a detergent additive that acts as a cleansing agent in small passages in the carburetor or fuel injectors. This in turn serves to ensure a consistent air and fuel mixture that will contribute to better gas mileage.

Europe

It appears that only one NMA based product for use as an octane enhancer is registered with ECHA / REACH. Because it is not an oxygenate this component does not appear on 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.

Worldwide Fuel Charter

Because it is not an oxygenate NMA does not appear on 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.” Under policies that are specific to those countries NMA is banned in China and Russia. Most other countries follow the environmental rules of registration of the United States and Europe for the use of this component as an octane enhancer in gasoline / petrol.

Other reactions

It maybe reacted with diglycidyl aniline to produce a complex mixture of cyclic products including 7 and 8 membered rings.^[6]

References

^ ^a ^b ^c ^d ^e ^f NIOSH Pocket Guide to Chemical Hazards. "#0436". National Institute for Occupational Safety and Health (NIOSH).
^ "Monomethyl aniline". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
^ "TOXNET". toxnet.nlm.nih.gov. Archived from the original on 2018-09-20. Retrieved 2016-05-28.
^ "GB17930-2013 Gasoline for Motor Vehicles" (PDF).
^ "The Asian Clean Fuels Association: ACFA | Promotion of clean fuels in Asia". www.acfa.org.sg. Retrieved 2016-05-28.
^ Matějka, L.; Tkaczyk, M.; Pokorný, S.; Dušek, K. (1986-05-01). "Cyclization in the reaction between diglycidylaniline and amine". Polymer Bulletin. 15 (5): 389–396. doi:10.1007/BF00265719. ISSN 1436-2449.

External links

(in English) MSDS sheet for N-methylaniline (pdf)

[PGCH-1] ^ ^a ^b ^c ^d ^e ^f NIOSH Pocket Guide to Chemical Hazards. "#0436". National Institute for Occupational Safety and Health (NIOSH).

[2] "Monomethyl aniline". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).

[3] "TOXNET". toxnet.nlm.nih.gov. Archived from the original on 2018-09-20. Retrieved 2016-05-28.

[4] "GB17930-2013 Gasoline for Motor Vehicles" (PDF).

[:0-5] "The Asian Clean Fuels Association: ACFA | Promotion of clean fuels in Asia". www.acfa.org.sg. Retrieved 2016-05-28.

[6] Matějka, L.; Tkaczyk, M.; Pokorný, S.; Dušek, K. (1986-05-01). "Cyclization in the reaction between diglycidylaniline and amine". Polymer Bulletin. 15 (5): 389–396. doi:10.1007/BF00265719. ISSN 1436-2449.

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