N-METHYL-2-PYRROLIDONE

CAS NUMBER : 872-50-4
EINECS Number: 212-828-1

synonyms:
N-Metil-2-pirrolidon; C5H11N; N-METHYLPRROLIDONE; n-methylprrolidone; N-methylprrolidone; n-methylprolidone; n-methyl prrolidon; n-methylprrolidon; n-methylprrolidone; N-methylprolidon; N-methylprolidone; N-methylprrolidon; nmethylprrolidone;nmethylprrolidon; nmethylprolidone; N-METHYLPROLİDON; N-METHYLPRROLİDONE; N-METHYLPROLİDONE; C5H9; N-METHYLPRROLIDONE; N-METHYLPYRROLİDON; N-METHYLPROLİDON; N-METHYLPYRROLIDON;n-methylpyrrolidone; n-methylpyrrolidon; nmethylpyrolidone; nmethylpyrolidon; N-METİLPROLİDON; N-METİLPROLİDON; N-metilprolidon; n-metil prolidone; n-metilpyrolidone; n-metil pyrolidon; N-Metilprolidon; Methyl-2-pyrrolidinon; Methyl-2-pyrrolidone; Pyrrolidone; 1-methyl; methylpyrrolidin; 1-Methyl-2-pyrrolidone; nmp; NMP; N-MP; n-mp; C5H9NO; n-Methyl 2 Pyrrolidone (NMP); 1-methyl-2-pyrrolidone; 1-methyl-2-oxopyrrolidine; 1-methyl-2-pyrrolidinone; 1-methyl-5-pyrrolidinone; 1-methyl-5-pyrrolidone; 1-methyl-alpha-pyrrolidinone; 1-methylazacyclopentan-2-one; 1-methyl-gammabutyrolactam; 1-methylpyrrolid-2-one;N-Metil-2-pirrolidon;  1-methylpyrrolidinone; 1-methylpyrrolidone; 1-methylpyrrolidone-2; 2-pyrrolidinone, 1-methyl-; methyl-alpha-pyrrolidone; methylpyrrolidone; N-methyl-2-pyrrolidinone; n-methyl-2-pyrrolidone; N-methyl-alphapyrrolidinone; N-methyl-alpha-pyrrolidone; N-methyl-gamma-butyrolactam; Nmethylpyrrolidinone; N-methylpyrrolidone; NMP(=n-methyl-2-pyrrolidone); N-Méthyl-2-pyrrolidone; N-Metil Pirolidon; 872-50-4; 1-Metil-Pirolidon; Metil Pirolidon; Metil Pirrolidon; N-Metil-2-Pirolidon; n-methyl-2-pyrrolidone; N-Metilpirolidinon; N-Metil-2-Pirolidinon; 1-Metil-Pirolidin-2-on; 1-Metilpirolidin-2-on; N-Metil-2-pirolidon; C10H18N2O2    ; N-Méthyl-2-pyrrolidone N-methylpyrrolidone; NMP n-methyl-2-pyrrolidone; NMP;  N-Methyl-2-pyrrolidinone; SCHEMBL1255511; VWBWQOUWDOULQN-UHFFFAOYSA-N; n-methyl-2-pyrrolidone ; N-Metil-2-pirrolidon ; N-Méthyl-2-pyrrolidone; NMP; N-Méthyl-2-pyrrolidone; N-Metil Pirolidon; 872-50-4; 1-Metil-Pirolidon; Metil Pirolidon; Metil Pirrolidon; N-Metil-2-Pirolidon; n-methyl-2-pyrrolidone; N-Metilpirolidinon; N-Metil-2-Pirolidinon; 1-Metil-Pirolidin-2-on; 1-Metilpirolidin-2-on; N-Metil-2-pirolidon; C10H18N2O2    ; N-Méthyl-2-pyrrolidone N-methylpyrrolidone; NMP n-methyl-2-pyrrolidone; NMP;  N-Methyl-2-pyrrolidinone; SCHEMBL1255511; VWBWQOUWDOULQN-UHFFFAOYSA-N; n-methyl-2-pyrrolidone ; N-Metil-2-pirrolidon ; N-Méthyl-2-pyrrolidone; NMP; N-Metil 2-pirrolidon; NMetil2pirrolidon; N Metil 2 pirrolidon; N Metil-2 pirrolidon;  N-Metil 2-pirolidon; NMetil2pirolidon; N Metil 2 pirolidon; N Metil-2 pirolidon; n-methyl-2-pyrrolidone ; n-methyl-2-pyrrolidone; NMethyl2pyrrolidone; N-Methyl 2-pyrrolidone; N Methyl 2 pyrrolidone; N Methyl-2 pyrrolidone;  N-Methyl-2-pyrrolidon; NMethyl2pyrrolidoe; N-Methyl 2-pyrrolidon; N Methyl 2 pyrrolidon; N Methyl-2 pyrrolidon; metil pirolidon;  N-Metil-2-pirrolidon; N Metil-2-pirrolidone; N-Metil-2-pirrolidone; N Metil 2- pirrolidone; N-metil-2-pirrolidon
 

N-methyl-2-pyrrolidone 

Description
Catalogue Number    806072
Synonyms    NMP, n-methyl-2-pyrrolidone
Overview    EMPLURA® is our low-cost alternative to high-purity qualities. With EMPLURA® we offer a range of solvents for a plurality of basic applications in non-regulated industries and for less demanding applications, preparative laboratory work and cleaning purposes. EMPLURA® solvents provide adequate specifications with the most important parameters.
Product Information
CAS number of n-methyl-2-pyrrolidone:     872-50-4
EC index number of n-methyl-2-pyrrolidone:     606-021-00-7
EC number of n-methyl-2-pyrrolidone: 212-828-1
Hill Formula of n-methyl-2-pyrrolidone:     C₅H₉NO
Molar Mass of n-methyl-2-pyrrolidone:     99.13 g/mol
HS Code     of n-methyl-2-pyrrolidone: 2933 79 00
Structure formula Image    Structure formula Image
Quality Level of n-methyl-2-pyrrolidone:     MQ200
Physicochemical Information of n-methyl-2-pyrrolidone: 
Boiling point of n-methyl-2-pyrrolidone:     202 °C (1013 hPa)
Density     of n-methyl-2-pyrrolidone: 1.03 g/cm3 (20 °C)
Explosion limit of n-methyl-2-pyrrolidone:     1.3 - 9.5 %(V)
Flash point of n-methyl-2-pyrrolidone:     91 °C
Ignition temperature of n-methyl-2-pyrrolidone:     245 °C
Melting Point of n-methyl-2-pyrrolidone:     -24 °C
pH value of n-methyl-2-pyrrolidone:     8.5 - 10.0 (100 g/l, H₂O, 20 °C)
Vapor pressure of n-methyl-2-pyrrolidone:     0.32 hPa (20 °C)
Solubility of n-methyl-2-pyrrolidone:     1000 g/l
Toxicological Information of n-methyl-2-pyrrolidone: 
LD 50 oral    LD50 Rat 3598 mg/kg
LD 50 dermal    LD50 Rabbit 8000 mg/kg
Safety Information according to GHS
Hazard Pictogram(s)    Hazard Pictogram(s)
Hazard Pictogram(s)
Hazard Statement(s)    H360D: May damage the unborn child.
H315: Causes skin irritation.
H319: Causes serious eye irritation.
H335: May cause respiratory irritation.
Precautionary Statement(s)    P201: Obtain special instructions before use.
P302 + P352: IF ON SKIN: Wash with plenty of soap and water.
P305 + P351 + P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P308 + P313: IF exposed or concerned: Get medical advice/ attention.
Signal Word    Danger
RTECS    UY5790000
Storage class    6.1C Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
WGK    WGK 1 slightly hazardous to water
Disposal    3
Relatively unreactive organic reagents should be collected in container A. If halogenated, they should be collected in container B. For solid residues use container C.
Safety Information
Hazard Symbols    Hazard SymbolsToxic
Categories of danger    toxic for reproduction, irritant
R Phrase    R 61-36/37/38
May cause harm to the unborn child.Irritating to eyes, respiratory system and skin.
S Phrase    S 53-45
Avoid exposure - obtain special instructions before use.In case of accident or if you feel unwell, seek medical advice immediately (show the label where possible).
Storage and Shipping Information
Storage    Store at +5°C to +30°C.
Specifications
Purity (GC)    ≥ 99.5 %
Identity (IR)    conforms
Color    ≤ 10 Hazen
Density (d 20 °C/ 4 °C)    1.031 - 1.033
Refractive index (n 20/D)    1.4680 - 1.4730
Acidity    ≤ 0.0002 meq/g
Alkalinity    ≤ 0.003 meq/g
Water    ≤ 0.10 %

n-methyl-2-pyrrolidone

n-methyl-2-pyrrolidone (NMP) is an organic compound consisting of a 5-membered lactam. It is a colorless liquid, although impure samples can appear yellow. It is miscible with water and with most common organic solvents. It also belongs to the class of dipolar aprotic solvents such as dimethylformamide and dimethyl sulfoxide. It is used in the petrochemical and plastics industries as a solvent, exploiting its nonvolatility and ability to dissolve diverse materials.[3]

Preparation
n-methyl-2-pyrrolidone:  is produced industrially by a typical ester-to-amide conversion, by treating butyrolactone with methylamine. Alternative routes include the partial hydrogenation of N-methylsuccinimide and the reaction of acrylonitrile with methylamine followed by hydrolysis. About 20,000 to 30,000 tons are produced annually.[3]

Applications
n-methyl-2-pyrrolidone:  is used to recover certain hydrocarbons generated in the processing of petrochemicals, such as the recovery of 1,3-butadiene and acetylene. It is used to absorb hydrogen sulfide from sour gas and hydrodesulfurization facilities. Due to its good solvency properties n-methyl-2-pyrrolidone:  is used to dissolve a wide range of polymers. It is also used as a solvent for surface treatment of textiles, resins, and metal coated plastics or as a paint stripper. n-methyl-2-pyrrolidone is utilized as a solvent in the commercial preparation of polyphenylene sulfide. In the pharmaceutical industry, n-methyl-2-pyrrolidone is used in the formulation for drugs by both oral and transdermal delivery routes.[4] It is also used heavily in lithium ion battery fabrication, as a solvent for electrode preparation, though there is much effort to replace it with solvents of less environmental concern, like water.[5]

Biological aspects
In rats, n-methyl-2-pyrrolidone:  is absorbed rapidly after inhalation, oral, and dermal administration, distributed throughout the organism, and eliminated mainly by hydroxylation to polar compounds, which are excreted via urine. About 80% of the administered dose is excreted as n-methyl-2-pyrrolidone:  and n-methyl-2-pyrrolidone:  metabolites within 24 hours. A probably dose dependent yellow coloration of the urine in rodents is observed. The major metabolite is 5-hydroxy-n-methyl-2-pyrrolidone.

Studies in humans show comparable results. Dermal penetration through human skin has been shown to be very rapid. n-methyl-2-pyrrolidone:  is rapidly biotransformed by hydroxylation to 5-hydroxy-n-methyl-2-pyrrolidone, which is further oxidized to N-methylsuccinimide; this intermediate is further hydroxylated to 2-hydroxy-N-methylsuccinimide. These metabolites are all colourless. The excreted amounts of n-methyl-2-pyrrolidone:  metabolites in the urine after inhalation or oral intake represented about 100% and 65% of the administered doses, respectively. n-methyl-2-pyrrolidone:  has a low potential for skin irritation and a moderate potential for eye irritation in rabbits. Repeated daily doses of 450 mg/kg body weight administered to the skin caused painful and severe haemorrhage and eschar formation in rabbits. These adverse effects have not been seen in workers occupationally exposed to pure n-methyl-2-pyrrolidone: , but they have been observed after dermal exposure to n-methyl-2-pyrrolidone:  used in cleaning processes. No sensitization potential has been observed.[6]

n-methyl-2-pyrrolidone is a water-like liquid with a mild amine odor. It is stable and soluble in water. Materials to avoid are strong oxidizing or reducing agents.n-methyl-2-pyrrolidone(NMP) is a solvent used in a variety of industries and applications, such as paint and coating removal, petrochemical processing, engineering plastics coatings, agricultural chemicals, electronic cleaning and industrial/domestic cleaning. n-methyl-2-pyrrolidone is produced and imported into the United States, with use estimated at over 184 million pounds per year. 
Uses of N-Methyl-2-pyrrolidone: In commercial processes to strip paint, in the electronics industry for cleaning and degreasing silicon wafers, in immersion and ultrasonic equipment to clean engine parts, remove printing ink residues, and as a solvent for surface coatings.
-The final risk assessment for n-methyl-2-pyrrolidoneevaluated health risks to consumers and workers using n-methyl-2-pyrrolidonein paint and coating removal products, as well as occupants in residences and the workplace where NMP paint and coating removers are used. Paint and coating removal products pose some of the highest exposures among the various uses of N-Methyl-2-pyrrolidone.
-The final risk assessment identified risks to pregnant women and women of childbearing age, who have high exposure to n-methyl-2-pyrrolidone through paint or coating removal. Acute and chronic risks identified for people who use n-methyl-2-pyrrolidonefor less than four hours per day may be reduced by use of specific types of chemical-resistant gloves. However, gloves and respirators do not adequately reduce risks to people who use n-methyl-2-pyrrolidonefor more than four hours per day on a single day or repeatedly over a succession of days. 
Product names and ingredients change. Searching the Internet using the terms "N-Methylpyrrolidone", "1-methyl-2-pyrrolidinone" or "NMP" and "paint and coating removal" produces results that include names of NMP-containing products.
One approach is to prohibit the manufacture (including import), processing, and distribution in commerce of N-Methyl-2-pyrrolidone for consumer and commercial paint and coating removal; to prohibit commercial use of N-Methyl-2-pyrrolidone; and to require manufacturers, processors, and distributors, except for retailers, of NMP to provide downstream notification of these prohibitions throughout the supply chain; and to require limited recordkeeping.
The second approach is a combination of requirements to address unreasonable risks to workers and consumers. Specifically, the approach would limit the amount of NMP in paint removal products to no more than 35 percent by weight; require formulators to evaluate and identify specialized gloves that protect against skin absorption; require occupational users to have worker protection programs to require that workers wear personal protective equipment to prevent skin and inhalation exposures, require hazard communication for commercial users; and require warning labels for consumers with detailed information on proper ways to reduce exposure. The warning labels would advise consumers to wear protective gear, to not spray apply N-Methyl-2-pyrrolidone, and to increase ventilation in the work area.