1-Methyl-2-pyrrolidon

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:

Use water spray, powder, alcohol-resistant foam, carbon dioxide.

Fresh air, rest. 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.

Rinse mouth. Refer for medical attention .

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.

Biological Exposure Indices (BEI) [ACGIH] - 5-Hydroxy-N-methyl-2-pyrrolidone in urine = 100 mg/L at end of shift;

20.0 [ppm], (can also occur as vapor and aerosol)[German Research Foundation (DFG)]

Small quantities can be stored in polyethylene, polypropylene, or clear glass bottles.

Safe Storage: Separated from oxidants, rubber, plastics, aluminum and light metals. Dry. Ventilation along the floor.

Spillage Disposal: Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

SMALL SPILLS AND LEAKAGE: If you should spill this chemical, use absorbent paper to pick up all liquid spill material. Seal the absorbent paper, as well as any of your clothing which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Wash any surfaces you may have contaminated with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

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 quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Collect leaking liquid in sealable containers. Absorb liquid in sand or inert absorbent. Store and dispose of according to local regulations. Wash away remainder with plenty of water.

Do not eat, drink, or smoke during work.

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

The ability of N-methylpyrrolidone and polar lipids to increase the percutaneous delivery of metronidazole was investigated across full thickness human nonoccluded skin in vitro. Fatty acids and ethyl alcohol were also tested and were effected in penetration enhancement in propylene glycol vehicles; N-methylpyrrolidone increased metronidazole penetration from isopropyl myristate vehicles but not from propylene glycol. N-methylpyrrolidone premeated skin readily when applied in the neat state or in a mixture with isopropyl myristate. Results indicated that variations in barrier permeability to metronidazole were associated with the rate of N-methylpyrrolidone permeating the skin.

The effect of a penetration enhancer, N-methylpyrrolidone (N-methyl-2-pyrrolidone) or isopropyl myristate, on the in vitro permeability of gonadorelin (luteinizing hormone-releasing hormone; LHRH) through porcine epidermis was investigated. The permeability coefficient of gonadorelin significantly increased through penetration enhancer treated epidermis in comparison to the control. It was concluded that both penetration enhancers can enhance the percutaneous absorption of peptides such as gonadorelin.

Laurocapram (Azone; 1-dodecylazacycloheptan-2-one; I), N-methylpyrrolidone (N-methyl-2-pyrrolidone; II) and dodecyl-L-pyroglutamate (III) were studied in permeation cells in vitro, for their ability to improve the absorption of insulin (IV) and FD&C Blue No. 1 (brilliant blue FCF; V) through skin; the compounds were formulated into a 40% solution of propylene glycol in increasing concentrations. ... The permeation of V was improved in the presence of II, with concentrations of II ranging from 6.0 to 20.0% exhibiting the same efficacy. In experiments with IV, the optimum efficacy of II was found at a concentration close to 10.0%, with a decline in efficacy in higher and lower concentrations. ...

LC50; Species: Daphnia magna (Water Flea) age <24 hr; Conditions: freshwater, static, 23 °C, pH 7, dissolved oxygen 7.8 mg/L; Concentration: 2500 ug/L for 24 hr (95% confidence interval: 1800-3500 ug/L) />99.9% purity/

LC50; Species: Daphnia magna (Water Flea) age <24 hr; Conditions: freshwater, static, 23 °C, pH 7, dissolved oxygen 7.8 mg/L; Concentration: 1230 ug/L for 48 hr (95% confidence interval: 1000-1500 ug/L) />99.9% purity/

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 4.3(SRC), determined from a log Kow of -0.38(2) and a regression-derived equation(3), indicates that 1-methyl-2-pyrrolidone is expected to have very high mobility in soil(SRC). Volatilization of 1-methyl-2-pyrrolidone from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 3.20X10-9 atm-cu m/mole(4). 1-Methyl-2-pyrrolidone is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.345 mm Hg at 25 °C(5). Utilizing the Japanese MITI test, 73% of the Theoretical BOD was reached in 4 weeks(6) indicating that biodegradation is an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 4.6(SRC), determined from a log Kow of -0.38(2) and a regression-derived equation(3), indicates that 1-methyl-2-pyrrolidone is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon a Henry's Law constant of 3.20X10-9 atm-cu m/mole(5). According to a classification scheme(6), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Utilizing the Japanese MITI test, 73% of the Theoretical BOD was reached in 4 weeks(7) indicating that biodegradation is an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1-methyl-2-pyrrolidone, which has a vapor pressure of 0.345 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1-methyl-2-pyrrolidone 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 5.2 hrs(SRC), calculated from its rate constant of 7.40X10-11 cu cm/molecule-sec at 25 °C(3). 1-Methyl-2-pyrrolidone does not absorb light at wavelengths >290 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

Headache.

MAY BE ABSORBED! Redness. Pain.

Redness. Pain. Blurred vision.

Burning sensation in the throat and chest.

Rapid, irregular respiration, shortnessof breath, decreased pain reflex, and slight bloody nasalsecretion.

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical.[Available from, as of October 25, 2012: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=872-50-4]

1-Methyl-2-pyrrolidinone was detected in 1 of 46 US industrial effluent samples(1). 1-Methyl-2-pyrrolidone is present in shale oil retort water(2,3). 1-Methyl-2-pyrrolidinone was found in shale retort water at a concentration of 3 mg/L(2). Retort Water Treatment Cell analysis showed an influent concentration of 2.8 and effluent concentrations of not detected, 1.4, 3.3, and 10.1 mg/L at 1, 3, 5 and 7 weeks of treatment cell operation, respectively, suggesting a desorption from solids over time(3). The compound was detected at concentrations of 66.3 and 33.7 ug/L in wastewaters from a petrochemical plant sampled in January and March 1997, respectively; it was not detected in a July 1996 sample. 1-Methyl-2-pyrroldinone was detected at concentrations of 0.2 and 3.9 ug/L in leachate from an industrial landfill sampled in December 1996 and March 1997, respectively; locations not specified; limit of detection was 0.2 ug/L(4). 1-Methyl-2-pyrrolidinone was detected at 68.9 ug/L in leachate from a municipal waste landfill in Japan(5).

1-Methyl-2-pyrrolidinone was detected in the raw effluent from a textile finishing plant, North Carolina, concentration not provided(1). The compound was detected in spraybooth scrubber automotive painting operation at a concentration of 300 mg/L of boothwater, 1.51X10-8 ar partial pressure, atm in air; the compound was applied in spray at 7700 kg/annum(2).

The Koc of 1-methyl-2-pyrrolidone is estimated as 5(SRC), using a log Kow of -0.38(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 1-methyl-2-pyrrolidone is expected to have very high mobility in soil. 1-Methyl-2-pyrrolidinone had Rf values of 0.74, 0.65, 0.67, and 1.0 in silt, loam, clay and sand, respectively, in laboratory soil thin layer chromatography (TLC) experiments(4) which is consistent with significant mobility in soil(SRC).

/HUMAN EXPOSURE STUDIES/ Six male volunteers were exposed for eight hours on four different days to 0, 10, 25, and 50 mg/cu m N-methyl-2-pyrrolidone. Plasma was collected and urine was sampled during and after the exposure. Changes in nasal volume were measured by acoustic rhinometry and in airway resistance by spirometry. The eight-hour experimental exposure to 10, 25, and 50 mg/cu m did not induce discomfort to eyes or upper airways. Acute changes in nasal volume were not found, and no changes in the spirometric data could be registered. ... N-Methyl-2-pyrrolidone was absorbed through the respiratory tract and readily eliminated from the body, mainly by biotransformation to other compounds. Exposure to 10, 25, or 50 mg/cu m N-methyl-2-pyrrolidone did not cause nose, eye, or airway irritation. Thus, N-methyl-2-pyrrolidone is a mild irritant.

/SIGNS AND SYMPTOMS/ It can cause dermatitis with blistering, edema, and erythema with prolonged or repeated contact.

/SIGNS AND SYMPTOMS/ In the semiconductor industry, headaches and chronic eye irritation were described in some employees exposed to levels as low as 0.7 ppm. Levels of 49 to 83 ppm were found unbearable by the workers.

/SURVEILLANCE/ Several workers in a small electrotechnical company in Norway experienced irritant reaction of the skin after a few days of working with the solvent N-methyl-2-pyrrolidone. ... After 2 days of work with N-methyl-2-pyrrolidone, 10 of the 12 involved workers displayed acute irritant contact dermatitis of the hands. ...

/ALTERNATIVE and IN VITRO TESTS/ The effects of absorption enhancers such as laurocapram (Azone), N-methylpyrrolidone, propylene glycol, and oleic acid on the percutaneous absorption of heparin sodium through excised human skin were investigated. Laurocapram, N-methylpyrrolidone, and propylene glycol promomted heparin flux, while oleic acid did not.

Residues of n-methylpyrrolidone are exempted from the requirement of a tolerance when used in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to growing crops only. Use: solvent, cosolvent.

Used as a solvent for chemicals and resins in the microelectronics and pharmaceutical industries; [HSDB] Widely used to replace other solvents, e.g., for paint stripping and lube oil extraction; it is used as a solvent for pesticides, coatings, adhesives, dyes, pigments, polymers, and polyurethane foam cleanup. [ACGIH]

Metal Degreasing [Category: Clean]

Important areas of use:[Table#5034]

Solvent for resins, acetylene, etc., pigment dispersant, petroleum processing, spinning agent for polyvinyl chloride, microelectronics industry plastic solvent applications, intermediate.

SOLVENT FOR CARBON DIOXIDE REMOVAL IN AMMONIA GENERATORS, POLYMER PREPN, & PROCESSING ACETYLENE; SOLVENT FOR EXTRACTION OF BTX AROMATICS & BUTADIENE

Pharmaceutical applications make use of the properties of 1-methyl-2-pyrrolidone as a penetration enhancer for a more rapid transfer of substances through the skin. ... Approved as a solvent for slimicide application to food packaging materials.

(1976) 1.16X10+9 GRAMS

(1978) 1.57X10+9 GRAMS

2023: 100,000,000 - <250,000,000 lb

(1977) PROBABLY GREATER THAN 2.3X10+6 GRAMS

(1979) PROBABLY GREATER THAN 2.3X10+6 GRAMS

Annual production has been estimated at 36-39,000 tons a year (1991 OSHA).

World capacity of NMP is currently estimated at 200,000 - 250,000 t/a.

For more U.S. Production (Complete) data for 1-METHYL-2-PYRROLIDINONE (7 total), please visit the HSDB record page.

Large-scale production of NMP /N-methyl-2-pyrrolidone/ is predominantly carried out by reacting gamma-butyrolactone with an excess of pure or aqueous methylamine in a high-pressure tube reactor (6-12 MPa). The reaction is exothermic and often run under adiabatic conditions with reactor temperatures in the range of 250-400 °C. The resulting product mixture is decompressed and distilled. The NMP yield is normally more than 97%.

NMP /N-methyl-2-pyrrolidone/ can also be produced by hydrogenation of N-hydroxymethyl-2-pyrrolidone or by reaction of acrylonitrile with methylamine in the presence of a peroxide radical initiator.

... Hydrogenation of N-methylsuccinimide or mixtures of maleic or succinic anhydride and methylamine.

High-pressure synthesis from acetylene and formaldehyde.

Cosmetics product ingredient: N-Methylpyrrolidone (Methyl pyrrolidone)

Information on 105 consumer products that contain N-Methylpyrrolidone in the following categories is provided:

Pesticide, Fertilizer, and Other Agricultural Chemical Manufacturing

2-Pyrrolidinone, 1-methyl-: ACTIVE

Due to it's low toxicity and non-halogenated structure, 1-methyl-2-pyrrolidinone is increasingly being used in paint thinners and industrial solvents.