7/29/2019 N-Methyl-2-Pyrrolidone - Wikipedia, The Free Encyclopedia

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N-Methyl-2-pyrrolidone

1-Methyl-2-pyrrolidone

N-Methylpyrrolidone;N-methylpyrrolidinone; NMP

Identifiers

CAS

number

872-50-4

PubChem 13387

ChemSpider 12814

UNII JR9CE63FPM

KEGG C11118

ChEBI CHEBI:7307

ChEMBL CHEMBL12543

Jmol-3D

images

Image 1

(http://chemapps.stolaf.edu/jmol/jmol.php?

model=CN1CCCC1%3DO)

Properties

Molecular

formula

C5H9NO

Molar mass 99.13 g mol1

Density 1.028 g/cm3

Melting

point-24 C, 249 K, -11 F

Boiling

point 202-204 C, 475-477 K, 396-399 F

Hazards

NFPA 704

-Methyl-2-pyrrolidoneFrom Wikipedia, the free encyclopedia

(Redirected from Methylpyrrolidone)

-Methyl-2-pyrrolidone (NMP) is a chemical

compound with 5-membered lactam structure. It is a

clear to slightly yellow liquid miscible with water and

solvents like ethyl acetate, chloroform, benzene and

lower alcohols or ketones. It alsobelongs to the class of

dipolar aprotic solvents which includes also

dimethylformamide, dimethylacetamide and dimethyl

sulfoxide. Other names for this compound are: 1-methyl-

2-pyrrolidone,N-methylpyrrolidone,N-

methylpyrrolidinone and the brand name Pharmasolve.

NMP is used to recoverpure hydrocarbons while

processing petrochemicals (such as the recovery of 1,3-butadiene using NMP as an extractive distillation

solvent) and in the desulfurization of gases. Due to its

good solvency propertiesN-methyl-2-pyrrolidone is

used to dissolve a wide range of chemicals, especially in

the polymers field. It also used as a solvent for surface

treatment of textiles, resins and metal coated plastics or

as a paint stripper.[1] It 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 byboth oral and transdermaldelivery routes.[2]

NMP and its derivatives are used as intermediates for

the synthesis of agrochemicals, pharmaceuticals, textile

auxiliaries, plasticizers, stabilizers and specialty inks. It is

also employed as a nylon precursor. The rubber industry

uses it forSBR latex production and the electronics

industry for printed circuitboard manufacturing.[1]

World production capacity for NMP was 226 million lbin 2006. NMP has desirable properties such as low

volatility, low flammability and relatively low toxicity.

However, it has been identified as a reproductive

toxicant, first by California in 2001[3] and then by the

European Commission in 2003.[citation needed] In the

face of increasing regulation, some manufacturers are

considering alternative solvents for some applications,

especially where worker exposure is difficult to control,

such as in paint stripping, graffiti removal and

agriculture.[4]

See also

IUPAC name

Other names

SMILES

InChI

2

https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/CHEMBL12543https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/CHEMBL12543http://fdasis.nlm.nih.gov/srs/srsdirect.jsp?regno=JR9CE63FPMhttp://en.wikipedia.org/wiki/ChemSpiderhttp://www.chemspider.com/12814http://fdasis.nlm.nih.gov/srs/srsdirect.jsp?regno=JR9CE63FPMhttp://www.commonchemistry.org/ChemicalDetail.aspx?ref=872-50-4http://en.wikipedia.org/wiki/File:N-Methylpyrrolidone_Structural_Formulae.pnghttp://en.wikipedia.org/wiki/File:N-Methylpyrrolidone_Structural_Formulae.pnghttp://en.wikipedia.org/wiki/Methylpyrrolidone#cite_note-3http://en.wikipedia.org/wiki/Molar_masshttp://en.wikipedia.org/wiki/Methylpyrrolidone#cite_note-BASF-1http://en.wikipedia.org/wiki/Nylonhttp://en.wikipedia.org/wiki/Agrochemicalhttp://en.wikipedia.org/wiki/Jmolhttp://en.wikipedia.org/wiki/Methylpyrrolidone#cite_note-ISP-2http://en.wikipedia.org/wiki/Unique_Ingredient_Identifierhttp://en.wikipedia.org/wiki/Poly(p-phenylene_sulfide)http://en.wikipedia.org/wiki/ChemSpiderhttp://en.wikipedia.org/wiki/Paint_stripperhttp://en.wikipedia.org/wiki/Methylpyrrolidone#cite_note-BASF-1http://en.wikipedia.org/wiki/PubChemhttp://en.wikipedia.org/wiki/Polymerhttp://en.wikipedia.org/wiki/Textilehttp://en.wikipedia.org/wiki/Textilehttp://en.wikipedia.org/wiki/CAS_registry_numberhttp://en.wikipedia.org/wiki/Desulfurizationhttp://en.wikipedia.org/wiki/1,3-butadienehttp://en.wikipedia.org/wiki/1,3-butadienehttp://en.wikipedia.org/wiki/Dimethyl_sulfoxidehttp://en.wikipedia.org/wiki/Dimethyl_sulfoxidehttp://en.wikipedia.org/wiki/Aprotichttp://en.wikipedia.org/wiki/Alcoholhttp://en.wikipedia.org/wiki/Ethyl_acetatehttp://en.wikipedia.org/wiki/Ketonehttp://en.wikipedia.org/wiki/Chloroformhttp://en.wikipedia.org/wiki/Benzenehttp://en.wikipedia.org/wiki/Chemical_compoundhttp://en.wikipedia.org/wiki/Lactamhttp://en.wikipedia.org/wiki/Chemical_compoundhttp://en.wikipedia.org/wiki/Chemical_compoundhttp://chemapps.stolaf.edu/jmol/jmol.php?model=CN1CCCC1%3DOhttp://en.wikipedia.org/wiki/International_Chemical_Identifierhttp://en.wikipedia.org/wiki/Simplified_molecular-input_line-entry_systemhttp://en.wikipedia.org/wiki/International_Union_of_Pure_and_Applied_Chemistry_nomenclaturehttp://en.wikipedia.org/wiki/Methylpyrrolidone#cite_note-4http://en.wikipedia.org/wiki/Wikipedia:Citation_neededhttp://en.wikipedia.org/wiki/Methylpyrrolidone#cite_note-3http://en.wikipedia.org/wiki/Methylpyrrolidone#cite_note-BASF-1http://en.wikipedia.org/wiki/Nylonhttp://en.wikipedia.org/wiki/Agrochemicalhttp://en.wikipedia.org/wiki/Methylpyrrolidone#cite_note-ISP-2http://en.wikipedia.org/wiki/Poly(p-phenylene_sulfide)http://en.wikipedia.org/wiki/Methylpyrrolidone#cite_note-BASF-1http://en.wikipedia.org/wiki/Paint_stripperhttp://en.wikipedia.org/wiki/Textilehttp://en.wikipedia.org/wiki/Polymerhttp://en.wikipedia.org/wiki/Desulfurizationhttp://en.wikipedia.org/wiki/Extractive_distillationhttp://en.wikipedia.org/wiki/1,3-butadienehttp://en.wikipedia.org/wiki/Hydrocarbonshttp://en.wikipedia.org/wiki/Dimethyl_sulfoxidehttp://en.wikipedia.org/wiki/Dimethylacetamidehttp://en.wikipedia.org/wiki/Dimethylformamidehttp://en.wikipedia.org/wiki/Aprotichttp://en.wikipedia.org/wiki/Ketonehttp://en.wikipedia.org/wiki/Alcoholhttp://en.wikipedia.org/wiki/Benzenehttp://en.wikipedia.org/wiki/Chloroformhttp://en.wikipedia.org/wiki/Ethyl_acetatehttp://en.wikipedia.org/wiki/Water_(molecule)http://en.wikipedia.org/wiki/Lactamhttp://en.wikipedia.org/wiki/Chemical_compoundhttp://en.wikipedia.org/w/index.php?title=Methylpyrrolidone&redirect=nohttp://en.wikipedia.org/wiki/NFPA_704http://en.wikipedia.org/wiki/Boiling_pointhttp://en.wikipedia.org/wiki/Melting_pointhttp://en.wikipedia.org/wiki/Densityhttp://en.wikipedia.org/wiki/Molar_masshttp://en.wikipedia.org/wiki/Molecular_formulahttp://chemapps.stolaf.edu/jmol/jmol.php?model=CN1CCCC1%3DOhttp://en.wikipedia.org/wiki/Jmolhttps://www.ebi.ac.uk/chembldb/index.php/compound/inspect/CHEMBL12543http://en.wikipedia.org/wiki/ChEMBLhttps://www.ebi.ac.uk/chebi/searchId.do?chebiId=7307http://en.wikipedia.org/wiki/ChEBIhttp://www.kegg.jp/entry/C11118http://en.wikipedia.org/wiki/KEGGhttp://fdasis.nlm.nih.gov/srs/srsdirect.jsp?regno=JR9CE63FPMhttp://en.wikipedia.org/wiki/Unique_Ingredient_Identifierhttp://www.chemspider.com/12814http://en.wikipedia.org/wiki/ChemSpiderhttp://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=13387http://en.wikipedia.org/wiki/PubChemhttp://www.commonchemistry.org/ChemicalDetail.aspx?ref=872-50-4http://en.wikipedia.org/wiki/CAS_registry_numberhttp://en.wikipedia.org/wiki/File:N-Methylpyrrolidone_Structural_Formulae.png

7/29/2019 N-Methyl-2-Pyrrolidone - Wikipedia, The Free Encyclopedia

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Except where noted otherwise, data are given for

materials in their standard state (at 25 C, 100 kPa)

Infobox references

2-Pyrrolidone

1,3-Dimethyl-2-imidazolidinone (DMI)

References

1. ^ ab "Products: N-Methylpyrrolidone"

(http://www.basf.com/diols/bcdiolsnmp.html) .

BASF. http://www.basf.com/diols/bcdiolsnmp.html.Retrieved 2007-11-11.

2. ^ "Pharmasolve Drug Solubilizer" (http://online1.ispcorp.com/Brochures/Pharma/PharmaGuide.pdf) .

PharmaGuide (International Specialty Products, a division of Ashland Inc.): Page 9.

http://online1.ispcorp.com/Brochures/Pharma/PharmaGuide.pdf. Retrieved 2012-06-06.

3. ^ "List of Chemicals as Known to the State of California to Cause Cancer or Reproductive Toxicity"

(http://www.oehha.ca.gov/prop65/prop65_list/files/P65single091009.pdf) . California OEHHA.

http://www.oehha.ca.gov/prop65/prop65_list/files/P65single091009.pdf. Retrieved 4 December 2012.

4. ^ Reisch, Mark (July 21, 2008). "Solvent users look to replace NMP". Chemical & Engineering News: 32.

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Categories: Amide solvents Pyrrolidones Excipients

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