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Revision as of 15:19, 28 January 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: ChEMBL KEGG.← Previous edit		Latest revision as of 06:27, 19 October 2024 edit undoWikiCleanerBot (talk | contribs)Bots925,164 editsm v2.05b - Bot T20 CW#61 - Fix errors for CW project (Reference before punctuation)Tag: WPCleaner
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		⚫	{{DISPLAYTITLE:''N''-Methyl-2-pyrrolidone}}
	{{chembox		{{chembox
			| Verifiedfields = changed
⚫	| verifiedrevid = 402498108
			| Watchedfields = changed
	| Name = Methylpyrrolidone
		⚫	| verifiedrevid = 410572798
⚫	| ImageFile = N-Methylpyrrolidone Structural Formulae.png
		⚫	| Name = ''N''-Methyl-2-pyrrolidone
	| ImageSize = 110px
	| ImageName =		| ImageFile =
		⚫	| ImageFileL1 = N-Methylpyrrolidone Structural Formulae.png
⚫	| IUPACName = 1-Methyl-2-pyrrolidone
			| ImageSizeL1 = 120px
⚫	| OtherNames = N-Methyl-2-pyrrolidone
			| ImageNameL1 =
			| ImageFileR1 = N-Methylpyrrolidone molecule ball.png
			| ImageSizeR1 = 120px
			| ImageNameR1 =
			| PIN = 1-Methylpyrrolidin-2-one
			| SystematicName =
			| OtherNames = 1-Methyl-2-pyrrolidone<br />''N''-Methylpyrrolidone<br />''N''-Methylpyrrolidinone<br />Pharmasolve
			| IUPACName =
	| Section1 = {{Chembox Identifiers		| Section1 = {{Chembox Identifiers
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 12814		| ChemSpiderID = 12814
	| PubChem = 13387		| PubChem = 13387
	| UNII_Ref = {{fdacite|correct|FDA}}		| UNII_Ref = {{fdacite|correct|FDA}}
	| UNII = JR9CE63FPM		| UNII = JR9CE63FPM
			| KEGG_Ref = {{keggcite|correct|kegg}}
	| KEGG = C11118		| KEGG = C11118
	| InChI = 1/C5H9NO/c1-6-4-2-3-5(6)7/h2-4H2,1H3		| InChI = 1/C5H9NO/c1-6-4-2-3-5(6)7/h2-4H2,1H3
	| InChIKey = SECXISVLQFMRJM-UHFFFAOYAL		| InChIKey = SECXISVLQFMRJM-UHFFFAOYAL
			| ChEMBL_Ref = {{ebicite|correct|EBI}}
	| ChEMBL = 12543		| ChEMBL = 12543
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
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	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo = 872-50-4		| CASNo = 872-50-4
			| ChEBI_Ref = {{ebicite|correct|EBI}}
⚫	| SMILES = CN1CCCC1=O
			| ChEBI = 7307
		⚫	| SMILES = CN1CCCC1=O
	}}		}}
	| Section2 = {{Chembox Properties		| Section2 = {{Chembox Properties
			| C=5|H=9|N=1|O=1
	| Formula = C<sub>5</sub>H<sub>9</sub>NO
		⚫	| Density = 1.028{{nbsp}}g/cm<sup>3</sup>
	| MolarMass = 99.13 g/mol
			| MeltingPtC = -24
⚫	| Density = 1.028 g/cm<sup>3</sup>
			| BoilingPtC = 202 to 204
	| MeltingPt = &minus;24 °C
			<!--| Dielectric Constant = 32.2 (25 °C)-->
	| BoilingPt = 202-204°C
			| Solubility = Soluble<ref name="Sigma">{{Sigma-Aldrich|sial|id=328634|accessdate=22 March 2022|name=1-Methyl-2-pyrrolidinone}}</ref>
			| SolubleOther = Soluble<ref name="Sigma"/>
			| Solvent = ], ], ], ], ], ]
			| LogP = −0.40<ref name="chemsrc">{{Cite web|url=https://www.chemsrc.com/en/cas/872-50-4_820838.html|title=N-Methylpyrrolidone_msds}}</ref>
	}}		}}
			| Section3 =
			| Section4 =
			| Section5 =
			| Section6 =
	| Section7 = {{Chembox Hazards		| Section7 = {{Chembox Hazards
	| NFPA-H = 1		| NFPA-H = 2
	| NFPA-F = 2		| NFPA-F = 2
	| NFPA-R = 1		| NFPA-R = 1
	}}		}}
	}}		}}
	'''''N''-Methyl-2-pyrrolidone''' (NMP) is a ] with 5-membered ] structure. It is a clear to slightly yellow liquid miscible with ] and solvents like ], ], ] and lower ]s or ]s. It also belongs to the class of dipolar ] solvents which includes also ], ] and ]. Other names for this compound are: 1-methyl-2-pyrrolidone, ''N''-methyl-2-pyrrolidinone, and m-pyrrole, and pharmasolve.		'''''N''-Methyl-2-pyrrolidone''' ('''NMP''') is an ] consisting of a 5-membered ]. 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 ] solvents such as ] and ]. It is used in the petrochemical, polymer and battery industries as a solvent, exploiting its nonvolatility and ability to dissolve diverse materials (including ], PVDF).<ref name=Ull>{{Ullmann|first1=Albrecht Ludwig|last1=Harreus|first2=R.|last2=Backes|first3=J.-O.|last3=Eichler|first4=R.|last4=Feuerhake|first5=C. |last5=Jäkel|first6=U.|last6=Mahn|first7=R.|last7=Pinkos|first8=R.|last8=Vogelsang"2-Pyrrolidone|year=2011|doi=10.1002/14356007.a22_457.pub2}}</ref>
			The low toxicity is also a reason to use this solvent.
			==Preparation==
	N-Methylpyrrolidone is used to recover pure ] while processing petrochemicals (such as the recovery of ] using NMP as an ] solvent) and in the ] of gases. Due to its good solvency properties ''N''-methyl-2-pyrrolidone is used to dissolve a wide range of chemicals, especially in the ]s field. It also used as a solvent for surface treatment of ]s, resins and metal coated plastics or as a ].<ref name = BASF>{{cite web | publisher = ] | title = Products: N-Methylpyrrolidone | url = http://www.basf.com/diols/bcdiolsnmp.html | accessdate = 2007-11-11}}</ref> In the pharmaceutical industry, ''N''-methyl-2-pyrrolidone is used in the formulation for drugs by both oral and transdermal delivery routes.<ref name = ISP>{{cite web | publisher = ] | title = "Pharmasolve" | url = http://www.ispcorp.com/products/pharma/content/brochure/pharmasolve/Pharmasolve%20ver98.pdf | accessdate = 2008-04-15}} {{Dead link|date=October 2010|bot=H3llBot}}</ref>
			NMP is produced industrially by a typical ester-to-amide conversion, by treating ] with ]. Alternative routes include the partial ] of ] and the reaction of ] with methylamine followed by ]. About 200,000 to 250,000 tons are produced annually.<ref name=Ull/>
			==Applications==
	''N''-Methyl-2-pyrrolidone and its derivatives are used as intermediates for the synthesis of ]s, pharmaceuticals, textile auxiliaries, plasticizers, stabilizers and specialty inks. It is also employed as a ] precursor. The rubber industry uses it for SBR latex production and the electronics industry for printed circuit board manufacturing.<ref name = BASF/>
			NMP is used to recover certain ] generated in the processing of ]s, such as the recovery of ] and ]. It is used to absorb ] from ] and hydrodesulfurization facilities. Its good solvency properties have led to NMP's use to dissolve a wide range of ]s. Specifically, it is used as a solvent for surface treatment of ]s, resins, and metal coated plastics or as a ]. It is also used as a solvent in the commercial preparation of ].
	World production capacity for NMP was 226 million lb in 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 and then by the European Commission in 2003. 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.<ref>{{cite journal |author=Reisch, Mark |journal=Chemical & Engineering News |date=July 21, 2008 |pages=32 |title=Solvent users look to replace NMP}}</ref>
			NMP is used in the production of ] fibers ] and ]. In the pharmaceutical industry, ''N''-methyl-2-pyrrolidone is used in the formulation for drugs by both oral and transdermal delivery routes.<ref name = ISP>{{cite journal | publisher = ] | journal = PharmaGuide | title = Pharmasolve® Drug Solubilizer | page = Page 9 | url = http://online1.ispcorp.com/Brochures/Pharma/PharmaGuide.pdf | accessdate = 2012-06-06}}</ref> It is also used heavily in ] fabrication, as a solvent for electrode preparation, because NMP has a unique ability to dissolve ] binder.
			==Safety==
			N-Methyl-2-pyrrolidone (NMP) is classified as a reproductive toxicant (H360D: May damage the unborn child) and can cause skin and eye irritation and respiratory irritation (H315, H319, H335).<ref>{{cite web|url=https://www.sigmaaldrich.com/GB/en/sds/sial/328634 |title=Sigma-Aldrich NMP Safety Data Sheet |publisher=Sigma-Aldrich |access-date=October 15, 2024}}</ref> Studies show NMP exposure can increase the risk of developmental toxicity, including miscarriage and fetal death.<ref>{{cite web|url=https://www.regulations.gov/document/EPA-HQ-OPPT-2016-0231-0001 |title=Regulation of Certain Uses under Toxic Substances Control Act: Methylene Chloride and N-Methylpyrrolidone |publisher=Environmental Protection Agency |access-date=October 15, 2024}}</ref> Good ventilation and PPE are recommended for safe handling.<ref>{{cite web|url=https://www.jmnspecialties.com/downloads/sds/2839-nmp-sds/file |title=JMNSpecialties NMP Safety Data Sheet |publisher=JMNSpecialties |access-date=October 15, 2024}}</ref>
	==See also==		==See also==
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	{{reflist}}		{{reflist}}
			{{DEFAULTSORT:Methyl-2-pyrrolidone, N-}}
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