Misplaced Pages

N-Methyl-2-pyrrolidone: Difference between revisions

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Browse history interactively← Previous editContent deleted Content addedVisualWikitext
Revision as of 11:16, 15 December 2010 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:WikiProject_Ch← Previous edit Latest revision as of 07:34, 11 January 2025 edit undoPreimage (talk | contribs)Extended confirmed users1,356 edits →Chembox: Update solubility + add flash point, autoignition point 
(129 intermediate revisions by 82 users not shown)
Line 1: Line 1:
⚫ {{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
| 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
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C5H9NO/c1-6-4-2-3-5(6)7/h2-4H2,1H3 | StdInChI = 1S/C5H9NO/c1-6-4-2-3-5(6)7/h2-4H2,1H3
Line 21: Line 34:
| 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 = ]<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 | FlashPtC = 91
| FlashPt_ref = <ref name="Sigma"/>
⚫ | NFPA-F = 2
| NFPA-R = 1 | AutoignitionPtC = 245
| AutoignitionPt_ref = <ref name="Sigma"/>
| NFPA-H = 2
⚫ | NFPA-F = 2
| NFPA-R = 1
}} }}
}} }}


'''''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> It has a strong dipole moment and hydrogen bonding due to its cis-amide conformation.<ref>{{Citation |last=Chenault |first=H. Keith |title=Introduction to Pyrrolidone and Caprolactam Chemistry |date=2021 |work=Handbook of Pyrrolidone and Caprolactam Based Materials |pages=1–69 |url=https://onlinelibrary.wiley.com/doi/10.1002/9781119468769.hpcbm001 |access-date=2025-01-08 |publisher=John Wiley & Sons, Ltd |language=en |doi=10.1002/9781119468769.hpcbm001 |isbn=978-1-119-46876-9}}</ref>{{rp|at=Fig. 5(b)}}
'''''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.


==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> Furthermore, small amounts of ''N''-Methyl-2-pyrrolidone are contained in various medical devices like self-hardening ], ] and subcutaneous drug delivery devices.<br />
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/>
<ref name = OJSC Novocherkassk Plant Of Synthetic Products>{{cite web | publisher = ] | title = Products: N-Methylpyrrolidone | url = http://www.nzsp.ru | accessdate = 2010-09-09}}</ref>


==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 also used in ] creation.


NMP is used to recover certain ] generated in the processing of ]s, such as the recovery of ] and ]. Its good solvency properties have also 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.

===Purisol process===
In the '''Purisol process''', developed by ] in the 1960s, a cold (ca. -15 °C) aqueous solution of NMP is used to remove ] from ] and from ] facilities.<ref>{{Cite book |last=Kohl |first=Arthur L. |url=https://books.google.com/books?id=rpzrIZW-OcEC&pg=PA1210 |title=Gas Purification |last2=Nielsen |first2=Richard |date=1997-08-28 |publisher=Elsevier |isbn=978-0-08-050720-0 |pages=1210-1211 |language=en}}</ref> It offers some advantages over the ] process in that it is more selective for hydrogen sulfide. Furthermore, it promotes the hydrolysis of some ], a common component of sour gas:
:{{chem2|COS + H2O -> CO2 + H2S}}
This hydrolysis step further enriches the hydrogen sulfide content of the off-gas when the NMP is stripped. The sulfur-rich gas is well suited for a ], which affords solid ].<ref>{{cite book |doi=10.1002/14356007.o12_o02 |chapter=Gas Production, 3. Gas Treating |title=Ullmann's Encyclopedia of Industrial Chemistry |date=2011 |last1=Boll |first1=Walter |last2=Hochgesand |first2=Gerhard |last3=Higman |first3=Christopher |last4=Supp |first4=Emil |last5=Kalteier |first5=Peter |last6=Müller |first6=Wolf-Dieter |last7=Kriebel |first7=Manfred |last8=Schlichting |first8=Holger |last9=Tanz |first9=Heiner |isbn=978-3-527-30385-4 }}</ref>

==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=] |date=January 19, 2017 |access-date=October 15, 2024 |id=EPA-HQ-OPPT-2016-0231-0001}}</ref><ref name=EPA2020>{{cite web |title=Risk Evaluation for n-Methylpyrrolidone (2-Pyrrolidinone, 1-Methyl-) (NMP) |url=https://www.epa.gov/sites/default/files/2020-12/documents/1_risk_evaluation_for_n-methylpyrrolidone_nmp_casrn_872-50-4.pdf |date=December 22, 2020 |access-date=January 11, 2025 |work=] |archive-url=http://web.archive.org/web/20241002042225/https://www.epa.gov/sites/default/files/2020-12/documents/1_risk_evaluation_for_n-methylpyrrolidone_nmp_casrn_872-50-4.pdf |archive-date=October 2, 2024}}</ref>{{rp|page=24}} 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==
Line 53: Line 89:
{{reflist}} {{reflist}}


{{DEFAULTSORT:Methyl-2-pyrrolidone, N-}}
] ]
] ]
] ]
]

]
]
]
]
]
]
]
]
]
]

Latest revision as of 07:34, 11 January 2025

N-Methyl-2-pyrrolidone
Names
Preferred IUPAC name 1-Methylpyrrolidin-2-one
Other names 1-Methyl-2-pyrrolidone
N-Methylpyrrolidone
N-Methylpyrrolidinone
Pharmasolve
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.011.662 Edit this at Wikidata
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C5H9NO/c1-6-4-2-3-5(6)7/h2-4H2,1H3Key: SECXISVLQFMRJM-UHFFFAOYSA-N
  • InChI=1/C5H9NO/c1-6-4-2-3-5(6)7/h2-4H2,1H3Key: SECXISVLQFMRJM-UHFFFAOYAL
SMILES
  • CN1CCCC1=O
Properties
Chemical formula C5H9NO
Molar mass 99.133 g·mol
Density 1.028 g/cm
Melting point −24 °C (−11 °F; 249 K)
Boiling point 202 to 204 °C (396 to 399 °F; 475 to 477 K)
Solubility in water Miscible
Solubility in Ethanol, acetone, diethylether, ethyl acetate, chloroform, benzene Soluble
log P −0.40
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
2 2 1
Flash point 91 °C (196 °F; 364 K)
Autoignition
temperature 		245 °C (473 °F; 518 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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, polymer and battery industries as a solvent, exploiting its nonvolatility and ability to dissolve diverse materials (including polyvinylidene difluoride, PVDF). It has a strong dipole moment and hydrogen bonding due to its cis-amide conformation.

Preparation

NMP is produced industrially by a typical ester-to-amide conversion, by treating gamma-butyrolactone with methylamine. Alternative routes include the partial hydrogenation of N-methylsuccinimide and the reaction of acrylonitrile with methylamine followed by hydrolysis. About 200,000 to 250,000 tons are produced annually.

Applications

NMP is used to recover certain hydrocarbons generated in the processing of petrochemicals, such as the recovery of 1,3-butadiene and acetylene. Its good solvency properties have also led to NMP's use to dissolve a wide range of polymers. Specifically, it is used as a solvent for surface treatment of textiles, resins, and metal coated plastics or as a paint stripper. It is also used as a solvent in the commercial preparation of polyphenylene sulfide. NMP is used in the production of aramid fibers Twaron and Kevlar. In the pharmaceutical industry, N-methyl-2-pyrrolidone is used in the formulation for drugs by both oral and transdermal delivery routes. It is also used heavily in lithium ion battery fabrication, as a solvent for electrode preparation, because NMP has a unique ability to dissolve polyvinylidene fluoride binder.

Purisol process

In the Purisol process, developed by Lurgi AG in the 1960s, a cold (ca. -15 °C) aqueous solution of NMP is used to remove hydrogen sulfide from sour gas and from hydrodesulfurization facilities. It offers some advantages over the Selexol process in that it is more selective for hydrogen sulfide. Furthermore, it promotes the hydrolysis of some carbonyl sulfide, a common component of sour gas:

COS + H2O → CO2 + H2S

This hydrolysis step further enriches the hydrogen sulfide content of the off-gas when the NMP is stripped. The sulfur-rich gas is well suited for a Claus unit, which affords solid elemental sulfur.

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). Studies show NMP exposure can increase the risk of developmental toxicity, including miscarriage and fetal death. Good ventilation and PPE are recommended for safe handling.

See also

References

  1. ^ Sigma-Aldrich Co., 1-Methyl-2-pyrrolidinone. Retrieved on 22 March 2022.
  2. "N-Methylpyrrolidone_msds".
  3. ^ Harreus, Albrecht Ludwig; Backes, R.; Eichler, J.-O.; Feuerhake, R.; Jäkel, C.; Mahn, U.; Pinkos, R.; Vogelsang"2-Pyrrolidone, R. (2011). Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_457.pub2. ISBN 978-3527306732.{{cite encyclopedia}}: CS1 maint: numeric names: authors list (link)
  4. Chenault, H. Keith (2021), "Introduction to Pyrrolidone and Caprolactam Chemistry", Handbook of Pyrrolidone and Caprolactam Based Materials, John Wiley & Sons, Ltd, pp. 1–69, doi:10.1002/9781119468769.hpcbm001, ISBN 978-1-119-46876-9, retrieved 2025-01-08
  5. "Pharmasolve® Drug Solubilizer" (PDF). PharmaGuide. International Specialty Products, a division of Ashland Inc.: Page 9. Retrieved 2012-06-06.
  6. Kohl, Arthur L.; Nielsen, Richard (1997-08-28). Gas Purification. Elsevier. pp. 1210–1211. ISBN 978-0-08-050720-0.
  7. Boll, Walter; Hochgesand, Gerhard; Higman, Christopher; Supp, Emil; Kalteier, Peter; Müller, Wolf-Dieter; Kriebel, Manfred; Schlichting, Holger; Tanz, Heiner (2011). "Gas Production, 3. Gas Treating". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.o12_o02. ISBN 978-3-527-30385-4.
  8. "Sigma-Aldrich NMP Safety Data Sheet". Sigma-Aldrich. Retrieved October 15, 2024.
  9. "Regulation of Certain Uses under Toxic Substances Control Act: Methylene Chloride and N-Methylpyrrolidone". Environmental Protection Agency. January 19, 2017. EPA-HQ-OPPT-2016-0231-0001. Retrieved October 15, 2024.
  10. "Risk Evaluation for n-Methylpyrrolidone (2-Pyrrolidinone, 1-Methyl-) (NMP)" (PDF). Environmental Protection Agency. December 22, 2020. Archived from the original (PDF) on October 2, 2024. Retrieved January 11, 2025.
  11. "JMNSpecialties NMP Safety Data Sheet". JMNSpecialties. Retrieved October 15, 2024.
Categories:
N-Methyl-2-pyrrolidone: Difference between revisions Add topic