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1-Methyl-2-pyrrolidinone (NMP) is a colorless to yellowish transparent liquid with a slight smell of ammonia. It is easily soluble in water, ethanol, ether, acetone, ethyl acetate, chloroform and benzene. It can be dissolved in most organic and inorganic compounds, polar gases, natural and synthetic polymer compounds. Water is miscible in any proportion, and is soluble in various organic solvents such as ether, acetone and esters, halogenated hydrocarbons and aromatic hydrocarbons, Almost completely mixed with all solvents. This product is an excellent high-grade solvent, a polar solvent with strong selectivity and stability, and an excellent cleaning agent for high-precision electronics, circuit boards and lithium batteries.
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Chemical Formula |
C5H9NO |
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Exact Mass |
99.07 |
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Molecular Weight |
99.13 |
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m/z |
99.07 (100.0%), 100.07 (5.4%) |
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Elemental Analysis |
C, 60.58; H, 9.15; N, 14.13; O, 16.14 |
1-Methyl-2-pyrrolidinone (NMP) is a polar aprotic solvent. It has low toxicity, high boiling point, and outstanding solubility. It has the advantages of strong selectivity and good stability. It is widely used in aromatic extraction, purification of acetylene, olefins, and dienes, solvents for polyvinylidene fluoride, electrode auxiliary materials for lithium-ion batteries, synthesis gas desulfurization, lubricant refining, lubricant antifreeze, olefin extractant, solvent for polymerization of insoluble engineering plastics, agricultural herbicides, insulating materials, integrated circuit production, semiconductor industry precision instruments, circuit board cleaning, PVC tail gas recovery, cleaning agent, dye additive, dispersant, etc. It is also used as a solvent for polymers and a medium for polymerization reactions, such as engineering plastics and aramid fibers. It can also be used in pesticides, medicines, and detergents.
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Lithium Battery Manufacturing: NMP serves as a key solvent in the production of lithium-ion batteries, particularly in the preparation of electrode slurries.
Semiconductor Processing: It is used in the cleaning and etching processes of semiconductor wafers, ensuring high purity and performance.
Circuit Board Coating: NMP aids in the uniform coating of circuit boards, enhancing their electrical conductivity and durability.
Polymer Solutions: As an effective solvent, NMP is used in the preparation of polymer solutions for various applications.
Resin Production: It facilitates the production of resins by dissolving and mixing resin components uniformly.
Paint Formulations: NMP helps in formulating paints with desired viscosity and flow properties.
Drug Synthesis: NMP is employed in the synthesis of certain pharmaceutical compounds, enabling the formation of specific chemical bonds.
Drug Delivery Systems: It is used in the formulation of drug delivery systems, such as transdermal patches and implants, to control the release of active ingredients.
Dye and Textile Auxiliaries: NMP acts as a solvent for dyes and textile auxiliaries, ensuring uniform dyeing and finishing of textiles.
Pesticide Formulations: It is used in the formulation of pesticides, enhancing their solubility and effectiveness.
Synthesis Method
Gamma-Butyrolactone (GBL) Method
This is a commonly used method where gamma-butyrolactone (GBL) reacts with dimethylamine in the presence of a catalyst such as hydrogen chloride or sulfuric acid. The reaction typically proceeds at elevated temperatures and pressures, yielding NMP and water as products. The water is then removed by distillation, leaving pure NMP.
Raw Materials
The primary raw materials for this synthesis are γ-butyrolactone (GBL) and methylamine. The purity and ratio of these raw materials directly affect the reaction efficiency and product purity.
Reaction Mechanism
In this reaction, methylamine undergoes an aminolysis reaction with γ-butyrolactone. The key step involves the interaction between the molecular structures of methylamine and γ-butyrolactone. Specifically, the nitrogen atom in methylamine reacts with the carbon atom in γ-butyrolactone, leading to the oxidation of the carbonyl group in the γ-butyrolactone molecule and the formation of an intermediate compound. This intermediate then undergoes further reaction and reorganization to ultimately produce.
The first step of the reaction is that γ-butyrolactone and methylamine generate 4-hydroxy-N-methylbutyramide, and the second step is to further dehydrate to generate N-methylpyrrolidone. The two-step reaction can be arranged in a tubular reactor for continuous operation. The molar ratio of γ-butyrolactone to methylamine is 1:1.15, the pressure is about 6MPa, and the temperature is 250℃. After the reaction is completed, the finished product is obtained by concentration and vacuum distillation. The yield is 90%. If a kettle reactor is used for production, the amount of methylamine is 1.5-2.5 times the theoretical amount. Take laboratory preparation as an example. In a 500ml autoclave, add 2mol of γ-butyrolactone and 4mol of liquid methylamine, heat in a closed manner, and keep warm at 280℃ for 4h. After cooling, release the excess methylamine, distill, collect the 201-202℃ fraction, and obtain about 180g of product with a yield of about 90%.
Catalytic Synthesis from Succinic Acid and Methylamine
Conditions
This method involves reacting succinic acid with methylamine in an inert solvent, catalyzed by Raney nickel, at temperatures ranging from 200 to 300°C and pressures of 5 to 20 MPa.
Process
Under these conditions, the reaction proceeds to form the product. However, detailed reaction steps and mechanisms for this specific catalytic synthesis may vary and are often proprietary to specific manufacturing processes.
Other Description
1-Methyl-2-pyrrolidinone (NMP) is a versatile and highly effective organic solvent with a wide range of applications across various industries. Chemically, it is an amide derived from gamma-butyrolactone and methylamine, characterized by its colorless, odorless (or slightly ammonia-like), and hygroscopic properties. Its chemical formula is C5H9NO, and it boasts a high boiling point, making it stable under high temperatures, which enhances its suitability for numerous industrial processes.
One of the primary uses of NMP lies in the production of lithium-ion batteries, where it serves as a key component in the manufacture of electrode coatings and separators, facilitating the uniform distribution of active materials and enhancing battery performance. Additionally, it finds application in the pharmaceutical industry, acting as a solvent in the synthesis and purification of active pharmaceutical ingredients due to its ability to dissolve a broad spectrum of polar and non-polar compounds.
In the electronics sector, NMP is employed in the production of semiconductors and liquid crystal displays (LCDs), aiding in the cleaning and etching processes required for the precise manufacturing of these devices. Its use in paints and coatings ensures the formation of smooth, defect-free films, enhancing the durability and aesthetic appeal of coated surfaces.
Moreover, NMP exhibits good biocompatibility and low toxicity, making it a preferred choice for various medical applications, such as in the formulation of transdermal patches and as a carrier for drug delivery systems. Despite its benefits, the handling of NMP requires caution due to its potential for skin and eye irritation, necessitating appropriate personal protective equipment and good industrial hygiene practices.
In conclusion, 1-Methyl-2-pyrrolidinone (NMP) stands as a multifaceted solvent, underpinning advancements in energy storage, healthcare, electronics, and more, through its unique solvency properties and stability.
The analytical methods for 1-methyl-2-pyrrolidinone (NMP) mainly include gas chromatography (GC), gas chromatography-mass spectrometry (GC-MS), high performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS), potentiometric titration, and other physical property measurement methods. The detailed introduction is as follows:
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Gas Chromatography (GC)
Principle: The components in the sample are separated by the chromatographic column, and detected using the Hydrogen Flame Ionization Detector (FID). The NMP content is quantitatively analyzed using the corrected area normalization method.
Instrument and conditions: Use high-sensitivity and stable gas chromatographs such as AGILENT 7820A. Under specific chromatographic operation conditions (such as chromatographic column type, temperature program, injection port temperature, etc.), the sample is vaporized and separated by the chromatographic column, and the peak areas of each component are detected and the content is calculated.
Application: Suitable for preparing standard solutions with similar impurity content to the test sample and for quantitative analysis of NMP. The absolute difference between two parallel determinations usually should not exceed 0.03%.
Gas Chromatography-Mass Spectrometry (GC-MS)
Principle: Combine the separation ability of gas chromatography with the qualitative ability of mass spectrometry to achieve high-precision qualitative and quantitative analysis of NMP.
Instrument and conditions: Use high-end configurations such as Agilent 7890B-5977B, equipped with an automatic injector. Analyze under specific chromatographic columns and temperature programs to ensure that NMP peaks are detected within a reasonable time and obtain good peak shapes.
Application: Suitable for occasions with higher requirements for analysis accuracy, such as in the lithium battery industry for precise determination of NMP.
High-Performance Liquid Chromatography-Tandem Mass Spectrometry (HPLC-MS/MS)
Principle: Utilize the separation ability of liquid chromatography and the high-sensitivity detection ability of tandem mass spectrometry to achieve quantitative analysis of NMP.
Instrument and conditions: Use specific chromatographic columns (such as InnovationTM C18) for separation, scan in positive ion mode using an electrospray ionization (ESI) source, and detect in multiple reaction monitoring mode.
Application: Suitable for the determination of NMP in complex matrices such as plastics, with advantages of simple sample processing, rapidity, and high sensitivity.
Potentiometric Titration
Principle: Determine the titration endpoint by measuring the change in potential, thereby calculating the content of free amine in NMP.
Instrument and conditions: Use precise instruments such as METTLER G10S potentiometric titrator, following specific standards (such as GB/T 9725) for determination.
Application: Suitable for the determination of the content of free amine in NMP, obtaining results by one-click titration after inputting the formula.
Other analytical methods
Physical property determination: including refractive index, density, colorimeter, pH value, etc. These determination methods are relatively simple and the recommended models are listed in the instrument's appendix.
Water content determination: for the determination of water content in NMP, methods such as Karl Fischer titration can be used. For the determination of water content in solid samples (such as positive electrode materials, negative electrode materials) and liquid samples (such as electrolyte, NMP solvent), different pretreatment methods need to be adopted.
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