5-Methyl-2-pyrrolidones

Levulinic acid Glucose, fructose, xylose 1,4-Pentanediol, 5-methyl-2-pyrrolidone, acrylic acid, diphenolic acid, methyl tetrahydofuran (MTHF), levulinate ester, succinic acid, jS-acetyl-acrylic acid, y-valero-lactone Bozell etal., 2000 Keenan etal., 2004 Werpy and Petersen, 2004 Chang etal., 2007... 

Dimethyl-2-pyrrolidone has been prepared by the reaction of 5-methyl-2-pyrrolidone with excess methyl iodide4 and by the catalytic hydrogenation of a mixture of levulinic acid and methylamine.6... 

Various 3,3-dialkyl-5-methyl-2-pyrrolidones have been prepared in this way. 

It has been demonstrated that a solvent-extraction procedure with N-methyl pyrrolidone is capable of producing coal-derived extract pitches with low-ash contents. Moreover, the properties of the pitches can be varied by partial hydrogenation of the coal prior to extraction. The yield of the pitches along with the physical and chemical properties of the cokes and graphites vai in an understandable fashion. 

Chemical Designations - Synonyms l-Methyl-2-pyrrolidinone N-Methylpyrrolidinone -Methyl-pyrrolidone -Methyl-alpha-pyrrolidone Chemioal Formula CjH,NO. 

N-Methyl pyrrolidone, dibasic ethers, and organic esters, substituting for more hazardous paint removers (Paint Removers, 1991 Davis et al., 1994)... 

Alcoholic potassium hydroxide or sodium hydroxide are normally used to convert the halohydrins to oxiranes. Other bases have also been employed to effect ring closure in the presence of labile functional groups such as a-ketols, e.g., potassium acetate in ethanol, potassium acetate in acetone or potassium carbonate in methanol.However, weaker bases can lead to solvolytic side reactions. Ring closure under neutral conditions employing potassiunT fluoride in dimethyl sulfoxide, dimethylformamide or A-methyl-pyrrolidone has been reported in the patent literature. 

Aprotic polar solvents have to be used for several reasons. They are often good solvents for both monomers (including phenolates) and amorphous polymers. In addition, they can also stabilize the Meisenheimer intermediates. Common aprotic polar solvents, such as DMSO, /V,/V-dimcthyl acetamide (DMAc), DMF, N-methyl pyrrolidone (NMP), and cyclohexylpyrrolidone (CHP) can be used. Under some circumstances, very high reaction temperature and boiling point solvents such as sulfolane and diphenyl sulfone (DPS) have to be used due to the poor reactivity of the monomers or poor solubility of the resulting, possibly semicrystalline polymers, as in the PEEK systems. 

Die Reduktion von 9-Brom-ll/3-hydroxy-steroiden mit Chrom(II)-Salzen, insbeson-dere mit Chrom(II)-acetat fiihrt zu 11/3-Hydroxy-steroiden (s. S.515), A9 (11)-Ste-roiden (s. S.518) und 5,9-Cyclo-steroiden. Die Cyclopropan-Bildung wird durch Chrom(II)-acetat in Dimethylsulfoxid bzw. Dimethylformamid begiinstigt. So laufen beim 9a-Brom-l l/3-hydroxy-3-oxo-l 7/ -acetyl-ostren-(510) in waBr. Aceton, THF, 1,4-Di-oxan oder N-Methyl-pyrrolidon Substitution, Eliminierung und Cyclisierung nebeneinan-der ab, in Dimethylsulfoxid oder Dimethylformamid erhalt man fast ausschlieBlich ///3-Hydroxy-3-oxo-17 3-acetyl-5,9-cyclo-dstran5 ... 

Cyanations of quinoline 877 and isoquinoline N-oxide 879 in DMF or N-methyl-pyrrolidone provides the cyano compounds 878 and 880 in 90 and 79% yield, respectively (Scheme 7.4) it was expected, e.g., that pyrimidine N-oxides would react analogously [6]. 

The electrode active masses were prepared by mixing the active material with 10 wt.% of polyvynilidene fluoride slurred in 1-methyl-pyrrolidone solvent. The actual mass was then pasted onto one side of precleaned Co foil, dried for 4 h at 100°C, pressed and the disks of 15,6 mm diameter were cut and placed into the cell s coins. Large excess of Li metal (foil) was used as a counter electrode. 1M LiPF6 solution in mixture of ethylene carbonate (50 vol.%) and methyl carbonate was used as an electrolyte (Merck product LP30). 

In recent years researchers at West Virginia University have developed coal-derived pitches on a laboratory scale in quantities sufficient to make 1 kg samples of calcined coke for fashioning graphite test specimens. The pitches were derived by utilizing solvent extraction with N-methyl pyrrolidone (NMP). This solvent is able to isolate coal-based pitches m high yield and with low mineral matter content [13]. It is this work that will form the basis of the discussion for the later part of this chapter. 

DISTAPEX A process for removing aromatic hydrocarbons from pyrolysis gasoline or coke-oven benzole by extractive distillation with added N-methyl pyrrolidone. The operating temperature is at least 170°C. Developed by Lurgi. First announced in 1961 by 1993, 22 plants had been built. 

EXOL N Also called EXOL N Extraction. A solvent extraction process for purifying feedstocks for making lubricating oil. The solvent is N-methyl pyrrolidone. Developed and licensed by Exxon Research Engineering Compary. Seventeen units had been installed by 1994. 

Sachsse Also called the Flame cracking process, and the Sachsse-Bartholome process. A process for making acetylene by the partial combustion of methane. The product gases are quenched rapidly and the acetylene is extracted with methyl pyrrolidone. First operated by IG Farbenindustrie at Oppau, Germany, in 1942. Worldwide, 13 plants used the process, of which 7 were still in operation in 1991. 

When dopa was oxidized using the PIPo-Cu catalyst, the distinguished acceleration was observed as compared with the PVIm-Cu or imidazole-Cu catalysts (Fig. 6). An increase in content of the N-vinylpyrrolidone residue in the PIPo copolymer caused higher activity of the Cu complex for the dopa oxidation. The similar acceleration was also produced when N-methyl-pyrrolidone was added to the system of PVIm-Cu. However, nearly 103 fold concentration of the pyrrolidone residue was necessary as compared with the PIPo copolymer. Addition of homopolymer of N-vinyl-pyrrolidone to PVIm-Cu caused no acceleration. 

Solvent extraction of benzene works the same way. But instead of water, the various solvents used are sulfolane, liquid SO2, diethylene-glycol, and NMP (N-methyl pyrrolidone). The paint thinner/salt/water process described above might be called a batch solvent process, since it consists of sequential steps that can be repeated, batch after batch. Some low-volume commercial processes still operate that way. 

Like the solvent extraction process, extractive distillation relies on the intimate contact of the liquid solvent and the aromatics concentrate vapors to allow the aromatics to be preferentially dissolved in the solvent. The usual list of solvents includes DEG (Diethylene glycol), TEG (Triethylene glycol), NMP (N-methyl pyrrolidone), or methyl formamide. 

Arosolvan A solvent extrachon process for removing aromatic hydrocarbons from petroleum mixtures, using N-methyl pyrrolidone (NMP) containing 12 to 14 percent water at 20 to 40°C. Developed by Luigi, and first used commercially in Japan in 1961. 

Typically, this rearrangement process is catalyzed by an inorganic Lewis acid and inorganic or quaternary onium iodide in a polar, aprotic solvent (e.g., ZnR, KI, N-methyl pyrrolidone) (8,9). For years, however, commercial processes utilizing this chemistry were unattractive due to the high cost of 1 and poor reaction selectivity. 

A reactor was charged with ZV-methyl pyrrolidone, 2-hydroxyethyl methacrylate (0.78 g), and the step 2 product (1.50 g) and then stirred overnight at ambient temperature. The mixture was precipitated by pouring into 0.1 M hydrochloric acid and the solid isolated. The precipitate was washed with deionized water, dried in a vacuum oven at ambient temperature overnight 1 mmHg, and 1.53 g of product isolated. 

METHYL- PYRROLIDONE 1-Methyl-2-pyrrolidone, N-Methyl-pyrroUdone NL 2 1 0... 

Abbreviations. IV, intravascular IM, intramuscular SC, subcutaneous NMP, JV-methyl pyrrolidone PEG, polyethylene glycol. 

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