Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1994-08-08
1995-12-26
Springer, David B.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
548554, C07D20108, C07D207267
Patent
active
054789508
DESCRIPTION:
BRIEF SUMMARY
FIELD OF THE INVENTION
The application relates to a process for producing pyrrolidone and N-alkyl pyrrolidones from saturated or unsaturated 1,4-dicarboxylic acids and their anhydrides; hydrogen; and a primary amine or ammonia.
BACKGROUND
N-alkyl pyrrolidones, particularly N-methylpyrrolidone, are technically very important solvents in industrial petrochemistry and are also used as starting substances for various syntheses.
N-methylpyrrolidone is generally produced industrially using the Reppe process (Chem. Ing. Technik (22) 17, 1950, pp. 361 ff.), in which monomethylamine and gamma-butyrolactone are maintained with a suitable diluent for a certain period of time at temperatures exceeding 250.degree. C. and reacted with each other via a dehydrating catalyst. Due to the freely occurring dimerization of N-methylpyrrolidone as a result of the reaction, the yield is only 85-90%, however.
In U.S. Pat. No. 4,885,371, a process for producing N-methylpyrrolidone is described in which monomethylamine and gamma-butyrolactone are reacted with each other via a borohydride catalyst.
A number of other publications (JP 01-190667, JP 01-186864, JP 01-186863) also describe the synthesis of N-alkyl pyrrolidones, starting from gamma-butyrolactone, with primary, secondary, or tertiary amines. The mean reaction time is 3 h at 250.degree. C.
According to the Soviet application no. 1558903, N-methylpyrrolidone is produced by reaction of gammabutyrolactone and an excess of monomethylamine at 250.degree. C. via a Y zeolite as a catalyst. According to K. Hatada et al. (Bull. Chem. Soc. Japan .50(10), 1977, pp. 2517-2521), a copper-exchanged Y zeolite is used as a catalyst for the same reaction.
In the process of JP 49-020585, N-methylpyrrolidone is obtained by reaction of monomethylamine, diluted with a large amount of water, and gamma-butyrolactone at 250.degree. C. and 2 hours reaction time.
The process of JP 51-042107 uses gammabutyrolactone, methylamine, and water in the ratio of 1:1.4:4 to produce N-methylpyrrolidone as the end product at a temperature of 250.degree. C. and a pressure of 45-50 kg/cm.sup.2. The excess water serves as a carrier for the reuse of unreacted methylamine.
In accordance with JP 49-000259, N-methylpyrrolidone is obtained by heating a mixture of gamma-butyrolactone, alkylamine, and hydrogen for 3 hours at 270.degree. C. A mixture of copper and a metallic oxide (Cu Plus SiO.sub.2, Al.sub.2 O.sub.3, SiO.sub.2 -Al.sub.2 O.sub.3, TiO.sub.2, ZrO.sub.2, or Cr.sub.2 O.sub.3) is used as a catalyst. The reaction takes place in the gaseous phase, and the yield is only about 60%.
According to JP 47-021420, N-methylpyrrolidone is obtained with a yield of 99% when monomethylamine and gamma-butyrolactone are allowed to react with each other in the aqueous phase for a sufficient length of time.
JP 49-020582 describes a process in which monomethylamine is first allowed to react with gammabutyrolactone, followed by a cyclization, such as via an aluminum oxide catalyst.
Finally, DE 2200600 describes a process for producing N-methylpyrrolidone from maleic anhydride, hydrogen, and an amine compound, in which a palladium-carbon catalyst is used. A yield of only at most 78.4% is obtained at a reaction temperature of 275.degree. C. and a pressure of 119 arm. The reaction occurs in an excess of water.
Furthermore, very long reaction times are prescribed and the reaction occurs under very high pressure, so that expensive process-related measures are needed.
All the aforementioned processes have the disadvantage either that the yield is low or that the product is unsatisfactorily impure and must undergo expensive purification following the process. In a manner similar to that described in DE-A 2200600, processes are also disclosed in U.S. Pat. No. 3,109,005, U.S. Pat. No. 3,448,118, and U.S. Pat. No. 3,198,808 in which pyrrolidone or pyrrolidones are produced using a so-called one-vessel process. These processes have the disadvantages previously mentioned. However, the synthesis usually starts from gamma-butyrolactone, whic
REFERENCES:
patent: 2267757 (1941-12-01), Schuster et al.
patent: 3109005 (1963-10-01), Lidov
patent: 3115500 (1963-12-01), Dunlop et al.
patent: 3136780 (1964-06-01), Kolyer et al.
patent: 3198808 (1965-08-01), Himmele et al.
patent: 3235562 (1966-02-01), Shilling
patent: 3448118 (1969-06-01), Chichery et al.
patent: 3775431 (1973-11-01), Roderwald, Jr.
patent: 3884936 (1975-05-01), Hollstein
patent: 4885371 (1989-12-01), Tracy et al.
patent: 5101045 (1992-03-01), Koehler et al.
"Synthetic zeolites as Catalysts for the Ring Conversion of gamma-Butyrolactone into 1-substituted 2-Pyrrolidones" Bulletin of the Chemical Society of Japan, Bd. 50 Nr. 10, Oct. 1977, Tokyo Japan, pp. 2517-2521.
"Ring Transformations of gamma-Butyrolactone into 2-Pyrrolidone over Zeolites", Hatada et al., Journal of Catalysis, 1975, pp. 166-175.
"Ring Transformations of Oxygen Containing Heterocycles Into Nitrogen Containing Heterocycles over Synthetic Zeolties", Hatada et al., Chemistry Letters, 1974, pp. 439-442.
Bergfeld Manfred
Wiesgickl Gunter
Akzo Nobel N.V.
Springer David B.
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