Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1997-02-20
1997-12-16
Owens, Amelia A.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C07D30726
Patent
active
056987137
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP95/00589 filed Feb. 17, 1995.
The present invention relates to a process for vapour phase catalytic hydrogenation of maleic anhydride to gamma-butyrolactone using a three-component catalyst composition comprising copper-, zinc- and zirconium oxides. Gamma-butyrolactone (GBL) became industrially available in the 1940's as a result of the work of W. Reppe. The Reppe process starts from acetylene and formaldehyde to yield 1,4-butanediol (BDO), which is dehydrogenated to GBL. The main use of GBL is as an intermediate for pyrrolidone, N-methylpyrrolidone, N-vinylpyrrolidone, herbicides, pharmaceuticals and rubber additives. In smaller amounts it is used as a solvent mainly in the polymers field. After maleic anhydride (MA) price has lowered, due to new industrial processes that use butane as a feedstock instead of benzene, fluidized bed and non-aqueous product recovery, this molecule is regarded as a building block for several derivatives. Hydrogenation of MA or its esters to GBL, tetrahydrofuran (THF) and BDO has been widely studied. Liquid phase hydrogenation of MA to GBL has been employed in commercial production, but never got great industrial importance. Vapour phase catalytic hydrogenation of MA or its esters to GBL has been disclosed in many patents, but did not reach industrial realisation. The only process that met industrial practice is diethylmaleate hydrogenation to produce BDO as disclosed in WO 86/03189. A similar process was disclosed for GBL production in WO 86/07358 but from the economical point of view direct hydrogenation of MA to derivatives must be preferred. Dunlop in U.S. Pat. No. 3,065,243 disclosed a process for hydrogenation of maleic or succinic anhydride or their esters to GBL in the vapour phase, using copper chromite as a catalyst but conversion and selectivity, were not satisfactory. Similar results were obtained using a copper-zinc oxide catalyst, as disclosed in British patent 1 168 220. Miller in U.S. Pat. No. 4,001,282 suggested the addition of water to improve catalyst life by reducing tar formation, but did nor mention improvements in conversion or selectivity. Noble metal based catalysts such as Cu/Pd and Cu/Pt were disclosed by De Thomas in U.S. Pat. No. 4,105,674.
Cu/Zn/Cr catalysts were described by Miya in U.S. Pat. No. 3,580,930 and Cu/Zn/Cr/Al catalysts by Attig in EP 332 140. None of these processes have reached industrial application, probably because of not completely satisfactory results in terms of GBL yield, productivity or byproducts. Moreover it has to be pointed out that chromium containing catalysts should be avoided for environmental reasons. Recently a process has been disclosed by Taylor in WO 91/16132, concerning MA vapour phase hydrogenation over a Cu/Zn/Al catalyst activated at 400.degree.-525.degree. C. Process conditions are also described to achieve commercial operation, but the need of high temperature activation is a disadvantage in terms of plant design and operation. The object of the invention is to provide a process for the production of gamma-butyrolactone from maleic anhydride or succinic anhydride which exhibits a very high selectivity at an essentially quantitative conversion of the starting material without requiring noble metals or toxic compounds. A further object of the invention is to provide a catalyst for this process which is easy to prepare and maintains its activity even after prolonged operation.
The present invention provides a process for the hydrogenation of maleic or succinic anhydride to GBL over a Cu/Zn/Zr catalyst. The Cu/Zn/Zr catalyst comprises a catalytically active oxide material and optionally an essentially inert support. The catalytically active oxide material comprises a mixed oxide of copper, zinc and zirconium, the metals content of which is composed of 10-40 wt % of copper, 10-40 wt % of zinc, and 30-70 wt % of zirconium. Preferably the composition comprises 20-30 wt % of copper, 20-30 wt % of zinc and 40-60 wt % of zirconium. In the active state, the catalytically active oxid
REFERENCES:
patent: 3065243 (1962-11-01), Dunlop et al.
patent: 3580930 (1971-05-01), Miya et al.
patent: 4001282 (1977-01-01), Miller
patent: 4105674 (1978-08-01), De Thomas et al.
patent: 4965378 (1990-10-01), Budge et al.
patent: 5072009 (1991-12-01), Budge et al.
patent: 5347021 (1994-09-01), Taylor et al.
Chemical Abstracts, vol. 117, No. 15 (1992), 150868n (English translation).
Armbruster Erich
Fumagalli Carlo
Lancia Rosa
Vaccari Angelo
Lonza S.P.A.
Owens Amelia A.
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