Liquid Phase Hydrogenation of Maleic Anhydride and Intermediates on Copper-Based and Noble Metal Catalysts

Herrmann, Uwe; Emig, G.

doi:10.1021/ie960229g

Cited by 65 publications

(77 citation statements)

References 12 publications

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“…The active sites for hydrogenation and hydrogenolysis reactions are provided by metallic copper. The role of ZnO as an adsorbent for succinic anhydride has been elucidated recently by Herrmann and Emig who investigated the hydrogenation of maleic acid anhydride in the liquid (slurry) phase [10,11]. The gas-phase conversion of dimethyl maleate has been studied by Turek and coworkers [8,12].…”

Section: Introductionmentioning

confidence: 99%

Extrusion of Cu/ZnO catalysts for the single-stage gas-phase processing of dimethyl maleate to tetrahydrofuran

Müller

Kucher

Ohlinger

et al. 2003

Journal of Catalysis

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Bifunctional catalysts consisting of copper, zinc oxide, and γ -alumina have been produced by means of extrusion. The effects of formulation and forming conditions on morphology, pore texture, and copper surface area are discussed. These extruded catalysts have been employed in the fixed-bed gas-phase conversion of dimethyl maleate at temperatures between 453 and 493 K and space velocities ranging from 0.2 to 2.4 h −1 . Copper catalyzes the hydrogenation and hydrogenolysis reactions yielding γ -butyrolactone, and 1,4-butanediol. γ -Alumina provides weakly acidic sites which promote the subsequent dehydration of 1,4-butanediol to tetrahydrofuran. Coupled products are methanol and water. Through choice of composition and pore texture of the extrudates it is possible to achieve tetrahydrofuran yields of 100% (basis the C 4 -products) at a low pressure (2.5 MPa) in a single stage.

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Section: Introductionmentioning

confidence: 99%

Extrusion of Cu/ZnO catalysts for the single-stage gas-phase processing of dimethyl maleate to tetrahydrofuran

Müller

Kucher

Ohlinger

et al. 2003

Journal of Catalysis

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“…However, the selectivity of THP decreased to 85.9% after further increasing the temperature to 290 • C, due to the intensive formation of 1-pentanol. Generally, 1-pentanol was generated from excessive hydrogenolysis of THFA via the acid-catalyzed ring-opening of THP coupled with metal-catalyzed hydrogenation [42]. Table 6 shows the effect of hydrogen pressure on the activity and selectivity in THFA hydrogenolysis over the A 4-1-10 catalyst.…”

Section: Effect Of Reaction Temperature and H 2 Pressurementioning

confidence: 99%

Synthesis of Tetrahydropyran from Tetrahydrofurfuryl Alcohol over Cu–Zno/Al2O3 under a Gaseous-Phase Condition

Zhang

Wang

et al. 2018

Catalysts

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Tetrahydropyran (THP) represents an O-containing hetero-cyclic compound that can be used as a promising solvent or monomer for polymer synthesis. In this work, Cu-ZnO/Al 2 O 3 catalysts have been prepared by a facile precipitation-extrusion method and used for the synthesis of THP through gaseous-phase hydrogenolysis of tetrahydrofurfuryl alcohol (THFA). The effect of the molar ratio of Cu/Zn/Al, reaction temperature, and hydrogen pressure was investigated. An 89.4% selectivity of THP was achieved at 270 • C and 1.0 MPa H 2 . Meanwhile, the optimum molar ratio of Cu/Zn/Al was determined to be 4:1:10. The Cu-ZnO/Al 2 O 3 catalyst exhibited high catalytic activity and stability for 205 h on-stream. A possible reaction mechanism involving several consecutive reactions was proposed: THFA was firstly rearranged to 2-hydroxytetrahydropyran (2-HTHP), followed by the dehydration of 2-HTHP to 3,4-2H-dihydropyran (DHP) over acid sites; finally, the DHP was hydrogenated to THP. The synergy of acid sites and metal sites of Cu-ZnO/Al 2 O 3 played an important role during the production of THP.

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“…The hydrogenation of lactic acid under mild conditions to 1,2-propanediol has long been known, for instance [79]. Likewise, 1,3-propanediol [80] and 1,4-butanediol [81] may be obtained from corresponding three or four carbon lactones or esters or through biological routes [82]. Dupont's Sorona ® (a polytrimethylene terephthalate) and Cerenol™ (polyether polyol) polymers are made of fully renewable 1,3-propanediol and illustrate the viability of these latter routes.…”

Section: Telomerization Of Other 12-and Linear Diolsmentioning

confidence: 99%

Pd-Catalyzed Telomerization of 1,3-Dienes with Multifunctional Renewable Substrates: Versatile Routes for the Valorization of Biomass-Derived Platform Molecules

Bruijnincx

Jastrzebski

Hausoul

et al. 2012

Organometallics and Renewables

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The dimerization of 1,3-dienes (e.g. butadiene) with the addition of a protic nucleophile (e.g. methanol) yields 2,7-octadienyl ethers in the so-called telomerization reaction. This reaction is most efficiently catalyzed by homogeneous palladium complexes. The field has experienced a renaissance in recent years as many of the platform molecules that can be renewably obtained from biomass are well-suited to act as multifunctional nucleophiles in this reaction. In addition, the process adheres to many of the principles of green chemistry, given that the reaction is 100% atom efficient and produces little waste. The telomerization reaction thus provides a versatile route for the production of valuable bulk and specialty chemicals that are (at least partly) green and renewable. The use of various multifunctional substrates that can be obtained from biomass is covered in this review, as well as mechanistic aspects of the telomerization reaction.

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Liquid Phase Hydrogenation of Maleic Anhydride and Intermediates on Copper-Based and Noble Metal Catalysts

Cited by 65 publications

References 12 publications

Extrusion of Cu/ZnO catalysts for the single-stage gas-phase processing of dimethyl maleate to tetrahydrofuran

Extrusion of Cu/ZnO catalysts for the single-stage gas-phase processing of dimethyl maleate to tetrahydrofuran

Synthesis of Tetrahydropyran from Tetrahydrofurfuryl Alcohol over Cu–Zno/Al2O3 under a Gaseous-Phase Condition

Pd-Catalyzed Telomerization of 1,3-Dienes with Multifunctional Renewable Substrates: Versatile Routes for the Valorization of Biomass-Derived Platform Molecules

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