Catalyst for dehydrogenation of amino alcohols to amino carboxyl

Catalyst – solid sorbent – or support therefor: product or process – Catalyst or precursor therefor – Metal – metal oxide or metal hydroxide

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502227, 502244, 502300, 502305, 502306, 502313, 502314, 562526, 562539, 562553, 562566, 562572, B01J 2300, C07C 5116

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active

061598941

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BRIEF SUMMARY
DESCRIPTION

The invention relates to a new catalyst suitable for dehydrogenating amino alcohols to aminocarboxylic acids or ethylene glycol (derivatives) to oxycarboxylic acids, said catalyst containing zirconium, copper, and possibly an additional metal, whereby the cited metals are precipitated as hydroxides, washed, dried, calcined, and reduced.
Moreover, the invention relates to a process for preparing a catalyst usable for dehydrogenating amino alcohols to aminocarboxylic acids or ethylene glycol (derivatives) to oxycarboxylic acids, said catalyst containing zirconium, copper and possibly an additional metal, whereby the cited metals are precipitated as hydroxides, washed, dried, calcined, and reduced.
A number of processes have been disclosed for preparing a catalyst for the aforementioned reactions. These processes can be categorized essentially into four groups, which are described in the following.
Anchor catalysts: In WO-A1-96/01146, the preparation of catalysts with anchor metals is described. A noble metal such as gold, platinum, palladium, or ruthenium is bound as a so-called anchor to an alkali-resistant carrier such as zirconium dioxide, titanium dioxide, or carbon. Metals other than noble metals, such as copper, cobalt, nickel, or cadmium, are deposited on the surface of the anchor using a reduction agent such as formaldehyde.
Raney catalysts: In DE-C2-3505208, Raney copper or Raney nickel is used as a catalyst. In EP-A1-0513396, Raney copper is used as a catalyst with specified values for BET area and for nickel content. In EP-A1-0506973, Raney copper is used as a catalyst, whereby aluminum or an aluminum compound is added to the reaction mixture during the catalytic dehydrogenation. In WO-A1-94/24091 and U.S. Pat. No. 5,367,112, Raney copper is used as a catalyst with 10 to 50000 ppm of one of the elements comprising chromium, titanium, niobium, tantalum, zirconium, vanadium, molybdenum, tungsten, cobalt, nickel, bismuth, tin, antimony, lead, germanium, magnesium, and their mixtures.
Impregnated zirconium oxide: In JP-A1-61-93146 and GB-A1-2148287, a catalyst is described whose preparation comprises impregnating zirconium oxide with an aqueous solution of copper nitrate, drying, calcining in air for 6 hours at 500.degree. C., and reducing for 6 hours at 230.degree. C. in a hydrogen stream.
Simultaneous precipitation of zirconium, copper and possibly an additional metal: In JP-A1-61-93146, DE-C2-3505208, EP-A1-0506973, EP-A1-0513396, and GB-A1-2148287, a catalyst is described whose preparation comprises initially preparing an aqueous solution containing zirconium oxychloride and copper nitrate. Aqueous sodium hydroxide is added to this solution, whereby zirconium and copper are simultaneously precipitated as hydroxides. The washed and dried precipitate is calcined in air for 3 hours at 500.degree. C. and reduced for 6 hours at 230.degree. C. in a hydrogen stream. In accordance with WO-A1-94/24091, an aqueous solution is prepared containing zirconium oxychloride octahydrate, copper nitrate trihydrate, and bismuth nitrate pentahydrate or tin nitrate, and the remaining process is as previously described.
The anchor catalysts require expensive noble metals, which constitute 1 to 50 percent by weight of these catalysts. Catalysts made from Raney nickel are pyrogenic and therefore require increased safety expense during handling. The catalysts made from impregnated zirconium oxide and from simultaneously precipitated zirconium and copper require long reaction times for the catalytic dehydrogenation of amino alcohols. For example, in JP-A1-61-93146, a reaction time of 6.5 hours is required for the transformation of tetrahydroxyethylethylenediamine (THEEDA) to the tetrasodium salt of ethylenediamine tetraacetate ((EDTA)Na.sub.4) using a catalyst of impregnated zirconium oxide to produce an (EDTA)Na.sub.4 yield of 84.5%. Use of the catalyst also described in JP-A1-61-93146 comprising simultaneously precipitated zirconium and copper requires 6 hours to produce (EDTA)Na.sub.4 from THEEDA in a yield

REFERENCES:
patent: 5220054 (1993-06-01), Urano et al.
patent: 5292936 (1994-03-01), Franczyk
patent: 5367112 (1994-11-01), Franczyk
patent: 5739390 (1998-04-01), Franczyk et al.

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