Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Patent
1994-02-25
1995-04-11
Reamer, James H.
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
568342, 568836, 568910, 568311, C07C 4528
Patent
active
054060028
DESCRIPTION:
BRIEF SUMMARY
This invention relates to catalysts, more especially to a method of modifying catalysts, the modified catalysts themselves, and to an oxidation process using the catalysts produced by the method.
Zeolite catalysts of many types have been proposed for use in numerous chemical processes. Among such catalysts are catalysts based on silicon and titanium oxides and optionally other components.
U.S. Patent No. 3,329,481 describes a catalyst of the formula the valency of D, w represents 0.5 to 4, X represents one or more of titanium, zirconium, and hafnium, and y represents from 1 to 15, preferably from 2 to 10.
U.S. Pat. No. 3,702,886 describes crystalline zeolites denoted ZSM-5, their manufacture, and their use as catalysts in a number of hydrocarbon conversions.
U.S. Pat. No. 4,061,724 describes silicalite, processes for its manufacture, and its x-ray diffraction pattern.
GB-A-2071071 describes porous crystalline synthetic materials of the formula have a silicalite structure in which titanium is substituted for silicon.
In British Patent Application No. 2024790, silicalites modified by the inclusion in the structure of other oxides, inter alia titanium, are described, as are uses for the modified material as catalysts.
GB-A-2083816 and 2116974 describe similar materials and their uses as oxidation catalysts.
EP-A-226258 describes silicates containing titanium and iron, and their uses as catalysts in various organic reactions.
In EP-A-100119, there is described a process for epoxidation of olefinic compounds by H.sub.2 O.sub.2 using as catalyst a titanium-containing zeolite of the formula given in GB-A-2071071. The X-ray diffraction pattern and infra-red spectrum of the zeolite are described, and the material is designated TS-1. In EP-A-230949, the proportion of undesired by-products in the epoxidation reaction is reduced by employing a TS-1 catalyst treated with a base.
In WO 90/05126 there is described the oxidation of saturated hydrocarbon chains using a titanium-containing silicalite catalyst with an infra-red absorption band at about 950cm.sup.-1.
In EP-A-412596 there is described the oxidation of paraffins in the presence of a titanium silicalite.
A paper by M. Nakamura et al, Shokubai (Catalyst), Vol. 32 No. 2, 1990, 65th Catalyst Society of Japan meeting, Abstract No. B3, described the effect of treating a TS-1 catalyst with amines of varying molecular sizes on the catalyst's activity in olefin and paraffin oxidation reactions. It was noted that in the oxidation of n-hexane, addition of triethylamine terminated the reaction, while the addition of triphenylamine hardly affected the yield. In the oxidation of 2-hexene, triethylamine inhibited the reaction, whereas triphenylamine accelerated it. In the oxidation of cyclohexane, triphenylamine again increased the yield (no results being reported for triethylamine with this reaction).
The procedures described in WO 90/05126 and the Nakamura et al paper for the oxidation of paraffins, and saturated aliphatic chains in other molecules, e.g., alkyl aromatic compounds, have advantages over other methods for oxidizing saturated organic compounds to introduce functional groups. In particular, because the catalyst is not in the same phase as the reactants, separation is facilitated, and the catalyst is readily available.
However, the product yield, based on peroxide used, is in need of improvement, a substantial H.sub.2 O.sub.2 proportion being decomposed to water and oxygen, and the conversion rate of alkane to alkanol and alkanone is poor.
It has now surprisingly been found that a titanium-silicon zeolite catalyst treated with an organophosphine is an effective oxidation catalyst.
The present invention accordingly provides a titanium-containing zeolite catalyst that has been treated with an organophosphine.
The invention further provides a process for the oxidation of a hydrocarbon using an organophosphine-treated titanium-containing zeolite catalyst.
The invention still further provides the use of an organophosphine-treated titanium-containing zeolite as a catal
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Martens Luc R. M.
Mathys Georges M. K.
Exxon-Chemical Patents Inc.
Mahon John J.
Reamer James H.
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