Catalyst – solid sorbent – or support therefor: product or process – Catalyst or precursor therefor – Plural component system comprising a - group i to iv metal...
Reexamination Certificate
1999-07-08
2002-08-13
Lipman, Bernard (Department: 1713)
Catalyst, solid sorbent, or support therefor: product or process
Catalyst or precursor therefor
Plural component system comprising a - group i to iv metal...
C502S117000, C502S407000, C502S414000, C502S415000, C525S329100, C525S329300, C525S328700, C525S332800, C525S332900, C525S333100, C525S333200, C525S338000, C525S339000
Reexamination Certificate
active
06432861
ABSTRACT:
The present invention relates to a process for reacting organic compounds in the presence of a catalyst which comprises at least one metal of transition group VIII of the Periodic Table applied to a support, where the support has macropores and comprises boron(III) oxide. Furthermore, the present invention relates to such a catalyst support and such a catalyst itself, and also to processes for producing them. Among reactions of organic compounds, particular preference is given according to the present invention to the hydrogenation of polymers containing C—C multiple bonds.
In the past, homogeneous and heterogeneous catalysts have been described for reactions of organic compounds. For the prior art existing in this field, reference may be made to EP-A 0 814 098. That application relates to a process for reacting organic compounds in the presence of a catalyst comprising ruthenium or palladium and, if desired, one or more further metal(s) of transition groups I, VII and VIII of the Periodic Table as active metals on a support, where this support has a specific pore size distribution and both mesopores and macropores. Furthermore, that application gives a detailed description of the relevant prior art.
It is an object of the present invention to provide a further improved process for reacting organic compounds, in particular for the selective hydrogenation of polymers having C—C multiple bonds, which makes possible high conversions at high space velocities over the catalyst and long catalyst operating lives without further hydrogenatable units present in the polymer, e.g. aromatic units or nitrile or alcohol groups, being attacked.
We have found that this object is achieved by the use of a catalyst which comprises a support containing macropores and comprising boron(III) oxide. The catalyst used gives the desired target compound with high selectivity even at a high space velocity over the catalyst and enables long catalyst operating lives to be achieved.
The present invention accordingly provides a process for reacting an organic compound in the presence of a catalyst comprising, as active metal, at least one metal of transition group VIII of the Periodic Table, either alone or together with at least one metal of transition group I or VII of the Periodic Table, in an amount of from 0.01 to 30% by weight, based on the total weight of the catalyst, applied to a support containing macropores, wherein the catalyst comprises, as a support component, boron(III) oxide in an amount of from 10 to 100% by weight, based on the total weight of the support.
COMPOUNDS
The term “organic compound” as used for the purposes of the present invention encompasses all organic compounds which can be reacted catalytically, in particular those containing groups to be treated with hydrogen, e.g. C—C double bonds or C—C triple bonds. It encompasses both low molecular weight organic compounds and polymers. “Low molecular weight organic compounds” are, for the present purposes, compounds having a weight average molecular weight of less than 500. The term “polymer” refers to molecules having a weight average molecular weight of more than about 500.
In particular, the present invention provides a process for reacting an organic compound in the presence of a catalyst as defined herein where the reaction is a hydrogenation, dehydrogenation, hydrogenolysis, aminating hydrogenation or dehalogenation, preferably a hydrogenation.
Here, it is possible to use, in particular, organic compounds which contain one or more of the following structural units:
The process of the present invention is particularly suitable for the reaction, preferably hydrogenation, of an organic compound selected from the group consisting of aromatic compounds in which at least one hydroxyl group is bound to an aromatic ring, aromatic compounds in which at least one amino group is bound to an aromatic ring, ketones, aldehydes, carboxylic acids and derivatives thereof, polymers having at least one C—C double bond, polymers having at least one C═O group, polymers having at least one C═N group and mixtures of two or more thereof.
In the process of the present invention, it is also possible to react organic compounds which comprise units of different structures as defined above, e.g. organic compounds which have both C—C multiple bonds and carbonyl groups, since the catalysts used in the process of the present invention are able to selectively react, preferably hydrogenate, one of the two groups, i.e. one type of group can be hydrogenated to an extent of from about 90 to 100% while the other type of group is initially reacted, preferably hydrogenated, to an extent of less than 25% and generally to an extent of from 0 to about 7%. In general, the C—C multiple bonds are reacted or hydrogenated first and the C═O groups are reacted or hydrogenated subsequently.
The term “aromatic compound in which at least one hydroxyl group is bound to an aromatic ring” or “aromatic compound in which at least one amino group is bound to an aromatic ring” refers to all compounds which include a unit of the following structure (IX):
where R is a hydroxyl group or an amino group.
If aromatic compounds in which at least one hydroxyl group and, in addition, at least one substituted or unsubstituted C
1
-C
10
-alkyl radical and/or -alkoxy radical is bound to an aromatic ring are used in the process of the present invention, the isomer ratio of cis- to trans-configured products obtained can be varied within a wide range as a function of the reaction conditions (temperature, solvent). Furthermore, the compounds obtained can be processed further without additional purification steps. The formation of alkylbenzenes is virtually completely avoided.
As in the case of the above-described compounds in which at least one hydroxyl group is bound to an aromatic ring, the process of the present invention also makes it possible to hydrogenate aromatic compounds in which at least one amino group is bound to an aromatic ring with high selectivity to give the corresponding cycloaliphatic compounds. In the case of amines which are additionally substituted by a C
1
-C
10
-alkyl radical and/or -alkoxy radical, what has been said above in respect of the ratio of the cis and trans isomers also applies.
In particular, the formation of deamination products, for example cyclohexanes or partially hydrogenated dimerization products such as phenylcyclohexylamines, is virtually completely avoided in this embodiment.
Specifically, the following compounds can be reacted in the process of the present invention:
Aromatic-Compounds in Which at Least One Hydroxyl Group is Bound to an Aromatic Ring
The process of the present invention enables aromatic compounds in which at least one hydroxyl group and preferably also at least one substituted or unsubstituted C
1
-C
10
-alkyl radical and/or -alkoxy radical is bound to an aromatic ring to be reacted, preferably hydrogenated to give the corresponding cycloaliphatic compounds, with it also being possible to use mixtures of two or more of these compounds. The aromatic compounds can be monocyclic or polycyclic aromatic compounds. The aromatic compounds contain at least one hydroxyl group which is bound to an aromatic ring; the simplest compound of this group is phenol. The aromatic compounds preferably have one hydroxyl group per aromatic ring. The aromatic compounds can be substituted on the aromatic ring or rings by one or more alkyl and/or alkoxy radicals, preferably C
1
-C
10
-alkyl and/or -alkoxy radicals, particularly preferably C
1
-C
10
-alkyl radicals, in particular methyl, ethyl, propyl, isopropyl, butyl, isobutyl and/or tert-butyl radicals; among the alkoxy radicals, preference is given to C
1
-C
8
-alkoxy radicals such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy and/or tert-butoxy radicals. The aromatic ring or rings and also the alkyl and alkoxy radicals may, if desired, be substituted by halogen atoms, in particular fluorine atoms, or other suitable inert substituents.
Preferably, the compounds which can be reacted,
Böttcher Arnd
Breitscheidel Boris
Diehlmann Uwe
Henkelmann Jochem
Kindler Alois
BASF - Aktiengesellschaft
Keil & Weinkauf
Lipman Bernard
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