Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Patent
1986-08-22
1988-02-23
Reamer, James H.
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
568396, 568403, 568406, C07C 4545
Patent
active
047271965
DESCRIPTION:
BRIEF SUMMARY
This invention relates in general to the upgrading of oxygenated compounds. In one aspect, the invention relates to the preparation of higher carbonyl compounds from lower alcohols, and optionally lower carbonyl compounds, in the presence of a ruthenium supported catalyst. In another aspect, the invention relates to the upwarding of lower alcohols to higher alcohols in the presence of the same ruthenium supported catalyst.
Catalytic dehydrogenation, hydrogenation and condensation reactions are well known. More particularly, the one step conversion of alcohols such as isopropanol into ketones such as methyl isobutyl ketone has been widely reported.
It has now been found that carbonyl compounds can be prepared by reacting lower alcohols, optionally with lower carbonyl compounds, in the presence of a ruthenium metal or metal oxide supported catalyst.
In accordance with the present invention, a process is provided for the preparation of higher carbonyl compounds from C.sub.1 to C.sub.8 cyclic or acyclic alcohols containing at least one active hydrogen atom bonded to the beta carbon atom or readily convertible thereto under the reaction conditions, the process comprising reacting the alcohol in the presence of a catalyst at elevated temperatures characterised in that the catalyst is ruthenium metal or an oxide thereof supported on a solid support.
The alcohols of this invention are saturated C.sub.1 -C.sub.8 cyclic or acyclic alcohols containing at least one active hydrogen atom bonded to the beta carbon atom or readily convertible thereto under the reaction conditions employed. Examples of alcohols include but are not limited to methanol, ethanol, propanol, butanol pentanol, hexanol or combinations thereof.
The alcohols may also be reacted with lower carbonyl compounds to produce the higher carbonyl compounds. Useful lower carbonyl compounds are ketones or aldehydes having from 1 to 4 carbon atoms such as dimethyl ketone (acetone), ethyl methyl ketone, formamide, and the like.
In another embodiment of the present invention, the alcohol used in the above reaction to produce higher carbonyl compounds can be replaced by a lower carbonyl compound and a suitable amount of hydrogen. For example, in the preparation of methyl isobutyl ketone, isopropanol can be replaced with a suitable mixture of acetone and hydrogen. The ratio of lower carbonyl compound to hydrogen can vary from 3:1 to 1:1.
Provided that there is present an alcohol having at least one active hydrogen atom bonded to the beta carbon atom, other reactants need not contain an active hydrogen atom.
The higher carbonyl compounds prepared in accordance with this invention are aldehydes or ketones having at least one more carbon atom than the longest carbon chain alcohol or lower carbonyl compound reactant employed. These aldehydes and ketones may be saturated or unsaturated compounds and may be mono- or poly-aldehydes or ketones. The preferred higher carbonyl compounds produced herein are C.sub.4 to C.sub.10 saturated monoketones. Most preferred are methyl isobutyl ketone and diisobutyl ketone.
Higher alcohols, that is alcohols having at least one additional carbon atom than the reactant alcohol, may also be formed to a greater or lesser extent, depending on the nature of the alcohol reactant, the nature of the catalyst support and the reaction conditions employed.
The higher alcohols can be any alcohols having at least one additional carbon than the lower alcohol reactant. For example, ethanol can be converted into a higher alcohol such as propanel or butanol. While the higher alcohols will contain at least one additional carbon atom than the lower alcohol reactant, preferably the higher alcohol will contain 2 or more additional carbons. Butanol is the most preferred higher alcohol.
The catalysts useful in the reactions of the present invention are ruthenium metal and metal oxide supported catalysts. Suitable supports are any solid support matrix which is either acidic or basic and having the ability to catalyse condensation reactions.
The preferred conden
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MacApline Derek K.
Williams Bruce L.
Williams Peter S.
BP Chemicals Limited
Reamer James H.
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