Synthesis of high caloric fuels and chemicals via ketene and diketene intermediates
AssigneePioneer Energy, Inc.
InventorsJohn Henri, Jan Zygmunt, Mark Berggren, Robert Zubrin
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Abstract
In one embodiment, the present application discloses methods to selectively synthesize higher alcohols and hydrocarbons useful as fuels and industrial chemicals from syngas and biomass. Ketene and ketonization chemistry along with hydrogenation reactions are used to synthesize fuels and chemicals. In another embodiment, ketene used to form fuels and chemicals may be manufactured from acetic acid which in turn can be synthesized from synthesis gas which is produced from coal, biomass, natural gas, etc.
Claims14
A method for the preparation of a mixture of alkyl compounds, the method comprising:
- a) preparing a ketene of the formula I:
- b) reacting the ketene in a self-addition reaction to form a diketene of the formula II;
- and
- wherein:
- each R1 is independently H or C1-6 alkyl;
- and
- each R2 is independently H or C1-6 alkyl;
- c) hydrogenating the diketene of the formula II in the presence of a metal catalyst to form the mixture of alkyl compounds comprising 1-butanol, 2-butanol, 2-pentanol, 1-hexanol, 2-hexanol, 2-heptanol, 4-heptanol, 3-methyl cyclohexanol, and 2,6-dimethyl-4-heptanol.
A method for the preparation of 1-butanol, 2-butanol or a mixture thereof, the method comprising:
- a) preparing a ketene of the formula I:
- b) reacting the ketene in a self-addition reaction to form a diketene of the formula II;
- wherein:
- each R1 is independently H or C1-6 alkyl;
- and
- each R2 is independently H or C1-6 alkyl;
- c) the diketene of the formula II is further reacted with R—OH, wherein R—OH is methanol or butanol, to form an acetoacetate ester of the formula III;
- and
- d) the acetoacetate ester of the formula III is reduced in the presence of a metal to form 1-butanol or 2-butanol of the formula IV or V and R—OH, or mixtures thereof.
A method for the preparation of an alkyl compound or mixtures thereof, the method comprising:
- a) preparing a ketene of the formula I:
- b) reacting the ketene in a self-addition reaction to form a diketene of the formula II;
- wherein:
- each R1 is independently H or C1-6 alkyl;
- and
- each R2 is independently H or C1-6 alkyl;
- and
- c) converting the diketene of the formula II to dehydroacetic acid;
- and
- d) reducing the dehydroacetic acid in the presence of a catalyst to form a composition comprising the alkyl compounds or mixtures thereof.
Dependencies are inferred from the claim text.