Methods For Producing Fuels, Gasoline Additives, And Lubricants (BP Corporation)

CATEGORY: GASOLINE 
Methods For Producing Fuels, Gasoline Additives, And Lubricants (BP Corporation)
United States Patent Application 20160115143
SACIA; Eric ;   et al.   April 28, 2016
Assignee: The Regents of the University of California
Assignee: BP Corporation North America Inc.
Abstract

The present disclosure generally relates to the production of fuels, gasoline additives, and/or lubricants, and precursors thereof. The compounds used to produce the fuels, gasoline additives, and/or lubricants, and precursors thereof may be derived from biomass. The fuels, gasoline additives, and/or lubricants, and precursors thereof may be produced by a combination of intermolecular and/or intramolecular aldol condensation reactions, Guerbet reactions, hydrogenation reactions, and/or oligomerization reactions.
FIELD
[0002] The present disclosure generally relates to the production of fuels, gasoline additives, and/or lubricants, and precursors thereof.
BACKGROUND
[0003] Producing fuels and other value added chemicals such as gasoline additives and lubricants from renewable sources has become increasingly important as a means of reducing the production of greenhouse gases and of reducing the imports of petroleum. See L. D. Gomez, C. G. Steele-King, S. J. McQueen-Mason, New Phytologist, 2008, 178, 473-485. Lignocellulosic biomass is typically made up of cellulose, hemicellulose, and lignin. These biomass components are non-edible, carbohydrate-rich polymers that may serve as a renewable source of energy. They typically make up to at least 70% of the dry weight of biomass. As such, conversion of these non-edible biomass components into biofuels and other value added chemicals from renewable sources is of ongoing interest that can benefit the environment and reduce petroleum imports. See A. Demirbas, Energy Sources, Part B: Economics, Planning and Policy, 2008, 3, 177-185. Biomass may first be converted to intermediate compounds such as sugars, which may then be converted into other precursor molecules that may be converted to fuels (e.g., gasoline or diesel), gasoline additives, and/or lubricants.
BRIEF SUMMARY
[0004] In one aspect, provided is a method of producing one or more ketones by contacting a compound of formula (I) with basic catalyst and one or more alcohols or aldehydes of formula (II) to produce the one or more ketones,
wherein the compound of formula (I) and the compound of formula (II) have the following structures:
##STR00001##
[0005] wherein: [0006] each R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, and R.sub.6 is independently selected from hydrogen, alkyl, aryl, alkenyl, and alkynyl; provided that one or both of (i) and (ii) occurs: (i) at least two of R.sub.1, R.sub.2, and R.sub.3 are hydrogen; and (ii) at least two of R.sub.4, R.sub.5, and R.sub.6 are hydrogen; [0007] n is an integer greater than or equal to 0; [0008] R.sub.7 is selected from alkyl, aryl, alkenyl, alkynyl, and heteroaryl; [0009] X is OH or O; and [0010] the dashed line represents an optional double bond that is present when X is O.
[0011] In another aspect, provided is a method of producing one or more C.sub.24-C.sub.36 alkanes, by: (a) contacting an aldehyde and one or more alcohols with metal catalyst and optionally base to produce one or more higher aldehydes; (b) hydrogenating the one or more higher aldehydes to one or more higher alcohols; and (c) converting the one or more higher alcohols to the one or more C.sub.24-C.sub.36 alkanes. In some embodiments, the higher aldehydes have a greater number of carbon atoms than the number of carbon atoms in the ketone used in step (a) as a starting material.
[0012] In yet another aspect, provided is a method of producing one or more compounds of formula (IX), by contacting a ketone of formula (VII) with a diol of formula (VIII) to produce the one or more compounds of formula (IX),
wherein: [0013] the ketone of formula (VII) has the following structure:
##STR00002##
[0013] wherein: [0014] R.sub.14 is H or alkyl; and [0015] R.sub.15 is methyl; the diol of formula (VIII) has the following structure:
[0015] ##STR00003## [0016] wherein t is an integer greater than or equal to 4; and
[0017] the one or more compounds of formula (IX) have the following structure:
##STR00004## [0018] wherein: [0019] R.sub.14 is as described above for formula (VII) [0020] R.sub.16 is --CH.sub.2--; and [0021] t is as described above for formula (VIII).
[0022] In yet another aspect, provided is a method of producing a cyclic alkane, cyclic alcohol, or mixtures thereof, by: (a) contacting a diketone with basic catalyst to produce a cyclic ketone; and (b) hydrogenating the cyclic ketone to produce the cyclic alkane, cyclic alcohol, or mixtures thereof.
[0023] Provided is also a composition that includes: a diesel fuel, a gasoline additive, or a lubricant, or any mixtures thereof; and one or more alkanes, cyclic alkanes, or cyclic alcohols produced according to any of the methods described above.
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