Methods for producing fuels, gasoline additives, and lubricants

Patent metadata

Field	Value
Publication number	US-9738617-B2
Application number	US-201414895851-A
Country	US
Kind code	B2
Filing date	Jun 3, 2014
Priority date	Jun 3, 2013
Publication date	Aug 22, 2017
Grant date	Aug 22, 2017

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.

First claim

The invention claimed is:

1. A method of producing one or more ketones by contacting a compound of formula (I) with a 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:

 wherein:
R 7 is selected from the group consisting of alkyl, aryl, alkenyl, alkynyl, and heteroaryl;
X is OH or O; and
the dashed line represents an optional double bond that is present when X is O; and

wherein the basic catalyst:
(i) comprises an alkali metal hydroxide, an alkaline earth metal hydroxide, a mixed metal oxide, or K 3 PO 4 ; or
(ii) is a heterogeneous catalyst comprising Mg, Al, Zr, Ti, Ce, B, or Y, or any mixtures thereof.

2. The method of claim 1 , wherein the compound of formula (II) is:

wherein R 7 is C 1 -C 10 alkyl or C 4 -C 21 heteroaryl.

3. The method of claim 1 , wherein the compound of formula (II) is selected from the group consisting of furfural, 5-methylfurfural, and 5-hydroxymethylfurfural.

4. The method of claim 1 , wherein the compound of formula (II) is:

5. The method of claim 1 , wherein the one or more ketones are selected from the group consisting of:

or any mixtures thereof.

6. The method of claim 1 , wherein the basic catalyst comprises an alkali metal hydroxide, an alkaline earth metal hydroxide, or a mixed metal oxide.

7. The method of claim 6 , wherein the mixed metal oxide comprises MgZrO or MgAlO.

8. The method of claim 1 , wherein the compound of formula (I) is contacted with the basic catalyst in aqueous solvent, organic solvent, or biphasic aqueous and organic solvent.

9. The method of claim 8 , wherein the organic solvent comprises toluene, trimethylacetonitrile, dimethylformamide, propyl-acetate, dioxane, butanol, hexanol, or octanol, or any mixture thereof.

10. The method of claim 1 , wherein at least 70% of the one or more ketones are branched ketones.

11. The method of claim 1 , further comprising hydrogenating the one or more ketones to one or more alkanes.

12. The method of claim 11 , wherein the one or more alkanes are selected from the group consisting of:

or any mixtures thereof.

13. The method of claim 1 , wherein the basic catalyst comprises an alkali metal hydroxide, an alkaline earth metal hydroxide, a mixed metal oxide, or K 3 PO 4 .

14. The method of claim 1 , wherein the basic catalyst is a heterogeneous catalyst comprising Mg, Al, Zr, Ti, Ce, B, or Y, or any mixtures thereof.

Assignees

• Univ California
• Bp Corp North America Inc

Inventors

• Sacia Eric
• Pazhamalai Anbarasan
• Madhesan Balakrishnan
• Sreekumar Sanil
• Toste F Dean
• Gokhale Amit A
• Carrera Martin E
• Bell Alexis T
• Gunbas Gorkem

Classifications

• C10N2070/00

  Specific manufacturing methods for lubricant compositions · CPC title

• C07C2523/42

  Platinum · CPC title

• C07C45/68

  by increase in the number of carbon atoms · CPC title

• C10L1/182

  containing hydroxy groups; Salts thereof {(C10L1/1802, C10L1/1805, C10L1/1808, C10L1/1811, C10L1/1814, C10L1/1817 take precedence)} · CPC title

• C07C45/71

  being hydroxy groups · CPC title