IP Library Granted Patent US 8,507,700
Granted Patent B2
US 8,507,700 · App. 13/556,484 · Granted Aug 13, 2013

Method of carbon chain extension using novel aldol reaction

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Quick Facts
Patent No.
US 8,507,700
App. No.
13/556,484
Granted
Aug 13, 2013
Kind
B2
Abstract

Method of producing C 8 -C 15 hydrocarbons comprising providing a ketone starting material; providing an aldol starting material comprising hydroxymethylfurfural; mixing the ketone starting material and the aldol starting material in a reaction in the presence of a proline-containing catalyst selected from the group consisting of Zn(Pro) 2 , Yb(Pro) 2 , and combinations thereof, or a catalyst having one of the structures (I), (II) or (III), and in the presence of a solvent, wherein the solvent comprises water and is substantially free of organic solvents, where (I), (II) and (III) respectively are: where R 1 is a C 1 -C 6 alkyl moiety, X=(OH) and n= 2 . In (III), X may be CH 2 , sulfur or selenium, M may be Zn, Mg, or a lanthanide, and R 1 and R 2 each independently may be a methyl, ethyl, phenyl moiety.

Claims (8)

1. A method of producing a C 8 -C 15 hydrocarbon comprising:

a) providing a ketone starting material;

b) providing an aldol starting material comprising hydroxymethylfurfural; and

c) mixing the ketone starting material and the aldol starting material in a reaction in the presence of a piperidine-containing catalyst and a solvent, wherein the solvent comprises water that is substantially free of organic solvents, to produce the C 8 -C 15 hydrocarbon.

2. The method of claim 1 , wherein the ketone starting material comprises acetone, dihydroxyacetone, or combinations thereof.

3. The method of claim 1 , wherein the reaction occurs at about 25° C.

4. The method of claim 1 , wherein the solvent further comprises a salt.

5. The method of claim 1 , further comprising hydrogenating and dehydrating the C 8 -C 15 hydrocarbon.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 1, 2018
From: LOS ALAMOS NATIONAL SECURITY, LLC
To: TRIAD NATIONAL SECURITY, LLC
Reel/Frame 047401/0957 →
CONFIRMATORY LICENSE Recorded Sep 19, 2012
From: LOS ALAMOS NATIONAL SECURITY
To: U.S. DEPARTMENT OF ENERGY
Reel/Frame 029004/0934 →