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Title: Hydrogenated 5-carbon compound and method of making

Abstract

The present invention is based upon the surprising discovery that a 5-carbon compound selected from the group of 4-oxopentanoic acid, at least one lactone of 4-oxopentanoic acid, and combinations thereof, may be hydrogenated with a bimetallic catalyst of a noble metal in combination with a second metal and preserve the pendant methyl group. It was further unexpectedly discovered that the same conditions of bimetallic catalyst in the presence of hydrogen are useful for catalyzing the different intermediate reactions, for example, angelicalactone to gamma-valerolactone and gamma-valerolactone to 1,4-pentanediol. Finally, it was surprising that levulinic acid could be converted to 2-methyltetrahydrofuran with heating in the presence of the bimetallic catalyst and hydrogen in a single process vessel. The method of the present invention unexpectedly produced a fuel or fuel component having 2-methyltetrahydrofuran either in a yield greater than 4.5 mol % or in combination with alcohols. 8 figs.

Inventors:
;
Publication Date:
Research Org.:
Battelle Memorial Institute, Columbus, OH (United States)
Sponsoring Org.:
USDOE, Washington, DC (United States)
OSTI Identifier:
335448
Patent Number(s):
US 5,883,266/A/
Assignee:
Battelle Memorial Inst., Richland, WA (United States)
DOE Contract Number:  
AC06-76RL01830
Resource Type:
Patent
Resource Relation:
Other Information: PBD: 16 Mar 1999
Country of Publication:
United States
Language:
English
Subject:
10 SYNTHETIC FUELS; LIQUID FUELS; SYNTHESIS; CATALYSTS; HYDROGENATION; MONOCARBOXYLIC ACIDS; LACTONES; BIMETALS; MTHF; ALCOHOLS

Citation Formats

Elliott, D C, and Frye, J G. Hydrogenated 5-carbon compound and method of making. United States: N. p., 1999. Web.
Elliott, D C, & Frye, J G. Hydrogenated 5-carbon compound and method of making. United States.
Elliott, D C, and Frye, J G. 1999. "Hydrogenated 5-carbon compound and method of making". United States.
@article{osti_335448,
title = {Hydrogenated 5-carbon compound and method of making},
author = {Elliott, D C and Frye, J G},
abstractNote = {The present invention is based upon the surprising discovery that a 5-carbon compound selected from the group of 4-oxopentanoic acid, at least one lactone of 4-oxopentanoic acid, and combinations thereof, may be hydrogenated with a bimetallic catalyst of a noble metal in combination with a second metal and preserve the pendant methyl group. It was further unexpectedly discovered that the same conditions of bimetallic catalyst in the presence of hydrogen are useful for catalyzing the different intermediate reactions, for example, angelicalactone to gamma-valerolactone and gamma-valerolactone to 1,4-pentanediol. Finally, it was surprising that levulinic acid could be converted to 2-methyltetrahydrofuran with heating in the presence of the bimetallic catalyst and hydrogen in a single process vessel. The method of the present invention unexpectedly produced a fuel or fuel component having 2-methyltetrahydrofuran either in a yield greater than 4.5 mol % or in combination with alcohols. 8 figs.},
doi = {},
url = {https://www.osti.gov/biblio/335448}, journal = {},
number = ,
volume = ,
place = {United States},
year = {1999},
month = {3}
}

Works referenced in this record:

Levulinic Acid as a Basic Chemical Raw Material
journal, August 1956


The Hydrogenation of Unsaturated Lactones to Desoxy Acids
journal, July 1930


Normal Valerolactone
journal, December 1926


Rhenium and Its Compounds as Hydrogenation Catalysts. III. Rhenium Heptoxide 1,2,3
journal, December 1959


The Catalytic Hydrogenation of Some Organic Acids in Alkaline Solution
journal, April 1939


The Catalytic Hydrogenation of Esters to Alcohols. ii
journal, March 1932


The Reduction of Aldehydes and Ketones with Nickel—Aluminum Alloy in Aqueous Alkaline Solution 1
journal, November 1962


Selectivity versus reactivity: The safe, efficient metal hydride reduction of a bifunctional organic
journal, April 1993


Normal Valerolactone. iii. its Preparation by the Catalytic Reduction of Levulinic acid with Hydrogen in the Presence of Platinum Oxide
journal, July 1930


Anionic ruthenium iodorcarbonyl complexes as selective dehydroxylation catalysts in aqueous solution
journal, October 1991


Rhenium Catalysts. VI. Rhenium(IV) Oxide Hydrate 1
journal, September 1963


Derivatives of γ-Valerolactone, 1,4-Pentanediol and 1,4-Di-(β-cyanoethoxy)-pentane 1
journal, August 1947


Ueber γ-Pentylenglycol und sein Anhydrid (Tetrahydromethylfurfuran)
journal, July 1889


ChemInform Abstract: LEVULINIC ACID, A NEW CHEMICAL RAW MATERIAL. ITS CHEMISTRY AND USE
journal, January 1976