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Title: Hydrogenated 5-carbon compound and method of making

Patent ·
OSTI ID:335448
;

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.

Research Organization:
Battelle Memorial Institute, Columbus, OH (United States)
Sponsoring Organization:
USDOE, Washington, DC (United States)
DOE Contract Number:
AC06-76RL01830
Assignee:
Battelle Memorial Inst., Richland, WA (United States)
Patent Number(s):
US 5,883,266/A/
OSTI ID:
335448
Resource Relation:
Other Information: PBD: 16 Mar 1999
Country of Publication:
United States
Language:
English

References (19)

Levulinic Acid as a Basic Chemical Raw Material journal August 1956
Synthetic Methods and Reactions; 99 1 . Preparation of Cyclic Ethers over Superacidic Perfluorinated Resinsulfonic Acid (Nafion-H) Catalyst journal January 1981
Preparation and properties of hydride triphenyl-phosphine ruthenium complexes with 3-formyl (or acyl) propionate [RuH(ocochrchrcor′)(PPh3)3] (R  H, CH3, C2H5; R  H, CH3, C6H5) and with 2-formyl (or acyl) benzoate [RuH(o-OCCOC6H4COR′)(PPh3)3] (R′  H, CH3) journal May 1982
The Hydrogenation of Unsaturated Lactones to Desoxy Acids journal July 1930
Normal Valerolactone journal December 1926
Homogeneous hydrogenations in aqueous solutions catalyzed by transition metal phosphine complexes journal January 1977
Peculiar kinetics of hydrogenations catalyzed by chlorotris-(sulphonated triphenylphosphine)rhodium(I) in aqueous solutions journal April 1984
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
I.—The synthetical formation of closed carbon-chains. Part II. On some derivatives of tetramethylene journal January 1887
ChemInform Abstract: LEVULINIC ACID, A NEW CHEMICAL RAW MATERIAL. ITS CHEMISTRY AND USE journal January 1976

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