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.
- Inventors:
-
- Richland, WA
- Issue Date:
- Research Org.:
- Battelle Memorial Institute, Columbus, OH (United States)
- OSTI Identifier:
- 872198
- Patent Number(s):
- 5883266
- Assignee:
- Battelle Memorial Institute (Richland, WA)
- Patent Classifications (CPCs):
-
C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07D - HETEROCYCLIC COMPOUNDS
- DOE Contract Number:
- AC06-76RL01830
- Resource Type:
- Patent
- Country of Publication:
- United States
- Language:
- English
- Subject:
- hydrogenated; 5-carbon; compound; method; based; surprising; discovery; selected; 4-oxopentanoic; acid; lactone; combinations; bimetallic; catalyst; noble; metal; combination; preserve; pendant; methyl; unexpectedly; discovered; conditions; presence; hydrogen; useful; catalyzing; intermediate; reactions; example; angelicalactone; gamma-valerolactone; 4-pentanediol; finally; levulinic; converted; 2-methyltetrahydrofuran; heating; single; process; vessel; produced; fuel; component; yield; mol; alcohols; compound selected; noble metal; carbon compound; levulinic acid; metallic catalyst; bimetallic catalyst; process vessel; single process; fuel component; anoic acid; /999/
Citation Formats
Elliott, Douglas C, and Frye, John G. Hydrogenated 5-carbon compound and method of making. United States: N. p., 1999.
Web.
Elliott, Douglas C, & Frye, John G. Hydrogenated 5-carbon compound and method of making. United States.
Elliott, Douglas C, and Frye, John G. Fri .
"Hydrogenated 5-carbon compound and method of making". United States. https://www.osti.gov/servlets/purl/872198.
@article{osti_872198,
title = {Hydrogenated 5-carbon compound and method of making},
author = {Elliott, Douglas C and Frye, John 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.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {Fri Jan 01 00:00:00 EST 1999},
month = {Fri Jan 01 00:00:00 EST 1999}
}
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