Hydrogenated 5-carbon compound and method of making

Elliott, D C; Frye, J G

Advanced Search OptionsAdvanced Search queries use a traditional Term Search. For more info, see our FAQ.

All Fields:

Patent Title:

Abstract:

Assignee:

Inventor(s):

Patent Number:

Patent Classification (CPC):

All Classifications
A - human necessities
A01 - agriculture
A21 - baking
A22 - butchering
A23 - foods or foodstuffs
A24 - tobacco
A41 - wearing apparel
A42 - headwear
A43 - footwear
A44 - haberdashery
A45 - hand or travelling articles
A46 - brushware
A47 - furniture
A61 - medical or veterinary science
A62 - life-saving
A63 - sports
A99 - subject matter not otherwise provided for in this section
B - performing operations
B01 - physical or chemical processes or apparatus in general
B02 - crushing, pulverising, or disintegrating
B03 - separation of solid materials using liquids or using pneumatic tables or jigs
B04 - centrifugal apparatus or machines for carrying-out physical or chemical processes
B05 - spraying or atomising in general
B06 - generating or transmitting mechanical vibrations in general
B07 - separating solids from solids
B08 - cleaning
B09 - disposal of solid waste
B21 - mechanical metal-working without essentially removing material
B22 - casting
B23 - machine tools
B24 - grinding
B25 - hand tools
B26 - hand cutting tools
B27 - working or preserving wood or similar material
B28 - working cement, clay, or stone
B29 - working of plastics
B30 - presses
B31 - making articles of paper, cardboard or material worked in a manner analogous to paper
B32 - layered products
B33 - additive manufacturing technology
B41 - printing
B42 - bookbinding
B43 - writing or drawing implements
B44 - decorative arts
B60 - vehicles in general
B61 - railways
B62 - land vehicles for travelling otherwise than on rails
B63 - ships or other waterborne vessels
B64 - aircraft
B65 - conveying
B66 - hoisting
B67 - opening, closing {or cleaning} bottles, jars or similar containers
B68 - saddlery
B81 - microstructural technology
B82 - nanotechnology
B99 - subject matter not otherwise provided for in this section
C - chemistry
C01 - inorganic chemistry
C02 - treatment of water, waste water, sewage, or sludge
C03 - glass
C04 - cements
C05 - fertilisers
C06 - explosives
C07 - organic chemistry
C08 - organic macromolecular compounds
C09 - dyes
C10 - petroleum, gas or coke industries
C11 - animal or vegetable oils, fats, fatty substances or waxes
C12 - biochemistry
C13 - sugar industry
C14 - skins
C21 - metallurgy of iron
C22 - metallurgy
C23 - coating metallic material
C25 - electrolytic or electrophoretic processes
C30 - crystal growth
C40 - combinatorial technology
C99 - subject matter not otherwise provided for in this section
D - textiles
D01 - natural or man-made threads or fibres
D02 - yarns
D03 - weaving
D04 - braiding
D05 - sewing
D06 - treatment of textiles or the like
D07 - ropes
D10 - indexing scheme associated with sublasses of section d, relating to textiles
D21 - paper-making
D99 - subject matter not otherwise provided for in this section
E - fixed constructions
E01 - construction of roads, railways, or bridges
E02 - hydraulic engineering
E03 - water supply
E04 - building
E05 - locks
E06 - doors, windows, shutters, or roller blinds in general
E21 - earth drilling
E99 - subject matter not otherwise provided for in this section
F - mechanical engineering
F01 - machines or engines in general
F02 - combustion engines
F03 - machines or engines for liquids
F04 - positive - displacement machines for liquids
F05 - indexing schemes relating to engines or pumps in various subclasses of classes f01-f04
F15 - fluid-pressure actuators
F16 - engineering elements and units
F17 - storing or distributing gases or liquids
F21 - lighting
F22 - steam generation
F23 - combustion apparatus
F24 - heating
F25 - refrigeration or cooling
F26 - drying
F27 - furnaces
F28 - heat exchange in general
F41 - weapons
F42 - ammunition
F99 - subject matter not otherwise provided for in this section
G - physics
G01 - measuring
G02 - optics
G03 - photography
G04 - horology
G05 - controlling
G06 - computing
G07 - checking-devices
G08 - signalling
G09 - education
G10 - musical instruments
G11 - information storage
G12 - instrument details
G16 - information and communication technology [ict] specially adapted for specific application fields
G21 - nuclear physics
G99 - subject matter not otherwise provided for in this section
H - electricity
H01 - basic electric elements
H02 - generation
H03 - basic electronic circuitry
H04 - electric communication technique
H05 - electric techniques not otherwise provided for
H99 - subject matter not otherwise provided for in this section
Y - new / cross sectional technologies
Y02 - technologies or applications for mitigation or adaptation against climate change
Y04 - information or communication technologies having an impact on other technology areas
Y10 - technical subjects covered by former uspc

More Options ...

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:: Elliott, D C; Frye, J G

Issue Date:: Tue Mar 16 00:00:00 EST 1999

Research Org.:: Battelle Memorial Institute, Columbus, OH (United States)

Sponsoring Org.:: USDOE, Washington, DC (United States)

OSTI Identifier:: 335448

Patent Number(s):: 5883266

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.

Copy to clipboard


                    Elliott, D C, & Frye, J G. Hydrogenated 5-carbon compound and method of making.  United States.

Copy to clipboard


                    Elliott, D C, and Frye, J G. Tue .  
        "Hydrogenated 5-carbon compound and method of making".  United States.

Copy to clipboard


                    
@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          = {},

  journal      = {},
number       = ,

  volume       = ,

  place        = {United States},

  year         = {Tue Mar 16 00:00:00 EST 1999},

  month        = {Tue Mar 16 00:00:00 EST 1999}

}

Copy to clipboard

Patent:

Search for the full text at the U.S. Patent and Trademark Office

Save / Share:

Export Metadata

Save to My Library

Works referenced in this record:

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

Leonard, Reid H.
Industrial & Engineering Chemistry, Vol. 48, Issue 8
https://doi.org/10.1021/ie50560a033

Synthetic Methods and Reactions; 99 ¹ . Preparation of Cyclic Ethers over Superacidic Perfluorinated Resinsulfonic Acid (Nafion-H) Catalyst
journal, January 1981

Olah, George A.; Fung, Alexander P.; Malhotra, Ripudaman
Synthesis, Vol. 1981, Issue 06
https://doi.org/10.1055/s-1981-29494

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

Osakada, Kohtaro; Ikariya, Takao; Yoshikawa, Sadao
Journal of Organometallic Chemistry, Vol. 231, Issue 1
https://doi.org/10.1016/S0022-328X(00)89230-X

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

Jacobs, Walter A.; Scott, Albert B.
Journal of Biological Chemistry, Vol. 87, Issue 3
https://doi.org/10.1016/S0021-9258(18)76838-5

Normal Valerolactone
journal, December 1926

Schuette, H. A.; Sah, Peter P. T.
Journal of the American Chemical Society, Vol. 48, Issue 12
https://doi.org/10.1021/ja01691a022

Homogeneous hydrogenations in aqueous solutions catalyzed by transition metal phosphine complexes
journal, January 1977

Joó, F.; Tóth, Z.; Beck, M. T.
Inorganica Chimica Acta, Vol. 25
https://doi.org/10.1016/S0020-1693(00)95645-7

Peculiar kinetics of hydrogenations catalyzed by chlorotris-(sulphonated triphenylphosphine)rhodium(I) in aqueous solutions
journal, April 1984

Joó, F.; Somsák, L.; Beck, M. T.
Journal of Molecular Catalysis, Vol. 24, Issue 1
https://doi.org/10.1016/0304-5102(84)85040-3

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

Broadbent, H. Smith; Campbell, Graham C.; Bartley, William J.
The Journal of Organic Chemistry, Vol. 24, Issue 12
https://doi.org/10.1021/jo01094a003

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

Allen, Bruce B.; Wyatt, B. Woodrow.; Henze, Henry R.
Journal of the American Chemical Society, Vol. 61, Issue 4
https://doi.org/10.1021/ja01873a019

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

Folkers, Karl; Adkins, Homer
Journal of the American Chemical Society, Vol. 54, Issue 3
https://doi.org/10.1021/ja01342a043

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

Cook, Paul L.
The Journal of Organic Chemistry, Vol. 27, Issue 11
https://doi.org/10.1021/jo01058a027

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

Smith, Katrina; Beauvais, Robert; Holman, R. W.
Journal of Chemical Education, Vol. 70, Issue 4
https://doi.org/10.1021/ed070pA94

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

Schuette, H. A.; Thomas, Ralph W.
Journal of the American Chemical Society, Vol. 52, Issue 7
https://doi.org/10.1021/ja01370a069

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

Braca, Giuseppe; Raspolli Galletti, Anna Maria; Sbrana, Glauco
Journal of Organometallic Chemistry, Vol. 417, Issue 1-2, p. 41-49
https://doi.org/10.1016/0022-328X(91)80159-H

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

Broadbent, H. Smith; Selin, Terry G.
The Journal of Organic Chemistry, Vol. 28, Issue 9
https://doi.org/10.1021/jo01044a045

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

Christian, Robert V.; Brown, Horace D.; Hixon, R. M.
Journal of the American Chemical Society, Vol. 69, Issue 8
https://doi.org/10.1021/ja01200a036

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

Lipp, A.
Berichte der deutschen chemischen Gesellschaft, Vol. 22, Issue 2
https://doi.org/10.1002/cber.188902202147

I.—The synthetical formation of closed carbon-chains. Part II. On some derivatives of tetramethylene
journal, January 1887

Perkin, W. H.
J. Chem. Soc., Trans., Vol. 51, Issue 0
https://doi.org/10.1039/CT8875100001

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

Kitano, M.; Tanimoto, F.; Okabayashi, M.
Chemischer Informationsdienst, Vol. 7, Issue 3
https://doi.org/10.1002/chin.197603129

Similar Records in DOE Patents and OSTI.GOV collections:

Hydrogenated 5-carbon compound and method of making

Patent Elliott, Douglas C [Richland, WA]; Frye, John G [Richland, WA]

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 withmore » « less
Full Text Available
Hydrogenolysis of 5-carbon sugars, sugar alcohols, and methods of making propylene glycol

Patent Werpy, Todd A [West Richland, WA]; Zacher, Alan H [Kennewick, WA]; Miller, Dennis J [Okemos, MI]

Methods and compositions for reactions of hydrogen over a Re-containing catalyst with compositions containing a 5-carbon sugar, sugar alcohol, or lactic acid are described. It has been surprisingly discovered that reaction with hydrogen over a Re-containing multimetallic catalyst resulted in superior conversion and selectivity to desired products such as propylene glycol. A process for the synthesis of PG from lactate or lactic acid is also described.
Full Text Available
Method of making metal oxide ceramic powders by using a combustible amino acid compound

Patent Pederson, L R; Chick, L A; Exarhos, G J

This invention is directed to the formation of homogeneous, aqueous precursor mixtures of at least one substantially soluble metal salt and a substantially soluble, combustible co-reactant compound, typically an amino acid. This produces, upon evaporation, a substantially homogeneous intermediate material having a total solids level which would support combustion. The homogeneous intermediate material essentially comprises highly dispersed or solvated metal constituents and the co-reactant compound. The intermediate material is quite flammable. A metal oxide powder results on ignition of the intermediate product which combusts same to produce the product powder.
Production method for making rare earth compounds

Patent McCallum, R W; Ellis, T W; Dennis, K W; ...

A method of making a rare earth compound, such as a earth-transition metal permanent magnet compound, without the need for producing rare earth metal as a process step, comprises carbothermically reacting a rare earth oxide to form a rare earth carbide and heating the rare earth carbide, a compound-forming reactant (e.g., a transition metal and optional boron), and a carbide-forming element (e.g., a refractory metal) that forms a carbide that is more thermodynamically favorable than the rare earth carbide whereby the rare earth compound (e.g., Nd{sub 2}Fe{sub 14}B or LaNi{sub 5}) and a carbide of the carbide-forming element are formed.

Similar Records

Title: Hydrogenated 5-carbon compound and method of making

Abstract

Citation Formats

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

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