[미국특허]
Synthesis of liquid fuels and chemicals from oxygenated hydrocarbons
원문보기
IPC분류정보
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
C07C-001/00
C10L-001/185
C10G-003/00
C07C-002/86
C10L-001/182
C07C-001/20
출원번호
US-0163412
(2011-06-17)
등록번호
US-8933281
(2015-01-13)
발명자
/ 주소
Cortright, Randy D.
Blommel, Paul G.
출원인 / 주소
Virent, Inc.
대리인 / 주소
Quarles & Brady LLP
인용정보
피인용 횟수 :
5인용 특허 :
117
초록▼
Processes and reactor systems are provided for the conversion of oxygenated hydrocarbons to hydrocarbons, ketones and alcohols useful as liquid fuels, such as gasoline, jet fuel or diesel fuel, and industrial chemicals. The process involves the conversion of mono-oxygenated hydrocarbons, such as alc
Processes and reactor systems are provided for the conversion of oxygenated hydrocarbons to hydrocarbons, ketones and alcohols useful as liquid fuels, such as gasoline, jet fuel or diesel fuel, and industrial chemicals. The process involves the conversion of mono-oxygenated hydrocarbons, such as alcohols, ketones, aldehydes, furans, carboxylic acids, diols, triols, and/or other polyols, to C4+ hydrocarbons, alcohols and/or ketones, by condensation. The oxygenated hydrocarbons may originate from any source, but are preferably derived from biomass.
대표청구항▼
1. A method of making a C4+ compound comprising: providing a feedstock stream comprising water and a biomass-derived oxygenate having two or more carbon atoms and one to three oxygen atoms, andcatalytically reacting the oxygenate in the vapor phase with hydrogen in the presence of a base condensatio
1. A method of making a C4+ compound comprising: providing a feedstock stream comprising water and a biomass-derived oxygenate having two or more carbon atoms and one to three oxygen atoms, andcatalytically reacting the oxygenate in the vapor phase with hydrogen in the presence of a base condensation catalyst comprising a member selected from the group consisting of Li, Na, K, Cs, B, Rb, Mg, Ca, Sr, Si, Ba, Al, Zn, Ce, La, Y, Sc, Y, Zr, Ti, hydrotalcite, phosphate, base-treated aluminosilicate zeolite, zinc-aluminate, a basic resin, basic nitride, alloys or combinations thereof, at a condensation temperature in the range of about 80° C. to 500° C. and a condensation pressure of at least 0.1 atm., to produce the C4+ compound,wherein the C4+ compound comprises a member selected from the group consisting of C4+ alcohol, C4+ ketone, C4+ alkane, C4+ alkene, C5+ cycloalkane, C5+ cycloalkene, aryl, fused aryl, and a mixture thereof. 2. The method of claim 1, wherein the biomass-derived oxygenate is a product of a fermentation process, pyrolysis process or Fischer-Tropsch process. 3. The method of claim 1, wherein the oxygenate comprises a member selected from the group consisting of an alcohol, ketone, aldehyde, carboxylic acid, diol, furan, furfurals, and a mixture thereof. 4. The method of claim 1, wherein the base condensation catalyst further comprises an oxide selected from the group consisting of Ti, Zr, V, Nb, Ta, Mo, Cr, W, Mn, Re, Al, Ga, In, Co, Ni, Si, Cu, Zn, Sn, Cd, Mg, P, Fe, and combinations thereof. 5. The method of claim 1, wherein the condensation catalyst further comprises a metal selected from the group consisting of a Cu, Ag, Au, Pt, Ni, Fe, Co, Ru, Zn, Cd, Ga, In, Rh, Pd, Ir, Re, Mn, Cr, Mo, W, Sn, Os, alloys and combinations thereof. 6. The method of claim 1, wherein the condensation temperature is in the range of about 125° C. to 450° C. 7. The method of claim 1, wherein the condensation temperature is in the range of about 125° C. to 250° C., and wherein the condensation pressure is a pressure where at least a portion of the oxygenates are in the vapor phase. 8. The method of claim 1, wherein the oxygenate comprises one or more members selected from the group consisting of an alcohol, ketone, aldehyde, furan, diol, triol, hydroxy carboxylic acid, carboxylic acid, a mixture of any of the foregoing, methanol, ethanol, n-propyl alcohol, isopropyl alcohol, butyl alcohol, pentanol, hexanol, cyclopentanol, cyclohexanol, 2-methylcyclopentanol, hydroxyketones, cyclic ketones, acetone, propanone, butanone, pentanone, hexanone, 2-methyl-cyclopentanone, ethylene glycol, 1,3-propanediol, propylene glycol, butanediol, pentanediol, hexanediol, methylglyoxal, butanedione, pentanedione, diketohexane, hydroxyaldehydes, acetaldehyde, propionaldehyde, butyraldehyde, pentanal, hexanal, formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, lactic acid, glycerol, furan, tetrahydrofuran, dihydrofuran, 2-furan methanol, 2-methyltetrahydrofuran, 2,5-dimethyl-tetrahydrofuran, 2-ethyl-tetrahydrofuran, 2-methyl furan, 2,5-dimethyl furan, 2-ethyl furan, hydroxylmethylfurfural, 3-hydroxytetrahydrofuran, tetrahydro-3-furanol, 5-hydroxymethyl-2(5H)-furanone, dihydro-5-(hydroxymethyl)-2(3H)-furanone, tetrahydro-2-furoic acid, dihydro-5-(hydroxymethyl)-2(3H)-furanone, tetrahydrofurfuryl alcohol, 1-(2-furyl)ethanol, and hydroxymethyltetrahydrofurfural, isomers of any of methanol through hydroxymethyltetrahydrofurfural, and combinations of any of methanol through hydroxymethyltetrahydrofurfural, and wherein the oxygenate optionally further comprises recycled C1+O1−3 hydrocarbon. 9. The method of claim 1, wherein the C4+ compound comprises a member selected from a branched or straight chain C4−30 alkane; a branched or straight chain alkane selected from the group consisting of C4−9, C7−14, C12−24, and a mixture thereof; a branched or straight chain C4−30 alkene; a branched or straight chain alkene selected from the group consisting of C4−9, C7−14, C12−24, and a mixture thereof; a mono-substituted or multi-substituted C5+ cycloalkane, and wherein at least one substituted group is a member selected from the group consisting of a branched C3+ alkyl, a straight chain C1+ alkyl, a branched C3+ alkylene, a straight chain C1+ alkylene, a phenyl, and a combination thereof; a mono-substituted or multisubstituted C5+ cycloalkene, and wherein at least one substituted group is a member selected from the group consisting of a branched C3+ alkyl, a straight chain C1+ alkyl, a branched C3+ alkylene, a straight chain C2+ alkylene, a phenyl, and a combination thereof; an unsubstituted aryl; a mono-substituted or multi-substituted aryl, and wherein at least one substituted group is a member selected from the group consisting of a branched C3+ alkyl, a straight chain C1+ alkyl, a branched C3+ alkylene, a straight chain C2+ alkylene, a phenyl, and a combination thereof; an unsubstituted fused aryl; a mono-substituted or multi-substituted fused aryl, and wherein at least one substituted group is a member selected from the group consisting of a branched C3+ alkyl, a straight chain C1+ alkyl, a branched C3+ alkylene, a straight chain C2+ alkylene, a phenyl, and a combination thereof; a compound according to the formula R1—OH, and a compound according to the formula wherein R1 is a member selected from the group consisting of a branched C4+ alkyl, straight chain C4+ alkyl, a branched C4+ alkylene, a straight chain C4+ alkylene, a substituted C5+ cycloalkane, an unsubstituted C5+ cycloalkane, a substituted C5+ cycloalkene, an unsubstituted C5+ cycloalkene, an aryl, a phenyl, and a combination thereof, and wherein R3 and R4 are independently a member selected from the group consisting of a branched C3+ alkyl, a straight chain C1+ alkyl, a branched C3+ alkylene, a straight chain C2+ alkylene, a substituted C5+ cycloalkane, an unsubstituted C5+ cycloalkane, a substituted C5+ cycloalkene, an unsubstituted C5+ cycloalkene, an aryl, a phenyl, and a combination thereof.
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