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US 8,273,138 B2Granted
Liquid fuel compositions
AssigneesShell Oil Company, Virent, Inc.
InventorsJoanna Margaret Bauldreay, Paul George Blommel, Randy Douglas Cortright, Richard John Price
Life of this patent
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Abstract
Liquid fuel compositions comprising one or more C4+ compounds derived from a water-soluble oxygenated hydrocarbon.
Claims43
A fuel component comprising:
- a lighter fraction of a carbohydrate derived component having at least one C4+ compound, the lighter fraction exhibiting:
- a mean percentage of 99% or more biobased material, as determined by C14 testing;
- a final boiling point in the range of from 150 to 220 ° C.;
- a component density at 15° C. in the range of from 700 to 890 kg/m3;
- a component sulfur content of at most 5 mg/kg;
- a component RON in the range of from 80 to 110;
- a component MON in the range of from 70 to 100;
- a benzene content of at most 10 vol. %;
- and, 21.7 wt. % or less of one or more carbohydrate derived C4+ alkenes;
- the lighter fraction comprising:
- a combined total of about 18 wt. % or more of one or more of carbohydrate derived aromatics comprising (a) a combination of multi-substituted carbohydrate derived aromatic compounds comprising substituents selected from the group consisting of C1-4 alkyls and (b) one or more substituted or unsubstituted aromatic selected from the group consisting of fused aryls, indane, indene, isomers thereof, and combinations thereof, wherein substituents on substituted aromatic are selected from the group consisting of straight chain C1-4 alkyls and combinations thereof;
- a combined total of about 7.9 wt. % or more of one or more C5+ alkanes comprising a first quantity of one or more branched carbohydrate derived C5+ alkanes, and a second quantity of one or more straight chain carbohydrate derived C5+ alkanes;
- and
- a combined total of about 1 wt. % or more of (a) an unsubstituted carbohydrate derived C5+ cycloalkane, and (b) one or more substituted carbohydrate derived cycloalkane comprising one or more substituent selected from the group consisting of branched C3-4 alkyls, straight chain C1-4 alkyls, branched C3-4 alkylenes, and straight chain C1-4 alkylenes;
- wherein the lighter fraction is a product produced by a process comprising:
- (a) providing water and carbohydrate derived water-soluble oxygenated hydrocarbon comprising C1+O1+ hydrocarbon in an aqueous liquid phase and/or a vapor phase;
- (b) providing H2;
- (c) catalytically reacting in the liquid and/or vapor phase the carbohydrate derived water-soluble oxygenated hydrocarbon with the H2 in the presence of a deoxygenation catalyst at a deoxygenation temperature and deoxygenation pressure to produce carbohydrate derived oxygenate comprising C1+O1-3 hydrocarbon in a reaction stream;
- and
- (d) catalytically reacting in the liquid and/or vapor phase the carbohydrate derived oxygenate under condensation conditions comprising the presence of a condensation catalyst and a condensation temperature of 325° C. or higher, the condensation conditions being effective to produce the carbohydrate derived component having at least one C4+ compound;
- and,
- (e) separating the lighter fraction from the carbohydrate derived component.
19 more elements
A fuel component comprising:
- a lighter fraction of a carbohydrate derived component having at least one C4+ compound, the lighter fraction exhibiting a mean percentage of 99% or more biobased material, as determined by C14 testing, the lighter fraction exhibiting:
- a final boiling point in the range of from 150 to 220° C.;
- a component density at 15° C. in the range of from 700 to 890 kg/m3;
- a component sulfur content of at most 5 mg/kg;
- a component RON in the range of from 80 to 110;
- a component MON in the range of from 70 to 100;
- and a benzene content of at most 10 vol. %;
- the lighter fraction comprising:
- a combined total of from about 8.5 wt. % to about 29.6 wt. % of a combination of one or more branched and one or more straight chain carbohydrate derived C5+ alkanes;
- a combined total of about 1 wt. % or more of (a) an unsubstituted carbohydrate derived C5+ cycloalkane, and (b) one or more substituted carbohydrate derived cycloalkane comprising one or more substituent selected from the group consisting of branched C3-4 alkyls, straight chain C1-4 alkyls, branched C3-4 alkylenes, and straight chain C1-4 alkylenes;
- a combined total of from about 18 wt. % to about 79.1 wt. % of one or more carbohydrate derived aromatics comprising (a) a combination of multi-substituted carbohydrate derived aromatic compounds comprising substituents selected from the group consisting of C1-4 alkyls, and (b) one or more substituted or unsubstituted aromatic selected from the group consisting of fused aryls, indane, indene, isomers thereof, and combinations thereof, wherein substituents on substituted aromatic are selected from the group consisting straight chain C1-4 alkyls and combinations thereof;
- and,
- a combined total of from 0.1 wt. % to about 21.7 wt. %, based on the weight of the feed carbon, of one or more carbohydrate derived C5+ alkenes.
10 more elements
A fuel component comprising:
- a lighter fraction of a carbohydrate derived component having at least one C4+ compound, the lighter fraction exhibiting:
- a mean percentage of 99% or more biobased material, as determined by C14 testing;
- a final boiling point in the range of from 150 to 220° C.;
- a component density at 15° C. in the range of from 700 to 890 kg/m3;
- a component sulfur content of at most 5 mg/kg;
- a component RON in the range of from 80 to 110;
- and, a component MON in the range of from 70 to 100;
- a benzene content of at most 10 vol. %;
- and, about 21.7 wt. % or less of one or more carbohydrate derived C5+ alkenes;
- the lighter fraction comprising:
- a total of about 7.9 wt. % or more of one or more carbohydrate derived C5+ alkanes, at least some of the carbohydrate derived C5+ alkanes being branched alkanes, about 10 wt. % or more of the carbohydrate derived component having 6 carbon atoms or less and less than about 5 wt. % of the carbohydrate derived component having 7 carbon atoms;
- a combined total of about 1 wt. % or more of (a) an unsubstituted carbohydrate derived C5+ cycloalkane, and (b) one or more substituted carbohydrate derived cycloalkane comprising one or more substituent selected from the group consisting of branched C3-4 alkyls, straight chain C1-4 alkyls, branched C3-4 alkylenes, and straight chain C1-4 alkylenes;
- a combined total of about 48.4 wt. % or more of one or more carbohydrate derived aromatics comprising (a) a combination of multi-substituted carbohydrate derived aromatic compounds comprising substituents selected from the group consisting of C1-4 alkyls, and (b) one or more substituted or unsubstituted aromatic selected from the group consisting of fused aryls, indane, indene, isomers thereof, and combinations thereof, wherein substituents on substituted aromatic are selected from the group consisting, straight chain C1-4 alkyls and combinations thereof.
10 more elements
A gasoline composition comprising:
- a lighter fraction of a carbohydrate derived component having at least one C4+ compound, the lighter fraction exhibiting:
- a mean percentage of 99% or more biobased material, as determined by C14 testing;
- a final boiling point in the range of from 150 to 220° C.;
- a component density at 15° C. in the range of from 700 to 890 kg/m3;
- a component sulfur content of at most 5 mg/kg;
- a component RON in the range of from 80 to 110;
- a component MON in the range of from 70 to 100;
- a benzene content of at most 10 vol. %;
- and, about 21.7 wt. % or less of one or more carbohydrate derived C5+ alkenes;
- and,
- one or more different gasoline blend components;
- the lighter fraction comprising:
- a combined total of about 18 wt. % or more of an amount of carbohydrate derived aromatics comprising (a) a combination of multi-substituted carbohydrate derived aromatic compounds comprising substituents selected from the group consisting of C1-4 alkyls and (b) one or more substituted or unsubstituted aromatic selected from the group consisting of fused aryls, indane, indene, isomers thereof, and combinations thereof, wherein substituents on substituted aromatic are selected from the group consisting straight chain C1-4 alkyls and combinations thereof;
- a combined total of about 7.9 wt. % or more C5+ alkanes comprising a first quantity of one or more branched carbohydrate derived C5+ alkanes and a second quantity of one or more straight chain carbohydrate derived C5+ alkanes;
- a combined total of about 1 wt. % or more of (a) an unsubstituted carbohydrate derived C5+ cycloalkane, and (b) one or more substituted carbohydrate derived cycloalkane comprising one or more substituent selected from the group consisting of branched C3-4 alkyls, straight chain C1-4 alkyls, branched C3-4 alkylenes, and straight chain C1-4 alkylenes;
- wherein the lighter fraction is a product made by a process comprising:
- (a) providing water and carbohydrate derived water-soluble oxygenated hydrocarbon comprising C1+O1+ hydrocarbon in an aqueous liquid phase and/or a vapor phase;
- (b) providing H2;
- (c) catalytically reacting in the liquid and/or vapor phase the carbohydrate derived water-soluble oxygenated hydrocarbon with the H2 in the presence of a deoxygenation catalyst at a deoxygenation temperature and deoxygenation pressure to produce carbohydrate derived oxygenate comprising C1+O1-3 hydrocarbon in a reaction stream;
- (d) catalytically reacting in the liquid and/or vapor phase the carbohydrate derived oxygenate under condensation conditions comprising the presence of a condensation catalyst and a condensation temperature of 325° C. or higher, the condensation conditions being effective to produce the carbohydrate derived component having at least one C4+ compound;
- and,
- (e) separating the lighter fraction from the carbohydrate derived component;
- the gasoline composition having an initial boiling point in the range of from 15° C. to 70° C. (IP123), a final boiling point of at most 220° C. (IP123), a RON in the range of from 85 to 110 (ASTM D2699) and a MON in the range of from 75 to 100 (ASTM D2700), and, a benzene content of at most 5%.vol.
20 more elements
A gasoline composition comprising:
- a lighter fraction of a carbohydrate derived C4+ component having at least one C4+ compound, the lighter fraction exhibiting:
- a mean percentage of 99% or more biobased material, as determined by C14 testing;
- a final boiling point in the range of from 150 to 220° C.;
- a component density at 15° C. in the range of from 700 to 890 kg/m3;
- a component sulfur content of at most 5 mg/kg;
- a component RON in the range of from 80 to 110;
- a component MON in the range of from 70 to 100;
- and, a benzene content of at most 10 vol. %;
- one or more different gasoline blend components;
- the carbohydrate derived fuel component comprising:
- a combined total of about 8.5 wt. % or more of a combination of one or more branched and one or more straight chain carbohydrate derived C5+ alkanes;
- a combined total of about 1 wt. % or more of (a) an unsubstituted carbohydrate derived C5+ cycloalkane, and (b) one or more substituted carbohydrate derived cycloalkane comprising one or more substituent selected from the group consisting of branched C3-4 alkyls, straight chain C1-4 alkyls, branched C3-4 alkylenes, and straight chain C1-4 alkylenes;
- a combined total of from about 18 wt. % to about 79.1 wt. % of one or more carbohydrate derived aromatics comprising (a) a combination of multi-substituted carbohydrate derived aromatic compounds comprising substituents selected from the group consisting of C1-4 alkyls and (b) one or more substituted or unsubstituted aromatic selected from the group consisting of fused aryls, indane, indene, isomers thereof, and combinations thereof, wherein substituents on substituted aromatic are selected from the group consisting straight chain C1-4 alkyls and combinations thereof;
- and,
- a combined total of from 0.1 wt. % to about 21.7 wt. % of one or more carbohydrate derived C5+ alkenes;
- the gasoline composition having an initial boiling point in the range of from 15° C. to 70° C. (IP123), a final boiling point of at most 220° C. (IP123), a RON in the range of from 85 to 110 (ASTM D2699), a MON in the range of from 75 to 100 (ASTM D2700);
- and, a benzene content of at most 5 vol. %.
14 more elements
A gasoline composition comprising:
- a lighter fraction of a carbohydrate derived C4+ component having at least one C4+ compound, the lighter fraction exhibiting:
- a mean percentage of 99% or more biobased material, as determined by C14 testing;
- a final boiling point in the range of from 150 to 220° C.;
- a component density at 15° C. in the range of from 700 to 890 kg/m3;
- a component sulfur content of at most 5 mg/kg;
- a component RON in the range of from 80 to 110;
- a component MON in the range of from 70 to 100;
- a benzene content of at most 10 vol. %;
- and, about 21.7 wt. % or less of one or more carbohydrate derived C5+ alkenes;
- the lighter fraction comprising:
- a total of about 7.9 wt. % or more of one or more carbohydrate derived C5+ alkanes, at least some of the carbohydrate derived C5+ alkanes being branched alkanes, about 10 wt.% or more of the carbohydrate derived component having 6 carbon atoms or less and less than about 5 wt. % of the carbohydrate derived component having 7 carbon atoms;
- a combined total of about 18 wt. % or more of one or more of carbohydrate derived aromatics comprising (a) a combination of multi-substituted carbohydrate derived aromatic compounds comprising substituents selected from the group consisting of C1-4 alkyls and (b) one or more substituted or unsubstituted aromatic selected from the group consisting of fused aryls, indane, indene, isomers thereof, and combinations thereof, wherein substituents on substituted aromatic are selected from the group consisting straight chain C1-4 alkyls and combinations thereof;
- and,
- a combined total of about 1 wt. % or more of (a) an unsubstituted carbohydrate derived C5+ cycloalkane, and (b) one or more substituted carbohydrate derived cycloalkane comprising one or more substituent selected from the group consisting of branched C3-4 alkyls, straight chain C1-4 alkyls, branched C3-4 alkvlenes, and straight chain C1-4 alkylenes;
- wherein the gasoline composition has an initial boiling point in the range of from 15° C. to 70° C. (IP123), a final boiling point of at most 220° C. (IP123), a RON in the range of from 85 to 110 (ASTM D2699);
- a MON in the range of from 75 to 100 (ASTM D2700);
- and, a benzene content of at most 5 vol. %.
14 more elements
An aviation gasoline composition comprising:
- a lighter fraction of a carbohydrate derived C4+ component having at least one C4+ compound, the lighter fraction exhibiting:
- a mean percentage of 99% or more biobased material, as determined by C14 testing;
- a final boiling point of at most 170° C.;
- a component density at 15° C. in the range of from 700 to 890 kg/m3;
- a component sulfur content of at most 5 mg/kg;
- a component RON in the range of from 80 to 110;
- a component MON in the range of from 70 to 100;
- a benzene content of at most 10 vol. %;
- and, about 21.7 wt. % or less of one or more carbohydrate derived C5+ alkenes;
- and,
- one or more different gasoline blend components;
- the lighter fraction comprising:
- a combined total of about 18 wt. % or more of one or more carbohydrate derived aromatics comprising (a) a combination of multi-substituted carbohydrate derived aromatic compounds comprising substituents selected from the group consisting of C1-4 alkyls and (b) one or more substituted or unsubstituted aromatic selected from the group consisting of fused aryls, indane, indene, isomers thereof, and combinations thereof, wherein substituents on substituted aromatic are selected from the group consisting straight chain C1-4 alkyls and combinations thereof;
- a combined total of about 7.9 wt. % or more C5+ alkanes comprising a first quantity of one or more branched carbohydrate derived C5+ alkanes and a second quantity of one or more straight chain carbohydrate derived C5+ alkanes;
- a combined total of about 1 wt. % or more of (a) an unsubstituted carbohydrate derived C5+ cycloalkane, and (b) one or more substituted carbohydrate derived cycloalkane comprising one or more substituent selected from the group consisting of branched C3-4 alkyls, straight chain C1-4 alkyls, branched C3-4 alkylenes, and straight chain C1-4 alkylenes;
- wherein the lighter fraction is a product made by a process comprising:
- (a) providing water and carbohydrate derived water-soluble oxygenated hydrocarbon comprising C1+O1+ hydrocarbon in an aqueous liquid phase and/or a vapor phase;
- (b) providing H2;
- (c) catalytically reacting in the liquid and/or vapor phase the carbohydrate derived water-soluble oxygenated hydrocarbon with the H2 in the presence of a deoxygenation catalyst at a deoxygenation temperature and deoxygenation pressure to produce carbohydrate derived oxygenate comprising C1+O1-3 hydrocarbon in a reaction stream;
- (d) catalytically reacting in the liquid and/or vapor phase the carbohydrate derived oxygenate under condensation conditions comprising the presence of a condensation catalyst and a condensation temperature of 325° C. or higher, the condensation conditions being effective to produce the carbohydrate derived component having at least one C4+ compound;
- and,
- (e) separating the lighter fraction from the carbohydrate derived component;
- the aviation gasoline comprising a Reid Vapor Pressure at 37.8° C. in the range of from 38.0 to 49.0 kPa (ASTM D323), a final boiling point of at most 170° C. (IP123), a Lean Mixture Motor Octane Number of 80 or more, a Rich Mixture Octane Number of 87 or more, and a tetraethyl lead content of at most 0.85 gPb/l;
- and, a benzene content of at most 5 vol. %.
21 more elements
A fuel component comprising:
- a mixture of carbohydrate derived branched and unbranched C4-14 alkanes;
- one or more alkenes selected from the group consisting of unbranched and branched carbohydrate derived C4-14 alkenes;
- one or more unsubstituted carbohydrate derived C5+ cycloalkane;
- one or more substituted carbohydrate derived C5+ cycloalkane comprising one or more substituent selected from the group consisting of branched C3-4 alkyls, straight chain C1-4 alkyls, branched C3-4 alkylenes, and straight chain C1-4 alkylenes;
- one or more unsubstituted carbohydrate derived C5+ cycloalkene;
- one or more substituted carbohydrate derived C5+ cycloalkene comprising one or more substituent selected from the group consisting of branched C3-4 alkyls, straight chain C1-4 alkyls, branched C3-4 alkylenes, and straight chain C1-4 alkylenes;
- one or more unsubstituted carbohydrate derived aromatic;
- one or more substituted carbohydrate derived aromatic comprising one or more substituent selected from the group consisting of branched C3-4 alkyls and straight chain C1-4 alkyls;
- one or more unsubstituted carbohydrate derived aromatic selected from the group consisting of fused aryls, indanes, indenes, isomers thereof, and combinations thereof, wherein substituents on substituted aromatic are selected from the group consisting straight chain C1-4 alkyls and combinations thereof;
- and,
- one or more substituted carbohydrate derived aromatic selected from the group consisting of fused aryls, indanes, indenes, isomers thereof, and combinations thereof, comprising one or more substituent selected from the group consisting of branched C3-4 alkyls and straight chain C1-4 alkyls;
- the fuel component exhibiting:
- a mean percentage of 99% or more biobased material, as determined by C14 testing;
- a final boiling point in the range of from 150 to 220° C.;
- a component density at 15° C. in the range of from 700 to 890 kg/m3;
- a component sulfur content of at most 5 mg/kg;
- a component RON in the range of from 80 to 110;
- a component MON in the range of from 70 to 100;
- a benzene content of at most 10 vol. %;
- and, about 21.7 wt. % or less of one or more carbohydrate derived C5+ alkenes.
17 more elements
Dependencies are inferred from the claim text.