US20130172546A1 - Compositions comprising c5 and c6 oligosaccharides - Google Patents
Compositions comprising c5 and c6 oligosaccharides Download PDFInfo
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- US20130172546A1 US20130172546A1 US13/649,294 US201213649294A US2013172546A1 US 20130172546 A1 US20130172546 A1 US 20130172546A1 US 201213649294 A US201213649294 A US 201213649294A US 2013172546 A1 US2013172546 A1 US 2013172546A1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
- C07H3/02—Monosaccharides
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
- C07H3/06—Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages
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- C—CHEMISTRY; METALLURGY
- C13—SUGAR INDUSTRY
- C13B—PRODUCTION OF SUCROSE; APPARATUS SPECIALLY ADAPTED THEREFOR
- C13B50/00—Sugar products, e.g. powdered, lump or liquid sugar; Working-up of sugar
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- C—CHEMISTRY; METALLURGY
- C13—SUGAR INDUSTRY
- C13K—SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
- C13K1/00—Glucose; Glucose-containing syrups
- C13K1/02—Glucose; Glucose-containing syrups obtained by saccharification of cellulosic materials
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- C—CHEMISTRY; METALLURGY
- C13—SUGAR INDUSTRY
- C13K—SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
- C13K1/00—Glucose; Glucose-containing syrups
- C13K1/02—Glucose; Glucose-containing syrups obtained by saccharification of cellulosic materials
- C13K1/04—Purifying
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- C—CHEMISTRY; METALLURGY
- C13—SUGAR INDUSTRY
- C13K—SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
- C13K11/00—Fructose
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- C—CHEMISTRY; METALLURGY
- C13—SUGAR INDUSTRY
- C13K—SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
- C13K13/00—Sugars not otherwise provided for in this class
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- C—CHEMISTRY; METALLURGY
- C13—SUGAR INDUSTRY
- C13K—SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
- C13K13/00—Sugars not otherwise provided for in this class
- C13K13/002—Xylose
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- C—CHEMISTRY; METALLURGY
- C13—SUGAR INDUSTRY
- C13K—SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
- C13K13/00—Sugars not otherwise provided for in this class
- C13K13/007—Separation of sugars provided for in subclass C13K
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E50/00—Technologies for the production of fuel of non-fossil origin
- Y02E50/10—Biofuels, e.g. bio-diesel
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
Definitions
- the present invention generally relates to compositions comprising C5 and C6 saccharides of varying degrees of polymerization and/or containing maximum levels of undesirable impurities, such as compounds containing sulfur, nitrogen, or metals, especially those processed from lignocellulosic biomass using supercritical, subcritical, and/or near critical fluid extraction.
- Processes using hot compressed water may have two distinct operations: pre-treatment and cellulose hydrolysis.
- the pre-treatment process hydrolyzes the hemicellulose component of the lignocellulosic biomass and cellulose hydrolysis (CH) process, as its name infers, hydrolyzes the cellulose fibers.
- CH cellulose hydrolysis
- the resultant five carbon (C5) and six carbon (C6) sugar streams are recovered separately.
- the remaining solids, which consist mostly of lignin, are preferably recovered, such as through filtration, and may be used as a fuel to provide thermal energy to the process itself or for other processes.
- the sugar streams may be converted to ethanol through fermentation using yeast or bacteria that feed on the sugars. As the sugars are consumed, ethanol and carbon dioxide are produced.
- the invention is directed to these compositions, as well as and other important ends.
- compositions comprising:
- At least one water-soluble C6 oligosaccharide hydrolysate especially those hydrolysates processed from lignocellulosic biomass using supercritical or near critical fluid extraction;
- said elements are Al, As, B, Ba, Be, Ca, Cd, Co, Cr, Cu, Fe, K, Li, Mg, Mn, Mo, Na, Ni, P, Pb, S, Sb, Se, Si, Sn, Sr, Ti, Tl, V, and Zn.
- compositions comprising:
- At least one water-soluble C6 oligosaccharide hydrolysate especially those hydrolysates processed from lignocellulosic biomass using supercritical or near critical fluid extraction;
- compositions comprising:
- At least one water-soluble C6 oligosaccharide hydrolysate especially those hydrolysates processed from lignocellulosic biomass using supercritical or near critical fluid extraction;
- compositions comprising:
- At least one water-soluble C6 oligosaccharide hydrolysate especially those hydrolysates processed from lignocellulosic biomass using supercritical or near critical fluid extraction;
- compositions comprising:
- At least one water-soluble C6 oligosaccharide hydrolysate especially those hydrolysates processed from lignocellulosic biomass using supercritical or near critical fluid extraction;
- compositions comprising:
- At least one water-soluble C6 oligosaccharide hydrolysate especially those hydrolysates processed from lignocellulosic biomass using supercritical or near critical fluid extraction;
- compositions comprising:
- compositions comprising:
- water-soluble C6 oligosaccharides have a degree of polymerization of about 2 to about 15.
- compositions comprising:
- At least one water-soluble C5 oligosaccharide hydrolysate especially those hydrolysates processed from lignocellulosic biomass using supercritical or near critical fluid extraction;
- said elements are Al, As, B, Ba, Be, Ca, Cd, Co, Cr, Cu, Fe, K, Li, Mg, Mn, Mo, Na, Ni, P, Pb, S, Sb, Se, Si, Sn, Sr, Ti, Tl, V, and Zn.
- compositions comprising:
- At least one water-soluble C5 oligosaccharide hydrolysate especially those hydrolysates processed from lignocellulosic biomass using supercritical or near critical fluid extraction;
- compositions comprising:
- At least one water-soluble C5 oligosaccharide hydrolysate especially those hydrolysates processed from lignocellulosic biomass using supercritical or near critical fluid extraction;
- compositions comprising:
- At least one water-soluble C5 oligosaccharide hydrolysate especially those hydrolysates processed from lignocellulosic biomass using supercritical or near critical fluid extraction;
- compositions comprising:
- At least one water-soluble C5 oligosaccharide hydrolysate especially those hydrolysates processed from lignocellulosic biomass using supercritical or near critical fluid extraction;
- compositions comprising:
- At least one water-soluble C5 oligosaccharide hydrolysate especially those hydrolysates processed from lignocellulosic biomass using supercritical or near critical fluid extraction;
- the invention is directed to methods of reducing the level of enzyme required for enzymatically hydrolyzing first water-soluble C6 saccharides having an average degree of polymerization to about 2 to about 15, preferably about 2 to about 10, and more preferably about 2 to about 6, to second water-soluble C6 saccharides having a lower average degree of polymerization than said average degree of polymerization of said first water-soluble C6 saccharides, comprising:
- hydrolysate comprising said first water-soluble C6 saccharides and less than about 5250 ppm in total, based on total weight of water-soluble C6 saccharide hydrolysate in said composition, of elements;
- said elements are Al, As, B, Ba, Be, Ca, Cd, Co, Cr, Cu, Fe, K, Li, Mg, Mn, Mo, Na, Ni, P, Pb, S, Sb, Se, Si, Sn, Sr, Ti, Tl, V, and Zn.
- the invention is directed to methods of reducing the level of enzyme required for enzymatically hydrolyzing first water-soluble C5 saccharides having an average degree of polymerization to about 2 to about 28, preferably about 2 to about 15, more preferably about 2 to about 13, even more preferably about 2 to about 6, to second water-soluble C5 saccharides having a lower average degree of polymerization than said average degree of polymerization of said first water-soluble C5 saccharides, comprising:
- hydrolysate comprising said first water-soluble C5 saccharides and less than about 3700 ppm in total, based on total weight of water-soluble C5 saccharide hydrolysate in said composition, of elements;
- said elements are Al, As, B, Ba, Be, Ca, Cd, Co, Cr, Cu, Fe, K, Li, Mg, Mn, Mo, Na, Ni, P, Pb, S, Sb, Se, Si, Sn, Sr, Ti, Tl, V, and Zn.
- FIG. 1A is a scan from a DIONEX high pressure liquid chromatography device with an electrochemical detector of a C6 oligosaccharide composition of one embodiment of the invention.
- FIG. 1B is a scan from a DIONEX high pressure liquid chromatography device with an electrochemical detector of a C6 oligosaccharide composition of one embodiment of the invention.
- FIG. 2A is a scan from a DIONEX high pressure liquid chromatography device with an electrochemical detector of a C5 oligosaccharide composition of one embodiment of the invention.
- FIG. 2B is a scan from a DIONEX high pressure liquid chromatography device with an electrochemical detector of a C5 oligosaccharide composition of one embodiment of the invention.
- the phrase “substantially free” means have no more than about 1%, preferably less than about 0.5%, more preferably, less than about 0.1%, by weight of a component, based on the total weight of any composition containing the component.
- a supercritical fluid is a fluid at a temperature above its critical temperature and at a pressure above its critical pressure.
- a supercritical fluid exists at or above its “critical point,” the point of highest temperature and pressure at which the liquid and vapor (gas) phases can exist in equilibrium with one another. Above critical pressure and critical temperature, the distinction between liquid and gas phases disappears.
- a supercritical fluid possesses approximately the penetration properties of a gas simultaneously with the solvent properties of a liquid. Accordingly, supercritical fluid extraction has the benefit of high penetrability and good solvation.
- Reported critical temperatures and pressures include: for pure water, a critical temperature of about 374.2° C., and a critical pressure of about 221 bar; for carbon dioxide, a critical temperature of about 31° C. and a critical pressure of about 72.9 atmospheres (about 1072 psig).
- Near critical water has a temperature at or above about 300° C. and below the critical temperature of water (374.2° C.), and a pressure high enough to ensure that all fluid is in the liquid phase.
- Sub-critical water has a temperature of less than about 300° C. and a pressure high enough to ensure that all fluid is in the liquid phase.
- Sub-critical water temperature may be greater than about 250° C. and less than about 300° C., and in many instances sub-critical water has a temperature between about 250° C.
- hot compressed water is used interchangeably herein for water that is at or above its critical state, or defined herein as near-critical or sub-critical, or any other temperature above about 50° C. (preferably, at least about 100° C.) but less than subcritical and at pressures such that water is in a liquid state.
- a fluid which is “supercritical” indicates a fluid which would be supercritical if present in pure form under a given set of temperature and pressure conditions.
- “supercritical water” indicates water present at a temperature of at least about 374.2° C. and a pressure of at least about 221 bar, whether the water is pure water, or present as a mixture (e.g. water and ethanol, water and CO 2 , etc).
- a mixture of sub-critical water and supercritical carbon dioxide indicates a mixture of water and carbon dioxide at a temperature and pressure above that of the critical point for carbon dioxide but below the critical point for water, regardless of whether the supercritical phase contains water and regardless of whether the water phase contains any carbon dioxide.
- a mixture of sub-critical water and supercritical CO 2 may have a temperature of about 250° C. to about 280° C. and a pressure of at least about 225 bar.
- lignocellulosic biomass or a component part thereof refers to plant biomass containing cellulose, hemicellulose, and lignin from a variety of sources, including, without limitation (1) agricultural residues (including corn stover and sugarcane bagasse), (2) dedicated energy crops, (3) wood residues (including hardwoods, softwoods, sawmill and paper mill discards), and (4) municipal waste, and their constituent parts including without limitation, lignocellulose biomass itself, lignin, saccharides (including cellulose, cellobiose, C 6 oligosaccharides, C 6 monosaccharides, C 6 saccharides (including hemicellulose, C 6 oligosaccharides, and C 6 monosaccharides), and mixtures thereof.
- agricultural residues including corn stover and sugarcane bagasse
- wood residues including hardwoods, softwoods, sawmill and paper mill discards
- municipal waste and their constituent parts including without limitation, lignocellulose biomass itself, lignin, saccharides (including cellulose, cellobio
- ash refers to the non-aqueous residue that remains after a sample is burned, and consists mostly of metal oxides. Ash content may be measured in accordance with ASTM Standard Method No. E1755-01 “Standard Method for the Determination of Ash in Biomass.” This test method covers the determination of ash, expressed as the percentage of residue remaining after dry oxidation at 550 to 600° C. All results are reported relative to the 105° C. oven dry weight of the sample.” See also: http://www.nrel.gov/biomass/pdfs/42622.pdf and http://www.astm.org/Standards/E1755.htm, which are both incorporated herein by reference in their entirety.
- degree of polymerization refers to the number of monomeric units in a macromolecule or polymer or oligomer molecule, including those monomeric units that are not identical (such as in a oligomer with different monomeric residues).
- the degree of polymerization (DP) of the various saccharides in the compositions of the invention may be measured using gel permeation chromatography (GPC), high pressure liquid chromatography (HPLC), such as DIONEX with an electrochemical detector, matrix-assisted laser desorption/ionization time-of-flight (MALDI-TOF) mass spectrometry, or other conventional molecular weight determination methods.
- compositions comprising C6 saccharides.
- compositions comprise:
- said elements are Al, As, B, Ba, Be, Ca, Cd, Co, Cr, Cu, Fe, K, Li, Mg, Mn, Mo, Na, Ni, P, Pb, S, Sb, Se, Si, Sn, Sr, Ti, Tl, V, and Zn.
- the elements are present at a level of less than about 5100 ppm in total by weight, based on total weight of said water-soluble C6 oligosaccharide hydrolysate and said water-soluble C6 monosaccharide hydrolysate in said composition.
- compositions comprising:
- compositions further comprise:
- said elements are Al, As, B, Ba, Be, Ca, Cd, Co, Cr, Cu, Fe, K, Li, Mg, Mn, Mo, Na, Ni, P, Pb, S, Sb, Se, Si, Sn, Sr, Ti, Tl, V, and Zn.
- compositions comprising:
- compositions further comprise:
- said elements are Al, As, B, Ba, Be, Ca, Cd, Co, Cr, Cu, Fe, K, Li, Mg, Mn, Mo, Na, Ni, P, Pb, S, Sb, Se, Si, Sn, Sr, Ti, Tl, V, and Zn.
- compositions comprising:
- compositions further comprise:
- said elements are Al, As, B, Ba, Be, Ca, Cd, Co, Cr, Cu, Fe, K, Li, Mg, Mn, Mo, Na, Ni, P, Pb, S, Sb, Se, Si, Sn, Sr, Ti, Tl, V, and Zn.
- compositions comprising:
- compositions further comprise:
- said elements are Al, As, B, Ba, Be, Ca, Cd, Co, Cr, Cu, Fe, K, Li, Mg, Mn, Mo, Na, Ni, P, Pb, S, Sb, Se, Si, Sn, Sr, Ti, Tl, V, and Zn.
- compositions comprising:
- compositions further comprise:
- said elements are Al, As, B, Ba, Be, Ca, Cd, Co, Cr, Cu, Fe, K, Li, Mg, Mn, Mo, Na, Ni, P, Pb, S, Sb, Se, Si, Sn, Sr, Ti, Tl, V, and Zn.
- the water-soluble C6 oligosaccharide hydrolysate has a degree of polymerization of about 2 to about 15. In other embodiments, water-soluble C6 oligosaccharide hydrolysate has a degree of polymerization of about 2 to about 13. In other embodiments, water-soluble C6 oligosaccharide hydrolysate has a degree of polymerization of about 2 to about 10. In other embodiments, water-soluble C6 oligosaccharide hydrolysate has a degree of polymerization of about 2 to about 6.
- compositions further comprise at least one water-soluble C6 monosaccharide hydrolysate.
- the water-soluble C6 monosaccharide hydrolysate is glucose, galactose, mannose, fructose, or a mixture thereof.
- compositions further comprise less than about 10 ppm, based on total weight of said water-soluble C6 oligosaccharide hydrolysate and said water-soluble C6 monosaccharide hydrolysate in said composition, of aluminum, preferably less than about 5 ppm by weight, based on total weight of said water-soluble C6 oligosaccharide hydrolysate and said water-soluble C6 monosaccharide hydrolysate in said composition, of aluminum.
- compositions further comprise less than about 3000 ppm by weight, based on total weight of said water-soluble C6 oligosaccharide hydrolysate and said water-soluble C6 monosaccharide hydrolysate in said composition, of calcium, preferably less than about 2950 ppm by weight, based on total weight of said water-soluble C6 oligosaccharide hydrolysate and said water-soluble C6 monosaccharide hydrolysate in said composition, of calcium.
- compositions further comprise less than about 350 ppm by weight, based on total weight of said water-soluble C6 oligosaccharide hydrolysate and said water-soluble C6 monosaccharide hydrolysate in said composition, of iron, preferably less than about 325 ppm by weight, based on total weight of said water-soluble C6 oligosaccharide hydrolysate and said water-soluble C6 monosaccharide hydrolysate in said composition, of iron.
- compositions further comprise less than about 1000 ppm by weight, based on total weight of said water-soluble C6 oligosaccharide hydrolysate and said water-soluble C6 monosaccharide hydrolysate in said composition, of sulfur, preferably less than about 975 ppm by weight, based on total weight of said water-soluble C6 oligosaccharide hydrolysate and said water-soluble C6 monosaccharide hydrolysate in said composition, of sulfur.
- the ratio of the total weight of said water-soluble C6 oligosaccharide hydrolysate and said water-soluble C6 monosaccharide hydrolysate to said elements is greater than about 45:1, preferably greater than about 47:1.
- the level of said elements are measured by inductively coupled plasma emission spectroscopy.
- compositions less than about 1500 mg of nitrogen per kg of total weight of water-soluble C6 saccharides, preferably less than about 1450 of nitrogen per kg of total weight of water-soluble C6 saccharides.
- Nitrogen may be measured by thermal conductivity detection after combustion and reduction.
- the weight ratio of the collective mass of hydrogen and nitrogen to mass of carbon present in said water-soluble C6 oligosaccharide hydrolysate and said water-soluble C6 monosaccharide hydrolysate is less than about 0.14.
- Carbon, hydrogen, and nitrogen levels may be measured by thermal conductivity detection after combustion and reduction.
- compositions comprising the C6 saccharides further comprise less than a maximum of any of the elements, individually or in combination, in the table listed below:
- compositions comprise:
- water-soluble C6 oligosaccharides have a degree of polymerization of about 2 to about 15.
- said water-soluble C6 oligosaccharides are present at a level of about 80% by weight to about 92.5% by weight, based on total weight of C6 saccharides present in said composition.
- said water-soluble C6 oligosaccharides have a degree of polymerization of about 2 to about 13, preferably, about 2 to about 10, and more preferably about 2 to about 6.
- the compositions further comprise about 5% by weight to about 20% by weight, based on total weight of C6 saccharides present in said composition, of C6 monosaccharides.
- said water-soluble C6 oligosaccharide hydrolysate comprises:
- compositions further comprise:
- compositions further comprise:
- compositions comprise:
- said C6 disaccharides are present at a level of about 10% by weight to about 20% by weight, based on total weight of C6 saccharides present in said composition.
- said C6 trisaccharides are present at a level of about 10% by weight to about 20% by weight, based on total weight of C6 saccharides present in said composition.
- said C6 tetrasaccharides are present at a level of about 10% by weight to about 20% by weight, based on total weight of C6 saccharides present in said composition.
- said C6 pentasaccharides are present at a level of about 10% by weight to about 20% by weight, based on total weight of C6 saccharides present in said composition.
- said C6 saccharides having at a degree of polymerization of at least about 6 are present at a level of about 10% by weight to about 20% by weight, based on total weight of C6 saccharides present in said composition.
- compositions further comprise:
- compositions further comprise about 7.5% by weight to about 20% by weight, based on total weight of said water-soluble C6 oligosaccharide hydrolysate and said water-soluble C6 monosaccharide hydrolysate in said composition, of C6 monosaccharides.
- compositions further comprise water.
- the water-soluble C6 oligosaccharide hydrolysate and the water-soluble C6 monosaccharide hydrolysate are processed from lignocellulosic biomass using supercritical, subcritical, or near critical fluid extraction, or a combination thereof.
- compositions comprising C5 oligosaccharides.
- the compositions comprise:
- said elements are Al, As, B, Ba, Be, Ca, Cd, Co, Cr, Cu, Fe, K, Li, Mg, Mn, Mo, Na, Ni, P, Pb, S, Sb, Se, Si, Sn, Sr, Ti, Tl, V, and Zn.
- compositions comprising:
- the elements are present at a level of less than about 3610 ppm in total by weight, based on total weight of said water-soluble C5 oligosaccharide hydrolysate and said water-soluble C5 monosaccharide hydrolysate in said composition.
- compositions comprising:
- compositions comprising:
- compositions comprising:
- compositions comprising:
- compositions described herein further comprise:
- said elements are Al, As, B, Ba, Be, Ca, Cd, Co, Cr, Cu, Fe, K, Li, Mg, Mn, Mo, Na, Ni, P, Pb, S, Sb, Se, Si, Sn, Sr, Ti, Tl, V, and Zn.
- the water-soluble C5 oligosaccharide hydrolysate has a degree of polymerization of at least about 2 to about 28. In other embodiments, water-soluble C5 oligosaccharide hydrolysate has a degree of polymerization of at least about 2 to about 15. In other embodiments, water-soluble C5 oligosaccharide hydrolysate has a degree of polymerization of at least about 2 to about 10. In other embodiments, water-soluble C5 oligosaccharide hydrolysate has a degree of polymerization of at least about 2 to about 6.
- compositions further comprise:
- At least one water-soluble C5 monosaccharide hydrolysate at least one water-soluble C5 monosaccharide hydrolysate.
- the water-soluble C5 monosaccharide hydrolysate is xylose, arabinose, lyxose, ribose, or a mixture thereof.
- compositions further comprise less than about 10 ppm by weight, based on total weight of said water-soluble C5 oligosaccharide hydrolysate and said water-soluble C5 monosaccharide hydrolysate in said composition, of aluminum, preferably less than about 5 ppm by weight, based on total weight of said water-soluble C5 oligosaccharide hydrolysate and said water-soluble C5 monosaccharide hydrolysate in said composition, of aluminum.
- compositions further comprise less than about 2300 ppm by weight, based on total weight of said water-soluble C5 oligosaccharide hydrolysate and said water-soluble C5 monosaccharide hydrolysate in said composition, of calcium, preferably less than about 2250 ppm by weight, based on total weight of said water-soluble C5 oligosaccharide hydrolysate and said water-soluble C5 monosaccharide hydrolysate in said composition, of calcium.
- compositions further comprise less than about 50 ppm by weight, based on total weight of said water-soluble C5 oligosaccharide hydrolysate and said water-soluble C5 monosaccharide hydrolysate in said composition, of iron, preferably less than about 30 ppm by weight, based on total weight of said water-soluble C5 oligosaccharide hydrolysate and said water-soluble C5 monosaccharide hydrolysate in said composition, of iron.
- compositions further comprise less than about 150 ppm by weight, based on total weight of said water-soluble C5 oligosaccharide hydrolysate and said water-soluble C5 monosaccharide hydrolysate in said composition, of sulfur, preferably less than about 140 ppm by weight, based on total weight of said water-soluble C5 oligosaccharide hydrolysate and said water-soluble C5 monosaccharide hydrolysate in said composition, of sulfur.
- the ratio of total weight of said water-soluble C5 oligosaccharide hydrolysate and said water-soluble C5 monosaccharide hydrolysate in said composition to said elements is greater than about 75:1, preferably greater than about 80:1.
- the water-soluble C5 oligosaccharide hydrolysate is processed from lignocellulosic biomass using supercritical, subcritical, or near critical fluid extraction, or a combination thereof.
- the level of said elements are measured by inductively coupled plasma emission spectroscopy.
- compositions comprise less than about 350 ppm of nitrogen per kg of total weight of water-soluble C5 saccharides, preferably less than about 325 ppm of nitrogen per kg of total weight of water-soluble C5 saccharides. Nitrogen may be measured by thermal conductivity detection after combustion and reduction.
- the weight ratio of the collective mass of hydrogen and nitrogen to mass of carbon present in said water-soluble C5 oligosaccharide hydrolysate and said water-soluble C5 monosaccharide hydrolysate is less than about 0.14.
- Carbon, hydrogen, and nitrogen levels may be measured by thermal conductivity detection after combustion and reduction.
- compositions comprising the C5 saccharides further comprise less than a maximum of any of the elements, individually or in combination, in the table listed below:
- compositions comprise:
- water-soluble C5 oligosaccharides have a degree of polymerization of about 2 to about 28.
- said water-soluble C5 oligosaccharides are present at a level of about 80% by weight to about 90% by weight, based on total weight of said water-soluble C5 oligosaccharide hydrolysate and said water-soluble C5 monosaccharide hydrolysate in said composition.
- said water-soluble C5 oligosaccharides have a degree of polymerization of about 2 to about 16, preferably, about 2 to about 10, and more preferably, about 2 to about 5.
- compositions further comprise about 10% by weight, to about 25% by weight, based on total weight of said water-soluble C5 oligosaccharide hydrolysate and said water-soluble C5 monosaccharide hydrolysate in said composition, of C5 monosaccharides.
- said water-soluble C5 oligosaccharide hydrolysate comprises:
- said water-soluble C5 oligosaccharides have a degree of polymerization of about 2 to about 16, preferably, about 2 to about 10, and more preferably, about 2 to about 5.
- the compositions further comprise about 10% by weight, to about 25% by weight, based on total weight of said water-soluble C5 oligosaccharide hydrolysate and said water-soluble C5 monosaccharide hydrolysate in said composition, of C5 monosaccharides.
- compositions further comprise about 12.5% by weight, to about 20% by weight, based on total weight of said water-soluble C5 oligosaccharide hydrolysate and said water-soluble C5 monosaccharide hydrolysate in said composition, of C5 monosaccharides.
- said C5 disaccharides are present at a level of about 17.5% by weight to about 25% by weight, based on total weight of said water-soluble C5 oligosaccharide hydrolysate and said water-soluble C5 monosaccharide hydrolysate in said composition.
- said C5 trisaccharides are present at a level of about 12.5% by weight to about 17.5% by weight, based on total weight of said water-soluble C5 oligosaccharide hydrolysate and said water-soluble C5 monosaccharide hydrolysate in said composition.
- said C5 tetrasaccharides are present at a level of about 10% by weight to about 20% by weight, based on total weight of said water-soluble C5 oligosaccharide hydrolysate and said water-soluble C5 monosaccharide hydrolysate in said composition.
- said C5 pentasaccharides are present at a level of about 2.5% by weight to about 15% by weight, based on total weight of said water-soluble C5 oligosaccharide hydrolysate and said water-soluble C5 monosaccharide hydrolysate in said composition.
- said C5 saccharides having at a degree of polymerization of at least about 6 are present at a level of about 12.5% by weight to about 30% by weight, based on total weight of said water-soluble C5 oligosaccharide hydrolysate and said water-soluble C5 monosaccharide hydrolysate in said composition.
- compositions described herein further comprise about 10% by weight, to about 25% by weight, based on total weight of said water-soluble C5 oligosaccharide hydrolysate and said water-soluble C5 monosaccharide hydrolysate in said composition, of C5 monosaccharides.
- compositions described herein further comprise water.
- the water-soluble C6 oligosaccharide hydrolysate and the water-soluble C6 monosaccharide hydrolysate are processed from lignocellulosic biomass using supercritical, subcritical, or near critical fluid extraction, or a combination thereof.
- the invention is directed to methods of reducing the level of enzyme required for enzymatically hydrolyzing first water-soluble C6 saccharides having an average degree of polymerization to about 2 to about 15, preferably about 2 to about 10, and more preferably about 2 to about 6, to second water-soluble C6 saccharides having a lower average degree of polymerization than said average degree of polymerization of said first water-soluble C6 saccharides, comprising:
- hydrolysate comprising said first water-soluble C6 saccharides and less than about 5250 ppm in total, based on total weight of water-soluble C6 saccharide hydrolysate in said composition, of elements;
- said elements are Al, As, B, Ba, Be, Ca, Cd, Co, Cr, Cu, Fe, K, Li, Mg, Mn, Mo, Na, Ni, P, Pb, S, Sb, Se, Si, Sn, Sr, Ti, Tl, V, and Zn.
- the C6 saccharides are extracted from lignocellulosic biomass.
- the C6 saccharides are processed from lignocellulosic biomass using supercritical, subcritical, or near critical fluid extraction, or a combination thereof.
- the invention is directed to methods of reducing the level of enzyme required for enzymatically hydrolyzing first water-soluble C5 saccharides having an average degree of polymerization to about 2 to about 28, preferably about 2 to about 15, more preferably about 2 to about 13, even more preferably about 2 to about 6, to second water-soluble C5 saccharides having a lower average degree of polymerization than said average degree of polymerization of said first water-soluble C5 saccharides, comprising:
- hydrolysate comprising said first water-soluble C5 saccharides and less than about 3700 ppm in total, based on total weight of water-soluble C5 saccharide hydrolysate in said composition, of elements;
- said elements are Al, As, B, Ba, Be, Ca, Cd, Co, Cr, Cu, Fe, K, Li, Mg, Mn, Mo, Na, Ni, P, Pb, S, Sb, Se, Si, Sn, Sr, Ti, Tl, V, and Zn.
- compositions further comprise less than about 0.5% by weight, based on the total weight of said C5 saccharides or C6 saccharides, of organic solvent, such as alcohols, including water miscible lower aliphatic C 1 -C 4 alcohols (e.g., methanol, ethanol, isopropanol, t-butanol).
- organic solvent such as alcohols, including water miscible lower aliphatic C 1 -C 4 alcohols (e.g., methanol, ethanol, isopropanol, t-butanol).
- the compositions contain less than about 0.1% by weight, based on the total weight of said of said C5 saccharides or C6 saccharides of organic solvent.
- the compositions contain substantially no organic solvent.
- compositions of the invention are preferably prepared from biomass by processes employing supercritical, subcritical, and/or near critical water, preferably without the addition of acid.
- the processes may include pretreatment step or steps using supercritical or near critical water to separate the C5 sugars (monomers and/or oligomers) from cellulose and lignin.
- suitable temperatures are about 130° C. to about 250° C.
- suitable pressures are about 4 bars to about 100 bars
- suitable residence times are about 0.5 minutes to about 5 hours.
- the processes may also include a cellulose hydrolysis step or steps using supercritical or near critical water to separate the cellulose (which may processed to form C6 monomeric and/or oligomeric sugars) from the lignin.
- suitable temperatures are about 250° C. to about 450° C.
- suitable pressures are about 40 bars to about 260 bars
- suitable residence times are about 0.1 seconds to about 3 minutes.
- the compositions may be prepared in any suitable reactor, including, but not limited to, a tubular reactor, a digester (vertical, horizontal, or inclined), or the like.
- Suitable digesters include the digester system described in U.S. Pat. No. 8,057,639, which include a digester and a steam explosion unit, the entire disclosure of which is incorporated by reference.
- compositions of the invention comprising C5 saccharides or C6 saccharides may be utilized in a wide variety of applications, where C5 and C6 sugars are conventionally utilized, including, but not limited to, the production of various chemicals and fuels using fermentative, enzymatic, catalytic, and non-catalytic (e.g., thermal decomposition) processes.
- Such processes are useful for preparing feedstocks for the preparation of the following non-exhaustive list:
- fuels such as gasoline, jet fuel, butanol, and the like
- chemicals such as acetic acid, acetic anhydride, acetone, acrylic acid, adipic acid, benzene, ethanol, ethylene, ethylene glycol, ethylene oxide, methanol, polypropylene, terephthalic acid, toluene, xylene, 1,3-propanediol, 1,4-butanediol, and the like);
- pharmaceuticals and foods such as acetoin, alanine, arabitol, ascorbic acid, aspartic acid, citric acid, coumaric acid, fumaric acid, glycerol, glycine, kojic acid, lactic acid, lysine, malonic acid, proline, propionic acid, serine, sorbitol, succinic acid, threonine, xylitol, sugar acids (glucaric acid, gluconic acid, xylonic acids), and the like);
- pharmaceuticals and foods such as acetoin, alanine, arabitol, ascorbic acid, aspartic acid, citric acid, coumaric acid, fumaric acid, glycerol, glycine, kojic acid, lactic acid, lysine, malonic acid, proline, propionic acid, serine, sorbitol, succinic acid, threonine, xylitol, sugar acids (glucaric
- specialty chemicals such as acontic acid, glutamic acid, malic acid, oxalic acid, and the like
- the C5 oligosaccharide and C6 oligosaccharide compositions of the invention were prepared using supercritical, subcritical, and near critical water extraction in a two stage process.
- Particulate lignocellulosic biomass consisting of mixed hardwood chips of 140 mesh or less was mixed with water to form a slurry (about 20% by weight solids).
- the slurry was heated to a temperature of about 170-245° C. and then feed into a pretreatment reactor for about 1-120 minutes under sufficient pressure to keep the water in the liquid phase.
- the pretreated slurry was then cooled to a temperature less than about 100° C. under little (less than about 10 bar) or no pressure.
- the pretreated solids were then separated from the liquid stream using a filter press.
- the solids may be separated using a centrifugal filter pressor.
- the pretreated solids were then mixed with water to form a slurry and the slurry was heated to a temperature of about 150-250° C.
- the slurry was then subjected to supercritical water at about 374-600° C. in a hydrolysis reactor for about 0.05-10 seconds under a pressure of about 230-300 bar.
- the hydrolyzed slurry was quenched with water and then flashed to about ambient temperature and pressure to remove water.
- the lignin solids were then separated from the liquid stream using a centrifugal decanter and air dried.
- the C5 oligosaccharides and the C6 oligosaccharides streams were first concentrated to about 200 g/L, adjusted to about pH 3-4 and filtered using 0.45 micron filter.
- Oligomer Oligomer (C6) (C5) Species g/liter or ppm g/liter or ppm A1 4.63 4.05 As 0.39 0.54 B 0.61 2.31 Ba 2.49 3.94 Be 0.00 0.01 Ca 2945.00 2245.00 Cd 0.05 0.11 Co 0.04 0.08 Cr 0.14 0.12 Cu 0.97 0.70 Fe 309.00 22.94 K 127.35 329.00 Li 0.03 0.02 Mg 178.00 545.50 Mn 14.40 126.40 Mo 0.58 0.32 Na 368.50 44.80 Ni 0.78 0.69 P 10.99 90.20 Pb 0.21 0.32 S 946.00 132.45 Sb 0.21 0.30 Se 0.45 0.66 Si 80.65 22.10 Sn 0.18 0.39 Sr 3.51 13.66 Ti 0.00 0.00 Tl 0.45 0.67 V 0.02 0.01 Zn 61.35 17.48
- the C5 oligosaccharide and C6 oligosaccharide compositions of the invention were prepared using supercritical, subcritical, and near critical water extraction in a two stage process as described in Example 1. The samples were then diluted ten times. The degree of polymerization was qualitatively determined, i.e., not quantifying the amount of each oligomer, using gel permeation chromatography.
- a degree of polymerization were detected up to at least a DP of 13, with small peaks visible above DP of 13 for the C6 oligosaccharide compositions.
- a degree of polymerization were detected up to at least a DP of 28, with small peaks visible above DP of 28 for the C5 oligosaccharide compositions.
- the C6 saccharide compositions of the invention were prepared using supercritical, subcritical, and near critical water extraction in a two stage process as described in Example 1. Representative samples bracketing the extremes/possibilities of feed material source (tubular reactor), reactor temperature (348.2-383.4° C.), reactor residence time (0.19-1.48 seconds), and feed aqueous slurry concentration (6.4-14.77%) were selected.
- the C5 saccharide compositions of the invention were prepared using supercritical, subcritical, and near critical water extraction in the first stage of the two stage process as described in Example 1. Representative samples bracketing the extremes/possibilities of reactor feed concentration (10.66-13.78 weight %, reactor temperature (249-261° C.), and reactor residence time (2-3 minutes) were selected.
- the C5 and C6 saccharide compositions of the invention were prepared using supercritical, subcritical, and near critical water extraction in the two stage process as described in Example 1. Representative samples were selected.
- DIONEX averaged results (varying residence time in hemihydrolysis reactor; varying slurry loading) Residence Slurry C5 monomer time loading (xylose) C5 dimer C5 trimer C5 tetramer C5 pentamer C5 hexamer minutes % g/L wt % g/L wt % g/L wt % g/L wt % g/L wt% g/L wt% 2 11.39 0.28835 6.9 1.7517 42.0 1.4432 34.6 0.0981 2.4 0.1817 4.4 0.4095 9.8 3 10.95 0.91497 19.8 1.6926 36.7 1.248 27.0 0.35397 7.7 0.2271 4.9 0.18023 3.9
- DIONEX averaged results (varying residence time in hemihydrolysis reactor; varying slurry loading)
- Residence Slurry time loading C5 monomer C5 dimer C5 trimer C5 tetramer C5 pentamer C5 hexamer minutes % g/L wt % g/L wt % g/L wt % g/L wt % g/L wt % g/L wt % 2 11.39 0.28835 6.9 1.7517 42.0 1.4432 34.6 0.0981 2.4 0.1817 4.4 0.4095 9.8 3 10.95 0.91497 19.8 1.6926 36.7 1.248 27.0 0.35397 7.7 0.2271 4.9 0.18023 3.9
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Priority Applications (42)
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CA2804993A CA2804993C (en) | 2011-12-30 | 2012-12-03 | Compositions comprising c5 and c6 oligosaccharides |
EP17197851.3A EP3296307B1 (en) | 2011-12-30 | 2012-12-03 | Compositions comprising c5 oligosaccharides |
RU2012154202/15A RU2012154202A (ru) | 2011-12-30 | 2012-12-03 | Композиции, включающие с5 и с6 олигосахариды |
CN201280065283.7A CN104024268A (zh) | 2011-12-30 | 2012-12-03 | 包含c5和c6寡糖的组合物 |
PCT/US2012/067644 WO2013101403A1 (en) | 2011-12-30 | 2012-12-03 | Compositions comprising c5 and c6 oligosaccharides |
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PCT/US2012/067641 WO2013101402A1 (en) | 2011-12-30 | 2012-12-03 | Compositions comprising c5 and c6 oligosaccharides |
AU2012362942A AU2012362942B2 (en) | 2011-12-30 | 2012-12-03 | Compositions comprising C5 and C6 oligosaccharides |
KR1020147020084A KR20140108301A (ko) | 2011-12-30 | 2012-12-03 | C5 및 c6 올리고당류를 포함하는 조성물 |
IN1516KON2014 IN2014KN01516A (ja) | 2011-12-30 | 2012-12-03 | |
EP20186626.6A EP3778926A3 (en) | 2011-12-30 | 2012-12-03 | Compositions comprising c6 oligosaccharides |
KR1020147020083A KR20140108300A (ko) | 2011-12-30 | 2012-12-03 | C5 및 c6 올리고당류를 포함하는 조성물 |
BR112014015908A BR112014015908A8 (pt) | 2011-12-30 | 2012-12-03 | composição |
KR1020147020085A KR20140109441A (ko) | 2011-12-30 | 2012-12-03 | C5 및 c6 단당류를 포함하는 조성물 |
BR112014016008-2A BR112014016008B1 (pt) | 2011-12-30 | 2012-12-03 | Composição compreendendo oligossacarídeo c6 e hidrolisatos de monossacrídeo solúveis em água |
EP12863319.5A EP2797944B1 (en) | 2011-12-30 | 2012-12-03 | Compositions comprising c6 oligosaccharides |
BR112014015910A BR112014015910A8 (pt) | 2011-12-30 | 2012-12-03 | composição |
JP2014550308A JP6325454B2 (ja) | 2011-12-30 | 2012-12-03 | C5およびc6オリゴ糖を含む組成物 |
KR1020147020086A KR20140108302A (ko) | 2011-12-30 | 2012-12-03 | C5 및 c6 단당류를 포함하는 조성물 |
JP2014550307A JP2015503558A (ja) | 2011-12-30 | 2012-12-03 | C5およびc6単糖を含む組成物 |
PCT/US2012/067537 WO2013101398A1 (en) | 2011-12-30 | 2012-12-03 | Compositions comprising c5 and c6 monosaccharides |
PCT/US2012/067538 WO2013101399A1 (en) | 2011-12-30 | 2012-12-03 | Compositions comprising c5 and c6 monosaccharides |
RU2014131379A RU2014131379A (ru) | 2011-12-30 | 2012-12-03 | Композиции, содержащие с5 и с6 сахариды |
BR112014015909A BR112014015909B1 (pt) | 2011-12-30 | 2012-12-03 | composição compreendendo oligossacarídeo c5 e c6 e hidrolisatos de monossacarídeo |
CA2860704A CA2860704A1 (en) | 2011-12-30 | 2012-12-03 | Compositions comprising c5 and c6 monosaccharides |
CN201280064644.6A CN104039803A (zh) | 2011-12-30 | 2012-12-03 | 包含c5和c6单糖的组合物 |
CA2817235A CA2817235C (en) | 2011-12-30 | 2012-12-03 | Compositions comprising c5 and c6 oligosaccharides |
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RU2012154203/04A RU2012154203A (ru) | 2011-12-30 | 2012-12-03 | Композиции, включающие с5 и с6 олигосахариды |
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US10385140B2 (en) | 2014-09-26 | 2019-08-20 | Renmatix, Inc. | Cellulose-containing compositions and methods of making same |
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BR112012032999B1 (pt) | 2010-06-26 | 2022-11-29 | Virdia, Llc | Hidrolisado lignocelulósico e métodos de hidrólise ácida e desacidificação para gerar misturas de açúcar a partir de lignocelulose |
IL206678A0 (en) | 2010-06-28 | 2010-12-30 | Hcl Cleantech Ltd | A method for the production of fermentable sugars |
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