WO2000042225A1 - Process for the separation of sugars - Google Patents
Process for the separation of sugars Download PDFInfo
- Publication number
- WO2000042225A1 WO2000042225A1 PCT/US1999/030877 US9930877W WO0042225A1 WO 2000042225 A1 WO2000042225 A1 WO 2000042225A1 US 9930877 W US9930877 W US 9930877W WO 0042225 A1 WO0042225 A1 WO 0042225A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- carbohydrate
- recited
- resin
- liquor
- aqueous phase
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C13—SUGAR INDUSTRY
- C13B—PRODUCTION OF SUCROSE; APPARATUS SPECIALLY ADAPTED THEREFOR
- C13B20/00—Purification of sugar juices
- C13B20/14—Purification of sugar juices using ion-exchange materials
- C13B20/146—Purification of sugar juices using ion-exchange materials using only anionic ion-exchange material
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
- B01D15/10—Selective adsorption, e.g. chromatography characterised by constructional or operational features
- B01D15/18—Selective adsorption, e.g. chromatography characterised by constructional or operational features relating to flow patterns
- B01D15/1814—Selective adsorption, e.g. chromatography characterised by constructional or operational features relating to flow patterns recycling of the fraction to be distributed
- B01D15/1821—Simulated moving beds
- B01D15/185—Simulated moving beds characterized by the components to be separated
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J41/00—Anion exchange; Use of material as anion exchangers; Treatment of material for improving the anion exchange properties
- B01J41/04—Processes using organic exchangers
- B01J41/05—Processes using organic exchangers in the strongly basic form
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J41/00—Anion exchange; Use of material as anion exchangers; Treatment of material for improving the anion exchange properties
- B01J41/20—Anion exchangers for chromatographic processes
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2215/00—Separating processes involving the treatment of liquids with adsorbents
- B01D2215/02—Separating processes involving the treatment of liquids with adsorbents with moving adsorbents
- B01D2215/023—Simulated moving beds
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/88—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86
- G01N2030/8809—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86 analysis specially adapted for the sample
- G01N2030/8813—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86 analysis specially adapted for the sample biological materials
- G01N2030/8836—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86 analysis specially adapted for the sample biological materials involving saccharides
Definitions
- This invention pertains to processes for separating sugars and sugar alcohols, such as xylose, mannose, galactose, arabinose, glucose, xylitol, arabitol, sorbitol, galactitol, or mannitol from mixtures with other sugars or sugar alcohols, mixtures such as hardwood or softwood liquors.
- sugars and sugar alcohols such as xylose, mannose, galactose, arabinose, glucose, xylitol, arabitol, sorbitol, galactitol, or mannitol from mixtures with other sugars or sugar alcohols, mixtures such as hardwood or softwood liquors.
- xylose production is currently based on recovery from hardwood liquors (USA, Russia, Finland, Norway, Austria), with smaller quantities from sugarcane bagasse (China), and possibly other hemicellulose-rich feedstocks.
- Most industrially produced xylose is hydrogenated to produce xylitol, a specialty sweetener with outstanding properties as a component of oral hygiene products, diabetic foods and other specialty products.
- Alternate routes to xylitol are via fermentation of glucose with osmiophilic yeast and enzymatic isomerization, or via xylonic acid by oxidation of glucose, fructose, or galactose.
- Mannitol another specialty sweetener widely used in sugarless chewing gums, is produced industrially by simultaneous chemical isomerization and hydrogenation of fructose, or by enzymatic isomerization of fructose and hydrogenation of the purified mannose. Fermentations of sugars to mannitol are known, and some biomass feedstocks high in mannose do exist. It has been reported that coffee extraction residues and ivory nut meal are good sources of mannose, as are the softwood liquors. Mannitol is also produced by direct extraction from seaweed in China. In chemical isomerization processes, the product mix may contain 60-70% sorbitol and 30-40% mannitol, depending on the hydrogenation conditions; the two are then typically separated by fractional crystallization.
- hemicellulose hydrolysates typically contain mixtures of five- and six-carbon sugars, the pentoses and hexoses.
- the sugar xylose predominates in hydrolysates from hardwoods and annual plants, while softwood liquors typically comprise primarily mannose, with smaller quantities of xylose, glucose and other sugars.
- Typical sugar profiles are shown in Table I, whose data are taken from U.S. Patent 5,084,104 and U.S. Patent 3,677,818.
- Table I Typical sugar profiles in hardwood and softwood liquors, expressed as percentages of total sugars.
- xylose can be recovered by crystallization. After crystallization a non-crystallizing syrup remains, "xylose molasses,” which is a mixture of xylose, glucose, mannose, and other sugars.
- xylose molasses is a mixture of xylose, glucose, mannose, and other sugars.
- hydrolyzed and purified softwood liquors, rich in mannose do not crystallize readily, even where the liquors are nearly free of non-sugar constituents. The reason may be that xylose, glucose, and possibly other sugars inhibit mannose crystallization.
- a chloride-form anion exchange resin may readily be converted to a hydroxyl-form resin by passing a hydroxyl-containing solution (typically 1 M NaOH) over the resin.
- a hydroxyl-containing solution typically 1 M NaOH
- sugars then bind to the resin too tightly for the process to be commercially useful.
- Chromatogr. 1991, 558(1), 89-104 discloses the use of various cation exchange resins to separate certain mixtures of carbohydrates.
- U.S. Patent 4,837,315 discloses the separation of mannose from mixtures with glucose and other saccharides by adsorption of sulfonated polystyrene divinylbenzene crosslinked ion exchange resins in calcium and ammonium form.
- U.S. Patent 4,471,114 discloses a process for separating mannose from glucose by adsorption on zeolites.
- U.S. Patent 4,075,406 discloses a method for recovering xylose from pentosan-, preferably xylan-containing raw materials by hydrolyzing the raw material, purifying the hydrolysate by ion exclusion and color removal, and subjecting the purified solution to chromatographie fractionation.
- a previously unattained objective in the chromatographie separation of sugars or sugar alcohols, particularly from plant extracts, is to identify a suitable combination of sorbent and solvent such that the differential affinity of the sorbent for the components to be separated is sufficient to give separation on a system of reasonable size, on a preparative scale, in an economically efficient manner; so that the sorbent does not bind any of the components so strongly that frequent periodic regeneration is necessary.
- a strong base anion exchange resin such as a chloride-form strong base anion exchange resin
- a strong base anion exchange resin such as a chloride-form strong base anion exchange resin
- a low concentration of hydroxyl for example, an NaOH solution with a concentration between 0.1 and 1000 mM, preferably between 0.1 and 100 mM, most preferably between 1 and 10 mM
- the conditioned resin separates a number of sugars and sugar alcohols from one another, while still allowing ready desorption of those carbohydrates from the resin.
- the novel process is efficient in separating glucose, mannose, xylose, arabinose, and galactose, the principal sugar constituents of biomass.
- the novel process is also efficient in separating sugar alcohols, such as xylitol, arabitol, sorbitol, galactitol, and mannitol, from one another or from sugars.
- the feedstock is first passed over a column containing this conditioned resin, followed by a mobile phase solvent, preferably water. If desired, continued application of the mobile phase to the column may optionally be used for the selective recovery of other organic materials as well.
- the novel process may economically be performed on industrial-scale separations, particularly when used in a preferred simulated moving bed chromatographie system.
- Strong base anion exchange resins for example in chloride form, may for example be conditioned with dilute solutions of hydroxide, or dilute mixtures of chloride and hydroxide. Increasing concentrations of hydroxide improve separation efficiencies, but increase residence times, while the opposite holds for chloride concentrations.
- the novel method is suitable for continuous countercurrent separation techniques, such as simulated moving bed chromatography. Separations achieved with the novel system are superior to those obtained with sulfate-form anion exchangers. (Compare, e.g., the results shown in Figure 2 here with those reported in U.S. Patent 5,084,104.)
- Figure 1 illustrates a xylose/mannose separation achieved with an embodiment of the present invention.
- Figure 2 illustrates a separation of a purified softwood hydrolysate liquor achieved with an embodiment of the present invention.
- Figure 3 illustrates the results of a separation of sugar alcohols achieved with an embodiment of the present invention.
- Anion exchange resins have usually been used in the past for demineralization of solutions, i.e., for ion exchange, or for decolorization, i.e., for adsorption. By contrast, in the present invention there is little or no net ion exchange or adso ⁇ tion between the resin and the solution. Although an anion-type ion exchange resin is used, it is used for its properties as a chromatographie substrate, rather than in a column intended primarily for net exchange of ions.
- Chromatographie separation differs from other column-based separations (e.g., ion- exchange or adsorption) in that no major component in the feed mixture is retained by the sorbent so strongly as to require that additional reagents be routinely used between cycles to regenerate the column by removing strongly retained components before the next separation cycle.
- ion-exchange or adso ⁇ tion column the function of an ion-exchange or adso ⁇ tion column is to bind components tightly, necessarily requiring frequent regeneration for the resin to be reused.
- a chromatographie column By contrast, the function of a chromatographie column is to provide differential mobility for components moving through the column to effect a separation, but not to bind too tightly to the principal components. Regeneration of a chromatographie column may be needed from time to time due to incidental binding of minor components or impurities to the resin.
- the minimal quantity of reagents needed for resin regeneration is a major advantage of chromatographie separations over ion-exchange separations.
- the operational cost of chromatographie separations is due primarily to the energy needed to evaporate water (or other solvent) from dilute products, and to a lesser extent to the infrequent replacement or regeneration of resin.
- SMB simulated moving bed method
- the SMB method uses a number of columns (e.g., 8 to 12 in number) packed with a suitable sorbent and connected in series. There are inlet ports for feed and solvent (which may include recycled solvent), and outlet ports for two or more products (or other separated fractions). The positions of the ports relative to the columns are periodically switched along the direction of the liquid flow, thereby simulating continuous motion of the sorbent relative to the ports and to the liquid.
- the advantages of the SMB method are those generally associated with counter-current-type operations, namely lower solvent (e.g., water) and sorbent requirements.
- the water input to the SMB system preferably comprises a mixture of fresh water and water recycled within the system.
- the SMB process may readily be optimized by adjusting the flow rates (of feed, fresh water, recycled water, and products), and by adjusting the switch time (the time period between moving the ports one column downstream).
- the flow rates of feed, fresh water, recycled water, and products
- the switch time the time period between moving the ports one column downstream.
- the eluant preferably has traces of a base present (e.g., 1 to 10 mM NaOH), such as to just offset the loss of hydroxyl groups on the surface of the resin that will slowly occur as a result of other anions present in the water (e.g., carbonate, bicarbonate, or chloride), or in the feed to be separated (e.g., chloride or sulphate).
- a base e.g., 1 to 10 mM NaOH
- the concentration of base should not be high enough to convert the core of the resin to hydroxyl form.
- Mannose and xylose were chosen as the critical pair for proof of concept and for optimizing the separation, due both to the historical difficulty in efficiently separating these sugars from one another, and the potential interest in fractionating these sugars from softwood hydrolysate liquors. The separation of other sugars was also monitored.
- a preparative WatersTM R-400 differential refractometer was used to monitor the separation on-line, and was connected to a chart recorder. 10 mL fractions were collected from the exit of the column, and their sugar profiles were determined off-line with a Dionex (Sunnyvale, CA) DX 500 chromatography system, equipped with a Dionex CarboPacTM PA 10 4 x 250 mm column.
- Figure 1 illustrates a xylose/mannose separation achieved with an embodiment of the present invention.
- the column was a 1 x 100 cm, Bio-Rad AG MP-1 (150 - 300 ⁇ m).
- the eluant was deionized water at 2.5 mL/min.
- the degree of separation shown in Figure 1 was quantified by measuring the retention volume of a peak t in mL (elution time at peak maximum multiplied by the flow rate), peak width W (mL) at half height (peak width at half height in units of time multiplied by the flow rate).
- the resolution factor R. was calculated as
- Table III Effect of resin conditioning with dilute solutions of NaOH and NaCl on the separation of xylose and mannose (10 g/ L each). 1 x 100 cm column, Bio-Rad AG MP-1 (150 - 300 ⁇ m particle size) anion exchange resin. Flow rate: 2.5 mL/min.
- FIG. 2 A separation of a purified softwood hydrolysate liquor is illustrated in Figure 2.
- the column was a 1 x 100 cm, Bio-Rad AG MP-1 (150 - 300 ⁇ m).
- the eluant was deionized water at 2.5 mL/min.
- the sugars were separated from one another reasonably well, with mannose (the major component) eluting last, preceded by xylose and glucose.
- the xylose/mannose resolution R s was 0.35, somewhat higher than was seen for a synthetic 1:1 solution at the same experimental conditions, presumably because of the lower relative xylose concentration in the softwood hydrolysate sample. All results shown in Tables III - V and Figures 1 and 2 were obtained at ambient temperature. At temperatures of 45 °C and higher (data not shown) the monosaccharides can degrade in contact with the OH- surface, and their recoveries are correspondingly low. The ionic content of the feed solution may affect both optimum C Na0H levels and the required frequency of re-conditioning of the columns. It is preferred that the feed solutions be demineralized before chromatography to prevent rapid deactivation of the anion exchanger.
- softwood sugars may, for example, be separated into three fractions: Fraction 1 (arabinose, galactose, glucose); Fraction 2 (xylose); and Fraction 3 (mannose).
- Fraction 1 arabinose, galactose, glucose
- Fraction 2 xylose
- Fraction 3 mannose
- the novel technique can be used not only to separate sugars from other sugars, but also sugars from sugar alcohols, and different sugar alcohols from one another.
- Tables VI, VII, and VIII give examples of such separations.
- Table VI Effect of NaOH concentration on retention time of sugar alcohols. 1 x 100 cm column, Bio-Rad AG MP-1 (150-300 ⁇ m particle size). The injected sample was the supernatant following a partial crystallization of a demineralized, hydrogenated softwood liquor. Total sample concentration (weight percentage of total solids) was 5%. Retention times shown are in mL of eluted solution. Flow Rate, 2.5 mL/min. C NaCl 0.
- Table VIII Separations of mixtures of sugars and sugar alcohols at total sample concentrations of 4-5%. 1 x 100 cm column, Bio-Rad AG MP-1 (150-300 ⁇ m particle size). This Table combines results obtained in separate separations of sugars and of sugar alcohols.
- the injected sample for the sugars was as in Figure 2.
- the injected sample for the sugar alcohols was as in Table VI.
- Figure 3 depicts the separation of Table VI, bottom row.
- the separations be performed with one of the variants known in the art for a counter-current, simulated moving bed, chromatographie system capable of three- fraction separations.
- the extracts or liquors are preferably first demineralized in a conventional manner, e.g., by passing through a column packed with a strong acid cation exchange resin followed by a column packed with a strong base anion exchange resin, or a single column with a mixed bed of cation and anion exchange resins.
- feeds that are optically clear, with a concentration of suspended solids less than about 100 mg/1.
- Standard processes for clarification may be used, including centrifugation, filtration, settling, flocculation, or a combination of these techniques.
- the clarification is preferably performed prior to demineralization, to protect the demineralization resins from fouling as well.
- chloride-form resins are preferred, anion exchange resins other than in chloride form (before conditioning with base) will also work in practicing the present invention.
- the anion should not be strongly basic, or as is the case when a hydroxide-form resin is used, the sugars will bind the resin too tightly. Additionally, the physical size of the anion should not be so large (e.g., some polymeric anions) as to block access to the resin. Otherwise, most common anions will work in the present invention.
- Illustrative of anions that may be substituted for chloride in practicing the present invention are fluoride, bromide, iodide, nitrite, nitrate, sulphate, bisulphate, monobasic or dibasic phosphate, chlorate, citrate, chlorate, cyanide, sulfite, bisulfite, bromate, carbonate, bicarbonate, iodate, formate, propionate, and acetate.
- the conditioning of the bed is preferably performed with one to ten bed volumes of hydroxyl ion at a concentration between 1 and 10 mM, it will also be possible to practice the present invention by conditioning the bed with at least one-tenth bed volume of hydroxyl ion in a concentration between 0.1 mM and 1000 mM.
- sugar alcohol feeds may, for example, be prepared by hydrogenating such feeds by reaction of sugars in such raw feeds with hydrogen gas - feeds for separating sugar alcohols may thus include, for example, hydrogenated hardwood or softwood liquor hydrolysates, hydrogenated bagasse liquor hydrolysate, hydrogenated oat hull liquor hydrolysate, and other hydrogenated biomass liquor hydrolysates.
Abstract
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU23872/00A AU2387200A (en) | 1999-01-14 | 1999-12-22 | Process for the separation of sugars |
CA002359337A CA2359337C (en) | 1999-01-14 | 1999-12-22 | Process for the separation of sugars |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US23119399A | 1999-01-14 | 1999-01-14 | |
US09/231,193 | 1999-01-14 |
Publications (2)
Publication Number | Publication Date |
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WO2000042225A1 true WO2000042225A1 (en) | 2000-07-20 |
WO2000042225A9 WO2000042225A9 (en) | 2001-09-13 |
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Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1999/030877 WO2000042225A1 (en) | 1999-01-14 | 1999-12-22 | Process for the separation of sugars |
Country Status (3)
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AU (1) | AU2387200A (en) |
CA (1) | CA2359337C (en) |
WO (1) | WO2000042225A1 (en) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2003010339A1 (en) * | 2001-07-24 | 2003-02-06 | Arkenol, Inc. | Separation of xylose and glucose |
WO2003080872A1 (en) * | 2002-03-27 | 2003-10-02 | Danisco Sweeteners Oy | Separation of sugars, sugar alcohols, carbohydrates and mixtures thereof |
US6773512B2 (en) | 2001-12-31 | 2004-08-10 | Danisco Sweeteners Oy | Method for the recovery of sugars |
WO2005001145A1 (en) | 2003-06-27 | 2005-01-06 | Danisco Sweeteners Oy | A method for recovering galactose from a solution derived from plant-based biomass using chromatographic fractionation steps and crystallisation |
US7722721B2 (en) | 2003-06-27 | 2010-05-25 | Danisco Sweeteners Oy | Separation method |
WO2014158558A1 (en) * | 2013-03-14 | 2014-10-02 | Orochem Technologies, Inc. | L-glucose production from l-glucose/l-mannose mixtures using simulated moving bed separation |
JP2015508174A (en) * | 2012-02-27 | 2015-03-16 | デル マー ファーマシューティカルズ | An improved analytical method for the analysis and determination of contaminants in dianhydrogalactitol |
JP2016538574A (en) * | 2013-11-18 | 2016-12-08 | デル マー ファーマシューティカルズ | HPLC analysis of impurities in dianhydrogalactitol |
WO2020260028A1 (en) * | 2019-06-28 | 2020-12-30 | IFP Energies Nouvelles | Liquid phase separation of second-generation sugars by adsorption on fau zeolite having a si/al atomic ratio of less than 1.5 |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114686532A (en) | 2015-07-24 | 2022-07-01 | 安尼基有限责任公司 | Method for the enzymatic production of oxidation products and reduction products of mixed sugars |
JP6774494B2 (en) | 2016-02-19 | 2020-10-21 | インターコンチネンタル グレート ブランズ エルエルシー | Process for forming multiple useful streams from a biomass source |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3806363A (en) * | 1970-12-09 | 1974-04-23 | Ind Science And Technology | Method for separating fructose |
US5084104A (en) * | 1989-12-05 | 1992-01-28 | Cultor, Ltd. | Method for recovering xylose |
EP0481603A1 (en) * | 1990-10-15 | 1992-04-22 | The Dow Chemical Company | Separation of weak organic acids from liquid mixtures |
US5482631A (en) * | 1994-10-06 | 1996-01-09 | Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College | Separation of inositols from sugars and sugar alcohols |
-
1999
- 1999-12-22 WO PCT/US1999/030877 patent/WO2000042225A1/en active Application Filing
- 1999-12-22 AU AU23872/00A patent/AU2387200A/en not_active Abandoned
- 1999-12-22 CA CA002359337A patent/CA2359337C/en not_active Expired - Fee Related
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3806363A (en) * | 1970-12-09 | 1974-04-23 | Ind Science And Technology | Method for separating fructose |
US5084104A (en) * | 1989-12-05 | 1992-01-28 | Cultor, Ltd. | Method for recovering xylose |
EP0481603A1 (en) * | 1990-10-15 | 1992-04-22 | The Dow Chemical Company | Separation of weak organic acids from liquid mixtures |
US5482631A (en) * | 1994-10-06 | 1996-01-09 | Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College | Separation of inositols from sugars and sugar alcohols |
Non-Patent Citations (3)
Title |
---|
LARSSON L: "an automated procedure for separation of monosaccharides on ion exchange resins", ACTA CHEMICA SCANDINAVICA, vol. 19, 1965, pages 1357 - 1364, XP000891838 * |
SAMUELSSON O ET AL.: "Partition Chromatography of mixtures containing polyols and carbonyl compounds (including sugars) on ion exchange resin", ACTA CHEM. SCAND., vol. 22, 1968, pages 1252 - 1258, XP000901832 * |
ZILL L. ET AL.: "Further studies on the separation of the borate complexes of sugars and related compounds by ion-exchange chromatography", J.AM CHEM.SOC., vol. 75, 1953, XP000891837 * |
Cited By (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2003010339A1 (en) * | 2001-07-24 | 2003-02-06 | Arkenol, Inc. | Separation of xylose and glucose |
US6773512B2 (en) | 2001-12-31 | 2004-08-10 | Danisco Sweeteners Oy | Method for the recovery of sugars |
US7361273B2 (en) | 2002-03-27 | 2008-04-22 | Saniscosweetners Oy | Separation of sugars, sugar alcohols, carbohydrates and mixtures thereof |
WO2003080872A1 (en) * | 2002-03-27 | 2003-10-02 | Danisco Sweeteners Oy | Separation of sugars, sugar alcohols, carbohydrates and mixtures thereof |
US7722721B2 (en) | 2003-06-27 | 2010-05-25 | Danisco Sweeteners Oy | Separation method |
JP2007520195A (en) * | 2003-06-27 | 2007-07-26 | ダニスコ スィートナーズ オイ | A method for recovering galactose from a solution derived from plant-based biomass using a chromatographic fractionation step and crystallization. |
WO2005001145A1 (en) | 2003-06-27 | 2005-01-06 | Danisco Sweeteners Oy | A method for recovering galactose from a solution derived from plant-based biomass using chromatographic fractionation steps and crystallisation |
JP2015508174A (en) * | 2012-02-27 | 2015-03-16 | デル マー ファーマシューティカルズ | An improved analytical method for the analysis and determination of contaminants in dianhydrogalactitol |
US9759698B2 (en) | 2012-02-27 | 2017-09-12 | Del Mar Pharmaceuticals | Analytical methods for analyzing and determining impurities in dianhydrogalactitol |
US10145824B2 (en) | 2012-02-27 | 2018-12-04 | Del Mar Pharmaceuticals (Bc) Ltd. | Analytical methods for analyzing and determining impurities in dianhydrogalactitol |
WO2014158558A1 (en) * | 2013-03-14 | 2014-10-02 | Orochem Technologies, Inc. | L-glucose production from l-glucose/l-mannose mixtures using simulated moving bed separation |
JP2016538574A (en) * | 2013-11-18 | 2016-12-08 | デル マー ファーマシューティカルズ | HPLC analysis of impurities in dianhydrogalactitol |
WO2020260028A1 (en) * | 2019-06-28 | 2020-12-30 | IFP Energies Nouvelles | Liquid phase separation of second-generation sugars by adsorption on fau zeolite having a si/al atomic ratio of less than 1.5 |
FR3097855A1 (en) * | 2019-06-28 | 2021-01-01 | IFP Energies Nouvelles | Liquid phase separation of second generation sugars by adsorption on FAU-type zeolite with Si / Al atomic ratio less than 1.5 |
Also Published As
Publication number | Publication date |
---|---|
WO2000042225A9 (en) | 2001-09-13 |
CA2359337C (en) | 2005-09-13 |
CA2359337A1 (en) | 2000-07-20 |
AU2387200A (en) | 2000-08-01 |
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