CN103059071A - Nanofiltration separation method of monosaccharide - Google Patents
Nanofiltration separation method of monosaccharide Download PDFInfo
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- CN103059071A CN103059071A CN2013100069708A CN201310006970A CN103059071A CN 103059071 A CN103059071 A CN 103059071A CN 2013100069708 A CN2013100069708 A CN 2013100069708A CN 201310006970 A CN201310006970 A CN 201310006970A CN 103059071 A CN103059071 A CN 103059071A
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Abstract
The invention relates to a nanofiltration separation method of monosaccharide. The method comprises the following steps: preparing a monosaccharide mixture to be separated to form an aqueous solution with the concentration of 1 to 30 wt%; carrying out a nanofiltration separation on the aqueous solution by using a nanofiltration membrane, wherein the conditions for the nanofiltration separation are as follows: the pressure is controlled in the range from 0.1 bar to 45 bar, the surface flow velocity of the nanofiltration membrane is controlled in the range from 0.1 m/s to 10 m/s and the solution temperature is controlled in the range from 1 DEG C to 55 DEG C; and regulating the ion concentration of the aqueous solution prepared from the monosaccharide mixture to be separated to reach 0 to 2 mol/L by adding ions, wherein the pH value of the solution is controlled in the range from 0 to 9. In addition, the monosaccharide mixture to be separated has the carbon atom number of 4 to 7. Compared with the prior art, the method provided by the invention has the advantages of being small in investment, high in efficiency, good in economical effect, simple to operate and the like.
Description
Technical field
The invention belongs to sugar and separation engineering field, relate to the nanofiltration membrane separation method of a kind of small molecules isomers or analog, especially a kind of nanofiltration separation method of monose.
Background technology
Sugar is the abundantest in the world organic compound, is present in natural animal and plant and the microorganism with forms such as Mierocrystalline cellulose, hemicellulose and chitins.Carbohydrate is important feature and the functionally active material that the mankind depend on for existence, and carbohydrate research is significant in the industry such as food, medicine, fermentation with production, the status is important.Because glycan molecule complicated, various singularity on regioselectivity control and steric configuration, conformation is so that the design of saccharide compound, preparation, separation and sign are all difficult.
Because all needs obtain the monose that various forms is naturally occurring or prepare by methods such as physics, biology, chemistry, academia and industrial community are shown great attention to this field both at home and abroad at present foodstuffs industry and the biological medicine industry.Yet these monose are generally all accompanied and are deposited other forms of monose or derivatives thereof in extraction, preparation and purge process, and the technical difficulty for preparing highly purified monose is larger.CN1500796A has announced a kind of force method with nanofiltration purifying oligose; In order to impurity monose and disaccharides inferior separating effect in the technology before solving, need to use more pure water, waste water reclamation is difficult, the problems such as the major product rate of recovery is low: xylo-oligosaccharide or dextrinosan syrup are passed through nanofiltration membrane treatment, the working pressure that adopts is the 1-4 MPa, service temperature is 20-70 ℃, the 2-15 of the dialysis water yield doubly, this invention is different based on the molecular weight (molecular dimension) of monose and oligose, monose that will be less based on the different sieve effects that produce of the molecular dimension of nanofiltration membrane sees through film, larger oligose is held back purifying, and this invention is mainly used in the purifying of functional oligose.
The bibliographical information that the isomers monose of using nanofiltration membrane sepn same molecular amount is not yet arranged at present.Because the molecular weight ratio of monose is more approaching, particularly the isomers monose molecular weight of same carbon atoms number is identical, only be rotational isomerism or epimer, can not utilize molecular weight difference to carry out membrane sepn on the principle, therefore at present separate monose particularly isomers monose can only carry out chromatographic separation for the affine or adsorptive power difference of certain resin etc. by utilizing each monose.The equipment complex and expensive that adopts chromatography to separate, and mainly grasped by American-European countries.As preparing glucose by starch at present, prepare fructose by allomerase again, and separating of fructose and glucose can only separate with chromatography at present, equipment cost is high, operation easier is large; The residual pectinose of meeting in mother liquor during industrial preparation wood sugar, and wood sugar and pectinose also can only be processed through chromatographic separation by seeking suitable chromatography resin as isomers, face simultaneously the difficulty that equipment investment cost is high, operation easier is large; High fructose syrup is extensive sweeting agent commonly used in the foodstuffs industry, wherein the content of glucose is restriction and the important factor that affects the high fructose syrup quality, industrial feasible method only has chromatography at present, the method that glucose is fallen in the microbial fermentation metabolism of possible in theory can affect quality product, can not the industrialization practical application.Using membrane separating technology has potential industrial applications and is worth the extensive separation and purification of sugar component.
Because the monose molecule exists complicated space conformation and configuration, even if isomers, its molecular structure, polarity, pKa value etc. still there are differences, and also exist differently from the interaction of metal ion, acid ion, and also there is certain species diversity in the interaction of separating medium.Nanofiltration membrane is the separatory membrane of a class between ultrafiltration and reverse osmosis, molecular weight cut-off 100～1000Da, and material own is with positive charge, negative charge or neutral.Nanofiltration is main in research and in using traditionally considers its molecular weight cut-off difference, i.e. sieving action mechanism is separated the material of different molecular weight, and it is generally acknowledged for separation identical or very close Middle Molecular Substance and can not adopt the nanofiltration method.There is no both at home and abroad at present by Nanofiltration Membrane Separation Technology the research that the monose of isomers or similar separates, more do not have practical application.We are by the research in early stage, proposed based on various physical properties differences and space structure difference between the above-mentioned monose, selectivity by nanofiltration membrane and the regulation and control of material physical property, theory and the method that monose isomers or various structure can be separated with the close or similar mixture of monosaccharides of molecular weight.
The present invention passes through regulation and control and the molecular modification to the material physical properties of monose solution, variation in conjunction with nanofiltration membrane surface charge character and trapped molecular weight, by regulation and control nanofiltration process stalling characteristic, 4～7 carbon such as fructose, glucose sugar monose is carried out high efficiency separation, separate for Nanofiltration-membrane technique being applied to Separation of fructose and glucose, wood sugar pectinose, and other separation with mixture of monosaccharides of the monose of same molecular amount or close molecular weight provide method and foundation.
Summary of the invention
Purpose of the present invention be exactly provide in order to overcome the defective that above-mentioned prior art exists a kind of invest little, efficient is high, the nanofiltration separation method of good economy performance, monose simple to operate.
Purpose of the present invention can be achieved through the following technical solutions: a kind of nanofiltration separation method of monose, it is characterized in that, mixture of monosaccharides to be separated is mixed with the aqueous solution that concentration is 1wt%-30wt%, adopt nanofiltration membrane to carry out nanofiltration separation, the condition of nanofiltration separation is: pressure range is controlled at 0.1bar～45bar, the nanofiltration membrane surface velocity is controlled at 0.1m/s～10m/s, solution temperature is controlled at 1 ℃～55 ℃, add ion take the ionic concn of the aqueous solution of regulating mixture of monosaccharides preparation to be separated as 0～2mol/L, pH value of solution is controlled at 0～9; Described mixture of monosaccharides to be separated is the mixture of monosaccharides of carbonatoms 4～7.
Described mixture of monosaccharides to be separated comprises the mixture of the isomers of same carbon atoms number.
The monose of carbonatoms 4～7 comprises erythrose, threose, erythrulose, wood sugar, ribose, lyxose, pectinose, ribulose, xylulose, allose, glucose, fructose, altrose, seminose, gulose, idose, semi-lactosi, talose, psicose, sorbose, tagatose, Fucose, black algae angle sugar, rhamnosyl, sedoheptulose, mannoheptulose or glucosamine.
The trapped molecular weight of described nanofiltration membrane is 100Da～1000Da, and nanofiltration membrane surface lotus is positive electricity, bear electricity or electric neutrality.
Add ion take the ionic concn of the aqueous solution of regulating mixture of monosaccharides preparation to be separated as 0～2mol/L, the ionic concn Li of the aqueous solution of described mixture of monosaccharides preparation to be separated
+, Na
+, K
+, Ca
2+, Mg
2+, Cl
-, SO
4 2-, SO
3 2-, HSO
3 -In one or more regulate.
The mode that described nanofiltration membrane is carried out nanofiltration separation comprises one-level nanofiltration membrane or multistage nanofiltration membrane, and the nanofiltration membrane of every one-level adopts same or different nanofiltration membrane; The side of holding back of the film in nanofiltration membrane is added water from diffusion, and the diafiltration multiple is 0-100 times of initial syrup volume.
The filtration progression of described nanofiltration membrane is the 1-100 level, and described water from diffusion comprises pure water, regulate water that pH is 0-9, add electrolytical water.
Compared with prior art, the present invention passes through regulation and control and the molecular modification to the material physical properties of monose solution, variation in conjunction with nanofiltration membrane surface charge character and trapped molecular weight, by regulation and control nanofiltration process stalling characteristic, 4～7 carbon such as fructose, glucose sugar monose is carried out high efficiency separation, separate for Nanofiltration-membrane technique being applied to Separation of fructose and glucose, wood sugar pectinose, and other separation with mixture of monosaccharides of the monose of same molecular amount or close molecular weight provide method and foundation.
Embodiment
The present invention is described in detail below in conjunction with specific embodiment.
Embodiment 1:
Fructose and glucose were mixed according to 1: 1, and add CaCl
2Regulating fructose and glucose mixture concentration of aqueous solution is 0.01mol/L, total sugar concentration 20wt%, at crossflow velocity 3m/s, pressure 28bar, 25 ℃ of temperature, pH=6.5, use nanofiltration membrane with negative electric charge, the molecular weight cut-off of film is under the condition of 1000Da, filters through 10 grades of membrane sepn, the diafiltration multiple is 6 times of beginning syrup volume, and obtaining fructose purity is 95% syrupy product.
Embodiment 2:
Wood sugar and the pectinose of carbonatoms 4～7 were mixed according to 2: 1, total sugar concentration 28wt%, at crossflow velocity 5m/s, pressure 38bar, 35 ℃ of temperature, pH=8.5, use nanofiltration membrane with negative electric charge, the molecular weight cut-off of film is under the condition of 250Da, filters through 5 grades of membrane sepn, the diafiltration multiple is 16 times of beginning syrup volume, obtains wood sugar purity and is 90% syrupy product.
Embodiment 3:
Fructose and the glucose of carbonatoms 4～7 were mixed according to 1: 1, and add KHSO
3Regulating fructose and glucose mixture concentration of aqueous solution is 0.1mol/L, total sugar concentration 15wt%, at crossflow velocity 2m/s, pressure 16bar, 48 ℃ of temperature, pH=4.5, use positively charged nanofiltration membranes, the molecular weight cut-off of film is under the condition of 850Da, filters through 6 grades of membrane sepn, the diafiltration multiple is 5 times of beginning syrup volume, and obtaining glucose purity is 75% syrupy product.
Embodiment 4:
Ribulose and the xylulose of carbonatoms 4～7 were mixed according to 3: 1, and add Na
2SO
3Regulating ribulose and xylulose mixture aqueous solution concentration is 0.05mol/L, total sugar concentration 22wt%, at crossflow velocity 2.7m/s, pressure 26bar, 28 ℃ of temperature, pH=5, use the electric neutrality nanofiltration membrane, the molecular weight cut-off of film is under the condition of 450Da, filters through 6 grades of membrane sepn, the diafiltration multiple is 25 times of beginning syrup volume, and obtaining ribulose purity is 90% syrupy product.
Embodiment 5:
Erythrose, the erythrulose of carbonatoms 4～7 were mixed according to 1: 1, and add CaCl
2Adjusting erythrose, erythrulose mixture aqueous solution concentration are 0.05mol/L, total sugar concentration 12wt%, at crossflow velocity 4.6m/s, pressure 20bar, 38 ℃ of temperature, pH=4.5, use nanofiltration membrane with negative electric charge, the molecular weight cut-off of film is under the condition of 500Da, filters through 4 grades of membrane sepn, the diafiltration multiple is 8 times of beginning syrup volume, and obtaining erythrose purity is 88% syrupy product.
Embodiment 6:
Sorbose, the tagatose of carbonatoms 4～7 were mixed according to 1.5: 1, and interpolation KCl regulates sorbose and tagatose mixture aqueous solution concentration is 0.01mol/L, and total sugar concentration 25wt% is at crossflow velocity 4.1m/s, pressure 25bar, 30 ℃ of temperature, pH=2.6 uses positively charged nanofiltration membranes, the molecular weight cut-off of film is under the condition of 350Da, filter through 5 grades of membrane sepn, the diafiltration multiple is 15 times of beginning syrup volume, obtains tagatose purity 92% syrupy product.
Semi-lactosi, the talose of carbonatoms 4～7 were mixed according to 2.5: 1, and add MgSO
4Regulating semi-lactosi and talose mixture aqueous solution concentration is 0.015mol/L, total sugar concentration 8wt%, at crossflow velocity 5m/s, pressure 17bar, 18 ℃ of temperature, pH=4.5, use nanofiltration membrane with negative electric charge, the molecular weight cut-off of film is under the condition of 950Da, filters through 10 grades of membrane sepn, the diafiltration multiple is 5 times of beginning syrup volume, and obtaining talose purity is 98% syrupy product.
Embodiment 8:
Gulose, the idose of carbonatoms 4～7 were mixed according to 1: 2, and add K
2SO
3Regulating gulose and idose mixture aqueous solution concentration is 0.05mol/L, total sugar concentration 1wt%, at crossflow velocity 2.7m/s, pressure 26bar, temperature 45 C, pH=9, use on schedule nanofiltration membrane of lotus, the molecular weight cut-off of film is under the condition of 450Da, filters through 12 grades of membrane sepn, the diafiltration multiple is 0.5 times of beginning syrup volume, and obtaining gulose purity is 99% syrupy product.
Embodiment 9:
Sedoheptulose, the mannoheptulose of carbonatoms 4～7 were mixed according to 1: 1, and interpolation LiCl regulates gulose and idose mixture aqueous solution concentration is 0.25mol/L, and total sugar concentration 15wt% is at crossflow velocity 3.2m/s, pressure 10bar, 48 ℃ of temperature, pH=4.2 uses nanofiltration membrane with negative electric charge, the molecular weight cut-off of film is under the condition of 800Da, filter through 3 grades of membrane sepn, the diafiltration multiple is 12 times of beginning syrup volume, and obtaining ketoheptose purity is 75% syrupy product.
Embodiment 10:
Glucosamine, the mannoheptulose of carbonatoms 4～7 were mixed according to 1: 1, and interpolation LiCl regulates glucosamine and mannoheptulose mixture aqueous solution concentration is 0.3mol/L, and total sugar concentration 1wt% is at crossflow velocity 0.1m/s, pressure 0.1bar, 1 ℃ of temperature, pH=0 uses nanofiltration membrane with negative electric charge, the molecular weight cut-off of film is under the condition of 100Da, filter through 3 grades of membrane sepn, the diafiltration multiple is 0 times of beginning syrup volume, obtains the glucosamine product.
Embodiment 11:
Two kinds of glucosamine isomerss of carbonatoms 7 were mixed according to 1: 1, and add MgSO
4Regulating glucosamine mixture aqueous solution concentration is 2mol/L, total sugar concentration 3wt%, at crossflow velocity 10m/s, pressure 45bar, 55 ℃ of temperature, pH=9, use nanofiltration membrane with negative electric charge, the molecular weight cut-off of film is under the condition of 1000Da, filters through 100 grades of membrane sepn, the diafiltration multiple is 100 times of beginning syrup volume, the glucosamine product after obtaining separating.
Claims (7)
1. the nanofiltration separation method of a monose, it is characterized in that, mixture of monosaccharides to be separated is mixed with the aqueous solution that concentration is 1wt%-30wt%, adopt nanofiltration membrane to carry out nanofiltration separation, the condition of nanofiltration separation is: pressure range is controlled at 0.1bar～45bar, and the nanofiltration membrane surface velocity is controlled at 0.1m/s～10m/s, and solution temperature is controlled at 1 ℃～55 ℃, add ion take the ionic concn of the aqueous solution of regulating mixture of monosaccharides preparation to be separated as 0～2mol/L, pH value of solution is controlled at 0～9; Described mixture of monosaccharides to be separated is the mixture of monosaccharides of carbonatoms 4～7.
2. the nanofiltration separation method of a kind of monose according to claim 1 is characterized in that, described mixture of monosaccharides to be separated comprises the mixture of the isomers of same carbon atoms number.
3. the nanofiltration separation method of a kind of monose according to claim 1, it is characterized in that, the monose of carbonatoms 4～7 comprises erythrose, threose, erythrulose, wood sugar, ribose, lyxose, pectinose, ribulose, xylulose, allose, glucose, fructose, altrose, seminose, gulose, idose, semi-lactosi, talose, psicose, sorbose, tagatose, Fucose, black algae angle sugar, rhamnosyl, sedoheptulose, mannoheptulose or glucosamine.
4. the nanofiltration separation method of a kind of monose according to claim 1 is characterized in that, the trapped molecular weight of described nanofiltration membrane is 100Da～1000Da, and nanofiltration membrane surface lotus is positive electricity, bear electricity or electric neutrality.
5. the nanofiltration separation method of a kind of monose according to claim 1 is characterized in that, adds ion take the ionic concn of the aqueous solution of regulating mixture of monosaccharides preparation to be separated as 0～2mol/L, and the ion of interpolation comprises Li
+, Na
+, K
+, Ca
2+, Mg
2+, Cl
-, SO
4 2-, SO
3 2-, HSO
3 -In one or more.
6. the nanofiltration separation method of a kind of monose according to claim 1 is characterized in that, the mode that described nanofiltration membrane is carried out nanofiltration separation comprises one-level nanofiltration membrane or multistage nanofiltration membrane, and the nanofiltration membrane of every one-level adopts same or different nanofiltration membrane; The side of holding back of the film in nanofiltration membrane is added water from diffusion, and the diafiltration multiple is 0-100 times of initial syrup volume.
7. according to claim 1 or the nanofiltration separation method of 6 described a kind of monose, it is characterized in that, the filtration progression of described nanofiltration membrane is the 1-100 level, and described water from diffusion comprises pure water, regulate water that pH is 0-9, add electrolytical water.
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| CN103694280A (en) * | 2013-11-29 | 2014-04-02 | 安徽丰原发酵技术工程研究有限公司 | Method for extracting glucosamine hydrochloride from glucosamine hydrochloride-containing mother liquor |
| CN104861005A (en) * | 2015-05-26 | 2015-08-26 | 华东理工大学 | Electric field and flow field coupling and regulation nanofiltration and separation method of glucosamine |
| CN105283188A (en) * | 2013-03-21 | 2016-01-27 | 维也纳医科大学 | Use of sedoheptulose for prevention or treatment of inflammation |
| CN107142336A (en) * | 2017-05-08 | 2017-09-08 | 丁宁 | The sugar-free brown sugar preparation method and applications of sucrose in brown sugar are sloughed in a kind of nanofiltration |
| JP2020514294A (en) * | 2017-01-05 | 2020-05-21 | ロケット フレールＲｏｑｕｅｔｔｅ Ｆｒｅｒｅｓ | Method for producing D-allulose crystals |
| CN113825410A (en) * | 2019-03-29 | 2021-12-21 | Cj第一制糖株式会社 | Mixed sugar compositions |
| US11439168B2 (en) | 2017-01-05 | 2022-09-13 | Roquette Freres | Non-crystallisable D-allulose syrups |
| US11766062B2 (en) | 2017-01-05 | 2023-09-26 | Roquette Freres | Crystallisable d-allulose syrups |
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| CN105283188A (en) * | 2013-03-21 | 2016-01-27 | 维也纳医科大学 | Use of sedoheptulose for prevention or treatment of inflammation |
| CN103694280A (en) * | 2013-11-29 | 2014-04-02 | 安徽丰原发酵技术工程研究有限公司 | Method for extracting glucosamine hydrochloride from glucosamine hydrochloride-containing mother liquor |
| CN103694280B (en) * | 2013-11-29 | 2015-11-25 | 安徽丰原发酵技术工程研究有限公司 | From containing the method extracting glucosamine hydrochloride glucosamine hydrochloride mother liquid |
| CN104861005B (en) * | 2015-05-26 | 2020-12-04 | 华东理工大学 | Electric field and flow field coupling regulation nanofiltration separation method of glucosamine |
| CN104861005A (en) * | 2015-05-26 | 2015-08-26 | 华东理工大学 | Electric field and flow field coupling and regulation nanofiltration and separation method of glucosamine |
| JP2020514294A (en) * | 2017-01-05 | 2020-05-21 | ロケット フレールＲｏｑｕｅｔｔｅ Ｆｒｅｒｅｓ | Method for producing D-allulose crystals |
| US11439168B2 (en) | 2017-01-05 | 2022-09-13 | Roquette Freres | Non-crystallisable D-allulose syrups |
| JP2023011728A (en) * | 2017-01-05 | 2023-01-24 | ロケット フレール | Method for producing D-allulose crystals |
| US11766062B2 (en) | 2017-01-05 | 2023-09-26 | Roquette Freres | Crystallisable d-allulose syrups |
| US11945835B2 (en) | 2017-01-05 | 2024-04-02 | Roquette Freres | Method for producing D-allulose crystals |
| EP4378325A3 (en) * | 2017-01-05 | 2024-08-07 | Roquette Freres | Crystallizable syrups for d-allulose |
| CN107142336A (en) * | 2017-05-08 | 2017-09-08 | 丁宁 | The sugar-free brown sugar preparation method and applications of sucrose in brown sugar are sloughed in a kind of nanofiltration |
| CN113825410A (en) * | 2019-03-29 | 2021-12-21 | Cj第一制糖株式会社 | Mixed sugar compositions |
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