CN102329340A - Method for preparing D-mannose - Google Patents
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Abstract
The invention discloses a method for preparing D-mannose. The method comprises the following steps of: epimerizing glucose to partially transform the glucose into mannose to obtain a mixed solution of the glucose and the mannose, separating the mixed solution for three times by a simulated moving bed to obtain C1 which is rich in a mannose component as well as A2, B2 and C2 which are rich in a glucose component, and desalting the C1, concentrating, crystallizing, centrifuging and drying to obtain high-purity D-mannose. The separated liquid which is obtained through first-time separation by the simulated moving bed and is rich in the glucose component is filtered by a membrane filtration device, then dialysate is epimerized, and the separated liquid B2 and the separated liquid C2 which are obtained through second-time separation and third-time separation by the simulated moving bed enter the simulated moving bed and are separated for the first time again. In the process, a membrane separation technology and a high-efficiency separation effect of the simulated moving bed are utilized, and a crystal product with the purity of over 99 percent is directly obtained in a way of the combination of cooling crystallization and organic solvent crystallization through one-step crystallization without a refinement link; and the process is simple and the product can be produced easily.
Description
Technical field
The present invention relates to a kind of D-seminose preparation method.
Background technology
The D-seminose is the white powder crystallization, and crystal formation has α type and β type.(250%) soluble in water is insoluble in ethanol (0.4%), is insoluble to ether.D-sweet dew flavour of candy is sweet, is 0.6 times of sucrose, about 0.86 times of glucose, has a little bitter aftertaste, has reductibility, can be by microbial fermentation.Natural seminose is many to be existed with polymeric species, for example is present in the konjaku of aroid, is called Oligomeric manna sugar.Seminose can be applied to food, medicine and other fields.Some research datas of the U.S. show that seminose is a kind of sugar with special efficacy function, has good sterilization, inflammation-diminishing function, and it has the effect of good assisting therapy to diseases such as diabetics, obesity, constipation, hypercholesterolemias.
The acquisition of crystallization D-seminose is main with extraction method mainly in the prior art, is raw material with ivory reality, Exocarpium cocois (Cocos nucifera L), palm powder mainly, obtains the mixed solution of seminose and other oligosaccharides through degraded, and crystallization obtains the D-seminose then.But there is numerous defectives in extraction method: there is environmental pollution problems in the acid system degraded, and the enzymic degradation cost is high.The degraded product that utilizes extraction method to obtain is generally the mixture of multiple material, because separation condition is limited, the yield of product and purity are all lower, are difficult to obtain high purity D-seminose.
Chinese patent CN101851689A discloses the technology that a kind of synthesis method prepares seminose.With glucose is that raw material carries out the mixed solution that chemical isomerization obtains seminose and glucose; Through parting material is the simulation moving-bed separation one time of gel PS calcium type resin; After concentrating through twice, the parting liquid that obtains being rich in the seminose component carries out aqueous crystallization; Last 60-100h, after centrifugal coarse-grain.Improve purity with soaked in absolute ethyl alcohol washing coarse-grain, obtain content at the seminose goods more than 99%.This method can obtain highly purified crystallization D-seminose, but the solubleness of seminose in water is 250g/g, the aqueous crystallization difficulty; Need increase energy consumption cost through twice concentration technology before the aqueous crystallization; Need the control cooling rate in the aqueous crystallization process, temperature controlling instruments is required high; Crystallization lasts 60-100h, and the time is long, efficient is low; It is refining that the bullion seminose that aqueous crystallization obtains need be proceeded absolute ethyl alcohol, and technology is loaded down with trivial details; And this technology uses in the separation and purification process is gel PS Ca type resin, and separation rate is less than 60%.
Summary of the invention
To above-mentioned defective and deficiency that the method for preparing seminose in the prior art exists, the object of the invention has just provided the D-seminose preparation method that a kind of technology is simple, crystalline rate is high, easy to operate.The present invention adopts the simulation moving-bed separate mode that combines with membrane filter appts, guarantees the epimerization transformation efficiency; Need not pass through refining link, simplify production technique; The used parting material of the present invention is special Ca-type molecular sieve, and the separation rate of molecular sieve is far longer than resin.
For realizing the foregoing invention purpose, the present invention adopts following technical proposals to be achieved:
A kind of D-seminose preparation method may further comprise the steps:
(1) isomery: glucose is diluted with water to mass concentration 55-65%; Add the catalyzer ammonium molybdate that accounts for glucose quality 0.09-0.1%; Under 105-125 ℃, 0.12Mpa condition, carry out epimerization, obtain glucose, seminose mixed solution that mannose content is 29-32%;
(2) decolouring desalination: with said glucose, seminose mixed solution decolour, desalting refinement gets glucose, the seminose mixed liquor A;
(3) separate: said glucose, seminose mixed liquor A are through the simulation moving-bed A2 that separates to such an extent that be rich in the A1 of seminose component and be rich in the glucose component;
(4) concentrate: the said A1 that is rich in the seminose component is carried out evaporation concentration get feed liquid B;
(5) separate: the simulation moving-bed B2 that separates to such an extent that be rich in the B1 of seminose component and be rich in the glucose component of said feed liquid B process;
(6) concentrate: the said B1 that is rich in the seminose component is carried out evaporation concentration get feed liquid C;
(7) separate: the simulation moving-bed C2 that separates to such an extent that be rich in the C1 of seminose component and be rich in the glucose component of said feed liquid C process;
(8) concentrate: said feed liquid C1 desalination, evaporation concentration are got the D that the seminose mass concentration is 65-85%;
(9) crystallization: D is carried out crystallization, and centrifugal, dry D-seminose goods D1 and the seminose mother liquor D2 of getting, D2 advance C solution through simulation moving-bed separation more for the third time, organic solvent recycling use after concentrating and removing organic solvent;
The A2 that (10) will be rich in the glucose component handles laggard epimerization through membrane filter appts, and the B2, the C2 that are rich in the glucose component advance the simulation moving-bed separation of first pass.
Further improvement to technical scheme: said step (3), (5) and (7) are simulation moving-bed is the binary tripping device, and filtration film device is a nf membrane, and the minimum molecular weight that can hold back material is 200-250.
Further improvement to technical scheme: mannose content 79-84% among said step (3) A1, assorted sugared content 0.4-0.5%, mannose content 8-15% among the A2, assorted sugared content 1.8-2.5%.
Further improvement to technical scheme: mannose content 92-94% among said step (5) B1, assorted sugared content 0.22-0.31%, mannose content 32-36% among the B2, assorted sugared content 1.1-1.5%.
Further improvement to technical scheme: mannose content 97.5-98% among said step (7) C1, assorted sugared content 0.2-0.3%, mannose content 63-68% among the C2, assorted sugared content 0.7-1.0%.
Further improvement to technical scheme: the seminose crystallization comprises organic solvent crystallization and crystallisation by cooling in the said step (9), and organic solvent content 56.5-63% in the crystallization control system controls sugared concentration 28.3-31.5%; Stir, carry out crystallisation by cooling, when the crystallizing system temperature is reduced to 25-38 ℃; Add crystal seed, control stirring velocity 2-10r/min, whole crystallisation process lasts 4.5-6h; Centrifugal, drying obtains the seminose crystal, crystallization yield 58.5-64%.
Further improvement to technical scheme: the crystallization organic solvent is a water-miscible organic solvent in the said step (9), and said water-miscible organic solvent is ethanol, acetone, methyl alcohol, is preferably ethanol.
Further improvement to technical scheme: said seminose crystalline crystal formation is regular six prismatics.
Further improvement to technical scheme: the A2 that is rich in the glucose component in the said step (10) is through behind the membrane filter appts, and assorted sugared content is 0.26-0.57%.
Further improvement to technical scheme: use gac to decolour in the said step (2), make the spent ion exchange resin desalination.
Compared with prior art, advantage of the present invention and positively effect are:
(1) the present invention adopts the simulation moving-bed separate mode that combines with membrane filter appts, mixed solution behind the epimerization through simulation moving-bed separate two phases, promptly be rich in the parting liquid and the parting liquid that is rich in the glucose component of seminose component.Wherein, the parting liquid that is rich in the seminose component through desalination, concentrate after direct crystallization; Be rich in and be rich in assorted sugar among the A2 of glucose component simultaneously; The parting liquid that is rich in the glucose component through obtaining after the simulation moving-bed first pass separation uses membrane filter appts to handle; Assorted sugared content is below 0.5% in the dialyzate; Thereby the content that reduces assorted sugar in the parting liquid reduces it to epimeric restraining effect, guarantees the epimerization transformation efficiency.
If use ternary simulation moving-bed; After going over separation, be rich in the seminose component assorted sugared content seldom, below 0.5%, continue through the simulation moving-bed separation of ternary; Mannose content can continue to improve; It is very little that but assorted sugared content reduces, and lost the isolating meaning of ternary, increased separation costs.Therefore, be under the purpose situation to obtain the high-content seminose, use the simulation moving-bed separate mode that combines with membrane filtration to have a bigger advantage than ternary is simulation moving-bed.
(2) preparation method of the present invention has made full use of simulation moving-bed high efficiency separation effect and has designed, through three times simulation moving-bed, the content of seminose is increased to 97.5-98% by 29-32%.Process is separated the content of back seminose all more than 97%, can directly carry out the crystalline articles that organic solvent one step crystallization obtains mannose content 99.1-99.7%, need not pass through refining link, has simplified production technique.
(3) the organic solvent crystallization of technology of the present invention lasts 4.5-6h, and than aqueous crystallization time spent 60-100h, crystallization time shortens greatly, has improved crystalline rate; The organic solvent crystallization need be concentrated into feed liquid between the 65-85%, needs at twice feed liquid to be concentrated into 90-95% than aqueous crystallization, has saved concentrated cost, has reduced energy consumption, has simplified operation.The natural cooling crystallization method is adopted in the organic solvent crystallization, only needs control crystal seed joining day and stirring velocity, needs strict control cooling rate than aqueous crystallization, and operation and equipment are simpler.
(4) the used parting material of method of the present invention is special Ca-type molecular sieve, and it has uniform pore structure, bigger surface-area, higher surface polarity and skeleton structure stability.Through test, when using this molecular sieve to separate as parting material, the separating size of seminose, glucose is 1.25,1.13 when being higher than with resin.With seminose, the glucose mixed solution of this molecular sieving mannose content 30%, separate the back mannose content and can reach 79-84%, as if being parting material with the resin, mannose content then is lower than 60%, and the separation rate of molecular sieve is far longer than resin.Therefore use special Ca-type molecular sieve to have better separating effect than resin as parting material.
After advantages embodiment of the present invention, other characteristics of the present invention and advantage will become clearer.
Description of drawings
Fig. 1 is the preparation flow figure of D-seminose of the present invention.
Fig. 2 is the analysis of spectra of embodiment 2 through mixed solution liquid phase collection of illustrative plates after the epimerization.
Fig. 3 is rich in the analysis of spectra of the parting liquid liquid phase collection of illustrative plates of seminose component through three times simulation moving-bed after separatings for embodiment 2.
Fig. 4 be the D-seminose crystalline articles that obtains of embodiment 2 the analysis of spectra of liquid phase collection of illustrative plates.
Embodiment
Below in conjunction with accompanying drawing and embodiment technical scheme of the present invention is done further detailed explanation.
Embodiment 1
The preparation method of D-seminose of the present invention may further comprise the steps:
(1) using pure water to be diluted to concentration 5kg anhydrous crystal glucose is 65%; Add catalyzer ammonium molybdate 5g; Under 125 ℃, 0.12Mpa condition, carry out epimerization, glucose moiety is converted into seminose, the content that isomery finishes seminose in the mixed solution of back is 31.6%.
(2) with glucose that obtains behind the isomery and seminose mixed solution process activated carbon decolorizing, the ion exchange resin desalting refinement obtains glucose and seminose mixed liquor A.
(3) said mixed liquor A gets into simulation moving-bed separation and purification; Obtain being rich in the component A1 and the component A2 that is rich in glucose of seminose; Be rich in wherein that mannose content is 81% among the A1 of seminose component; Assorted sugared content 0.42% is rich in mannose content 11% in the glucose component, assorted sugared content 2.1%.
The component A1 that (4) will be rich in seminose obtains feed liquid B through evaporation concentration.
(5) with the simulation moving-bed separation of said feed liquid B process; Obtain being rich in the B component 1 and the B component 2 that is rich in glucose of seminose, wherein be rich in mannose content 94% among the B1 of seminose component, assorted sugared content 0.24%; Be rich in mannose content 34% in the glucose component, assorted sugared content 1.16%.
The B component 1 that (6) will be rich in seminose obtains feed liquid C through evaporation concentration.
(7) with the simulation moving-bed separation of said feed liquid C process; Obtain being rich in the component C1 and the component C2 that is rich in glucose of seminose; The content that wherein is rich in seminose among the C1 of seminose component is 97.8%; Assorted sugared content 0.29% is rich in mannose content 65% in the glucose component, assorted sugared content 0.75%.
The component C1 that (8) will be rich in seminose concentrates through ion exchange resin desalination, single vaporization, mannose concentration is 74.8% feed liquid D.
(9) in feed liquid D, add absolute ethyl alcohol 2.76L, the concentration 27.5% of liquid glucose is carried out the organic solvent crystallization in the system, control stirring velocity 5r/min; When temperature is reduced to 32 ℃, add crystal seed, continue stirred crystallization, control stirring velocity 5r/min; Centrifugal after the 6h, it is wet brilliant to obtain the D-seminose, and drying obtains crystalline articles 0.717kg; Content is 99.1%, and crystal formation is six prismatics, and the product crystallization yield is 60.4%.
Crystalline mother solution D2 concentrates and to remove ethanol, takes off mannose content 95.8% behind the ethanol, advances the 3rd time and simulation moving-bedly separates again, and ethanol reclaims and uses.
(10) forward that the assorted sugar that contains high level in the A2 parting liquid that is rich in the glucose component that obtains after the simulation moving-bed separation, the enrichment of assorted sugar have influenced the epimerization reaction carries out, and finally influences product yield and quality product.Parting liquid is through behind the membrane filter appts, and assorted sugared content is reduced to 0.41% by 2.1%, and dialyzate is proceeded epimerization, and assorted sugar reduces the restraining effect of epimerization reaction, and the isomery transformation efficiency 28.5% brings up to 31.5% when not removing assorted sugar.B2, C2 advance the simulation moving-bed separation of first pass.
Embodiment 2
The preparation method of D-seminose of the present invention may further comprise the steps:
(1) using pure water to be diluted to concentration 5kg anhydrous crystal glucose is 65%; Add catalyzer ammonium molybdate 5g; Under 125 ℃, 0.12Mpa condition, carry out epimerization, glucose moiety is converted into seminose, the content that isomery finishes seminose in the mixed solution of back is 31.6%.
(2) glucose that obtains behind the isomery and seminose mixed solution are obtained glucose, seminose mixed liquor A through activated carbon decolorizing, ion exchange resin desalting refinement.
(3) with the simulation moving-bed separation and purification of said mixed liquor A process; Obtain being rich in the component A1 and the component A2 that is rich in glucose of seminose, wherein mannose content is 81% among the A1, assorted sugared content 0.42%; Be rich in mannose content 11% in the glucose component, assorted sugared content 2.1%.
The component A1 that (4) will be rich in seminose obtains feed liquid B through evaporation concentration.
(5) with the simulation moving-bed separation of said feed liquid B process; Obtain being rich in the B component 1 and the B component 2 that is rich in glucose of seminose, mannose content 94% among the B1 wherein, assorted sugared content 0.24%; Be rich in mannose content 34% in the glucose component, assorted sugared content 1.16%.
The B component 1 that (6) will be rich in seminose obtains feed liquid C through evaporation concentration.
(7) with the simulation moving-bed separation and purification of said feed liquid C process; Obtain being rich in the component C1 and the component C2 that is rich in glucose of seminose, wherein the content of seminose is 97.8% among the C1, assorted sugared content 0.29%; Be rich in mannose content 65% in the glucose component, assorted sugared content 0.75%.
The component C1 that (8) will be rich in seminose concentrates through ion exchange resin desalination, single vaporization, the feed liquid D of concentration 74.8%.
(9) in feed liquid D, add absolute ethyl alcohol 2.32L, the concentration 30.5% of liquid glucose is carried out the organic solvent crystallization in the system, control stirring velocity 5r/min; When temperature is reduced to 32 ℃, add crystal seed, continue stirred crystallization, control stirring velocity 5r/min; 5.5h centrifugal afterwards, it is wet brilliant to obtain the D-seminose, drying obtains crystalline articles 0.752kg; Content is 99.6%, and crystal formation is six prismatics, and the product crystallization yield is 63.7%.
Crystalline mother solution concentrates and to remove ethanol, takes off mannose content 95.8% behind the ethanol, simulation moving-bedly separates for laggard the 3rd time again, and ethanol reclaims and uses.
The A2 that (10) will be rich in the glucose component removes assorted sugar through the nf membrane filtration unit, and assorted sugared content is reduced to 0.41% by 2.1%, and dialyzate advances epimerization, and the isomery transformation efficiency 28.5% brings up to 31.5% when not removing assorted sugar.B2, C2 advance the simulation moving-bed separation of first pass.
Table 1: through mixed solution liquid chromatography diagram data after the epimerization
| Behind the isomery | RT | Area percentage |
| Unknown | 9.847 | 1.20 |
| Glucose | 12.109 | 66.92 |
| Seminose | 13.812 | 31.6 |
| Fructose | 15.633 | 0.28 |
Can find out that by table 1 through after the epimerization, glucose moiety is converted into seminose, generates a spot of assorted sugar simultaneously.This moment, the content of glucose was 66.92%, and the content of seminose is 31.6%, and the content (comprising unknown component and fructose) of assorted sugar is 1.48%.
Table 2: the parting liquid liquid chromatography diagram data that is rich in the seminose component through three times simulation moving-bed after separatings
| After simulation moving-bed | RT | Area percentage |
| Unknown | 10.876 | 0.08 |
| Glucose | 12.101 | 1.91 |
| Seminose | 13.801 | 97.8 |
| Fructose | 16.517 | 0.21 |
Can be found out that by chart 2 after three times simulation moving-bed separation and purification, mannose content reaches 97.8%, purification effect is better, and this fashion contains a spot of glucose and assorted sugar, and content is respectively 1.91%, 0.29%.
Table 3:D-seminose crystalline articles liquid chromatography diagram data
| After the crystallization | RT | Area percentage |
| Unknown | 10.901 | 0.05 |
| Glucose | 11.783 | 0.10 |
| Seminose | 13.779 | 99.6 |
| Fructose | 16.938 | 0.25 |
Can find out that by chart 3 through crystallization, seminose separates with glucose moiety; Seminose purity continues to improve; Mannose content is 99.6% in the crystalline articles, and the content of a spot of glucose and assorted sugar is respectively 0.1%, 0.3%, and (the performance liquid chromatography model is Waters 2414, and employed detector is a differential refraction detector; Moving phase is high purity water, and flow velocity is 0.5ml/min.)。
Above embodiment is only in order to explaining technical scheme of the present invention, but not limits it; Although the present invention has been carried out detailed explanation with reference to previous embodiment, for the person of ordinary skill of the art, still can make amendment to the technical scheme that previous embodiment is put down in writing, perhaps part technical characterictic wherein is equal to replacement; And these modifications or replacement do not make the essence of relevant art scheme break away from the spirit and the scope of the present invention's technical scheme required for protection.
Claims (10)
1. D-seminose preparation method is characterized in that may further comprise the steps:
(1) isomery: glucose is diluted with water to mass concentration 55-65%; Add the catalyzer ammonium molybdate that accounts for glucose quality 0.09-0.1%; Under 105-125 ℃, 0.12Mpa condition, carry out epimerization, obtain glucose, seminose mixed solution that mannose content is 29-32%;
(2) decolouring desalination: with said glucose, seminose mixed solution decolour, desalting refinement gets glucose, the seminose mixed liquor A;
(3) separate: said glucose, seminose mixed liquor A are through the simulation moving-bed A2 that separates to such an extent that be rich in the A1 of seminose component and be rich in the glucose component;
(4) concentrate: the said A1 that is rich in the seminose component is carried out evaporation concentration get feed liquid B;
(5) separate: the simulation moving-bed B2 that separates to such an extent that be rich in the B1 of seminose component and be rich in the glucose component of said feed liquid B process;
(6) concentrate: the said B1 that is rich in the seminose component is carried out evaporation concentration get feed liquid C;
(7) separate: the simulation moving-bed C2 that separates to such an extent that be rich in the C1 of seminose component and be rich in the glucose component of said feed liquid C process;
(8) concentrate: said feed liquid C1 desalination, evaporation concentration are got the D that the seminose mass concentration is 65-85%;
(9) crystallization: D is carried out crystallization, and centrifugal, dry D-seminose goods D1 and the seminose mother liquor D2 of getting, D2 advance C solution through simulation moving-bed separation more for the third time, organic solvent recycling use after concentrating and removing organic solvent;
The A2 that (10) will be rich in the glucose component handles laggard epimerization through membrane filter appts, and the B2, the C2 that are rich in the glucose component advance the simulation moving-bed separation of first pass.
2. a kind of D-seminose preparation method according to claim 1 is characterized in that said step (3), (5) and (7) are simulation moving-bed and is the binary tripping device that filtration film device is a nf membrane, and the minimum molecular weight that can hold back material is 200-250.
3. a kind of D-seminose preparation method according to claim 2 is characterized in that mannose content 79-84% among said step (3) A1, assorted sugared content 0.4-0.5%, mannose content 8-15% among the A2, assorted sugared content 1.8-2.5%.
4. a kind of D-seminose preparation method according to claim 3 is characterized in that mannose content 92-94% among said step (5) B1, assorted sugared content 0.22-0.31%, mannose content 32-36% among the B2, assorted sugared content 1.1-1.5%.
5. a kind of D-seminose preparation method according to claim 4 is characterized in that mannose content 97.5-98% among said step (7) C1, assorted sugared content 0.2-0.3%, mannose content 63-68% among the C2, assorted sugared content 0.7-1.0%.
6. a kind of D-seminose preparation method according to claim 1 is characterized in that the seminose crystallization comprises organic solvent crystallization and crystallisation by cooling, organic solvent content 56.5-63% in the crystallization control system in the said step (9); Control sugared concentration 28.3-31.5%, stir, carry out crystallisation by cooling; When the crystallizing system temperature is reduced to 25-38 ℃; Add crystal seed, control stirring velocity 2-10r/min, whole crystallisation process lasts 4.5-6h; Centrifugal, drying obtains the seminose crystal, crystallization yield 58.5-64%.
7. a kind of D-seminose preparation method according to claim 6 is characterized in that the crystallization organic solvent is a water-miscible organic solvent in the said step (9), and said water-miscible organic solvent is ethanol, acetone, methyl alcohol, is preferably ethanol.
8. a kind of D-seminose preparation method according to claim 7 is characterized in that said seminose crystalline crystal formation is regular six prismatics.
9. a kind of D-seminose preparation method according to claim 1, the A2 that it is characterized in that being rich in the glucose component in the said step (10) is through behind the membrane filter appts, and assorted sugared content is 0.26-0.57%.
10. a kind of D-seminose preparation method according to claim 1 is characterized in that using in the said step (2) gac to decolour, and makes the spent ion exchange resin desalination.
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Cited By (9)
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| CN102807593A (en) * | 2012-06-21 | 2012-12-05 | 白心亮 | Preparation method of mannose |
| CN103387593A (en) * | 2013-08-20 | 2013-11-13 | 青岛明月海藻集团有限公司 | High-yield co-production method of D-gluconic acid-delta-lactone, mannose and mannitol |
| CN103497221A (en) * | 2013-10-17 | 2014-01-08 | 山东福田药业有限公司 | Preparation method for D-mannose crystals |
| CN103831122A (en) * | 2014-01-30 | 2014-06-04 | 内蒙古民族大学 | Mixed catalyst for enhancing conversion rate of glucose to mannose |
| CN103992361A (en) * | 2014-02-21 | 2014-08-20 | 黑龙江八一农垦大学 | Separation process for mannose and glucose by using sequential simulated moving bed chromatography |
| CN104045670A (en) * | 2013-03-15 | 2014-09-17 | 大连中科格莱克生物科技有限公司 | Preparation method for mannose |
| CN104478948A (en) * | 2014-11-20 | 2015-04-01 | 青岛明月海藻生物科技有限公司 | Preparation method for producing mannose and animal nutrition auxiliary material and application of animal nutrition auxiliary material |
| CN106632524A (en) * | 2016-12-21 | 2017-05-10 | 南京凯通粮食生化研究设计有限公司 | Method for preparing high-content mannose |
| CN109320400A (en) * | 2018-09-30 | 2019-02-12 | 湖南华诚生物资源股份有限公司 | A method of natural mannitol is extracted from mogroside production waste liquid |
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Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102807593A (en) * | 2012-06-21 | 2012-12-05 | 白心亮 | Preparation method of mannose |
| CN104045670B (en) * | 2013-03-15 | 2017-06-06 | 大连中科格莱克生物科技有限公司 | A kind of preparation method of mannose |
| CN104045670A (en) * | 2013-03-15 | 2014-09-17 | 大连中科格莱克生物科技有限公司 | Preparation method for mannose |
| CN103387593A (en) * | 2013-08-20 | 2013-11-13 | 青岛明月海藻集团有限公司 | High-yield co-production method of D-gluconic acid-delta-lactone, mannose and mannitol |
| CN103387593B (en) * | 2013-08-20 | 2016-01-20 | 青岛明月海藻集团有限公司 | A kind of method of coproduction maltonic acid-delta-lactone, seminose and N.F,USP MANNITOL |
| CN103497221A (en) * | 2013-10-17 | 2014-01-08 | 山东福田药业有限公司 | Preparation method for D-mannose crystals |
| CN103831122A (en) * | 2014-01-30 | 2014-06-04 | 内蒙古民族大学 | Mixed catalyst for enhancing conversion rate of glucose to mannose |
| CN103831122B (en) * | 2014-01-30 | 2017-01-18 | 内蒙古民族大学 | Mixed catalyst for enhancing conversion rate of glucose to mannose |
| CN103992361A (en) * | 2014-02-21 | 2014-08-20 | 黑龙江八一农垦大学 | Separation process for mannose and glucose by using sequential simulated moving bed chromatography |
| CN104478948A (en) * | 2014-11-20 | 2015-04-01 | 青岛明月海藻生物科技有限公司 | Preparation method for producing mannose and animal nutrition auxiliary material and application of animal nutrition auxiliary material |
| CN104478948B (en) * | 2014-11-20 | 2017-08-25 | 青岛明月海藻生物科技有限公司 | A kind of application of the preparation method and Animal nutrition auxiliary material of mannose and Animal nutrition auxiliary material coproduction |
| CN106632524A (en) * | 2016-12-21 | 2017-05-10 | 南京凯通粮食生化研究设计有限公司 | Method for preparing high-content mannose |
| CN109320400A (en) * | 2018-09-30 | 2019-02-12 | 湖南华诚生物资源股份有限公司 | A method of natural mannitol is extracted from mogroside production waste liquid |
| CN109320400B (en) * | 2018-09-30 | 2021-08-10 | 湖南华诚生物资源股份有限公司 | Method for extracting natural mannitol from waste liquid of mogroside production |
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