CN1219782C - Cane sugar material high-yield joint production process of crystalline fructose and manna sugar - Google Patents
Cane sugar material high-yield joint production process of crystalline fructose and manna sugar Download PDFInfo
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- CN1219782C CN1219782C CN 03134957 CN03134957A CN1219782C CN 1219782 C CN1219782 C CN 1219782C CN 03134957 CN03134957 CN 03134957 CN 03134957 A CN03134957 A CN 03134957A CN 1219782 C CN1219782 C CN 1219782C
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Abstract
The present invention a technique for crystallizing fructose and mannitol by using sucrose or white sugar as raw material through chemical processing and separation with high yields. The yields of the fructose and the mannitol total 70%(measured according to the batch charging amount of the sucrose). In the implementation process, the present invention adopts the chemical reaction processes or chemical operation processes, for example hydrolyzation, adsorption separation, epimerization, ion exchange, concentration, crystallization, centrifugal separation, drying, etc., so as to obtain the main products of the crystallized fructose and the mannitol, and the byproduct of a small amount of sorbitol water solution.
Description
Technical field:
The invention belongs to the preparation field of organic compound.
Background technology:
Crystal diabetin has following several in industrial production method by the raw material sources mode: (1) is raw material with sucrose, elder generation's hydrolysis, obtain fructose and glucose mixture (is called Nulomoline, wherein fructose content is 46～50%), through fractionation by adsorption, obtain high-purity fructose (fructose content is more than 90%) and glucose, high-purity fructose through Crystallization Separation, can be got crystal diabetin.(2) with glucose be raw material, carry out isomerization reaction with glucose isomerase, obtain the mixture (wherein fructose content is about 42%) of fructose and glucose, with getting high-purity fructose (fructose content is more than 90%) and glucose after the fractionation by adsorption processing, after crystallization, separation, can obtain crystal diabetin.
More than two kinds of production methods in fact very similar, all be the main method of industrial production crystal diabetin.But the crystal diabetin productive rate of above-mentioned two methods is very low, is generally 20～26% of glucose (or sucrose) charging capacity, and a large amount of glucose components and fructose mother liquor behind the production crystal diabetin can't effectively be utilized.In addition, glucose isomerase in the method (2) costs an arm and a leg, if being carried out the enzyme isomery again, resulting glucose component behind the separating levulose changes into fructose about 42%, repeat the separation of fructose glucose, such treatment process is possible in theory, but can not adopt in the actual production, because the production cost of crystal diabetin can't reduce.In a word, the fundamental drawback of above-mentioned two methods is to utilize glucose component and fructose mother liquor economically.
In addition, crystal diabetin also has following method for making: (3) are carried out enzymatic conversion with the seminose raw material and are generated fructose under the effect of mannose isomerase, transformation efficiency can reach more than 80%, can obtain crystal diabetin through crystallization again.But be a problem in the source of seminose very much, and mannose isomerase can't supply in a large number in industrialization, and therefore, this method can't realize suitability for industrialized production at all; (4) synanthrin is hydrolyzed transforms generation fructose in 100% ground.But mainly extract from plant materials jerusalem artichoke fruit in the source of synanthrin, and the suitability for industrialized production raw material sources are extremely difficult.
In a word, produce crystal diabetin, must make high-purity fructose (fructose content 90%) earlier, just might crystallization.Content is lower than at 90% o'clock, and fructose is difficult to crystallization and separates out.Preparing high-purity fructose industrial generally is to adopt the isolating method and apparatus of simulated moving bed adsorption, can realize economically.
Above-described crystal diabetin method for making, what have can't realize suitability for industrialized production at all, a large amount of glucose components that have can't utilize.Therefore cause the few valency height of crystal diabetin amount, it is required to satisfy market in a large number.
The working system of N.F,USP MANNITOL has following several approach: (1) sea-tangle extraction method: contain N.F,USP MANNITOL 5～10% in the dried sea-tangle, can be through after concentrating, method with physical crystal is extracted, N.F,USP MANNITOL that this method is produced of poor quality, sad filter, the thermal source height is unsuitable for pharmaceutical, and this method expends a large amount of steam, energy and manpower, the production cost height.(2) electrolytic reduction: the mixture of glucose (or Nulomoline) reducible generation N.F,USP MANNITOL and sorbyl alcohol under electrolytic condition, again through crystallization extract and N.F,USP MANNITOL, this method long reaction time, efficient is low, power consumption is big, and N.F,USP MANNITOL productive rate low (only reaching 15%) is eliminated already.(3) be raw material with fructose: behind the fructose hydrogenation, get N.F,USP MANNITOL and sorbyl alcohol and respectively account for the mixed alcohol of half, can make N.F,USP MANNITOL with crystallization treatment, theoretical yield is 50%.But the price of fructose is higher, is not suitable for industrial production reality with pure fructose or high-purity fructose for raw material production N.F,USP MANNITOL.(4) with the seminose be raw material: seminose can all transform generation N.F,USP MANNITOL through hydrogenation.But be a problem in the source of pure seminose, is not suitable for industrial production reality.(5) be the synthesis method of raw material with sucrose: with sucrose hydrolysis, get fructose and glucose and respectively account for the Nulomoline of half, after handing over processing, carry out hydrogenation reaction, mannitol content is about 25% in the mixed alcohol of gained, and surplus is sorbyl alcohol.Through from hand over, concentrate, crystallization, centrifugation, drying can make the N.F,USP MANNITOL product, productive rate is about 19～20%.This method has in fact only been utilized the fructose component behind the sucrose hydrolysis, and the productive rate of gained N.F,USP MANNITOL is lower, and most product is the low sorbyl alcohol of value, and contained N.F,USP MANNITOL is about 8% in the sorbyl alcohol, and is second-rate.The industrial existing production of this method.(6) with glucose be raw material: glucose is carried out epimerization change into seminose (transformation efficiency is generally 30%),, can obtain the N.F,USP MANNITOL product through crystallization with transforming the N.F,USP MANNITOL sorbitol mixture that back liquid glucose hydrogenation can obtain 30% left and right sides content.This method has industrial installation, but the yield of N.F,USP MANNITOL is not high, only reaches 24～26%.If the liquid glucose behind the epimerization is carried out the enzyme isomery with glucose isomerase again, to there be the conversion of glucose about 30% to generate fructose, like this, behind epimerization and enzyme isomery, containing seminose in the liquid glucose is 30～33%, contains fructose 28～30%, surplus is glucose, the mannitol content that mixes alcohol through gained behind the hydrogenation can reach about 42%, and the N.F,USP MANNITOL productive rate that crystallization is extracted is about 35%, and all the other are sorbyl alcohol.This with glucose be raw material improvement working system be main N.F,USP MANNITOL production method, abroad generally adopt.
Above-described various N.F,USP MANNITOL working system, the not possibility industrialization that has is the method for raw material with fructose or seminose for example; The current consumption that has, the consumption quantity of steam higher, the production cost height is eliminated, for example electrolytic reduction and sea-tangle extraction method; Though suitability for industrialized production that has and running, but the N.F,USP MANNITOL productive rate is lower, only reach 19～20% as sucrose hydrolysis technology hydrogenation method productive rate, the productive rate of glucose epimerization and enzyme isomery repeated hydrogenation technology only reaches 35%, all the other are a large amount of low, ropy sorbyl alcohol liquid products of value, and economic benefit has much room for improvement.
The industrial production method of comprehensive crystal diabetin and N.F,USP MANNITOL, all exist the productive rate of high-value product (as crystal diabetin and N.F,USP MANNITOL) low, the too high rough sledding of productive rate of low-value product (as glucose or sorbyl alcohol), cause that production cost is higher, raw material consumption is high, the dissatisfactory unfavorable situation of economic benefit.Although the productive rate of glucose epimerization and enzyme isomery system N.F,USP MANNITOL reaches 35%, the cost of the used immobilized enzyme of enzyme isomery is very high, also makes the production cost of N.F,USP MANNITOL high.
Improve the productive rate of high-value product, reduce the productive rate of low-value product, thereby the economic benefit of increasing substantially is the main contents of current crystal diabetin and N.F,USP MANNITOL process study, exploitation and reform as far as possible always.
Summary of the invention:
The present invention is improving one's methods that head it off proposes, utilize method of the present invention, can make the productive rate of higher crystal diabetin of sucrose material productive value and N.F,USP MANNITOL product amount to 70%, produce the economic benefit of crystal diabetin and N.F,USP MANNITOL product increasing substantially sucrose material.
Method of the present invention is divided into following eight steps.
(1) with sucrose material A complete hydrolysis, from hand over refining after, obtain Nulomoline B;
(2) Nulomoline B is separated with the simulation moving-bed fructose glucose that carries out, obtain being rich in the fructose component C and be rich in glucose component D;
(3) the fructose component C that is rich in (2) is carried out from handing over, concentrate, after the crystallization, centrifugal, drying, obtaining crystal diabetin product E and fructose mother liquor F;
(4) the glucose component D that is rich in (2) is carried out epimerization reaction, through refining, obtain epimerized sugar liquid G again from handing over;
(5) epimerized sugar liquid G is separated with simulation moving-bed, obtain being rich in seminose component H and be rich in glucose component I;
(6) will be rich in glucose component I and get back to (4), merge, repeat epimerization reaction with D;
(7) will be rich in after fructose mother liquor F merges in seminose component H and (3), carry out hydrogenation reaction, obtain mixing pure J;
(8) hydrogenation is mixed pure J and filters, from handing over, concentrate, obtaining the N.F,USP MANNITOL product K after the crystallization, centrifugal, drying.
Description of drawings:
Fig. 1 is a process flow sheet of the present invention.
The treating processes that the present invention may be better understood in conjunction with the accompanying drawings.
The first step of the present invention is with sucrose A complete hydrolysis, this is known technology, can adopt hydrochloric acid or sulfuric acid as hydrolyst, and the suitable condition of hydrolysis is: sugar concentration is 40～60%, pH value about 2, stirring reaction is 0.5～2 hour under 90～105 ℃ of temperature.After the sucrose complete hydrolysis, obtain the mixed solution of fructose glucose, refining with the positive and negative ion-exchange resins, remove the ion in the liquid glucose, obtain Nulomoline B, wherein contain fructose 46～49.5%, glucose 48～49.8%, other impurity 0.5～2%.Must make the sucrose complete hydrolysis, otherwise the effect of back of the present invention will be affected.
Second step of the present invention is to utilize simulation moving-bed separating levulose glucose, and this also is the operation that has realized suitability for industrialized production.The present invention selects for use calcium type Zeo-karb as separate sorbent, as eluent, separation temperature is 40～85 ℃ with water, carries out charging, water inlet, discharging operation continuously, the fructose content that is rich in the fructose component C of gained is 90～96%, and concentration is 20～35%; The fructose content that is rich among the glucose component D of gained is 4～9%, and concentration is 16～30%.After the simulation moving-bed separation of the present invention, fructose in the Nulomoline is effectively separated with the glucose component, and this step also is a key of the present invention, and is not thorough if high fructose syrup separates, the effect of back of the present invention will be had a strong impact on, even the crystal diabetin product can't be obtained.Used fructose-the glucose of the present invention isolating simulation moving-bed be end to end by several pillars, each capital all has feed-pipe, water inlet pipe, circulation tube, all there is discharge nozzle each column bottom, each Guan Shangjun is equipped with by-pass valve control; It is mobile relatively to utilize recycle pump that material is produced in post; The described simulation moving-bed two kinds of operative configuration that have: a kind of is to add Controlling System with magnetic valve, and another is the rotary valve control forms.
The 3rd step was to be rich in fructose component C process cationic, anionic exchange resin after handing over deionizing, being concentrated in vacuo to concentration is more than 75%, add levulose seed crystal, slowly cooling, obtain fructose crystals, through obtaining the crystal diabetin product after centrifugation, the drying, it is 230～250 grams that per 1000 gram sucrose materials can obtain the crystal diabetin product again, and resulting fructose mother liquor output is 230～250 grams (by dry-matter).The crystallization key of fructose is to be rich in the fructose component C whether to reach requirement, and preferably fructose content is more than 93%.The crystallization processes of fructose has also been realized suitability for industrialized production.
The 4th step: the resulting fructose content that is rich among the glucose component D in high fructose syrup simulation moving-bed separation back is 4～9%, glucose content is 91～96%, concentration is 16～30%, being concentrated in vacuo to concentration earlier is 40～60%, adds molybdate catalyst and appropriate hydrochloric acid then and carries out epimerization reaction.Epimerization reaction is at 90～105 ℃, add sugar substance amount 0.05～2% molybdate catalyst, liquid glucose pH value is to react 1～5 hour under 0.5～5 the condition, after carrying out epimerization reaction according to this condition, the mannose content of resulting reaction back liquid glucose is 28～33%, and fructose content is 2～7%, and glucose is 60～72%, handle from handing over cationic, anionic exchange resin, obtain epimerized sugar liquid G.Improve the isomerization reaction temperature, increase the molybdate catalyst consumption, reduce liquid glucose pH value, prolong reaction times etc. more seminose is generated, but side reaction also aggravates, cause the intensification of liquid glucose color and luster.
The 5th goes on foot: carry out simulation moving-bed separation seminose glucose after epimerized sugar liquid G is made with extra care, the present invention selects for use calcium type Zeo-karb as separate sorbent, with water as eluent, separation temperature is 40～85 ℃, carries out charging, water inlet, discharging operation continuously, through after the simulation moving-bed separation, the mannose content that is rich among the seminose component H of gained is 70～85%, fructose content is 2～10%, and all the other are glucose, and concentration is 18～34%; The seminose component content that is rich among the glucose component I of gained is 2～6%, and glucose component content is 92～98%, fructose 0, and concentration is 15～28%.Like this, seminose is separated preferably with the glucose component.Used seminose-the glucose of the present invention isolating simulation moving-bed be end to end by several pillars, each capital all has feed-pipe, water inlet pipe, circulation tube, all there is discharge nozzle each column bottom, each Guan Shangjun is equipped with by-pass valve control; It is mobile relatively to utilize recycle pump that material is produced in post; Can adopt magnetic valve to add Controlling System or two kinds of operative configuration of employing rotary valve.
The 6th step: separate the resulting glucose component I that is rich in back and get back in the 4th step, the resulting glucose component D that is rich in merges with second step, repeats epimerization reaction again after concentrating.This step cycle epimerization reaction is the step that guarantees to obtain at last the hydrogenation liquid of higher mannitol content.
The 7th step: be rich in seminose component H and resulting fructose mother liquor F merging in the 3rd step with resulting in the 5th step, the mixture of seminose, fructose, glucose will be obtained, wherein contain seminose 50～65%, fructose 25～35%, glucose 10～20%, after process positive and negative ion-exchange resins is refining, add hydrogenation catalyst, hydrogenation reaction is 1～3 hour under 100～180 ℃ of temperature, 4～7Mpa hydrogen pressure condition.Behind the hydrogenation, seminose changes into N.F,USP MANNITOL, and conversion of glucose becomes sorbyl alcohol, and fructose transforms and generates half N.F,USP MANNITOL and half sorbyl alcohol.Mannitol content is 70～75% in the mixed alcoholic liquid behind the hydrogenation, and sorbyl alcohol is 25～30%.Hydrogenation reaction in this step is industrial very proven technique.
The 8th step, with mixed alcoholic liquid behind the hydrogenation through filtering, remove nickel catalyzator after, with positive and negative ion-exchange resins refinement treatment, pass through vacuum concentration, decrease temperature crystalline, centrifugal, drying treatment again after, obtain the N.F,USP MANNITOL product.After per 1000 gram sucrose materials were handled through aforesaid method, resulting N.F,USP MANNITOL product was 460～480 grams.After sucrose material was handled through method of the present invention, resulting crystal diabetin and N.F,USP MANNITOL product yield added up to more than 70%.
The advantage that the present invention gives prominence to is that resulting glucose component recirculation is carried out epimerization reaction after making the preparation crystal diabetin, constantly generates the seminose component that obtains high-content (generally reaching more than 70%), thereby produces the N.F,USP MANNITOL product through hydrogenation.Like this, fructose component and glucose component have all obtained effective application, thus combined production of crystallized fructose and N.F,USP MANNITOL product with high yield, and resulting low-value product---sorbyl alcohol (or glucose) productive rate is very low.Therefore, the present invention can improve the economic benefit of sucrose deep processing effectively.
Characteristics of the present invention are: behind sucrose material hydrolysis, separating levulose glucose, be divided into the two-way feed separation and handle: but the component direct crystallization that is rich in fructose is produced crystal diabetin product and fructose mother liquor; After being rich in the glucose component and repeating the epimerization art breading, after obtaining being rich in seminose component and fructose mother liquor and merging, can transform the mixed alcoholic liquid that generation contains higher N.F,USP MANNITOL through hydrogenation again with epimerization, fractionation by adsorption and circulation.Therefore, use method of the present invention, can produce the product of crystal diabetin and two high values of N.F,USP MANNITOL with high yield, productive rate reaches 70%, and the productive rate of by product sorbitol aqueous solution is lower.
Embodiment:
Below, describe in detail in conjunction with the embodiments.
The edible white sugar of embodiment 1:1000 gram, be dissolved in the deionized water of 1000ml, obtain concentration and be 50.14% aqueous sucrose solution, add the 50ml technical hydrochloric acid, the pH value of liquid glucose is adjusted to 2.18, stirring reaction 1.5 hours under 98 ℃ temperature condition is removed impurity with the cationic, anionic exchange resin post from handing over again then, obtains conversion liquid glucose 1940 grams after refining, sugar concentration is 51.55%, wherein contain fructose 49.75%, contain glucose 49.82%, other small amount of impurities 0.43%.
Utilize this conversion liquid glucose of simulation moving-bed device separating treatment, input concentration is 51.55%, under 58 ℃ separation temperature, as adsorption separating agent, be eluent with water with calcium type Zeo-karb, carry out charging, water inlet, discharging operation continuously, obtain being rich in the discharging of fructose component and be rich in the discharging of glucose component, the quality that is rich in the discharging of fructose component is 1680 grams, and concentration is 28.55%, contain fructose 94.13%, contain glucose 5.87%; The quality that is rich in the discharging of glucose component is 2138 grams, and concentration is 24.32%, contains fructose 6.2%, glucose 93.4%, other impurity 0.4%.
To separate resulting fructose component 1680 grams that are rich in back, after the processing of positive and negative ion-exchange resins, in vacuum tightness is that to be concentrated to concentration under the 0.07Mpa condition be 86%, slow crystallisation by cooling, with resulting fructose xln with 3500 rev/mins whizzer centrifugation 15 minutes, get the fructose xln under 80 ℃, vacuum tightness 0.06Mpa condition dry 3 hours, obtain crystal diabetin product 245 grams.Centrifugal resulting fructose mother liquor is 235 grams (doing meter), wherein contains fructose 88.1%, contains glucose 11.9%.
To separate resulting glucose component 2138 gram that is rich in back, be that to be concentrated to concentration under the 0.06Mpa condition be 50.44% in vacuum tightness, adds Sodium orthomolybdate 1 gram, add hydrochloric acid 15ml again, liquid glucose pH value is adjusted to 2.86, and stirring reaction is 3 hours under the temperature condition about 98 ℃, handles from handing over cationic, anionic exchange resin then, obtain epimerized sugar liquid 1040 grams, concentration is 50%, and mannose content is 30.35%, and fructose content is 5.12%, glucose 64.05%, other impurity 0.48%.
Utilize simulation moving-bed device separating treatment epimerized sugar liquid 1040 grams, input concentration is 50.0%, under 58 ℃ separation temperature, as adsorption separating agent, be eluent with water with calcium type Zeo-karb, carry out charging, water inlet, discharging operation continuously, obtain being rich in the discharging of seminose component and be rich in the discharging of glucose component, being rich in seminose component discharging concentration is 28.40%, contains seminose 75.40%, contain fructose 4.13%, contain glucose 20.47%; Being rich in glucose component discharging concentration is 24.32%, contains seminose 3.8%, glucose 95.4%, other impurity 0.8%.Be rich in the discharging of glucose component and get back in the 4th step and merge, after concentrating, repeat epimerization reaction generation seminose component with the glucose component.
Get above seminose component discharging 1830 grams that are rich in, after resulting fructose mother liquor 235 gram merging, through after handing over processing, add 80 gram Raney's nickels, in the high-pressure hydrogenation still, under the 7Mpa pressure condition, be warmed up to 165 ℃ and carried out hydrogenation reaction 2 hours, obtain mixing alcohol behind the hydrogenation, containing N.F,USP MANNITOL is 74.66%, and containing sorbyl alcohol is 25.34%, remove by filter nickel catalyzator, with the positive and negative ion-exchange resins refining after, be concentrated to 52%, cooling, crystallization treatment, pass through centrifugation again, drying treatment obtains N.F,USP MANNITOL product 472 grams.The N.F,USP MANNITOL productive rate counts 47.2% by the sucrose charging capacity, and the crystal diabetin productive rate counts 24.5% by the sucrose charging capacity.Two products add up to productive rate to count 71.7% by the sucrose charging capacity.
Claims (6)
1, a kind of is the high yield combined production of crystallized fructose of raw material and the technology of N.F,USP MANNITOL with sucrose, it is characterized in that comprising following eight steps:
(1) with sucrose material A complete hydrolysis, from hand over refining after, obtain Nulomoline B;
(2) Nulomoline B is separated with the simulation moving-bed fructose glucose that carries out, obtain being rich in the fructose component C and be rich in glucose component D;
(3) the fructose component C that is rich in (2) is carried out from handing over, concentrate, after the crystallization, centrifugal, drying, obtaining crystal diabetin product E and fructose mother liquor F;
(4) the glucose component D that is rich in (2) is carried out epimerization reaction, through refining, obtain epimerized sugar liquid G again from handing over;
(5) epimerized sugar liquid G is separated with simulation moving-bed, obtain being rich in seminose component H and be rich in glucose component I;
(6) will be rich in glucose component I and get back to (4), merge, repeat epimerization reaction with D;
(7) will be rich in after fructose mother liquor F merges in seminose component H and (3), carry out hydrogenation reaction, obtain mixing pure J;
(8) hydrogenation is mixed pure J and filters, from handing over, concentrate, obtaining the N.F,USP MANNITOL product K after the crystallization, centrifugal, drying.
2, according to claim 1 is the high yield combined production of crystallized fructose of raw material and the technology of N.F,USP MANNITOL with sucrose, it is characterized in that: will be rich in the fructose component C and carry out crystallization and centrifugation, after obtaining crystal diabetin E, resulting fructose mother liquor F carries out hydrogenation reaction after seminose component H merges and produces the high N.F,USP MANNITOL product K of content with being rich in.
3, according to claim 1 is the high yield combined production of crystallized fructose of raw material and the technology of N.F,USP MANNITOL product with sucrose, it is characterized in that: separate and to be rich in the resulting glucose component D that is rich in after the fructose component C, adopt epimerization reaction to obtain epimerized sugar liquid G.
4, according to claim 1 is the high yield combined production of crystallized fructose of raw material and the technology of N.F,USP MANNITOL with sucrose, it is characterized in that: the epimerized sugar liquid G that is generated, contain seminose 28～33%, separate with simulated moving bed adsorption, obtain being rich in seminose component H and be rich in glucose component I, separation condition is 40～85 ℃, is separating agent with the Zeo-karb, be continuous feeding and discharging operation under the condition of eluent with water, obtain being rich in seminose component H and be rich in glucose component I.
5, according to claim 1 is the high yield combined production of crystallized fructose of raw material and the technology of N.F,USP MANNITOL with sucrose, its described fructose-glucose that is used for separates and two kinds of isolating simulation moving-bed being characterised in that of seminose-glucose: several pillars are end to end, each capital all has feed-pipe, water inlet pipe, circulation tube, all there is discharge nozzle each column bottom, and each Guan Shangjun is equipped with by-pass valve control; It is mobile relatively to utilize recycle pump that material is produced in post; The described simulation moving-bed two kinds of operative configuration that have: a kind of is to add Controlling System with magnetic valve, and another is the rotary valve control forms.
6, according to claim 1 is the high yield combined production of crystallized fructose of raw material and the technology of N.F,USP MANNITOL with sucrose, it is characterized in that: simulation moving-bed fructose-glucose separates and simulation moving-bed seminose-glucose separation all is at 40～85 ℃, input concentration 40～70%, making eluent with water, is to carry out under the condition of separating agent with the Zeo-karb.
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| CN 03134957 CN1219782C (en) | 2003-09-28 | 2003-09-28 | Cane sugar material high-yield joint production process of crystalline fructose and manna sugar |
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Families Citing this family (7)
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| CN1328386C (en) * | 2005-04-13 | 2007-07-25 | 南宁市化工研究设计院 | Method for preparing mannitol from raw material of cane sugar |
| CN100385016C (en) * | 2006-06-28 | 2008-04-30 | 山东西王糖业有限公司 | Crystal fructose production process by corn starch |
| CN100540674C (en) * | 2006-12-27 | 2009-09-16 | 山东西王糖业有限公司 | The method of a kind of high yield combined production of crystallized fructose, N.F,USP MANNITOL and sorbyl alcohol |
| CN103205513A (en) * | 2012-09-07 | 2013-07-17 | 上海华茂药业有限公司 | Extraction method for fructose from waste dextran fermentation broth |
| 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 |
| CN103508848B (en) * | 2013-10-15 | 2015-04-15 | 山东百龙创园生物科技有限公司 | Method for producing mannitol and sorbitol through waste fructooligosaccharide liquid |
| KR102389709B1 (en) * | 2019-11-29 | 2022-04-22 | 씨제이제일제당 주식회사 | Composition for producing allulose and method of producing allulose using thereof |
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