CN1724678A - Method of producing mannitol using starch as raw material - Google Patents
Method of producing mannitol using starch as raw material Download PDFInfo
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- CN1724678A CN1724678A CN 200510012606 CN200510012606A CN1724678A CN 1724678 A CN1724678 A CN 1724678A CN 200510012606 CN200510012606 CN 200510012606 CN 200510012606 A CN200510012606 A CN 200510012606A CN 1724678 A CN1724678 A CN 1724678A
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Abstract
The invention relates to a method to make manna sugar that uses starch as raw material. The method is saccharifying and epimerisming the starch that has been fluidified to gain the mixture liquid of dextrose and mannose; separating the mixture liquid to gain liquid that is rich in mannose; iso-merizing enzyme column by dextrose and transform the rest dextrose in the liquid that is rich in mannose to fructose, and the mixture liquid of dextrose, mannose and fructose would be gained; adding hydrogen into the mixture to make the mixture liquid of sorbitol and manna sugar; after crystallizing and refining, the manna sugar crystalloid would be gained. The invention is also suited for industrial manufacturing to improve the utilization ratio from 85% to 95-98%.
Description
Technical field
The present invention relates to a kind of preparation method of hexavalent alcohol, specifically a kind of is the method that raw material is produced N.F,USP MANNITOL with starch.
Background technology
In the prior art, N.F,USP MANNITOL can make by seminose or fructose hydrogenation.And be the processing method of seminose (utilizing molybdate to be catalyzer) with conversion of glucose, report (Chem.Zvesti., 26, P183-186 (1972)) was just arranged in the seventies in 20th century.United States Patent (USP) 4173514 discloses the technology that the two isomeries of a kind of glucose warp are produced N.F,USP MANNITOL, and this technology is that glucose produces seminose through molybdate catalysis earlier; Residue glucose is through the effect of glucose isomerase, and part generates fructose; With above-mentioned mixing solutions hydrogenation, can obtain containing the alcohol mixture solution of N.F,USP MANNITOL.But the yield for preparing N.F,USP MANNITOL with this method is lower, generally only is 40-42%.
Chinese patent ZL97106616.7 discloses a kind of method of producing D-N.F,USP MANNITOL with D-glucose, this method is to be that catalyzer carries out epimerization with the molybdate earlier with D-glucose, the gained mixed sugar liquid is by fixed glucose isomerase post bed, generate the mixed solution of seminose, fructose and glucose, the gained mixed solution adopts fixed bed or continuous chromatography to separate, the component that obtains being rich in the component of seminose and fructose respectively and be rich in glucose.To be rich in the component of glucose again through the isomerization again of fixation glucose allomerase post bed.And the component that will be rich in seminose and fructose through concentrate, behind the high-pressure hydrogenation alcohol mixture, after refining, concentrated, crystallization, isolate N.F,USP MANNITOL again.This method with separating obtained glucose isomery again, is improved the yield of N.F,USP MANNITOL by increasing chromatrographic separation step.But,, thereby cause in subsequent technique, having to increase the processing step of evaporation concentration owing to the total dry matter concentration of carrying out chromatographic separation gained solution is lower.So, complicated process of preparation, the cost of N.F,USP MANNITOL are raise, and in industrial production, when utilizing chromatographic separation technology to separate, also to often utilize chemical reagent such as acid, alkali, calcium chloride that used resin is made the transition, increased the discharging of " three wastes " thus, environment has been caused certain harm.In addition, when carrying out suitability for industrialized production, along with the carrying out that produces, the calcium in the resin can constantly be lost, and therefore, separating effect also can have bigger fluctuation along with the continuous regeneration of resin, has increased control of process condition difficulty in the production process thus.
Before this, the applicant has also applied for the Chinese patent (CN1524837) of " is the method that raw material is produced N.F,USP MANNITOL with glucose ", and this method at first is to be raw material is produced seminose, glucose through epimerization mixing solutions with glucose; Utilize crystallization process that the part glucose crystallization in the gained mixed solution is separated out then, to improve the content of seminose in the mixed sugar liquid; Again by the glucose isomerase post with crystallization separate out the back mother liquid obtained in remaining glucose moiety be converted into fructose, obtain the mixed solution of glucose, seminose and fructose, and technology hydrogenation routinely, refining etc., make the N.F,USP MANNITOL crystal.This method has overcome many technological deficiencies of ZL97106616.7, has that technology is simple, environmental friendliness, is suitable for suitability for industrialized production, and can improves plurality of advantages such as N.F,USP MANNITOL yield.
Above-mentioned each method all is to be that raw material is produced N.F,USP MANNITOL with glucose, and used glucose feed, generally all be with starch after amylase liquefaction, saccharifying enzyme saccharification, make through postprocessing working procedures such as crystallization, centrifugal and oven dry again.In glucose crystallization technology, have only 85% glucose formation crystal, make crystalline glucose through centrifugal, oven dry.Also be to have only 85% composition to enter next procedure in the starch glucose, be used to produce N.F,USP MANNITOL.The glucose near 10-13% contained in the crystalline mother solution is then sold at a bargain as industry byproduct.Like this, the effective rate of utilization of glucose has only 85% in the starch.Starch resource this than poor efficiency not only can cause the waste of starch resource, and the production cost of N.F,USP MANNITOL is raise; Not only can cause the enterprise profit spatial to reduce, also can make the ultimate consumer have to accept the N.F,USP MANNITOL product of high price.And be that raw material is produced in the technological process of N.F,USP MANNITOL with glucose, need earlier crystalline dextrose to be made concentration and be 50% glucose solution, after transforming, the subsequent technique flow process just can be used to produce N.F,USP MANNITOL again.Like this, when the system glucose solution, also need to expend in addition a large amount of deionized waters.
" starch and Dian Fentang " magazine 1999 (3) phase P14-19 have published Zhou Zhongkai's the paper of " is the novel process of raw material production N.F,USP MANNITOL with starch ", it is the possibility of feedstock production N.F,USP MANNITOL that this article has been studied with starch, its technological process is to utilize catalyzer to make that glucose moiety changes into seminose in the starch saccharificating liquid, through glucose isomerase remaining conversion of glucose is become seminose again, hydrogenation makes N.F,USP MANNITOL then.This paper record, the content that transforms seminose can reach 42%.But carry out repetition test by this paper technology, the content that transforms seminose can only reach about 33～35%.This shows that this paper technology transforms the content instability of seminose, and transformation efficiency is not high.Make the technology of this paper still not possess the possibility that realizes suitability for industrialized production at present.In addition, not seeing other as yet relevant is the bibliographical information of feedstock production N.F,USP MANNITOL with starch.
Summary of the invention
Purpose of the present invention just provide a kind of be suitable for suitability for industrialized production, be the method that raw material is produced N.F,USP MANNITOL with starch, can stably produce N.F,USP MANNITOL by this preparation method with high yield.
The present invention is that the processing step that raw material is produced N.F,USP MANNITOL is with starch: the starch after 1, will liquefying carries out saccharification, epimerization, obtains seminose and glucose mixed solution; 2, above-mentioned gained mixed solution is separated, obtain being rich in the solution of seminose; 3, by the glucose isomerase post, gained of last step is rich in remaining glucose moiety is converted into fructose in the mother liquor of seminose, obtain the mixed solution of glucose, seminose and fructose; 4, with the above-mentioned mixed solution that contains glucose, seminose and fructose technology hydrogenation routinely, make the mixed solution that contains sorbyl alcohol and N.F,USP MANNITOL, this mixed solution is through crystallization, refining, the N.F,USP MANNITOL crystal.
In preparation method's of the present invention the 1st step, can carry out according to the following steps when the starch after the liquefaction is converted into seminose and glucose solution: the starch after at first will liquefying makes saccharification liquid through the saccharifying enzyme saccharification; Again with saccharification liquid under temperature 60-160 ℃, acidic conditions, be that catalyzer carries out epimerization with the molybdate, make glucose moiety be converted into seminose, obtain seminose and glucose mixed solution.
When carrying out starch liquefacation, the concentration after the starch liquefacation is preferably 30%, and the DE value is preferably in 15-18%.And when carrying out saccharification, saccharification DE value should be preferably 98% between 96-98%; The DX value should be not less than 95-97%, is preferably 97%.Otherwise glucose is difficult for crystallization.With this understanding, the concentration of the made saccharification liquid of starch is 30%, and this saccharification liquid is converted into seminose and glucose mixed solution under the situation that catalyzer exists.When carrying out epimerization, the pH value of saccharification liquid can transfer between the 3-4.5, is preferably between the 4.0-4.2.Should be the 0.15-0.3% of solution dry matter weight as the add-on of the molybdic acid of catalyzer or molybdate, be preferably between the 0.2-0.25%.Invert point should be between 60-160 ℃.If invert point is 100-105 ℃, then take 90-120min.The better conversion temperature is 120-130 ℃, takes 15-20min under this temperature.After the conversion, the total concn of solution is 30%, and the shared ratio of seminose is 29-31%.
Preparation method's of the present invention the 2nd step is that the mixed solution with above-mentioned gained seminose and glucose separates, and obtains being rich in the solution of seminose.Preferably adopt the applicant's disclosed perfectly crystallization process in the CN1524837 patent application during separation, to obtain glucose crystal and the mother liquor that is rich in seminose.After the separation, the glucose crystal returns previous step and carries out epimerization again; The mother liquor that is rich in seminose then enters subsequent processing.Before Crystallization Separation, should with go up step gained dry substance concentration be 30% glucose, seminose mixed solution to be concentrated into concentration be 65-75%, be preferably 71-73%, could guarantee like this glucose well crystallization separate out.Because the solubleness of glucose is less than seminose, so glucose can be separated out with lenticular.After the glucose crystal was separated out, the glucose content in the mother liquor was reduced to 57-58% by initial 68-69%, and mannose content then rises to 38-42% by 29-30%, and the solution total concn is 66-69%.
Mixed solution in this step separates, and removes and can adopt perfectly crystallization process, can also adopt chromatography (analog stream movable bed, also available single-column carry out discontinuous to be separated), also can adopt other feasible methods.
Adopt perfectly crystallization process, the crystallizer of producing crystalline dextrose by liquid glucose in the time of can utilizing Starch Production glucose is implemented this separating step, so just can save purchasing of Crystallization Separation equipment.Adopt chromatography, must inject capital into and purchase required equipment, but this method can obtain the high component of mannose content, mannose content can reach 50-58%.
Above-mentioned different separation method can be selected for use according to factory's self-condition, appointed condition, fund state, technical qualification.
Preparation method's of the present invention the 3rd step is the 2nd step gained to be rich in that remaining glucose moiety is converted into fructose in the solution of seminose by the glucose isomerase post, obtains the mixed solution of glucose, seminose and fructose.Before carrying out the enzyme isomery, the concentration that gained should be rich in the solution of seminose transfers to 50-55%, in order to the carrying out of enzyme isomerization reaction.By the glucose isomerase post, be fructose with contained conversion of glucose, in the gained liquid after the conversion, glucose content is 29-30%, and seminose is 37-38%, and fructose is 30-31%.
Preparation method's of the present invention the 4th step is a mixed sugar liquid that the 3rd step was transformed gained fructose, glucose, seminose under 150 ℃, 5-12MPa air pressure, and shortening obtains the mixed solution of sorbyl alcohol and N.F,USP MANNITOL, and wherein mannitol content reaches more than 50%.This mixed solution is through conventional technology crystallization, refining N.F,USP MANNITOL crystal.
Preparation method of the present invention has following beneficial effect:
1, be raw material when producing N.F,USP MANNITOL with the glucose crystal in prior art (CN1524837), conversion of glucose is that the transformation efficiency of N.F,USP MANNITOL is 50%.Consider that starch has only 85% yield when producing the glucose crystal, therefore, the starch conversion of glucose is that the transformation efficiency of N.F,USP MANNITOL only is about 42%.And in the present invention, be raw material with starch, utilize it directly to carry out epimerization through the liquid glucose that saccharification produces, can make glucose compositions all in the liquid glucose all participate in the epimerization reaction.This just makes the utilization ratio of starch glucose bring up to 95-98% by 85%, is that the transformation efficiency of N.F,USP MANNITOL can be up to more than 49% thereby make the starch conversion of glucose.Thus, improved the transformation efficiency of starch glucose.
2, preparation method of the present invention has saved multistep operations such as the crystallization of producing in the crystalline dextrose technological process, centrifugal, oven dry, packing, transportation, storage, remove and shortened technical process, outside enhancing productivity, also can be descended accordingly at aspects such as energy consumption, labor cost and storehouse resource occupation.In addition, directly carry out isomery, also saved original operation of crystalline glucose being made when being raw material certain density glucose solution, also with regard to the corresponding spent a large amount of deionized waters of this operation that saved with the crystalline glucose with liquid glucose.Like this, manufacturing enterprise just needn't purchase the desalter of producing deionized water, has also alleviated the production task of additional water making device simultaneously, has saved in a large number precious water resource day by day.
3, adopt preparation method of the present invention, under the situation that does not increase any investment, can realize with starch being the high yield preparation technology that raw material is produced N.F,USP MANNITOL, the glucose feed that cost is high (2300 yuan/ton) substitutes with the low starch material of cost (1800 yuan/ton), thereby has reduced the production cost of N.F,USP MANNITOL.
4, of the present invention is the production technique that raw material is produced N.F,USP MANNITOL with starch, existing be that raw material adopts two isomerate process to produce on the basis of production unit of N.F,USP MANNITOL with glucose, with used crystallizer in the starch system glucose crystal process, be diverted to the Crystallization Separation of implementing glucose in seminose behind the epimerization, the glucose mixed solution.Like this, under the precondition that need not to increase any new installation investment, can improve before the enzyme isomery content of seminose in the mixing solutions, and then improve the content that gained in the post-order process mixes N.F,USP MANNITOL in the alcoholic solution.This is the place of a key of the present invention.
Because preparation method of the present invention need not to increase new equipment, saved corresponding investment, and technology controlling and process is succinctly clear and definite, the existence of these factors, make preparation method of the present invention very easily drop into suitability for industrialized production, also more meet the management aim that manufacturing enterprise spends less, handles affairs more.This will be of great advantage for the production cost that reduces enterprise, the raising N.F,USP MANNITOL competitiveness of product in market.
As seen by above-mentioned, preparation method of the present invention is the production method that raw material is produced the practicality of N.F,USP MANNITOL with starch for N.F,USP MANNITOL manufacturing enterprise provides a kind of.This method not only is suitable for suitability for industrialized production, and can stably produce N.F,USP MANNITOL with high yield, thereby reduces the production cost of enterprise, improves raw-material utilization ratio, improves the transformation efficiency of starch glucose.Thus, make the manufacturing enterprise of preparation N.F,USP MANNITOL need not to carry out to adopt this preparation method that the share of market of this product and the market competitiveness of enterprise product are greatly improved under the situation that any equipment drops into.
Embodiment
Embodiment 1:
Get 872 gram starch and (containing wet) size mixing, make concentration and be 2.5 liters of 30% starch milks.Add α-Dian Fenmei, make that starch liquefacation makes that concentration is 30%, the DE value is 15% starch fluid.
High temperature makes the α-Dian Fenmei inactivation, gets 2.5 liters of this starch fluids, the saccharifying enzyme of adding 0.08% and 0.25% ammonium molybdate (by the starch dry weight), and transferring the solution pH value with hydrochloric acid is 4.0, carries out saccharification and glucose epimerization under 60 ℃ of temperature condition.After the saccharification 48 hours, make the saccharifying enzyme inactivation with high temperature.Sampling detects with high pressure lipuid chromatography (HPLC) (Tianjin, island RID-10AJ), seminose ingredients constitute 23.1%, and the glucose component accounts for 73.4%.
The feed liquid of gained is dropped in 3 liters of autoclaves, under 120-130 ℃ of temperature, be incubated 15 minutes and carry out epimerization.Epimerization is finished, and obtains seminose and glucose mixed solution.Sampling analysis, wherein the seminose ingredients constitute 30%, and the glucose component accounts for 66.8%.
The strength of solution of above-mentioned gained solution is concentrated into 73%, is put in the stainless steel crystallizer tank of TDA-8002 type temperature adjustment water-bath, stir with D-7401 stepless time adjustment electric mixer, stirring velocity is 8 rev/mins.When treating that solution temperature is reduced to 42 ℃, in solution, drop into the dried glucose crystal seed (Shijiazhuang City China battalion grape sugar refinery produces) that accounts for dry-matter gross weight 10% in the mixed solution, with the thermograde cooling of solution, make the glucose crystallization in the solution again with 0.5 ℃/h.After the crystallization 42 hours, adopt the method for vacuum filtration that the glucose crystallization thing is leached.After leaching the glucose crystal, seminose ingredients constitute 39% in the crystalline mother solution, the glucose component accounts for 56%, and strength of solution is 68%.
The concentration that is 68% crystalline mother solution to above-mentioned concentration transfers to 55%, again by being installed in the 160ml glucose isomerase post (Novozymes Company's production) in 2.5 * 80cm heating jacket, under 60 ℃ of temperature, carry out glucose isomerase, obtain containing the mixed sugar liquid of glucose 29%, seminose 37%, fructose 31%.
This mixing sugar solution is joined experiment with in the autoclave (GSH-3 type), press 10% of solution weight and add Raney's nickel catalyst, the pressure of reactor is transferred to 6MPa, hydrogenation is 110 minutes under 145 ℃ of temperature, make with extra care with usual manner again, can obtain containing the alcohol mixture liquid of sorbyl alcohol and N.F,USP MANNITOL.Detect through high pressure liquid chromatography, contain N.F,USP MANNITOL 52%, sorbyl alcohol 44.5% in this alcohol mixture liquid.
This alcohol mixture liquid through crystallization, refining promptly get medical N.F,USP MANNITOL crystal 2 97 and restrain.
Embodiment 2:
Get 872 gram starch and (containing wet) size mixing, make concentration and be 2.5 liters of 30% starch milks.Add α-Dian Fenmei, make starch liquefacation, make concentration and be 30%, the DE value is 15% starch fluid.
High temperature makes the α-Dian Fenmei inactivation, gets 2.5 liters of this starch fluids, adds 0.08% saccharifying enzyme (by the starch dry weight), carries out saccharification under 60 ℃ of temperature condition, makes saccharification DE value and be 98%, the DX value is 97% saccharification liquid.
Get 2.5 liters of above-mentioned saccharification liquid, add in 3 liters of autoclaves, add 0.25% ammonium molybdate (by the starch dry weight) again, and to transfer pH value with hydrochloric acid be 4.0.Be warming up to 120-130 ℃, be incubated 20 minutes and carry out epimerization.Epimerization is finished, and obtains seminose and glucose mixed solution.Sampling is with high pressure liquid chromatographic analysis, and wherein the seminose ingredients constitute 29.6%, and the glucose component accounts for 68%.
This mixed sugar liquid is carried out crystallization by the method for embodiment 1.After the Crystallization Separation, mannose content is 38.6% in the crystalline mother solution, and glucose content is 58%, and mother liquid concentration is 66%.The concentration of this crystalline mother solution is adjusted to 55%, by example 1 described mode, glucose is carried out isomery then, obtain containing the mixing solutions of glucose, seminose and fructose by the glucose isomerase post.Mannose content in this mixing solutions is 37%, and fructose content is 30%, and glucose content is 30%.
By the method for embodiment 1 this mixing solutions is carried out hydrogenation again, make with extra care, obtain containing the alcohol mixture liquid of N.F,USP MANNITOL 52%, sorbyl alcohol 45%.This alcohol mixture liquid promptly obtains N.F,USP MANNITOL crystal 2 95 grams through crystallization and refining.
Embodiment 3:
Prepare 5 liters of seminose behind the epimerization and glucose mixed solutions by example 2 methods, the concentration of this mixed solution is adjusted to 45%.In the resin column of 3 * 130cm band heating jacket, pack into 001 * 7 calcium type ion exchange resin (production of Shijiazhuang resin processing plant) of 500ml.
Above-mentioned mixed solution is added in the resin column, be heated to 40-45 ℃ of insulation.Treat after the system balancing, the flow velocity of 2ml/min, the effusive component that is rich in glucose, wherein glucose content is 84%, and mannose content is 13%, and strength of solution is 15%.Use 40 ℃-45 ℃ salt-free water elution then, flow velocity is 2ml/min, and when wash-out concentration began to descend, collecting the component mean concns that is rich in seminose was 30%, and wherein mannose content is 51%, and glucose content is 48%.
Get 3 liters of feed liquids that are rich in the seminose component, and to be concentrated into concentration be 55%.Carry out the enzyme isomery by the method for example 1 again, the solution that obtains contains seminose 49%, glucose 27%, fructose 23%.
Carry out hydrogenation by the method for example 1 equally again, the content of N.F,USP MANNITOL is 60% in the alcohol mixture liquid of making, and the content of sorbyl alcohol is 39%.Alcohol mixture liquid is through crystallization, the refining N.F,USP MANNITOL crystal that obtains.
Claims (6)
1, a kind of is the method that raw material is produced N.F,USP MANNITOL with starch, it is characterized in that the processing step of this method is:
(1) starch after will liquefying carries out saccharification, epimerization, obtains seminose and glucose mixed solution;
(2) above-mentioned gained mixed solution is separated, obtain being rich in the solution of seminose;
(3) by the glucose isomerase post, gained of last step is rich in remaining glucose moiety is converted into fructose in the solution of seminose, obtain the mixed solution of glucose, seminose and fructose;
(4) with the above-mentioned mixed solution that contains glucose, seminose and fructose technology hydrogenation routinely, make the mixed solution that contains sorbyl alcohol and N.F,USP MANNITOL, this mixed solution is through crystallization, refining, the N.F,USP MANNITOL crystal.
2, according to claim 1 is the method that raw material is produced N.F,USP MANNITOL with starch, it is characterized in that seminose and separating of glucose mixed solution are to adopt perfectly crystallization process.
3, according to claim 2 is the method that raw material is produced N.F,USP MANNITOL with starch, it is characterized in that seminose and glucose mixed solution Crystallization Separation before, strength of solution is concentrated into 71-73%.
4, according to claim 1 is the method that raw material is produced N.F,USP MANNITOL with starch, it is characterized in that seminose and separating of glucose mixed solution are to adopt chromatography.
5, according to claim 1 is the method that raw material is produced N.F,USP MANNITOL with starch, it is characterized in that the concentration after the starch liquefacation is 30%.
6, according to claim 1 is the method that raw material is produced N.F,USP MANNITOL with starch, it is characterized in that the solution that (2) step gained is rich in seminose is to carry out the enzyme isomery after concentration transfers to 50-55%.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN103508848A (en) * | 2013-10-15 | 2014-01-15 | 山东百龙创园生物科技有限公司 | Method for producing mannitol and sorbitol through waste fructooligosaccharide liquid |
| CN109942375A (en) * | 2019-04-25 | 2019-06-28 | 浙江华康药业股份有限公司 | A method of prevent liquid sorbitol from crystallizing |
| CN115784838A (en) * | 2022-12-07 | 2023-03-14 | 浙江华康药业股份有限公司 | Method for co-producing mannitol crystal and sorbitol crystal by using crystalline glucose |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN87103681A (en) * | 1986-05-01 | 1987-12-09 | 昆士兰大学 | Utilize the amyloglucosidase and the ferment single bacteria that moves about to change into ethanol through the starch of pre-treatment and liquefaction |
| CN86108681A (en) * | 1986-12-21 | 1987-07-15 | 柳州市味精厂 | A kind of method of producing Glucose Liquid |
| CN1412324A (en) * | 2001-10-18 | 2003-04-23 | 山东中舜科技发展有限公司 | Technological improvement on glucose production |
| CN1216022C (en) * | 2003-09-17 | 2005-08-24 | 谭卫星 | Method for preparing mannitol utilizing dextrose |
-
2005
- 2005-06-15 CN CNB2005100126068A patent/CN100408688C/en not_active Expired - Fee Related
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN103508848A (en) * | 2013-10-15 | 2014-01-15 | 山东百龙创园生物科技有限公司 | Method for producing mannitol and sorbitol through waste fructooligosaccharide liquid |
| 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 |
| CN109942375A (en) * | 2019-04-25 | 2019-06-28 | 浙江华康药业股份有限公司 | A method of prevent liquid sorbitol from crystallizing |
| CN109942375B (en) * | 2019-04-25 | 2022-03-04 | 浙江华康药业股份有限公司 | Method for preventing liquid sorbitol from crystallizing |
| CN115784838A (en) * | 2022-12-07 | 2023-03-14 | 浙江华康药业股份有限公司 | Method for co-producing mannitol crystal and sorbitol crystal by using crystalline glucose |
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| CN100408688C (en) | 2008-08-06 |
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