CN101190932A - Method for preparing high purity maltitol crystal powder - Google Patents
Method for preparing high purity maltitol crystal powder Download PDFInfo
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- CN101190932A CN101190932A CNA2007100003207A CN200710000320A CN101190932A CN 101190932 A CN101190932 A CN 101190932A CN A2007100003207 A CNA2007100003207 A CN A2007100003207A CN 200710000320 A CN200710000320 A CN 200710000320A CN 101190932 A CN101190932 A CN 101190932A
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- maltose
- maltitol
- solution
- post
- crystal powder
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B61/00—Other general methods
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
Abstract
The invention provides a method of preparation of high-grade maltitol crystal powder, which includes the following steps: (1) through adopting a plurality of simulated moving bed chromatogram of a pillar which concentrates a strong acid cation resin, a maltose solution containing a pure maltose of a concentration greater than 96% is prepared by a rough maltose solution containing maltose of a 70-75% concentration ;(2) maltitol solution containing pure maltitol whose concentration is greater than 95% can be prepared by a hydrogenation which has a percent conversion greater than 99% under the condition that the reaction is carried out in the existence of ruthenium catalyst, at the temperature of 120-130 DEG C and at the pressure of 40-50kg/cm<SUP>2</SUP>;(3) the maltitol solution after concentrated, dried ,grinded and crystallized is used to prepare the maltitol crystal powder of a concentration greater than 98%.
Description
Background of invention
Invention field
The present invention relates to high purity maltitol crystal powder greater than 98% and preparation method thereof.More particularly, the present invention relates to a kind of method for preparing high purity maltitol crystal powder, this maltitol crystal powder has following characteristic: i) can be by microbial fermentation; Ii) can not cause carious tooth; Iii) hardly by the human digestive enzymic digestion; Iv) low calory functionality; And the physical property and the thermostability of v) separating moisture absorption (dehygroscopicity).
Description of the Prior Art
Maltose alcohol has been used to the different field of food, medicine and makeup.Its preparation method has obtained open in many prior aries, as Japanese Laid-Open Patent Application 57-134498, and Japanese Laid-Open Patent Application 61-180797, Japanese Laid-Open Patent Application 57-134498 and Japanese Laid-Open Patent Application 61-180797.
In Japanese Laid-Open Patent Application 9-132587, the method for preparing the high purity maltose alcohol crystals is disclosed.This preparation method comprises step: i) utilize enzyme glycolysis method or chromatography can be gone out the high purity maltose of 81-90% content by the maltose raw material preparing of 50-80% content; Ii) in the presence of nickel catalyzator, as 110-145 ℃ of temperature and 40-200kg/cm
2Under the reaction conditions of pressure, can make the maltitol solution of 50-90% by high purity maltose by hydrogenation; Iii) utilize chromatography and continuous crystallisation device, can make purity greater than 95% maltose alcohol crystal by the resulting maltitol solution of purifying.
Yet, there is following defective in the high purity maltose alcohol preparation method who enumerates in these patent publications, as i) formation that increased by product in hydriding process ii) has difficulties for removing separation and the purification process that by product carries out, and this needs a plurality of steps of chromatographic separation and recrystallization; And the productivity that has iii) reduced maltose alcohol, this has caused the problem of commercial exploitation maltose alcohol.
In order to address the above problem, improved the present invention.The present invention who is used to prepare high purity maltitol crystal powder is accomplished by following preparation method, this method comprises: the i) simulated moving bed chromatography of the post by using resin cation (R.C.) intensive goes out to contain maltose solution greater than 96% pure maltose by the thick formulations prepared from solutions of the maltose that contains 70-75% maltose; Ii) in the presence of ruthenium catalyst, transform and prepare the maltitol solution that contains greater than 95% pure maltose alcohol by method for hydrogenation; Iii) concentrate resulting maltitol solution and under 60-80 ℃, keep a night still and do not contain crystal seed; And iv) dry, grind and the resulting maltose alcohol of crystallization, be used to prepare purity greater than 98% maltitol crystal powder.
Summary of the invention
The purpose of this invention is to provide a kind of method for preparing high purity maltitol crystal powder, it comprises step: the i) simulated moving bed chromatography of a series of posts by using strong acidic ion resin intensive, by the thick solution separating of the maltose that contains 70-75% maltose with prepare the maltose solution that contains greater than 96% pure maltose; Ii) in the presence of ruthenium catalyst, as 120-130 ℃ of temperature and 40-50kg/cm
2The reaction conditions of pressure can transform and prepare the maltitol solution that contains greater than 95% pure maltose alcohol by the method for hydrogenation greater than 99% transformation efficiency down; And iii) concentrate, dry, grind and the resulting maltitol solution of crystallization is used to prepare purity greater than 98% maltitol crystal powder.
Further, the used post of the present invention is intensive at least a strong acidic ion resin, it is selected from Amberlite CG6000 series, Diaion UBK 530K, Dowex M4340 and MitsubisiFRK-01.
On the other hand, the present invention's method of preparing high purity maltitol crystal powder further comprises the ii) step of resulting maltitol solution of enrichment step; And under 60-80 ℃, kept still spissated maltitol solution 42-54 hour and do not contain crystal seed.
Accompanying drawing is described
Fig. 1 has shown the illustrative process of separating and prepare high purity maltose among the present invention by simulated moving bed chromatography system,
Fig. 2 has shown the synoptic diagram of the structure of the post that is used to separate and prepare high purity maltose solution among the present invention and equipment.
Detailed Description Of The Invention
For the preparation of the present invention of high purity maltitol crystal powder by following preparation method Developed, the method comprises: i) simulation of the post by using resin cation intensive is moved The bed chromatogram is prepared by the maltose that contains 70-75% maltose thick solution and to be contained greater than 96% The maltose solution of pure maltose; Ii) in the presence of ruthenium catalyst, transformed and preparation by hydrogenation Go out to have the maltitol solution greater than 95% pure maltitol; Iii) concentrate resulting maltose Alcoholic solution also keeps still a night and does not contain crystal seed under 60-80 ℃; And iv) dry, grind Mill and the resulting maltitol of crystallization, for the preparation of purity greater than 98% maltol crystal powder The end.
By under 90-110 ℃, preparing wheat with α-amylasehydrolysis and liquefied starch soln Bud sugar juice (DE 8-12). And then resulting maltose solution is used β under 50-60 ℃-amylase saccharification 8-48 hour. At last, obtained containing the maltose of 60% maltose composition Solution. Yet, fail to obtain more highly purified maltose solution, this is because beta amylase can not Cracking 1-6 glycosidic bond.
In the situation with the beta amylase hydrolysed corn starch, can obtain the Fructus Hordei Germinatus of 40-55% The maltotriose of sugar, 18-23% and greater than the 18-23%'s of the DP4 that contains the 1-6 glycosidic bond The side chain dextrin. Recently, proposed to increase for the maltose content with the maltose composition Technology to 70-75%. This technology has utilized the enzyme of amylopectase and beta amylase to mix Thing comes cracking 1-6 glycosidic bond. Adopt the commerce that contains the 70-75% maltose content of this technology Title Highmaltose comes into the market.
The maltose solution that contains 70-75% maltose has been used as the parent material for preparing maltose alcohol of the present invention according to following preparation process.
1) step 1
By preparing the maltose solution that contains 70-75% maltose by starch according to liquefaction, saccharification, filtration, decolouring, ion-exchange and enrichment step.
2) step 2
The maltose solution of the resulting 70-75% of containing maltose has been condensed to the solids content of 53-56%.By the intensive simulated moving bed chromatography of Zeo-karb, spissated maltose solution is separated and be purified to high-purity maltose solution greater than 96%.
Continuous simulation bed system of the present invention is a kind of chromatogram, it is characterized in that the size according to molecular weight, utilizes the difference of mobility, with the constant flow rate sorbent material and supply solution is moved to opposite direction.Yet in actual applications, sorbent material is fixed in the post, and the mobile post that supply position by will supplying with solution and desorb water (desorbent water) move to is separately supplied with solution and desorb water with the sorbent circulation of volume of voids.The principal character of this system is mobile charging and discharging position, and sorbent material is fixed and charging, discharging and circulation are carried out continuously.
As the sorbent material that separates the maltose composition, the ion exchange resin of strongly-acid gel form has Na
+The linking agent of type functional group, 4-8% and 40-80 purpose particle size.As preferred separation resin, can use Amberlite CG6000 series, Diaion UBK 530K, DowexM4340 and Mitsubisi FRK-01.
3) step 3
The high-purity maltose that obtains in step 2 has been condensed to the solids content of 45-50%.So, in the presence of the 0.03-0.1% ruthenium catalyst, as 120-130 ℃ of temperature and 40-50kg/cm
2Carried out under the reaction conditions of pressure hydrogenation 3-5 hour.Can obtain high-purity maltitol solution by hydrogenation greater than 95%.Then, by removing catalyzer, concentrate and the resulting maltitol solution of purifying.
4) step 4
High-purity maltitol solution of 82-85% concentration keeps static being used for to solidify 48 hours down at 60-80 ℃.Behind removal and the dry water constituent, high-purity maltose alcohol granule is pulverized and is cut so that add grinding.After the grinding, resulting maltitol crystal powder is selected to the purity greater than 98%.
Simulated moving bed chromatography in the step 2 can be as follows by specific explanations.
Separating device of the present invention is by having diameter: the length ratio is 1: the post of 2.5-5 is formed.Divider is positioned at the upper position of post, and collector is positioned at the lower position of post, thereby fluidic disperses and to flow be constant speed.Supply with solution and desorb water by heating and maintenance, the temperature in the post should be 58-62 ℃.
Four posts (or 8,12 posts) are configured to the annular position for 5 entrance and exit circulating fluid.The entrance and exit that is arranged in the post is as follows: i) maltose is supplied with the inlet of solution, the ii) inlet of desorb water, the iii) outlet of side chain dextrin (component A), the iv) outlet of trisaccharide maltose (B component) and the v) outlet of high-purity maltose (component C) of 96%.
Solution supplied with by maltose and desorb water is recycled in all posts that are provided with.Therefore, component A, B component and component C will be distributed in all posts.So, the lock out operation of above-mentioned 3 components should be by the carrying out that shows among Fig. 1.
Separating the cyclical operation first time of 3 components is made up of 4 operation stepss.The first step of operation comprises i) supply with maltose supply solution at the No.3 post, ii) supply with desorb water, iii) at No.2 post emission components B at the No.1 post.Second step of operation comprises i) supply with desorb water at the No.2 post, ii) at No.4 post emission components A, iii) at No.2 post emission components C.The 3rd step of operation comprises i) supply with desorb water at the No.3 post, ii) at No.1 post emission components A, iii) at No.3 post emission components C.The 4th step of operation comprises i) supply with desorb water at the No.4 post, ii) at No.2 post emission components A, iii) at No.4 post emission components C.
Cyclical operation for the second time repeats cyclical operation for the first time.Maltose is supplied with solution and is comprised component A, B component and component C.In them, component A has macromolecule and mobility fast, and B component has intermediate molecular weight and middling speed mobility and component C and has small molecular weight and low speed mobility.As above shown, component A comprises the side chain dextrin that contains the 1-6 key, and B component comprises that the trisaccharide maltose and the component C that contain the 1-4 key comprise glucose and maltose.
The concentration that maltose is supplied with the solids component of solution should be that amount that 53-55wt% and maltose are supplied with solution should be the 3.57v/w% that is equivalent to the resin total amount that a cyclical operation uses.Further, the amount of desorb water should be the 22.59v/w% that is equivalent to the resin total amount that a cyclical operation uses.
On the other hand, the quantity discharged that comprises the component A of desorb water should be the 5.46v/w% that is equivalent to the resin total amount that a cyclical operation uses (1.82v/w% 3 times).The quantity discharged that comprises the B component of desorb water should be the 4.74v/w% that is equivalent to the resin total amount that a cyclical operation uses.The quantity discharged that comprises the component C of desorb water should be the 15.96v/w% that is equivalent to the resin total amount that a cyclical operation uses (5.32v/w% 3 times).
The linear velocity of circulate soln should be that 2.5m/hr and post void volume should be filled with circulate soln consistently.The single job required time of circulation should be less than 23 minutes.The discharging of component A and component C should begin simultaneously.When having arranged component C, should repeat emission components A and component C direction to next post to flow of solution.After finishing altogether the discharging of 3 component A and component C, maltose solution the No.3 post supply with and simultaneously desorb water supply with at the No.1 post and be used for circulation.Then, B component will be discharged at the No.2 post.Use the simulated moving bed chromatography of these 3 components, component C (the high-purity maltose greater than 96%) is with separated.Then, resulting high-purity maltose is condensed into 40-50w/v%.
The present invention will obtain more clearly explaining by the following examples.Yet, should be appreciated that this embodiment is intended to illustrate, but and limit the scope of the invention never in any form.
Embodiment
(embodiment 1) preparation contains the supply solution of 70-75% maltose content
114kg W-Gum and 886L water mix and are dispersed in the 1500L solubilising bowl of belt stirrer.Add the heat-resisting amylase of 60ml (trade mark: Novozyme AA) also stir to obtain starch size solution.At 2kg/cm
2Pressure under, use single pump, utilize the starch size of the gained speed with 10L/min to be moved in the S type holding device from 120 ℃ steam of Z-pulp digester (water heater).Subsequently, the pulp solution of transfer kept 3 minutes at 100 ℃, then at 90 ℃ of digestion tanks that described pulp solution moved into the 500L belt stirrer.
From digestion tank, the aged slurry is moved into the 500L saccharifying tank.Then, utilize water jacket at 65 ℃ of cooling slurries.SPEZYME BBA 1500) and 100ml Starch debranching enzyme (trade mark: PROMOZYME 600L) add in the slurry after 1 hour, with 100ml beta-amylase (trade mark: to obtain saccharification solution.
After 72 hours, collect saccharification solution and be used for high performance liquid chromatography (HPLC) analysis.The composition of the saccharification solution that records comprises maltotetrose and other oligose of 0.8% glucose, 72.4% maltose, 8.4% trisaccharide maltose and 18.4%.Utilization is filtered resulting saccharification solution with perlite and carbon dust as the pressure filter that filters adjuvant.Then, using K, A and/or MB-post to carry out ion-exchange purifies.At last, resulting material concentrates at 55% time under reduced pressure.
(embodiment 2) utilize simulated moving bed chromatography to prepare maltose
Disposed the post of 4 diameter 67cm and length 1m, Amberlite CG6020 sodium type resin tamped post.Therefore, the resin volume becomes the 352L/ post.As shown in Figure 2, the temperature that column system was equipped with and supplied with solution and desorb water is set in 60 ℃, with temperature identical in the post.
Four posts are arranged, from the right No.1, No.2, No.3 and No.4, from No.4 to No.1 with the flow of counter clockwise direction Fluid Computation.Heating contains the maltose supply solution of 75% solids content and is also heated down at 60 ℃ by the desorb water of deionization purifying under 60 ℃.The volumetric velocity of recycle pump is 882L/hr.
1 cyclical operation that is used for separated portion is made up of 4 operation stepss.4 operation stepss (are recycled and repeat from step 1 to step 4) with charging and discharging process.
The first step of operation comprises i) supply with 33.5L maltose supply solution 2.28 minutes with the flow rate of 882L/hr at the No.3 post, ii) supply with 16.5L desorb water 45 seconds at the No.1 post, iii) discharged the 50L B component 3.4 minutes at the No.2 post with the flow rate of 1314L/hr.Therefore, obtained the trisaccharide maltose of B component with 10% solids content concn.
Second step of operation comprises i) supply with 100.7L desorb water 4.6 minutes with the flow rate of 1314L/hr at the No.2 post, ii) discharged 25.7L component A 1.2 minutes at the No.4 post, iii) discharged 75L component C 3.4 minutes at the No.2 post.Therefore, the maltose of component C and the side chain dextrin that has obtained component A with 2.1% concentration have been obtained with 6.1% concentration.
The 3rd step of operation comprises i) supply with 100.7L desorb water 4.6 minutes with the flow rate of 1314L/hr at the No.3 post, ii) discharged 25.7L component A 1.2 minutes at the No.1 post, iii) discharged 75L component C 3.4 minutes at the No.3 post.
The 4th step of operation comprises i) supply with 100.7L desorb water 4.6 minutes with the flow rate of 1314L/hr at the No.4 post, ii) discharged the 25.7L component A1.2 minute at the No.2 post, iii) discharged 75L component C 3.4 minutes at the No.4 post.
The operation cycle of being made up of described 4 operation stepss is repeated continuously.Utilize this operation steps will comprise that the maltose of the glucose of 23% the oligose greater than DP4,22% trisaccharide maltose, 53% maltose and 2% supplies with solution separating.At last, separate and obtained to have the component A (greater than the oligose of DP4) of 95.2% purity; B component (trisaccharide maltose) with 94.5% purity; And component C (maltose) with 96.1% purity.
Then, resulting high purity maltose is by mixed bed formula exchange resin tower, and the resulting material of result is concentrated.Fig. 2 has shown the structure of the post and the equipment that are used to separate and prepare high purity maltose solution.
(embodiment 3) transform high purity maltose alcohol by hydrogenation in the presence of ruthenium catalyst
Heat the stainless steel bowl that heating jacket is installed down at 120 ℃.In this bowl, add the 50g ruthenium catalyst and add the high purity maltose solution (Bx 48) that 50kg obtains simultaneously in embodiment 2.Then, at 50kg/cm
2Carry out 3 hours hydrogenations under the hydrogenation pressure.By NaOH solution adjustment pH is maintained 6.5-7.5 with 10%.After finishing hydrogenation, resulting material comprises the maltotriose alcohol of 1.2% Sorbitol Powder, 95.5% maltose alcohol and 3.3% and greater than the sugar alcohol of DP4.Then, the resulting maltitol solution of filtering and purify.At last, it is concentrated with Bx 85.
Purification, drying and the crystallization of (embodiment 4) high purity maltose alcohol
Preparation 30cm is wide * stainless steel vessel that 30cm length * 45cm is high.Then, do not concentrate maltose alcohol (Bx85) 65 ℃ of following addings with the 28L of crystal seed.Its storage after 48 hours, is removed supernatant liquor.At last, resulting solid maltitol is cut into 20-30cm
2Size.Use the vacuum drier of 60Torr, it is following dry 5 hours at 80 ℃.At last, obtain the maltose alcohol of 0.5% water content.Then, pulverize and the resulting maltose alcohol of powdered with 60 purpose sieves.Resulting maltose alcohol comprises the maltotriose alcohol of 0.2% Sorbitol Powder, 98.9% maltose alcohol and 0.9% and contains sugar alcohol greater than DP4.
Claims (4)
1. method for preparing high purity maltitol crystal powder, it may further comprise the steps:
I) simulated moving bed chromatography of a series of posts by using strong acidic ion resin intensive contains maltose solution greater than 96% pure maltose by the thick formulations prepared from solutions of the maltose that contains 70-75% maltose;
Ii) in the presence of ruthenium catalyst, as 120-130 ℃ of temperature and 40-50kg/cm
2The reaction conditions of pressure can transform and prepare the maltitol solution that contains greater than 95% pure maltose alcohol by the hydrogenation greater than 99% transformation efficiency down; And
Iii) concentrate, dry, grinding and the resulting maltitol solution of crystallization be used to prepare purity greater than 98% maltitol crystal powder.
2. the method for claim 1, wherein said post is intensive at least a strong acidic ion resin, it is selected from Amberlite CG6000 series, Diaion UBK 530K, DowexM4340 and Mitsubisi FRK-01.
3. the method for claim 1, it further comprises step: the ii) resulting maltitol solution of enrichment step; And under 60-80 ℃, kept still spissated maltitol solution 42-54 hour and do not contain crystal seed.
4. high-purity maltose alcohol according to the preparation of the method for claim 1.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020060120506 | 2006-12-01 | ||
| KR1020060120506A KR20080049924A (en) | 2006-12-01 | 2006-12-01 | Process for preparing high purity maltitol crystalline powder |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN101190932A true CN101190932A (en) | 2008-06-04 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA2007100003207A Pending CN101190932A (en) | 2006-12-01 | 2007-01-08 | Method for preparing high purity maltitol crystal powder |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JP2008137982A (en) |
| KR (1) | KR20080049924A (en) |
| CN (1) | CN101190932A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101744215B (en) * | 2008-12-03 | 2012-08-22 | 山东福田投资有限公司 | Process method for separating maltitol solution ternary component by molecular sieve |
| CN109734756A (en) * | 2019-02-28 | 2019-05-10 | 山东兆光色谱分离技术有限公司 | A kind of method of chromatographic isolation maltitol |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20120034366A1 (en) * | 2010-08-05 | 2012-02-09 | Tate & Lyle Ingredients Americas, Inc. | Carbohydrate compositions |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57134498A (en) * | 1981-02-12 | 1982-08-19 | Hayashibara Biochem Lab Inc | Anhydrous crystalline maltitol and its preparation and use |
| JPS5823799A (en) * | 1981-08-03 | 1983-02-12 | 株式会社林原生物化学研究所 | Production of high purity maltose |
| JPS6067000A (en) * | 1983-09-19 | 1985-04-17 | 三菱化学株式会社 | Maltose separating method |
| JPS6092299A (en) * | 1983-10-25 | 1985-05-23 | Sanwa Kosan Kk | Production of powdery maltose |
| FR2575180B1 (en) * | 1984-12-20 | 1987-02-06 | Roquette Freres | HIGH MALTITOL CONTENT, USES THEREOF AND PROCESS FOR PRODUCING THE SAME |
| JP2663134B2 (en) * | 1988-04-26 | 1997-10-15 | 東和化成工業株式会社 | Method for producing high purity maltitol |
| JP2696534B2 (en) * | 1988-09-29 | 1998-01-14 | 東和化成工業株式会社 | Process for producing high-purity maltose and its reduced product |
| JPH0614880B2 (en) * | 1989-04-22 | 1994-03-02 | 株式会社林原生物化学研究所 | Method for producing high-purity maltose |
| JP3070890B2 (en) * | 1993-02-12 | 2000-07-31 | オルガノ株式会社 | Method for producing starch sugar |
| JP3089146B2 (en) * | 1993-10-01 | 2000-09-18 | オルガノ株式会社 | Method for producing starch sugar |
| JP3602903B2 (en) * | 1995-05-02 | 2004-12-15 | 東和化成工業株式会社 | Crystal maltitol and method for producing nectar-containing crystals containing the same |
| JP4106078B2 (en) * | 1995-11-08 | 2008-06-25 | 三菱商事フードテック株式会社 | Method for producing crystalline maltitol |
| JP3786990B2 (en) * | 1995-11-08 | 2006-06-21 | 東和化成工業株式会社 | Purification method of maltitol |
| JP4711471B2 (en) * | 1996-07-05 | 2011-06-29 | 三菱商事フードテック株式会社 | Crystalline maltitol and method for producing honey-containing crystals containing the same |
| FR2769023B1 (en) * | 1997-09-26 | 2000-08-25 | Roquette Freres | PROCESS FOR THE MANUFACTURE OF A MALTOSE-RICH SYRUP |
| FR2787809B1 (en) * | 1998-12-29 | 2002-01-18 | Roquette Freres | PROCESS FOR THE MANUFACTURE OF A MALTOSE-RICH SYRUP |
| JP4737796B2 (en) * | 2000-04-21 | 2011-08-03 | 三井製糖株式会社 | Liver function enhancer |
| DK1656388T3 (en) * | 2003-07-18 | 2012-05-14 | Cargill Inc | Process for providing Maltitol-enriched products |
-
2006
- 2006-12-01 KR KR1020060120506A patent/KR20080049924A/en not_active Application Discontinuation
- 2006-12-26 JP JP2006350452A patent/JP2008137982A/en active Pending
-
2007
- 2007-01-08 CN CNA2007100003207A patent/CN101190932A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101744215B (en) * | 2008-12-03 | 2012-08-22 | 山东福田投资有限公司 | Process method for separating maltitol solution ternary component by molecular sieve |
| CN109734756A (en) * | 2019-02-28 | 2019-05-10 | 山东兆光色谱分离技术有限公司 | A kind of method of chromatographic isolation maltitol |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2008137982A (en) | 2008-06-19 |
| KR20080049924A (en) | 2008-06-05 |
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