CN1328386C - Method for preparing mannitol from raw material of cane sugar - Google Patents
Method for preparing mannitol from raw material of cane sugar Download PDFInfo
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- CN1328386C CN1328386C CNB2005100185653A CN200510018565A CN1328386C CN 1328386 C CN1328386 C CN 1328386C CN B2005100185653 A CNB2005100185653 A CN B2005100185653A CN 200510018565 A CN200510018565 A CN 200510018565A CN 1328386 C CN1328386 C CN 1328386C
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Abstract
The present invention relates to a method for preparing mannitol by using cane sugar as raw materials. Ingredients rich in glucose obtained after fructose and glucose separation through a simulated moving bed carry out enzyme isomerization reaction; obtain isomerized sugar solutions are refined through ion exchange; ingredients rich in the fructose are separated through the simulated moving bed from the obtained materials and invert sugar; the merged ingredients rich in the fructose carry out hydrogenation reaction; obtained mixed alcohol liquid is treated by a conventional method to obtain mannitol products. In the method of the present invention, the cane sugar is used as the raw materials to prepare the mannitol; the ingredients rich in the glucose obtained through the separation through the simulated moving bed after the cane sugar hydrolysis are converted through the enzyme isomerization reaction to generate the fructose, so both of the ingredients rich in the fructose and the ingredients rich in the glucose are effectively utilized, the mannitol yield reaches 42%, and the production benefits are obviously improved.
Description
Technical field
The invention belongs to sucrose is the method for feedstock production N.F,USP MANNITOL.
Background technology
N.F,USP MANNITOL is a kind of of hexan-hexol, be a kind of hydragog(ue) commonly used, dehydrant, also be one of a large amount of pharmaceutical preparations that use and transfusion medication, industrial also can be applicable to made sugar-free chewing gum, polyethers, explosive etc., is widely used in industries such as medicine, food and chemical industry.
The existing at present method that much prepares N.F,USP MANNITOL though still there are many weak points in the technology comparative maturity, is for example extracted N.F,USP MANNITOL from sea-tangle, sad filter, and the thermal source height, the production cost height, the N.F,USP MANNITOL of output is of poor quality, is unsuitable for pharmaceutical; With glucose (or Nulomoline) be raw material, under electrolytic condition the mixture of reducible generation N.F,USP MANNITOL and sorbyl alcohol, again through crystallization extract N.F,USP MANNITOL, but long reaction time, efficient is low, power consumption is big, the N.F,USP MANNITOL productive rate only reaches 15%; So two class methods are eliminated substantially.With fructose is the raw material hydrotreatment, and theoretical yield is 50%, but the price of fructose is higher, industrial production cost height; When being feedstock production N.F,USP MANNITOL with the seminose purely, seminose can all transform generation N.F,USP MANNITOL through hydrogenation, and theoretical yield is 100%, but is a problem in the source of pure seminose.When being feedstock production N.F,USP MANNITOL with glucose, glucose is carried out epimerization change into seminose (transformation efficiency is generally 30%), the N.F,USP MANNITOL sorbitol mixture that back liquid glucose hydrogenation can obtain 30% left and right sides content will be transformed, can obtain the N.F,USP MANNITOL product through crystallization, but the yield of N.F,USP MANNITOL can only reach 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, containing seminose in the liquid glucose dry-matter is 30～33%, contain 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.But because of glucose generally contains crystal water, the yield of glucose still is on the low side.
In Chinese patent application " is that raw material is produced hexavalent alcohol with sucrose " (application number 86107626), proposed with sucrose hydrolysis, fructose and glucose respectively account for half Nulomoline, after handing over processing, Nulomoline is carried out hydrogenation reaction, mannitol content is about 25% in the mixed pure dry-matter of gained, surplus is sorbyl alcohol, more after filtration, from hand over, concentrate, crystallization, centrifugation, drying can make the N.F,USP MANNITOL product, productive rate is about 19～20%; This method flow process is short, the technology simple possible, but in fact only utilized the fructose component behind the sucrose hydrolysis, and the fructose hydrogenation can generate half N.F,USP MANNITOL and half sorbyl alcohol, glucose hydrogenation then all generates sorbyl alcohol, therefore the content that mixes N.F,USP MANNITOL in the pure dry-matter behind the hydrogenation of this method gained has only 25%, and the productive rate of N.F,USP MANNITOL is lower, and most product is for being worth low sorbyl alcohol.
The average price of sucrose and glucose is similar, but because crystalline dextrose contains 1 crystal water molecule usually, can reduce by about 9% dry matter weight after water-soluble, and dry-matter can be gained in weight on the contrary behind the sucrose hydrolysis, is that raw material production N.F,USP MANNITOL is more worthwhile with sucrose therefore.For abounding with the sucrose area, more biasing toward with sucrose is raw material production N.F,USP MANNITOL.
Summary of the invention
The technical problem to be solved in the present invention provide a kind of be feedstock production N.F,USP MANNITOL with sucrose, make the productive rate of N.F,USP MANNITOL from 19～20% original methods of bringing up to more than 29% even 42%.
The present invention solves the problems of the technologies described above with following technical scheme:
To carry out enzyme isomerize reaction through the glucose component that is rich in that separation obtains, epimerized sugar liquid is through refining from handing over, be rich in the fructose component with simulation moving-bed isolating again with Nulomoline, front and back operation gained is rich in the fructose component merges and to carry out hydrogenation reaction, the mixed alcoholic liquid that obtains after filtration, from hand over, concentrate, crystallization, centrifugation, drying treatment obtain the N.F,USP MANNITOL product.
Simulation moving-bed separating levulose glucose is at 45～70 ℃, input concentration 40～66%, makes eluent, is separating agent with calcium type Zeo-karb with water, carries out continuously carrying out under the condition of charging, water inlet, discharging.
Simulation moving-bed is end to end with 12 posts or 24 posts, and each post all is connected to discharge port, opening for feed, circulation port, water-in, and it is mobile relatively to utilize recycle pump that material is produced in post.
Simulation moving-bed operative configuration is to add Controlling System with magnetic valve, or the rotary valve Controlling System.
With the resulting glucose component that is rich in behind the separating levulose glucose, being concentrated in vacuo to concentration earlier is 40～60%, utilize fixed glucose isomerase to carry out isomerization reaction then, handle through the yin, yang ion-exchange resins again and remove impurity and ion, obtain epimerized sugar liquid.
The resulting fructose component that is rich in through after friendship is refining, adds hydrogenation catalyst, and hydrogenation reaction is 1～3 hour under 100～180 ℃ of temperature, 4～7Mpa hydrogen pressure condition, generates the mixed alcoholic liquid that contains N.F,USP MANNITOL.
Also can will carry out enzyme isomerize reaction through the simulation moving-bed isolated glucose component that is rich in, epimerized sugar liquid be rich in the fructose component and merge and to carry out hydrogenation reaction, perhaps epimerized sugar liquid be rich in the fructose component and carry out respectively remerging after the hydrogenation reaction, the mixed alcoholic liquid that obtains after filtration, from hand over, concentrate, crystallization, centrifugation, drying treatment obtain the N.F,USP MANNITOL product.The technical scheme of the condition of simulation moving-bed separating levulose glucose, structure, technology and hydrogenation, mixed alcohol processing etc. is same as described above.
With method of the present invention is feedstock production N.F,USP MANNITOL with sucrose, the resulting glucose component that is rich in transforms generation fructose by enzyme isomerize reaction, make to be rich in the fructose component and to be rich in the glucose component and all obtained effective utilization, thereby make the yield of N.F,USP MANNITOL can reach 42%, obviously improved productivity effect.
Description of drawings
Fig. 1 is that the present invention is the process flow sheet of feedstock production N.F,USP MANNITOL method with sucrose.
Fig. 2 is that the present invention is the schema that feedstock production N.F,USP MANNITOL method is simplified technology with sucrose.
Embodiment
The present invention has adopted conventional method for hydrolysis to sucrose hydrolysis, can adopt hydrochloric acid as hydrolyst, the suitable condition of hydrolysis is: sugar concentration (weight percent, as follows) is 40～60%, pH value 1～4, 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, contain fructose, glucose half and half in its dry-matter.Need make the sucrose complete hydrolysis, otherwise the effect of back of the present invention will be affected.
Utilize the simulation moving-bed technology of from Nulomoline, isolating fructose and glucose also to have open.Used in the present invention simulation moving-bed be end to end with 12 posts or 24 posts, each post all is connected to discharge port, opening for feed, circulation port, water-in, it is mobile relatively to utilize recycle pump that material is produced in post.Simulation moving-bed have two kinds of operative configuration: a kind of is to add Controlling System with magnetic valve, another is the rotary valve control forms, this dual mode can constantly change the position of opening for feed, discharge port, water-in, circulation import and export, reaches isolating purpose.
The present invention selects for use calcium type Zeo-karb as separate sorbent, the concentration of charging liquid glucose is 40～66%, with water as eluent, separation temperature is 45～70 ℃, carry out charging, water inlet, discharging operation continuously, the fructose content that is rich in dry-matter in the fructose component of gained is 90～96%, and concentration is 20～35%; The fructose content that is rich in dry-matter in the glucose component of gained is lower than 9%, and glucose content is 91～96%, and concentration is 16～30%.After simulation moving-bed separation, fructose in the Nulomoline is effectively separated with glucose, and this step is a key of the present invention, and is not thorough if fructose separates with Portugal's glucose, will have a strong impact on the effect of the inventive method back, even can make the yield of N.F,USP MANNITOL not reach requirement.
Be rich in the glucose component to be concentrated in vacuo to concentration earlier be 40～60% resulting behind simulation moving-bed separating levulose, the glucose, utilize fixed glucose isomerase to carry out isomerization reaction then, a part of conversion of glucose is generated fructose, after impurity and ion are removed in the processing of yin, yang ion-exchange resins, obtain epimerized sugar liquid again.
The used fixed glucose isomerase of enzyme isomerize reaction is when the Sweetzyme T that selects for use Denmark's promise and company to produce, and the enzyme isomerize reaction condition is as follows: temperature of reaction is 57～60 ℃, and the liquid glucose pH value is 7.0～8.0, and the sugared dry-matter of per 1000 grams adds MgSO
47H
2O solid 1～3 gram, the flow velocity that liquid glucose flows through the enzyme post remains per hour 1～2 times of enzyme post bed volume.Add an amount of sal epsom and help to improve the catalytic activity of enzyme, reduce the restraining effect of the existence of calcium enzymic activity.Fixed bed enzyme reactor of the present invention is a Glass tubing, and interior dress immobilized enzyme, liquid glucose flow through enzyme post bed from top to bottom, and Glass tubing has the chuck insulation outward, the recirculated water heating is housed keeps corresponding temperature.The easy inactivation of the too high enzyme of isomerization reaction temperature is crossed low-conversion and is not reached requirement.The too high meeting of liquid glucose flow velocity make the reaction times not enough, transformation efficiency is low, cross low then throughput and descend.According to condition of the present invention, be rich in the glucose component through behind the enzyme isomery, the component in the dry-matter of resulting epimerized sugar liquid is: fructose content 40～44%, glucose content are 56～60%, concentration is 40～60%.
Epimerized sugar liquid can be carried out simulation moving-bed separating levulose and glucose once more on the technology, also can will epimerized sugar liquid and Nulomoline carry out simulation moving-bed separating levulose glucose again after merging, used simulation moving-bed separating technology and requiring all with above-mentioned.
From the last resulting fructose component that is rich in, contain fructose 90～96%, glucose 4～10% in the dry-matter, 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, conversion of glucose becomes sorbyl alcohol, and fructose transforms and generates half N.F,USP MANNITOL and half sorbyl alcohol.The dry-matter mannitol content is 45～50% in the mixed alcoholic liquid behind the hydrogenation, and sorbyl alcohol is 50～55%.
With the mixed alcoholic liquid behind the hydrogenation after filtration, remove nickel catalyzator after, with positive and negative ion-exchange resins refinement treatment, through obtaining the N.F,USP MANNITOL crystal after vacuum concentration, decrease temperature crystalline, the centrifugation, after the drying treatment, obtain the N.F,USP MANNITOL product again.The N.F,USP MANNITOL product yield can reach 42%.
If will carry out the separation of fructose glucose to epimerized sugar liquid with simulation moving-bed, change into epimerized sugar liquid no longer separated and be rich in the fructose component and merge back end hydrogenation, perhaps epimerized sugar liquid be rich in the fructose component and carry out respectively remerging behind the hydrogenation, obtain containing the mixed alcoholic liquid of N.F,USP MANNITOL, can simplify technology like this, its technical process as shown in Figure 2, but because the fructose content of epimerized sugar liquid is far below the fructose content that is rich in the fructose component, therefore the mannitol content of simplifying in the resultant hydrogenation liquid of technology is about 34%, and the N.F,USP MANNITOL yield can only reach about 29%.
Embodiment 1:
The edible white sugar of 1000 grams, be dissolved in the deionized water of 1500ml, obtain concentration and be 40.14% aqueous sucrose solution, add the 40ml technical hydrochloric acid, the pH value of liquid glucose is adjusted to 1.2, stirring reaction 1.5 hours under 92 ℃ temperature condition is removed impurity with the cationic, anionic exchange resin post from handing over again then, obtains conversion liquid glucose 2410 grams after refining, sugar concentration is 41.55%, contain fructose 49.75% in its dry-matter, contain glucose 49.82%, other small amount of impurities 0.43%.
Utilize this conversion liquid glucose of simulation moving-bed device separating treatment of 12 posts, input concentration is 51.55%, under 58 ℃ separation temperature, as adsorption separating agent, be eluent with water with calcium type Zeo-karb CR1320, carry out charging, water inlet, discharging operation continuously, obtain being rich in the fructose component and be rich in the glucose component, the quality that is rich in the fructose component is 1680 grams, and concentration is 28.55%, dry-matter contains fructose 94.13%, contains glucose 5.87%; The quality that is rich in the glucose component is 2138 grams, and concentration is 24.32%, and dry-matter contains fructose 6.2%, glucose 93.4%, other impurity 0.4%.
To separate resulting glucose component 2138 gram (concentration is 24.32%) that is rich in back, be that to be concentrated to concentration under the 0.06Mpa condition be 40.44% in vacuum tightness, and the liquid glucose pH value is adjusted to 7.7, adds MgSO
47H
2O solid 0.55 gram, enzyme isomerization reaction temperature is 57 ℃, after immobilized enzyme isomery post carries out isomerization reaction, handle from handing over cationic, anionic exchange resin, obtain epimerized sugar liquid 1300 grams, concentration is 40%, and the fructose content in the epimerized sugar liquid dry-matter is 43.6%, glucose 55.9%, other impurity 0.5%.
Utilize simulation moving-bed this epimerized sugar liquid of device separating treatment of 12 posts, input concentration is 40.1%, under 58 ℃ separation temperature, as adsorption separating agent, is eluent with water with calcium type Zeo-karb CR1320, carries out charging, water inlet, discharging operation continuously, obtain being rich in the fructose component and be rich in the glucose component, being rich in fructose component concentration is 28.40%, contains fructose 93.40% in the dry-matter, contains glucose 6.60%; Being rich in glucose component concentration is 24.32%, contains fructose 6.8% in the dry-matter, glucose 93.2%.Be rich in the glucose component again through being concentrated to after concentration is 40%, repeat enzyme isomerize reaction and generate the fructose component.
With resulting fructose component 1830 grams (concentration is 28.40%) that are rich in behind the simulation moving-bed separating levulose glucose, 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, remove by filter nickel catalyzator, mixed alcoholic liquid 3510 restrains (concentration is 28.5%) after obtaining hydrogenation, containing N.F,USP MANNITOL in this mixed pure dry-matter is 46.70%, and containing sorbyl alcohol is 53.30%, with sun, after cloudy ion-exchange resins is refining, be concentrated to 61%, cooling, crystallization treatment is passed through centrifugation again, drying treatment obtains N.F,USP MANNITOL product 424 grams.The N.F,USP MANNITOL productive rate of present embodiment counts 42.4% by the sucrose charging capacity.
Embodiment 2:
Take by weighing 3540 gram white sugars, be dissolved in the deionized water of 1900ml, obtain concentration and be 65.0% aqueous sucrose solution, add the 140ml technical hydrochloric acid, the pH value of liquid glucose is adjusted to 3.7, then stirring reaction 0.5 hour under 102 ℃ temperature condition, remove impurity with the cationic, anionic exchange resin post from handing over again, conversion liquid glucose 5510 grams after obtaining making with extra care, sugar concentration is 65.5%, contains fructose 49.8%, glucose 49.9%, other small amount of impurities 0.3% in the dry-matter.
Utilize this conversion liquid glucose of simulation moving-bed device separating treatment of 24 posts, input concentration is 65.5%, under 68 ℃ separation temperature, as adsorption separating agent, be eluent with water with calcium type Zeo-karb CR1320, carry out charging, water inlet, discharging operation continuously, obtain being rich in the fructose component and be rich in the glucose component, the quality that is rich in the fructose component is 6420 grams, and concentration is 27.57%, contain fructose 94.35% in the dry-matter, contain glucose 5.65%; The quality that is rich in the glucose component is 7660 grams, and concentration is 24.02%, contains fructose 7.0% in the dry-matter, glucose 92.4%, other impurity 0.6%.
To separate resulting glucose component 7660 gram (concentration is 24.02%) that is rich in back, be that to be concentrated to concentration under the 0.06Mpa condition be 49.6% in vacuum tightness, and regulating the liquid glucose pH value is 7.2, adds MgSO
47H
2O solid 5.5 grams, enzyme isomerization reaction temperature is 59.6 ℃, after immobilized enzyme isomery post carries out isomerization reaction, handle from handing over cationic, anionic exchange resin, obtain epimerized sugar liquid 3680 grams, concentration is 50%, and fructose content is 44% in the epimerized sugar liquid dry-matter, glucose 55.7%, other impurity 0.3%.
Utilize simulation moving-bed this epimerized sugar liquid of device separating treatment of 24 posts, input concentration is 50.0%, under 58 ℃ separation temperature, as adsorption separating agent, is eluent with water with calcium type Zeo-karb CR1320, carries out charging, water inlet, discharging operation continuously, obtain being rich in the fructose component and be rich in the glucose component, being rich in fructose component concentration is 28.5%, and dry-matter contains fructose 94.40%, contains glucose 5.60%; Being rich in glucose component concentration is 24.82%, and dry-matter contains fructose 6.8%, glucose 93.2%.Be rich in the glucose component again through being concentrated to after concentration is 50%, repeat enzyme isomerize reaction and generate the fructose component.
Be rich in fructose component 12640 gram (concentration is 28.5% resulting behind the simulation moving-bed separating levulose glucose, fructose content is 94.4% in the dry-matter), through after handing over processing, add 300 gram Raney's nickels, in the high-pressure hydrogenation still, under the 4Mpa pressure condition, be warmed up to 175 ℃ and carried out hydrogenation reaction 160 minutes, remove by filter nickel catalyzator, obtain mixed alcoholic liquid 12630 grams (concentration is 28.2%) behind the hydrogenation, this mixes, and to contain N.F,USP MANNITOL in pure dry-matter be 47.43%, containing sorbyl alcohol is 52.57%, use sun, after cloudy ion-exchange resins is refining, be concentrated to 60%, cooling, crystallization treatment, pass through centrifugation again, drying treatment obtains N.F,USP MANNITOL product 1530 grams.Present embodiment N.F,USP MANNITOL productive rate counts 43.2% by the sucrose charging capacity.
Embodiment 3:
Take by weighing 3540 gram white sugars, be dissolved in the deionized water of 3500ml, obtain concentration and be 50.48% aqueous sucrose solution, add the 140ml technical hydrochloric acid, the pH value of liquid glucose is adjusted to 2.25, 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 6870 grams after refining, sugar concentration is 52.55%, contain fructose 49.8% in the dry-matter, contain glucose 49.9%, other small amount of impurities 0.3%.
Utilize this conversion liquid glucose of simulation moving-bed device separating treatment of 12 posts, input concentration is 52.55%, under 58 ℃ separation temperature, as adsorption separating agent, be eluent with water with calcium type Zeo-karb CR1320, carry out charging, water inlet, discharging operation continuously, obtain being rich in the fructose component and be rich in the glucose component, the quality that is rich in the fructose component is 6420 grams, and concentration is 27.57%, contain fructose 94.35% in the dry-matter, contain glucose 5.65%; The quality that is rich in the glucose component is 7660 grams, and concentration is 24.02%, contains fructose 7.0% in the dry-matter, glucose 92.4%, other impurity 0.6%.
To separate resulting glucose component 7660 gram (concentration is 24.02%) that is rich in back, be that to be concentrated to concentration under the 0.06Mpa condition be 49.6% in vacuum tightness, adds MgSO
47H
2O solid 5.5 grams, transferring the liquid glucose pH value is 7.9, enzyme isomerization reaction temperature is 59 ℃, after immobilized enzyme isomery post carries out isomerization reaction, handle from handing over, obtain epimerized sugar liquid 3680 grams with cationic, anionic exchange resin, concentration is 50%, fructose content is 44% in the epimerized sugar liquid dry-matter, glucose 55.7%, other impurity 0.3%.
(concentration is 50% with epimerized sugar liquid 3680 grams, fructose content is 44% in the dry-matter), (concentration is 27.57% with separate fructose component 6420 grams that are rich in that obtain through simulation moving-bed device, fructose content is 94.35% in the dry-matter) merge after, through handling, add 300 gram Raney's nickels, in the high-pressure hydrogenation still from handing over, under the 4Mpa pressure condition, be warmed up to 175 ℃ and carried out hydrogenation reaction 2 hours, remove by filter nickel catalyzator, obtain mixed alcoholic liquid 10100 grams (concentration is 35.64%) behind the hydrogenation, containing N.F,USP MANNITOL in this mixed pure dry-matter is 34.4%, containing sorbyl alcohol is 65.4%, other 0.2%, with the sun, after cloudy ion-exchange resins is refining, be concentrated to 67%, cooling, crystallization treatment is passed through centrifugation again, drying treatment obtains N.F,USP MANNITOL product 1030 grams.Present embodiment N.F,USP MANNITOL productive rate counts 29.1% by the sucrose charging capacity.
Embodiment 3 is with epimerized sugar liquid and be rich in fructose component merging back end hydrogenation, and resulting N.F,USP MANNITOL productive rate is lower than embodiment 1 and embodiment 2.But the productive rate that embodiment 3 produces N.F,USP MANNITOL than sucrose hydrolysis hydrogenation method in the past still improves.
Claims (1)
1. one kind is the method for feedstock production N.F,USP MANNITOL with sucrose, with the sucrose material complete hydrolysis, the Nulomoline that after friendship is refining, obtains, separate with the simulation moving-bed fructose glucose that carries out, obtain being rich in the fructose component and be rich in the glucose component, it is characterized in that utilizing glucose isomerase to carry out enzyme isomerize reaction to the glucose component that is rich in that separation obtains, epimerized sugar liquid is through refining from handing over, be rich in the fructose component with simulation moving-bed isolating again with Nulomoline, front and back operation gained is rich in the fructose component carries out hydrogenation reaction, the mixed alcoholic liquid that obtains after filtration, from friendship, concentrate, crystallization, centrifugation, drying treatment gets the N.F,USP MANNITOL product.
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| CNB2005100185653A CN1328386C (en) | 2005-04-13 | 2005-04-13 | Method for preparing mannitol from raw material of cane sugar |
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| CN1328386C true CN1328386C (en) | 2007-07-25 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101215580B (en) * | 2007-12-26 | 2012-03-21 | 广西南宁化学制药有限责任公司 | Method for preparing D-mannitol from konjak refined powder |
| CN102584534B (en) * | 2012-01-18 | 2014-02-19 | 浙江华康药业股份有限公司 | Method for producing mannite through adopting Raney's nickel and Raney's copper in coordination with catalytic hydrogenation |
| CN105255961A (en) * | 2015-10-22 | 2016-01-20 | 邓和超 | Isomerization method for glucose in fructose production process |
| 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 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1528916A (en) * | 2003-09-28 | 2004-09-15 | 南宁市化工研究设计院 | Cane sugar material high-yield joint production process of crystalline fructose and manna sugar |
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| CN1528916A (en) * | 2003-09-28 | 2004-09-15 | 南宁市化工研究设计院 | Cane sugar material high-yield joint production process of crystalline fructose and manna sugar |
Non-Patent Citations (3)
| Title |
|---|
| 甘露醇的性质，生产与发展建议 黎颖，广西华工，第1999卷第4期 1999 * |
| 甘露醇的性质，生产与发展建议 黎颖，广西华工，第1999卷第4期 1999;甘露醇的研究进展 王瑞芝，河北化工，第2001卷第2期 2001 * |
| 甘露醇的研究进展 王瑞芝，河北化工，第2001卷第2期 2001 * |
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