CN105001279B - The method that isomalt is prepared by catalytic hydrogenation by isomaltoketose - Google Patents
The method that isomalt is prepared by catalytic hydrogenation by isomaltoketose Download PDFInfo
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- CN105001279B CN105001279B CN201510361774.1A CN201510361774A CN105001279B CN 105001279 B CN105001279 B CN 105001279B CN 201510361774 A CN201510361774 A CN 201510361774A CN 105001279 B CN105001279 B CN 105001279B
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- isomaltoketose
- isomalt
- catalyst
- nickel
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- SERLAGPUMNYUCK-DCUALPFSSA-N 1-O-alpha-D-glucopyranosyl-D-mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O SERLAGPUMNYUCK-DCUALPFSSA-N 0.000 title claims abstract description 32
- 239000000905 isomalt Substances 0.000 title claims abstract description 32
- 235000010439 isomalt Nutrition 0.000 title claims abstract description 32
- HPIGCVXMBGOWTF-UHFFFAOYSA-N isomaltol Natural products CC(=O)C=1OC=CC=1O HPIGCVXMBGOWTF-UHFFFAOYSA-N 0.000 title claims abstract description 32
- 238000000034 method Methods 0.000 title claims abstract description 23
- 238000009903 catalytic hydrogenation reaction Methods 0.000 title claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims abstract description 34
- 239000003054 catalyst Substances 0.000 claims abstract description 22
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000001257 hydrogen Substances 0.000 claims abstract description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
- YOCUPQPZWBBYIX-UHFFFAOYSA-N copper nickel Chemical compound [Ni].[Cu] YOCUPQPZWBBYIX-UHFFFAOYSA-N 0.000 claims abstract description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims abstract description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 5
- 238000001704 evaporation Methods 0.000 claims description 4
- 230000008020 evaporation Effects 0.000 claims description 4
- 238000005469 granulation Methods 0.000 claims description 3
- 230000003179 granulation Effects 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 3
- 238000001694 spray drying Methods 0.000 claims description 3
- -1 malt ketone Chemical class 0.000 claims description 2
- 239000011259 mixed solution Substances 0.000 claims description 2
- 150000005846 sugar alcohols Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 16
- 238000002360 preparation method Methods 0.000 abstract description 3
- 238000011160 research Methods 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 229930195725 Mannitol Natural products 0.000 description 4
- 229910000564 Raney nickel Inorganic materials 0.000 description 4
- 238000001514 detection method Methods 0.000 description 4
- 239000000594 mannitol Substances 0.000 description 4
- 235000010355 mannitol Nutrition 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000006188 syrup Substances 0.000 description 4
- 235000020357 syrup Nutrition 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000007868 Raney catalyst Substances 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 238000012797 qualification Methods 0.000 description 2
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 2
- 235000019345 sodium thiosulphate Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- 208000007976 Ketosis Diseases 0.000 description 1
- GVJNTKYYZXDYAH-UHFFFAOYSA-K [Cu+3].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O Chemical class [Cu+3].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O GVJNTKYYZXDYAH-UHFFFAOYSA-K 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001323 aldoses Chemical class 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- AVVWPBAENSWJCB-UKFBFLRUSA-N alpha-D-glucofuranose Chemical compound OC[C@@H](O)[C@H]1O[C@H](O)[C@H](O)[C@H]1O AVVWPBAENSWJCB-UKFBFLRUSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 108010051210 beta-Fructofuranosidase Proteins 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000001573 invertase Substances 0.000 description 1
- 235000011073 invertase Nutrition 0.000 description 1
- 150000002584 ketoses Chemical class 0.000 description 1
- 239000006101 laboratory sample Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
Landscapes
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
The invention discloses a kind of methods preparing isomalt by catalytic hydrogenation by isomaltoketose, it is added in autoclave after isomaltoketose and water are mixed in a certain ratio, isomalt, reaction temperature is obtained by the reaction under the conditions of existing for catalyst with hydrogen：110~120 DEG C；Hydrogenation pressure：0.5~0.7MPa；PH value in reaction：5.0‑6.0；Catalyst compounds for independent research：The weight of the mixture of the mixture of skeletal nickel catalyst and nickel-copper catalyst, wherein skeletal nickel catalyst and nickel-copper catalyst is the 1%~2% of isomaltoketose weight；The weight ratio of skeletal nickel catalyst and nickel-copper catalyst is 1:1~1:0.5.The purpose of the present invention is to provide a kind of reaction condition is mild, high conversion rate, safe isomalt preparation method.
Description
Technical field
The present invention relates to aldoses and ketose catalytic hydrogenation field, specifically a kind of to be added by catalysis by isomaltoketose
The method that hydrogen prepares isomalt.
Background technology
It is existing to be mostly used greatly through invertase by the method that catalytic hydrogenation prepares isomalt by isomaltoketose
The isomaltoketose generated after method isomery is hydrogenating materials, and α-D- furans are hydroconverted under Raney nickel, high temperature, condition of high voltage
It mutters glucityl -1,6-D- sorbierites（GPS）With α-D- glucofuranose base -1,1-D- mannitol（GPM）, in reaction product this two
Kind sugar alcohol is equimolar mixing（Collection of illustrative plates has two peaks）, referred to as isomalt.Using adopting on traditional hydrogenation technique
With skeleton nickel single catalyst, need to also only have into the method for horizontal high voltage, high temperature, high-speed stirred, conversion ratio to improve reaction speed
97-98%, machine utilization is big, and safety operation risk is high, so that domestic isomalt manufacturer is fewer.
Invention content
The purpose of the present invention is to provide a kind of isomalt systems that reaction condition is mild, high conversion rate, safe
Preparation Method.
The present invention specific technical solution be：One kind preparing isomalt by isomaltoketose by catalytic hydrogenation
Method, be added in autoclave after isomaltoketose and water are mixed in a certain ratio, the condition existing for catalyst
Isomalt is obtained by the reaction in lower and hydrogen.Specific process parameter：
Reaction temperature：110~120 DEG C；
Hydrogenation pressure：0.5~0.7MPa；
Speed of agitator：200-300r/ points
PH value in reaction：5.0-6.0；
Catalyst is voluntarily to be compounded before facing production, and formula is independent research：Skeletal nickel catalyst and nickel-copper catalyst it is mixed
Object is closed, the wherein weight of the mixture of skeletal nickel catalyst and nickel-copper catalyst is the 1%~2% of isomaltoketose weight；Skeleton
The weight ratio of Raney nickel and nickel-copper catalyst is 1:1~1:0.5.
In the method that above-mentioned isomaltoketose prepares isomalt by catalytic hydrogenation, the different malt ketone
The weight ratio of sugar and water is 1:1~1.4:1.
In the method that above-mentioned isomaltoketose prepares isomalt by catalytic hydrogenation, the reaction time 0.5
~1 hour, the conversion ratio of isomaltoketose was more than 99.8%.
In the method that above-mentioned isomaltoketose prepares isomalt by catalytic hydrogenation, the control of the pH value
Method processed is：The mixed solution of isomaltoketose and water is 5.0-6.0 by being adjusted to pH value with 2wt% liquid caustic soda or 2wt% hydrochloric acid.
In the method that above-mentioned isomaltoketose prepares isomalt by catalytic hydrogenation, also wrap after reaction
It includes through the highly concentrated evaporation of single-action, spray drying granulation and is packaged to be finished solid isomalt.
Compared with prior art, the beneficial effects of the present invention are：
The present invention is special catalyst compounded using independent research, and hydrogenation reaction pressure is made to be reduced from tradition from 10-12Mpa
To 0.5-0.7Mpa, reaction temperature is reduced to 110-120 from tradition from 130-145 DEG C, and speed of agitator is from traditional 700-800r/
Divide and be reduced to 200-300r/ points, conversion ratio is increased to 99-99.5% from former 97-98%, and overhaul of the equipments is once delayed by original half a year
To equipment operation ratio annually, is improved every year, as reaction condition becomes mild, machine utilization is alleviated, improves behaviour
Make safety, product purity higher.Skeletal nickel catalyst and nickel-copper catalyst can effectively improve conversion ratio, make reaction condition temperature
With, reduction production difficulty, raising processing safety.
Specific implementation mode
With reference to embodiment, technical scheme of the present invention is described in further detail, but do not constituted pair
Any restrictions of the present invention.
Embodiment 1
1, the isomaltoketose 1200g that purity is 98wt% is weighed, adds water 1200g to autoclave, dissolving is deployed into about
2000Ml, 50% solution is to get syrup；
2, skeletal nickel catalyst 8g, nickel-copper catalyst 6g are weighed, is added in syrup and stirs evenly, in reaction process, mixing speed
For 200-300r/min；Wherein, skeletal nickel catalyst is the Raney's nickel of the triumphant Chemical Industry Science Co., Ltd's production of upper Hisoon, nickel-copper
Method for preparing catalyst such as The Journal of Catalysis 81,204-13, recorded in 1983.
3, syrup pH value is adjusted to 5.0-6.0 with 2% liquid caustic soda and 2% hydrochloric acid；
4, airtight test is carried out to autoclave, Hydrogen Vapor Pressure is filled with to 1MPa, cyclic permutation 3 times after passed examination
Detecting oxygen in hydrogen, to being less than 0.3%, it is 0.6MPa to be then charged with hydrogen；
5, start heating.100 DEG C of set temperature closes heating key when temperature reaches 100 DEG C.Controlling reaction temperature 110-
120℃。
6, pressurize adds hydrogen.It is careful to adjust reaction pressure 0.6Mpa, during the reaction as isomaltoketose constantly adds hydrogen,
Hydrogen is consumed and pressure declines, and opens hydrogen valve pressurising again when dropping to 0.5Mpa to 0.6Mpa, so constantly repeats to add
Hydrogen is until Hydrogen Vapor Pressure no longer falls to reaction end after pressurising.Close hydrogen inlet valve.
7, continue out stirring, stop heating.Blow-off valve is opened, about 50ml samples is carefully taken to be less than to laboratory detection reduced sugar
0.04% is qualification, and PH about 7 confirms that reaction terminates.1 hour reaction time.
8, cool down；Coil pipe cooling water is connected, is cooled to 95 DEG C.
9, discharge is flashed；Stirring is opened in holding, carefully opens blow-off valve；Collect reaction product.
10, nitrogen is replaced；After operation, nitrogen valve, such as above-mentioned 4th step replacement reaction kettle 3 times, notice are opened
Laboratory sample, detection examination it is quick-fried without explosion for qualification.Pressure 1Mpa, band nitrogen storage with pressure is adjusted in reaction kettle when not used.
11, the reaction product of step 9 is concentrated into after a concentration of 85wt% by single-action standard pan on 110 DEG C of left sides
Right evaporation and concentration removes partial moisture therein, and concentration rises to 95~96% by 85% or so, obtains isomalt height
Concentrated sugar is starched.
12, the highly concentrated syrup of isomalt after the highly concentrated evaporation and concentration of single-action is injected to solid by gas stream atomizer
Determine in fluid bed spray drying granulation machine, is dried to moisture<0.5%, and solid Isomalt is obtained, subsequently into
It is finally dried and is cooled down in Vibratingfluidbeddrier.
13, the solid Isomalt after drying-granulating is filled in special packaging bag by automatic ration and obtains into
Product solid Isomalt.
The purity of isomalt is 99.8%, and the content of reduced sugar is 0.08%.
Embodiment 2：
It is substantially the same with embodiment 1, different places is, isomaltoketose 1400g, water 1000g；Skeleton nickel is urged
Agent 18.5g, nickel-copper catalyst 9.5g.Skeletal nickel catalyst is the Raney's nickel of the triumphant Chemical Industry Science Co., Ltd's production of upper Hisoon,
For nickel-copper method for preparing catalyst as recorded in Chinese patent application CN201310028518.1, ambrose alloy ratio is 1:1.
It is careful to adjust reaction pressure 0.7Mpa in step 6, during the reaction as isomaltoketose constantly adds hydrogen, hydrogen
Gas is consumed and pressure declines, and opens hydrogen valve pressurising again when dropping to 0.55Mpa to 0.7Mpa, so constantly repeats to add hydrogen
Until Hydrogen Vapor Pressure no longer falls to reaction end after pressurising.Close hydrogen inlet valve.
The purity of isomalt is 99.84%, and the content of reduced sugar is 0.05%.
Detection method
The detection of isomalt：High performance liquid chromatography
Chromatographic condition：
Mobile phase：The ultra-pure water filtered through 0.45 μm of filtering vacuum；
Chromatographic column：300*7.8mmCOREGEL-87C column；
Flow velocity：0.5-0.8ml/min；
Column temperature：60-85℃；
Sampling volume：20μL；
Standard items prepare：
A certain amount of isomalt standard items, mannitol standard items and sorbierite standard items are weighed to be dissolved in the water,
With obtain a concentration of 20mg/ml isomaltoketose alcoholic solution and a concentration of 0.1mg/mL mannitol mark solution and sorbierite it is molten
Liquid；
Preparation of samples：
About 1000mg samples are weighed, in 50mL volumetric flasks, with water constant volume.
It measures
The standard solution and sample solution for injecting same volume respectively, record the peak face of GPS, GPM, mannitol, sorbierite
Product calculates the content of GPS and GPM.
The measurement of reduced sugar：
3.3g samples are weighed in iodine flask, 25ml water is added, is slowly added to dissolve, the examination of 20ml alkalinity copper citrates is added
Liquid and several beades, solution comes to life after heated solution about 4min, and 3min is boiled in holding, it is rapid it is cooling after, 100ml is added
Diluted acetic acid solution and 20.0ml, 0.025mol/l iodine titration solutions, while rocking solution, 25ml dilute hydrochloric acid solutions are added in side, when
After precipitation dissolving, extra iodine solution is titrated with 0.05mol/L sodium thiosulfate, and in nearly titration end-point, 2ml, 1% shallow lake is added
Powder indicator, the sodium thiosulfate volume consumed are no less than 12.8ml.
It is above-described be only presently preferred embodiments of the present invention, it is all within the scope of the spirit and principles in the present invention made by appoint
What modifications, equivalent substitutions and improvements etc., should all be included in the protection scope of the present invention.
Claims (5)
1. a kind of method preparing isomalt by catalytic hydrogenation by isomaltoketose mixes isomaltoketose with water
After be added in autoclave, isomalt is obtained by the reaction under the conditions of existing for catalyst with hydrogen, feature exists
In：
Reaction temperature：110~120 DEG C；
Hydrogenation pressure：0.5~0.7MPa；
Speed of agitator：200-300r/ points；
PH value in reaction：5.0-6.0；
Catalyst is：The mixture of skeletal nickel catalyst and nickel-copper catalyst, wherein skeletal nickel catalyst and nickel-copper catalyst
Mixture weight be isomaltoketose weight 1%~2%；The weight ratio of skeletal nickel catalyst and nickel-copper catalyst is
1:1~1:0.5.
2. the method that isomaltoketose according to claim 1 prepares isomalt by catalytic hydrogenation, feature
It is, the weight ratio of the isomaltoketose and water is 1:1~1.4:1.
3. the method that isomaltoketose according to claim 2 prepares isomalt by catalytic hydrogenation, feature
It is, the reaction time is 0.5~1 hour, and the conversion ratio of isomaltoketose is more than 99.8%.
4. the method that isomaltoketose according to claim 2 prepares isomalt by catalytic hydrogenation, feature
It is, the control method of the pH value is：The mixed solution of isomaltoketose and water is by with 2wt% liquid caustic soda or 2wt% hydrochloric acid
It is 5.0~6.0 to be adjusted to pH value.
5. the method that isomaltoketose according to claim 2 prepares isomalt by catalytic hydrogenation, feature
It is, further includes by the highly concentrated evaporation of single-action, spray drying granulation and being packaged to be the different malt ketone of finished solid after reaction
Sugar alcohol.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
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| CN201510361774.1A CN105001279B (en) | 2015-06-26 | 2015-06-26 | The method that isomalt is prepared by catalytic hydrogenation by isomaltoketose |
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| CN105969824A (en) * | 2016-07-25 | 2016-09-28 | 山东百龙创园生物科技有限公司 | Preparation method of palatinitol |
| CN110813297B (en) * | 2019-10-15 | 2021-04-30 | 厦门大学 | A kind of synthetic method of sugar alcohol |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4117173A (en) * | 1975-05-06 | 1978-09-26 | Suddeutsche Zucker-Aktiengesellschaft | Use of glucopyranosido-1,6-mannitol as a sugar substitute |
| US6103894A (en) * | 1997-01-17 | 2000-08-15 | Sudzucker Aktiengesellschaft | Process for the hydrogenation of sugars |
| CN101597309A (en) * | 2009-06-30 | 2009-12-09 | 广西投资集团维科特生物技术有限公司 | A kind of method of producing hydroxyl isomaltulose by Palatinose |
| CN103055870A (en) * | 2013-01-24 | 2013-04-24 | 中国科学院青岛生物能源与过程研究所 | Nickel/copper catalyst and preparation method thereof, and method for directly preparing 1,2-hexanediol from cellulosan by using nickel/copper catalyst |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19911504B4 (en) * | 1999-03-16 | 2006-02-23 | Südzucker AG Mannheim/Ochsenfurt | Process for the industrial oxidation of alcohols, aldehydes or polyhydroxy compounds |
| WO2008077640A1 (en) * | 2006-12-22 | 2008-07-03 | Cargill, Incorporated | A process for the hydrogenation of a sugar or sugar mixture |
-
2015
- 2015-06-26 CN CN201510361774.1A patent/CN105001279B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4117173A (en) * | 1975-05-06 | 1978-09-26 | Suddeutsche Zucker-Aktiengesellschaft | Use of glucopyranosido-1,6-mannitol as a sugar substitute |
| US6103894A (en) * | 1997-01-17 | 2000-08-15 | Sudzucker Aktiengesellschaft | Process for the hydrogenation of sugars |
| CN101597309A (en) * | 2009-06-30 | 2009-12-09 | 广西投资集团维科特生物技术有限公司 | A kind of method of producing hydroxyl isomaltulose by Palatinose |
| CN103055870A (en) * | 2013-01-24 | 2013-04-24 | 中国科学院青岛生物能源与过程研究所 | Nickel/copper catalyst and preparation method thereof, and method for directly preparing 1,2-hexanediol from cellulosan by using nickel/copper catalyst |
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Denomination of invention: Preparation of isomaltulose alcohol from isomaltulose by catalytic hydrogenation Effective date of registration: 20220523 Granted publication date: 20180717 Pledgee: China Co. truction Bank Corp Zhaoqing branch Pledgor: ZHAOQING CORUSCATE BIOLOGICAL TECHNOLOGY CO.,LTD. Registration number: Y2022980006098 |
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