CN104447888B - A kind of preparation method and applications of psicose - Google Patents
A kind of preparation method and applications of psicose Download PDFInfo
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Abstract
The invention provides a kind of preparation method and applications of psicose.The preparation method is using glucose as raw material, using molybdate as catalyst, through catalyzed conversion, separating-purifying, produces the psicose of respective configuration.The method of the invention, it is main to include using chemical method, using glucose as raw material, crystal psicose product is prepared through the process such as chemical difference phase isomery, refined chromatographic purification, condensing crystallizing, technique is simple, and time-consuming short, reaction speed is fast, efficiency high, overcomes traditional enzyme process and prepares that the enzyme stability that D-psicose product is present is poor, the low problem of efficiency.
Description
Technical field
The invention belongs to technical field of functional sugar production, and in particular to a kind of preparation method and applications of psicose.
Background technology
D-Psicose is a kind of naturally occurring few rare sugar of nature, is a kind of new with special healthcare function
Type feature monose, its sugariness is equivalent to the 70% of sucrose, with high-dissolvability, extremely low calorie value and hypoglycemic reaction, eats
After be difficult by body metabolism, be nearly free from energy, it is corrosion-free, and with good food processing characteristic, food can be used as
The middle preferable substitute of sucrose.In August, 2011, FDA（FDA）It is universal public affairs to determine D-psicose
Recognize safety food（GRAS）, and can as food or food additives constituent, gathered around in meals, health care, medicine and other fields
Have broad application prospects.
On the production of D-psicose, someone is studied using D-Fructose as substrate, passes through D-Tag -3- epimerases
Biological enzyme conversion production D-Psicose, but product is the mixture of D-psicose and D-Fructose, and D-Fructose content
Higher, D-psicose purity is relatively low, is unfavorable for the application of D-psicose.Chinese patent《It is prepared by microbial transformation of D-levulose
The strain and method of D-psicose》（Publication number：CN101177672A）Disclose and a kind of obtained using being screened from the bed mud of fish pond
The method that the Rhodobacter transformation of D-levulose obtained prepares D-psicose, through 0.5-48h, contains D-psicose in conversion fluid
2—50g/L；Chinese patent《Utilize D-psicose production method of D-psicose epimerase》（Publication number：
CN101189332A）Disclose a kind of D-psicose epimerase production D-A Luo ketone for utilizing and being derived from Agrobacterium tumdfaciens
The method of sugar, main protein and D-Fructose using with amino acid sequence and with psicose 3- epimerase activities
Reaction production D-psicose；Chinese patent《The production technology of D-psicose》（Publication number：CN103333935A）Disclose
A kind of production technology of D-psicose using pure biological preparation method, including 50% sucrose, 1% recombination yeast, 1% glucose,
1%KH2PO4、1%K2HPO4·3H2O、0.5%MgSO4·7H2O and 45.5% water, the purity of products obtained therefrom can reach 98% and more than.
Carried out in the method for D-psicose made above in the way of biological enzyme, but it is the stability due to biology enzyme, activity, right
The factors such as the adaptability of environment influence, and the conversion ratio of the D-psicose typically produced is relatively low, and reaction speed is slow, time-consuming,
Low-quality D-psicose product can only be prepared, the demand of application market is can not meet.
The content of the invention
It is an object of the invention to provide a kind of preparation method of psicose, to solve to have problem in the prior art.
Psicose preparation method of the present invention, using glucose as raw material, using molybdate as catalyst, turns through catalysis
Change, separating-purifying, produce the psicose of respective configuration.
In the present invention, the psicose of respective configuration refers to that the configuration of psicose is consistent with the configuration of raw materials of glucose,
I.e. using D-Glucose as raw material, D-Psicose is prepared；Using L- glucose as raw material, L- psicoses are prepared.
Glucose, psicose are all monose, and its configuration is by the asymmetric carbon atom farthest from carbonyl carbon（No. 5 carbon atoms）
Configuration determine.In the present invention, glucose is converted into psicose under molybdate catalysis, and change is No. 3 carbon atoms
Configuration, the configuration of No. 5 farthest carbon atoms does not change, so using D-Glucose as raw material, preparing D-Psicose；
Using L- glucose as raw material, L- psicoses are prepared.
Present invention also offers application of the preparation method of the psicose in D-Psicose is prepared.
According to application of the present invention, mainly comprise the following steps：
（1）The preparation of feed liquid：The 10-30% D-Glucose aqueous solution is prepared, molybdate is added, regulation pH is 2.5-5.0；
（2）Catalyzed conversion：80-120 DEG C is heated to, insulation reaction 2-5 hours obtains the solution containing D-Psicose；
（3）Decolorization filtering：In at 70-80 DEG C, the solution containing D-Psicose is added into powder by the 1-15% of its amount of dry matter
Last activated carbon, insulated and stirred 30-40 minutes, is filtrated to get destainer；
（4）Electrodialysis desalination is refined：To destainer electrodialysis desalination is carried out to refine, make the electrical conductivity of destainer by
10000-20000us/cm is reduced to 100-500us/cm, obtains desalting refinement liquid；
（5）Concentrate chromatographic isolation：The technology being combined with steam raising concentration is concentrated using continuous film desalination is smart
Liquid processed is concentrated to dryness amount of substance concentration for 40-60%, is then separated using continuous chromatography, obtains amount of dry matter concentration for 5-
20%th, D-psicose purity is 70-90% solution；
（6）Condensing crystallizing：By step（5）It is 70- that obtained D-psicose solution, which is concentrated by evaporation to amount of dry matter concentration,
90%, crystal D-psicose product is obtained by organic solvent method decrease temperature crystalline, its content is 98.5-99.5%.
According to one of embodiment of the present invention, the molybdate is ammonium molybdate.
It is preferred that, the consumption of ammonium molybdate is the 1.0-10% of glucose.
According to another embodiment of the invention, step（1）The pH is 3.0-3.5.
Experiment is proved, when pH is in 3.0-3.5, and reaction conversion reaches peak, and reaction efficiency is higher.
According to a further embodiment of the present invention, the step（5）The separation temperature of continuous chromatography separation is 40-80 DEG C.
The method of the invention, it is main to include using chemical method, using glucose as raw material, through chemical difference phase isomery, essence
The processes such as chromatographic purification processed, condensing crystallizing prepare crystal psicose product, and technique is simple, and time-consuming short, reaction speed is fast,
Efficiency high, overcomes traditional enzyme process and prepares that the enzyme stability that D-psicose product is present is poor, the low problem of efficiency, meanwhile, color
The glucose cut liquid obtained after spectrum separation can back within " chemical isomerization reaction " process, again different as initiation material
D-psicose product is constituted, raw material availability is high, and production cost is low, be worth with preferable economic benefit and society generalization.
Brief description of the drawings
Fig. 1 is the HPLC chromatogram for the D-Psicose that embodiment 3 is prepared.
Embodiment
Influence of the material liquid pH of test example 1 to conversion ratio
Reaction condition：Using D-Glucose as raw material, with ammonium molybdate（Consumption is the 5% of D-Glucose quality）For catalyst,
100 DEG C, react under normal pressure, reaction time 120min determines the mass content of D-Psicose in reaction solution（Account for total dry matter
Percentage）, reaction result is as follows：
Glucose is easier to be converted into psicose in sour environment, when pH value is less than 2.5, the conversion ratio of psicose
Less than 28%, reaction efficiency is relatively low, brings very big pressure to subsequent purification, concentration, with pH rise, conversion ratio is also raised, when
PH is in 3.0-3.5, and reaction conversion reaches peak, and reaction efficiency is higher, and pH value continues to raise, and conversion ratio starts progressively to drop
Low, when pH is 5.0, conversion ratio, which maintains essentially in 30% or so, pH, to be continued to raise, and conversion ratio drastically declines, therefore in order to improve
Conversion ratio, the pH of isomerization reaction is preferably controlled in 2.5-5.0, especially 3.0-3.5.
Influence of the reaction time of test example 2 to conversion ratio
Reaction condition：Using D-Glucose as raw material, with ammonium molybdate（Consumption is the 5% of D-Glucose quality）For catalyst,
100 DEG C, react under the conditions of pH3.5, determine the mass content of D-Psicose in reaction solution（Account for the percentage of total dry matter）, instead
Answer result as follows：
Learnt from analysis of experimental data, the conversion ratio of psicose increases with the increase in reaction time, in reaction
Between when reaching 2 hours, drastically accelerate, reaction conversion ratio is raised rapidly, when reacted between when reaching 4 hours, reaction tends to be steady,
Balance is basically reached, reaction efficiency and conversion ratio is considered, it is 2-5h, especially 2-4h preferably to select the reaction time.
Influence of the catalyst amount of test example 3 to conversion ratio
Reaction condition：Using D-Glucose as raw material, using molybdate as catalyst, 100 DEG C, pH3.5, anti-under condition of normal pressure
Should, reaction time 120min determines the mass content of D-Psicose in reaction solution（Account for the percentage of total dry matter）, reaction knot
Fruit is as follows：
Learnt from analysis of experimental data, the conversion ratio of psicose increases, molybdic acid with the increase of co-catalyst consumption
When ammonium consumption is 0.5%, conversion ratio is relatively low, reacts not thorough, when ammonium molybdate consumption reaches 1.0%, the conversion ratio of psicose can
To reach more than 25%, when the consumption of ammonium molybdate reaches 5.0%, reaction more thoroughly, continues to increase the consumption of ammonium molybdate, conversion ratio
Lifting amplitude is smaller, tends to be steady substantially.Control experiment is carried out using sodium molybdate, ammonium molybdate simultaneously, ammonium molybdate is to psicose
Influence is larger, and the conversion ratio of reaction is higher, considers production cost and follow-up refining and edulcoration, catalyst is made from ammonium molybdate,
Its consumption is preferably selected in 1.0-10%.
Embodiment one
1st, solution is prepared：1000g glucose is taken, 9000g pure water is added, it is 10% to be configured to mass percent mass concentration
Glucose solution 10000g.
2nd, chemical isomerization reacts：Ammonium molybdate 10g is added by the 1% of glucose amount of dry matter, the pH value of regulation solution is 2.5,
80 DEG C are warming up to, insulation reaction 2 hours makes glucose isomerase turn to D-psicose, obtains D-psicose and glucose
Mixed liquor, its amount of dry matter concentration is that the 8%, purity of D-psicose is that 28%, electrical conductivity is 10000us/cm.
3rd, decolorization filtering：By isomery liquid at 70 DEG C, Powdered Activated Carbon 10g is added by the 1% of its amount of dry matter, insulation is stirred
Mix after 30 minutes, isomery destainer is filtrated to get with flame filter press, its index is：Amount of dry matter concentration is 8%, D-A Luo ketone
The purity of sugar is that 28.56%, electrical conductivity is 10050us/cm.
4th, electrodialysis desalination is refined：By isomery destainer by membrane area be 40m2Electrodialysis plant system, control electricity
Current density is 10mA/cm2, feed liquid rate of circulating flow be 15L/h, pole velocity of water circulation be 60L/h, equipment running temperature be 20 DEG C,
Continuous circular flow 4 hours, makes the electrical conductivity of isomery destainer be reduced to 100us/cm by 10050us/cm, reaches refined purification
The purpose of isomery destainer.
5th, chromatographic isolation is concentrated：Use continuous film concentration technology technology will purify isomery liquid be concentrated to dryness amount of substance concentration for
15%, then use triple effect steam vaporizer that feed liquid is concentrated to dryness into amount of substance concentration and be passed through for 40%, finally equipped with calcium type chromatogram
In the Simulation moving bed apparatus system of separation resin, it is 40 DEG C to control separation temperature, and feeding liquid is separated into D-psicose and evaporated
Divide liquid and glucose cut liquid, the index of wherein D-psicose cut liquid is：Amount of dry matter concentration is 5%, D-psicose
Purity be 90%；The index of glucose cut liquid is：Amount of dry matter concentration is that the purity of 20%, glucose is 80%.Glucose evaporates
Divide liquid to back within " chemical isomerization reaction " process, re-used as initiation material.
6th, condensing crystallizing：The D being collected into-psicose cut liquid is concentrated to dryness material using continuous film condensing device
It is 15% to measure concentration, then uses quadruple effect steam vaporizer to be concentrated by evaporation to amount of dry matter concentration as 70%, by adding alcohol, drop
Temperature crystallization obtains crystal D-psicose product, and its content is 99.5%.
Embodiment two
1st, solution is prepared：3000g glucose is taken, 7000g pure water is added, it is 30% to be configured to mass percent mass concentration
Glucose solution 10000g.
2nd, chemical isomerization reacts：Ammonium molybdate 300g is added by the 10% of glucose amount of dry matter, the pH value of regulation solution is
5.0,120 DEG C are warming up to, insulation reaction 5 hours makes glucose isomerase turn to D-psicose, obtains D-psicose and Portugal
The mixed liquor of grape sugar, its amount of dry matter concentration is that the 28%, purity of D-psicose is that 35%, electrical conductivity is 20000us/cm.
3rd, decolorization filtering：By isomery liquid at 80 DEG C, Powdered Activated Carbon 450g, insulation are added by the 15% of its amount of dry matter
After stirring 40 minutes, isomery destainer is filtrated to get with flame filter press, its index is：Amount of dry matter concentration is 28%, D-Ah
The purity of Lip river ketose is that 35.27%, electrical conductivity is 20000us/cm.
4th, electrodialysis desalination is refined：By isomery destainer by membrane area be 40m2Electrodialysis plant system, control electricity
Current density is 20mA/cm2, feed liquid rate of circulating flow be 25L/h, pole velocity of water circulation be 100L/h, equipment running temperature be 35 DEG C,
Continuous circular flow 10 hours, makes the electrical conductivity of isomery destainer be reduced to 500us/cm by 20000us/cm, reaches refined net
Change the purpose of isomery destainer.
5th, chromatographic isolation is concentrated：Use triple effect steam vaporizer that feed liquid is concentrated to dryness into amount of substance concentration for 60%, be passed through dress
In the Simulation moving bed apparatus system for having lead-type chromatographic isolation resin, control separation temperature be 80 DEG C, feeding liquid be separated into D-
Psicose cut liquid and glucose cut liquid, the index of wherein D-psicose cut liquid is：Amount of dry matter concentration be 20%,
The purity of D-psicose is 70%；The index of glucose cut liquid is：Amount of dry matter concentration is that the purity of 50%, glucose is
99%.Glucose cut liquid backs within " chemical isomerization reaction " process, is re-used as initiation material.
6th, condensing crystallizing：The D being collected into-psicose cut liquid is concentrated by evaporation to dry using quadruple effect steam vaporizer
Amount of substance concentration is 90%, by adding alcohol, and decrease temperature crystalline obtains crystal D-psicose product, and its content is 98.5%.
Embodiment three
1st, solution is prepared：2000g glucose is taken, 8000g pure water is added, it is 20% to be configured to mass percent mass concentration
Glucose solution 10000g.
2nd, chemical isomerization reacts：Ammonium molybdate 100g is added by the 5% of glucose amount of dry matter, the pH value of regulation solution is
4.0, be warming up to 100 DEG C, insulation reaction 3.5 hours makes glucose isomerase turn to D-psicose, obtain D-psicose with
The mixed liquor of glucose, its amount of dry matter concentration is that the 18%, purity of D-psicose is that 32%, electrical conductivity is 15000us/cm.
3rd, decolorization filtering：By isomery liquid at 75 DEG C, Powdered Activated Carbon 200g, insulation are added by the 10% of its amount of dry matter
After stirring 35 minutes, isomery destainer is filtrated to get with flame filter press, its index is：Amount of dry matter concentration is 18%, D-Ah
The purity of Lip river ketose is that 32.17%, electrical conductivity is 15000us/cm.
4th, electrodialysis desalination is refined：By isomery destainer by membrane area be 40m2Electrodialysis plant system, control electricity
Current density is 15mA/cm2, feed liquid rate of circulating flow be 20L/h, pole velocity of water circulation be 80L/h, equipment running temperature be 30 DEG C,
Continuous circular flow 7 hours, makes the electrical conductivity of isomery destainer be reduced to 300us/cm by 15000us/cm, reaches refined purification
The purpose of isomery destainer.
5th, chromatographic isolation is concentrated：Use quadruple effect steam vaporizer that feed liquid is concentrated to dryness into amount of substance concentration for 50%, be passed through dress
In the Simulation moving bed apparatus system for having sodium form chromatographic isolation resin, control separation temperature be 60 DEG C, feeding liquid be separated into D-
Psicose cut liquid and glucose cut liquid, the index of wherein D-psicose cut liquid is：Amount of dry matter concentration be 13%,
The purity of D-psicose is 80%；The index of glucose cut liquid is：Amount of dry matter concentration is that the purity of 35%, glucose is
90%.Glucose cut liquid backs within " chemical isomerization reaction " process, is re-used as initiation material.
6th, condensing crystallizing：The D being collected into-psicose cut liquid is concentrated by evaporation to dry using five effect steam vaporizers
Amount of substance concentration is 80%, adds alcohol, takes crystallization massecuite, massecuite decrease temperature crystalline is obtained into crystal D-psicose product, its
Content is 99.0%.
7th, using high performance liquid chromatograph, the purity of D-Psicose is detected, testing conditions are：Chromatographic column：
SUPELCOGEL Ca（Calcium type）Resin type sugar post, mobile phase is ultra-pure water, and detector is differential refraction detector, D- A Luo ketone
Sugared reference substance is that the mass content that reference substance is D-Psicose in control, dry is 95.5%, and chromatogram is as shown in Figure 1.
Claims (7)
1. a kind of preparation method of psicose, it is characterised in that mainly comprise the following steps：
(1) preparation of feed liquid：10-30% D/W is prepared, molybdate is added, regulation pH is 2.5-5.0；
(2) catalyzed conversion：80-120 DEG C is heated to, insulation reaction 2-5 hours obtains the solution containing psicose；
(3) decolorization filtering：In at 70-80 DEG C, the solution containing psicose is added into powder by the 1-15% of its amount of dry matter and lived
Property charcoal, insulated and stirred 30-40 minutes is filtrated to get destainer；
(4) electrodialysis desalination is refined：Electrodialysis desalination is carried out to destainer to refine, and makes the electrical conductivity of destainer by 10000-
20000us/cm is reduced to 100-500us/cm, obtains desalting refinement liquid；
(5) chromatographic isolation is concentrated：Concentrated using continuous film and steam raising concentrates the technology that is combined by desalting refinement liquid
Amount of substance concentration is concentrated to dryness for 40-60%, is then separated using continuous chromatography, amount of dry matter concentration is obtained for 5-
20%th, psicose purity is 70-90% solution；
(6) condensing crystallizing：It is 70-90% that the psicose solution that step (5) is obtained, which is concentrated by evaporation to amount of dry matter concentration, is led to
Cross organic solvent method decrease temperature crystalline and obtain crystal psicose product, its content is 98.5-99.5%.
2. application of the preparation method of psicose described in claim 1 in D-Psicose is prepared.
3. application as claimed in claim 2, it is characterised in that mainly comprise the following steps：
(1) preparation of feed liquid：The 10-30% D-Glucose aqueous solution is prepared, molybdate is added, regulation pH is 2.5-5.0；
(2) catalyzed conversion：80-120 DEG C is heated to, insulation reaction 2-5 hours obtains the solution containing D-Psicose；
(3) decolorization filtering：In at 70-80 DEG C, the solution containing D-Psicose is added into powder by the 1-15% of its amount of dry matter
Activated carbon, insulated and stirred 30-40 minutes, is filtrated to get destainer；
(4) electrodialysis desalination is refined：Electrodialysis desalination is carried out to destainer to refine, and makes the electrical conductivity of destainer by 10000-
20000us/cm is reduced to 100-500us/cm, obtains desalting refinement liquid；
(5) chromatographic isolation is concentrated：Concentrated using continuous film and steam raising concentrates the technology that is combined by desalting refinement liquid
Amount of substance concentration is concentrated to dryness for 40-60%, is then separated using continuous chromatography, amount of dry matter concentration is obtained for 5-
20%th, D-Psicose purity is 70-90% solution；
(6) condensing crystallizing：It is 70-90% that the D-Psicose solution that step (5) is obtained, which is concentrated by evaporation to amount of dry matter concentration,
Crystal D-Psicose product is obtained by organic solvent method decrease temperature crystalline, its content is 98.5-99.5%.
4. application as claimed in claim 3, it is characterised in that the molybdate is ammonium molybdate.
5. application as claimed in claim 4, it is characterised in that the consumption of ammonium molybdate is the 1.0-10% of glucose.
6. application as claimed in claim 3, it is characterised in that step (1) described pH is 3.0-3.5.
7. application as claimed in claim 3, it is characterised in that the separation temperature of step (5) the continuous chromatography separation is 40-80
℃。
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| CN105219756A (en) * | 2015-07-17 | 2016-01-06 | 江南大学 | A kind of L-rhamnulose-1-phosphate aldolase is catalyzing and synthesizing the application in rare sugar |
| KR102072695B1 (en) * | 2016-12-08 | 2020-03-02 | 주식회사 삼양사 | Method of preparing psicose with recycling |
| KR101988441B1 (en) * | 2016-12-27 | 2019-06-12 | 주식회사 삼양사 | Method of purification allulose |
| FR3061414B1 (en) | 2017-01-05 | 2021-07-16 | Roquette Freres | D-ALLULOSE CRYSTALLIZABLE SYRUPS |
| FR3061415B1 (en) * | 2017-01-05 | 2021-07-16 | Roquette Freres | NON-CRYSTALLIZABLE D-ALLULOSE SYRUPS |
| FR3061413B1 (en) * | 2017-01-05 | 2021-08-27 | Roquette Freres | PROCESS FOR MANUFACTURING D-ALLULOSE CRYSTALS |
| CN106929545A (en) * | 2017-02-14 | 2017-07-07 | 榆林学院 | A kind of vegetables residue as resources Application way |
| KR102004940B1 (en) * | 2017-06-30 | 2019-07-29 | 주식회사 삼양사 | production of allulose as sweetener |
| CN109022625A (en) * | 2018-09-18 | 2018-12-18 | 上海立足生物科技有限公司 | A method of producing the D-Psicose of concentration |
| CN108866247A (en) * | 2018-09-18 | 2018-11-23 | 上海立足生物科技有限公司 | The method and apparatus that continuous large-scale separation prepares D-Psicose |
| MX2022014802A (en) | 2020-05-27 | 2023-01-16 | Savanna Ingredients Gmbh | Crystallization of allulose under reduced pressure. |
| EP4211142A1 (en) | 2020-09-07 | 2023-07-19 | Savanna Ingredients GmbH | Extrusion process for the preparation of a solid allulose composition |
| EP4000419A1 (en) | 2020-11-23 | 2022-05-25 | Savanna Ingredients GmbH | Drying of allulose crystals |
| CN114456215A (en) * | 2022-03-04 | 2022-05-10 | 河南中大恒源生物科技股份有限公司 | D-psicose crystal and preparation method thereof |
| CN115028667A (en) * | 2022-06-10 | 2022-09-09 | 山东星光首创生物科技有限公司 | Preparation method of psicose with low water activity and psicose |
| WO2024047122A1 (en) | 2022-09-01 | 2024-03-07 | Savanna Ingredients Gmbh | Process for the preparation of a particulate allulose composition |
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| CN101851689B (en) * | 2010-06-11 | 2012-01-11 | 谭卫星 | Preparation process of D-mannose |
| CN101891773B (en) * | 2010-07-15 | 2012-07-25 | 山东福田药业有限公司 | Process for preparing L-ribose |
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