CN101215580B - Method for preparing D-mannitol from konjak refined powder - Google Patents
Method for preparing D-mannitol from konjak refined powder Download PDFInfo
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Abstract
The invention relates to a process for preparing D-mannitol, which uses konjaku flour as raw material. The process for preparation comprises following steps: selecting konjaku fine flour whose glucomannan content is more than 70-80%, firstly, using beta-mannase to hydrolyze the konjaku fine flour under 45-50 DEG C, secondly, using mineral acid 1-3%(V/V) as catalyst to hydrolyze oligosaccharide inhydrolysate of the first step and obtain mannose-glucose mixture, obtaining the mixture whose mannose content is 58-70% through refining, hydrogenating, and then generating mannitol from the mannose, wherein the mannitol content in mixed alcohol is more than 60%, D-mannitol product can be obtained through refining again and drying, and the yield of the mannitol is more than 50% of total material. The invention is a method for producing the D-mannitol with simple operation and high yield and the raw material which is adopted is renewable natural resource.
Description
(1) technical field
The present invention relates to the method that a kind of biochemical industry prepares D-N.F,USP MANNITOL, particularly a kind of method of utilizing konjaku powder to prepare D-N.F,USP MANNITOL.
(2) background technology
Rhizoma amorphophalli glucomannan (Konjac Glucomannan) is the polymer resource of a kind of very abundant natural reproducible after starch and Mierocrystalline cellulose.Biodegradable, heavy water-soluble, have good physicochemical property, be the good raw material of chemical industry, medicine, food, functional materials.
D-N.F,USP MANNITOL (D-mannitol) molecular weight 182.17, white needle-like crystals or crystalline powder, nothing is smelt, and is pleasantly sweet.Density 1.489g/cm3.166～170 ℃ of fusing points.290～295 ℃ (15.7 * 103Pa) of boiling point.Specific rotation+23～+ 24 degree, deliquescence is not soluble in hot water, hot ethanol, diluted acid, rare solution that subtracts, and is insoluble in cold ethanol, is insoluble to ether.Sugariness is suitable, and heat is low, has no side effect, and has nothing to do with Regular Insulin the human body metabolism, does not improve blood glucose value, and unlikely carious tooth can be used for one of sweeting agent of especial patient such as mellitus, adiposis patient, also is used on the food service industry such as chewing gum.Solubility with temperature raises and increases in water.Can be under alkaline condition by water generation reaction dissolubility salt such as copper, lead, cobalts.Mainly as the raw material of medicine industry, be used to prepare diuretic(s), dewatering agent, disaccharide and substitute agent, transfusion usefulness, medicine vehicle etc.Plastics industry is as plasticizer for polyvinyl chloride.Organic synthesis industry is as the raw material of making three rosin esters and artificial glycerine resin.As chemical reagent, measure hydroxyl mark Huaihe River reagent as metal shadowing agent, organic microanalysis, be used for calibrating and measure boron, germanium, kidney function test and haploid breeding.Be a kind of natural hexose alcohol, with sorbyl alcohol be isomers.Can obtain the N.F,USP MANNITOL and the sorbyl alcohol of equivalent after the fructose hydrogenation, or obtain the N.F,USP MANNITOL of 100%-102% after the complete hydrogenation of seminose.
In existing industrial production technology, preparation N.F,USP MANNITOL mainly is to be that raw material is produced with glucose, sucrose, sea-tangle etc.Disclose a kind of method of from sea-tangle, extracting N.F,USP MANNITOL like Chinese patent 200510044407.5, characteristics are the fresh sea-tangle choppings of selecting harvesting for use, and the water logging that adds 2 times of sea-tangle weight was steeped 30～50 minutes; Get soak solution and add alkali adjustment pH value, static floating mistake filters the clear liquid that contains iodine and N.F,USP MANNITOL; Clear liquid produces free-iodine through the acidifying oxidation; Through exchange resin absorption, iodine extracts; After carrying soak solution behind the iodine and adding the adjusting PH with base value, evaporation concentration is separated out deposition, again decrease temperature crystalline behind the salinity is separated out in the feed liquid evaporation, centrifugal, wash the N.F,USP MANNITOL work in-process; Work in-process adding distil water heating for dissolving adds activated carbon decolorizing, the filtering gac, dilution filtrating, desalination, concentrating under reduced pressure again, crystallisation by cooling, spinning, dry refining N.F,USP MANNITOL.This method because the PT is long, energy consumption is big, the pollution of yield low environment is big etc. is eliminated.
With sucrose is the synthetic N.F,USP MANNITOL of raw material; Sucrose hydrolysis is obtained the glucose and the fructose of equivalent; Decolouring, carry out the hydrogenation result and obtain N.F,USP MANNITOL and account for and mix pure total amount about 25% from hand over handling; Sorbyl alcohol accounts for 75%, through decolouring, IX, concentrate, operations such as crystallization, separation, drying obtain the N.F,USP MANNITOL product at last, yield is at 17-20%.This method main drawback is that yield is low, produces a large amount of sorbyl alcohol sub products at a low price.Also have through multistep and handle the yield improved N.F,USP MANNITOL; Announced with sucrose to be the method for feedstock production N.F,USP MANNITOL like Chinese patent 200510018565.3; To carry out enzyme isomerize reaction through the simulation moving-bed glucose component that is rich in that carries out obtaining after fructose glucose separates; The epimerized sugar liquid that obtains is rich in the fructose component with simulation moving-bed isolating through refining from handing over Nulomoline again; The fructose component that is rich in after merging is carried out hydrogenation reaction, and the mixed alcoholic liquid that obtains is handled through routine and is obtained the N.F,USP MANNITOL product.Use method of the present invention to be feedstock production N.F,USP MANNITOL with sucrose; Sucrose hydrolysis after simulation moving-bed resulting separation be rich in the glucose component; Transform generation fructose through enzyme isomerize reaction; Make to be rich in the fructose component and to be rich in the glucose component all to have obtained effective utilization, thereby make the yield of N.F,USP MANNITOL can reach 42%.
It is raw material production N.F,USP MANNITOL method that U.S. Pat 4292451 discloses with glucose, utilizes ammonium molybdate catalytic isomerization glucose to become seminose hydrogenation preparing N.F,USP MANNITOL then, in 50～60% glucose solution, adds 0.25～0.5% ammonium molybdate; PH3～4; Temperature is at 90～100 ℃, and last yield is about 35%, and yield is low; Production cycle is long, and certain environmental pollution is arranged; It is raw material that Chinese patent 03143297.2 discloses with glucose, and glucose solution under 60～160 ℃ of the temperature, is a catalyzer with the molybdate under acidic conditions, and part is converted into seminose; Add the glucose crystal seed to above-mentioned gained mixed solution, the part glucose crystallization in the solution is separated out; Through the glucose isomerase post with crystallization separate out the back mother liquid obtained in remaining glucose moiety be converted into fructose, obtain the mixed solution of glucose, seminose and fructose; With the above-mentioned mixed solution hydrogenation that contains glucose, seminose and fructose; Make the alcohol mixture solution that contains sorbyl alcohol and N.F,USP MANNITOL, this mixed solution is through crystallization, refining N.F,USP MANNITOL crystal, and a little methods adopt crystallizations and enzyme isomerate process; The crystallisation process time is long; Need 24～48 hours, simultaneously because seminose and molybdenum have restraining effect to enzyme, so will consume a large amount of expensive enzymes.This method integrated chemical method and biological enzyme, long, envrionment conditions of production cycle require that lotus is carved, the zymin cost is high, because seminose and partly metal-salt exist the enzyme life-span shortened greatly, and this salt pair environment has adverse influence.Chinese patent 03134955.2 has announced that glucose obtains seminose-glucose mixture through epimerization reaction under acidic conditions; Carrying out seminose-glucose with simulation moving-bed device separates; In separation temperature is 40～85 ℃, is sorbent material, is under the condition of eluent with water with calcium type Zeo-karb, can obtain being rich in the glucose component continuously and be rich in the seminose component; The former can repeat epimerization reaction; The latter can generate N.F,USP MANNITOL through hydrogenation, and the mannitol content that mixes behind the hydrogenation of gained in the alcohol reaches more than 75%, after crystallization, centrifugal, drying, obtains the N.F,USP MANNITOL product again.This method adopts simulation moving-bed separation purification seminose, though yield is higher, facility investment money is big, the lock out operation step is many, troublesome poeration, and it is unfavorable that calcium type weak point resin life is used in separation, regenerating resin consumes a large amount of acid base pair environment.All exist operation to repeat repeatedly in the technology of above-mentioned public reported, shortcoming such as facility investment is big, yield is not high, environmental pollution is big.
(3) summary of the invention
The purpose of this invention is to provide a kind of method of utilizing konjaku powder to prepare D-N.F,USP MANNITOL, its technology is simple, easy to operate, raw material is easy to get, D-N.F,USP MANNITOL yield high.
The present invention realizes above-mentioned purpose through following technical scheme: a kind of method of utilizing konjaku powder to prepare D-N.F,USP MANNITOL is provided, and this method comprises the steps:
(1) macromolecule polysaccharidase of selecting for use glucose and seminose in the konjac glucomanna molecule in the konjaku powder to be formed by connecting through β-1,4 glycosidic link,
(2) earlier with beta-mannase enzymic hydrolysis saccharan, obtain X
1Solution, X
1Solution is the mixed solution of monose, oligose,
(3) then use mineral acid hydrolysis X
1Solution obtains X
2Solution, X
2Solution is the muscovado liquid of glucose and seminose,
(4) regulate acid hydrolysis liquid with sodium hydroxide solution,
(5) with X
2Solution filters, decolorizing with activated carbon, IX, and vacuum concentration obtains X
3Liquid concentrator, X3 liquid concentrator are the concentrated muscovado liquid of glucose and seminose,
(6) with X
3Liquid concentrator hydrogenation obtains the mixed alcoholic solution of N.F,USP MANNITOL and sorbyl alcohol, and Crystallization Separation obtains N.F,USP MANNITOL finished product and liquid sorbitol,
The control condition of aforesaid method step is:
(1) to account for konjaku powder content be more than the 70-80% to the konjac glucomanna in the used konjaku powder,
(2) beta-mannase enzymic hydrolysis saccharan condition is: the beta-mannase enzyme concn is 0.002-0.004% (W/W), and temperature is 45-50 ℃, and the pH value is 5～6,4～6 hours time,
(3) mineral acid hydrolysis X
1Solution condition is: inorganic acid concentration is at 1～5% (V/V), pH2～2.5 pressure, 0.1～0.15MPa, and temperature is at 120～130 ℃, and hydrolysis 30-90 minute,
(4) regulate acid hydrolysis liquid pH to 6～7 with the sodium hydroxide solution of 1～5% (V/V),
(5) used discoloring agent is an activated carbon, and institute's spent ion exchange resin is that general sugar use resin, and vacuum concentration mixing sugar concentration arrives 45-55% (W/W),
(6) hydrogenation conditions is: pH value 7.5～9.5, temperature are 140～160 ℃, and pressure is 8.0～10.5MPa, and the time is 50～80 minutes, and catalyzer Raney's nickel consumption is 5～10% (W/W).
Said mineral acid hydrolysis concentration is preferably at 1～3% (V/V).
The concrete operations step is following:
Elder generation's compound concentration is the beta-mannase enzyme aqueous solution of 0.002～0.004% (W/W); Heated soln makes temperature rise to 45～50 ℃ then; Be 150～160 rev/mins of stirrings with rotating speed on one side,, account for solution 35～45% (W/W) up to the konjaku powder total amount Yi Bian add konjaku powder; Stop to add konjaku powder, improve rotating speed to 250～270 rev/min.Adding concentration is the mineral acid of 1～5% (V/V), in pH2～2.5, pressure 0.1-0.15MPa, 120～130 ℃ of temperature, hydrolysis 30-90 minute, after be cooled to 70～50 ℃, filter cleaner is got filtrating, obtains containing the muscovado solution of 58～70% seminoses.Regulate pH value to 6～7 with 1～5mol/l sodium hydroxide solution, using decolorizing with activated carbon, IX, being concentrated in vacuo to concentration is 45～55% (W/W).Regulate pH to 7.5～9.5 with sodium hydroxide again, deliver to and carry out hydrogenation in the hydrogenation still.Catalyzer uses Raney's nickel, and consumption is 5～10% (W/W), and pressure is 8.0～10.5Mpa, and temperature is at 140～160 ℃, and the time is 50～80 minutes, obtains containing 60～65% N.F,USP MANNITOL (accounting for hexa-atomic mixed alcohol).Mixed alcohol obtains purity after making with extra care be 99.3% above D-N.F,USP MANNITOL product, and fusing point is at 165～167 ℃.The yield (accounting for the total amount that feeds intake) of final N.F,USP MANNITOL is more than 50%.
Know-why: cubical expansion was big 50～80 times after konjaku powder absorbed water in water; General 1 gram konjaku powder is dissolved in 100 milliliters water or the normal temperature acid solution will become the hydrating solution that gel can't obtain the high density konjaku powder; Its hydrolysis is also incomplete generally speaking simultaneously, and partly hydrolysis generates seminose, glucose and oligose.Selecting suitable hydrolyst and hydrolysis method is the key that the konjaku powder complete hydrolysis becomes seminose and glucose.It is complete that single stage method is difficult to hydrolysis, during singly with beta-mannase enzymic hydrolysis konjaku powder, has 10～15% konjac glucomannas not to be hydrolyzed, and hydrolysis concentration is low, has to 10% left and right sides liquid glucose.If list is used acid hydrolysis, sour consumption is very big, and acid is 1: 4 with the ratio of water, and aftertreatment is pretty troublesome, at first uses a large amount of alkali neutralizing acids, desalination again, concentrates etc.And the present invention adopts biology and Chemical bond to be hydrolyzed, and obtains good effect.
The present invention compares with existing working method, has following characteristics:
1. adopt beta-mannase enzymic hydrolysis saccharan earlier, use the mineral acid hydrolysis oligose again, work simplification, processing ease.
2. the yield (accounting for the total amount that feeds intake) of final N.F,USP MANNITOL is more than 50%, and yield is high, and product reaches the requirement of bulk drug.
3. utilize konjaku powder to prepare D-N.F,USP MANNITOL, raw material is easy to get, and belongs to the renewable energy resource.
4. technology is without chemical isomerization and chromatographic separation, and is low in the pollution of the environment, with short production cycle.
(4) embodiment
Below through specific embodiment technical scheme of the present invention is further described.
Embodiment 1
Take by weighing the konjaku powder 100.0g that contains konjac glucomanna 75%, under 170 rev/mins of stirrings, slowly be added on the beta-mannase enzyme aqueous solution of 240ml concentration 0.002% (W/W), temperature is 45 ℃, and pH is 6.0, hydrolysis 6 hours.Add the back and bring up to 285 rev/mins to rotating speed, using concentration is that 0.5% sulfuric acid is transferred pH to 2.1, and the pressure that raises immediately is to 0.15Mpa; Keep this state release after 35 minutes after temperature rises to 126 ℃, cool to 65 ℃, obtain the muscovado filtrating 300ml of reddish-brown with 120 order filtering net filter cleaners; Regulate muscovado liquid pH value to 6.0 with 5% (V/V) sodium hydroxide solution; Be faint yellow with decolorizing with activated carbon to solution, carry out IX, vacuum concentration to 45% then.Performance liquid chromatography detects and concentrates that mannose content is 61.83% in the mixed sugar liquid.Transfer the pH to 8.5 that concentrates mixed sugar liquid with 1% sodium hydroxide solution, muscovado liquid is placed hydrogenation in the hydrogenation still, add 7.5% Raney's nickel, hydrogenation temperature is 140 ℃, and pressure 8.0MPa obtains N.F,USP MANNITOL and sorbyl alcohol mixed alcoholic liquid after 65 minutes time.Mixed alcoholic liquid obtains mixing alcohol through decolouring, IX, concentrated.Using performance liquid chromatography to record the content that mixes N.F,USP MANNITOL in the alcohol is 62.28%.After crystallization, obtain purity and be 99.9% D-N.F,USP MANNITOL 51.6g, the N.F,USP MANNITOL total recovery is 51.6%, and the sorbyl alcohol yield is 33.5%.
Embodiment 2
Take by weighing the konjaku powder 120.0g that contains konjac glucomanna 70%, under 180 rev/mins of stirrings, slowly be added on the beta-mannase enzyme aqueous solution of 250ml concentration 0.003% (W/W), temperature is 50 ℃, and pH is 5.5, hydrolysis 5 hours.Add the back and bring up to 270 rev/mins to rotating speed, transfer pH to 2.3 with 2.5% (V/V) hydrochloric acid, the pressure that raises immediately is to 0.12Mpa; Keep this state release after 45 minutes after temperature rises to 124 ℃, cool to 60 ℃, obtain the muscovado filtrating 350ml of reddish-brown with 120 order filtering net filter cleaners; Regulate muscovado liquid pH value to 6.5 with 2.5% (V/V) sodium hydroxide solution; Be faint yellow with decolorizing with activated carbon to solution, IX then, vacuum concentration to 50%.Use performance liquid chromatography to detect to concentrate that mannose content is 64.5% in the muscovado liquid.Transfer the pH to 8.0 that concentrates muscovado liquid with 3% sodium hydroxide solution, muscovado liquid is placed in the hydrogenation still, add 10% Raney's nickel, hydrogenation temperature is 150 ℃, obtains N.F,USP MANNITOL and sorbyl alcohol after 65 minutes pressure 10.5MPa time and mixes alcoholic solution.Mix alcohol through decolouring, IX, concentrated, using performance liquid chromatography to record the content that mixes N.F,USP MANNITOL in the alcohol is 66.7%.After crystallization, obtain purity and be 99.7% D-N.F,USP MANNITOL 63.1g, the N.F,USP MANNITOL total recovery is 52.6%, and the sorbyl alcohol yield is 34.6%.
Embodiment 3
Take by weighing the konjaku powder 150.0g that contains konjac glucomanna 78%, under 150 rev/mins of stirrings, slowly be added on the beta-mannase enzyme aqueous solution of 320ml concentration 0.004% (W/W), temperature is 50 ℃, and pH is 5.0, hydrolysis 4 hours.Add the back and bring up to 260r/min to rotating speed, transfer pH to 2.5 with 1.0% (V/V) hydrochloric acid, the power of boosting immediately is to 0.1Mpa; High-temperature to 121 ℃ keeps this state release after 50 minutes, cools to 50 ℃ with 120 order filtering net filter cleaners; Obtain the muscovado filtrating 370ml of reddish-brown, regulate muscovado liquid pH value to 6.8, be faint yellow with decolorizing with activated carbon to solution with 1.0% (V/V) sodium hydroxide solution; IX then, vacuum concentration to 50%.Performance liquid chromatography detects and concentrates that mannose content is 65.1% in the muscovado liquid.Transfer the pH to 8.5 that concentrates muscovado liquid with 5% sodium hydroxide solution, muscovado liquid is placed in the hydrogenation still, add 5% Raney's nickel, pressure is 9.0Mpa, and hydrogenation temperature is 160 ℃, obtains N.F,USP MANNITOL and sorbyl alcohol after 80 minutes time and mixes alcoholic solution.Mix alcohol through decolouring, IX, concentrated, using performance liquid chromatography to record the content that mixes N.F,USP MANNITOL in the alcohol is 60.9%.After crystallization, obtain purity and be 99.8% D-N.F,USP MANNITOL 76.4g, the N.F,USP MANNITOL total recovery is 50.9%, sorbyl alcohol yield 35%.
Claims (2)
1. a method of utilizing konjaku powder to prepare D-N.F,USP MANNITOL is characterized in that this method comprises the steps:
(1) select for use glucose and seminose in the konjac glucomanna molecule wherein to be connected to form the konjaku powder of macromolecule polysaccharidase through β-1,4 glycosidic link,
(2) earlier with beta-mannase enzymic hydrolysis konjaku powder, obtain X
1Solution, X
1Solution is the mixed solution of monose, oligose,
(3) then use mineral acid hydrolysis X
1Solution obtains X
2Solution, X
2Solution is the muscovado liquid of glucose and seminose,
(4) regulate acid hydrolysis liquid with sodium hydroxide solution,
(5) with X
2Solution filters, decolorizing with activated carbon, IX, and vacuum concentration obtains X
3Liquid concentrator, X
3Liquid concentrator is the concentrated muscovado liquid of glucose and seminose,
(6) with X
3Liquid concentrator hydrogenation obtains the mixed alcoholic solution of N.F,USP MANNITOL and sorbyl alcohol, and Crystallization Separation obtains N.F,USP MANNITOL finished product and liquid sorbitol,
The control condition of aforesaid method step is:
(1) to account for konjaku powder content be 70-80% to the konjac glucomanna in the used konjaku powder,
(2) beta-mannase enzymic hydrolysis konjaku powder condition is: the beta-mannase enzyme concn is 0.002-0.004% (W/W), and temperature is 45-50 ℃, and the pH value is 5～6,4～6 hours time,
(3) mineral acid hydrolysis X1 solution condition is: inorganic acid concentration is at 1～5% (V/V), pH2～2.5 pressure, 0.1～0.15MPa, and temperature is at 120～130 ℃, and hydrolysis 30-90 minute,
(4) regulate acid hydrolysis liquid pH to 6～7 with the sodium hydroxide solution of 1～5% (V/V),
(5) used discoloring agent is an activated carbon, and institute's spent ion exchange resin is that general sugar is used resin, and vacuum concentration mixing sugar concentration arrives 45-55% (W/W),
(6) hydrogenation conditions is: pH value 7.5～9.5, temperature are 140～160 ℃, and pressure is 8.0～10.5MPa, and the time is 50～80 minutes, and catalyzer Raney's nickel consumption is 5～10% (W/W).
2. the method for utilizing konjaku powder to prepare D-N.F,USP MANNITOL according to claim 1 is characterized in that said mineral acid hydrolysis concentration is at 1～3% (V/V).
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102321701B (en) * | 2011-08-16 | 2013-01-23 | 张家港市华昌药业有限公司 | Biological preparation method of D-mannose |
| CN103193896B (en) * | 2013-03-12 | 2015-09-16 | 武汉纤浓生物科技有限公司 | A kind of preparation method of Konjac Glucomannan and the thin-film evaporator adopted thereof |
| CN105087717A (en) * | 2015-07-31 | 2015-11-25 | 丽江玉元食品有限公司 | Method of utilizing acidic mannase to hydrolyze refined konjac powder to prepare konjac oligosaccharide |
| CN108949855B (en) * | 2017-05-23 | 2021-11-05 | 罗盖特公司 | Konjac glucomannan hydrolysate |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4292451A (en) * | 1978-03-30 | 1981-09-29 | Ici Americas Inc. | High mannitol process (alkaline hydrogenation in presence of alkali metal carbonate) |
| CN1524837A (en) * | 2003-09-17 | 2004-09-01 | 谭卫星 | Method for preparing mannitol utilizing dextrose |
| CN1528728A (en) * | 2003-09-28 | 2004-09-15 | 南宁市化工研究设计院 | High-yield manna sugar preparation process |
| CN1687432A (en) * | 2005-04-13 | 2005-10-26 | 南宁市化工研究设计院 | Method for preparing mannitol from raw material of cane sugar |
| CN1840518A (en) * | 2005-08-18 | 2006-10-04 | 山东寻山水产集团有限公司 | Process for extracting mannitol from kelp |
-
2007
- 2007-12-26 CN CN2007103035074A patent/CN101215580B/en not_active Expired - Fee Related
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4292451A (en) * | 1978-03-30 | 1981-09-29 | Ici Americas Inc. | High mannitol process (alkaline hydrogenation in presence of alkali metal carbonate) |
| CN1524837A (en) * | 2003-09-17 | 2004-09-01 | 谭卫星 | Method for preparing mannitol utilizing dextrose |
| CN1528728A (en) * | 2003-09-28 | 2004-09-15 | 南宁市化工研究设计院 | High-yield manna sugar preparation process |
| CN1687432A (en) * | 2005-04-13 | 2005-10-26 | 南宁市化工研究设计院 | Method for preparing mannitol from raw material of cane sugar |
| CN1840518A (en) * | 2005-08-18 | 2006-10-04 | 山东寻山水产集团有限公司 | Process for extracting mannitol from kelp |
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