CN103194495A - Method for preparing levulinic acid from starch type traditional Chinese medicine residues - Google Patents
Method for preparing levulinic acid from starch type traditional Chinese medicine residues Download PDFInfo
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- CN103194495A CN103194495A CN2013101354564A CN201310135456A CN103194495A CN 103194495 A CN103194495 A CN 103194495A CN 2013101354564 A CN2013101354564 A CN 2013101354564A CN 201310135456 A CN201310135456 A CN 201310135456A CN 103194495 A CN103194495 A CN 103194495A
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Abstract
The invention discloses a method for preparing levulinic acid from starch type traditional Chinese medicine residues. The process A of the method comprises the following steps of: crushing and soaking the medicine residues with the starch content of below 40%, adding alpha-amylase to perform hydrolysis reaction, adding glucoamylase into an amylase hydrolysate to perform saccharification hydrolysis reaction, adding concentrated acid into a glucoamylase hydrolysate to obtain a gluconic acid solution, and performing reaction on the gluconic acid solution in a reaction kettle to obtain a reaction solution containing the levulinic acid; and the process B of the method comprises the following steps of: crushing and soaking the medicine residues, adding the glucoamylase to perform the saccharification hydrolysis reaction, adding the concentrated acid into the glucoamylase hydrolysate to obtain the gluconic acid solution, and performing the reaction on the gluconic acid solution in the reaction kettle to obtain the reaction solution containing the levulinic acid. The method for utilizing the starch type traditional Chinese medicine residues, disclosed by the invention, has the advantages of economic benefits of low cost and high efficiency and environmental benefit of green process.
Description
Technical field
The present invention relates to a kind of method that is prepared levulinic acid by the starch based Chinese medicine slag, belong to the biomass waste resource conversion and utilize technical field.
Background technology
China is the source region of herbal medicine, is also the resource big country of Chinese medicinal materials, and current domestic 1636 traditional Chinese medicine enterprises that have, account for 32% of national pharmaceutical manufacturer, and the annual Chinese medicine slag that produces is more than 1,300 ten thousand tons (wherein plant medicine dregs accounts for more than 87%).Chinese medicine slag is as a kind of abandoned biomass resource, and annual quantum of output is large, difficult treatment, but collects conveniently, thereby has good application prospect.The general water content of Chinese medicine slag is high, and contains certain nutritive substance, very easily corrupt, if store up from rotten, not only take a large amount of soils, and environmental pollution is serious, so dealing carefully with of the dregs of a decoction becomes the thorny problem that traditional Chinese medicine enterprise faces.
Starch is the very high a kind of biomass of content in the plant dregs of a decoction, by glucose polymerisation, is formed, and amylose starch and amylopectin two classes are arranged.Can make glucose by the amylase effectively hydrolyzing, this is the first step of starch based dregs of a decoction exploitation.Amylase can be divided into α-amylase and beta-amylase according to the difference of hydrolysate; According to the difference of hydrolytic process, can be divided into again α-amylase (being hydrolyzed into dextrin) and saccharifying enzyme (being hydrolyzed into monose).Different diastatic hydrolysis results are different, therefore, correctly choose and combine enzyme, and the optimization enzymatic hydrolysis condition is one of efficient core technology of utilizing of the starch based dregs of a decoction.
At present, also exist feed stock conversion low aspect the comprehensive utilization after starch based dregs of a decoction enzymolysis, the shortcoming such as added value of product is low, production cost is high.According to the character of dregs of a decoction enzymolysis product glucose, researching and developing is the preferred plan of rationally utilizing the starch based dregs of a decoction.On chemical industry, glucose is usually used in synthetic multiple important platform chemicals.Wherein, levulinic acid is a kind of important platform chemicals.Because of in its structure because thering is ketone group and carboxyl, therefore there is good reactivity, can be used as the starting material of many bulk chemical, spices, agricultural chemicals and fuel.For example, take levulinic acid as the synthetic levulinate of raw material, γ-valerolactone and 5-ALA, can be used for respectively synthetic perfume raw material, fuel dope and pesticide intermediate.But traditional technology Raw cost is high, environmental pollution is serious, conversion rate of products is low, become the bottleneck problem of restriction glucose high-value-use.Therefore; from low-cost raw material (the starch based dregs of a decoction); based on various chemistry and conversion technology; exploitation " enzymolysis and chemical conversion " is in the complete process flow of one; prepare the multiple important hardware and software platform compounds such as glucose and derivative chemical thereof; progressively set up the biorefining economic model, be of great significance solving the problem tools such as our times energy dilemma, environmental pollution.
Summary of the invention
The object of the present invention is to provide a kind of method that is prepared levulinic acid by the starch based Chinese medicine slag, the method process is simple, realizes turning waste into wealth, and has environmental protection and economic implications.
The present invention is realized by the following technical programs, a kind of method that is prepared levulinic acid by the starch based Chinese medicine slag, described starch based Chinese medicine slag comprises: shriveled wheat, lily and lotus seeds, and wherein starch quality content, lower than 40%, is characterized in that comprising following process:
(1) Chinese medicine slag being carried out to wet pulverization to order number through ball mill is 20 ~ 120 purpose powder, the drying water content is 0 ~ 20w%, it is damping fluid that the Sodium phosphate dibasic that the mass ratio of take is 0.06 ~ 4.2:1 and SODIUM PHOSPHATE, MONOBASIC are mixed with the mixed solution that pH is 5.5 ~ 7.5, by α-amylase and Chinese medicine slag mass ratio, be 0.005 ~ 0.1:1, and by 10 ~ 100 milliliters of damping fluids for every gram Chinese medicine slag, Chinese medicine slag and α-amylase are added in damping fluid, under 50 ~ 75 ℃ of temperature and stirring, hydrolysis reaction is 1 ~ 12 hour, obtains enzyme digestion reaction liquid
;
(2) enzyme digestion reaction liquid step (1) obtained, remove filter residue through separating, the filtrate obtained is determined the glucan content in filtrate by analysis, add sodium hydroxide adjusting pH to 6.5 ~ 7.5 in filtrate, regulate filtrate pH to 4.7 ~ 4.9 with citric acid afterwards, content according to dextran in filtrate, add by every gram dextran the standard that saccharifying enzyme is 5 ~ 60AGU, in temperature, be that 30 ~ 60 ℃ and rotating speed are under 20 ~ 300 rev/mins, add Glucoamylase hydrolysis reaction 2 ~ 72 hours in filtrate, obtain glucose solution, the glucose content in this glucose solution of Analysis deterrmination;
(3) add the 98w% sulphuric acid soln in the glucose solution of step (2) gained, to making h 2 so 4 concentration in glucose solution, be 0.1 ~ 10%, and the acid solution containing glucose adds in reactor by gained, under 140 ~ 190 ℃ of temperature and 100 ~ 600 rev/mins of stirrings of rotating speed, react 10 minutes ~ 6 hours, obtain containing the reaction solution that levulinic acid is 4.0 ~ 15.0 grams per liters.
Two of method, a kind of method that is prepared levulinic acid by the starch based Chinese medicine slag, described starch based Chinese medicine slag comprises: the dregs of a decoction of Semen Coicis, Root of coastal Glehnia, wherein starch content, higher than 40%, is characterized in that comprising following process:
(1) Chinese medicine slag being carried out to wet pulverization to order number through ball mill is 20 ~ 120 purpose powder, the drying water content is 0 ~ 20w%, the citric acid that the pH of take is 4.7 ~ 4.9 is damping fluid, content according to starch in the dregs of a decoction, add by every gram starch the standard that saccharifying enzyme is 5 ~ 60AGU, and, by 10 ~ 100 milliliters of damping fluids for every gram Chinese medicine slag, Chinese medicine slag and saccharifying enzyme are added in damping fluid, under 30 ~ 60 ℃ of temperature and stirring, hydrolysis reaction is 2 ~ 72 hours, obtains enzyme digestion reaction liquid;
(2) to the enzyme digestion reaction liquid of step (1) gained, through separating, remove filter residue, the filtrate obtained is determined the glucose content in filtrate by analysis; Add the 98w% sulphuric acid soln in the filtrate of gained, to making h 2 so 4 concentration in filtrate, be 0.1 ~ 10%, obtain the acid solution that contains glucose, then gluconic acid solution is added in reactor, under 140 ~ 190 ℃ of temperature and 100 ~ 600 rev/mins of stirrings of rotating speed, react 10 minutes ~ 6 hours, obtain containing the reaction solution that levulinic acid is 5.0 ~ 18.0 grams per liters.
The economic benefit of utilizing method to have advantages of that cost is low, efficiency is high of the starch based Chinese medicine slag provided and the environmental benefit of technique green are provided.
The accompanying drawing explanation
Fig. 1. in the embodiment of the present invention 1, the high performance liquid chromatography of glucose solution detects figure.
Fig. 2. in the embodiment of the present invention 2, the high performance liquid chromatography of filtrate detects figure.
Fig. 3. the high performance liquid chromatography that contains the reaction solution of levulinic acid in the embodiment of the present invention 1 detects figure.
Embodiment
Embodiment 1
By the lotus seeds dregs of a decoction, through ball mill pulverizing to order number, be 20 ~ 120 purpose powder, take 178.92 gram Sodium phosphate dibasics and 493.2 gram SODIUM PHOSPHATE, MONOBASIC, to be mixed with 20 liters of mixed solutions that pH is 6.5 be damping fluid, 1000 gram lotus seeds dregs of a decoction powder and 80 gram α-amylase dry powder that drying is 0 by water content add in damping fluid, enzyme digestion reaction 48h under 65 ℃ of temperature and 120 rev/mins of stirrings.Reaction solution after enzyme digestion reaction finishes, carry out solid-liquid separation through vortex centrifugal, suction filtration, obtains 731 gram filter residues and 19.9 liters of filtrates.Filter residue is after drying as fertilizer application.The filtrate obtained determines that the glucan content in filtrate is 17 grams per liters by analysis.Neutralized to adding 265.2 gram sodium hydroxide in filtrate, make pH reach 7.0.Afterwards, adding 210 gram lemon acid for adjusting pH to 4.8, is that 50 ℃ and rotating speed are under 80 rev/mins in temperature, to adding the reaction 20 hours that is hydrolyzed of 170AGU saccharifying enzyme in filtrate, obtains glucose solution.After high performance liquid chromatography (HPLC) detects, the glucose yield is 51.3%, and high performance liquid chromatography detects figure as shown in Figure 1.
Add 1.1 liters of 98w% sulphuric acid solns in 19.9 liters of glucose solutions, and gained is added in reactor and reacted containing the acid solution of glucose.Reaction conditions is: 190 ℃, and rotating speed: 100 rev/mins, 10 minutes reaction times.21 liters of levulinic acids that the reaction solution main component is 5.9 grams per liters after acidolysis, yield reaches 34%, and high performance liquid chromatography detects figure as shown in Figure 3.
Embodiment 2
By the Semen Coicis dregs of a decoction, through ball mill pulverizing to order number, be 20 ~ 120 purpose powder, the 315 gram citric acids of take are mixed with 30 liters of the damping fluids that pH is 4.8, the Semen Coicis dregs of a decoction 1000 grams that drying is 20w% by water content are placed in damping fluid, and add 8000AGU glucoamylase enzyme liquid, 50 ℃ of temperature and 100 rev/mins of lower enzymolysis of rotating speed 24 hours.Reaction solution after enzyme digestion reaction is finished, carry out solid-liquid separation through vortex centrifugal, suction filtration, obtains 29.8 liters of filtrates and 817 gram filter residues.Can be used as fertilizer application after filter residue and drying.Filtrate is detected the solution be defined as containing glucose through high performance liquid chromatography (HPLC), the glucose yield is 69.6%, and high performance liquid chromatography detects figure as shown in Figure 2.
Add 17 milliliters of 98w% sulphuric acid solns in 29.8 liters of filtrates, obtain the acid solution that contains glucose; Gained gluconic acid solution is added in reactor and reacted.Reaction conditions is: 140 ℃, and rotating speed: 600 rev/mins, 6 hours reaction times.29.8 liters of levulinic acids that the reaction solution main component is 4.9 grams per liters after acidolysis, yield reaches 35%.
Embodiment 3
By the Root of coastal Glehnia dregs of a decoction, through ball mill pulverizing to order number, be 20 ~ 120 purpose powder, take 69.86 gram Sodium phosphate dibasics and 631.44 gram SODIUM PHOSPHATE, MONOBASIC, to be mixed with 20 liters of mixed solutions that pH is 6.0 be damping fluid, 1000 gram lotus seeds dregs of a decoction powder and 70 gram α-amylase dry powder that drying is 10w% by water content add in damping fluid, enzyme digestion reaction 48h under 65 ℃ of temperature and 100 rev/mins of stirrings.Reaction solution after enzyme digestion reaction finishes, carry out solid-liquid separation through vortex centrifugal, suction filtration, obtains 712 gram filter residues and 19.9 liters of filtrates.Filter residue is after drying as fertilizer application.The filtrate obtained determines that the glucan content in filtrate is 16.5 grams per liters by analysis.Neutralized to adding 244.2 gram sodium hydroxide in filtrate, make pH reach 6.5.Afterwards, add 180 gram lemon acid for adjusting pH to 4.8, under temperature is 60 rev/mins of 50 ℃ and rotating speeds, to adding the reaction 20 hours that is hydrolyzed of 247.5AGU saccharifying enzyme in filtrate, obtain glucose solution.After high performance liquid chromatography (HPLC) detects, the glucose yield is 61.5%.
Add 0.5 liter of 98w% sulphuric acid soln in 19.9 liters of glucose solutions, and gained is added in reactor and reacted containing the acid solution of glucose.Reaction conditions is: 165 ℃, and rotating speed: 350 rev/mins, 3 hours reaction times.20.4 liters of levulinic acids that the reaction solution main component is 8.4 grams per liters after acidolysis, yield reaches 37%.
Lily being mixed to the dregs of a decoction (ratio of mixture 1:1) is 20 ~ 120 purpose powder with shriveled wheat through ball mill pulverizing to order number, 520 gram citric acids are mixed with 50 liters of the damping fluids that pH is 4.8, the mixing dregs of a decoction 1000 grams that drying is 5w% by water content are placed in damping fluid, and add 10000AGU glucoamylase enzyme liquid, 55 ℃ of temperature and 180 rev/mins of lower enzymolysis of rotating speed 20 hours.Reaction solution after enzyme digestion reaction is finished, carry out solid-liquid separation through vortex centrifugal, suction filtration, obtains 49.7 liters of filtrates and 911 gram filter residues.Can be used as fertilizer application after filter residue and drying.Filtrate is detected the solution be defined as containing glucose through high performance liquid chromatography (HPLC), the glucose yield is 45.6%.
Add 1.1 liters of 98w% sulphuric acid solns in 49.7 liters of filtrates, obtain the acid solution that contains glucose; Gained gluconic acid solution is added in reactor and reacted.Reaction conditions is: 170 ℃, and rotating speed: 200 rev/mins, 1 hour reaction times.50.8 liters of levulinic acids that the reaction solution main component is 2.9 grams per liters after acidolysis, yield reaches 36%.
Embodiment 5
By the lily dregs of a decoction, through ball mill pulverizing to order number, be 20 ~ 120 purpose powder, take 89.46 gram Sodium phosphate dibasics and 246.6 gram SODIUM PHOSPHATE, MONOBASIC, to be mixed with 10 liters of mixed solutions that pH is 6.0 be damping fluid, 1000 gram lily dregs of a decoction powder and 70 gram α-amylase dry powder that drying is 15w% by water content add in damping fluid, enzyme digestion reaction 48h under 65 ℃ of temperature and 100 rev/mins of stirrings.Reaction solution after enzyme digestion reaction finishes, carry out solid-liquid separation through vortex centrifugal, suction filtration, obtains filter residue 708 grams and 9.9 liters of filtrates.Filter residue is after drying as fertilizer application.The filtrate obtained determines that the glucan content in filtrate is 15.5 grams per liters by analysis.To being neutralized containing adding 122.1 gram sodium hydroxide in the filtrate of dextran, make pH reach 7.5.Afterwards, add 92 gram lemon acid for adjusting pH to 4.8, under temperature is 60 rev/mins of 50 ℃ and rotating speeds, to adding the reaction 20 hours that is hydrolyzed of 232.5AGU saccharifying enzyme in filtrate, obtain glucose solution.After high performance liquid chromatography (HPLC) detects, the glucose yield is 58.7%.
Add 0.4 liter of 98w% sulphuric acid soln in 9.9 liters of glucose solutions, and gained is added in reactor and reacted containing the acid solution of glucose.Reaction conditions is: 150 ℃, and rotating speed: 400 rev/mins, 3 hours reaction times.10.3 liters of levulinic acids that the reaction solution main component is 13.1 grams per liters after acidolysis, yield reaches 34%.
Claims (2)
1. a method that is prepared levulinic acid by the starch based Chinese medicine slag, described starch based Chinese medicine slag comprises: shriveled wheat, lily and lotus seeds, wherein starch quality content, lower than 40%, is characterized in that comprising following process:
It is 20 ~ 120 purpose powder that Chinese medicine slag is carried out to wet pulverization to order number through ball mill, the drying water content is 0 ~ 20w%, it is damping fluid that the Sodium phosphate dibasic that the mass ratio of take is 0.06 ~ 4.2:1 and SODIUM PHOSPHATE, MONOBASIC are mixed with the mixed solution that pH is 5.5 ~ 7.5, by α-amylase and Chinese medicine slag mass ratio, be 0.005 ~ 0.1:1, and by 10 ~ 100 milliliters of damping fluids for every gram Chinese medicine slag, Chinese medicine slag and α-amylase are added in damping fluid, under 50 ~ 75 ℃ of temperature and stirring, hydrolysis reaction is 1 ~ 12 hour, obtains enzyme digestion reaction liquid
;
The enzyme digestion reaction liquid that step (1) is obtained, remove filter residue through separating, the filtrate obtained is determined the glucan content in filtrate by analysis, add sodium hydroxide adjusting pH to 6.5 ~ 7.5 in filtrate, regulate filtrate pH to 4.7 ~ 4.9 with citric acid afterwards, content according to dextran in filtrate, add by every gram dextran the standard that saccharifying enzyme is 5 ~ 60AGU, in temperature, be that 30 ~ 60 ℃ and rotating speed are under 20 ~ 300 rev/mins, add Glucoamylase hydrolysis reaction 2 ~ 72 hours in filtrate, obtain glucose solution, the glucose content in this glucose solution of Analysis deterrmination;
Add the 98w% sulphuric acid soln in the glucose solution of step (2) gained, to making h 2 so 4 concentration in glucose solution, be 0.1 ~ 10%, and the acid solution containing glucose adds in reactor by gained, under 140 ~ 190 ℃ of temperature and 100 ~ 600 rev/mins of stirrings of rotating speed, react 10 minutes ~ 6 hours, obtain containing the reaction solution that levulinic acid is 4.0 ~ 15.0 grams per liters.
2. a method that is prepared levulinic acid by the starch based Chinese medicine slag, described starch based Chinese medicine slag comprises: the dregs of a decoction of Semen Coicis, Root of coastal Glehnia, wherein starch content, higher than 40%, is characterized in that comprising following process:
It is 20 ~ 120 purpose powder that Chinese medicine slag is carried out to wet pulverization to order number through ball mill, the drying water content is 0 ~ 20w%, the citric acid that the pH of take is 4.7 ~ 4.9 is damping fluid, content according to starch in the dregs of a decoction, add by every gram starch the standard that saccharifying enzyme is 5 ~ 60AGU, and, by 10 ~ 100 milliliters of damping fluids for every gram Chinese medicine slag, Chinese medicine slag and saccharifying enzyme are added in damping fluid, under 30 ~ 60 ℃ of temperature and stirring, hydrolysis reaction is 2 ~ 72 hours, obtains enzyme digestion reaction liquid;
To the enzyme digestion reaction liquid of step (1) gained, remove filter residue through separating, the filtrate obtained is determined the glucose content in filtrate by analysis; Add the 98w% sulphuric acid soln in the filtrate of gained, to making h 2 so 4 concentration in filtrate, be 0.1 ~ 10%, obtain the acid solution that contains glucose, then gluconic acid solution is added in reactor, under 140 ~ 190 ℃ of temperature and 100 ~ 600 rev/mins of stirrings of rotating speed, react 10 minutes ~ 6 hours, obtain containing the reaction solution that levulinic acid is 5.0 ~ 18.0 grams per liters.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1900300A (en) * | 2006-07-20 | 2007-01-24 | 南京工业大学 | Low-temperature saccharification process of corn flour |
| US20090053770A1 (en) * | 2007-08-22 | 2009-02-26 | Susan Marie Hennessey | Biomass Pretreatment |
| CN101509017A (en) * | 2008-12-25 | 2009-08-19 | 李浪辉 | Process for preparing fermented alcohol by using residue of traditional Chinese medicine |
| CN101591246A (en) * | 2009-06-30 | 2009-12-02 | 华南理工大学 | Utilize the method for the synthetic 4-hydroxypentanoic acid methyl esters of biomass sugar hydrolysis hydrogenation and esterification |
-
2013
- 2013-04-18 CN CN2013101354564A patent/CN103194495A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1900300A (en) * | 2006-07-20 | 2007-01-24 | 南京工业大学 | Low-temperature saccharification process of corn flour |
| US20090053770A1 (en) * | 2007-08-22 | 2009-02-26 | Susan Marie Hennessey | Biomass Pretreatment |
| CN101509017A (en) * | 2008-12-25 | 2009-08-19 | 李浪辉 | Process for preparing fermented alcohol by using residue of traditional Chinese medicine |
| CN101591246A (en) * | 2009-06-30 | 2009-12-02 | 华南理工大学 | Utilize the method for the synthetic 4-hydroxypentanoic acid methyl esters of biomass sugar hydrolysis hydrogenation and esterification |
Non-Patent Citations (2)
| Title |
|---|
| CHA J Y ET AL: "Levulinic acid production based on extrusion and pressurized batch reaction", 《INDUSTRIAL CROPS AND PRODUCTS》, vol. 16, 31 December 2002 (2002-12-31), pages 109 - 118, XP055070392, DOI: doi:10.1016/S0926-6690(02)00033-X * |
| 杨莉等: "花生壳常压酸水解制备乙酰丙酸", 《花生学报》, vol. 41, no. 3, 31 December 2012 (2012-12-31), pages 27 - 32 * |
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Application publication date: 20130710 |