CN101205238A - Extraction method of phytic acid in rice bran - Google Patents
Extraction method of phytic acid in rice bran Download PDFInfo
- Publication number
- CN101205238A CN101205238A CNA2007101706892A CN200710170689A CN101205238A CN 101205238 A CN101205238 A CN 101205238A CN A2007101706892 A CNA2007101706892 A CN A2007101706892A CN 200710170689 A CN200710170689 A CN 200710170689A CN 101205238 A CN101205238 A CN 101205238A
- Authority
- CN
- China
- Prior art keywords
- phytic acid
- rice bran
- solution
- turbid liquid
- beige
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Images
Abstract
The invention relates to a method for extracting the phytic acid from rice bran, in particular to an extraction method for utilizing the microwave treatment technology to obtain the phytic acid from the rice bran. The method of the invention comprises the steps that: the samples are treated using the microwave with a power ranging from 500W to 1200W after the rice bran is broken and is extracted using the hydrogen chloride solution; then the pH of the obtained solution is adjusted to range from 1.0 to 3.0 using the sodium hydroxide solution and then the processed solution is driven to rest in a static state and is stirred for 0.5 to 1 hour; the beige suspension liquid is obtained through filtration and the pH of the filtrate is first adjusted to 4.0 using the 10 per cent calcium hydroxide emulsion and then the pH of the processed solution is adjusted to exceed 7.0 using the sodium hydroxide solution with a concentration of 1mol/L instead of 10 per cent calcium hydroxide emulsion so as to obtian the beige turbid liquid in which the white precipitates are contained; the beige turbid liquid is stirred uniformly before the turbid liquid rests for 1 to 2 hours so as to completely precipitate the turbid liquid; after the turbid liquid is filtered, the intermediates, calcium phytate pulps ranging from grey to drab in color, are obtained; the intermediates are converted into the existence in the form of ions through dissolution and then the phytic acids, which are the final products, are prepared through ion exchange, decoloration and concentration. Compared with the prior art, the invention has the advantages of high extraction rate, short time, high product quality, excellent color, simple and convenient operation, suitability for the industrialized production, etc.
Description
Technical field
The present invention relates to the extracting method of phytic acid in a kind of rice bran, particularly relate to a kind of method of utilizing the microwave treatment technology from rice bran, to extract phytic acid.
Background technology
According to studies show that of the Mitsui East Asia chemical company of world industry production phytic acid output maximum, the production method of phytic acid mainly contains three kinds at present, that is: chemical synthesis, biological synthesis process and solvent extration.Wherein, solvent extration is the cardinal principle of traditional technology.
The content of phytic acid only is 1%~3% not wait in the rice bran, more the form with the calcium magnesium salts exists, content can reach 10%~15%, so the extracting method of phytic acid mainly is the utilization solvent extration at present, from rice bran, extract luxuriant and rich with fragrance spit of fland (general name of phytic acid ca, magnesium salts), obtain phytic acid with the displacement of methods such as ion-exchange again.
Solvent extration mainly is to soak the raw material that contains phytate with rare strong acid solution phytate is dissolved in the steeping fluid, neutralize with alkali again, rising along with the pH value, the complexing action of phytic acid and metal ion strengthens gradually, when pH reached certain value, phytic acid and metal ion formed double salt again and precipitate.The dissolving of phytic acid ca after purifying is changed into ionic species, again through ion-exchange, decolouring, concentrate and make.This is the method for the extraction phytic acid of present widespread use.But problem such as the phytic acid extraction yield of solvent extration gained is low, the time is long, product quality is low and color and luster is not good.
Summary of the invention
Extracting from rice bran in the bibliographical information of phytic acid, intermediate product phytic acid ca yield is generally at 10-11%, and color and luster is pale brown to light yellow, and extraction time reaches 6-8 hour.Shortcoming such as thereby the extraction yield that causes final phytic acid is low, extraction time is long, product quality is low and color and luster is not good.
The objective of the invention is in order to solve existing above-mentioned defective in the prior art, a kind of method of utilizing the microwave treatment technology to extract phytic acid from rice bran is proposed, extraction process after optimizing, the optimum extraction rate of intermediate product phytic acid ca is 13.88%, extraction time is 3-4 hour, it is light yellow to white that the color and luster of product is, and is similar to the color and luster of pure phytic acid ca sample.Because in the intermediate product phytic acid ca leaching process, extraction yield height, extraction time shorten, product color is good etc. makes the acquisition of follow-up phytic acid product have the extraction yield height, the time is short, product quality is high, color and luster is good, easy and simple to handle etc. is suitable for the advantage of suitability for industrialized production.
So far, the method for utilizing the microwave treatment technology to extract phytic acid from rice bran is not appeared in the newspapers both at home and abroad.
Principle of the present invention:
The leaching of traditional solvent extration is not carried out cytoclasis before operating in extraction, and cell walls and cytolemma bring very big extraction resistance, and extraction time is long, reagent consumption is big; On the other hand, the leaching operation can not make the rapid inactivation of lytic enzyme in the born of the same parents, has promoted the degraded of enzyme to target product owing to slowly heat up on the contrary, and precious raw material resources are not fully utilized.
Characteristics at the general Heat stability is good of natural product, the plant vacuole at phytic acid ca place heats up rapidly under the effect of microwave field, moisture vaporization born of the same parents internal pressure increases suddenly, cell walls and cytolemma can not bear so big interior pressure, fragmentation forms small hole so cell breach occurs under the microwave of certain intensity impacts.Further heating causes cell interior and cell walls moisture to reduce, cellular contraction, and crackle appears in the surface.The existence of hole or crackle enters in the cell the outer solvent of born of the same parents easily, dissolve and discharge intracellular product, thereby lixiviate goes out most of phytic acid.So the present invention proposes a kind of method of utilizing the microwave treatment technology to extract phytic acid from rice bran.
Technical scheme of the present invention:
The present invention includes with the rice bran is that raw material is pulverized it, gets the rice bran of a certain amount of pulverizing, adds the hydrochloric acid soln of 0.1mol/L, and the control solid-liquid ratio is in 1: 5 to 1: 10 scope, and lixiviate 3-6h is the microwave treatment sample of 700~1200W with power, and the time is 3min; Regulating pH with the sodium hydroxide solution of 1mol/L afterwards is 1.0~3.0 scope, leaves standstill then and stirs 3h~6h.Filtration obtains beige suspension liquid body, filtrate is regulated pH to 4.0 with 10% calcium hydroxide emulsion earlier, use the sodium hydroxide solution of 1mol/L again instead and regulate pH>7.0, obtain the sedimentary turbid liquid of adularescent in the beige, leave standstill 2~3h after stirring, make precipitation fully, obtain grey after the filtration to filemot intermediate product phytic acid ca soup compound, again through dissolving, ion-exchange, decolouring, concentrate and make the final product phytic acid.
In the leaching process, pulverising step is for to be broken to bran powder below 150 orders.
In leaching process, the best solid-liquid ratio of the used hydrochloric acid of the rice bran of pulverizing and lixiviate 1: 7, best extraction time is 4h.
In leaching process, use microwave treatment after the lixiviate, after the power of microwave surpassed 700W, along with the increase of microwave power, the yield and the purity of phytic acid descended on the contrary.This is owing to contain 33%~53% starch in the rice bran, starch produces " microwave bulking " under more high-power condition, the expansion rate that makes starch reaches maximum value in the relatively shorter time, and the expansion rate increase of starch can have influence on the extraction yield of product phytic acid in the rice bran.
And increase along with microwave heating time, beginning obviously descended after the yield of phytic acid ca and purity progressively were incremented to 3min before this, when especially heating 5min, the rice bran sample that obtains is dry substantially, this also is that " microwave bulking " takes place when arriving certain temperature owing to the starch that contains 33%~53% in the rice bran, make the expansion rate of starch in the relatively shorter time, reach maximum value, thereby have influence on the extraction yield of product phytic acid ca.The best microwave power of microwave treatment of the present invention is 700W, the microwave treatment Best Times is 3min, in leaching process, through transferring pH neutralization precipitation after-filtration to obtain grey to filemot intermediate product phytic acid ca pulpous state, take by weighing phytic acid ca 0.5000g, put into the 100mL beaker, the plant acid solution that adds 2mL distilled water and 0.75mL50% in the small beaker, stir 2min, add a certain amount of RH strong acidic ion resin, stir 15min, pour the long 20cm that is into, internal diameter is in the ion exchange column of 2.0cm, replaces phytic acid at normal temperatures and pressures, washs at twice with 50mL distilled water again, displacement fully as far as possible, gained exchange solution at 58 ℃, is concentrated under the condition of vacuum tightness 12.62 kPa, promptly get end product phytic acid product.
Technique effect of the present invention:
Utilize the microwave treatment technology to extract and compare with the conventional solvent extraction process, extraction time shortens greatly, and product purity, extraction yield all increase.In addition, because extraction time shortens, subsequent technique waits also than advantages such as traditional method are easy as filtering.
Description of drawings
Fig. 1 utilizes the microwave treatment technology to extract the process flow sheet of the method for phytic acid from rice bran.
Embodiment
Embodiment 1:
With the rice bran is that raw material was pulverized 150 mesh sieves with it, take by weighing rice bran 5g, the hydrochloric acid soln that adds 0.1mol/L, the control solid-liquid ratio is 1: 5,1: 6,1: 7,1: 8,1: 9,1: 10, control pH is 3.0, lixiviate 3h is a microwave treatment sample under moderate heat (about 1000W) condition with power, and the time is 3min.Regulating pH with the sodium hydroxide solution of 1mol/L afterwards is 3.0 scope, leaves standstill then and stirs 3h.Filtration obtains beige suspension liquid body, filtrate is regulated pH to 4.0 with 10% calcium hydroxide emulsion earlier, use the sodium hydroxide solution of 1mol/L again instead and regulate pH>7.0, obtain the sedimentary turbid liquid of adularescent in the beige, leave standstill 2h after stirring, make precipitation fully, obtain grey after the filtration to filemot intermediate product phytic acid ca soup compound.Calculate the amount and the purity thereof of intermediate product phytic acid ca, solid-liquid ratio the results are shown in Table 1 to the influence of middle product phytic acid ca purity during lixiviate.Take by weighing phytic acid ca 0.5000g, put into the 100mL beaker, the plant acid solution that adds 2mL distilled water and 0.75mL50% in the small beaker, stir 2min, add a certain amount of RH strong acidic ion resin, stir 15min, pour the long 20cm that is into, internal diameter is in the ion exchange column of 2.0cm, replaces phytic acid at normal temperatures and pressures, washs at twice with 50mL distilled water again, displacement fully as far as possible, gained exchange solution at 58 ℃, is concentrated under the condition of vacuum tightness 12.62 kPa, promptly get end product phytic acid product.
Table 1 solid-liquid ratio is to the influence of middle product phytic acid ca purity
The experiment number | Get solid-liquid ratio | Phytic acid ca (g) | Purity (%) |
1 2 3 4 5 6 | 1∶5 1∶6 1∶7 1∶8 1∶9 1∶10 | 0.6843 1.4971 2.4715 2.3574 2.4035 2.2926 | 27.10 51.66 78.81 72.47 74.09 75.24 |
Embodiment 2:
With the rice bran is that raw material was pulverized 150 mesh sieves with it, takes by weighing rice bran 5g, adds the hydrochloric acid soln of 0.1mol/L, control solid-liquid ratio 1: 7, control pH is 3.0, lixiviate 3h, with power is microwave treatment sample under 500W, 700W, 1000W, 1200W condition, and the time is 3min.Regulating pH with the sodium hydroxide solution of 1mol/L afterwards is 3.0 scope, leaves standstill then and stirs 3h.Filtration obtains beige suspension liquid body, filtrate is regulated pH to 4.0 with 10% calcium hydroxide emulsion earlier, use the sodium hydroxide solution of 1mol/L again instead and regulate pH>7.0, obtain the sedimentary turbid liquid of adularescent in the beige, leave standstill 2h after stirring, make precipitation fully, obtain grey after the filtration to filemot phytic acid ca soup compound.Calculate the amount and the yield thereof of intermediate product phytic acid ca, microwave power the results are shown in Table 2 to the influence of middle product phytic acid ca yield.Take by weighing phytic acid ca 0.5000g, put into the 100mL beaker, the plant acid solution that adds 2mL distilled water and 0.75mL50% in the small beaker, stir 2min, add a certain amount of RH strong acidic ion resin, stir 15min, pour the long 20cm that is into, internal diameter is in the ion exchange column of 2.0cm, replaces phytic acid at normal temperatures and pressures, washs at twice with 50mL distilled water again, displacement fully as far as possible, gained exchange solution at 58 ℃, is concentrated under the condition of vacuum tightness 12.62 kPa, promptly get end product phytic acid product.
Table 2 microwave power is to the influence of yield
The experiment number | Microwave power | Color and luster | Gained phytic acid ca (g) | Yield (%) |
1 2 3 4 | The high fire of insulation (about 700W) low fire (about 800W) moderate heat (about 1000W) (about 1200W) | White solid white solid pale solid light yellow solid | 0.694 0.681 0.623 0.625 | 13.88 13.62 12.46 12.50 |
Embodiment 3:
With the rice bran is that raw material was pulverized 150 mesh sieves with it, takes by weighing rice bran 5g, adds the hydrochloric acid soln of 0.1mol/L, control solid-liquid ratio 1: 7, control pH is 3.0, lixiviate 3h, with power is microwave treatment sample under 500W, 700W, 1000W, 1200W condition, and the time is 3min.Regulating pH with the sodium hydroxide solution of 1mol/L afterwards is 3.0 scope, leaves standstill then and stirs 3h.Filtration obtains beige suspension liquid body, filtrate is regulated pH to 4.0 with 10% calcium hydroxide emulsion earlier, use the sodium hydroxide solution of 1mol/L again instead and regulate pH>7.0, obtain the sedimentary turbid liquid of adularescent in the beige, leave standstill 2h after stirring, make precipitation fully, obtain grey after the filtration to filemot intermediate product phytic acid ca soup compound.Calculate the amount and the yield thereof of intermediate product phytic acid ca, microwave treatment time the results are shown in Table 3 to the influence of middle product phytic acid ca yield.Take by weighing phytic acid ca 0.5000g, put into the 100mL beaker, the plant acid solution that adds 2mL distilled water and 0.75mL50% in the small beaker, stir 2min, add a certain amount of RH strong acidic ion resin, stir 15min, pour the long 20cm that is into, internal diameter is in the ion exchange column of 2.0cm, replaces phytic acid at normal temperatures and pressures, washs at twice with 50mL distilled water again, displacement fully as far as possible, gained exchange solution at 58 ℃, is concentrated under the condition of vacuum tightness 12.62 kPa, promptly get end product phytic acid product.
Table 3 microwave treatment time is to the influence of middle product phytic acid ca yield
The experiment number | The microwave time (min) | Color and luster | Gained phytic acid ca (g) | Yield (%) |
1 2 3 4 5 | 1 2 3 4 5 | The beige solid, middle adularescent small-particle brown solid, middle adularescent small-particle pale solid pale solid tawny solid, middle adularescent small-particle | 0.585 0.588 0.674 0.542 0.480 | 10.70 10.76 13.48 9.84 8.60 |
Embodiment 4:
With the rice bran is that raw material was pulverized 150 mesh sieves with it, takes by weighing rice bran 5g, adds the hydrochloric acid soln of 0.1mol/L, control solid-liquid ratio 1: 7, and control pH is 3.0, and lixiviate is respectively 3h, 4h, 5h, 6h, is microwave treatment sample under the 700W condition with power, and the time is 3min.Regulating pH with the sodium hydroxide solution of 1mol/L afterwards is 3.0 scope, leaves standstill then and stirs 3h.Filtration obtains beige suspension liquid body, filtrate is regulated pH to 4.0 with 10% calcium hydroxide emulsion earlier, use the sodium hydroxide solution of 1mol/L again instead and regulate pH>7.0, obtain the sedimentary turbid liquid of adularescent in the beige, leave standstill 2h after stirring, make precipitation fully, obtain grey after the filtration to filemot intermediate product phytic acid ca soup compound.Calculate the amount and the purity thereof of intermediate product phytic acid ca, extraction time the results are shown in Table 4 to the influence of middle product phytic acid ca purity.Take by weighing phytic acid ca 0.5000g, put into the 100mL beaker, the plant acid solution that adds 2mL distilled water and 0.75mL50% in the small beaker, stir 2min, add a certain amount of RH strong acidic ion resin, stir 15min, pour the long 20cm that is into, internal diameter is in the ion exchange column of 2.0cm, replaces phytic acid at normal temperatures and pressures, washs at twice with 50mL distilled water again, displacement fully as far as possible, gained exchange solution at 58 ℃, is concentrated under the condition of vacuum tightness 12.62 kPa, promptly get end product phytic acid product.
Table 4 extraction time is to the influence of middle product phytic acid ca purity
The experiment number | Extraction time (h) | Phytic acid ca (g) | Purity (%) |
1 2 3 4 | 3 4 5 6 | 1.1359 1.3357 1.3333 1.3011 | 61.69 82.77 77.00 67.12 |
Embodiment 5:
With the rice bran is that raw material was pulverized 150 mesh sieves with it, takes by weighing rice bran 5g, adds the hydrochloric acid soln of 0.1mol/L, control solid-liquid ratio 1: 7, control pH is 2.0,3.0,4.0,5.0, lixiviate is respectively 4h, with power is microwave treatment sample under the 700W condition, and the time is 3min.Regulating pH with the sodium hydroxide solution of 1mol/L afterwards is 3.0, leaves standstill then to stir 3h.Filtration obtains beige suspension liquid body, filtrate is regulated pH to 4.0 with 10% calcium hydroxide emulsion earlier, use the sodium hydroxide solution of 1mol/L again instead and regulate pH>7.0, obtain the sedimentary turbid liquid of adularescent in the beige, leave standstill 2h after stirring, make precipitation fully, obtain grey after the filtration to filemot intermediate product phytic acid ca soup compound.Calculate the amount and the purity thereof of intermediate product phytic acid ca, pH the results are shown in Table 5 to the influence of middle product phytic acid ca purity during lixiviate.Take by weighing phytic acid ca 0.5000g, put into the 100mL beaker, the plant acid solution that adds 2mL distilled water and 0.75mL50% in the small beaker, stir 2min, add a certain amount of RH strong acidic ion resin, stir 15min, pour the long 20cm that is into, internal diameter is in the ion exchange column of 2.0cm, replaces phytic acid at normal temperatures and pressures, washs at twice with 50mL distilled water again, displacement fully as far as possible, gained exchange solution at 58 ℃, is concentrated under the condition of vacuum tightness 12.62 kPa, promptly get end product phytic acid product.
The pH value is to the influence of middle product phytic acid ca purity during table 5 lixiviate
The experiment number | Lixiviate pH | Phytic acid ca (g) | Purity (%) |
1 2 3 4 | 2.0 3.0 4.0 5.0 | 1.1359 1.3357 1.3333 1.3011 | 78.88 91.99 91.70 90.23 |
Claims (5)
1. the extracting method of phytic acid in the rice bran is characterized in that concrete extraction step is:
(1), be that raw material is pulverized it with the rice bran;
(2) get the rice bran of a certain amount of pulverizing, add the hydrochloric acid soln of 0.1mol/L, the control solid-liquid ratio is in 1: 5 to 1: 10 scope, and extraction time is 3-6h;
(3) be the microwave treatment sample of 500~1200W with power, the time is 3min;
(4) regulating pH with the sodium hydroxide solution of 1mol/L is 1.0~3.0 scope, leave standstill then and stir 3h~6h, filtration obtains beige suspension liquid body, filtrate is regulated pH to 4.0 with 10% calcium hydroxide emulsion earlier, use the sodium hydroxide solution of 1mol/L again instead and regulate pH>7.0, obtain the sedimentary turbid liquid of adularescent in the beige, leave standstill 2~3h after stirring, make precipitation fully;
(5) obtain grey after the filtration to filemot intermediate product phytic acid ca soup compound;
(6) take by weighing phytic acid ca 0.5000g, put into the 100mL beaker, add the plant acid solution of 2mL distilled water and 0.75mL50% in the small beaker, stir 2min;
(7) add a certain amount of RH strong acidic ion resin, stir 15min, pour the long 20cm that is into, internal diameter is in the ion exchange column of 2.0cm, replaces phytic acid at normal temperatures and pressures;
(8) wash at twice with 50mL distilled water, displacement fully as far as possible;
(9) gained is exchanged solution at 58 ℃, concentrate under the condition of vacuum tightness 12.62 kPa, promptly get the end product phytic acid.
2. according to the extracting method of claim 1, it is characterized in that: best solid-liquid ratio 1: 7.
3. according to the extracting method of claim 1, it is characterized in that: best extraction time is 4h.
4. according to the extracting method of claim 1, it is characterized in that: best microwave power is 700W, and microwave treatment time is 3min.
5. according to the preparation method of claim 1, it is characterized in that: lixiviate pH is 3.0.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNA2007101706892A CN101205238A (en) | 2007-11-21 | 2007-11-21 | Extraction method of phytic acid in rice bran |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNA2007101706892A CN101205238A (en) | 2007-11-21 | 2007-11-21 | Extraction method of phytic acid in rice bran |
Publications (1)
Publication Number | Publication Date |
---|---|
CN101205238A true CN101205238A (en) | 2008-06-25 |
Family
ID=39565736
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNA2007101706892A Pending CN101205238A (en) | 2007-11-21 | 2007-11-21 | Extraction method of phytic acid in rice bran |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN101205238A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102127108A (en) * | 2010-12-08 | 2011-07-20 | 东北电力大学 | Method for extracting phytic acid from rice bran |
CN104530118A (en) * | 2015-01-12 | 2015-04-22 | 国家电网公司 | Method for extracting phytic acid from rice bran |
-
2007
- 2007-11-21 CN CNA2007101706892A patent/CN101205238A/en active Pending
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102127108A (en) * | 2010-12-08 | 2011-07-20 | 东北电力大学 | Method for extracting phytic acid from rice bran |
CN104530118A (en) * | 2015-01-12 | 2015-04-22 | 国家电网公司 | Method for extracting phytic acid from rice bran |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN105482890B (en) | A kind of method of microwave-ultrasonic auxiliary extracting linseed oil by water-enzyme process | |
CN106631753B (en) | Method for producing gallic acid by using superfine gallnut powder | |
CN103694374A (en) | Method for extracting agar, fucoidin and protein from gracilaria as raw material by using enzyme process | |
CN102452902A (en) | Preparation method for phloroglucinol | |
US20020098553A1 (en) | Process for producing carrageenan with reduced amount of insoluble material | |
CN103539869A (en) | Method for improving enzymolysis efficiency of crude heparin sodium extraction technology | |
CN103483403B (en) | A kind of circulation extracting method of hesperidine of purifying from tangerine slag | |
CN105420511A (en) | Method for reducing osmium absorption liquid | |
CN103804172A (en) | Method for improving organic acid product quality | |
CN101693907A (en) | Method for using dried potato flour to prepare potassium citrate | |
CN101205238A (en) | Extraction method of phytic acid in rice bran | |
CN106749752A (en) | A kind of preparation method of ultra-low viscosity alginate | |
CN101456920A (en) | Method for producing high transparent sodium alginate | |
CN105272887A (en) | Method for extracting taurine and polysaccharides from abalone's viscera simultaneously | |
CN104762333B (en) | Method for preparing xylitol by utilizing winter bamboo shoot shells | |
CN102875367A (en) | Method for preparing gallic acid by means of microwave assisted tannin containing biomass hydrolysis | |
CN103695571B (en) | Subcritical water process vinasse are utilized to prepare the method for wood sugar and protolysate | |
CN101100435A (en) | Method for preparing L-ornithine-L-aspartate | |
CN100396614C (en) | Method for desiliconizing green liquor of sodium aluminate under normal pressure | |
CN101429118A (en) | Process for producing gallic acid with gall flower extract and one-step method | |
CN112209858B (en) | Preparation method of 2- [ [ tri (hydroxymethyl) methyl ] amino ] ethanesulfonic acid | |
CN106699624A (en) | Production method of lutein | |
CN107140662A (en) | A kind of new method for producing cesium hydroxide | |
CN102775296A (en) | Preparation method of 2,2-dimethylolbutanoicacid | |
CN109694311B (en) | Method for synthesizing isoliquiritigenin |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
WD01 | Invention patent application deemed withdrawn after publication |
Open date: 20080625 |