CN103833559A - Extraction process of ephedrine - Google Patents
Extraction process of ephedrine Download PDFInfo
- Publication number
- CN103833559A CN103833559A CN201210489938.5A CN201210489938A CN103833559A CN 103833559 A CN103833559 A CN 103833559A CN 201210489938 A CN201210489938 A CN 201210489938A CN 103833559 A CN103833559 A CN 103833559A
- Authority
- CN
- China
- Prior art keywords
- ephedra
- ephedrine
- oxalic acid
- dimethylbenzene
- extraction
- 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
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 title claims abstract description 61
- 238000000605 extraction Methods 0.000 title claims abstract description 49
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 title claims abstract description 32
- 229960002179 ephedrine Drugs 0.000 title claims abstract description 31
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims abstract description 99
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims abstract description 68
- 235000006408 oxalic acid Nutrition 0.000 claims abstract description 33
- 241000218671 Ephedra Species 0.000 claims abstract description 28
- 239000000284 extract Substances 0.000 claims description 19
- 241001465251 Ephedra sinica Species 0.000 claims description 18
- 239000007788 liquid Substances 0.000 claims description 17
- 238000001035 drying Methods 0.000 claims description 10
- 238000010992 reflux Methods 0.000 claims description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical class [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 5
- 238000002425 crystallisation Methods 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 239000012535 impurity Substances 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 230000007935 neutral effect Effects 0.000 claims description 5
- 238000002203 pretreatment Methods 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 abstract description 14
- 239000008096 xylene Substances 0.000 abstract 2
- 229940126680 traditional chinese medicines Drugs 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 241000723281 Ephedra equisetina Species 0.000 description 2
- BALXUFOVQVENIU-GNAZCLTHSA-N Ephedrine hydrochloride Chemical compound Cl.CN[C@@H](C)[C@H](O)C1=CC=CC=C1 BALXUFOVQVENIU-GNAZCLTHSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 229960002534 ephedrine hydrochloride Drugs 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- FMCGSUUBYTWNDP-ONGXEEELSA-N (1R,2S)-2-(dimethylamino)-1-phenyl-1-propanol Chemical compound CN(C)[C@@H](C)[C@H](O)C1=CC=CC=C1 FMCGSUUBYTWNDP-ONGXEEELSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000723237 Ephedra intermedia Species 0.000 description 1
- FMCGSUUBYTWNDP-UHFFFAOYSA-N N-Methylephedrine Natural products CN(C)C(C)C(O)C1=CC=CC=C1 FMCGSUUBYTWNDP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 230000009193 crawling Effects 0.000 description 1
- -1 demethyl ephedrine Chemical compound 0.000 description 1
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 229940073569 n-methylephedrine Drugs 0.000 description 1
- 239000002953 phosphate buffered saline Substances 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- BALXUFOVQVENIU-KXNXZCPBSA-N pseudoephedrine hydrochloride Chemical compound [H+].[Cl-].CN[C@@H](C)[C@@H](O)C1=CC=CC=C1 BALXUFOVQVENIU-KXNXZCPBSA-N 0.000 description 1
- 229960003447 pseudoephedrine hydrochloride Drugs 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to an extraction process of ephedrine, and belongs to the technical field of extraction of effective components in traditional Chinese medicines. The process provided by the invention comprises the following steps: pretreatment of ephedra; alkalization; extraction with xylene; extraction; concentration; and the like. By adopting the processes such as alkalization, extraction with xylene and extraction with oxalic acid, tedious processes in the prior art can be simplified, and high purity ephedrine can be quickly and effectively extracted.
Description
Technical field
The present invention relates to the extraction process of effective constituent in a kind of Chinese medicine, more particularly, the present invention relates to a kind of extraction process of ephedrine, belong to extracts active ingredients technical field in Chinese medicine.
Background technology
Chinese ephedra is Chinese medicine or claims the wind-cold-dispersing medicinal in Chinese medicine; Ancient times is called imperial sand, inferior phase.Include the plant of three kinds of Ephedras: ephedra sinica (Ephedra sinica), ephedra equisetina (Ephedra equisetina) and epheday intermedia (Ephedra intermedia), employing position is herb stem.Ephedra sinica ephedra sinica is undershrub, is often draft shape, the high 20-40 centimetre of stem.Branch is less, and woody stems is short and small, the shape of crawling; Sprig circle, to raw or verticillate, the long 2.5-6 centimetre of internode, 2 millimeters of diameters.
Main effective constituent in Chinese ephedra is alkaloid, example hydrochloric acid ephedrine, pseudoephedrine hydrochloride and N-Methylephedrine and demethyl ephedrine.
It is 200410042762.4 that State Intellectual Property Office discloses an application number in 2007.6.6, name is called the patent of invention of " Zeo-karb separates ephedrine method with expanding bed integrated technology single step purification ", this patent provides a kind of purification process of eco-friendly ephedrine, concrete steps are as follows: 2-3 times of buffer A diluted through conventional Chinese ephedra plant extraction method, synthesis method, the original liquid of the hydrochloric ephedrine through the processing of 0.05M dilute hydrochloric acid that microbe fermentation method or cell culture method obtain, adopt the one step absorption ephedrine hydrochloride of the expanding bed with particular design liquid distributor of polystyrene resin cation (R.C.) 001 × 7 Styrene DVB filling, adopt the 0.01M phosphate buffered saline buffer of the pH7.2 that contains 0.1M NaCl and 1.0M NaCl to carry out two step step elutes, collect the elutriant of second elution peak, obtain the ephedrine hydrochloride of purifying.Present method has been avoided the use of organic solvent dimethylbenzene, and the more traditional organic solvent extractionprocess of yield of product has improved 22%, reaches 86%, and product purity reaches 85%.
The method for purifying and separating of above-mentioned ephedrine cannot extract ephedrine efficiently, and technique is loaded down with trivial details, and cost is high.
Summary of the invention
The present invention is intended to solve in above-mentioned prior art and cannot extracts efficiently ephedrine, and technique is loaded down with trivial details, and the problem that cost is high provides a kind of extraction process of ephedrine, can extract fast and effectively the ephedrine in Chinese ephedra.
In order to realize foregoing invention object, its concrete technical scheme is as follows:
An extraction process for ephedrine, is characterized in that: comprise following processing step:
A, Chinese ephedra pre-treatment
Chinese ephedra is carried out to drying treatment, and removal of impurities is also pulverized, and obtains Ephedra;
B, alkalization
Ephedra is immersed in saturated sodium hydroxide, soaks 1-3 hour, filter, obtain the Ephedra that alkalizes;
C, dimethylbenzene extract
In the alkalization Ephedra obtaining in step B, add dimethylbenzene, described alkalization Ephedra and the mass volume ratio of dimethylbenzene are 1:2-5(g/ml), reflux, extracts 2-3 time, obtains dimethylbenzene extracting solution;
D, extraction
Think to add 2% oxalic acid in dimethylbenzene extracting solution, mix, in the water-bath of 50-80 DEG C, heat, obtain oxalic acid extraction liquid simultaneously;
E, concentrated
The oxalic acid extraction liquid concentrating under reduced pressure that step D is obtained, crystallisation by cooling obtains ephedrine solid extract.
Preferably, the present invention is in steps A, and described drying treatment is dry 2-5 hour at 70-80 DEG C.
Preferably, the present invention is in step C, and described Heating temperature is 80-105 DEG C.
Preferably, the present invention is in step C, and the described reflux time is 2-8 hour.
Preferably, the present invention is in step D, and the volume of 2% described oxalic acid is the 1/20-1/35 of dimethylbenzene extracting solution.
Preferably, the present invention, in step D, when described oxalic acid extraction liquid pH value is neutral, adds 2% oxalic acid, makes pH value remain 3-5.
The useful technique effect that the present invention brings:
1, alkalization, the dimethylbenzene that the present invention adopts extracts, the technique of oxalic acid extraction, can simplify loaded down with trivial details technique of the prior art, and fast and effeciently extract highly purified ephedrine.
2, before extraction, just Ephedra is immersed in saturated sodium hydroxide, soaks 1-3 hour, filters, and the alkalization process of this step can make Chinese ephedra technique in the time of extraction and purifying more smooth and easy, improves extraction yield and purification effect.
3, the processing parameter that the present invention adopts in step C and the processing parameter adopting in step D can effectively and stably extract in conjunction with dimethylbenzene and two steps of oxalic acid extraction, make two kinds of extraction effects reach best, improve follow-up purification effect.
Embodiment
embodiment 1
An extraction process for ephedrine, comprises following processing step:
A, Chinese ephedra pre-treatment
Chinese ephedra is carried out to drying treatment, and removal of impurities is also pulverized, and obtains Ephedra;
B, alkalization
Ephedra is immersed in saturated sodium hydroxide, soaks 1 hour, filter, obtain the Ephedra that alkalizes;
C, dimethylbenzene extract
In the alkalization Ephedra obtaining in step B, add dimethylbenzene, described alkalization Ephedra and the mass volume ratio of dimethylbenzene are 1:2, and reflux is extracted 2 times, obtains dimethylbenzene extracting solution;
D, extraction
Think to add 2% oxalic acid in dimethylbenzene extracting solution, mix, in the water-bath of 50 DEG C, heat, obtain oxalic acid extraction liquid simultaneously;
E, concentrated
The oxalic acid extraction liquid concentrating under reduced pressure that step D is obtained, crystallisation by cooling obtains ephedrine solid extract.
embodiment 2
An extraction process for ephedrine, comprises following processing step:
A, Chinese ephedra pre-treatment
Chinese ephedra is carried out to drying treatment, and removal of impurities is also pulverized, and obtains Ephedra;
B, alkalization
Ephedra is immersed in saturated sodium hydroxide, soaks 3 hours, filter, obtain the Ephedra that alkalizes;
C, dimethylbenzene extract
In the alkalization Ephedra obtaining in step B, add dimethylbenzene, described alkalization Ephedra and the mass volume ratio of dimethylbenzene are 1:5, and reflux is extracted 3 times, obtains dimethylbenzene extracting solution;
D, extraction
Think to add 2% oxalic acid in dimethylbenzene extracting solution, mix, in the water-bath of 80 DEG C, heat, obtain oxalic acid extraction liquid simultaneously;
E, concentrated
The oxalic acid extraction liquid concentrating under reduced pressure that step D is obtained, crystallisation by cooling obtains ephedrine solid extract.
embodiment 3
An extraction process for ephedrine, comprises following processing step:
A, Chinese ephedra pre-treatment
Chinese ephedra is carried out to drying treatment, and removal of impurities is also pulverized, and obtains Ephedra;
B, alkalization
Ephedra is immersed in saturated sodium hydroxide, soaks 2 hours, filter, obtain the Ephedra that alkalizes;
C, dimethylbenzene extract
In the alkalization Ephedra obtaining in step B, add dimethylbenzene, described alkalization Ephedra and the mass volume ratio of dimethylbenzene are 1:3.5, and reflux is extracted 3 times, obtains dimethylbenzene extracting solution;
D, extraction
Think to add 2% oxalic acid in dimethylbenzene extracting solution, mix, in the water-bath of 65 DEG C, heat, obtain oxalic acid extraction liquid simultaneously;
E, concentrated
The oxalic acid extraction liquid concentrating under reduced pressure that step D is obtained, crystallisation by cooling obtains ephedrine solid extract.
embodiment 4
On the basis of embodiment 1-3:
Preferably, the present invention is in steps A, and described drying treatment is to be dried 2 hours at 70 DEG C.
Preferably, the present invention is in step C, and described Heating temperature is 80 DEG C.
Preferably, the present invention is in step C, and the described reflux time is 2 hours.
Preferably, the present invention is in step D, and the volume of 2% described oxalic acid is 1/35 of dimethylbenzene extracting solution.
Preferably, the present invention, in step D, when described oxalic acid extraction liquid pH value is neutral, adds 2% oxalic acid, makes pH value remain 3.
embodiment 5
On the basis of embodiment 1-3:
Preferably, the present invention is in steps A, and described drying treatment is to be dried 5 hours at 80 DEG C.
Preferably, the present invention is in step C, and described Heating temperature is 105 DEG C.
Preferably, the present invention is in step C, and the described reflux time is 8 hours.
Preferably, the present invention is in step D, and the volume of 2% described oxalic acid is 1/20 of dimethylbenzene extracting solution.
Preferably, the present invention, in step D, when described oxalic acid extraction liquid pH value is neutral, adds 2% oxalic acid, makes pH value remain 5.
embodiment 6
On the basis of embodiment 1-3:
Preferably, the present invention is in steps A, and described drying treatment is to be dried 3.5 hours at 75 DEG C.
Preferably, the present invention is in step C, and described Heating temperature is 90 DEG C.
Preferably, the present invention is in step C, and the described reflux time is 5 hours.
Preferably, the present invention is in step D, and the volume of 2% described oxalic acid is 1/30 of dimethylbenzene extracting solution.
Preferably, the present invention, in step D, when described oxalic acid extraction liquid pH value is neutral, adds 2% oxalic acid, makes pH value remain 4.
Claims (6)
1. an extraction process for ephedrine, is characterized in that: comprise following processing step:
A, Chinese ephedra pre-treatment
Chinese ephedra is carried out to drying treatment, and removal of impurities is also pulverized, and obtains Ephedra;
B, alkalization
Ephedra is immersed in saturated sodium hydroxide, soaks 1-3 hour, filter, obtain the Ephedra that alkalizes;
C, dimethylbenzene extract
In the alkalization Ephedra obtaining in step B, add dimethylbenzene, described alkalization Ephedra and the mass volume ratio of dimethylbenzene are 1:2-5, and reflux, extracts 2-3 time, obtains dimethylbenzene extracting solution;
D, extraction
Think to add 2% oxalic acid in dimethylbenzene extracting solution, mix, in the water-bath of 50-80 DEG C, heat, obtain oxalic acid extraction liquid simultaneously;
E, concentrated
The oxalic acid extraction liquid concentrating under reduced pressure that step D is obtained, crystallisation by cooling obtains ephedrine solid extract.
2. the extraction process of a kind of ephedrine according to claim 1, is characterized in that: in steps A, described drying treatment is dry 2-5 hour at 70-80 DEG C.
3. the extraction process of a kind of ephedrine according to claim 1, is characterized in that: in step C, described Heating temperature is 80-105 DEG C.
4. the extraction process of a kind of ephedrine according to claim 1, is characterized in that: in step C, the described reflux time is 2-8 hour.
5. the extraction process of a kind of ephedrine according to claim 1, is characterized in that: in step D, the volume of 2% described oxalic acid is the 1/20-1/35 of dimethylbenzene extracting solution.
6. the extraction process of a kind of ephedrine according to claim 1, is characterized in that: in step D, when described oxalic acid extraction liquid pH value is neutral, add 2% oxalic acid, make pH value remain 3-5.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210489938.5A CN103833559A (en) | 2012-11-27 | 2012-11-27 | Extraction process of ephedrine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210489938.5A CN103833559A (en) | 2012-11-27 | 2012-11-27 | Extraction process of ephedrine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN103833559A true CN103833559A (en) | 2014-06-04 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201210489938.5A Pending CN103833559A (en) | 2012-11-27 | 2012-11-27 | Extraction process of ephedrine |
Country Status (1)
| Country | Link |
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| CN (1) | CN103833559A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106957234A (en) * | 2017-03-23 | 2017-07-18 | 陕西金冠牧业有限公司 | A kind of preparation method of pseudoephedrine hydrochloride |
| CN108823963A (en) * | 2018-07-24 | 2018-11-16 | 中国农业科学院麻类研究所 | A kind of Chinese fiber crops antibacterial fiber material preparation method |
| CN109251149A (en) * | 2018-09-13 | 2019-01-22 | 安徽佛子岭面业有限公司 | A method of extracting ephedrine from Chinese ephedra |
-
2012
- 2012-11-27 CN CN201210489938.5A patent/CN103833559A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106957234A (en) * | 2017-03-23 | 2017-07-18 | 陕西金冠牧业有限公司 | A kind of preparation method of pseudoephedrine hydrochloride |
| CN108823963A (en) * | 2018-07-24 | 2018-11-16 | 中国农业科学院麻类研究所 | A kind of Chinese fiber crops antibacterial fiber material preparation method |
| CN109251149A (en) * | 2018-09-13 | 2019-01-22 | 安徽佛子岭面业有限公司 | A method of extracting ephedrine from Chinese ephedra |
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Application publication date: 20140604 |