CN1132740A - Ephedrine extracting process - Google Patents
Ephedrine extracting process Download PDFInfo
- Publication number
- CN1132740A CN1132740A CN 95117443 CN95117443A CN1132740A CN 1132740 A CN1132740 A CN 1132740A CN 95117443 CN95117443 CN 95117443 CN 95117443 A CN95117443 A CN 95117443A CN 1132740 A CN1132740 A CN 1132740A
- Authority
- CN
- China
- Prior art keywords
- solvent
- ephedrine
- kerosene
- oxalic acid
- octanol
- 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.)
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- 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 40
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 229960002179 ephedrine Drugs 0.000 title claims abstract description 18
- 238000000034 method Methods 0.000 title claims abstract description 10
- 239000002904 solvent Substances 0.000 claims abstract description 24
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims abstract description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 18
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000003350 kerosene Substances 0.000 claims abstract description 13
- 238000000605 extraction Methods 0.000 claims abstract description 11
- 235000006408 oxalic acid Nutrition 0.000 claims abstract description 7
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 3
- 150000002191 fatty alcohols Chemical class 0.000 claims abstract description 3
- 239000003960 organic solvent Substances 0.000 claims abstract description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 claims description 22
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims description 8
- BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical compound CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- 238000005984 hydrogenation reaction Methods 0.000 claims description 5
- 239000012074 organic phase Substances 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 238000002425 crystallisation Methods 0.000 claims description 4
- 230000008025 crystallization Effects 0.000 claims description 4
- 229950003070 racephedrine Drugs 0.000 claims description 4
- 239000000243 solution Substances 0.000 claims description 4
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 3
- 239000000284 extract Substances 0.000 claims description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 3
- 229960003908 pseudoephedrine Drugs 0.000 claims description 3
- KWGRBVOPPLSCSI-WCBMZHEXSA-N pseudoephedrine Chemical compound CN[C@@H](C)[C@@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WCBMZHEXSA-N 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 238000004140 cleaning Methods 0.000 claims description 2
- 239000012141 concentrate Substances 0.000 claims description 2
- -1 crystallization Substances 0.000 claims description 2
- 238000005649 metathesis reaction Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 239000012188 paraffin wax Substances 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 239000006228 supernatant Substances 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 abstract description 2
- 230000003000 nontoxic effect Effects 0.000 abstract description 2
- 231100000419 toxicity Toxicity 0.000 abstract description 2
- 230000001988 toxicity Effects 0.000 abstract description 2
- 241000218671 Ephedra Species 0.000 abstract 1
- BALXUFOVQVENIU-GNAZCLTHSA-N Ephedrine hydrochloride Chemical compound Cl.CN[C@@H](C)[C@H](O)C1=CC=CC=C1 BALXUFOVQVENIU-GNAZCLTHSA-N 0.000 abstract 1
- 150000001335 aliphatic alkanes Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 229960002534 ephedrine hydrochloride Drugs 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- 229930013930 alkaloid Natural products 0.000 description 2
- 150000003797 alkaloid derivatives Chemical group 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 206010002198 Anaphylactic reaction Diseases 0.000 description 1
- 241000723281 Ephedra equisetina Species 0.000 description 1
- 241001465251 Ephedra sinica Species 0.000 description 1
- 230000036783 anaphylactic response Effects 0.000 description 1
- 208000003455 anaphylaxis Diseases 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 241000411851 herbal medicine Species 0.000 description 1
- BALXUFOVQVENIU-GHXDPTCOSA-N hydron;(1s,2r)-2-(methylamino)-1-phenylpropan-1-ol;chloride Chemical compound Cl.CN[C@H](C)[C@@H](O)C1=CC=CC=C1 BALXUFOVQVENIU-GHXDPTCOSA-N 0.000 description 1
- 208000030603 inherited susceptibility to asthma Diseases 0.000 description 1
- 210000002850 nasal mucosa Anatomy 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
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- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A process for extracting ephedrine features use of non-toxic extracting solvent instead of existing organic solvent for reducing toxicity of product and solvent consumption and increasing yield, and includes adding extractive liquid of ephedra herb with compound extracting solvent which may be C6-C8 fatty alcohols, kerosene, high-boiling-point straight chain alkane and aromatic hydrocarbon, toluene, or xylene, extraction, addition of solution of oxalic acid, back extraction, pressure reducing concentration and crystallizing to obtain ephedrine hydrochloride.
Description
The present invention relates to a kind of ephedrine extracting process, belong to the pharmaceutical technology field.
Racephedrine is the herbal medicine that has won fame both at home and abroad, and its medicinal effective constituent is alkaloid, mainly is contained in ephedra sinica and the ephedra equisetina, and its structural formula is
Be a basic cpd, so be referred to as ephedrine.This alkaloid mainly is made up of (one) ephedrine and (+) pseudoephedrine.Ephedrine is an adrenomimetic drug, the clinical treatment of conditions such as bronchial asthma, anaphylaxis, nasal mucosa swelling and ypotension that are used for, and medicinal racephedrine commonly used is its hydrochloride.The Production Flow Chart of racephedrine hydrochloride is shown in the technical process of Fig. 1 at present.In Herba Ephedrae production process shown in Figure 1, all adopt solvent extration from the Herba Ephedrae leach liquor, to extract ephedrine, and extraction solvent adopt toluene or dimethylbenzene more.The main drawback of this extraction process is: it is on the low side 1. to extract yield; 2. solvent loss is bigger than normal; 3. solvent is toxic.
The objective of the invention is to design a kind of new ephedrine extracting process, replace existing solvent with new nontoxic extraction solvent system replacement or part, and raising extracts yield, reduces solvent consumption.
The ephedrine extracting process of the present invention's design, form by following each step:
(1) gets the Herba Ephedrae leach liquor, add NaOH solution and transfer PH to 11.5-12.
(2) use double solvents that above-mentioned leach liquor is extracted by two kinds of solvent compositions, wherein first solvent is any in the Fatty Alcohol(C12-C14 and C12-C18) of 6-8 carbon, comprise hexanol, hexalin, enanthol and octanol (n-Octanol, isooctyl alcohol, secondary octanol), second solvent is any in kerosene (hydrogenation kerosene, sulfonated kerosene), high boiling straight-chain paraffin and the aromatic hydrocarbons, if do not consider toxicity, also can adopt toluene, dimethylbenzene as second solvent, the volume ratio between first kind of solvent and the second kind of solvent is 1: 0-10; Two kinds of solvents can be formed different permutation and combination.The extracting operation temperature is 40-80 ℃, and extract stream is 0.6-1.2: 1 than organic phase and water volume ratio.
(3) with above-mentioned come together organic phase concentration be that 5-10% oxalic acid aqueous solution is stripped, the back extraction temperature is room temperature or a little higher than room temperature, and is multiplexing after the organic solvent alkali cleaning after the back extraction.
(4) to the aqueous solution of above-mentioned strip liquor after concentrating under reduced pressure, crystallization, (+) pseudoephedrine is separated with oxalic acid (one) ephedrine, in oxalic acid (one) ephedrine, add saturated CaCl by stoichiometric relation
2Solution is made replacement(metathesis)reaction, to reacted supernatant liquor decolour, concentrate, crystallization, hydrochloric acid (one) ephedrine, be racephedrine.
Description of drawings:
Fig. 1 is the prior art process flow sheet.
Table 1 is embodiments of the invention.
Table 1: process implementing example
| Sequence number | The ephedrine input concentration | Extraction system | Benzene is got stream than (organic phase and water volume ratio) | Percentage extraction % |
| ????1 | ?????0.15％ | 20% isooctyl alcohol+80% dimethylbenzene | ??????0.8∶1 | ????99.0％ |
| ????2 | ?????0.1％ | 30% isooctyl alcohol+70% hydrogenation kerosene | ????????1∶1 | ????99.5％ |
| ????3 | ?????0.1％ | 20% secondary octanol+80% dimethylbenzene | ????????1∶1 | ????99.0％ |
| ????4 | ?????0.08％ | 30% secondary octanol+70% sulfonated kerosene | ??????0.6∶1 | ????98.5％ |
| ????5 | ?????0.06％ | 20% n-hexyl alcohol+80% toluene | ??????0.8∶1 | ????99.2％ |
| ????6 | ?????0.06％ | 10% isooctyl alcohol+90% toluene | ??????1.2∶1 | ????98.0％ |
| ????7 | ?????0.1％ | 100% isooctyl alcohol | ??????0.6∶1 | ????99.0％ |
| ????8 | ?????0.05％ | 80% n-hexyl alcohol+20% dimethylbenzene | ??????0.6∶1 | ????99.2％ |
| ????9 | ?????0.05％ | 60% n-Octanol+40% sulfonated kerosene | ??????0.8∶1 | ????99.6％ |
| ????10 | ?????0.08％ | 60% n-Heptyl alcohol+50% hydrogenation kerosene | ??????0.9∶1 | ????99.2％ |
| ????11 | ?????0.08％ | 40% secondary octanol+60% hydrogenation kerosene | ??????0.8∶1 | ????98.5％ |
| ????12 | ?????0.08％ | 100% secondary octanol | ??????0.6∶1 | ????99.1％ |
| ????13 | ?????0.08％ | 30% hexalin+70% kerosene | ????????1∶1 | ????98.5％ |
Claims (1)
1, a kind of ephedrine extracting process is characterized in that this technology is made up of following each step:
(1) gets the Herba Ephedrae leach liquor, add NaOH solution and transfer PH to 11.5-12;
(2) use double solvents that above-mentioned leach liquor is extracted by two kinds of solvent compositions, wherein first solvent is any in the Fatty Alcohol(C12-C14 and C12-C18) of 6-8 carbon, comprise hexanol, hexalin, enanthol and octanol (n-Octanol, isooctyl alcohol, secondary octanol), second solvent is any in kerosene (hydrogenation kerosene, sulfonated kerosene), high boiling straight-chain paraffin and aromatic hydrocarbons or toluene, the dimethylbenzene, and the volume ratio between first kind of solvent and the second kind of solvent is 1: 0-10; The extracting operation temperature is 40-80 ℃, and extract stream is 0.6-1.2: 1 than organic phase and water volume ratio;
(3) with above-mentioned come together organic phase concentration be that 5-10% oxalic acid aqueous solution is stripped, the back extraction temperature is room temperature or a little higher than room temperature, and is multiplexing after the organic solvent alkali cleaning after the back extraction;
(4) to the aqueous solution of above-mentioned strip liquor after concentrating under reduced pressure, crystallization, (+) pseudoephedrine is separated with oxalic acid (one) ephedrine, in oxalic acid (one) ephedrine, add saturated CaCl by stoichiometric relation
2Solution is made replacement(metathesis)reaction, to reacted supernatant liquor decolour, concentrate, crystallization, hydrochloric acid (one) ephedrine, be racephedrine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN95117443A CN1054120C (en) | 1995-11-10 | 1995-11-10 | Ephedrine extracting process |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN95117443A CN1054120C (en) | 1995-11-10 | 1995-11-10 | Ephedrine extracting process |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1132740A true CN1132740A (en) | 1996-10-09 |
| CN1054120C CN1054120C (en) | 2000-07-05 |
Family
ID=5081233
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN95117443A Expired - Fee Related CN1054120C (en) | 1995-11-10 | 1995-11-10 | Ephedrine extracting process |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1054120C (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1061643C (en) * | 1996-10-15 | 2001-02-07 | 薄学璞 | Ephedrine leaching method |
| 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 |
| CN107892652A (en) * | 2017-11-07 | 2018-04-10 | 何本科 | A kind of extracting method of ephedrine |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55122786A (en) * | 1979-03-15 | 1980-09-20 | Takeda Chem Ind Ltd | Ephedrazine compound and its preparation |
| JPS5857383A (en) * | 1981-10-01 | 1983-04-05 | Suntory Ltd | Novel flavonoid |
| JPS61263925A (en) * | 1985-05-20 | 1986-11-21 | Kanebo Ltd | Carcinostatic adjuvant |
-
1995
- 1995-11-10 CN CN95117443A patent/CN1054120C/en not_active Expired - Fee Related
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1061643C (en) * | 1996-10-15 | 2001-02-07 | 薄学璞 | Ephedrine leaching method |
| 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 |
| CN107892652A (en) * | 2017-11-07 | 2018-04-10 | 何本科 | A kind of extracting method of ephedrine |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1054120C (en) | 2000-07-05 |
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| C06 | Publication | ||
| PB01 | Publication | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
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