GB645876A - Improvements in and relating to the extraction and purification of organic compounds - Google Patents
Improvements in and relating to the extraction and purification of organic compoundsInfo
- Publication number
- GB645876A GB645876A GB12763/47A GB1276347A GB645876A GB 645876 A GB645876 A GB 645876A GB 12763/47 A GB12763/47 A GB 12763/47A GB 1276347 A GB1276347 A GB 1276347A GB 645876 A GB645876 A GB 645876A
- Authority
- GB
- United Kingdom
- Prior art keywords
- membrane
- solvent
- solution
- hyoscyamine
- outlet
- 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.)
- Expired
Links
- 238000000605 extraction Methods 0.000 title abstract 6
- 150000002894 organic compounds Chemical class 0.000 title 1
- 238000000746 purification Methods 0.000 title 1
- 239000002904 solvent Substances 0.000 abstract 32
- 239000012528 membrane Substances 0.000 abstract 24
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 abstract 12
- 239000000243 solution Substances 0.000 abstract 12
- 239000000126 substance Substances 0.000 abstract 10
- RKUNBYITZUJHSG-FXUDXRNXSA-N (S)-atropine Chemical compound C1([C@@H](CO)C(=O)O[C@H]2C[C@H]3CC[C@@H](C2)N3C)=CC=CC=C1 RKUNBYITZUJHSG-FXUDXRNXSA-N 0.000 abstract 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 8
- STECJAGHUSJQJN-GAUPFVANSA-N Hyoscine Natural products C1([C@H](CO)C(=O)OC2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-GAUPFVANSA-N 0.000 abstract 8
- STECJAGHUSJQJN-UHFFFAOYSA-N N-Methyl-scopolamin Natural products C1C(C2C3O2)N(C)C3CC1OC(=O)C(CO)C1=CC=CC=C1 STECJAGHUSJQJN-UHFFFAOYSA-N 0.000 abstract 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 abstract 8
- 229930005342 hyoscyamine Natural products 0.000 abstract 8
- 229960003210 hyoscyamine Drugs 0.000 abstract 8
- 239000007788 liquid Substances 0.000 abstract 8
- 229960002646 scopolamine Drugs 0.000 abstract 8
- STECJAGHUSJQJN-FWXGHANASA-N scopolamine Chemical compound C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-FWXGHANASA-N 0.000 abstract 8
- 229930013930 alkaloid Natural products 0.000 abstract 6
- 229920000915 polyvinyl chloride Polymers 0.000 abstract 6
- 239000004800 polyvinyl chloride Substances 0.000 abstract 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 abstract 4
- 229930003347 Atropine Natural products 0.000 abstract 4
- BXSVDJUWKSRQMD-ITMJLNKNSA-N O.O.CN1[C@@H]2CC[C@H]1C[C@H](C2)OC(=O)[C@H](CO)c3ccccc3.CN4[C@@H]5CC[C@H]4C[C@H](C5)OC(=O)[C@H](CO)c6ccccc6.OS(=O)(=O)O Chemical compound O.O.CN1[C@@H]2CC[C@H]1C[C@H](C2)OC(=O)[C@H](CO)c3ccccc3.CN4[C@@H]5CC[C@H]4C[C@H](C5)OC(=O)[C@H](CO)c6ccccc6.OS(=O)(=O)O BXSVDJUWKSRQMD-ITMJLNKNSA-N 0.000 abstract 4
- 229960000396 atropine Drugs 0.000 abstract 4
- RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 abstract 4
- 239000012530 fluid Substances 0.000 abstract 4
- 239000011521 glass Substances 0.000 abstract 4
- 229920006395 saturated elastomer Polymers 0.000 abstract 4
- 238000000926 separation method Methods 0.000 abstract 4
- 229920001817 Agar Polymers 0.000 abstract 2
- GERIGMSHTUAXSI-UHFFFAOYSA-N Belladonnin Natural products CN1C(C2)CCC1CC2OC(=O)C(C1=CC=CC=C11)CCC1(C(=O)OC1CC2CCC(N2C)C1)C1=CC=CC=C1 GERIGMSHTUAXSI-UHFFFAOYSA-N 0.000 abstract 2
- GERIGMSHTUAXSI-KZYONXTKSA-N Belladonnine Chemical compound C1([C@]2(CC[C@@H](C3=CC=CC=C32)C(=O)OC2CC3CCC(C2)N3C)C(=O)OC2CC3CCC(N3C)C2)=CC=CC=C1 GERIGMSHTUAXSI-KZYONXTKSA-N 0.000 abstract 2
- GERIGMSHTUAXSI-ALLNTMHVSA-N Belladonnine Natural products O=C(OC1C[C@H]2N(C)[C@H](C1)CC2)[C@@H]1c2c([C@@](C(=O)OC3C[C@@H]4N(C)[C@H](C3)CC4)(c3ccccc3)CC1)cccc2 GERIGMSHTUAXSI-ALLNTMHVSA-N 0.000 abstract 2
- 241000206672 Gelidium Species 0.000 abstract 2
- 241001495123 Hyoscyamus muticus Species 0.000 abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 2
- 235000010419 agar Nutrition 0.000 abstract 2
- 239000012670 alkaline solution Substances 0.000 abstract 2
- 229940072049 amyl acetate Drugs 0.000 abstract 2
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 abstract 2
- 239000007864 aqueous solution Substances 0.000 abstract 2
- 229920001971 elastomer Polymers 0.000 abstract 2
- 239000004744 fabric Substances 0.000 abstract 2
- 238000005194 fractionation Methods 0.000 abstract 2
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 abstract 2
- 230000002209 hydrophobic effect Effects 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 239000011088 parchment paper Substances 0.000 abstract 2
- 230000000149 penetrating effect Effects 0.000 abstract 2
- 229920000642 polymer Polymers 0.000 abstract 2
- 239000005060 rubber Substances 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 2
- 235000011149 sulphuric acid Nutrition 0.000 abstract 2
- 239000001117 sulphuric acid Substances 0.000 abstract 2
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
- B01D61/24—Dialysis ; Membrane extraction
- B01D61/246—Membrane extraction
Landscapes
- Health & Medical Sciences (AREA)
- Urology & Nephrology (AREA)
- Engineering & Computer Science (AREA)
- Water Supply & Treatment (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Extraction Or Liquid Replacement (AREA)
Abstract
<PICT:0645876/IV (b)/1> The extraction of organic substances, e.g. alkaloids, in solution in one solvent is effected by another solvent, the two liquids being separated by a membrane which is permeable to the substance but not to more than one of the solvents and is insoluble in both solvents under the conditions of operation. If the two solvents are miscible, as in the case of water of different pH values, the membrane is impermeable to both liquids. If the solvents are immiscible and the membrane is permeable to one solvent only, an excess pressure is maintained on the second solvent in order to prevent the first solvent from penetrating the membrane. The membrane, which may be in tubular or sheet form and supported if desired, is saturated either with water (hydrophilic) or with a water immiscible solvent (hydrophobic) and may be made from parchment paper, agar-agar, rubber or polyvinyl chloride. A preferred membrane is one of polyvinyl chloride made by passing a fabric through a hot solution of the polymer, the membrane being saturated with a suitable solvent such as chloroform, chlorobenzene, o-dichlorobenzene and amyl acetate or a blend of solvents which swell the membrane to a suitable degree. The process may be employed for the separation of two organic substances, e.g. hyoscine from hyoscyamine, by countercurrent extraction fractionation, or for the separation of crystal-line substances from resinous bodies of otherwise similar chemical structure, as for example, atropine and belladonnine. As applied to the extraction of hyoscine and hyoscyamine (including atropine) from an alkaline aqueous solution of hyoscyamus muticus, a polyvinyl chloride tubular membrane 1 is employed. The membrane is enclosed by a spaced glass tube 2, the aqueous liquids passing through the space between the glass and the membrane and the immiscible solvent passing countercurrently inside the tubular membrane. An excess pressure is maintained on the aqueous liquid. In stage 1, the aqueous alkaline solution flows into tube 2 through pipe 3 and the alkaloids are extracted by a solvent, e.g. chloroform or chlorobenzene flowing countercurrently through pipe 4. In stage 2 the alkaloids are extracted from the solvent in pipe 4 by N/10 sulphuric acid flowing countercurrently through entry 5 into tube 2; Substage A strips the fluid issuing at outlet 7 of hyoscyamine which is returned to stage 2 in solution in the solvent. Substage B strips the fluid issuing at outlet 6 of hyoscine which is returned to the appropriate place in stage 2. A solution of the salts of volatile bases with some hyoscyamine sulphate is obtained from outlet 10, a solution of pure hyoscyamine sulphate from outlet 11 and a solution of hyoscine sulphate mixed with some hyoscyamine from outlet 8.ALSO:<PICT:0645876/III/1> The extraction of organic substances, e.g. alkaloids, in solution in one solvent is effected by another solvent, the two liquids being separated by a membrane which is permeable to the substance but not to more than one of the solvents and is insoluble in both solvents under the conditions of operation. If the two solvents are miscible, as in the case of water of different pH values, the membrane is impermeable to both liquids. If the solvents are immiscible and the membrane is permeable to one solvent only, an excess pressure is maintained on the second solvent in order to prevent the first solvent from penetrating the membrane. The membrane, which may be in tubular or sheet form and supported if desired, is saturated either with water (hydrophilic) or with a water-immiscible solvent (hydrophobic) and may be made from parchment paper, agar-agar, rubber or polyvinyl chloride. A preferred membrane is one of polyvinyl chloride made by passing a fabric through a hot solution of the polymer, the membrane being saturated with a suitable solvent such as chloroform, chlorobenzene, o-dichlorobenzene and amyl acetate or a blend of solvents which swell the membrane to a suitable degree. The process may be employed for the separation of two organic substances, e.g. hyoscine from hyoscyamine, by counter-current extractive fractionation, or for the separation of crystalline substances from resinous bodies of otherwise similar chemical structure, as, for example, atropine and belladonnine. As applied to the extraction of hyoscine and hyoscyamine (including atropine) from an alkaline aqueous solution of hyoscyamus muticus, a polyvinyl chloride tubular membrane 1 is employed. The membrane is enclosed by a spaced glass tube 2, the aqueous liquids passing through the space between the glass and the membrane and the immiscible solvent passing countercurrently inside the tubular membrane. An excess pressure is maintained on the aqueous liquid. In stage 1, the aqueous alkaline solution flows into tube 2 through pipe 3 and the alkaloids are extracted by a solvent, e.g. chloroform or chlorobenzene flowing countercurrently through pipe 4. In stage 2 the alkaloids are extracted from the solvent in pipe 4 by N/10 sulphuric acid flowing countercurrently through entry 5 into tube 2. Substage A strips the fluid issuing at outlet 7 of hyoscyamine which is returned to stage 2 in solution in the solvent. Substage B strips the fluid issuing at outlet 6 of hyoscine which is returned to the appropriate place in stage 2. A solution of the salts of volatile bases with some hyoscyamine sulphate is obtained from outlet 10, a solution of pure hyoscyamine sulphate from outlet 11 and a solution of hyoscine sulphate mixed with some hyoscyamine from outlet 8.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB12763/47A GB645876A (en) | 1947-05-12 | 1947-05-12 | Improvements in and relating to the extraction and purification of organic compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB12763/47A GB645876A (en) | 1947-05-12 | 1947-05-12 | Improvements in and relating to the extraction and purification of organic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB645876A true GB645876A (en) | 1950-11-08 |
Family
ID=10010676
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB12763/47A Expired GB645876A (en) | 1947-05-12 | 1947-05-12 | Improvements in and relating to the extraction and purification of organic compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB645876A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2212163A1 (en) * | 1973-01-02 | 1974-07-26 | Allied Chem | |
| FR2333546A1 (en) * | 1975-12-01 | 1977-07-01 | Monsanto Co | PROCESS FOR SEPARATION BY MEMBRANE OF NEUTRAL ORGANIC PRODUCTS FROM AN AQUEOUS SOLUTION AND NEW PRODUCTS THUS OBTAINED |
| FR2404404A1 (en) * | 1977-09-28 | 1979-04-27 | Gen Foods Corp | DECAFEINATION USING MEMBRANES |
| EP0088458A2 (en) * | 1982-03-04 | 1983-09-14 | Shell Internationale Researchmaatschappij B.V. | Process for the separation of a liquid mixture |
| GB2399039A (en) * | 2003-03-07 | 2004-09-08 | Membrane Extraction Tech Ltd | Removal of undissociated organic acids or bases from a fluid stream |
-
1947
- 1947-05-12 GB GB12763/47A patent/GB645876A/en not_active Expired
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2212163A1 (en) * | 1973-01-02 | 1974-07-26 | Allied Chem | |
| FR2333546A1 (en) * | 1975-12-01 | 1977-07-01 | Monsanto Co | PROCESS FOR SEPARATION BY MEMBRANE OF NEUTRAL ORGANIC PRODUCTS FROM AN AQUEOUS SOLUTION AND NEW PRODUCTS THUS OBTAINED |
| FR2404404A1 (en) * | 1977-09-28 | 1979-04-27 | Gen Foods Corp | DECAFEINATION USING MEMBRANES |
| EP0088458A2 (en) * | 1982-03-04 | 1983-09-14 | Shell Internationale Researchmaatschappij B.V. | Process for the separation of a liquid mixture |
| EP0088458A3 (en) * | 1982-03-04 | 1984-03-07 | Shell Internationale Research Maatschappij B.V. | Process for the separation of a liquid mixture |
| GB2399039A (en) * | 2003-03-07 | 2004-09-08 | Membrane Extraction Tech Ltd | Removal of undissociated organic acids or bases from a fluid stream |
| GB2399039B (en) * | 2003-03-07 | 2005-05-25 | Membrane Extraction Tech Ltd | Process for removing undissociated organic acids or bases dissolved in a fluid stream |
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