PL424B1 - Method of obtaining ricinostearolic acid diiodide. - Google Patents
Method of obtaining ricinostearolic acid diiodide. Download PDFInfo
- Publication number
- PL424B1 PL424B1 PL424A PL42420A PL424B1 PL 424 B1 PL424 B1 PL 424B1 PL 424 A PL424 A PL 424A PL 42420 A PL42420 A PL 42420A PL 424 B1 PL424 B1 PL 424B1
- Authority
- PL
- Poland
- Prior art keywords
- acid
- obtaining
- ricinostearolic
- acetic acid
- iodine
- Prior art date
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- 239000002253 acid Substances 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 20
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 239000011630 iodine Substances 0.000 claims description 6
- WLIGEPWCQYIUNZ-QGZVFWFLSA-N (12r)-12-hydroxyoctadec-9-ynoic acid Chemical compound CCCCCC[C@@H](O)CC#CCCCCCCCC(O)=O WLIGEPWCQYIUNZ-QGZVFWFLSA-N 0.000 claims description 3
- 230000026045 iodination Effects 0.000 claims 1
- 238000006192 iodination reaction Methods 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 229960000583 acetic acid Drugs 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 2
- 239000002934 diuretic Substances 0.000 description 2
- 230000001882 diuretic effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- 244000075850 Avena orientalis Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
Description
Wedlug sposobu Arnaud i Poster- nack'a jod daje sie latwo przylaczyc w roztworze lodowatego kwasu octowego do kwasów szeregu Cn H2n-4 02; taka reakcja daje sie przeniesc i na kwas ry- cynostearolowy, jednak obecnosc grupy wodorotlenowej pobudza kwas rycyno- stearolowy do róznych reakcji pobocz¬ nych (Berichte 46, Str. 2091). Z jednej strony wystepuje duzo smaru przy two¬ rzeniu sie ciemno-zabarwionych produk¬ tów-, z drugiej strony kwas rycynostearo- lowy podlega acetylowaniu, dzieki czemu wytworzony dwujodek kwasu rycynoste¬ arolowego jest stale mocno zanieczysz¬ czony przez oleiste dodatki. Wystepo¬ wania tych produktów pobocznych trzeba w ten sposób unikac, ze kwas rycyno- stearolowy joduje sie przy 40°, lub przy zwyklej temperaturze, w ciagu 40 godzin (loc. cit.).Przylaczenie jodu jest prawie ilo¬ sciowe, jednakze i dwujodek otrzymany w ten sposób jest zanieczyszczony ciem- nemi, lepkiemi produktami, które znacz¬ nie zmniejszaja i wydajnosc czystego, kry¬ stalicznego dwujodku i odpornosc suro¬ wego dwujodku na srodki rozpuszcza¬ jace. W znacznie silniejszym stopniu daje sie stwierdzic szkodliwy wplyw kwasu octowego, jesli pracowac wedlug wskazanego sposobu na wieksza skale.Tymczasem stwierdzono, ze mozna uniknac acetylowania i kondensacji, wy¬ wolywanej przez nadmiar kwasu octo¬ wego, juz przy zwyklej temperaturze, a takze i wystepowania wtedy szkodli¬ wych produktów ubocznych, jezeli jodo-wac w wodnym roztworze kwasu octo¬ wego. Po wydzieleniu niewielkiej ilosci nadmiaru jodu otrzymuje sie, bez dalszej przeróbki, przez krystalizacje masy re¬ akcyjnej i stracenie lugu pokrystalicznego woda, staly, prawie bezbarwny dwujo- dek, który mozna latwo przekrystali- zowac.Otrzymany produkt moze miec, jako taki, zastosowanie terapeutyczne.Przyklad. Rozpuszcza sie przy zupel¬ nie slabem ogrzewaniu 100 cz. kwasu ry- cynostearolowego w mniej wiecej 250 cz. 75°/0 kwasu octowego i dodaje odrazu obliczona ilosc jodu do roztworu. Na¬ stepnie wstrzasa sie lub miesza mocno przy zwyklej temperaturze, dopóki wszy¬ stek jod nie przejdzie do roztworu. Masa reakcyjna zastyga wkrótce na kasze kry¬ staliczna, zadaje sie taka sama objetoscia wody, a obecne male ilosci nadmiaru jodu wydziela sie kwasem siarkawym. Po¬ wstaly, prawie czysty, d wuj odek kwasu rycynostearolowego odsacza sie i prze¬ mywa woda. Preparat po jednorazowem przekrystalizowaniu jest zupelnie czysty. PLAccording to the method of Arnaud and Pernack, iodine can be easily attached in glacial acetic acid solution to acids of the Cn H2n-4 02 series; such a reaction is transferable to ricinostearolic acid, but the presence of the hydroxyl group induces ricin-stearolic acid into various side reactions (Berichte 46, p. 2091). On the one hand, a lot of lubricant is present in the formation of dark-colored products, and on the other hand, ricinostearolic acid is acetylated, so that the produced ricinostearol acid diodeide is constantly heavily contaminated by oily additives. The occurrence of these byproducts must thus be avoided that ricinstearolic acid is iodinated at 40 ° C, or at ordinary temperature, for 40 hours (loc. Cit.). The incorporation of iodine is almost quantitative, however, the diuretic the resultant material is contaminated with dark, sticky products which greatly reduce the yield of pure crystalline diodide and the resistance of the crude di-iodide to dissolving agents. The detrimental effect of acetic acid can be found to a much greater extent when working as indicated on a larger scale, while it has been found that acetylation and condensation, caused by excess acetic acid, can be avoided even at ordinary temperature, as well as the presence of then harmful by-products if iodinate in aqueous acetic acid. After the isolation of a small amount of excess iodine, the crystallization of the reaction mass and loss of the post-crystalline slurry with water are obtained, without further processing, a solid, almost colorless diuretic that can easily be recrystallized. .Example. It dissolves with completely weak heating of 100 parts. of ricinostearolic acid in about 250 parts. 75% acetic acid and immediately adds the calculated amount of iodine to the solution. The mixture is then shaken or stirred vigorously at ordinary temperature until all the iodine is in solution. The reaction mass soon solidifies to a crystalline groats, the same volume of water is added, and the small amounts of excess iodine present are released with sulfurous acid. The resulting, almost pure, ricinostearolic acid stomach is drained off and washed with water. After recrystallization once, the preparation is completely pure. PL
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL424B1 true PL424B1 (en) | 1924-08-30 |
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