PL19505B1 - The method of obtaining adenosine phosphoric acid. - Google Patents
The method of obtaining adenosine phosphoric acid. Download PDFInfo
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- PL19505B1 PL19505B1 PL19505A PL1950532A PL19505B1 PL 19505 B1 PL19505 B1 PL 19505B1 PL 19505 A PL19505 A PL 19505A PL 1950532 A PL1950532 A PL 1950532A PL 19505 B1 PL19505 B1 PL 19505B1
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- Prior art keywords
- phosphoric acid
- barium
- calcium
- adenosine phosphoric
- acid
- Prior art date
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- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 title claims description 25
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 title claims description 24
- 239000002126 C01EB10 - Adenosine Substances 0.000 title claims description 13
- 229960005305 adenosine Drugs 0.000 title claims description 13
- 229910000147 aluminium phosphate Inorganic materials 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 7
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims description 6
- 210000003205 muscle Anatomy 0.000 claims description 6
- 210000001557 animal structure Anatomy 0.000 claims description 5
- 229910052788 barium Inorganic materials 0.000 claims description 5
- 239000000706 filtrate Substances 0.000 claims description 5
- AUHDWARTFSKSAC-HEIFUQTGSA-N (2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)-2-(6-oxo-1H-purin-9-yl)oxolane-2-carboxylic acid Chemical compound [C@]1([C@H](O)[C@H](O)[C@@H](CO)O1)(N1C=NC=2C(O)=NC=NC12)C(=O)O AUHDWARTFSKSAC-HEIFUQTGSA-N 0.000 claims description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 4
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 4
- 229910001863 barium hydroxide Inorganic materials 0.000 claims description 4
- 239000011575 calcium Substances 0.000 claims description 4
- 229910052791 calcium Inorganic materials 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 238000002425 crystallisation Methods 0.000 claims description 4
- 230000008025 crystallization Effects 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- GRSZFWQUAKGDAV-UHFFFAOYSA-N Inosinic acid Natural products OC1C(O)C(COP(O)(O)=O)OC1N1C(NC=NC2=O)=C2N=C1 GRSZFWQUAKGDAV-UHFFFAOYSA-N 0.000 claims description 3
- 159000000009 barium salts Chemical class 0.000 claims description 3
- 239000000284 extract Substances 0.000 claims description 3
- 229910052816 inorganic phosphate Inorganic materials 0.000 claims description 3
- 229940028843 inosinic acid Drugs 0.000 claims description 3
- 235000013902 inosinic acid Nutrition 0.000 claims description 3
- 239000004245 inosinic acid Substances 0.000 claims description 3
- 239000002002 slurry Substances 0.000 claims description 3
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 2
- 239000000920 calcium hydroxide Substances 0.000 claims description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000000354 decomposition reaction Methods 0.000 claims description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 2
- -1 adenosine phosphoric acid salt Chemical class 0.000 claims 2
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- 235000021317 phosphate Nutrition 0.000 claims 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 150000002903 organophosphorus compounds Chemical class 0.000 description 3
- 239000010802 sludge Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WRYNUJYAXVDTCB-UHFFFAOYSA-M acetyloxymercury Chemical compound CC(=O)O[Hg] WRYNUJYAXVDTCB-UHFFFAOYSA-M 0.000 description 2
- 239000006286 aqueous extract Substances 0.000 description 2
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 159000000007 calcium salts Chemical class 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 210000004907 gland Anatomy 0.000 description 2
- 210000002216 heart Anatomy 0.000 description 2
- 229940046892 lead acetate Drugs 0.000 description 2
- 210000000944 nerve tissue Anatomy 0.000 description 2
- 150000003018 phosphorus compounds Chemical class 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- 241001192924 Parna Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- XRBNGVUPCIBZIL-MCDZGGTQSA-L barium(2+);[(2r,3s,4r,5r)-3,4-dihydroxy-5-(6-oxo-3h-purin-9-yl)oxolan-2-yl]methyl phosphate Chemical compound [Ba+2].O[C@@H]1[C@H](O)[C@@H](COP([O-])([O-])=O)O[C@H]1N1C(NC=NC2=O)=C2N=C1 XRBNGVUPCIBZIL-MCDZGGTQSA-L 0.000 description 1
- AYJRCSIUFZENHW-DEQYMQKBSA-L barium(2+);oxomethanediolate Chemical compound [Ba+2].[O-][14C]([O-])=O AYJRCSIUFZENHW-DEQYMQKBSA-L 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- XCAUINMIESBTBL-UHFFFAOYSA-N lead(ii) sulfide Chemical compound [Pb]=S XCAUINMIESBTBL-UHFFFAOYSA-N 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- QXKXDIKCIPXUPL-UHFFFAOYSA-N sulfanylidenemercury Chemical compound [Hg]=S QXKXDIKCIPXUPL-UHFFFAOYSA-N 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
Description
Wiadomo, ze wszystkie narzady zwie¬ rzece (krew, serce, miesnie, tkanka nerwo¬ wa, mózg, gruczoly, jak nerka, watroba i t. d.) oraz drozdze zawieraja wolny kwas adenozynofosforowy miesniowy (Drury i Szent-Gyórgy, Parnas i Ostern i in.). Zna¬ ne dotychczas sposoby otrzymywania tego kwasu, podane przez Embdena i Zimmer- manna, Lohmanna, A. Hahna i i. wymagaja znacznych ilosci kosztownych odczynników i daja w rezultacie tylko bardzo male ilosci czystego kwasu adenozynofosforowego. We¬ dlug sposobów tych sporzadza sie z narza¬ dów zwierzecych wyciag wodny, który od- bialcza sie zupelnie kwasem trójchloro- octowym albo sublimatem i kwasem solnym.Nastepnie wytraca sie z odbialczonego wy¬ ciagu wszystkie zwiazki fosforowe razem, zarówno nieorganiczne jak i organiczne, za- pomoca octanu rteci lub olowiu i oczyszcza osad zapomoca róznych zabiegów z zawar¬ tosci nieorganicznych a nastepnie organicz¬ nych, fizjologicznie nieczynnych, zwiazków fosforowych az do izolowania kwasu adeno¬ zynofosforowego, który otrzymuje sie wreszcie z rozczynu wodno-acetonowego przez krystalizacje.Wynalazek niniejszy polega na tern, ze wyciag wodny z narzadów zwierzecych jak np. z krwi, serc, miesni, tkanki nerwowej,gruczolów i t d. albo z drozdzy piwnych odbialcza sie poczatkowo tylko zgrubsza przez zagotowanie z mala iloscia kwasu octowego i nastepujace zobojetnienie zapo- moca lugu sodowego lub potasowego, po- czem wodorotlenkiem baru albo wapnia straca sie tylko fosforany nieorganiczne a z przesaczu otrzymuje organiczne zwiazki fo¬ sforowe, jako sole olowiowe, przez zada¬ nie octanem olowiu. Po rozlozeniu soli olo¬ wiowych zapomoca siarkowodoru zageszcza sie przesacz tak, aby przez krystalizacje wydzielic zen sól barowa wzglednie wapnio¬ wa kwasu inozynowego a utrzymac w roz¬ tworze latwiej rozpuszczalna i nie krystali¬ zujaca sól kwasu adenozynofosforowego.Rozdzielenie solKobu tych kwasów w tern stadjum przeróbki umozliwia otrzymanie pózniejsze czystego kwasu adenozynofosfo¬ rowego miesniowego, który w przeciwsta¬ wieniu do swych soli barowych i wapniowych krystalizuje z wyciagu wodnego, podczas kiedy naodwrót kwas inozynowy tworzy niekrystalizujaca mase o konsystencji syro¬ pu. Po odsaczeniu soli kwasu inozynowego wytraca sie z przesaczu sól barowa wzgl. wapniowa kwasu adenozynofosforowego oc¬ tanem rteci i uwalnia sie ja od baru wzgl. wapnia a wreszcie otrzymuje sie wolny kwas adenozynofosforowy miesniowy przez krystalizacje z rozczynu wodno-alkoholowe- go. Sposób ten wymaga tylko tanich wzgl. nieznacznych ilosci kosztownych odczynni¬ ków i daje znaczna czesc kwasu adenozyno¬ fosforowego zawartego w wyjsciowych na¬ rzadach zwierzecych albo drozdzach.Przyklad I. 10 kg swiezych miesni zwierzecych gotuje sie przez kilka minut z równa iloscia wody. Podczas wrzenia doda¬ je sie kwasu octowego az do oddzialywania kwasnego na lakmus, nastepnie lugu sodo¬ wego do reakcji slabo alkalicznej, wreszcie znowu odrobiny kwasu octowego az do reakcji slabo kwasnej.Miazge zagotowana oziebia sie szybko i przesacza, przesacz zadaje wodorotlenkiem baru az do zupelnego wytracenia fosfora¬ nów nieorganicznych i odwirowuje albo odsacza. Po oddzieleniu osadu zobojetnia sie przesacz i wytraca zen zapomoca octanu olowiu (Pb. acetic. bas.) organiczne zwiaz¬ ki fosforowe. Osad przemyty kilkakrotnie zawiesza sie w wodzie i rozklada siarkowo¬ dorem. Po odsaczeniu siarczku olowiu zo¬ bojetnia sie przesacz weglanem baru, zage¬ szcza w prózni i pozostawia w lodowni przez 24 do 48 godzin, poczem wykrystalizowuje inozynian baru. Odsaczony flyn klarowny zadaje sie octanem rteci az do zupelnego wytracenia. Powstaly lekko zóltawy osad przemywa sie kilkakrotnie woda, zawiesza w wodzie i rozklada siarkowodorem, po¬ czem odsacza sie klarowny plyn od siarcz¬ ku rteci, uwalnia starannie od baru zapomo¬ ca kwasu siarkowego, po odsaczeniu siar¬ czanu baru ,zageszcza w prózni, zadaje 96%-alkoholem, az plyn wyraznie zmet¬ nieje, i wstawia na 24 godzin do lodowni. Po uplywie tego czasu wydziela sie kwas ade¬ nozynofosforowy miesniowy z roztworu wodno-alkoholowego w postaci igielek, któ¬ re mozna ewentualnie ponownie lub kilka¬ krotnie przekrystalizowac, rozpuszczajac krysztalki w cieplej wodzie i zadajac roz¬ twór wodny wystarczajaca iloscia alkoho¬ lu 96% -go.Przyklad II. 5 kg drozdzy piwnych go¬ tuje sie z 10 litrami wody z dodatkiem 10 cm3 kwasu octowego przez kilka minut. Go¬ racy plyn zadaje sie wodorotlenkiem baro¬ wym tak dlugo, az próbka przesaczu nie da¬ je dalszego osadu i wówczas plyn pozosta¬ wia sie w spokoju przez kilkanascie godzin, a nastepnie odwirowuje. Przesacz, zawiera¬ jacy kwas adenozynofosforowy miesniowy wytrzasa sie srodkami adsorbujacemi, ce¬ lem usuniecia domieszek koloidalnych, i od¬ wirowuje.Otrzymany przesacz zobojetnia sie i wy¬ traca zen zapomoca zasadowego octanu olo¬ wiu organiczne zwiazki fosforowe. Dalsza przeróbka jak w przykladzie I. — 2 - PLIt is known that all animal organs (blood, heart, muscles, nerve tissue, brain, glands, such as kidney, liver, etc.) and yeast contain free adenosine phosphoric acid (Drury and Szent-Gyórgy, Parnas and Ostern et al. .). The hitherto known methods for the preparation of this acid, as given by Embden and Zimmermann, Lohmann, A. Hahn and i., Require considerable amounts of expensive reagents and result in only very small amounts of pure adenosine phosphoric acid. According to these methods, an aqueous extract is prepared from animal organs, which is completely bleached with trichloroacetic acid or sublimate and hydrochloric acid. Then all phosphorus compounds, both inorganic and organic, are removed from the bleached extract. with the aid of mercury or lead and purifying the sludge by various treatments from the content of inorganic and then organic, physiologically inactive phosphorus compounds until the isolation of adenosine phosphoric acid, which is finally obtained from the aqueous-acetone solution by crystallization. the present one consists in the fact that the water extract from animal organs, such as blood, hearts, muscles, nerve tissue, glands, etc. or from beer yeast is initially only thickened by boiling it with a small amount of acetic acid and the subsequent neutralization of the sodium or potassium liquor, only inorganic phosphates are converted into barium or calcium hydroxide and the slurry obtained organic phosphorus compounds as lead salts by quenching with lead acetate. After decomposition of the lead salts with hydrogen sulphide, the filtrate thickens so as to release the zen barium or calcium salt of inosinic acid by crystallization and to keep the more soluble and non-crystallizing salt of adenosine phosphoric acid in the solution. The processing makes it possible to obtain later pure muscle adenosine phosphoric acid, which, in contrast to its barium and calcium salts, crystallizes from the aqueous extract, while the inosinic acid, conversely, forms a syrupy non-crystallizing mass. After filtering off the inosinic acid salt, the barium salt or calcium of adenosine phosphoric acid with mercury acetate and freed from barium or of calcium and finally free muscle adenosine phosphoric acid is obtained by crystallization from a hydroalcoholic solution. This method requires only cheap or small amounts of expensive reagents and yields a significant proportion of the adenosine phosphoric acid contained in the original organs or yeasts. Example 1 10 kg of fresh animal muscles are boiled for a few minutes with an equal amount of water. During boiling, acetic acid is added until the acid reaction to litmus, then soda lye for a weakly alkaline reaction, and finally a little acetic acid again until the reaction is slightly acid. The boiled pulp is cooled quickly and filtered, the filtrate is added with barium hydroxide until complete precipitation of the inorganic phosphates and centrifugation or filtration. After the sludge has been separated, the filtrate is neutralized and the Zen is destroyed with lead acetate (Pb. Acetic. Bass) organic phosphorus compounds. The sludge washed several times is suspended in water and decomposed with sulfur hydride. After the lead sulphide has been filtered off, the filtrate becomes carbonated with barium carbonate, compacted in a vacuum and left in the refrigerator for 24 to 48 hours, during which the barium inosinate crystallizes out. Desecrated, clear flyn is mixed with mercury acetate until complete dissolution. The slightly yellowish precipitate formed is washed several times with water, suspended in water and decomposed with hydrogen sulphide, then the clear liquid is drained from mercury sulphide, carefully freed from barium by means of sulfuric acid, after the barium sulphate is drained off, concentrated in a vacuum, Add 96% alcohol until the liquid is visibly turbid, and put it in the freezer for 24 hours. After this time has elapsed, the adenosine phosphoric acid is separated from the water-alcoholic solution in the form of needles, which can possibly be recrystallized again or several times by dissolving the crystals in warm water and giving an aqueous solution of a sufficient amount of 96% alcohol. -go Example II. 5 kg of brewer's yeast are boiled with 10 liters of water with the addition of 10 cm 3 of acetic acid for several minutes. The hot liquid is treated with barium hydroxide until the flow sample gives no further sediment, then the liquid remains undisturbed for several hours and then centrifuged. The slurry, containing adenosine phosphoric acid, is shaken with adsorbing agents to remove colloidal impurities, and centrifuged. The sluice obtained is neutralized and the zen is lost with alkaline acetate and organic phosphorus compounds. Further modification as in example I. - 2 - PL
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Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL19505B1 true PL19505B1 (en) | 1934-01-31 |
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