CH464953A - Process for preparing the lithium salt of para-dihydroxy-benzenesulfonic acid - Google Patents
Process for preparing the lithium salt of para-dihydroxy-benzenesulfonic acidInfo
- Publication number
- CH464953A CH464953A CH1569267A CH1569267A CH464953A CH 464953 A CH464953 A CH 464953A CH 1569267 A CH1569267 A CH 1569267A CH 1569267 A CH1569267 A CH 1569267A CH 464953 A CH464953 A CH 464953A
- Authority
- CH
- Switzerland
- Prior art keywords
- dihydroxy
- lithium salt
- lithium
- salt
- para
- Prior art date
Links
- 229910003002 lithium salt Inorganic materials 0.000 title claims description 10
- 159000000002 lithium salts Chemical class 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 229940092714 benzenesulfonic acid Drugs 0.000 title description 5
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 10
- CTLTUPWEUCZSIP-UHFFFAOYSA-N 1,4-dihydroxycyclohexa-2,4-diene-1-sulfonic acid Chemical compound OC1=CCC(O)(S(O)(=O)=O)C=C1 CTLTUPWEUCZSIP-UHFFFAOYSA-N 0.000 claims description 8
- 238000000354 decomposition reaction Methods 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- FEWJPZIEWOKRBE-UHFFFAOYSA-M 3-carboxy-2,3-dihydroxypropanoate Chemical compound OC(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-M 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- MHCFAGZWMAWTNR-UHFFFAOYSA-M lithium perchlorate Chemical compound [Li+].[O-]Cl(=O)(=O)=O MHCFAGZWMAWTNR-UHFFFAOYSA-M 0.000 claims description 4
- 229910001486 lithium perchlorate Inorganic materials 0.000 claims description 4
- 239000006227 byproduct Substances 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 150000001768 cations Chemical class 0.000 description 5
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 3
- 229910052808 lithium carbonate Inorganic materials 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- DKBULPCELGQKPL-UHFFFAOYSA-M OC1(CC=C(C=C1)O)S(=O)(=O)[O-].[Li+] Chemical compound OC1(CC=C(C=C1)O)S(=O)(=O)[O-].[Li+] DKBULPCELGQKPL-UHFFFAOYSA-M 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- AXZAYXJCENRGIM-UHFFFAOYSA-J dipotassium;tetrabromoplatinum(2-) Chemical compound [K+].[K+].[Br-].[Br-].[Br-].[Br-].[Pt+2] AXZAYXJCENRGIM-UHFFFAOYSA-J 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- -1 piperazinium ion Chemical class 0.000 description 2
- KYKNRZGSIGMXFH-ZVGUSBNCSA-M potassium bitartrate Chemical group [K+].OC(=O)[C@H](O)[C@@H](O)C([O-])=O KYKNRZGSIGMXFH-ZVGUSBNCSA-M 0.000 description 2
- 229910001487 potassium perchlorate Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000007790 solid phase Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- VZYDKJOUEPFKMW-UHFFFAOYSA-N 2,3-dihydroxybenzenesulfonic acid Chemical compound OC1=CC=CC(S(O)(=O)=O)=C1O VZYDKJOUEPFKMW-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 206010047073 Vascular fragility Diseases 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-O diethylammonium Chemical compound CC[NH2+]CC HPNMFZURTQLUMO-UHFFFAOYSA-O 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- ZPPPLBXXTCVBNC-UHFFFAOYSA-M lithium;2,3-dihydroxybutanedioate;hydron Chemical compound [H+].[Li+].[O-]C(=O)C(O)C(O)C([O-])=O ZPPPLBXXTCVBNC-UHFFFAOYSA-M 0.000 description 1
- 229910001425 magnesium ion Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000016337 monopotassium tartrate Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229940081543 potassium bitartrate Drugs 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 229910001427 strontium ion Inorganic materials 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical compound OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Procédé de préparation du sel de lithium de l'acide para-dihydroxy-benzène-sulfonique
Le brevet principal No 448126 concerne un procédé de préparation des sels de l'acide para-dihydroxy-ben zène-sulfonique, qui ont pour forme:
EMI1.1
dans laquelle R est le cation d'une base organique ou minérale, à l'exclusion du potassium, et n est un nombre égal à la valence du cation R.
Lorsque R est le cation d'une base organique, ce peut être l'ion diéthylammonium, triéthanolammonium ou pipérazinium, auquel cas n est égal à un. Lorsque R est le cation d'une base minérale, ce peut être l'ion calcium, strontium ou magnésium, auquel cas n est égal à deux.
Le procédé du brevet principal est caractérisé en ce que l'on effectue une double décomposition entre le sel de potassium de l'acide para-dihydroxy-benzène-sulfonique et un sel d'acide minéral ou organique du cation R dans un liquide dans lequel le sel désiré de l'acide para dihydroxy-benzène-sulfonique est soluble et dans lequel le sel de potassium formé comme sous-produit est peu ou pas soluble.
On a trouvé que le sel de lithium de l'acide p-dihydroxy-benzène-sulfonique, sel qui n'est pas mentionné dans le brevet principal, possède des propriétés pharmacologiques particulièrement intéressantes et est utile dans la thérapie des affections relatives à la coagulation du sang et la fragilité vasculaire.
Le procédé de la présente invention est donc caractérisé en ce que l'on effectue une double décomposition entre le sel de potassium de l'acide p-dihydroxy-benzènesulfonique et un sel de lithium d'un acide minéral ou organique, dans un liquide dans lequel le sel de lithium de l'acide p-dihydroxy-benzène-sulfonique est soluble et dans lequel le sel de potassium formé comme sous-produit est peu ou pas soluble.
On peut par exemple utiliser, comme matière de départ, le perchlorate et le bitartrate de lithium. Dans les deux cas, le liquide dans lequel la réaction est effectuée peut être de l'eau ou de l'éthanol aqueux. On peut accé lérer la réaction en chauffant légèrement ; lorsqu'elle est terminée, on peut refroidir le produit dans le récipient où la réaction a été effectuée pour parfaire la précipitation du sel de potassium (bitartrate, perchlorate), filtrer au moyen d'une plaque poreuse pour séparer les phases liquide et solide, rejeter la phase solide constituée par le sel de potassium, concentrer la phase liquide en chauffant légèrement et en faisant le vide afin d'éviter une oxydation, puis laisser cristalliser la solution concentrée.
Le perchlorate et le bitartrate de lithium s'obtiennent facilement par exemple par addition à une solution d'acide perchlorique ou tartrique de la quantité requise de carbonate de lithium.
Exemple I
Une solution aqueuse de 200 ml, contenant 100 g d'acide perchlorique, est neutralisée en y ajoutant avec précaution 37 g de carbonate de lithium.
On dissout 228 g de sel de potassium de l'acide p-dihvdroxy-benzène-sulfonique dans 500ml d'eau, en chauffant pour faciliter la dissolution. A cette solution chaude, on ajoute en agitant la solution du perchlorate de lithium préparée préalablement.
Après une minute, il se forme un abondant précipité cristallin de perchlorate de potassium, dont la quantité augmente encore lors du refroidissement de la solution sous agitation.
Le mélange froid ainsi obtenu est filtré et le perchlorate de potassium est éliminé. La solution aqueuse est concentrée en l'absence d'air, sous vide, jusqu'à ce que la cristallisation du sel de lithium désiré commence.
La masse cristalline est séparée par filtration des eaux mères et recristallisée dans de l'alcool de 50 %. On obtient ainsi 188 g du sel de lithium de l'acide p-dihydroxybenzène-sulfonique, dont les cristaux sont très solubles dans l'eau, moins solubles dans l'alcool et insolubles dans l'éther. Le point de décomposition est d'environ 2500 C.
Exemple 2
Une solution aqueuse de 350 ml, contenant 150 g d'acide tartrique, est neutralisée à moitié en y ajoutant par portions et en agitant 37 g de carbonate de lithium.
On obtient ainsi une solution de bitartrate de lithium (C4HjO6Li)
Cette solution, filtrée en cas de besoin, est ajoutée à une solution chaude de 228 g du sel de potassium de l'acide p-dihydroxy-benzène-sulfonique dans 500 mi d'eau. On mélange les deux solutions en agitant et la température augmente encore pendant quelques minutes.
On continue à agiter et il se forme un précipité blanc et cristallin de bitartrate de potassium, dont la quantité augmente lors du refroidissement du mélange. On maintient ce dernier pendant 6 heures dans une armoire frigorifique et sépare ensuite le bitartrate de potassium par filtration.
La solution du p-dihydroxy-benzène-sulfonate de lithium est concentrée à basse température, en l'absence d'air et en agitant sous vide. Quand la concentration est suffisante, une cristallisation spontanée se manifeste. Les cristaux sont séparés par filtration des eaux mères, lavés avec un peu d'alcool-éther (1:1) et recristallisés dans de l'alcool de 50 %.
On obtient ainsi 114 g de p-dihydroxy-benzène-sulfonate de lithium sous forme de cristaux incolores, très solubles dans l'eau, moins solubles dans l'alcool et insolubles dans l'éther. Le point de décomposition est d'environ 2500 C.
Process for preparing the lithium salt of para-dihydroxy-benzenesulfonic acid
Main Patent No. 448126 relates to a process for the preparation of salts of para-dihydroxy-ben zene-sulfonic acid, which have the form:
EMI1.1
in which R is the cation of an organic or inorganic base, excluding potassium, and n is a number equal to the valence of the cation R.
When R is the cation of an organic base, it can be diethylammonium, triethanolammonium or piperazinium ion, in which case n is equal to one. When R is the cation of an inorganic base, it may be the calcium, strontium or magnesium ion, in which case n is equal to two.
The process of the main patent is characterized in that a double decomposition is carried out between the potassium salt of para-dihydroxy-benzene-sulfonic acid and an inorganic or organic acid salt of the cation R in a liquid in which the desired salt of para dihydroxy-benzenesulfonic acid is soluble and in which the potassium salt formed as a by-product is little or not soluble.
The lithium salt of p-dihydroxy-benzene-sulfonic acid, a salt which is not mentioned in the main patent, has been found to have particularly interesting pharmacological properties and to be useful in the therapy of conditions relating to coagulation. blood and vascular fragility.
The process of the present invention is therefore characterized in that a double decomposition is carried out between the potassium salt of p-dihydroxy-benzenesulfonic acid and a lithium salt of a mineral or organic acid, in a liquid in wherein the lithium salt of p-dihydroxy-benzenesulfonic acid is soluble and in which the potassium salt formed as a by-product is little or not soluble.
For example, lithium perchlorate and bitartrate can be used as the starting material. In either case, the liquid in which the reaction is carried out can be water or aqueous ethanol. The reaction can be accelerated by heating slightly; when it is finished, the product can be cooled in the vessel where the reaction was carried out to complete the precipitation of the potassium salt (bitartrate, perchlorate), filter through a porous plate to separate the liquid and solid phases, discard the solid phase constituted by the potassium salt, concentrate the liquid phase by heating slightly and evacuating in order to avoid oxidation, then allow the concentrated solution to crystallize.
Lithium perchlorate and bitartrate are easily obtained, for example, by adding the required amount of lithium carbonate to a solution of perchloric or tartaric acid.
Example I
An aqueous solution of 200 ml, containing 100 g of perchloric acid, is neutralized by carefully adding 37 g of lithium carbonate to it.
228 g of potassium salt of p-dihvdroxy-benzene-sulfonic acid are dissolved in 500 ml of water, with heating to facilitate dissolution. To this hot solution is added with stirring the lithium perchlorate solution prepared previously.
After one minute, an abundant crystalline precipitate of potassium perchlorate is formed, the amount of which increases further on cooling of the solution with stirring.
The cold mixture thus obtained is filtered and the potassium perchlorate is removed. The aqueous solution is concentrated in the absence of air, under vacuum, until crystallization of the desired lithium salt begins.
The crystalline mass is separated by filtration from the mother liquors and recrystallized from 50% alcohol. 188 g of the lithium salt of p-dihydroxybenzenesulfonic acid are thus obtained, the crystals of which are very soluble in water, less soluble in alcohol and insoluble in ether. The decomposition point is approximately 2500 C.
Example 2
An aqueous solution of 350 ml, containing 150 g of tartaric acid, is neutralized halfway by adding to it in portions and stirring 37 g of lithium carbonate.
This gives a solution of lithium bitartrate (C4HjO6Li)
This solution, filtered if necessary, is added to a hot solution of 228 g of the potassium salt of p-dihydroxy-benzenesulfonic acid in 500 ml of water. The two solutions are mixed with stirring and the temperature increases further for a few minutes.
Stirring is continued and a white crystalline precipitate of potassium bitartrate forms, the quantity of which increases when the mixture cools. The latter is kept for 6 hours in a refrigerated cabinet and then the potassium bitartrate is separated by filtration.
The solution of lithium p-dihydroxy-benzene-sulfonate is concentrated at low temperature, in the absence of air and with stirring under vacuum. When the concentration is sufficient, spontaneous crystallization occurs. The crystals are separated by filtration from the mother liquors, washed with a little alcohol-ether (1: 1) and recrystallized from 50% alcohol.
114 g of lithium p-dihydroxy-benzene-sulfonate are thus obtained in the form of colorless crystals, very soluble in water, less soluble in alcohol and insoluble in ether. The decomposition point is approximately 2500 C.
Claims (1)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1569267A CH464953A (en) | 1966-06-08 | 1967-11-09 | Process for preparing the lithium salt of para-dihydroxy-benzenesulfonic acid |
| ES356108A ES356108A2 (en) | 1967-11-09 | 1968-07-05 | Procedure for obtaining salts from paradylidroxy-benzene-sulforic acid. (Machine-translation by Google Translate, not legally binding) |
| BE722746D BE722746A (en) | 1967-11-09 | 1968-10-23 | |
| GB1233798D GB1233798A (en) | 1967-11-09 | 1968-10-29 | |
| DE19681806926 DE1806926A1 (en) | 1967-11-09 | 1968-10-29 | Lithium salt of hydroquinone sulfonic acid |
| US771977A US3629327A (en) | 1967-11-09 | 1968-10-30 | Lithium salt of hydroquinone sulfonic acid |
| FR172904A FR8285M (en) | 1967-11-09 | 1968-11-07 | |
| FR1590923D FR1590923A (en) | 1967-11-09 | 1968-11-07 | |
| US00129154A US3764700A (en) | 1967-11-09 | 1971-03-29 | Treatment of the circulatory system with the lithium salt of hydroquinone sulfonic acid |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH825166A CH448126A (en) | 1966-06-08 | 1966-06-08 | Process for the preparation of salts of paradihydroxy-benzene-sulfonic acid |
| CH1569267A CH464953A (en) | 1966-06-08 | 1967-11-09 | Process for preparing the lithium salt of para-dihydroxy-benzenesulfonic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH464953A true CH464953A (en) | 1968-11-15 |
Family
ID=25703032
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1569267A CH464953A (en) | 1966-06-08 | 1967-11-09 | Process for preparing the lithium salt of para-dihydroxy-benzenesulfonic acid |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH464953A (en) |
-
1967
- 1967-11-09 CH CH1569267A patent/CH464953A/en unknown
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