CH304183A - Process for the preparation of an organic salt of hydrofluoric acid. - Google Patents
Process for the preparation of an organic salt of hydrofluoric acid.Info
- Publication number
- CH304183A CH304183A CH304183DA CH304183A CH 304183 A CH304183 A CH 304183A CH 304183D A CH304183D A CH 304183DA CH 304183 A CH304183 A CH 304183A
- Authority
- CH
- Switzerland
- Prior art keywords
- salt
- hydrofluoric acid
- preparation
- fluorine
- organic salt
- Prior art date
Links
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 title claims description 13
- 150000003839 salts Chemical class 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 6
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000013078 crystal Substances 0.000 claims description 4
- PTOKDFKDUYQOAK-UHFFFAOYSA-N 2-aminoethanol;hydrofluoride Chemical compound F.NCCO PTOKDFKDUYQOAK-UHFFFAOYSA-N 0.000 claims description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 150000002221 fluorine Chemical class 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 235000019441 ethanol Nutrition 0.000 description 7
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 6
- 229910052731 fluorine Inorganic materials 0.000 description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 4
- 235000011164 potassium chloride Nutrition 0.000 description 3
- 239000001103 potassium chloride Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229940031098 ethanolamine Drugs 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 235000003270 potassium fluoride Nutrition 0.000 description 2
- 239000011698 potassium fluoride Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 208000002925 dental caries Diseases 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- -1 fluorine-substituted benzene Chemical class 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000004812 organic fluorine compounds Chemical class 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
- A61K8/20—Halogens; Compounds thereof
- A61K8/21—Fluorides; Derivatives thereof
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines organischen Salzes der FluorwasserstoffsÏure.
Es ist bekannt, dass zur Prophylaxe von Zahnkaries Fluorverbindungen mit Erfolg verwendet werden, wobei bisher meist anorga- nisehe Fhmride verabfolgt wurden. Ander- seits hat sich gezeigt, dass orga-nische Verbin dungen mit fklorsubstituiertell Benzolkernen, in denen also Fluor in fester organischer Bindung vorliegt, grundsÏtzlich gleichartig wirken. Diese organischen Fluorverbindungen verdienen auf Ground ihrer gr¯¯eren Verwandtschaft zu körpereigenen Stoffen an sich den Vorzug, doeh ist durch die feste Bindung des Fluors im Molekül die Fluorwir- kung'aufdieZä.hnebisweiiLen stark verzögert.
Es wurde nun in dem fluorwasserstoff- sauren Salz des Monoa. thanolamins ein Stoff gefunden, in dem das Fluoratom leicht ab spaltbar bzw. ionisierbar ist. Neuere Versuehe haben nun ergeben, dass ionisiertes Fluor dureh den Zahnschmelz direkt zur Resorption gelant. Anderseits bildet die gleichzeitige Anwesenheit einer OH- und NH2-Gruppe im Molekül für die Anwendung des Stoffes die günstigsten Voraussetzungen, insbesondere f r die Resorption und Eindringungsfähig- keit durch die Mundsehleimhäute. Au¯erdem zeichnet sich die Verbindung durch eine besonders gute VertrÏglichkeit aus.
Die neue Verbindung wird erfindungsge- mass dadureh gewonnen, da¯ man Fluorwas- serstoffsäure oder ein Fluorid mit Mono äthanolamin oder einem Salz desselben umsetzt. Die Umsetzung wird zweekmäRig in Ge genwart eines Lösungsmittels vorgenommen.
Wenn man ein Fluorsalz mit einem Säuresalz des Äthanolamins in Gegenwart eines Losungsmittels umsetzt, so werden zweckmässig solehe Sa. lze verwendet, dass bei der doppelten Umsetzung neben dem ¯thanol amin-hydrofluorid ein Salz entsteht, welches im L¯sungsmittel, z. B. Wasser oder verdünntem Alkohol, einen unlöslichen Niederschlag bildet.
Die neue Verbindung ist in Wasser und absoluten und verdünnten Alkoholen löslieh ; sie kann sowohl in fester Form, z. B. in Ta blette, als Zusatz zu Pasten oder auch in flüssiger Form in einem L¯sungsmittel gelost, angewendet werden.
Beispiel 1:
61 g reines Äthanolamin werden mit 50 g 40%iger FluorwasserstoffsÏure vermischt.
Aus der entstehenden viskosen Lösung wird das Wasser a. uf dem Wasserbad verdampft, der Rückstand mit Alkohol aufgenommen und die alkoholische Losung wiederum verdampft.
Es hinterbleiben sta. rk hygroskopische Kristalle, die bei 35-37 C schmelzen. Die Ausbeute ist praktisch quantitativ. Durch Kri stallisieren aus Äthylalkohol werden Kristalle vom Smp. 42-45 C erhalten.
Beispiel 2 :
29, 25 g MonoÏthanolamin-hydrochlorid und 17, 4 g Kaliumflluorid werden mit 400 cm3 absolutem. Äthylalkohol 6 Stunden auf dem Wasserbad unter Rüekfluss erhitzt. Dabei geht Kaliumfluorid unter Abseheidung von Kaliumchlorid allmÏhlich in L¯sung. Nach starkem Kühlen wird vom ausgeschiedenen Kaliumehlorid abgesaugt, mit kaltem Äthanol gewaschen und das Filtrat im Vakuum zur Trackne verdampft. Es hinterbleibt ein dickes, hellgelbes 61, das im Eissehrank vollkommen kristallin erstarrt.
Im Reaktionsprodukt gegebenenfalls noch vorhandene geringe Mengen Kaliumchlorid werden durch nochmaliges Losen in Äthylalkohol, Filtrieren und Verdampfen des Filtrats entfernt. Die beim Abkühlen auf 0 C erhaltenen Kristalle schmelzen bei 42-45 C.
Die Ausbeute ist prao-, ktisch quantitativ.
Process for the production of an organic salt of hydrofluoric acid.
It is known that fluorine compounds are successfully used for the prophylaxis of dental caries, with mostly inorganic fhmrides having been administered to date. On the other hand, it has been shown that organic compounds with fluorine-substituted benzene nuclei, in which fluorine is present in a firm organic bond, basically act in the same way. These organic fluorine compounds deserve to be preferred because they are more closely related to the body's own substances, but the effect of fluorine on the teeth is sometimes severely delayed due to the firm binding of fluorine in the molecule.
It was now in the hydrofluoric acid salt of Monoa. thanolamins found a substance in which the fluorine atom can easily be split off or ionized. Recent experiments have shown that ionized fluorine is directly absorbed through the tooth enamel. On the other hand, the simultaneous presence of an OH and NH2 group in the molecule creates the most favorable conditions for the application of the substance, in particular for absorption and penetration through the oral mucous membranes. In addition, the connection is characterized by particularly good compatibility.
According to the invention, the new compound is obtained by reacting hydrofluoric acid or a fluoride with monoethanolamine or a salt thereof. The reaction is carried out twice in the presence of a solvent.
If a fluorine salt is reacted with an acid salt of ethanolamine in the presence of a solvent, salts are expediently used that in the double reaction, in addition to the ethanol amine hydrofluoride, a salt is formed which is in the solvent, e.g. B. water or dilute alcohol, forms an insoluble precipitate.
The new compound is soluble in water and absolute and dilute alcohols; it can be in solid form, e.g. B. in tablet, as an additive to pastes or in liquid form in a solvent, can be used.
Example 1:
61 g of pure ethanolamine are mixed with 50 g of 40% hydrofluoric acid.
From the resulting viscous solution the water becomes a. Evaporated in a water bath, the residue was taken up with alcohol and the alcoholic solution evaporated again.
It remains behind. rk hygroscopic crystals that melt at 35-37 C. The yield is practically quantitative. Crystals with a melting point of 42-45 ° C. are obtained by crystallizing from ethyl alcohol.
Example 2:
29.25 g monoÏthanolamine hydrochloride and 17.4 g potassium fluoride are with 400 cm3 absolute. Ethyl alcohol heated under reflux on a water bath for 6 hours. In the process, potassium fluoride gradually dissolves with the separation of potassium chloride. After strong cooling, the precipitated potassium chloride is suctioned off, washed with cold ethanol and the filtrate is evaporated in vacuo to form a trackne. What remains is a thick, light yellow 61 that solidifies in a completely crystalline manner in the ice tank.
Any small amounts of potassium chloride still present in the reaction product are removed by repeated dissolving in ethyl alcohol, filtration and evaporation of the filtrate. The crystals obtained on cooling to 0 C melt at 42-45 C.
The yield is practically quantitative.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE304183X | 1950-12-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH304183A true CH304183A (en) | 1954-12-31 |
Family
ID=6116071
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH307875D CH307875A (en) | 1950-12-04 | 1951-11-28 | Process for the preparation of an organic salt of hydrofluoric acid. |
| CH304183D CH304183A (en) | 1950-12-04 | 1951-11-28 | Process for the preparation of an organic salt of hydrofluoric acid. |
| CH307874D CH307874A (en) | 1950-12-04 | 1951-11-28 | Process for the preparation of an organic salt of hydrofluoric acid. |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH307875D CH307875A (en) | 1950-12-04 | 1951-11-28 | Process for the preparation of an organic salt of hydrofluoric acid. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH307874D CH307874A (en) | 1950-12-04 | 1951-11-28 | Process for the preparation of an organic salt of hydrofluoric acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (3) | CH307875A (en) |
-
1951
- 1951-11-28 CH CH307875D patent/CH307875A/en unknown
- 1951-11-28 CH CH304183D patent/CH304183A/en unknown
- 1951-11-28 CH CH307874D patent/CH307874A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH307875A (en) | 1955-06-15 |
| CH307874A (en) | 1955-06-15 |
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