DE903574C - Process for the preparation of Pentaerythritdiiodohydrinphosphoric acid - Google Patents
Process for the preparation of Pentaerythritdiiodohydrinphosphoric acidInfo
- Publication number
- DE903574C DE903574C DEC1023D DEC0001023D DE903574C DE 903574 C DE903574 C DE 903574C DE C1023 D DEC1023 D DE C1023D DE C0001023 D DEC0001023 D DE C0001023D DE 903574 C DE903574 C DE 903574C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- pentaerythritol
- preparation
- pentaerythritdiiodohydrinphosphoric
- calcium salt
- 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
- 239000002253 acid Substances 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title description 3
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 8
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 7
- 159000000007 calcium salts Chemical class 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- YQNSMGUFZYPDOO-UHFFFAOYSA-N [P].[I] Chemical compound [P].[I] YQNSMGUFZYPDOO-UHFFFAOYSA-N 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung von Pentaerythritdijodhydrinphosphorsäure Jod- und phosphorhaltige Verbindungen haben als therapeutisch wirksame Substanzen Bedeutung. In der Patentscbrift 711539 ist die Herstellung einer Verbindung beschrieben, die Jod und Phosphorsäure enthält, in der aliphatisch gebundenes Jod auch in wäßriger Lösung beständig,ist, sofern der pH-Wert der Lösung neutral oder sauer eingestellt ist. In alkalischem Bereich dagegen tritt eine verhältnismäßig rasche Abspaltung des Jods ein. Gegenstand der vorliegenden Erfindung ist die Herstellung von Pentaerythritdijodhydrinphosphorsäure bzw. deren Calciumsalz, die auch in alkalischer Lösung praktisch kein Jod abspaltet. Man erhält diese noch nicht beschriebene Verbindung dadurch, daß man Pentaerythritdijodhydrin mit Phosphoroxychlorid in an sich bekannter Weise in einen saueren Phosphorsäureester bzw. sein Calciumsalz überführt.Process for the preparation of pentaerythritol iodohydrinphosphoric acid Iodine- and phosphorus-containing compounds are important therapeutically effective substances. Patent 711 539 describes the preparation of a compound containing iodine and phosphoric acid, in which aliphatically bound iodine is also stable in aqueous solution, provided the pH of the solution is neutral or acidic. In the alkaline range, on the other hand, the iodine is split off relatively quickly. The subject of the present invention is the production of pentaerythritol iodohydrinphosphoric acid or its calcium salt, which splits off practically no iodine even in alkaline solution. This compound, which has not yet been described, is obtained by converting pentaerythritol iodohydrin with phosphorus oxychloride in a manner known per se into an acidic phosphoric acid ester or its calcium salt.
Beispiel: 14,2 Teile (o,04 Mol) Pentaerythritdijodhydrin werden mit 9,1 Teilen (o,o6 Mol) Phosphoroxychlorid versetzt und allmählich am Rückfluß erhitzt. Bei 6o bis 7o° löst sich das Reaktionsgemisch homogen unter Chlorwasserstoffabspaltung. Durch weiteres Erhitzen während 2 bis 3 Stunden in siedendem Wasserbad ist die Chlorwasserstoffabspaltung beendet. Überschüssiges Phosphoroxychlorid wird unter vermindertem Druck abgesaugt, der Rückstand mit g enig Wasser ausgewaschen. Das Reaktionsprodukt erstarrt zu einem Kristallbrei. Aus wenig g6°/oigem Alkohol umkristallisiert, besitzt die erhaltene Pentaerythritdijodhydrinphosphorsäure den Schmelzpunkt 182 bis r83'. Die Säure ist leicht löslich in heißem Alkohol, schwer löslich in Äther und fast unlöslich in Wasser. Die Ausbeute beträgt etwa 15 Teile (go% der Theorie). Das Calciumsalz wird erhalten, indem eine alkoholische Lösung der Säure mit wäßrig alkoholischemAmmoniak neutralisiert und mit wenigüberschüssigeralkoholischer Calciumchloridlösung versetzt wird. Das ausgefallene Salz wird abgesaugt und mit wäßrigem Alkoholausgewaschen. Ausbeute 1q. Teile (etwa 8o (l/o der Theorie).Example: 9.1 parts (0.06 mol) of phosphorus oxychloride are added to 14.2 parts (0.04 mol) of pentaerythritol diiodohydrin and the mixture is gradually refluxed. At 6o to 7o ° the reaction mixture dissolves homogeneously with elimination of hydrogen chloride. The elimination of hydrogen chloride is complete by further heating for 2 to 3 hours in a boiling water bath. Excess phosphorus oxychloride is filtered off with suction under reduced pressure, and the residue is washed out with g enig water. The reaction product solidifies to form a crystal paste. Recrystallized from a little 6% alcohol, the pentaerythritol iodohydrinphosphoric acid obtained has a melting point of 182 to r83 '. The acid is easily soluble in hot alcohol, sparingly soluble in ether and almost insoluble in water. The yield is about 15 parts (20% of theory). The calcium salt is obtained by neutralizing an alcoholic solution of the acid with aqueous alcoholic ammonia and adding a little excess alcoholic calcium chloride solution. The precipitated salt is filtered off with suction and washed out with aqueous alcohol. Yield 1q. Parts (about 8o (l / o of theory).
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC1023D DE903574C (en) | 1942-02-01 | 1942-02-01 | Process for the preparation of Pentaerythritdiiodohydrinphosphoric acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC1023D DE903574C (en) | 1942-02-01 | 1942-02-01 | Process for the preparation of Pentaerythritdiiodohydrinphosphoric acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE903574C true DE903574C (en) | 1954-02-08 |
Family
ID=7012490
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC1023D Expired DE903574C (en) | 1942-02-01 | 1942-02-01 | Process for the preparation of Pentaerythritdiiodohydrinphosphoric acid |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE903574C (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE696317C (en) * | 1930-08-12 | 1940-09-18 | I G Farbenindustrie Akt Ges | eestern |
-
1942
- 1942-02-01 DE DEC1023D patent/DE903574C/en not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE696317C (en) * | 1930-08-12 | 1940-09-18 | I G Farbenindustrie Akt Ges | eestern |
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