DE242613C - - Google Patents
Info
- Publication number
- DE242613C DE242613C DENDAT242613D DE242613DA DE242613C DE 242613 C DE242613 C DE 242613C DE NDAT242613 D DENDAT242613 D DE NDAT242613D DE 242613D A DE242613D A DE 242613DA DE 242613 C DE242613 C DE 242613C
- Authority
- DE
- Germany
- Prior art keywords
- ether
- chloroform
- esters
- phosphoric anhydride
- phosphoric
- 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.)
- Active
Links
- DLYUQMMRRRQYAE-UHFFFAOYSA-N Phosphorus pentoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 4
- 150000001983 dialkylethers Chemical class 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229960000583 Acetic Acid Drugs 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N Silver nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000005591 charge neutralization Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-N meta-phosphoric acid Chemical class OP(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-N 0.000 description 1
- 230000001264 neutralization Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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 System
- 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
- C07F9/098—Esters of polyphosphoric acids or anhydrides
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Die Alkylester der Phosphorsäure sind bisher nur schwer zugänglich gewesen. Das vorliegende Verfahren gestattet eine billige und leicht ausführbare Gewinnung der Ester. Das Verfahren beruht darauf, daß Älkyläther der allgemeinen Formel R1 · O · R2 mit Phosphorsäureanhydrid beim Kochen Phosphorsäureester bilden. Bei Anwendung von Phosphorsäüreanhydrid entstehen Metaphosphorsäureester. Die stattfindende Reaktion entspricht der allgemeinen GleichungThe alkyl esters of phosphoric acid have hitherto been accessible only with difficulty. The present process permits the esters to be recovered cheaply and easily. The process is based on the fact that alkyl ethers of the general formula R 1 · O · R 2 form phosphoric acid esters with phosphoric anhydride on boiling. When using phosphoric anhydride, metaphosphoric acid esters are formed. The reaction that takes place corresponds to the general equation
R1. O- R2 + P2O5 R 1 . O- R 2 + P 2 O 5
= R1 - O ' PO2 + R2 · O ' PO2, = R 1 - O 'PO 2 + R 2 · O' PO 2 ,
wobei R1 und R2 einwertige Alkyle darstellen.where R 1 and R 2 represent monovalent alkyls.
Die Alkyle können voneinander verschieden oder gleich sein. Es können also!' einfache oder gemischte Äther Anwendung finden.The alkyls can be different from one another or the same. So it can! ' simple or mixed ethers are used.
Beispiel: 10 kg Phosphorpentoxyd werdenExample: 10 kg of phosphorus pentoxide will be
.3 Tage mit 10 kg Äther, der über Natrium vorher getrocknet war, gekocht. Das Ende der Reaktion erkennt man daran, daß das Phosphorpentoxyd vollständig verschwunden ist und sich in einen klaren Sirup verwandeltBoiled for 3 days with 10 kg of ether that had previously been dried over sodium. The end of The reaction can be recognized by the fact that the phosphorus pentoxide has completely disappeared and turns into a clear syrup
hat. Der sich abscheidende, in Äther unlösliche, dickflüssige Sirup wird von dem überschüssigen Äther getrennt, in Chloroform gelöst und dann mit Äther gefällt. Der Prozeß findet seinen Ausdruck in folgender Formel:Has. The thick syrup which separates and is insoluble in ether is replaced by the excess Ether separated, dissolved in chloroform and then precipitated with ether. The process is expressed in the following formula:
(C2 HJ2 O + P2[O5 = 2]C2*H5'pyP O2.(C 2 HJ 2 O + P 2 [O 5 = 2 ] C 2 * H 5 'pyP O 2 .
Das Produkt ist leicht ■ löslich in Alkohol, Eisessig, Aceton und Chloroform, schwer löslich in Benzol, unlöslich in Äther und Ligroin. Es kann durch Aufnehmen mit Chloroform und Fällen mit Äther gereinigt werden. Die Phosphorbestimmung an einem doppelt gefällten Produkt ergab: 0,2456 g gaben 0,2474 g Mg2P2O1. The product is easily ■ soluble in alcohol, glacial acetic acid, acetone and chloroform, hardly soluble in benzene, insoluble in ether and ligroin. It can be purified by absorbing it with chloroform and precipitating it with ether. The phosphorus determination on a doubly precipitated product gave: 0.2456 g gave 0.2474 g of Mg 2 P 2 O 1 .
Berechnet für (C2H5)PO3: 28,70 Prozent. Gefunden: 28,05 Prozent.Calculated for (C 2 H 5 ) PO 3 : 28.70 percent. Found: 28.05 percent.
In Wasser löst es sich unter Erwärmung. Durch sehr verdünnte gekühlte Natronlauge wird der Ester leicht verseift. Die Lösung gibt nach dem Neutralisieren mit Salpetersäure einen weißen Niederschlag mit Silbernitrat und koaguliert, mit Essigsäure angesäuert, Eiweiß.It dissolves in water when heated. With very dilute, cooled sodium hydroxide solution the ester is easily saponified. The solution gives after neutralization with nitric acid a white precipitate with silver nitrate and coagulated, acidified with acetic acid, Protein.
Die Verbindungen sind für pharmazeutische Zwecke sowie als Ausgangsmaterialien für andere organische Verbindungen bestimmt.The compounds are for pharmaceutical uses as well as starting materials for others organic compounds determined.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE242613C true DE242613C (en) |
Family
ID=501803
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT242613D Active DE242613C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE242613C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2492153A (en) * | 1947-05-10 | 1949-12-27 | Eastman Kodak Co | Preparation of insecticidal polyphosphate esters |
-
0
- DE DENDAT242613D patent/DE242613C/de active Active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2492153A (en) * | 1947-05-10 | 1949-12-27 | Eastman Kodak Co | Preparation of insecticidal polyphosphate esters |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE734743C (en) | Process for the production of polyamide-like compounds | |
| DE1290535B (en) | Process for the separation and recovery of rhodium from hydroformylation products | |
| DE242613C (en) | ||
| DE528741C (en) | Process for the preparation of a water-soluble polymerisation product | |
| DE2855860C2 (en) | Process for the purification of organic peroxides containing water | |
| DE2511807C3 (en) | Process for the production of esters of polyhydric alcohols and monocarboxylic fatty acids with 5 to 9 carbon atoms | |
| DE2235373C3 (en) | Process for the preparation of alkylene oxide adducts | |
| DE2604751C2 (en) | ||
| DE922166C (en) | Process for converting olefinic aldehydes into oxyaldehydes | |
| DE168408C (en) | ||
| DE619348C (en) | Process for the production of pure diacetyl from wood vinegar or other mixtures containing diacetyl | |
| AT157582B (en) | Process for the preparation of l-ascorbic acid. | |
| DE499523C (en) | Process for the production of ª ‡ -oxy acids from their nitriles | |
| DE554783C (en) | Process for processing cellulose ester raw solutions | |
| DE514150C (en) | Process for the preparation of cellulose esters of inorganic acids | |
| DE203717C (en) | ||
| DE857951C (en) | Production of ª ‡ -substituted acroleins | |
| DE667605C (en) | Process for the production of conversion products of rubber | |
| AT70784B (en) | Process for the production of gallic acid from gall apples. | |
| AT237583B (en) | Process for purifying alcohols | |
| DE892440C (en) | Process for the preparation of substituted glutaraldehyde | |
| DE347139C (en) | Process for the preparation of metal compounds of sulfinides | |
| DE1904537C (en) | Process for the preparation of sulfate ion-free tetrabromophthalic acid monoesters | |
| CH260994A (en) | Process for the production of vitamin A acid. | |
| DE1081443B (en) | Process for the production of pure alkali, alkaline earth or ammonium salts of 1,4-sugar acid lactone |