DE1032746B - Process for the production of neutral aromatic triesters of orthophosphoric acid - Google Patents
Process for the production of neutral aromatic triesters of orthophosphoric acidInfo
- Publication number
- DE1032746B DE1032746B DEF9459A DEF0009459A DE1032746B DE 1032746 B DE1032746 B DE 1032746B DE F9459 A DEF9459 A DE F9459A DE F0009459 A DEF0009459 A DE F0009459A DE 1032746 B DE1032746 B DE 1032746B
- Authority
- DE
- Germany
- Prior art keywords
- orthophosphoric acid
- production
- phosphorus
- neutral
- neutral aromatic
- 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.)
- Pending
Links
- -1 aromatic triesters Chemical class 0.000 title claims description 12
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 7
- 230000007935 neutral effect Effects 0.000 title claims description 6
- 235000011007 phosphoric acid Nutrition 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 7
- 229910052698 phosphorus Inorganic materials 0.000 claims description 7
- 239000011574 phosphorus Substances 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- VOHMIHACEYNATI-UHFFFAOYSA-N dichloro(triphenoxy)-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1OP(Cl)(OC=1C=CC=CC=1)(Cl)OC1=CC=CC=C1 VOHMIHACEYNATI-UHFFFAOYSA-N 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229960003750 ethyl chloride Drugs 0.000 description 2
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000008646 thermal stress Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005406 washing Methods 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 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
- C07F9/12—Esters of phosphoric acids with hydroxyaryl compounds
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)
Description
Verfahren zur Herstellung neutraler aromatischer Triester der Orthophosphorsäure Durch Reaktion von Phosphorpentachlorid mit Phenol lassen sich bekanntlich Verbindungen der allgemeinen Formel O = P (OR)x . C1" herstellen. Auch der neutrale, pentakoordinierte Ester des Phenols P(OR)5 ist in -Liebigs Annalen der Chemie« (1927), Bd. 454, S. 119, beschrieben. Er wurde erhalten durch Umsetzen von Triphenoxyphosphordichlorid mit Phenol. Schließlich kann man das teilveresterte Pentaderivat der Bruttoformel (P (0 R)3 C12 mit Wasser zum neutralen Phenylester der Orthophosphorsäure umsetzen.Process for the production of neutral aromatic triesters of orthophosphoric acid It is known that compounds can be formed by reaction of phosphorus pentachloride with phenol the general formula O = P (OR) x. C1 ". Also the neutral, penta-coordinated one Ester of the phenol P (OR) 5 is described in Liebigs Annalen der Chemie (1927), vol. 454, p. 119. It was obtained by reacting triphenoxyphosphorus dichloride with phenol. Finally, one can use the partially esterified pentad derivative of the gross formula React (P (0 R) 3 C12 with water to form the neutral phenyl ester of orthophosphoric acid.
Gegenstand der Erfindung ist ein Verfahren zur Herstellung neutraler aromatischer Triester der Orthophosphorsäure, dsa darin besteht, daß Pentaderivate des Phosphors der allgemeinen Formel P (0 R), Hal(; -,), in der R einen aromatischen Rest, x die Zahl 3, 4 oder 5 und Hal ein Halogenatom bedeutet, mit aliphatischen einwertigen Alkoholen oder Estersäuren des Phosphors umgesetzt werden.The invention relates to a process for producing neutral aromatic triester of orthophosphoric acid, which consists of pentad derivatives of phosphorus of the general formula P (0 R), Hal (; -,), in which R is an aromatic Radical, x is the number 3, 4 or 5 and Hal is a halogen atom, with aliphatic monohydric alcohols or ester acids of phosphorus are implemented.
Gemäß dem neuen Verfahren werden reinere Produkte als nach den bisherigen Verfahren erhalten, insbesondere solche, die weniger saure Nebenprodukte enthalten. Außerdem kann als wertvolles Nebenprodukt Alkylhalogenid erhalten werden, beispielsweise bei der Umsetzung von Triphenoxyphosphordichlorid mit einem Alkohol.The new process results in cleaner products than the previous ones Processes obtained, especially those that contain less acidic by-products. In addition, alkyl halide can be obtained as a valuable by-product, for example in the reaction of triphenoxyphosphorus dichloride with an alcohol.
Als Pentaderivat des Phosphors von der allgemeinen Formel P (O R)
x Ha1(5 _ x) ist z. B. das Triphenoxyphosphordichlorid zu nennen, das erfindungsgemäß
mit aliphatischen Alkoholen entsprechend der Gleichung
Pentaphenylphosphat setzt sich mit aliphatischem einwertigem Alkohol
gemäß der Gleichung
Beispiel 1 In vorgelegte 343 g Phenol werden bei + 50'C unter Rühren 214 g Phosphorpentachlorid eingetragen. Anschließend wird am Rückflußkühler evakuiert, allmählich zum Sieden erhitzt und etwa 30 Minuten lang auf Siedetemperatur gehalten, wobei sich Triphenoxyphosphordichlorid bildet. In das entgaste Reaktionsgemisch werden dann 62 ccm Äthanol eingetragen. Zur Isolierung des entstandenen Äthylchlorids wird bei 100'C ein trockener Luftstrom durch die Flüssigkeit geleitet, der eine auf 20'C gehaltene Waschflasche mit lmolarer Natronlauge und eine Kühlfalle nachgeschaltet sind. Ausbeute an Äthylchlorid etwa 800/,. Die anschließende Vakuumdestillation des Kolbeninhaltes ergibt nach dem Entfernen des geringen Vorlaufes eine praktisch quantitative Ausbeute an praktisch säurefreiem Triphenylphosphat. F. = 49,0 bis 49,3'C.Example 1 214 g of phosphorus pentachloride are introduced into 343 g of phenol initially introduced at + 50 ° C. with stirring. It is then evacuated in the reflux condenser, gradually heated to the boil and kept at the boiling temperature for about 30 minutes, during which triphenoxyphosphorus dichloride is formed. 62 cc of ethanol are then introduced into the degassed reaction mixture. To isolate the resulting ethyl chloride, a stream of dry air is passed through the liquid at 100.degree. C., followed by a washing bottle kept at 20.degree. C. with 1 molar sodium hydroxide solution and a cold trap. Yield of ethyl chloride about 800 / ,. The subsequent vacuum distillation of the contents of the flask gives a practically quantitative yield of practically acid-free triphenyl phosphate after the small forerun has been removed. F. = 49.0 to 49.3 ° C.
Beispiel 2 Triphenylphosphat, das etwa infolge thermischer Beanspruchung
bei der Synthese und Aufbereitung mit laugeverbrauchenden Körpern, wie sauren Estern
des
Phosphors, die im einzelnen nicht identifiziert sind, verunreinigt
ist, wird mit 5010 Pentaphenylphosphat versetzt und anschließend im Vakuum
destilliert. Es wird ein praktisch säurefreies Destillat erhalten. F. = 49,0 bis
49,3°C. Die Umsetzung verläuft gemäß der Gleichung
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF9459A DE1032746B (en) | 1952-07-10 | 1952-07-10 | Process for the production of neutral aromatic triesters of orthophosphoric acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF9459A DE1032746B (en) | 1952-07-10 | 1952-07-10 | Process for the production of neutral aromatic triesters of orthophosphoric acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1032746B true DE1032746B (en) | 1958-06-26 |
Family
ID=7086146
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF9459A Pending DE1032746B (en) | 1952-07-10 | 1952-07-10 | Process for the production of neutral aromatic triesters of orthophosphoric acid |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1032746B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0595597A1 (en) * | 1992-10-28 | 1994-05-04 | Teijin Chemicals, Ltd. | Process for producing triaryl phosphate |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR797449A (en) * | 1934-11-10 | 1936-04-27 | Du Pont | Esters of phosphorus acids and their manufacturing process |
| GB452508A (en) * | 1934-01-24 | 1936-08-24 | Chemische Fabriek Servo Nv | A process of manufacturing washing, cleansing, wetting and emulsifying agents and treatment baths containing the same |
-
1952
- 1952-07-10 DE DEF9459A patent/DE1032746B/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB452508A (en) * | 1934-01-24 | 1936-08-24 | Chemische Fabriek Servo Nv | A process of manufacturing washing, cleansing, wetting and emulsifying agents and treatment baths containing the same |
| FR797449A (en) * | 1934-11-10 | 1936-04-27 | Du Pont | Esters of phosphorus acids and their manufacturing process |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0595597A1 (en) * | 1992-10-28 | 1994-05-04 | Teijin Chemicals, Ltd. | Process for producing triaryl phosphate |
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