DE1078558B - Process for the preparation of dialkyl phosphites with dissimilar alkyl groups - Google Patents
Process for the preparation of dialkyl phosphites with dissimilar alkyl groupsInfo
- Publication number
- DE1078558B DE1078558B DEB50098A DEB0050098A DE1078558B DE 1078558 B DE1078558 B DE 1078558B DE B50098 A DEB50098 A DE B50098A DE B0050098 A DEB0050098 A DE B0050098A DE 1078558 B DE1078558 B DE 1078558B
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- moles
- dialkyl phosphites
- phosphorus
- alkyl groups
- 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
- 238000000034 method Methods 0.000 title claims description 12
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 title claims description 7
- 125000000217 alkyl group Chemical group 0.000 title description 3
- 238000002360 preparation method Methods 0.000 title description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 239000012442 inert solvent Substances 0.000 claims description 7
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 7
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 6
- -1 alkyl radicals Chemical class 0.000 claims description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 5
- 239000011574 phosphorus Substances 0.000 claims description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 239000011261 inert gas Substances 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 2
- 239000001569 carbon dioxide Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 150000002903 organophosphorus compounds Chemical class 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 150000008282 halocarbons Chemical class 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 3
- 238000007664 blowing Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- YTPOJOIRRIMIAK-UHFFFAOYSA-N ethyl-trihydroxy-methyl-$l^{5}-phosphane Chemical compound CCP(C)(O)(O)O YTPOJOIRRIMIAK-UHFFFAOYSA-N 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZWUOWRYPAGDEPY-UHFFFAOYSA-N C(C)(C)(C)P(O)(O)O Chemical compound C(C)(C)(C)P(O)(O)O ZWUOWRYPAGDEPY-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical class OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- FRXOFPPOFAYWHE-UHFFFAOYSA-N butyl methyl hydrogen phosphite Chemical compound CCCCOP(O)OC FRXOFPPOFAYWHE-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- VYOQLHASHLBTCL-UHFFFAOYSA-N dichloro ethenyl phosphate Chemical compound ClOP(=O)(OCl)OC=C VYOQLHASHLBTCL-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- IXLIDZMVNVBMIT-UHFFFAOYSA-N ethyl methyl hydrogen phosphite Chemical compound CCOP(O)OC IXLIDZMVNVBMIT-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- ZQMUVWLMQNOSBO-UHFFFAOYSA-N methyl propan-2-yl hydrogen phosphite Chemical compound COP(O)OC(C)C ZQMUVWLMQNOSBO-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-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
- C07F9/141—Esters of phosphorous acids
- C07F9/142—Esters of phosphorous acids with hydroxyalkyl compounds without further substituents on alkyl
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 von Dialkylphosphiten mit ungleichen Alkylresten Es ist bereits bekannt, Dialkylphosphite mit zwei gleichen Alkylresten herzustellen (vgl.Berichte, Bd. 38, 5. 1171 [1901]; Berichte, Bd. 62, 5. 1871 [1929-]; J. Chem. Soc., 1945, S.3803 Die Herstellung erfolgt üblicherweise durch Umsetzung von Phosphortrichlorid mit 3 Molen eines Alkohols und anschließende Abspaltung des leicht hydrolisierbaren dritten Alkylrestes, beispielsweise mit Wasser bei Zimmertemperatur.Process for the preparation of dialkyl phosphites with dissimilar alkyl groups It is already known to produce dialkyl phosphites with two identical alkyl radicals (See reports, Vol. 38, 5. 1171 [1901]; Reports, Vol. 62, 5. 1871 [1929-]; J. Chem. Soc., 1945, S.3803 The production is usually carried out by reacting phosphorus trichloride with 3 moles of an alcohol and subsequent cleavage of the easily hydrolyzable third alkyl radical, for example with water at room temperature.
Ferner ist es nach Ko sol apo f f Organophosphorus Compounds, 1950, S. 182, bekannt, daß diese Reaktion in einem inerten Lösungsmittel durchgeführt werden kann. Im allgemeinen reagieren niedere Alkohole leichter mit Phosphortrichlorid als höhere Alkohole. Furthermore, according to Ko sol apo f f Organophosphorus Compounds, 1950, S. 182, known that this reaction was carried out in an inert solvent can be. In general, lower alcohols react more easily with phosphorus trichloride than higher alcohols.
Man hat auch bereits Methyiäthylphosphit, also ein Dialkylphosphit mit ungleichen -Alkylresten hergestellt. Gemäß der USA.-Patentschrift 2 559 854 gelingt die Herstellung in 770/oiger Ausbeute durch Umsetzung von -c H3 0 P C12 mit Äthanol in Äther unter starker Kühlung und Durchblasen von Luft. Nach der im J. Chem. Soc., 1953, S. 2233, angegebenen Verfahrensweise wird die Substanz durch Umsetzung von C2 H5 O P Cl2 mit 2 Äquivalenten Natriummethylat und Verseifung des in 400/oiger Ausbeute gebildeten Dimethyläthylphosphits erhalten. You also have methyl phosphite, a dialkyl phosphite produced with unequal -alkyl radicals. According to U.S. Patent 2,559,854 the production succeeds in 770% yield by reaction of -c H3 0 P C12 with ethanol in ether with strong cooling and bubbling with air. According to the im J. Chem. Soc., 1953, p. 2233, indicated procedure, the substance is by Implementation of C2 H5 O P Cl2 with 2 equivalents of sodium methylate and saponification of the Obtained dimethylethylphosphite formed in a yield of 400%.
Beide Verfahren gehen von Alkoxyphosphordichloriden aus, die in bestem Falle in 700/auger Ausbeute aus Phosphortrichlorid und dem entsprechenden Alkohol erhalten werden; als Nebenprodukte bilden sich roter Phosphor und Alkylchloride (s. Zentralblatt, 1897, II, s. 333). Both processes are based on alkoxyphosphorus dichlorides, which in the best Fall in 700 / auger yield from phosphorus trichloride and the corresponding alcohol obtained; red phosphorus and alkyl chlorides are formed as by-products (see Zentralblatt, 1897, II, p. 333).
Eine Anwendung dieser beiden Verfahren auf andere Dialkylphosphite mit ungleichen Alkylgruppen ist nicht bekannt. An application of these two methods to other dialkyl phosphites with dissimilar alkyl groups is not known.
Es wurde nun gefunden, daß man Dialkylphosphite mit ungleichen Alkylresten der Formel in der R einen Äthyl-, Propyl-, i-Propyl- Butyl- oder i-Butylrest bedeutet, in guter Ausbeute und in einfacher Weise erhalten kann, wenn man 2 Mol Methanol und 1 Mol ROH mit 1 Mol Phophortrihalogenid in einem inerten Lösungsmittel bei Temperaturen von -10 bis + 100 C unter völlig wasserfreien Bedingungen umsetzt und das bei der Reaktion abgespaltene Methylhalogenid mittels eines inerten Gases aus dem Reaktionsgemisch entfernt.It has now been found that dialkyl phosphites with dissimilar alkyl radicals of the formula in which R is an ethyl, propyl, i-propyl, butyl or i-butyl radical, can be obtained in good yield and in a simple manner if 2 moles of methanol and 1 mole of ROH are added with 1 mole of phosphorus trihalide in an inert solvent Reacts temperatures of -10 to + 100 C under completely anhydrous conditions and the methyl halide split off during the reaction is removed from the reaction mixture by means of an inert gas.
Erfindungsgemäß kann man z. B. 2 Mol wasserfreies Methanol und 1 Mol wasserfreies Äthanol (bzw. Propanol, i-Propanol, Butanol oder i-Butanol) in einem inerten Lösungsmittel lösen und unter- Kühlung auf -5 bis 0° C 1 Mol Phosphortrichlorid, gelöst in einem inerten Lösungsmittel, zutropfen. According to the invention you can, for. B. 2 moles of anhydrous methanol and 1 Moles of anhydrous ethanol (or propanol, i-propanol, butanol or i-butanol) in one Dissolve inert solvent and cool to -5 to 0 ° C 1 mole of phosphorus trichloride, dissolved in an inert solvent, added dropwise.
Als Lösungsmittel für die umzusetzenden Alkohole und das Phosphortrihalogenid werden inerte Lösungsmittel verwendet; besonders geeignet sind chlorierte Kohlenwasserstoffe, wie Tetrachlorkohlenstoff, Chloroform oder Dichloräthan. As a solvent for the alcohols to be converted and the phosphorus trihalide inert solvents are used; chlorinated hydrocarbons are particularly suitable, such as carbon tetrachloride, chloroform or dichloroethane.
Für das erfindungsgemäße Verfahren ist es wesentlich, daß die Reaktionstemperatur zwischen -10 und + 100 C, vorzugsweise zwischen - 10 und 0° C, gehalten wird. Bei höheren Temperaturen fällt die Ausbeute stark ab. Die Reaktionstemperatur darf + 100 C auf keinen Fall überschreiten. Weiterhin ist für eine gute Ausbeute völlige Wasserfreiheit der Reaktionskomponenten der verwendeten Lösungsmittel und des inerten Gases unbedingt erforderlich. For the process according to the invention, it is essential that the reaction temperature between -10 and + 100 C, preferably between -10 and 0 ° C, is kept. at The yield drops sharply at higher temperatures. The reaction temperature may be + Do not exceed 100 C under any circumstances. Furthermore, it is complete for a good yield The reactants, the solvents used and the inert solvent are free from water Gas absolutely necessary.
Versucht man, die Reaktion unter Verwendung von 2 Mol des höheren Alkohols und 1 Mol Methanol durchzuführen, so erhält man keine einheitliche Verbindung, sondern ein Gemisch verschiedener Phosphite. Trying to run the reaction using 2 moles of the higher Alcohol and 1 mole of methanol, no uniform compound is obtained, but a mixture of different phosphites.
Die Ester sind farblose Flüssigkeiten. Sie dienen als Zwischenprodukte für Schädlingsbekämpfungs -mittel, Schmiermittel und Pharmazeutika. Durch das erfindungsgemäße Verfahren wird eine Reihe bisher schwer oder gar nicht herstellbarer organischer Phosphorverbindungen leicht zugänglich. Man erhält z. B. durch Umsetzung der erfindungsgemäß erhaltenen Verbindungen mit Chloral neue Dialkyl-dichlorvinylphosphate, durch Umsetzung mit Schwefel neue Dialkylthiophosphate; beide Gruppen von Verbindungen sind hochwirksame Schädlingsbekämpfungsmittel. The esters are colorless liquids. They serve as intermediate products for pesticides, lubricants and pharmaceuticals. By the invention Process becomes a number of organic ones that were previously difficult or impossible to manufacture Phosphorus compounds easily accessible. One obtains z. B. by implementing the invention obtained compounds with chloral new dialkyl dichlorovinyl phosphate, by reaction with sulfur, new dialkyl thiophosphates; both groups of compounds are highly effective Pesticides.
Beispiel 1 Methyläthylphosphit 64 Teile Methanol und 46 Teile Äthanol werden in 200 Teilen Tetrachlorkohlenstoff gelöst und auf - 50 C abgekühlt. Unter Rühren und gleichzeitigem C O2-Einblasen werden 137,5 Teile Phosphortrichlorid innerhalb von 11/2 Stunden zugetropft. Nach weiterem 3stündigem Durchblasen von Kohlendioxyd bei 0° C wird das Lösungsmittel abdestilliert. Der Ester wird im Vakuum destilliert. Kp.1,5 = 530 Ausbeute: 97,5 Teile (78 0/o der Theorie). Example 1 Methylethylphosphite 64 parts of methanol and 46 parts of ethanol are dissolved in 200 parts of carbon tetrachloride and heated to -50 ° C cooled down. 137.5 parts of phosphorus trichloride are formed while stirring and simultaneously blowing in C O2 added dropwise within 11/2 hours. After blowing through for a further 3 hours Carbon dioxide at 0 ° C, the solvent is distilled off. The ester is in vacuo distilled. Bp 1.5 = 530 Yield: 97.5 parts (78% of theory).
Beispiel 2 Methylisopropylphosphit 64 Teile Methanol und 60 Teile i-Propanol werden, wie im Beispiel 1 beschrieben, umgesetzt. Die Ausbeute beträgt 81,5 Teile (590/0 der Theorie); Kp.2=53 bis 550 C. Example 2 Methyl isopropyl phosphite 64 parts of methanol and 60 parts i-Propanol are, as described in Example 1, implemented. The yield is 81.5 parts (590/0 of theory); Kp.2 = 53 to 550 C.
Beispiel 3 Methyl-n-butylphosphit 64 Teile Methanol und 74 Teile n-Butanol werden, wie im Beispiel 1 beschrieben, umgesetzt. Kr.2,5=65 bis 680 C. Example 3 Methyl n-butyl phosphite 64 parts of methanol and 74 parts As described in Example 1, n-butanol is reacted. Kr.2,5 = 65 to 680 C.
Beispiel 4 Methyl-äthylphosphit 96 g Methanol und 69 g Äthanol werden in 250 ccm Toluol gelöst und die Lösung auf -50 C abgekühlt. Example 4 Methyl ethyl phosphite 96 g of methanol and 69 g of ethanol are used dissolved in 250 ccm of toluene and the solution cooled to -50 ° C.
Unter Rühren und gleichzeitigem C O2-Einblasen werden 206 g Phosphortrichlorid, die in 150 ccm Toluoyl gelöst sind, innerhalb 1t/2 Stunden zugetropft. Danach wird 3 Stunden lang bei 00 C weiter C O2 durch das Reaktionsgemisch durchgeblasen. Anschließend wird im Vakuum (20 bis 30 ccm) 150 bis 200 ccm Toluol abdestilliert. Ausbeute quantitativ.While stirring and simultaneously blowing in C O2, 206 g of phosphorus trichloride, which are dissolved in 150 ccm of toluoyl, added dropwise within 1t / 2 hours. After that, will For 3 hours at 00 C, further C O2 was bubbled through the reaction mixture. Afterward 150 to 200 cc of toluene is distilled off in vacuo (20 to 30 ccm). Quantitative yield.
Die Lösung des Methyl-äthyl-phosphits in Toluol kann direkt, mit Chloral beispielsweise, weiter umgesetzt werden. The solution of the methyl-ethyl-phosphite in toluene can directly, with Chloral, for example, can be further implemented.
Claims (5)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB50098A DE1078558B (en) | 1958-08-25 | 1958-08-25 | Process for the preparation of dialkyl phosphites with dissimilar alkyl groups |
| BE581865A BE581865A (en) | 1958-08-25 | 1959-08-20 | Process for preparing dialkylated phosphites containing different alkyl residues |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB50098A DE1078558B (en) | 1958-08-25 | 1958-08-25 | Process for the preparation of dialkyl phosphites with dissimilar alkyl groups |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1078558B true DE1078558B (en) | 1960-03-31 |
Family
ID=6969078
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB50098A Pending DE1078558B (en) | 1958-08-25 | 1958-08-25 | Process for the preparation of dialkyl phosphites with dissimilar alkyl groups |
Country Status (2)
| Country | Link |
|---|---|
| BE (1) | BE581865A (en) |
| DE (1) | DE1078558B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2309563A1 (en) * | 1975-04-30 | 1976-11-26 | Hoechst Ag | PROCESS FOR PREPARATION OF ESTERS CONTAINING PHOSPHORUS |
| US8309736B2 (en) | 2007-02-16 | 2012-11-13 | Centre National De La Recherche Scientifique (Cnrs) | Alkyl H-phosphonates of N,N′-dialkylimidazoliums and of quaternary ammoniums and uses thereof |
-
1958
- 1958-08-25 DE DEB50098A patent/DE1078558B/en active Pending
-
1959
- 1959-08-20 BE BE581865A patent/BE581865A/en unknown
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2309563A1 (en) * | 1975-04-30 | 1976-11-26 | Hoechst Ag | PROCESS FOR PREPARATION OF ESTERS CONTAINING PHOSPHORUS |
| US8309736B2 (en) | 2007-02-16 | 2012-11-13 | Centre National De La Recherche Scientifique (Cnrs) | Alkyl H-phosphonates of N,N′-dialkylimidazoliums and of quaternary ammoniums and uses thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| BE581865A (en) | 1960-12-16 |
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