DE1085870B - Process for the preparation of bis-dialkylphosphoryl sulfoxides - Google Patents
Process for the preparation of bis-dialkylphosphoryl sulfoxidesInfo
- Publication number
- DE1085870B DE1085870B DEF25188A DEF0025188A DE1085870B DE 1085870 B DE1085870 B DE 1085870B DE F25188 A DEF25188 A DE F25188A DE F0025188 A DEF0025188 A DE F0025188A DE 1085870 B DE1085870 B DE 1085870B
- Authority
- DE
- Germany
- Prior art keywords
- sulfoxides
- bis
- dialkylphosphoryl
- preparation
- reaction
- 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
- 150000003462 sulfoxides Chemical class 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 3
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- -1 sulfonic acid chlorides Chemical class 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 150000001805 chlorine compounds Chemical class 0.000 description 3
- AFVJGYRAILXFPC-UHFFFAOYSA-N [chlorosulfinyl(methyl)amino]methane Chemical compound CN(C)S(Cl)=O AFVJGYRAILXFPC-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- RDPAIXGJGMTFIJ-UHFFFAOYSA-N C(C)P(=O)(CC)S(=O)P(=O)(CC)CC Chemical compound C(C)P(=O)(CC)S(=O)P(=O)(CC)CC RDPAIXGJGMTFIJ-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000126 substance 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 Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/1658—Esters of thiopolyphosphoric acids or anhydrides
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 Bis-dialkylphosphorylsulfoxyden Es wurde gefunden, daß 0, O-Dialkylphosphite mit Dialkylaminosulfinsäurechloriden reagieren, wobei Bisdialkylphosphoryl-sulfoxyde erhalten werden. Diese Reaktion kann durch folgendes Formelschema veranschaulicht werden: Die erfindungsgemäß erhältlichen Bis-dialkylphosphoryl-sulfoxyde sind schon aus der USA.-Patentschrift 2 508 364 bekannt. Nach den Angaben dieser Patentschrift werden jedoch die Bis-dialkylphosphoryl-sulfoxyde erhalten durch Reaktion von Trialkylphosphiten mit Thionylchlorid. Diese Umsetzung muß mit den technisch nicht leicht zugänglichen Trialkylphosphiten durchgeführt werden, während erfindungsgemäß die auf sehr einfache Weise zugänglichen O,O-Dialkylphosphite verwendet werden können. Es war nicht vorauszusehen, daß bei der Reaktion von O,O-Dialkylphosphiten mit Dialkylaminosulfinsäurechloriden die Bis-dialkylphosphoryl-sulfoxyde in guter Ausbeute erhältlich sind.Process for the preparation of bis-dialkylphosphoryl sulfoxides It has been found that 0, O-dialkyl phosphites react with dialkylaminosulfinic acid chlorides to give bisdialkylphosphoryl sulfoxides. This reaction can be illustrated by the following equation: The bis-dialkylphosphoryl-sulfoxides obtainable according to the invention are already known from US Pat. No. 2,508,364. According to the information in this patent specification, however, the bis-dialkylphosphoryl sulfoxides are obtained by reacting trialkyl phosphites with thionyl chloride. This reaction must be carried out with the trialkyl phosphites which are technically not easily accessible, while the O, O-dialkyl phosphites which are very easily accessible can be used according to the invention. It could not be foreseen that the bis-dialkylphosphoryl-sulfoxides would be obtainable in good yield in the reaction of O, O-dialkyl phosphites with dialkylaminosulfinic acid chlorides.
Die zur Herstellung der Bis-dialkylphosphoryl-sulfoxyde nach dem erfindungsgemäßen Verfahren benötigten Dialkylaminosulfinsäurechloride sind bis heute aus der Literatur noch nicht bekannt. Wohl sind die entsprechenden Sulfonsäurechloride schon nach den Angaben der deutschen Patentschrift 820001 zu entsprechenden Thiophosphorsäureesteranhydriden umgesetzt worden. For the preparation of the bis-dialkylphosphoryl sulfoxides according to the Dialkylaminosulfinic acid chlorides required processes according to the invention are to not yet known from literature today. The corresponding sulfonic acid chlorides are probably already according to the information in German patent 820001 on corresponding thiophosphoric ester anhydrides implemented.
Es konnte jedoch nicht erwartet werden, daß die chemisch völlig andersartig sich verhaltenden Sulfinsäurechloride analog reagieren würden, wobei in ausgezeichneter Ausbeute und hoher Reinheit entsprechende Phosphorylsulfoxyde gebildet werden.However, it could not be expected that the chemically completely different behaving sulfinic acid chlorides would react analogously, with excellent Corresponding phosphoryl sulfoxides are formed in a high yield and high purity.
Die folgenden Beispiele mögen das erfindungsgemäße Verfahren erläutern. The following examples are intended to illustrate the process according to the invention.
Beispiel 1 64 g Dimethylaminosulfinsäurechlorid (Kp.3=68°C) werden in 60 ccm Toluol gelöst. Diese Lösung tropft man unter Rühren zu einer Lösung von 70 g (ll2 Mol) O,O-Diäthylphosphit in 100 ccm Toluol bei etwa 85" C. Nach Abklingen der Reaktion kühlt man das Reaktionsprodukt auf Zimmertemperatur ab und saugt das entstandene salzsaure Dimethylamin ab. Beim anschließenden Fraktionieren des Filtrates werden 40 g des Bis-diäthylphosphoryl-sulfoxydes vom Kp. o,o, = 65 bis 70" C erhalten.example 1 64 g of dimethylaminosulfinic acid chloride (boiling point 3 = 68 ° C.) are dissolved in 60 cc of toluene. This solution is added dropwise with stirring to a solution of 70 g (112 mol) of O, O-diethyl phosphite in 100 cc of toluene at about 85 ° C. After the reaction has subsided, the reaction product is cooled to room temperature and the hydrochloric acid dimethylamine formed is filtered off with suction. During the subsequent fractionation of the filtrate, 40 g of bis-diethylphosphoryl sulfoxide with a boiling point of o, o, = 65 to 70 ° C. are obtained.
Ausbeute 5001, der Theorie.Yield 5001, the theory.
Berechnet für ein Molgewicht von 322 P19,201,, OC2H3 55'901o' S9,9%; gefunden . ...... P19,701,, OC2H554,5%, S9,8%. Calculated for a molecular weight of 322 P19,201 ,, OC2H3 55'9010 'S9.9%; found . ...... P19.701 ,, OC2H554.5%, S9.8%.
Beispiel 2 64 g Dimethylaminosulfinsäurechlorid (½ Mol) werden in 60 ccm Toluol gelöst. Diese Lösung gibt man wie im Beispiel 1 unter Rühren zu einer Lösung von 83 g O,O-n-Dipropylphosphit in 100 ccm Toluol bei 70" C.Example 2 64 g of dimethylaminosulfinic acid chloride (½ mol) are dissolved in 60 cc of toluene. This solution is added as in Example 1 with stirring to a solution of 83 g of O, On-dipropyl phosphite in 100 cc of toluene at 70 ° C.
Man hält die Temperatur bei 70° C ll2 Stunde, kühlt dann auf Zimmertemperatur ab und saugt das entstandene salzsaure Dimethylamin ab. Nach dem Abdestillieren des Lösemittels erhält man 86 g des Bis-n-dipropylphosphoryl-sulfoxyds. Beim Fraktionieren geht die Substanz bei Kp. 0,01 = 90 bis 95° C als farblose, wenig wasserlösliche Flüssigkeit überThe temperature is maintained at 70 ° C. for 112 hours and then cooled to room temperature and sucks off the hydrochloric acid dimethylamine formed. After distilling off of the solvent, 86 g of bis-n-dipropylphosphoryl sulfoxide are obtained. When fractionating the substance is colorless and slightly soluble in water at b.p. 0.01 = 90 to 95 ° C Liquid over
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF25188A DE1085870B (en) | 1958-03-06 | 1958-03-06 | Process for the preparation of bis-dialkylphosphoryl sulfoxides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF25188A DE1085870B (en) | 1958-03-06 | 1958-03-06 | Process for the preparation of bis-dialkylphosphoryl sulfoxides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1085870B true DE1085870B (en) | 1960-07-28 |
Family
ID=7091522
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF25188A Pending DE1085870B (en) | 1958-03-06 | 1958-03-06 | Process for the preparation of bis-dialkylphosphoryl sulfoxides |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1085870B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111138489A (en) * | 2020-01-14 | 2020-05-12 | 中节能万润股份有限公司 | Novel lithium ion battery electrolyte additive and electrolyte containing same |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE820001C (en) * | 1949-09-07 | 1951-11-08 | Bayer Ag | Process for the preparation of thiopyrophosphoric acid esters |
-
1958
- 1958-03-06 DE DEF25188A patent/DE1085870B/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE820001C (en) * | 1949-09-07 | 1951-11-08 | Bayer Ag | Process for the preparation of thiopyrophosphoric acid esters |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111138489A (en) * | 2020-01-14 | 2020-05-12 | 中节能万润股份有限公司 | Novel lithium ion battery electrolyte additive and electrolyte containing same |
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