DE930210C - Process for the preparation of sultam-N-phosphoric acid dialkyl esters or sultam-N-thiophosphoric acid dialkyl esters - Google Patents
Process for the preparation of sultam-N-phosphoric acid dialkyl esters or sultam-N-thiophosphoric acid dialkyl estersInfo
- Publication number
- DE930210C DE930210C DER11947A DER0011947A DE930210C DE 930210 C DE930210 C DE 930210C DE R11947 A DER11947 A DE R11947A DE R0011947 A DER0011947 A DE R0011947A DE 930210 C DE930210 C DE 930210C
- Authority
- DE
- Germany
- Prior art keywords
- sultam
- dialkyl esters
- acid dialkyl
- preparation
- phosphoric acid
- 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
- 150000002148 esters Chemical class 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 title claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 title claims description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- 239000003513 alkali Substances 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- HPFKOFNYNQMWEF-UHFFFAOYSA-N chloro-dihydroxy-sulfanylidene-$l^{5}-phosphane Chemical compound OP(O)(Cl)=S HPFKOFNYNQMWEF-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000012230 colorless oil Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ITVPBBDAZKBMRP-UHFFFAOYSA-N chloro-dioxido-oxo-$l^{5}-phosphane;hydron Chemical compound OP(O)(Cl)=O ITVPBBDAZKBMRP-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- VLCIZRGGXDWGSO-UHFFFAOYSA-N 5-methyl-1,2-thiazolidine 1,1-dioxide Chemical compound CC1CCNS1(=O)=O VLCIZRGGXDWGSO-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- NGFFLHMFSINFGB-UHFFFAOYSA-N [chloro(methoxy)phosphoryl]oxymethane Chemical group COP(Cl)(=O)OC NGFFLHMFSINFGB-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 1
- LGTLXDJOAJDFLR-UHFFFAOYSA-N diethyl chlorophosphate Chemical compound CCOP(Cl)(=O)OCC LGTLXDJOAJDFLR-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011874 heated mixture Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6536—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and sulfur atoms with or without oxygen atoms, as the only ring hetero atoms
- C07F9/6544—Six-membered rings
-
- 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6536—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and sulfur atoms with or without oxygen atoms, as the only ring hetero atoms
- C07F9/6539—Five-membered rings
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
BUNDESREPUBLIK DEUTSCHLANDFEDERAL REPUBLIC OF GERMANY
AUSGEGEBEN AM 11. JULI 1955ISSUED JULY 11, 1955
DEUTSCHES PATENTAMTGERMAN PATENT OFFICE
PATENTSCHRIFTPATENT LETTERING
KLASSE 12p GRUPPE 4CLASS 12p GROUP 4
R 11947 IVc 112 pR 11947 IVc 112 p
Dr. Hans Feichtinger, Duisburg-Beeck und Dr. Hans Tummes, Duisburg-MeiderichDr. Hans Feichtinger, Duisburg-Beeck and Dr. Hans Tummes, Duisburg-Meiderich
sind als Erfinder genannt wordenhave been named as inventors
Ruhrchemie Aktiengesellschaft, Oberhausen (RhId.)-HoltenRuhrchemie Aktiengesellschaft, Oberhausen (RhId.) - Holten
Verfahren zur Herstellung von Sultam-N-phosphorsäuredialkylestem oderSultam-N-thiophosphorsäuredialkylesternProcess for the preparation of Sultam-N-phosphoric acid dialkyl esters or Sultam-N-thiophosphoric acid dialkyl esters
Patentiert im Gebiet der Bundesrepublik Deutschland vom 23. Juni 1953 anPatented in the territory of the Federal Republic of Germany on June 23, 1953
Patentanmeldung bekanntgemacht am 20. Januar 1955Patent application published January 20, 1955
Patenterteilung bekanntgemacht am 16. Juni 1955Patent issued June 16, 1955
Es wurde gefunden, daß sich Verbindungen der allgemeinen FormelIt has been found that compounds of the general formula
SO,SO,
!Ν —P^OR' bzw.
OR'! Ν —P ^ OR 'resp.
OR '
so«so"
N — Ρς-OR'
XOR'N - Ρς-OR '
X OR '
in der R eine geradkettige oder verzweigte gesättigte Kohlenwasserstoffbrücke von 3 bis 6 Kohlenstoffatomen und R' eine Methyl- oder Äthylgruppe bedeutet, herstellen lassen, wenn man diein which R is a straight-chain or branched saturated hydrocarbon bridge of 3 to 6 carbon atoms and R 'is a methyl or ethyl group, can be prepared if the
Alkalisalze der Sultame der allgemeinen FormelAlkali salts of the sultams of the general formula
NMeNMe
mit Chlorphosphorsäuredialkylestern oder Chlorthiophosphorsäuredialkylestern der Formelwith chlorophosphoric acid dialkyl esters or chlorothiophosphoric acid dialkyl esters the formula
Cl-P —OR'Cl-P —OR '
OR'OR '
umsetzt, wobei R' und R die oben angegebene Be-converts, where R 'and R have the above
deutung haben, Me ein Alkalimetall darstellt und das mi't dem Phosphoratom doppelt gebundene
Sauerstoffatom durch ein Schwefelatom ersetzt werden kann.
Die Reaktion verläuft nach folgender Gleichung:have meaning, Me represents an alkali metal and the oxygen atom doubly bonded to the phosphorus atom can be replaced by a sulfur atom.
The reaction proceeds according to the following equation:
:NMe: NMe
SO2 SO 2
I — P.^ OR' OR'I - P. ^ OR 'OR'
R\ y° , R \ y °,
SO9 SUN 9
+MeCl+ MeCl
OR'OR '
Die für das Verfahren geeigneten SuItarne können aus Derivaten von substituierten Alkansulfonsäuren durch eine Cyclisiemngsreaktion, z. B-. aus den Aminoalkansulfochlorid-hydrochloriden durch Alkali, aus Chloralkansulfonamiden durch Erhitzen und aus Oxyalkansulfonsäure durch Einwirken von Ammoniak, dargestellt werden. Als Beispiel seien y-Propansultam, <5-Butansultam und a-Methyl-y-propansultatn ,genannt.The SuItarne suitable for the procedure can from derivatives of substituted alkanesulfonic acids by a Cyclisiemngsreaktion, z. B-. the end the aminoalkanesulphochloride hydrochlorides by alkali, from chloralkanesulphonamides by heating and from oxyalkanesulfonic acid by the action of ammonia. As an an example let y-propanesultam, <5-butanesultam and a-methyl-y-propane results, called.
Die Überführung der Sultame in die Alkalisalze erfolgt im allgemeinen durch Einwirkung einer äquivalenten Menge von Alkali alkoholat auf eine alkoholische Lösung der Sultame und Eindampfen der Reaktionslösung im Vakuum. Hierbei werden die N-Alkalisultame in fester Form erhalten.The conversion of the sultams into the alkali salts is generally carried out by the action of a equivalent amount of alkali alcoholate to an alcoholic solution of the sultame and evaporation the reaction solution in vacuo. The N-alkali ultams are obtained in solid form.
Zur Umsetzung mit den Chlorphosphorsäureestern wird das Alkalisultam in einem inerten Lösungsmittel, wie Benzol·, Äther oder Dioxan, suspendiert und unter Rühren mit der äquivalenten Menge Chlorphosphorsäuredimethyl- oder -äthylester versetzt.To react with the chlorophosphoric acid esters, the alkali sultam is in an inert Solvent, such as benzene, ether or dioxane, suspended and stirring with the equivalent Amount of chlorophosphoric acid dimethyl or ethyl ester added.
Die Reaktionstemperatur kann zwischen 20 und 8o° liegen. Die Reaktion ist beendet, wenn das basische Alkalisultam vollständig verbraucht ist, was leicht daran erkannt werden kann, daß der suspendierte Niederschlag der Reaktionsmischung nach Zugabe von Wasser nicht mehr basisch reagiert. Im allgemeinen ist dazu eine 2- bis 3stündige Reaktionszeit erforderlich.The reaction temperature can be between 20 and 80 °. The reaction is over when that basic Alkalisultam is completely consumed, which can easily be recognized by the fact that the suspended Precipitation of the reaction mixture no longer reacts as a base after the addition of water. In general, this takes 2 to 3 hours Response time required.
Die Isolierung der Sultamphosphorsäuredimethyl- oder -äthylester erfolgt durch Eindampfen der Reaktionslösung im Vakuum, wobei das Reaktionsprodukt schon meist in genügender Reinheit erhalten wird. Gegebenenfalls kann es durch Hochvakuumdestillation weiter gereinigt werden.The isolation of the sultamphosphorsäuredimethyl- or -äthylester takes place by evaporation of the Reaction solution in vacuo, the reaction product usually being obtained in sufficient purity will. If necessary, it can be further purified by high vacuum distillation.
Die Sultamphosphorsäuredimethyl- oder -äthylester sind farblose öle, die mit Wasser sowie den meisten organischen Lösungsmitteln mischbar sind. Sie können als Schädlingsbekämpfungsmittel Verwendung finden.The Sultamphosphorsäuredimethyl- or -äthylester are colorless oils that with water as well as the most organic solvents are miscible. They can use as a pesticide Find.
Das Verfahren ist auch zur Herstellung von Sultam-N-thiophosphorsäuredialkylestern geeignet. Die Sultame werden dabei statt mit Chlorphosphorsäuredialkylestern mit Chlorthiophosphorsäuredi-The process is also suitable for the preparation of sultam-N-thiophosphoric acid dialkyl esters. The sultams are used instead of dialkyl chlorophosphoric acid esters with chlorothiophosphoric acid
alkylestern umgesetzt. In diesem Falle entstehen Verbindungen der allgemeinen Formelalkyl esters implemented. In this case, compounds of the general formula are formed
^N— P^- OR' oJ 0R'^ N— P ^ - OR 'oJ 0R '
B-ei spiel iB-ei game i
Zu einer Lösung von 37 g Natriummethylat in 1000 cm3 absolutem Methanol wurden 67,5 g a-Methyl-y-propansultam zugegeben, und das Lösungsmittel wurde im Vakuum abgedampft, bis das Natriumsultam als fester weißer Rückstand zurückblieb. Nach Zugabe von 1000 cm3 absolutem Benzol wurde durch kräftiges Rühren das Natriumsultam möglichst fein suspendiert, worauf man in die auf 500 erwärmte Mischung 86 g Chlorphosphorsäurediäthylester langsam zutropfen ließ. Nach zweistündigem Rühren wurde das Benzol auf dem Wasserbade eingedampft und anschließend im Hochvakuum bei 1500 so lange erhitzt, bis nichts mehr überging. Der Destillationsrückstand wog ίβΟΐδ S und war ein schwach riechendes, farbloses Öl. Dichte d f = 1,2689, Brechungsindex η *°= 1,4665.67.5 g of α-methyl-γ-propanesultam were added to a solution of 37 g of sodium methylate in 1000 cm 3 of absolute methanol, and the solvent was evaporated off in vacuo until the sodium sultam remained as a solid white residue. After addition of 1000 cm 3 of absolute benzene was suspended finely as possible the Natriumsultam by vigorous stirring, followed by g in the 50 0 86 Chlorphosphorsäurediäthylester heated mixture was slowly added dropwise. After two hours of stirring, the benzene was evaporated on a water bath and then heated for so long in a high vacuum at 150 0 until nothing passed more. The distillation residue weighed ίβΟΐδ S was un d e i n weak smelling, colorless oil. Density d f = 1.2689, refractive index η * ° = 1.4665.
Die Analyse ergab die Zusammensetzung eines a - Methyl - γ - propansultam - N - diäthoxy - oxyphosphins der FormelThe analysis showed the composition of an α-methyl-γ -propanesultam-N-diethoxy-oxyphosphine of the formula
HoC — CHoHoC - CHo
,0, 0
CH,-HC N — Pr-ICH, -HC N - Pr-I
SO,SO,
OC9H,OC 9 H,
Formel: C8H18O5NSP, Molgewicht: 271,28. Berechnet:Formula: C 8 H 18 O 5 NSP, Molecular Weight: 271.28. Calculated:
C 35,42%, H 6,69%, N 5,16%, S 11,82°/», gefunden:C 35.42%, H 6.69%, N 5.16%, S 11.82%, found:
C 36,04%, H 6,59%, N 4,74%, S 11,20%.C 36.04%, H 6.59%, N 4.74%, S 11.20%.
Zu einer gut gerührten Suspension von 15,7 g N-Natrium-o-butansultam in 200 cm3 Benzol wurden bei 35° langsam 17,2 g Chlorphosphoirsäurediäthylester zugegeben. Nach 1 Stunde wurde die i™ Reaktionslösung im Vakuum auf dem Wasserbade eingedampft und das zurückbleibende farblose öl im Hochvakuum bei 1500 so lange erhitzt, bis nichts mehr überdestillierte. Dabei verblieben 25 g eines . farblosen Öles, das auf Grund der chemischen Zu- 11S sammensetzung weitgehend reines (5-Butansultam-N-diäthoxy-oxyphosphin der nachstehenden Formel war:17.2 g of diethyl chlorophosphorate were slowly added at 35 ° to a well-stirred suspension of 15.7 g of N-sodium-o-butanesultam in 200 cm 3 of benzene. After 1 hour, the i ™ reaction solution was evaporated in vacuo on a water bath and heated the residual colorless oil in high vacuum at 150 0 until no more distilled over. This left 25 g of one. colorless oil, which due to the chemical supply 11 S composition substantially pure (5-Butansultam-N-diethoxy-oxyphosphin the following formula was:
CH,CH,
i C.
i
SO2 \ /
SO 2
Claims (1)
^0R'Γ - P ς— OR 'or
^ 0R '
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DER11947A DE930210C (en) | 1953-06-22 | 1953-06-23 | Process for the preparation of sultam-N-phosphoric acid dialkyl esters or sultam-N-thiophosphoric acid dialkyl esters |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE761913X | 1953-06-22 | ||
DER11947A DE930210C (en) | 1953-06-22 | 1953-06-23 | Process for the preparation of sultam-N-phosphoric acid dialkyl esters or sultam-N-thiophosphoric acid dialkyl esters |
Publications (1)
Publication Number | Publication Date |
---|---|
DE930210C true DE930210C (en) | 1955-07-11 |
Family
ID=25947814
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DER11947A Expired DE930210C (en) | 1953-06-22 | 1953-06-23 | Process for the preparation of sultam-N-phosphoric acid dialkyl esters or sultam-N-thiophosphoric acid dialkyl esters |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE930210C (en) |
-
1953
- 1953-06-23 DE DER11947A patent/DE930210C/en not_active Expired
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