DE1002354C2 - Process for the production of new organic compounds containing halogen and phosphorus - Google Patents
Process for the production of new organic compounds containing halogen and phosphorusInfo
- Publication number
- DE1002354C2 DE1002354C2 DE1952C0006441 DEC0006441A DE1002354C2 DE 1002354 C2 DE1002354 C2 DE 1002354C2 DE 1952C0006441 DE1952C0006441 DE 1952C0006441 DE C0006441 A DEC0006441 A DE C0006441A DE 1002354 C2 DE1002354 C2 DE 1002354C2
- Authority
- DE
- Germany
- Prior art keywords
- phosphorus
- organic compounds
- production
- compounds containing
- containing halogen
- 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
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title claims description 4
- 229910052736 halogen Inorganic materials 0.000 title claims description 4
- 150000002367 halogens Chemical class 0.000 title claims description 4
- 150000002894 organic compounds Chemical class 0.000 title claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 title claims description 4
- 239000011574 phosphorus Substances 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 238000000034 method Methods 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 15
- -1 substituted Chemical class 0.000 claims description 5
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 10
- 239000007859 condensation product Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 6
- CZHYKKAKFWLGJO-UHFFFAOYSA-N dimethyl phosphite Chemical compound COP([O-])OC CZHYKKAKFWLGJO-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 241000607479 Yersinia pestis Species 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- QPKOILOWXGLVJS-UHFFFAOYSA-N bis(2-methylpropoxy)-oxophosphanium Chemical compound CC(C)CO[P+](=O)OCC(C)C QPKOILOWXGLVJS-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000346 nonvolatile oil Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 2
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- GGCXLVWDCPTFMN-UHFFFAOYSA-N bis(2-chloroethyl) hydrogen phosphite Chemical compound ClCCOP(O)OCCCl GGCXLVWDCPTFMN-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- NFORZJQPTUSMRL-UHFFFAOYSA-N dipropan-2-yl hydrogen phosphite Chemical compound CC(C)OP(O)OC(C)C NFORZJQPTUSMRL-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- SJMLNDPIJZBEKY-UHFFFAOYSA-N ethyl 2,2,2-trichloroacetate Chemical compound CCOC(=O)C(Cl)(Cl)Cl SJMLNDPIJZBEKY-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001424 substituent group Chemical group 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have 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)
- Lubricants (AREA)
Description
DEUTSCHESGERMAN
PATENTAMTPATENT OFFICE
BEKANNTHACHONG DER ANMELDUNG UND AUSGABE DER AUSLEGESCHRIFT:KNOWN THACHONG THE REGISTRATION AND ISSUE OF EDITORIAL:
AUSGABE DER PATENTSCHRIFTISSUE OF PATENT LETTERING
DBP 1002354 kl. 12 ο 26/01 DBP 1002354 kl. 12 ο 26/01
INTERNAT. KL C 07 f 22. SEPTEMBER 1952INTERNAT. KL C 07 f SEPTEMBER 22, 1952
14. FEBRUAR 1957 18. JULI 1957FEBRUARY 14, 1957 JULY 18, 1957
stimmt Oberein mit auslegeschriftagrees with the exposition
1 002 ?S4 (C 6441IV b /12 o)1 002? S4 (C 6441IV b / 12 o)
Es wurde gefunden, daß man zu neuen Halogen und Phosphor enthaltenden, organischen Verbindungen der wahrscheinlichen allgemeinen FormelIt has been found that new halogen and phosphorus-containing organic compounds of the likely general formula
R1-OR 1 -O
R2-OR 2 -O
OHOH
0-R4 0-R 4
0-R5 0-R 5
R1-On
R2-O'R 1 -O n
R 2 -O '
:p-o-rs Verfahren zur Herstellung von neuen Halogen und Phosphor enthaltenden, organischen Verbindungen : por s Process for the production of new organic compounds containing halogen and phosphorus
worin R1, R2, R4 und R5 gegebenenfalls substituierte aliphatische Reste bedeuten, gelangt, wenn man eine Verbindung der allgemeinen Formelin which R 1 , R 2 , R 4 and R 5 are optionally substituted aliphatic radicals obtained when a compound of the general formula
IO Patentiert für: IO patented for:
CIBA Aktiengesellschaft, Basel (Schweiz)CIBA Aktiengesellschaft, Basel (Switzerland)
Beanspruchte Priorität: Schweiz vom 25. September 1951Claimed priority: Switzerland from September 25, 1951
worin R1, R2 und R3 einen — gegebenenfalls substituierten — aliphatischen Rest bedeuten, mit einer Verbindung der allgemeinen Formelwherein R 1 , R 2 and R 3 denote an - optionally substituted - aliphatic radical, with a compound of the general formula
OH
R*~°\ I »5 OH
R * ~ ° \ I »5
^p-O-C-Ca3 ^ pOC-Ca 3
5"~ H 5 "~ H
worin R4, R5 die eingangs erwähnte Bedeutung haben, im molekularen Verhältnis umsetzt, wobei' R3Cl abgespalten wLrd. wherein R 4 , R 5 have the meaning mentioned at the beginning, are converted in the molecular ratio, where 'R 3 Cl is split off.
Die aliphatischen Reste, die diurch die Symbole R1, R2, R3, R4 und R5 dargestellt werden, können geradkettig, verzweigt, 'gesättigt oder ungesättigt sein; ferner können sie substituiert oder (unsuibstituiert sein. Genannt seien z. B. folgende Gruppen: Methyl-, Äthyl-, Propyl-, Isopropyl-, Butyl-, Hexyl-, 2-Äthylbuthyl-, Octyl-, 2-ButyJ-octyl-, Lauryl-, Octadecyl-, Allyl-, 2-Chloräthyl-; ferner Radikale mit Rhodan-, Cyan- oder Estergruppen. Die drei1 Reste R1, R8 und R3 können gleich odör verschieden sein. Beispielsweise seien folgende Verbindlungen genannt: Trimethylphosphiit, Triäthylphosphit, Tdpropylphosphit, Di>äthyl-laurylphosphit oder Tiri-2-chloräthylphosphit.The aliphatic radicals which are represented by the symbols R 1 , R 2 , R 3 , R 4 and R 5 can be straight-chain, branched, saturated or unsaturated; They can also be substituted or unsubstituted. Examples include the following groups: methyl, ethyl, propyl, isopropyl, butyl, hexyl, 2-ethylbutyl, octyl, 2-butyl-octyl- , Lauryl, octadecyl, allyl, 2-chloroethyl; furthermore radicals with rhodium, cyano or ester groups. The three 1 radicals R 1 , R 8 and R 3 can be identical or different. The following compounds may be mentioned as examples: Trimethylphosphite, triethylphosphite, Tdpropylphosphit, diethyl-laurylphosphite or Tiri-2-chloroethylphosphite.
Die als zweite Komponente zu verwendenden Verbindungen, die der allgemeinen FormelThe compounds to be used as the second component, those of the general formula
OHOH
^P-O-C-CCl3 ^ POC-CCl 3
R5-O^ IR 5 -O ^ I
worin R4 und R5 die eingangs erwähnte Bedeutung Dr. Richard Sallmann, Basel (Schweiz), ist als Erfinder genannt worden w orin R 4 and R 5 the meaning mentioned at the beginning Dr. Richard Sallmann, Basel (Switzerland), has been named as the inventor
haben, entsprechen, sind aus Chloral und Verbindungen der allgemeinen Formelhave, correspond, are composed of chloral and compounds of the general formula
4-0, 4 -0,
R5-O'R 5 -O '
-OH-OH
worin R4 und R5 die oben gegebene Bedeutung besitzen, zugänglich. Die SubstituentenR4 und R5 können die weiter oben bei der Beschreibung der Verbindungen der Formelwherein R 4 and R 5 have the meaning given above, accessible. The substituents R 4 and R 5 can be those given above in the description of the compounds of the formula
Ri-On Ri-O n
R4-O'R 4 -O '
;p-o—R3 ; po — R 3
angegebene Bedeutung besitzen. Unter den für die Herstellung der Chloraladditionsprodukte geeigneten Verbindungen seien beispielsweise Dimefchylphosphit, Diäthylphosphit, Diisopropylphosphit oder Diisobutylphosphit genannt.have given meaning. Among those suitable for the preparation of the chloral addition products Compounds are, for example, dimefchyl phosphite, Diethyl phosphite, diisopropyl phosphite or diisobutyl phosphite called.
Die erfindungsgeraäße Kondensation erfolgt diurch Umsetzung der Komponenten in. molekularem Verhältnis. The condensation according to the invention takes place through this Implementation of the components in a molecular ratio.
Weil die Reaktion oft exotherm verlauft, ist es gegebenenfalls notwendig, die Reaktionskomponenten unter Kühlung zu vereinigen und sie mit inerten Lösungsmitteln, wie Benzol, Toluol, Äther, Dioxan, Hexan oder tiefsiedendem Benzin, zu verdünnen. Zweckmäßig wird die Umsetzung durch Erwärmen beendet. In vielen Fällen genügt ein Erhitzen auf 50 bis 1ÜO' . Bei Verwendung von reaktionsträgeren Verbindungen werden höhere Temperaturen benötigt, z. B. 130 bis 150°.Because the reaction is often exothermic, it may be necessary to add the reaction components to combine with cooling and they with inert Solvents such as benzene, toluene, ether, dioxane, hexane or low-boiling gasoline. The reaction is expediently terminated by heating. In many cases, heating to 50 is sufficient to 1ÜO '. When using less reactive compounds higher temperatures are required, e.g. B. 130 to 150 °.
Die neuen, erfindungsgemaßen Produkte sind im allgemeinen schwere, ziemlich viskose öle, die sich auch unter stark vermindertem Druck nicht ohne Zersetzung destillieren lassen. Sie können als Zwischenprodukte für die verschiedensten Zwecke verwendet werden, instesondere zur Herstellung von gegenüber Schädlingen wirksamen Verbindungen.The new products of the invention are generally Heavy, rather viscous oils, which do not decompose even under greatly reduced pressure let distill. They can be used as intermediates for a wide variety of purposes, in particular for the preparation of compounds effective against pests.
Da die neuen Kondensationsprodukte selber schon große Wirksamkeit gegenüber tierischen Schädlingen besitzen, ist es auch möglich, sie selber Schädlimgsbekämpfungspräparaten als Wirkstoffe einzuverleiben.Since the new condensation products themselves are already very effective against animal pests own, it is also possible to use pest control preparations yourself to be incorporated as active ingredients.
In der britischen Patentanmeldung 12350 vom Jahre 1949 werden Schmiermittel beschrieben, welche als Zusätze zur Verbesserung der Eigenschaften Kondensationsprodukte aus Phosphaten und Polyhalogenverbindungen, z. B. Tetrachlorkohlenstoff, Chloral oder Trichloressigsäureäthylester, enthalten. In dieser Anmeldung sind keine Angaben vorhanden über eine eventuelle Wirksamkeit der Verbindungen gegenüber Schädlingen. In der USA.-Patentschrift 2 485 573 werden Kondensationsprodukte aus Dialkylphosphiten und Aldehyden, instesondere Chloral, als Schädlingsbekämpfungsmittel beschrieben. Gegenüber den Kondensationsprodukten aus Dimethyl- bzw: Diathylphosphit und Cloral besitzen die geprüften erfindungsgemaßen Verbindungen eine größere kontaktinsektizide Wirkung, wie Vergleichsversuche gezeigt haben.In British patent application 12350, dated 1949, lubricants are described which as additives to improve the properties of condensation products from phosphates and polyhalogen compounds, z. B. carbon tetrachloride, chloral or ethyl trichloroacetate. In this application there is no information available about a possible effectiveness of the compounds against Pests. U.S. Patent 2,485,573 discloses condensation products from dialkyl phosphites and aldehydes, especially chloral, are described as pesticides. Compared to the condensation products From dimethyl or diethyl phosphite and Cloral, the tested compounds according to the invention have greater contact insecticides Effect, as comparative tests have shown.
In den folgenden Beispielen bedeuten Teile Gewichtsteile. Das Verhältnis zwischen Gewichtsteil und Volumteil ist das gleiche wie dasjenige zwischen dem Kilogramm und dem Liter.In the following examples, parts mean parts by weight. The ratio between part by weight and Volume part is the same as that between the kilogram and the liter.
8,6 Teile des unten beschriebenen Produktes aus Dimethylphosphit und Chloral werden mit 5,6 Teilen Triäthylphosphit während I1A Stunden auf 140° erhitzt. Es setzt sofort eine heftige Gasentwicklung ein, welche bald beendigt ist. Anschließend wird die Reaktionsmasse zur Entfernung von wenig leichtflüchtigen Bestandteilen unter vermindertem Druck erwärmt. Das Kondensationsprodukt bleibt als nicht flüchtiges öl zurück.8.6 parts of the below-described product of dimethyl phosphite and chloral are heated with 5.6 parts of triethyl phosphite while I 1 A hours at 140 °. A violent evolution of gas sets in immediately, which is soon over. The reaction mass is then heated under reduced pressure to remove less volatile components. The condensation product remains as a non-volatile oil.
Das oben verwendete Produkt aus Dimethylphosphit und Chloral kann wie folgt hergestellt werden: 11 Teile Dimethylphosphit werden mit 14,8 Teilen Chloral vermischt. Nach kurzer Zeit beginnt die Reaktion. Durch vorsichtige Kühlung wird die Temperatur auf 50 bis 60° gehalten. Wenn keine Temperatursteigerung mehr erfolgt, wird das Gemisch während 1 Stunde auf dem Dampfbad erhitzt und über Nacht bei Raumtemperatur stehengelassen. Die Reaktionsmasse erstarrt dann zu einem Krietallbrei. Nach Lösen in der etwa ofachen Menge Äther und Kuhlen wird das Produkt in farblosen Kristallen erhalten, welche bei 76 bis 77° schmelzen.The product of dimethyl phosphite and chloral used above can be made as follows: 11 parts Dimethyl phosphite are mixed with 14.8 parts of chloral. The reaction begins after a short time. Through careful cooling, the temperature is kept at 50 to 60 °. If no temperature increase If more occurs, the mixture is heated on the steam bath for 1 hour and at room temperature overnight ditched. The reaction mass then solidifies to form a crystal pulp. After solving in the the product becomes about an open amount of ether and cooling obtained in colorless crystals which melt at 76 to 77 °.
12,8 Teile des nach Absatz 2 des Beispiels 1 erhaltenen Produktes aus Dimethylphosphit und Chloral werden mit 6,4 Teilen Trimethylphosphit während 1 Stunde auf dem Dampfbad erhitzt. Es tritt lebhafte Gasentwicklung ein.12.8 parts of that obtained in accordance with paragraph 2 of Example 1 Product made from dimethyl phosphite and chloral are mixed with 6.4 parts of trimethyl phosphite during Heated on the steam bath for 1 hour. Vigorous evolution of gas occurs.
Anschließend wird die Reaktionsma&se zur Entfernung von wenig leichtflüchtigen Bestandteilen unter vermindertem Druck erwärmt. Das KondensationsprodSukt bleibt als nicht flüchtiges öl zurück.Then the reaction measure is used for removal heated by low volatile components under reduced pressure. The condensation product remains as a non-volatile oil.
An Stelle des Kondensationsproduktes aus Chloral und Dimethylphosphit kann man auch eine äquivalente ao Menge der aus Diisobutylphosphit oder Di-(2-chloräthyl)-phosphit und Chloral erhältlichen Verbindungen benutzen.Instead of the condensation product of chloral and dimethyl phosphite, an equivalent can also be used ao amount of the compounds obtainable from diisobutyl phosphite or di- (2-chloroethyl) phosphite and chloral use.
Claims (1)
USA.-Patentschrift Nc. 2 485 573;
britische Patentanmeldung Nr. 12350 aus dem Jahre 1949. Considered publications:
U.S. Patent Nc. 2,485,573;
British Patent Application No. 12350 from 1949.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1002354X | 1951-09-25 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1002354B DE1002354B (en) | 1957-02-14 |
| DE1002354C2 true DE1002354C2 (en) | 1957-07-18 |
Family
ID=4552112
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1952C0006441 Expired DE1002354C2 (en) | 1951-09-25 | 1952-09-22 | Process for the production of new organic compounds containing halogen and phosphorus |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1002354C2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE617821A (en) * | 1961-05-19 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB191112350A (en) * | 1911-05-22 | 1911-11-16 | Leo Wallerstein | Treatment of Beer or Ale. |
| US2485573A (en) * | 1945-10-05 | 1949-10-25 | Rohm & Haas | Thiocyanated phosphite esters |
-
1952
- 1952-09-22 DE DE1952C0006441 patent/DE1002354C2/en not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB191112350A (en) * | 1911-05-22 | 1911-11-16 | Leo Wallerstein | Treatment of Beer or Ale. |
| US2485573A (en) * | 1945-10-05 | 1949-10-25 | Rohm & Haas | Thiocyanated phosphite esters |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1002354B (en) | 1957-02-14 |
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