DE1443711A1 - Process for the production of thiolphosphoric acid triesters from thionophosphoric acid triesters - Google Patents
Process for the production of thiolphosphoric acid triesters from thionophosphoric acid triestersInfo
- Publication number
- DE1443711A1 DE1443711A1 DE19631443711 DE1443711A DE1443711A1 DE 1443711 A1 DE1443711 A1 DE 1443711A1 DE 19631443711 DE19631443711 DE 19631443711 DE 1443711 A DE1443711 A DE 1443711A DE 1443711 A1 DE1443711 A1 DE 1443711A1
- Authority
- DE
- Germany
- Prior art keywords
- acid triesters
- acid
- thiolphosphoric
- production
- triesters
- 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
- 239000002253 acid Substances 0.000 title claims description 11
- 150000005691 triesters Chemical class 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 6
- 239000002841 Lewis acid Substances 0.000 claims description 5
- -1 alkyl radical Chemical group 0.000 claims description 5
- 150000007517 lewis acids Chemical class 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 230000000737 periodic effect Effects 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 5
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- TYKUWERMJPOFTH-UHFFFAOYSA-N (2,3-dimethyl-4-nitrophenoxy)-dihydroxy-sulfanylidene-$l^{5}-phosphane Chemical compound CC1=C(C)C([N+]([O-])=O)=CC=C1OP(O)(O)=S TYKUWERMJPOFTH-UHFFFAOYSA-N 0.000 description 1
- CLGNSHMVZBJLJV-UHFFFAOYSA-N 3,4-dibromo-2-(4-butoxyphenyl)-2h-furan-5-one Chemical compound C1=CC(OCCCC)=CC=C1C1C(Br)=C(Br)C(=O)O1 CLGNSHMVZBJLJV-UHFFFAOYSA-N 0.000 description 1
- 241001596957 Brama Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical class OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 1
- 229910003074 TiCl4 Inorganic materials 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 230000027455 binding Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- QHFQAJHNDKBRBO-UHFFFAOYSA-L calcium chloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].[Cl-].[Ca+2] QHFQAJHNDKBRBO-UHFFFAOYSA-L 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- XWSLYQXUTWUIKM-UHFFFAOYSA-N trimethoxy(sulfanylidene)-$l^{5}-phosphane Chemical compound COP(=S)(OC)OC XWSLYQXUTWUIKM-UHFFFAOYSA-N 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
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
auaThionophoaphoraanretrientern aus Thionophoaphoraäuretriestern @s ist bekannt, daß Thiolphosphorsäuretriester im allgemeinen weniger bequom zug@nglich sind als Thionophosphorsäuretriester.auaThionophoaphoraanretrientern from Thionophoaphoraäuretriestern @s it is known that thiolphosphoric acid triesters are generally less easily accessible are called thionophosphoric acid triesters.
@ur Herstellung von Thiolphoaphorwäuretriewtern ist daher häufig der @eg der thermischen Isomerisierung von thionephosphorsäuretriestern eingeschlagen worden. Dieses Verfahre erfordert oft hohe Temperaturen und lange Reaktionszeiten und versagt daher, wenn die entstahenden Thiolphosphate thermisch weniger stabil aiad ale ihre Thiono-Isocaeren. Das ist z.B. der Fall in der Reihe der Trialkyl-und Dialkylaryl-thiophosphate. So erleiden Trimethyl-, Dimethylphenyl- und Dimethylp-nitrophenyl-thionophosphat beim Erhitzen unter Bedingungen, unter donen der Thionoeohwefel) nom Verschwinden gebracht werden kann, eine stürmische, gegebenenfalls explosionsartige Zersetzung zu airupoeen Produkten, die keinen Thiclester @@@@ enthalten.@ur production of Thiolphoaphorwäuretriewtern is therefore often the @eg the thermal isomerization of thionephosphoric acid triesters been. This process often requires high temperatures and long reaction times and therefore fails if the thiol phosphates formed are less thermally stable aiad ale their Thiono-Isocaeren. This is e.g. the case in the series of trialkyl and Dialkylaryl thiophosphates. So suffer trimethyl, dimethylphenyl and dimethylp-nitrophenyl thionophosphate on heating under conditions under which the thionohulphurum disappears can be brought about a stormy, possibly explosive decomposition to airupoeen products that do not contain a Thiclester @@@@.
Es wurde nun gefunden, daß Thionophosphorsäuretriester der allgemeinen Formel worin ar sinen Alkylrest und R2 und R3 alkyl-, Aryl- eder su@. stituierte Arylreste badeuten, mit Lewissäuren wie FeCl3, AlCl3 *der Sncl4 Additionsverbindungen der allgemeinen Fermal bilden, in denen die isomeren Thiolphosphorsäureester vorliegan, und da diese Additionaverbindungen umter Gewinnung der Thielphesphorsäureester zerlegt werden können. Bewchl die Bildung als auch die Zerlegung der Additiens@@bindungen verlanfon ohnwärmg'zufUhruagüBdino&eaAsabasneEsaitia<iB@ ins einfache MathedezurUbayfüh?Mav<snTM'@BQiB.i<Ses&s= §uratrl dissiehaaäs?ss&aeSsteaBeEls @@@ Fater arwo@@@@ IBBcderathwrmishaIe@aaB'isiws'aagaia@l&@&&e @@@ mög@ ich ist.It has now been found that thionophosphoric acid triesters of the general formula wherein ar sinen alkyl radical and R2 and R3 alkyl, aryl eder su @. Substituted aryl radicals bathed with Lewis acids such as FeCl3, AlCl3 * of the Sncl4 addition compounds of the general Fermal form, in which the isomeric thiolphosphoric esters are present, and since these addition compounds can be broken down in order to obtain the thiolphosphoric esters. Bewchl the formation as well as the dismantling of the additiens @@ bindings verlanfon ohnwärmg'zufUhruagüBdino & eaAsabasneEsaitia <iB @ ins simple MathedezurUbayfüh? Mav <snTM'@BQiB.i <Ses & s = §uratrl dissiehaaBes? @ SsBe@ amisha@arels@sathea@s aaB'isiws'aagaia @ l & @ && e @@@ mög @ I is.
Die Heratellung der Addukten erfolgt zweaknößig durch zwssen@@-gbande?KaapsamtwnbeiaaBma<@sMiaieacnaees @@@@ @@@ frwianLSea&gsaitelß,geeeanafailstms'aBMiByEaM&gs frolon verwandet stöchionstri@@@ Mangan der Eespsmemten, wetei es keine Relle spielt, ob de@ @ster vorgelegt @@@ die Lewissäure zugegeben oder umgeker@@ verfakren wird. Die S@@@@@@-setrie der Addukte hängt von der Lewisäure eb@ bei den Addu ten des FeCl3 ist a = 3, b = @@ AlCl3 " a = 1, b = @@ )M&wdwAdAaMeMsaa.dX's&saSasy.a§b$da&AM& top dey FeCl3 ist a = 3, b = @@ AlCl3 " a = 1, b = 1 : SnCl4, SaBr, TiCl4 " a = @@ b = 1.The addition of the adducts is made by zwssen @@ - gbande? KaapsamtwnbeiaaBma <@sMiaieacnaees @@@@ @@@ frwianLSea & gsaitelß, geeeanafailstms'aBMiByEaM & gs frolon related stöchionstri @@@ Mangan der Eespsmemten, it doesn't matter whether de @ @ster submitted @@@ the Lewis acid is added or umgeker @@ defaced. The S @@@@@@ - setrie the adduct depends on the Lewis acid eb @ with the adducts of FeCl3 is a = 3, b = @@ AlCl3 "a = 1, b = @@) M & wdwAdAaMeMsaa.dX's & saSasy.a§b $ da & AM & top dey FeCl3 is a = 3, b = @@ AlCl3 "a = 1, b = 1: SnCl4, SaBr, TiCl4" a = @@ b = 1.
Die Zerlegung der Addukte geschieht durch Behandleng mit ein@@ wässrigen Lösung einen Metallhalegaaids, das i@@tande ist, die eingesetzte Lewisasäure als Halegememstell@@ nu bindam: in Estrsg@t kemren dafür vorzugsweise die @elegenide rder Elenemte i farwakßaAhiaaMtvaiaantMesae<Ai<SeettBWN der Additionsverbindung unterbleibt; die Lewissäure wird dann is in gerimgem Überschu@ Thiolphosphors @u@etriester könnan auf Grund ihrer insekti-@i@e@ and physiologischen Wirksamkeit vor allem in der khXdlingsbekämpfung vielseitige Verwendung finden.The breakdown of the adducts is done by treating with an @@ aqueous solution Solution of a Metallhalegaaids, which is i @@ tande, the Lewisa acid used as Halegememstell @@ nu bindam: in Estrsg @ t kemren preferably the @elegenide rder Elenemte i farwakßaAhiaaMtvaiaantMesae <Ai <SeettBWN of the addition compound does not take place; the Lewis acid is then in small excess Thiol phosphorus @ u @ etriester can because of their insecti- @ i @ e @ and physiological effectiveness especially in the fight against khXdlings.
Die folgenden Beispiele erläutern das Verfahren.The following examples illustrate the process.
@eispiel 1 @@@@@@ @@ner Lösung von 47 g @rimethylthionophosphat in 100 @@@ IetrolHther fUgt man unter Rühren portionsweise 33,5 g wasserfraies @isen(III)-chlorid, wobei, gegebenenfalls unter Kühlung, die Temperatur unter 25° gehalten wird Man rührt noch 2 Stuads nsch, ießt die Mutterlauge ab und Serkleinert da tritttllkuchen unter Petroläther. Nach Absugen, Waschen mit Fetreläther und Trocknen erhält man 77 g (95,8 % d.Th.) einem 3:2-Adduktes aus Trimethylthielphosphat und Eisen(III)-ahlerid, P. 135 bis 138°. @Example 1 @@@@@@ @@ ner solution of 47 g @rimethylthionophosphate in 100 @@@ IetrolHther are added in portions while stirring 33.5 g of anhydrous iron (III) chloride, where, optionally with cooling, the temperature is kept below 25 ° Man stirs another 2 hours, pours off the mother liquor and crushes the cake under petroleum ether. After suctioning off, washing with petroleum ether and drying, one obtains 77 g (95.8% of theory) of a 3: 2 adduct of trimethyl thiophosphate and iron (III) haleride, P. 135 to 138 °.
40 g dieser Verbindung tragt man unter Rühren in eine Läsung von 90 g Calciumchlorid-hexahydrat in 200 ecm Wasser ein und fügt @ach 10 Minuten 120 ecm Bensol zu. Mach weiteren 10 Mi@@-ton tronnt n die Benzol-Schicht ab, gibt zu der wäasrig@@ Schieht nochmals 70 oom Bonsol und 90 g Caleiumehleri@-@@@@@@-hydrat und ruant veine Stutda. Man trennt dann die Benselseheht ab und schüttelt dia wässrige Schieht dreimal mit je @@ @@@ Bensol aus. Die Bensolextrakte werden vereinigt, über Hatri@@-s getrocknet und nach Abtrennen des Bensols fraktiemiert.40 g of this compound are added to a solution of 90 with stirring g calcium chloride hexahydrate in 200 ecm of water and add 120 ecm after 10 minutes Bensol too. Do another 10 Mi @@ - ton separates the benzene layer off, adds to the wäasrig @@ Make another 70 oom Bonsol and 90 g Caleiumehleri @ - @@@@@@ - hydrate and ruant veine Stutda. The Benselseheht is then separated off and the watery one is shaken Looks three times with @@ @@@ Bensol each. The bensol extracts are combined over Hatri @@ - s dried and fractionated after separating off the benzene.
Man erhält 21,5 g (91 % d.Th.) Trimethylthielphesphat vem 17 g wasserfreies Eisen(III)-chlerid fügt man umter Rähran und Eiskühlung zu einer Lösung von 24 g Trimethylthionephosphat is 130 cam Bwnsol. Man entfernt dann das Kältebad, rührt eine Stunde nach und läßt über Nacht stehen, Dann zersetst man in gleicher Weise, wie unter Beispiel 1 angegeben. Man erhält 19,8 g (82,4 % d. Th.) Trimethylthielphesphat vem Kp.17 103°. zu eimer Suspension von 17 g wasserfreiem Eisem (III)-ahlorid in 100 os Brama tropft man umter Rühren 26,2 g Dimethyl-phanylthionophosphat. Mach besndeter Zngabe rährt man 2 Stu@@@@@ @@it@r und lUt übertMhtatwhtn.D<Mgi«metijMMewvm CalelM-eMorid-tMtM!imZOO«MWtMWum,rMaMe<<m au uad trnat tl B<nMMmi<M<b.ZwfeMfttMWtmttWM«M. weitere 90 g Caleinmehlerid her@hydrat und 100 eem Eemsel @@@@-test. Man rührt eine Stumde, trammt dann die @e@@el@@@@icht @@ und a chüttelt die wäsdsrige @hase viermal mit je 38 sem @ansel -" mut. Dis vereinigten Benssllösungen worden über Matrimmrulfst getreskmat und nach Abzichem des Benamls i.Vak. fraktiamiert.21.5 g (91% of theory) of trimethylthielphesphate are obtained 17th g of anhydrous iron (III) chleride are added umter rähran and ice cooling to one Solution of 24 g trimethylthione phosphate is 130 cam Bwnsol. You then remove that Cold bath, stir for an hour and let stand overnight, then decompose in in the same way as indicated under Example 1. 19.8 g (82.4% of theory) are obtained Trimethylthielphesphate vem bp 17 103 °. to bucket suspension of 17 g of anhydrous Eisem (III) -ahlorid in 100 os Brama is added dropwise with stirring, 26.2 g of dimethyl-phanylthionophosphate. After making the appropriate announcement, one rises 2 hours @@@@@ @@ it @ r and lUt aboutMhtatwhtn.D <Mgi «metijMMewvm CalelM-eMorid-tMtM! ImZOO «MWtMWum, rMaMe << m au uad trnat tl B <nMMmi <M <b.ZwfeMfttMWtmttWM« M. another 90 g Caleinmehlerid her @ hydrate and 100 eem Eemsel @@@@ - test. One stirs one Stumde, then tram the @ e @@ el @@@@ icht @@ and a shakes the watery @bunny four times each with 38 sem @ansel - "mut. The combined Bensslösungen were over Matrimmrulfst Getreskmat and after signing the Benamls i.Vak. fractiamed.
Xb rb 2191 g (80,5 % d.Th.) 0,8-dismthyl-O-phenylthi@l@@@@@@@ phat, Kp.10-2 104-106@.Xb rb 2191 g (80.5% of theory) 0.8-dismthyl-O-phenylthi @ l @@@@@@@ phat, Kp.10-2 104-106 @.
Belspiel 4 Eine Lösung von 15 g dimethyl-p-nitrephenylthienephesphat in 100 os Bnsol versetzt man unter Rähren mit 6,32 g wasserfreiem Elson (III)-ehlorid. Man rührt noch 2 Stunden nach, läßt dann einige Stunden stehen und rührt 1 Stunde mit einer Lösung von 90 g Caleiumehlerid-hezahydrat in 200 con or ut trennen der Benzolschieht wird die wäsarige Phase nochmals mit 50 ccm : Benzol versetzt und eine weitere Stunde auagerührt. Man triant die @chichten, @chüttelt die wässrige Phase nochmals mit wenig Benzol aus und trocknet die vereinigten Bensollösungen über Natriumsulfat. das Lösungsmittel wird t. k. bli 40-45° abgezongan, wobei eine schwach gelbliches Öl himterbleibt. Belspiel 4 A solution of 15 g of dimethyl-p-nitrephenylthiene-phesphate in 100 os Bnsol, 6.32 g of anhydrous Elson (III) chloride are added while stirring. The mixture is stirred for a further 2 hours, then left to stand for a few hours and stirred for 1 hour with a solution of 90 g of Caleiumehlerid hezahydrate in 200 con or ut separate the The aqueous phase is mixed again with benzene 50 cc: benzene added and stirred for a further hour. Man triant the @chichten, @ shakes the aqueous phase again with a little benzene and dries the combined Bensol solutions over sodium sulfate. the solvent is t. k. bli 40-45 °, with one pale yellowish oil remains.
@ine Reinigung der @ubstanz kann erfolgen durch Zusetz ven 4 cam methanol, Absaugen, Abkühlen auf -80°, Abdekantieres des LsunssmittJ und entfernen der letzten Lösungsmittelreste i. Vak. bei Raumtemperatur. Man erhält so 13,7 g 491,3 % d.Th.) O,@-dimethyl-O-p-nitrophenylthielphesphat, nD2@ 1,5626. novez Methylenchlerid gelöst und unter @äyhrem @@ einer S@@@@@@@@@@@ @@@ 7.62 g feingepulvertem wasserfreiem alumini@@@@@@@@@@@lerid in 70 @@@ Petroläther gatropft. Wenn alles Alumimiumchlerid in Lä@@@@ @@@ w ist, rährt man nech 2 Stunden sech und @@beitet @@@@ @@@ Petroläther getropft. Wenn slles Alumini@@chl@@id in Lä@@@@ @@@ gangen ist, rührt man nech 2 Stunden @@@@ @@@ arbeitet @@@@ @@@ in Beispiel 4 beschriebes weiter. Men erhält 13,5 g (90 % d.Th.) 0,8-Dimethyl-0-p-aitrephemyithielpheephat, @@@@ 1,9512. The substance can be cleaned by adding 4 cam methanol, suction, cooling to -80 °, decanting of the solution and removing the last remaining solvent i. Vac. at room temperature. 13.7 g are obtained in this way 491.3% of theory) O, @ - dimethyl-O-p-nitrophenylthielphesphate, nD2 @ 1.5626. novez methylene cheride solved and at @ äyhrem @@ a S @@@@@@@@@@@ @@@ 7.62 g finely powdered anhydrous alumini @@@@@@@@@@@ lerid in 70 @@@ petroleum ether gatropft. If everything is aluminum chloride in Lä @@@@ @@@ w is, after 2 hours you get six and @@ beitet @@@@ @@@ petroleum ether dripped. When slles Alumini @@ chl @@ id has gone into Lä @@@@ @@@, one stirs after 2 Hours @@@@ @@@ works @@@@ @@@ as described in example 4. Men receives 13.5 g (90% of theory) 0,8-dimethyl-0-p-aitrephemyithielpheephat, @@@@ 1.9512.
Claims (2)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DED0042423 | 1963-09-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1443711A1 true DE1443711A1 (en) | 1968-11-28 |
Family
ID=7046836
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19631443711 Pending DE1443711A1 (en) | 1963-09-07 | 1963-09-07 | Process for the production of thiolphosphoric acid triesters from thionophosphoric acid triesters |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1443711A1 (en) |
-
1963
- 1963-09-07 DE DE19631443711 patent/DE1443711A1/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE830509C (en) | Process for the preparation of neutral esters of thiophosphoric acid | |
| DE1815999C3 (en) | B-chloroethane pyrophosphonic acid and its use as a plant growth hormone | |
| DE1443711A1 (en) | Process for the production of thiolphosphoric acid triesters from thionophosphoric acid triesters | |
| DE830508C (en) | Process for the preparation of neutral esters of thiophosphoric acid | |
| DE848041C (en) | Process for the preparation of esters of orthophosphoric acid and thiophosphoric acid | |
| DE1945645A1 (en) | Process for the preparation of diorganochlorophosphines | |
| DE1903356A1 (en) | Process for the preparation of substituted vinyl esters of phosphoric acids | |
| DE946056C (en) | Process for the preparation of neutral esters of thiolphosphoric acid | |
| DE2916991C3 (en) | Process for the preparation of 1,4-bis- (arylmethyl) -pipera ~ yne compounds | |
| DE818046C (en) | Process for the preparation of acyl compounds of dialkyl selenophosphoric acids | |
| DE1206425B (en) | Process for the production of phosphoric acid esters | |
| DE1443711C (en) | Process for the preparation of thiolphosphoric acid triesters by isomerization of the corresponding thionophosphoric acid triesters | |
| DE1092464B (en) | Process for the preparation of O, S-dialkylthiophosphoric acid chlorides | |
| DE1039070B (en) | Process for the preparation of dialkyl-thionophosphoric acid esters of 4-oxyphenylsulfonamides | |
| DE1443711B (en) | Process for the preparation of thiolphosphoric acid triesters by isomerization of the corresponding thionophosphoric acid triesters | |
| EP0144743A1 (en) | Process for the preparation of organic chlorophosphanes | |
| DE1119861B (en) | Process for the production of lower alkyl dichlorophosphines with recovery of aluminum chloride | |
| DE2421462C3 (en) | Process for the preparation of dithiophosphoric acid-0,0-diesters | |
| DE1034612B (en) | Process for the preparation of esters of phosphoric acid and thiophosphoric acid | |
| DE1250425B (en) | Process for the production of organophosphorus compounds | |
| US2033540A (en) | Mixed phenoxyphenyl-alkyl ketones | |
| DE1026323B (en) | Process for the preparation of insecticidally active O, O-dialkyl-S-phenyl-thionothiolphosphoric acid esters | |
| DE2116369A1 (en) | Oximino derivatives containing phosphorus, process for their preparation and their use | |
| DE1166192B (en) | Process for the preparation of secondary diarylphosphine oxides | |
| DE1235913B (en) | Process for the production of hexavalent phosphorus compounds |