DE836349C - Process for the preparation of neutral esters of thiophosphoric acid - Google Patents
Process for the preparation of neutral esters of thiophosphoric acidInfo
- Publication number
- DE836349C DE836349C DEF1406A DEF0001406A DE836349C DE 836349 C DE836349 C DE 836349C DE F1406 A DEF1406 A DE F1406A DE F0001406 A DEF0001406 A DE F0001406A DE 836349 C DE836349 C DE 836349C
- Authority
- DE
- Germany
- Prior art keywords
- preparation
- thiophosphoric acid
- alkyl
- neutral esters
- neutral
- 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
- 238000000034 method Methods 0.000 title claims description 4
- 230000007935 neutral effect Effects 0.000 title claims description 4
- 150000002148 esters Chemical class 0.000 title description 3
- 238000002360 preparation method Methods 0.000 title description 2
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical compound OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 title 1
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- HPFKOFNYNQMWEF-UHFFFAOYSA-N chloro-dihydroxy-sulfanylidene-$l^{5}-phosphane Chemical class OP(O)(Cl)=S HPFKOFNYNQMWEF-UHFFFAOYSA-N 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000003756 stirring Methods 0.000 description 5
- 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 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- -1 thiophosphoric acid ester chlorides Chemical class 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- KMJJJTCKNZYTEY-UHFFFAOYSA-N chloro-diethoxy-sulfanylidene-$l^{5}-phosphane Chemical compound CCOP(Cl)(=S)OCC KMJJJTCKNZYTEY-UHFFFAOYSA-N 0.000 description 1
- XFBJRFNXPUCPKU-UHFFFAOYSA-N chloro-dimethoxy-sulfanylidene-$l^{5}-phosphane Chemical compound COP(Cl)(=S)OC XFBJRFNXPUCPKU-UHFFFAOYSA-N 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 239000004567 concrete Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 150000003580 thiophosphoric acid esters Chemical class 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
- C07F9/1651—Esters of thiophosphoric acids with hydroxyalkyl compounds with 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 neutralen Estern der Thi6phosphorsäure I:s wurde gefunden, daß man neutrale Thiophospho@s@iu@ee,ie@ erhält, wenn man 1)ialkyIchlorthiophosphate mit aliphati,chen, schwefelhaltigen Alkoholen der allgemeinen Formel H O - Alkyl - S - R umsetzt. In dieser Formel kann R für einen alipliatischen, aromatischen oder araliphatischen Rest stehen. Die mit Alkyl bezeichnete Kette kann ihrerseits durch O oder S unterbrochen sein. Die Umsetzung der genannten Esterchloride der Thiophosphc@rsäiire kann entweder mit den Alkalisalzen derdie Formel gekennzeichneten Alkohole vccrgenc@mmen werden ()der zweckmüßiger mit den Alko- holen seihst in Gegenwart eines Säurebindemittels, z. B. von wasserfreiem Natriumcarhonat. Zur Durchführung der Umsetzung arbeitet mau zweckmäßig in inerten N"erdünnungsmitteln ; als solche kommen z. B. Iiohlenwas,crstccffe, wie Benzol, Toluol usw., Chlor-Benzol u. ä., oder auch Betone, wie Aceton, llethyläthylketon, Methylpropylketon, in Frage. Die Umsetzung kann in bekannter Weise durch Zusatz von metallischem Kupfer katalytisch beschleunigt werden.Process for the preparation of neutral esters of thi6phosphoric acid I: s it has been found that neutral thiophospho @ s @ iu @ ee, ie @ are obtained if 1) alkali chlorothiophosphates with aliphatic, sulfur-containing alcohols of the general formula HO - alkyl - S - R implements. In this formula, R can stand for an aliphatic, aromatic or araliphatic radical. The chain denoted by alkyl can in turn be interrupted by O or S. The reaction of the thiophosphoric acid ester chlorides mentioned can either be carried out with the alkali metal salts of the alcohols characterized by the formula B. of anhydrous sodium carbonate. To carry out the reaction, it is expedient to work in inert diluents; such compounds include, for example, benzene, toluene, etc., chlorobenzene and the like, or concretes such as acetone, ethyl ethyl ketone, methyl propyl ketone, The reaction can be accelerated catalytically in a known manner by adding metallic copper.
Die erhaltenen Verbindungen können als Insektizide Verwendung finden. Sie zeichnen sich durch starke kc>ntaktinsektizide Wirkung aus und besitzen auch innertherapeutische insektizide Wirkung. Beispiel i i2 g feingepulvertes metallisches Natrium werden in 5o ccm trockenem Benzol angeschlämmt. Zu dieser Anschlämmung tropft man 50 g des ß-Oxäthylmethylsulfids (KP, 72°, beschrieben in Journal of the American chemical society 1930, Bd. 52, S. 2576) und hält die Temperatur eine halbe Stunde bei :Io bis 5o°. Nach dieser Zeit ist das Natrium in Lösung gegangen. Nun kühlt man auf 2ö' ab und tropft unter Rühren 87 g Dimethylchlorthiophosphat (KP, 38 bis 39') bei 1o bis 20' zu. Man hält unter weiterem Rühren diese Temperatur noch 2 Stunden, gibt dann zum Auflösen des Salzes 50 ccm Wasser hinzu, trennt die wäBrige Schicht ab und fraktioniert die Benzolschicht. 'Man erhält 7o g des 0, 0-Dimethyl-O-methylmercaptoäthylthiophosphates vom Kp2 115'. Die Ausbeute beträgt 640o der Theorie. Das erhaltene Produkt ist ein wenig wasserlösliches, farbloses 01 von charakteristischem Geruch. Beispiel 2 12 g feingepulvertes Natrium werden wie im Beispiel 1 in 5o ccm Benzol angeschlämmt. Dann gibt man unter Rühren 5o g ß-Oxäthvlmethylsulfid hinzu und erwärmt eine halbe Stunde auf 4o bis 5o', bis das Natrium in Lösung gegangen ist. Darauf tropft man unter Rühren 95 g Diäthylchlorthiophosphat@zu und hält die Temperatur unter weiterem Rühren 2 Stunden auf io°. Beim Aufarbeiten des erhaltenen Produktes bekommt man 8o g des 0, 0-Diäthyl-0-methylmercaptoäthylthiophosphats vom KP, 131 bis Z32° entsprechend einer Ausbeute von 650/0.The compounds obtained can be used as insecticides. They are characterized by a strong tactile insecticidal effect and also have an internal therapeutic insecticidal effect. Example i 2 g of finely powdered metallic sodium are suspended in 50 cc of dry benzene. 50 g of β-oxethylmethylsulfide (KP, 72 °, described in Journal of the American chemical society 1930, vol. 52, p. 2576) are added dropwise to this slurry and the temperature is maintained at: 10 ° to 50 ° for half an hour. After this time the sodium has gone into solution. It is then cooled to 20 'and 87 g of dimethylchlorothiophosphate (KP, 38 to 39') are added dropwise at 10 to 20 'with stirring. This temperature is maintained for a further 2 hours with further stirring, 50 cc of water are then added to dissolve the salt, the aqueous layer is separated off and the benzene layer is fractionated. 'One receives 70 g of 0, 0-dimethyl-O-methylmercaptoethylthiophosphate of bp2 115'. The yield is 640o of theory. The product obtained is a slightly water-soluble, colorless oil with a characteristic odor. Example 2 12 g of finely powdered sodium are suspended in 50 cc of benzene as in Example 1. Then, while stirring, 50 g of β-oxetholmethyl sulfide are added and the mixture is heated to 40 to 50 'for half an hour until the sodium has dissolved. 95 g of diethyl chlorothiophosphate are then added dropwise with stirring and the temperature is kept at 10 ° for 2 hours with further stirring. When the product obtained is worked up, 80 g of 0, 0-diethyl-0-methylmercaptoethylthiophosphate from KP.131 to Z32 °, corresponding to a yield of 650/0.
Beispiel 3 11o g ß-Oxäthyläthylsulfid (Kp" 8o', beschrieben Liebigs Annalen der Chemie, 1887, Bd. 240, S.310; Berichte der Deutschen chemischen Gesellschaft, 192o, Bd. 53, S. 107 und 1935, Bd. 68, S. 588) werden in Zoo ccm Toluol gelöst. Zu der Lösung gibt man 2 g Kupferpulver und 11o g wasserfreies Natriumcarbonat. Unter Rühren gibt man bei 8o bis 9o' 19o g Diäthylchlorthiophosphat und hält die Temperatur unter Rühren bei 8o bis 9o°. Dann wird auf Zimmertemperatur abgekühlt. Die entstandenen Salze werden durch Zugabe von Zoo ccm Wasser in Lösung gebracht. Die wäßrige Schicht wird abgetrennt. Nach dem Abdestillieren des Toluols bleiben 193 g roher 0, 0-Diäthyl-O-äthy lmercaptoäthylthiophosphat zurück entsprechend einer Ausbeute von 75°/0. Der neue Ester ist in reinem Zustand ein farbloses, schwach riechendes 01 vom KP, 134'. Nach den unter Beispiel 1 bis 3 beschriebenen Methoden lassen sich folgende Thiophosphorsäureester hersiellen: Example 3 110 g ß-Oxäthyläthylsulfid (bp "8o ', described Liebigs Annalen der Chemie, 1887, vol. 240, p.310; reports of the German chemical society, 192o, vol. 53, p. 107 and 1935, vol. 68 , P. 588) are dissolved in zoo cc of toluene. 2 g of copper powder and 11o g of anhydrous sodium carbonate are added to the solution. It is then cooled to room temperature. The resulting salts are dissolved by adding zoo cc of water. The aqueous layer is separated off. After the toluene has been distilled off, 193 g of crude 0.0-diethyl-O-ethyl mercaptoethyl thiophosphate remain, corresponding to a yield of 75%. In the pure state, the new ester is a colorless, weakly smelling oil from KP, 134 '. The following thiophosphoric acid esters can be prepared using the methods described in Examples 1 to 3:
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF1406A DE836349C (en) | 1950-05-10 | 1950-05-10 | Process for the preparation of neutral esters of thiophosphoric acid |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF1406A DE836349C (en) | 1950-05-10 | 1950-05-10 | Process for the preparation of neutral esters of thiophosphoric acid |
Publications (1)
Publication Number | Publication Date |
---|---|
DE836349C true DE836349C (en) | 1952-04-10 |
Family
ID=7082859
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEF1406A Expired DE836349C (en) | 1950-05-10 | 1950-05-10 | Process for the preparation of neutral esters of thiophosphoric acid |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE836349C (en) |
Cited By (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE931106C (en) * | 1953-03-19 | 1955-08-01 | Bayer Ag | Process for the preparation of thiophosphoric acid esters of polyhydric aliphatic alcohols |
DE936037C (en) * | 1953-04-23 | 1955-12-01 | Bayer Ag | Process for the production of thiophosphoric acid and phosphoric acid esters |
DE956503C (en) * | 1953-07-22 | 1957-01-17 | Geigy Ag J R | Process for the production of new phosphoric or thiophosphoric acid esters |
DE1007770B (en) * | 1954-09-01 | 1957-05-09 | Sandoz Ag | Process for the production of new thionophosphoric acid esters |
DE1014107B (en) * | 1954-12-28 | 1957-08-22 | Wolfen Filmfab Veb | Process for the preparation of esters of phosphorus-containing acids |
DE1014988B (en) * | 1955-09-07 | 1957-09-05 | Bayer Ag | Process for the production of neutral thionophosphoric acid triesters |
DE1036846B (en) * | 1956-12-21 | 1958-08-21 | Bayer Ag | Process for the preparation of thiophosphoric acid esters |
DE1044503B (en) * | 1954-10-27 | 1958-11-20 | Hoechst Ag | Pest repellants |
DE1047775B (en) * | 1957-03-29 | 1958-12-31 | Basf Ag | Process for the preparation of O, O-dialkylphosphorus or thiophosphoric acid esters of hydroxyketones |
DE1047776B (en) * | 1958-03-28 | 1958-12-31 | Bayer Ag | Process for the preparation of thionophosphoric acid esters |
DE1056121B (en) * | 1957-02-27 | 1959-04-30 | Bayer Ag | Process for the preparation of thiophosphoric acid esters |
DE1062239B (en) * | 1956-07-28 | 1959-07-30 | Bayer Ag | Process for the preparation of thiophosphoric acid esters |
DE1063155B (en) * | 1957-10-09 | 1959-08-13 | Bayer Ag | Process for the preparation of thiophosphoric acid esters |
DE1063153B (en) * | 1956-12-10 | 1959-08-13 | Bayer Ag | Process for the preparation of esters of thiophosphoric acid containing sulfide, sulfoxide or sulfone groups |
DE1063154B (en) * | 1950-05-09 | 1959-08-13 | Bayer Ag | Process for the preparation of thiophosphoric acid esters |
DE1078124B (en) * | 1957-06-18 | 1960-03-24 | Bayer Ag | Process for the preparation of thionophosphonic acid esters |
DE1085887B (en) * | 1956-04-27 | 1960-07-28 | Bayer Ag | Process for the preparation of new, insecticidally active thionophosphoric acid esters |
US2952700A (en) * | 1955-11-22 | 1960-09-13 | Bayer Ag | Thiophosphoric acid esters and their production |
DE1101406B (en) * | 1956-03-22 | 1961-03-09 | Bayer Ag | Process for the preparation of thionophosphoric acid esters |
DE1116656B (en) * | 1958-05-28 | 1961-11-09 | Bayer Ag | Process for the preparation of thionophosphoric acid esters |
DE1117110B (en) * | 1957-06-14 | 1961-11-16 | Bayer Ag | Process for the preparation of thionophosphoric acid esters |
DE1163831B (en) * | 1956-06-04 | 1964-02-27 | Bayer Ag | Process for the preparation of thionophosphoric acid esters |
DE1185858B (en) * | 1960-08-18 | 1965-01-21 | Basf Ag | Insecticides |
DE1187849B (en) * | 1955-11-22 | 1965-02-25 | Bayer Ag | Insecticides |
DE1242602B (en) * | 1964-03-31 | 1967-06-22 | Wolfen Filmfab Veb | Process for the preparation of beta-alkylmercaptoethyl-dialkyl-thiophosphoric acid triesters |
-
1950
- 1950-05-10 DE DEF1406A patent/DE836349C/en not_active Expired
Cited By (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1063154B (en) * | 1950-05-09 | 1959-08-13 | Bayer Ag | Process for the preparation of thiophosphoric acid esters |
DE931106C (en) * | 1953-03-19 | 1955-08-01 | Bayer Ag | Process for the preparation of thiophosphoric acid esters of polyhydric aliphatic alcohols |
DE936037C (en) * | 1953-04-23 | 1955-12-01 | Bayer Ag | Process for the production of thiophosphoric acid and phosphoric acid esters |
DE956503C (en) * | 1953-07-22 | 1957-01-17 | Geigy Ag J R | Process for the production of new phosphoric or thiophosphoric acid esters |
DE1007770B (en) * | 1954-09-01 | 1957-05-09 | Sandoz Ag | Process for the production of new thionophosphoric acid esters |
DE1044503B (en) * | 1954-10-27 | 1958-11-20 | Hoechst Ag | Pest repellants |
DE1014107B (en) * | 1954-12-28 | 1957-08-22 | Wolfen Filmfab Veb | Process for the preparation of esters of phosphorus-containing acids |
DE1014988B (en) * | 1955-09-07 | 1957-09-05 | Bayer Ag | Process for the production of neutral thionophosphoric acid triesters |
DE1187849B (en) * | 1955-11-22 | 1965-02-25 | Bayer Ag | Insecticides |
US2952700A (en) * | 1955-11-22 | 1960-09-13 | Bayer Ag | Thiophosphoric acid esters and their production |
DE1101406B (en) * | 1956-03-22 | 1961-03-09 | Bayer Ag | Process for the preparation of thionophosphoric acid esters |
DE1085887B (en) * | 1956-04-27 | 1960-07-28 | Bayer Ag | Process for the preparation of new, insecticidally active thionophosphoric acid esters |
DE1163831B (en) * | 1956-06-04 | 1964-02-27 | Bayer Ag | Process for the preparation of thionophosphoric acid esters |
DE1062239B (en) * | 1956-07-28 | 1959-07-30 | Bayer Ag | Process for the preparation of thiophosphoric acid esters |
DE1063153B (en) * | 1956-12-10 | 1959-08-13 | Bayer Ag | Process for the preparation of esters of thiophosphoric acid containing sulfide, sulfoxide or sulfone groups |
DE1036846B (en) * | 1956-12-21 | 1958-08-21 | Bayer Ag | Process for the preparation of thiophosphoric acid esters |
DE1056121B (en) * | 1957-02-27 | 1959-04-30 | Bayer Ag | Process for the preparation of thiophosphoric acid esters |
DE1047775B (en) * | 1957-03-29 | 1958-12-31 | Basf Ag | Process for the preparation of O, O-dialkylphosphorus or thiophosphoric acid esters of hydroxyketones |
DE1117110B (en) * | 1957-06-14 | 1961-11-16 | Bayer Ag | Process for the preparation of thionophosphoric acid esters |
DE1078124B (en) * | 1957-06-18 | 1960-03-24 | Bayer Ag | Process for the preparation of thionophosphonic acid esters |
DE1063155B (en) * | 1957-10-09 | 1959-08-13 | Bayer Ag | Process for the preparation of thiophosphoric acid esters |
DE1047776B (en) * | 1958-03-28 | 1958-12-31 | Bayer Ag | Process for the preparation of thionophosphoric acid esters |
DE1116656B (en) * | 1958-05-28 | 1961-11-09 | Bayer Ag | Process for the preparation of thionophosphoric acid esters |
DE1185858B (en) * | 1960-08-18 | 1965-01-21 | Basf Ag | Insecticides |
DE1242602B (en) * | 1964-03-31 | 1967-06-22 | Wolfen Filmfab Veb | Process for the preparation of beta-alkylmercaptoethyl-dialkyl-thiophosphoric acid triesters |
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