GB785141A - Process for the production of o,o-dimethyl phosphorothiolic acid esters - Google Patents
Process for the production of o,o-dimethyl phosphorothiolic acid estersInfo
- Publication number
- GB785141A GB785141A GB21975/55A GB2197555A GB785141A GB 785141 A GB785141 A GB 785141A GB 21975/55 A GB21975/55 A GB 21975/55A GB 2197555 A GB2197555 A GB 2197555A GB 785141 A GB785141 A GB 785141A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dimethyl
- mixture
- ethyl
- phosphite
- phosphorothiolate
- 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 abstract 4
- 239000002253 acid Substances 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 6
- CZHYKKAKFWLGJO-UHFFFAOYSA-N dimethyl phosphite Chemical compound COP([O-])OC CZHYKKAKFWLGJO-UHFFFAOYSA-N 0.000 abstract 5
- 239000000203 mixture Substances 0.000 abstract 4
- 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 abstract 3
- 229910052708 sodium Inorganic materials 0.000 abstract 3
- 239000011734 sodium Substances 0.000 abstract 3
- -1 substituted alkyl thiocyanate Chemical compound 0.000 abstract 3
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 abstract 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 abstract 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 abstract 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 230000000749 insecticidal effect Effects 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 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)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Esters of O,O-dimethyl phosphorothiolic acid are obtained by mixing dimethyl phosphite with an alkyl or substituted alkyl thiocyanate and contacting the mixture with an alkali metal in at least the stoichiometric amount required to form the alkali metal salt of the dimethyl phosphite. The process is preferably carried out in an inert solvent such as benzene, dibutyl ether or dioxane and the reaction temperature is generally between 0 DEG and 150 DEG C. and preferably between 30 DEG and 80 DEG C. In examples: (1) to (6) the S-methyl-, S-ethyl-, S-propyl-, S-isopropyl-, S-benzyl-, and S-hexyl-, esters of O,O-dimethyl phosphorothiolic acid are obtained by adding a suspension of powdered sodium in a solvent to a mixture of dimethyl phosphite with the appropriate organic thiocyanate; (7) a mixture of dimethyl phosphite and b -ethyl-mercaptoethylthiocyanate is reacted with powdered sodium in dibutyl ether to yield O,O-dimethyl-S - b - ethylmercaptoethyl phosphorothiolate; (8) O,O - dimethyl - S - a - carbethoxy ethyl phosphorothiolate is obtained by adding a mixture of dimethyl phosphite and a -thiocyanogen propionic acid ethyl ester to finely divided sodium in benzene; (9) and (10) O,O-dimethyl-O,O-dimethyl-S-carbohexoxyethyl phosphorothiolate are obtained similarly using a -thio cyanogenpropionic acid-n-propyl (and n-hexyl-) esters respectively. The products are stated to have strong insecticidal action. Specification 691,374 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE785141X | 1954-08-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB785141A true GB785141A (en) | 1957-10-23 |
Family
ID=6698697
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB21975/55A Expired GB785141A (en) | 1954-08-02 | 1955-07-29 | Process for the production of o,o-dimethyl phosphorothiolic acid esters |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB785141A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3340330A (en) * | 1964-05-19 | 1967-09-05 | Olin Mathieson | Bis-mercaptoalkylene spirophosphorodithioates |
-
1955
- 1955-07-29 GB GB21975/55A patent/GB785141A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3340330A (en) * | 1964-05-19 | 1967-09-05 | Olin Mathieson | Bis-mercaptoalkylene spirophosphorodithioates |
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