GB898755A - Method for the manufacture of mixed phosphorothioate esters - Google Patents
Method for the manufacture of mixed phosphorothioate estersInfo
- Publication number
- GB898755A GB898755A GB3603559A GB3603559A GB898755A GB 898755 A GB898755 A GB 898755A GB 3603559 A GB3603559 A GB 3603559A GB 3603559 A GB3603559 A GB 3603559A GB 898755 A GB898755 A GB 898755A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkali metal
- metal hydroxide
- lower alkyl
- phenolic compound
- weight
- 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
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical class OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 title 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- -1 alkyl radical Chemical class 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 3
- 150000002989 phenols Chemical class 0.000 abstract 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 150000005840 aryl radicals Chemical group 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- HPFKOFNYNQMWEF-UHFFFAOYSA-N chloro-dihydroxy-sulfanylidene-$l^{5}-phosphane Chemical compound OP(O)(Cl)=S HPFKOFNYNQMWEF-UHFFFAOYSA-N 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 238000010908 decantation Methods 0.000 abstract 1
- WSRVOHKCZFFHPZ-UHFFFAOYSA-N diethoxy-sulfanylidene-(2,4,5-trichlorophenoxy)-$l^{5}-phosphane Chemical compound CCOP(=S)(OCC)OC1=CC(Cl)=C(Cl)C=C1Cl WSRVOHKCZFFHPZ-UHFFFAOYSA-N 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 239000003973 paint Substances 0.000 abstract 1
- 239000000123 paper Substances 0.000 abstract 1
- 230000000361 pesticidal effect Effects 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 239000003755 preservative agent Substances 0.000 abstract 1
- 150000003254 radicals Chemical group 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 238000003756 stirring Methods 0.000 abstract 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 abstract 1
- 239000002023 wood 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
- C07F9/18—Esters of thiophosphoric acids with hydroxyaryl compounds
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)
Abstract
O-aromatic O,O-di(lower alkyl)phosphorothioates are obtained by reacting in the absence of a catalyst and at from 40 DEG C. to 70 DEG C. one molecular proportion of an O,O-di(lower alkyl) phosphorochloridothioate wherein the lower alkyl radical contains 1 to 5 carbon atoms with a mixture comprising at least one molecular proportion of each of an alkali metal hydroxide and a phenolic compound ROH wherein R is a naphthyl or anthryl radical or an aryl radical whose nucleus is substituted with one or more atoms or radicals selected from chlorine, bromine, C1-C5 alkyl, C1-C5 alkoxy, cyclohexyl, benzyl, or phenyl, said alkali metal hydroxide being employed in the form of aqueous solution containing at least 10% by weight, and preferably from 10% to 25% by weight, of the alkali metal hydroxide based upon the weight of water employed. The product, if a solid, may be separated by filtration, successively washed with aqueous alkali metal hydroxide and water, and air-dried; and, if a liquid it may be separated by decantation and then washed as above. It is preferred to use a mixture containing from 1.25 to 1.5 molecular proportions of each of the alkali metal hydroxide and phenolic compound. In carrying out the reaction the O,O-di(lower alkyl)phosphorochloridothioate is generally added portionwise, with stirring to a mixture of the alkali metal hydroxide (e.g. NaOH or KOH), phenolic compound and water or the order of addition may be reversed. Examples are given for the production of O-(2,4,5-trichlorophenyl)-, O - (2, 4 - dichlorophenyl)-, O - (2 - chloro - 4 - tertiarybutylphenyl) -, and O - (b - naphthyl) O,O-dimethylphosphorothioates, and O-(2,4,5-trichlorophenyl) O,O-diethyl phosphorothioate. Several other phosphorothioate products obtainable by the process are also specified. The products have pesticidal properties and are useful as preservatives for paper, paint and wood. Reference has been directed by the Comptroller to Specification 699,064.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3603559A GB898755A (en) | 1959-10-23 | 1959-10-23 | Method for the manufacture of mixed phosphorothioate esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3603559A GB898755A (en) | 1959-10-23 | 1959-10-23 | Method for the manufacture of mixed phosphorothioate esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB898755A true GB898755A (en) | 1962-06-14 |
Family
ID=10384245
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3603559A Expired GB898755A (en) | 1959-10-23 | 1959-10-23 | Method for the manufacture of mixed phosphorothioate esters |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB898755A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3530206A (en) * | 1966-03-25 | 1970-09-22 | Ciba Ltd | O,o-diloweralkyl-o - (2-chloro - 4 - bromo phenyl) phosphates and thiophosphates |
-
1959
- 1959-10-23 GB GB3603559A patent/GB898755A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3530206A (en) * | 1966-03-25 | 1970-09-22 | Ciba Ltd | O,o-diloweralkyl-o - (2-chloro - 4 - bromo phenyl) phosphates and thiophosphates |
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