GB882338A - Process for the manufacture of o-aryl-phosphorodichloridothioates - Google Patents
Process for the manufacture of o-aryl-phosphorodichloridothioatesInfo
- Publication number
- GB882338A GB882338A GB3759559A GB3759559A GB882338A GB 882338 A GB882338 A GB 882338A GB 3759559 A GB3759559 A GB 3759559A GB 3759559 A GB3759559 A GB 3759559A GB 882338 A GB882338 A GB 882338A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenyl
- chloro
- employed
- sulphur
- phosphorodichloridite
- 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
- -1 2,4,5-trichlorophenyl Chemical group 0.000 abstract 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 5
- 239000005864 Sulphur Substances 0.000 abstract 5
- ZDTQJPVEXIUREJ-UHFFFAOYSA-N dichlorophosphinous acid Chemical compound OP(Cl)Cl ZDTQJPVEXIUREJ-UHFFFAOYSA-N 0.000 abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 4
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 abstract 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 abstract 2
- 125000004429 atom Chemical group 0.000 abstract 2
- OOFVSLAKBNBEEH-UHFFFAOYSA-N dichloro-hydroxy-sulfanylidene-$l^{5}-phosphane Chemical compound OP(Cl)(Cl)=S OOFVSLAKBNBEEH-UHFFFAOYSA-N 0.000 abstract 2
- 239000011541 reaction mixture Substances 0.000 abstract 2
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 abstract 1
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000000950 dibromo group Chemical group Br* 0.000 abstract 1
- LXHWDUISRBUGRA-UHFFFAOYSA-N dichloro(phenoxy)phosphane Chemical class ClP(Cl)OC1=CC=CC=C1 LXHWDUISRBUGRA-UHFFFAOYSA-N 0.000 abstract 1
- 229910001629 magnesium chloride Inorganic materials 0.000 abstract 1
- 150000002989 phenols Chemical class 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- WQYSXVGEZYESBR-UHFFFAOYSA-N thiophosphoryl chloride Chemical compound ClP(Cl)(Cl)=S WQYSXVGEZYESBR-UHFFFAOYSA-N 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
- C07F9/20—Esters of thiophosphoric acids containing P-halide groups
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
A phosphorodichloridothioate having the formula R.O.P(S)Cl2 wherein R is phenyl or substituted phenyl is obtained by reacting sulphur at elevated temperature with a phosphorodichloridite of the formula R.O.P.Cl2 the reaction being carried out in the presence of phosphorus trichloride which is applied in a proportion at least high enough to chemically bind substantially all unreacted sulphur remaining after completion of the reaction. The substituted phenyl radical may suitably be a mono-or poly-chloro- (or bromo)-phenyl, or 2-chloro (or bromo)-4-lower (C1-C4) alkyl phenyl. Increased yields can be obtained if an amount of the desired phosphorodichloridothioate product is initially added to the reaction mixture, preferably from 0.25 to 1.5 mole being added for each mole of the dichlorodite contained in the reaction mixture. The reaction temperature is preferably from 160 DEG C. to 180 DEG C. and atmospheric or elevated pressure may be used. The amount of sulphur added is advantageously at least 1 gram atom for each gram mol. of the phosphorodichloridite employed but less than one gram atom of sulphur should be used for each molecular proportion of total phosphorodichloridite and phosphorus trichloride employed. Also, the amount of phosphorus trichloride employed should generally not exceed 0.8 molecular proportion for each molecular proportion of phosphorodichloridite employed. In some cases part of the sulphur may be replaced by its molar equivalent of phosphorus thiochloride with a corresponding reduction in the amount of PC13 used. Examples are given for the production of compounds of the first given formula in which R is 2,4,5-trichlorophenyl and 0-(2- chloro-4-tertiarybutyl) phenyl and other specified products obtainable by the process are those in which R in the formula is 2-bromophenyl, 2, 4-dichlorophenyl, 2,4-dibromophenyl, 2,5-dichloro (or dibromo) phenyl, 2,6-dichlorophenyl, 2-chloro-4-methylphenyl, 2-bromo-4-ethylphenyl, and 2-chloro-4-isopropyl phenyl. The O-halophenyl- and O-(2-halo-4-lower (C1-C4) alkyl) phenyl-phosphorodichloridites used as starting materials may be obtained by reacting phosphorus trichloride with the corresponding substituted phenol in the presence of magnesium chloride as catalyst, the reactants being mixed together and heated at the boiling temperature. At least 7 moles of PC13 are employed for each mole of the phenol.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3759559A GB882338A (en) | 1959-11-05 | 1959-11-05 | Process for the manufacture of o-aryl-phosphorodichloridothioates |
| FR811601A FR1244007A (en) | 1959-11-05 | 1959-11-30 | Process for preparing dichlorophosphothionates |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3759559A GB882338A (en) | 1959-11-05 | 1959-11-05 | Process for the manufacture of o-aryl-phosphorodichloridothioates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB882338A true GB882338A (en) | 1961-11-15 |
Family
ID=10397623
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3759559A Expired GB882338A (en) | 1959-11-05 | 1959-11-05 | Process for the manufacture of o-aryl-phosphorodichloridothioates |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB882338A (en) |
-
1959
- 1959-11-05 GB GB3759559A patent/GB882338A/en not_active Expired
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