GB785030A - Process for the production of sulphinyl ethyl thiophosphates - Google Patents
Process for the production of sulphinyl ethyl thiophosphatesInfo
- Publication number
- GB785030A GB785030A GB2034954A GB2034954A GB785030A GB 785030 A GB785030 A GB 785030A GB 2034954 A GB2034954 A GB 2034954A GB 2034954 A GB2034954 A GB 2034954A GB 785030 A GB785030 A GB 785030A
- Authority
- GB
- United Kingdom
- Prior art keywords
- sulphinyl
- ethane
- salt
- bromo
- thiophosphoric acid
- 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
- PGUWEIDBHABKNA-UHFFFAOYSA-N 4-ethoxy-4-sulfanylidene-1,3,2,4lambda5-dioxathiaphosphetane 2-oxide Chemical class P1(=S)(OS(=O)O1)OCC PGUWEIDBHABKNA-UHFFFAOYSA-N 0.000 title 1
- -1 Sulphinyl compounds Chemical class 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical compound OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 abstract 3
- 239000003153 chemical reaction reagent Substances 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- 229910018894 PSCl3 Inorganic materials 0.000 abstract 2
- 238000004810 partition chromatography Methods 0.000 abstract 2
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 abstract 2
- 150000003582 thiophosphoric acids Chemical class 0.000 abstract 2
- WQYSXVGEZYESBR-UHFFFAOYSA-N thiophosphoryl chloride Chemical compound ClP(Cl)(Cl)=S WQYSXVGEZYESBR-UHFFFAOYSA-N 0.000 abstract 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 abstract 1
- SBNMMJGHHUVOBO-UHFFFAOYSA-N 1-(2-bromoethylsulfinyl)butane Chemical compound BrCCS(=O)CCCC SBNMMJGHHUVOBO-UHFFFAOYSA-N 0.000 abstract 1
- HPLOHMRPEJYXQC-UHFFFAOYSA-N 1-(2-bromoethylsulfinyl)propane Chemical compound BrCCS(=O)CCC HPLOHMRPEJYXQC-UHFFFAOYSA-N 0.000 abstract 1
- XNZCRRCSKWHTNV-UHFFFAOYSA-N 1-bromo-2-ethylsulfinylethane Chemical compound CCS(=O)CCBr XNZCRRCSKWHTNV-UHFFFAOYSA-N 0.000 abstract 1
- YIXKGNQEGITUGN-UHFFFAOYSA-N 1-bromo-2-methylsulfinylethane Chemical compound CS(=O)CCBr YIXKGNQEGITUGN-UHFFFAOYSA-N 0.000 abstract 1
- LIPRCTSGLFLUNJ-UHFFFAOYSA-N 1-chloro-2-ethylsulfinylethane Chemical compound CCS(=O)CCCl LIPRCTSGLFLUNJ-UHFFFAOYSA-N 0.000 abstract 1
- OKPWTEPQYVOQLV-UHFFFAOYSA-N 2-(2-bromoethylsulfinyl)propane Chemical compound BrCCS(=O)C(C)C OKPWTEPQYVOQLV-UHFFFAOYSA-N 0.000 abstract 1
- SXZARPFFQCBYHF-UHFFFAOYSA-N BrC(C)(S)CC Chemical compound BrC(C)(S)CC SXZARPFFQCBYHF-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- KQYPMOAGWMNYDC-UHFFFAOYSA-N dihydroxy-propan-2-yloxy-sulfanylidene-$l^{5}-phosphane Chemical compound CC(C)OP(O)(O)=S KQYPMOAGWMNYDC-UHFFFAOYSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 230000000749 insecticidal effect Effects 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 229910052698 phosphorus Inorganic materials 0.000 abstract 1
- 239000011574 phosphorus Substances 0.000 abstract 1
- 230000002285 radioactive effect Effects 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 125000002123 sulfanediylbis(methylene) group Chemical group [H]C([H])(*)SC([H])([H])* 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- C07F9/1651—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)
Abstract
Sulphinyl compounds having the general formul (RO)(R1O)P(O)S.C2H4S(O)R11 wherei the R's represent alkyl groups, the same or different, containing not more than 4 carbon atoms are prepared by reacting a salt of a thiophosphoric acid of the formula (RO)(R1O) P(O)SH with a halo-alkyl sulphinyl ethane of the formula XC2H4S(O)R11 where X is an halogen and the R's are as defined above, preferably using equimolar amounts of the reagents. The thiophosphoric acid salt may be used in admixture with a salt of the tautomeric acid (RO)(R1O)P(S)OH, in which case the tautomeric compounds of the formula (RO) (R1O)P(S)OC2H4S(O)R11 are also formed. A solvent such as a lower aliphatic alcohol or ketone may be present. A reaction temperature of 70-80 DEG C. is preferred. The mixture of the two tautomers may be separated by partition chromatography; the compounds have insecticidal properties. In the example: 1-bromo-2-ethyl sulphinyl ethane and the sodium salt of OO1 - diethyl - thiophosphate (obtained as described below) are refluxed in absolute ethanol; the product is isolated and subjected to partition chromatography using water and benzene or trichlorethylene, whereby 80 per cent of the product is shown to be the compound (C2H5O)2P(O)SC2H4S(O)C2H5\t and the remainder is believed to be the corresponding tautomeric compound. In like manner there may be reacted OO1-dimethyl thiophosphoric acid N a salt with 1-bromo-2-methyl sulphinyl ethane, o-methyl-o1-ethyl thiophosphoric acid Na salt and 1-bromo-2-n-propyl sulphinyl ethane and OO1-diethyl thiophosphoric acid Na salt with 1-bromo-2-isopropyl sulphinyl ethane. Other specified reagents are OO1-di-n or isopropyl thiophosphoric acid, 1-chloro-2-ethyl sulphinyl ethane and 1-bromo-2-n-butyl sulphinyl ethane. Alkali metal salts of OO1-dialkyl thiophosphoric acids may be prepared in admixture with the corresponding tautomers by reacting PSCl3 with a single or two different alcohols ROH and R1OH to yield the dialkyl thiophosphoric acid chloride which is then reacted with an alkali metal hydroxide. In the example, (C2H5O)2PSCl is prepared from PSCl3 containing radio-active phosphorus and then treated with aqueous NaOH. The halo-alkyl sulphinyl ethane reagents may be prepared by oxidation of the corresponding halo-alkyl mercapto ethanes with H2O2. In the example, 100 vol. H2O2 is added dropwise to an acetone solution of bromo-ethyl mercapto ethane at 20-30 DEG C. Specification 742,796 is referred to.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2034954A GB785030A (en) | 1954-07-12 | 1954-07-12 | Process for the production of sulphinyl ethyl thiophosphates |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2034954A GB785030A (en) | 1954-07-12 | 1954-07-12 | Process for the production of sulphinyl ethyl thiophosphates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB785030A true GB785030A (en) | 1957-10-23 |
Family
ID=10144481
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2034954A Expired GB785030A (en) | 1954-07-12 | 1954-07-12 | Process for the production of sulphinyl ethyl thiophosphates |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB785030A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1119849B (en) * | 1959-06-27 | 1961-12-21 | Bayer Ag | Process for the preparation of O-allyl-O-alkyl-thiol-phosphoric acid esters |
| DE1221627B (en) * | 1960-11-08 | 1966-07-28 | Monsanto Co | Process for the preparation of carbamoylmethylthiophosphoric acid esters |
-
1954
- 1954-07-12 GB GB2034954A patent/GB785030A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1119849B (en) * | 1959-06-27 | 1961-12-21 | Bayer Ag | Process for the preparation of O-allyl-O-alkyl-thiol-phosphoric acid esters |
| DE1221627B (en) * | 1960-11-08 | 1966-07-28 | Monsanto Co | Process for the preparation of carbamoylmethylthiophosphoric acid esters |
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