GB740444A - Manufacture of sulphur derivatives of organic phosphorus compounds - Google Patents
Manufacture of sulphur derivatives of organic phosphorus compoundsInfo
- Publication number
- GB740444A GB740444A GB2647551A GB2647551A GB740444A GB 740444 A GB740444 A GB 740444A GB 2647551 A GB2647551 A GB 2647551A GB 2647551 A GB2647551 A GB 2647551A GB 740444 A GB740444 A GB 740444A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ethyl
- dissolved
- product
- hydrogen sulphide
- methylene chloride
- 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
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical class [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title abstract 3
- 150000002903 organophosphorus compounds Chemical class 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 21
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 abstract 7
- 150000001875 compounds Chemical class 0.000 abstract 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 4
- -1 dithiophosphoethane Chemical class 0.000 abstract 4
- 235000019441 ethanol Nutrition 0.000 abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 3
- 239000005864 Sulphur Substances 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- 238000000354 decomposition reaction Methods 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 2
- 239000012442 inert solvent Substances 0.000 abstract 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- MKBLKBBEGPAQLP-UHFFFAOYSA-N CCOP(=S)SCC Chemical compound CCOP(=S)SCC MKBLKBBEGPAQLP-UHFFFAOYSA-N 0.000 abstract 1
- LAAXPPFWBDOGEJ-UHFFFAOYSA-N CCP(=O)=S Chemical compound CCP(=O)=S LAAXPPFWBDOGEJ-UHFFFAOYSA-N 0.000 abstract 1
- CBMSILXIHXEWDK-UHFFFAOYSA-N CP(=O)=S Chemical compound CP(=O)=S CBMSILXIHXEWDK-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- XVMMHZIPFQOCRP-UHFFFAOYSA-K P(Cl)(Cl)Cl.[Cl-].[Al+3].CCl.[Cl-].[Cl-] Chemical compound P(Cl)(Cl)Cl.[Cl-].[Al+3].CCl.[Cl-].[Cl-] XVMMHZIPFQOCRP-UHFFFAOYSA-K 0.000 abstract 1
- GPWHDDKQSYOYBF-UHFFFAOYSA-N ac1l2u0q Chemical compound Br[Br-]Br GPWHDDKQSYOYBF-UHFFFAOYSA-N 0.000 abstract 1
- 125000005907 alkyl ester group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000005233 alkylalcohol group Chemical group 0.000 abstract 1
- PQLAYKMGZDUDLQ-UHFFFAOYSA-K aluminium bromide Substances Br[Al](Br)Br PQLAYKMGZDUDLQ-UHFFFAOYSA-K 0.000 abstract 1
- YSVOSSACTPSYNX-UHFFFAOYSA-K aluminum chloroethane trichlorophosphane trichloride Chemical compound [Cl-].[Al+3].P(Cl)(Cl)Cl.C(C)Cl.[Cl-].[Cl-] YSVOSSACTPSYNX-UHFFFAOYSA-K 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
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 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
- FLQUDUCNBDGCRI-UHFFFAOYSA-N hydroxy-sulfanyl-sulfidophosphanium Chemical class SP(S)=O FLQUDUCNBDGCRI-UHFFFAOYSA-N 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 238000012986 modification Methods 0.000 abstract 1
- 230000004048 modification Effects 0.000 abstract 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 239000012188 paraffin wax Substances 0.000 abstract 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 238000010792 warming Methods 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/42—Halides thereof
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
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
Organic phosphorus compounds containing sulphur are obtained by reacting a complex compound of an organic chloride of the formula RCl (in which R is as defined below), phosphorus trichloride or tribromide, and anhydrous aluminium chloride or bromide, with hydrogen sulphide at elevated temperature and subjecting the resulting sulphur-containing complex compound to controlled hydrolytic decomposition to form an organic monothiophosphonyl compound, e.g. ethyl thiophosphonyl dichloride, or a dithiophospho compound, e.g. dithiophosphoethane, or a monothiophospho compound. In a modification the product of the reaction with hydrogen sulphide is dissolved in an inert solvent, e.g. methylene chloride, and treated with an alkyl alcohol, e.g. ethyl alcohol and the product decomposed with water to form an alkyl ester of an R-substituted dithiophosphonic acid, e.g. O-ethyl ethyl dithiophosphonate. The radical R is defined as an alkyl, cycloalkyl, or aralkyl radical, or an alkenyl radical containing at least three carbon atoms, or a chloroalkyl radical, which term includes polychlorinated methyl but only includes higher radicals above methyl containing one chlorine atom. Examples of the radical R are methyl, ethyl, n-propyl, isopropyl, n-, iso-, secondary- and tertiary-butyl, cetyl, benzyl, and cyclohexyl. The formula RCl also includes chlorinated paraffins of indefinite composition such as chlorinated white spirit or chlorinated paraffin wax. The hydrolytic decomposition may be effected by treatment with water and when it is continued at raised temperature various products may be formed, thus by warming dithiophosphoethane (C2H5PS2) with water it is converted to monothio phosphoethane (C2H5.POS). In an alternative method for decomposing the complex compound obtained by the hydrogen sulphide treatment the product is dissolved in an inert solvent, e.g. methylene chloride, and decomposed by concentrated hydrochloric acid to produce an organic dithiophospho compound. In examples, an ethyl chloride-phosphorus trichloride-aluminium chloride 1 : 1 : 1-complex is treated with (1) hydrogen sulphide at 90-100 DEG C. for 200 hours and the product dissolved in methylene chloride and then decomposed with cold water at 15 DEG C. to yield dithiophosphoethane; (2) with hydrogen sulphide at 140-145 DEG C. for four hours and the product dissolved in methylene chloride and treated with cold water to form ethylthiophosphonyl dichloride (C2H5.P(S)Cl2); (3) with hydrogen sulphide at 130 DEG C. for 72 hours, the product being dissolved in methylene chloride and the solution divided into two parts, one of which is hydrolysed with concentrated hydrochloric acid to yield dithiophosphoethane, while the second part is treated with ethyl alcohol, the solvent and alcohol distilled off, and the residue dissolved in methylene chloride and treated with cold water to yield O-ethyl ethyl dithiophosphonate-C2H5PS(SH) (OC2H5). In another example, (4) a methyl chloride - phosphorus trichloride - aluminium chloride 1 : 1 : 1 complex is treated with hydrogen sulphide at 130 DEG C. for 100 hours and the product is dissolved in methylene chloride and hydrolysed with cold water to yield monothiophosphomethane (CH3POS).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2647551A GB740444A (en) | 1951-11-12 | 1951-11-12 | Manufacture of sulphur derivatives of organic phosphorus compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2647551A GB740444A (en) | 1951-11-12 | 1951-11-12 | Manufacture of sulphur derivatives of organic phosphorus compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB740444A true GB740444A (en) | 1955-11-16 |
Family
ID=10244228
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2647551A Expired GB740444A (en) | 1951-11-12 | 1951-11-12 | Manufacture of sulphur derivatives of organic phosphorus compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB740444A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3155709A (en) * | 1962-02-27 | 1964-11-03 | Monsanto Co | Method of making hydrocarbylphosphonodithioic acids |
| US3155708A (en) * | 1962-01-26 | 1964-11-03 | Monsanto Co | Process for making hydrocarbylphosphonothionic acid monoaryl esters |
| US3233010A (en) * | 1959-10-02 | 1966-02-01 | Bayer Ag | Dithiophosphonic acid esters and process for their production |
| US3268629A (en) * | 1962-10-11 | 1966-08-23 | Hooker Chemical Corp | Monoesters of phosphonic acids |
-
1951
- 1951-11-12 GB GB2647551A patent/GB740444A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3233010A (en) * | 1959-10-02 | 1966-02-01 | Bayer Ag | Dithiophosphonic acid esters and process for their production |
| US3155708A (en) * | 1962-01-26 | 1964-11-03 | Monsanto Co | Process for making hydrocarbylphosphonothionic acid monoaryl esters |
| US3155709A (en) * | 1962-02-27 | 1964-11-03 | Monsanto Co | Method of making hydrocarbylphosphonodithioic acids |
| US3268629A (en) * | 1962-10-11 | 1966-08-23 | Hooker Chemical Corp | Monoesters of phosphonic acids |
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