DE2156718C3 - Tetramethyl-dithiolpyrophosphorsäureester und Verfahren zu seiner Herstellung - Google Patents
Tetramethyl-dithiolpyrophosphorsäureester und Verfahren zu seiner HerstellungInfo
- Publication number
- DE2156718C3 DE2156718C3 DE2156718A DE2156718A DE2156718C3 DE 2156718 C3 DE2156718 C3 DE 2156718C3 DE 2156718 A DE2156718 A DE 2156718A DE 2156718 A DE2156718 A DE 2156718A DE 2156718 C3 DE2156718 C3 DE 2156718C3
- Authority
- DE
- Germany
- Prior art keywords
- acid ester
- preparation
- dithiolpyrophosphoric
- tetramethyl
- 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
- 239000002253 acid Substances 0.000 title claims description 18
- 150000002148 esters Chemical class 0.000 title claims description 8
- 238000000034 method Methods 0.000 title description 8
- 238000002360 preparation method Methods 0.000 title description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
- 229910052717 sulfur Inorganic materials 0.000 description 11
- 229910052760 oxygen Inorganic materials 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 8
- 229910021529 ammonia Inorganic materials 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- -1 ester Salts Chemical class 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000013067 intermediate product Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- CZHYKKAKFWLGJO-UHFFFAOYSA-N dimethyl phosphite Chemical compound COP([O-])OC CZHYKKAKFWLGJO-UHFFFAOYSA-N 0.000 description 1
- WWJJVKAEQGGYHJ-UHFFFAOYSA-N dimethyl thiophosphate Chemical compound COP(O)(=S)OC WWJJVKAEQGGYHJ-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000001035 methylating effect Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 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
- C07F9/1658—Esters of thiopolyphosphoric acids or anhydrides
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing acyclic or cycloaliphatic radicals
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE791391D BE791391A (fr) | 1971-11-16 | Nouvel ester tetramethylique d'acide dithiol-pyrophosphorique, son procede de preparation et son application comme produit intermediaire dans la synthese de pesticides | |
| DE2156718A DE2156718C3 (de) | 1971-11-16 | 1971-11-16 | Tetramethyl-dithiolpyrophosphorsäureester und Verfahren zu seiner Herstellung |
| US00303302A US3845170A (en) | 1971-11-16 | 1972-11-02 | Tetramethyl-dithiolpyrophosphoric acid ester and method of preparation |
| JP11259872A JPS5654319B2 (enExample) | 1971-11-16 | 1972-11-11 | |
| NL7215348A NL7215348A (enExample) | 1971-11-16 | 1972-11-13 | |
| IL40813A IL40813A (en) | 1971-11-16 | 1972-11-13 | Tetramethyl-dithiolpyrophosphoric acid ester,process for its preparation and its use as an intermediate for pesticide synthesis |
| BR007979/72A BR7207979D0 (pt) | 1971-11-16 | 1972-11-14 | Processo de preparacao de ester de acido tetrametil-ditiolpirofosforico |
| CH1653072A CH586714A5 (enExample) | 1971-11-16 | 1972-11-14 | |
| IT31647/72A IT970491B (it) | 1971-11-16 | 1972-11-14 | Estere tetrametil ditiolpirofosfo rico processo per la sua produzio ne e suo uso come prodotto interme dio per la sintesi di agenti anti parassitari |
| GB5277272A GB1349228A (en) | 1971-11-16 | 1972-11-15 | Tetramethyl dithiolpyrophosphoric acid ester process for its preparation and its use as an intermediate for pesticide synthesis |
| FR7240765A FR2160554B1 (enExample) | 1971-11-16 | 1972-11-16 | |
| US05/455,486 US4001353A (en) | 1971-11-16 | 1974-03-27 | Preparation of o,s-dimethyl-thiol-phosphoric acid diester-amide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2156718A DE2156718C3 (de) | 1971-11-16 | 1971-11-16 | Tetramethyl-dithiolpyrophosphorsäureester und Verfahren zu seiner Herstellung |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2156718A1 DE2156718A1 (de) | 1973-05-24 |
| DE2156718B2 DE2156718B2 (de) | 1979-05-17 |
| DE2156718C3 true DE2156718C3 (de) | 1980-01-10 |
Family
ID=5825198
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2156718A Expired DE2156718C3 (de) | 1971-11-16 | 1971-11-16 | Tetramethyl-dithiolpyrophosphorsäureester und Verfahren zu seiner Herstellung |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3845170A (enExample) |
| JP (1) | JPS5654319B2 (enExample) |
| BE (1) | BE791391A (enExample) |
| BR (1) | BR7207979D0 (enExample) |
| CH (1) | CH586714A5 (enExample) |
| DE (1) | DE2156718C3 (enExample) |
| FR (1) | FR2160554B1 (enExample) |
| GB (1) | GB1349228A (enExample) |
| IL (1) | IL40813A (enExample) |
| IT (1) | IT970491B (enExample) |
| NL (1) | NL7215348A (enExample) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2434357A (en) * | 1943-09-27 | 1948-01-13 | Minerec Corp | Tetra-alkyl carbonyl tetrathio diphosphates and process for their preparation |
-
0
- BE BE791391D patent/BE791391A/xx unknown
-
1971
- 1971-11-16 DE DE2156718A patent/DE2156718C3/de not_active Expired
-
1972
- 1972-11-02 US US00303302A patent/US3845170A/en not_active Expired - Lifetime
- 1972-11-11 JP JP11259872A patent/JPS5654319B2/ja not_active Expired
- 1972-11-13 NL NL7215348A patent/NL7215348A/xx not_active Application Discontinuation
- 1972-11-13 IL IL40813A patent/IL40813A/xx unknown
- 1972-11-14 IT IT31647/72A patent/IT970491B/it active
- 1972-11-14 CH CH1653072A patent/CH586714A5/xx not_active IP Right Cessation
- 1972-11-14 BR BR007979/72A patent/BR7207979D0/pt unknown
- 1972-11-15 GB GB5277272A patent/GB1349228A/en not_active Expired
- 1972-11-16 FR FR7240765A patent/FR2160554B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL7215348A (enExample) | 1973-05-18 |
| DE2156718A1 (de) | 1973-05-24 |
| IL40813A0 (en) | 1973-01-30 |
| DE2156718B2 (de) | 1979-05-17 |
| JPS5654319B2 (enExample) | 1981-12-24 |
| IL40813A (en) | 1975-03-13 |
| BR7207979D0 (pt) | 1973-08-09 |
| GB1349228A (en) | 1974-04-03 |
| FR2160554A1 (enExample) | 1973-06-29 |
| IT970491B (it) | 1974-04-10 |
| FR2160554B1 (enExample) | 1976-06-04 |
| CH586714A5 (enExample) | 1977-04-15 |
| US3845170A (en) | 1974-10-29 |
| JPS4857931A (enExample) | 1973-08-14 |
| BE791391A (fr) | 1973-05-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |