DE1058992B - Verfahren zur Herstellung von Thiophosphonsaeureestern - Google Patents
Verfahren zur Herstellung von ThiophosphonsaeureesternInfo
- Publication number
- DE1058992B DE1058992B DEF23322A DEF0023322A DE1058992B DE 1058992 B DE1058992 B DE 1058992B DE F23322 A DEF23322 A DE F23322A DE F0023322 A DEF0023322 A DE F0023322A DE 1058992 B DE1058992 B DE 1058992B
- Authority
- DE
- Germany
- Prior art keywords
- ester
- stirring
- preparation
- ecm
- water
- 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.)
- Pending
Links
- 150000002148 esters Chemical class 0.000 title claims description 22
- 239000002253 acid Substances 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 5
- 238000003756 stirring Methods 0.000 claims description 16
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 11
- 239000011734 sodium Substances 0.000 claims description 11
- 229910052708 sodium Inorganic materials 0.000 claims description 11
- -1 alkyl radicals Chemical class 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 8
- 241001454295 Tetranychidae Species 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- 150000003254 radicals Chemical group 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 230000003151 ovacidal effect Effects 0.000 description 3
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 206010058667 Oral toxicity Diseases 0.000 description 2
- 241000488583 Panonychus ulmi Species 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 235000013601 eggs Nutrition 0.000 description 2
- 231100000418 oral toxicity Toxicity 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- YBDSNEVSFQMCTL-UHFFFAOYSA-N 2-(diethylamino)ethanethiol Chemical compound CCN(CC)CCS YBDSNEVSFQMCTL-UHFFFAOYSA-N 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- SELLGGZNVHTHDU-UHFFFAOYSA-N COP(C1=CC=CC=C1)(O)=S.Cl Chemical compound COP(C1=CC=CC=C1)(O)=S.Cl SELLGGZNVHTHDU-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 150000003008 phosphonic acid esters Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003580 thiophosphoric acid esters Chemical class 0.000 description 1
- 238000010626 work up procedure Methods 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
- C07F9/28—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
- C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4075—Esters with hydroxyalkyl 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)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE568845D BE568845A (US07816562-20101019-C00012.png) | 1957-06-24 | ||
| DEF23322A DE1058992B (de) | 1957-06-24 | 1957-06-24 | Verfahren zur Herstellung von Thiophosphonsaeureestern |
| DEF24304A DE1137012B (de) | 1957-06-24 | 1957-11-02 | Verfahren zur Herstellung von Phosphon- bzw. Thionophosphonsaeureestern |
| CH6043058A CH376917A (de) | 1957-06-24 | 1958-06-10 | Verfahren zur Herstellung von Phosphon- bzw. Thiophosphonsäureestern |
| GB2008558A GB847550A (en) | 1957-06-24 | 1958-06-23 | Phosphonic acid esters |
| FR1207524D FR1207524A (fr) | 1957-06-24 | 1958-06-24 | Procédé de préparation d'esters phosphoniques et thiophosphoniques |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF23322A DE1058992B (de) | 1957-06-24 | 1957-06-24 | Verfahren zur Herstellung von Thiophosphonsaeureestern |
| DEF24304A DE1137012B (de) | 1957-06-24 | 1957-11-02 | Verfahren zur Herstellung von Phosphon- bzw. Thionophosphonsaeureestern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1058992B true DE1058992B (de) | 1959-06-11 |
Family
ID=25974041
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF23322A Pending DE1058992B (de) | 1957-06-24 | 1957-06-24 | Verfahren zur Herstellung von Thiophosphonsaeureestern |
| DEF24304A Pending DE1137012B (de) | 1957-06-24 | 1957-11-02 | Verfahren zur Herstellung von Phosphon- bzw. Thionophosphonsaeureestern |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF24304A Pending DE1137012B (de) | 1957-06-24 | 1957-11-02 | Verfahren zur Herstellung von Phosphon- bzw. Thionophosphonsaeureestern |
Country Status (5)
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1137012B (de) * | 1957-06-24 | 1962-09-27 | Bayer Ag | Verfahren zur Herstellung von Phosphon- bzw. Thionophosphonsaeureestern |
| US3215721A (en) * | 1959-12-23 | 1965-11-02 | Bayer Ag | 5-alkyl o-aminoalkyl esters of alkyl, aryl, and cyclohexyl dithiophosphonic acids |
| US4012464A (en) * | 1965-09-24 | 1977-03-15 | The United States Of America As Represented By The Secretary Of The Army | S-(2-diisopropylamino-ethyl)O-ethyl methylphosphonothioate stabilized with soluble carbodiimides |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE594550A (US07816562-20101019-C00012.png) * | 1959-09-03 | 1900-01-01 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE845801C (de) * | 1949-05-30 | 1952-08-04 | Jan Marcel Didier Aron Samuel | Verfahren zur Herstellung von Orthophosphorsaeuremonoestern tertiaerer Aminoalkohole |
| BE568845A (US07816562-20101019-C00012.png) * | 1957-06-24 |
-
0
- BE BE568845D patent/BE568845A/xx unknown
-
1957
- 1957-06-24 DE DEF23322A patent/DE1058992B/de active Pending
- 1957-11-02 DE DEF24304A patent/DE1137012B/de active Pending
-
1958
- 1958-06-10 CH CH6043058A patent/CH376917A/de unknown
- 1958-06-23 GB GB2008558A patent/GB847550A/en not_active Expired
- 1958-06-24 FR FR1207524D patent/FR1207524A/fr not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1137012B (de) * | 1957-06-24 | 1962-09-27 | Bayer Ag | Verfahren zur Herstellung von Phosphon- bzw. Thionophosphonsaeureestern |
| US3215721A (en) * | 1959-12-23 | 1965-11-02 | Bayer Ag | 5-alkyl o-aminoalkyl esters of alkyl, aryl, and cyclohexyl dithiophosphonic acids |
| US4012464A (en) * | 1965-09-24 | 1977-03-15 | The United States Of America As Represented By The Secretary Of The Army | S-(2-diisopropylamino-ethyl)O-ethyl methylphosphonothioate stabilized with soluble carbodiimides |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1137012B (de) | 1962-09-27 |
| FR1207524A (fr) | 1960-02-17 |
| CH376917A (de) | 1964-04-30 |
| GB847550A (en) | 1960-09-07 |
| BE568845A (US07816562-20101019-C00012.png) |
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