DE3228868A1 - Verfahren zur herstellung von o,s-dimethylthiolophosphorsaeureamid - Google Patents
Verfahren zur herstellung von o,s-dimethylthiolophosphorsaeureamidInfo
- Publication number
- DE3228868A1 DE3228868A1 DE19823228868 DE3228868A DE3228868A1 DE 3228868 A1 DE3228868 A1 DE 3228868A1 DE 19823228868 DE19823228868 DE 19823228868 DE 3228868 A DE3228868 A DE 3228868A DE 3228868 A1 DE3228868 A1 DE 3228868A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- organic solvent
- compound
- methylation
- 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.)
- Withdrawn
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 24
- 239000003960 organic solvent Substances 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 19
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 18
- 238000007069 methylation reaction Methods 0.000 claims description 18
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Substances [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 18
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 claims description 14
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 13
- 238000005755 formation reaction Methods 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 238000000605 extraction Methods 0.000 claims description 11
- 230000011987 methylation Effects 0.000 claims description 11
- 230000015572 biosynthetic process Effects 0.000 claims description 9
- 238000004821 distillation Methods 0.000 claims description 9
- 229940102396 methyl bromide Drugs 0.000 claims description 7
- 239000003513 alkali Substances 0.000 claims description 6
- 239000008346 aqueous phase Substances 0.000 claims description 6
- 150000004820 halides Chemical class 0.000 claims description 6
- 229940050176 methyl chloride Drugs 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 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 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 239000011591 potassium Substances 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000000284 extract Substances 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 10
- 150000001408 amides Chemical class 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 229960004592 isopropanol Drugs 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- 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
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical compound OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- NNKVPIKMPCQWCG-UHFFFAOYSA-N methamidophos Chemical compound COP(N)(=O)SC NNKVPIKMPCQWCG-UHFFFAOYSA-N 0.000 description 1
- -1 methyl halide Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 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
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823228868 DE3228868A1 (de) | 1982-08-03 | 1982-08-03 | Verfahren zur herstellung von o,s-dimethylthiolophosphorsaeureamid |
| US06/516,167 US4537730A (en) | 1982-08-03 | 1983-07-21 | Preparation of O,S-dimethyl-thiolophosphoric acid amide |
| DE8383107310T DE3361068D1 (en) | 1982-08-03 | 1983-07-26 | Process for the preparation of the 0,s-dimethyl ester of thiophosphoric-acid amide |
| EP83107310A EP0104352B1 (de) | 1982-08-03 | 1983-07-26 | Verfahren zur Herstellung von O,S-Dimethyl-thiolophosphorsäureamid |
| JP58137886A JPS5944395A (ja) | 1982-08-03 | 1983-07-29 | Ｏ，ｓ−ジメチル−チオロ燐酸アミドの製造方法 |
| DD83253606A DD210282A5 (de) | 1982-08-03 | 1983-08-01 | Verfahren zur herstellung von o,s-dimethyl-thiolophosphorsaeureamid |
| IL69387A IL69387A (en) | 1982-08-03 | 1983-08-01 | Preparation of o,s-dimethyl-thiolophosphoric acid amide |
| DK353783A DK353783A (da) | 1982-08-03 | 1983-08-02 | Fremgangsmaade til fremstilling af o,s-dimethylthiolo-phosphorsyreamid |
| BR8304127A BR8304127A (pt) | 1982-08-03 | 1983-08-02 | Processo para a preparacao de amida de acido o,s-dimetil-tiolofosforico |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823228868 DE3228868A1 (de) | 1982-08-03 | 1982-08-03 | Verfahren zur herstellung von o,s-dimethylthiolophosphorsaeureamid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3228868A1 true DE3228868A1 (de) | 1984-02-09 |
Family
ID=6169960
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19823228868 Withdrawn DE3228868A1 (de) | 1982-08-03 | 1982-08-03 | Verfahren zur herstellung von o,s-dimethylthiolophosphorsaeureamid |
| DE8383107310T Expired DE3361068D1 (en) | 1982-08-03 | 1983-07-26 | Process for the preparation of the 0,s-dimethyl ester of thiophosphoric-acid amide |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8383107310T Expired DE3361068D1 (en) | 1982-08-03 | 1983-07-26 | Process for the preparation of the 0,s-dimethyl ester of thiophosphoric-acid amide |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4537730A (https=) |
| EP (1) | EP0104352B1 (https=) |
| JP (1) | JPS5944395A (https=) |
| BR (1) | BR8304127A (https=) |
| DD (1) | DD210282A5 (https=) |
| DE (2) | DE3228868A1 (https=) |
| DK (1) | DK353783A (https=) |
| IL (1) | IL69387A (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2548112Y2 (ja) * | 1988-01-27 | 1997-09-17 | 東洋濾機製造株式会社 | エアークリーナ用フィルタエレメント |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA494562A (en) * | 1948-02-04 | 1953-07-21 | American Cyanamid Company | Carbamylalkyl phosphates and method of preparation |
| BE581598A (https=) * | 1958-08-12 | |||
| DE1210835B (de) * | 1964-07-02 | 1966-02-17 | Bayer Ag | Verfahren zur Herstellung von Amidothiolphosphorsaeureestern |
| US3309266A (en) * | 1965-07-01 | 1967-03-14 | Chevron Res | Insecticidal compositions containing oalkyl-s-alkyl phosphoroamidothioates and methods for killing insects therewith |
| US3670057A (en) * | 1969-11-10 | 1972-06-13 | Sumitomo Chemical Co | S(alkllthio ethyl) phosphorothioamidate |
| US3832425A (en) * | 1972-12-21 | 1974-08-27 | Chevron Res | N-acyl-o-hydrocarbylphosphoroamidothioate salts and process for making same |
-
1982
- 1982-08-03 DE DE19823228868 patent/DE3228868A1/de not_active Withdrawn
-
1983
- 1983-07-21 US US06/516,167 patent/US4537730A/en not_active Expired - Fee Related
- 1983-07-26 EP EP83107310A patent/EP0104352B1/de not_active Expired
- 1983-07-26 DE DE8383107310T patent/DE3361068D1/de not_active Expired
- 1983-07-29 JP JP58137886A patent/JPS5944395A/ja active Granted
- 1983-08-01 IL IL69387A patent/IL69387A/xx unknown
- 1983-08-01 DD DD83253606A patent/DD210282A5/de not_active IP Right Cessation
- 1983-08-02 BR BR8304127A patent/BR8304127A/pt not_active IP Right Cessation
- 1983-08-02 DK DK353783A patent/DK353783A/da not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| DK353783A (da) | 1984-02-04 |
| US4537730A (en) | 1985-08-27 |
| IL69387A (en) | 1987-10-30 |
| BR8304127A (pt) | 1984-03-13 |
| JPH0363554B2 (https=) | 1991-10-01 |
| DE3361068D1 (en) | 1985-11-28 |
| EP0104352A1 (de) | 1984-04-04 |
| IL69387A0 (en) | 1983-11-30 |
| EP0104352B1 (de) | 1985-10-23 |
| JPS5944395A (ja) | 1984-03-12 |
| DK353783D0 (da) | 1983-08-02 |
| DD210282A5 (de) | 1984-06-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE60128012T2 (de) | Verfahren und vorrichtung zur herstellung von hydrazodicarbonsäureamid unter verwendung von harnstoff als ausgangsmaterial | |
| DE2449492A1 (de) | Verfahren zur herstellung von optisch aktivem p-hydroxyphenylglycin | |
| DE2212604A1 (de) | Verfahren zur Herstellung von 2-Halogenaethylphosphonsaeuren | |
| DE69604513T2 (de) | Verfahren zur Herstellung substituierter Carbodiimide | |
| DE2756560C2 (de) | Verfahren zur Herstellung von Piperonal | |
| DE69904545T2 (de) | Verfahren zum Herstellen von Allyl 2-hydroxyisobutyrat | |
| EP0087585A1 (de) | Verfahren zur Herstellung von 3-Alkoxi-acrylnitrilen | |
| EP0104352B1 (de) | Verfahren zur Herstellung von O,S-Dimethyl-thiolophosphorsäureamid | |
| DE2519314C2 (de) | Verfahren zur Herstellung von 3-Trichlormethyl-5-niederalkoxy- 1,2,4-thiadiazol | |
| EP0676390B1 (de) | Verfahren zur Herstellung von 1-Aminocyclopropancarbonsäurehydrochlorid | |
| EP1902042B1 (de) | Verfahren zur herstellung von 3,4-dichlor-isothiazolcarbonsäure | |
| DE1643275B2 (de) | Verfahren zur Herstellung von 1,3-Diaminopropanol-(2) | |
| EP0497210B1 (de) | Verfahren zur Herstellung von Dialkylaminopropandiol | |
| DE3538747C2 (https=) | ||
| DE2944030A1 (de) | Verfahren zur herstellung von aminophenolaether | |
| DE10311763A1 (de) | Verfahren zur Herstellung von 2-Cyan-3-hydroxy-N-(phenyl)but-2-enamiden | |
| EP1077210A2 (de) | Verfahren zur Herstellung von 4,6-Dichlor-5-fluorpyrimidin und seine Verwendung als Biocid | |
| WO2001077062A1 (de) | Verfahren zur herstellung von 4-brom- und 4-chlor-2-nitro-1-trifluormethoxybenzol | |
| DE2065698A1 (de) | Verfahren zur herstellung von 2isopropyl-6-methyl-4(3h)-pyrimidon | |
| DE2601782C3 (de) | Verfahren zur Herstellung von o-Dialkylaminomethylphenolen | |
| DE69227890T2 (de) | Verfahren zur herstellung von 5-amino-3-methylpyrazol | |
| DE2101359C3 (de) | Verfahren zur Herstellung von 4-Mercaptophenolen | |
| DE3150929A1 (de) | "verfahren zur herstellung von cytosin" | |
| EP0083010A1 (de) | Diether von m- oder p-Hydroxyphenolen und Verfahren zur Herstellung der Diether oder Monoether von m- oder p-Hydroxyphenolen | |
| DE1089749B (de) | Verfahren zur kontinuierlichen Herstellung von Vinylthioaethern |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |