BE568504A - - Google Patents
Info
- Publication number
- BE568504A BE568504A BE568504DA BE568504A BE 568504 A BE568504 A BE 568504A BE 568504D A BE568504D A BE 568504DA BE 568504 A BE568504 A BE 568504A
- Authority
- BE
- Belgium
- Prior art keywords
- methyl
- benzene
- sodium
- boiling
- mixture
- Prior art date
Links
- 239000002253 acid Substances 0.000 claims description 12
- 150000007513 acids Chemical class 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- 150000003462 sulfoxides Chemical class 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 125000005027 hydroxyaryl group Chemical group 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- 125000001174 sulfone group Chemical group 0.000 claims description 2
- 150000003457 sulfones Chemical class 0.000 claims description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 18
- 150000002148 esters Chemical class 0.000 description 15
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- 238000009835 boiling Methods 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 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 description 4
- 241000700159 Rattus Species 0.000 description 4
- 241001454295 Tetranychidae Species 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 231100000419 toxicity Toxicity 0.000 description 4
- 230000001988 toxicity Effects 0.000 description 4
- 241001124076 Aphididae Species 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
- 238000006243 chemical reaction Methods 0.000 description 3
- -1 ester chloride Chemical class 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- MVZLIWASNYWCQD-UHFFFAOYSA-N 4-(4-hydroxy-2-methylphenyl)sulfinyl-3-methylphenol Chemical compound CC1=CC(O)=CC=C1S(=O)C1=CC=C(O)C=C1C MVZLIWASNYWCQD-UHFFFAOYSA-N 0.000 description 2
- QASBCTGZKABPKX-UHFFFAOYSA-N 4-(methylsulfanyl)phenol Chemical compound CSC1=CC=C(O)C=C1 QASBCTGZKABPKX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 2
- CDSAPDHBCYSHAQ-UHFFFAOYSA-N ethoxy-hydroxy-methylperoxy-sulfanylidene-lambda5-phosphane Chemical compound COOP(OCC)(O)=S CDSAPDHBCYSHAQ-UHFFFAOYSA-N 0.000 description 2
- ZHLJHXUVDLRSRE-UHFFFAOYSA-N ethylperoxy-hydroxy-propan-2-yloxy-sulfanylidene-lambda5-phosphane Chemical compound C(C)OOP(OC(C)C)(O)=S ZHLJHXUVDLRSRE-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 2
- 229940031826 phenolate Drugs 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- XOXIKTPTJGGZHG-UHFFFAOYSA-N 4-(3,4-dimethylphenyl)sulfinyl-1,2-dimethylbenzene Chemical compound C1=C(C)C(C)=CC=C1S(=O)C1=CC=C(C)C(C)=C1 XOXIKTPTJGGZHG-UHFFFAOYSA-N 0.000 description 1
- AKHZFKHOIVFHCH-UHFFFAOYSA-N 4-(4-hydroxy-2-methylphenyl)sulfonyl-3-methylphenol Chemical compound CC1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1C AKHZFKHOIVFHCH-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 241000254171 Curculionidae Species 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- WABAEEDHTRIFPM-UHFFFAOYSA-N hydroxy-sulfanyl-sulfanylidene-$l^{4}-sulfane Chemical compound SS(S)=O WABAEEDHTRIFPM-UHFFFAOYSA-N 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- RBXVOQPAMPBADW-UHFFFAOYSA-N nitrous acid;phenol Chemical class ON=O.OC1=CC=CC=C1 RBXVOQPAMPBADW-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007858 starting material 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
- C07F9/18—Esters of thiophosphoric acids with hydroxyaryl 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE568504A true BE568504A (enrdf_load_stackoverflow) |
Family
ID=187819
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE568504D BE568504A (enrdf_load_stackoverflow) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE568504A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3322863A (en) * | 1963-09-09 | 1967-05-30 | Dow Chemical Co | Aminoalkyl phosphonates and preparation thereof |
-
0
- BE BE568504D patent/BE568504A/fr unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3322863A (en) * | 1963-09-09 | 1967-05-30 | Dow Chemical Co | Aminoalkyl phosphonates and preparation thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| BE568504A (enrdf_load_stackoverflow) | ||
| EP0089859B1 (fr) | Procédé de préparation de perfluoroalcoyl-2-éthanols | |
| CH642614A5 (fr) | Procede de preparation d'acides trichlorophenoxyalcanoiques et de leurs derives exempts de dibenzo-p-dioxines chlorees. | |
| EP0233432A1 (fr) | Composés polyfluoroalkylthio-méthyliques, leurs procédés de préparation et leurs applications comme agents tensio-actifs ou précurseurs de ces derniers | |
| CH392483A (fr) | Procédé de préparation de nouveaux esters d'acides 4-halo-3-sulfamoyl-benzoïques | |
| EP0059659B1 (fr) | Nouveaux dérivés de l'acide 4-méthyl 3-formyl pentanoique, leur procédé de préparation et leur application à la préparation de dérivés cycliques | |
| EP0040140A1 (fr) | Procédé de préparation d'acides métaphénoxybenzoiques et de leurs esters alkyliques | |
| EP0216659A1 (fr) | Nouveaux halogénoformiates de dihalogéno-2,2 vinyle, leur procédé de préparation et leurs applications | |
| SK58893A3 (en) | Phosphinyloxy propanaminium inner salt derivatives | |
| FR2486526A1 (fr) | Procede de preparation de derives de l'oxyde de diphenyle | |
| EP0290319B1 (fr) | Fluoro-1 Halogéno-1 dioxa-3,6 bicyclo [4.1.0] heptane, procédé de préparation et utilisation | |
| BE396105A (enrdf_load_stackoverflow) | ||
| BE595781A (enrdf_load_stackoverflow) | ||
| FR2560191A1 (fr) | Derives de nitrodiaryl sulfoxyde, procede pour leur preparation et compositions pharmaceutiques et pesticides les contenant comme ingredient actif | |
| BE568089A (enrdf_load_stackoverflow) | ||
| BE507032A (enrdf_load_stackoverflow) | ||
| BE566666A (enrdf_load_stackoverflow) | ||
| BE558542A (enrdf_load_stackoverflow) | ||
| BE632152A (enrdf_load_stackoverflow) | ||
| BE518457A (enrdf_load_stackoverflow) | ||
| BE613786A (enrdf_load_stackoverflow) | ||
| BE568697A (enrdf_load_stackoverflow) | ||
| BE583148A (enrdf_load_stackoverflow) | ||
| BE572562A (enrdf_load_stackoverflow) | ||
| BE565804A (enrdf_load_stackoverflow) |