CH426776A - Verfahren zur Herstellung von O,O-Dialkyl-S-alkylthiolphosphaten - Google Patents
Verfahren zur Herstellung von O,O-Dialkyl-S-alkylthiolphosphatenInfo
- Publication number
- CH426776A CH426776A CH11563A CH11563A CH426776A CH 426776 A CH426776 A CH 426776A CH 11563 A CH11563 A CH 11563A CH 11563 A CH11563 A CH 11563A CH 426776 A CH426776 A CH 426776A
- Authority
- CH
- Switzerland
- Prior art keywords
- methyl
- theory
- yield
- mol
- dialkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 5
- 229910019142 PO4 Inorganic materials 0.000 title description 5
- 235000021317 phosphate Nutrition 0.000 title description 5
- 239000002253 acid Substances 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
- 239000011593 sulfur Substances 0.000 claims description 11
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims description 5
- 230000029936 alkylation Effects 0.000 claims description 4
- 238000005804 alkylation reaction Methods 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 4
- 229940100198 alkylating agent Drugs 0.000 claims description 3
- 239000002168 alkylating agent Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 150000003333 secondary alcohols Chemical class 0.000 claims description 3
- 150000003138 primary alcohols Chemical class 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
- 241000607479 Yersinia pestis Species 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 48
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- 238000003756 stirring Methods 0.000 description 18
- -1 alkyl radicals Chemical class 0.000 description 17
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 14
- 150000002148 esters Chemical group 0.000 description 12
- 239000000203 mixture Substances 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 229910052698 phosphorus Inorganic materials 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 7
- 241000700159 Rattus Species 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 231100000419 toxicity Toxicity 0.000 description 6
- 230000001988 toxicity Effects 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- GBOPMYXLQQCATA-UHFFFAOYSA-N CC(OC(C)SCCl)SCCl Chemical compound CC(OC(C)SCCl)SCCl GBOPMYXLQQCATA-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- JCMOMRVGBDYJCH-UHFFFAOYSA-N 1-(chloromethylsulfanyl)-2-[2-(chloromethylsulfanyl)ethoxy]ethane Chemical compound ClCSCCOCCSCCl JCMOMRVGBDYJCH-UHFFFAOYSA-N 0.000 description 1
- JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 description 1
- QXRYSTFZBZQNDU-UHFFFAOYSA-N 1-chlorobutane-2-thiol Chemical compound CCC(S)CCl QXRYSTFZBZQNDU-UHFFFAOYSA-N 0.000 description 1
- XPKDQBYOXNXKGG-UHFFFAOYSA-N 2-(chloromethyl)-4-methyl-1-methylsulfanylbenzene Chemical compound CSC1=CC=C(C)C=C1CCl XPKDQBYOXNXKGG-UHFFFAOYSA-N 0.000 description 1
- HOZLOOPIXHWKCI-UHFFFAOYSA-N 2-chloro-n-methylacetamide Chemical compound CNC(=O)CCl HOZLOOPIXHWKCI-UHFFFAOYSA-N 0.000 description 1
- GNHMRTZZNHZDDM-UHFFFAOYSA-N 3-chloropropionitrile Chemical compound ClCCC#N GNHMRTZZNHZDDM-UHFFFAOYSA-N 0.000 description 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 231100001224 moderate toxicity Toxicity 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 150000003573 thiols Chemical group 0.000 description 1
- 125000005490 tosylate group Chemical group 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01R—ELECTRICALLY-CONDUCTIVE CONNECTIONS; STRUCTURAL ASSOCIATIONS OF A PLURALITY OF MUTUALLY-INSULATED ELECTRICAL CONNECTING ELEMENTS; COUPLING DEVICES; CURRENT COLLECTORS
- H01R33/00—Coupling devices specially adapted for supporting apparatus and having one part acting as a holder providing support and electrical connection via a counterpart which is structurally associated with the apparatus, e.g. lamp holders; Separate parts thereof
- H01R33/05—Two-pole devices
- H01R33/06—Two-pole devices with two current-carrying pins, blades or analogous contacts, having their axes parallel to each other
- H01R33/08—Two-pole devices with two current-carrying pins, blades or analogous contacts, having their axes parallel to each other for supporting tubular fluorescent lamp
-
- 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
-
- 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
-
- 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
-
- 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
- C07F9/1651—Esters of thiophosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- 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
- C07F9/1653—Esters of thiophosphoric acids with arylalkanols
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)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF35839A DE1172667B (de) | 1962-01-24 | 1962-01-24 | Verfahren zur Herstellung von O, O-Dialkyl-S-alkylthiolphosphorsaeureestern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH426776A true CH426776A (de) | 1966-12-31 |
Family
ID=7096175
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH11563A CH426776A (de) | 1962-01-24 | 1963-01-07 | Verfahren zur Herstellung von O,O-Dialkyl-S-alkylthiolphosphaten |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3294874A (enrdf_load_stackoverflow) |
| BR (1) | BR6346394D0 (enrdf_load_stackoverflow) |
| CH (1) | CH426776A (enrdf_load_stackoverflow) |
| DE (1) | DE1172667B (enrdf_load_stackoverflow) |
| DK (1) | DK109851C (enrdf_load_stackoverflow) |
| GB (1) | GB977819A (enrdf_load_stackoverflow) |
| NL (2) | NL288076A (enrdf_load_stackoverflow) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2023034A1 (enrdf_load_stackoverflow) * | 1968-11-12 | 1970-08-07 | Sumitomo Chemical Co | |
| US3897552A (en) * | 1971-08-18 | 1975-07-29 | Bayer Ag | Fungicidal and bactericidal O-alkyl-O-cyclohexyl-S-alkyl-, haloalkyl-or alkenyl-phosphorothiolates |
| US3927148A (en) * | 1971-08-19 | 1975-12-16 | Exxon Research Engineering Co | O,S{40 -Dialkyl-S-hydrocarbylthioalkyl dithiophosphates |
| JPS51136654A (en) * | 1976-04-27 | 1976-11-26 | Nippon Tokushu Noyaku Seizo Kk | Process for preparation of o-cyclohexyl-o-alkyl-s-(halo or alkenyl)pho sphorothiolate |
| US4755311A (en) * | 1986-08-14 | 1988-07-05 | The Lubrizol Corporation | Phosphorus-, sulfur- and boron-containing compositions, and lubricant and functional fluid compositions containing same |
| US5449769A (en) * | 1989-03-06 | 1995-09-12 | Gen-Probe Incorporated | Method and reagent for sulfurization of organophosphorous compounds |
| WO1992004358A1 (en) * | 1990-09-04 | 1992-03-19 | Gen-Probe Incorporated | Method and reagent for sulfurization of organophosphorous compounds |
| DE19502197A1 (de) * | 1995-01-25 | 1996-08-01 | Bayer Ag | Verfahren zur Herstellung von Thiophosphorsäure-O,O'-diestern und ihrer Salze sowie deren Verwendung |
Family Cites Families (9)
| 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 |
| US2494284A (en) * | 1949-01-12 | 1950-01-10 | American Cyanamid Co | Cyanoalkyl phosphates and method of preparation |
| US2597534A (en) * | 1949-05-07 | 1952-05-20 | Bayer Ag | Neutral esters of thiolphosphoric acid |
| BE539662A (enrdf_load_stackoverflow) * | 1954-09-29 | |||
| DE949231C (de) * | 1955-05-03 | 1956-09-13 | Bayer Ag | Verfahren zur Herstellung von chlkorierten Benzylestern der Thiol- bzw. Thionothiolphosphorsaeuren |
| DE1024509B (de) * | 1956-03-03 | 1958-02-20 | Bayer Ag | Verfahren zur Herstellung von O, O-Dialkyl-thiol-phosphorsaeure- und -thiol-thiono-phsphorsaeureestern |
| DE1074034B (de) * | 1958-02-06 | 1960-01-28 | Farbenfabriken Bayer Aktiengesellschaft, Leverkusen-Bayerwerk | Verfahren zur Herstellung von Thiophosphorsäureestern |
| US3020305A (en) * | 1958-08-25 | 1962-02-06 | Monsanto Chemicals | Halogen substituted alkenylthioalkyl esters of phosphorus acids |
| DE1116657B (de) * | 1960-01-22 | 1961-11-09 | Bayer Ag | Verfahren zur Herstellung von Derivaten der Thiosaeuren des Phosphors |
-
0
- NL NL136286D patent/NL136286C/xx active
- NL NL288076D patent/NL288076A/xx unknown
-
1962
- 1962-01-24 DE DEF35839A patent/DE1172667B/de active Pending
-
1963
- 1963-01-07 CH CH11563A patent/CH426776A/de unknown
- 1963-01-22 US US253070A patent/US3294874A/en not_active Expired - Lifetime
- 1963-01-23 DK DK31963AA patent/DK109851C/da active
- 1963-01-24 GB GB3042/63A patent/GB977819A/en not_active Expired
- 1963-01-24 BR BR146394/63A patent/BR6346394D0/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK109851C (da) | 1968-07-15 |
| NL288076A (enrdf_load_stackoverflow) | |
| BR6346394D0 (pt) | 1973-08-09 |
| US3294874A (en) | 1966-12-27 |
| GB977819A (en) | 1964-12-16 |
| DE1172667B (de) | 1964-06-25 |
| NL136286C (enrdf_load_stackoverflow) |
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