CA1113094A - Process for the manufacture of diazinon - Google Patents
Process for the manufacture of diazinonInfo
- Publication number
- CA1113094A CA1113094A CA345,584A CA345584A CA1113094A CA 1113094 A CA1113094 A CA 1113094A CA 345584 A CA345584 A CA 345584A CA 1113094 A CA1113094 A CA 1113094A
- Authority
- CA
- Canada
- Prior art keywords
- diazinon
- alcohol
- sodium
- pyrimidinolate
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims abstract description 16
- 230000008569 process Effects 0.000 title claims abstract description 16
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 title claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 27
- 238000006243 chemical reaction Methods 0.000 claims abstract description 10
- 150000001408 amides Chemical class 0.000 claims abstract description 5
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 9
- 238000009835 boiling Methods 0.000 claims description 7
- KMJJJTCKNZYTEY-UHFFFAOYSA-N chloro-diethoxy-sulfanylidene-$l^{5}-phosphane Chemical compound CCOP(Cl)(=S)OCC KMJJJTCKNZYTEY-UHFFFAOYSA-N 0.000 claims description 6
- OBQUUTUULQEKSI-UHFFFAOYSA-M sodium;pyrimidin-2-olate Chemical compound [Na+].[O-]C1=NC=CC=N1 OBQUUTUULQEKSI-UHFFFAOYSA-M 0.000 claims description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000008096 xylene Substances 0.000 claims description 4
- 239000012454 non-polar solvent Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 230000001376 precipitating effect Effects 0.000 claims 1
- 230000026731 phosphorylation Effects 0.000 abstract description 2
- 238000006366 phosphorylation reaction Methods 0.000 abstract description 2
- 239000007858 starting material Substances 0.000 abstract description 2
- RMQSINXLELHUAE-UHFFFAOYSA-N 1-[chloro(ethylsulfanyl)phosphoryl]oxyethane Chemical compound CCOP(Cl)(=O)SCC RMQSINXLELHUAE-UHFFFAOYSA-N 0.000 abstract 1
- 229910019142 PO4 Inorganic materials 0.000 abstract 1
- 239000002917 insecticide Substances 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 239000010452 phosphate Substances 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 238000007363 ring formation reaction Methods 0.000 description 5
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- AJPIUNPJBFBUKK-UHFFFAOYSA-N 2-isopropyl-6-methylpyrimidin-4-ol Chemical compound CC(C)C1=NC(C)=CC(O)=N1 AJPIUNPJBFBUKK-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- BHMLFPOTZYRDKA-IRXDYDNUSA-N (2s)-2-[(s)-(2-iodophenoxy)-phenylmethyl]morpholine Chemical compound IC1=CC=CC=C1O[C@@H](C=1C=CC=CC=1)[C@H]1OCCNC1 BHMLFPOTZYRDKA-IRXDYDNUSA-N 0.000 description 1
- JBKZUDJFOSCJDL-XQRVVYSFSA-N (z)-3-(2-methylpropanoylamino)but-2-enamide Chemical compound CC(C)C(=O)N\C(C)=C/C(N)=O JBKZUDJFOSCJDL-XQRVVYSFSA-N 0.000 description 1
- VDOKWPVSGXHSNP-UHFFFAOYSA-N 2-methylprop-1-en-1-one Chemical compound CC(C)=C=O VDOKWPVSGXHSNP-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical class 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 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000792765 Minous Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 150000001409 amidines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- LSACYLWPPQLVSM-UHFFFAOYSA-N isobutyric acid anhydride Chemical compound CC(C)C(=O)OC(=O)C(C)C LSACYLWPPQLVSM-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002730 mercury Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- QPYHDDZDAZRLJN-UHFFFAOYSA-M potassium;pyrimidin-2-olate Chemical compound [K+].[O-]C1=NC=CC=N1 QPYHDDZDAZRLJN-UHFFFAOYSA-M 0.000 description 1
- -1 propylate Chemical compound 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical group 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C07F9/6512—Six-membered rings having the nitrogen atoms in positions 1 and 3
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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792907773 DE2907773A1 (de) | 1979-02-28 | 1979-02-28 | Verfahren zur herstellung von diazinon |
| DEP2907773.4 | 1979-02-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1113094A true CA1113094A (en) | 1981-11-24 |
Family
ID=6064094
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA345,584A Expired CA1113094A (en) | 1979-02-28 | 1980-02-13 | Process for the manufacture of diazinon |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4323678A (cg-RX-API-DMAC10.html) |
| EP (1) | EP0015503B1 (cg-RX-API-DMAC10.html) |
| JP (1) | JPS5837319B2 (cg-RX-API-DMAC10.html) |
| CA (1) | CA1113094A (cg-RX-API-DMAC10.html) |
| DE (2) | DE2907773A1 (cg-RX-API-DMAC10.html) |
| ES (1) | ES488979A1 (cg-RX-API-DMAC10.html) |
| IL (1) | IL59090A (cg-RX-API-DMAC10.html) |
| IN (1) | IN151910B (cg-RX-API-DMAC10.html) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3344429A1 (de) * | 1983-12-08 | 1985-06-20 | Wacker-Chemie GmbH, 8000 München | Verfahren zur herstellung von 2-isopropyl-4-methyl-6-hydroxypyrimidin |
| IL76705A (en) * | 1985-10-14 | 1990-09-17 | Makhteshim Chem Works Ltd | Process for manufacturing diazinon |
| US5034529A (en) * | 1988-04-28 | 1991-07-23 | Ciba-Geigy Corporation | Process for the production of thiophosphoric acid esters of hydroxypyrimidines |
| US5231180A (en) * | 1989-09-28 | 1993-07-27 | Makhteshim Chemical Works, Ltd. | Process for the manufacture of diazinon |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LU31414A1 (cg-RX-API-DMAC10.html) * | 1951-04-20 | 1900-01-01 | ||
| US2928864A (en) * | 1958-01-08 | 1960-03-15 | Dow Chemical Co | Method for the manufacture of mixed phosphorothioate esters |
| FR1473812A (cg-RX-API-DMAC10.html) * | 1962-08-16 | 1967-03-24 | ||
| US3367935A (en) * | 1965-10-14 | 1968-02-06 | Geigy Chem Corp | Process for the preparation of phosphoric acid esters |
| DE1806867C3 (de) * | 1968-11-04 | 1974-07-18 | Byk-Gulden Lomberg Chemische Fabrik Gmbh, 7750 Konstanz | Verfahren zur Herstellung substituierter 4-Hydroxy pyrimidine |
| DE2065698C3 (de) * | 1969-11-17 | 1979-08-30 | Chisso Corp., Osaka (Japan) | Verfahren zur Herstellung von 2-Isopropyl-6-methyl-4(3H)-pyrimidon |
| US3862273A (en) * | 1973-03-28 | 1975-01-21 | Dow Chemical Co | Preparation of 0-aryl 0,0-dialkyl phosphorothioates |
| GB1418784A (en) * | 1973-03-29 | 1975-12-24 | Ici Ltd | Phosphorus containing pyrimidine compounds and pesticidal compositions comprising them |
| US4066642A (en) * | 1973-11-01 | 1978-01-03 | Ciba-Geigy Corporation | Process for the production of thiophosphoric acid esters |
| US4012506A (en) * | 1975-07-03 | 1977-03-15 | Ciba-Geigy Corporation | Pyrimidyl thio- and dithio-phosphoric acid esters |
| US4052397A (en) * | 1976-11-22 | 1977-10-04 | Ciba-Geigy Corporation | Process for the production of 2-alkyl or 2-cycloalkyl-4-methyl-6-hydroxypyrimidines |
| GB2011415B (en) * | 1977-12-27 | 1982-06-30 | Ciba Geigy Ag | Process for the production of thiophosphoric acid esters |
-
1979
- 1979-02-28 DE DE19792907773 patent/DE2907773A1/de not_active Withdrawn
- 1979-12-25 JP JP54169101A patent/JPS5837319B2/ja not_active Expired
-
1980
- 1980-01-08 IL IL59090A patent/IL59090A/xx unknown
- 1980-02-11 US US06/120,411 patent/US4323678A/en not_active Expired - Lifetime
- 1980-02-13 CA CA345,584A patent/CA1113094A/en not_active Expired
- 1980-02-27 ES ES488979A patent/ES488979A1/es not_active Expired
- 1980-02-28 IN IN233/CAL/80A patent/IN151910B/en unknown
- 1980-02-28 DE DE8080100987T patent/DE3060908D1/de not_active Expired
- 1980-02-28 EP EP80100987A patent/EP0015503B1/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS55118471A (en) | 1980-09-11 |
| EP0015503B1 (de) | 1982-10-06 |
| DE3060908D1 (en) | 1982-11-11 |
| IL59090A0 (en) | 1980-05-30 |
| US4323678A (en) | 1982-04-06 |
| DE2907773A1 (de) | 1980-09-11 |
| JPS5837319B2 (ja) | 1983-08-15 |
| IN151910B (cg-RX-API-DMAC10.html) | 1983-09-03 |
| ES488979A1 (es) | 1980-09-16 |
| EP0015503A1 (de) | 1980-09-17 |
| IL59090A (en) | 1983-07-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry | ||
| MKEX | Expiry |
Effective date: 19981124 |