DD153553A5 - Verfahren zur herstellung von thiophosphorsaeureestern - Google Patents
Verfahren zur herstellung von thiophosphorsaeureestern Download PDFInfo
- Publication number
- DD153553A5 DD153553A5 DD80224433A DD22443380A DD153553A5 DD 153553 A5 DD153553 A5 DD 153553A5 DD 80224433 A DD80224433 A DD 80224433A DD 22443380 A DD22443380 A DD 22443380A DD 153553 A5 DD153553 A5 DD 153553A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- formula
- reaction
- compounds
- item
- alkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 20
- 238000002360 preparation method Methods 0.000 title claims description 11
- 150000003580 thiophosphoric acid esters Chemical class 0.000 title description 4
- 238000006243 chemical reaction Methods 0.000 claims abstract description 37
- 150000001875 compounds Chemical class 0.000 claims abstract description 23
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 239000001301 oxygen Substances 0.000 claims abstract description 8
- 150000001768 cations Chemical class 0.000 claims abstract description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 23
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
- 239000007789 gas Substances 0.000 claims description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
- 229910052717 sulfur Chemical group 0.000 claims description 11
- 239000011593 sulfur Chemical group 0.000 claims description 11
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 10
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 10
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 10
- 239000008096 xylene Substances 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 8
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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
- 150000001805 chlorine compounds Chemical group 0.000 claims description 3
- 238000000605 extraction Methods 0.000 claims description 3
- 239000012429 reaction media Substances 0.000 claims description 3
- 239000011734 sodium Chemical group 0.000 claims description 3
- 238000010626 work up procedure Methods 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical group [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 229910052708 sodium Chemical group 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims 2
- QQGISFDJEJMKIL-JAIQZWGSSA-N (5z)-5-[[3-(hydroxymethyl)thiophen-2-yl]methylidene]-10-methoxy-2,2,4-trimethyl-1h-chromeno[3,4-f]quinolin-9-ol Chemical compound C1=CC=2NC(C)(C)C=C(C)C=2C2=C1C=1C(OC)=C(O)C=CC=1O\C2=C/C=1SC=CC=1CO QQGISFDJEJMKIL-JAIQZWGSSA-N 0.000 claims 1
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 229910019142 PO4 Inorganic materials 0.000 abstract description 2
- 235000021317 phosphate Nutrition 0.000 abstract description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 18
- 239000012071 phase Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000012074 organic phase Substances 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 7
- 235000011121 sodium hydroxide Nutrition 0.000 description 7
- 239000002351 wastewater Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 239000002585 base Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- CZHYKKAKFWLGJO-UHFFFAOYSA-N dimethyl phosphite Chemical compound COP([O-])OC CZHYKKAKFWLGJO-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- LWRYJFJUTLBKPU-UHFFFAOYSA-M sodium;dimethoxy-oxido-sulfanylidene-$l^{5}-phosphane Chemical compound [Na+].COP([O-])(=S)OC LWRYJFJUTLBKPU-UHFFFAOYSA-M 0.000 description 3
- GBNVXYXIRHSYEG-UHFFFAOYSA-N 1-chloro-2-ethylsulfanylethane Chemical compound CCSCCCl GBNVXYXIRHSYEG-UHFFFAOYSA-N 0.000 description 2
- LNRIEBFNWGMXKP-UHFFFAOYSA-N 2-ethylsulfanylethanol Chemical compound CCSCCO LNRIEBFNWGMXKP-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 230000002140 halogenating effect Effects 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- -1 (2-ethylmercapto) -1-methyl-ethyl Chemical group 0.000 description 1
- NUTVORGGYDQIDD-UHFFFAOYSA-N 1-ethylsulfanylethanol Chemical compound CCSC(C)O NUTVORGGYDQIDD-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- WWJJVKAEQGGYHJ-UHFFFAOYSA-M Dimethylthiophosphate Chemical compound COP([O-])(=S)OC WWJJVKAEQGGYHJ-UHFFFAOYSA-M 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000002051 biphasic effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- 238000004065 wastewater treatment 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
- C07F9/06—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
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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792941587 DE2941587A1 (de) | 1979-10-13 | 1979-10-13 | Verfahren zur herstellung von thiophosporsaeureestern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD153553A5 true DD153553A5 (de) | 1982-01-13 |
Family
ID=6083456
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD80224433A DD153553A5 (de) | 1979-10-13 | 1980-10-09 | Verfahren zur herstellung von thiophosphorsaeureestern |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4416834A (da) |
| EP (1) | EP0027230B1 (da) |
| JP (1) | JPS5661394A (da) |
| BR (1) | BR8006533A (da) |
| DD (1) | DD153553A5 (da) |
| DE (2) | DE2941587A1 (da) |
| DK (1) | DK429580A (da) |
| HU (1) | HU184933B (da) |
| IL (1) | IL61247A (da) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7049456B2 (en) * | 2003-03-07 | 2006-05-23 | Bayer Cropscience Lp | Method for preparing O,O-dialkyl S-[2-(alkylthio)alkyl] phosphorodithioates |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE830509C (de) * | 1950-05-24 | 1952-02-04 | Bayer Ag | Verfahren zur Herstellung von neutralen Estern der Thiophosphorsaeure |
| GB748299A (en) * | 1952-08-01 | 1956-04-25 | Bayer Ag | Neutral esters of dithiophosphoric acid |
| US2873228A (en) * | 1956-07-16 | 1959-02-10 | Fmc Corp | Pesticidal phosphorus esters |
| NL105707C (da) * | 1958-06-04 | |||
| CH387620A (fr) * | 1960-07-08 | 1965-02-15 | Sandoz Sa | Procédé de préparation d'esters contenant du phosphore |
| DE1183495B (de) * | 1963-05-28 | 1964-12-17 | Bayer Ag | Verfahren zur Herstellung von Thiol- bzw. Thionothiolphosphor-(-phosphon-, -phosphin-)saeureestern |
| DE1768399C3 (de) * | 1968-05-09 | 1976-01-08 | Bayer Ag, 5090 Leverkusen | O-Alkyl-O-aryl-thiolphosphorsäureester, Verfahren zu deren Herstellung und diese Verbindungen enthaltende insektizide und akarizide Mittel |
| US3829535A (en) * | 1969-03-04 | 1974-08-13 | Exxon Research Engineering Co | Preparation of s-2-hydrocarbylthioalkyl esters of thiophosphorus acids |
| JPS5241332B1 (da) * | 1969-05-09 | 1977-10-18 | ||
| US3742097A (en) * | 1969-12-10 | 1973-06-26 | Exxon Research Engineering Co | Process for preparing diadducts of hydrocarbylthiophosphoric acids |
-
1979
- 1979-10-13 DE DE19792941587 patent/DE2941587A1/de not_active Withdrawn
-
1980
- 1980-09-12 HU HU802254A patent/HU184933B/hu unknown
- 1980-09-24 US US06/190,288 patent/US4416834A/en not_active Expired - Lifetime
- 1980-10-06 DE DE8080106040T patent/DE3062454D1/de not_active Expired
- 1980-10-06 EP EP80106040A patent/EP0027230B1/de not_active Expired
- 1980-10-09 JP JP14064180A patent/JPS5661394A/ja active Granted
- 1980-10-09 DD DD80224433A patent/DD153553A5/de unknown
- 1980-10-10 BR BR8006533A patent/BR8006533A/pt unknown
- 1980-10-10 DK DK429580A patent/DK429580A/da not_active Application Discontinuation
- 1980-10-10 IL IL61247A patent/IL61247A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0027230B1 (de) | 1983-03-23 |
| DK429580A (da) | 1981-04-14 |
| DE3062454D1 (en) | 1983-04-28 |
| JPS648635B2 (da) | 1989-02-14 |
| US4416834A (en) | 1983-11-22 |
| BR8006533A (pt) | 1981-04-14 |
| IL61247A (en) | 1986-01-31 |
| HU184933B (en) | 1984-11-28 |
| DE2941587A1 (de) | 1981-05-07 |
| EP0027230A1 (de) | 1981-04-22 |
| IL61247A0 (en) | 1980-12-31 |
| JPS5661394A (en) | 1981-05-26 |
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