DE1153746B - Verfahren zur Herstellung von Thiophosphor-(-phosphon, -phosphin)- bzw. Dithiophosphor-(-phosphon, -phosphin)-saeureestern - Google Patents
Verfahren zur Herstellung von Thiophosphor-(-phosphon, -phosphin)- bzw. Dithiophosphor-(-phosphon, -phosphin)-saeureesternInfo
- Publication number
- DE1153746B DE1153746B DEF34866A DEF0034866A DE1153746B DE 1153746 B DE1153746 B DE 1153746B DE F34866 A DEF34866 A DE F34866A DE F0034866 A DEF0034866 A DE F0034866A DE 1153746 B DE1153746 B DE 1153746B
- Authority
- DE
- Germany
- Prior art keywords
- phosphine
- acid
- phosphon
- acid esters
- phosphonic
- 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.)
- Granted
Links
- 150000002148 esters Chemical class 0.000 title claims description 26
- 239000002253 acid Substances 0.000 title claims description 24
- 238000000034 method Methods 0.000 title claims description 7
- 229910000073 phosphorus hydride Inorganic materials 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 3
- -1 alkyl radical Chemical class 0.000 claims description 8
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000005109 alkynylthio group Chemical group 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 239000011574 phosphorus Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 2
- 241000251730 Chondrichthyes Species 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 40
- 239000000460 chlorine Substances 0.000 description 31
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 241001124076 Aphididae Species 0.000 description 5
- 241001454295 Tetranychidae Species 0.000 description 5
- 230000000749 insecticidal effect Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- UHMZHYUCMREDRI-UHFFFAOYSA-N ethyl thiohypochlorite Chemical compound CCSCl UHMZHYUCMREDRI-UHFFFAOYSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
- HFVYUQVSWQURMK-UHFFFAOYSA-N (3-ethyl-1-sulfanylidenethiophen-2-yl)phosphonic acid Chemical compound C(C)C1=C(S(C=C1)=S)P(O)(=O)O HFVYUQVSWQURMK-UHFFFAOYSA-N 0.000 description 2
- 241000273311 Aphis spiraecola Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000131102 Oryzaephilus Species 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- AXEAPLILIDYLCJ-UHFFFAOYSA-N C1(=CC=CC=C1)C1=C(S(C=C1)=S)P(O)(=O)O Chemical compound C1(=CC=CC=C1)C1=C(S(C=C1)=S)P(O)(=O)O AXEAPLILIDYLCJ-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000256113 Culicidae Species 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- 241000258916 Leptinotarsa decemlineata Species 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical class OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- DDCYYCUMAFYDDU-UHFFFAOYSA-N methyl thiohypochlorite Chemical compound CSCl DDCYYCUMAFYDDU-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009885 systemic effect Effects 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4075—Esters with hydroxyalkyl compounds
-
- 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
- A01N57/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having alternatively specified atoms bound to the phosphorus atom and not covered by a single one of groups A01N57/10, A01N57/18, A01N57/26, A01N57/34
-
- 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
- C07F9/173—Esters of thiophosphoric acids with unsaturated acyclic alcohols
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/32—Esters thereof
- C07F9/3258—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/3264—Esters with hydroxyalkyl compounds
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/32—Esters thereof
- C07F9/3258—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/327—Esters with unsaturated acyclic alcohols
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4078—Esters with unsaturated acyclic alcohols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (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)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE622125D BE622125A (en, 2012) | 1961-09-06 | ||
| NL282904D NL282904A (en, 2012) | 1961-09-06 | ||
| DEF34866A DE1153746B (de) | 1961-09-06 | 1961-09-06 | Verfahren zur Herstellung von Thiophosphor-(-phosphon, -phosphin)- bzw. Dithiophosphor-(-phosphon, -phosphin)-saeureestern |
| CH973362A CH420122A (de) | 1961-09-06 | 1962-08-14 | Verfahren zur Herstellung von Thiophosphor-(-phosphon-, -phosphin)- bzw. Dithiophosphor-(-phosphon-, -phosphin)-säureestern |
| US218506A US3153664A (en) | 1961-09-06 | 1962-08-22 | S-(3-alkylmercapto 2-halo propyl) and s-(3-alkylmercapto 2-halo propenyl) esters of pentavalent phosphorus acids |
| FR908095A FR1339003A (fr) | 1961-09-06 | 1962-08-29 | Esters thio- ou dithiophosphoriques, -phosphoniques ou -phosphiniques et leur procédé de préparation |
| GB33831/62A GB957827A (en) | 1961-09-06 | 1962-09-04 | New phosphorus-containing esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF34866A DE1153746B (de) | 1961-09-06 | 1961-09-06 | Verfahren zur Herstellung von Thiophosphor-(-phosphon, -phosphin)- bzw. Dithiophosphor-(-phosphon, -phosphin)-saeureestern |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1153746B true DE1153746B (de) | 1963-09-05 |
| DE1153746C2 DE1153746C2 (en, 2012) | 1964-03-26 |
Family
ID=7095751
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF34866A Granted DE1153746B (de) | 1961-09-06 | 1961-09-06 | Verfahren zur Herstellung von Thiophosphor-(-phosphon, -phosphin)- bzw. Dithiophosphor-(-phosphon, -phosphin)-saeureestern |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3153664A (en, 2012) |
| BE (1) | BE622125A (en, 2012) |
| CH (1) | CH420122A (en, 2012) |
| DE (1) | DE1153746B (en, 2012) |
| FR (1) | FR1339003A (en, 2012) |
| GB (1) | GB957827A (en, 2012) |
| NL (1) | NL282904A (en, 2012) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3340332A (en) * | 1963-09-30 | 1967-09-05 | Exxon Research Engineering Co | Dialkyldithiophosphoric acid esters |
| US3483278A (en) * | 1966-01-25 | 1969-12-09 | Exxon Research Engineering Co | Monoadducts of alkylthiophosphoric acids and process for preparing same |
| US4299783A (en) * | 1980-04-28 | 1981-11-10 | Chevron Research Company | 1-Alkylsulfonyl-3-substituted phosphinylthio- or phosphinothioylthio-propenes |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1032247B (de) * | 1954-12-04 | 1958-06-19 | Bayer Ag | Verfahren zur Herstellung von organischen Phosphorverbindungen |
| US2870209A (en) * | 1957-02-21 | 1959-01-20 | Monsanto Chemicals | Ketone products |
| DE1099525B (de) * | 1959-08-21 | 1961-02-16 | Bayer Ag | Verfahren zur Herstellung von Estern der Thiosaeuren des Phosphors |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE15647C (de) * | E. PONGS in Odenkirchen | Kugellager für Rauhmaschinen | ||
| DE16085C (de) * | B. SIMON in Plefs, Schlesien | Fleischhackmaschine | ||
| IT573971A (en, 2012) * | 1955-10-29 | |||
| BE552774A (en, 2012) * | 1955-11-22 |
-
0
- NL NL282904D patent/NL282904A/xx unknown
- BE BE622125D patent/BE622125A/xx unknown
-
1961
- 1961-09-06 DE DEF34866A patent/DE1153746B/de active Granted
-
1962
- 1962-08-14 CH CH973362A patent/CH420122A/de unknown
- 1962-08-22 US US218506A patent/US3153664A/en not_active Expired - Lifetime
- 1962-08-29 FR FR908095A patent/FR1339003A/fr not_active Expired
- 1962-09-04 GB GB33831/62A patent/GB957827A/en not_active Expired
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1032247B (de) * | 1954-12-04 | 1958-06-19 | Bayer Ag | Verfahren zur Herstellung von organischen Phosphorverbindungen |
| US2870209A (en) * | 1957-02-21 | 1959-01-20 | Monsanto Chemicals | Ketone products |
| DE1099525B (de) * | 1959-08-21 | 1961-02-16 | Bayer Ag | Verfahren zur Herstellung von Estern der Thiosaeuren des Phosphors |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1339003A (fr) | 1963-10-04 |
| NL282904A (en, 2012) | |
| DE1153746C2 (en, 2012) | 1964-03-26 |
| BE622125A (en, 2012) | |
| CH420122A (de) | 1966-09-15 |
| GB957827A (en) | 1964-05-13 |
| US3153664A (en) | 1964-10-20 |
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