CH377816A - Verfahren zur Herstellung von Phosphonsäureestern - Google Patents
Verfahren zur Herstellung von PhosphonsäureesternInfo
- Publication number
- CH377816A CH377816A CH6042958A CH6042958A CH377816A CH 377816 A CH377816 A CH 377816A CH 6042958 A CH6042958 A CH 6042958A CH 6042958 A CH6042958 A CH 6042958A CH 377816 A CH377816 A CH 377816A
- Authority
- CH
- Switzerland
- Prior art keywords
- water
- added
- ester
- hours
- dissolved
- Prior art date
Links
- 150000003008 phosphonic acid esters Chemical class 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000002253 acid Substances 0.000 claims description 10
- -1 ester chlorides Chemical class 0.000 claims description 9
- 150000001348 alkyl chlorides Chemical class 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- QLZHNIAADXEJJP-UHFFFAOYSA-N Phenylphosphonic acid Chemical compound OP(O)(=O)C1=CC=CC=C1 QLZHNIAADXEJJP-UHFFFAOYSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 239000000575 pesticide Substances 0.000 claims 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
- 150000002148 esters Chemical class 0.000 description 27
- 238000003756 stirring Methods 0.000 description 22
- 239000000243 solution Substances 0.000 description 21
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- 239000003921 oil Substances 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000007795 chemical reaction product Substances 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- SHHNZMWZZCIDHE-UHFFFAOYSA-N ethoxy-hydroxy-phenyl-sulfanylidene-lambda5-phosphane hydrochloride Chemical compound Cl.CCOP(O)(=S)C1=CC=CC=C1 SHHNZMWZZCIDHE-UHFFFAOYSA-N 0.000 description 13
- 238000009835 boiling Methods 0.000 description 12
- 241000700159 Rattus Species 0.000 description 7
- 230000001988 toxicity Effects 0.000 description 7
- 231100000419 toxicity Toxicity 0.000 description 7
- SELLGGZNVHTHDU-UHFFFAOYSA-N COP(C1=CC=CC=C1)(O)=S.Cl Chemical compound COP(C1=CC=CC=C1)(O)=S.Cl SELLGGZNVHTHDU-UHFFFAOYSA-N 0.000 description 5
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 5
- 238000010626 work up procedure Methods 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
- 229940073608 benzyl chloride Drugs 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- HBFNIDYFNYYMOB-UHFFFAOYSA-N ethoxy-hydroxy-phenyl-sulfanylidene-$l^{5}-phosphane Chemical compound CCOP(O)(=S)C1=CC=CC=C1 HBFNIDYFNYYMOB-UHFFFAOYSA-N 0.000 description 2
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- YZIFVWOCPGPNHB-UHFFFAOYSA-N 1,2-dichloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C(Cl)=C1 YZIFVWOCPGPNHB-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
- XPJUCMIJGVAEGF-UHFFFAOYSA-N 1-chloro-4-(chloromethylsulfanyl)benzene Chemical compound ClCSC1=CC=C(Cl)C=C1 XPJUCMIJGVAEGF-UHFFFAOYSA-N 0.000 description 1
- GCDPERPXPREHJF-UHFFFAOYSA-N 1-iodododecane Chemical compound CCCCCCCCCCCCI GCDPERPXPREHJF-UHFFFAOYSA-N 0.000 description 1
- MQGPCVJRNARRNC-UHFFFAOYSA-N 2-(chloromethoxy)thiophene Chemical compound ClCOC1=CC=CS1 MQGPCVJRNARRNC-UHFFFAOYSA-N 0.000 description 1
- YMDNODNLFSHHCV-UHFFFAOYSA-N 2-chloro-n,n-diethylethanamine Chemical compound CCN(CC)CCCl YMDNODNLFSHHCV-UHFFFAOYSA-N 0.000 description 1
- 241001556567 Acanthamoeba polyphaga mimivirus Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical group CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- ARFLASKVLJTEJD-UHFFFAOYSA-N ethyl 2-bromopropanoate Chemical compound CCOC(=O)C(C)Br ARFLASKVLJTEJD-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000007787 solid 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
- C07F9/28—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
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0023318 | 1957-06-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH377816A true CH377816A (de) | 1964-05-31 |
Family
ID=7090793
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH6042958A CH377816A (de) | 1957-06-24 | 1958-06-10 | Verfahren zur Herstellung von Phosphonsäureestern |
Country Status (2)
| Country | Link |
|---|---|
| BE (1) | BE568844A (zh) |
| CH (1) | CH377816A (zh) |
-
0
- BE BE568844D patent/BE568844A/xx unknown
-
1958
- 1958-06-10 CH CH6042958A patent/CH377816A/de unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE568844A (zh) |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH426776A (de) | Verfahren zur Herstellung von O,O-Dialkyl-S-alkylthiolphosphaten | |
| CH377816A (de) | Verfahren zur Herstellung von Phosphonsäureestern | |
| DE963872C (de) | Verfahren zur Herstellung von Thiophosphorsaeureestern | |
| DE1138048B (de) | Verfahren zur Herstellung von (Thiono)Phosphon- bzw. (Thiono)Phosphinsaeureestern der ª- und ª-Naphthole | |
| AT208360B (de) | Verfahren zur Herstellung von neuen Thionophosphonsäureestern | |
| AT210438B (de) | Verfahren zur Herstellung von neuen Phosphon- bzw. Thiophosphonsäureestern | |
| AT214940B (de) | Verfahren zur Herstellung von neuen Thiophosphor-, Thiophosphon- bzw. Thiophosphinsäureestern | |
| AT220158B (de) | Verfahren zur Herstellung neuer Thiophosphor-, Thiophosphon- oder Thiophosphinsäureester | |
| CH303086A (de) | Verfahren zur Herstellung eines Cumarinderivates. | |
| DE1026323B (de) | Verfahren zur Herstellung von insekticid wirksamen O, O-Dialkyl-S-phenyl-thionothiolphosphorsaeureestern | |
| AT226252B (de) | Verfahren zur Herstellung neuer Thionothiol-phosphor-, -phosphon- oder -phosphinsäureester | |
| AT268233B (de) | Verfahren zur Herstellung neuer Cyclopropancarbonsäureester | |
| AT230901B (de) | Verfahren zur Herstellung von neuen Thionothiolphosphonsäureestern | |
| AT137670B (de) | Verfahren zur Darstellung organischer Quecksilberbindungen. | |
| AT226254B (de) | Verfahren zur Herstellung von neuen Thionothiolphosphorsäureestern | |
| AT271095B (de) | Schädlingsbekämpfungsmittel | |
| AT218537B (de) | Verfahren zur Herstellung von neuen Phosphonsäureestern | |
| DE1014105B (de) | Verfahren zur Herstellung von O,O-Dialkyl-thiophosphorsaeuretriestern | |
| DE837700C (de) | Verfahren zur Herstellung von Furanderivaten | |
| AT225718B (de) | Verfahren zur Herstellung von neuen Dithiophosphonsäure-O-aminoalkyl-S-äthylestern | |
| DE1058055B (de) | Verfahren zur Herstellung von Phenylthionophosphonsaeureestern | |
| CH361566A (de) | Verfahren zur Herstellung von Thiol- und Thionothiolphosphorsäureestern | |
| DE1146883B (de) | Verfahren zur Herstellung von Dithiophosphinsaeureestern | |
| CH298403A (de) | Verfahren zur Herstellung eines phosphorhaltigen Abkömmlings von m-Amino-phenolen. | |
| CH269082A (de) | Verfahren zur Herstellung eines Diaryl-butenyl-amins. |