CH398559A - Verfahren zur Herstellung von Phosphonsäureestern und Thionophosphonsäureester - Google Patents

Verfahren zur Herstellung von Phosphonsäureestern und Thionophosphonsäureester

Info

Publication number: CH398559A
Authority: CH; Switzerland
Prior art keywords: sep; mol; acid esters; thionophosphonic; methane
Prior art date: 1959-12-04

Application number

CH1310160A

Other languages

German (de)

English (en)

Inventor

Reimer Dr Coelln

Schrader Gerhard Dr Dr H C

Original Assignee

Bayer Ag

Priority date (The priority date 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 date listed.)

1959-12-04

Filing date

1960-11-22

Publication date

1966-03-15

1960-11-22 Application filed by Bayer Ag filed Critical Bayer Ag

1966-03-15 Publication of CH398559A publication Critical patent/CH398559A/de

Links

239000002253 acid Substances 0.000 title claims description 24
238000000034 method Methods 0.000 title claims description 17
150000002148 esters Chemical class 0.000 title claims description 15
150000003008 phosphonic acid esters Chemical class 0.000 title claims description 5
238000002360 preparation method Methods 0.000 title description 3
241000607479 Yersinia pestis Species 0.000 claims 1
239000003795 chemical substances by application Substances 0.000 claims 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 63
238000003756 stirring Methods 0.000 description 19
-1 ester halides Chemical class 0.000 description 16
235000019256 formaldehyde Nutrition 0.000 description 12
125000000217 alkyl group Chemical group 0.000 description 11
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
229910052698 phosphorus Inorganic materials 0.000 description 10
239000011734 sodium Substances 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 9
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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 9
229910052708 sodium Inorganic materials 0.000 description 9
239000007795 chemical reaction product Substances 0.000 description 8
239000000203 mixture Substances 0.000 description 8
BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 7
239000002904 solvent Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
241000700159 Rattus Species 0.000 description 6
238000009835 boiling Methods 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
241001454295 Tetranychidae Species 0.000 description 5
150000001875 compounds Chemical class 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
239000007788 liquid Substances 0.000 description 5
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
231100000419 toxicity Toxicity 0.000 description 4
230000001988 toxicity Effects 0.000 description 4
241001124076 Aphididae Species 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
238000001816 cooling Methods 0.000 description 3
230000000749 insecticidal effect Effects 0.000 description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
PMCCSSODVYHTNA-UHFFFAOYSA-N 1-sulfanylpropylphosphonic acid Chemical compound CCC(S)P(O)(O)=O PMCCSSODVYHTNA-UHFFFAOYSA-N 0.000 description 2
VKALYYFVKBXHTF-UHFFFAOYSA-N 4-(methylsulfanyl)-m-cresol Chemical compound CSC1=CC=C(O)C=C1C VKALYYFVKBXHTF-UHFFFAOYSA-N 0.000 description 2
QASBCTGZKABPKX-UHFFFAOYSA-N 4-(methylsulfanyl)phenol Chemical compound CSC1=CC=C(O)C=C1 QASBCTGZKABPKX-UHFFFAOYSA-N 0.000 description 2
VZXOZSQDJJNBRC-UHFFFAOYSA-N 4-chlorobenzenethiol Chemical compound SC1=CC=C(Cl)C=C1 VZXOZSQDJJNBRC-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
HXQIIKJFEAVWLU-UHFFFAOYSA-N CCC(P(Cl)(Cl)=O)S Chemical compound CCC(P(Cl)(Cl)=O)S HXQIIKJFEAVWLU-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
238000007014 Michaelis-Becker reaction Methods 0.000 description 2
206010058667 Oral toxicity Diseases 0.000 description 2
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 2
125000004414 alkyl thio group Chemical group 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000005457 ice water Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
231100000418 oral toxicity Toxicity 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
ZIVHDUSDPIPJLN-UHFFFAOYSA-N 1-(dichlorophosphorylmethylsulfanyl)ethane Chemical compound CCSCP(Cl)(Cl)=O ZIVHDUSDPIPJLN-UHFFFAOYSA-N 0.000 description 1
FTTKKJQNGIJGOC-UHFFFAOYSA-N 1-[ethoxy(ethylsulfanylmethyl)phosphoryl]oxyethane Chemical compound CCOP(=O)(OCC)CSCC FTTKKJQNGIJGOC-UHFFFAOYSA-N 0.000 description 1
LHJGJYXLEPZJPM-UHFFFAOYSA-N 2,4,5-trichlorophenol Chemical compound OC1=CC(Cl)=C(Cl)C=C1Cl LHJGJYXLEPZJPM-UHFFFAOYSA-N 0.000 description 1
HFZWRUODUSTPEG-UHFFFAOYSA-N 2,4-dichlorophenol Chemical compound OC1=CC=C(Cl)C=C1Cl HFZWRUODUSTPEG-UHFFFAOYSA-N 0.000 description 1
GMLJPYJTJXEGAE-UHFFFAOYSA-N 3-methyl-4-sulfanylphenol Chemical compound CC1=CC(O)=CC=C1S GMLJPYJTJXEGAE-UHFFFAOYSA-N 0.000 description 1
JKYJNJJOOAKMLB-UHFFFAOYSA-N 4-chlorobenzenethiol;sodium Chemical compound [Na].SC1=CC=C(Cl)C=C1 JKYJNJJOOAKMLB-UHFFFAOYSA-N 0.000 description 1
WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001348 alkyl chlorides Chemical class 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
239000012320 chlorinating reagent Substances 0.000 description 1
GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
230000001771 impaired effect Effects 0.000 description 1
238000002955 isolation Methods 0.000 description 1
YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical class CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 description 1
239000012071 phase Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
238000005292 vacuum distillation 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
- C07F9/28—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
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have 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)

CH1310160A 1959-12-04 1960-11-22 Verfahren zur Herstellung von Phosphonsäureestern und Thionophosphonsäureester CH398559A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DEF30002A DE1142865B (de)	1959-12-04	1959-12-04	Verfahren zur Herstellung von Phosphonsaeureestern

Publications (1)

Publication Number	Publication Date
CH398559A true CH398559A (de)	1966-03-15

Family

ID=7093557

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1310160A CH398559A (de)	1959-12-04	1960-11-22	Verfahren zur Herstellung von Phosphonsäureestern und Thionophosphonsäureester

Country Status (4)

Country	Link
BE (1)	BE597767A (fr)
BR (1)	BR6024672D0 (fr)
CH (1)	CH398559A (fr)
DE (1)	DE1142865B (fr)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE948241C (de) *	1954-09-04	1956-08-30	Bayer Ag	Verfahren zur Herstellung von sulfongruppenhaltigen Estern der Saeuren des Phosphors

1959
- 1959-12-04 DE DEF30002A patent/DE1142865B/de active Pending
1960
- 1960-11-22 CH CH1310160A patent/CH398559A/de unknown
- 1960-12-02 BR BR12467260A patent/BR6024672D0/pt unknown
- 1960-12-02 BE BE597767A patent/BE597767A/fr unknown

Also Published As

Publication number	Publication date
DE1142865B (de)	1963-01-31
BE597767A (fr)	1961-06-02
BR6024672D0 (pt)	1973-05-17

Publication	Publication Date	Title
DE1032247B (de)	1958-06-19	Verfahren zur Herstellung von organischen Phosphorverbindungen
DE1077215B (de)	1960-03-10	Verfahren zur Herstellung von amido-O-alkyl-S-substituierten Phosphorsaeureestern
CH389605A (de)	1965-03-31	Verfahren zur Herstellung neuer Phosphinsäurederivate und deren Verwendung
DE1078124B (de)	1960-03-24	Verfahren zur Herstellung von Thionophosphonsaeureestern
DE1047776B (de)	1958-12-31	Verfahren zur Herstellung von Thionophosphorsaeureestern
DE1089376B (de)	1960-09-22	Verfahren zur Herstellung von Thiophosphorsaeureestern bzw. Thiophosphonsaeureestern
CH398559A (de)	1966-03-15	Verfahren zur Herstellung von Phosphonsäureestern und Thionophosphonsäureester
DE921870C (de)	1954-12-30	Verfahren zur Herstellung von 0, 0-Dimethyl-0-4-nitro-3-chlorphenyl-thiophosphat
DE1099533B (de)	1961-02-16	Verfahren zur Herstellung von Dithio- oder Thiolphosphor-, -phosphon- oder -phosphinsaeureestern
DE1024509B (de)	1958-02-20	Verfahren zur Herstellung von O, O-Dialkyl-thiol-phosphorsaeure- und -thiol-thiono-phsphorsaeureestern
DE961083C (de)	1957-04-04	Verfahren zur Herstellung von S-ª‰-Merkapto-aethyl-O, O-dialkyl-thiol-phosphorsaeureestern
US3299188A (en)	1967-01-17	Phosphoric, phosphonic, phosphinic or thionophosphoric, -phosphonic, -phosphinic acid esters
US3320261A (en)	1967-05-16	Pyridyl and quinolyl mercapto methyl phosphorus esters
DE1062239B (de)	1959-07-30	Verfahren zur Herstellung von Thiophosphorsaeureestern
AT214940B (de)	1961-05-10	Verfahren zur Herstellung von neuen Thiophosphor-, Thiophosphon- bzw. Thiophosphinsäureestern
AT229326B (de)	1963-09-10	Verfahren zur Herstellung von Thiophosphonsäureestern
DE1518060C (de)	1973-03-15	0.0-Dialkyl-S- eckige Klammer auf 2-(acetamido)-äthyl eckige Klammer zu -dithiophosphate und Verfahren zur Herstellung dieser Verbindungen
AT221871B (de)	1962-06-25	Ungeziefervertilgungsmittel
DE1026323B (de)	1958-03-20	Verfahren zur Herstellung von insekticid wirksamen O, O-Dialkyl-S-phenyl-thionothiolphosphorsaeureestern
DE3425701A1 (de)	1986-01-16	Verfahren zur herstellung von chlorierten phosphorylmethylcarbonyl-derivaten und neue zwischenprodukte zu ihrer herstellung
AT200157B (de)	1958-10-25	Verfahren zur Herstellung von neuen Thiophosphorsäureestern
CH428704A (de)	1967-01-31	Verfahren zur Herstellung von 0,0-Dialkyl-0-dichlorvinylphosphaten
AT230394B (de)	1963-12-10	Verfahren zur Herstellung neuer Organophosphorverbindungen
AT228803B (de)	1963-08-12	Verfahren zur Herstellung von organischen Phosphorverbindungen
DE1051851B (de)	1959-03-05	Verfahren zur Herstellung von ª‰-Alkoxyvinyldithiophosphonsaeureestern