IL33775A - Method of producing thiono-or dithio-phosphonic acid esters - Google Patents

Method of producing thiono-or dithio-phosphonic acid esters

Info

Publication number: IL33775A
Authority: IL; Israel
Prior art keywords: reaction; reactor; phosphonic acid; dithio; thiono
Prior art date: 1969-01-27

Application number

IL33775A

Other languages

English (en)

Other versions

IL33775A0 (en

Original Assignee

Stauffer Chemical Co

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.)

1969-01-27

Filing date

1970-01-26

Publication date

1973-06-29

1970-01-26 Application filed by Stauffer Chemical Co filed Critical Stauffer Chemical Co

1970-03-22 Publication of IL33775A0 publication Critical patent/IL33775A0/xx

1973-06-29 Publication of IL33775A publication Critical patent/IL33775A/en

Links

238000000034 method Methods 0.000 title claims description 16
FLQUDUCNBDGCRI-UHFFFAOYSA-N hydroxy-sulfanyl-sulfidophosphanium Chemical class SP(S)=O FLQUDUCNBDGCRI-UHFFFAOYSA-N 0.000 title description 6
MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 claims description 7
229910000388 diammonium phosphate Inorganic materials 0.000 claims description 5
235000019838 diammonium phosphate Nutrition 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
239000011593 sulfur Substances 0.000 claims description 4
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 claims description 2
150000001875 compounds Chemical class 0.000 claims 1
238000006243 chemical reaction Methods 0.000 description 32
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 21
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
238000009833 condensation Methods 0.000 description 10
230000005494 condensation Effects 0.000 description 10
AATNZNJRDOVKDD-UHFFFAOYSA-N 1-[ethoxy(ethyl)phosphoryl]oxyethane Chemical compound CCOP(=O)(CC)OCC AATNZNJRDOVKDD-UHFFFAOYSA-N 0.000 description 8
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 8
239000012071 phase Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
-1 alkali metal salt Chemical class 0.000 description 6
150000002148 esters Chemical class 0.000 description 5
239000007789 gas Substances 0.000 description 5
238000006317 isomerization reaction Methods 0.000 description 5
239000007788 liquid Substances 0.000 description 5
150000003008 phosphonic acid esters Chemical class 0.000 description 5
238000007280 thionation reaction Methods 0.000 description 5
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
229910052783 alkali metal Inorganic materials 0.000 description 4
125000005600 alkyl phosphonate group Chemical group 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
229910052740 iodine Inorganic materials 0.000 description 4
239000011630 iodine Substances 0.000 description 4
239000000463 material Substances 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 4
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
229910052786 argon Inorganic materials 0.000 description 3
239000003518 caustics Substances 0.000 description 3
239000011521 glass Substances 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000002904 solvent Substances 0.000 description 3
229910000619 316 stainless steel Inorganic materials 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
239000002253 acid Substances 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
238000013019 agitation Methods 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
238000006482 condensation reaction Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
230000000269 nucleophilic effect Effects 0.000 description 2
230000000361 pesticidal effect Effects 0.000 description 2
239000000376 reactant Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
LKYIPGJOXSVWPX-UHFFFAOYSA-M sodium;thiophene-2-carboxylate Chemical compound [Na+].[O-]C(=O)C1=CC=CS1 LKYIPGJOXSVWPX-UHFFFAOYSA-M 0.000 description 2
OSUKSSHOHKZSJC-UHFFFAOYSA-N 12591-02-5 Chemical compound ClP(=O)=O OSUKSSHOHKZSJC-UHFFFAOYSA-N 0.000 description 1
150000001340 alkali metals Chemical group 0.000 description 1
150000001348 alkyl chlorides Chemical class 0.000 description 1
150000001351 alkyl iodides Chemical class 0.000 description 1
230000004075 alteration Effects 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000012300 argon atmosphere Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
230000001276 controlling effect Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000007857 degradation product Substances 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
230000001627 detrimental effect Effects 0.000 description 1
HGELWZQRZUOEOJ-UHFFFAOYSA-N ethyl-dihydroxy-sulfanylidene-$l^{5}-phosphane Chemical compound CCP(O)(O)=S HGELWZQRZUOEOJ-UHFFFAOYSA-N 0.000 description 1
KVGLBTYUCJYMND-UHFFFAOYSA-N fonofos Chemical compound CCOP(=S)(CC)SC1=CC=CC=C1 KVGLBTYUCJYMND-UHFFFAOYSA-N 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000013505 freshwater Substances 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000008188 pellet Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
238000005406 washing 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

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)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

IL33775A 1969-01-27 1970-01-26 Method of producing thiono-or dithio-phosphonic acid esters IL33775A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US79438769A	1969-01-27	1969-01-27

Publications (2)

Publication Number	Publication Date
IL33775A0 IL33775A0 (en)	1970-03-22
IL33775A true IL33775A (en)	1973-06-29

Family

ID=25162503

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL33775A IL33775A (en)	1969-01-27	1970-01-26	Method of producing thiono-or dithio-phosphonic acid esters

Country Status (11)

Country	Link
US (1)	US3642960A (fr)
JP (1)	JPS5220474B1 (fr)
BE (1)	BE744917A (fr)
BR (1)	BR7016285D0 (fr)
CH (1)	CH531542A (fr)
DE (1)	DE2002629C3 (fr)
DK (1)	DK136265B (fr)
FR (1)	FR2029472A1 (fr)
GB (1)	GB1303841A (fr)
IL (1)	IL33775A (fr)
NL (1)	NL162392C (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3862276A (en) *	1971-07-03	1975-01-21	Bayer Ag	Preparation of 0-(2,2-dichlorovinyl)-thionophosphoric acid ester dichloride
US4268508A (en) *	1979-12-28	1981-05-19	Mobil Oil Corporation	0-Alkyl-s-branched alkyl-alkylphosphonodithioate
US4284626A (en) *	1979-12-31	1981-08-18	Mobil Oil Corporation	O-aryl S-branched alkyl alkylphosphonodithioate insecticides and nematocides
US4948787A (en) *	1989-01-04	1990-08-14	Imperial Chemical Industries Plc	Inhibition of mercaptan odor in organothiophosphate biocides
US5295690A (en) *	1992-07-30	1994-03-22	John Johnson	Apparatus and method for improving a golf swing
US7300906B2 (en) *	2005-04-07	2007-11-27	Gowan Company, L.L.C.	Control of sulfhydryl compound odor in organothiophosphate formulations

1969
- 1969-01-27 US US794387*A patent/US3642960A/en not_active Expired - Lifetime
1970
- 1970-01-15 GB GB202470A patent/GB1303841A/en not_active Expired
- 1970-01-22 DE DE2002629A patent/DE2002629C3/de not_active Expired
- 1970-01-24 JP JP45006041A patent/JPS5220474B1/ja active Pending
- 1970-01-26 BE BE744917D patent/BE744917A/fr not_active IP Right Cessation
- 1970-01-26 CH CH105970A patent/CH531542A/de not_active IP Right Cessation
- 1970-01-26 FR FR7002691A patent/FR2029472A1/fr not_active Withdrawn
- 1970-01-26 IL IL33775A patent/IL33775A/en unknown
- 1970-01-27 DK DK36870AA patent/DK136265B/da not_active IP Right Cessation
- 1970-01-27 NL NL7001117.A patent/NL162392C/xx not_active IP Right Cessation
- 1970-01-28 BR BR21628570A patent/BR7016285D0/pt unknown

Also Published As

Publication number	Publication date
DK136265B (da)	1977-09-19
NL7001117A (fr)	1970-07-29
CH531542A (de)	1972-12-15
BE744917A (fr)	1970-07-27
DK136265C (fr)	1978-02-20
DE2002629B2 (de)	1980-05-08
NL162392C (nl)	1980-05-16
IL33775A0 (en)	1970-03-22
GB1303841A (fr)	1973-01-24
FR2029472A1 (fr)	1970-10-23
DE2002629C3 (de)	1981-01-22
JPS5220474B1 (fr)	1977-06-03
NL162392B (nl)	1979-12-17
BR7016285D0 (pt)	1973-01-25
US3642960A (en)	1972-02-15
DE2002629A1 (de)	1970-07-30

Publication	Publication Date	Title
US3502750A (en)	1970-03-24	Process for the preparation of dialkyl phosphorochloridothioates
IL33775A (en)	1973-06-29	Method of producing thiono-or dithio-phosphonic acid esters
Maier	1990	Organic Phosphorus Compounds 90. l A Convenient, One-Step Synthesis of Alkyl-and Arylphosphonyl Dichlorides
Capson et al.	1988	Synthesis of ammonium analogs of carbocationic intermediates in the conversion of presqualene diphosphate to squalene
US4371509A (en)	1983-02-01	Oxidizing phosphorus compounds with chlorosulfonic acid
US4521347A (en)	1985-06-04	Process for preparing chlorophenylphosphanes
EP0010799B1 (fr)	1982-05-19	Procédé de préparation de dérivés d'aza-3 bicyclo(3.1.0)hexane et leurs modifications
US5177238A (en)	1993-01-05	Preparation of dialkyl allylphosphonic acid diesters
US4470933A (en)	1984-09-11	Preparation of S-brom-dithiophosphoric, dithiophosphonic and dithiophosphinic acid derivatives
EP0044558B1 (fr)	1984-05-02	Procédé pour la préparation de composés d'alcynes
EP0227918B1 (fr)	1988-12-14	Procédé de préparation de dichlorures d'acides phosphoniques
US4633005A (en)	1986-12-30	Method for the preparation of allyl phosphonate diesters
US4096182A (en)	1978-06-20	Process for the simultaneous preparation of 2,5-dioxo-1,2-oxa-phospholanes and β-halogenpropionic acid halide
US4368162A (en)	1983-01-11	Process for producing aminomethylphosphonic acid
US4740608A (en)	1988-04-26	(Phosphonomethyl)trifluoromethyl sulfonates
CA1067910A (fr)	1979-12-11	Production de s-aklylphosphorodihalogenidodithioate
EP0130439B1 (fr)	1987-04-15	Procédé de préparation de dérivés de l'acide vinylphosphonique ou vinylpyrophosphonique
JP2645101B2 (ja)	1997-08-25	アリファチルホスフィン酸誘導体の製造方法
US4855087A (en)	1989-08-08	Process for the preparation of 2-chloroethanephosphonyl dichloride
US2495799A (en)	1950-01-31	Chloroalkyl phosphorous oxy and sulfodichlorides
CA2134633A1 (fr)	1995-05-01	Procede de preparation des anhydrides alcanephosphoniques
RU1828862C (ru)	1993-07-23	Способ получени цианалкиловых эфиров фосфорной кислоты
US3770853A (en)	1973-11-06	Marshall dann
US4020129A (en)	1977-04-26	Production of dithiophosphoric acid-O,O-diesters
US2887506A (en)	1959-05-19	Method for the manufacture of o-aryl o-lower alkyl phosphorochloridothioates