CS208691B2 - Method of preparation of the alkyl-or arylphosphonothiodichlorides - Google Patents

Method of preparation of the alkyl-or arylphosphonothiodichlorides Download PDF

Info

Publication number: CS208691B2
Authority: CS; Czechoslovakia
Prior art keywords: product; autoclave; reaction; alkyl; hcl
Prior art date: 1972-02-18

Application number

CS731139A

Other languages

Czech (cs)

English (en)

Inventor

Eugene H Uhing

Arthur D Toy

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.)

1972-02-18

Filing date

1973-02-16

Publication date

1981-09-15

1973-02-16 Application filed by Stauffer Chemical Co filed Critical Stauffer Chemical Co

1981-09-15 Publication of CS208691B2 publication Critical patent/CS208691B2/cs

Links

238000000034 method Methods 0.000 title claims description 12
238000002360 preparation method Methods 0.000 title claims description 7
239000006227 byproduct Substances 0.000 claims abstract description 16
125000000217 alkyl group Chemical group 0.000 claims abstract description 13
-1 biphenylyl Chemical group 0.000 claims abstract description 9
125000003118 aryl group Chemical group 0.000 claims abstract description 7
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
238000006243 chemical reaction Methods 0.000 claims description 38
150000002430 hydrocarbons Chemical class 0.000 claims description 16
229910052698 phosphorus Inorganic materials 0.000 claims description 15
229930195733 hydrocarbon Natural products 0.000 claims description 12
239000004215 Carbon black (E152) Substances 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
239000011574 phosphorus Substances 0.000 claims description 6
125000001931 aliphatic group Chemical group 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 abstract description 11
239000000126 substance Substances 0.000 abstract description 8
239000000203 mixture Substances 0.000 abstract description 7
150000001875 compounds Chemical class 0.000 abstract description 6
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 4
239000007795 chemical reaction product Substances 0.000 abstract description 4
239000000376 reactant Substances 0.000 abstract description 4
125000003710 aryl alkyl group Chemical group 0.000 abstract description 3
239000002917 insecticide Substances 0.000 abstract description 3
238000004519 manufacturing process Methods 0.000 abstract description 3
238000011065 in-situ storage Methods 0.000 abstract description 2
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 abstract 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 abstract 1
NNPRGLSFQDCKSK-UHFFFAOYSA-N 1-chloro-3,3-dimethyl-1-sulfanylidene-1lambda5-phosphetane Chemical compound ClP1(CC(C1)(C)C)=S NNPRGLSFQDCKSK-UHFFFAOYSA-N 0.000 abstract 1
KKVDUJRKQVHKBU-UHFFFAOYSA-N [ethoxy(ethyl)phosphoryl]sulfanylbenzene Chemical compound CCOP(=O)(CC)SC1=CC=CC=C1 KKVDUJRKQVHKBU-UHFFFAOYSA-N 0.000 abstract 1
FRNHPBDNOSCJNW-UHFFFAOYSA-N dichloro-ethyl-sulfanylidene-$l^{5}-phosphane Chemical compound CCP(Cl)(Cl)=S FRNHPBDNOSCJNW-UHFFFAOYSA-N 0.000 abstract 1
150000004820 halides Chemical class 0.000 abstract 1
239000000460 chlorine Substances 0.000 description 37
239000000047 product Substances 0.000 description 29
239000007788 liquid Substances 0.000 description 16
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 11
239000007789 gas Substances 0.000 description 11
238000009835 boiling Methods 0.000 description 10
238000001816 cooling Methods 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000001257 hydrogen Substances 0.000 description 9
229910052739 hydrogen Inorganic materials 0.000 description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 description 9
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 9
238000001228 spectrum Methods 0.000 description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
238000004817 gas chromatography Methods 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
229910001220 stainless steel Inorganic materials 0.000 description 6
239000010935 stainless steel Substances 0.000 description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
239000003085 diluting agent Substances 0.000 description 5
238000004821 distillation Methods 0.000 description 5
229910000619 316 stainless steel Inorganic materials 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
CRSOQBOWXPBRES-UHFFFAOYSA-N neopentane Chemical compound CC(C)(C)C CRSOQBOWXPBRES-UHFFFAOYSA-N 0.000 description 4
230000035484 reaction time Effects 0.000 description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 3
239000001294 propane Substances 0.000 description 3
230000009257 reactivity Effects 0.000 description 3
229910052717 sulfur Inorganic materials 0.000 description 3
239000011593 sulfur Substances 0.000 description 3
WQYSXVGEZYESBR-UHFFFAOYSA-N thiophosphoryl chloride Chemical compound ClP(Cl)(Cl)=S WQYSXVGEZYESBR-UHFFFAOYSA-N 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000001273 butane Substances 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical group CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
239000007787 solid Substances 0.000 description 2
125000003944 tolyl group Chemical group 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
FDQGNLOWMMVRQL-UHFFFAOYSA-N Allobarbital Chemical compound C=CCC1(CC=C)C(=O)NC(=O)NC1=O FDQGNLOWMMVRQL-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
241000288906 Primates Species 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
230000000735 allogeneic effect Effects 0.000 description 1
230000033228 biological regulation Effects 0.000 description 1
USJRLGNYCQWLPF-UHFFFAOYSA-N chlorophosphane Chemical compound ClP USJRLGNYCQWLPF-UHFFFAOYSA-N 0.000 description 1
238000012790 confirmation Methods 0.000 description 1
239000013256 coordination polymer Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
150000001924 cycloalkanes Chemical class 0.000 description 1
230000007423 decrease Effects 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
239000003814 drug Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical class [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
150000002431 hydrogen Chemical group 0.000 description 1
229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
230000002427 irreversible effect Effects 0.000 description 1
239000001282 iso-butane Substances 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
150000002903 organophosphorus compounds Chemical class 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
239000002516 radical scavenger Substances 0.000 description 1
239000004576 sand Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000012265 solid product Substances 0.000 description 1
238000010183 spectrum analysis Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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)]
- C07F9/42—Halides thereof
- 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)]
- C07F9/34—Halides 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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CS731139A 1972-02-18 1973-02-16 Method of preparation of the alkyl-or arylphosphonothiodichlorides CS208691B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US22761672A	1972-02-18	1972-02-18

Publications (1)

Publication Number	Publication Date
CS208691B2 true CS208691B2 (en)	1981-09-15

Family

ID=22853790

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS731139A CS208691B2 (en)	1972-02-18	1973-02-16	Method of preparation of the alkyl-or arylphosphonothiodichlorides

Country Status (17)

Country	Link
US (1)	US3790629A (fr)
JP (1)	JPS5328415B2 (fr)
AR (1)	AR196655A1 (fr)
AU (1)	AU471617B2 (fr)
BE (1)	BE795532A (fr)
BR (1)	BR7301187D0 (fr)
CA (1)	CA1000734A (fr)
CH (1)	CH589098A5 (fr)
CS (1)	CS208691B2 (fr)
DE (1)	DE2306108C2 (fr)
FR (1)	FR2172223B1 (fr)
GB (1)	GB1362357A (fr)
IL (1)	IL41415A (fr)
IT (1)	IT977374B (fr)
NL (1)	NL7301722A (fr)
SU (1)	SU625615A3 (fr)
ZA (1)	ZA731104B (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5320974B2 (fr) *	1974-06-22	1978-06-29
US4133830A (en) *	1977-02-04	1979-01-09	Stauffer Chemical Company	Process for preparing alkyl or aryl thiophosphorus halides and mixed isomers thereof
USD946961S1 (en) *	2020-06-23	2022-03-29	Barebones Systems, Llc	Fire pit

1972
- 1972-02-18 US US00227616A patent/US3790629A/en not_active Expired - Lifetime
1973
- 1973-01-29 IL IL41415A patent/IL41415A/xx unknown
- 1973-01-30 AU AU51579/73A patent/AU471617B2/en not_active Expired
- 1973-01-31 CA CA162,545A patent/CA1000734A/en not_active Expired
- 1973-02-07 NL NL7301722A patent/NL7301722A/xx not_active Application Discontinuation
- 1973-02-07 GB GB602873A patent/GB1362357A/en not_active Expired
- 1973-02-08 DE DE2306108A patent/DE2306108C2/de not_active Expired
- 1973-02-14 FR FR7305189A patent/FR2172223B1/fr not_active Expired
- 1973-02-14 AR AR246592A patent/AR196655A1/es active
- 1973-02-15 JP JP1883873A patent/JPS5328415B2/ja not_active Expired
- 1973-02-15 CH CH219173A patent/CH589098A5/xx not_active IP Right Cessation
- 1973-02-16 IT IT48290/73A patent/IT977374B/it active
- 1973-02-16 ZA ZA731104A patent/ZA731104B/xx unknown
- 1973-02-16 BR BR731187A patent/BR7301187D0/pt unknown
- 1973-02-16 SU SU731883163A patent/SU625615A3/ru active
- 1973-02-16 BE BE795532D patent/BE795532A/fr unknown
- 1973-02-16 CS CS731139A patent/CS208691B2/cs unknown

Also Published As

Publication number	Publication date
NL7301722A (fr)	1973-08-21
GB1362357A (en)	1974-08-07
CA1000734A (en)	1976-11-30
AR196655A1 (es)	1974-02-12
ZA731104B (en)	1973-11-28
AU5157973A (en)	1974-08-01
FR2172223B1 (fr)	1977-02-04
IL41415A (en)	1975-07-28
CH589098A5 (fr)	1977-06-30
US3790629A (en)	1974-02-05
IT977374B (it)	1974-09-10
IL41415A0 (en)	1973-03-30
BR7301187D0 (pt)	1973-09-25
FR2172223A1 (fr)	1973-09-28
BE795532A (fr)	1973-08-16
DE2306108C2 (de)	1982-09-23
SU625615A3 (ru)	1978-09-25
JPS4886823A (fr)	1973-11-15
AU471617B2 (en)	1976-04-29
DE2306108A1 (de)	1973-08-23
JPS5328415B2 (fr)	1978-08-15

Publication	Publication Date	Title
Maier	1990	Organic Phosphorus Compounds 90. l A Convenient, One-Step Synthesis of Alkyl-and Arylphosphonyl Dichlorides
CS208691B2 (en)	1981-09-15	Method of preparation of the alkyl-or arylphosphonothiodichlorides
JP3726248B2 (ja)	2005-12-14	フオスフオロジクロリドジチオエートの製造法
EP0008164B1 (fr)	1983-04-20	Phosphinites et phosphonites, leur préparation et leur utilisation comme catalyseurs de dimérisation d'acrylonitrile
US4536350A (en)	1985-08-20	Process for making chlorophosphanes, phosphinic acid chlorides or thiophosphinic acid chloride, and novel isomeric mixture consisting of chloro-phosphabicyclononanes
US5177238A (en)	1993-01-05	Preparation of dialkyl allylphosphonic acid diesters
US3974217A (en)	1976-08-10	Preparation of substituted phenyl phosphonous dichlorides
US3879500A (en)	1975-04-22	Process for Preparing mono- and di-alkylmercaptophosphorothionochloridates
EP0070235A1 (fr)	1983-01-19	Procédé de préparation d'aluminium-alkyls
US5057633A (en)	1991-10-15	Synthesis of perfluoroalkyl bromides
US3962323A (en)	1976-06-08	Process for preparing alkyl- or aryl-phosphonothioic dihalides
CA1067910A (fr)	1979-12-11	Production de s-aklylphosphorodihalogenidodithioate
JPS5949233B2 (ja)	1984-12-01	Ｏ，ｏ−ジアルキルチオノ燐酸クロリドの製造法
CA1302428C (fr)	1992-06-02	Procede pour la preparation de dichlorures phosphorodithioiques
US3726918A (en)	1973-04-10	Process for preparing alkyl and aryl phosphonothioic and phosphinothioic halides
US4000190A (en)	1976-12-28	Process for preparing alkyl- and aryl phosphonothioic dihalides
US4133830A (en)	1979-01-09	Process for preparing alkyl or aryl thiophosphorus halides and mixed isomers thereof
JACOBS et al.	1961	Reaction of 2-Alkoxymethylthiiranes with Lithium Aluminum Hydride and with Secondary Amines
US4855087A (en)	1989-08-08	Process for the preparation of 2-chloroethanephosphonyl dichloride
US4150058A (en)	1979-04-17	Production of alkyl phosphines
US3968156A (en)	1976-07-06	Process for preparing alkyl-or arylphosphonothioic dihalides
US4076746A (en)	1978-02-28	Process for preparing dialkyl and diaryl phosphonothioic halides
EP0203827B1 (fr)	1989-04-05	Procédé pour la préparation d'ortho(alkylthio)phénols
Smith et al.	1983	A convenient synthesis of dimethyl [(alkylthio) methyl] phosphonates and dimethyl [(arylthio) methyl] phosphonates
US4749524A (en)	1988-06-07	Process for the preparation of 2-chloroethanephosphonic dichloride