CS208691B2 - Method of preparation of the alkyl-or arylphosphonothiodichlorides - Google Patents
Method of preparation of the alkyl-or arylphosphonothiodichlorides Download PDFInfo
- Publication number
- CS208691B2 CS208691B2 CS731139A CS113973A CS208691B2 CS 208691 B2 CS208691 B2 CS 208691B2 CS 731139 A CS731139 A CS 731139A CS 113973 A CS113973 A CS 113973A CS 208691 B2 CS208691 B2 CS 208691B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- product
- autoclave
- reaction
- alkyl
- hcl
- Prior art date
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)
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 (es) |
| JP (1) | JPS5328415B2 (es) |
| AR (1) | AR196655A1 (es) |
| AU (1) | AU471617B2 (es) |
| BE (1) | BE795532A (es) |
| BR (1) | BR7301187D0 (es) |
| CA (1) | CA1000734A (es) |
| CH (1) | CH589098A5 (es) |
| CS (1) | CS208691B2 (es) |
| DE (1) | DE2306108C2 (es) |
| FR (1) | FR2172223B1 (es) |
| GB (1) | GB1362357A (es) |
| IL (1) | IL41415A (es) |
| IT (1) | IT977374B (es) |
| NL (1) | NL7301722A (es) |
| SU (1) | SU625615A3 (es) |
| ZA (1) | ZA731104B (es) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5320974B2 (es) * | 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 AR AR246592A patent/AR196655A1/es active
- 1973-02-14 FR FR7305189A patent/FR2172223B1/fr not_active Expired
- 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 ZA ZA731104A patent/ZA731104B/xx unknown
- 1973-02-16 BR BR731187A patent/BR7301187D0/pt unknown
- 1973-02-16 CS CS731139A patent/CS208691B2/cs unknown
- 1973-02-16 BE BE795532D patent/BE795532A/xx unknown
- 1973-02-16 IT IT48290/73A patent/IT977374B/it active
- 1973-02-16 SU SU731883163A patent/SU625615A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| BR7301187D0 (pt) | 1973-09-25 |
| ZA731104B (en) | 1973-11-28 |
| FR2172223A1 (es) | 1973-09-28 |
| CA1000734A (en) | 1976-11-30 |
| JPS5328415B2 (es) | 1978-08-15 |
| AU5157973A (en) | 1974-08-01 |
| SU625615A3 (ru) | 1978-09-25 |
| CH589098A5 (es) | 1977-06-30 |
| AU471617B2 (en) | 1976-04-29 |
| DE2306108C2 (de) | 1982-09-23 |
| BE795532A (fr) | 1973-08-16 |
| JPS4886823A (es) | 1973-11-15 |
| IT977374B (it) | 1974-09-10 |
| IL41415A (en) | 1975-07-28 |
| IL41415A0 (en) | 1973-03-30 |
| NL7301722A (es) | 1973-08-21 |
| FR2172223B1 (es) | 1977-02-04 |
| AR196655A1 (es) | 1974-02-12 |
| GB1362357A (en) | 1974-08-07 |
| US3790629A (en) | 1974-02-05 |
| DE2306108A1 (de) | 1973-08-23 |
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