CH623828A5 - - Google Patents
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- Publication number
- CH623828A5 CH623828A5 CH1195076A CH1195076A CH623828A5 CH 623828 A5 CH623828 A5 CH 623828A5 CH 1195076 A CH1195076 A CH 1195076A CH 1195076 A CH1195076 A CH 1195076A CH 623828 A5 CH623828 A5 CH 623828A5
- Authority
- CH
- Switzerland
- Prior art keywords
- reaction
- compounds
- catalyst
- formula
- sulfurization
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 80
- 238000006243 chemical reaction Methods 0.000 claims description 76
- 239000003054 catalyst Substances 0.000 claims description 35
- 238000005987 sulfurization reaction Methods 0.000 claims description 30
- 239000000047 product Substances 0.000 claims description 29
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 27
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 22
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 20
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 16
- 229910052698 phosphorus Inorganic materials 0.000 claims description 16
- 239000011574 phosphorus Substances 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 239000011593 sulfur Substances 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 13
- 239000007795 chemical reaction product Substances 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 2
- 238000006277 sulfonation reaction Methods 0.000 claims 2
- VKCLPVFDVVKEKU-UHFFFAOYSA-N S=[P] Chemical compound S=[P] VKCLPVFDVVKEKU-UHFFFAOYSA-N 0.000 claims 1
- 238000009835 boiling Methods 0.000 description 20
- 230000015572 biosynthetic process Effects 0.000 description 11
- -1 alkyl mercaptans Chemical class 0.000 description 9
- 238000004821 distillation Methods 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 8
- 239000000376 reactant Substances 0.000 description 7
- 238000005292 vacuum distillation Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 6
- 150000003018 phosphorus compounds Chemical class 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- SUVIGLJNEAMWEG-UHFFFAOYSA-N propane-1-thiol Chemical compound CCCS SUVIGLJNEAMWEG-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 101000998897 Homo sapiens Serine protease HTRA3 Proteins 0.000 description 3
- 102100033197 Serine protease HTRA3 Human genes 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 230000003750 conditioning effect Effects 0.000 description 2
- 230000001186 cumulative effect Effects 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000007970 thio esters Chemical class 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- FLGXTUHKUDIKBA-UHFFFAOYSA-N butan-2-ylsulfanyl-dichloro-sulfanylidene-$l^{5}-phosphane Chemical compound CCC(C)SP(Cl)(Cl)=S FLGXTUHKUDIKBA-UHFFFAOYSA-N 0.000 description 1
- ODTQZMHKOTZREO-UHFFFAOYSA-N butylsulfanyl-dichloro-sulfanylidene-$l^{5}-phosphane Chemical compound CCCCSP(Cl)(Cl)=S ODTQZMHKOTZREO-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- SWRNIYAQKATHDJ-UHFFFAOYSA-N dichloro(dichlorophosphanyl)phosphane Chemical compound ClP(Cl)P(Cl)Cl SWRNIYAQKATHDJ-UHFFFAOYSA-N 0.000 description 1
- ADOQWWHENXUSIR-UHFFFAOYSA-N dichloro-(2,2-dimethylpropylsulfanyl)-sulfanylidene-$l^{5}-phosphane Chemical compound CC(C)(C)CSP(Cl)(Cl)=S ADOQWWHENXUSIR-UHFFFAOYSA-N 0.000 description 1
- QDQRCKABESUJMJ-UHFFFAOYSA-N dichloro-(2-methylpropylsulfanyl)-sulfanylidene-$l^{5}-phosphane Chemical compound CC(C)CSP(Cl)(Cl)=S QDQRCKABESUJMJ-UHFFFAOYSA-N 0.000 description 1
- YTDXTPNEDPPXFX-UHFFFAOYSA-N dichloro-(3-methylbutylsulfanyl)-sulfanylidene-lambda5-phosphane Chemical compound P(=S)(SCCC(C)C)(Cl)Cl YTDXTPNEDPPXFX-UHFFFAOYSA-N 0.000 description 1
- RWLHKBQJTQSZOU-UHFFFAOYSA-N dichloro-(4-methylpentylsulfanyl)-sulfanylidene-$l^{5}-phosphane Chemical compound CC(C)CCCSP(Cl)(Cl)=S RWLHKBQJTQSZOU-UHFFFAOYSA-N 0.000 description 1
- NWQMEQZPDPMMGK-UHFFFAOYSA-N dichloro-ethylsulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound CCSP(Cl)(Cl)=S NWQMEQZPDPMMGK-UHFFFAOYSA-N 0.000 description 1
- IHEGCIBKGPVKPL-UHFFFAOYSA-N dichloro-pentylsulfanyl-sulfanylidene-lambda5-phosphane Chemical compound CCCCCSP(Cl)(Cl)=S IHEGCIBKGPVKPL-UHFFFAOYSA-N 0.000 description 1
- DDIWVROBLCQVNC-UHFFFAOYSA-N dichloro-propan-2-ylsulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound CC(C)SP(Cl)(Cl)=S DDIWVROBLCQVNC-UHFFFAOYSA-N 0.000 description 1
- LYNQYRBGWINIFJ-UHFFFAOYSA-N dichloro-propylsulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound CCCSP(Cl)(Cl)=S LYNQYRBGWINIFJ-UHFFFAOYSA-N 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 238000000926 separation method 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/20—Esters of thiophosphoric acids containing P-halide groups
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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/625,345 US4035449A (en) | 1975-10-23 | 1975-10-23 | Process for the production of S-alkyl phosphoro dihalogenidodithioate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH623828A5 true CH623828A5 (un) | 1981-06-30 |
Family
ID=24505637
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1195076A CH623828A5 (un) | 1975-10-23 | 1976-09-21 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4035449A (un) |
| JP (1) | JPS5949234B2 (un) |
| AT (1) | AT344730B (un) |
| BE (1) | BE847542A (un) |
| BR (1) | BR7607079A (un) |
| CA (1) | CA1067910A (un) |
| CH (1) | CH623828A5 (un) |
| DE (1) | DE2647058C3 (un) |
| DK (1) | DK145002C (un) |
| FR (1) | FR2328714A1 (un) |
| GB (1) | GB1515815A (un) |
| IL (1) | IL50731A (un) |
| IT (1) | IT1069003B (un) |
| NL (1) | NL188040C (un) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4770806A (en) * | 1983-06-09 | 1988-09-13 | Monsanto Company | Deodorized compositions |
| US5457221A (en) * | 1993-03-03 | 1995-10-10 | Akzo Nobel N.V. | Process for the manufacture of poly (hydrocarbylene aryl phosphate) compositions |
| US5543543A (en) * | 1995-05-17 | 1996-08-06 | Bayer Corporation | Process for preparing phosphorodichloridodithioates by reacting alkyl mercaptans with PCI3 PSCI3 and sulfur |
| US5523449A (en) * | 1995-05-17 | 1996-06-04 | Bayer Corporation | Process for preparing phosphorodichlorido-dithioates by reacting alkylmercaptans with phosphorus trichloride in the presence of sulfur |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2943107A (en) * | 1959-11-19 | 1960-06-28 | Chemagro Corp | Process of preparing tributyl phosphorotrithioate |
| US3457306A (en) * | 1965-12-22 | 1969-07-22 | Monsanto Co | Preparation of organothiophosphorus halides |
| CH493203A (de) * | 1968-03-01 | 1970-07-15 | Ciba Geigy | Herbizides Mittel |
| US3879500A (en) * | 1973-10-15 | 1975-04-22 | Stauffer Chemical Co | Process for Preparing mono- and di-alkylmercaptophosphorothionochloridates |
-
1975
- 1975-10-23 US US05/625,345 patent/US4035449A/en not_active Expired - Lifetime
-
1976
- 1976-09-07 CA CA260,615A patent/CA1067910A/en not_active Expired
- 1976-09-21 CH CH1195076A patent/CH623828A5/de not_active IP Right Cessation
- 1976-10-19 DE DE2647058A patent/DE2647058C3/de not_active Expired
- 1976-10-20 IL IL50731A patent/IL50731A/xx unknown
- 1976-10-20 NL NLAANVRAGE7611604,A patent/NL188040C/xx not_active IP Right Cessation
- 1976-10-21 AT AT784676A patent/AT344730B/de not_active IP Right Cessation
- 1976-10-21 IT IT28580/76A patent/IT1069003B/it active
- 1976-10-21 GB GB43724/76A patent/GB1515815A/en not_active Expired
- 1976-10-21 JP JP51125581A patent/JPS5949234B2/ja not_active Expired
- 1976-10-22 BR BR7607079A patent/BR7607079A/pt unknown
- 1976-10-22 DK DK480676A patent/DK145002C/da not_active IP Right Cessation
- 1976-10-22 FR FR7631951A patent/FR2328714A1/fr active Granted
- 1976-10-22 BE BE171709A patent/BE847542A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DK480676A (da) | 1977-04-24 |
| NL188040B (nl) | 1991-10-16 |
| AT344730B (de) | 1978-08-10 |
| FR2328714B1 (un) | 1980-09-12 |
| JPS5949234B2 (ja) | 1984-12-01 |
| FR2328714A1 (fr) | 1977-05-20 |
| CA1067910A (en) | 1979-12-11 |
| NL188040C (nl) | 1992-03-16 |
| DK145002B (da) | 1982-07-26 |
| DK145002C (da) | 1982-12-13 |
| ATA784676A (de) | 1977-12-15 |
| DE2647058A1 (de) | 1977-05-05 |
| JPS5251322A (en) | 1977-04-25 |
| DE2647058B2 (de) | 1981-01-08 |
| US4035449A (en) | 1977-07-12 |
| GB1515815A (en) | 1978-06-28 |
| BE847542A (fr) | 1977-04-22 |
| IL50731A0 (en) | 1976-12-31 |
| NL7611604A (nl) | 1977-04-26 |
| IL50731A (en) | 1979-11-30 |
| IT1069003B (it) | 1985-03-21 |
| BR7607079A (pt) | 1977-09-06 |
| DE2647058C3 (de) | 1982-03-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |