SU450414A3 - Способ получен циклических дикарбоксиимидов 0,0,-диалкилтиофосфорных кислот - Google Patents
Способ получен циклических дикарбоксиимидов 0,0,-диалкилтиофосфорных кислотInfo
- Publication number
- SU450414A3 SU450414A3 SU1848407A SU1848407A SU450414A3 SU 450414 A3 SU450414 A3 SU 450414A3 SU 1848407 A SU1848407 A SU 1848407A SU 1848407 A SU1848407 A SU 1848407A SU 450414 A3 SU450414 A3 SU 450414A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- mol
- cyclic
- acids
- chlorothiophosphate
- dicarboxyimide
- Prior art date
Links
- -1 cyclic dicarboxyimide Chemical class 0.000 title claims description 23
- 238000000034 method Methods 0.000 title claims description 14
- 239000002253 acid Substances 0.000 title claims description 5
- 150000007513 acids Chemical class 0.000 title claims description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
- 239000003054 catalyst Substances 0.000 claims description 11
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
- 150000003509 tertiary alcohols Chemical class 0.000 claims description 5
- HPFKOFNYNQMWEF-UHFFFAOYSA-N chloro-dihydroxy-sulfanylidene-$l^{5}-phosphane Chemical class OP(O)(Cl)=S HPFKOFNYNQMWEF-UHFFFAOYSA-N 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000005544 phthalimido group Chemical group 0.000 claims description 2
- 229920005549 butyl rubber Polymers 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 description 13
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000003153 chemical reaction reagent Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- MTBZIGHNGSTDJV-UHFFFAOYSA-N Ditalimfos Chemical compound C1=CC=C2C(=O)N(P(=S)(OCC)OCC)C(=O)C2=C1 MTBZIGHNGSTDJV-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- WLLGXSLBOPFWQV-UHFFFAOYSA-N MGK 264 Chemical compound C1=CC2CC1C1C2C(=O)N(CC(CC)CCCC)C1=O WLLGXSLBOPFWQV-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 150000001339 alkali metal compounds Chemical class 0.000 description 2
- KMJJJTCKNZYTEY-UHFFFAOYSA-N chloro-diethoxy-sulfanylidene-$l^{5}-phosphane Chemical compound CCOP(Cl)(=S)OCC KMJJJTCKNZYTEY-UHFFFAOYSA-N 0.000 description 2
- DEGPIRUPAKWDBU-UHFFFAOYSA-N isoindole-1,3-dione;sodium Chemical compound [Na].C1=CC=C2C(=O)NC(=O)C2=C1 DEGPIRUPAKWDBU-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- CTMHWPIWNRWQEG-UHFFFAOYSA-N 1-methylcyclohexene Chemical compound CC1=CCCCC1 CTMHWPIWNRWQEG-UHFFFAOYSA-N 0.000 description 1
- KYWXRBNOYGGPIZ-UHFFFAOYSA-N 1-morpholin-4-ylethanone Chemical compound CC(=O)N1CCOCC1 KYWXRBNOYGGPIZ-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- FRDAATYAJDYRNW-UHFFFAOYSA-N 3-methylpentanol-3 Natural products CCC(C)(O)CC FRDAATYAJDYRNW-UHFFFAOYSA-N 0.000 description 1
- ABCGRFHYOYXEJV-UHFFFAOYSA-N 4-methylisoindole-1,3-dione Chemical compound CC1=CC=CC2=C1C(=O)NC2=O ABCGRFHYOYXEJV-UHFFFAOYSA-N 0.000 description 1
- OEMSKMUAMXLNKL-UHFFFAOYSA-N 5-methyl-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical group C1C(C)=CCC2C(=O)OC(=O)C12 OEMSKMUAMXLNKL-UHFFFAOYSA-N 0.000 description 1
- UKRUJPIJOJHCOB-UHFFFAOYSA-N 5-methylisoindole-1,3-dione Chemical compound CC1=CC=C2C(=O)NC(=O)C2=C1 UKRUJPIJOJHCOB-UHFFFAOYSA-N 0.000 description 1
- CHLCGLVMIQCUNA-UHFFFAOYSA-N CCOC(C)(C)OP(O)(Cl)=S Chemical compound CCOC(C)(C)OP(O)(Cl)=S CHLCGLVMIQCUNA-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- JWHIIHSWAUCTDL-UHFFFAOYSA-N chloro-hydroxy-methoxy-sulfanylidene-$l^{5}-phosphane Chemical compound COP(O)(Cl)=S JWHIIHSWAUCTDL-UHFFFAOYSA-N 0.000 description 1
- GWIDYCSWQMCWRB-UHFFFAOYSA-N chloro-hydroxy-sulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound OP(S)(Cl)=S GWIDYCSWQMCWRB-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 150000003388 sodium compounds Chemical class 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003513 tertiary aromatic amines Chemical class 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- LZTRCELOJRDYMQ-UHFFFAOYSA-N triphenylmethanol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(O)C1=CC=CC=C1 LZTRCELOJRDYMQ-UHFFFAOYSA-N 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
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
-
- 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/5537—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom the heteroring containing the structure -C(=O)-N-C(=O)- (both carbon atoms belong to the heteroring)
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)
- Indole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00199714A US3803167A (en) | 1971-11-17 | 1971-11-17 | Process for preparing cyclicdicarboximido-substituted phosphonothioates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU450414A3 true SU450414A3 (ru) | 1974-11-15 |
Family
ID=22738718
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1848407A SU450414A3 (ru) | 1971-11-17 | 1972-11-16 | Способ получен циклических дикарбоксиимидов 0,0,-диалкилтиофосфорных кислот |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US3803167A (enExample) |
| JP (1) | JPS4861469A (enExample) |
| BE (1) | BE791527A (enExample) |
| CA (1) | CA967967A (enExample) |
| CH (1) | CH576481A5 (enExample) |
| CS (1) | CS176210B2 (enExample) |
| ES (1) | ES408616A1 (enExample) |
| FR (1) | FR2160491B1 (enExample) |
| GB (1) | GB1400875A (enExample) |
| HU (1) | HU165801B (enExample) |
| IL (1) | IL40675A (enExample) |
| IT (1) | IT974827B (enExample) |
| NL (1) | NL159108B (enExample) |
| SU (1) | SU450414A3 (enExample) |
| YU (1) | YU35265B (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1398663A (en) * | 1973-10-23 | 1975-06-25 | Dow Chemical Co | Process for preparing cyclicdicarboximido-substituted phos phonithioates |
| US4204996A (en) * | 1978-11-02 | 1980-05-27 | Dow Chemical Company Limited | Preparation of O,O-dialkyl phthalimido-phosphonothioate |
-
0
- BE BE791527D patent/BE791527A/xx unknown
-
1971
- 1971-11-17 US US00199714A patent/US3803167A/en not_active Expired - Lifetime
-
1972
- 1972-10-26 IL IL40675A patent/IL40675A/xx unknown
- 1972-10-27 CA CA155,030A patent/CA967967A/en not_active Expired
- 1972-11-07 CH CH1621072A patent/CH576481A5/xx not_active IP Right Cessation
- 1972-11-07 CS CS7509A patent/CS176210B2/cs unknown
- 1972-11-09 NL NL7215167.A patent/NL159108B/xx unknown
- 1972-11-15 ES ES408616A patent/ES408616A1/es not_active Expired
- 1972-11-15 IT IT54017/72A patent/IT974827B/it active
- 1972-11-15 FR FR7240550A patent/FR2160491B1/fr not_active Expired
- 1972-11-16 YU YU2848/72A patent/YU35265B/xx unknown
- 1972-11-16 SU SU1848407A patent/SU450414A3/ru active
- 1972-11-17 GB GB5334172A patent/GB1400875A/en not_active Expired
- 1972-11-17 HU HUDO370A patent/HU165801B/hu unknown
- 1972-11-17 JP JP47115508A patent/JPS4861469A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| GB1400875A (en) | 1975-07-16 |
| BE791527A (fr) | 1973-05-17 |
| CS176210B2 (enExample) | 1977-06-30 |
| YU35265B (en) | 1980-10-31 |
| CA967967A (en) | 1975-05-20 |
| HU165801B (enExample) | 1974-11-28 |
| FR2160491B1 (enExample) | 1976-10-29 |
| ES408616A1 (es) | 1975-10-01 |
| NL159108B (nl) | 1979-01-15 |
| YU284872A (en) | 1980-04-30 |
| DE2256253A1 (de) | 1973-05-24 |
| CH576481A5 (enExample) | 1976-06-15 |
| US3803167A (en) | 1974-04-09 |
| FR2160491A1 (enExample) | 1973-06-29 |
| JPS4861469A (enExample) | 1973-08-28 |
| IL40675A (en) | 1975-07-28 |
| NL7215167A (enExample) | 1973-05-21 |
| IL40675A0 (en) | 1972-12-29 |
| IT974827B (it) | 1974-07-10 |
| DE2256253B2 (de) | 1975-10-16 |
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