PL81406B1 - - Google Patents
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- Publication number
- PL81406B1 PL81406B1 PL1971151289A PL15128971A PL81406B1 PL 81406 B1 PL81406 B1 PL 81406B1 PL 1971151289 A PL1971151289 A PL 1971151289A PL 15128971 A PL15128971 A PL 15128971A PL 81406 B1 PL81406 B1 PL 81406B1
- Authority
- PL
- Poland
- Prior art keywords
- formula
- carbon atoms
- hydrogen peroxide
- branched
- reaction medium
- Prior art date
Links
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 7
- 150000002466 imines Chemical class 0.000 claims description 6
- 150000002825 nitriles Chemical class 0.000 claims description 6
- 150000004843 oxaziridines Chemical class 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000012429 reaction media Substances 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- -1 N-substituted chloramine Chemical class 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- XRRUENXWJXWJGS-UHFFFAOYSA-N 2,3-di(propan-2-yl)oxaziridine Chemical compound CC(C)C1ON1C(C)C XRRUENXWJXWJGS-UHFFFAOYSA-N 0.000 description 3
- PWJGXKUEOXHYIA-UHFFFAOYSA-N 2-cyclohexyl-3-propan-2-yloxaziridine Chemical compound CC(C)C1ON1C1CCCCC1 PWJGXKUEOXHYIA-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- ZSHFXXXPOYYSQW-UHFFFAOYSA-N [N+](=O)([O-])ClOC Chemical compound [N+](=O)([O-])ClOC ZSHFXXXPOYYSQW-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 150000003951 lactams Chemical class 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- SJGALSBBFTYSBA-UHFFFAOYSA-N oxaziridine Chemical compound C1NO1 SJGALSBBFTYSBA-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- SOJXDJJIMYWISJ-UHFFFAOYSA-N 2-methyl-n-(2-methylpropyl)propan-1-imine Chemical compound CC(C)CN=CC(C)C SOJXDJJIMYWISJ-UHFFFAOYSA-N 0.000 description 1
- KJKJRUBDVLWGLI-UHFFFAOYSA-N 2-methyl-n-propan-2-ylpropan-1-imine Chemical compound CC(C)C=NC(C)C KJKJRUBDVLWGLI-UHFFFAOYSA-N 0.000 description 1
- KAKTYJNRNJXBDQ-UHFFFAOYSA-N 2-tert-butyl-3-propan-2-yloxaziridine Chemical compound CC(C)C1ON1C(C)(C)C KAKTYJNRNJXBDQ-UHFFFAOYSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- CKSLWUURQITAIP-UHFFFAOYSA-N ONOS(=O)=O Chemical compound ONOS(=O)=O CKSLWUURQITAIP-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical compound COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 description 1
- JCJVGEYCNKQCQC-UHFFFAOYSA-N n-cyclohexyl-2-methylpropan-1-imine Chemical compound CC(C)C=NC1CCCCC1 JCJVGEYCNKQCQC-UHFFFAOYSA-N 0.000 description 1
- QAFRYXRYDOBFEF-UHFFFAOYSA-N n-cyclohexylcyclohexanimine Chemical compound C1CCCCC1N=C1CCCCC1 QAFRYXRYDOBFEF-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N ortho-diethylbenzene Natural products CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000003595 spectral effect Effects 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7039204A FR2110787A5 (OSRAM) | 1970-10-30 | 1970-10-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL81406B1 true PL81406B1 (OSRAM) | 1975-08-30 |
Family
ID=9063552
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1971151289A PL81406B1 (OSRAM) | 1970-10-30 | 1971-10-29 |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US3819653A (OSRAM) |
| JP (1) | JPS5327270B1 (OSRAM) |
| AT (1) | AT310770B (OSRAM) |
| BE (1) | BE774685A (OSRAM) |
| BR (1) | BR7107225D0 (OSRAM) |
| CA (1) | CA941382A (OSRAM) |
| CH (1) | CH546781A (OSRAM) |
| DE (1) | DE2152210A1 (OSRAM) |
| DK (1) | DK131568B (OSRAM) |
| ES (1) | ES396340A1 (OSRAM) |
| FR (1) | FR2110787A5 (OSRAM) |
| GB (1) | GB1313455A (OSRAM) |
| HU (1) | HU162995B (OSRAM) |
| IT (1) | IT942750B (OSRAM) |
| LU (1) | LU64171A1 (OSRAM) |
| NL (1) | NL7114945A (OSRAM) |
| PL (1) | PL81406B1 (OSRAM) |
| RO (1) | RO58561A (OSRAM) |
| SE (1) | SE374372B (OSRAM) |
| SU (1) | SU431676A3 (OSRAM) |
| ZA (1) | ZA717077B (OSRAM) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4178292A (en) * | 1972-11-03 | 1979-12-11 | Produits Chimiques Ugine Kuhlmann | Process for the preparation of oxaziridine |
| DE10033079A1 (de) * | 2000-07-07 | 2002-01-17 | Bayer Ag | Verfahren zur Herstellung von 2-tert.-Butyl-3-phenyloxaziridin |
-
1970
- 1970-10-30 FR FR7039204A patent/FR2110787A5/fr not_active Expired
-
1971
- 1971-10-20 DE DE19712152210 patent/DE2152210A1/de active Pending
- 1971-10-22 GB GB4923971A patent/GB1313455A/en not_active Expired
- 1971-10-22 ZA ZA717077A patent/ZA717077B/xx unknown
- 1971-10-25 IT IT70498/71A patent/IT942750B/it active
- 1971-10-25 ES ES396340A patent/ES396340A1/es not_active Expired
- 1971-10-28 US US00193564A patent/US3819653A/en not_active Expired - Lifetime
- 1971-10-28 LU LU64171D patent/LU64171A1/xx unknown
- 1971-10-28 JP JP8521571A patent/JPS5327270B1/ja active Pending
- 1971-10-29 BE BE774685A patent/BE774685A/xx not_active IP Right Cessation
- 1971-10-29 HU HUKU455A patent/HU162995B/hu unknown
- 1971-10-29 NL NL7114945A patent/NL7114945A/xx unknown
- 1971-10-29 SU SU1710724A patent/SU431676A3/ru active
- 1971-10-29 AT AT935771A patent/AT310770B/de not_active IP Right Cessation
- 1971-10-29 CH CH1581671A patent/CH546781A/fr not_active IP Right Cessation
- 1971-10-29 CA CA126,507*7A patent/CA941382A/en not_active Expired
- 1971-10-29 BR BR7225/71A patent/BR7107225D0/pt unknown
- 1971-10-29 SE SE7113813A patent/SE374372B/xx unknown
- 1971-10-29 DK DK529471AA patent/DK131568B/da unknown
- 1971-10-29 PL PL1971151289A patent/PL81406B1/pl unknown
- 1971-10-30 RO RO68612A patent/RO58561A/ro unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SU431676A3 (OSRAM) | 1974-06-05 |
| ZA717077B (en) | 1972-07-26 |
| CA941382A (en) | 1974-02-05 |
| IT942750B (it) | 1973-04-02 |
| AU3507171A (en) | 1973-05-03 |
| US3819653A (en) | 1974-06-25 |
| LU64171A1 (OSRAM) | 1972-05-15 |
| CH546781A (fr) | 1974-03-15 |
| JPS5327270B1 (OSRAM) | 1978-08-07 |
| BR7107225D0 (pt) | 1973-04-12 |
| AT310770B (de) | 1973-10-10 |
| DK131568B (da) | 1975-08-04 |
| FR2110787A5 (OSRAM) | 1972-06-02 |
| HU162995B (OSRAM) | 1973-05-28 |
| GB1313455A (en) | 1973-04-11 |
| SE374372B (OSRAM) | 1975-03-03 |
| ES396340A1 (es) | 1974-05-01 |
| BE774685A (fr) | 1972-02-14 |
| DK131568C (OSRAM) | 1975-12-29 |
| NL7114945A (OSRAM) | 1972-05-03 |
| DE2152210A1 (de) | 1972-05-04 |
| RO58561A (OSRAM) | 1975-08-15 |
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