DE1568504C - - Google Patents
Info
- Publication number
- DE1568504C DE1568504C DE19661568504 DE1568504A DE1568504C DE 1568504 C DE1568504 C DE 1568504C DE 19661568504 DE19661568504 DE 19661568504 DE 1568504 A DE1568504 A DE 1568504A DE 1568504 C DE1568504 C DE 1568504C
- Authority
- DE
- Germany
- Prior art keywords
- cyclohexanone
- hydrogen peroxide
- ammonia
- aqueous
- oxime
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 53
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 44
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 30
- 229910021529 ammonia Inorganic materials 0.000 claims description 14
- 239000007864 aqueous solution Substances 0.000 claims description 11
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical class ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 238000004821 distillation Methods 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 239000000243 solution Substances 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 159000000000 sodium salts Chemical class 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 2
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 2
- PBYZMCDFOULPGH-UHFFFAOYSA-N tungstate Chemical compound [O-][W]([O-])(=O)=O PBYZMCDFOULPGH-UHFFFAOYSA-N 0.000 claims 5
- 239000008346 aqueous phase Substances 0.000 claims 4
- -1 ethylenediamino Chemical group 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 150000002978 peroxides Chemical class 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 239000003054 catalyst Substances 0.000 claims 3
- WHXCGIRATPOBAY-VOTSOKGWSA-N (ne)-n-hexan-2-ylidenehydroxylamine Chemical compound CCCC\C(C)=N\O WHXCGIRATPOBAY-VOTSOKGWSA-N 0.000 claims 2
- ZUYKJZQOPXDNOK-UHFFFAOYSA-N 2-(ethylamino)-2-thiophen-2-ylcyclohexan-1-one;hydrochloride Chemical class Cl.C=1C=CSC=1C1(NCC)CCCCC1=O ZUYKJZQOPXDNOK-UHFFFAOYSA-N 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 2
- 239000012736 aqueous medium Substances 0.000 claims 2
- 239000012071 phase Substances 0.000 claims 2
- 238000005191 phase separation Methods 0.000 claims 2
- 239000000376 reactant Substances 0.000 claims 2
- 241001440267 Cyclodes Species 0.000 claims 1
- 241001072332 Monia Species 0.000 claims 1
- 239000004698 Polyethylene Substances 0.000 claims 1
- 239000004743 Polypropylene Substances 0.000 claims 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 238000010533 azeotropic distillation Methods 0.000 claims 1
- 230000009286 beneficial effect Effects 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 239000002609 medium Substances 0.000 claims 1
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 claims 1
- 239000012074 organic phase Substances 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 239000004033 plastic Substances 0.000 claims 1
- 229920003023 plastic Polymers 0.000 claims 1
- 229920000573 polyethylene Polymers 0.000 claims 1
- 229920001155 polypropylene Polymers 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- 239000010453 quartz Substances 0.000 claims 1
- 230000000717 retained effect Effects 0.000 claims 1
- 150000004760 silicates Chemical class 0.000 claims 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 1
- 239000003381 stabilizer Substances 0.000 claims 1
- 229910001220 stainless steel Inorganic materials 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 238000001256 steam distillation Methods 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 229910052715 tantalum Inorganic materials 0.000 claims 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 claims 1
- 239000010936 titanium Substances 0.000 claims 1
- 229910052719 titanium Inorganic materials 0.000 claims 1
- 229910052721 tungsten Inorganic materials 0.000 claims 1
- 239000010937 tungsten Substances 0.000 claims 1
- 238000010626 work up procedure Methods 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- VGVHNLRUAMRIEW-UHFFFAOYSA-N 4-methylcyclohexan-1-one Chemical compound CC1CCC(=O)CC1 VGVHNLRUAMRIEW-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- YKFKEYKJGVSEIX-UHFFFAOYSA-N cyclohexanone, 4-(1,1-dimethylethyl)- Chemical compound CC(C)(C)C1CCC(=O)CC1 YKFKEYKJGVSEIX-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- MQWCXKGKQLNYQG-UHFFFAOYSA-N methyl cyclohexan-4-ol Natural products CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- QIVUCLWGARAQIO-OLIXTKCUSA-N (3s)-n-[(3s,5s,6r)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2-oxospiro[1h-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide Chemical compound C1([C@H]2[C@H](N(C(=O)[C@@H](NC(=O)C=3C=C4C[C@]5(CC4=NC=3)C3=CC=CN=C3NC5=O)C2)CC(F)(F)F)C)=C(F)C=CC(F)=C1F QIVUCLWGARAQIO-OLIXTKCUSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- IZYSFFFJIOTJEV-UHFFFAOYSA-P diazanium;dioxido(dioxo)tungsten Chemical compound [NH4+].[NH4+].[O-][W]([O-])(=O)=O IZYSFFFJIOTJEV-UHFFFAOYSA-P 0.000 description 1
- XQARYSVUDNOHMA-UHFFFAOYSA-N n-(4-methylcyclohexylidene)hydroxylamine Chemical compound CC1CCC(=NO)CC1 XQARYSVUDNOHMA-UHFFFAOYSA-N 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0048711 | 1966-03-19 | ||
| DEF0048711 | 1966-03-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1568504A1 DE1568504A1 (de) | 1970-04-09 |
| DE1568504C true DE1568504C (cs) | 1973-03-22 |
Family
ID=7102436
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661568504 Granted DE1568504A1 (de) | 1966-03-19 | 1966-03-19 | Verfahren zur Herstellung von gegebenenfalls alkylsubstituiertem Cyclohexanonoxim |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3655759A (cs) |
| JP (1) | JPS5138703B1 (cs) |
| AT (1) | AT270613B (cs) |
| BE (1) | BE695655A (cs) |
| CH (1) | CH487859A (cs) |
| DE (1) | DE1568504A1 (cs) |
| ES (1) | ES338211A1 (cs) |
| FR (1) | FR1516523A (cs) |
| GB (1) | GB1177495A (cs) |
| NL (1) | NL158484B (cs) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1255745B (it) * | 1992-04-01 | 1995-11-15 | Enichem Anic Srl | Processo in due stadi per la produzione in fase liquida di ossime |
-
1966
- 1966-03-19 DE DE19661568504 patent/DE1568504A1/de active Granted
-
1967
- 1967-03-01 CH CH304067A patent/CH487859A/de not_active IP Right Cessation
- 1967-03-07 GB GB00624/67A patent/GB1177495A/en not_active Expired
- 1967-03-13 AT AT238767A patent/AT270613B/de active
- 1967-03-16 JP JP42016143A patent/JPS5138703B1/ja active Pending
- 1967-03-17 FR FR99234A patent/FR1516523A/fr not_active Expired
- 1967-03-17 BE BE695655D patent/BE695655A/xx unknown
- 1967-03-17 NL NL6704080.A patent/NL158484B/xx unknown
- 1967-03-18 ES ES338211A patent/ES338211A1/es not_active Expired
-
1969
- 1969-11-13 US US871587A patent/US3655759A/en not_active Expired - Lifetime
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