BE499518A - - Google Patents
Info
- Publication number
- BE499518A BE499518A BE499518DA BE499518A BE 499518 A BE499518 A BE 499518A BE 499518D A BE499518D A BE 499518DA BE 499518 A BE499518 A BE 499518A
- Authority
- BE
- Belgium
- Prior art keywords
- solution
- oxime
- methyl alcohol
- nitro derivatives
- sodium hydroxide
- Prior art date
Links
- 150000002923 oximes Chemical class 0.000 claims description 11
- 150000002828 nitro derivatives Chemical group 0.000 claims description 7
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000000243 solution Substances 0.000 description 14
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- -1 alkali metal salts Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 4
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 4
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- NJNQUTDUIPVROZ-UHFFFAOYSA-N nitrocyclohexane Chemical compound [O-][N+](=O)C1CCCCC1 NJNQUTDUIPVROZ-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- FZENGILVLUJGJX-IHWYPQMZSA-N (Z)-acetaldehyde oxime Chemical compound C\C=N/O FZENGILVLUJGJX-IHWYPQMZSA-N 0.000 description 1
- WFMBIXFCBWYGBZ-UHFFFAOYSA-N 1-methyl-3-nitrocyclohexane Chemical compound CC1CCCC([N+]([O-])=O)C1 WFMBIXFCBWYGBZ-UHFFFAOYSA-N 0.000 description 1
- JSZOAYXJRCEYSX-UHFFFAOYSA-N 1-nitropropane Chemical compound CCC[N+]([O-])=O JSZOAYXJRCEYSX-UHFFFAOYSA-N 0.000 description 1
- KNGSAYHEXMAZMM-UHFFFAOYSA-N 2-nitrohexane Chemical compound CCCCC(C)[N+]([O-])=O KNGSAYHEXMAZMM-UHFFFAOYSA-N 0.000 description 1
- FGLBSLMDCBOPQK-UHFFFAOYSA-N 2-nitropropane Chemical compound CC(C)[N+]([O-])=O FGLBSLMDCBOPQK-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE499518A true BE499518A (d) |
Family
ID=141900
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE499518D BE499518A (d) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE499518A (d) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2696505A (en) * | 1949-11-30 | 1954-12-07 | Bayer Ag | Production of oximes |
| US2709179A (en) * | 1950-03-31 | 1955-05-24 | Directie Staatsmijnen Nl | Production of cycloalkanone oximes by the reduction of cyclic nitro paraffins |
| US2712032A (en) * | 1951-12-21 | 1955-06-28 | Basf Ag | Production of oximes |
| US2822394A (en) * | 1954-08-05 | 1958-02-04 | Olin Mathieson | Recovery of cyclohexanone oxime |
| US2822393A (en) * | 1954-08-05 | 1958-02-04 | Olin Mathieson | Recovery of cyclohexanone oxime |
| US2885440A (en) * | 1952-10-23 | 1959-05-05 | Hoechst Ag | Process of preparing cycloalkanone-oximes |
-
0
- BE BE499518D patent/BE499518A/fr unknown
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2696505A (en) * | 1949-11-30 | 1954-12-07 | Bayer Ag | Production of oximes |
| US2709179A (en) * | 1950-03-31 | 1955-05-24 | Directie Staatsmijnen Nl | Production of cycloalkanone oximes by the reduction of cyclic nitro paraffins |
| US2712032A (en) * | 1951-12-21 | 1955-06-28 | Basf Ag | Production of oximes |
| US2885440A (en) * | 1952-10-23 | 1959-05-05 | Hoechst Ag | Process of preparing cycloalkanone-oximes |
| US2822394A (en) * | 1954-08-05 | 1958-02-04 | Olin Mathieson | Recovery of cyclohexanone oxime |
| US2822393A (en) * | 1954-08-05 | 1958-02-04 | Olin Mathieson | Recovery of cyclohexanone oxime |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| BE499518A (d) | ||
| CH666888A5 (fr) | Procede de dedoublement optique d'un derive de l'acide phenylacetique. | |
| EP0024983B1 (fr) | Dérivés d'amino-14 stéroides et procédé pour leur préparation | |
| EP1247795A1 (fr) | Procédé de fabrication d'acrylates de 2-éthylhexyle | |
| EP0821697B1 (fr) | Procede de preparation de streptogramines | |
| EP0004257A1 (fr) | Nouveau dérivé de benzonitrile, son procédé de préparation et son application | |
| BE503775A (d) | ||
| BE582143A (d) | ||
| FR2609287A1 (fr) | Procede de preparation d'un acide 4-trifluoromethyl-2-nitrobenzoique et d'un nouvel isomere | |
| BE583999A (d) | ||
| BE450358A (d) | ||
| BE539991A (d) | ||
| BE380800A (d) | ||
| FR2664593A1 (fr) | Procede de preparation de la dimethyl-2,5 hydroxy-4 (2h) furanone-3. | |
| BE661312A (d) | ||
| BE544381A (d) | ||
| BE531816A (d) | ||
| BE878446A (fr) | Acides trichloro-phenoxy-alcanoiques exempts de dibenzo-p-dioxines chlorees et leur preparation | |
| BE827580A (fr) | Preparation de d et l-2-amino-1-butanol | |
| BE442051A (d) | ||
| BE534440A (d) | ||
| BE552282A (d) | ||
| BE904929A (fr) | PROCEDE DE PREPARATION DE LA 1-(2-PIPERIDINOETHYL)-4,4-bis-(4-METHOXYPHENYL)2,5-IMIDAZOLIDINEDIONE. | |
| BE562335A (d) | ||
| BE402739A (d) |