DE1228248B - Verfahren zum Gewinnen von reinen Oximen aus mineralsauren Loesungen - Google Patents
Verfahren zum Gewinnen von reinen Oximen aus mineralsauren LoesungenInfo
- Publication number
- DE1228248B DE1228248B DEF42519A DEF0042519A DE1228248B DE 1228248 B DE1228248 B DE 1228248B DE F42519 A DEF42519 A DE F42519A DE F0042519 A DEF0042519 A DE F0042519A DE 1228248 B DE1228248 B DE 1228248B
- Authority
- DE
- Germany
- Prior art keywords
- oxime
- mineral acid
- dilute
- acid solutions
- oximes
- 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.)
- Pending
Links
- 150000002923 oximes Chemical class 0.000 title claims description 29
- 239000002253 acid Substances 0.000 title claims description 20
- 229910052500 inorganic mineral Inorganic materials 0.000 title claims description 19
- 239000011707 mineral Substances 0.000 title claims description 19
- 238000000034 method Methods 0.000 title claims description 9
- 238000000605 extraction Methods 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 230000002378 acidificating effect Effects 0.000 claims description 6
- 150000002894 organic compounds Chemical class 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000010494 dissociation reaction Methods 0.000 claims description 2
- 230000005593 dissociations Effects 0.000 claims description 2
- 238000001704 evaporation Methods 0.000 claims description 2
- 230000008020 evaporation Effects 0.000 claims description 2
- 239000000284 extract Substances 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 13
- 239000000243 solution Substances 0.000 description 12
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 4
- -1 aromatic hydroxy compounds Chemical class 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- ZKALVNREMFLWAN-VOTSOKGWSA-N (ne)-n-(4-methylpentan-2-ylidene)hydroxylamine Chemical compound CC(C)C\C(C)=N\O ZKALVNREMFLWAN-VOTSOKGWSA-N 0.000 description 2
- SXVPOSFURRDKBO-UHFFFAOYSA-N Cyclododecanone Chemical compound O=C1CCCCCCCCCCC1 SXVPOSFURRDKBO-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- DQNLLSNNESIVOE-UHFFFAOYSA-N 2-chlorooctadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(Cl)C(O)=O DQNLLSNNESIVOE-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 239000004157 Nitrosyl chloride Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000007860 aryl ester derivatives Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- SCRFXJBEIINMIC-UHFFFAOYSA-N n-cyclododecylidenehydroxylamine Chemical compound ON=C1CCCCCCCCCCC1 SCRFXJBEIINMIC-UHFFFAOYSA-N 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- VPCDQGACGWYTMC-UHFFFAOYSA-N nitrosyl chloride Chemical compound ClN=O VPCDQGACGWYTMC-UHFFFAOYSA-N 0.000 description 1
- 235000019392 nitrosyl chloride Nutrition 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C251/44—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups being part of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
- C07C249/08—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes by reaction of hydroxylamines with carbonyl compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF42519A DE1228248B (de) | 1964-04-04 | 1964-04-04 | Verfahren zum Gewinnen von reinen Oximen aus mineralsauren Loesungen |
| CH401665A CH452502A (de) | 1964-04-04 | 1965-03-23 | Verfahren zum Gewinnen von reinen Oximen aus mineralsauren Lösungen |
| US444402A US3423460A (en) | 1964-04-04 | 1965-03-31 | Process for extraction of oximes from mineral acid solutions |
| GB13870/65A GB1029096A (en) | 1964-04-04 | 1965-04-01 | A process for extraction of aliphatic or cycloaliphatic oximes from mineral acid solutions |
| NL6504152A NL6504152A (cg-RX-API-DMAC10.html) | 1964-04-04 | 1965-04-01 | |
| BE661988D BE661988A (cg-RX-API-DMAC10.html) | 1964-04-04 | 1965-04-02 | |
| SE4298/65A SE300418B (cg-RX-API-DMAC10.html) | 1964-04-04 | 1965-04-02 | |
| FR11866A FR1429753A (fr) | 1964-04-04 | 1965-04-03 | Procédé pour l'extraction des oximes des solutions d'acides minéraux |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF42519A DE1228248B (de) | 1964-04-04 | 1964-04-04 | Verfahren zum Gewinnen von reinen Oximen aus mineralsauren Loesungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1228248B true DE1228248B (de) | 1966-11-10 |
Family
ID=7099130
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF42519A Pending DE1228248B (de) | 1964-04-04 | 1964-04-04 | Verfahren zum Gewinnen von reinen Oximen aus mineralsauren Loesungen |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3423460A (cg-RX-API-DMAC10.html) |
| BE (1) | BE661988A (cg-RX-API-DMAC10.html) |
| CH (1) | CH452502A (cg-RX-API-DMAC10.html) |
| DE (1) | DE1228248B (cg-RX-API-DMAC10.html) |
| GB (1) | GB1029096A (cg-RX-API-DMAC10.html) |
| NL (1) | NL6504152A (cg-RX-API-DMAC10.html) |
| SE (1) | SE300418B (cg-RX-API-DMAC10.html) |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2248035A (en) * | 1938-03-24 | 1941-07-01 | Sharp & Dohme Inc | Process of nitrosating aromatic alkyl ketones |
| US2719116A (en) * | 1954-03-19 | 1955-09-27 | Olin Mathieson | Photochemical preparation of oximes |
| US2822393A (en) * | 1954-08-05 | 1958-02-04 | Olin Mathieson | Recovery of cyclohexanone oxime |
| US2822394A (en) * | 1954-08-05 | 1958-02-04 | Olin Mathieson | Recovery of cyclohexanone oxime |
| DE1250814B (de) * | 1959-07-31 | 1967-09-28 | Allied Chemical Corporation, New York, N.Y. (V. St. A.) | Verfahren zur Herstellung eines gesättigten, aliphatischen oder cycloaliphatischen Oxims |
| US3267143A (en) * | 1962-02-03 | 1966-08-16 | Edison Soc | Process for obtaining alpha-chloro-oximes and sulphates thereof |
| NL301254A (cg-RX-API-DMAC10.html) * | 1962-12-05 |
-
1964
- 1964-04-04 DE DEF42519A patent/DE1228248B/de active Pending
-
1965
- 1965-03-23 CH CH401665A patent/CH452502A/de unknown
- 1965-03-31 US US444402A patent/US3423460A/en not_active Expired - Lifetime
- 1965-04-01 NL NL6504152A patent/NL6504152A/xx unknown
- 1965-04-01 GB GB13870/65A patent/GB1029096A/en not_active Expired
- 1965-04-02 BE BE661988D patent/BE661988A/xx unknown
- 1965-04-02 SE SE4298/65A patent/SE300418B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL6504152A (cg-RX-API-DMAC10.html) | 1965-10-05 |
| GB1029096A (en) | 1966-05-11 |
| SE300418B (cg-RX-API-DMAC10.html) | 1968-04-29 |
| CH452502A (de) | 1968-03-15 |
| US3423460A (en) | 1969-01-21 |
| BE661988A (cg-RX-API-DMAC10.html) | 1965-08-02 |
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