JPH0142890B2 - - Google Patents
Info
- Publication number
- JPH0142890B2 JPH0142890B2 JP55060823A JP6082380A JPH0142890B2 JP H0142890 B2 JPH0142890 B2 JP H0142890B2 JP 55060823 A JP55060823 A JP 55060823A JP 6082380 A JP6082380 A JP 6082380A JP H0142890 B2 JPH0142890 B2 JP H0142890B2
- Authority
- JP
- Japan
- Prior art keywords
- cyclohexanone
- column
- hydrogen sulfate
- ammonium hydrogen
- sulfate solution
- 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 83
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 claims description 58
- WWILHZQYNPQALT-UHFFFAOYSA-N 2-methyl-2-morpholin-4-ylpropanal Chemical compound O=CC(C)(C)N1CCOCC1 WWILHZQYNPQALT-UHFFFAOYSA-N 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 14
- YCAWQMGAYOBYAN-UHFFFAOYSA-N NO.OS(O)(=O)=O.N Chemical compound NO.OS(O)(=O)=O.N YCAWQMGAYOBYAN-UHFFFAOYSA-N 0.000 claims description 10
- 238000000746 purification Methods 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 3
- 238000010533 azeotropic distillation Methods 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 34
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
- 229910052799 carbon Inorganic materials 0.000 description 11
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 3
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 3
- 235000011130 ammonium sulphate Nutrition 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 229910000378 hydroxylammonium sulfate Inorganic materials 0.000 description 2
- VGYYSIDKAKXZEE-UHFFFAOYSA-L hydroxylammonium sulfate Chemical compound O[NH3+].O[NH3+].[O-]S([O-])(=O)=O VGYYSIDKAKXZEE-UHFFFAOYSA-L 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000006146 oximation reaction Methods 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- WEWZILAIHLFVHK-UHFFFAOYSA-N 2-hex-1-enylcyclohexan-1-one Chemical compound CCCCC=CC1CCCCC1=O WEWZILAIHLFVHK-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- ZRJUCHNILNOEKV-UHFFFAOYSA-N hexan-2-one hydrate Chemical compound O.CCCCC(C)=O ZRJUCHNILNOEKV-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01C—AMMONIA; CYANOGEN; COMPOUNDS THEREOF
- C01C1/00—Ammonia; Compounds thereof
- C01C1/24—Sulfates of ammonium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C45/82—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
- C07C45/84—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation by azeotropic distillation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792921649 DE2921649A1 (de) | 1979-05-28 | 1979-05-28 | Verfahren zur behandlung von cyclohexanon und cyclohexanonoxim enthaltenden ammoniumhydrogensulfatloesungen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS55157556A JPS55157556A (en) | 1980-12-08 |
| JPH0142890B2 true JPH0142890B2 (en]) | 1989-09-18 |
Family
ID=6071879
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6082380A Granted JPS55157556A (en) | 1979-05-28 | 1980-05-09 | Treatment of ammonium hydrogensulfate solution containing cyclohexanone and cyclohexanoneoxime |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP0019767B1 (en]) |
| JP (1) | JPS55157556A (en]) |
| DE (2) | DE2921649A1 (en]) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3942334A1 (de) * | 1989-12-21 | 1991-06-27 | Basf Ag | Verfahren zur aufarbeitung von salzsaeure, schwefelsaeure und deren hydroxylammonium- und ammoniumsalze enthaltenden waessrigen mutterlaugen |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3940442A (en) * | 1969-12-06 | 1976-02-24 | Stamicarbon B.V. | Recycle process for the preparation and processing of a hydroxylammonium salt solution |
| NL7001905A (en]) * | 1970-02-11 | 1971-08-13 | ||
| DE2508247C3 (de) * | 1975-02-26 | 1981-03-12 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von Cyclohexanonoxim |
-
1979
- 1979-05-28 DE DE19792921649 patent/DE2921649A1/de not_active Withdrawn
-
1980
- 1980-05-08 EP EP80102512A patent/EP0019767B1/de not_active Expired
- 1980-05-08 DE DE8080102512T patent/DE3068785D1/de not_active Expired
- 1980-05-09 JP JP6082380A patent/JPS55157556A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| EP0019767A3 (en) | 1981-09-09 |
| JPS55157556A (en) | 1980-12-08 |
| DE2921649A1 (de) | 1980-12-11 |
| DE3068785D1 (en) | 1984-09-06 |
| EP0019767B1 (de) | 1984-08-01 |
| EP0019767A2 (de) | 1980-12-10 |
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