DE2059582C3 - Kreislaufverfahren zur Herstellung von Cyclohexanonoxim - Google Patents
Kreislaufverfahren zur Herstellung von CyclohexanonoximInfo
- Publication number
- DE2059582C3 DE2059582C3 DE2059582A DE2059582A DE2059582C3 DE 2059582 C3 DE2059582 C3 DE 2059582C3 DE 2059582 A DE2059582 A DE 2059582A DE 2059582 A DE2059582 A DE 2059582A DE 2059582 C3 DE2059582 C3 DE 2059582C3
- Authority
- DE
- Germany
- Prior art keywords
- oxime
- hydroxylamine
- cyclohexanone
- cyclohexanone oxime
- nitric acid
- 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
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 title claims description 38
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 5
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 28
- 230000015572 biosynthetic process Effects 0.000 claims description 26
- 238000003786 synthesis reaction Methods 0.000 claims description 25
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 16
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 16
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 14
- 150000002923 oximes Chemical class 0.000 claims description 14
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 12
- 229910017604 nitric acid Inorganic materials 0.000 claims description 12
- 229910002651 NO3 Inorganic materials 0.000 claims description 11
- -1 nitrate ions Chemical class 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 9
- 229910052763 palladium Inorganic materials 0.000 claims description 8
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 6
- 150000002894 organic compounds Chemical class 0.000 claims description 6
- 238000004821 distillation Methods 0.000 claims description 5
- 239000012429 reaction media Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 description 17
- 230000000694 effects Effects 0.000 description 10
- 239000000872 buffer Substances 0.000 description 7
- 235000011007 phosphoric acid Nutrition 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 239000012530 fluid Substances 0.000 description 6
- 150000002576 ketones Chemical class 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000012295 chemical reaction liquid Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000000926 separation method Methods 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000012431 aqueous reaction media Substances 0.000 description 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 239000001166 ammonium sulphate Substances 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000000337 buffer salt Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- VLUZIHGARVHSCE-UHFFFAOYSA-N cyclohexanone;n-cyclohexylidenehydroxylamine Chemical compound O=C1CCCCC1.ON=C1CCCCC1 VLUZIHGARVHSCE-UHFFFAOYSA-N 0.000 description 1
- 230000001934 delay Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- RBLWMQWAHONKNC-UHFFFAOYSA-N hydroxyazanium Chemical compound O[NH3+] RBLWMQWAHONKNC-UHFFFAOYSA-N 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 239000002912 waste gas Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B21/00—Nitrogen; Compounds thereof
- C01B21/082—Compounds containing nitrogen and non-metals and optionally metals
- C01B21/14—Hydroxylamine; Salts thereof
- C01B21/1409—Preparation
- C01B21/1418—Preparation by catalytic reduction of nitrogen oxides or nitrates with hydrogen
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL6918366A NL6918366A (enExample) | 1969-12-06 | 1969-12-06 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2059582A1 DE2059582A1 (de) | 1971-06-16 |
| DE2059582B2 DE2059582B2 (de) | 1979-11-22 |
| DE2059582C3 true DE2059582C3 (de) | 1980-08-07 |
Family
ID=19808575
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2059582A Expired DE2059582C3 (de) | 1969-12-06 | 1970-12-03 | Kreislaufverfahren zur Herstellung von Cyclohexanonoxim |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPS4835256B1 (enExample) |
| AT (1) | AT318540B (enExample) |
| BE (1) | BE759915A (enExample) |
| BG (1) | BG20318A3 (enExample) |
| CA (1) | CA944362A (enExample) |
| CH (1) | CH563355A5 (enExample) |
| CS (1) | CS174807B2 (enExample) |
| DE (1) | DE2059582C3 (enExample) |
| ES (1) | ES386192A1 (enExample) |
| FR (1) | FR2080887B1 (enExample) |
| GB (1) | GB1283496A (enExample) |
| NL (1) | NL6918366A (enExample) |
| PL (1) | PL80791B1 (enExample) |
| SE (1) | SE372525B (enExample) |
| ZA (1) | ZA708125B (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3997607A (en) * | 1974-04-26 | 1976-12-14 | Stamicarbon B.V. | Recycling process for the preparation of cyclohexanone oxime |
| US6844469B2 (en) * | 2000-06-05 | 2005-01-18 | Dsm Ip Assets B.V. | Process for the production of cyclohexanone oxime |
| EP1299353B1 (en) * | 2000-06-05 | 2006-04-12 | DSM IP Assets B.V. | Process for the preparation of cyclohexanone oxime |
| CN1200928C (zh) * | 2000-06-05 | 2005-05-11 | Dsmip财产有限公司 | 制备环己酮肟的方法 |
| AU2002347664A1 (en) * | 2001-12-04 | 2003-06-17 | Dsm Ip Assets B.V. | Process for treating an aqueous medium containing phosphate salt and organic compounds |
| PL1901994T3 (pl) * | 2005-07-08 | 2010-06-30 | Dsm Ip Assets Bv | Sposób ciągłego wytwarzania hydroksyloaminy |
| CN117446763B (zh) * | 2023-10-11 | 2025-09-19 | 浙江锦华新材料股份有限公司 | 一种环己酮肟催化水解制备羟胺水溶液的方法 |
-
0
- BE BE759915D patent/BE759915A/xx unknown
-
1969
- 1969-12-06 NL NL6918366A patent/NL6918366A/xx unknown
-
1970
- 1970-11-30 GB GB56740/70A patent/GB1283496A/en not_active Expired
- 1970-12-01 ZA ZA708125A patent/ZA708125B/xx unknown
- 1970-12-03 DE DE2059582A patent/DE2059582C3/de not_active Expired
- 1970-12-04 FR FR7043713A patent/FR2080887B1/fr not_active Expired
- 1970-12-04 CA CA099,821A patent/CA944362A/en not_active Expired
- 1970-12-04 AT AT1092670A patent/AT318540B/de not_active IP Right Cessation
- 1970-12-04 CS CS8201A patent/CS174807B2/cs unknown
- 1970-12-04 CH CH1801970A patent/CH563355A5/xx not_active IP Right Cessation
- 1970-12-04 ES ES386192A patent/ES386192A1/es not_active Expired
- 1970-12-04 JP JP45107531A patent/JPS4835256B1/ja active Pending
- 1970-12-05 PL PL1970145607A patent/PL80791B1/pl unknown
- 1970-12-05 BG BG016224A patent/BG20318A3/xx unknown
- 1970-12-07 SE SE7016545A patent/SE372525B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BG20318A3 (bg) | 1975-11-05 |
| CH563355A5 (enExample) | 1975-06-30 |
| GB1283496A (en) | 1972-07-26 |
| FR2080887B1 (enExample) | 1974-05-10 |
| PL80791B1 (en) | 1975-08-30 |
| CA944362A (en) | 1974-03-26 |
| FR2080887A1 (enExample) | 1971-11-26 |
| AT318540B (de) | 1974-10-25 |
| ES386192A1 (es) | 1973-03-16 |
| SE372525B (enExample) | 1974-12-23 |
| DE2059582B2 (de) | 1979-11-22 |
| ZA708125B (en) | 1971-08-25 |
| DE2059582A1 (de) | 1971-06-16 |
| BE759915A (fr) | 1971-06-04 |
| NL6918366A (enExample) | 1971-06-08 |
| CS174807B2 (enExample) | 1977-04-29 |
| JPS4835256B1 (enExample) | 1973-10-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |