DE2518259A1 - Kreislaufverfahren zur herstellung von cyclohexanonoxim - Google Patents
Kreislaufverfahren zur herstellung von cyclohexanonoximInfo
- Publication number
- DE2518259A1 DE2518259A1 DE19752518259 DE2518259A DE2518259A1 DE 2518259 A1 DE2518259 A1 DE 2518259A1 DE 19752518259 DE19752518259 DE 19752518259 DE 2518259 A DE2518259 A DE 2518259A DE 2518259 A1 DE2518259 A1 DE 2518259A1
- Authority
- DE
- Germany
- Prior art keywords
- cyclohexanone
- hydroxylammonium
- salt
- cyclohexanone oxime
- zone
- 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
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 title claims description 46
- 238000000034 method Methods 0.000 title claims description 15
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 239000007789 gas Substances 0.000 claims description 33
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 claims description 28
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 26
- 239000012530 fluid Substances 0.000 claims description 21
- -1 nitrate ions Chemical class 0.000 claims description 19
- 230000015572 biosynthetic process Effects 0.000 claims description 17
- 238000003786 synthesis reaction Methods 0.000 claims description 15
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 14
- 239000007788 liquid Substances 0.000 claims description 12
- 238000010438 heat treatment Methods 0.000 claims description 10
- 229910002651 NO3 Inorganic materials 0.000 claims description 7
- 239000012431 aqueous reaction media Substances 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 239000000337 buffer salt Substances 0.000 claims description 4
- 150000003863 ammonium salts Chemical class 0.000 claims description 3
- 238000010531 catalytic reduction reaction Methods 0.000 claims description 2
- LSRPARCOXAUYNP-UHFFFAOYSA-N cyclohexylidene(oxido)oxidanium Chemical compound [O-][O+]=C1CCCCC1 LSRPARCOXAUYNP-UHFFFAOYSA-N 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 17
- 239000003054 catalyst Substances 0.000 description 15
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 238000010521 absorption reaction Methods 0.000 description 7
- MGWGWNFMUOTEHG-UHFFFAOYSA-N 4-(3,5-dimethylphenyl)-1,3-thiazol-2-amine Chemical compound CC1=CC(C)=CC(C=2N=C(N)SC=2)=C1 MGWGWNFMUOTEHG-UHFFFAOYSA-N 0.000 description 5
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 229910017604 nitric acid Inorganic materials 0.000 description 5
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 5
- 231100000614 poison Toxicity 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000002574 poison Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- RBLWMQWAHONKNC-UHFFFAOYSA-N hydroxyazanium Chemical compound O[NH3+] RBLWMQWAHONKNC-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 235000011007 phosphoric acid Nutrition 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
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229910001260 Pt alloy Inorganic materials 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
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- LFVGISIMTYGQHF-UHFFFAOYSA-N ammonium dihydrogen phosphate Chemical compound [NH4+].OP(O)([O-])=O LFVGISIMTYGQHF-UHFFFAOYSA-N 0.000 description 1
- 229910000387 ammonium dihydrogen phosphate Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 238000007084 catalytic combustion reaction Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000003946 cyclohexylamines Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000019837 monoammonium phosphate Nutrition 0.000 description 1
- 239000006012 monoammonium phosphate Substances 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 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
- JRTYPQGPARWINR-UHFFFAOYSA-N palladium platinum Chemical compound [Pd].[Pt] JRTYPQGPARWINR-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- 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
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL7405630A NL7405630A (nl) | 1974-04-26 | 1974-04-26 | Kringloopproces voor de bereiding van cyclohexanonoxim. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2518259A1 true DE2518259A1 (de) | 1975-11-06 |
Family
ID=19821235
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752518259 Pending DE2518259A1 (de) | 1974-04-26 | 1975-04-24 | Kreislaufverfahren zur herstellung von cyclohexanonoxim |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPS50154224A (enExample) |
| AR (1) | AR202611A1 (enExample) |
| BE (1) | BE828393A (enExample) |
| BR (1) | BR7502549A (enExample) |
| CH (1) | CH609335A5 (enExample) |
| CS (1) | CS199266B2 (enExample) |
| DE (1) | DE2518259A1 (enExample) |
| ES (1) | ES436961A1 (enExample) |
| FR (1) | FR2268794B1 (enExample) |
| GB (1) | GB1506437A (enExample) |
| IT (1) | IT1035465B (enExample) |
| NL (1) | NL7405630A (enExample) |
| PL (1) | PL94769B1 (enExample) |
| RO (1) | RO73094A (enExample) |
| SU (1) | SU586838A3 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1303480B1 (en) | 2000-06-05 | 2009-03-18 | DSM IP Assets B.V. | Process for the production of cyclohexanone oxime |
| BR0111439B1 (pt) * | 2000-06-05 | 2011-08-09 | processo para a produção de ciclohexanona oxima. | |
| KR100917544B1 (ko) * | 2001-12-04 | 2009-09-16 | 디에스엠 아이피 어셋츠 비.브이. | 인산염 및 유기 화합물을 함유하는 수성 매질의 처리 방법 |
-
1974
- 1974-04-26 NL NL7405630A patent/NL7405630A/xx not_active Application Discontinuation
-
1975
- 1975-04-22 GB GB1666/75A patent/GB1506437A/en not_active Expired
- 1975-04-24 DE DE19752518259 patent/DE2518259A1/de active Pending
- 1975-04-24 FR FR7512794A patent/FR2268794B1/fr not_active Expired
- 1975-04-24 CS CS752884A patent/CS199266B2/cs unknown
- 1975-04-24 JP JP50050167A patent/JPS50154224A/ja active Pending
- 1975-04-24 SU SU752126766A patent/SU586838A3/ru active
- 1975-04-24 IT IT49299/75A patent/IT1035465B/it active
- 1975-04-25 CH CH530775A patent/CH609335A5/xx not_active IP Right Cessation
- 1975-04-25 RO RO7582088A patent/RO73094A/ro unknown
- 1975-04-25 PL PL1975179927A patent/PL94769B1/pl unknown
- 1975-04-25 ES ES436961A patent/ES436961A1/es not_active Expired
- 1975-04-25 BR BR3233/75A patent/BR7502549A/pt unknown
- 1975-04-25 BE BE155775A patent/BE828393A/xx unknown
- 1975-04-28 AR AR258525A patent/AR202611A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| BE828393A (nl) | 1975-10-27 |
| FR2268794B1 (enExample) | 1979-10-05 |
| RO73094A (ro) | 1982-02-26 |
| GB1506437A (en) | 1978-04-05 |
| FR2268794A1 (enExample) | 1975-11-21 |
| CH609335A5 (en) | 1979-02-28 |
| SU586838A3 (ru) | 1977-12-30 |
| ES436961A1 (es) | 1976-12-01 |
| CS199266B2 (en) | 1980-07-31 |
| NL7405630A (nl) | 1975-10-28 |
| IT1035465B (it) | 1979-10-20 |
| PL94769B1 (pl) | 1977-08-31 |
| BR7502549A (pt) | 1976-03-03 |
| JPS50154224A (enExample) | 1975-12-12 |
| AR202611A1 (es) | 1975-06-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |