CH630332A5 - Verfahren zur aufarbeitung von cyclohexanol und cyclohexanon enthaltenden reaktionsgemischen. - Google Patents
Verfahren zur aufarbeitung von cyclohexanol und cyclohexanon enthaltenden reaktionsgemischen. Download PDFInfo
- Publication number
- CH630332A5 CH630332A5 CH1339377A CH1339377A CH630332A5 CH 630332 A5 CH630332 A5 CH 630332A5 CH 1339377 A CH1339377 A CH 1339377A CH 1339377 A CH1339377 A CH 1339377A CH 630332 A5 CH630332 A5 CH 630332A5
- Authority
- CH
- Switzerland
- Prior art keywords
- stage
- cyclohexanone
- reaction mixture
- cyclohexanol
- via line
- Prior art date
Links
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 title claims description 40
- 239000011541 reaction mixture Substances 0.000 title claims description 32
- 238000000034 method Methods 0.000 title claims description 20
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 title claims description 19
- 239000000243 solution Substances 0.000 claims description 24
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 17
- 239000002699 waste material Substances 0.000 claims description 17
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 15
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 14
- 239000011261 inert gas Substances 0.000 claims description 14
- 239000007789 gas Substances 0.000 claims description 13
- 230000003647 oxidation Effects 0.000 claims description 10
- 238000007254 oxidation reaction Methods 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 9
- 229910001385 heavy metal Inorganic materials 0.000 claims description 9
- 150000002736 metal compounds Chemical class 0.000 claims description 7
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 6
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 5
- 229910001882 dioxygen Inorganic materials 0.000 claims description 5
- 239000007791 liquid phase Substances 0.000 claims description 4
- ZWAJLVLEBYIOTI-OLQVQODUSA-N (1s,6r)-7-oxabicyclo[4.1.0]heptane Chemical compound C1CCC[C@@H]2O[C@@H]21 ZWAJLVLEBYIOTI-OLQVQODUSA-N 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 48
- 239000002253 acid Substances 0.000 description 10
- 150000007513 acids Chemical class 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
- 239000008346 aqueous phase Substances 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- 239000006227 byproduct Substances 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 150000001450 anions Chemical class 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 150000001924 cycloalkanes Chemical class 0.000 description 3
- 239000002351 wastewater Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- -1 alkyl radical Chemical class 0.000 description 2
- 150000001869 cobalt compounds Chemical class 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- TVACALAUIQMRDF-UHFFFAOYSA-N dodecyl dihydrogen phosphate Chemical compound CCCCCCCCCCCCOP(O)(O)=O TVACALAUIQMRDF-UHFFFAOYSA-N 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- WRKCIHRWQZQBOL-UHFFFAOYSA-N phosphoric Acid Monooctyl Ester Natural products CCCCCCCCOP(O)(O)=O WRKCIHRWQZQBOL-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UZZYXUGECOQHPU-UHFFFAOYSA-N sulfuric acid monooctyl ester Natural products CCCCCCCCOS(O)(=O)=O UZZYXUGECOQHPU-UHFFFAOYSA-N 0.000 description 2
- 239000002912 waste gas Substances 0.000 description 2
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
- QWHHBVWZZLQUIH-UHFFFAOYSA-N 2-octylbenzenesulfonic acid Chemical compound CCCCCCCCC1=CC=CC=C1S(O)(=O)=O QWHHBVWZZLQUIH-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- OAEOHDYTAZVCMS-UHFFFAOYSA-L P(=O)(OCCCCCCCCCCCC)(OCCCCCCCCCCCC)[O-].[Co+2].C(CCCCCCCCCCC)OP(=O)(OCCCCCCCCCCCC)[O-] Chemical compound P(=O)(OCCCCCCCCCCCC)(OCCCCCCCCCCCC)[O-].[Co+2].C(CCCCCCCCCCC)OP(=O)(OCCCCCCCCCCCC)[O-] OAEOHDYTAZVCMS-UHFFFAOYSA-L 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- JTXUVYOABGUBMX-UHFFFAOYSA-N didodecyl hydrogen phosphate Chemical compound CCCCCCCCCCCCOP(O)(=O)OCCCCCCCCCCCC JTXUVYOABGUBMX-UHFFFAOYSA-N 0.000 description 1
- HTDKEJXHILZNPP-UHFFFAOYSA-N dioctyl hydrogen phosphate Chemical compound CCCCCCCCOP(O)(=O)OCCCCCCCC HTDKEJXHILZNPP-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical class CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 125000005609 naphthenate group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C27/00—Processes involving the simultaneous production of more than one class of oxygen-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C27/00—Processes involving the simultaneous production of more than one class of oxygen-containing compounds
- C07C27/10—Processes involving the simultaneous production of more than one class of oxygen-containing compounds by oxidation of hydrocarbons
- C07C27/12—Processes involving the simultaneous production of more than one class of oxygen-containing compounds by oxidation of hydrocarbons with oxygen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C27/00—Processes involving the simultaneous production of more than one class of oxygen-containing compounds
- C07C27/26—Purification; Separation; Stabilisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic
- C07C35/08—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic containing a six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/29—Saturated compounds containing keto groups bound to rings
- C07C49/303—Saturated compounds containing keto groups bound to rings to a six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/385—Saturated compounds containing a keto group being part of a ring
- C07C49/403—Saturated compounds containing a keto group being part of a ring of a six-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2650892A DE2650892C3 (de) | 1976-11-06 | 1976-11-06 | Verfahren zur Aufarbeitung von Cyclohexanol und Cyclohexanon enthaltenden Reaktionsgemischen |
| DE2745448A DE2745448C3 (de) | 1977-10-08 | 1977-10-08 | Verfahren zur Aufarbeitung von Cyclohexanol und Cyclohexanon enthaltenden Reaktionsgemischen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH630332A5 true CH630332A5 (de) | 1982-06-15 |
Family
ID=25771116
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1339377A CH630332A5 (de) | 1976-11-06 | 1977-11-03 | Verfahren zur aufarbeitung von cyclohexanol und cyclohexanon enthaltenden reaktionsgemischen. |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4163027A (en, 2012) |
| CH (1) | CH630332A5 (en, 2012) |
| FR (1) | FR2370018A1 (en, 2012) |
| GB (1) | GB1586836A (en, 2012) |
| IT (1) | IT1115535B (en, 2012) |
| NL (1) | NL184060C (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0212217A1 (de) * | 1985-07-24 | 1987-03-04 | BASF Aktiengesellschaft | Verfahren zur Stabilisierung von sauren Waschwässern |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7904651A (nl) * | 1979-06-14 | 1980-12-16 | Stamicarbon | Werkwijze voor het verwijderen van alkalimetaalcarboxy- laten uit cycloalkanon en cycloalkanol bevattende meng- sels verkregen bij oxidatie van cycloalkanen. |
| DE3513568A1 (de) * | 1985-04-16 | 1986-10-16 | Basf Ag, 6700 Ludwigshafen | Verfahren zur aufarbeitung von cyclohexanol, cyclohexanon sowie cyclohexylhydroperoxid enthaltenden reaktionsgemischen |
| BE1009662A3 (nl) * | 1995-10-13 | 1997-06-03 | Dsm Nv | Werkwijze voor het ontleden van cycloalkylhydroperoxide. |
| US7956221B2 (en) | 2004-12-22 | 2011-06-07 | Dsm Ip Assets B.V. | Process for decomposing cyclohexylhydroperoxide |
| CN101734689B (zh) * | 2008-11-27 | 2013-08-07 | 华东理工大学 | 对环己烷氧化液中的废碱进行分离回收的方法和装置 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2931834A (en) * | 1960-04-05 | Ctclohexane oxidation process | ||
| DE1046610B (de) * | 1955-06-15 | 1958-12-18 | Basf Ag | Verfahren zur Herstellung von Cyclohexanol und Cyclohexanon durch Oxydation von Cyclohexan |
| NL95163C (nl) * | 1955-06-15 | 1960-08-15 | Basf Ag | Werkwijze ter bereiding van alcoholen en ketonen door oxydatie van cycloalifatische koolwaterstoffen |
| BE659166A (en, 2012) * | 1964-02-03 | 1965-08-02 | ||
| DE1518255B1 (de) * | 1965-01-30 | 1969-12-11 | Vickers Zimmer Ag | Verfahren zur Aufarbeitung des Reaktionsgemisches der Oxydation von Cyclohexan mit sauerstoffhaltigen Gasen in fluessiger Phase |
| US3551482A (en) * | 1966-06-14 | 1970-12-29 | Vickers Zimmer Ag | Cyclohexane oxidation products recovery |
| NL7004497A (en) * | 1970-03-28 | 1971-09-30 | Cyclohexanol and cyclohexanone from cyclohexane oxidn | |
| DE2127520A1 (de) * | 1971-06-03 | 1972-12-14 | Badische Anilin- & Soda-Fabrik Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von Cycloalkanol- und Cycloalkanon-Gemischen |
| DE2315350C3 (de) * | 1973-03-28 | 1979-02-15 | Bayer Ag, 5090 Leverkusen | Verfahren zur Oxidation von aliphatischen und cycloaliphatischen C5-C12-Kohlenwasserstoffen |
-
1977
- 1977-10-25 US US05/844,985 patent/US4163027A/en not_active Expired - Lifetime
- 1977-10-31 NL NLAANVRAGE7711954,A patent/NL184060C/xx not_active IP Right Cessation
- 1977-11-03 IT IT29344/77A patent/IT1115535B/it active
- 1977-11-03 CH CH1339377A patent/CH630332A5/de not_active IP Right Cessation
- 1977-11-04 FR FR7733182A patent/FR2370018A1/fr active Granted
- 1977-11-04 GB GB45922/77A patent/GB1586836A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0212217A1 (de) * | 1985-07-24 | 1987-03-04 | BASF Aktiengesellschaft | Verfahren zur Stabilisierung von sauren Waschwässern |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1586836A (en) | 1981-03-25 |
| IT1115535B (it) | 1986-02-03 |
| NL184060C (nl) | 1989-04-03 |
| FR2370018A1 (fr) | 1978-06-02 |
| NL7711954A (nl) | 1978-05-09 |
| FR2370018B1 (en, 2012) | 1983-09-23 |
| US4163027A (en) | 1979-07-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |