CH378873A - Verfahren zur Herstellung von Cyclohexanol und Cyclohexanon - Google Patents
Verfahren zur Herstellung von Cyclohexanol und CyclohexanonInfo
- Publication number
- CH378873A CH378873A CH6390758A CH6390758A CH378873A CH 378873 A CH378873 A CH 378873A CH 6390758 A CH6390758 A CH 6390758A CH 6390758 A CH6390758 A CH 6390758A CH 378873 A CH378873 A CH 378873A
- Authority
- CH
- Switzerland
- Prior art keywords
- cyclohexane
- oxidation
- cyclohexanol
- cyclohexanone
- oxygen
- Prior art date
Links
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 title claims description 44
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 title claims description 23
- 238000000034 method Methods 0.000 title claims description 15
- 238000004519 manufacturing process Methods 0.000 title claims 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 51
- 230000003647 oxidation Effects 0.000 claims description 30
- 238000007254 oxidation reaction Methods 0.000 claims description 30
- 238000004821 distillation Methods 0.000 claims description 22
- 239000007789 gas Substances 0.000 claims description 22
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 15
- 239000001301 oxygen Substances 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 7
- 238000007127 saponification reaction Methods 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 6
- 230000001590 oxidative effect Effects 0.000 claims description 6
- 238000005406 washing Methods 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 5
- 239000007791 liquid phase Substances 0.000 claims description 5
- 150000002978 peroxides Chemical class 0.000 claims description 5
- 238000004508 fractional distillation Methods 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 230000006378 damage Effects 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- 230000001419 dependent effect Effects 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
- 239000006227 byproduct Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000006386 neutralization reaction Methods 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 238000001256 steam distillation Methods 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 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
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- -1 35.1 Vol. 1% Chemical compound 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 150000001934 cyclohexanes Chemical class 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- FGGJBCRKSVGDPO-UHFFFAOYSA-N hydroperoxycyclohexane Chemical compound OOC1CCCCC1 FGGJBCRKSVGDPO-UHFFFAOYSA-N 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/48—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups
- C07C29/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups with molecular oxygen only
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
-
- 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
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
-
- 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
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/53—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of hydroperoxides
-
- 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
- C07C45/83—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation by extractive distillation
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH6390758A CH378873A (de) | 1958-09-13 | 1958-09-13 | Verfahren zur Herstellung von Cyclohexanol und Cyclohexanon |
| DK260159AA DK90173C (da) | 1958-09-13 | 1959-07-21 | Fremgangsmåde ved fremstilling af cyclohexanol og cyclohexanon. |
| AT537459A AT212299B (de) | 1958-09-13 | 1959-07-22 | Verfahren zur Herstellung von Cyclohexanol und Cyclohexanon |
| ES0251039A ES251039A1 (es) | 1958-09-13 | 1959-07-24 | Un procedimiento para la fabricaciën de ciclohexanol y ciclohexanona |
| NL241980A NL103690C (en)) | 1958-09-13 | 1959-08-04 | |
| FR802582A FR1233829A (fr) | 1958-09-13 | 1959-08-11 | Procédé d'oxydation du cyclohexane |
| DEI16883A DE1100020B (de) | 1958-09-13 | 1959-08-24 | Verfahren zur destillativen Zerlegung von Reaktionsgemischen, die aus der Oxydation von Cyclohexan stammen |
| GB29670/59A GB878066A (en) | 1958-09-13 | 1959-08-31 | Process for producing cyclohexanol and cyclohexanone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH6390758A CH378873A (de) | 1958-09-13 | 1958-09-13 | Verfahren zur Herstellung von Cyclohexanol und Cyclohexanon |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH378873A true CH378873A (de) | 1964-06-30 |
Family
ID=4525301
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH6390758A CH378873A (de) | 1958-09-13 | 1958-09-13 | Verfahren zur Herstellung von Cyclohexanol und Cyclohexanon |
Country Status (8)
| Country | Link |
|---|---|
| AT (1) | AT212299B (en)) |
| CH (1) | CH378873A (en)) |
| DE (1) | DE1100020B (en)) |
| DK (1) | DK90173C (en)) |
| ES (1) | ES251039A1 (en)) |
| FR (1) | FR1233829A (en)) |
| GB (1) | GB878066A (en)) |
| NL (1) | NL103690C (en)) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3274254A (en) * | 1966-09-20 | Oxidation of cyclohexane | ||
| DE1150674B (de) * | 1961-06-05 | 1963-06-27 | Huels Chemische Werke Ag | Verfahren zur mehrstufigen Fluessigphasenoxydation von Cyclohexan |
| NL283634A (en)) * | 1961-09-26 | |||
| US3452047A (en) * | 1965-11-23 | 1969-06-24 | Cincinnati Milling Machine Co | Oxidation of olefinic compounds with solutions of thallium(iii) salts |
| PL70457B1 (en)) * | 1970-03-11 | 1974-02-28 | ||
| DE2127520A1 (de) * | 1971-06-03 | 1972-12-14 | Badische Anilin- & Soda-Fabrik Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von Cycloalkanol- und Cycloalkanon-Gemischen |
| PL227792B1 (pl) * | 2012-03-23 | 2018-01-31 | Korzeniowski Waclaw Chemenergia | Sposób otrzymywania estrów syntetycznych |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE859465C (de) * | 1941-04-13 | 1952-12-15 | Basf Ag | Verfahren zur Herstellung cycloaliphatischer Ketone und Alkohole neben Dicarbonsaeuren |
| FR886795A (fr) * | 1941-12-10 | 1943-10-25 | Ig Farbenindustrie Ag | Procédé de préparation de produits d'oxydation d'hydrocarbures cycliques saturés |
| DE969501C (de) * | 1951-12-13 | 1958-06-12 | Huels Chemische Werke Ag | Verfahren zum Entfernen von stoerenden Verunreinigungen aus Cyclohexanol-Cyclohexanon-Gemischen |
| US2825742A (en) * | 1954-05-04 | 1958-03-04 | Du Pont | Liquid phase oxidation of cyclohexane |
| DE1002754B (de) * | 1954-05-12 | 1957-02-21 | Du Pont | Verfahren zur Herstellung von zur Adipinsaeureherstellung geeigneten Gemischen aus Cyclohexanon und Cyclohexanol |
| DE1067429B (de) * | 1956-02-08 | 1959-10-22 | Basf Ag | Verfahren zur destillativen Zerlegung von Gemischen cycloaliphatischer Kohlenwasserstoffe und deren Oxydationsprodukten |
-
1958
- 1958-09-13 CH CH6390758A patent/CH378873A/de unknown
-
1959
- 1959-07-21 DK DK260159AA patent/DK90173C/da active
- 1959-07-22 AT AT537459A patent/AT212299B/de active
- 1959-07-24 ES ES0251039A patent/ES251039A1/es not_active Expired
- 1959-08-04 NL NL241980A patent/NL103690C/nl active
- 1959-08-11 FR FR802582A patent/FR1233829A/fr not_active Expired
- 1959-08-24 DE DEI16883A patent/DE1100020B/de active Pending
- 1959-08-31 GB GB29670/59A patent/GB878066A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DK90173C (da) | 1960-12-27 |
| GB878066A (en) | 1961-09-27 |
| FR1233829A (fr) | 1960-10-12 |
| AT212299B (de) | 1960-12-12 |
| NL103690C (en)) | 1963-01-15 |
| DE1100020B (de) | 1961-02-23 |
| ES251039A1 (es) | 1960-03-01 |
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