GB878066A - Process for producing cyclohexanol and cyclohexanone - Google Patents
Process for producing cyclohexanol and cyclohexanoneInfo
- Publication number
- GB878066A GB878066A GB29670/59A GB2967059A GB878066A GB 878066 A GB878066 A GB 878066A GB 29670/59 A GB29670/59 A GB 29670/59A GB 2967059 A GB2967059 A GB 2967059A GB 878066 A GB878066 A GB 878066A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cyclohexane
- oxidation
- cyclohexanone
- cyclohexanol
- reaction mixture
- 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 title abstract 8
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 title abstract 4
- 238000000034 method Methods 0.000 title abstract 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 abstract 7
- 230000003647 oxidation Effects 0.000 abstract 6
- 238000007254 oxidation reaction Methods 0.000 abstract 6
- 239000002253 acid Substances 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 239000007789 gas Substances 0.000 abstract 2
- 239000007788 liquid Substances 0.000 abstract 2
- 239000011541 reaction mixture Substances 0.000 abstract 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 229910001882 dioxygen Inorganic materials 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 238000004508 fractional distillation Methods 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 230000003472 neutralizing effect Effects 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 150000002978 peroxides Chemical class 0.000 abstract 1
- 238000004064 recycling Methods 0.000 abstract 1
- 238000007670 refining Methods 0.000 abstract 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)
- Chemical Kinetics & Catalysis (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
A process for the manufacture of cyclohexanone and cyclohexanol by partial oxidation of cyclohexane with molecular oxygen-containing gases at elevated temperatures and pressures in a liquid system, comprises limiting the oxidation of said cyclohexane to not more than 10% by weight calculated on the input of cyclohexane, using a retention-time in the reactor of one half to two hours and by using a gas for the oxidation containing at the most 10% by volume oxygen; decomposing the peroxides formed during oxidation; saponifying the esters formed and neutralising the acids formed during the oxidation and removing the saponified esters and neutralised acids; expanding the reaction mixture for distillation; drawing off cyclohexane vapours thus liberated and compressing them; using the heat evolved to heat the reaction mixture to be distilled; conducting part of the now liquid cyclohexane to the still head and recycling the remainder; separating the crude cyclohexanone and cyclohexanol from unreacted cyclohexane in the still bottoms and refining the cyclohexanol and cyclohexanone by fractional distillation. The continuous oxidation of cyclohexane by the above process and an apparatus therefor is described.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH6390758A CH378873A (en) | 1958-09-13 | 1958-09-13 | Process for the production of cyclohexanol and cyclohexanone |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB878066A true GB878066A (en) | 1961-09-27 |
Family
ID=4525301
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB29670/59A Expired GB878066A (en) | 1958-09-13 | 1959-08-31 | Process for producing cyclohexanol and cyclohexanone |
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) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3274254A (en) * | 1966-09-20 | Oxidation of cyclohexane | ||
| WO2013141726A1 (en) * | 2012-03-23 | 2013-09-26 | Chemenergia Korzeniowski Wacław | Method of manufacturing synthetic esters |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1150674B (en) * | 1961-06-05 | 1963-06-27 | Huels Chemische Werke Ag | Process for the multistage liquid phase oxidation of cyclohexane |
| 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 (en) * | 1971-06-03 | 1972-12-14 | Badische Anilin- & Soda-Fabrik Ag, 6700 Ludwigshafen | Process for the preparation of cycloalkanol and cycloalkanone mixtures |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE859465C (en) * | 1941-04-13 | 1952-12-15 | Basf Ag | Process for the production of cycloaliphatic ketones and alcohols in addition to dicarboxylic acids |
| FR886795A (en) * | 1941-12-10 | 1943-10-25 | Ig Farbenindustrie Ag | Process for the preparation of oxidation products of saturated cyclic hydrocarbons |
| DE969501C (en) * | 1951-12-13 | 1958-06-12 | Huels Chemische Werke Ag | Process for removing disruptive impurities from cyclohexanol-cyclohexanone mixtures |
| US2825742A (en) * | 1954-05-04 | 1958-03-04 | Du Pont | Liquid phase oxidation of cyclohexane |
| DE1002754B (en) * | 1954-05-12 | 1957-02-21 | Du Pont | Process for the production of mixtures of cyclohexanone and cyclohexanol suitable for the production of adipic acid |
| DE1067429B (en) * | 1956-02-08 | 1959-10-22 | Basf Ag | Process for the decomposition of mixtures of cycloaliphatic hydrocarbons and their oxidation products by distillation |
-
1958
- 1958-09-13 CH CH6390758A patent/CH378873A/en unknown
-
1959
- 1959-07-21 DK DK260159AA patent/DK90173C/en active
- 1959-07-22 AT AT537459A patent/AT212299B/en active
- 1959-07-24 ES ES0251039A patent/ES251039A1/en not_active Expired
- 1959-08-04 NL NL241980A patent/NL103690C/nl active
- 1959-08-11 FR FR802582A patent/FR1233829A/en not_active Expired
- 1959-08-24 DE DEI16883A patent/DE1100020B/en active Pending
- 1959-08-31 GB GB29670/59A patent/GB878066A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3274254A (en) * | 1966-09-20 | Oxidation of cyclohexane | ||
| WO2013141726A1 (en) * | 2012-03-23 | 2013-09-26 | Chemenergia Korzeniowski Wacław | Method of manufacturing synthetic esters |
| CN104024195A (en) * | 2012-03-23 | 2014-09-03 | 瓦茨瓦夫·科热日尼奥夫斯基化工能源公司 | Method of manufacturing synthetic esters |
| CN104024195B (en) * | 2012-03-23 | 2015-12-02 | 瓦茨瓦夫·科热日尼奥夫斯基化工能源公司 | Prepare the method for synthetic ester |
Also Published As
| Publication number | Publication date |
|---|---|
| NL103690C (en) | 1963-01-15 |
| FR1233829A (en) | 1960-10-12 |
| ES251039A1 (en) | 1960-03-01 |
| DE1100020B (en) | 1961-02-23 |
| CH378873A (en) | 1964-06-30 |
| DK90173C (en) | 1960-12-27 |
| AT212299B (en) | 1960-12-12 |
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