US1892011A - Process for the production of ketones from secondary alcohols - Google Patents
Process for the production of ketones from secondary alcohols Download PDFInfo
- Publication number
- US1892011A US1892011A US458934A US45893430A US1892011A US 1892011 A US1892011 A US 1892011A US 458934 A US458934 A US 458934A US 45893430 A US45893430 A US 45893430A US 1892011 A US1892011 A US 1892011A
- Authority
- US
- United States
- Prior art keywords
- ketones
- production
- steam
- secondary alcohols
- catalysts
- 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 - Lifetime
Links
- 150000002576 ketones Chemical class 0.000 title description 10
- 238000000034 method Methods 0.000 title description 7
- 150000003333 secondary alcohols Chemical class 0.000 title description 7
- 238000004519 manufacturing process Methods 0.000 title description 6
- 239000003054 catalyst Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 238000006356 dehydrogenation reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 2
- NFLGAXVYCFJBMK-RKDXNWHRSA-N (+)-isomenthone Natural products CC(C)[C@H]1CC[C@@H](C)CC1=O NFLGAXVYCFJBMK-RKDXNWHRSA-N 0.000 description 2
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 2
- NFLGAXVYCFJBMK-UHFFFAOYSA-N Menthone Chemical compound CC(C)C1CCC(C)CC1=O NFLGAXVYCFJBMK-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229940041616 menthol Drugs 0.000 description 2
- 229930007503 menthone Natural products 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical compound C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical compound CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DTGKSKDOIYIVQL-MRTMQBJTSA-N Isoborneol Natural products C1C[C@@]2(C)[C@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-MRTMQBJTSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- XPNGNIFUDRPBFJ-UHFFFAOYSA-N alpha-methylbenzylalcohol Natural products CC1=CC=CC=C1CO XPNGNIFUDRPBFJ-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- CKDOCTFBFTVPSN-UHFFFAOYSA-N borneol Natural products C1CC2(C)C(C)CC1C2(C)C CKDOCTFBFTVPSN-UHFFFAOYSA-N 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- DTGKSKDOIYIVQL-UHFFFAOYSA-N dl-isoborneol Natural products C1CC2(C)C(O)CC1C2(C)C DTGKSKDOIYIVQL-UHFFFAOYSA-N 0.000 description 1
- 239000007792 gaseous phase Substances 0.000 description 1
- ZRJUCHNILNOEKV-UHFFFAOYSA-N hexan-2-one hydrate Chemical compound O.CCCCC(C)=O ZRJUCHNILNOEKV-UHFFFAOYSA-N 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
Classifications
-
- 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
- C07C45/002—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by dehydrogenation
Definitions
- Example J From a distillation apparatus charged with menthol a menthol-steam mixture is passed by means of steam through a tube system filled with dehyclrogenating catalysts and heated to about 185 (1, the end of which is provided with an efficient condenser.
- the condensate consists of water and menthone and is separated as usual. The yield of menthone amounts to 96%.
- Example 2 From a distillation apparatus charged with cyclohexanol a cyclohexanol-steam mixture is passed by means of steam through a tube system filled with dehydrogenating catalysts and heated up to about 180% 0., the end of which is provided with an efficient condenser.
- the condensate consists of water and cyclohexanone and is separated as usual.
- the cyclohexanone is formed in a 95% yield.
- Example 3 From a distillation apparatus isoborneol is passed by means of steam through a tube system filled with dehydrogenating catalysts and heated to about 180- 195 (3., the end of which is provided with a condenser.
- the solid reaction product obtained consists of about 99.5% camphor.
- methyl-phenyl-carbinol is led by means of steam at a temperature of l70180 C. through a tube system filled with dehydrogenating catalysts, the end of which is pro-- vided with an eificient condenser.
- the con densate consists of water and acetophenone and is separated as usual. The acetophenone is obtained in a yield of 97%.
- WVhat I claim is 1.
- a process for the production of ketones from secondary alcohols of the same number of carbon atoms which consists in leading the alcohol in the gaseous state with steam but in the absence of oxygen over dehydrogenating catalysts at a temperature not exceeding 300 C.
- a process for the production of ketones from secondary alcohols of the same number of carbon atoms which consists in leading the alcohol vapor from a distilling apparatus by means of steam but in the absence of oxygen over dehydrogenating catalysts at a temperature not exceeding 300 C.
- a process for the production of ketones from secondary alcohols of the same number of carbon atoms which consists in leading the alcohol vapor from a distilling apparatus by means of steam but in the absence of oxygen through a tube system filled with dehydrogenating catalysts at a temperature not exceeding 300 C.
- a process for the production of ketones from secondary alcohols of the same number of carbon atoms which consists in leading the alcohol vapor and steam from a distilling apparatus in the absence of oxygen through a tube system filled with dehydrogenating catalysts and provided with a condenser at a temperature not exceeding 300 C.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Patented Dec. 27, 1932 UNITED STATES PATENT OFFICE HERBMAN SANDKUHL, OF BUDERICH, GERMANY, .ASSIGNOR T0 FIRM: RI-IEINISOHE KAMPFER-FABRIK GESELLSCHAFT MIT BESCHRANKTER HAFTUNG AT DUSSELDORF- OBEB-KASSEL, GERMANY PROCESS FOR THE PRODUCTION OF KETONES FROM SECONDARY ALCOHOLS No Drawing. Application filed May 31, 1930, Serial No. 458,934, and in Germany June 14, 1929.
It is known that secondary alcohols, such as isopropyl alcohol, menthol, borneo-l and others, may be converted into the corresponding ketones by leading them over dehydrogenating catalysts. This dehydrogenation, however, never proceeds to completion, because the hydrogen formed itself further hydrogenates the ketone, so that the reaction product still contains considerable quantities of alcohol which must be separated from the ketone by particular methods.
It has now been found, that a 97100% dehydrogenation of the alcohols can be attained if they are led over the dehydrogenation catalysts in the presence of steam. The presence of the steam hinders the further hydrogenation of the already formed ketone and has at the same time the advantage, that the operation can be effected in the gaseous phase at temperatures which lie below the boiling point of the alcohols. In general temperatures of 120-300 C. can be employed. As catalysts there can be employed metals such as nickel, cobalt, copper, preferably in a powdered form eventually admixed with hydrates or oxides of the alkali or alkaline earth metals.
Example J.From a distillation apparatus charged with menthol a menthol-steam mixture is passed by means of steam through a tube system filled with dehyclrogenating catalysts and heated to about 185 (1, the end of which is provided with an efficient condenser. The condensate consists of water and menthone and is separated as usual. The yield of menthone amounts to 96%.
Example 2.From a distillation apparatus charged with cyclohexanol a cyclohexanol-steam mixture is passed by means of steam through a tube system filled with dehydrogenating catalysts and heated up to about 180% 0., the end of which is provided with an efficient condenser. The condensate consists of water and cyclohexanone and is separated as usual. The cyclohexanone is formed in a 95% yield.
Example 3.-From a distillation apparatus isoborneol is passed by means of steam through a tube system filled with dehydrogenating catalysts and heated to about 180- 195 (3., the end of which is provided with a condenser. The solid reaction product obtained consists of about 99.5% camphor.
'Emample 4.-From a distillation apparatus methyl-phenyl-carbinol is led by means of steam at a temperature of l70180 C. through a tube system filled with dehydrogenating catalysts, the end of which is pro-- vided with an eificient condenser. The con densate consists of water and acetophenone and is separated as usual. The acetophenone is obtained in a yield of 97%.
WVhat I claim is 1. A process for the production of ketones from secondary alcohols of the same number of carbon atoms which consists in leading the alcohol in the gaseous state with steam but in the absence of oxygen over dehydrogenating catalysts at a temperature not exceeding 300 C.
2. A process for the production of ketones from secondary alcohols of the same number of carbon atoms which consists in leading the alcohol vapor from a distilling apparatus by means of steam but in the absence of oxygen over dehydrogenating catalysts at a temperature not exceeding 300 C.
3. A process for the production of ketones from secondary alcohols of the same number of carbon atoms which consists in leading the alcohol vapor from a distilling apparatus by means of steam but in the absence of oxygen through a tube system filled with dehydrogenating catalysts at a temperature not exceeding 300 C.
4. A process for the production of ketones from secondary alcohols of the same number of carbon atoms which consists in leading the alcohol vapor and steam from a distilling apparatus in the absence of oxygen through a tube system filled with dehydrogenating catalysts and provided with a condenser at a temperature not exceeding 300 C.
In testimony hereof I hereunto afiix my signature this 19th day of May 1930.
HERRMAN SANDKUHL.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1892011X | 1929-06-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1892011A true US1892011A (en) | 1932-12-27 |
Family
ID=7747914
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US458934A Expired - Lifetime US1892011A (en) | 1929-06-14 | 1930-05-31 | Process for the production of ketones from secondary alcohols |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1892011A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2692289A (en) * | 1949-05-06 | 1954-10-19 | Distillers Co Yeast Ltd | Manufacture of 1:1:3-trimethylcyclohexanone-5 |
| US2970172A (en) * | 1959-04-21 | 1961-01-31 | Monsanto Chemicals | Preparation of cyclohexanone |
| US3006958A (en) * | 1958-11-18 | 1961-10-31 | Basf Ag | Production of cyclohexanone |
| US3149166A (en) * | 1959-12-28 | 1964-09-15 | Basf Ag | Process for the production of pure cyclohexanone |
| US3350456A (en) * | 1960-07-28 | 1967-10-31 | Inventa Ag | Process for preparing cyclohexanone from cyclohexanol |
| US3937735A (en) * | 1972-11-23 | 1976-02-10 | Stamicarbon B.V. | Process for the preparation of cyclohexanone |
| US4670605A (en) * | 1985-05-31 | 1987-06-02 | Industrial Technology Research Institute | Process and catalyst for the conversion of cyclohexanol to cyclohexanone |
-
1930
- 1930-05-31 US US458934A patent/US1892011A/en not_active Expired - Lifetime
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2692289A (en) * | 1949-05-06 | 1954-10-19 | Distillers Co Yeast Ltd | Manufacture of 1:1:3-trimethylcyclohexanone-5 |
| US3006958A (en) * | 1958-11-18 | 1961-10-31 | Basf Ag | Production of cyclohexanone |
| US2970172A (en) * | 1959-04-21 | 1961-01-31 | Monsanto Chemicals | Preparation of cyclohexanone |
| US3149166A (en) * | 1959-12-28 | 1964-09-15 | Basf Ag | Process for the production of pure cyclohexanone |
| US3350456A (en) * | 1960-07-28 | 1967-10-31 | Inventa Ag | Process for preparing cyclohexanone from cyclohexanol |
| US3937735A (en) * | 1972-11-23 | 1976-02-10 | Stamicarbon B.V. | Process for the preparation of cyclohexanone |
| US4670605A (en) * | 1985-05-31 | 1987-06-02 | Industrial Technology Research Institute | Process and catalyst for the conversion of cyclohexanol to cyclohexanone |
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