GB804132A - Process for the dehydrogenation of alcohols - Google Patents
Process for the dehydrogenation of alcoholsInfo
- Publication number
- GB804132A GB804132A GB5769/55A GB576955A GB804132A GB 804132 A GB804132 A GB 804132A GB 5769/55 A GB5769/55 A GB 5769/55A GB 576955 A GB576955 A GB 576955A GB 804132 A GB804132 A GB 804132A
- Authority
- GB
- United Kingdom
- Prior art keywords
- oxide
- copper
- chromium
- carriers
- catalyst
- 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
- 238000006356 dehydrogenation reaction Methods 0.000 title abstract 4
- 150000001298 alcohols Chemical class 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 abstract 12
- QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical compound O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 abstract 10
- 239000003054 catalyst Substances 0.000 abstract 8
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 7
- 229910052802 copper Inorganic materials 0.000 abstract 7
- 239000010949 copper Substances 0.000 abstract 7
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 abstract 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 6
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 abstract 6
- 239000000969 carrier Substances 0.000 abstract 6
- 229910052804 chromium Inorganic materials 0.000 abstract 6
- 239000011651 chromium Substances 0.000 abstract 6
- 229960004643 cupric oxide Drugs 0.000 abstract 6
- 229910000423 chromium oxide Inorganic materials 0.000 abstract 5
- 239000005751 Copper oxide Substances 0.000 abstract 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 4
- 229910000431 copper oxide Inorganic materials 0.000 abstract 4
- 229910000272 alkali metal oxide Inorganic materials 0.000 abstract 3
- 150000003138 primary alcohols Chemical class 0.000 abstract 3
- 150000003333 secondary alcohols Chemical class 0.000 abstract 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- 239000005749 Copper compound Substances 0.000 abstract 2
- JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 abstract 2
- 239000005750 Copper hydroxide Substances 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000001299 aldehydes Chemical class 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- -1 alkali metal salt Chemical class 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 150000001880 copper compounds Chemical class 0.000 abstract 2
- 229910001956 copper hydroxide Inorganic materials 0.000 abstract 2
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 abstract 2
- KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 abstract 2
- 229940112669 cuprous oxide Drugs 0.000 abstract 2
- 235000019441 ethanol Nutrition 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 150000002576 ketones Chemical class 0.000 abstract 2
- 239000000463 material Substances 0.000 abstract 2
- 239000005909 Kieselgur Substances 0.000 abstract 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical group CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 abstract 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 239000011230 binding agent Substances 0.000 abstract 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical group OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 abstract 1
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical group OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 229920000609 methyl cellulose Polymers 0.000 abstract 1
- 239000001923 methylcellulose Substances 0.000 abstract 1
- 235000010981 methylcellulose Nutrition 0.000 abstract 1
- 239000008262 pumice Substances 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 abstract 1
- 229910001948 sodium oxide Inorganic materials 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/85—Chromium, molybdenum or tungsten
- B01J23/86—Chromium
- B01J23/868—Chromium copper and chromium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises catalysts, optionally applied on to carriers, consisting of reduced copper containing small amounts of unreduced copper oxide and small amounts of chromium and/or at least one chromium oxide and an alkali metal oxide, the chromium content amounting to between 0.5 and 3 per cent by weight calculated as chromium oxide Cr2O3 based on the total amount of chromium and copper calculated, as oxides Cr2O3 and CuO, and the alkali metal oxide corresponding to at least double and at most six times the molar quantity of the chromium oxide Cr2O3. The catalysts may be prepared, for example, by impregnating reducible copper compounds, such as copper hydroxide, cuprous oxide or cupric oxide with an alkali metal salt of chromic or perchromic acid, the compounds being applied, if required, on to carriers and then dried; the material thus obtained is reduced, for instance by treatment with hydrogen at 200-300 DEG C. resulting in the substantial reduction of the copper oxide into copper. Suitable carriers are, for example, pumice and diatomaceous earth. If no carriers is present a binder, e.g. an aqueous solution of methyl cellulose, may be added to facilitate the production of shaped bodies or tablets.ALSO:Aldehydes or ketones are prepared by the dehydrogenation of saturated aliphatic or cycloaliphatic primary or secondary alcohols containing 2-6 carbon atoms at 250 DEG to 380 DEG C. in the presence of a copper catalyst optionally applied on to carriers, the copper catalyst being a reduced copper catalyst containing small amounts of copper oxide as well as 0.5 to 3 per cent by weight of chromium and/or a chromium oxide, the total chromium content being calculated as Cr2O3 and being referred to the total quantity of the copper and chromium content, calculated as oxides CuO and Cr2O3, and containing also from double to six times the molar quantity of alkali metal oxide referred to the chromium oxide. The catalyst may be prepared, for example, by impregnating reducible copper compounds, such as copper hydroxide, cuprous oxide or cupric oxide with an alkali metal salt of chromic or perchromic acid, the compounds being applied, if required, on to carriers, and then dried. The material, thus obtained, is reduced advantageously before the start of the reaction by heating with hydrogen at low temperatures. Any saturated primary or secondary alcohol, e.g. ethyl alcohol, isopropyl alcohol, butanol, secondary butanol, primary or secondary pentanols, cyclopentanol and cyclohexanol, may be used as starting material. For the dehydrogenation of secondary alcohols to the corresponding ketones preferred temperatures are in the range 250-360 DEG C. and for the dehydrogenation of primary alcohols to the corresponding aldehydes preferred temperatures are in the range 280-340 DEG C. In the examples: (a) isopropyl alcohol is passed over a catalyst, consisting of copper oxide which is present for the most part in reduced form, chromic oxide and sodium oxide on a pumic support, to give acetone; and (b) ethyl alcohol is passed over a similar catalyst to give acetaldehyde.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE804132X | 1954-02-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB804132A true GB804132A (en) | 1958-11-05 |
Family
ID=6722045
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5769/55A Expired GB804132A (en) | 1954-02-26 | 1955-02-25 | Process for the dehydrogenation of alcohols |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB804132A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0023699A1 (en) * | 1979-07-30 | 1981-02-11 | Mitsubishi Kasei Corporation | Process for the preparation of cyclohexanone |
| US4453015A (en) * | 1981-10-16 | 1984-06-05 | Shell Oil Company | Methyl ethyl ketone process |
| US4472593A (en) * | 1981-10-16 | 1984-09-18 | Shell Oil Company | Conversion of isopropyl alcohol to acetone |
| EP0781793A1 (en) | 1995-12-19 | 1997-07-02 | Chevron Chemical Company | Reductive amination process for manufacturing a fuel additive from polyoxybutylene alcohol with ethylene diamine |
| EP0781794A1 (en) | 1995-12-19 | 1997-07-02 | Chevron Chemical Company | Very long chain alkylphenyl polyoxyalkylene amines and fuel compositions containing the same |
-
1955
- 1955-02-25 GB GB5769/55A patent/GB804132A/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0023699A1 (en) * | 1979-07-30 | 1981-02-11 | Mitsubishi Kasei Corporation | Process for the preparation of cyclohexanone |
| US4453015A (en) * | 1981-10-16 | 1984-06-05 | Shell Oil Company | Methyl ethyl ketone process |
| US4472593A (en) * | 1981-10-16 | 1984-09-18 | Shell Oil Company | Conversion of isopropyl alcohol to acetone |
| EP0781793A1 (en) | 1995-12-19 | 1997-07-02 | Chevron Chemical Company | Reductive amination process for manufacturing a fuel additive from polyoxybutylene alcohol with ethylene diamine |
| EP0781794A1 (en) | 1995-12-19 | 1997-07-02 | Chevron Chemical Company | Very long chain alkylphenyl polyoxyalkylene amines and fuel compositions containing the same |
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