GB825602A - Process for the dehydrogenation of alcohols - Google Patents
Process for the dehydrogenation of alcoholsInfo
- Publication number
- GB825602A GB825602A GB3977/56A GB397756A GB825602A GB 825602 A GB825602 A GB 825602A GB 3977/56 A GB3977/56 A GB 3977/56A GB 397756 A GB397756 A GB 397756A GB 825602 A GB825602 A GB 825602A
- Authority
- GB
- United Kingdom
- Prior art keywords
- copper
- oxide
- alkali metal
- chromium
- 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 3
- 150000001298 alcohols Chemical class 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- 229910052802 copper Inorganic materials 0.000 abstract 9
- 239000010949 copper Substances 0.000 abstract 9
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 7
- 229910000272 alkali metal oxide Inorganic materials 0.000 abstract 6
- 239000003054 catalyst Substances 0.000 abstract 5
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 abstract 4
- 229910052804 chromium Inorganic materials 0.000 abstract 4
- 239000011651 chromium Substances 0.000 abstract 4
- 238000010438 heat treatment Methods 0.000 abstract 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 abstract 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 3
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 abstract 3
- 229910000423 chromium oxide Inorganic materials 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 abstract 2
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 abstract 2
- 239000005751 Copper oxide Substances 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 abstract 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 150000001340 alkali metals Chemical class 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 229910000431 copper oxide Inorganic materials 0.000 abstract 2
- -1 copper tetramine complexes Chemical class 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
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 150000003138 primary alcohols Chemical class 0.000 abstract 2
- 150000003333 secondary alcohols Chemical class 0.000 abstract 2
- 239000011701 zinc Substances 0.000 abstract 2
- 229910052725 zinc Inorganic materials 0.000 abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 abstract 1
- 239000005909 Kieselgur Substances 0.000 abstract 1
- 229910002651 NO3 Inorganic materials 0.000 abstract 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 abstract 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 229940116318 copper carbonate Drugs 0.000 abstract 1
- GEZOTWYUIKXWOA-UHFFFAOYSA-L copper;carbonate Chemical compound [Cu+2].[O-]C([O-])=O GEZOTWYUIKXWOA-UHFFFAOYSA-L 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 239000008262 pumice Substances 0.000 abstract 1
- AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000011787 zinc oxide Substances 0.000 abstract 1
Classifications
-
- 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
-
- 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
-
- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/03—Precipitation; Co-precipitation
-
- 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
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
-
- 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
-
- 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
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
-
- 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)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Abstract
A catalyst for the dehydrogenation of saturated aliphatic or cycloaliphatic primary and secondary alcohols containing 2-6 carbon atoms consists of a carrier, copper and at least 0.1% by weight of an alkali metal oxide (referred to the total quantity of copper and alkali metal calculated as cuprous oxide and alkali metal oxide), the copper content having been obtained by heating copper tetramine complexes followed by subsequent heating with hydrogen and consisting of reduced copper with small amounts of unreduced copper oxide. The catalyst may additionally contain 0.5-3% by weight of chromium and/or chromium oxide, the alkali metal oxide being present in an amount from double to six times the molar quantity of chromium oxide or chromium calculated as chromium oxide or the chromium content may be partially or wholly replaced by bivalent zinc calculated as zinc oxide. Suitable copper tetramine complexes are obtained by reacting copper carbonate, acetate, formate, nitrate or hydroxide with ammonia. Suitable carriers are, for example, pumice and diatomaceous earth.ALSO:Aldehydes and ketones are prepared by dehydrogenating saturated aliphatic or cycloaliphatic primary or secondary alcohols containing 2-6 carbon atoms at temperatures of from 250 DEG to 380 DEG C. in the presence of a catalyst applied on to a carrier, comprising reduced copper containing small amounts of unreduced copper oxide and alkali metal oxide, the catalyst having been obtained by heating a copper tetramine complex followed by subsequent heating with hydrogen and containing at least 0.1% by weight of alkali metal oxide referred to the total quantity of copper and alkali metal content calculated as cuprous oxide and alkali metal oxide. If desired, small amounts of chromium and/or zinc may also be present in the catalyst. Examples are given of the dehydrogenation of (a) ethanol to give acetaldehyde, (b) isopropanol to give acetone, (c) secondary butyl alcohol to give methyl ethyl ketone, and (d) n-butyl alcohol to give n-butyraldehyde.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE825602X | 1955-02-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB825602A true GB825602A (en) | 1959-12-16 |
Family
ID=6747589
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3977/56A Expired GB825602A (en) | 1955-02-08 | 1956-02-08 | Process for the dehydrogenation of alcohols |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB825602A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3209034A (en) * | 1961-12-08 | 1965-09-28 | Kancgafuchi Spinning Co Ltd | Oxidation of olefines |
| US3217041A (en) * | 1962-08-08 | 1965-11-09 | Universal Oil Prod Co | Preparation of olefinic oxygencontaining compounds |
| US4891446A (en) * | 1988-09-30 | 1990-01-02 | Shell Oil Company | Process for preparing aldehydes from alcohols |
| US4935538A (en) * | 1986-05-29 | 1990-06-19 | The Standard Oil Company | Oxygenate condensation |
| WO2021037990A1 (en) | 2019-08-30 | 2021-03-04 | Covestro Deutschland Ag | Method for the hydrogenation of aromatic nitro compounds |
| WO2022184614A1 (en) | 2021-03-01 | 2022-09-09 | Covestro Deutschland Ag | Method for the hydrogenation of aromatic nitro compounds |
-
1956
- 1956-02-08 GB GB3977/56A patent/GB825602A/en not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3209034A (en) * | 1961-12-08 | 1965-09-28 | Kancgafuchi Spinning Co Ltd | Oxidation of olefines |
| US3217041A (en) * | 1962-08-08 | 1965-11-09 | Universal Oil Prod Co | Preparation of olefinic oxygencontaining compounds |
| US4935538A (en) * | 1986-05-29 | 1990-06-19 | The Standard Oil Company | Oxygenate condensation |
| US4891446A (en) * | 1988-09-30 | 1990-01-02 | Shell Oil Company | Process for preparing aldehydes from alcohols |
| WO2021037990A1 (en) | 2019-08-30 | 2021-03-04 | Covestro Deutschland Ag | Method for the hydrogenation of aromatic nitro compounds |
| WO2022184614A1 (en) | 2021-03-01 | 2022-09-09 | Covestro Deutschland Ag | Method for the hydrogenation of aromatic nitro compounds |
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