GB1111416A - Dehydrogenation process - Google Patents
Dehydrogenation processInfo
- Publication number
- GB1111416A GB1111416A GB2766865A GB2766865A GB1111416A GB 1111416 A GB1111416 A GB 1111416A GB 2766865 A GB2766865 A GB 2766865A GB 2766865 A GB2766865 A GB 2766865A GB 1111416 A GB1111416 A GB 1111416A
- Authority
- GB
- United Kingdom
- Prior art keywords
- catalyst
- zinc oxide
- nickel
- roasting
- sec
- 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
- 238000000034 method Methods 0.000 title abstract 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 abstract 12
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 11
- 239000003054 catalyst Substances 0.000 abstract 10
- 239000011787 zinc oxide Substances 0.000 abstract 6
- 239000000463 material Substances 0.000 abstract 5
- 239000011701 zinc Substances 0.000 abstract 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000000203 mixture Substances 0.000 abstract 3
- 229910000480 nickel oxide Inorganic materials 0.000 abstract 3
- 238000002360 preparation method Methods 0.000 abstract 3
- 239000008262 pumice Substances 0.000 abstract 3
- 239000002002 slurry Substances 0.000 abstract 3
- 229910052725 zinc Inorganic materials 0.000 abstract 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-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
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 2
- 150000001298 alcohols Chemical class 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 abstract 2
- 238000001816 cooling Methods 0.000 abstract 2
- 229910052802 copper Inorganic materials 0.000 abstract 2
- 239000010949 copper Substances 0.000 abstract 2
- 229910000431 copper oxide Inorganic materials 0.000 abstract 2
- 238000001035 drying Methods 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- QNVRIHYSUZMSGM-UHFFFAOYSA-N hexan-2-ol Chemical compound CCCCC(C)O QNVRIHYSUZMSGM-UHFFFAOYSA-N 0.000 abstract 2
- 238000002156 mixing Methods 0.000 abstract 2
- 150000002815 nickel Chemical class 0.000 abstract 2
- 229910052759 nickel Inorganic materials 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical class CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 abstract 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 1
- 239000012159 carrier gas Substances 0.000 abstract 1
- 230000000052 comparative effect Effects 0.000 abstract 1
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 229910052749 magnesium Inorganic materials 0.000 abstract 1
- 239000011777 magnesium Substances 0.000 abstract 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 abstract 1
- 239000000395 magnesium oxide Substances 0.000 abstract 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 abstract 1
- HZPNKQREYVVATQ-UHFFFAOYSA-L nickel(2+);diformate Chemical compound [Ni+2].[O-]C=O.[O-]C=O HZPNKQREYVVATQ-UHFFFAOYSA-L 0.000 abstract 1
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 abstract 1
- 150000003138 primary alcohols Chemical class 0.000 abstract 1
- 150000003333 secondary alcohols Chemical class 0.000 abstract 1
- ZTYDCVBIHYGLSF-UHFFFAOYSA-M zinc nickel(2+) oxygen(2-) formate Chemical compound [O-2].[Zn+2].C(=O)[O-].[Ni+2] ZTYDCVBIHYGLSF-UHFFFAOYSA-M 0.000 abstract 1
Classifications
-
- 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
- B01J23/80—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 zinc, cadmium or mercury
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Exhaust Gas Treatment By Means Of Catalyst (AREA)
Abstract
Preparation of an aldehyde or ketone by the dehydrogenation of the corresponding primary or secondary alcohol respectively by contacting the alcohol at elevated temperature with a catalyst comprising elemental nickel and zinc oxide. Suitable feed alcohols include isopropanol, n- or sec-butanol, sec-pentanol or n- or sec-hexanol. The dehydrogenation catalyst, which may be supported on an inert material such as kieselguhr or pumice, preferably has a weight ratio of Ni to Zn in the range 1:100 to 10:1 and may be prepared by roasting a suitable support material, cooling it, then mixing the cooled support with an aqueous slurry formed from a nickel salt and zinc oxide, drying the mixture, roasting the residue in air or oxygen and, finally, heating (e.g. to 300 DEG to 400 DEG C.) in a stream of hydrogen. The dehydrogenation is preferably carried out at 250 DEG to 450 DEG C. by passing the feed alcohol in the vapour phase over the catalyst optionally in a stream of carrier gas such as hydrogen. The preparation of hexanones from sec-hexanols using a catalyst containing 2.3% Ni and 5.5% Zn is described. Comparative examples describe the use of catalysts containing copper and zinc oxide and copper and magnesium oxide.ALSO:A catalyst, suitable for dehydrogenating alcohols, comprising p elemental nickel and zinc oxide, preferably having a weight ratio of Ni to Zn in the range 1:100 to 10:1 and a combined weight of nickel and zinc oxide representing 0.1 to 98% by weight of the total catalyst, is prepared by roasting a suitable support material (e.g. pumice or kieselguhr), cooling the support material, mixing the cooled support material with a aqueous slurry formed from the nickel salt (e.g. nickel formate) and zinc oxide, drying the mixture, roasting the residue in a stream of air or oxygen and, finally, heating in a stream of hydrogen. The slurried catalyst composition is preferably dried at a temperature between 80 DEG and 150 DEG C., roasted in air at a temperature between 350 DEG and 450 DEG C. and reduced at a temperature between 300 DEG and 400 DEG C. The example described the preparation of a catalyst containing 2.3% nickel and 5.5% zinc by weight wherein 10-18 mesh pumice is roasted at 550 DEG C., cooled in vacuo, mixed with a slurry containing nickel formate zinc oxide and aqueous ammonia, dried and roasted in air and reduced with hydrogen prior to use. Catalysts containing 7.3% Cu and 12.6% Zn, and 7.5% Cu and 13.5% Mg are prepared by a similar method for comparison.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2766865A GB1111416A (en) | 1965-06-30 | 1965-06-30 | Dehydrogenation process |
| DE19661717151 DE1717151B1 (en) | 1965-06-30 | 1966-06-10 | Process for the preparation of hexanone (2) or hexanone (3) by catalytic dehydrogenation of hexanol (2) or hexanol (3) |
| FR66468A FR1484317A (en) | 1965-06-30 | 1966-06-22 | Process for the dehydrogenation of a primary or secondary aliphatic alcohol to the corresponding aladehyde or ketone, process for the preparation of a dehydrogenation catalyst, products and catalysts obtained |
| NL6608721A NL148299B (en) | 1965-06-30 | 1966-06-23 | PROCESS FOR DEHYDROGENING PRIMARY OR SECONDARY ALKANOLS. |
| BE683448D BE683448A (en) | 1965-06-30 | 1966-06-30 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2766865A GB1111416A (en) | 1965-06-30 | 1965-06-30 | Dehydrogenation process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1111416A true GB1111416A (en) | 1968-04-24 |
Family
ID=10263333
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2766865A Expired GB1111416A (en) | 1965-06-30 | 1965-06-30 | Dehydrogenation process |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE683448A (en) |
| DE (1) | DE1717151B1 (en) |
| GB (1) | GB1111416A (en) |
| NL (1) | NL148299B (en) |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE854351C (en) * | 1940-02-16 | 1952-11-04 | Basf Ag | Process for the production of propionaldehyde |
| DE863459C (en) * | 1946-07-08 | 1953-01-19 | Trico Folberth Ltd | Device for attaching a windscreen wiper arm to a reciprocating spindle |
| DE832292C (en) * | 1950-03-07 | 1952-02-21 | Farbwerke Hoechst Vormals Meis | Process for the production of butyraldehyde |
| DE1016695B (en) * | 1954-02-26 | 1957-10-03 | Knapsack Ag | Process for the dehydrogenation of secondary alcohols to ketones |
| DE1026739B (en) * | 1955-02-08 | 1958-03-27 | Knapsack Ag | Process for the dehydrogenation of low molecular weight, aliphatic, secondary alcohols to the corresponding ketones |
| DE1055520B (en) * | 1956-01-31 | 1959-04-23 | Rheinpreussen Ag | Process for the dehydration of alcohols |
| BE567030A (en) * | 1957-04-25 | |||
| DE1147933B (en) * | 1958-01-30 | 1963-05-02 | Rheinpreussen Ag | Process for the catalytic dehydrogenation of alcohols by thermal decomposition |
| US3053898A (en) * | 1959-07-21 | 1962-09-11 | Exxon Research Engineering Co | Preparation of ketones from secondary alcohols |
-
1965
- 1965-06-30 GB GB2766865A patent/GB1111416A/en not_active Expired
-
1966
- 1966-06-10 DE DE19661717151 patent/DE1717151B1/en active Pending
- 1966-06-23 NL NL6608721A patent/NL148299B/en unknown
- 1966-06-30 BE BE683448D patent/BE683448A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE683448A (en) | 1966-12-30 |
| NL148299B (en) | 1976-01-15 |
| NL6608721A (en) | 1967-01-02 |
| DE1717151B1 (en) | 1971-10-21 |
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