GB2038320A - Process for the manufacture of ketones - Google Patents
Process for the manufacture of ketones Download PDFInfo
- Publication number
- GB2038320A GB2038320A GB7938620A GB7938620A GB2038320A GB 2038320 A GB2038320 A GB 2038320A GB 7938620 A GB7938620 A GB 7938620A GB 7938620 A GB7938620 A GB 7938620A GB 2038320 A GB2038320 A GB 2038320A
- Authority
- GB
- United Kingdom
- Prior art keywords
- per cent
- process according
- catalyst
- aldehyde
- oxide
- 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.)
- Withdrawn
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- 238000000034 method Methods 0.000 title claims description 24
- 150000002576 ketones Chemical class 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 239000003054 catalyst Substances 0.000 claims description 33
- 150000001299 aldehydes Chemical class 0.000 claims description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 24
- 239000007789 gas Substances 0.000 claims description 17
- 239000011787 zinc oxide Substances 0.000 claims description 12
- 150000003254 radicals Chemical class 0.000 claims description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- 229910002804 graphite Inorganic materials 0.000 claims description 10
- 239000010439 graphite Substances 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 7
- 229910052802 copper Inorganic materials 0.000 claims description 7
- 239000010949 copper Substances 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 6
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052748 manganese Inorganic materials 0.000 claims description 6
- 239000011572 manganese Substances 0.000 claims description 6
- 239000011701 zinc Substances 0.000 claims description 6
- 229910052725 zinc Inorganic materials 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 claims description 4
- LGYNIFWIKSEESD-UHFFFAOYSA-N 2-ethylhexanal Chemical compound CCCCC(CC)C=O LGYNIFWIKSEESD-UHFFFAOYSA-N 0.000 claims description 2
- 125000002015 acyclic group Chemical group 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 239000003701 inert diluent Substances 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 230000006324 decarbonylation Effects 0.000 description 8
- 238000006606 decarbonylation reaction Methods 0.000 description 8
- 230000001590 oxidative effect Effects 0.000 description 8
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 3
- 229910001431 copper ion Inorganic materials 0.000 description 3
- QKSIFUGZHOUETI-UHFFFAOYSA-N copper;azane Chemical compound N.N.N.N.[Cu+2] QKSIFUGZHOUETI-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 2
- 239000005751 Copper oxide Substances 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 125000005024 alkenyl aryl group Chemical group 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910000431 copper oxide Inorganic materials 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 2
- 150000002736 metal compounds Chemical class 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000007210 heterogeneous catalysis Methods 0.000 description 1
- 229940071125 manganese acetate Drugs 0.000 description 1
- 229910001437 manganese ion Inorganic materials 0.000 description 1
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- -1 steam Chemical compound 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000010414 supernatant solution Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Inorganic materials [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 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
- C07C45/27—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
Description
SPECIFICATION
Process for the manufacture of ketones Selective manufacture of acetone by oxidative decarbonylation in the gas phase, under heterogeneous catalysis, of an aldehyde containing one more carbon atom, namely isobutanal, has been proposed (German laid-open Patent Application DOS 2,802,672). In the manufacture of acetone by this process, isobutanal is subjected to oxidative decarbonylation in the gas phase on metal oxide catalysts to give acetone. No other processes in which aldehydes are selectively decarbonylated oxidatively in the gas phase to give the corresponding ketones which contain one carbon atom less are known in the literature, so that it is reasonable to assume that the high selectivity of the oxidative decarbonylation of an aldehyde in the gas phase is restricted to the one case of isobutanal/acetone.This assumption was even initially confirmed by a number of experiments carried out by us using other aldehydes (Comparison Examples 5 to 9).
However, we have now found that it is possible to provide a process of this type for the selective manufacture of ketones with at least 4 C atoms.
According to the invention there is provided a process for the manufacture of a ketone with at least 4 carbon atoms wherein a vaporisable aldehyde with at least 5 carbon atoms and having a tertiary carbon atom bearing a single hydrogen atom in a-position to the carbonyl group is oxidatively decarbonylated by reacting it with oxygen in the gas phase in the presence of a catalyst which comprises an oxide of copper and/or an oxide of manganese at a temperature from 120 to 270[deg]C and with a contact time of 0.2 to 10 seconds, the concentration of the aldehyde in the starting gas being 1 to 8 per cent by volume.
In particular, the process enables ketones with at least 4 C atoms and having the general formula
in which R' and R independently denote linear or branched, acyclic or cyclic, saturated or olefinically unsaturated hydrocarbon radicals of up to 18 carbon atoms and optionally aryl-substituted, particularly alkyl, alkenyl, alkylaryl, alkenylaryl, alkylcycloalkyl, alkenylcycloalkyl, alkylcycloalkenyl or alkenylcycloalkenyl radicals with 1 to 18 C atoms, or together form a macrocyclic ring with 5 to 18 C atoms, and may bear one or more hetero-atom-containing substituents, to be produced from aldehydes having the general formula
in which R' and R have the meanings given above.
It has therefore been found, surprisingly, that selective oxidative decarbonylation of an aldehyde in the gas phase to give a ketone is not restricted to isobutanal/acetone, but is a general reaction principle provided that copper oxide and/or manganese oxide are used as catalyst and the aldehyde used has, in the a-position relative to the carbonyl group, a tertiary carbon atom, i.e. bearing a single hydrogen atom.
In the formula
the radicals R' and R can represent alkyl, alkenyl, alkylaryl, alkenylaryl, alkylcycloalkyl, alkenylcycloalkyl, alkylcycloalkenyl or alkenylcycloalkenyl radicals with 1 to 18 C atoms. The radicals R' and R can together also form a macrocyclic ring with 5 to 18 C atoms. The limitation of the radicals with regard to their number of C atoms is not a result of the reaction mechanism, the conversion or the selectivity, but is due to the necessity of vapourising the aldehydes. Thus, at correspondingly low pressures, aldehydes with more C atoms can also be employed. Since aldehydes with radicals which contain more than 18 C atoms are found relatively rarely in practice and these aldehydes are difficult to transfer into the gas phase, aldehydes with radicals which contain not more than 18 C atoms are preferred.
-C-
N =C-O
The radicals R' and R can also contain one or more hetero-atoms, for example Si, N, P, As, 0, S, Se, F, Cl, Br or I, it being possible for the hetero-atoms to be located by themselves on one or more C atoms, such as, for example, -C-Cl and -C-C-, o or between two or more C atoms, for example and -C-N-C-
or between two or more C atoms, for example
depending on their nature.
During the oxidative decarbonylation, the groups containing hetero-atoms can remain inert or can themselves undergo reactions, depending on their nature. Because of the large number of possible groups with hetero-atoms in the radicals R' and R , in an individual case tests must be carried out to determine whether the group with the hetero-atoms impairs the selectivity in the oxidative decarbonylation of the aldehyde. The process is particularly suitable for oxidative decarbonylation of 2-ethyl-hexanal to give heptan-3-one.
The catalysts according to the invention can be manufactured as pure catalysts or supported catalysts by customary methods. Supported catalysts are preferred, since they are more stable mechanically and are cheaper. The copper and/or manganese content of the finished catalyst should preferably be 0.1 to 6 per cent by weight. Below 0.1 per cent by weight, the conversion becomes too low for industrial purposes, and concentrations of over 6 per cent by weight no longer bring further improvement. In addition, at higher concentrations the extent of total combustion of the aldehyde increases. A content of copper and/or manganese in the form of the oxides of 1 to 3 per cent by weight is particularly preferred. Preferably the catalyst also contains zinc oxide and/or graphite. The zinc content of the finished catalyst in the form of the oxide can be 0.1 to 80 per cent by weight.As a rule, contents of 0.1 to 20 per cent by weight are used. Zinc contents of 1 to 5 per cent by weight are particularly preferred. At zinc contents of greater than 20 per cent by weight, the zinc oxide as a rule simultaneously serves as the supportforthe other catalyst components. It has proved advantageous to add to the zinc oxide 2 to 20 per cent by weight of colloidal graphite, relative to the zinc oxide. Graphite contents of 2 to 5 per cent by weight, relative to the zinc oxide, are preferred, since larger amounts of graphite bring no further advantages.
Possible supports for the active metal oxides are materials which either are inert under the reaction conditions or have an inherent activity for the oxidative decarbonylation, as is the case, for example, with zinc oxide/graphite. Commercially available aluminium oxide, zinc oxide and titanium dioxide have proved particularly suitable support materials. Because of the many differences in the case of the individual support materials, for example in the case of the various aluminium oxides, it is necessary to test the particular support for selectivity-reducing inherent activity under the reaction conditions.
The catalytic components may be applied to the support by methods customary in the art, for example by impregnating the supports with aqueous salt solutions of the metals, drying the impregnated supports and converting the salts to the corresponding oxides at elevated temperatures. In this procedure, the metal compounds can be applied to the supports in one step by using solutions which contain all the required metal ions, or in individual steps by first applying one metal compound to the support, drying and calcining the product and then applying the next component by the same processing steps, and so on. Suitable external forms for the catalyst are spheres, tablets, extrudates, pellets or lumps.
The concentration of the aldehyde in the inlet gas mixture varies between 1 and 8 per cent by volume. However, higher and lower concentrations are also possible, but the low concentrations are of no interest economically, and at the higher concentrations the problem of removal of heat becomes difficult. Concentrations of between 2 and 5 per cent by volume are particularly preferred.
The oxygen used may be pure oxygen or an oxygen-containing gas. The oxygen concentration in the inlet gas depends on the aldehyde concentration. The minimum molar ratio should be 1 : 1.2. At even smaller ratios, the conversion decreases rapidly. Molar ratios of aldehyde : oxygen of 1 : 2 to 1 : 3 are preferred. The aldehyde : oxygen ratio can, however, also exceed these ratios. Thus, it is also possible to carry outthe reaction with pure oxygen if the aldehyde concentration chosen is not too high. Air is preferably used as the oxidising agent. An inert diluent is as a rule added to the inlet gas. Possible diluents are: nitrogen, steam, carbon dioxide or carbon monoxide. Preferred diluents are nitrogen and/or steam, the nitrogen originating from the air used as the preferred oxidising agent.
The reaction temperature depends on the aldehyde used. It is 120 to 270[deg]C. The residence time of the starting substances in the catalyst bed (contact time) depends on the composition of the starting mixture and the reaction temperature and varies within a range of from 0.2 to 10 seconds. It is preferably in a range of from 1 to 6 seconds. The reaction is usually carried out under normal pressure or slightly elevated pressures of up to about 5 bars. However, higher pressures can also be applied. In the case of relatively high-boiling aldehydes, the reaction may be carried out in vacuo. The extent of the vacuum depends on the aldehyde used.
With the aid of the process according to the invention, it is possible for ketones which were hitherto accessible with difficulty to be manufactured selectively in a simple manner.
Example 1 (Preparation of the catalyst) 200 g of activated aluminium oxide (extrudates: 0 1.6 mm, length 4 mm, Katalysatorenwerke Houdry-Hüls) are impregnated with 213 g of an aqueous coppertetrammine carbonate solution which contains 4.3 per cent by weight of copper ions. The supernatant solution is decanted off. The catalyst is dried at 110[deg]C for 16 hours and calcined at 350[deg]C for 4 hours. The content of copper in the form of the oxide is 2.5 per cent by weight, relative to the finished catalyst.
Example 2 (Preparation of the catalyst) 112 g of activated aluminium oxide are impregnated with 98 ccs of an aqueous solution which contains 20.5 g of Zn(NO3)2 . 6 H20 and are dried at 110[deg]C for 16 hours and calcined at 350[deg]C for 16 hours. The calcined catalyst is then impregnated with 98 ccs of an aqueous copper tetrammine carbonate solution which has a concentration of copper ions of 14.1 per cent, and is again dried at 110[deg]C for 16 hours and calcined at 350[deg]C for 16 hours. The finished catalyst contains 2.3 per cent by weight of copper and 2.3 per cent by weight of zinc in the form of their oxides.
Example 3 (Preparation of the catalyst) 960 g of zinc oxide are mixed intimately with 40 g of colloidal graphite and 30 g of water and the mixture is pressed to tablets (diameter 4 mm, thickness 4 mm). The tablets are then dried at 110[deg]C for 16 hours and then subjected to heat treatment at 350[deg]C for 16 hours. The finished tablets are impregnated with 122 g of copper tetrammine carbonate solution which contains 13.9 per cent by weight of copper ions and are dried at 110[deg]C for 16 hours and calcined at 350[deg]C for 16 hours. The copper oxide content of the finished catalyst is 2.1 per cent by weight and the graphite content is 3.9 per cent by weight.
Example 4 (Preparation of the catalyst) 85 g of commercially available zinc oxide and 10 g of commercially available colloidal graphite are suspended in 120 ccs of an aqueous manganese acetate solution which contains 5 g of manganese ions. The suspension is evaporated to dryness and the residue is dried at 110[deg]C for 16 hours, ground and pressed to tablets (0 4 mm, height 4 mm) and the tablets are subjected to heat treatment at 350[deg]C for 16 hours. The content of manganese in the form of the oxide is 5 per cent by weight, relative to the finished catalyst.
Examples 5 to 9 (Comparison Examples) 60 ccs of the catalyst described in Example 2 are introduced into a steel reaction tube which is thermostatically controlled with boiling water and has an internal diameter of 20 mm, and the tube is charged, at the temperatures indicated in Table 1, with contact times of 2 seconds and under internal reactor pressures of 1.5 bars (unless stated otherwise), with gas mixtures which consist of 2.5 per cent by volume of an aldehyde which does not have, in the a-position relative to the carbonyl group, a tertiary C atom with one hydrogen atom 44.5 per cent by volume of air and 53.0 per cent by volume of steam. The gas mixtures leaving the reactor are investigated by gas chromatography. The results obtained are summarised in Table 1.
Examples 10 to 14 Aldehydes which have, in the a-position relative to the carbonyl group, a tertiary C atom with one hydrogen atom are used under the experimental conditions given in Examples 5 to 9. The results obtained are shown in Table 2.
Similar results are obtained if the catalysts described in Examples 1,3 and 4 are employed in Examples 5 to 14.
TABLE 1 (Comparison Examples)
Claims (11)
1. A process for the manufacture of a ketone with at least 4 carbon atoms wherein a vaporisable aldehyde with at least 5 carbon atoms and having a tertiary carbon atom bearing a single hydrogen atom in a-position to the carbonyl group is oxidatively decarbonylated by reacting it with oxygen in the gas phase in the presence of a catalyst which comprises an oxide of copper and/or an oxide of manganese at a temperature from 120 to 270[deg]C and with a contact time of 0.
2 to 10 seconds, the concentration of the aldehyde in the starting gas being 1 to 8 per cent by volume.
2. A process according to claim 1 wherein a ketone with at least 4 C atoms and having the general formula
in which R' and R independently denote linear or branched acyclic or cyclic saturated or olefinically unsaturated hydrocarbon radicals optionally aryl-substituted and having up to 18 C atoms, or together form a macrocyclic ring with 5 to 18 C atoms, and may bear one or more hetero-atom-containing substituents is manufactured from an aldehyde having the general formula
in which R' and R have the meanings given above.
3. A process according to claim 1 or 2, wherein the amount of copper and/or manganese in the form of the oxide(s) is 0.1 to 6 per cent by weight, relative to the finished catalyst.
4. A process according to any of claims 1 to 3, wherein the catalyst also includes zinc oxide and/or graphite.
5. A process according to claim 4, wherein the catalyst includes 0.1 to 20 per cent by weight of zinc in the form of zinc oxide, relative to the finished catalyst.
6. A process according to claim 4, wherein the catalyst includes 20 to 80 per cent by weight of zinc in the form of the oxide, relative to the finished catalyst, and from 2 to 20 per cent by weight of colloidal graphite, relative to the zinc oxide.
7. A process according to any of claims 1 to 6, wherein the inlet gas phase contains from 1 to 8 per cent by volume of the aldehyde, oxygen in an amount to provide a molar ratio of aldehyde : oxygen of at least 1 :
1.2 and one or more inert diluents.
8. A process according to any of claims 2 to 7, wherein 2-ethylhexanal is converted into heptan-3-one.
9. A process according to any of claims 1 to 8, wherein a catalyst prepared by a process substantially as described in any of the foregoing Examples 1 to 4 is used.
10. A process for the manufacture of a ketone of at least 4 carbon atoms carried out substantially as described in any of the foregoing Examples 10 to 14.
11. A ketone of at least 4 carbon atoms when manufactured by a process according to any of claims 1 to
10.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2848400A DE2848400C2 (en) | 1978-11-08 | 1978-11-08 | Process for the production of ketones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB2038320A true GB2038320A (en) | 1980-07-23 |
Family
ID=6054137
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7938620A Withdrawn GB2038320A (en) | 1978-11-08 | 1979-11-07 | Process for the manufacture of ketones |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP0011098A1 (en) |
| JP (1) | JPS5566526A (en) |
| AT (1) | ATA713279A (en) |
| BE (1) | BE879893A (en) |
| DE (1) | DE2848400C2 (en) |
| ES (1) | ES485791A1 (en) |
| FR (1) | FR2440932A1 (en) |
| GB (1) | GB2038320A (en) |
| IT (1) | IT7950781A0 (en) |
| NL (1) | NL7908147A (en) |
| RO (1) | RO79022A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5606081A (en) * | 1994-05-20 | 1997-02-25 | Basf Aktiengesellschaft | Preparation of cyclic ether ketones |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1133882A (en) * | 1966-09-08 | 1968-11-20 | Ici Ltd | A process for the production of ketones |
| FR2053423A6 (en) * | 1969-07-07 | 1971-04-16 | Melle Bezons | |
| US3496197A (en) * | 1969-03-05 | 1970-02-17 | Upjohn Co | Oxidation of aldehydes to ketones employing copper ions as catalysts |
| US3804902A (en) * | 1970-11-21 | 1974-04-16 | Daicel Ltd | Process for producing acetone |
| FR2265712B1 (en) * | 1974-03-29 | 1978-12-29 | Huels Chemische Werke Ag | |
| DE2738269C3 (en) * | 1977-08-25 | 1980-02-21 | Chemische Werke Huels Ag, 4370 Marl | Process for the production of acetone from isobutyraldehyde |
| DE2802672A1 (en) * | 1978-01-21 | 1979-07-26 | Huels Chemische Werke Ag | PROCESS FOR PRODUCING ACETONE FROM ISOBUTYRALDEHYDE |
-
1978
- 1978-11-08 DE DE2848400A patent/DE2848400C2/en not_active Expired
-
1979
- 1979-09-07 EP EP79103323A patent/EP0011098A1/en not_active Withdrawn
- 1979-10-31 FR FR7926990A patent/FR2440932A1/en not_active Withdrawn
- 1979-11-06 AT AT0713279A patent/ATA713279A/en unknown
- 1979-11-07 ES ES485791A patent/ES485791A1/en not_active Expired
- 1979-11-07 NL NL7908147A patent/NL7908147A/en not_active Application Discontinuation
- 1979-11-07 BE BE0/198023A patent/BE879893A/en unknown
- 1979-11-07 JP JP14343079A patent/JPS5566526A/en active Pending
- 1979-11-07 GB GB7938620A patent/GB2038320A/en not_active Withdrawn
- 1979-11-08 IT IT7950781A patent/IT7950781A0/en unknown
- 1979-11-08 RO RO7999177A patent/RO79022A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5606081A (en) * | 1994-05-20 | 1997-02-25 | Basf Aktiengesellschaft | Preparation of cyclic ether ketones |
Also Published As
| Publication number | Publication date |
|---|---|
| BE879893A (en) | 1980-05-07 |
| IT7950781A0 (en) | 1979-11-08 |
| FR2440932A1 (en) | 1980-06-06 |
| NL7908147A (en) | 1980-05-12 |
| DE2848400C2 (en) | 1982-07-08 |
| JPS5566526A (en) | 1980-05-20 |
| ATA713279A (en) | 1982-07-15 |
| EP0011098A1 (en) | 1980-05-28 |
| RO79022A (en) | 1982-10-11 |
| DE2848400A1 (en) | 1980-05-14 |
| ES485791A1 (en) | 1980-05-16 |
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