CN104368359A - Catalyst for preparing 3-pentanol through 3-pentanone hydrogenation and preparation method of catalyst for preparing 3-pentanol through 3-pentanone hydrogenation - Google Patents
Catalyst for preparing 3-pentanol through 3-pentanone hydrogenation and preparation method of catalyst for preparing 3-pentanol through 3-pentanone hydrogenation Download PDFInfo
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Abstract
The invention discloses a catalyst for preparing 3-pentanol through 3-pentanone hydrogenation. The catalyst comprises a carbon-based carrier and a multi-metal component recorded as M1-M2-M3/C, wherein M1 is selected from one of Ru, Mn and Ag; M2 is selected from one of Ir, Au and Cu; and M3 is selected from one of La, Ce and Y. The catalyst is applied to the liquid phase 3-pentanone hydrogenation process. The conversion rate of 3-pentanone can be 100 percent within a short time, and the selectivity of the 3-pentanol is 100 percent. The invention also provides a method for preparing the catalyst, and the industrial preparation is easily realized.
Description
Technical field
The present invention relates to catalyst, particularly relate to a kind of Catalysts and its preparation method of propione Hydrogenation 3-amylalcohol.
Background technology
3-amylalcohol is a kind of important industrial chemicals, and it is except can be used for organic synthesis, and be also used to flotation agent and solvent use, belonging to a kind of medicine intermediate, material intermediate, is a kind of fine chemicals.3-amylalcohol can be obtained by propione Hydrogenation, yet there are no the patent of associated catalytic technology, once has catalyst and the technique of patent literature ketone compounds Hydrogenation alcohol compound.Patent CN1152744C, report the method that secondary octanone hydrogenating prepares sec-octyl alcohol in CN1114490C and CN1347758A, use its homemade catalyst system (Cu-contained catalyst, nickel-containing catalyst), adopt fixed bed liquid-phase hydrogenatin technique to realize, reaction temperature is 100 ~ 250 DEG C.The selective of sec-octyl alcohol is 96% ~ 99.5%.CN1974514A reports the method for methyln-hexyl ketone hydrogenating reduction sec-n-octyl alcohol, add in magnetically stabilized bed reactor and there is ferromagnetic hydrogenation catalyst, temperature 70 ~ 120 DEG C, pressure 0.3 ~ 2.5MPa, liquid volume air speed is 1 ~ 50h-1, hydrogen is 2 ~ 100:1 with the liquor capacity ratio containing methyln-hexyl ketone, and react under the condition of magnetic field intensity 10 ~ 50kA/m, sec-n-octyl alcohol can reach the yield of 70%.Patent CN1083415C adopts the CuO-ZnO mixture of compression molding to be catalyst, under the condition of reaction temperature 150 ~ 250 DEG C preparing isopropanol through gas phase hydrogenation of acetone conversion ratio and selectively reach 99%.The technique of the Ru/Al2O3 catalysis acetone hydrogenation of Japan Patent flat 2-279643 report is harsh, and reaction pressure is at 9MPa, and the investment of equipment is larger.Japan Patent flat-41038, Russian Patent SU1118632A describes the acetone hydrogenation method adopting Cu-Cr catalyst, Russ P RU2047590 employs containing NiO, the catalyst of the compositions such as CuO, but the conversion ratio of these catalyst is not high, and selective poor, the pollution of environment can be caused while the use of Cr2O3 as auxiliary agent, do not meet the requirement of green chemical industry.CN103030525A reports a kind of method that isopropyl alcohol is prepared in acetone liquid-phase hydrogenatin, but reaction temperature is higher, and at 100 ~ 200 DEG C, in the reaction time longer (4 hours), the conversion ratio of acetone is more than 96%, and the selective of isopropyl alcohol is greater than 95%.CN1962588 reports the gas phase hydrogenation continuous reaction of catalyst for acetone loading to active carbon with nickel cobalt dual-metal, reaction temperature at 100 ~ 150 DEG C, pressure at 1.0 ~ 1.5MPa, higher acetone conversion can be obtained and isopropyl alcohol selective.CN103706365 reports ambrose alloy bimetal supported catalyst and fixes bed hydroprocessing for acetone atmospheric gas, and reaction temperature is at 100 ~ 150 DEG C, and isopropyl alcohol is selective reaches 100%, and the conversion ratio of acetone can reach more than 85.5%.CN103706377A, CN103752327A report with Pt, Fe, Sn, Co to be the metallic catalyst of main component isopropyl alcohol is prepared in acetone liquid-phase hydrogenatin, and reaction temperature is at 100 ~ 150 DEG C, and the reaction time is 4h.USP4,182,721 report the catalytic hydrogenation that a kind of skeletal nickel catalyst by molybdenum modification is used for ketone compounds, although gentleer (60 DEG C of the condition of reaction, 2.1MPa), but selectivity of product is poor, and the reaction time longer (6h).USP4,459, the 419 a kind of methods reporting organic ketone or aldehyde hydrogenation, the catalyst of use is the ruthenium catalyst loaded on molecular sieve, and lists the application of preparing tetrahydrofurfuryl alcohol by furfuralcohol hydrogenation, but pressure needed for this reaction system is higher, reaches 12.7MPa.The temperature of the ketone hydrogenation that patent has been reported is higher, or the reaction time is longer, or the operating condition of pressure is higher to equipment requirement, or conversion ratio and the selective of product cannot reach high standard simultaneously, if the high activity developing a kind of low-temp reaction is in short-term held concurrently, high-selectivity catalyst will greatly reduce the cost of production process, alleviating the later stage is separated the burden of link, on the whole low energy consumption and efficiently carry out producing the requirement meeting green chemical industry.
Summary of the invention
The object of the invention is to the deficiency overcoming prior art, a kind of Catalysts and its preparation method of propione Hydrogenation 3-amylalcohol is provided.
The technical solution adopted for the present invention to solve the technical problems is to provide a kind of catalyst of propione Hydrogenation 3-amylalcohol, and on carbon-based material, load many components metal, is denoted as M1-M2-M3/C.Wherein M1 selects the one in Ru, Mn, Ag, and M2 selects the one in Ir, Au, Cu, and M3 selects the one in La, Ce, Y.Described carbon-based material is active carbon, carbon black or CNT.The load capacity of the load capacity of M1 to be the load capacity of 0.1% ~ 1.7%, M2 be 0.1% ~ 1.7%, M3 is 0.1% ~ 0.6%.
The catalyst application of propione Hydrogenation 3-amylalcohol of the present invention is when propione Hydrogenation 3-amylalcohol, adopt intermittent high-pressure reactor liquid-phase hydrogenatin process, its process Hydrogen Vapor Pressure is 1 ~ 5.5MPa, reaction temperature is 50 ~ 100 DEG C, described catalyst inventory/substrate is 0.001 ~ 0.01g/ml, and the reaction time is 20min ~ 1.5h.
The present invention also provides a kind of method preparing above-mentioned catalyst, comprises the following steps:
(1) immerse in the metal salt solution of M3 by carbon-based material, stir certain hour after regulating pH, wherein the slaine of M3 can be nitrate, acetylacetonate or chloride, and solution can be water, acetone, or the solution of ethylene glycol;
(2) after filtration, washing, drying, the carbon-based material being adsorbed with M3 is carried out roasting, obtain M3/C, wherein sintering temperature is 200 ~ 800 DEG C, and the time is 2 ~ 8h.
(3) immerse in the metal salt solution of M1 and M2 by M3/C, stir certain hour after regulating pH, wherein the slaine of M1, M2 can be nitrate, acetylacetonate or chloride, and solution can be water, acetone, or the solution of ethylene glycol;
(4) after filtration, washing, drying, the carbon-based material being adsorbed with M3, M1 and M2 is carried out roasting, obtain M1-M2-M3/C, wherein sintering temperature is 200 ~ 800 DEG C, and the time is 2 ~ 8h.
Preferably, in step (1) and step (3), pH value is adjusted to 0.5 ~ 5.5 or 8 ~ 13.
Preferably, in step (1), mixing time is 2-5h.
Preferably, in step (3), stirring carries out at the temperature of 25 ~ 250 DEG C, and mixing time is 2-12h.
Preferably, in step (4), described drying is vacuum drying 10-14h at 40-80 DEG C.
Preferably, in step (2) and step (4), calcination atmosphere is nitrogen, hydrogen or hydrogen nitrogen mixed gas, and heating rate is 2 ~ 6 DEG C/min.
Catalyst of the present invention first adds M3 in preparation process, namely first introduces the characteristic electron that rare earth element effectively can improve carrier, and the introducing of rare earth element simultaneously effectively can increase the decentralization of metal.The introducing of M3 mainly serves the effect of Structure promoter.The combination of M1 and M2 needs to meet the collaborative rule in two center, and the ability that such as M1 activates substrate is comparatively strong, and the ability that M2 activates hydrogen is comparatively strong, and so two centers synergy of M1 and M2 just can be embodied.It is important to note that be directly connected to the selective of product to the activation absorption of substrate is strong and weak.Selecting suitable atmosphere and suitable temperature to carry out roasting can the strong interaction of enhanced activity center and carrier effectively, and this strong interaction can improve the activity of catalyst effectively.
The invention has the beneficial effects as follows:
(1) use the operating temperature of the liquid-phase hydrogenatin process of this catalyst relative with operating pressure gentle, energy consumption is lower, and equipment investment is little.
(2) catalyst presents high activity, and the reaction time is shorter, enhances productivity.
(3) reach the selective of 3-amylalcohol while 100% at propione conversion ratio and reach 100%, greatly alleviate late-stage products and be separated burden, reduce production cost.
(4) catalyst preparing is relative with production method simple, is applicable to producing in enormous quantities using.
Following examples are described in further detail the present invention; But the Catalysts and its preparation method of a kind of propione Hydrogenation 3-amylalcohol of the present invention is not limited to embodiment.
Detailed description of the invention
Embodiment 1
Take the six water cerous nitrates of 0.008g, put into 50ml deionized water, add the active carbon of 0.6g, after stirring 3h, regulate pH=10 with ammoniacal liquor, and Keep agitation 3h, filtration washing.60 DEG C of vacuum drying 12h.In nitrogen, be warming up to 400 DEG C with 5 DEG C/min, constant temperature 3h is down to room temperature.Obtained Ce/C.
Take the chloride hydrate ruthenium of 0.024g, 0.024g Hydrated copper chloride puts into 50ml ethylene glycol, stirs 30min.Ce/C obtained by upper step is put into above-mentioned solution, regulates pH=10 with NaOH, stir and be warming up to 230 DEG C of maintenance 2h.Be down to room temperature, filtration washing, 60 DEG C of vacuum drying 12h.In nitrogen, be warming up to 400 DEG C with 6 DEG C/min, be down to room temperature after constant temperature 2h, obtained Ru-Cu-Ce/C catalyst, wherein the load capacity of the load capacity of Ru to be the load capacity of 0.1% ~ 1.7%, Cu be 0.1% ~ 1.7%, Ce is 0.1% ~ 0.6%.When being applied to propione Hydrogenation 3-amylalcohol, catalyst inventory/substrate is 0.01g/ml, and in intermittent high-pressure reaction kettle for reaction, reaction temperature 100 DEG C, the reaction time is 1.5h, and Hydrogen Vapor Pressure is 5.3MPa, and stir speed (S.S.) is 500 turns/min.The conversion ratio recording propione hydrogenation is that the selective of 83.3%, 3-amylalcohol reaches 99.6%.
Embodiment 2
Take the lanthanum nitrate hexahydrate of 0.008g, put into 50ml deionized water, add the carbon black of 0.6g, after stirring 3h, regulate pH=12 with NaOH, and Keep agitation 2h, filtration washing.40 DEG C of vacuum drying 14h.In nitrogen, be warming up to 500 DEG C with 5 DEG C/min, constant temperature 3h is down to room temperature.Obtained La/C.
Take the chloride hydrate ruthenium of 0.015g, the gold chloride of 0.015g, put into the deionized water of 50ml, stir 30min.La/C obtained by upper step is put into above-mentioned solution, regulates pH=3 with hydrochloric acid, stirring at room temperature 12h.Infrared lamp rapid draing, 60 DEG C of vacuum drying 10h.In hydrogen, be warming up to 230 DEG C with 3 DEG C/min, be down to room temperature after constant temperature 8h, obtained Ru-Au-La/C catalyst, wherein the load capacity of the load capacity of Ru to be the load capacity of 0.1% ~ 1.7%, Au be 0.1% ~ 1.7%, La is 0.1% ~ 0.6%.When being applied to propione Hydrogenation 3-amylalcohol, catalyst inventory/substrate is 0.005g/ml, and in intermittent high-pressure reaction kettle for reaction, reaction temperature 100 DEG C, the reaction time is 1.5h, and Hydrogen Vapor Pressure is 1MPa, and stir speed (S.S.) is 500 turns/min.The conversion ratio recording propione hydrogenation is that the selective of 35.7%, 3-amylalcohol reaches 100%.
Embodiment 3
Take the six water yttrium nitrates of 0.008g, put into 50ml deionized water, add the CNT of 0.6g, after stirring 3h, regulate pH=12 with NaOH, and Keep agitation 5h, filtration washing, 80 DEG C of vacuum drying 12h.In nitrogen, be warming up to 500 DEG C with 5 DEG C/min, constant temperature 3h is down to room temperature.Obtained Y/C.
Take the hydration chloro-iridic acid of 0.01g and the silver nitrate of 0.01g, put into 50ml deionized water, stir 30min.Y/C obtained by upper step is put into above-mentioned solution, and the hydrochloric acid with 10% regulates pH=2, stirring at room temperature 8h.Infrared lamp rapid draing, 60 DEG C of vacuum drying 12h.In hydrogen, be warming up to 200 DEG C with 2 DEG C/min, be down to room temperature after constant temperature 6h, obtained Ag-Ir-Y/C catalyst, wherein the load capacity of the load capacity of Ag to be the load capacity of 0.1% ~ 1.7%, Ir be 0.1% ~ 1.7%, Y is 0.1% ~ 0.6%.When being applied to propione Hydrogenation 3-amylalcohol, catalyst inventory/substrate is 0.01g/ml, and in intermittent high-pressure reaction kettle for reaction, reaction temperature 100 DEG C, the reaction time is 1.5h, and Hydrogen Vapor Pressure is 5.3MPa, and stir speed (S.S.) is 500 turns/min.The conversion ratio recording propione hydrogenation is that the selective of 99.7%, 3-amylalcohol reaches 100%.
Embodiment 4
Take the six water yttrium nitrates of 0.008g, put into 50ml deionized water, add the CNT of 0.6g, after stirring 3h, regulate pH=13 with NaOH, and Keep agitation 3h, filtration washing.60 DEG C of vacuum drying 12h.In nitrogen, be warming up to 500 DEG C with 5 DEG C/min, constant temperature 3h is down to room temperature.Obtained Y/C.
Take the chloride hydrate ruthenium of 0.015g and the hydration chloro-iridic acid of 0.015g, put into 50ml acetone, stir 30min.Y/C obtained by upper step is put into above-mentioned solution, and the hydrochloric acid with 20% regulates pH=1 and stirring at room temperature 12h.Infrared lamp rapid draing, 60 DEG C of vacuum drying 12h.300 DEG C are warming up to 2 DEG C/min in hydrogen nitrogen mixed gas (10% hydrogen), be down to room temperature after constant temperature 3h, obtained Ru-Ir-Y/C catalyst, wherein the load capacity of Ru is 0.1% ~ 1.7%, the load capacity of Ir is the load capacity of 0.1% ~ 1.7%, Y is 0.1% ~ 0.6%.When being applied to propione Hydrogenation 3-amylalcohol, catalyst inventory/substrate is 0.01g/ml, and in intermittent high-pressure reaction kettle for reaction, reaction temperature 50 DEG C, the reaction time is 35min, and Hydrogen Vapor Pressure is 5.3MPa, and stir speed (S.S.) is 500 turns/min.The conversion ratio recording propione hydrogenation is that the selective of 100%, 3-amylalcohol reaches 100%.
Embodiment 5
Take the lanthanum nitrate hexahydrate of 0.008g, put into 50ml deionized water, add the carbon black of 0.6g, after stirring 3h, regulate pH=12 with NaOH, and Keep agitation 3h, filtration washing.60 DEG C of vacuum drying 12h.In nitrogen, be warming up to 500 DEG C with 5 DEG C/min, constant temperature 3h is down to room temperature.Obtained La/C.
Take manganese acetylacetonate and the 0.024g Hydrated copper chloride of 0.015g, put into 50ml acetone, stir 30min.La/C obtained by upper step is put into above-mentioned solution, the hydrochloric acid with 10% regulates pH=2, stirring at room temperature 12h.Infrared lamp rapid draing, 60 DEG C of vacuum drying 12h.In hydrogen, be warming up to 800 DEG C with 2 DEG C/min, be down to room temperature after constant temperature 3h, obtained Mn-Cu-La/C catalyst, wherein the load capacity of the load capacity of Mn to be the load capacity of 0.1% ~ 1.7%, Cu be 0.1% ~ 1.7%, La is 0.1% ~ 0.6%.When being applied to propione Hydrogenation 3-amylalcohol, catalyst inventory/substrate is 0.01g/ml, and in intermittent high-pressure reaction kettle for reaction, reaction temperature 50 DEG C, the reaction time is 20min, and Hydrogen Vapor Pressure is 5.3MPa, and stir speed (S.S.) is 500 turns/min.The conversion ratio recording propione hydrogenation is the selective of 17.5%, 3-amylalcohol is 100%.
Embodiment 6
Take the six water cerous nitrates of 0.008g, put into 50ml deionized water, add the active carbon of 0.6g, after stirring 3h, regulate pH=8 with ammoniacal liquor, and Keep agitation 3h, filtration washing.60 DEG C of vacuum drying 12h.In nitrogen, be warming up to 400 DEG C with 5 DEG C/min, constant temperature 2h is down to room temperature.Obtained Ce/C.
Take the hydration chloro-iridic acid of 0.008g and the manganese acetylacetonate of 0.015g, put into 50ml acetone, stir 30min.Ce/C obtained by upper step is put into above-mentioned solution, and the hydrochloric acid with 5% regulates pH=4.5, stirring at room temperature 12h.Infrared lamp rapid draing, 60 DEG C of vacuum drying 12h.In hydrogen, be warming up to 600 DEG C with 2 DEG C/min, be down to room temperature after constant temperature 3h, obtained Mn-Ir-Ce/C catalyst, wherein the load capacity of the load capacity of Mn to be the load capacity of 0.1% ~ 1.7%, Ir be 0.1% ~ 1.7%, Ce is 0.1% ~ 0.6%.When being applied to propione Hydrogenation 3-amylalcohol, catalyst inventory/substrate is 0.001g/ml, and in intermittent high-pressure reaction kettle for reaction, reaction temperature 50 DEG C, the reaction time is 20min, and Hydrogen Vapor Pressure is 3MPa, and stir speed (S.S.) is 500 turns/min.The conversion ratio recording propione hydrogenation is 87.9%., the selective of 3-amylalcohol reaches 100%.
Above-described embodiment is only used for further illustrating the Catalysts and its preparation method of a kind of propione Hydrogenation 3-amylalcohol of the present invention; but the present invention is not limited to embodiment; every above embodiment is done according to technical spirit of the present invention any simple modification, equivalent variations and modification, all fall in the protection domain of technical solution of the present invention.
Claims (8)
1. a catalyst for propione Hydrogenation 3-amylalcohol, is characterized in that load many components metal on carbon-based material, is denoted as M1-M2-M3/C.Wherein M1 selects the one in Ru, Mn, Ag, and M2 selects the one in Ir, Au, Cu, and M3 selects the one in La, Ce, Y.Described carbon-based material is active carbon, carbon black or CNT.The load capacity of the load capacity of M1 to be the load capacity of 0.1% ~ 1.7%, M2 be 0.1% ~ 1.7%, M3 is 0.1% ~ 0.6%.
2. the catalyst of propione Hydrogenation 3-amylalcohol according to claim 1, it is characterized in that: described catalyst application is in the reaction of propione Hydrogenation 3-amylalcohol, adopt intermittent high-pressure reactor liquid-phase hydrogenatin process, its process Hydrogen Vapor Pressure is 1 ~ 5.5MPa, reaction temperature is 50 ~ 100 DEG C, described catalyst inventory/substrate is 0.001 ~ 0.01g/ml, and the reaction time is 20min ~ 1.5h.
3. prepare a method for the catalyst of propione Hydrogenation 3-amylalcohol as claimed in claim 1, it is characterized in that comprising the following steps:
(1) immerse in the metal salt solution of M3 by carbon-based material, stir certain hour after regulating pH, wherein the slaine of M3 can be nitrate, acetylacetonate or chloride, and solution can be water, acetone, or the solution of ethylene glycol;
(2) after filtration, washing, drying, the carbon-based material being adsorbed with M3 is carried out roasting, obtain M3/C, wherein sintering temperature is 200 ~ 800 DEG C, and the time is 2 ~ 8h.
(3) immerse in the metal salt solution of M1 and M2 by M3/C, stir certain hour after regulating pH, wherein the slaine of M1, M2 can be nitrate, acetylacetonate or chloride, and solution can be water, acetone, or the solution of ethylene glycol;
(4) after filtration, washing, drying, the carbon-based material being adsorbed with M3, M1 and M2 is carried out roasting, obtain M1-M2-M3/C, wherein sintering temperature is 200 ~ 800 DEG C, and the time is 2 ~ 8h.
4. preparation method according to claim 2, is characterized in that: in step (1) and step (3), pH value is adjusted to 0.5 ~ 5.5 or 8 ~ 13.
5. preparation method according to claim 2, is characterized in that: in step (1), and mixing time is 2-5h.
6. preparation method according to claim 2, is characterized in that: in step (3), and stirring carries out at the temperature of 25 ~ 250 DEG C, and mixing time is 2-12h.
7. preparation method according to claim 2, is characterized in that: in step (4), and described drying is vacuum drying 10-14h at 40-80 DEG C.
8. preparation method according to claim 2, it is characterized in that in step (2) and step (4), calcination atmosphere is nitrogen, hydrogen or hydrogen nitrogen mixed gas, heating rate is 2 ~ 6 DEG C/min.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108993577A (en) * | 2018-06-13 | 2018-12-14 | 厦门大学 | A kind of catalyst and its preparation method and application of prepared from benzene and hydrogen cyclohexyl benzene |
| CN109046430A (en) * | 2018-08-29 | 2018-12-21 | 浙江工业大学 | Nitrogen-dopped activated carbon supported palladium-iron catalyst and its application for benzophenone catalytic hydrogenation synthesis benzhydrol |
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| CN102600858A (en) * | 2012-02-09 | 2012-07-25 | 厦门大学 | Preparation method of hydrogenation demetallization catalyst |
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| CN109046430A (en) * | 2018-08-29 | 2018-12-21 | 浙江工业大学 | Nitrogen-dopped activated carbon supported palladium-iron catalyst and its application for benzophenone catalytic hydrogenation synthesis benzhydrol |
| CN109046430B (en) * | 2018-08-29 | 2021-07-27 | 浙江工业大学 | Nitrogen-doped activated carbon-supported palladium-iron catalyst for synthesizing benzhydryl alcohol by catalytic hydrogenation of benzophenone and application thereof |
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