CN104368359B - A kind of catalyst of propione Hydrogenation 3-amylalcohol and preparation method thereof - Google Patents
A kind of catalyst of propione Hydrogenation 3-amylalcohol and preparation method thereof Download PDFInfo
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Abstract
The invention discloses the catalyst of a kind of 3 pentanone Hydrogenation 3 amylalcohols, including carbon-based supports and many metal components, be denoted as M1 M2 M3/C.Wherein M1 selects Ru, and the one in Mn, Ag, M2 selects Ir, the one in Au, Cu, and M3 selects La, the one in Ce, Y.Above-mentioned catalyst is applied to 3 pentanone liquid-phase hydrogenatin processes, and the conversion ratio of 3 pentanones can be made within a short period of time to reach 100%, and the selectivity of 3 amylalcohols is 100% simultaneously.Present invention simultaneously provides the preparation method of above-mentioned catalyst, it is easy to preparation of industrialization.
Description
Technical field
The present invention relates to catalyst, particularly relate to catalyst of a kind of propione Hydrogenation 3-amylalcohol and preparation method thereof.
Background technology
3-amylalcohol is a kind of important industrial chemicals, and it is in addition to can be used for organic synthesis, is also used for flotation agent and solvent uses,
Belong to a kind of medicine intermediate, material intermediate, be a kind of fine chemicals.3-amylalcohol can be obtained by propione Hydrogenation, mesh
Before yet there are no the patent of associated catalytic technology, once had the catalyst of patent literature ketone compounds Hydrogenation alcohol compound
And technique.Patent CN1152744C, reports secondary octanone hydrogenating and prepares sec-octyl alcohol in CN1114490C and CN1347758A
Method, uses its homemade catalyst system (Cu-contained catalyst, nickel-containing catalyst), uses fixed bed liquid-phase hydrogenatin technique
Realizing, reaction temperature is 100～250 DEG C.The selectivity of sec-octyl alcohol is 96%～99.5%.It is pungent that CN1974514A reports 2-
The method of ketone hydrogenating reduction sec-n-octyl alcohol, adds in magnetically stabilized bed reactor and has ferromagnetic hydrogenation catalyst, in temperature
70～120 DEG C, pressure 0.3～2.5MPa, liquid volume air speed is 1～50h-1, and hydrogen with the liquor capacity ratio containing methyln-hexyl ketone is
2～100:1, react under conditions of magnetic field intensity 10～50kA/m, sec-n-octyl alcohol can reach the yield of 70%.Patent
CN1083415C uses the CuO-ZnO mixture of compression molding to be catalyst, under conditions of reaction temperature 150～250 DEG C
Conversion ratio and the selectivity of preparing isopropanol through gas phase hydrogenation of acetone reach 99%.The Ru/Al2O3 of Japan Patent flat 2-279643 report urges
The technique changing acetone hydrogenation is harsh, and reaction pressure is at 9MPa, and the investment of equipment is bigger.Japan Patent flat-41038, the Soviet Union is special
Profit SU1118632A describe use Cu-Cr catalyst acetone hydrogenation method, Russ P RU2047590 employ containing
The catalyst of the compositions such as NiO, CuO, but the conversion ratio of these catalyst is the highest, and selectivity is poor, Cr2O3 is as auxiliary agent
Use while can cause the pollution of environment, do not meet the requirement of green chemical industry.CN103030525A reports a kind of acetone
The method of isopropanol is prepared in liquid-phase hydrogenatin, but reaction temperature is higher, at 100～200 DEG C, and the response time longer (4 hours),
The conversion ratio of acetone is more than 96%, and the selectivity of isopropanol is more than 95%.CN1962588 reports and loads with nickel cobalt bimetallic
To the catalyst of activated carbon for the gas phase hydrogenation continuous reaction of acetone, reaction temperature at 100～150 DEG C, pressure 1.0～
1.5MPa, can obtain higher acetone conversion and isopropanol selectivity.CN103706365 reports ambrose alloy bimetallic support type
Catalyst fixes bed hydroprocessing for acetone atmospheric gas, and reaction temperature is at 100～150 DEG C, and isopropanol selectivity reaches 100%,
The conversion ratio of acetone is up to more than 85.5%.CN103706377A, CN103752327A report with Pt, Fe, Sn, Co
Isopropanol is prepared in acetone liquid-phase hydrogenatin for the metallic catalyst of main component, reaction temperature at 100～150 DEG C, the response time
For 4h.USP4,182,721 report a kind of catalytic hydrogenation that the skeletal nickel catalyst that molybdenum is modified is used for ketone compounds, although
The condition gentleer (60 DEG C, 2.1MPa) of reaction, but selectivity of product is poor, and the response time longer (6h).
USP4,459, the 419 a kind of methods reporting organic ketone or aldehyde hydrogenation, the catalyst of use is to load to the ruthenium catalysis on molecular sieve
Agent, and list the application of preparing tetrahydrofurfuryl alcohol by furfuralcohol hydrogenation, but the pressure needed for this reaction system is higher, reaches 12.7MPa.Specially
The temperature of the ketone hydrogenation that profit has been reported is higher, or the response time is longer, or the operating condition of pressure is higher to equipment requirements,
Or the selectivity of conversion ratio and product cannot reach high standard simultaneously, the height if the high activity developing a kind of low-temp reaction in short-term is held concurrently
Catalysts selective will greatly reduce the cost of production process, alleviates the later stage and separates 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
It is an object of the invention to overcome the deficiency of prior art, it is provided that the catalyst of a kind of propione Hydrogenation 3-amylalcohol and
Preparation method.
The technical solution adopted for the present invention to solve the technical problems is to provide the catalyst of a kind of propione Hydrogenation 3-amylalcohol,
On carbon-based material, load many components metal, be denoted as M1-M2-M3/C.Wherein M1 selection Ru, the one in Mn, Ag,
M2 selects Ir, the one in Au, Cu, and M3 selects La, the one in Ce, Y.Described carbon-based material is activated carbon,
White carbon black or CNT.The load capacity of M1 is 0.1%～1.7%, and the load capacity of M2 is 0.1%～1.7%, the load capacity of M3
It is 0.1%～0.6%.
When the catalyst of the propione Hydrogenation 3-amylalcohol of the present invention is applied to propione Hydrogenation 3-amylalcohol, use batch (-type) high
Pressure reactor liquid-phase hydrogenatin process, its process Hydrogen Vapor Pressure is 1～5.5MPa, and reaction temperature is 50～100 DEG C, described in urge
Agent inventory/substrate is 0.001～0.01g/ml, and the response time is 20min～1.5h.
The present invention also provides for a kind of method preparing above-mentioned catalyst, comprises the following steps:
(1) carbon-based material is immersed in the metal salt solution of M3, after regulation pH, stir certain time, the wherein metal of M3
Salt can be nitrate, acetylacetonate or chloride, and solution can be the solution of water, acetone, or ethylene glycol；
(2) filter, wash, after drying the carbon-based material being adsorbed with M3 carried out roasting, it is thus achieved that M3/C, wherein roasting temperature
Degree is 200～800 DEG C, and the time is 2～8h.
(3) M3/C is immersed in the metal salt solution of M1 and M2, regulation pH after stir certain time, wherein M1,
The slaine of M2 can be nitrate, acetylacetonate or chloride, and solution can be the solution of water, acetone, or ethylene glycol；
(4) filter, wash, after drying the carbon-based material being adsorbed with M3, M1 and M2 carried out roasting, it is thus achieved that 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 regulates to 0.5～5.5 or 8～13.
Preferably, in step (1), mixing time is 2-5h.
Preferably, in step (3), stirring is to carry out at a temperature of 25～250 DEG C, and mixing time is 2-12h.
Preferably, in step (4), described being dried 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.
The catalyst of the present invention is initially charged M3 in preparation process, the most first introduces rare earth element and can effectively improve carrier
Characteristic electron, the introducing of rare earth element simultaneously can be effectively increased the dispersion of metal.The introducing of M3 has primarily served structure
The effect of type auxiliary agent.The combination of M1 Yu M2 needs to meet the rule that double center is collaborative, and the ability of such as M1 activation substrate is relatively
By force, the ability of M2 activation hydrogen is stronger, then double centers synergism of M1 with M2 just can be embodied.Need especially
It is noted that the activation adsorption power of substrate to be directly connected to the selectivity of product.Select suitable atmosphere and suitable temperature
Carrying out roasting and can effectively strengthen the strong interaction in active center and carrier, this strong interaction can be effectively improved and urge
The activity of agent.
The invention has the beneficial effects as follows:
(1) the operation temperature using the liquid-phase hydrogenatin process of this catalyst is relatively mild with operation pressure, and energy consumption is relatively low, and equipment is thrown
Money is little.
(2) catalyst presents high activity, and the response time is shorter, improves production efficiency.
(3) reach the selectivity of 3-amylalcohol while 100% at propione conversion ratio, up to 100%, greatly to alleviate late-stage products and divide
From burden, reduce production cost.
(4) catalyst preparation and production method are relatively easy easy, are suitable for producing use in enormous quantities.
The present invention is described in further detail by following example；But the catalysis of a kind of propione Hydrogenation 3-amylalcohol of the present invention
Agent and preparation method thereof is not limited to embodiment.
Detailed description of the invention
Embodiment 1
Weigh the six water cerous nitrates of 0.008g, put in 50ml deionized water, add the activated carbon of 0.6g, use after stirring 3h
Ammonia regulation pH=10, and continuously stirred 3h, filtration washing.60 DEG C of vacuum drying 12h.With 5 DEG C/min liter in nitrogen
Temperature is to 400 DEG C, and constant temperature 3h is down to room temperature.Prepare Ce/C.
Weighing the chloride hydrate ruthenium of 0.024g, 0.024g Hydrated copper chloride is put in 50ml ethylene glycol, stirs 30min.By upper
Ce/C obtained by step puts in above-mentioned solution, regulates pH=10 with sodium hydroxide, and stirring is warming up to 230 DEG C and keeps 2h.
It is down to room temperature, filtration washing, 60 DEG C of vacuum drying 12h.It is warming up to 400 DEG C with 6 DEG C/min, after constant temperature 2h in nitrogen
Be down to room temperature, prepare Ru-Cu-Ce/C catalyst, wherein the load capacity of Ru is 0.1%～1.7%, the load capacity of Cu be 0.1%～
The load capacity of 1.7%, Ce is 0.1%～0.6%.When being applied to propione Hydrogenation 3-amylalcohol, catalyst inventory/substrate is
0.01g/ml, in intermittent high-pressure reaction kettle for reaction, reaction temperature 100 DEG C, the response time is 1.5h, and Hydrogen Vapor Pressure is
5.3MPa, stir speed (S.S.) is 500 turns/min.The conversion ratio recording propione hydrogenation is 83.3%, and the selectivity of 3-amylalcohol reaches
99.6%.
Embodiment 2
Weigh the lanthanum nitrate hexahydrate of 0.008g, put in 50ml deionized water, add the white carbon black of 0.6g, after stirring 3h, use hydrogen
Sodium oxide regulation pH=12, and continuously stirred 2h, filtration washing.40 DEG C of vacuum drying 14h.With 5 DEG C/min in nitrogen
Being warming up to 500 DEG C, constant temperature 3h is down to room temperature.Prepare La/C.
Weigh the chloride hydrate ruthenium of 0.015g, the gold chloride of 0.015g, put in the deionized water of 50ml, stir 30min.
La/C obtained by upper step is put in above-mentioned solution, regulates pH=3 with hydrochloric acid, 12h is stirred at room temperature.Infrared lamp rapid draing,
60 DEG C of vacuum drying 10h.In hydrogen, it is warming up to 230 DEG C with 3 DEG C/min, after constant temperature 8h, is down to room temperature, prepare
Ru-Au-La/C catalyst, wherein the load capacity of Ru is 0.1%～1.7%, and the load capacity of Au is 0.1%～1.7%, La's
Load capacity is 0.1%～0.6%.When being applied to propione Hydrogenation 3-amylalcohol, catalyst inventory/substrate is 0.005g/ml,
In intermittent high-pressure reaction kettle for reaction, reaction temperature 100 DEG C, the response time is 1.5h, and Hydrogen Vapor Pressure is 1MPa, stirring
Speed is 500 turns/min.The conversion ratio recording propione hydrogenation is 35.7%, and the selectivity of 3-amylalcohol reaches 100%.
Embodiment 3
Weigh the six water Yttrium trinitrates of 0.008g, put in 50ml deionized water, add the CNT of 0.6g, after stirring 3h
PH=12, and continuously stirred 5h, filtration washing, 80 DEG C of vacuum drying 12h are regulated with sodium hydroxide.With 5 DEG C/min in nitrogen
Being warming up to 500 DEG C, constant temperature 3h is down to room temperature.Prepare Y/C.
Weigh hydration chloro-iridic acid and the silver nitrate of 0.01g of 0.01g, put in 50ml deionized water, stir 30min.Will
Y/C obtained by upper step puts in above-mentioned solution, and the hydrochloric acid with 10% regulates pH=2, and 8h is stirred at room temperature.The fast rapid-curing cutback of infrared lamp
Dry, 60 DEG C of vacuum drying 12h.In hydrogen, it is warming up to 200 DEG C with 2 DEG C/min, after constant temperature 6h, is down to room temperature, prepare
Ag-Ir-Y/C catalyst, wherein the load capacity of Ag is 0.1%～1.7%, and the load capacity of Ir is 0.1%～1.7%, the load of Y
Amount is 0.1%～0.6%.When being applied to propione Hydrogenation 3-amylalcohol, catalyst inventory/substrate is 0.01g/ml,
Reacting in formula of having a rest autoclave, reaction temperature 100 DEG C, the response time is 1.5h, and Hydrogen Vapor Pressure is 5.3MPa, stirring speed
Rate is 500 turns/min.The conversion ratio recording propione hydrogenation is 99.7%, and the selectivity of 3-amylalcohol reaches 100%.
Embodiment 4
Weigh the six water Yttrium trinitrates of 0.008g, put in 50ml deionized water, add the CNT of 0.6g, after stirring 3h
PH=13, and continuously stirred 3h, filtration washing is regulated with sodium hydroxide.60 DEG C of vacuum drying 12h.With 5 DEG C/min in nitrogen
Being warming up to 500 DEG C, constant temperature 3h is down to room temperature.Prepare Y/C.
Weigh the chloride hydrate ruthenium of 0.015g and the hydration chloro-iridic acid of 0.015g, put in 50ml acetone, stir 30min.
Putting in above-mentioned solution by the Y/C obtained by upper step, the hydrochloric acid with 20% regulates pH=1 and 12h is stirred at room temperature.Infrared lamp is fast
Rapid-curing cutback is dry, 60 DEG C of vacuum drying 12h.It is warming up to 300 DEG C with 2 DEG C/min in hydrogen nitrogen mixed gas (10% hydrogen), permanent
Being down to room temperature after temperature 3h, prepare Ru-Ir-Y/C catalyst, wherein the load capacity of Ru is 0.1%～1.7%, the load capacity of Ir
Being 0.1%～1.7%, the load capacity of 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 response time is 35min, hydrogen
Atmospheric pressure is 5.3MPa, and stir speed (S.S.) is 500 turns/min.The conversion ratio recording propione hydrogenation is 100%, the choosing of 3-amylalcohol
Selecting property reaches 100%.
Embodiment 5
Weigh the lanthanum nitrate hexahydrate of 0.008g, put in 50ml deionized water, add the white carbon black of 0.6g, after stirring 3h, use hydrogen
Sodium oxide regulation pH=12, and continuously stirred 3h, filtration washing.60 DEG C of vacuum drying 12h.With 5 DEG C/min in nitrogen
Being warming up to 500 DEG C, constant temperature 3h is down to room temperature.Prepare La/C.
Weigh manganese acetylacetonate and the 0.024g Hydrated copper chloride of 0.015g, put in 50ml acetone, stir 30min.Will
La/C obtained by upper step puts in above-mentioned solution, the hydrochloric acid with 10% regulates pH=2, and 12h is stirred at room temperature.Infrared lamp is fast
Rapid-curing cutback is dry, 60 DEG C of vacuum drying 12h.In hydrogen, it is warming up to 800 DEG C with 2 DEG C/min, after constant temperature 3h, is down to room temperature, system
Obtaining Mn-Cu-La/C catalyst, wherein the load capacity of Mn is 0.1%～1.7%, and the load capacity of Cu is 0.1%～1.7%, La
Load capacity be 0.1%～0.6%.When being applied to propione Hydrogenation 3-amylalcohol, catalyst inventory/substrate is 0.01g/ml,
In intermittent high-pressure reaction kettle for reaction, reaction temperature 50 DEG C, the response time is 20min, and Hydrogen Vapor Pressure is 5.3MPa, stirs
Mixing speed is 500 turns/min.The conversion ratio recording propione hydrogenation is 17.5%, and the selectivity of 3-amylalcohol is 100%.
Embodiment 6
Weigh the six water cerous nitrates of 0.008g, put in 50ml deionized water, add the activated carbon of 0.6g, use after stirring 3h
Ammonia regulation pH=8, and continuously stirred 3h, filtration washing.60 DEG C of vacuum drying 12h.Nitrogen heats up with 5 DEG C/min
To 400 DEG C, constant temperature 2h is down to room temperature.Prepare Ce/C.
Weigh hydration chloro-iridic acid and the manganese acetylacetonate of 0.015g of 0.008g, put in 50ml acetone, stir 30min.
Putting in above-mentioned solution by the Ce/C obtained by upper step, the hydrochloric acid with 5% regulates pH=4.5, and 12h is stirred at room temperature.Infrared lamp
Rapid draing, 60 DEG C of vacuum drying 12h.In hydrogen, it is warming up to 600 DEG C with 2 DEG C/min, after constant temperature 3h, is down to room temperature,
Preparing Mn-Ir-Ce/C catalyst, wherein the load capacity of Mn is 0.1%～1.7%, and the load capacity of Ir is 0.1%～1.7%, Ce
Load capacity be 0.1%～0.6%.When being applied to propione Hydrogenation 3-amylalcohol, catalyst inventory/substrate is 0.001g/ml,
In intermittent high-pressure reaction kettle for reaction, reaction temperature 50 DEG C, the response time is 20min, and Hydrogen Vapor Pressure is 3MPa, stirs
Mixing speed is 500 turns/min.The conversion ratio recording propione hydrogenation is 87.9%., the selectivity of 3-amylalcohol reaches 100%.
Above-described embodiment is only used for further illustrating catalyst and the preparation side thereof of a kind of propione Hydrogenation 3-amylalcohol of the present invention
Method, but the invention is not limited in embodiment, every according to the technical spirit of the present invention above example is made any simply
Amendment, equivalent variations and modification, each fall within the protection domain of technical solution of the present invention.
Claims (7)
1. a catalyst for propione Hydrogenation 3-amylalcohol, is characterized in that loading many components metal on carbon-based material,
It is denoted as M1-M2-M3/C；Wherein M1 selects Ru, and the one in Mn, Ag, M2 selects Ir, in Au, Cu
One, M3 selects La, the one in Ce, Y；Described carbon-based material is activated carbon, white carbon black or CNT；
The load capacity of M1 is 0.1%～1.7%, and the load capacity of M2 is 0.1%～1.7%, the load capacity of M3 be 0.1%～
0.6%.
The catalyst of propione Hydrogenation 3-amylalcohol the most according to claim 1, it is characterised in that urge described in:
Agent is applied in the reaction of propione Hydrogenation 3-amylalcohol, uses intermittent high-pressure reactor liquid-phase hydrogenatin process, its mistake
Journey Hydrogen Vapor Pressure is 1～5.5MPa, and reaction temperature is 50～100 DEG C, described catalyst inventory/substrate be 0.001～
0.01g/ml, the response time is 20min～1.5h.
3. a preparation method for the catalyst of propione Hydrogenation 3-amylalcohol as claimed in claim 1, its feature
It is to comprise the following steps:
(1) carbon-based material is immersed in the metal salt solution of M3, after regulation pH, stir certain time, wherein M3
Slaine be nitrate, acetylacetonate or chloride, solution is the solution of water, acetone or ethylene glycol；
(2) filter, wash, after drying the carbon-based material being adsorbed with M3 carried out roasting, it is thus achieved that M3/C, wherein
Sintering temperature is 200～800 DEG C, and the time is 2～8h；
(3) M3/C is immersed in the metal salt solution of M1 and M2, stir certain time, wherein after regulation pH
The slaine of M1, M2 is nitrate, acetylacetonate or chloride, and solution is the solution of water, acetone or ethylene glycol；
(4) filter, wash, after drying the carbon-based material being adsorbed with M3, M1 and M2 carried out roasting, it is thus achieved that
M1-M2-M3/C, wherein sintering temperature is 200～800 DEG C, and the time is 2～8h.
Preparation method the most according to claim 3, it is characterised in that: in step (1) and step (3), pH
Value regulation is to 0.5～5.5 or 8～13.
Preparation method the most according to claim 3, it is characterised in that: in step (1), mixing time is 2-5h.
Preparation method the most according to claim 3, it is characterised in that: in step (3), stirring be 25～
Carrying out at a temperature of 250 DEG C, mixing time is 2-12h.
Preparation method the most according to claim 3, it is characterised in that: in step (4), described be dried be
10-14h it is vacuum dried at 40-80 DEG C.
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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 |
| 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 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU1397423A1 (en) * | 1986-03-13 | 1988-06-15 | Предприятие П/Я Р-6830 | Method of producing pentanol-2 |
| CN102274734A (en) * | 2010-06-13 | 2011-12-14 | 中化蓝天集团有限公司 | Catalyst used for gas phase catalytic hydrogenation of hexafluoroacetone hydrate for preparing hexafluoroisopropanol and preparation method and application thereof |
| CN102600858A (en) * | 2012-02-09 | 2012-07-25 | 厦门大学 | Preparation method of hydrogenation demetallization catalyst |
| CN102746087A (en) * | 2012-08-01 | 2012-10-24 | 厦门大学 | Method for preparing cyclohexane by catalyzing and hydrogenising benzene at room temperature |
| CN103566930A (en) * | 2013-11-01 | 2014-02-12 | 山东新和成药业有限公司 | Pd/SiO2 catalyst and preparation method and application thereof |
-
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU1397423A1 (en) * | 1986-03-13 | 1988-06-15 | Предприятие П/Я Р-6830 | Method of producing pentanol-2 |
| CN102274734A (en) * | 2010-06-13 | 2011-12-14 | 中化蓝天集团有限公司 | Catalyst used for gas phase catalytic hydrogenation of hexafluoroacetone hydrate for preparing hexafluoroisopropanol and preparation method and application thereof |
| CN102600858A (en) * | 2012-02-09 | 2012-07-25 | 厦门大学 | Preparation method of hydrogenation demetallization catalyst |
| CN102746087A (en) * | 2012-08-01 | 2012-10-24 | 厦门大学 | Method for preparing cyclohexane by catalyzing and hydrogenising benzene at room temperature |
| CN103566930A (en) * | 2013-11-01 | 2014-02-12 | 山东新和成药业有限公司 | Pd/SiO2 catalyst and preparation method and application thereof |
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