CN105037066B - One step realizes the preparation of Pt/C catalyst and the method for hexahydrotoluene dehydrogenation - Google Patents
One step realizes the preparation of Pt/C catalyst and the method for hexahydrotoluene dehydrogenation Download PDFInfo
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- CN105037066B CN105037066B CN201510467908.8A CN201510467908A CN105037066B CN 105037066 B CN105037066 B CN 105037066B CN 201510467908 A CN201510467908 A CN 201510467908A CN 105037066 B CN105037066 B CN 105037066B
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- acetylacetone
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- pentanedione platinum
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Abstract
The invention discloses a step and realize the preparation of Pt/C catalyst and the method for hexahydrotoluene dehydrogenation；Configuration acetylacetone,2,4-pentanedione platinum ethanol solution and the mixing of carbon ball deionized water solution, prepare acetylacetone,2,4-pentanedione platinum/carbon ball suspension sucking filtration, through being dried to obtain acetylacetone,2,4-pentanedione platinum/carbon ball powder；By acetylacetone,2,4-pentanedione platinum/carbon ball pressed powder, being placed in atmospheric fixed bed reactor, be passed through hexahydrotoluene, entering temperature of reactor is 280 DEG C 320 DEG C, hexahydrotoluene dehydrogenation.The present invention is directed to existing preparation catalyst process complicated, the problems such as oxidation easily occur.Utilizing the feature of high temperature in hexahydrotoluene catalytic reaction process, generate Pt characteristic in combination with acetylacetone,2,4-pentanedione platinum pyrolytic, in catalytic process, a step prepares Pt/C catalyst, and obtains efficient hexahydrotoluene dehydrogenation.The synthetic method of the present invention is simple and convenient to operate, easily controllable, no coupling product and impurity, belongs to fabricated in situ and eco-friendly green synthesis process.
Description
Technical field
The present invention is to achieve the preparation of Pt/C catalyst and the method for hexahydrotoluene dehydrogenation about a step, utilizes particularly to one
In catalytic process, hot conditions one step is prepared Pt/C catalyst and accelerates the process of catalytic reaction.
Background technology
Hydrogen Energy has the advantages such as rich reserves, wide material sources, energy density height as a kind of " green energy resource ", at fuel electricity
The aspect such as pond and substitute fossil fuels presents good application prospect.During utilizing, it stores and transport is crucial.When
When hydrogen is as a kind of fuel, necessarily there is dispersibility and the intermittent feature used, therefore allow for storing within a period of time and
Transport is to given place.International Energy Agency specifies, practical its quality hydrogen-storage density of hydrogen storage system must reach 5wt%, Er Qieti
Store up hydrogen density to also require that more than 40kg/m3。
At present, report that more hydrogen storage method mainly has low temperature liquid hydrogen storage, high-pressure gaseous hydrogen storage, metal alloy hydrogen storage, material with carbon element
The methods such as adsorption hydrogen-storing, chemical hydride hydrogen storage and metal-organic framework materials (MOFs) hydrogen storage.These methods all achieve one
Fixed progress, but also need to consider further in terms of quality hydrogen-storage density, volume hydrogen-storage density, energy efficiency, safety, cost etc..
Therefore, find high efficiency, low cost and can just become crucial by the hydrogen storage method that utilizes of scale again.See: the primary human relations of Zhu Gang profit poplar, liquid
Body organic hydride hydrogen storage progress. chemical progress 21 (2009) 2760-2770.
Hexahydrotoluene is with its high hydrogen-storage density: quality hydrogen-storage density is as 6.1wt%, and volume hydrogen-storage density is 47Kg/m3, and by
Gradually cause people's extensive concern；Secondly, hexahydrotoluene is industrial large-scale production chemical article；Furthermore, hexahydrotoluene
Hydrogen storage is circulating and reversible process, i.e. methylbenzene-hexahydrotoluene can be hydrogenated with and dehydrogenation under the agent structure not destroying carbocyclic ring, this
It is the non-sensitive reaction of structure, while c h bond ruptures, does not affect the structure of C-C skeleton, and it is reversible for reacting.Meanwhile,
Owing to hydrogenation process is that Gibbs free energy reduces process, and absolute value is very big, and thermodynamics is extremely advantageous, i.e. hydrogenation process is non-
Chang Rongyi is carried out；And certain embodiments is strong endothermic reaction, react more difficult carrying out, need to use catalyst to reduce reaction barrier.
It mostly is two-step method about hexahydrotoluene dehydrogenation preparation method at present, i.e. needs first to prepare catalyst, afterwards
Reapplying in catalytic reaction, be the most more typically infusion process, mix with carbon ball dipping initially with chloroplatinic acid, repeated hydrogenation is also afterwards
Former Pt/C catalyst of preparing, finally reapplies in this course of reaction of hexahydrotoluene dehydrogenation.See: Cui
Zhang,Shuangxi Liu etal.Hydrogen production by catalytic dehydrogenation of
methylcyclohexane over Pt catalysts supported on pyrolytic waste tire
Char.International Journal Of Hydrogen Energy 36 (2011) 8902-8907. but it is being prepared by catalyst
Problem of oxidation all can be there is afterwards in participation reaction placement process, even precious metals pt is also can hardly be avoided, and in catalytic process,
Only atomic state Pt just can play catalytic action, and oxidation state Pt can not play catalytic action.So being badly in need of a kind of novel process
Method, a step can realize catalyst preparation in-situ applications in hexahydrotoluene dehydrogenation.One-step method is urged in hexahydrotoluene dehydrogenation
Changing in course of reaction and prepare catalyst, feed back acceleration hexahydrotoluene dehydrogenation simultaneously, centre is not related to first prepare urge
Agent, is then transferred in reaction unit, is different from common two-step method, can be prevented effectively from catalyst and aoxidize and obtain efficient first
Butylcyclohexane dehydrogenation.
Summary of the invention
The purpose of the present invention, is complicated for existing preparation catalyst process, and the problems such as oxidation easily occur.Utilize hexahydrotoluene
The feature of high temperature in catalytic reaction process, generates Pt characteristic, a step in catalytic process in combination with acetylacetone,2,4-pentanedione platinum pyrolytic
Prepare Pt/C catalyst, and obtain efficient hexahydrotoluene dehydrogenation.
The present invention is achieved by following technical solution.
One step achieves the preparation of Pt/C catalyst and the method for hexahydrotoluene dehydrogenation, and step is as follows:
(1) acetylacetone,2,4-pentanedione platinum ethanol solution and the mixing of carbon ball deionized water solution will be configured, prepare acetylacetone,2,4-pentanedione platinum/carbon ball suspension
Sucking filtration, through being dried to obtain acetylacetone,2,4-pentanedione platinum/carbon ball powder；
(2) by acetylacetone,2,4-pentanedione platinum/carbon ball pressed powder, it is placed in atmospheric fixed bed reactor, is passed through hexahydrotoluene, enter reaction
Device temperature is 280 DEG C-320 DEG C, hexahydrotoluene dehydrogenation.
The mass concentration of described acetylacetone,2,4-pentanedione platinum ethanol solution is preferably: 0.25g/L-1.5g/L.
Described carbon ball deionized water solution mass concentration is preferably: 20g/L-50g/L.
Described acetylacetone,2,4-pentanedione platinum ethanol solution is added drop-wise in carbon ball deionized water solution.Acetylacetone,2,4-pentanedione platinum ethanol solution and carbon ball go from
Sub-aqueous solution volume ratio is preferably 1:1-2:1.
Described hexahydrotoluene charging rate is preferably 0.03mL/min-0.05ml/min.
During the charging of described hexahydrotoluene, being passed through nitrogen, N2 flow is preferably 5mL/min-7ml/min.
Described its purity of acetylacetone,2,4-pentanedione platinum is preferably 99.999%.
Agilent 7700x type proton inductivity coupled plasma mass spectrometry combined instrument can be used, analyze the content of Pt in sample.
GC-7800 type gas chromatograph can be used to be analyzed, hexahydrotoluene and hydrogen content .GC-7800 in assay products
Type gas chromatograph is SE-54 capillary column, use flame ionization ditector (FID), constant temperature 80 DEG C, vaporizer 230 DEG C,
Detector 230 DEG C.
The present invention, with acetylacetone,2,4-pentanedione platinum for Pt source, utilizes acetylacetone,2,4-pentanedione platinum high temperature to decompose and generates the characteristic of catalyst Pt；Secondly,
Utilize hot properties in hexahydrotoluene certain embodiments.Ingenious combine both, when hexahydrotoluene dehydrogenation reaction, one
Footwork prepares Pt/C catalyst, and completes hexahydrotoluene dehydrogenation reaction.One-step synthesis in course of reaction, i.e. catalyst one
Prepare, immediately come into operation, be not related to catalyst transfer, effectively prevent catalyst oxidation, thus obtain one efficiently
Catalytic performance, i.e. hexahydrotoluene hydrogen-producing speed and conversion ratio all reach one the most high-level.
The present invention has the effect that
(1) instant invention overcomes existing preparation technology and prepare the deficiencies such as catalyst is oxidizable, surface is the cleanest, it is provided that be a kind of
One step is prepared Pt/C catalyst and completes hexahydrotoluene dehydrogenation.A step high-temp in-situ system in hexahydrotoluene catalytic reaction process
For going out Pt/C catalyst, feedback accelerates hexahydrotoluene dehydrogenation simultaneously.Centre is not related to catalyst transfer, effectively prevent catalysis
Agent in use problem of oxidation.Additionally, the synthetic method of the present invention is simple and convenient to operate, easily controllable, no coupling product
And impurity, belong to fabricated in situ and eco-friendly green synthesis process.
(2) present invention is a kind of universality method, can be suitable for the reaction of other high-temperature catalytics with Pt as catalyst.
Accompanying drawing explanation
Fig. 1 is the thermal multigraph that the present invention prepares Pt/C loaded catalyst；
Fig. 2 is Pt/C loaded catalyst high power transmission electron microscope photo of the present invention；
Fig. 3 is Pt/C loaded catalyst particle diameter distribution statistics of the present invention；
Fig. 4 is Pt/C loaded catalyst of the present invention whole x-ray photoelectron energy spectrogram；
Fig. 5 is hydrogen-producing speed figure under Pt/C support type different loads amount of the present invention；
Fig. 6 is conversion ratio figure under Pt/C support type different loads amount of the present invention.
Detailed description of the invention
Raw material used by the present invention is commercially available analytical pure raw material
Embodiment 1:
Weighing 5mg purity is 99.999% acetylacetone,2,4-pentanedione platinum, is dissolved in 20ml ethanol solution, stirs 30min, is configured to
0.25g/L acetylacetone,2,4-pentanedione platinum ethanol solution；Weigh 1g carbon ball, be scattered in 20ml deionized water, ultrasonic 30min, be configured to
50g/L carbon ball aqueous solution；Acetylacetone,2,4-pentanedione platinum ethanol solution and carbon ball deionized water solution volume ratio are 1:1；Use dropping side afterwards
Acetylacetone,2,4-pentanedione platinum ethanol solution is added drop-wise in carbon ball aqueous solution by formula, is sufficiently stirred for 3h afterwards, it is ensured that acetylacetone,2,4-pentanedione platinum is the most
Absorption, sucking filtration afterwards, be dried 5h at 80 DEG C, through ICP-MS test in acetylacetone,2,4-pentanedione platinum/carbon ball platinum load capacity be 0.18%.
Taking 0.3g acetylacetone,2,4-pentanedione platinum/carbon ball, tabletting afterwards, be placed in fixing reaction bed device, hexahydrotoluene charging rate is
0.03ml/min, N2 flow is 5mL/min, and vaporizer, preheater, temperature of reactor are 280 DEG C, high temperature in catalytic process
Promoting acetylacetone,2,4-pentanedione platinum and decompose generation Pt nano-particle, feed back catalysis hexahydrotoluene dehydrogenation simultaneously, a step achieves urges
Agent preparation and dehydrogenation test.
Embodiment 2:
Weighing 15mg purity is 99.999% acetylacetone,2,4-pentanedione platinum, is dissolved in 40ml ethanol solution, stirs 30min, is configured to
0.375g/L acetylacetone,2,4-pentanedione platinum ethanol solution；Weigh 1g carbon ball, be scattered in 30ml deionized water, ultrasonic 30min, preparation
Become 33.3g/L carbon ball aqueous solution；Acetylacetone,2,4-pentanedione platinum ethanol solution and carbon ball deionized water solution volume ratio are 1.33:1；Use and drip
Acetylacetone,2,4-pentanedione platinum ethanol solution is added drop-wise in carbon ball aqueous solution by add mode, is sufficiently stirred for 3h afterwards, it is ensured that acetylacetone,2,4-pentanedione platinum to the greatest extent may be used
Can adsorb, afterwards sucking filtration more, at 80 DEG C, be dried 5h, through ICP-MS test in acetylacetone,2,4-pentanedione platinum/carbon ball platinum load capacity be 0.37%.
Taking 0.3g acetylacetone,2,4-pentanedione platinum/carbon ball, tabletting afterwards, be placed in fixing reaction bed device, hexahydrotoluene charging rate is
0.04ml/min, N2 flow is 6mL/min, and vaporizer, preheater, temperature of reactor are 300 DEG C, high temperature in catalytic process
Promoting acetylacetone,2,4-pentanedione platinum and decompose generation Pt nano-particle, feed back catalysis hexahydrotoluene dehydrogenation simultaneously, a step achieves urges
Agent preparation and dehydrogenation test.Wherein, acetylacetone,2,4-pentanedione platinum purity is 99.999%.
Embodiment 3:
Weighing 25mg purity is 99.999% acetylacetone,2,4-pentanedione platinum, is dissolved in 60ml ethanol solution, stirs 30min, is configured to
0.417g/L acetylacetone,2,4-pentanedione platinum ethanol solution；Weigh 1g carbon ball, be scattered in 40ml deionized water, ultrasonic 30min, preparation
Become 25g/L carbon ball aqueous solution；Acetylacetone,2,4-pentanedione platinum ethanol solution and carbon ball deionized water solution volume ratio are 1.5:1；Use dropping
Acetylacetone,2,4-pentanedione platinum ethanol solution is added drop-wise in carbon ball aqueous solution by mode, is sufficiently stirred for 3h afterwards, it is ensured that acetylacetone,2,4-pentanedione platinum is as far as possible
Many absorption, sucking filtration afterwards, be dried 5h at 80 DEG C, through ICP-MS test in acetylacetone,2,4-pentanedione platinum/carbon ball platinum load capacity be 0.68%.
Taking 0.3g acetylacetone,2,4-pentanedione platinum/carbon ball, tabletting afterwards, be placed in fixing reaction bed device, hexahydrotoluene charging rate is
0.05ml/min, N2 flow is 7mL/min, and vaporizer, preheater, temperature of reactor are 320 DEG C, high temperature in catalytic process
Promoting acetylacetone,2,4-pentanedione platinum and decompose generation Pt nano-particle, feed back catalysis hexahydrotoluene dehydrogenation simultaneously, a step achieves urges
Agent preparation and dehydrogenation test.
Embodiment 4:
Weighing 150mg purity is 99.999% acetylacetone,2,4-pentanedione platinum, is dissolved in 100ml ethanol solution, stirs 30min, is configured to
1.5g/L acetylacetone,2,4-pentanedione platinum ethanol solution；Weigh 1g carbon ball, be scattered in 50ml deionized water, ultrasonic 30min, be configured to
20g/L carbon ball aqueous solution；Acetylacetone,2,4-pentanedione platinum ethanol solution and carbon ball deionized water solution volume ratio are 2:1；Employing dropping mode will
Acetylacetone,2,4-pentanedione platinum ethanol solution is added drop-wise in carbon ball aqueous solution, is sufficiently stirred for 3h afterwards, it is ensured that the many as far as possible absorption of acetylacetone,2,4-pentanedione platinum,
Sucking filtration afterwards, is dried 5h at 80 DEG C, through ICP-MS test in acetylacetone,2,4-pentanedione platinum/carbon ball platinum load capacity be 2.83%.Take afterwards
0.3g acetylacetone,2,4-pentanedione platinum/carbon ball, tabletting, it is placed in fixing reaction bed device, hexahydrotoluene charging rate is 0.05ml/min,
N2 flow is 5mL/min, and vaporizer, preheater, temperature of reactor are 320 DEG C, and in catalytic process, high temperature promotes levulinic
Ketone platinum decomposes generation Pt nano-particle, feeds back catalysis hexahydrotoluene dehydrogenation simultaneously, and a step achieves catalyst preparation and takes off
Hydrogen performance test.
The invention will be further described below in conjunction with the accompanying drawings.
Showing from Fig. 1 heavy load amount 2.83% acetylacetone,2,4-pentanedione platinum/carbon ball sample thermogravimetric analysis, acetylacetone,2,4-pentanedione platinum is at 220 DEG C-320 DEG C
Really there occurs change, but not can determine that acetylacetone,2,4-pentanedione platinum there occurs that what changes on earth.
Fig. 2 (a) (c) is sample after load capacity 0.45% acetylacetone,2,4-pentanedione platinum/320 DEG C of carbon ball annealing 1h and 320 DEG C of 10h dehydrogenations,
B () (d) is sample after load capacity 0.68% acetylacetone,2,4-pentanedione platinum/320 DEG C of carbon ball annealing 1h and 320 DEG C of 10h dehydrogenations.Demonstrate
High temperature action promotes acetylacetone,2,4-pentanedione platinum to be decomposed to form Pt nano-particle.
Fig. 3 is heavy load amount 2.83% acetylacetone,2,4-pentanedione platinum/320 DEG C of carbon ball sample annealing 1h particle diameter distribution statistics, particle mean size
For 1.28nm.
Fig. 4 is heavy load amount 2.83% acetylacetone,2,4-pentanedione platinum/carbon ball x-ray photoelectron energy spectrogram, and the respectively X after dehydrogenation reaction penetrates
Photoelectron spectra figure, the x-ray photoelectron energy spectrogram of 320 DEG C of annealing 1h and acetylacetone,2,4-pentanedione platinum x-ray photoelectron energy spectrogram.
Wherein after 320 DEG C of annealing 1h, show that acetylacetone,2,4-pentanedione platinum has occurred that decomposition, generate 0 valency Pt, but this part 0 valency Pt
Expose and there occurs oxidation in atmosphere and then generate Pt II with Pt IV；Sample after dehydrogenation, acetylacetone,2,4-pentanedione platinum is decomposed to form completely
0 valency Pt, exposes some generation oxidation in atmosphere and generates Pt II.
Fig. 1,2,3,4 demonstrate high temperature action has promoted acetylacetone,2,4-pentanedione platinum to decompose formation Pt nanometer, and average chi really
Very little for 1.28nm.
It is respectively hydrogen-producing speed under different loads amount by Fig. 5, Fig. 6, with conversion ratio, to reach maximum when load capacity is 0.37% and produce hydrogen
Speed 570mmol/g/min.Conversion ratio increases also with load capacity, is gradually increased, when load capacity is 0.68% close to one
100% conversion ratio.
The present invention is open and all methods of proposing and technology of preparing, and those skilled in the art can be by using for reference present disclosure, suitably
The link such as feed change and process route realizes, although the method for the present invention and technology of preparing are carried out by preferred embodiment
Describing, person skilled substantially can be to methods and techniques described herein road in without departing from present invention, spirit and scope
Line is modified or reconfigures, and realizes final technology of preparing.Special needs to be pointed out is, all similar replacements and
Changing apparent to those skilled in the art, they are considered as being included in present invention spirit, scope and content.
Claims (7)
1. a step achieves the preparation of Pt/C catalyst and the method for hexahydrotoluene dehydrogenation, it is characterized in that step is as follows:
(1) acetylacetone,2,4-pentanedione platinum ethanol solution and the mixing of carbon ball deionized water solution will be prepared, prepare acetylacetone,2,4-pentanedione platinum/carbon ball suspension, sucking filtration, obtaining acetylacetone,2,4-pentanedione platinum/carbon ball powder through being dried；
(2) by acetylacetone,2,4-pentanedione platinum/carbon ball pressed powder, being placed in atmospheric fixed bed reactor, be passed through hexahydrotoluene, temperature of reactor is 280 DEG C-320 DEG C, carries out hexahydrotoluene dehydrogenation reaction.
2. the method for claim 1, is characterized in that the mass concentration of acetylacetone,2,4-pentanedione platinum ethanol solution is: 0.25g/L-1.5g/L.
3. the method for claim 1, is characterized in that carbon ball deionized water solution mass concentration is: 20g/L-50g/L.
4. the method for claim 1, is characterized in that acetylacetone,2,4-pentanedione platinum ethanol solution is added drop-wise in carbon ball deionized water solution.
5. the method for claim 1, is characterized in that acetylacetone,2,4-pentanedione platinum ethanol solution and carbon ball deionized water solution volume ratio are 1:1-2:1.
6. the method for claim 1, is characterized in that hexahydrotoluene charging rate is 0.03mL/min-0.05ml/min.
7. the method for claim 1, is characterized in that when hexahydrotoluene feeds, and is passed through nitrogen, N2Flow is 5mL/min-7ml/min.
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Non-Patent Citations (4)
| Title |
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| Continuous hydrogen evolution from cyclohexanes over platinum catalysts supported on activated carbon fibers;Pham Dung Tien et al.;《FUEL PROCESSING TECHNOLOGY》;20081231;第89卷;415-418 * |
| Hydrogen production by catalytic dehydrogenation of methylcyclohexane over Pt catalysts supported on pyrolytic waste tire char;Cui Zhang et al.;《international journal of hydrogen energy》;20110531;第36卷;8902-8907 * |
| Synthesis of highly dispersed platinum particles on carbon nanotubes by an in situ vapor-phase method;C. Mercado-Zúñiga et al.;《Journal of Alloys and Compounds》;20140226;第615卷;S538-S541 * |
| 不同活性炭上Pt催化剂的分散性及其在甲基环己烷脱氢反应中的催化性能;李晓芸等;《催化学报》;20080330;第29卷(第3期);259-263 * |
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