CN105597752B - C5, the load type carbon material catalyst of C6 alkane and preparation method thereof are produced in a kind of sugar alcohol selective hydrogenation deoxidation - Google Patents
C5, the load type carbon material catalyst of C6 alkane and preparation method thereof are produced in a kind of sugar alcohol selective hydrogenation deoxidation Download PDFInfo
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Abstract
The present invention relates to a kind of sugar alcohol selective hydrogenation deoxidation to produce C5, the load type carbon material catalyst of C6 alkane, catalyst carrier is used as using one kind in activated carbon, graphene and CNT, metal Ru is active metal, the first auxiliary agent or the second auxiliary agent are added, first auxiliary agent is selected from one or both of Mo, Re and W oxide, and second auxiliary agent is phosphorus, the mass percent that the metal Ru accounts for carrier is 1~5wt%, and the mass percent that the phosphorus accounts for carrier is 2~20%.The present invention introduces metal active centres and auxiliary agent after acidified processing using activated carbon, graphene, CNT as carrier with infusion process substep.The catalyst, which is used for sugar alcohol aqueous phase hydrogenation deoxidation, has very good reactivity and stability, and sugar alcohol conversion ratio is 100%, C5, and C6 paraffin selectivities are up to 80%.
Description
Technical field
The invention belongs to catalytic field and chemical technology field, and in particular to a kind of sugar alcohol selective hydrogenation deoxidation is produced
Load type carbon material catalyst of C5, C6 alkane and preparation method thereof.
Background technology
Although the fossil resources such as current oil, coal, natural gas are still the main source of liquid fuel, it has obvious
Dependent resource.The increasingly severe and environmental problem of fossil resource supply conditions is on the rise, and forcing us to find being capable of generation
The new type resource of current energy general layout is replaced or supplements, biomass resource is considered as the optimal choosing for substituting fossil resource at present
Select.Saccharide compound is also known as carbohydrate, is naturally synthesized by photosynthesis by plant, be distributed in nature most extensively,
The most type organic of quantity.Wherein there are the construction unit of animals and plants, such as cellulose, hemicellulose, chitin etc., also have
Energy unit, such as glycogen, starch, chrysanthemum root powder etc..They can obtain sugar (mainly glucose by hydrolysis and oxygenation means
And xylose) or sugar alcohol (mainly sorbierite and xylitol).These sugar/sugar alcohols are considered as biomass energy hardware and software platform of new generation
Compound, hydrogen, alkane and chemicals can be synthesized by being catalyzed hydro-denitrification or aqueous phase reforming technology.
In the world, Dumesic and Huber (Angew Chem Int Ed, 2004,43:1549) first proposed by sugar alcohol
Hydrogenation deoxidation prepares the new method of C5, C6 alkane, is prepared for a kind of Pt/Si02-A1203Catalyst, effectively sugar alcohol can be turned
C1~C6 alkane (C5, C6 paraffin selectivity reach 60%) is turned to, so as to rise a kind of hair of bio liquid alkane technology
Exhibition.
It is domestic to prepare C5/C6 alkane technology also in sugar alcohol while carried out research and development.Wherein, Chinese patent
CN101550350A discloses the preparation method and catalyst of a kind of biogasoline, and its feature is using sorbitol aqueous solution as original
Material, using carried noble metal Pt/HZM-5 catalyst, hydrogenation deoxidation reaction is carried out in miniature paste state bed reactor, obtain compared with
The C5/C6 alkane of high selectivity.In addition, in order to substitute noble metal catalyst, Chinese patent CN102389832 discloses a kind of general
Logical metallic Ni catalyst, carrier is HZSM-5 and MCM-41 complex form.The expensive and reserves of one side precious metals pt
Rareness, and loss of active component and carbon distribution in use, cause catalyst cost of a relatively high, make in its commercial Application by
To certain limitation.Although still further aspect sieve and silica-sesquioxide or molecular sieve can provide acidic site to be advantageous to hydroxyl as carrier
The dehydration of base.But under thermal and hydric environment, sieve and silica-sesquioxide or molecular sieve will face hydrothermal stability deficiency and aluminium loss
The problems such as, so as to cause catalyst stability poor, the development and application for catalyst is a big obstacle.
The content of the invention
It is an object of the invention to provide a kind of sugar alcohol selective hydrogenation deoxidation to produce C5, the load type carbon material of C6 alkane
Catalyst, there is very good reactivity and stability for sugar alcohol aqueous phase hydrogenation deoxidation, sugar alcohol conversion ratio is 100%,
C5, C6 paraffin selectivity are up to 80%, while solve the technical barrier of carried catalyst hydrothermal stability difference.
It is another object of the present invention to provide a kind of sugar alcohol selective hydrogenation deoxidation to produce C5, the support type of C6 alkane
The preparation method of carbon material catalyst, metal active centres and auxiliary agent, energy consumption are introduced with infusion process substep after acidified processing
It is low, technical process is simple, be easy to the popularization of industrialized production.
In order to realize foregoing invention purpose, technical scheme is as follows：
C5 is produced in a kind of sugar alcohol selective hydrogenation deoxidation, the load type carbon material catalyst of C6 alkane, the catalyst
Structural formula is A-Z1-Z2/C or A-Z1/C, and support C is carried using one kind in activated carbon, graphene and CNT as catalyst
Body, component A are metal Ru, and the one kind of auxiliary agent Z1 in Mo, Re and W, auxiliary agent Z2 is phosphorus, and the metal Ru accounts for the quality of carrier
Percentage is 1~5%, and the mass percent that the auxiliary agent Z1 accounts for carrier is 2~20%, and the phosphorus accounts for the mass percent of carrier
For 2~20%.
Preferably, the metal Ru and Mo or Re or W atomic molar ratio is 1:0.5~1:2.
Based on the metal Ru good by the catalyst carrier load resistance to acids and bases with the good modification of hydro-thermal of the invention
Active sites, while it is used as auxiliary agent by adding Mo, Re or W oxide to improve the electro of metal Ru, suppress metal Ru's
Methanation activity, improve the selectivity of liquid alkane.
C5, the preparation method of the load type carbon material catalyst of C6 alkane, bag are produced in a kind of sugar alcohol selective hydrogenation deoxidation
Include following steps：
(1) with activated carbon, graphene and CNT one kind for carrier, by carrier mass percent be 30% with
On phosphoric acid solution 1~8h is stirred at 60~120 DEG C, wash, and at 80~150 DEG C dry drying；
(2) carbon carrier obtained by step (1) is impregnated into solution of ruthenium trichloride, keep metal Ru contents 1~
5wt%, roasting, obtains Ru-P/C catalyst；
(3) first auxiliary agent is added into step (2) to be made in Ru-P/C catalyst, by mixture drying process；
(4) drying sample obtained in step (3) is obtained the sugar alcohol and added in 300~420 DEG C of 2~8h of hydrogen reducing
Hydrogen deoxidation load type carbon material catalyst.
Preferably, it is the step of roasting described in step (2)：The catalyst carrier incipient impregnation ruthenium trichloride is molten
After liquid, supersound process or 1~8h of stir process, 80~150 DEG C of dryings, 300~420 DEG C of roastings under gaseous nitrogen or argon.
Preferably, the mixture is ultrasonically treated or 1~8h of stir process in step (3), 80~150 DEG C of dryings.
Preferably, the first auxiliary agent described in step (3) is selected from one or both of Mo, Re and W oxide.
Preferably, the mass percent that the phosphorus accounts for carrier is 2~20%.
The present invention also protects load type carbon material catalyst to produce C5 in sugar alcohol selective hydrogenation deoxidation, and C6 alkane is answered
With being catalyzed sugar alcohol hydrogenation deoxygenation using the load type carbon material catalyst prepared in the present invention can be in low pressure and relatively low temperature
The lower progress of degree, energy consumption is low, technical process is simple and easy to control, there is good industrial applications prospect.
A kind of load type carbon material catalyst produces C5 in sugar alcohol selective hydrogenation deoxidation, and the application of C6 alkane is described negative
Load type carbon material catalyst is catalyzed sugar/sugar alcohol in hydrothermal system and hydrogenation deoxidation reaction occurs, and sugar alcohol is urged in load type carbon material
The lower generation hydrogenolysis of agent effect ultimately produces C5/C6 alkane, reacts in intermittent high-pressure reactor or continous way trickle bed
Carried out in reactor, 250~360 DEG C of reaction temperature, 1~10MPa of Hydrogen Vapor Pressure.Liquid volume air speed is in 0.1~5.0h-1It
Between, gas volume air speed is in 1000~5000h-1Between.The product of hydrogenolysis generation uses gas-chromatography hydrogen flameionization
Detector (FID) and thermal conductivity detector (TCD) (TCD) detection.
Preferably, the sugar alcohol is selected from glucose solution, xylose solution, sorbitol solution, xylitol solution, isobide
One or more in solution, the sugar/sugar alcohol aqueous solution mass concentration are 10~60%.Sugar alcohol can be planted by high-content of starch
Thing, such as potato, fermentation or hydrolysis are made, and have broken away from existing liquid fuel production technology to the dependence of oil.
Preferably, C5, C6 alkane is pentane and hexane and their isomers, selected from 2- methylpentanes, 3- first
One or more in base pentane, methyl cyclopentane, hexamethylene and pentamethylene.
The beneficial effects of the invention are as follows：
(1) for the present invention using activated carbon, graphene, CNT as carrier, these carbon material surfaces have the micropore knot of prosperity
Structure, hydrophobicity is strong, and acidified and oxidation processes can have very strong selective absorption performance；
(2) catalyst proposed by the present invention, which is used for sugar alcohol aqueous phase hydrogenation deoxidation, has very good reactivity and stably
Property, sugar alcohol conversion ratio is 100%, C5, and C6 paraffin selectivities are up to 80%.
Embodiment
With reference to instantiation, the present invention is furture elucidated.It should be understood that these embodiments are merely to illustrate this hair
It is bright, rather than limit protection scope of the present invention.The improvement and tune that technical staff makes according to the present invention in actual applications
It is whole, still fall within protection scope of the present invention.
The equipment and reagent used except special instruction, the present invention is the art routine commercial products.Activated carbon is purchased from
Tangshan Huaneng Group science and technology Tan Ye Co., Ltds, graphene and CNT are purchased from the organic Suo Zhong sections epoch nanosecond science and technology in Chinese Academy of Sciences Chengdu
Co., Ltd, phosphoric acid solution used in the present invention are that chemical analysis is pure.
Embodiment 1
C5, the preparation method of the load type carbon material catalyst of C6 alkane, bag are produced in a kind of sugar alcohol selective hydrogenation deoxidation
Include following steps：
Claim 5g activated carbons (70-120 mesh) add round-bottomed flask in, be then slowly added into 100mL phosphoric acid solutions (85wt%),
100mL deionized waters and stirring magneton, then the condensation reflux unit on round-bottomed flask, places it in oil bath pan and heats and protect
Hold magneton and stir 450 revs/min, 90 DEG C of constant temperature processing 5h of oil bath, cool down normal temperature, filtration washing, filter cake is washed with deionized 3
After secondary, it be put into 120 DEG C of drying box and be dried overnight, you can obtains the absorbent charcoal carrier of phosphoric acid processing activation.
Weigh the absorbent charcoal carrier of 2 grams of phosphoric acid processing activation, incipient impregnation ruthenium trichloride (Ru contents 37%,
RuCl3.xH2O:0.05g) solution, be ultrasonically treated 1h after stand 8h, then in baking oven 120 DEG C be dried overnight, place into nitrogen
400 DEG C of roastings of muffle furnace, after being cooled to room temperature, then incipient impregnation ammonium heptamolybdate (Mo contents 54%, (NH4)6Mo7O24.4H2O:
0.04g) solution, be ultrasonically treated 1h after stand 8h, then in baking oven 120 DEG C overnight, gained catalyst be designated as Cat1 (Ru load
Measure as 1%, Ru:Mo=1:1).
Take dried catalyst 4mL to load reaction tube, silica wool and filler (quartz are separately added into before and after beds
Sand), device is then connected, hydrogen heating is passed through and prepares reduction, 320 DEG C of reduction are overnight.Sugar alcohol solution is in load type carbon material
Hydrogenolysis occurs under catalyst action and ultimately produces C5/C6 alkane, reacts and is carried out in continous way trickle bed reactor, reacted
320 DEG C of temperature, Hydrogen Vapor Pressure 4MPa.Liquid volume air speed is in 0.1~5.0h-1Between, gas volume air speed 1000~
5000h-1Between.The product of hydrogenolysis generation uses gas-chromatography flame ionization ditector (FID) and thermal conductivity detector (TCD)
(TCD) detect.
Sugar alcohol solution is sorbitol solution in the present embodiment, and its mass concentration is 20%.Activated carbon in the present invention is purchased from
Tangshan Huaneng Group science and technology Tan Ye Co., Ltds, model HN-Y14,70-120 mesh.
Embodiment 2
Same as Example 1, difference is：
The quality of the ammonium molybdate of incipient impregnation is 0.08g, and the mass concentration of sorbitol solution is 10%.
Embodiment 3
Same as Example 1, difference is：
The mass concentration of sorbitol solution is 40%.
Embodiment 4
Same as Example 1, difference is：
The mass concentration of sorbitol solution is 20%, 280 DEG C of reaction temperature, reaction pressure 2MPa.
Embodiment 5
Same as Example 1, difference is：
The mass concentration of sorbitol solution is 20%, 300 DEG C of reaction temperature.
Embodiment 6
Same as Example 1, difference is：
Sugar alcohol solution is glucose solution, and the mass concentration of glucose solution is 20%.
Embodiment 7
Same as Example 1, difference is：
Sugar alcohol solution is xylose solution, and the mass concentration of xylose solution is 20%.
Embodiment 8
Same as Example 1, difference is：
Sugar alcohol solution is xylitol solution, and the mass concentration of xylitol solution is 20%.
Embodiment 9
Same as Example 1, difference is：
It is to add 50mL phosphoric acid solutions (85wt%) and the mixing of 100mL deionized waters, condensation during Activated Carbon Pretreatment
Backflow.Sugar alcohol solution is sorbitol solution, and the mass concentration of sorbitol solution is 20%.
Embodiment 10
Claim 2g graphenes to add in round-bottomed flask, be then slowly added into 100mL phosphoric acid solutions (85wt%), 100mL go from
Sub- water and stirring magneton, then the condensation reflux unit on round-bottomed flask, places it in oil bath pan and heats and keep magneton to stir
450 revs/min are mixed, 90 DEG C of constant temperature processing 5h of oil bath, normal temperature is cooled down, filtration washing, after filter cake is washed with deionized 3 times, puts
Enter 120 DEG C of drying box to be dried overnight, you can obtain the absorbent charcoal carrier of phosphoric acid processing activation.
Weigh the absorbent charcoal carrier of 2 grams of phosphoric acid processing activation, incipient impregnation ruthenium trichloride (Ru contents 37%,
RuCl3.xH2O:0.05g) solution, be ultrasonically treated 1h after stand 8h, then in baking oven 120 DEG C be dried overnight, place into nitrogen
400 DEG C of roastings of muffle furnace, after being cooled to room temperature, then incipient impregnation ammonium molybdate is prepared (Ru-Mo/GC), quiet after supersound process 1h
Put 8h, then in baking oven 120 DEG C overnight, gained catalyst is designated as Cat10.
Course of reaction is same as Example 1,320 DEG C, Hydrogen Vapor Pressure 4MPa of reaction temperature, the mass concentration of sorbitol solution
For 20%.
Embodiment 11
Claim 2g CNTs to add in round-bottomed flask, be then slowly added into 100mL phosphoric acid solutions (85wt%), 100mL is gone
Ionized water and stirring magneton, then the condensation reflux unit on round-bottomed flask, places it in oil bath pan and heats and keep magneton
450 revs/min of stirring, 90 DEG C of constant temperature processing 5h of oil bath, cooling normal temperature, filtration washing, after filter cake is washed with deionized 3 times,
It is put into 120 DEG C of drying box to be dried overnight, you can obtain the absorbent charcoal carrier of phosphoric acid processing activation.
Weigh the absorbent charcoal carrier of 2 grams of phosphoric acid processing activation, incipient impregnation ruthenium trichloride (Ru contents 37%,
RuCl3.xH2O:0.05g) solution, be ultrasonically treated 1h after stand 8h, then in baking oven 120 DEG C be dried overnight, place into nitrogen
400 DEG C of roastings of muffle furnace, after being cooled to room temperature, then incipient impregnation ammonium molybdate is prepared (Ru-Mo/CNT), quiet after supersound process 1h
Put 8h, then in baking oven 120 DEG C overnight, gained catalyst is designated as Cat11.
Course of reaction is same as Example 1,320 DEG C, Hydrogen Vapor Pressure 4MPa of reaction temperature, the mass concentration of sorbitol solution
For 20%.
Embodiment 12
Identical with embodiment 11, difference is：
The Ru-P/CNT prepared incipient impregnation ammonium perrhenate (Ru-ReP/CNT) solution again.Sugar alcohol solution is sorbierite
Solution, the mass concentration of sorbitol solution is 20%.
Embodiment 13
Same as Example 1, difference is：
The Ru-P/C prepared incipient impregnation ammonium metatungstate (Ru-WP/CNT) solution again.Sugar alcohol solution is that sorbierite is molten
Liquid, the mass concentration of sorbitol solution is 20%.
Comparative example 1
Same as Example 1, difference is：
It is to add 100mL salpeter solutions (60wt%) and 50mL deionized waters and stirring, Ran Houleng during Activated Carbon Pretreatment
Solidifying backflow.Sugar alcohol solution is sorbitol solution, and the mass concentration of sorbitol solution is 20%.
Embodiment reaction condition and reaction result are shown in Table 1.
It can see from the experimental result of embodiment 1 and embodiment 10-13, the RuMoP/C catalyst is not only more preferable
Alkane yield, under the same conditions, the selectivity of its target product are also more superior.From embodiment 1~3 and embodiment 6-8
Contrast and experiment can be seen that the catalyst system and catalyzing and have for various concentrations and different types of sugar alcohol raw material urges well
Change effect.In addition, in conjunction with the embodiments 4, the investigation that embodiment 5 is carried out for differential responses condition, different reaction pressure has
Certain influence, but optimal reaction condition is (320 DEG C, 4MPa).Embodiment 1 and embodiment 9 and comparative example 1 are to catalyst
The investigation of Vehicle element process phosphorus acid content and different liquids acid is as can be seen that the reaction effect of the phosphoric acid processing of high concentration
Fruit is more preferably.Although the contrast that embodiment 10 and 11 is carried out can be seen that CNT (CNT) and graphene (GC) as carrier
Catalyst alkane overall yield is not high, but the selectivity of target alkane is fine.Embodiment 12, embodiment 13 is for different auxiliary agent Z1
Composition investigate, find Re with W as Mo, with Ru-MoP/AC too big on the reaction effect of these catalyst
Difference.In a word, the present invention is carried out under low pressure and relatively low temperature, energy consumption is low, technical process is simple and easy to control, there is good industry
Change application prospect.
Above-listed detailed description is illustrating for possible embodiments of the present invention, and the embodiment simultaneously is not used to limit this hair
Bright the scope of the claims, all equivalence enforcements or change without departing from carried out by the present invention, it is intended to be limited solely by the scope of patent protection of this case
In.
Claims (8)
1. C5 is produced in a kind of sugar alcohol selective hydrogenation deoxidation, the preparation method of the load type carbon material catalyst of C6 alkane, it is special
Sign is, comprises the following steps：
（1）With mass percent it is more than 30wt% by carrier with one kind in activated carbon, graphene and CNT for carrier
Phosphoric acid solution 1 ~ 8 h is stirred at 60 ~ 120 DEG C, wash, and at 80 ~ 150 DEG C dry drying；
（2）By step（1）In obtained by carbon carrier dipping solution of ruthenium trichloride, keep metal Ru contents in 1 ~ 5 wt%, roasting
Burn, obtain Ru-P/C catalyst intermediates；
（3）First auxiliary agent is added into step（2）It is made in Ru-P/C catalyst intermediates, by mixture drying process；
（4）By step（3）In obtained drying sample in 300 ~ 420 DEG C of 2 ~ 8h of hydrogen reducing, obtain the load type carbon material
Catalyst；
Wherein, step（3）Described in the first auxiliary agent be selected from Mo, Re and W one or both of oxide, first auxiliary agent
The mass percent for accounting for carrier is 2 ~ 20%, and the mass percent that the phosphorus accounts for carrier is 2 ~ 20%.
2. C5, the load type carbon material catalyst of C6 alkane are produced in sugar alcohol selective hydrogenation deoxidation according to claim 1
Preparation method, it is characterised in that step（2）Specially：By the catalyst carrier incipient impregnation solution of ruthenium trichloride, surpass
After 1 ~ 8h of sonication or stir process, 80 ~ 150 DEG C of dryings, 300 ~ 420 DEG C of roastings under gaseous nitrogen or argon.
3. C5, the load type carbon material catalyst of C6 alkane are produced in sugar alcohol selective hydrogenation deoxidation according to claim 1
Preparation method, it is characterised in that step（3）It is middle to be first ultrasonically treated the mixture or the h of stir process 1 ~ 8, then 80
~ 150 DEG C of dryings.
4. C5, the load type carbon material catalyst of C6 alkane are produced in the sugar alcohol selective hydrogenation deoxidation described in a kind of claim 1
The load type carbon material catalyst that is prepared of preparation method, it is characterised in that the structural formula of the catalyst is A-Z1-
Z2/C, support C is using one kind in activated carbon, graphene and CNT as catalyst carrier, and component A is metal Ru, auxiliary agent
The one kind of Z1 in Mo, Re and W, auxiliary agent Z2 are phosphorus, and the mass percent that the metal Ru accounts for carrier is 1 ~ 5 %, described to help
The mass percent that agent Z1 accounts for carrier is 2 ~ 20%, and the mass percent that the phosphorus accounts for carrier is 2 ~ 20%.
5. load type carbon material catalyst according to claim 4, it is characterised in that the metal Ru and Mo or Re
Or W atomic molar ratio is 1:0.5~1:2.
6. the load type carbon material catalyst described in a kind of claim 4 produces C5, C6 alkane in sugar alcohol selective hydrogenation deoxidation
Application, it is characterised in that the load type carbon material catalyst be catalyzed in hydrothermal system sugar alcohol occur hydrogenation deoxidation reaction,
Hydrogenolysis generation C5 occurs under the effect of load type carbon material catalyst for sugar alcohol, C6 alkane, reacts and is reacted in intermittent high-pressure
Carried out in kettle or continous way trickle bed reactor, 250 ~ 360 DEG C of reaction temperature, 1 ~ 10MPa of Hydrogen Vapor Pressure.
7. load type carbon material catalyst according to claim 6 produces C5, C6 alkane in sugar alcohol selective hydrogenation deoxidation
Application, it is characterised in that the one kind or several of the sugar alcohol in sorbitol solution, xylitol solution, Ismotic
Kind, the sugar alcohol aqueous solution mass concentration is 10 ~ 60%.
8. load type carbon material catalyst according to claim 6 produces C5, C6 alkane in sugar alcohol selective hydrogenation deoxidation
Application, it is characterised in that C5, C6 alkane is pentane and hexane and their isomers, selected from 2- methylpentanes, 3-
One or more in methylpentane, methyl cyclopentane, hexamethylene and pentamethylene.
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| CN106268888B (en) * | 2016-07-21 | 2019-06-11 | 中国科学院广州能源研究所 | A kind of catalyst of aqueous catalysis sugar alcohol waste C5, C6 alkane and its application |
| CN107008485B (en) * | 2017-05-08 | 2019-05-03 | 齐鲁工业大学 | A kind of nitrogen-doped graphene load Ru and WO3Catalyst and preparation method and application |
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| CN109304161B (en) * | 2017-07-28 | 2020-06-09 | 中国石油化工股份有限公司 | Catalyst for hydrogenation of 1, 4-cyclohexane dicarboxylic acid |
| CN109305887B (en) * | 2017-07-28 | 2021-10-01 | 中国石油化工股份有限公司 | Method for hydrogenation of 1, 4-cyclohexanedicarboxylic acid |
| CN110354877B (en) * | 2019-07-31 | 2022-06-03 | 青岛科技大学 | Catalyst for preparing 1, 6-hexanediol by reducing adipic acid and preparation method |
| CN112010726B (en) * | 2020-08-20 | 2023-02-24 | 中国科学院广州能源研究所 | Method for selectively preparing micromolecular alkane by catalyzing cellulose |
| CN112076749B (en) * | 2020-09-28 | 2023-01-17 | 中国科学院广州能源研究所 | Catalyst for preparing liquid fuel by hydrogenating and deoxidizing lignin oil and preparation method and application thereof |
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