CN106566575B - Prepare the method for hydrocarbon and its compositions of hydrocarbons of preparation - Google Patents
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- CN106566575B CN106566575B CN201510655642.XA CN201510655642A CN106566575B CN 106566575 B CN106566575 B CN 106566575B CN 201510655642 A CN201510655642 A CN 201510655642A CN 106566575 B CN106566575 B CN 106566575B
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Abstract
The present invention relates to a kind of compositions of hydrocarbons for the method and its preparation preparing hydrocarbon, mainly solving the prior art, there are biomass derivatives aqueous phase reforming serious, the selectively low problems low with energy efficiency of liquid alkane that prepare C C keys fracture in liquid alkane technique.The present invention is by using including biomass derivatives and C1~C6The technical solution that the step of water phase is total to reforming reaction occurs in the presence of a catalyst for alcohol preferably solves the problems, such as this, can be used in the industrial production that biomass derivatives prepare liquid alkane.
Description
Technical field
The present invention relates to a kind of compositions of hydrocarbons for the method and its preparation preparing hydrocarbon.
Background technology
Increasingly depleted with fossil resource and a series of environment excessively caused by, the gas fossil energy
Time problem is had become a top priority using reproducible green energy resource gradually to substitute fossil energy.Biomass resource is current
Unique renewable organic carbon source, and it is cheap and easy to get.Liquid fuel and fine chemicals are prepared by biomass and its derivative
In recent years by the extensive concern of domestic and international chemist.2004, the Dumesic research groups of Univ Wisconsin-Madison USA
It reports for the first time and prepares reproducible C through aqueous phase reforming process by sorbierite1-C6Alkane (Angew.Chem.Int.Ed.2004,
43,1549-1551).This process is to pass through two step realities on the solid acid bifunctional catalyst of a noble-metal-supported
It is existing.Sorbierite (such as Pt) in noble metal component, which reform, first generates H2And CO2, while sorbierite again solid acid (such as
Silica-alumina dehydration occurs under catalysis).Then, under the catalysis of noble metal component, in the dehydration of sorbierite
Mesosome utilizes the H generated in situ2Deoxidation hydrogenation reaction occurs and finally obtains alkane.The final result entirely reacted is sorbierite
It is converted into alkane, CO2And water.But the aqueous phase reforming of itself of sorbierite produces fracture of the hydrogen process along with a large amount of C-C keys,
Generate a large amount of CO2(CO2Carbon yield accounts for about 40-50%), that entire technique finally obtains is mostly CO2With added value compared with
Small C1-C4Gas phase alkane (carbon yield reaches 81-95% in gas-phase product), only about 10% or so carbon has ultimately generated liquid
Alkane (pentane and hexane), liquid alkane yield and energy efficiency are low.Later, Dumesic research groups report from HMF and chaff
Aldehyde prepare long chain alkane (gasoline and diesel oil) Catalytic processes (Science, 2005,308:1446-1450).But HMF's is honest and clean
It is one of the bottleneck for restricting the technological development to prepare on a large scale to valence.In addition, it is all using costliness that these, which are studied without exception,
And it is difficult to the business H transported2As reaction hydrogen source, the commercial Application of these Catalytic processes is greatly limited.
It is broken seriously in short, the prior art prepares C-C keys in liquid alkane technique there are biomass derivatives aqueous phase reforming,
The selectively low problem low with energy efficiency of liquid alkane.
Invention content
The purpose of the present invention is to provide a kind of methods preparing hydrocarbon.For achieving the above object, the present invention takes
Technical solution is as follows：A method of preparing hydrocarbon, including biomass derivatives and C1~C6Water phase occurs in the presence of a catalyst for alcohol
The step of reforming reaction altogether；The C1~C6Alcohol general formula is CnH2n+2Om, the integer that wherein n is 1~6, the integer that m is 1~6.
In above-mentioned technical proposal, it is preferable that the biomass derivatives are selected from glucose, fructose, sucrose, synanthrin, fiber
Disaccharides, sorbierite, mannitol, xylose, xylitol, isobide, furfural, 5 hydroxymethyl furfural, sugar alcohol, aldehyde alcohol, cellulose spread out
In biology, lignin derivative, maltose, lactose, mannose, arabitol, erythrite, isomaltose, lactitol or maliol
At least one.
In above-mentioned technical proposal, it is preferable that general formula CnH2n+2Om, in, the integer that n is 1~3, the integer that m is 1~3.
In above-mentioned technical proposal, it is preferable that the C1~C6Alcohol be methanol, ethyl alcohol, ethylene glycol, propyl alcohol, 1,2- propylene glycol,
At least one of 1,3- propylene glycol or glycerine.
In above-mentioned technical proposal, it is preferable that the hydrocarbon is C1~C6Hydrocarbon.
In above-mentioned technical proposal, it is preferable that by weight percentage, the C1~C6In hydrocarbon, C1~C4The content of hydrocarbon is 20
~70%, C5~C6The content of hydrocarbon is 30~80%.
In above-mentioned technical proposal, it is preferable that the catalyst is the solid acid catalyst of Metal Supported；Wherein, metal accounts for
0.1~80% of total catalyst weight including solid acid.
In above-mentioned technical proposal, it is preferable that the metal include selected from the metal of Group VIIIB, its alloy and
Its mixture.
In above-mentioned technical proposal, it is preferable that the metal includes the gold selected from nickel, cobalt, iron, palladium, rhodium, ruthenium, platinum, iridium, osmium
Category, its alloy and its mixture.
In above-mentioned technical proposal, it is preferable that the metal further with selected from IB races metal, Group IIB metal, group vib gold
Belong to, the additional metal of VIIB races metal forms alloy or mixing；The content of the additional metal is no more than Group VIIIB
The 30% of content.
In above-mentioned technical proposal, it is preferable that the metal further with the additional metal selected from copper, manganese, chromium, molybdenum, zinc, rhenium
Form alloy or mixing.
In above-mentioned technical proposal, it is preferable that the solid acid is selected from SiO2、Al2O3、SiO2-Al2O3、Nb2O5、NbOPO4、
ZrOSO4, montmorillonite, attapulgite, H-ZSM-5, H- β, H-Y, sulfonation charcoal, at least one of carbon nanotube or carbon fullerene.
In above-mentioned technical proposal, it is preferable that the water phase is total to reforming reaction and is carried out under liquid phase.
In above-mentioned technical proposal, it is preferable that the water phase is total to reforming reaction and carries out in the presence of water.
In above-mentioned technical proposal, it is preferable that biomass derivatives and C1~C6It is raw in the aqueous phase reforming start material of alcohol
The weight percent concentration of material derivant is 1~90%, C1~C6The weight ratio of alcohol and biomass derivatives is 0.1~5.
In above-mentioned technical proposal, it is preferable that biomass derivatives and C1~C6It is raw in the aqueous phase reforming start material of alcohol
The weight percent concentration of material derivant is 10~70%, C1~C6The weight ratio of alcohol and biomass derivatives is 0.5~3.
In above-mentioned technical proposal, it is preferable that biomass derivatives and the weight ratio of catalyst are 1~100, and reaction temperature is
150~300 DEG C, pressure is self-generated pressure, and the reaction time is 0.5~60 hour.
The present invention also aims to provide a kind of described to prepare composition made from the method for hydrocarbon.With weight percent
It counts, in the composition, C1~C4The content of hydrocarbon is 20~70%, C5~C6The content of hydrocarbon is 30~80%.
The present invention also aims to provide a kind of described to prepare composition made from the method for hydrocarbon as liquid fuel
Purposes.
In the method for the present invention, " reforming altogether " is defined as biomass starting material derivative and C1~C6Alcohol is reacted with water respectively, jointly
Generate the process of hydrocarbon and/or hydrogen and carbon dioxide.So the method for the present invention carries out in the presence of water, be under liquid phase into
Capable.
Biomass starting material derivative for use in the present invention is selected from glucose, fructose, sucrose, synanthrin, cellobiose, sorb
It is alcohol, mannitol, xylose, xylitol, isobide, furfural, 5 hydroxymethyl furfural, sugar alcohol, aldehyde alcohol, cellulose derivative, wooden
At least one in plain derivative, maltose, lactose, mannose, arabitol, erythrite, isomaltose, lactitol or maliol
Kind.It is preferred that glucose, fructose, sucrose, synanthrin, cellobiose, sorbierite, mannitol, xylose, xylitol, isobide, furfural
And 5 hydroxymethyl furfural.
Another raw material C for use in the present invention1~C6Alcohol general formula is CnH2n+2Om, the integer that wherein n is 1~6, m is 1~6
Integer.It is preferred that the integer that n is 1~3, the integer that m is 1~3.Such as methanol, ethyl alcohol, ethylene glycol, propyl alcohol, 1,2- can be selected from
At least one of propylene glycol, 1,3- propylene glycol or glycerine.
Hydrocarbon described in the method for the present invention is C1~C6Hydrocarbon.By weight percentage, the C1~C6In hydrocarbon, C1~C4Hydrocarbon
Content is 20~70%, C5~C6The content of hydrocarbon is 30~80%.C1~C6Hydrocarbon includes but not limited to methane, ethane, ethylene, third
Alkane, propylene, normal butane, iso-butane, 1- butylene, 2- butylene, isobutene, 1,3- butadiene, pentane, isopentane, 1,3- diformazans
Base propane, pentamethylene, 1- amylenes, 2- amylenes, 2-methyl-1-butene alkene, 2- methyl-2-butenes, 3-methyl-1-butene, cyclopentene,
1,3- pentadienes, 1,4- pentadienes, 2- methyl-1s, 3- butadiene, 1,3- cyclopentadiene, n-hexane, 2- methylpentanes, 3- methyl
Pentane, 2,2- dimethylbutanes, 2,3- dimethylbutanes, methyl cyclopentane, 1- hexenes, 2- hexenes, 3- hexenes, 2- methyl-1s-
Amylene, 2- methyl -2- amylenes, 4- methyl -2- amylenes, 4-methyl-1-pentene, 3- Methyl-1-pentenes, 3- methyl -2- amylenes, 3,
3- dimethyl -1- butylene, 2,3- dimethyl -1- butylene, 2,3- dimethyl -2- butylene, cyclohexene, 1- methyl cyclopentenes, 2- first
Cyclopentene, 3- methyl cyclopentenes, 1,3- hexadienes, 1,4- hexadienes, 1,5- hexadienes, 2- methyl-1,3-pentylenes, 2- first
Base -1,4- pentadienes, 4- methyl-1,3-pentylenes, 3- methyl-1,3-pentylenes, 3- methyl-1s, 4- pentadienes, ethyl -1 2-,
3- butadiene, 2,3- dimethyl -1,3- butadiene, 1- methyl-cyclopentadiene, 2- methyl cyclopentadienes, 5- methyl cyclopentadienes.
In the methods of the invention, biomass starting material derivative and C1~C6Alcohol is mixed with water, generates aqueous solution.In solution
The weight percent concentration of biomass derivatives is 1~90%, C1~C6The weight ratio of alcohol and biomass derivatives is 0.1~5.
Preferred scope is that the weight percent concentration of biomass derivatives is 10~70%, C1~C6The weight of alcohol and biomass derivatives
Than being 0.5~3.
The catalyst used in the method for the present invention is the solid acid catalyst of carried metal, wherein metal should be urged with accounting for
0.1~80% amount of agent total weight (weight of solid acid is included) exists, preferably to account for the 1~50% of total weight
Amount exists.The metal is selected from metal, its alloy and its mixture of Group VIIIB.In these metals, preferably
It is nickel, cobalt, iron, palladium, rhodium, ruthenium, platinum, iridium, osmium, its alloy and its mixture.Preferably, Group VIIIB optionally with choosing
Alloy or mixing are formed from the metal of IB races metal, Group IIB metal, group vib metal, VIIB races metal.These additional metals
The 30% of Group VIIIB content is not to be exceeded in content.The optional metals for preferably comprising in the catalyst be copper, manganese, chromium,
Molybdenum, zinc, rhenium, its alloy and its mixture.Preferred scheme includes Pt-Re, Rh-Re, Pd-Re, Ir-Re, Pt-Co, Pt-Ni,
Pt-Re-Ni, Rh-Re-Ru, Pd-Re-Co.The solid acid includes but not limited to SiO2、Al2O3、SiO2-Al2O3、Nb2O5、
NbOPO4、ZrOSO4, montmorillonite, attapulgite, H-ZSM-5, H- β, H-Y, sulfonation charcoal, in carbon nanotube or carbon fullerene extremely
Few one kind, preferably SiO2And Al2O3.The usage amount of catalyst is：Biomass derivatives are 1~100 with catalyst weight ratio, excellent
Select 4~10.Solid acid can be prepared by conventional method known to those skilled in the art, such as sol-gal process, hydro-thermal
Synthetic method, coprecipitation, template etc..Metal Supported equally can also be by those skilled in the art in the method for solid acid
Prepared by well known conventional method, such as incipient impregnation, co-precipitation, deposition sedimentation etc..
The liquid phase of the present invention, which is total to reforming reaction, to be carried out at a temperature of being conducive to thermodynamics of reactions, General reactions temperature
It is 150~300 DEG C, preferably 220~270 DEG C.The selection of reaction pressure makes reaction be carried out under liquid phase.Reactor includes
Batch still and fixed bed reactors.
The method of the present invention uses C that is cheap and being easy to shipping storage1~C6Alcohol is hydrogen source, under bifunctional catalyst effect
It is carried out at the same time reaction with biomass derivatives.Due to C1~C6It is anti-that aqueous phase reforming more easily occurs compared to biomass derivatives for alcohol
It answers, so C1~C6Aqueous phase reforming and water gas shift reation occur first on metal for alcohol, can be in the H for generating isodose2Lower production
Raw less CO2, reduce CO2Discharge；Simultaneously because there are chemical balance, these H generated2And CO2It can press down again in turn
Biomass derivatives processed occur to reform side reaction, more to participate in deoxidation hydrogenation reaction, greatly reduce in biomass derivatives
The fracture of C-C keys, increases C5~C6The selectivity and yield of liquid alkane are made to make entirely to be catalyzed from biomass derivatives
The carbon utilisation rate and energy efficiency of standby liquid alkane promote a very big step, realize low cost, carry out to high production the energy turn
Change.Using the method for the present invention, biomass derivatives conversion ratio reaches as high as 100%, C5~C6The yield of liquid alkane reaches as high as
63%, achieve preferable technique effect.
The present invention will be further described below by way of examples.
Specific implementation mode
The embodiment of specific embodiment is as described below, and specific embodiment is listed in table.
Batch still reacts：By biomass derivatives aqueous solution, C1~C6Alcohol and catalyst put into glass inner bag not
Become rusty steel autoclave, sealing, is warming up to required temperature under fast stirring, and reaction stops after 0.5~60 hour, divides after cooling
Liquid obtains corresponding liquid alkane.Biomass derivatives mass concentration is 1~66%, C1~C6Alcohol and biomass derivatives weight
Amount is than being 0.2~5, and biomass derivatives are 1~100 with catalyst weight ratio, 180~300 DEG C of reaction temperature, and reaction pressure is
Self-generated pressure.
Fixed bed reaction：0.2~2g catalyst is packed into the stainless steel tubular reactor that internal diameter is 6mm, long 20mm, remaining
It is filled with 40~60 mesh quartz sands to reduce dead volume part.Reaction tube is put into reacting furnace after fixing and hunting leak whole device
1~10MPa is boosted to inert gas (nitrogen, argon gas or helium), to ensure that entire reaction carries out in the liquid state.Control reaction
Temperature is 180~300 DEG C, and gas flow rate is 0~10ml/min, biomass derivatives and C1~C6Alcohol wiring solution-forming soluble in water,
A concentration of 1~66%, C of biomass derivatives1~C6Alcohol is 0.2~5 with biomass derivatives mass ratio, and solution is noted with liquid phase pump
Enter, air speed is 0.1~10 hour-1, reaction solution after bed through condensation, reservoir, reaction solution liquid separation are flowed into after gas-liquid separation
Obtain corresponding liquid alkane afterwards.
C obtained by the reaction1-C6Hydrocarbon product is analyzed using on-line chromatograph, C1-C4Hydrocarbon product mainly include methane,
Ethane, ethylene, propane, propylene, normal butane, iso-butane, 1- butylene, 2- butylene, isobutene, 1,3-butadiene etc., C5-C6Liquid
Hydrocarbon product mainly has：Pentane, isopentane, pentamethylene, 1- amylenes, n-hexane, 2- methylpentanes, methyl cyclopentane, 1- oneself
Alkene etc..
Technical scheme of the present invention is further illustrated with reference to embodiment, but protection scope of the present invention is not limited to
This.
Embodiment 1-15 uses 5%Pt-Re/Al2O3(molar ratio of Pt and Re are 1:1) it is used as catalyst, in differential responses
Under the conditions of react, reaction condition and reaction result are shown in Table 1.
Table 1
Alcohol/derivative：Weight ratio, derivative/catalyst：Weight ratio.
Embodiment 16-30 uses catalyst prepared by distinct methods, catalyzing sorbitol and methanol in different reactor
Water phase is total to reforming reaction, and reaction result is shown in Table 2.
Table 2
In batch still, reaction condition is：Sorbitol concentration 10%, methanol and sorbierite weight ratio be 1, sorbierite with urge
Agent weight ratio is 4, and 250 DEG C of reaction temperature, pressure is self-generated pressure, 24 hours reaction time.
In fixed bed, reaction condition is：Sorbitol concentration 10%, methanol and sorbierite weight ratio are 1, and air speed 1.25 is small
When-1, 250 DEG C of temperature, pressure 6MPa.
Solid acid is SiO2-Al2O3When, SiO2/Al2O3Weight ratio is 1:2.
Claims (16)
1. a kind of method preparing hydrocarbon, including biomass derivatives and C1~C6Alcohol occurs water phase and reforms altogether in the presence of a catalyst
The step of reaction；The C1~C6Alcohol general formula is CnH2n+2Om, the integer that wherein n is 1~6, the integer that m is 1~6；The biology
Matter derivative is selected from glucose, fructose, sucrose, synanthrin, cellobiose, sorbierite, mannitol, xylose, xylitol, different sorb
In alcohol, sugar alcohol, aldehyde alcohol, maltose, lactose, mannose, arabitol, erythrite, isomaltose, lactitol or maliol at least
It is a kind of；
The catalyst is the solid acid catalyst of Metal Supported；Wherein, metal accounts for the total catalyst weight including solid acid
0.1~80%；The metal includes metal, its alloy and its mixture selected from Group VIIIB；The metal is into one
Step alloy or is mixed with the additional metal formation selected from Group IIB metal, group vib metal, VIIB races metal；The additional metal
Content is no more than the 30% of Group VIIIB content.
2. the method for preparing hydrocarbon according to claim 1, it is characterised in that general formula CnH2n+2Om, in, the integer that n is 1~3, m
For 1~3 integer.
3. the method for preparing hydrocarbon according to claim 1, it is characterised in that the C1~C6Alcohol be methanol, ethyl alcohol, ethylene glycol,
At least one of propyl alcohol, 1,2- propylene glycol, 1,3- propylene glycol or glycerine.
4. the method for preparing hydrocarbon according to claim 1, it is characterised in that the hydrocarbon is C1~C6Hydrocarbon.
5. the method for preparing hydrocarbon according to claim 4, it is characterised in that by weight percentage, the C1~C6In hydrocarbon, C1
~C4The content of hydrocarbon is 20~70%, C5~C6The content of hydrocarbon is 30~80%.
6. the method for preparing hydrocarbon according to claim 1, it is characterised in that the metal include selected from nickel, cobalt, iron, palladium, rhodium,
Ruthenium, platinum, iridium, the metal of osmium, its alloy and its mixture.
7. the method for preparing hydrocarbon according to claim 1, it is characterised in that the metal further with selected from copper, manganese, chromium,
Molybdenum, zinc, the additional metal formation alloy of rhenium or mixing.
8. the method for preparing hydrocarbon according to claim 1, it is characterised in that the solid acid is selected from SiO2、Al2O3、SiO2-
Al2O3、Nb2O5、NbOPO4、ZrOSO4, montmorillonite, attapulgite, H-ZSM-5, H- β, H-Y, sulfonation charcoal, carbon nanotube or carbon it is rich
Strangle at least one of alkene.
9. the method for preparing hydrocarbon according to claim 1, it is characterised in that the water phase is total to reforming reaction and is carried out under liquid phase.
10. the method for preparing hydrocarbon according to claim 1, it is characterised in that the water phase be total to reforming reaction in the presence of water into
Row.
11. the method for preparing hydrocarbon according to claim 1, it is characterised in that biomass derivatives and C1~C6The water phase weight of alcohol
In whole start material, the weight percent concentration of biomass derivatives is 1~90%, C1~C6Alcohol and biomass derivatives
Weight ratio is 0.1~5.
12. according to the method for preparing hydrocarbon described in claim 11, it is characterised in that biomass derivatives and C1~C6The water phase weight of alcohol
In whole start material, the weight percent concentration of biomass derivatives is 10~70%, C1~C6Alcohol and biomass derivatives
Weight ratio is 0.5~3.
13. the method for preparing hydrocarbon according to claim 1, it is characterised in that biomass derivatives and the weight ratio of catalyst are
1~100, reaction temperature is 150~300 DEG C, and pressure is self-generated pressure, and the reaction time is 0.5~60 hour.
14. a kind of described preparing composition made from the method for hydrocarbon by the way that claim 1~13 is any.
15. composition according to claim 14, it is characterised in that by weight percentage, in the composition, C1~C4
The content of hydrocarbon is 20~70%, C5~C6The content of hydrocarbon is 30~80%.
16. any purposes for preparing composition made from the method for hydrocarbon and being used as liquid fuel of claim 1~13.
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