CN106316733A - Method for preparing aromatic hydrocarbons by aromatization of alcohol compounds - Google Patents
Method for preparing aromatic hydrocarbons by aromatization of alcohol compounds Download PDFInfo
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Abstract
The invention relates to a method for preparing aromatic hydrocarbons by aromatization of alcohol compounds. Under aromatization conditions, C4-6 alcohol is in contact with a catalyst to generate an aromatic hydrocarbon stream containing benzene, toluene and xylene; the catalyst is selected from composite zirconium oxide XaOb/ZrO2, wherein x is at one kind of compounds selected from tungsten, molybdenum, cerium, lanthanum or manganese, a and b are chemical metering numbers; and in the composite zirconium oxide, in parts by weight, the use amount of XaOb is 0.1-40 parts, and the use amount of ZrO2 is 60-99.9 parts. The method can be used in the field of non-fossil resource aromatic hydrocarbon preparation.
Description
Technical field
A kind of method that the present invention relates to alcohol compound aromatisation aromatic hydrocarbons.
Background technology
Biomass are the Renewable resources that nature is widely present, and have neutral carbon environment amenable
Feature.The whole world annual yield of biomass is about 200,000,000,000 tons, rich reserves, and wide material sources are honest and clean
Valency is easy to get.The aromatic hydrocarbon product being widely used from the preparation of reproducible biomass resource causes section
Educational circles and the extensive concern of industrial quarters.
Cellulose and hemicellulose are one of mainly comprising of biomass, and its internal construction unit is
Pentose and hexose, such as glucose and fructose.From pentose and hexose through reforming
Etc. step, it is possible to obtain carbon pentol and carbon six alcohol, both have application at field of medicaments and perfume industry.
Still further aspect, five carbon alcohol and six carbon alcohol can obtain carbon five and the alkene of carbon six through converting, double
Key can be alkylated further under the effect of acid catalyst and obtain more product.Such as penta
Alkene can form amylbenzene or toluene with the aromatic hydrocarbons such as benzene, toluene, and further cyclisation can obtain methyl and take
The naphthalene in generation.
At present, benzene, toluene and dimethylbenzene are the important basic organic chemical industry raw materials of social development, its
Self or multiple product chain can be derived through reproduction, product be widely used in polyester, chemical fibre,
The numerous areas such as rubber, medicine and fine chemistry industry, domestic consumption amount reaches up to ten million ton, to state
People's economic development has material impact.Benzene is a kind of basic petrochemical material of multipurpose, can produce it
Derivative numerous products, including ethyl benzene/styrene, cumene/phenol etc..Xylol is mainly used
In manufacturing p-phthalic acid, by p-phthalic acid (PTA) or diethyl terephthalate (DMT)
Mesosome, is used for producing poly-cruel fiber such as polyethylene terephthalate (PET), resin and thin film.
This three classes aromatic hydrocarbons is typical light aromatics, is abbreviated as BTX.The production master of BTX the most both at home and abroad
Depend on non-renewable fossil resource, such as by a catalyst by oil through hydrogenation,
The technical processs such as reformation, aromatic hydrocarbons conversion and separation obtain.But, fossil resource reserves finite sum is not
Recyclability so that more see surging with the cost that oil is mainly refining raw material production aromatic hydrocarbons.It addition,
The utilization of continually developing of fossil resource produces a large amount of greenhouse gas emissions, caused a series of environment
Problem is on the rise, and therefore develops and application significant from Renewable resource route production aromatic hydrocarbons
It is worth.
For biomass-based carbon pentol and carbon six alcohol, aldehyde or acid can be further oxidized to, or
It is dehydrated into alkene.But rarely have report that carbon pentol and carbon six alcohol aromatization are turned to aromatic hydrocarbons at present.
Summary of the invention
A kind of method that it is an object of the invention to provide alcohol compound aromatisation aromatic hydrocarbons.Such
Alcohol compound can be obtained by the biomass material of wide material sources rich reserves, can make on a large scale
Standby.This method increase traditional aromatics production method, the benefit of aromatic hydrocarbons can be produced as fossil resource
Fill, there is low cost, high and that easily industrialization the is amplified feature of aromatisation efficiency.
For achieving the above object, the technical solution used in the present invention is as follows: a kind of alcohols chemical combination
The method of thing aromatisation aromatic hydrocarbons, under aromatization conditions, makes C4～6Alcohol contacts generation with catalyst
Arene stream containing benzene, toluene and dimethylbenzene；
Described catalyst is selected from compound Zirconium oxide XaOb/ZrO2；Wherein, X selected from tungsten, molybdenum, cerium,
At least one in lanthanum or manganese, a and b is stoichiometric number；In described compound Zirconium oxide, with weight
Amount number meter, XaObConsumption be 0.1～40 part, ZrO2Consumption be 60～99.9 parts.
In technique scheme, described C4～6Alcohol selected from n-butyl alcohol, 2-butanol, 1-amylalcohol, 2-amylalcohol,
3-amylalcohol, 1,2-pentanediol, 1,3-pentanediol, 1,4-pentanediol, 1,5-pentanediol, 1-hexanol, 2-
Hexanol, 3-hexanol, 1,2-hexanediol, 1,3-hexanediol, 1,4-hexanediol, 1,5-hexanediol, 1,6-
At least one in hexanediol, 1,2,3-hexanetriol, sorbitol or xylitol.
In technique scheme, it is preferable that described C4～6Alcohol is from biological material.
In technique scheme, it is preferable that described C4～6Alcohol is from glucose, cellobiose, half fibre
At least one in dimension element or lignin.
In technique scheme, it is preferable that described C4～6Alcohol from bagasse, glucose, timber,
At least one in corn stalk or Caulis et Folium Oryzae straw.
In technique scheme, it is preferable that in described compound Zirconium oxide, in terms of parts by weight, XaOb
Consumption be 1～40 part, ZrO2Consumption be 60～99 parts.
In technique scheme, it is preferable that described aromatization conditions is: reaction temperature 300～800 DEG C,
Hydrogen Vapor Pressure in terms of gauge pressure 0.1～5MPa, raw material weight air speed 0.3～10 hours-1.It is highly preferred that
Described aromatization conditions is: reaction temperature 300～650 DEG C, Hydrogen Vapor Pressure in terms of gauge pressure 0.5～4MPa,
Raw material weight air speed 0.3～5 hours-1。
Heretofore described compound Zirconium oxide XaOb/ZrO2；Wherein, X selected from tungsten, molybdenum, cerium,
At least one in lanthanum or manganese, a and b is stoichiometric number, and this is relevant with the quantivalence of selected metal.
When selected metal determines, each subscript i.e. has the numerical value determined.Its preparation can use this area institute
Known to infusion process or the sedimentation method.Infusion process is with saline solution form by tungsten, molybdenum, cerium, lanthanum or manganese
It is impregnated on zirconium oxide, after impregnating 12～48 hours, outwells surplus liquid, 100～200 DEG C of dried,
Moisture is evaporated and leaves active component, more i.e. obtain height after roast, activation procedure process
Scattered carrier catalysis is other.The sedimentation method can be by by water-soluble for the slaine of tungsten, molybdenum, cerium, lanthanum or manganese
Liquid, the aqueous metal solution of zirconium and precipitant ammonia are simultaneously introduced, and generate solid precipitation.Generate is heavy
Form sediment scrubbed, filter, be dried, at 400～600 DEG C roasting through after available catalyst.
As an embodiment of the invention, raw material of the present invention is biomass-based alcoholic compound.
Such alcoholic compound can pass through wide material sources, the biomass material of rich reserves obtains, and can advise greatly
Prepared by mould.Such as, n-butyl alcohol and isobutanol can obtain (China by the method for fermentation of biomass
Patent CN201210509488.1；CN201280029221.0；CN201110396100.7)；Mountain
The sugar alcohols such as pears alcohol and xylitol, can be obtained by modes such as hydrocellulose or squeezing sugar, i.e. obtain
After the sugar such as glucose, sucrose, cellobiose and fructose, obtain sorbitol and xylitol by hydrogenation
(Conversion of Cellulose into Sorbitol over Carbon Nanotube-Supported
Ruthenium Catalyst, Catalysis Letters, 133 (1), 167-174,2009；Glucose
Hydrogenation to Sorbitol over a Skeletal NiP Amorphous Alloy Catalyst
(Raney NiP), Journal of Catalysis, 191 (1), 257-260,2000；).It addition,
Carbon four～the monohydric alcohol of carbon six and polyhydric alcohol, it is also possible to by sugar such as aqueous-phase reforming glucose and fructose
Class, and the acquisition of the sugar alcohol such as aqueous-phase reforming such as sorbitol, mannitol.(Catalytic conversion of
Biomass to monofunctional hydrocarbons and targeted liquid-fuel classes,
Science.2008,322 (5900): 417-21.)
The invention provides a new way preparing aromatic hydrocarbons from biomass-based alcoholic compound, with saccharide
Compound convert after hexanol and amylalcohol as aromatisation platform.Using the inventive method, raw material turns
Rate can reach 99%, and the selectivity of benzene,toluene,xylene target product, up to 93%, obtains
Preferable technique effect.
Below by embodiment, the present invention is further elaborated.
Detailed description of the invention
[embodiment 1]
Weigh 5 grams to be dried except the water WO of 12 hours at 120 DEG C3/ZrO2Catalyst, burning
The share ratio of thing is 3/97, loads fixed bed reactors.Reaction substrate is n-butyl alcohol, and weight is empty
Speed 0.5 hour-1, Hydrogen Vapor Pressure 1.0MPa, flow 20ml min-1, temperature 450 DEG C.Reaction knot
Shu Hou, uses mass spectrum that reaction result is carried out qualitative analysis, and reaction result is quantitatively divided by chromatograph
Analysis.Reaction substrate conversion ratio is 97%, and the selectivity of BTX is 88%.
[embodiment 2]
Weigh 5 grams to be dried except the water WO of 12 hours at 120 DEG C3/ZrO2Catalyst, burning
The share ratio of thing is 5/95, loads fixed bed reactors.Reaction substrate is 2-butanol, weight space velocity
1.0 hour-1, Hydrogen Vapor Pressure 1.0MPa, flow 50ml min-1, temperature 400 DEG C.Reaction terminates
After, use mass spectrum that reaction result is carried out qualitative analysis, chromatograph carries out quantitative analysis to reaction result.
Reaction substrate conversion ratio is 90%, and the selectivity of BTX is 93%.
[embodiment 3]
Aqueous-phase reforming glucose prepares amylalcohol: loads 5 grams in fixed bed reactors and takes infusion process
The PtRe/C catalyst of preparation, in this catalyst, tenor is 5%, and the ratio of Pt and Re is
50:50.Temperature reaction device, keeps 2 hours in 350 DEG C in nitrogen atmosphere, cools to 210 afterwards
DEG C, it is 1h at blanket of nitrogen weight space velocity-1Under conditions of put into the D/W of 40% concentration and enter
Row liquid phase reforming reaction.This raw material is after beds, and product stream cooling is collected, upper strata
It is 2-amylalcohol that oil phase characterizes discriminating primary product by analysis.Reaction conversion ratio is 99%, amylalcohol
Selectivity is 85%.
Weigh 5 grams to be dried except the water WO of 12 hours at 120 DEG C3/ZrO2Catalyst, burning
The share ratio of thing is 20/80, loads fixed bed reactors.Reaction substrate is 2-amylalcohol, and weight is empty
Speed 3.5 hours-1, Hydrogen Vapor Pressure 2.0MPa, flow 20ml min-1, temperature 380 DEG C.Reaction knot
Shu Hou, uses mass spectrum that reaction result is carried out qualitative analysis, and reaction result is quantitatively divided by chromatograph
Analysis.Reaction substrate conversion ratio is 91%, and the selectivity of BTX is 86%.
[embodiment 4]
Weigh 5 grams to be dried except the water MoO of 12 hours at 120 DEG C3/ZrO2Catalyst, metal oxygen
The share ratio of compound is 20/80, loads fixed bed reactors.Reaction substrate is 2-amylalcohol, weight
Air speed 3.0 hours-1, Hydrogen Vapor Pressure 1.0MPa, flow 20ml min-1, temperature 480 DEG C.Reaction
After end, using mass spectrum that reaction result is carried out qualitative analysis, reaction result is carried out quantitatively by chromatograph
Analyze.Reaction substrate conversion ratio is 92%, and the selectivity of BTX is 84%.
[embodiment 5]
Weigh 5 grams to be dried except the water CeO of 12 hours at 120 DEG C2/ZrO2Catalyst, metal oxygen
The share ratio of compound is 10/90, loads fixed bed reactors.Reaction substrate is 3-amylalcohol, weight
Air speed 3.0 hours-1, Hydrogen Vapor Pressure 1.0MPa, flow 20ml min-1, temperature 450 DEG C.Reaction
After end, using mass spectrum that reaction result is carried out qualitative analysis, reaction result is carried out quantitatively by chromatograph
Analyze.Reaction substrate conversion ratio is 88%, and the selectivity of BTX is 89%.
[embodiment 6]
Weigh 5 grams to be dried except the water WO of 12 hours at 120 DEG C3/ZrO2Catalyst, metal oxygen
The share ratio of compound is 15/85, loads fixed bed reactors.Reaction substrate is 1-amylalcohol, weight
Air speed 5.0 hours-1, Hydrogen Vapor Pressure 3.0MPa, flow 20ml min-1, temperature 500 DEG C.Reaction
After end, using mass spectrum that reaction result is carried out qualitative analysis, reaction result is carried out quantitatively by chromatograph
Analyze.Reaction substrate conversion ratio is 92%, and the selectivity of BTX is 85%.
[embodiment 7]
Weigh 5 grams to be dried except the water MoO of 12 hours at 120 DEG C3/ZrO2Catalyst, metal oxygen
The share ratio of compound is 13/87, loads fixed bed reactors.Reaction substrate is 1,2-pentanediol,
Weight space velocity 1.5 hours-1, Hydrogen Vapor Pressure 1.5MPa, flow 20ml min-1, temperature 420 DEG C.
After reaction terminates, using mass spectrum that reaction result is carried out qualitative analysis, reaction result is carried out by chromatograph
Quantitative analysis.Reaction substrate conversion ratio is 90%, and the selectivity of BTX is 89%.
[embodiment 8]
Weigh 5 grams to be dried except the water La of 12 hours at 120 DEG C2O3/ZrO2Catalyst, metal oxygen
The share ratio of compound is 15/85, loads fixed bed reactors.Reaction substrate is 1,2-pentanediol,
Weight space velocity 1.5 hours-1, Hydrogen Vapor Pressure 1.5MPa, flow 20ml min-1, temperature 440 DEG C.
After reaction terminates, using mass spectrum that reaction result is carried out qualitative analysis, reaction result is carried out by chromatograph
Quantitative analysis.Reaction substrate conversion ratio is 95%, and the selectivity of BTX is 92%.
[embodiment 9]
Weigh 5 grams to be dried except the water WO of 12 hours at 120 DEG C3/ZrO2Catalyst, metal oxygen
The share ratio of compound is 10/90, loads fixed bed reactors.Reaction substrate is 1-hexanol, weight
Air speed 1.5 hours-1, Hydrogen Vapor Pressure 1.5MPa, flow 20ml min-1, temperature 390 DEG C.Reaction
After end, using mass spectrum that reaction result is carried out qualitative analysis, reaction result is carried out quantitatively by chromatograph
Analyze.Reaction substrate conversion ratio is 98%, and the selectivity of BTX is 91%.
[embodiment 10]
Weigh 5 grams to be dried except the water WO of 12 hours at 120 DEG C3/ZrO2Catalyst, metal oxygen
The share ratio of compound is 40/60, loads fixed bed reactors.Reaction substrate is 1-hexanol, weight
Air speed 1.0 hours-1, Hydrogen Vapor Pressure 1.5MPa, flow 40ml min-1, temperature 450 DEG C.Reaction
After end, using mass spectrum that reaction result is carried out qualitative analysis, reaction result is carried out quantitatively by chromatograph
Analyze.Reaction substrate conversion ratio is 99%, and the selectivity of BTX is 89%.
[embodiment 11]
Weigh 5 grams to be dried except the water MoO of 12 hours at 120 DEG C3/ZrO2Catalyst, metal oxygen
The share ratio of compound is 30/70, loads fixed bed reactors.Reaction substrate 2-hexanol, weight is empty
Speed 1.0 hours-1, Hydrogen Vapor Pressure 2.5MPa, flow 40ml min-1, temperature 450 DEG C.Reaction knot
Shu Hou, uses mass spectrum that reaction result is carried out qualitative analysis, and reaction result is quantitatively divided by chromatograph
Analysis.Reaction substrate conversion ratio is 97%, and the selectivity of BTX is 89%.
[embodiment 12]
Weigh 5 grams to be dried except the water MnO of 12 hours at 120 DEG C3/ZrO2Catalyst, metal oxygen
The share ratio of compound is 8/92, loads fixed bed reactors.Reaction substrate is 3-hexanol, weight
Air speed 1.0 hours-1, Hydrogen Vapor Pressure 1.5MPa, flow 40ml min-1, temperature 450 DEG C.Reaction
After end, using mass spectrum that reaction result is carried out qualitative analysis, reaction result is carried out quantitatively by chromatograph
Analyze.Reaction substrate conversion ratio is 92%, and the selectivity of BTX is 89%.
[embodiment 13]
Weigh 5 grams to be dried except the water MnO of 12 hours at 120 DEG C2-WO3/ZrO2Catalyst, gold
The share ratio belonging to oxide is 8/92, loads fixed bed reactors.Reaction substrate is 1,2-hexanediol,
Weight space velocity 1.0 hours-1, Hydrogen Vapor Pressure 1.5MPa, flow 40ml min-1, temperature 450 DEG C.
After reaction terminates, using mass spectrum that reaction result is carried out qualitative analysis, reaction result is carried out by chromatograph
Quantitative analysis.Reaction substrate conversion ratio is 93%, and the selectivity of BTX is 89%.
[embodiment 14]
Weigh 5 grams to be dried except the water La of 12 hours at 120 DEG C2O3-WO3/ZrO2Catalyst, gold
The share ratio belonging to oxide is 8/92, loads fixed bed reactors.Reaction substrate is 1,2-hexanediol,
Weight space velocity 1.0 hours-1, Hydrogen Vapor Pressure 1.5MPa, flow 40ml min-1, temperature 450 DEG C.
After reaction terminates, using mass spectrum that reaction result is carried out qualitative analysis, reaction result is carried out by chromatograph
Quantitative analysis.Reaction substrate conversion ratio is 87%, and the selectivity of BTX is 84%.
[embodiment 15]
Weigh 5 grams to be dried except the water CeO of 12 hours at 120 DEG C2-WO3/ZrO2Catalyst, gold
The share ratio belonging to oxide is 8/92, loads fixed bed reactors.Reaction substrate is 1-amylalcohol,
Weight space velocity 1.0 hours-1, Hydrogen Vapor Pressure 1.5MPa, flow 40ml min-1, temperature 450 DEG C.
After reaction terminates, using mass spectrum that reaction result is carried out qualitative analysis, reaction result is carried out by chromatograph
Quantitative analysis.Reaction substrate conversion ratio is 89%, and the selectivity of BTX is 91%.
[embodiment 16]
Weigh 50 grams of celluloses, merge 300 milliliters of water, add 2 grams of 10%Ni load capacity
Ni/C catalyst, reacts 1 hour at 240 DEG C, and reactant liquor is taken out in cooling, by analysis, fine
The conversion ratio of dimension element is 96%, and the productivity of sorbitol is 75%.
Weigh 5 grams to be dried except the water CeO of 12 hours at 120 DEG C2-WO3Catalyst, loads fixing
Bed reactor.Reaction substrate is sorbitol, weight space velocity 3.0 hours-1, Hydrogen Vapor Pressure 1.0MPa,
Flow 50ml min-1, temperature 400 DEG C.After reaction terminates, use mass spectrum that reaction result is carried out fixed
Property analyze, chromatograph carries out quantitative analysis to reaction result.Reaction substrate conversion ratio is 98%, BTX
Selectivity be 85%.
Table 1 embodiment collects
| Embodiment | Substrate | Catalyst | Conversion ratio/% | BTX selectivity/% |
| 1 | N-butyl alcohol | WO3/ZrO2 | 97 | 88 |
| 2 | 2-butanol | WO3/ZrO2 | 90 | 93 |
| 3 | 2-amylalcohol | WO3/ZrO2 | 91 | 86 |
| 4 | 2-amylalcohol | MoO3/ZrO2 | 92 | 84 |
| 5 | 3-amylalcohol | CeO2/ZrO2 | 88 | 89 |
| 6 | 1-amylalcohol | WO3/ZrO2 | 92 | 85 |
| 7 | 1,2-pentanediol | MoO3/ZrO2 | 90 | 89 |
| 8 | 1,2-pentanediol | La2O3/ZrO2 | 95 | 92 |
| 9 | 1-hexanol | WO3/ZrO2 | 98 | 91 |
| 10 | 1-hexanol | WO3/ZrO2 | 99 | 89 |
| 11 | 2-hexanol | MoO3/ZrO2 | 97 | 89 |
| 12 | 3-hexanol | MnO2/ZrO2 | 92 | 89 |
| 13 | 1,2-hexanediol | MnO2-WO3/ZrO2 | 93 | 89 |
| 14 | 1,2-hexanediol | La2O3-WO3/ZrO2 | 87 | 84 |
| 15 | 1-amylalcohol | CeO2-WO3/ZrO2 | 89 | 91 |
| 16 | Sorbitol | CeO2-WO3 | 98 | 85 |
Claims (8)
1. a method for alcohol compound aromatisation aromatic hydrocarbons, under aromatization conditions, makes C4～6
Alcohol contacts generation containing benzene, toluene and the arene stream of dimethylbenzene with catalyst；
Described catalyst is selected from compound Zirconium oxide XaOb/ZrO2；Wherein, X selected from tungsten, molybdenum, cerium,
At least one in lanthanum or manganese, a and b is stoichiometric number；In described compound Zirconium oxide, with weight
Amount number meter, XaObConsumption be 0.1～40 part, ZrO2Consumption be 60～99.9 parts.
The most according to claim 1, the method for alcohol compound aromatisation aromatic hydrocarbons, its feature exists
With described C4～6Alcohol is selected from n-butyl alcohol, 2-butanol, 1-amylalcohol, 2-amylalcohol, 3-amylalcohol, 1,2-penta 2
Alcohol, 1,3-pentanediol, 1,4-pentanediol, 1,5-pentanediol, 1-hexanol, 2-hexanol, 3-hexanol, 1,2-
Hexanediol, 1,3-hexanediol, 1,4-hexanediol, 1,5-hexanediol, 1,6-HD, 1,2,3-hexanetriol,
At least one in sorbitol or xylitol.
The most according to claim 1, the method for alcohol compound aromatisation aromatic hydrocarbons, its feature exists
In described C4～6Alcohol is from biological material.
The most according to claim 1, the method for alcohol compound aromatisation aromatic hydrocarbons, its feature exists
In described C4～6Alcohol is from least one in glucose, cellobiose, hemicellulose or lignin.
The most according to claim 1, the method for alcohol compound aromatisation aromatic hydrocarbons, its feature exists
In described C4～6Alcohol is from least one in bagasse, glucose, timber, corn stalk or Caulis et Folium Oryzae straw.
The most according to claim 1, the method for alcohol compound aromatisation aromatic hydrocarbons, its feature exists
In described compound Zirconium oxide, in terms of parts by weight, XaObConsumption be 1～40 part, ZrO2
Consumption be 60～99 parts.
The method of alcohol compound aromatisation aromatic hydrocarbons the most according to claim 1, it is characterised in that
Described aromatization conditions is: reaction temperature 300～800 DEG C, Hydrogen Vapor Pressure in terms of gauge pressure 0.1～5MPa,
Raw material weight air speed 0.3～10 hours-1。
The most according to claim 1, the method for alcohol compound aromatisation aromatic hydrocarbons, its feature exists
In described aromatization conditions be: reaction temperature 300～650 DEG C, Hydrogen Vapor Pressure in terms of gauge pressure 0.5～
4MPa, raw material weight air speed 0.3～5 hours-1。
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|---|---|---|---|---|
| CN108484360A (en) * | 2018-04-04 | 2018-09-04 | 中国科学技术大学 | A kind of preparation method of alcohol compound |
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| WO2012174205A1 (en) * | 2011-06-15 | 2012-12-20 | Ut-Battelle, Llc | Zeolitic catalytic conversion of alcohols to hydrocarbons |
| CN103131456A (en) * | 2011-11-29 | 2013-06-05 | 中国科学院大连化学物理研究所 | Method for synthesizing liquefied petroleum gas and BTX aromatics by butyl alcohol |
| CN104428060A (en) * | 2012-07-25 | 2015-03-18 | 科莱恩公司 | Hydrodeoxygenation catalyst |
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2015
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012174205A1 (en) * | 2011-06-15 | 2012-12-20 | Ut-Battelle, Llc | Zeolitic catalytic conversion of alcohols to hydrocarbons |
| CN103131456A (en) * | 2011-11-29 | 2013-06-05 | 中国科学院大连化学物理研究所 | Method for synthesizing liquefied petroleum gas and BTX aromatics by butyl alcohol |
| CN104428060A (en) * | 2012-07-25 | 2015-03-18 | 科莱恩公司 | Hydrodeoxygenation catalyst |
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| CN108484360A (en) * | 2018-04-04 | 2018-09-04 | 中国科学技术大学 | A kind of preparation method of alcohol compound |
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