CN106316762B - The production method of aromatic hydrocarbons - Google Patents
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Abstract
The present invention relates to a kind of production methods of aromatic hydrocarbons, under aromatization conditions, contact raw material with compound Zirconium oxide catalyst and generate the arene stream containing benzene, toluene and dimethylbenzene；Wherein, the raw material has structure formula (I):In formula (I), R1For hydrogen, optionally the C replaced1‑20Linear or branched alkyl group, the C optionally replaced2‑20Linear chain or branched chain alkenyl, the C optionally replaced2‑20Linear chain or branched chain alkynyl, the C optionally replaced3‑20Naphthenic base or the C optionally replaced6‑20Aryl；R2For the C optionally replaced1‑20Linear chain or branched chain carboxyl, furyl or hydroxyl alkyl furyl；Wherein, the hydroxyl alkyl furyl has structural formula (II):In formula (II), R3For the C optionally replaced1‑20Linear or branched alkyl group, the C optionally replaced2‑20Linear chain or branched chain alkenyl, the C optionally replaced2‑20Linear chain or branched chain alkynyl.This method can be used for non-fossil sources aromatic hydrocarbons field.
Description
Technical field
The present invention relates to a kind of production methods of aromatic hydrocarbons, prepare benzene, toluene and dimethylbenzene lightweight virtue more particularly to a kind of
The method of hydrocarbon.
Background technique
Benzene, toluene and dimethylbenzene are the important basic organic chemical industry raw materials of social development, its own or pass through reproduction
Multiple product chain can be derived, product is widely used in the numerous areas such as polyester, chemical fibre, rubber, medicine and fine chemistry industry, state
Interior consumption figure reaches up to ten million tons, has great influence to the national economic development.Benzene is a kind of basic petrochemical material of multipurpose, can
To produce numerous products, including ethyl benzene/styrene, cumene/phenol etc. derived from it.Paraxylene is mainly for the manufacture of right
Phthalic acid gathers cruel fiber such as producing by terephthalic acid (TPA) (PTA) or diethyl terephthalate (DMT) intermediate
Polyethylene terephthalate (PET), resin and film.These three types of aromatic hydrocarbons are typical light aromatics, are abbreviated as BTX.Mesh
The production of preceding domestic and international BTX depends on non-renewable fossil resource, such as can be by a catalyst by petroleum by adding
The technical process such as hydrogen, reformation, aromatic hydrocarbons conversion and separation obtain.But fossil resource reserves are limited and non-renewable, so that with
Petroleum is that the cost that main refining raw material produces aromatic hydrocarbons is more shown in surging.In addition, continually developing for fossil resource is a large amount of using generating
Greenhouse gas emission, caused a series of environmental problems are on the rise, therefore develop from renewable resource route and produce aromatic hydrocarbons
Significant and application value.
The plant that nature is widely present is a kind of typical renewable resource, belongs to one kind of biomass.Global biology
The annual yield of matter is about 200,000,000,000 tons, and rich reserves are from a wealth of sources, cheap and easy to get.From reproducible biomass resource
It is prepared with the extensive concern that widely applied aromatic hydrocarbon product causes scientific circles and industry.
In recent years, biological legal system aromatic hydrocarbons is studied by global more research institutions, makes some progress.It removes
Outside fermentative routes, the route with certain development prospect has 4: biomass is through synthesis gas aromatisation again；Fast pyrogenation aromatic hydrocarbons；
Biomass sugar platform is through catalytic cracking aromatic hydrocarbons；Biomass-based isobutanol aromatisation etc..Below to certain economy
Technology is analyzed.
Anellotech company develops the Biomassto Aromatic of the catalytic pyrolysis aromatic hydrocarbons of lignocellulosicTMWork
Skill [Katherine Bourzac.From biomass to chemicals in one step.MIT Technology
Review, 2010-03-29.], and be dedicated to pushing it against industrialized production.The technique is with non-grain biomass such as plant straw
Stalk, culled wood etc. are raw material, by catalysis fast pyrolysis technology aromatic hydrocarbons, have built up demonstration experimental provision in 2011.CFP skill
Art will be ground to powder after biomass material drying at 600 DEG C, mixes with powdery ZSM-5 catalyst and is sent into high temperature circulation fluidisation
In bed reactor, it is sufficiently mixed and is heated in the form of air whirl, raw material powder is partially converted into aromatic hydrocarbons through catalytic pyrolysis, together
When catalyst coking and deactivation, light aromatics (US20090227823) can be obtained in separating catalyst and purified product later.
Virent company develops BioFormingTMTechnology, based on sugared platform, using the technology of aqueous-phase reforming to life
Materials compounds deoxidation is reformate, and further aromatization turns to aromatic hydrocarbons on ZSM-5 catalyst.Its raw material includes corn, sugarcane
With the biomass such as lignocellulosic.Main process is using aqueous-phase reforming (APR) technology, by carbohydrate admixture through pallium-on-carbon-rhenium
Catalyst deoxidation is converted into alcohol, aldehyde list oxygen compound, and product carbochain after condensation hydrogenation is increased, further aromatisation system
Standby oil product and aromatic hydrocarbons (US20110257416A1).The process can theoretically reduce even from hydrogen producing without using external hydrogen source.
Above-mentioned technology path respectively has feature, emphasizes particularly on different fields, there is also there is different degrees of problem, such as the utilization of raw material
The problems such as rate, the price of raw material, the stability of aromatisation system.
Summary of the invention
The present invention is intended to provide a kind of production method of aromatic hydrocarbons.
For achieving the above object, the technical solution adopted by the present invention is as follows: a kind of production method of aromatic hydrocarbons, in aromatization
Under the conditions of change, contacts raw material with catalyst and generate the arene stream containing benzene, toluene and dimethylbenzene；Wherein, the raw material has
Structure formula (I):
In formula (I), R1For hydrogen, optionally the C replaced1-20Linear or branched alkyl group, the C optionally replaced2-20Linear chain or branched chain alkene
Base, the C optionally replaced2-20Linear chain or branched chain alkynyl, the C optionally replaced3-20Naphthenic base or the C optionally replaced6-20Aryl；R2
For the C optionally replaced1-20Linear chain or branched chain carboxyl, furyl or hydroxyl alkyl furyl；Wherein, the hydroxyl alkyl furyl
With structure formula (II):
In formula (II), R3For the C optionally replaced1-20Linear or branched alkyl group, the C optionally replaced2-20Linear chain or branched chain alkene
Base, the C optionally replaced2-20Linear chain or branched chain alkynyl；
The catalyst is selected from compound Zirconium oxide XaOb/ZrO2；Wherein, X in tungsten, molybdenum, cerium, lanthanum or manganese at least
One kind, a and b are stoichiometric number；In the compound Zirconium oxide, based on parts by weight, XaObDosage be 0.1~40 part,
ZrO2Dosage be 60~99.9 parts.
In above-mentioned technical proposal, it is preferable that in formula (I), R1For the C optionally replaced2-10Linear or branched alkyl group optionally takes
The C in generation2-10Linear chain or branched chain alkenyl.
In above-mentioned technical proposal, it is preferable that in formula (I), R2For the C optionally replaced2-10Linear chain or branched chain carboxyl.
In above-mentioned technical proposal, it is preferable that in formula (II), R3For the C optionally replaced2-10Linear or branched alkyl group optionally takes
The C in generation2-10Linear chain or branched chain alkenyl.
In above-mentioned technical proposal, it is preferable that in the compound Zirconium oxide, based on parts by weight, XaObDosage be 1~
40 parts, ZrO2Dosage be 60~90 parts.
In above-mentioned technical proposal, it is preferable that the aromatization conditions are as follows: 300~800 DEG C of reaction temperature, Hydrogen Vapor Pressure with
Gauge pressure 0.1~5MPa of meter, raw material weight air speed 0.3~10 hour-1.It is highly preferred that the aromatization conditions are as follows: reaction temperature
300~650 DEG C, Hydrogen Vapor Pressure 0.5~4MPa in terms of gauge pressure, raw material weight air speed 0.3~5 hour-1。
In above-mentioned technical proposal, it is preferable that the raw material comes from biological material.
In above-mentioned technical proposal, it is preferable that the raw material comes from xylitol, glucose, fructose, cellobiose, hemicellulose
At least one of element or lignin.
In above-mentioned technical proposal, it is preferable that the raw material from bagasse, glucose, timber, corn stalk, corncob or
At least one of straw straw.
As an embodiment of the invention, raw material of the present invention is biomass-based carbonyl complex, such as
Furfural, 5 hydroxymethyl furfural, levulic acid.Such carbonyl complex can be former by biomass from a wealth of sources, rich reserves
Material obtains, can be with large scale preparation.For example, levulic acid can be in Zirconium oxide, metal chloride, organic acid or inorganic acid
In the presence of, (Efficient Conversion of Cellulose to is produced by the biomass substrate such as cellulose, stalk
Levulinic Acid by Hydrothermal Treatment Using Zirconium Dioxide as a
Recyclable Solid Acid Catalyst, Ind.Eng.Chem.Res., 2014,53 (49), pp 18796-18805；
Production of levulinic acid from cellulose by hydrothermal decomposition
Combined with aqueous phase dehydration with a solid acid catalyst, Energy
Environ.Sci.,2012,5,7559-7574；Effective Production of Levulinic Acid from
Biomass through Pretreatment Using Phosphoric Acid,Hydrochloric Acid,or Ionic
Liquid, Ind.Eng.Chem.Res., 2014,53 (29), pp11611-11621).Furfural can be made with corn stalk or corncob
For raw material, produce to obtain by acid catalysis.5 hydroxymethyl furfural can by biomass such as acid catalysis fructose, glucose, celluloses,
(Phase modifiers promote efficient production of is obtained by dehydration
hydroxymethylfurfural from fructose.Science.2006Jun30；312(5782):1933-7.；
Catalytic conversion of carbohydrates into5-hydroxymethylfurfural over
Cellulose-derived carbonaceous catalyst in ionic liquid, Bioresour
Technol.2013Nov；148:501-507.).
Heretofore described compound Zirconium oxide XaOb/ZrO2；Wherein, X in tungsten, molybdenum, cerium, lanthanum or manganese at least
One kind, a and b are stoichiometric number, this is related with the chemical valence of selected metal.When selected metal determines, each subscript has
Determining numerical value.Infusion process or the precipitation method known in the art can be used in its preparation.Infusion process is by tungsten, molybdenum, cerium, lanthanum or manganese
It is impregnated on zirconium oxide in the form of salting liquid, dipping outwells surplus liquid after 12~48 hours, 100~200 DEG C of drying process will
Moisture, which is evaporated, leaves active component, using other up to the carrier catalysis of high degree of dispersion after roast, activation procedure processing.It is heavy
Shallow lake method can by the way that the aqueous metal solution of the aqueous metal salt of tungsten, molybdenum, cerium, lanthanum or manganese, zirconium and precipitating reagent ammonium hydroxide are added simultaneously,
Generate solid precipitating.The precipitating of generation is washed, filtering, dry, catalyst can be obtained in roasting after at 400~600 DEG C.
The method of the present invention has preferable conversion ratio to carbonyl complex, has preferable choosing to benzene,toluene,xylene product
Selecting property, aromatics yield is low long with reaction step during solving the problems, such as previous biomass aromatic hydrocarbons.Using the method for the present invention,
Feed stock conversion can reach 99%；The selectivity of benzene,toluene,xylene target product reaches as high as 93%, achieve compared with
Good technical effect.
The present invention will be further described below by way of examples.
Specific embodiment
[embodiment 1]
5 grams are weighed through the WO for removing water 12 hours dry at 120 DEG C3/ZrO2The share ratio of catalyst, metal oxide is
3/97, it is packed into fixed bed reactors.Reaction substrate is furfuralWeight space velocity 0.5 hour-1, Hydrogen Vapor Pressure
1.0MPa, flow 20ml min-1, 400 DEG C of temperature.After reaction, qualitative analysis, chromatography are carried out to reaction result using mass spectrum
Quantitative analysis is carried out to reaction result.The selectivity that reaction substrate conversion ratio is 75%, BTX is 89%.
[embodiment 2]
60 grams of corn stalks are weighed, is placed in autoclave pressure and is added 700 grams of water, add the sulphur of the 5mol/L of water quality 7%
Acid solution is warming up at 180 DEG C and reacts 45 minutes, cools down later, reaction solution after cooling is filtered, filter cake and filtering are obtained
Liquid, filtered fluid are that the hydrolyzate of cellulose uses mass spectrum to carry out identifying primary product for acetyl to reaction result after reaction
Propionic acid, yield are 18 grams.
5 grams are weighed through the WO for removing water 12 hours dry at 120 DEG C3/ZrO2The share ratio of catalyst, metal oxide is
5/95, it is packed into fixed bed reactors.Reaction substrate is levulic acidWeight space velocity 1.0 hours-1, hydrogen
Atmospheric pressure 1.0MPa, flow 50ml min-1, 450 DEG C of temperature.After reaction, qualitative point is carried out to reaction result using mass spectrum
Analysis, chromatography carry out quantitative analysis to reaction result.The selectivity that reaction substrate conversion ratio is 93%, BTX is 84%.
[embodiment 3]
60 grams of straw straw are weighed, is placed in autoclave pressure and is added 700 grams of water, add the sulphur of the 5mol/L of water quality 7%
Acid solution is warming up at 210 DEG C and reacts 30 minutes, cools down later, reaction solution after cooling is filtered, filter cake and filtering are obtained
Liquid, filtered fluid are that the hydrolyzate of cellulose uses mass spectrum to carry out identifying primary product for acetyl to reaction result after reaction
Propionic acid, yield are 22.8 grams.
5 grams are weighed through the WO for removing water 12 hours dry at 120 DEG C3/ZrO2The share ratio of catalyst, metal oxide is
20/80, it is packed into fixed bed reactors.Reaction substrate is levulic acidWeight space velocity 2.5 hours-1,
Hydrogen Vapor Pressure 2.0MPa, flow 20ml min-1, 380 DEG C of temperature.After reaction, reaction result is carried out using mass spectrum qualitative
Analysis, chromatography carry out quantitative analysis to reaction result.The selectivity that reaction substrate conversion ratio is 97%, BTX is 86%.
[embodiment 4]
5 grams are weighed through the MoO for removing water 12 hours dry at 120 DEG C3/ZrO2The share ratio of catalyst, metal oxide is
10/90, it is packed into fixed bed reactors.Reaction substrate is levulic acidWeight space velocity 3.0 hours-1,
Hydrogen Vapor Pressure 1.0MPa, flow 20ml min-1, 480 DEG C of temperature.After reaction, reaction result is carried out using mass spectrum qualitative
Analysis, chromatography carry out quantitative analysis to reaction result.The selectivity that reaction substrate conversion ratio is 91%, BTX is 81%.
[embodiment 5]
30 grams of timber are weighed, is placed in autoclave pressure and is added 400 grams of water, add the sulfuric acid of the 5mol/L of water quality 7%
Solution is warming up at 200 DEG C and reacts 30 minutes, cools down later, reaction solution after cooling is filtered, filter cake and filtered fluid are obtained,
Filtered fluid is that the hydrolyzate of cellulose uses mass spectrum to carry out identifying primary product for levulinic to reaction result after reaction
Acid, yield are 10.5 grams.
5 grams are weighed through the CeO for removing water 12 hours dry at 120 DEG C2/ZrO2The share ratio of catalyst, metal oxide is
10/90, it is packed into fixed bed reactors.Reaction substrate is levulic acidWeight space velocity 3.0 hours-1,
Hydrogen Vapor Pressure 1.0MPa, flow 20ml min-1, 450 DEG C of temperature.After reaction, reaction result is carried out using mass spectrum qualitative
Analysis, chromatography carry out quantitative analysis to reaction result.The selectivity that reaction substrate conversion ratio is 86%, BTX is 80%.
[embodiment 6]
5 grams are weighed through the WO for removing water 12 hours dry at 120 DEG C3/ZrO2The share ratio of catalyst, metal oxide is
15/85, it is packed into fixed bed reactors.Reaction substrate is furfuralWeight space velocity 5.0 hours-1, Hydrogen Vapor Pressure
3.0MPa, flow 20ml min-1, 500 DEG C of temperature.After reaction, qualitative analysis, chromatography are carried out to reaction result using mass spectrum
Quantitative analysis is carried out to reaction result.The selectivity that reaction substrate conversion ratio is 99%, BTX is 93%.
[embodiment 7]
5 grams are weighed through the MoO for removing water 12 hours dry at 120 DEG C3/ZrO2The share ratio of catalyst, metal oxide is
13/87, it is packed into fixed bed reactors.Reaction substrate is furfuralWeight space velocity 1.5 hours-1, Hydrogen Vapor Pressure
1.5MPa, flow 20ml min-1, 420 DEG C of temperature.After reaction, qualitative analysis, chromatography are carried out to reaction result using mass spectrum
Quantitative analysis is carried out to reaction result.The selectivity that reaction substrate conversion ratio is 89%, BTX is 88%.
[embodiment 8]
5 grams are weighed through the La for removing water 12 hours dry at 120 DEG C2O3/ZrO2Catalyst, the share ratio of metal oxide
It is 15/85, is packed into fixed bed reactors.Reaction substrate is furfuralWeight space velocity 1.5 hours-1, Hydrogen Vapor Pressure
1.5MPa, flow 20ml min-1, 440 DEG C of temperature.After reaction, qualitative analysis, chromatography are carried out to reaction result using mass spectrum
Quantitative analysis is carried out to reaction result.The selectivity that reaction substrate conversion ratio is 82%, BTX is 83%.
[embodiment 9]
5 grams are weighed through the WO for removing water 12 hours dry at 120 DEG C3/ZrO2The share ratio of catalyst, metal oxide is
10/90, it is packed into fixed bed reactors.Reaction substrate is 5 hydroxymethyl furfuralWeight space velocity 1.5 is small
When-1, Hydrogen Vapor Pressure 1.5MPa, flow 20ml min-1, 390 DEG C of temperature.After reaction, reaction result is carried out using mass spectrum
Qualitative analysis, chromatography carry out quantitative analysis to reaction result.The selectivity that reaction substrate conversion ratio is 93%, BTX is 81%.
[embodiment 10]
5 grams are weighed through the WO for removing water 12 hours dry at 120 DEG C3/ZrO2The share ratio of catalyst, metal oxide is
40/60, it is packed into fixed bed reactors.Reaction substrate is 5 hydroxymethyl furfuralWeight space velocity 1.0 is small
When-1, Hydrogen Vapor Pressure 1.5MPa, flow 40ml min-1, 450 DEG C of temperature.After reaction, reaction result is carried out using mass spectrum
Qualitative analysis, chromatography carry out quantitative analysis to reaction result.The selectivity that reaction substrate conversion ratio is 95%, BTX is 78%.
[embodiment 11]
5 grams are weighed through the MoO for removing water 12 hours dry at 120 DEG C3/ZrO2The share ratio of catalyst, metal oxide is
30/70, it is packed into fixed bed reactors.Reaction substrate is 5 hydroxymethyl furfuralWeight space velocity 1.0 is small
When-1, Hydrogen Vapor Pressure 2.5MPa, flow 40ml min-1, 450 DEG C of temperature.After reaction, reaction result is carried out using mass spectrum
Qualitative analysis, chromatography carry out quantitative analysis to reaction result.The selectivity that reaction substrate conversion ratio is 90%, BTX is 72%.
[embodiment 12]
5 grams are weighed through the MnO for removing water 12 hours dry at 120 DEG C3/ZrO2The share ratio of catalyst, metal oxide is
8/92, it is packed into fixed bed reactors.Reaction substrate is 5 hydroxymethyl furfural, weight space velocity 1.0 hours-1, Hydrogen Vapor Pressure 1.5MPa,
Flow 40ml min-1, 450 DEG C of temperature.After reaction, qualitative analysis is carried out to reaction result using mass spectrum, chromatography is to reaction
As a result quantitative analysis is carried out.The selectivity that reaction substrate conversion ratio is 87%, BTX is 86
Table 1
| Embodiment | Substrate | Catalyst | Metal oxide ratio | Conversion ratio/% | BTX selectivity/% |
| 1 | Furfural | WO3/ZrO2 | 3/97 | 75 | 89 |
| 2 | Levulic acid | WO3/ZrO2 | 5/95 | 93 | 84 |
| 3 | Levulic acid | WO3/ZrO2 | 20/80 | 97 | 86 |
| 4 | Levulic acid | MoO3/ZrO2 | 10/90 | 91 | 81 |
| 5 | Levulic acid | CeO2/ZrO2 | 10/90 | 86 | 80 |
| 6 | Furfural | WO3/ZrO2 | 15/85 | 99 | 93 |
| 7 | Furfural | MoO3/ZrO2 | 13/87 | 89 | 88 |
| 8 | Furfural | La2O3/ZrO2 | 15/85 | 82 | 83 |
| 9 | 5 hydroxymethyl furfural | WO3/ZrO2 | 10/90 | 93 | 81 |
| 10 | 5 hydroxymethyl furfural | WO3/ZrO2 | 40/60 | 95 | 78 |
| 11 | 5 hydroxymethyl furfural | MoO3/ZrO2 | 30/70 | 90 | 72 |
| 12 | 5 hydroxymethyl furfural | MnO2/ZrO2 | 8/92 | 87 | 86 |
Claims (6)
1. a kind of production method of aromatic hydrocarbons makes raw material contact generation with catalyst containing benzene, toluene and diformazan under aromatization conditions
The arene stream of benzene；Wherein, the raw material has structure formula (I):
In formula (I), R1For hydrogen, C2-10Straight chained alkyl；R2For C2-10Straight-chain carboxyl group, furyl or hydroxyl alkyl furyl；Wherein,
The hydroxyl alkyl furyl has structural formula (II):
In formula (II), R3For C2-10Straight chained alkyl；
The catalyst is selected from compound Zirconium oxide XaOb/ZrO2；Wherein, X is selected from least one of tungsten, molybdenum, cerium, lanthanum or manganese,
A and b is stoichiometric number；In the compound Zirconium oxide, based on parts by weight, XaObDosage be 3~40 parts, ZrO2Use
Amount is 60~99 parts.
2. the production method of aromatic hydrocarbons according to claim 1, it is characterised in that the aromatization conditions are as follows: reaction temperature 300
~800 DEG C, Hydrogen Vapor Pressure 0.1~5MPa in terms of gauge pressure, raw material weight air speed 0.3~10 hour-1。
3. the production method of aromatic hydrocarbons according to claim 2, it is characterised in that the aromatization conditions are as follows: reaction temperature 300
~650 DEG C, Hydrogen Vapor Pressure 0.5~4MPa in terms of gauge pressure, raw material weight air speed 0.3~5 hour-1。
4. the production method of aromatic hydrocarbons according to claim 1, it is characterised in that the raw material comes from biological material.
5. the production method of aromatic hydrocarbons according to claim 1, it is characterised in that the raw material comes from xylitol, glucose, fruit
At least one of sugar, cellobiose, hemicellulose or lignin.
6. the production method of aromatic hydrocarbons according to claim 1, it is characterised in that the raw material comes from bagasse, glucose, wood
At least one of material, corn stalk, corncob or straw straw.
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510344592.3A CN106316762B (en) | 2015-06-19 | 2015-06-19 | The production method of aromatic hydrocarbons |
| DK16810696.1T DK3312153T3 (en) | 2015-06-19 | 2016-06-17 | PROCEDURES FOR THE PRODUCTION OF AROMATIC CARBOHYDRATE, PARAXYLENE AND TEREPHTHALIC ACID |
| KR1020187001728A KR102454225B1 (en) | 2015-06-19 | 2016-06-17 | Process for the preparation of aromatic hydrocarbons, paraxylene and terephthalic acid |
| JP2017565948A JP6877367B2 (en) | 2015-06-19 | 2016-06-17 | Method for producing aromatic hydrocarbons, p-xylene and terephthalic acid |
| BR112017027347-0A BR112017027347B1 (en) | 2015-06-19 | 2016-06-17 | Processes for the production of aromatic hydrocarbon, paraxylene and terephthalic acid |
| US15/738,063 US10358606B2 (en) | 2015-06-19 | 2016-06-17 | Process for producing aromatics, p-xylene and terephthalic acid |
| ES16810696T ES2880326T3 (en) | 2015-06-19 | 2016-06-17 | Methods for making aromatic hydrocarbon, paraxylene, and terephthalic acid |
| PCT/CN2016/000315 WO2016201955A1 (en) | 2015-06-19 | 2016-06-17 | Methods for manufacturing aromatic hydrocarbon, paraxylene and terephthalic acid |
| EP16810696.1A EP3312153B1 (en) | 2015-06-19 | 2016-06-17 | Methods for manufacturing aromatic hydrocarbon, paraxylene and terephthalic acid |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20080216391A1 (en) * | 2007-03-08 | 2008-09-11 | Cortright Randy D | Synthesis of liquid fuels and chemicals from oxygenated hydrocarbons |
| CN102992931A (en) * | 2012-12-11 | 2013-03-27 | 中国科学院大连化学物理研究所 | Method for synthesizing light aromatic hydrocarbon and liquefied petroleum gas from low carbon number oxygen-containing compound mixed raw material |
-
2015
- 2015-06-19 CN CN201510344592.3A patent/CN106316762B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20080216391A1 (en) * | 2007-03-08 | 2008-09-11 | Cortright Randy D | Synthesis of liquid fuels and chemicals from oxygenated hydrocarbons |
| CN102992931A (en) * | 2012-12-11 | 2013-03-27 | 中国科学院大连化学物理研究所 | Method for synthesizing light aromatic hydrocarbon and liquefied petroleum gas from low carbon number oxygen-containing compound mixed raw material |
Non-Patent Citations (2)
| Title |
|---|
| elective Production of Aromatics from Alkylfurans over Solid Acid Catalysts;Dong Wang等;《ChemCatChem》;20131231;第5卷;第2044-2050页 |
| 生物质催化转化制备芳烃;赵岩;《中国博士学位论文全文数据库 工程科技I辑》;20141015(第10期);第98页-118页 |
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