CN106316762A - Production method of aromatic hydrocarbons - Google Patents
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Abstract
The invention relates to a production method of aromatic hydrocarbons. The method is characterized in that a raw material is in contact with a composite zirconium oxide catalyst under aromatization conditions to generate aromatic hydrocarbon flow containing benzene, toluene and xylene, and the raw material has structural formula (I) shown in the description; in the formula (I), R1 is hydrogen, an optionally substituted C1-20 linear or branched alkyl group, an optionally substituted C2-C20 linear or branched alkenyl group, an optionally substituted C2-20 linear or branched alkynyl group, an optionally substituted C3-C20 cycloalkyl group or an optionally substituted C6-20 aryl group, R2 is an optionally substituted C1-20 linear or branched carboxyl group, a furyl group or a hydroxyalkylfuryl group, and the hydroxyalkylfuryl group has structural formula (II) shown in the description; and in the formula (II), R3 is an optionally substituted C1-20 linear or branched alkyl group, an optionally substituted C2-C20 linear or branched alkenyl group, an optionally substituted C2-20 linear or branched alkynyl group. The method can be used in the field of production of aromatic hydrocarbons from non-fossil resources.
Description
Technical field
The present invention relates to the production method of a kind of aromatic hydrocarbons, particularly relate to one prepare benzene, toluene and
The method of dimethylbenzene light aromatics.
Background technology
Benzene, toluene and dimethylbenzene are the important basic organic chemical industry raw materials of social development, himself or
Can to derive multiple product chain through reproduction, product be widely used in polyester, chemical fibre, rubber,
The numerous areas such as medicine and fine chemistry industry, domestic consumption amount reaches up to ten million ton, to national economy
Development has material impact.Benzene is a kind of basic petrochemical material of multipurpose, can produce what it derived
Numerous products, including ethyl benzene/styrene, cumene/phenol etc..Xylol mainly for the manufacture of
P-phthalic acid, by p-phthalic acid (PTA) or diethyl terephthalate (DMT) intermediate,
For producing poly-cruel fiber such as polyethylene terephthalate (PET), resin and thin film.This three class
Aromatic hydrocarbons is typical light aromatics, is abbreviated as BTX.The production of BTX the most both at home and abroad relies primarily on
In non-renewable fossil resource, such as by a catalyst by oil through hydrogenation, reform,
The technical processs such as aromatic hydrocarbons conversion and separation obtain.But, fossil resource reserves finite sum is non-renewable
Property so that more see surging with the cost that oil is mainly refining raw material production aromatic hydrocarbons.It addition, fossil
The utilization of continually developing of resource produces a large amount of greenhouse gas emissions, caused series of environmental problems
It is on the rise, therefore develops and using value significant from Renewable resource route production aromatic hydrocarbons.
The plant that nature is widely present is the Renewable resource of a quasi-representative, belongs to the one of biomass
Kind.The whole world annual yield of biomass is about 200,000,000,000 tons, rich reserves, wide material sources, inexpensively
It is easy to get.The aromatic hydrocarbon product being widely used from the preparation of reproducible biomass resource causes science
Boundary and the extensive concern of industrial quarters.
In recent years, biological legal system aromatic hydrocarbons is all studied by whole world Duo Jia research institution, achieves
Certain progress.In addition to fermentative routes, the route with certain development prospect has 4: biomass
Through synthesis gas aromatisation again；Fast pyrogenation aromatic hydrocarbons；Biomass sugar platform is through catalytic cracking aromatic hydrocarbons；
Biomass-based isobutanol aromatisation etc..Below the technology with certain economy is analyzed.
Anellotech company develops the Biomassto of the catalytic pyrolysis preparing aromatic hydrocarbons of lignocellulose
AromaticTMTechnique [Katherine Bourzac.From biomass to chemicals in one step.
MIT Technology Review, 2010-03-29.], and be devoted to push it against industrialized production.
This technique is with non-grain biomass such as straw, culled wood etc. as raw material, by catalysis quickly
Pyrolytic technique aromatic hydrocarbons, built up demonstration experimental provision in 2011.CFP technology is at 600 DEG C
Biomass material is ground to after drying powder, mixes feeding high temperature with powdery ZSM-5 catalyst and follow
In circulation fluidized bed reactor, being sufficiently mixed with the form of air whirl and heat, material powder is through urging
Heat-transformation solution is partially converted into aromatic hydrocarbons, simultaneously catalyst coking and deactivation, afterwards separating catalyst and purification
Product can get light aromatics (US20090227823).
Virent company develops BioFormingTMTechnology, based on sugar platform, uses liquid phase
The technology reformed is reformate to biomass compound deoxidation, further virtue on ZSM-5 catalyst
Structure turns to aromatic hydrocarbons.Its raw material includes the biomass such as Semen Maydis, Caulis Sacchari sinensis and lignocellulose.Main process
For using aqueous-phase reforming (APR) technology, carbohydrate admixture is turned through pallium-on-carbon-rhenium catalyst deoxidation
Turning to alcohol, aldehyde list oxygen compound, product carbochain after condensation hydrogenation is increased, further virtue
Structure prepares oil product and aromatic hydrocarbons (US20110257416A1).This process is from hydrogen producing, in theory
Can reduce and even not use external hydrogen source.
Above-mentioned technology path is respectively arranged with feature, emphasizes particularly on different fields, and there is also problem in various degree,
Such as problems such as the utilization rate of raw material, the price of raw material, the stability of aromatisation system.
Summary of the invention
It is desirable to provide the production method of a kind of aromatic hydrocarbons.
For achieving the above object, the technical scheme that the present invention takes is as follows: the life of a kind of aromatic hydrocarbons
Product method, under aromatization conditions, makes raw material contact generation with catalyst containing benzene, toluene and diformazan
The arene stream of benzene；Wherein, described raw material has a structure formula (I):
In formula (I), R1For hydrogen, optionally substituted C1-20Straight or branched alkyl, optionally substituted C2-20
Straight or branched thiazolinyl, optionally substituted C2-20Straight or branched alkynyl, optionally substituted C3-20Ring
Alkyl or optionally substituted C6-20Aryl；R2For optionally substituted C1-20Straight or branched carboxyl,
Furyl or hydroxyl alkyl furyl；Wherein, described hydroxyl alkyl furyl has a structural formula (II):
In formula (II), R3For optionally substituted C1-20Straight or branched alkyl, optionally substituted C2-20Directly
Chain or branched-chain alkenyl, optionally substituted C2-20Straight or branched alkynyl；
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, it is preferable that in formula (I), R1For optionally substituted C2-10Straight chain or
Branched alkyl, optionally substituted C2-10Straight or branched thiazolinyl.
In technique scheme, it is preferable that in formula (I), R2For optionally substituted C2-10Straight chain or
Side chain carboxyl.
In technique scheme, it is preferable that in formula (II), R3For optionally substituted C2-10Straight chain
Or branched alkyl, optionally substituted C2-10Straight or branched thiazolinyl.
In technique scheme, it is preferable that in described compound Zirconium oxide, in terms of parts by weight,
XaObConsumption be 1～40 part, ZrO2Consumption be 60～90 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。
In technique scheme, it is preferable that described raw material is from biological material.
In technique scheme, it is preferable that described raw material from xylitol, glucose, fructose,
At least one in cellobiose, hemicellulose or lignin.
In technique scheme, it is preferable that described raw material from bagasse, glucose, timber,
At least one in corn stalk, corn cob or Caulis et Folium Oryzae straw.
As an embodiment of the invention, raw material of the present invention is biomass-based carbonyl class
Compound, such as furfural, 5 hydroxymethyl furfural, levulic acid.Such carbonyl complex can pass through
Wide material sources, the biomass material of rich reserves obtain, and can prepare on a large scale.Such as, acetyl
Propanoic acid can be in the presence of Zirconium oxide, metal chloride, organic acid or mineral acid, by fiber
The biomass substrates such as element, straw produce (Efficient Conversion of Cellulose to Levulinic
Acid by Hydrothermal Treatment Using Zirconium Dioxide as a Recyclable
Solid Acid Catalyst, Ind.Eng.Chem.Res., 2014,53 (49), pp 18,796 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), pp
11611–11621).Furfural can produce using corn stalk or corn cob as raw material through acid catalysis
Obtain.5 hydroxymethyl furfural can be passed through by biomass such as acid catalysis fructose, glucose, celluloses
Dehydration obtains (Phase modifiers promote efficient production of
hydroxymethylfurfural from fructose.Science.2006Jun
30；312(5782):1933-7.；Catalytic conversion of carbohydrates into
5-hydroxymethylfurfural over cellulose-derived carbonaceous catalyst in ionic
Liquid, Bioresour Technol.2013Nov；148:501-507.).
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.
The inventive method has preferable conversion ratio to carbonyl complex, to benzene,toluene,xylene
Product has preferable selectivity, and during solving conventional biomass aromatic hydrocarbons, aromatics yield is low and anti-
The problem answering step length.Using the inventive method, feed stock conversion can reach 99%；Benzene,
Toluene, the selectivity of dimethylbenzene target product reach as high as 93%, achieve preferable technique effect.
Below by embodiment, the invention will be 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 furfural
Weight space velocity 0.5 hour-1, Hydrogen Vapor Pressure 1.0MPa, flow 20ml min-1, temperature 400 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 75%, and the selectivity of BTX is 89%.
[embodiment 2]
Weigh 60 grams of corn stalk, be placed in autoclave pressure and add 700 grams of water, adding water quality 7%
The sulfuric acid solution of 5mol/L, be warmed up at 180 DEG C reaction 45 minutes, cool down afterwards, will cooling
After reacting liquid filtering, obtain filter cake and filtrate, filtrate is the hydrolyzed solution of cellulose, reaction
After end, use mass spectrum that reaction result being identified, primary product is levulic acid, its generation amount
It it is 18 grams.
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 levulic acidWeight space velocity 1.0 hours-1, Hydrogen Vapor Pressure 1.0MPa, flow 50ml min-1,
Temperature 450 DEG C.After reaction terminates, using mass spectrum that reaction result is carried out qualitative analysis, chromatograph is to instead
Result should carry out quantitative analysis.Reaction substrate conversion ratio is 93%, and the selectivity of BTX is 84%.
[embodiment 3]
Weigh 60 grams of Caulis et Folium Oryzae straw, be placed in autoclave pressure and add 700 grams of water, adding water quality 7%
The sulfuric acid solution of 5mol/L, be warmed up at 210 DEG C reaction 30 minutes, cool down afterwards, will cooling
After reacting liquid filtering, obtain filter cake and filtrate, filtrate is the hydrolyzed solution of cellulose, reaction
After end, use mass spectrum that reaction result being identified, primary product is levulic acid, its generation amount
It it is 22.8 grams.
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 levulic acidWeight space velocity 2.5 hours-1, Hydrogen Vapor Pressure 2.0MPa, flow 20ml min-1,
Temperature 380 DEG C.After reaction terminates, using mass spectrum that reaction result is carried out qualitative analysis, chromatograph is to instead
Result should carry out quantitative analysis.Reaction substrate conversion ratio is 97%, 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 10/90, loads fixed bed reactors.Reaction substrate is levulic acidWeight space velocity 3.0 hours-1, Hydrogen Vapor Pressure 1.0MPa, flow 20ml min-1,
Temperature 480 DEG C.After reaction terminates, using mass spectrum that reaction result is carried out qualitative analysis, chromatograph is to instead
Result should carry out quantitative analysis.Reaction substrate conversion ratio is 91%, and the selectivity of BTX is 81%.
[embodiment 5]
Weigh 30 grams of timber, be placed in autoclave pressure and add 400 grams of water, adding water quality 7%
The sulfuric acid solution of 5mol/L, be warmed up at 200 DEG C reaction 30 minutes, cool down afterwards, will cooling
After reacting liquid filtering, obtain filter cake and filtrate, filtrate is the hydrolyzed solution of cellulose, reaction
After end, use mass spectrum that reaction result being identified, primary product is levulic acid, its generation amount
It it is 10.5 grams.
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 levulic acidWeight space velocity 3.0 hours-1, Hydrogen Vapor Pressure 1.0MPa, flow 20ml min-1,
Temperature 450 DEG C.After reaction terminates, using mass spectrum that reaction result is carried out qualitative analysis, chromatograph is to instead
Result should carry out quantitative analysis.Reaction substrate conversion ratio is 86%, and the selectivity of BTX is 80%.
[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 furfuralWeight space velocity 5.0 hours-1, Hydrogen Vapor Pressure 3.0MPa, flow 20ml min-1,
Temperature 500 DEG C.After reaction terminates, using mass spectrum that reaction result is carried out qualitative analysis, chromatograph is to instead
Result should carry out quantitative analysis.Reaction substrate conversion ratio is 99%, and the selectivity of BTX is 93%.
[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 furfuralWeight 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, chromatograph is to instead
Result should carry out quantitative analysis.Reaction substrate conversion ratio is 89%, and the selectivity of BTX is 88%.
[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 furfuralWeight 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, chromatograph is to instead
Result should carry out quantitative analysis.Reaction substrate conversion ratio is 82%, and the selectivity of BTX is 83%.
[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 5 hydroxymethyl furfuralWeight space velocity 1.5 hours-1, Hydrogen Vapor Pressure 1.5MPa, flow 20ml min-1,
Temperature 390 DEG C.After reaction terminates, using mass spectrum that reaction result is carried out qualitative analysis, chromatograph is to instead
Result should carry out quantitative analysis.Reaction substrate conversion ratio is 93%, and the selectivity of BTX is 81%.
[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 5 hydroxymethyl furfuralWeight 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, chromatograph is to instead
Result should carry out quantitative analysis.Reaction substrate conversion ratio is 95%, and the selectivity of BTX is 78%.
[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 is 5 hydroxymethyl furfuralWeight space velocity 1.0 hours-1, Hydrogen Vapor Pressure 2.5MPa, flow 40ml min-1,
Temperature 450 DEG C.After reaction terminates, using mass spectrum that reaction result is carried out qualitative analysis, chromatograph is to instead
Result should carry out quantitative analysis.Reaction substrate conversion ratio is 90%, and the selectivity of BTX is 72%.
[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 5 hydroxymethyl furfural,
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 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 (10)
1. a production method for aromatic hydrocarbons, under aromatization conditions, makes raw material contact with catalyst raw
Become containing benzene, toluene and the arene stream of dimethylbenzene；Wherein, described raw material has a structure formula (I):
In formula (I), R1For hydrogen, optionally substituted C1-20Straight or branched alkyl, optionally substituted C2-20
Straight or branched thiazolinyl, optionally substituted C2-20Straight or branched alkynyl, optionally substituted C3-20Ring
Alkyl or optionally substituted C6-20Aryl；R2For optionally substituted C1-20Straight or branched carboxyl,
Furyl or hydroxyl alkyl furyl；Wherein, described hydroxyl alkyl furyl has a structural formula (II):
In formula (II), R3For optionally substituted C1-20Straight or branched alkyl, optionally substituted C2-20Directly
Chain or branched-chain alkenyl, optionally substituted C2-20Straight or branched alkynyl；
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 production method of aromatic hydrocarbons the most according to claim 1, it is characterised in that in formula (I),
R1For optionally substituted C2-10Straight or branched alkyl, optionally substituted C2-10Straight or branched thiazolinyl.
The production method of aromatic hydrocarbons the most according to claim 1, it is characterised in that in formula (I),
R2For optionally substituted C2-10Straight or branched carboxyl.
The production method of aromatic hydrocarbons the most according to claim 1, it is characterised in that in formula (II),
R3For optionally substituted C2-10Straight or branched alkyl, optionally substituted C2-10Straight or branched thiazolinyl.
The production method of aromatic hydrocarbons the most according to claim 1, it is characterised in that described compound zirconium oxygen
In compound, in terms of parts by weight, XaObConsumption be 1～40 part, ZrO2Consumption be 60～99
Part.
The production method of aromatic hydrocarbons the most according to claim 1, it is characterised in that described aromatisation bar
Part 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 production method of aromatic hydrocarbons the most according to claim 6, it is characterised in that described aromatisation bar
Part 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。
The production method of aromatic hydrocarbons the most according to claim 1, it is characterised in that described raw material from
Biological material.
The production method of aromatic hydrocarbons the most according to claim 1, it is characterised in that described raw material from
At least one in xylitol, glucose, fructose, cellobiose, hemicellulose or lignin.
The production method of aromatic hydrocarbons the most according to claim 1, it is characterised in that described raw material comes
At least one in bagasse, glucose, timber, corn stalk, corn cob or Caulis et Folium Oryzae 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 |
| JP2017565948A JP6877367B2 (en) | 2015-06-19 | 2016-06-17 | Method for producing aromatic hydrocarbons, p-xylene 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 |
| 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 |
| BR112017027347-0A BR112017027347B1 (en) | 2015-06-19 | 2016-06-17 | Processes for the production of 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 |
| PCT/CN2016/000315 WO2016201955A1 (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 |
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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 |
|---|
| DONG WANG等: "elective Production of Aromatics from Alkylfurans over Solid Acid Catalysts", 《CHEMCATCHEM》 * |
| 赵岩: "生物质催化转化制备芳烃", 《中国博士学位论文全文数据库 工程科技I辑》 * |
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