CN106316767B - Lactone compound aromatization method - Google Patents
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Abstract
The present invention relates to a kind of lactone compound aromatization methods.This method is included under aromatization conditions, and lactone compound is made to contact the step of generating the arene stream containing benzene, toluene and dimethylbenzene with strong solid acid catalyst, wherein the lactone compound has structure formula (I):In formula (I), R1For 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, the C optionally replaced3‑20Naphthenic base or the C optionally replaced6‑20Aryl；R2For hydrogen, optionally the C 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 lactone compound aromatization method, in particular to a kind of lactone compound aromatisation system
The method of standby benzene,toluene,xylene light aromatics.
Background technique
BTX is the abbreviation of benzene, toluene and dimethylbenzene these three types aromatic hydrocarbon substance.BTX is the important substantially organic of social development
Industrial chemicals, its own or multiple product chain can be derived by reproduction, product be widely used in polyester, chemical fibre, rubber,
Numerous areas, the domestic consumption amount such as medicine and fine chemistry industry reach up to ten million tons, have great influence to the national economic development.
Benzene is a kind of basic petrochemical material of multipurpose, can produce numerous products derived from it, including ethyl benzene/styrene, isopropylbenzene/benzene
Phenol etc..Paraxylene passes through terephthalic acid (TPA) (PTA) or diethyl terephthalate mainly for the manufacture of terephthalic acid (TPA)
(DMT) intermediate gathers cruel fiber such as polyethylene terephthalate (PET), resin and film for producing.At present both at home and abroad
The production of aromatic hydrocarbons depends on non-renewable fossil resource, such as can by a catalyst by petroleum by plus hydrogen, reformation,
The technical process such as aromatic hydrocarbons conversion and separation obtain.But fossil resource reserves are limited and non-renewable, so that based on petroleum
Refine raw material production aromatic hydrocarbons cost more see it is surging.In addition, continually developing for fossil resource utilizes a large amount of greenhouse gases of generation
Discharge, caused a series of environmental problems are on the rise, therefore development has important meaning from renewable resource route production aromatic hydrocarbons
Justice and application value.
Biomass lactone compound typical case such as valerolactone can be obtained after hydrolyzing deoxidation by cellulose.Gamma-valerolactone
One of biomass platform chemicals are had been cited as, gasoline, additive and other chemicals can be converted by the means of catalysis.
For example, the noble metal catalyst effect of acid carrier load is lower to use H2Reduction, can obtain valeric acid.Valeric acid by cerium oxide and
Decarboxylation coupling reaction can occur for the mixture through catalytic of zirconium oxide, butyl ketone be generated, using the available gasoline of hydrogenating reduction
Component.Use Pd/NbO2Catalyst, at 325 DEG C, 3.5MPa adds hydrogen to 50% gamma-valerolactone aqueous solution, and the yield of valeric acid is
92% (J.C.Serrano-Ruiz, D.Wang, J.A.Dumesic, Catalytic upgrading of levulinic
acid to 5-nonanone,Green Chemistry 2010,12,574-577.)。
On the whole, the conversion of valerolactone, which is concentrated mainly on, is converted into the essences such as oil product, oil dope and pyrrolidones
Thin chemicals is rarely reported and is translated into the aromatic hydrocarbons such as benzene,toluene,xylene.
Summary of the invention
The present invention is intended to provide a kind of lactone compound aromatization method.This method has at low cost, aromatisation efficiency
Height, BTX selectively high feature.
For achieving the above object, The technical solution adopted by the invention is as follows: a kind of lactone compound aromatisation side
Method is included under aromatization conditions, and lactone compound is made to contact generation with strong solid acid catalyst containing benzene, toluene and dimethylbenzene
Arene stream the step of；Wherein, the lactone compound has structure formula (I):
In formula (I), R1For 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, the C optionally replaced3-20Naphthenic base or the C optionally replaced6-20Aryl；R2For
Hydrogen, 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.
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 the strong solid acid catalyst is selected from SO4 2-/ZrO2、S2O8 2-/ZrO2、
SO4 2-/TiO2、SO4 2-/ZrO2-Fe3O4、Pt/SO4 2-/TiO2、SO4 2-/TiO2-ZrO2、SO4 2-/TiO2-Al2O3、SO4 2-/
TiO2-WO3、SO4 2-/ZrO2-Fe2O3-Cr2O3、SbF5/SiO2-Al2O3、SO4 2-/ZrO2-WO3、SO4 2-/TiO2-MoO3、PF3/
Al2O3-B2O3、AsF3/Al2O3-B2O3、SbF3/Al2O3-B2O3、BiF3/Al2O3-B2O3、TaF3/Al2O3-B2O3、VF3/Al2O3-
B2O3、NbF3/Al2O3-B2O3、SO4 2-/ZrO2-Fe2O3-MnO2Or AlCl3-CuCl2At least one of.
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 0.1~10 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 lactone compound comes from biological material.
In above-mentioned technical proposal, it is preferable that the lactone compound comes from xylitol, glucose, fructose, fiber two
At least one of sugar, hemicellulose or lignin.
In above-mentioned technical proposal, it is preferable that the lactone compound from bagasse, glucose, timber, corn stalk or
At least one of straw straw.
In above-mentioned technical proposal, it is preferable that the lactone compound be selected from propiolactone, butyrolactone, gamma-valerolactone, when
Return at least one of lactone, δ-valerolactone, caprolactone or decalactone.
In the method for the present invention, the lactone compound comes from biological material.Such as valerolactone, it can be passed through by cellulose
It is obtained after hydrolysis deoxidation, reference can be made to document " Direct conversion of cellulose to levulinic acid
And gamma-valerolactone using solid acid catalysts, Catal.Sci.Technol., 2013,3,
927-931；Production of levulinic acid and gamma-valerolactone(GVL)from
Cellulose using GVL as a solvent in biphasic systems, Energy Environ.Sci.,
2012,5,8199-8203”。
In the present invention, the preparation method of strong solid acid catalyst is can to use precipitation-impregnation to be known in the art
Method.For details, reference can be made to document " solid acid and fine chemistry industry " and " SO4 2-/MxOyThe progress of type solid super acid catalyst, is answered
With chemical industry, 2014, vol43,1879-1883 ".
The method of the present invention has preferable conversion ratio to lactone compound, 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 can reach 94%, achieve
Preferable technical effect.
Below by embodiment, the present invention is further elaborated.
Specific embodiment
[embodiment 1]
50 grams of bagasse are weighed, is placed in autoclave pressure and is added 500 grams of water, add the salt of the 5mol/L of water quality 5%
Acid solution is warming up to 1 hour of reaction at 180 DEG C, 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 16 grams.Obtained levulic acid adds hydrogen to obtain in fixed bed on the RuSn/C of 2% content of metal
Gamma-valerolactone, conversion ratio 99%, product yield 98%.
5 grams are weighed through the SO for removing water 12 hours dry at 120 DEG C4 2-/ZrO2Catalyst is packed into fixed bed reactors.Reaction
Substrate is gamma-valerolactoneWeight space velocity 0.3 hour-1, Hydrogen Vapor Pressure 1.0MPa, flow 50ml min-1, temperature
400 DEG C of degree.After reaction, qualitative analysis is carried out to reaction result using mass spectrum, chromatography carries out quantitative analysis to reaction result.
The selectivity that reaction substrate conversion ratio is 99%, BTX is 83%.
[embodiment 2]
5 grams are weighed through the S for removing water 12 hours dry at 120 DEG C2O8 2-/ZrO2Catalyst is packed into fixed bed reactors.Instead
Answering substrate is third dodecalactoneWeight space velocity 1.0 hours-1, Hydrogen Vapor Pressure 1.0MPa,
Flow 20ml 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 93%, BTX is 93%.
[embodiment 3]
5 grams are weighed through the SO for removing water 12 hours dry at 120 DEG C4 2-/TiO2Catalyst is packed into fixed bed reactors.Reaction
Substrate is third caprolactoneWeight space velocity 3.0 hours-1, Hydrogen Vapor Pressure 1.0MPa, flow 20ml min-1,
400 DEG C of temperature.After reaction, qualitative analysis is carried out to reaction result using mass spectrum, chromatography quantitatively divides reaction result
Analysis.The selectivity that reaction substrate conversion ratio is 84%, BTX is 87%.
[embodiment 4]
5 grams are weighed through the SO for removing water 12 hours dry at 120 DEG C4 2-/ZrO2-Fe3O4Catalyst is packed into fixed bed reaction
Device.Reaction substrate is gamma decalactoneWeight space velocity 5.0 hours-1, Hydrogen Vapor Pressure
1.0MPa, 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 86%, BTX is 81%.
[embodiment 5]
5 grams are weighed through the Pt/SO for removing water 12 hours dry at 120 DEG C4 2-/TiO2Catalyst is packed into fixed bed reactors.
Reaction substrate is third heptalactoneWeight space velocity 2.0 hours -1, Hydrogen Vapor Pressure 3.0MPa, flow 20ml
min-1, 450 DEG C of temperature.After reaction, qualitative analysis is carried out to reaction result using mass spectrum, chromatography determines reaction result
Amount analysis.The selectivity that reaction substrate conversion ratio is 85%, BTX is 82%.
[embodiment 6]
5 grams are weighed through the SO for removing water 12 hours dry at 120 DEG C4 2-/TiO2-ZrO2Catalyst is packed into fixed bed reaction
Device.Reaction substrate is third caprylolactoneWeight space velocity 0.8 hour-1, Hydrogen Vapor Pressure
1.0MPa, flow 40ml 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 84%, BTX is 87%.
[embodiment 7]
5 grams are weighed through the SO for removing water 12 hours dry at 120 DEG C4 2-/TiO2-Al2O3Catalyst is packed into fixed bed reaction
Device.Reaction substrate is gamma-butyrolactonWeight space velocity 1.0 hours-1, Hydrogen Vapor Pressure 1.0MPa, flow 20ml min-1, 400 DEG C of temperature.After reaction, qualitative analysis is carried out to reaction result using mass spectrum, chromatography quantifies reaction result
Analysis.The selectivity that reaction substrate conversion ratio is 81%, BTX is 85%.
[embodiment 8]
5 grams are weighed through the SO for removing water 12 hours dry at 120 DEG C4 2-/ZrO2-Fe2O3-Cr2O3Catalyst is packed into fixed bed
Reactor.Reaction substrate is 6-caprolactoneWeight space velocity 2.0 hours-1, Hydrogen Vapor Pressure 1.0MPa, flow 50ml
min-1, 450 DEG C of temperature.After reaction, qualitative analysis is carried out to reaction result using mass spectrum, chromatography determines reaction result
Amount analysis.The selectivity that reaction substrate conversion ratio is 93%, BTX is 85%.
[embodiment 9]
5 grams are weighed through the SbF for removing water 12 hours dry at 120 DEG C5/SiO2-Al2O3Catalyst is packed into fixed bed reaction
Device.Reaction substrate is δ-valerolactoneWeight space velocity 3.0 hours-1, Hydrogen Vapor Pressure 1.0MPa, flow 20ml min-1, 400 DEG C of temperature.After reaction, qualitative analysis is carried out to reaction result using mass spectrum, chromatography quantifies reaction result
Analysis.The selectivity that reaction substrate conversion ratio is 83%, BTX is 89%.
[embodiment 10]
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.Obtained levulic acid is in fixed bed in the Cu/SiO of 20% content of metal2Upper plus hydrogen obtains
To gamma-valerolactone, conversion ratio 99%, product yield 98%.
5 grams are weighed through the SO for removing water 12 hours dry at 120 DEG C4 2-/TiO2-WO3Catalyst is packed into fixed bed reactors.
Reaction substrate is gamma-valerolactoneWeight space velocity 1.0 hours-1, Hydrogen Vapor Pressure 1.0MPa, flow 20ml min-1, 500 DEG C of temperature.After reaction, qualitative analysis is carried out to reaction result using mass spectrum, chromatography quantifies reaction result
Analysis.The selectivity that reaction substrate conversion ratio is 86%, BTX is 86%.
[embodiment 11]
5 grams are weighed through the SO for removing water 12 hours dry at 120 DEG C4 2-/ZrO2-WO3Catalyst is packed into fixed bed reactors.
Reaction substrate is angelica lactone, weight space velocity 1.0 hours-1, Hydrogen Vapor Pressure 1.0MPa, flow 20ml min-1, 380 DEG C of temperature.
After reaction, qualitative analysis is carried out to reaction result using mass spectrum, chromatography carries out quantitative analysis to reaction result.Reaction substrate
The selectivity that conversion ratio is 92%, BTX is 88%.
[embodiment 12]
5 grams are weighed through the SO for removing water 12 hours dry at 120 DEG C4 2-/TiO2-MoO3Catalyst is packed into fixed bed reactors.
Reaction substrate is gamma-valerolactoneWeight space velocity 2.0 hours-1, Hydrogen Vapor Pressure 1.0MPa, flow 20ml min-1, 380 DEG C of temperature.After reaction, qualitative analysis is carried out to reaction result using mass spectrum, chromatography quantifies reaction result
Analysis.The selectivity that reaction substrate conversion ratio is 82%, BTX is 83%.
[embodiment 13]
5 grams are weighed through the BiF for removing water 12 hours dry at 120 DEG C3/Al2O3-B2O3Catalyst is packed into fixed bed reactors.
Reaction substrate is beta-propiolactoneWeight space velocity 1.0 hours-1, Hydrogen Vapor Pressure 1.0MPa, flow 20ml min-1, temperature
420 DEG C of degree.After reaction, qualitative analysis is carried out to reaction result using mass spectrum, chromatography carries out quantitative analysis to reaction result.
The selectivity that reaction substrate conversion ratio is 86%, BTX is 86%.
[embodiment 14]
5 grams are weighed through the NbF for removing water 12 hours dry at 120 DEG C3/Al2O3-B2O3Catalyst is packed into fixed bed reactors.
Reaction substrate is third caprolactoneWeight space velocity 2.0 hours-1, Hydrogen Vapor Pressure 1.0MPa, flow 20ml
min-1, 360 DEG C of temperature.After reaction, qualitative analysis is carried out to reaction result using mass spectrum, chromatography determines reaction result
Amount analysis.The selectivity that reaction substrate conversion ratio is 88%, BTX is 94%.
[embodiment 15]
5 grams are weighed through the SO for removing water 12 hours dry at 120 DEG C4 2-/ZrO2-Fe2O3-MnO2Catalyst is packed into fixed bed
Reactor.Reaction substrate is gamma-butyrolactonWeight space velocity 2.0 hours-1, Hydrogen Vapor Pressure 1.0MPa, flow 20ml
min-1, 400 DEG C of temperature.After reaction, qualitative analysis is carried out to reaction result using mass spectrum, chromatography determines reaction result
Amount analysis.The selectivity that reaction substrate conversion ratio is 89%, BTX is 85%.
[embodiment 16]
5 grams are weighed through the SO for removing water 12 hours dry at 120 DEG C4 2-/ZrO2-Fe2O3-Cr2O3Catalyst is packed into fixed bed
Reactor.Reaction substrate is angelica lactone, weight space velocity 1.0 hours-1, Hydrogen Vapor Pressure 1.0MPa, flow 20ml min-1, temperature
380℃.After reaction, qualitative analysis is carried out to reaction result using mass spectrum, chromatography carries out quantitative analysis to reaction result.Instead
Answering the selectivity that the substrate transformation rate is 92%, BTX is 84%.
[embodiment 17]
5 grams are weighed through the AlCl for removing water 12 hours dry at 120 DEG C3-CuCl2Catalyst is packed into fixed bed reactors.Instead
Answer substrate for gamma-valerolactone, weight space velocity 2.5 hours-1, Hydrogen Vapor Pressure 1.0MPa, flow 20ml min-1, 400 DEG C of temperature.Instead
After answering, qualitative analysis is carried out to reaction result using mass spectrum, chromatography carries out quantitative analysis to reaction result.Reaction substrate turns
The selectivity that rate is 83%, BTX is 82%.
Table 1
| Embodiment | Substrate | Catalyst | Conversion ratio/% | BTX selectivity/% |
| 1 | Gamma-valerolactone | SO4 2-/ZrO2 | 99 | 83 |
| 2 | Third dodecalactone | S2O8 2-/ZrO2 | 93 | 93 |
| 3 | Third caprolactone | SO4 2-/TiO2 | 84 | 87 |
| 4 | Gamma decalactone | SO4 2-/ZrO2-Fe3O4 | 86 | 81 |
| 5 | Third heptalactone | Pt/SO4 2-/TiO2 | 85 | 82 |
| 6 | Third caprylolactone | SO4 2-/TiO2-ZrO2 | 84 | 87 |
| 7 | Gamma-butyrolacton | SO4 2-/TiO2-Al2O3 | 81 | 85 |
| 8 | 6-caprolactone | SO4 2-/ZrO2-Fe2O3-Cr2O3 | 93 | 85 |
| 9 | δ-valerolactone | SbF5/SiO2-Al2O3 | 83 | 89 |
| 10 | Gamma-valerolactone | SO4 2-/TiO2-WO3 | 86 | 86 |
| 11 | Angelica lactone | SO4 2-/ZrO2-WO3 | 92 | 88 |
| 12 | Gamma-valerolactone | SO4 2-/TiO2-MoO3 | 82 | 83 |
| 13 | Beta-propiolactone | BiF3/Al2O3-B2O3 | 86 | 86 |
| 14 | Third caprolactone | NbF3/Al2O3-B2O3 | 88 | 94 |
| 15 | Gamma-butyrolacton | SO4 2-/ZrO2-Fe2O3-MnO2 | 89 | 85 |
| 16 | Angelica lactone | SO4 2-/ZrO2-Fe2O3-Cr2O3 | 92 | 84 |
| 17 | Gamma-valerolactone | AlCl3-CuCl2 | 83 | 82 |
Claims (9)
1. a kind of lactone compound aromatization method, is included under aromatization conditions, makes lactone compound and solid strong acid
The step of catalyst contact generates the arene stream containing benzene, toluene and dimethylbenzene；Wherein, the lactone compound has structure
Formula (I):
In formula (I), R1For C1-20Linear or branched alkyl group, C2-20Linear chain or branched chain alkenyl, C2-20Linear chain or branched chain alkynyl, C3-20Ring
Alkyl or C6-20Aryl；R2For hydrogen, C1-20Linear chain or branched chain carboxyl, furyl or hydroxyl alkyl furyl；Wherein, the hydroxyl
Alkyl furyl has structural formula (II):
In formula (II), R3For C1-20Linear or branched alkyl group, C2-20Linear chain or branched chain alkenyl, C2-20Linear chain or branched chain alkynyl；
The strong solid acid catalyst is selected from SO4 2-/ZrO2、S2O8 2-/ZrO2、SO4 2-/TiO2、SO4 2-/ZrO2-Fe3O4、Pt/
SO4 2-/TiO2、SO4 2-/TiO2-ZrO2、SO4 2-/TiO2-Al2O3、SO4 2-/TiO2-WO3、SO4 2-/ZrO2-Fe2O3-Cr2O3、
SbF5/SiO2-Al2O3、SO4 2-/ZrO2-WO3、SO4 2-/TiO2-MoO3、PF3/Al2O3-B2O3、AsF3/Al2O3-B2O3、SbF3/
Al2O3-B2O3、BiF3/Al2O3-B2O3、TaF3/Al2O3-B2O3、VF3/Al2O3-B2O3、NbF3/Al2O3-B2O3、SO4 2-/ZrO2-
Fe2O3-MnO2Or AlCl3-CuCl2At least one of.
2. lactone compound aromatization method according to claim 1, it is characterised in that in formula (I), R1For C2-10Straight chain or
Branched alkyl, C2-10Linear chain or branched chain alkenyl.
3. lactone compound aromatization method according to claim 1, it is characterised in that in formula (I), R2For C2-10Straight chain or
Branch carboxyl.
4. lactone compound aromatization method according to claim 1, it is characterised in that in formula (II), R3For C2-10Straight chain
Or branched alkyl, C2-10Linear chain or branched chain alkenyl.
5. lactone compound aromatization method according to claim 1, it is characterised in that the aromatization conditions are as follows: reaction
300~800 DEG C of temperature, Hydrogen Vapor Pressure 0.1~5MPa in terms of gauge pressure, raw material weight air speed 0.3~10 hour-1。
6. lactone compound aromatization method according to claim 5, it is characterised in that the aromatization conditions are as follows: reaction
300~650 DEG C of temperature, Hydrogen Vapor Pressure 0.5~4MPa in terms of gauge pressure, raw material weight air speed 0.3~5 hour-1。
7. lactone compound aromatization method according to claim 1, it is characterised in that the raw material comes from biological material
Material.
8. lactone compound aromatization method according to claim 1, it is characterised in that the raw material comes from xylitol, Portugal
At least one of grape sugar, cellobiose, hemicellulose or lignin.
9. lactone compound aromatization method according to claim 1, it is characterised in that the raw material comes from bagasse, Portugal
At least one of grape sugar, timber, corn stalk or straw straw.
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