WO2017162900A1 - Procedimiento para la valorización de compuestos oxigenados presentes en fracciones acuosas derivadas de biomasa - Google Patents
Procedimiento para la valorización de compuestos oxigenados presentes en fracciones acuosas derivadas de biomasa Download PDFInfo
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- WO2017162900A1 WO2017162900A1 PCT/ES2017/070167 ES2017070167W WO2017162900A1 WO 2017162900 A1 WO2017162900 A1 WO 2017162900A1 ES 2017070167 W ES2017070167 W ES 2017070167W WO 2017162900 A1 WO2017162900 A1 WO 2017162900A1
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- Prior art keywords
- catalyst
- process according
- elements
- biomass
- reactor
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- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- PZSJOBKRSVRODF-UHFFFAOYSA-N vanillin acetate Chemical compound COC1=CC(C=O)=CC=C1OC(C)=O PZSJOBKRSVRODF-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- IPCAPQRVQMIMAN-UHFFFAOYSA-L zirconyl chloride Chemical compound Cl[Zr](Cl)=O IPCAPQRVQMIMAN-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/002—Mixed oxides other than spinels, e.g. perovskite
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G3/00—Production of liquid hydrocarbon mixtures from oxygen-containing organic materials, e.g. fatty oils, fatty acids
- C10G3/42—Catalytic treatment
- C10G3/44—Catalytic treatment characterised by the catalyst used
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/10—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of rare earths
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/20—Vanadium, niobium or tantalum
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/24—Chromium, molybdenum or tungsten
- B01J23/30—Tungsten
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/847—Vanadium, niobium or tantalum or polonium
- B01J23/8474—Niobium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/85—Chromium, molybdenum or tungsten
- B01J23/888—Tungsten
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/30—Catalysts, in general, characterised by their form or physical properties characterised by their physical properties
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/0236—Drying, e.g. preparing a suspension, adding a soluble salt and drying
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/08—Heat treatment
- B01J37/10—Heat treatment in the presence of water, e.g. steam
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/03—Precipitation; Co-precipitation
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/10—Feedstock materials
- C10G2300/1011—Biomass
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/70—Catalyst aspects
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
- C10G2400/30—Aromatics
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P30/00—Technologies relating to oil refining and petrochemical industry
- Y02P30/20—Technologies relating to oil refining and petrochemical industry using bio-feedstock
Definitions
- This invention belongs to the field of synthesis and application of catalysts for the conversion of biomass mainly of the lignocellulosic type and its derivatives into liquid fuels for transport.
- Biomass, together with C0 2 is one of the primary and renewable sources of coal.
- the valorization of biomass (mainly vegetable or lignocellulosic type) and its derivatives is a sustainable alternative to the use of fossil sources for the production of fuels and chemical products, thus reducing the obvious problems of depletion of non-renewable resources and the environmental issues associated with them [GW Huber, S. Iborra, A. Corma. Chemical Reviews, 106 (2006) 4044].
- GW Huber, S. Iborra, A. Corma. Chemical Reviews, 106 (2006) 4044 In this sense, in the new concept of bio-refinery and bio-economy, it is essential to co-produce biofuels together with other chemical products of interest.
- bio-liquid oils can be obtained mostly.
- biomass mainly vegetable or lignocellulosic type
- bio-liquid oils can be obtained mostly.
- bio-liquids are complex mixtures of more than 200 components, containing different proportions of water and mainly compounds organic oxygenates (ie alcohols, ketones, acids, polyalcohols, furans, phenols, among others) of different molecular sizes that are characterized by their high oxygen content and great reactivity.
- the bio-liquids also have a high acidity due to the presence of short chain carboxylic acids (C1-C4), which makes storage and direct use difficult.
- an organic phase can be obtained, on the one hand, containing various organic compounds of interest for later use as fuels; and on the other hand aqueous fractions and effluents containing C1-C4 short chain carboxylic acids (mainly acetic acid) together with other compounds such as aldehydes, ketones or alcohols and small amounts of furanic compounds and / or heavier compounds, which are not being currently used and constitute residual currents in bio-refineries [M. Asadieraghi et al., Renewable and Sustainable Energy Reviews, 36 (2014) 286, E. E. lojoiu et al., Applied Catalysis A: Gen. 323 (2007) 147].
- C1-C4 short chain carboxylic acids mainly acetic acid
- oxygenated organic compounds mostly short chain ( ⁇ C5) have little value in themselves, but can be efficiently transformed to generate mixtures of longer chain hydrocarbons and aromatic compounds that are very useful as precursors, components and / or additives in automotive liquid fuels.
- These compounds (hydrocarbons and aromatics) are produced by the formation of carbon-carbon bonds through reactions of condensation, ketoneization, alkylation with alcohols, which occur consecutively [CA Gaertner et al. Journal of Catalysis, 266 (2009) 71].
- other reactions such as decarboxylations, dehydrations or esterifications when treating these complex aqueous mixtures.
- the present invention relates to a process for the production of mixtures of hydrocarbons and aromatic compounds, which may comprise at least the following steps:
- step (c) recover the products obtained in step (b) by a process of liquid / liquid separation of the aqueous and organic phases.
- the process of the present invention for the catalytic transformation of oxygenated compounds present in aqueous fractions derived from biomass in mixtures of hydrocarbons and aromatic compounds (preferably C5-C16) can use a catalyst having the empirical formula:
- - A is a metal of the group of alkali and alkaline earth metals
- - B is a chemical element of the group of transition metals, rare earths or elements of groups III, IV and V.
- - a and b are between 0 and 12.0, with a + b other than zero (a + b ⁇ 0)
- - d is between 0 and 4.0
- - e has a value that depends on the oxidation state of elements W, Nb and element B.
- the catalyst must comply with the condition that the catalyst comprises at least W and / or Nb and that, in its calcined form, it has at least one material arranged along one of the crystallographic axes and a diffractogram of X-rays in which at least diffraction lines corresponding to angles 2 ⁇ to 22.7 ⁇ 0.4 and 46.6 ⁇ 0.4 are observed.
- Said catalyst can be prepared by conventional methods from solutions of compounds of the different elements, solutions of the same pure elements, or mixing thereof, with the desired atomic ratios.
- Said solutions are preferably aqueous solutions.
- the catalyst is obtained by a process comprising at least:
- the mixing stage can be carried out from the compounds of the different elements, from the pure elements themselves in solution, or by hydrothermal methods.
- the elements W, Nb and metals A and B can be incorporated into the mixing stage as pure metal elements, as salts, as oxides, as hydroxides, as alkoxides, or as mixtures of two or more of the aforementioned forms.
- Sulfates, nitrates, oxalates or halides, and more preferably sulfates are preferably used as salts.
- the W may be incorporated into the mixing stage preferably as tungsamic acid, ammonium tungsten, ammonium metawolframto, ammonium parawolframto or tungsten oxide.
- the Nb can be incorporated into the mixing step preferably as niobium pentoxide, niobium oxalate, niobium chloride or Nb metal.
- the mixing step can be followed by a period of static permanence in the reactor, or the mixing can be carried out with stirring. Both static permanence and agitation can be performed in a normal reactor or in an autoclave.
- the mixing step can be carried out in solution or by hydrothermal treatment.
- the drying step can be carried out by conventional methods in an oven, evaporation with stirring, evaporation in a rotary evaporator, or vacuum drying.
- the step of calcining the dry solid can be carried out under an inert gas atmosphere, such as nitrogen, helium, argon or mixtures thereof, as well as of air or mixtures of air with other gases.
- an inert gas atmosphere such as nitrogen, helium, argon or mixtures thereof, as well as of air or mixtures of air with other gases.
- This calcination step can be carried out by passing a flow of inert gas (with space velocities between 1 and 400 h "1 ) or static.
- the temperature is preferably in a range between 250 and 850 ° C and more. preferably between 450 and 650 ° C.
- the calcination time is not determinative, but it is preferred that it is in a range of between 0.5 hours and 20.
- the heating rate is not determinant, but is preferred in a range of between 0.1 ° C / minute and 10 ° C / minute
- the catalyst may also be initially calcined in an oxidizing atmosphere to a temperature between 200 and 350 ° C, and more preferably between 240 and 290 ° C, and be Subsequently subjected to calcination in an inert atmosphere.
- the catalyst is obtained, as indicated above, using hydrothermal methods (containing two or more elements in the synthesis, especially containing W, Nb, and elements A and B).
- the temperature and time of synthesis can be decisive using hydrothermal methods.
- the synthesis temperature is preferably between 100 and 250 ° C and, more preferably, between 150 and 180 ° C.
- the synthesis time is preferably between 6 and 500 hours, and more preferably between 24 and 200 hours.
- the catalyst is obtained by co-precipitation of the elements, either from precursor compounds containing the different elements or from the pure elements themselves in solution.
- precursor compounds containing elements W, Nb and elements A and B salts, oxides, hydroxides, alkoxides or mixtures of two or more of the aforementioned forms can be used.
- Sulfates, nitrates, oxalates or halides, and more preferably sulfates are preferably used as salts.
- solvent water, methanol, ethanol, isopropanol, acetonitrile, dioxane, or mixtures thereof, preferably water, can be used.
- Co-precipitation of the elements in the solution is carried out by controlled change of pH by the addition of a basic compound selected from hydroxides of alkali metals, alkaline earth metal hydroxides, ammonium hydroxide or ammonia water, and alkali metal hypochlorites, without being these limiting examples.
- a basic compound selected from hydroxides of alkali metals, alkaline earth metal hydroxides, ammonium hydroxide or ammonia water, and alkali metal hypochlorites, without being these limiting examples.
- the catalyst described can be used for the inventive process as it is obtained once calcined.
- the catalyst described above can be supported and / or diluted on a solid such as: silica, alumina, titanium oxide or mixtures thereof, as well as silicon carbide.
- the fixing of the different catalyst elements on the support can be carried out by conventional impregnation methods, such as pore volume, excess solution, or simply by precipitation on the support of a solution containing the active elements.
- a catalyst can be used that starting from the formula with the composition W a Nb b A c B d O e , where d is zero, has the following empirical formula:
- - A is a metal of the group of alkali or alkaline earth metals
- - a and b are between 0 and 12, with a + b other than zero (a + b ⁇ 0)
- - e has a value that depends on the oxidation state of the elements W and Nb.
- the above formula must comply with the condition that the catalyst comprises at least W and / or Nb and that, in its calcined form, it has at least one material arranged along one of the crystallographic axes and a ray diffractogram X in which at least diffraction lines corresponding to angles 2 ⁇ to 22.7 ⁇ 0.4 and 46.6 ⁇ 0.4 are observed.
- Said catalyst can be prepared by conventional methods from solutions of compounds of the different elements, solutions of the same pure elements, or mixing thereof, with the desired atomic ratios. Said solutions are preferably aqueous solutions.
- the mixing stage can be carried out from the compounds of the different elements, from the pure elements themselves in solution, or by hydrothermal methods.
- the elements W, Nb and the metal A can be incorporated into the mixing stage as pure metal elements, as salts, as oxides, as hydroxides, as alkoxides, or as mixtures of two or more of the aforementioned forms.
- Sulfates, nitrates, oxalates or halides, and more preferably sulfates are preferably used as salts.
- the W may be incorporated into the mixing stage preferably as tungsamic acid, ammonium tungsten, ammonium metawolframto, ammonium parawolframto or tungsten oxide.
- the Nb can be incorporated into the mixing step preferably as niobium pentoxide, niobium oxalate, niobium chloride or Nb metal.
- the mixing step can be followed by a period of static permanence in the reactor, or the mixing can be carried out with stirring. Both static permanence and agitation can be performed in a normal reactor or in an autoclave.
- the mixing step can be carried out in solution or by hydrothermal treatment.
- the drying step can be carried out by conventional methods in an oven, evaporation with stirring, evaporation in a rotary evaporator, or vacuum drying.
- the step of calcining the dry solid can be carried out under an inert gas atmosphere, such as nitrogen, helium, argon or mixtures thereof, as well as air or mixtures of air with other gases.
- an inert gas atmosphere such as nitrogen, helium, argon or mixtures thereof, as well as air or mixtures of air with other gases.
- This calcination step can be carried out by passing a flow of inert gas (with space velocities between 1 and 400 h "1 ) or static.
- the temperature is preferably in a range between 250 and 850 ° C and more. preferably between 450 and 650 ° C.
- the calcination time is not decisive, but it is preferred that it is in a range of between 0.5 hours and 20.
- the heating rate is not determinant, but is preferred in a range between 0.1 ° C / minute and 10 ° C / minute
- the catalyst can also be initially calcined in an oxidizing atmosphere to a temperature between 200 and 350 ° C, and more preferably between 240 and 290 ° C, and be subsequently subjected to calcination in an inert atmosphere.
- the catalyst is obtained, as indicated above, using hydrothermal methods (containing two or more elements in the synthesis, especially containing W, Nb and metal A).
- the temperature and time of synthesis can be decisive using hydrothermal methods.
- the synthesis temperature is preferably between 100 and 250 ° C and, more specifically, between 150 and 180 ° C.
- the synthesis time is preferably between 6 and 500 hours, and more specifically between 24 and 200 hours.
- the catalyst is obtained by co-precipitation of the elements, either from precursor compounds containing the various elements or of the pure elements themselves in solution.
- precursor compounds containing elements W, Nb and element A salts, oxides, hydroxides, alkoxides or mixtures of two or more of the aforementioned forms can be used.
- Sulfates, nitrates, oxalates or halides, and more preferably sulfates are preferably used as salts.
- Water, methanol, ethanol, isopropanol, acetonitrile, dioxane and mixtures thereof, preferably water, can be used as the solvent.
- the co-precipitation of the elements in the solution is carried out by controlled change of pH by the addition of a basic compound selected from alkali metal hydroxides, alkaline earth metal hydroxides, ammonium hydroxide or ammonia water, alkali metal hypochlorites, without being these limiting examples.
- a basic compound selected from alkali metal hydroxides, alkaline earth metal hydroxides, ammonium hydroxide or ammonia water, alkali metal hypochlorites, without being these limiting examples.
- the catalyst described above in this invention can be supported and / or diluted on a solid such as: silica, alumina, titanium oxide or mixtures thereof, as well as silicon carbide.
- a solid such as: silica, alumina, titanium oxide or mixtures thereof, as well as silicon carbide.
- the fixing of the different catalyst elements on the support can be carried out by conventional impregnation methods, such as pore volume, excess solution, or simply by precipitation on the support of a solution containing the active elements.
- a catalyst can be used that starting from the formula with the composition W a Nb b A c B d O e , in which c is zero, has the following empirical formula:
- - B is a chemical element of the group of transition metals, rare earths or elements of groups III, IV and V - a and b are between 0 and 12.0, with a + b other than zero (a + b ⁇ 0)
- - d is between 0.0001 and 4.0
- - e has a value that depends on the oxidation state of elements W, Nb and element B.
- the catalyst comprises at least W and / or Nb and that, in its calcined form, it has at least one material arranged along one of the crystallographic axes and an X-ray diffractogram in which the less diffraction lines corresponding to angles 2 ⁇ to 22.7 ⁇ 0.4 and 46.6 ⁇ 0.4 are observed.
- Said catalyst can be prepared by conventional methods from solutions of compounds of the different elements, solutions of the same pure elements, or mixing thereof, with the desired atomic ratios.
- Said solutions are preferably aqueous solutions.
- the catalyst is obtained by a process comprising at least:
- the mixing stage can be carried out from the compounds of the different elements, from the pure elements themselves in solution, or by hydrothermal methods.
- the elements W, Nb and the metal B can be incorporated into the mixing stage as pure metal elements, as salts, as oxides, as hydroxides, as alkoxides, or as mixtures of two or more of the aforementioned forms.
- Sulfates, nitrates, oxalates or halides, and more preferably sulfates are preferably used as salts.
- the W can be incorporated into the mixing stage preferably as tungsamic acid, ammonium wolfram, ammonium metawolfram, ammonium parawolfram tungsten oxide.
- the Nb can be incorporated into the mixing step preferably as niobium pentoxide, niobium oxalate, niobium chloride or Nb metal.
- the mixing step can be followed by a period of static permanence in the reactor, or the mixing can be carried out with stirring. Both static permanence and agitation can be performed in a normal reactor or in an autoclave.
- the mixing step can be carried out in solution or by hydrothermal treatment.
- the drying step can be carried out by conventional methods in an oven, evaporation with stirring, evaporation in a rotary evaporator, or vacuum drying.
- the step of calcining the dry solid can be carried out under an inert gas atmosphere, such as nitrogen, helium, argon or mixtures thereof, as well as air or mixtures of air with other gases.
- an inert gas atmosphere such as nitrogen, helium, argon or mixtures thereof, as well as air or mixtures of air with other gases.
- This calcination step can be carried out by passing a flow of inert gas (with space velocities between 1 and 400 h "1 ) or static.
- the temperature is preferably in a range between 250 and 850 ° C and more. preferably between 450 and 650 ° C.
- the calcination time is not decisive, but it is preferred that it is in a range of between 0.5 hours and 20.
- the heating rate is not determinant, but is preferred in a range between 0.1 ° C / minute and 10 ° C / minute
- the catalyst can also be initially calcined in an oxidizing atmosphere to a temperature between 200 and 350 ° C, and more preferably between 240 and 290 ° C, and be subsequently subjected to calcination in an inert atmosphere.
- the catalyst is obtained, as indicated above, using hydrothermal methods (containing two or more elements in the synthesis, especially containing W, Nb and element B).
- the temperature and time of synthesis can be decisive using hydrothermal methods.
- the synthesis temperature is preferably between 100 and 250 ° C and, more specifically, between 150 and 180 ° C.
- the synthesis time is preferably between 6 and 500 hours, and more specifically between 24 and 200 hours.
- the catalyst is obtained by co-precipitation of the elements, either from precursor compounds containing the different elements or from the pure elements themselves in solution.
- precursor compounds containing elements W, Nb and element B salts, oxides, hydroxides, alkoxides or mixtures of two or more of the aforementioned forms can be used.
- Sulfates, nitrates, oxalates or halides, and more preferably sulfates are preferably used as salts.
- Water, methanol, ethanol, isopropanol, acetonitrile, dioxane and mixtures thereof, preferably water, can be used as the solvent.
- the co-precipitation of the elements in the solution is carried out by controlled change of pH by the addition of a basic compound selected from alkali metal hydroxides, alkaline earth metal hydroxides, ammonium hydroxide or ammonia water, alkali metal hypochlorites, without being these limiting examples.
- a basic compound selected from alkali metal hydroxides, alkaline earth metal hydroxides, ammonium hydroxide or ammonia water, alkali metal hypochlorites, without being these limiting examples.
- the catalyst described can be used for the inventive process as it is obtained once calcined.
- the catalyst described above in this invention can be supported and / or diluted on a solid such as: silica, alumina, titanium oxide or mixtures thereof, as well as silicon carbide.
- a solid such as: silica, alumina, titanium oxide or mixtures thereof, as well as silicon carbide.
- the fixing of the different catalyst elements on the support can be carried out by conventional impregnation methods, such as pore volume, excess solution, or simply by precipitation on the support of a solution containing the active elements.
- a catalyst can be used that starting from the formula with the composition W a Nb b A c B d O e , in which c and d are zero, has the following empirical formula:
- - a and b are between 0 and 12, with a + b other than zero (a + b ⁇ 0)
- - e has a value that depends on the oxidation state of the elements W and Nb.
- the catalyst comprises at least W and / or Nb and that, in its calcined form, it has at least one material arranged along one of the crystallographic axes and an X-ray diffractogram in which at least they observe diffraction lines corresponding to angles 2 ⁇ to 22.7 ⁇ 0.4 and 46.6 ⁇ 0.4.
- Said catalyst can be prepared by conventional methods from solutions of compounds of the different elements, from solutions of the same pure elements, or from mixing of both, with the desired atomic ratios.
- Said solutions are preferably aqueous solutions.
- the catalyst can be obtained by a process comprising at least:
- the mixing stage can be carried out from the compounds of the different elements, from the pure elements themselves in solution, or by hydrothermal methods.
- the elements W and Nb can be incorporated into the mixing stage as pure metal elements, as salts, as oxides, as hydroxides, as alkoxides, or as mixtures of two or more of the aforementioned forms. Sulfates, nitrates, oxalates or halides, and more preferably sulfates are preferably used as salts.
- the W may be incorporated into the mixing stage preferably as tungsamic acid, ammonium tungsten, ammonium metawolframto, ammonium parawolframto or tungsten oxide.
- the Nb can be incorporated into the mixing step preferably as niobium oxalate, niobium pentoxide, niobium chloride or Nb metal.
- the mixing step can be followed by a period of static permanence in the reactor, or the mixing can be carried out with stirring. Both static permanence and agitation can be performed in a normal reactor or in an autoclave.
- the mixing step can be carried out in solution or by hydrothermal treatment.
- the drying step can be carried out by conventional methods in an oven, evaporation with stirring, evaporation in a rotary evaporator, or vacuum drying.
- the step of calcining the dry solid can be carried out under an inert gas atmosphere, such as nitrogen, helium, argon or mixtures thereof, as well as air or mixtures of air with other gases.
- an inert gas atmosphere such as nitrogen, helium, argon or mixtures thereof, as well as air or mixtures of air with other gases.
- This calcination stage can be carried out by passing a flow of inert gas (with space velocities between 1 and 400 h "1 ) or static.
- the temperature is preferably in a range between 250 and 850 ° C and more preferably between 450 and 650 ° C.
- the calcination time is not determinant, but it is preferred that it is in a range between 0.5 hours and 20 hours
- the heating rate is not decisive, but is preferred in a range between 0.1 ° C / minute and 10 ° C / minute
- the catalyst may also be initially calcined in an oxidizing atmosphere to a temperature between 200 and 350 ° C, and more preferably between 240 and 290 ° C, and subsequently subjected to calcination in an inert atmosphere.
- the catalyst can be obtained, as indicated above, using hydrothermal methods (containing two or more elements in the synthesis, especially containing W and Nb).
- the temperature and time of synthesis can be decisive using hydrothermal methods.
- the synthesis temperature is preferably between 100 and 250 ° C and, more specifically, between 150 and 180 ° C.
- the synthesis time is preferably between 6 and 500 hours, and more specifically between 24 and 200 hours.
- the catalyst can be obtained by co-precipitation of the elements, either from precursor compounds containing the different elements or from the pure elements themselves in solution.
- precursor compounds containing the elements W and Nb salts, oxides, hydroxides, alkoxides or mixtures of two or more of the aforementioned forms can be used.
- Sulfates, nitrates, oxalates or halides, and more preferably sulfates are preferably used as salts.
- solvent water, methanol, ethanol, iso-propanol, acetonitrile, dioxane and mixtures thereof, preferably water, can be used.
- the co-precipitation of the elements in the solution is carried out by controlled change of pH by the addition of a basic compound selected from alkali metal hydroxides, alkaline earth metal hydroxides, ammonium hydroxide or ammonia water, alkali metal hypochlorites, without being these limiting examples.
- a basic compound selected from alkali metal hydroxides, alkaline earth metal hydroxides, ammonium hydroxide or ammonia water, alkali metal hypochlorites, without being these limiting examples.
- other elements such as an alkali metal or alkaline earth metal, can also be incorporated after the calcination step by impregnation or precipitation.
- the resulting solid will be subjected to a second calcination stage.
- the catalyst described according to this embodiment can be used for the inventive process as it is obtained once calcined.
- the catalyst described above in this invention can be supported and / or diluted on a solid such as: silica, alumina, titanium oxide or mixtures thereof, as well as silicon carbide.
- a solid such as: silica, alumina, titanium oxide or mixtures thereof, as well as silicon carbide.
- the fixing of the different catalyst elements on the support can be carried out by conventional impregnation methods, such as pore volume, excess solution, or simply by precipitation on the support of a solution containing the active elements.
- the catalyst metal A may be selected from the group of alkali and alkaline earth metals, preferably Li, Na, K, Cs, Be, Mg, Ca, Sr, Ba, and combinations thereof and more preferably Na, K, Cs, Mg, Ca and combinations thereof.
- element B may be selected from the group of transition metals, preferably Ti, V, Cr, Mn, Fe, Co, Ni, Cu, Zn, Zr, Mo, Ta, TI, Re and combinations of the themselves; rare earths, preferably La, Ce and combinations thereof; and elements of group III, IV and V, preferably B, Al, Ga, Si, Sn, and Sb.
- transition metals preferably Ti, V, Cr, Mn, Fe, Co, Ni, Cu, Zn, Zr, Mo, Ta, TI, Re and combinations of the themselves
- rare earths preferably La, Ce and combinations thereof
- elements of group III, IV and V preferably B, Al, Ga, Si, Sn, and Sb.
- element B is selected from Ti, V, Mn, Cu, Zn, Zr, La, Ce, Al, Si and combinations thereof.
- the product obtained can be selected from linear, branched, cyclic aliphatic hydrocarbons of between 5 and 16 C atoms, and may also contain between 0 and 4 O atoms, and more preferably between 0 and 2 atoms from O.
- the product obtained may be selected from among aromatic compounds of between 5 and 16 C atoms, and may also contain between 0 and 4 O atoms.
- the aqueous mixture derived from the biomass that is introduced in the first step may contain oxygenated compounds having between 1 and 12 carbon atoms, preferably between 1 and 9 carbon atoms, and in addition, they can have between 1 and 9 oxygen atoms, preferably between 1 and 6 oxygen atoms.
- the total concentration of the oxygenated compounds present in the aqueous mixture derived from the biomass are preferably in a range of between 0.5 and 99.5% by weight, and more preferably between 1.0 and 70.0% by weight.
- the contact between the aqueous mixture and the catalyst is carried out in a reactor preferably selected from a discontinuous reactor, a continuous stirred tank reactor, a continuous fixed bed reactor and a continuous reactor of fluidized bed
- the reactor is a discontinuous reactor and the reaction is carried out in a liquid phase at a pressure preferably selected from 1 to 120 bars, and more preferably at a pressure between 1 and 80 bars.
- the reaction can be carried out at a temperature between 50 ° C and 350 ° C, preferably between 120 ° C and 280 ° C.
- the contact time between the aqueous mixture containing the oxygenated compounds derived from the biomass and the catalyst may range from 2 minutes to 200 hours, preferably from 1 hour to 100 hours.
- the weight ratio between the aqueous mixture containing the oxygenated compounds derived from the biomass and the catalyst can be preferably between 1 and 200, and more preferably between 2.5 and 100.
- the reactor that is used in the process of the present invention can be a fixed bed reactor or a fluidized bed reactor.
- the reaction temperature is preferably in a range of between 50 ° C and 450 ° C and more preferably between 150 ° C and 350 ° C;
- the contact time (W / F) is between 0.001 and 200 s; and the working pressure of between 1 and 100 bars and more preferably between 1 and 60 bars.
- the contact between the aqueous fraction containing the oxygenated compounds and the catalyst can be carried out under nitrogen, argon, hydrogen, air atmosphere, nitrogen enriched air, argon enriched air, or combinations thereof.
- the process is preferably carried out in a nitrogen atmosphere.
- the process is preferably carried out in an atmosphere of air or air enriched with nitrogen.
- the present invention describes the use of the catalyst obtained as described above to obtain mixtures of hydrocarbons and aromatic compounds, preferably between 5 and 16 C (C5-C16) atoms useful in liquid fuels, a from the catalytic transformation of oxygenated compounds present in aqueous fractions derived from biomass.
- the aqueous fractions derived from the biomass containing different oxygenated compounds to be treated by the process of the present invention may be selected from among the aqueous fractions obtained by liquid-liquid separation of the bio-liquids produced by thermal and / or catalytic pyrolysis of biomass, aqueous fractions obtained by chemical and / or enzymatic biomass hydrolysis, aqueous fractions obtained by liquefaction under sub- or super-critical biomass conditions, and aqueous fractions obtained from biomass fermentation for the selective production of ethanol, butanol, succinic acid, and lactic acid, without this being limiting examples.
- the aqueous fractions derived from the biomass to be treated by the process of the present invention may contain different oxygenated compounds possessing between 1 and 12 Carbon atoms, preferably between 1 and 9 Carbon atoms.
- the aqueous fractions derived from the biomass to be treated by the The process of the present invention may contain different oxygenated compounds possessing between 1 and 9 Oxygen atoms, preferably between 1 and 6 O atoms.
- the aqueous fractions derived from the biomass to be treated by the process of the present invention may contain different oxygenated compounds in concentrations in a range of between 0.5 and 99.5% by weight with respect to the amount of water, preferably between 1.0 and 70.0% by weight with respect to the amount of water.
- the aqueous fractions derived from the biomass to be treated by the process of the present invention may contain different oxygenated compounds, including alcohols, aldehydes, ketones, acids and carboxylic di-acids, esters, ethers, diols, triols. and polyalcohols in general, sugars, furanic derivatives, and phenolic derivatives, without being these limiting examples.
- the aqueous fractions derived from the biomass to be treated by the process of the present invention may contain different oxygenated compounds of the alcohol type, including methanol, ethanol, 1-propanol, 2- propanol, 1-butanol, 2 -butanol, 1-pentanol, 2-pentanol, iso-pentanol, 1-hexanol, 2- hexanol, 3-hexanol, and furfuryl alcohol, without being these limiting examples.
- the aqueous fractions derived from the biomass to be treated by the process of the present invention may contain different oxygenated compounds of the aldehyde type, including formaldehyde, acetaldehyde, propanal, butanal, 2-butenal, pentanal, 2-pentenal , 3-pentenal, hexanal, 2-hexenal, 3- hexenal, 2-methyl-2-pentenal, 2-methyl-3-pentenal, 3-methyl-2-pentenal, furfural, and 5-hydroxymethyl-furfural, Without being these limiting examples.
- different oxygenated compounds of the aldehyde type including formaldehyde, acetaldehyde, propanal, butanal, 2-butenal, pentanal, 2-pentenal , 3-pentenal, hexanal, 2-hexenal, 3- hexenal, 2-methyl-2-pentenal, 2-methyl-3-pentenal, 3-methyl-2-pentenal, furfural, and 5-hydroxymethyl-
- the aqueous fractions derived from the biomass to be treated by the process of the present invention may contain different oxygenated compounds of the ketone type, including acetone, 2-butanone, 2- pentanone, penten-2-one, 3-pentanone, penten-3-one, 2-hexanone, hexen-2-one, 3- hexanone, hexen-3-one, iso-forone, vanillin, aceto-vanillin, syringone, and aceto-syringone, without being these limiting examples.
- the aqueous fractions derived from the biomass to be treated by the process of the present invention may contain different oxygenated compounds of the acid and di-acid type, including acetic acid, propionic acid, butyric acid, pentanoic acid, acid hexanoic, lactic acid, pyruvic acid, levulinic acid, tartronic acid, tartaric acid, glycolic acid, succinic acid, gluconic acid, and glucaric acid, without being these limiting examples.
- the aqueous fractions derived from the biomass to be treated by the process of the present invention may contain different oxygenated compounds of the ester type, including methyl acetate, ethyl acetate, propyl acetate, butyl acetate, propionate of methyl, ethyl propionate, propyl propionate, butyl propionate, methyl butyrate, ethyl butyrate, propyl butyrate, and butyl butyrate, but these are not limiting examples.
- the aqueous fractions derived from the biomass to be treated by the process of the present invention may contain different oxygenated compounds of the ether type, including di-methyl ether, di-ethyl ether, di-propyl ether, di- iso-propyl ether, di-butyl ether, di-sec-butyl ether, methyl-ethyl ether, methyl-propyl ether, methyl-iso-propyl ether, methyl-butyl ether, methyl-sec-butyl ether, ethyl-propyl ether , ethyl-iso-propyl ether, ethyl-butyl ether, ethyl-sec-butyl ether, propyl-butyl ether, and propyl-sec-butyl ether, without being these limiting examples.
- the aqueous fractions derived from the biomass to be treated by the process of the present invention may contain different oxygenated compounds of the diols type, including ethylene glycol, 1,2-propanediol, 1, 3- propanediol, 1, 2 -butanediol, 1,3-butanediol, 1,4-butanediol, 2,3-butanediol, 1, 2- pentanediol, 1,3-pentanediol, 1,4-pentanediol, 1,5-pentanediol, 2,3-pentanediol , 2,4-pentanediol, 1,2-hexanediol, 1,3-hexanediol, 1,4-hexanediol, 1,6-hexanediol, 2,3- hexane-diol, 2,4-hexanediol;
- the aqueous fractions derived from the biomass to be treated by the process of the present invention may contain different oxygenated compounds of the Furan derivatives type, including furan, 2-methyl-furan, 5-methyl-furan, 2, 5-dimethyl-furan, 2-ethyl-furan, 5-ethyl-furan, 2,5-diethyl-furan, benzofuran, methyl benzofuran, ethyl benzofuran, without being these limiting examples.
- Furan derivatives type including furan, 2-methyl-furan, 5-methyl-furan, 2, 5-dimethyl-furan, 2-ethyl-furan, 5-ethyl-furan, 2,5-diethyl-furan, benzofuran, methyl benzofuran, ethyl benzofuran, without being these limiting examples.
- the aqueous fractions derived from biomass to be treated by the process of the present invention may contain different oxygenated compounds of the phenolic derivatives type, including phenol, benzyl alcohol, acetol, o-cresol, m-cresol, p-cresol, guaiacol, vanillin alcohol, siringol, and aceto-siringol, without being these limiting examples.
- the mixtures of organic compounds of between 5 and 16 C atoms (C5-C16) obtained as a result of the transformation of the oxygenated compounds present in aqueous fractions derived from biomass may contain linear, branched, cyclic linear aliphatic hydrocarbon compounds of 5 and 16 C atoms, which may also contain between 0 and 4 O atoms, preferably between 0 and 2 O atoms.
- Mixtures of organic compounds of 5 and 16 C atoms (C5-C16) obtained as product of the transformation of the oxygenated compounds present in aqueous fractions derived from biomass they may contain aromatic compounds of between 5 and 16 C atoms, and may also contain between 0 and 4 O atoms, preferably between 0 and 2 atoms of O.
- aromatic compounds may have one, two, or more substituents in the ring, these substituents may be of the linear, branched and / or cyclic alkyl type, li alkoxide neal, branched and / or cyclic, acetyl, uranic, furonic, and aromatic tetrahydrof, without being these limiting examples.
- Fig. 1 Shows an x-ray diffractogram of the tungsten oxide based catalyst [W-0 hydrot.] Described in example 1.
- Fig. 2. Shows an x-ray diffractogram of the tungsten oxide based catalyst [W- 0 hydrot.] Described in example 2.
- Fig. 3 Shows an X-ray diffractogram of the catalyst based on tungsten and niobium oxides [W-Nb-0 (1, 8)] described in example 3.
- Fig. 4. Shows an x-ray diffractogram of the catalyst based on tungsten and niobium oxides [W-Nb-0 (1, 8)] described in example 4.
- Fig. 5 It shows an X-ray diffractogram of the catalyst based on tungsten and niobium oxides [W-Nb-0 (1.0)] described in example 5.
- Fig. 6 Shows an x-ray diffractogram of the catalyst based on oxides of tungsten and niobium [W-Nb-0 (0.7)] described in example 6.
- Fig. 7 Shows an X-ray diffractogram of the catalyst based on tungsten and niobium oxides [W-Nb-0 (0.3)] described in example 7.
- Fig. 8 Shows an x-ray diffractogram of the catalyst based on tungsten and niobium oxides [W-Nb-0 (1.0)] described in example 8.
- Fig. 9. Shows an x-ray diffractogram of the catalyst based on tungsten and niobium oxides [W-Nb-0 (1.0)] described in example 9.
- Fig. 10 Shows an x-ray diffractogram of the niobium oxide-based catalyst [Nb-0 hydrot.] Described in example 10.
- Fig. 11 Shows an x-ray diffractogram of the niobium oxide-based catalyst [Nb-0 hydrot.] Described in example 11.
- Fig. 12 Shows the X-ray diffractogram obtained for the catalyst based on cerium and zirconium oxides [Ce-Zr-O] described in example 12.
- Fig. 13 Shows the X-ray diffractogram obtained for the catalyst based on tungsten and niobium oxides [impregnated W-Nb-0] described in example 13.
- Fig. 14 Shows the X-ray diffractogram obtained for the catalyst based on tungsten and niobium oxides [W-Nb-0 co-precip.] Described in example 14.
- Fig. 15 Shows an x-ray diffractogram of the catalyst based on tungsten, niobium and potassium oxides [W-Nb-K-O] described in example 15.
- Fig. 18 Shows an X-ray diffractogram of the catalyst based on tungsten, niobium and cerium oxides [W-Nb-Ce-O] described in example 18.
- Fig. 19 Shows an X-ray diffractogram of the catalyst based on tungsten and zirconium oxides [W-Zr-O] described in example 19.
- Fig. 20 Shows a comparison of the stability and maintenance of the catalytic activity with the re-uses of the Ce-Zr-0 (Ex. 12) and W-Nb-0 (0.7) (Ex. 6) catalysts.
- Example 1 Preparation of a catalyst by hydrothermal method, based on tungsten oxide [W-O] and treated with nitrogen
- Example 10 Preparation of a catalyst by hydrothermal method, based on niobium oxide [Nb-0 hydrot.] And treated with nitrogen
- Example 11 Preparation of a catalyst similar to that of Example 10, but thermally activated in air
- the catalyst was prepared by the synthesis method by co-precipitation of the mixed oxide Ce-Zr adapting the procedure published by Serrano-Ruiz et al. [J. Catal., 241 (2006) 45-55].
- Ce 0.5 Zr 0, 5O 2 an aqueous solution of salts of both metals in equimolar ratio is prepared.
- Ce (N0 3 ) 3-6H 2 0 and ZrO (N0 3 ) 2 H 2 0 are used as precursors of both metals.
- 1,176 g of Ce (N0 3 ) 3 -6H 2 0 and 6.70 g of ZrO (N0 3 ) 2 H 2 0 are weighed and dissolved in 120 ml of distilled water. Then, a solution of 28% NH 4 OH is added dropwise until a pH of 10 is reached.
- the solution is transferred to a closed 250 ml balloon and under stirring, where the mixture is allowed to age at room temperature. for 65 hours
- the catalyst is washed with distilled water by vacuum filtration until it reaches a pH of 7.
- the catalyst is allowed to dry overnight at 100 ° C and finally, it is subjected to an activation process by calcination in air at 450 ° C, for 4.5 h.
- the amounts of Ce and Zr measured by ICP coincide with the formula Ce 0.5 Zr 0, 5O 2 and the X - ray diffractogram obtained for this sample indicates the presence of mixed oxides of Ce and Zr (Fig. 12)
- Example 13 Preparation of a catalyst based on mixed oxides of W and Nb [impregnated W-Nb-0] using a wet impregnation method
- This catalyst was synthesized to illustrate catalysts of the type W-Nb mixed oxides commonly used in literature [C. Yue et al., Appl. Catal. B: Environ., 163 (2015) 370-381].
- a mixed oxide catalyst was synthesized with a W-Nb ratio similar to that used for the catalyst of Example 6, so that it can be compared as to the catalytic activity with the catalysts of the present invention.
- the catalyst was prepared by the wet impregnation synthesis method of the mixed W-Nb oxide adapting the procedure published by C. Yue et al. [Appl. Catal. B. Environ., 763 (2015) 370-381].
- an aqueous solution of the salts of the two metals is prepared in the desired proportion.
- (NH 4 ) 6 H 2 W 12 0 4 oH 2 0 and C 4 H 4 NNb0 9 .H 2 0 are used as precursors of both metals.
- 3.84 g of (NH 4 ) 6 H 2 W 12 0 4 oH 2 0 and 2.36 g of C 4 H 4 NNb0 9 .H 2 0 are weighed and dissolved in 15 ml of distilled water. The mixture is placed under stirring at a temperature of 70 ° C and the solvent is allowed to evaporate slowly.
- the catalyst After 10 hours of drying at a temperature of 100 ° C, the catalyst is subjected to an activation process by calcination in air at 450 ° C for 3.5 h.
- the X-ray diffractogram obtained for this sample indicates the presence of mixed oxides of W and Nb (Fig. 13)
- Example 14 Preparation of a catalyst based on mixed oxides of W and Nb [W-Nb-0 co-precip.] By the co-precipitation method This catalyst was synthesized to illustrate catalysts of the type W-Nb mixed oxides commonly used in literature [D. Stosic et al., Catal. Today, 192 (2012) 160-168]. A mixed oxide type catalyst with a W-Nb ratio similar to that used for the catalyst of Example 6 was synthesized, in order to be compared in terms of catalytic activity with the catalysts of the present invention.
- an aqueous solution of the salts of the two metals is prepared in the desired proportion. It is used (NH 4 ) 6 H 2 W 12 0 4 or H 2 0 and 0 4 ⁇ 4 ⁇ as precursors of both metals.
- 2.96 g of (NH 4 ) 6 H2W 12 0 4 or H20 and 5.4536 g of 0 4 ⁇ 4 ⁇ ⁇ 0 9 ⁇ 2 0 are weighed and dissolved in 50 ml of distilled water .
- a solution of 28% NH 4 OH is added dropwise under stirring until a pH of 9 is reached.
- the solution is allowed to age at room temperature for 24 hours.
- the catalyst is washed with distilled water by vacuum filtration until a pH of 7 is reached.
- the catalyst is allowed to dry overnight at 100 ° C, and finally undergoes an activation process by calcination in nitrogen at 550 ° C, for 5h.
- the X-ray diffractogram obtained for this sample indicates the presence of mixed oxides of W and Nb (Fig. 14)
- Example 15 Modification of the catalyst of Example 6 by treatment with potassium salt
- a solution of 0.13 g of potassium bicarbonate in 100 g of water is prepared to which 8.0 g of the catalyst obtained in Example 6 is added.
- the mixture is kept under stirring at room temperature for 4 h.
- the solid is then separated from the solution and treated at 280 ° C for 2h in a stream of air.
- This catalyst is characterized by presenting an X-ray diffraction diagram as shown in Figure 15.
- the autoclave is kept at 175 ° C, in static for 2 days and the solid obtained is treated at 100 ° C for 16 h. Finally the material is heated at 550 ° C for 2 h under a stream of nitrogen.
- This catalyst is characterized by presenting an X-ray diffraction diagram as shown in Figure 16.
- a solution of 6.7 g of vanadyl sulfate in 30.1 g of water is prepared, which is added to the former.
- a solution of 37.5 g of niobium oxalate in 90.4 g of water at 80 ° C is then prepared, which is slowly added to the previous mixture.
- Example 18 Preparation of a catalyst based on W-Ce-Nb-0 mixed oxide by hydrothermal method and heat treated in nitrogen
- Example 19 Preparation of a catalyst based on tungsten and zirconium oxides [W-Zr-O] by hydrothermal method and heat treated in nitrogen
- Example 20 Comparative catalytic activity of the W-Nb series catalysts of Examples 1, 3, 6, 7 and 10
- the catalytic activity experiments were carried out in the liquid phase using 12 ml stainless steel autoclave type reactors with a reinforced PEEK (polyether-ethyl ketone) reinforced interior and equipped with magnetic stirrer, pressure gauge and inlet valve / output of gases and liquid samples.
- the reactors are located on an individual steel jacket support with closed loop temperature control.
- the initial feed consists of a model aqueous mixture containing oxygenated compounds simulating the residual aqueous currents that are obtained after a phase separation process, after the biomass pyrolysis.
- the composition of the model aqueous mixture is detailed below (Table 1): Content Component (wt%)
- the quantification of the products is carried out from the response factors calculated by internal standard (2% by weight solution of chlorobenzene in methanol) and species with more than 5 carbon atoms are classified and quantified in intervals, whose Response factors have been calculated from representative molecules thereof.
- internal standard 2% by weight solution of chlorobenzene in methanol
- species with more than 5 carbon atoms are classified and quantified in intervals, whose Response factors have been calculated from representative molecules thereof.
- main primary condensation reaction products such as acetone, ethyl acetate, 3-pentanone and 2-methyl-2-pentenal
- groups of molecules with 5, 6, 7, 8, 9, 10 or more are distinguished of 10 carbon atoms.
- these molecules are grouped into two large groups of compounds, namely: Products C5- C8 and Products C9-C10 +.
- the Total Organic Yield (in percentage by weight), was calculated from the following formula:
- Acetone acetic acid condensation product
- the intermediate condensation products C5-C8
- the increase in the conversion of propionaldehyde causes the amount of 2-methyl-2-pentenal (product of the first self-condensation of propionaldehyde) to grow.
- Condensation products in the range of C9-C10 + and Total Organic Yield have the same behavior.
- Example 21 Comparative catalytic activity of the W-Nb series catalysts (Examples 3, 6 and 10) against conventional W-Nb oxides (Examples 13 and 14) and commercial Nb 2 0 5 (Sigma-Aldrich, CAS 1313-96-8)
- Example 22 Comparative catalytic activity of the W-Nb-O series catalysts, prepared by hydrothermal method and treated in nitrogen at different temperatures (Examples 5, 8 and 9)
- Example 23 Comparative catalytic activity of the W-Nb-0 and Nb-O series catalysts, prepared by hydrothermal method (Examples 6 and 10) against a conventional Ce-Zr catalyst (Example 12)
- catalysts based structures that combine W and Nb exhibit similar to those exhibited by a catalyst such as Ce 0.5 Zr 0, 5O 2 traditionally used in the literature for reactions of this type results.
- the catalysts of Examples 6 and 12 once used are recovered after the reaction, subjected to a methanol wash and dried at 100 ° C overnight. Subsequently, they are characterized by Elemental Analysis (AE) and Thermogravimetry (TG).
- AE Elemental Analysis
- TG Thermogravimetry
- the AE study shows that the Ce-Zr type catalyst of Example 12 has 3.46% by weight of carbon (organic products deposited in the catalyst) after washing.
- the W-Nb-based catalyst of Example 6 only has 1.42% by weight of carbon, demonstrating that a lower deposition of carbonaceous substances occurs during the reactive process, and therefore is less sensitive to deactivation caused by the coke deposition
- the Ce-Zr catalyst of Example 12 has a mass loss of 11.5% at a temperature close to 300 ° C corresponding to the desorption of the absorbed organic products.
- the catalyst of Example 6 only shows a mass loss of 3.5% at said temperature.
- This catalyst also has a mass loss of 3.4% at a temperature close to 100 ° C corresponding to the water absorbed in the channels of the crystalline structure. This amount of absorbed water is also observed in the TG analysis of the catalyst before being used, so the presence of water in the reaction medium does not cause damage to the activity of the catalyst or its stability.
- Example 24 Comparative catalytic activity during reuse of catalysts W-Nb-0 (0.7) (Example 6) and Ce-Zr-0 (Example 12)
- the analyzes performed by AE and TG confirm the greater stability of the W-Nb-based catalyst of Example 6 compared to the mixed Ce-Zr oxide prepared in Example 12.
- the W-Nb material (Ex. 6) only 1.5% by weight of coal is determined by EA after the third reuse (R3); while the amount of carbon detected in the Ce-Zr catalyst (Ex. 12) after the same number of re-uses reached 4.8% by weight.
- Example 12 Comparative catalytic activity of catalysts based on W-Nb-O (Examples 3 and 6) and W-Nb-0 with the addition of an alkali metal, W-Nb-K-0 (Example 15)
- Example 26 Comparative catalytic activity of catalysts based on W-Nb-O (Examples 3 and 6) and W-Nb-VO, with the addition of V as the third metallic element (Examples 16 and 17) 3000 mg of the aqueous mixture model and 150 mg of one of the catalytic materials of Examples 3, 6, 16 and 17 in the autoclave reactor described above.
- the reactor was sealed tightly, initially pressurized with 13 bars of N 2 , and heated to 220 ° C under continuous stirring. Liquid samples ( ⁇ 50-100 ⁇ ) were taken at different time intervals up to 7 hours of reaction.
- the samples were filtered and diluted in a standard solution of 2% by weight of chlorobenzene in methanol, and analyzed by gas chromatography on a GC-Bruker 430 equipped with an FID detector and a TRB-624 capillary column.
- 60 m Products are identified by an Agilent 6890 N gas chromatograph coupled with an Agilent 5973 N mass detector (GC-MS) and equipped with an HP-5 MS capillary column 30 m long.
- Example 27 Comparative catalytic activity of catalysts based on W-Nb (Examples 3 and 6) and W-Nb-Ce-0 with the addition of Ce as the third metallic element (Example 18)
- Example 28 Comparative catalytic activity of catalysts based on W-Nb (Examples 3 and 6) and W-Zr-0 (Example 19) 3000 mg of the model aqueous mixture and 150 mg of one of the catalytic materials of the Examples 3, 6 and 19 in the autoclave reactor described above.
- the reactor was sealed tightly, initially pressurized with 13 bars of N 2 , and heated to 220 ° C under continuous stirring. Liquid samples ( ⁇ 50-100 ⁇ ) were taken at different time intervals up to 7 hours of reaction.
- the samples were filtered and diluted in a standard solution of 2% by weight of chlorobenzene in methanol, and analyzed by gas chromatography on a GC-Bruker 430 equipped with an FID detector and a TRB-624 capillary column.
- 60 m Products are identified by an Agilent 6890 N gas chromatograph coupled with an Agilent 5973 N mass detector (GC-MS) and equipped with an HP-5 MS capillary column 30 m long.
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Processing Of Solid Wastes (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Abstract
Description
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US16/087,803 US10876049B2 (en) | 2016-03-22 | 2017-03-22 | Method for recovering the oxygenated compounds contained in aqueous fractions derived from biomass |
BR112018069301-4A BR112018069301B1 (pt) | 2016-03-22 | 2017-03-22 | Procedimento para a valorização de compostos orgânicos oxigenados presentes em frações aquosas derivadas de biomassa |
JP2018550388A JP6944947B2 (ja) | 2016-03-22 | 2017-03-22 | バイオマス由来の水溶性分画に含まれる含酸素化合物を回収する方法 |
EP17769506.1A EP3434364A4 (en) | 2016-03-22 | 2017-03-22 | METHOD FOR RECOVERY OF OXYGEN COMPOUNDS FROM AQUEOUS FRACTIONS FROM BIOMASS |
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ESP201630339 | 2016-03-22 | ||
ES201630339A ES2638719B1 (es) | 2016-03-22 | 2016-03-22 | Procedimiento para la valorización de compuestos oxigenados presentes en fracciones acuosas derivadas de biomasa |
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US (1) | US10876049B2 (es) |
EP (1) | EP3434364A4 (es) |
JP (1) | JP6944947B2 (es) |
BR (1) | BR112018069301B1 (es) |
ES (1) | ES2638719B1 (es) |
WO (1) | WO2017162900A1 (es) |
Cited By (1)
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WO2019224412A1 (es) | 2018-05-25 | 2019-11-28 | Consejo Superior De Investigaciones Científicas (Csic) | Proceso catalítico para la producción de hidrocarburos y compuestos aromáticos a partir de compuestos oxigenados presentes en mezclas acuosas |
Citations (4)
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CN101870881A (zh) * | 2010-06-21 | 2010-10-27 | 中国科学院广州能源研究所 | 一种生物油水相催化提质制取液体烷烃燃料方法 |
US20120222349A1 (en) * | 2011-03-03 | 2012-09-06 | Conocophillips Company | One-step hydrodeoxygenation and reformation of alditols |
EP2631224A2 (en) * | 2010-10-21 | 2013-08-28 | SK Innovation Co., Ltd. | Method for producing hydrocarbons from biomass or organic waste |
US20140273118A1 (en) * | 2013-03-15 | 2014-09-18 | Virent, Inc. | Processes for Converting Biomass-Derived Feedstocks to Chemicals and Liquid Fuels |
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JP2012501338A (ja) * | 2008-08-27 | 2012-01-19 | ヴァイレント エナジー システムズ インク. | バイオマスからの液体燃料の合成 |
BR112013005821A2 (pt) | 2010-09-14 | 2019-09-24 | Radlein Desmond | métodos de transformação de bio-óleo em combustíveis de hidrocarboneto do tipo de transporte |
US20130079566A1 (en) | 2011-09-27 | 2013-03-28 | Nevada, | Catalytic process for conversion of biomass into hydrocarbon fuels |
KR102063945B1 (ko) * | 2013-06-05 | 2020-01-09 | 에스케이이노베이션 주식회사 | 바이오매스 유래 아세트산으로부터 방향족 화합물을 제조하는 방법 |
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2016
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2017
- 2017-03-22 BR BR112018069301-4A patent/BR112018069301B1/pt active IP Right Grant
- 2017-03-22 US US16/087,803 patent/US10876049B2/en active Active
- 2017-03-22 EP EP17769506.1A patent/EP3434364A4/en active Pending
- 2017-03-22 WO PCT/ES2017/070167 patent/WO2017162900A1/es active Application Filing
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CN101870881A (zh) * | 2010-06-21 | 2010-10-27 | 中国科学院广州能源研究所 | 一种生物油水相催化提质制取液体烷烃燃料方法 |
EP2631224A2 (en) * | 2010-10-21 | 2013-08-28 | SK Innovation Co., Ltd. | Method for producing hydrocarbons from biomass or organic waste |
US20120222349A1 (en) * | 2011-03-03 | 2012-09-06 | Conocophillips Company | One-step hydrodeoxygenation and reformation of alditols |
US20140273118A1 (en) * | 2013-03-15 | 2014-09-18 | Virent, Inc. | Processes for Converting Biomass-Derived Feedstocks to Chemicals and Liquid Fuels |
Non-Patent Citations (2)
Title |
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THIBODEAU T J ET AL.: "Composition of tungsten oxide bronzes active for hydrodeoxygenation", APPLIED CATALYSIS A: GENERAL 20101120, vol. 388, no. 1-2, 20 November 2010 (2010-11-20), pages 86 - 95, XP055424691, ISSN: 0926-860X * |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2019224412A1 (es) | 2018-05-25 | 2019-11-28 | Consejo Superior De Investigaciones Científicas (Csic) | Proceso catalítico para la producción de hidrocarburos y compuestos aromáticos a partir de compuestos oxigenados presentes en mezclas acuosas |
JP2021525303A (ja) * | 2018-05-25 | 2021-09-24 | コンセホ・スペリオル・デ・インベスティガシオネス・シエンティフィカス(セエセイセ)Consejo Superior De Investigaciones Cientificas(Csic) | 水性混合物に含まれる含酸素化合物を原料とした、炭化水素および芳香族化合物を製造するための触媒的方法 |
JP7389056B2 (ja) | 2018-05-25 | 2023-11-29 | コンセホ・スペリオル・デ・インベスティガシオネス・シエンティフィカス(セエセイセ) | 水性混合物に含まれる含酸素化合物を原料とした、炭化水素および芳香族化合物を製造するための触媒的方法 |
US11839867B2 (en) | 2018-05-25 | 2023-12-12 | Consejo Superior De Investigaciones Cientificas | Catalytic method for the production of hydrocarbons and aromatic compounds from oxygenated compounds contained in aqueous mixtures |
Also Published As
Publication number | Publication date |
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US10876049B2 (en) | 2020-12-29 |
ES2638719B1 (es) | 2018-08-01 |
EP3434364A4 (en) | 2020-05-27 |
EP3434364A1 (en) | 2019-01-30 |
BR112018069301B1 (pt) | 2022-03-29 |
US20190367816A1 (en) | 2019-12-05 |
ES2638719A1 (es) | 2017-10-23 |
JP6944947B2 (ja) | 2021-10-06 |
BR112018069301A2 (pt) | 2019-01-22 |
JP2019512530A (ja) | 2019-05-16 |
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