CN106367095A - Biomass co-processing product processing method - Google Patents
Biomass co-processing product processing method Download PDFInfo
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Abstract
The invention relates to a biomass co-processing product processing method, which comprises: I) adding a solid biomass, an monohydric alcohol and a fatty compound into a high-pressure container, co-processing at a temperature of 200-450 DEG C, carrying out solid-liquid separation on the products after completing the reaction, and collecting the liquid product; II) distilling the liquid product and collecting the distilling residue to obtain a biomass co-processing product; and III) contacting the biomass co-processing product with a hydrogenation catalyst to make the product be subjected to hydrogenation and deoxygenation. With the processing process of the present invention, the oil alcoholysis product is subjected to hydrogenation into the large molecule hydrocarbon while the biomass liquefaction product is subjected to hydrogenation into the small molecule hydrogenation so as to prepare the fuel or purify into the chemical industry product.
Description
Technical field
The invention belongs to the regeneration field of biomass material, relate to one living beings are refined altogetherThe processing method of product.
Background technology
Living beings are unique alternative conventional petroleum liquid fuel and other chemicals of changing intoRenewable carbon resource, and heat chemistry Efficient Conversion to utilize technology be biomass energy exploitation profitWith main approach, therefore Technology on High-pressure Liquefaction of Biomass receives many researchers' concern.High-pressure liquefaction refers in solvent medium, reaction temperature be 200 ?400 DEG C, reaction pressure be5 ?under the condition of 25MPa, biomass liquefying is produced to the technique of product liquid. High-pressure liquefaction mistakeIn journey, conventionally add the reducibility gas such as catalyst and H2, CO to improve liquefied fraction, improve liquidBody product characteristics.
At present the most frequently used high-pressure liquefaction solvent is water, other also comprise low-carbon alcohols, low-carbon ester,Acetone, naphthane, phenol or their mixture etc. The feature of these solvents be molecular weightLittle, poor to the high-temperature digestion of the large molecular product of biomass liquefying, solid residue is many, biologyMatter liquefaction yield is on the low side, generally all needs to add catalyst to improve biomass liquefying rate. Such asPublication number is that the patent application of CN1952043A has proposed the method that living beings liquefy in water,The method need to be used K2CO3Be the liquefaction that catalyst improves living beings in the alkali such as salt or KOHRate; Publication number is that the patent application of CN101560416A has proposed living beings at supercritical methanolIn liquifying method, the method also needs to use K2CO3Be that catalyst is carried in the alkali such as salt or KOHThe liquefied fraction of high living beings. Although add salt or alkali can improve biomass liquefying as catalystRate, but not only improved production cost, also can produce a large amount of waste pollution environment.
Summary of the invention
Present inventor's discovery, solid biomass and fat compound be refining altogether in monohydric alcohol(refining altogether referred to as living beings), also can improve the liquefied fraction of living beings. But the liquid phase of refining altogetherIn product, both, containing biomass liquefying product, also fatty compounds, was unfavorable for following process.
The present invention relates to a kind of living beings and refine altogether the processing method of product, comprising:
I) solid biomass, monohydric alcohol and fat compound are added in high-pressure bottle200～450 DEG C of refinings altogether, after having reacted, carry out Separation of Solid and Liquid to product, collect product liquid;
II) product liquid is distilled, collect and steam excess, obtain living beings and refine altogether product;
III) living beings are refined to product altogether and contact with hydrogenation catalyst, make product hydrogenation deoxidation.
Through above-mentioned process, grease alcoholysis product hydrogenation becomes more macromolecular hydro carbons, andBiomass liquefying product hydrogenation becomes the hydro carbons that molecule is relatively little, can prepare fuel or purificationFor chemical products.
Step I) in, described solid biomass refers to and utilizes atmosphere, water, soil etc. to pass through lightCooperation is used and the various organisms of generation, and discarded object and the extract of organism generation. InstituteState organism and comprise each Plants, animal and microorganism, for example timber, bamboo, algae etc.;Described discarded object include but not limited to agriculture and forestry organic waste material (such as wood chip, stalk, shell etc.),Human and animal excreta, domestic waste etc.; Described extract includes but not limited to lignin, fibreDimension element, hemicellulose, animal protein etc.
Described fat compound refer to contain at least one C10 ?the organising of the long carbochain of C24Compound, mainly refer to C10 ?C24 aliphatic acid, C10 ?C24 fatty alcohol, C10 ?the fat of C24Fat aldehyde, C10 ?C24 fatty acid amide, C10 ?C24 aliphatic acid C1 ?C18 alcohol ester, C10 ?C24Fatty glyceride and the mixture of above-claimed cpd composition etc., preferably C10 ?C24 fatAcid glyceride, i.e. animal and plant fat, as soybean oil, palm oil, lard, butter etc.
Described fat compound can pass through pre-hydrogenation, makes part contained in aliphatic chain or completePortion's ethylene linkage is saturated, and then participates in liquefaction reaction.
The weight that adds of described fat compound is 0.1～10 of solid biomass weightDoubly, preferably 1～8 times, more preferably 2～6 times.
Solid biomass of the present invention does not comprise the solid matter that is rich in fat compound,Such as animal tallow.
Said monohydric alcohol refer to C1 ?the monohydric alcohol of C10, include but not limited to methyl alcohol, ethanol,Propyl alcohol, isopropyl alcohol etc. or their mixture, particular methanol and ethanol, more preferably methyl alcohol.
The mass ratio of said monohydric alcohol and solid biomass be 1:5 ?20:1, preferably 1:1 ?10:1,More preferably 1.5:1 ?8:1.
Described biological particles size is without restriction, preferably 10～100 orders, more preferably 30～80 orders.
Described high-pressure bottle type is without restriction, can be reactor or tubular reactor. As beReactor, can stir reactant, and mixing speed is not limit; System pressure is used by reactantAmount, reactant solvents and reaction temperature determine, without manual adjustment. As be tubular reactor,Reaction pressure is 3～25MPa, preferably 8～20MPa, more preferably 10～18MPa.
Described reaction temperature is 200～450 DEG C, preferably 280～360 DEG C.
The described reaction time is 3min～6h, preferably 10min～2h.
Step II) in, said distillation refers to that living beings are refined to product liquid altogether distills,Remove light group that monohydric alcohol and boiling point generate lower than the biomass liquefying of 160 DEG C with all or part ofDivide (being A phase).
Said distillation mode comprises air-distillation or decompression distillation, can adopt specifically differenceVapo(u)rizing temperature, or take to distill at same temperature, also can use fractional condensaionMode separates.
Above-mentioned steps III) in said hydrogenation catalyst can be non-precious metal catalyst, also can beNoble metal catalyst, active component can be selected from Pt, Pd, Ru, Co, Mo, Ni, W etc.At least one in oxide or the sulfide of metal, by oxide weight, content is catalysis0.1～50% of agent gross weight, preferably 0.5～40%, more preferably 1～30%. Carrier can selectFrom active carbon, Al2O3、SiO2、TiO2In one or more mixture etc.
Described hydrogenation catalyst can be prepared according to existing method, for example can referenceThe disclosed method preparation of CN1229835A, CN1245204A.
Said hydrogenation deoxidation reaction condition is that reaction temperature is 150～450 DEG C, and Hydrogen Vapor Pressure is0.1～10MPa, reaction is carried out in intermittence or continuous flow reactor. In batch reactor,Catalyst amount is 0.1～10% of weight of oil, and the reaction time is 0.5～15h; In Continuous FlowIn moving reactor, standard state hydrogen to oil volume ratio is 100:1～5000:1, the volume sky of oilSpeed is 0.1～20h‐1。
Said batch reactor preferably, with the reactor of gas flowmeter and counterbalance valve, is used gasFlowmeter body control gas reactor flow velocity, by counterbalance valve control still internal pressure.
Preferably 220～400 DEG C of said reaction temperatures, more preferably 260～380 DEG C.
Preferably 0.5～8MPa of said Hydrogen Vapor Pressure, more preferably 1～5MPa.
Said catalyst weight content is preferably weight of oil 0.5～8%, and more preferably 1～5%.
Preferably 2～10h of said reaction time, more preferably 3～7h.
Preferred 300:1～the 3000:1 of said standard state hydrogen to oil volume ratio, more preferably 400:
1～2000：1。
Preferably 0.3～10h of the volume space velocity of said oil‐1, more preferably 0.5～5h‐1。
Above-mentioned steps III) in, if the active component of used catalyst is Co, Mo, Ni, WOxide, need to use CS2Or H2S carries out presulfurization, makes it be converted into metal sulfide.
Above-mentioned steps III) in, if the catalyst adopting is metal sulfide, can be in advance to biologyMatter is refined altogether in product and is added sulfur-containing compound, such as thiophene, to improve the life-span of catalyst. OneAs require that to add the weight content of sulphur be 0.05～0.7%.
Biomass high-pressure liquefaction products composition is complicated, and molecular weight is larger, and normal temperature is solid-state, straightConnect hydrogenation deoxidation more difficult, on document, more multiplex model compounds are studied, orBiomass high-pressure liquefaction products is dissolved in the organic solvent such as cyclohexane, naphthane, then carries outHydrogenation deoxidation. Method of the present invention is refining altogether in monohydric alcohol solid biomass and grease,When solid biomass liquefaction, grease and monohydric alcohol generation alcoholysis reaction, obtaining normal temperature is liquidThe solid biomass liquefaction products of state and grease alcoholysis product. Biomass liquefying product is dissolved inIn grease alcoholysis product, then hydrogenation deoxidation together, grease alcoholysis product hydrogenation becomesMacromolecular hydro carbons, and biomass liquefying product hydrogenation becomes the hydro carbons that molecule is relatively little, canTo prepare fuel or purification as chemical products. This process does not need additionally to add solvent, just can makeBiomass liquefying product has good dispersiveness, is beneficial to its hydrogenation deoxidation, also can make oil simultaneouslyLipidol hydrolysis products obtains effective hydrogenation.
Detailed description of the invention
Further illustrate the present invention below by embodiment, but the present invention is not limited to this.
Embodiment 1
Dry 20g Poplar Powder (100 order) is joined in 500ml autoclave, and add 80gMethyl alcohol and 80g soybean oil, after sealing, be warmed up under the condition of low whipping speed 600RPM320 DEG C, insulation 1h, stops heating, naturally cools to room temperature. Separating solid residue, liquid phaseWeight is 188.0g. Liquid phase is distilled under 100 DEG C, 5000Pa, obtain living beings and refine altogether liquidProduct 98.2g, its oxygen content of elementary analysis is 13.0%. That produces with Chang Ling catalyst plant adds(active component is NiO content 2.9wt%, WO to hydrogen desulphurization catalyst3Content 28wt%, carriesBody is Al2O3) living beings are refined to product altogether carry out hydrogenation deoxidation. Reaction condition is: catalystLoadings is 10mL, in fixed bed reactors, with containing 5%CS2Cyclohexane 360 DEG C,Under 4MPa, to presulfiding of catalyst 2h, liquid hourly space velocity (LHSV) is 2h‐1, under standard state, hydrogen-oil ratio is400, make metal oxide be converted into metal sulfide by presulfurization; Again same temperature,Under pressure, liquid hourly space velocity (LHSV), hydrogen-oil ratio condition, living beings are refined to product liquid altogether and carry out hydrogenation deoxidation,In product, add in advance 3000ppm thiophenic sulfur. After reaction finishes, elementary analysis shows, producesOxygen content 1.2% in thing has reduced by 90.7% compared with reaction raw materials.
Embodiment 2
Dry 50g Poplar Powder (100 order) is joined in 500ml autoclave, and add 80gMethyl alcohol and 80g soybean oil, after sealing, be warmed up under the condition of low whipping speed 600RPM300 DEG C, insulation 1h, stops heating, naturally cools to room temperature. Separating solid residue, liquid phaseWeight is 188.7g. Liquid phase is distilled under 100 DEG C, 5000Pa, obtain living beings and refine altogether liquidProduct 98.7g, its oxygen content of elementary analysis is 13.2%. Produce with Xi'an Kai Li chemical company5%Pt/Al2O3Catalyst carries out hydrogenation deoxidation to common refining product liquid. Reaction condition is:In fixed bed reactors, 320 DEG C of reaction temperatures, reaction pressure 4MPa, liquid hourly space velocity (LHSV) are 0.2h‐1，Under standard state, hydrogen-oil ratio is 800. After reaction finishes, elementary analysis shows, contains oxygen in productAmount 1.1% has reduced by 91.7% compared with reaction raw materials.
Embodiment 3
Dry 30g willow powder (100 order) is joined in 500ml autoclave, and add 100gMethyl alcohol and 80g palm oil, after sealing, be warmed up under the condition of low whipping speed 800RPM350 DEG C, insulation 1.5h, stops heating, naturally cools to room temperature. Separating solid residue, liquidPhase weight is 196.9g. Liquid phase is distilled under 100 DEG C, 5000Pa, obtain living beings and refine altogether liquidBody product 88.8g, its oxygen content of elementary analysis is 13.0%. Raw with Xi'an Kai Li chemical companyThe 10%Pd/C catalyst producing carries out hydrogenation deoxidation to common refining product liquid. Reaction condition is:In an autoclave with gas flowmeter and counterbalance valve, add product liquid weight 3%Pd/C catalyst, then at H2300 DEG C of flow velocity 100mL/min, pressure 2MPa, temperatureUnder condition, react 5h. After reaction finishes, elementary analysis shows, oxygen content 0.7% in product,Reduced by 94.6% compared with reaction raw materials.
Comparative example 1
Dry 20g Poplar Powder (100 order), 160g methyl alcohol are joined to 500ml reaction under high pressureIn still, after sealing, under the condition of low whipping speed 600RPM, be warmed up to 320 DEG C, insulation 1h,Stop heating, naturally cool to room temperature. Isolate after solid residue, distill out methyl alcohol, obtainPoplar Powder liquefaction products (normal temperature is solid-state), elementary analysis shows, oxygen content 31.2%. WithHydrobon catalyst that Chang Ling catalyst plant is produced (active component be NiO content 2.9wt%,
WO3Content 28wt%, carrier is Al2O3) Poplar Powder liquefaction products is carried out to hydrogenation deoxidation.Reaction condition is: liquefaction products dissolves with cyclohexane, and both ratios are 1:4,20g liquidChange product, 80g cyclohexane is encased in 500mL reactor, then adds catalyst 10g,
CS2Addition be 1.1g, Hydrogen Vapor Pressure is 50bar. After sealed reactor, low whipping speedAt 320 DEG C of 500RPM, temperature, to presulfiding of catalyst 2h, make burning by presulfurizationThing is converted into metal sulfide; Under 360 DEG C of conditions, liquefaction products is carried out to hydrogenation deoxidation again2h. After reaction finishes, chromatograph, contains oxygen 8.0%, compared with reaction raw materials in productReduce by 74.3%.
Comparative example 2
Dry 30g willow powder (100 order), 180g methyl alcohol are joined in 500ml autoclave,After sealing, be warmed up to 350 DEG C under the condition of low whipping speed 800RPM, insulation 1.5h, stopsOnly heating, cools to room temperature naturally. Isolate after solid residue, distill out methyl alcohol, obtain willowWood powder liquefaction products (normal temperature is solid-state), elementary analysis shows, oxygen content 30.8%. With westThe 10%Pd/C catalyst that An Kaili chemical company produces is to carrying out hydrogenation deoxidation. Reaction conditionFor: with 80g naphthane dissolving 20g liquefaction products, then join one with gas flowIn meter and the autoclave of counterbalance valve, then add the Pd/C catalyst of raw material weight 3%, then exist
H2Under flow velocity 100mL/min, pressure 2MPa, 300 DEG C of conditions of temperature, react reactionTime is 6h. After reaction finishes, chromatograph, containing oxygen 9.2%, and reacts former in productMaterial is compared and has been reduced by 70.1%.
Claims (12)
1. living beings are refined a processing method for product altogether, comprising:
I) solid biomass, monohydric alcohol and fat compound are added in high-pressure bottle 200～450 DEG C of refinings altogether, after having reacted, carry out Separation of Solid and Liquid to product, collect product liquid;
II) product liquid is distilled, collect and steam excess, obtain living beings and refine altogether product;
III) living beings are refined to product altogether and contact with hydrogenation catalyst, make product hydrogenation deoxidation.
2. in accordance with the method for claim 1, wherein, described solid biomass comprises variously havingDiscarded object and extract that body and organism produce.
3. in accordance with the method for claim 1, wherein, described fat compound refers to and containsHave at least one C10 ?the organic compound of the long carbochain of C24.
4. in accordance with the method for claim 1, wherein, described fat compound is selected fromC10 ?C24 aliphatic acid, C10 ?C24 fatty alcohol, C10 ?C24 fatty aldehyde, C10 ?C24Fatty acid amide, C10 ?C24 aliphatic acid C1 ?C18 alcohol ester, C10 ?the fat of C24The mixture of acid glyceride and above-claimed cpd composition.
5. in accordance with the method for claim 1, wherein, the adding of described fat compoundWeight is 0.1～10 times of solid biomass weight.
6. in accordance with the method for claim 1, wherein, said monohydric alcohol be selected from C1 ?C10Monohydric alcohol.
7. in accordance with the method for claim 1, wherein, said monohydric alcohol be selected from methyl alcohol and/Or ethanol.
8. in accordance with the method for claim 1, wherein, said monohydric alcohol and solid biomassMass ratio be 1:5 ?20:1.
9. in accordance with the method for claim 1, wherein, described high-pressure bottle be reactor orTubular reactor, reaction pressure is 3～25MPa.
10. in accordance with the method for claim 1, wherein, described reaction temperature is 200～
450℃。
11. in accordance with the method for claim 1, wherein, and the active component of said hydrogenation catalystBe selected from the oxide of Pt, Pd, Ru, Co, Mo, Ni, W metal or sulfideAt least one, by oxide weight, content is total catalyst weight 0.1～50%,Catalyst carrier is selected from active carbon, Al2O3、SiO2、TiO2In one or more mixedCompound.
12. according to side claimed in claim 1, and wherein, said hydrogenation deoxidation reaction condition is anti-Answering temperature is 150～450 DEG C, and Hydrogen Vapor Pressure is 0.1～10MPa, reaction intermittently orIn continuous flow reactor, carry out; In batch reactor, catalyst amount is weight of oil0.1～10%, the reaction time is 0.5～15h; In continuous flow reactor, markAccurate state hydrogen to oil volume ratio is 100:1～5000:1, the volume space velocity of oil is 0.1～
20h‐1。
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101113348A (en) * | 2007-09-06 | 2008-01-30 | 昆明理工大学 | Process for preparing bio-fuel by high-pressure fluid transformation technique |
| CN101906312A (en) * | 2009-06-05 | 2010-12-08 | 北京瑞增兰宇新能源有限公司 | Method for preparing hydrocarbon fuel oil by mixing biomass oil and animal and vegetable oil |
| US20110173875A1 (en) * | 2007-08-14 | 2011-07-21 | Bergen Teknologioverforing As | One-step conversion of solid lignin to liquid products |
| CN103384713A (en) * | 2011-01-05 | 2013-11-06 | 莱斯拉有限公司 | Processing of organic matter |
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- 2015-07-21 CN CN201510431251.XA patent/CN106367095B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20110173875A1 (en) * | 2007-08-14 | 2011-07-21 | Bergen Teknologioverforing As | One-step conversion of solid lignin to liquid products |
| CN101113348A (en) * | 2007-09-06 | 2008-01-30 | 昆明理工大学 | Process for preparing bio-fuel by high-pressure fluid transformation technique |
| CN101906312A (en) * | 2009-06-05 | 2010-12-08 | 北京瑞增兰宇新能源有限公司 | Method for preparing hydrocarbon fuel oil by mixing biomass oil and animal and vegetable oil |
| CN103384713A (en) * | 2011-01-05 | 2013-11-06 | 莱斯拉有限公司 | Processing of organic matter |
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