WO2001054837A1 - Composition produite au moyen du traitement d'une biomasse avec un solvant supercritique et procede de production associe - Google Patents

Composition produite au moyen du traitement d'une biomasse avec un solvant supercritique et procede de production associe Download PDF

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Publication number
WO2001054837A1
WO2001054837A1 PCT/JP2001/000456 JP0100456W WO0154837A1 WO 2001054837 A1 WO2001054837 A1 WO 2001054837A1 JP 0100456 W JP0100456 W JP 0100456W WO 0154837 A1 WO0154837 A1 WO 0154837A1
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Prior art keywords
biomass
supercritical
alcohol
organic solvent
derived
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PCT/JP2001/000456
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English (en)
Japanese (ja)
Inventor
Shiro Saka
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Japan Science And Technology Corporation
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Publication of WO2001054837A1 publication Critical patent/WO2001054837A1/fr

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    • 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
    • C10G1/00—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal
    • C10G1/04—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal by extraction
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/10—Natural spices, flavouring agents or condiments; Extracts thereof
    • A23L27/11—Natural spices, flavouring agents or condiments; Extracts thereof obtained by solvent extraction
    • 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
    • B01J3/00—Processes of utilising sub-atmospheric or super-atmospheric pressure to effect chemical or physical change of matter; Apparatus therefor
    • B01J3/008—Processes carried out under supercritical conditions
    • 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
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids

Definitions

  • the present invention relates to the use of lignocellulosic biomass, cellulosic biomass, nitrogen-containing polysaccharides and protein biomass resources (including unused biomass and waste resources).
  • a supercritical or subcritical organic solvent achieves a supercritical state at a relatively low temperature and pressure compared to water, which has been conventionally used as a material forming a supercritical solvent. When it is returned to normal temperature and normal pressure, it has good solubility in chemical products and forms a good ion-like reaction zone. Solvent decomposition (sometimes partial thermal decomposition may also occur), easily and effectively (less solvent-insoluble products) and efficiently convert to low-molecular-weight biomass-derived compositions The present invention relates to a composition obtained by the method. Background art
  • Japanese Patent Application Laid-Open No. 11-292979 describes that an aromatic compound contained in a plant and / or a plant is treated by treating the plant with supercritical water or subcritical water.
  • a technique has been reported for producing an aromatic compound or a polymer thereof by releasing an aromatic compound produced by decomposing the components inside the plant outside the plant body and isolating the released aromatic compound. ing.
  • Japanese Patent Application Laid-Open No. 9-2681666 focuses on the special properties of supercritical water, and reports a method for producing amino acids and peptides from proteins using such properties.
  • various organic solvents methyl alcohol, ethyl alcohol, acetate, etc.
  • the present invention has been made under such a circumstance, and an object of the present invention is to solve the above-described disadvantages in the prior art.
  • the present invention provides a useful substance obtained by subjecting the biomass resource to a solubilizing-solvent decomposition with an alcohol such as methanol or another organic solvent in a supercritical state or a subcritical state. It is an object of the present invention to provide a composition containing, particularly, a liquid fuel containing a component derived from biomass dissolved in an organic solvent. Further, the component derived from biomass dissolved in the obtained organic solvent can be used as a new composition by distilling off the solvent and then dissolving in another solvent as a new composition. Alternatively, the chemical product from which the solvent has been distilled off can be used for various purposes. Disclosure of the invention
  • one or more selected from the group consisting of lignocellulosic biomass, cellulosic biomass, nitrogen-containing polysaccharides, and protein biomass resources are placed in a supercritical state.
  • a method for obtaining the biomass-derived composition wherein the composition is treated in an organic solvent in a subcritical state.
  • the method for producing a composition derived from biomass is characterized in that alcohol is used as an organic solvent, and the product after the supercritical alcohol treatment is treated with an alcohol-soluble part and an insoluble part.
  • the biomass-derived composition is added to a supercritical or subcritical organic solvent with an effective amount of a catalyst selected from an acid (2% or less). Is the way.
  • one or more selected from the group consisting of lignocellulosic biomass, cellulosic biomass, nitrogen-containing polysaccharides and protein biomass resources are placed in a supercritical state.
  • an organic solvent is an alcohol represented by R 'OH (R 1 has a carbon number is an aliphatic group of 1-1 4)
  • R 1 has a carbon number is an aliphatic group of 1-1 4)
  • a composition comprising a compound, more preferably a composition comprising the organic solvent and a compound derived from biomass, wherein the organic solvent is methanol.
  • FIG. 1 is a schematic diagram of an example of an apparatus for implementing the present invention.
  • 1 is a soot bath for heating the contents of the reaction tube 3 that undergoes the supercritical reaction to the reaction conditions, and 2 is for rapidly cooling the contents of the reaction tube 3 to perform the supercritical reaction.
  • a water bath for stopping, and 4 and 5 are a thermometer and a pressure gauge, respectively, for monitoring the temperature and pressure in the reaction tube.
  • FIG. 2 shows the results of high-performance liquid chromatography (HPLC) analysis of a composition obtained by treating cedar wood flour in a supercritical methanol solvent.
  • HPLC high-performance liquid chromatography
  • Fig. 3 shows (a) the water obtained by treating cedar wood in supercritical water and distilling off the water, and then adding the same amount of pure water, and (b) the supercritical water. 3 shows the results of high-performance liquid chromatography (HPLC) analysis of the composition itself obtained by treating cedar wood with the method. (Indicates furfural.)
  • Fig. 4 shows cedar wood flour (mouth, crushed into about 80 mesh), Avicel ( ⁇ , Avicel), cotton line (dissolved) and dissolved pulp ( ⁇ ) biomass It shows the reaction characteristics (degradability) of raw materials in supercritical methanol. The present invention will be described in detail.
  • the biomass resources targeted in the present invention include not only lignocellulosic resources including lignin, but also cellulosic resources composed of cellulose and hemicellulose, nitrogen-containing polysaccharides and protein biomass. Resources are included. In other words, forest products such as lignocelluloses such as wood, agricultural products such as corn, marine plants such as seaweed, and all other cellulosic resources on the earth and other lignocellulosic resources, Nitrogen-containing polysaccharide resources such as chitin and chitosan, which are components of crab hulls, animal substances such as animal glue, casein blood albumin, and plant-based proteins such as soybean protein And other protein resources.
  • Some of these include forest thinnings such as thinned wood and waste wood that are discarded without being effectively used, agricultural waste such as rice husks and corn stover, and unused Biomass resources such as marine waste such as seaweed, shrimp husks and chitin, chitosan and other nitrogen-containing polysaccharides, animal substances, animal proteins such as animal glue and zein blood albumin Quality and vegetable proteins such as soybean protein, and waste resources such as municipal waste.
  • forest thinnings such as thinned wood and waste wood that are discarded without being effectively used
  • agricultural waste such as rice husks and corn stover
  • Biomass resources such as marine waste such as seaweed, shrimp husks and chitin, chitosan and other nitrogen-containing polysaccharides, animal substances, animal proteins such as animal glue and zein blood albumin Quality and vegetable proteins such as soybean protein, and waste resources such as municipal waste.
  • Alcohols useful as supercritical organic solvents include methanol, ethanol, 1-pronol, 2-butanol, 1-butanol, isoptyl alcohol, 2 - Bed evening Nord, t chromatography butanoate Ichiru, refers to a monovalent alcohols such as ⁇ Lil alcohol, represented by the formula R 1 0 H.
  • R 1 is an aliphatic group containing 124 carbon atoms.
  • Table 1 shows an example of the critical temperature (Tc) and critical pressure (Pc) of these alcohols.
  • the supercritical state refers to a state in which the temperature in the reaction system is equal to or higher than the critical temperature (Tc) and the pressure is equal to or higher than the critical pressure (Pc).
  • Tc critical temperature
  • Pc critical pressure
  • Subcritical means that the temperature in the reaction system is equal to or higher than the boiling point of the alcohol and approximately 150 ° C. or higher, and the pressure is equal to or higher than the vapor pressure of the alcohol at the reaction temperature, and approximately 2.0 OMPa or higher. State.
  • At least a temperature of 150-600 ° C .; a pressure of 2.0—20 OMP is required to form a supercritical or subcritical alcohol.
  • the temperature and pressure may be adjusted appropriately in the range of a.
  • the temperature is 220-400 ° C
  • the pressure is 3 — 100 MPa.
  • the reaction time is selected from the range of 1 second to 2 hours depending on the reaction conditions. More preferably, it is in the range of 130 minutes.
  • the reaction that occurs in a supercritical organic solvent, particularly in an alcohol, is essentially a solvolysis reaction, but also partially occurs in a thermal decomposition reaction. Therefore, in the present invention, the treatment in a supercritical solvent substantially means a solvolysis reaction.
  • a catalyst selected from an acid for example, an inorganic acid such as hydrochloric acid, sulfuric acid, or phosphoric acid, as in supercritical water, may be used for the alcohol in a supercritical or subcritical state, if necessary. It is also effective to add as a component in a concentration range of 2% or less. Also, the effect of the acid catalyst can be obtained by adding water. If the addition exceeds 2%, it is not preferable because complicated post-treatment is required. A more preferred catalyst concentration is 0.05% or less. That is, according to the present invention, the catalyst effect can be sufficiently exerted even when the catalyst concentration is 0.05% or less.
  • the type of the apparatus for carrying out the production method of the present invention is not particularly limited.
  • a batch type reactor for example, a continuous tank type reactor, a piston flow type single flow reactor, a tower type flow reactor
  • a material similar to that used for the reaction using supercritical water can be used.
  • a tin bath (approximately 350 ° C bath) was used as the heating bath, and a supercritical state with a pressure of 43 MPa and a temperature of 240-340 ° C was realized. It is possible.
  • a salt bath sodium sulfite, For example, potassium sulfate (1: 1)] can be used.
  • composition derived from biomass obtained by the production method of the present invention may be obtained by separating a useful component from an organic solvent as an energy source. It can be used as biomass energy while containing the organic solvent. It can also be used as a fuel by mixing it with light oil, kerosene, or Fuel Oil A.
  • saccharides such as cellulose, cellulose, glucose, xylose, mannose, and fructose as components derived from cellulose and hemicellulose And methylated derivatives thereof (specifically, methylated oligomers, methylose triose, methylcellulose pio- sis, methyl cellulose D-glucose, methyl-D-glucose, methylxylose, methyl) Mannose, methyl fructose, etc.), levoglucosan, hydroxymethylfurfural, furfural and methylated derivatives thereof as useful components, and can be recovered as lignin-derived components.
  • guaiacol 2,6-dimethoxyphenol, coniferylile alcohol, cinavir alcohol , P-coumaryl alcohol, coniferyl alcohol methyl ether, sinapyr alcohol methyl ether, and their derivatives and methylated derivatives. That is, in the case of coniferous trees, those derived from guaiacyl lignin are obtained, and in the case of hardwoods, other low molecular weight products derived from syringyl lignin are obtained. Also, for other plants such as grasses, low molecular weight products derived from lignin that constitute them can be obtained. Proteins are high molecular compounds in which an amino acid and an amino group are amide-bonded. However, when treated with supercritical ethanol, methyl monoamino acid is obtained by solvolysis. From the nitrogen-containing polysaccharide, a product is obtained which has undergone the same reaction as in the solvolysis of the cellulose and protein systems.
  • the supercritical solvent since the supercritical solvent has high solubility in the biochemical product derived from the raw material biomass and the temperature condition for making it supercritical is mild, it is substantially added. Since the solvent decomposition reaction progresses and the thermal decomposition reaction progresses slowly, the generation of volatile products by the thermal decomposition reaction is small.
  • the use of an organic solvent in the supercritical solvent reaction has a remarkable effect that a large amount of effective chemical products derived from high-boiling-point raw material biomass can be obtained in the form of a solution that is easy to handle. Be sent. In addition, at least a part of the organic solvent-soluble part can be separated and recovered by distillation, so that the composition obtained by supercritical processing can be obtained in a highly utilizable state.
  • an organic solvent particularly an alcohol such as methanol
  • the conventional supercritical solvent can be used. Can produce significant effects that cannot be predicted from the reaction is there.
  • the biomass-derived composition obtained by the treatment in the supercritical organic solvent of the present invention is as described above.
  • the effect of the organic solvent in the supercritical or subcritical state, particularly the effect of alcohol, is as follows. The following can be considered.
  • Supercritical or subcritical alcohols can easily and drastically change their dielectric constant and ion product by controlling temperature and pressure.
  • the dielectric constant of alcohol is 33.1 (25 ° C) for methanol and 23.8 (25 ° C) for ethanol, and they are four-molecule aggregates by hydrogen bonding. It has become.
  • hydrogen bonds are broken and become hydrophobic, permittivity decreases, and nonpolar substances are easily dissolved.
  • due to the temperature dependence of the ionic product of the alcohol at each pressure the higher the pressure, the higher the ionic product is maintained up to the high-temperature region, and even at extremely high temperatures, a good ion-like reaction (alcolysis reaction) is achieved.
  • the ionic product and the dielectric constant of the alcohol in the supercritical or subcritical state can be adjusted in a wide range by controlling the temperature and pressure, so that the alcohol in such a state can be used as a solvent for solvolysis. It is thought that an optimal environment for efficiently converting cellulose, hemicellulose and lignin constituting noomas to useful compounds was provided. It can be understood that an effective chemical product can be obtained efficiently and easily.
  • water in a subcritical or supercritical state has an extremely large ion product and acts as a strong acid.
  • FIG. 1 is a schematic explanatory view showing an apparatus for carrying out the present invention.
  • This device is of a batch type, 1 is a tin bath (for heating), 2 is a water bath (for quenching), 3 is a reaction tube, 4 is a temperature monitor, and 5 is a pressure gauge. The temperature and pressure in the reaction tube can be monitored in real time by 4 and 5, and the reaction tube of 3 can be shaken by pendulum movement.
  • the present invention was implemented using the apparatus shown in FIG. 1, and the effects of the present invention were confirmed.
  • Japanese cedar wood flour crushed to approximately 80 mesh was used as a biomass resource.
  • 20 g of the wood flour was charged into a reaction tube 3 having a capacity of 67 OmL, and methanol at room temperature was added thereto to make 67 OmL, and the temperature was raised to 350 ° C in advance.
  • FIG. 2 shows the results of the analysis of the obtained composition.
  • (a) is the result of analysis of methanol obtained by removing methanol from the obtained composition by distillation and then adding the same amount of pure methanol.
  • (b) is the analysis result of the obtained composition as it is. From this, it is understood that the methanol-soluble chemicals derived from biomass have a higher boiling point than methanol. In addition, the only substance that evaporates during the distillation [the component in which the detected peak disappeared in comparison with the chromatograms of (a) and (b)] was only furfural ( ⁇ ), and the other biomass degradation products were: It is understood that it is recovered as a solid (5—HMF is 5—hydroxymethylfurfural). This indicates that the biomass-derived components obtained are solubilized in methanol and that valuable substances can be recovered by simply distilling off the solvent.
  • Example 1 was repeated using water as a solvent and maintaining the mixture in a supercritical state (450 ° C., 200 MPa) for 5 seconds. Almost no wood flour residue was found, but 25% of oily substances insoluble in water at room temperature were obtained, and it was difficult to separate and separate from water-soluble substances.
  • a supercritical state 450 ° C., 200 MPa
  • the water-insoluble matter contains useful compounds derived from biomass raw materials
  • the use of solvents other than the reaction solvent is necessary for the recovery of useful substances.
  • a separation operation is required. Evaluation of the usefulness of the composition obtained in Example 1 and Comparative Example 1 When the methanol-soluble part obtained in Example 1 was put in an alcohol lamp and ignited, the same as in the case of methanol alone It showed good combustion conditions, all burned out, and were confirmed to be useful as fuel.
  • Example 2 The methanol-soluble portion obtained in Example 1 was subjected to component separation by thin layer chromatography (TLC).
  • TLC thin layer chromatography
  • a component derived from cellulose and hemicellulose a methylated derivative of sugar, conifuryl alcohol derived from lignin, p-comalyl alcohol, and a methylated product of these derivatives could be recovered.
  • Figure 4 shows the results. It can be understood that the characteristics (crystallinity, etc.) of the biomass and the form of the raw material, for example, the reactivity differ depending on the pretreatment. It is speculated that the reactivity of cedar wood powder is improved by pulverizing it more finely, because the reactivity differs greatly depending on the raw material form.
  • one or more organic solvents preferably alcohols, and more preferably methanol are used as the solvent in the supercritical or subcritical state as a solvent.
  • Reaction product, and the product composition obtained by the reaction can be used as a fuel as it is, and raw materials that can be easily handled to obtain useful chemical products can be obtained. Effects are obtained. Naturally, it is extremely favorable from the viewpoint of effective use of resources and utilization efficiency.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Polymers & Plastics (AREA)
  • Wood Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Food Science & Technology (AREA)
  • Nutrition Science (AREA)
  • Processing Of Solid Wastes (AREA)
  • Liquid Carbonaceous Fuels (AREA)

Abstract

On décrit un procédé de production d'une composition à partir d'au moins un type de biomasse sélectionné dans le groupe formé par une biomasse de type lignocellulose, une biomasse de type cellulose et une biomasse de type polysaccharide contenant de l'azote. Le procédé se caractérise en ce qu'au moins un des types de biomasse est traité dans un ou plusieurs solvants organiques à l'état supercritique ou à l'état sous-critique. Le solvant organique est de préférence un solvant alcool, de préférence du méthanol. On décrit également une composition produite au moyen dudit procédé.
PCT/JP2001/000456 2000-01-25 2001-01-24 Composition produite au moyen du traitement d'une biomasse avec un solvant supercritique et procede de production associe WO2001054837A1 (fr)

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JP2000015157A JP3755076B2 (ja) 2000-01-25 2000-01-25 バイオマスの超臨界溶媒処理による組成物及びその製造方法
JP2000-15157 2000-01-25

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US8603567B2 (en) 2002-10-30 2013-12-10 Suntory Holdings Limited Method of manufacturing plant finished product

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JP3405981B1 (ja) 2002-06-26 2003-05-12 日本財経株式会社 酢酸セルロースの製造方法
JP3522264B2 (ja) * 2002-12-16 2004-04-26 日本財経株式会社 キシロオリゴ糖の製造方法
JP4759227B2 (ja) * 2004-04-05 2011-08-31 志朗 坂 バイオマスの分解・液化方法
JP4982036B2 (ja) * 2004-04-16 2012-07-25 志朗 坂 バイオマスの分解・液化方法
JP2006223152A (ja) * 2005-02-16 2006-08-31 Hitachi Zosen Corp セルロース溶剤による溶解と加水分解の組合せによるバイオマス処理方法
JP4889286B2 (ja) * 2005-11-18 2012-03-07 日本ハム株式会社 蛋白質低分子化物及びそれを含有する飼料素材又は食品素材
JP4674723B2 (ja) * 2006-05-11 2011-04-20 パナソニック株式会社 木質系廃材の分解処理方法
JP4957661B2 (ja) 2007-07-25 2012-06-20 トヨタ自動車株式会社 バイオマスを原料とする液化燃料油の製造方法
FI20085275L (fi) * 2008-04-02 2009-10-09 Hannu Ilvesniemi Menetelmä biomassan käsittelemiseksi
CN102224220B (zh) * 2008-10-01 2014-07-16 莱斯拉有限公司 产生生物油的方法
KR101569013B1 (ko) 2009-02-16 2015-11-16 삼성전자주식회사 해조류 바이오매스의 전처리 및 당화 방법
JP2010280851A (ja) * 2009-06-05 2010-12-16 Toyota Motor Corp バイオマスからの炭化水素を主成分とする非水溶性液化燃料油の製造方法
JP2010280850A (ja) * 2009-06-05 2010-12-16 Toyota Motor Corp バイオマスからの非水溶性液化燃料油の製造方法
JP2011089000A (ja) * 2009-10-21 2011-05-06 Tokyo Univ Of Agriculture & Technology バイオマス液化燃料の製造方法
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US8383864B2 (en) 2009-12-08 2013-02-26 Iowa State University Research Foundation, Inc. Method for the conversion of cellulose and related carbohydrate materials to low-molecular-weight compounds
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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JP2001205070A (ja) 2001-07-31

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