JP5668469B2 - Method for thermal decomposition of plant biomass - Google Patents

Description

  The present invention relates to a method for obtaining useful organic compounds by pyrolyzing plant biomass.

  When plant biomass is pyrolyzed, many decomposition products derived from cellulose, hemicellulose, lignin, fats and oils, etc. contained in plant biomass are generated. While this pyrolyzate contains useful organic compounds such as phenol, it contains many other poorly useful substances. Extracting only certain compounds from such miscellaneous mixtures requires considerable effort and is not suitable for industrial applications. In order to solve such problems, for example, it may be possible to extract only cellulose by pretreatment of plant-based biomass raw material and pyrolyze, but the pretreatment itself is labor intensive and is also useful for industrial application. Is not suitable.

  Non-Patent Document 1 describes a compound generated when beech wood is pyrolyzed at 600 to 900 K, and discloses that compounds obtained by differences in pyrolysis temperature are different. Patent Document 1 discloses a process of taking out a useful compound through processes such as separation, concentration and hydrogenation from pyrolysis oil obtained from plant biomass.

Special table 2009-536237

Ind. Eng. Chem. Res., 2003, vol. 42, pp. 3190-3202

  Although the pyrolyzate of plant biomass contains a lot of useful organic compounds, a simple and effective method for extracting a desired compound therefrom is not known. In order to make effective use of plant-based biomass, a simple method suitable for industrial application that can extract a desired organic compound from plant-based biomass is required.

  As a result of the study, the inventor thermally decomposes the plant biomass by at least two stages of heating processes, and thereby a group of components derived from each component such as lignin and hemicellulose contained in the plant biomass only by heat treatment. It has been found that a compound or a specific compound can be separated and taken out. The gist of the present invention is as follows.

(1) A method for obtaining a useful organic compound by pyrolyzing plant biomass,
A first heating step of heating the biomass at a first heating temperature;
The said method including the 2nd heating process which heats either the gasification thing or biomass residue obtained at the 1st heating process at 2nd heating temperature higher than 1st heating temperature.

(2) The plant biomass is heated at a first heating temperature of 400 ° C. or lower in the first heating step, and the biomass residue is heated at a second heating temperature of 500 ° C. or higher in the second heating step to decompose lignin-derived degradation products. The method according to (1), wherein:

(3) In the second heating step, the third heating step of heating the biomass residue obtained in the first heating step, and further heating the generated biomass residue at a third heating temperature higher than the second heating temperature. The method according to (1) or (2), further comprising:

(4) The first heating temperature is 400 ° C. or less, the second heating temperature is in the range of 500 to 600 ° C., and the biomass residue is heated at the third heating temperature of 600 ° C. or more in the third heating step to form lignin. The method according to (3), wherein a degradation product is obtained.

(5) The method according to any one of (1) to (4), wherein the lignin-derived degradation product contains at least phenol or cresol.
(6) The biomass is heated at the first heating temperature in the range of 280 to 320 ° C in the first heating step, and the gasified product obtained in the first heating step is at the second heating temperature in the range of 600 to 800 ° C. The method according to any one of (1) to (5), wherein a decomposition product derived from hemicellulose is obtained by heating.
(7) The method according to (6), wherein the degradation product derived from hemicellulose contains at least furan.

  According to the method of the present invention, a group or a specific compound derived from each component such as lignin and hemicellulose contained in plant biomass can be separated and extracted only by heat treatment. Therefore, according to the present invention, useful compounds can be extracted from plant biomass with a certain degree of purity, and organic compounds such as phenols can be prepared without using petroleum or the like.

It is a flowchart which shows the outline | summary of the method of this invention. It is the chart obtained by GC / MS measurement of the volatile component produced when the cedar was pyrolyzed at 500 degreeC. It is a chart which shows transition of the weight decreasing rate of a cedar sample when it heats up at 50 degreeC / min and hold | maintains at 370 degreeC. It is the chart obtained by GC / MS measurement of the volatile component produced when the cedar was pyrolyzed at two stages of temperatures from 370 ° C. to 500 ° C. It is the chart obtained by GC / MS measurement of the volatile component produced when cypress was thermally decomposed at 500 degreeC. It is the chart obtained by GC / MS measurement of the volatile component produced when cypress was thermally decomposed at two stages of temperatures from 370 ° C. to 500 ° C. It is the chart obtained by GC / MS measurement of the volatile component produced when cypress was thermally decomposed at 270 degreeC or 330 degreeC. It is the schematic of the apparatus which has two heating zones used in Example 2-2. It is the chart obtained as a result of carrying out GPC analysis of the decomposition product obtained by thermally decomposing cypress at 300 degreeC and reheating the produced | generated gasification thing at 600-800 degreeC. It is the chart obtained by GC / MS measurement of the volatile component produced when eucalyptus was thermally decomposed at three stages of temperatures of 370 ° C. → 500 ° C. → 600 ° C. It is the chart obtained by GC / MS measurement of the volatile component produced when the palm kernel shell was thermally decomposed at a temperature of two stages of 500 ° C. → 600 ° C. It is the chart obtained by GC / MS measurement of the volatile component produced when the palm kernel shell was thermally decomposed at three stages of temperatures of 350 ° C. → 500 ° C. → 600 ° C.

  FIG. 1 is a flowchart showing an outline of the present invention. The method of this invention is demonstrated along this flowchart.

  The method of the present invention comprises a first heating step (A) for heating plant biomass at a first heating temperature, and a gasified product (a1) or biomass residue (a2) obtained in the first heating step. A second heating step (B or C) for heating at a second heating temperature higher than the first heating temperature is included. Further, the method of the present invention is configured so that the biomass residue (c2) generated in the second heating step (C) for heating the biomass residue (a2) obtained in the first heating step is higher than the second heating temperature. 3rd heating process (D) heated at the heating temperature of 3 may be included.

  In the present specification, “plant biomass” means a plant-derived raw material containing cellulose, hemicellulose, lignin and the like, and includes both woody biomass and herbaceous biomass. Woody biomass includes cedar, cypress, pine, cucumber, cherry, tamamo, zelkova, beech, oak, maple, ginkgo, giraffe, oak, chestnut, eucalyptus, teak, mahogany, hiba, poplar, acacia, fir, hippopotamus, Japanese timber such as waran, walnut, sawara, kayak, yew, oak, wig, fir, jatropha, etc. The material derived from the plant which has the wooded stem tissue which is made into an example is included. Herbaceous biomass is derived from plants that do not have woody stem tissue such as rice, wheat, sugarcane, corn, rape, soybean, palm, reed, sasa, bamboo, sugar beet, potato, legumes, algae Material is included. Naturally, residues of the above woody biomass and herbaceous biomass such as bagasse (sugarcane squeezed), soybeans, oilseed rape, palm palm, and the like are also included in plant biomass. As the plant biomass used in the method of the present invention, a woody biomass containing a large amount of lignin is more preferable for producing a large amount of phenols described later.

  The “useful organic compound” in the method of the present invention means an organic compound useful as a raw material in the chemical industry or as a fuel for an engine or a fuel cell. Specific examples of useful organic compounds include monohydric phenols, dihydric phenols, trihydric phenols, furans, levoglucosan, cellobiose and the like. Examples of useful organic compounds obtained by pyrolysis of plant biomass include phenol, cresol and furan.

  In each heating step (A to D) in the method of the present invention, a raw material (biomass, gasified product or biomass residue) to be heated is pyrolyzed. Therefore, in order to minimize the hydrolysis reaction and advance the thermal decomposition reaction, it is preferable that no excess water exists in the system when heating is performed. Each heating step is preferably performed, for example, in the presence of an inert gas and in the absence of moisture other than that originally contained in the raw material. If necessary, the raw material may be dried before being subjected to the heating step to remove moisture in advance.

  The method of the present invention includes, after each heating step (A to D), separating a gasified product generated by thermal decomposition from a residue remaining without being gasified. Separation is performed by a normal method known to those skilled in the art, for example, a condenser is provided in the exhaust system of the furnace to be heated to collect and collect the gasified product contained in the exhaust, and separately collect the residue remaining in the furnace after the heating. Is done.

  In the first heating step (A), it is preferable to heat the plant biomass at a temperature of 400 ° C. or lower, particularly 380 ° C. or lower. This is based on the knowledge that cellulose and hemicellulose among components contained in plant-based biomass cause thermal decomposition even at a relatively low temperature. At such a temperature, lignin is hardly decomposed among the components constituting the plant biomass, and only cellulose and hemicellulose are thermally decomposed and changed into a gasified product (a1). However, since the thermal decomposition does not proceed when the temperature is too low, it is preferable to heat the plant biomass at a temperature of 275 ° C. or higher, particularly 280 ° C. or higher.

  Although the optimal heating temperature (1st heating temperature) in a 1st heating process (A) changes with kinds of plant biomass, it is the range of 400 degrees C or less normally. For example, when the plant-based biomass is derived from woody biomass such as cedar or cypress, the first heating temperature is preferably 380 ° C. or lower, particularly 375 ° C. or lower, particularly 370 ° C. or lower. If the purpose is mainly to obtain a gasification product derived from hemicellulose, hemicellulose begins to thermally decompose at a lower temperature compared to cellulose, so the first heating temperature is, for example, 275 to 325 ° C., particularly 280 to 280 ° C. A range of 320 ° C. is preferable.

  In the second heating step (B or C), either the gasified product (a1) or the biomass residue (a2) generated in the first heating step is heated at a second heating temperature higher than the first heating temperature. . Here, the biomass residue means a residue after the gasified product generated by thermal decomposition is separated from the material subjected to heating. The second heating temperature is preferably set to a temperature of, for example, 450 ° C. or higher, particularly 500 ° C. or higher.

  The plant biomass is heated at a first heating temperature of 400 ° C. or lower in the first heating step (A), and the biomass residue (a2) is heated at a second heating temperature of 500 ° C. or higher in the second heating step (C). Then, a lignin-derived decomposition product is obtained as the gasified product (c1). Lignin-derived degradation products include phenol, cresol, guaiacol, hydroxymethoxytoluene, hydroxymethoxyethylbenzene, hydroxymethoxyvinylbenzene, hydroxymethoxypropylbenzene, dimethoxyphenol, hydroxydimethoxytoluene, hydroxydimethoxyethylbenzene, hydroxydimethoxypropylbenzene, pyrocatechol, Phenols such as benzofuran, dibenzofuran and vanillin are included. Of these phenols, phenol and cresol are particularly important compounds in the industry. The lignin-derived degradation product obtained here contains at least phenol or cresol. The content of phenol and / or cresol in the lignin-derived degradation product obtained here is preferably 20% by weight or more based on the total weight after the obtained gasified product (c1) is aggregated. More preferably, the lignin-derived degradation product obtained here consists essentially of phenol and / or cresol. Here, “consisting essentially of” means that impurities other than the target substance contained in the object are less than 5% by weight, particularly less than 3% by weight, especially less than 1% by weight.

  The biomass residue (c2) further generated after the biomass residue (a2) is heated in the second heating step (C) and the gasified product (c1) is released may be subjected to the third heating step (D). In the third heating step (D), heating is performed at a third heating temperature that is higher than the second heating temperature in the second heating step (C). The third heating temperature is preferably set to a temperature of, for example, 550 ° C. or higher, particularly 600 ° C. or higher. However, since the biomass residue (a2) is carbonized if the temperature is too high, the third heating temperature is preferably 650 ° C. or lower.

  The plant biomass is heated at a first heating temperature of 400 ° C. or less (more preferably 380 ° C. or less, particularly preferably 370 ° C. or less) in the first heating step (A), and the biomass residue (a2) in the second heating step (C) ) At a second heating temperature in the range of 500 to 600 ° C. (more preferably in the range of 500 to 550 ° C.), and further in the third heating step (D) at 600 ° C. or higher (more preferably 620 ° C. or higher). By heating the biomass residue (c2) at the third heating temperature, the lignin remaining without being decomposed is thermally decomposed to obtain a lignin-derived decomposed product as a gasified product (d1). The lignin-derived degradation product obtained here is the same as described above, and contains at least phenol or cresol. The content of phenol and / or cresol in the lignin-derived decomposition product obtained here is preferably 50% by weight or more based on the total weight after the obtained gasified product (d1) is aggregated. More preferably, the lignin-derived degradation product obtained here consists essentially of phenol and / or cresol. Since the biomass residue (d2) generated in the third heating step (D) no longer contains a useful compound, it is usually used as a heat source material.

  In the first heating step (A), the plant biomass is heated at a first heating temperature in the range of 280 to 320 ° C. (more preferably in the range of 300 to 320 ° C.), and in the second heating step (B), the gasified product ( By heating a1) at a second heating temperature in the range of 600 to 800 ° C (more preferably in the range of 630 to 660 ° C), a hemicellulose-derived decomposition product is obtained as the product (b1). The hemicellulose-derived decomposition products include furans such as furan and furfural. The hemicellulose-derived decomposition product obtained here contains at least furan. The furan content in the hemicellulose-derived decomposition product obtained here is preferably 30% by weight or more based on the total weight after the obtained product (b1) is aggregated. More preferably, the hemicellulose-derived degradation product obtained here consists essentially of furan.

  If the purpose is to obtain furan with higher purity, the second heating temperature is preferably 700 ° C. or higher, particularly 750 ° C. or higher. In this case, the content of furan in the obtained hemicellulose-derived decomposition product is preferably 50% by weight or more based on the total weight after the obtained product (b1) is aggregated. Moreover, even if it is a little inferior in terms of purity, if the purpose is to obtain furan in a high yield, the second heating temperature is in the range of 630 to 660 ° C., particularly in the range of 640 to 660 ° C. It is preferable.

  If a cellulose-derived degradation product is obtained in addition to the hemicellulose-derived degradation product, the first heating temperature in the first heating step (A) is 320 ° C. or higher, for example, a range of 320 to 400 ° C. (more preferably 350 to 380 ° C. Temperature). Cellulose-derived degradation products include hydroxymethylfurfural, levoglucosan, cellobiose and the like.

Each procedure mentioned above, ie, (i) A biomass residue (a2) is obtained from a plant biomass through the first heating step (A), and it is subjected to a second heating step (C) to give a gasified product (c1). Procedure to get,
(Ii) A biomass residue (a2) is obtained from the plant-based biomass through the first heating step (A), and the biomass residue (c2) generated by applying it to the second heating step (C) is subjected to the third heating. A procedure for obtaining a gasified product (d1) by subjecting it to the step (D), and (iii) obtaining a gasified product (a1) from the plant biomass through the first heating step (A), which is obtained in the second heating step ( The procedure for obtaining the product (b1) by attaching to B) may be performed all in parallel, or only one or two specific procedures may be performed.

  Performing each procedure in parallel means that the gasified product (a1) generated in the first heating step (A) is used for the procedure (iii) above, while the biomass residue (a2) is used in the procedure (i) above. This means that the biomass residue (c2) generated in the procedure and also in the procedure (ii) is used. By performing all the steps in parallel, useful organic compounds contained in the biomass can be taken out without waste.

  On the other hand, performing only one of the procedures means that, for example, only the procedure (i) is performed, and the gasified product (a1) generated in the first heating step (A) and the second heating step (C) are generated. This means that the biomass residue (c2) is not subjected to any further treatment and is used as a fuel or the like as a miscellaneous mixture or disposed of. Similarly, performing only two procedures means, for example, that only the procedures (i) and (iii) above are performed, and the biomass residue (c2) generated in the second heating step (C) is further processed. Means no. By performing only a specific procedure, it is possible to select conditions (such as heating temperature) at which a desired organic compound (for example, phenol or cresol) is obtained with excellent purity and / or maximum yield.

  The product (b1, c1, d1) obtained in each procedure may be further purified as necessary. According to the method of the present invention, since the compounds contained in these products are considerably less in kind compared to the pyrolyzate obtained by simply pyrolyzing plant biomass in one stage, it is particularly useful for purification. There is no difficulty. Purification can be performed by a conventionally known method such as distillation.

  EXAMPLES Hereinafter, although this invention is demonstrated in detail using an Example, this invention is not limited to these Examples.

1-1. Analysis of pyrolysis volatile components of cedar (500 ℃)
The cedar was pyrolyzed at 500 ° C., and GC / MS measurement of the generated volatile components was performed. The measuring devices used are as follows.
Pyrolyzer: PY-2020iD (manufactured by Frontier Lab)
GC / MS: GCMS-QP2010 (manufactured by Shimadzu Corporation)
Column: DB-17 (manufactured by Agilent Technologies)

  A cedar sample was placed in a pyrolyzer heating furnace (helium atmosphere) set at 500 ° C. for 5 minutes, and the generated volatile components were measured by GC / MS (1.5 to 30 minutes after the start of thermal decomposition). A chart obtained by the measurement is shown in FIG. As shown in the figure, the volatile components obtained by thermal decomposition at 500 ° C. contained many decomposition products derived from cellulose, hemicellulose, and lignin.

  In addition, the retention time (Retention Time) of main compounds in GC / MS measurement using the apparatus and measurement conditions used this time is as shown in Table 1 below (the same applies to the subsequent GC / MS measurements).

1-2. Analysis of thermal decomposition behavior of cedar (370 ℃)
Thermogravimetry (TG measurement) was performed to analyze the thermal decomposition behavior of cedar. FIG. 3 shows the transition of the weight reduction rate of the cedar sample when the temperature is raised at 50 ° C./min and held at 370 ° C. The weight of the cedar sample started to decrease from about 280 ° C., and after reaching 370 ° C., the decrease rate decreased in about 2 minutes. At this point, the residual weight was about 30% of the initial weight. From this, it was found that in the thermal decomposition of the cedar sample, almost all volatile components were removed in about 5 minutes.

1-3. Analysis of pyrolysis volatile components of cedar (370 ℃ → 500 ℃)
The cedar was thermally decomposed at two stages of temperature, and GC / MS measurement of the generated volatile components was performed. The measuring apparatus used is the same as 1-1. A cedar sample was placed in a pyrolyzer heating furnace (helium atmosphere) set at 370 ° C. for 5 minutes. Then, the cedar sample was once pulled up from the heating furnace and returned to room temperature. The heating furnace was set to 500 ° C., and the sample was put into the heating furnace again and held for 5 minutes. Volatile components generated at each temperature were measured by GC / MS. The obtained chart is shown in FIG. The components volatilized at 370 ° C. contained many hemicellulose-derived and cellulose-derived degradation products. On the other hand, the components volatilized at 500 ° C. contained a large amount of degradation products (phenols) derived from lignin. When the chart of FIG. 4 is compared with the chart of FIG. 2, when it is heated at 500 ° C. after being held at 370 ° C., the degradation products derived from hemicellulose and cellulose are reduced as compared with the case where it is directly heated to 500 ° C. (See regions A and B surrounded by broken lines in FIG. 4).

1-4. Analysis of pyrolysis volatile components of Japanese cypress (500 ° C)
The generated volatile components were measured by GC / MS in the same manner as in 1-1 above except that the sample was changed to cypress. A chart obtained by the measurement is shown in FIG. Similar to the cedar sample, many degradation products derived from cellulose, hemicellulose, and lignin were contained.

1-5. Analysis of thermal decomposition behavior of cypress (370 ℃ → 500 ℃)
GC / MS measurement was performed in the same manner as in 1-3 above except that the sample was changed to cypress. FIG. 6 shows a chart obtained by measuring volatile components generated at temperatures of 370 ° C. and 500 ° C. by GC / MS. Similar to the cedar sample, the components volatilized at 370 ° C. contained many hemicellulose-derived and cellulose-derived degradation products. On the other hand, the components volatilized at 500 ° C. contained a large amount of degradation products (phenols) derived from lignin. When the chart of FIG. 6 is compared with the chart of FIG. 5, the hemicellulose-derived and cellulose-derived degradation products are reduced when heated at 500 ° C. after being held at 370 ° C., as compared with the case of being directly heated to 500 ° C. (See regions A and B surrounded by a broken line in FIG. 6).

2-1. Cypress thermal decomposition test (270 ° C, 330 ° C)
Cypress was pyrolyzed at 270 ° C. or 330 ° C., and GC / MS measurement of the volatile components produced was performed. The measurement conditions and the like were the same as those in 1-1. A chart obtained by the measurement is shown in FIG. At 270 ° C., the temperature was too low, and no pyrolyzate peak was observed. On the other hand, at 330 ° C., it was found that not only the pyrolysis product derived from hemicellulose but also hydroxymethylfurfural derived from cellulose was produced. It was found that 280 to 320 ° C. is suitable as a temperature range for obtaining a thermal decomposition product derived from hemicellulose.

2-2. Reheating gasified product by thermal decomposition of cypress (300 ° C → 600-800 ° C)
A cypress sample (about 0.1 g) is set in the front stage of a tubular furnace having two heating zones (see FIG. 8), and the gasified product generated when heated in a helium atmosphere at 300 ° C. is heated in the rear stage. In a part (secondary decomposition reactor) was further heated (600 ° C., 650 ° C., 670 ° C. or 800 ° C.) for thermal decomposition, and the resulting decomposition product was analyzed by GPC. A chart obtained by GPC analysis is shown in FIG. The display of “300-600” in the chart means that the chart is obtained when the front stage is heated at 300 ° C. and the rear stage is heated at 600 ° C. (the same applies to others). In the chart, peaks corresponding to furan and water appear at the positions indicated by arrows in the chart “300-800”, respectively. The recovery rate with respect to the furan stoichiometric amount was as shown in Table 2 below.

  Furan was produced even when the secondary decomposition temperature was 600 ° C., and the production amount peaked when the secondary decomposition temperature was 650 ° C. Further, when the secondary decomposition temperature was 800 ° C., the product obtained by aggregating the decomposed product contained only furan and water. From this, it was found that the secondary decomposition temperature with the highest furan recovery rate was 650 ° C., and the secondary decomposition temperature with the highest furan selective recovery was 800 ° C.

3-1. Analysis of pyrolysis volatile components of eucalyptus (370 ℃ → 500 ℃ → 600 ℃)
Eucalyptus was thermally decomposed at three stages of temperature, and GC / MS measurement of the generated volatile components was performed. The measuring apparatus used is the same as 1-1. The eucalyptus sample was placed in a pyrolyzer heating furnace (helium atmosphere) set at 370 ° C. for 5 minutes. Then, the eucalyptus sample was once pulled up from the heating furnace and returned to room temperature. The heating furnace was set to 500 ° C., and the sample was put back into the heating furnace and held for 5 minutes. Similarly, after pulling up the eucalyptus sample once, the heating furnace was set to 600 ° C., and the sample was put in the heating furnace again and held for 5 minutes. Volatile components generated at each temperature were measured by GC / MS. The obtained chart is shown in FIG. It was found that when pyrolysis was performed at three stages of 370 ° C. → 500 ° C. → 600 ° C., a pyrolyzate mainly composed of phenol and cresol was generated at 600 ° C.

3-2. Analysis of pyrolysis volatile components of palm kernel shell (500 ℃ → 600 ℃ / 350 ℃ → 500 ℃ → 600 ℃)
The palm core shell was pyrolyzed at two stages (500 ° C. → 600 ° C.) or three stages (350 ° C. → 500 ° C. → 600 ° C.), and GC / MS measurement of the generated volatile components was performed. The measuring apparatus used is the same as 1-1. The procedure for thermal decomposition at two or three stages of temperature is the same as in 1-3 and 3-1. The obtained charts are shown in FIGS. 11 and 12, respectively. When pyrolysis was performed in two stages from 500 ° C. to 600 ° C. and the pyrolysis process was not performed at a low temperature, peaks of phenol and cresol were hardly observed in the pyrolysis at 600 ° C. On the other hand, when pyrolysis is performed in three stages of 350 ° C. → 500 ° C. → 600 ° C. including pyrolysis at 350 ° C., which is a relatively low temperature, phenol and cresol peaks are observed in the pyrolysis at 600 ° C. It was.

Claims (5)

A method for obtaining a decomposed product mainly composed of phenol and cresol by thermally decomposing plant biomass,
A first heating step of extracting biomass by heating biomass at a first heating temperature of 400 ° C. or lower;
A second heating step in which the biomass residue obtained in the first heating step is heated at a second heating temperature in the range of 500 to 600 ° C. to take out the gasified product ;
A third heating step, wherein the biomass residue further generated in the second heating step is heated at a third heating temperature of 600C or higher to obtain a decomposition product mainly comprising phenol and cresol . The method according to claim 1, wherein the decomposition product obtained in the third heating step contains 50% by weight or more of phenol and cresol based on the total weight after the obtained gasified product is aggregated. A method for obtaining a degradation product derived from hemicellulose containing at least furan by thermally decomposing plant biomass,
A first heating step of heating the biomass at a first heating temperature in the range of 280 to 320 ° C;
The said method including the 2nd heating process which heats the gasification product obtained at the 1st heating process at the 2nd heating temperature of the range of 600-800 degreeC, and obtains the decomposition product derived from hemicellulose. A method for obtaining a lignin-derived degradation product containing at least phenol or cresol and a hemicellulose-derived degradation product containing at least furan by thermally decomposing plant biomass,
Heating step A for heating the biomass at a heating temperature in the range of 280 to 320 ° C;
A heating step B in which the gasified product obtained in the heating step A is heated at a heating temperature in the range of 600 to 800 ° C. to obtain a decomposition product derived from hemicellulose;
The said process including the heating process C which heats the biomass residue obtained by the heating process A at the heating temperature of 500 degreeC or more, and obtains a lignin origin decomposition product.   The heating temperature in the heating step C is in the range of 500 to 600 ° C., and further includes a heating step D in which the biomass residue further generated in the heating step C is heated at a heating temperature of 600 ° C. or more to obtain a lignin-derived decomposition product. Item 5. The method according to Item 4.

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