Phenolic composition and method for enhancing biodegradability and / or photostability thereof

Abstract

Provided is a phenolic composition having enhanced biodegradability and / or photostability, said composition containing a phenol and at least one compound containing one or more atoms selected from among nitrogen, sulfur, and phosphorous.

Description

Phenolic composition and method for improving its biodegradability and / or photostability

[0001] The present disclosure relates to a phenolic composition and a method for improving the biodegradability and / or photostability thereof. More specifically, the present disclosure relates to a composition comprising a phenolic compound and at least one compound containing one or more atoms selected from a nitrogen atom, a sulfur atom, and a phosphorus atom, the composition exhibiting improved biodegradability and / or photostability compared to a composition containing a phenolic compound and not containing a compound containing one or more atoms selected from a nitrogen atom, a sulfur atom, and a phosphorus atom.

[0002] Phenol is used as a raw material for phenolic resins and is essential for the production of industrial products such as plastics, adhesives, and paints. Phenol is also used in the synthesis of pharmaceuticals, pesticides, dyes, and fragrances. Because phenol undergoes direct and indirect photolysis, it is typically stored in a dark place. Because phenol is biologically toxic, there is a need for a technology to prevent its inclusion in industrial wastewater and its release into the environment. For example, Patent Document 1 discloses a method for treating wastewater containing phenolic compounds using a biological process using activated sludge.

[0003] JP 2016-041393 A JP 2023-145381 A

[0004] It is a primary object of the present disclosure to provide phenolic compositions with improved biodegradability and / or photostability.

[0005] To solve the above problems, the present disclosure provides the following [1] to

[24] . [1] A biomass-derived phenolic composition comprising 50 wt% or more of at least one phenol represented by the following formula (1),

[0006] (R 1 ~R 5may be the same or different and each represent a hydroxyl group, a methyl group, a carboxyl group, or a hydrogen atom.) A phenolic composition comprising at least one compound containing one or more atoms selected from a nitrogen atom, a sulfur atom, and a phosphorus atom. [2] The phenolic composition according to [1], which contains a phenol and exhibits improved biodegradability compared to a composition not containing the compound containing one or more atoms selected from a nitrogen atom, a sulfur atom, and a phosphorus atom. [3] The phenolic composition according to [2], wherein the compound containing one or more atoms selected from a nitrogen atom, a sulfur atom, and a phosphorus atom is selected from the group consisting of urea, an ammonium salt compound, a nitrate compound, an amino acid, a sulfate, and a phosphorus compound. [4] The phenolic composition according to [3], wherein the phosphorus compound is a phosphate, a hydrogen phosphate, a phospholipid, or a nucleic acid. [5] The phenolic composition according to [3], wherein the amino acid is an α-amino acid. [6] The phenolic composition according to [5], wherein the α-amino acid is any one or more selected from the group consisting of glutamic acid, arginine, lysine, glycine, serine, glutamine, histidine, phenylalanine, alanine, and proline. [7] The phenolic composition according to [6], wherein the α-amino acid is any one or more selected from the group consisting of glutamic acid, arginine, lysine, and glycine. [8] The phenolic composition according to [6], wherein the α-amino acid is any one or more selected from the group consisting of serine, glutamine, histidine, and phenylalanine. [9] The phenolic composition according to [6], wherein the α-amino acid is alanine and / or proline.

[10] The phenolic composition according to [1], which contains phenols and exhibits improved photostability compared to a composition not containing the compound containing a phosphorus atom and / or a sulfur atom.

[11] The phenolic composition according to

[10] , wherein the compound containing one or more atoms selected from a nitrogen atom, a sulfur atom, and a phosphorus atom is selected from the group consisting of urea, an ammonium salt compound, a nitrate compound, an amino acid, a sulfate, and a phosphoric acid compound.

[12] The phenolic composition according to

[11] , wherein the phosphoric acid compound is a phosphate, a hydrogen phosphate, a phospholipid, or a nucleic acid.

[0007]

[13] The phenol composition according to any one of [1] to

[12] , wherein the phenol is selected from the group consisting of phenol, catechol, cresol, dimethylphenol, xylenol, resorcinol, hydroquinone, and 4-hydroxybenzoic acid.

[14] The composition according to any one of [1] to

[13] , wherein the compound containing one or more atoms selected from a nitrogen atom, a sulfur atom, and a phosphorus atom is contained in an amount of 0.01 to 1,000,000 ppm relative to the mass of the phenol.

[0008]

[15] A method for improving the biodegradability and / or photostability of phenols in a phenol composition, wherein the phenols are biomass-derived phenols represented by the following formula (1), and the phenol composition contains at least one of these phenols in an amount of 50 wt % or more:

[0009] (R 1 ~R 5may be the same or different and each represent a hydroxyl group, a methyl group, a carboxyl group, or a hydrogen atom.) A method characterized by containing at least one compound containing one or more atoms selected from a nitrogen atom, a sulfur atom, and a phosphorus atom in an amount of 0.01 to 1,000,000 ppm relative to the mass of the phenols in the composition.

[16] The method according to

[15] , wherein the compound containing one or more atoms selected from a nitrogen atom, a sulfur atom, and a phosphorus atom is selected from the group consisting of urea, an ammonium salt compound, a nitrate compound, an amino acid, a sulfate, and a phosphoric acid compound.

[17] The method according to

[16] , wherein the phosphoric acid compound is a phosphate, a hydrogen phosphate, a phospholipid, or a nucleic acid.

[18] The method according to

[16] , wherein the amino acid is an α-amino acid.

[19] The method according to

[18] , wherein the α-amino acid is one or more selected from the group consisting of glutamic acid, arginine, lysine, glycine, serine, glutamine, histidine, phenylalanine, alanine, and proline.

[20] The method according to

[19] , wherein the α-amino acid is one or more selected from the group consisting of glutamic acid, arginine, lysine, and glycine.

[21] The method according to

[19] , wherein the α-amino acid is one or more selected from the group consisting of serine, glutamine, histidine, and phenylalanine.

[22] The method according to

[19] , wherein the α-amino acid is alanine and / or proline.

[0010]

[23] The method according to any one of

[15] to

[22] , wherein the phenol is selected from the group consisting of phenol, catechol, cresol, dimethylphenol, xylenol, resorcinol, hydroquinone, and 4-hydroxybenzoic acid.

[0011]

[24] A method for decomposing phenols, comprising a step of contacting the phenol composition according to any one of [1] to

[14] with activated sludge.

[0012] The present disclosure also provides the following [1A] to [20A]. [1A] A composition or highly biodegradable composition comprising a phenol and at least one compound containing one or more atoms selected from a nitrogen atom, a sulfur atom, and a phosphorus atom. [2A] The composition of [1A], which contains a phenol and exhibits improved biodegradability compared to a composition not containing the compound containing one or more atoms selected from a nitrogen atom, a sulfur atom, and a phosphorus atom. [3A] The composition of [2A], wherein the compound containing one or more atoms selected from a nitrogen atom, a sulfur atom, and a phosphorus atom is selected from the group consisting of urea, an ammonium salt compound, a nitrate compound, an amino acid, a sulfate, and a phosphorus compound. [4A] The composition of [3A], wherein the phosphorus compound is a phosphate, a hydrogen phosphate, a phospholipid, or a nucleic acid. [5A] The composition of [3A], wherein the amino acid is an α-amino acid. [6A] The composition of [5A], wherein the α-amino acid is one or more selected from the group consisting of glutamic acid, arginine, lysine, glycine, serine, glutamine, histidine, phenylalanine, alanine, and proline. [7A] The composition of [6A], wherein the α-amino acid is one or more selected from the group consisting of glutamic acid, arginine, lysine, and glycine. [8A] The composition of [6A], wherein the α-amino acid is one or more selected from the group consisting of serine, glutamine, histidine, and phenylalanine. [9A] The composition of [6A], wherein the α-amino acid is alanine and / or proline. [10A] Any of the compositions [1A] to [9A], wherein the phenols are one or more selected from the group consisting of phenol, catechol, cresol, dimethylphenol, xylenol, resorcinol, and hydroquinone. [11A] Any of the compositions [1A] to [10A], containing a compound containing one or more atoms selected from a nitrogen atom, a sulfur atom, and a phosphorus atom in an amount of 0.01 to 10,000 ppm based on the mass of the phenols.

[0013] [12A] A method for improving the biodegradability of phenols in a phenol composition, comprising adding at least one compound containing one or more atoms selected from nitrogen, sulfur, and phosphorus to the composition in an amount of 0.01 to 10,000 ppm relative to the mass of the phenols. [13A] The method according to [12A], wherein the compound containing one or more atoms selected from nitrogen, sulfur, and phosphorus is selected from the group consisting of urea, ammonium salt compounds, nitrate compounds, amino acids, sulfates, and phosphate compounds. [14A] The method according to [13A], wherein the phosphate compound is a phosphate, hydrogen phosphate, phospholipid, or nucleic acid. [15A] The method according to [13A], wherein the amino acid is an α-amino acid. [16A] The method according to [15A], wherein the α-amino acid is one or more selected from the group consisting of glutamic acid, arginine, lysine, glycine, serine, glutamine, histidine, phenylalanine, alanine, and proline. [17A] The method of [16A], wherein the α-amino acid is any one or more selected from the group consisting of glutamic acid, arginine, lysine, and glycine. [18A] The method of [16A], wherein the α-amino acid is any one or more selected from the group consisting of serine, glutamine, histidine, and phenylalanine. [19A] The method of [16A], wherein the α-amino acid is alanine and / or proline. [20A] Any of the methods [12A] to [19A], wherein the phenols are any one or more selected from the group consisting of phenol, catechol, cresol, dimethylphenol, xylenol, resorcinol, and hydroquinone.

[0014] The present disclosure also provides the following [1B] to [10B]. [1B] A composition or a highly photostable composition comprising a phenol and at least one compound containing a phosphorus atom and / or a sulfur atom. [2B] The composition of [1B], which contains a phenol and exhibits improved photostability compared to a composition not containing the compound containing a phosphorus atom and / or a sulfur atom. [3B] The composition of [2B], in which the compound containing a phosphorus atom and / or a sulfur atom is a phosphate compound and / or a sulfate. [4B] The composition of [3B], in which the phosphate compound is a phosphate, a hydrogen phosphate, a phospholipid, or a nucleic acid. [5B] Any of the compositions [1B] to [4B], in which the phenol is any one or more selected from the group consisting of phenol, catechol, cresol, dimethylphenol, xylenol, resorcinol, and hydroquinone. [6B] Any of the compositions [1B] to [5B], containing the compound containing a phosphorus atom and / or a sulfur atom in an amount of 0.01 to 10,000 ppm based on the mass of the phenols.

[0015] [7B] A method for improving the photostability of phenols in a phenol composition, comprising adding a compound containing a phosphorus atom and / or a sulfur atom to the composition in an amount of 0.01 to 10,000 ppm based on the mass of the phenols. [8B] The method of [7B], wherein the compound containing a phosphorus atom and / or a sulfur atom is a phosphate compound and / or a sulfate. [9B] The method of [8B], wherein the phosphate compound is a phosphate, a hydrogen phosphate, a phospholipid, or a nucleic acid. [10B] Any of the methods [7B] to [9B], wherein the phenols are one or more selected from the group consisting of phenol, catechol, cresol, dimethylphenol, xylenol, resorcinol, and hydroquinone.

[0016] The present disclosure provides phenolic compositions with improved biodegradability and / or photostability.

[0017] Preferred embodiments for carrying out the present disclosure will be described below. Note that the embodiments described below are examples of typical embodiments of the present disclosure, and should not be construed as narrowing the scope of the present disclosure.

[0018] The phenolic composition according to the present disclosure includes at least one compound containing one or more atoms selected from a nitrogen atom, a sulfur atom, and a phosphorus atom. It has been found that by adding a compound containing one or more atoms selected from a nitrogen atom, a sulfur atom, and a phosphorus atom to the phenolic composition, the biodegradability and / or photostability of the phenolic compound can be improved.

[0019] In the present disclosure, "biodegradability" of phenols means that phenols can be metabolized by microorganisms and converted into other organic compounds. For example, phenols can be converted into organic compounds such as catechol, muconic acid, acetaldehyde, pyruvic acid, protocatechuic acid, acetyl-CoA, and succinyl-CoA through the metabolism of microorganisms. These organic compounds can then be further metabolized by microorganisms and decomposed into water, carbon dioxide, and the like.

[0020] The biodegradability of phenols can be evaluated by measuring the decrease in the amount of phenols in an environment where they can be metabolized by microorganisms. The quantification of phenols can be carried out by a conventionally known method, such as measuring biological oxygen demand, or by liquid chromatography, gas chromatography, colorimetry, or the like.

[0021] The "environment in which phenols can be metabolized by microorganisms" is not particularly limited, and may be any environment in which microorganisms capable of decomposing or assimilating phenols exist, such as soil, seawater, river water, activated sludge, and compost.

[0022] The "enhanced biodegradability" of the phenolic composition according to the present disclosure refers to biodegradability that is 1%, 2%, 3%, 4%, 5%, preferably 6%, 7%, 8%, 9%, 10%, more preferably 11%, 12%, 13%, 14%, 15%, even more preferably 16%, 17%, 18%, 19%, 20%, and particularly preferably 21%, 22%, 23%, 24%, 25% or more higher than that of a phenolic composition (control composition) that contains phenols but does not contain a compound containing one or more atoms selected from nitrogen, sulfur, and phosphorus. Specifically, the residual amount of phenols in the phenolic composition according to the present disclosure, measured by the above-mentioned measurement method involving, for example, 6 hours of activated sludge treatment, is 1%, 2%, 3%, 4%, 5%, preferably 6%, 7%, 8%, 9%, 10%, more preferably 11%, 12%, 13%, 14%, 15%, even more preferably 16%, 17%, 18%, 19%, 20%, and particularly preferably 21%, 22%, 23%, 24%, 25%, or even more less than that in the control composition. The activated sludge used in the treatment is not particularly limited as long as it allows for such a significant reduction in the residual phenols to be detected. Activated sludge with any physical properties (MLSS, MLVSS, SV30, etc.) and any constituent microbial flora can be used. Because the phenolic composition according to the present disclosure exhibits improved biodegradability, it can be decomposed more efficiently when contacted with activated sludge in an activated sludge treatment than conventional phenolic compositions.

[0023] In the present disclosure, the term "photostability" of phenols refers to the fact that phenols are not decomposed by light and converted into other organic compounds. For example, phenols can be converted into organic compounds such as quinones and polyphenols by direct and indirect photolysis.

[0024] The photostability of phenols can be evaluated by measuring the decrease in the amount of phenols under light irradiation conditions. The phenols can be quantified by a conventionally known method, such as liquid chromatography, gas chromatography, or colorimetry.

[0025] The "improved photostability" of the phenolic composition according to the present disclosure refers to a photostability that is 1%, 2%, 3%, 4%, 5%, preferably 6%, 7%, 8%, 9%, 10%, more preferably 11%, 12%, 13%, 14%, 15%, even more preferably 16%, 17%, 18%, 19%, 20%, and particularly preferably 21%, 22%, 23%, 24%, 25%, or more higher than that of a phenolic composition (control composition) that contains phenols but does not contain a compound containing one or more atoms selected from nitrogen, sulfur, and phosphorus. Specifically, the amount of decomposition of the phenolic composition according to the present disclosure, measured by the above-mentioned method involving 30 minutes of UV irradiation, is 1%, 2%, 3%, 4%, 5%, preferably 6%, 7%, 8%, 9%, 10%, more preferably 20%, 30%, 40%, or more lower than that of the control composition.

[0026] Phenols are compounds represented by the following formula (1).

[0027] (R 1 ~R 5 may be the same or different and each represents a hydroxyl group, a methyl group, a carboxyl group, or a hydrogen atom.

[0028] Specific examples of phenols include phenol, catechol, cresol, dimethylphenol, xylenol, resorcinol, hydroquinone, and 4-hydroxybenzoic acid.

[0029] Phenols may be produced by a chemical process (e.g., the cumene process) or a biological process. Furthermore, phenols may be produced using biomass as a raw material (biomass-derived phenols). Patent Document 2 discloses, as an example of the production of phenols by a biological process, a technology for producing phenol from biomass (so-called biophenols) using microorganisms capable of producing phenols. Furthermore, methods for producing biomass-derived phenols by chemical processes, such as by pyrolysis of biomass (e.g., lignin), are also known. Preferably, the phenols are biophenols obtained by a fermentation process.

[0030] In the present disclosure, a compound containing one or more atoms selected from a nitrogen atom, a sulfur atom, and a phosphorus atom may be added to phenols obtained by a chemical process or a biological process, or the phenols obtained by a chemical process or a biological process may contain a compound containing one or more atoms selected from a nitrogen atom, a sulfur atom, and a phosphorus atom. One or more selected from amino acids, organic acids, and salts thereof are preferably added to phenols obtained by a chemical process or a biological process, and more preferably to phenols obtained by a biological process.

[0031] Examples of methods for producing phenols by biological processes include fermentation, which involves fermenting biomass using microorganisms capable of producing phenol (phenol-producing microorganisms). Examples of phenol-producing microorganisms that can be used include Escherichia bacteria such as Escherichia coli; Pseudomonas bacteria such as Pseudomonas putida; Corynebacterium bacteria such as Corynebacterium glutamicum; Bacillus bacteria such as Bacillus subtilis; Pichia yeast such as Pichia pastoris; Saccharomyces yeast such as Saccharomyces cerevisiae; and Aspergillus filamentous fungi such as Aspergillus oryzae, Aspergillus nidulans, and Aspergillus niger. These microorganisms are not limited to commercially available strains or wild-type strains, and may be any strain, such as mutant strains obtained by commonly used mutation treatments such as UV irradiation or chemical treatment, or recombinant strains induced by genetic techniques such as cell fusion or gene recombination. Furthermore, the microorganisms may be used singly or in combination of two or more selected from these.

[0032] Biomass refers to organic resources derived from plants and animals that can be recycled into energy or materials and excludes fossil resources. In the present disclosure, biomass particularly refers to resources containing fermentable carbohydrates that can be subjected to microbial fermentation. Fermentable carbohydrates include, but are not limited to, glucose, xylose, sucrose, starch, blackstrap molasses, glycerol, ribitol, and erythritol. Biomass may also contain lipids, amino acids, organic acids, and alcohols that can be derived from these fermentable carbohydrates or that can be produced by metabolism of these fermentable carbohydrates. These biomasses can be used alone or in combination of two or more.

[0033] Fermentation can be carried out by culturing microorganisms using conventionally known techniques, and phenols are secreted and accumulated in the fermentation aqueous medium through the metabolism of biomass by the microorganisms. The aqueous medium (culture medium) containing the biomass used for cultivation is a solid or liquid medium containing sufficient nutrients, including at least one carbon source, in which the microorganisms can grow. Furthermore, additional biomass may be added in response to the decrease in biomass that occurs as the reaction progresses. The microbial fermentation process may be a process involving the growth of live bacteria, or a process involving a resting cell reaction using pre-cultured bacteria. For the resting cell reaction, a culture solution of pre-cultured microorganisms may be used as is, or cells recovered by filtration, centrifugation, or the like may be used. The cultivation and resting cell reaction can be carried out using conventionally known techniques.

[0034] Compounds containing one or more atoms selected from nitrogen atoms, sulfur atoms, and phosphorus atoms that are contained in the phenolic composition for improving biodegradability and / or photostability include urea, ammonium salt compounds, nitrate compounds, amino acids, sulfates, and phosphate compounds, one or more of which may be contained in the phenolic composition.

[0035] The phosphate compounds include phosphates, hydrogen phosphates, phospholipids, and nucleic acids. Phospholipids may include glycerophospholipids and sphingophospholipids. Nucleic acids may include deoxyribonucleic acid, ribonucleic acid, and their constituent nucleic acid bases such as adenine, guanine, cytosine, uracil, thymine, xanthine, and hypoxanthine, as well as their nucleosides and nucleotides.

[0036] The ammonium salt compounds, nitrate compounds, sulfates, phosphates and hydrogen phosphates are not particularly limited and may be sodium salts, potassium salts, calcium salts, magnesium salts, ammonium salts, chloride salts, bromide salts, fluoride salts, iodide salts, etc.

[0037] The amino acid may be any one or more α-amino acids selected from the group consisting of alanine, arginine, asparagine, aspartic acid, cysteine, glutamine, glutamic acid, glycine, histidine, isoleucine, leucine, lysine, methionine, phenylalanine, proline, serine, threonine, tryptophan, tyrosine, and valine. The amino acid is preferably any one or more selected from the group consisting of glutamic acid, arginine, lysine, glycine, serine, glutamine, histidine, phenylalanine, alanine, and proline, more preferably any one or more selected from the group consisting of glutamic acid, arginine, lysine, glycine, serine, glutamine, histidine, and phenylalanine, and even more preferably any one or more selected from the group consisting of glutamic acid, arginine, lysine, and glycine.

[0038] The salt of the amino acid is also not particularly limited, and may be a sodium salt, potassium salt, calcium salt, magnesium salt, ammonium salt, or the like.

[0039] The content of the compound containing one or more atoms selected from a nitrogen atom, a sulfur atom, and a phosphorus atom in the phenolic composition is not particularly limited as long as the technical effects of the present disclosure are achieved. In order to fully exhibit the performance of phenols and to also exhibit the effects of the phenolic composition, the upper limit of the compound containing one or more atoms selected from a nitrogen atom, a sulfur atom, and a phosphorus atom in the phenolic composition can be, for example, 1,000,000 ppm, preferably 900,000 ppm, more preferably 800,000 ppm, even more preferably 700,000 ppm, even more preferably 600,000 ppm, particularly preferably 500,000 ppm, and even more particularly preferably 400,000 ppm. Furthermore, since the performance of phenols can be fully exhibited and the effect of the phenol composition can also be achieved, the lower limit of the content of the compound containing one or more atoms selected from a nitrogen atom, a sulfur atom, and a phosphorus atom in the phenol composition can be, for example, 0.01 ppm or 0.02 ppm, preferably 0.03 ppm or 0.04 ppm, more preferably 0.05 ppm or 0.06 ppm, even more preferably 0.07 ppm or 0.08 ppm, and particularly preferably 0.09 ppm or 0.1 ppm. The above upper and lower limits can be combined as desired. For example, the content of the compound containing one or more atoms selected from a nitrogen atom, a sulfur atom, and a phosphorus atom in the phenol composition can be, for example, 0.01 ppm to 1,000,000 ppm or 0.02 ppm to 900,000 ppm, preferably 0.03 ppm to 800,000 ppm or 0.04 ppm to 700,000 ppm, more preferably 0.05 ppm to 600,000 ppm or 0.06 ppm to 500,000 ppm, even more preferably 0.07 ppm to 500,000 ppm or 0.08 ppm to 500,000 ppm, and particularly preferably 0.09 ppm to 500,000 ppm or 0.1 ppm to 400,000 ppm.The above-mentioned content may be the content of one compound containing one or more atoms selected from nitrogen atoms, sulfur atoms, and phosphorus atoms, or the total content of two or more compounds. The method for measuring compounds containing one or more atoms selected from nitrogen atoms, sulfur atoms, and phosphorus atoms contained in phenols is not particularly limited, and can be performed by known methods. For example, the measurement can be performed using methods such as liquid chromatography, gas chromatography, and mass spectrometry. Pretreatment such as derivatization can also be performed as necessary.

[0040] The content of phenols in the phenol composition is not particularly limited as long as the technical effects of the present disclosure are achieved, but may be, for example, 50 wt% or more of the total composition. Here, the phenol content of 50 wt% or more refers to the content of one type of phenol, and does not include cases where the total content of two or more types is 50 wt% or more. For example, if the phenol content is 25 wt% and the catechol content is 25 wt%, this does not constitute a "phenol content of 50 wt% or more." If the phenol content is 50 wt% and the catechol content is 25 wt%, this constitutes a "phenol content of 50 wt% or more."

[0041] The phenol composition according to the present disclosure may contain components other than phenols and compounds containing one or more atoms selected from a nitrogen atom, a sulfur atom, and a phosphorus atom, as long as the technical effects of the present disclosure are achieved. Examples of such components include inorganic salts such as magnesium chloride, calcium chloride, potassium chloride, and sodium chloride, and fats and oils such as triglycerides and diglycerides.

[0042] [Test Example 1: Test 1: Improvement of Phenol Biodegradability by Addition of Ammonium Chloride, Sodium Nitrate, Sodium Sulfate, or Dipotassium Hydrogen Phosphate] To evaluate the biodegradability of phenol by elemental addition, biological oxygen demand (BOD) was measured. Oxitop (Central Chemical Co., Ltd.) was used for BOD measurement. 100 mL of water containing 270 ppm phenol and various concentrations of additives was prepared as a substrate solution. Activated sludge was added to the substrate solution to achieve a MLSS of approximately 200 mg / L, and the solution was incubated at 30°C and 120 rpm in a TAITEC BR-43FM medium-sized thermostatic shaking incubator. The following activated sludge was used: Collection location: Mitsubishi Chemical Corporation's business facility. Physical properties: MLSS (activated sludge suspended solids amount): 8000 to 9000 mg / L, MLVSS (activated sludge organic suspended solids amount): 7000 to 8000 mg / L, SV30 (activated sludge sedimentation rate): 90 to 99%. Constituent bacterial flora: Acholeplasma sp., Anaerocella sp., Aquamicrobium sp., Blastopirellula sp., Brumimicrobium sp., Constrictibacter sp., Cryomorpha sp., Erysipelothrix sp. Erythrobacter, Flavobacterium, Gracilimonas, Halomonas, Leucobacter, Luteococcus, Marinobacter, Marinobacterium, Moheibacter, N ocardioides, Oceanibaculum, Parapusillimonas, Parvibaculum, Phyllobacterium, Proteiniclasticum, Pseudomonas, Pusillimonas, Rhod Bacteria belonging to the genus Ococcus, Rubellimicrobium, Sphaerochaeta, Sphingobium, Stenotrophomonas, Sulfurospirillum, Thiopseudomonas, and Truepera are present.

[0043] MLSS was measured according to the provisions of JIS K 0102, "14.1 Suspended Solids." MLVSS was measured with reference to JIS K 0102, "14.5 Loss on Ignition." SV30 was calculated as the percentage of sludge left to stand in a measuring cylinder for 30 minutes. Analysis of the bacterial flora of activated sludge was performed based on the base sequence information of 16S rRNA read by a next-generation sequencer.

[0044] The additives used were NH4Cl and NaNO3 as nitrogen-containing compounds, Na2SO4 as sulfur-containing compound, and K2HPO4 as phosphorus-containing compound. The amount of each salt added was calculated as the concentration of the N, S, and P atoms alone. As a reaction blank, a substrate solution containing only phenol was prepared and incubated in the same manner. The blank measurement value was subtracted from the measurement value of each sample, and the degree of decomposition was compared.

[0045] The results are shown in Tables 1 to 4. Improvement in biodegradation was confirmed for phenol to which each additive was added.

[0046]

[0047]

[0048]

[0049]

[0050] Test Example 2: Test 2 for improving the biodegradability of phenol by adding ammonium chloride, sodium nitrate, sodium sulfate, or dipotassium hydrogen phosphate 1. Materials and Methods Biophenol was produced with reference to the method described in Japanese Patent Application Laid-Open No. 2025-35380. It was confirmed that the biophenol did not contain aniline. A phenol composition was prepared by mixing 500 mg of biophenol with 50 mg or 150 mg of additive. A substrate solution with the composition shown in Table 5 was prepared using the phenol composition and activated sludge.

[0051]

[0052] The substrate solution was dispensed into 500 mL bottles, and biological oxygen demand (BOD) measurements were performed to evaluate the biodegradability of phenol with added elements. Oxitop (Central Chemical Co., Ltd.) was used for BOD measurements. The substrate solution was incubated at 30°C and 120 rpm in a TAITEC BR-43FM medium-sized constant temperature shaking incubator.

[0053] The following activated sludge was used. Collection location: Mitsubishi Chemical Corporation business facility. Physical properties: MLSS (activated sludge suspended solids): 8000-9000 mg / L, MLVSS (activated sludge organic suspended solids): 7000-8000 mg / L, SV30 (activated sludge settling rate): 90-99%. Constituent bacterial flora: Acholeplasma genus, Anaerocella genus, Aquamicrobium genus, Blastopirellula genus, Brumimicrobium genus, Constrictibacter genus, Cryomorpha genus, Erysipelothrix genus, Erythrobacter genus, Flavobacterium genus, Gracilimonas genus, Halomonas genus, Leucobacter genus, Luteococcus genus, Marinobacter genus, Marinobacterium genus, Moheibacter genus, N ocardioides, Oceanibaculum, Parapusillimonas, Parvibaculum, Phyllobacterium, Proteiniclasticum, Pseudomonas, Pusillimonas, Rhod Bacteria belonging to the genus Ococcus, Rubellimicrobium, Sphaerochaeta, Sphingobium, Stenotrophomonas, Sulfurospirillum, Thiopseudomonas, and Truepera are present.

[0054] MLSS was measured according to the provisions of JIS K 0102, "14.1 Suspended Solids." MLVSS was measured with reference to JIS K 0102, "14.5 Loss on Ignition." SV30 was calculated as the percentage of sludge left to stand in a measuring cylinder for 30 minutes. Analysis of the bacterial flora of activated sludge was performed based on the base sequence information of 16S rRNA read by a next-generation sequencer.

[0055] The additives used were NH4Cl and NaNO3 as nitrogen-containing compounds, Na2SO4 as sulfur-containing compound, and K2HPO4 as phosphorus-containing compound. A substrate solution containing only phenol was prepared as a reaction blank and incubated in the same manner. The blank measurement value was subtracted from the measurement value of each sample to compare the degree of decomposition.

[0056] 2. Results The results are shown in Tables 6 to 9. Improvement in biodegradation was confirmed after 320 hours for phenol with each additive added.

[0057]

[0058]

[0059]

[0060]

[0061] Test Example 3: Test 3 for improving the biodegradability of phenol by adding ammonium chloride, sodium nitrate, sodium sulfate, or dipotassium hydrogen phosphate 1. Materials and Methods Biophenol was produced with reference to the method described in Japanese Patent Application Laid-Open No. 2025-35380. It was confirmed that the biophenol did not contain aniline. A phenol composition was prepared by mixing 150 mg of two or more different additives with 500 mg of biophenol. A substrate solution with the composition shown in Table 10 was prepared using the phenol composition and activated sludge.

[0062]

[0063] The substrate solution was dispensed into 500 mL bottles, and biological oxygen demand (BOD) measurements were performed to evaluate the biodegradability of phenol with added elements. Oxitop (Central Chemical Co., Ltd.) was used for BOD measurements. The substrate solution was incubated at 30°C and 120 rpm in a TAITEC BR-43FM medium-sized constant temperature shaking incubator.

[0064] The following activated sludge was used. Collection location: Mitsubishi Chemical Corporation business facility. Physical properties: MLSS (activated sludge suspended solids): 8000-9000 mg / L, MLVSS (activated sludge organic suspended solids): 7000-8000 mg / L, SV30 (activated sludge settling rate): 90-99%. Constituent bacterial flora: Acholeplasma genus, Anaerocella genus, Aquamicrobium genus, Blastopirellula genus, Brumimicrobium genus, Constrictibacter genus, Cryomorpha genus, Erysipelothrix genus, Erythrobacter genus, Flavobacterium genus, Gracilimonas genus, Halomonas genus, Leucobacter genus, Luteococcus genus, Marinobacter genus, Marinobacterium genus, Moheibacter genus, N ocardioides, Oceanibaculum, Parapusillimonas, Parvibaculum, Phyllobacterium, Proteiniclasticum, Pseudomonas, Pusillimonas, Rhod Bacteria belonging to the genus Ococcus, Rubellimicrobium, Sphaerochaeta, Sphingobium, Stenotrophomonas, Sulfurospirillum, Thiopseudomonas, and Truepera are present.

[0065] MLSS was measured according to the provisions of JIS K 0102, "14.1 Suspended Solids." MLVSS was measured with reference to JIS K 0102, "14.5 Loss on Ignition." SV30 was calculated as the percentage of sludge left to stand in a measuring cylinder for 30 minutes. Analysis of the bacterial flora of activated sludge was performed based on the base sequence information of 16S rRNA read by a next-generation sequencer.

[0066] The additives used were NH4Cl as a nitrogen-containing compound, Na2SO4 as a sulfur-containing compound, and K2HPO4 as a phosphorus-containing compound. A substrate solution containing only phenol was prepared as a reaction blank and incubated in the same manner. The blank measurement value was subtracted from the measurement value of each sample to compare the degree of decomposition.

[0067] 2. Results The results are shown in Tables 11 to 14. Improvement in biodegradation was confirmed after 40 hours for phenol to which each additive was added.

[0068]

[0069]

[0070]

[0071]

[0072] Test Example 4: Test for improving phenol biodegradability by adding amino acids 1. Materials and methods Activated sludge was used to prepare a reaction solution with the following composition: Additives included amino acids: alanine, serine, sodium glutamate, glutamine, arginine, lysine, methionine, histidine, proline, phenylalanine, and glycine.

[0073]

[0074] The reaction mixture was dispensed into 14 mL polypropylene test tubes and incubated at 30°C and 180 rpm for approximately 6 hours in a TAITEC BR-43FM medium-sized thermostatic shaker. The reaction mixture was centrifuged at 15,000 rpm for 5 minutes, and the supernatant was subjected to HPLC analysis. The amount of residual phenol was quantified based on UV absorption at 210 nm.

[0075] The HPLC analysis conditions were as follows: Column: ULTRON PS-80H (ID 2.0 mm × 250 mm) Mobile phase: 0.1% perchloric acid aqueous solution Column temperature: 60°C Flow rate: 1 mL Analysis time: 36 min / sample

[0076] 2. Results The results are shown in Table 16. The phenol compositions containing glutamic acid, arginine, lysine, or glycine had a residual phenol content of 78.7% or less compared to the phenol composition (CTRL) without these additives, confirming improved phenol biodegradability. The phenol compositions containing serine, glutamine, histidine, or phenylalanine also had a residual phenol content of 88.4% or less compared to CTRL. The phenol compositions containing alanine or proline also had a residual phenol content of 95.2% or less compared to CTRL.

[0077]

[0078] [Test Example 5: Test for Improvement of Phenol Photostability by Addition of Ammonium Chloride, Sodium Nitrate, Sodium Sulfate, or Dipotassium Hydrogen Phosphate] A 5 mM aqueous phenol solution was supplemented with additives to form a reaction solution. The additives used were dipotassium hydrogen phosphate (KHPO) as a phosphorus-containing compound or sodium sulfate (NaSO) as a sulfur-containing compound. 10 mL of the reaction solution was dispensed into a 90 mm round dish, and a handy UV lamp (AS ONE #1-5479-07) was placed directly above the plate, with the light source facing upward. Two identical dishes were used as stands, with the dish containing the sample inserted in the center. The sample was irradiated with 252 nm light for 30 minutes. After the reaction, 200 μL of the sample was sampled, and the amount of phenol was quantified by LC analysis.

[0079] The results are shown in Table 17. The table shows the amount of phenol decomposition in the samples with each additive added, with the amount of phenol decomposed in the sample with no additives (CTRL) set at 100%. Improved photostability was confirmed for phenol with each additive added.

[0080]

[0081] Test Example 6: Test 2 for Improving Phenol's Photostability by Adding Ammonium Chloride, Sodium Nitrate, Sodium Sulfate, or Dipotassium Hydrogen Phosphate Biophenol was produced using a method described in Japanese Patent Publication (Kokai) No. 2025-35380. It was confirmed that the biophenol contained no aniline. A phenol composition was prepared by mixing 500 mg of biophenol with 50 mg or 150 mg of additive in a 10 mL glass vial. The additives used were NH4Cl and NaNO3 as nitrogen-containing compounds, Na2SO4 as a sulfur-containing compound, and K2HPO4 as a phosphorus-containing compound.

[0082] The bottom of the glass vial containing the phenol composition was placed in close contact with the light source of a handy UV lamp (AS ONE #1-5479-07), and the vial was surrounded by aluminum foil and irradiated with 252 nm light for 30 minutes. After irradiation, 8 mL of water was added to the vial to completely dissolve the phenol, and the amount of phenol was quantified by LC analysis.

[0083] The results are shown in Table 18 below. The table shows the amount of phenol decomposition in the samples with each additive added, with the amount of phenol decomposition in the sample with no additives (CTRL) set at 100%. Improvements in light stability were confirmed for phenol with each additive added.

[0084]

Claims

1. At least one biomass-derived phenol represented by the following formula (1) is contained in an amount of 50 wt% or more. (R 1 ~R 5 and may be the same or different and each represent a hydroxyl group, a methyl group, a carboxyl group, or a hydrogen atom.) A phenol composition comprising: at least one compound containing one or more atoms selected from a nitrogen atom, a sulfur atom, and a phosphorus atom; 2. The phenolic composition of claim 1, wherein the compound containing one or more atoms selected from nitrogen atoms, sulfur atoms, and phosphorus atoms is selected from the group consisting of urea, ammonium salt compounds, nitrate compounds, amino acids, sulfates, phosphates, hydrogen phosphates, phospholipids, and nucleic acids.

3. The composition of claim 1, wherein the phenolic compound is selected from the group consisting of phenol, catechol, cresol, dimethylphenol, xylenol, resorcinol, hydroquinone, and 4-hydroxybenzoic acid.

4. The composition according to claim 1, wherein the compound containing one or more atoms selected from nitrogen atoms, sulfur atoms, and phosphorus atoms is contained in an amount of 0.01 to 1,000,000 ppm based on the mass of the phenols.

5. A method for improving the biodegradability and / or photostability of phenols in a phenol composition, wherein the phenols are biomass-derived phenols represented by the following formula (1), and the phenol composition contains at least one of these phenols in an amount of 50 wt % or more: (R 1 ~R 5 may be the same or different and each represents a hydroxyl group, a methyl group, a carboxyl group, or a hydrogen atom.) A method for producing a phenol composition, comprising adding at least one compound containing one or more atoms selected from a nitrogen atom, a sulfur atom, and a phosphorus atom in an amount of 0.01 to 1,000,000 ppm relative to the mass of the phenols.

6. A method for decomposing phenols, comprising the step of contacting the phenolic composition of claim 1 with activated sludge.

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