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 one or more substances selected from among amino acids, organic acids, and salts of these acids.

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 containing a phenolic compound and one or more selected from an amino acid, an organic acid, and a salt thereof, which exhibits improved biodegradability and / or photostability compared to a composition containing a phenolic compound but not containing an amino acid, an organic acid, or a salt thereof.

[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

[22] . [1] A biomass-derived phenolic composition comprising 50 wt% or more of at least one phenol represented by the following formula (1), (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 one or more selected from an amino acid, an organic acid, and a salt thereof (with the proviso that the organic acid is not the phenol). [2] The phenolic composition according to [1], which contains a phenol and exhibits improved biodegradability compared to a composition not containing the amino acid, the organic acid, or a salt thereof. [3] The phenolic composition according to [2], in which the amino acid is an α-amino acid. [4] The phenolic composition according to [3], in which 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. [5] The phenolic composition according to [1], which contains a phenol and exhibits improved photostability compared to a composition not containing the amino acid, the organic acid, or a salt thereof. [6] The phenolic composition according to [5], in which the amino acid is an α-amino acid. [7] The phenolic composition according to [6], wherein the α-amino acid is any one or more selected from the group consisting of histidine, arginine, glutamic acid, glutamine, proline, methionine, glycine, and lysine. [8] The phenolic composition according to [2] or [5], wherein the organic acid is any one or more selected from the group consisting of a hydroxycarboxylic acid having 10 or less carbon atoms, a linear carboxylic acid having 6 or less carbon atoms, and a ketocarboxylic acid having 6 or less carbon atoms. [9] The phenolic composition according to [8], wherein the hydroxycarboxylic acid is lactic acid, shikimic acid, and / or chorismic acid.

[10] The phenolic composition according to [8], wherein the carboxylic acid is formic acid and / or acetic acid.

[11] The phenolic composition according to [8], wherein the ketocarboxylic acid is pyruvic acid.

[0006]

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

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

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

[12] , wherein the phenols contain one or more selected from the amino acids, organic acids, and salts thereof in an amount of 0.01 to 1,000,000 ppm based on the mass of the phenols.

[0007]

[14] 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:

[0008] (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 one or more selected from amino acids, organic acids, and salts thereof (with the proviso that the organic acids are not the phenols) in an amount of 0.01 to 1,000,000 ppm relative to the mass of the phenols in the phenol composition.

[15] The method according to

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

[16] The method according to

[15] , 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, or one or more selected from the group consisting of histidine, arginine, glutamic acid, glutamine, proline, methionine, glycine, and lysine.

[17] The method according to

[14] , wherein the organic acid is one or more selected from the group consisting of a hydroxycarboxylic acid having 10 or less carbon atoms, a linear carboxylic acid having 6 or less carbon atoms, and a ketocarboxylic acid having 6 or less carbon atoms.

[18] The method according to

[17] , wherein the hydroxycarboxylic acid is lactic acid, shikimic acid, and / or chorismic acid.

[19] The method according to

[17] , wherein the carboxylic acid is formic acid and / or acetic acid.

[20] The method according to

[17] , wherein the ketocarboxylic acid is pyruvic acid.

[0009]

[21] The method according to any one of

[14] to

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

[0010]

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

[13] with activated sludge.

[0011] The present disclosure also provides the following [1A] to [28A]. [1A] A composition or highly biodegradable composition comprising a phenol and one or more selected from an amino acid, an organic acid, and a salt thereof. [2A] The composition of [1A], which comprises a phenol and exhibits improved biodegradability compared to a composition not containing the amino acid, the organic acid, or a salt thereof. [3A] The composition of [2A], in which the amino acid is an α-amino acid. [4A] The composition of [3A], in which 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. [5A] The composition of [4A], in which the α-amino acid is any one or more selected from the group consisting of glutamic acid, arginine, lysine, and glycine. [6A] The composition of [4A], wherein the α-amino acid is any one or more selected from the group consisting of serine, glutamine, histidine, and phenylalanine. [7A] The composition of [4A], wherein the α-amino acid is alanine and / or proline. [8A] The composition of [2A], wherein the organic acid is a hydroxycarboxylic acid having 10 or less carbon atoms. [9A] The composition of [8A], wherein the hydroxycarboxylic acid is lactic acid, shikimic acid, and / or chorismic acid. [10A] The composition of [2A], wherein the organic acid is a straight-chain carboxylic acid having 6 or less carbon atoms. [11A] The composition of [10A], wherein the carboxylic acid is formic acid and / or acetic acid. [12A] The composition of [2A], wherein the organic acid is a ketocarboxylic acid having 6 or less carbon atoms. [13A] The composition of [12A], wherein the ketocarboxylic acid is pyruvic acid. [14A] Any of the compositions [1A] to [13A], wherein the phenols are any one or more selected from the group consisting of phenol, catechol, cresol, dimethylphenol, xylenol, resorcinol, and hydroquinone. [15A] Any of the compositions [1A] to [14A], wherein the phenols are any one or more selected from the group consisting of amino acids, organic acids, and salts thereof, in an amount of 0.01 to 10,000 ppm based on the mass of the phenols.

[0012] [16A] A method for improving the biodegradability of phenols in a phenol composition, comprising incorporating one or more selected from amino acids, organic acids, and salts thereof in the composition at 0.01 to 10,000 ppm relative to the mass of the phenols. [17A] The method according to [16A], wherein the amino acid is an α-amino acid. [18A] The method according to [17A], 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. [19A] The method according to [18A], wherein the α-amino acid is one or more selected from the group consisting of glutamic acid, arginine, lysine, and glycine. [20A] The method according to [18A], wherein the α-amino acid is one or more selected from the group consisting of serine, glutamine, histidine, and phenylalanine. [21A] The method of [18A], wherein the α-amino acid is alanine and / or proline. [22A] The method of [16A], wherein the organic acid is a hydroxycarboxylic acid having 10 or fewer carbon atoms. [23A] The method of [22A], wherein the hydroxycarboxylic acid is lactic acid, shikimic acid, and / or chorismic acid. [24A] The method of [16A], wherein the organic acid is a straight-chain carboxylic acid having 6 or fewer carbon atoms. [25A] The method of [24A], wherein the carboxylic acid is formic acid and / or acetic acid. [26A] The method of [16A], wherein the organic acid is a ketocarboxylic acid having 6 or fewer carbon atoms. [27A] The method of [26A], wherein the ketocarboxylic acid is pyruvic acid. [28A] Any of the methods [16A] to [27A], wherein the phenol is one or more selected from the group consisting of phenol, catechol, cresol, dimethylphenol, xylenol, resorcinol, and hydroquinone.

[0013] The present disclosure further provides the following [1B] to [26B]. [1B] A composition or a highly photostable composition comprising a phenol and one or more selected from an amino acid, an organic acid, and a salt thereof. [2B] The composition of [1B], which comprises a phenol and exhibits improved photostability compared to a composition not containing the amino acid, the organic acid, or a salt thereof. [3B] The composition of [2B], in which the amino acid is an α-amino acid. [4B] The composition of [3B], in which the α-amino acid is one or more selected from the group consisting of histidine, arginine, glutamic acid, glutamine, proline, methionine, glycine, and lysine. [5B] The composition of [4B], in which the α-amino acid is histidine and / or arginine. [6B] The composition of [4B], in which the α-amino acid is one or more selected from the group consisting of glutamic acid, glutamine, proline, methionine, glycine, and lysine. [7B] The composition of [2B], wherein the organic acid is a hydroxycarboxylic acid having 10 or less carbon atoms. [8B] The composition of [7B], wherein the hydroxycarboxylic acid is lactic acid, shikimic acid, and / or chorismic acid. [9B] The composition of [2B], wherein the organic acid is a straight-chain carboxylic acid having 6 or less carbon atoms. [10B] The composition of [9B], wherein the carboxylic acid is formic acid and / or acetic acid. [11B] The composition of [2B], wherein the organic acid is a ketocarboxylic acid having 6 or less carbon atoms. [12B] The composition of [11B], wherein the ketocarboxylic acid is pyruvic acid. [13B] Any of the compositions [1B] to [12B], wherein the phenol is one or more selected from the group consisting of phenol, catechol, cresol, dimethylphenol, xylenol, resorcinol, and hydroquinone. [14B] Any of the compositions [1B] to [13B], containing one or more selected from the amino acids, the organic acids, and salts thereof in an amount of 0.01 to 10,000 ppm based on the mass of the phenols.

[0014] [15B] A method for improving the photostability of phenols in a phenol composition, comprising incorporating one or more selected from amino acids, organic acids, and salts thereof in the composition at 0.01 to 10,000 ppm relative to the mass of the phenols. [16B] The method of [15B], wherein the amino acid is an α-amino acid. [17B] The method of [16B], wherein the α-amino acid is one or more selected from the group consisting of histidine, arginine, glutamic acid, glutamine, proline, methionine, glycine, and lysine. [18B] The method of [17B], wherein the α-amino acid is histidine and / or arginine. [19B] The method of [17B], wherein the α-amino acid is one or more selected from the group consisting of glutamic acid, glutamine, proline, methionine, glycine, and lysine. [20B] The method of [15B], wherein the organic acid is a hydroxycarboxylic acid having 10 or less carbon atoms. [21B] The method of [20B], wherein the hydroxycarboxylic acid is lactic acid, shikimic acid, and / or chorismic acid. [22B] The method of [15B], wherein the organic acid is a straight-chain carboxylic acid having 6 or less carbon atoms. [23B] The method of [22B], wherein the carboxylic acid is formic acid and / or acetic acid. [24B] The method of [15B], wherein the organic acid is a ketocarboxylic acid having 6 or less carbon atoms. [25B] The method of [24B], wherein the ketocarboxylic acid is pyruvic acid. [26B] Any of the methods [15B] to [25B], wherein the phenol is one or more selected from the group consisting of phenol, catechol, cresol, dimethylphenol, xylenol, resorcinol, and hydroquinone.

[0015] The present disclosure provides phenolic compositions with improved biodegradability and / or photostability.

[0016] 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.

[0017] The phenolic composition according to the present disclosure contains a phenol and one or more selected from amino acids, organic acids, and salts thereof other than phenols. It has been found that the biodegradability and / or photostability of the phenolic composition can be improved by including one or more selected from amino acids, organic acids, and salts thereof in the phenolic composition. One or more of the amino acids, organic acids, and salts thereof can be included in the phenolic composition.

[0018] 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.

[0019] 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.

[0020] 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.

[0021] 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 amino acids, organic acids, and salts thereof. 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.

[0022] 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.

[0023] 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.

[0024] The "improved photostability" of the phenolic composition according to the present disclosure means 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 amino acids, organic acids, and salts thereof. Specifically, the amount of decomposition of the phenolic composition according to the present disclosure, measured by the above-described measurement method involving 30 minutes of ultraviolet irradiation, is 1%, 2%, 3%, 4%, 5%, preferably 6%, 7%, 8%, 9%, 10%, more preferably 11%, 12%, 13%, 14%, 15%, and even more preferably 16%, 17%, 18%, 19%, 20% or more less than the amount of decomposition of the control composition.

[0025] Phenols are compounds represented by the following formula (1).

[0026] (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.

[0027] Specific examples of phenols include phenol, catechol, cresol, dimethylphenol, xylenol, resorcinol, hydroquinone, and 4-hydroxybenzoic acid.

[0028] 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 biomass-derived 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 fermentation.

[0029] In the present disclosure, one or more selected from amino acids, organic acids, and salts thereof 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 one or more selected from amino acids, organic acids, and salts thereof. The 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.

[0030] 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.

[0031] 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.

[0032] 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.

[0033] Examples of amino acids contained in the phenolic composition to improve biodegradability include 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 one or more selected from the group consisting of glutamic acid, arginine, lysine, glycine, serine, glutamine, histidine, phenylalanine, alanine, and proline, more preferably one or more selected from the group consisting of glutamic acid, arginine, lysine, glycine, serine, glutamine, histidine, and phenylalanine, and even more preferably one or more selected from the group consisting of glutamic acid, arginine, lysine, and glycine.

[0034] Examples of amino acids contained in the phenolic composition to improve photostability include 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 one or more selected from the group consisting of histidine, arginine, glutamic acid, glutamine, proline, methionine, glycine, and lysine, and more preferably histidine and / or arginine.

[0035] Examples of organic acids that are not phenols represented by formula (1) and that are contained in the phenol composition to improve biodegradability include hydroxycarboxylic acids having 10 or less carbon atoms, linear carboxylic acids having 6 or less carbon atoms, and ketocarboxylic acids having 6 or less carbon atoms.

[0036] Examples of organic acids that are not phenols represented by formula (1) and that are contained in the phenol composition to improve photostability include hydroxycarboxylic acids having 10 or less carbon atoms, linear carboxylic acids having 6 or less carbon atoms, and ketocarboxylic acids having 6 or less carbon atoms.

[0037] Examples of hydroxycarboxylic acids having 10 or fewer carbon atoms include one or more hydroxycarboxylic acids selected from the group consisting of glycolic acid (2-hydroxyacetic acid), lactic acid (2-hydroxypropionic acid), glyceric acid (2,3-dihydroxypropanoic acid), malic acid (2-hydroxybutanedioic acid), tartaric acid (2,3-dihydroxybutanedioic acid), tartronic acid (2-hydroxypropanedioic acid), citronic acid (2-hydroxy-1,2,3-propanetricarboxylic acid), gluconic acid (2,3,4,5,6-pentahydroxyhexanoic acid), mandelic acid (2-hydroxyphenylacetic acid), shikimic acid (3,4,5-trihydroxycyclohexa-1-carboxylic acid), chorismic acid (3-(3,4-dihydroxyphenyl)1-oxopropan-2-yloxyacetic acid), prephenic acid, and 7-phospho-2-dehydro-3-deoxyarabinoheptonic acid (DAH). The hydroxycarboxylic acids are preferably lactic acid, shikimic acid, and / or chorismic acid.

[0038] Examples of the straight-chain carboxylic acid having 6 or less carbon atoms include one or more straight-chain carboxylic acids selected from the group consisting of formic acid, acetic acid, propionic acid, malonic acid, butyric acid, succinic acid, valeric acid, glutaric acid, caproic acid, and adipic acid. The straight-chain carboxylic acid is preferably formic acid and / or acetic acid.

[0039] Examples of ketocarboxylic acids having 6 or less carbon atoms include one or more ketocarboxylic acids selected from the group consisting of pyruvic acid (2-oxopropionic acid), acetoacetic acid (3-oxobutanoic acid), levulinic acid (4-oxopentanoic acid), oxaloacetic acid (2-oxobutanoic acid), and α-ketoglutaric acid (2-oxopentanedioic acid). The ketocarboxylic acid is preferably pyruvic acid.

[0040] The salts of amino acids and organic acids are not particularly limited and may be sodium salts, potassium salts, calcium salts, magnesium salts, ammonium salts, etc.

[0041] The contents of the amino acids, organic acids, and salts thereof in the phenolic composition are 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 achieve the effects of the phenolic composition, the upper limit of the contents of the amino acids, organic acids, and salts thereof in the phenolic composition can be, for example, 1,000,000 ppm, preferably 800,000 ppm, more preferably 600,000 ppm, even more preferably 500,000 ppm, still more preferably 400,000 ppm, particularly preferably 300,000 ppm, and even particularly preferably 200,000 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 amino acids, organic acids, and salts thereof 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 in any desired manner. For example, the contents of amino acids, organic acids, and salts thereof in the phenolic composition can be, for example, 0.01 ppm to 1,000,000 ppm or 0.02 ppm to 800,000 ppm, preferably 0.03 ppm to 600,000 ppm or 0.04 ppm to 500,000 ppm, more preferably 0.05 ppm to 400,000 ppm or 0.06 ppm to 300,000 ppm, even more preferably 0.07 ppm to 200,000 ppm or 0.08 ppm to 200,000 ppm, and particularly preferably 0.09 ppm to 200,000 ppm or 0.1 ppm to 200,000 ppm. The above-mentioned contents may be the contents of one of the amino acids, organic acids, and salts thereof, or the total contents of two or more of them.The method for measuring the amino acids, organic acids, and salts thereof contained in phenols is not particularly limited, and can be performed by known methods. For example, 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.

[0042] 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, "a content of phenols of 50 wt% or more" refers to the content of one type, 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%, it is not considered a "phenol content of 50 wt% or more." If the phenol content is 50 wt% and the catechol content is 25 wt%, it is considered a "phenol content of 50 wt% or more."

[0043] The phenolic composition according to the present disclosure may contain components other than phenols, amino acids, organic acids, and their salts, as long as the technical effects of the present disclosure are achieved. Examples of such components include inorganic salts such as ammonium sulfate, ammonium chloride, ammonium nitrate, magnesium chloride, calcium chloride, potassium chloride, and sodium chloride, and fats and oils such as triglycerides and diglycerides.

[0044] Test Example 1: Evaluation of phenol biodegradability 1 1. Materials and methods Activated sludge was used to prepare a reaction solution with the composition shown in Table 1. The following activated sludge was used. Collection location: Mitsubishi Chemical Corporation business site. 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 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.

[0045] 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.

[0046] The additives used included amino acids such as alanine, serine, sodium glutamate, glutamine, arginine, lysine, methionine, histidine, proline, phenylalanine, and glycine, and organic acids such as shikimic acid, sodium pyruvate, sodium lactate, sodium acetate, and sodium formate.

[0047]

[0048] The reaction mixture was dispensed into 14 mL polypropylene test tubes and incubated at 30°C and 180 rpm for approximately 6 hours using 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.

[0049] 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

[0050] 2. Results The results are shown in Tables 2 and 3. The phenolic compositions containing glutamic acid, arginine, lysine, or glycine had a residual phenol content of 78.7% or less compared to the phenolic composition (CTRL) without these additives, confirming improved phenol biodegradability. The phenolic compositions containing serine, glutamine, histidine, or phenylalanine also had a residual phenol content of 88.4% or less compared to CTRL. The phenolic compositions containing alanine or proline also had a residual phenol content of 95.2% or less compared to CTRL. The phenolic compositions containing shikimic acid, sodium pyruvate, sodium lactate, sodium acetate, and sodium formate also had a reduced residual phenol content compared to CTRL, confirming improved phenol biodegradability.

[0051]

[0052]

[0053] Test Example 2: Evaluation of Phenol Biodegradability 2 1. Materials and Methods Biophenol was produced with reference to the method described in Japanese Patent Application Laid-Open No. 2025-35380. A phenol composition was prepared by mixing 500 mg of biophenol with 50 mg or 5 mg of additive. A reaction solution with the composition shown in Table 4 was prepared using the phenol composition and activated sludge. The following activated sludge was used: Collection location: Mitsubishi Chemical Corporation 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 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.

[0054] The additives used included amino acids such as alanine, serine, sodium glutamate monohydrate, glutamine, arginine, lysine, proline, phenylalanine, and glycine, and organic acids such as shikimic acid, sodium pyruvate, sodium lactate, sodium acetate, and sodium formate.

[0055]

[0056] The reaction mixture was dispensed into 14 mL polypropylene test tubes and incubated at 30°C and 180 rpm for approximately 5 hours using 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.

[0057] 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

[0058] 2. Results The results are shown in Tables 5 and 6. The residual phenol content of the phenolic compositions containing glutamic acid, glutamine, arginine, or phenylalanine was 38.3% or less compared to the phenolic composition (CTRL) without these additives, confirming improved phenol biodegradability. The residual phenol content of the phenolic compositions containing alanine, serine, or lysine was 73.9% or less compared to CTRL. The residual phenol content of the phenolic compositions containing proline or glycine was 86.4% or less compared to CTRL. The residual phenol content of the phenolic compositions containing shikimic acid, sodium pyruvate, sodium lactate, sodium acetate, and sodium formate was also reduced compared to CTRL, confirming improved phenol biodegradability.

[0059]

[0060]

[0061] Test Example 3: Evaluation of Phenol Photostability. A 5 mM aqueous phenol solution was supplemented with the following additives: sodium formate, sodium pyruvate, sodium lactate, sodium acetate, monosodium glutamate, glutamine, arginine, lysine, methionine, histidine, proline, glycine, and shikimic acid. This reaction mixture was prepared. 10 mL of the reaction mixture 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 positioned directly above. Two identical dishes were used as stands, with the sample dish inserted in the center. The mixture was then irradiated with 252 nm light for 30 minutes. After the reaction, 200 μL of the mixture was sampled, and the amount of phenol was quantified by LC analysis.

[0062] The results are shown in the table 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%. Improved photostability was confirmed for phenol with each additive added.

[0063]

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 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: one or more selected from amino acids, organic acids, and salts thereof (with the proviso that the organic acids are not the phenols); and 2. The phenolic composition of claim 1, wherein the amino acid is an α-amino acid.

3. The phenol composition according to claim 1, wherein the organic acid is at least one selected from the group consisting of hydroxycarboxylic acids having 10 or less carbon atoms, linear carboxylic acids having 6 or less carbon atoms, and ketocarboxylic acids having 6 or less carbon atoms.

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

5. The phenolic composition according to claim 1, which contains 0.01 to 1,000,000 ppm of one or more selected from the amino acids, organic acids and salts thereof based on the mass of the phenolic compound.

6. 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.) The method for producing a phenolic composition, characterized in that the phenolic composition contains one or more selected from amino acids, organic acids, and salts thereof (with the proviso that the organic acids are not the phenols) in an amount of 0.01 to 1,000,000 ppm relative to the mass of the phenols.

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

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