Method for producing branched alkyl glyceryl ether derived from organism and branched alkyl glyceryl ether derived from organism produced thereby

Abstract

The present invention provides a method for producing a branched alkyl glyceryl ether derived from a biological source, and a branched alkyl glyceryl ether derived from a biological source obtained by the production method. Said production method comprises a step wherein a biogenic linear primary alcohol selected from the group consisting of a linear alkyl group having 3-6 carbon atoms, a linear primary alcohol having a linear alkenyl group having 3-6 carbon atoms, a linear aldehyde having a linear alkyl group having 3-6 carbon atoms, and a linear aldehyde having 3-3 carbon atoms, a step for dimerizing one or more types of bioderived linear aldehydes having a linear alkenyl group having 6 to 12 carbon atoms to obtain a bioderived branched primary alcohol having a branched alkyl group having 6 to 12 carbon atoms; and a step for producing a bio-derived branched alkyl glyceryl ether using the obtained bio-derived branched primary alcohol.

Description

Technical Field

[0001] The present invention relates to a method for producing a bio-derived branched alkyl glyceryl ether, which can obtain a bio-derived branched alkyl glyceryl ether with suppressed odor using a bio-derived raw material. Background Art

[0002] Antimicrobial agents are generally used in cosmetics, detergents, and the like for the purpose of preservation, and among them, alkyl glyceryl ethers are known to be used as compounds that are highly safe for the human body (for example, Patent Documents 1 and 2).

[0003] However, it is known that such alkyl glyceryl ethers may cause oxidative degradation during storage, decomposition over time, and unpleasant odors depending on their structures and production methods. As a countermeasure, for example, Patent Document 3 describes a method for producing a composition containing glyceryl ether that can maintain quality over a long period of time.

[0004] In recent years, in the entire field of chemical products including cosmetic ingredients, it has been sought to use some or all of the raw materials used in production from the perspective of environmental considerations, etc. Influenced by this trend, the market has demanded the development of a method for producing a composition containing glyceryl ether, which can use raw materials of biological origin and maintain quality for a long time by a simple method. Prior art literature

[0005] Patent Literature Patent Document 1: Japanese Patent Application Laid-Open No. 51-076424 Patent Document 2: Japanese Patent Application Laid-Open No. 08-310947 Patent Document 3: International Publication No. 2020 / 066893 Summary of the invention Problems to be solved by the invention

[0006] An object of the present invention is to provide a method for producing a bio-derived branched alkyl glyceryl ether, which can obtain a bio-derived branched alkyl glyceryl ether with suppressed odor using a bio-derived raw material. Means of solving problems

[0007] Therefore, the present inventors have conducted intensive research and have completed the present invention. That is, the present invention is a method for producing a bio-derived branched alkyl glyceryl ether, which comprises the following steps: a step of dimerizing one or more selected from a bio-derived linear primary alcohol having a linear alkyl group having 3 to 6 carbon atoms, a bio-derived linear primary alcohol having a linear alkenyl group having 3 to 6 carbon atoms, a bio-derived linear aldehyde having a linear alkyl group having 3 to 6 carbon atoms, and a bio-derived linear aldehyde having a linear alkenyl group having 3 to 6 carbon atoms to obtain a bio-derived branched primary alcohol having a branched alkyl group having 6 to 12 carbon atoms; and a step of producing a bio-derived branched alkyl glyceryl ether using the obtained bio-derived branched primary alcohol. Effects of the Invention

[0008] According to the present invention, there is provided a method for producing a bio-derived branched alkyl glyceryl ether, which can obtain a bio-derived branched alkyl glyceryl ether with suppressed odor using a bio-derived raw material. DETAILED DESCRIPTION

[0009] The bio-derived straight-chain primary alcohol used in the present invention is one or more selected from bio-derived straight-chain primary alcohols having a straight-chain alkyl group having 3 to 6 carbon atoms and bio-derived straight-chain primary alcohols having a straight-chain alkenyl group having 3 to 6 carbon atoms obtained from plant resources, etc., for example, primary alcohols obtained by refining and / or separating plant oils such as palm oil, palm kernel oil, soybean oil, rapeseed oil, castor oil, olive oil, cottonseed oil, coconut oil, corn oil, safflower oil, sesame oil, sunflower seed oil, camellia oil, and linseed oil; Primary alcohols obtained by fermenting and / or metabolizing biomass from corn, sugar cane, beets, bananas, wheat, barley, rye, potatoes, sweet potatoes, cassava, taro, broad beans, lentils, peas, etc. using microorganisms; and primary alcohols obtained by synthesizing various biological compounds obtained from plant resources such as palm oil, palm kernel oil, soybean oil, rapeseed oil, castor oil, olive oil, cottonseed oil, coconut oil, corn oil, safflower oil, sesame oil, sunflower seed oil, camellia oil, linseed oil, etc. as raw materials.

[0010] The method for obtaining a bio-derived straight-chain primary alcohol having a straight-chain alkyl group having 3 to 6 carbon atoms or a bio-derived straight-chain primary alcohol having a straight-chain alkenyl group having 3 to 6 carbon atoms by refining and / or separating the above-mentioned vegetable oil is not particularly limited, and a known method can be used, or a method of producing the alcohol from a fatty acid obtained by hydrolyzing a fatty acid glyceride contained in the vegetable oil can be used. In this case, the method of producing a bio-derived straight-chain primary alcohol having a straight-chain alkyl group having 3 to 6 carbon atoms or a bio-derived straight-chain primary alcohol having a straight-chain alkenyl group having 3 to 6 carbon atoms from a fatty acid can be a known method, for example, a method of hydrogenating a fatty acid after methyl esterification, or a method of directly hydrogenating a fatty acid, etc.

[0011] In addition, the method for obtaining a bio-derived straight-chain primary alcohol having a straight-chain alkyl group with 3 to 6 carbon atoms or a bio-derived straight-chain primary alcohol having a straight-chain alkenyl group with 3 to 6 carbon atoms by fermenting the above-mentioned biomass using a microorganism is not particularly limited, and a known method can be used. For example, a method in which sugars such as cellulose obtained from biomass are fermented and / or metabolized by microorganisms such as fungi, enzymes, yeasts, etc. under an appropriate temperature, humidity, atmosphere, etc.

[0012] In addition, the method of synthesizing a bio-derived straight-chain primary alcohol having a straight-chain alkyl group with 3 to 6 carbon atoms or a bio-derived straight-chain primary alcohol having a straight-chain alkenyl group with 3 to 6 carbon atoms using various bio-derived compounds obtained from the above-mentioned plant resources and the like as raw materials is not particularly limited, and a known method can be used. In this case, a bio-derived straight-chain primary alcohol having a hydrocarbon group with the same carbon number as the bio-derived compound used as a raw material can be produced, and a bio-derived straight-chain primary alcohol having a hydrocarbon group with a different carbon number from the bio-derived compound used as a raw material can also be produced. As such a method, for example, a method of hydrogenating a bio-derived straight-chain aldehyde having a straight-chain alkyl group with 3 to 6 carbon atoms or a bio-derived straight-chain aldehyde having a straight-chain alkenyl group with 3 to 6 carbon atoms by a known method; a method of oxidizing or dehydrogenating a bio-derived alcohol such as ethanol or propanol by a known method to obtain an aldehyde compound, and then condensing and hydrogenating the obtained aldehyde compound, etc.

[0013] As the bio-derived straight-chain primary alcohol having a straight-chain alkyl group with 3 to 6 carbon atoms used in the present invention, there is no particular limitation as long as it is a bio-derived straight-chain primary alcohol having a straight-chain alkyl group and a hydroxyl group in the molecule, and specific examples thereof include: bio-derived n-propanol (1-propanol), bio-derived n-butanol (1-butanol), bio-derived n-pentanol (1-pentanol), bio-derived n-hexanol (1-hexanol), etc. As the bio-derived straight-chain primary alcohol having a straight-chain alkenyl group with 3 to 6 carbon atoms, there is no particular limitation as long as it is a bio-derived straight-chain primary alcohol having a straight-chain alkenyl group and a hydroxyl group in the molecule, and specific examples thereof include: bio-derived n-propenol (allyl alcohol), bio-derived n-butenol (butenol), bio-derived n-pentenol, bio-derived n-hexenol, etc. Among them, from the viewpoint of obtaining a bio-derived branched alkyl glyceryl ether with more suppressed odor, it is preferred to use bio-derived n-butanol (1-butanol) as the bio-derived straight-chain primary alcohol. These biologically derived linear primary alcohols are not particularly limited as long as they are obtained from plant resources or the like by a known method.

[0014] The bio-derived straight-chain aldehyde used in the present invention is one or more selected from bio-derived straight-chain aldehydes having a straight-chain alkyl group having 3 to 6 carbon atoms and bio-derived straight-chain aldehydes having a straight-chain alkenyl group having 3 to 6 carbon atoms obtained from plant resources, etc., for example, aldehydes obtained by fermenting and / or metabolizing biomass derived from corn, sugar cane, sugar beet, banana, wheat, barley, rye, potato, sweet potato, cassava, taro, broad bean, lentil, pea, etc. using microorganisms, and aldehydes synthesized using various bio-derived compounds such as bio-derived straight-chain primary alcohols obtained from plant resources such as palm oil, palm kernel oil, soybean oil, rapeseed oil, castor oil, olive oil, cottonseed oil, coconut oil, corn oil, safflower oil, sesame oil, sunflower seed oil, camellia oil, linseed oil, etc. as raw materials.

[0015] The method for obtaining a bio-derived linear aldehyde having a linear alkyl group with 3 to 6 carbon atoms or a bio-derived linear aldehyde having a linear alkenyl group with 3 to 6 carbon atoms by fermenting the above-mentioned biomass using a microorganism is not particularly limited, and a known method can be used. A method in which sugars such as cellulose obtained from biomass are fermented and / or metabolized by microorganisms such as fungi, enzymes, yeasts, etc. under an appropriate temperature, humidity, atmosphere, etc. can be used.

[0016] In addition, the method of synthesizing a bio-derived linear aldehyde having a linear alkyl group having 3 to 6 carbon atoms or a bio-derived linear aldehyde having a linear alkenyl group having 3 to 6 carbon atoms using various bio-derived compounds such as bio-derived linear primary alcohols obtained from the above-mentioned plant resources as raw materials is not particularly limited, and a known method can be used. In this case, a bio-derived linear aldehyde having a hydrocarbon group having the same carbon number as that of the bio-derived compound used as a raw material can be produced, and a bio-derived linear aldehyde having a hydrocarbon group having a different carbon number from that of the bio-derived compound used as a raw material can also be produced and used in the present invention. Examples of such methods include: a method of oxidizing or dehydrogenating a bio-derived linear primary alcohol having a linear alkyl group of 3 to 6 carbon atoms or a bio-derived linear primary alcohol having a linear alkenyl group of 3 to 6 carbon atoms by a known method; a method of producing an aldehyde having an increased carbon number by hydroformylation using an olefin having 2 to 5 carbon atoms, carbon monoxide, and hydrogen by an oxo method; a method of producing an aldehyde having an increased carbon number by condensing an aldehyde having 2 to 4 carbon atoms obtained by oxidizing or dehydrogenating a bio-derived alcohol such as ethanol or propanol by a known method, etc. In the present invention, as the bio-derived linear aldehyde, it is preferred to use a bio-derived linear primary alcohol having a linear alkyl group of 3 to 6 carbon atoms or a bio-derived linear primary alcohol having a linear alkenyl group of 3 to 6 carbon atoms by a known method, from the viewpoint of obtaining a bio-derived branched alkyl glyceryl ether with further suppressed odor.

[0017] As the bio-derived straight-chain aldehyde having a straight-chain alkyl group with 3 to 6 carbon atoms used in the present invention, there is no particular limitation as long as it is a bio-derived straight-chain aldehyde having a straight-chain alkyl group and an aldehyde group in the molecule and having 3 to 6 carbon atoms, and specific examples thereof include: bio-derived n-propanal (propanal), bio-derived n-butyraldehyde (butyraldehyde), bio-derived n-valeraldehyde (valeraldehyde), and bio-derived n-hexanal (hexanal). As the bio-derived straight-chain aldehyde having a straight-chain alkenyl group with 3 to 6 carbon atoms, there is no particular limitation as long as it is a bio-derived straight-chain aldehyde having a straight-chain alkenyl group and an aldehyde group in the molecule and having 3 to 6 carbon atoms, and specific examples thereof include: bio-derived n-acrolein (acrolein, acrolein), bio-derived n-butenal (butenal, crotonaldehyde), bio-derived n-pentenal (pentenal), and bio-derived n-hexenal (hexenal). Among them, from the viewpoint of obtaining a bio-derived branched alkyl glyceryl ether with further suppressed odor, it is preferred to use bio-derived n-butyraldehyde (butyraldehyde) as the bio-derived straight-chain aldehyde. These bio-derived straight-chain aldehydes can be used without particular limitation as long as they are obtained by a known method from plant resources, etc. For example, when using bio-derived n-butyraldehyde as the bio-derived straight-chain aldehyde having a straight-chain alkyl group with 3 to 6 carbon atoms, bio-derived n-butyraldehyde obtained by oxidizing or dehydrogenating bio-derived butanol by a known method, bio-derived n-butyraldehyde obtained by hydroformylating bio-derived propylene by an oxo method, etc. can be used. In the present invention, from the viewpoint of obtaining a bio-derived branched alkyl glyceryl ether having particularly suppressed odor, it is particularly preferable to use bio-derived n-butyraldehyde obtained by oxidizing or dehydrogenating bio-derived n-butanol by a known method as the bio-derived straight-chain aldehyde.

[0018] As a method for dimerizing one or more selected from a bio-derived linear primary alcohol having a linear alkyl group with 3 to 6 carbon atoms, a bio-derived linear primary alcohol having a linear alkenyl group with 3 to 6 carbon atoms, a bio-derived linear aldehyde having a linear alkyl group with 3 to 6 carbon atoms, and a bio-derived linear aldehyde having a linear alkenyl group with 3 to 6 carbon atoms, a known method can be used, for example, the method for dimerizing an alcohol described in Catal. Sci. Technol., 2015, vol. 5, p3876-3902; the method for dimerizing an aldehyde described in JP-A-09-124536, etc. Specifically, a method can be used in which, in the presence of a catalyst or a basic compound as needed, at 60 to 320° C., bioderived linear primary alcohols having a linear alkyl group having 3 to 6 carbon atoms, bioderived linear primary alcohols having a linear alkenyl group having 3 to 6 carbon atoms, bioderived linear aldehydes having a linear alkyl group having 3 to 6 carbon atoms, or bioderived linear aldehydes having a linear alkenyl group having 3 to 6 carbon atoms are reacted to dimerize. In the present invention, in a system where two or more selected from a bio-derived linear primary alcohol having a linear alkyl group having 3 to 6 carbon atoms, a bio-derived linear primary alcohol having a linear alkenyl group having 3 to 6 carbon atoms, a bio-derived linear aldehyde having a linear alkyl group having 3 to 6 carbon atoms, and a bio-derived linear aldehyde having a linear alkenyl group having 3 to 6 carbon atoms are mixed, the bio-derived linear primary alcohol having a linear alkyl group having 3 to 6 carbon atoms, the bio-derived linear primary alcohol having a linear alkenyl group having 3 to 6 carbon atoms, the bio-derived linear aldehyde having a linear alkyl group having 3 to 6 carbon atoms, or the bio-derived linear aldehyde having a linear alkenyl group having 3 to 6 carbon atoms are reacted under the above-mentioned conditions to dimerize them. In this case, the reaction can be carried out in a reduced or pressurized state in the reaction container.

[0019] As the catalyst that can be used when dimerizing a bio-derived linear primary alcohol or a bio-derived linear aldehyde, a known catalyst can be used, for example, metal powders of copper, silver, zinc, nickel, palladium, platinum, cobalt, rhodium, iridium, iron, ruthenium, manganese, chromium, molybdenum, etc., metal oxides, metal complexes, metal salts, metal alkoxides and other metal catalysts, 2,2,6,6-tetramethylpiperidinyl-1-oxyl (TEMPO) and other nitro radical catalysts, and one or more of them can be used. In addition, when a metal catalyst is used, a compound serving as a ligand may be used in combination. Examples of such ligands include olefin ligands such as ethylene, norbornene, norbornadiene, 1,7-octadiene, 1,5-cyclooctadiene, and pentamethylcyclopentadienyl; phosphine ligands such as ethylenebis(diphenylphosphine), cyclohexyldiphenylphosphine, dicyclohexylphenylphosphine, tri-tert-butylphosphine, and triphenylphosphine; nitrogen-containing ligands such as triethylamine, benzylamine, bipyridine, bisiminopyridine, and imidazole, and the like. One or more of these ligands may be used.

[0020] As the basic compound that can be used when dimerizing the biologically derived linear primary alcohol or the biologically derived linear aldehyde, for example, there can be mentioned oxides, hydroxides, carbonates, carboxylates, phosphates, amine salts, and alkoxide compounds of alkali metals such as lithium, sodium, and potassium, and oxides, hydroxides, carbonates, carboxylates, phosphates, amine salts, and alkoxide compounds of alkaline earth metals such as magnesium and calcium, and one or more of them can be used. In addition, these catalysts can be supported on zeolite, silica, alumina, zirconium oxide, magnesium oxide, activated carbon, graphite, carbon nanotubes, etc.

[0021] When dimerizing the bio-derived linear primary alcohol or the bio-derived linear aldehyde, a solvent may be used as necessary. Examples of such solvents include water, pentane, hexane, heptane, octane, decane, dodecane, benzene, toluene, xylene, ethylbenzene, dodecylbenzene, diethylene glycol dimethyl ether, triethylene glycol dimethyl ether, diphenyl ether, dibenzyl ether, diallyl ether, tetrahydrofuran, dimethicone ... Alkane, N-methyl-2-pyrrolidine, ethyl butyrate, butyl butyrate, ethyl acetate, butyl acetate, dimethylformamide, N,N-dimethylacetamide, acetonitrile, propionitrile, benzonitrile and the like, and one or more of them can be used.

[0022] As a step for obtaining the bio-derived branched primary alcohol having a branched alkyl group having 6 to 12 carbon atoms of the present invention, when only a bio-derived straight-chain primary alcohol is used as a raw material, it is sufficient as long as a step of dimerizing the bio-derived straight-chain primary alcohol is included. It may include only a step of dimerizing the bio-derived straight-chain primary alcohol, or may include other steps as required. For example, when a bio-derived branched primary alcohol having a branched alkyl group having 6 to 12 carbon atoms is obtained by dimerizing bio-derived straight-chain primary alcohols having straight-chain alkenyl groups having 3 to 6 carbon atoms as the bio-derived straight-chain primary alcohol, a hydrogenation step may be performed before or after the dimerization step. When a raw material containing a bio-derived linear aldehyde is used, the process may include only the step of dimerizing the bio-derived linear aldehyde and the step of hydrogenating the obtained compound, or may include other steps as necessary.

[0023] In the present invention, by carrying out the above-mentioned steps, when using bio-derived n-propanol or bio-derived n-propenol as the bio-derived straight-chain primary alcohol, bio-derived 2-methylpentanol (as a bio-derived branched-chain primary alcohol having a branched-chain alkyl group having 6 to 12 carbon atoms) can be produced, when using bio-derived n-butanol or bio-derived n-butenol, bio-derived 2-ethylhexanol (as a bio-derived branched-chain primary alcohol having a branched-chain alkyl group having 6 to 12 carbon atoms) can be produced, and when using bio-derived n-pentanol or bio-derived n-propenol, bio-derived 2-ethylhexanol (as a bio-derived branched-chain primary alcohol having a branched-chain alkyl group having 6 to 12 carbon atoms) can be produced. When bio-derived n-pentenol is used, bio-derived 2-propylheptanol (as a bio-derived branched primary alcohol having a branched alkyl group with 6 to 12 carbon atoms) can be produced. When bio-derived n-hexanol or bio-derived n-hexenol is used, bio-derived 2-butyloctanol (as a bio-derived branched primary alcohol having a branched alkyl group with 6 to 12 carbon atoms) can be produced. These bio-derived branched primary alcohols having a branched alkyl group with 6 to 12 carbon atoms can be used to easily produce bio-derived branched alkyl glyceryl ethers with suppressed odor. Similarly, by carrying out the above-mentioned steps, when using bio-derived n-propanal or bio-derived n-acrolein as the bio-derived straight-chain aldehyde, bio-derived 2-methylpentanol (as a bio-derived branched-chain primary alcohol having a branched-chain alkyl group having 6 to 12 carbon atoms) can be produced, when using bio-derived n-butyraldehyde or bio-derived n-crotonal, bio-derived 2-ethylhexanol (as a bio-derived branched-chain primary alcohol having a branched-chain alkyl group having 6 to 12 carbon atoms) can be produced, and when using bio-derived n-valeraldehyde or bio-derived n-pentenal When bio-derived n-pentenal is used, bio-derived 2-propylheptanol (as a bio-derived branched primary alcohol having a branched alkyl group with 6 to 12 carbon atoms) can be produced. When bio-derived n-hexanal or bio-derived n-hexenal is used, bio-derived 2-butyloctanol (as a bio-derived branched primary alcohol having a branched alkyl group with 6 to 12 carbon atoms) can be produced. These bio-derived branched primary alcohols having a branched alkyl group with 6 to 12 carbon atoms can easily produce bio-derived branched alkyl glyceryl ethers with suppressed odor.

[0024] In the present invention, from the viewpoint of suppressing the odor of the obtained bio-derived branched alkyl glyceryl ether and various properties, as the step of obtaining the bio-derived branched primary alcohol, it is preferred to carry out a step of dimerizing bio-derived n-butanol (1-butanol) to obtain bio-derived 2-ethylhexanol, a step of dimerizing bio-derived n-butyraldehyde and then hydrogenating bio-derived 2-ethylhexanol, or a step of dimerizing bio-derived n-butanol and bio-derived n-butyraldehyde separately and then hydrogenating bio-derived 2-ethylhexenol contained in the product to obtain bio-derived 2-ethylhexanol.

[0025] The process of producing the bio-derived branched alkyl glyceryl ether of the present invention is a process of producing the bio-derived branched alkyl glyceryl ether using the bio-derived branched primary alcohol obtained in the above process. As a method for producing the bio-derived branched alkyl glyceryl ether using the bio-derived branched primary alcohol, for example, there can be mentioned: a method of subjecting the bio-derived branched primary alcohol to a dehydration condensation reaction with glycerol, a method of subjecting the bio-derived branched primary alcohol to a dehydrogenation reaction with 1-chloro-2,3-propanediol, a method of subjecting the bio-derived branched primary alcohol to a reaction with epichlorohydrin and then hydrolyzing the obtained glycidyl ether, a method of subjecting the bio-derived branched primary alcohol to a reaction with glycidol, a method of subjecting the bio-derived branched primary alcohol to a dehydrogenation reaction with allyl chloride and then oxidizing with hydrogen peroxide or the like and then hydrolyzing the obtained glycidyl ether, etc. In these methods, the compound reacting with the bio-derived branched primary alcohol may be a compound derived from a plant resource or other organism, or may be a compound derived from a petroleum raw material, but from the viewpoint of environmental protection, it is preferred to use a bio-derived compound. In the present invention, it is particularly preferred to use a method in which a bio-derived branched primary alcohol is reacted with bio-derived epichlorohydrin and the resulting glycidyl ether is hydrolyzed.

[0026] Here, the biogenic epichlorohydrin that can be preferably used in the present invention refers to epichlorohydrin manufactured from plant resources, etc., for example, epichlorohydrin of biogenic origin manufactured using biomass from sources such as soybean oil, rapeseed oil or palm kernel oil as raw materials, corn, sugar cane, beet, wheat, barley, rye, etc. The method for manufacturing such biogenic epichlorohydrin is not particularly limited, and a known method can be used, for example, the method of manufacturing biogenic dichloropropane from glycerol fatty acid esters contained in vegetable oils such as soybean oil, rapeseed oil or palm kernel oil or glycerol fatty acid esters manufactured from biomass from sources such as corn, sugar cane, beet, wheat, barley, rye, etc. and a chlorinating agent, and then obtaining a method of biogenic epichlorohydrin by dehydrochlorination, etc. In addition, in the present invention, commercially available biogenic epichlorohydrin such as Epicerol (registered trademark) manufactured by Solvay can also be used.

[0027] As a method for producing the bio-derived branched alkyl glyceryl ether of the present invention, a method of hydrolyzing the glycidyl ether obtained by reacting a bio-derived branched primary alcohol with bio-derived epichlorohydrin can be preferably used. More specifically, the method includes the following steps: an alcoholization step of reacting a bio-derived branched primary alcohol with bio-derived epichlorohydrin to obtain an alcoholate; a ring-closing step of ring-closing the obtained alcoholate by a ring-closing reaction to obtain a closed-ring body; and a ring-opening step of ring-opening the obtained closed-ring body by a ring-opening reaction to obtain a bio-derived branched alkyl glyceryl ether. In the present invention, by using a method including such steps, a bio-derived branched alkyl glyceryl ether with suppressed odor can be produced by a simple method using a bio-derived raw material.

[0028] In the alcoholization step of reacting a biologically derived branched primary alcohol with biologically derived epichlorohydrin to obtain an alcoholate, the ratio of the amount of the biologically derived branched primary alcohol to the amount of the biologically derived epichlorohydrin used is not particularly limited. From the viewpoint of the odor suppression effect of the obtained biologically derived branched alkyl glyceryl ether, the amount of the biologically derived branched primary alcohol to the amount of the biologically derived epichlorohydrin used is preferably 1.0:0.1 to 1.0:1.2 in terms of molar ratio, more preferably 1.0:0.2 to 1.0:1.0, and further preferably 1:0.3 to 1:0.8. In addition, in the alcoholization step, the method for reacting the biologically derived branched primary alcohol with the biologically derived epichlorohydrin is not particularly limited. For example, a method of mixing the biologically derived branched primary alcohol with the biologically derived epichlorohydrin, heating and cooling as needed, and reacting at 20 to 150° C. for 1 minute to 24 hours can be cited. In addition, in the alcoholization step, a known catalyst can be used.

[0029] The ring-closing step of obtaining a ring-closed body by ring-closing the alcoholate obtained in the alcoholization step by a ring-closing reaction is specifically a step of removing a chlorine group from the alcoholate obtained in the alcoholization step to form an epoxy group. The method of ring-closing the alcoholate by a ring-closing reaction in the ring-closing step is not particularly limited, and for example, a method of adding a known alkali agent to the alcoholate to condense it can be used. At this time, as a known alkali agent, for example, alkali metal hydroxides such as sodium hydroxide, potassium hydroxide, calcium hydroxide, and lithium hydroxide, and their aqueous solutions can be used. When adding a known alkali agent to the alcoholate for dehydration condensation, the ratio of the amount of the alcoholate to the alkali agent used is not particularly limited, but from the viewpoint of the odor suppression effect of the obtained bio-derived branched alkyl glyceryl ether, the amount of the alcoholate to the alkali agent used is preferably 1:0.5 to 1:3 in terms of molar ratio, and more preferably 1:1 to 1:2. In addition, the specific method of adding a known alkali agent to the alcoholate for dehydration condensation is not particularly limited, and examples thereof include: adding a known aqueous alkali solution to the alcoholate and mixing, and reacting at 20 to 150° C. for 1 minute to 24 hours while heating and cooling as needed. In addition, a known catalyst can be used in the ring-closing reaction.

[0030] The ring-opening step of opening the ring-closed body obtained in the ring-closing step by a ring-opening reaction to obtain a branched alkyl glyceryl ether of biological origin is specifically a ring-opening step of opening the epoxy group of the ring-closed body obtained in the ring-closing step by a ring-opening reaction to become two hydroxyl groups to obtain a branched alkyl glyceryl ether of biological origin. In the ring-opening step, the method of opening the ring-closed body by a ring-opening reaction is not particularly limited, and for example, a method of opening the ring-closed body by hydrolyzing the ring-closed body can be used. The method of opening the ring-closed body by hydrolyzing the ring-closed body is not particularly limited, and for example, a method of adding water to the closed ring body, heating or cooling under a reduced pressure or a pressurized environment (0.01 kPa to 10 MPa) as needed, and reacting at 20 to 200° C. for 1 minute to 24 hours can be mentioned. In addition, in the ring-opening reaction, a known catalyst can be used, for example, an acid such as sulfuric acid, hydrochloric acid, perchloric acid, phosphoric acid, acetic acid, and peracetic acid can be used.

[0031] The method for producing a bio-derived branched alkyl glyceryl ether of the present invention may include a step of obtaining a bio-derived branched primary alcohol having a branched alkyl group having 6 to 12 carbon atoms (the step includes dimerizing one or more selected from the above-mentioned bio-derived straight-chain primary alcohol having a straight-chain alkyl group having 3 to 6 carbon atoms, a bio-derived straight-chain primary alcohol having a straight-chain alkenyl group having 3 to 6 carbon atoms, a bio-derived straight-chain aldehyde having a straight-chain alkyl group having 3 to 6 carbon atoms, and a bio-derived straight-chain aldehyde having a straight-chain alkenyl group having 3 to 6 carbon atoms), and a step of producing a bio-derived branched alkyl glyceryl ether using the obtained bio-derived branched primary alcohol, and may further include a distillation step of distilling the product by a known method. In the present invention, examples of the distillation step include a step of distilling a product containing a closed ring body after the ring closing step (intermediate distillation step), a step of distilling a product containing a bio-derived branched alkyl glyceryl ether after the ring opening step (final distillation), and the like. Any one of these steps may be performed, or both of these steps may be performed. In addition, the method for distilling the product is not particularly limited. For example, atmospheric distillation, reduced pressure distillation, molecular distillation, steam distillation and the like can be used. More specifically, single distillation, fractional distillation, flash distillation, steam distillation, vacuum distillation, short-path distillation, thin film distillation, reactive distillation, extractive distillation and the like can be used.

[0032] In the method for producing biologically derived branched alkyl glyceryl ether of the present invention, a deodorizing step of deodorizing the product containing biologically derived branched alkyl glyceryl ether may be further included after the ring-opening step. The method for deodorizing the product containing biologically derived branched alkyl glyceryl ether is not particularly limited, and for example, a method of contacting the product containing biologically derived branched alkyl glyceryl ether with water, water vapor, or an inert gas under normal pressure or reduced pressure may be used.

[0033] The bio-derived branched alkyl glyceryl ether of the present invention is a bio-derived branched alkyl glyceryl ether that can be produced by a method for producing a bio-derived branched alkyl glyceryl ether, the method comprising: a step of obtaining a bio-derived branched primary alcohol having a branched alkyl group having 6 to 12 carbon atoms (the step comprising dimerizing one or more selected from the above-mentioned bio-derived straight-chain primary alcohol having a straight-chain alkyl group having 3 to 6 carbon atoms, a bio-derived straight-chain primary alcohol having a straight-chain alkenyl group having 3 to 6 carbon atoms, a bio-derived straight-chain aldehyde having a straight-chain alkyl group having 3 to 6 carbon atoms, and a bio-derived straight-chain aldehyde having a straight-chain alkenyl group having 3 to 6 carbon atoms), and a step of producing a bio-derived branched alkyl glyceryl ether using the obtained bio-derived branched primary alcohol. The above-mentioned methods can be used for each step in the present invention, and the bio-derived branched alkyl glyceryl ether of the present invention can be a bio-derived branched alkyl glyceryl ether produced by the production method further comprising the above-mentioned distillation step and / or deodorization step.

[0034] Here, the biologically derived branched alkyl glyceryl ether of the present invention contains a trace amount of inevitable impurities derived from the raw materials. By identifying the inevitable impurities, the branched alkyl glyceryl ether of the present invention can be distinguished from branched alkyl glyceryl ethers produced from non-biological raw materials such as petroleum raw materials, but since the impurities contained are different depending on the type of plant or the like used as the raw material, the inevitable impurities cannot be identified in the same way. Therefore, the biologically derived branched alkyl glyceryl ether of the present invention is identified by limiting the production method of the raw materials.

[0035] From the viewpoint of long-term quality stability, the bio-derived branched alkyl glyceryl ether of the present invention can be made into a composition containing the bio-derived branched alkyl glyceryl ether, the composition containing the bio-derived branched alkyl glyceryl ether and 0.05 to 0.30 parts by mass of an antioxidant such as tocopherols based on 100 parts by mass of the bio-derived branched alkyl glyceryl ether. As the antioxidant, for example, tocopherols such as d-α-tocopherol, dl-α-tocopherol, d-α-tocopherol acetate, or other known antioxidants can be used, but from the viewpoint of further improving the long-term quality stability, the tocopherols in the total amount of the antioxidant in the composition containing the bio-derived branched alkyl glyceryl ether are preferably 50% by mass or more and 100% by mass or less, more preferably 75% by mass or more and 100% by mass or less, and particularly preferably 100% by mass (that is, the antioxidant is only tocopherols).

[0036] The cosmetic composition or detergent composition of the present invention is a cosmetic composition or detergent composition containing the above-mentioned biologically derived branched alkyl glyceryl ether. The amount of the biologically derived branched alkyl glyceryl ether in the cosmetic composition or detergent composition of the present invention is not particularly limited, but is preferably 0.01 to 20.0% by mass, more preferably 0.05 to 10.0% by mass, and even more preferably 0.10 to 5.0% by mass, relative to the total amount of the cosmetic composition or detergent composition. By including the above-mentioned biologically derived branched alkyl glyceryl ether in a cosmetic composition or a detergent composition, the biologically derived branched alkyl glyceryl ether acts as an antimicrobial agent (preservative) of the composition. In addition, the biologically derived branched alkyl glyceryl ether of the present invention suppresses odor, so when included in a cosmetic composition or a detergent composition, it is possible to prevent an adverse effect on the fragrance of the composition.

[0037] The specific usage of the cosmetic composition or detergent composition of the present invention is not particularly limited, and examples thereof include: shampoo, conditioner, conditioner, treatment agent, toner, cosmetic liquid, emulsion, cream, facial cleanser, skin cleanser, makeup remover, makeup remover oil, hair care agent, hair styling liquid, hair bleach, hair dye, perm liquid, lipstick, facial mask, foundation, cologne, sunscreen, deodorant, perfume and cosmetic oil.

[0038] In the cosmetic composition or detergent composition of the present invention, additives commonly used in cosmetics or detergents can be added during storage, use, or after use to improve various properties (solubility, dispersibility, stability, feel of use, coating, permeability, moisture retention, safety, appearance, optical properties, fragrance, whitening, etc.) according to the purpose of use. Such additives include, for example: higher alcohols, powder components, higher fatty acids, humectants, water-soluble polymers, metal ion blocking agents, lower alcohols, water, polyols, monosaccharides, oligosaccharides, polysaccharides, amino acids and their derivatives, organic amines, pH adjusters, vitamins, ultraviolet protection components, antioxidants, thickeners, surfactants, and other ingredients that can be added (preservatives, blood circulation promoters, anti-inflammatory agents, activators, whitening agents, anti-seborrheic agents, anti-inflammatory agents, various extracts and plant seaweed extracts, etc.), and any one or more of them can be added.

[0039] Examples of the higher alcohols include lauryl alcohol, cetyl alcohol, stearyl alcohol, behenyl alcohol, Straight-chain higher alcohols such as ethyl alcohol, myristyl alcohol, oleyl alcohol, and cetearyl alcohol; branched-chain higher alcohols such as monostearyl glyceryl ether (baty alcohol), 2-decyltetradecyl alcohol, lanolin alcohol, cholesterol, phytosterol, hexyldodecanol, isostearyl alcohol, and octyldodecanol, etc., and one or more of them can be used.

[0040] Examples of the powder component include inorganic powders (e.g., talc, kaolin, mica, sericite, muscovite, phlogopite, synthetic mica, red mica, biotite, vermiculite, magnesium carbonate, calcium carbonate, aluminum silicate, barium silicate, calcium silicate, magnesium silicate, strontium silicate, metal tungstate, magnesium, silicon dioxide, zeolite, barium sulfate, calcined calcium sulfate (calcined gypsum), calcium phosphate, fluoroapatite, hydroxyapatite, ceramic powder, metal soaps (e.g., zinc myristate, calcium palmitate, aluminum stearate), boron nitride, etc.); organic powders (e.g., polyamide resin, Grease powder (nylon powder), polyethylene powder, polymethyl methacrylate powder, polystyrene powder, styrene and acrylic copolymer resin powder, benzoguanamine resin powder, polytetrafluoroethylene powder, cellulose powder, etc.); inorganic white pigment (for example, titanium dioxide, zinc oxide, etc.); inorganic red pigment (for example, iron oxide (bengala), iron titanate, etc.); inorganic brown pigment (for example, γ-iron oxide, etc.); inorganic yellow pigment (for example, yellow iron oxide, loess, etc.); inorganic black pigment (for example, black iron oxide, low-order titanium oxide, etc.); inorganic Organic purple pigments (e.g., manganese violet, cobalt violet, etc.); inorganic green pigments (e.g., chromium oxide, chromium hydroxide, cobalt titanate, etc.); inorganic blue pigments (e.g., ultramarine, cyan blue, etc.); pearl pigments (e.g., titanium oxide-coated mica, titanium oxide-coated bismuth oxychloride, titanium oxide-coated talc, colored titanium oxide-coated mica, bismuth oxychloride, fish scale foil, etc.); metal powder pigments (e.g., aluminum powder, copper powder, etc.); organic pigments such as zirconium, barium or aluminum lakes (e.g., Red No. 201, Red No. 202, Red No. 204, Red No. 205, Red No. 220, etc.); , Red No. 226, Red No. 228, Red No. 405, Orange No. 203, Orange No. 204, Yellow No. 205, Yellow No. 401 and Blue No. 404, organic pigments such as Red No. 3, Red No. 104, Red No. 106, Red No. 227, Red No. 230, Red No. 401, Red No. 505, Orange No. 205, Yellow No. 4, Yellow No. 5, Yellow No. 202, Yellow No. 203, Green No. 3 and Blue No. 1), etc.; natural pigments (for example, chlorophyll, β-carotene, etc.), etc., and one or more of them can be used.

[0041] Examples of higher fatty acids include lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, Acid, oleic acid, undecylenic acid, tall oil fatty acid, isostearic acid, linoleic acid, linolenic acid, eicosapentaenoic acid (EPA), docosahexaenoic acid (DHA), etc., and one or more of them can be used.

[0042] Examples of the moisturizing agent include polyethylene glycol, xylitol, sorbitol, maltitol, chondroitin sulfate, hyaluronic acid, mucin sulfate, caronnic acid, atelocollagen, cholesterol-12-hydroxystearate, sodium lactate, bile acid salts, dl-pyrrolidonecarboxylate, short-chain soluble collagen, diglycerol (EO) PO adduct, Rosa sylvestris extract, Yarrow extract, and Melilotus plant extract, and one or more of these can be used.

[0043] As natural water-soluble polymers, for example, there can be mentioned: plant polymers (for example, gum arabic, tragacanth gum, galactan, guar gum, carob gum, karaya gum, carrageenan, pectin, agar, quince seeds (quinces), alginate (brown algae extract), starch (rice, corn, potato, wheat), glycyrrhizic acid); microbial polymers (for example, xanthan gum, dextran, succinoglycan, pullulan, gellan gum, etc.); animal polymers (for example, collagen, casein, albumin, gelatin, etc.), etc., and one or more of them can be used.

[0044] Examples of water-soluble polymers include: starch polymers (e.g., carboxymethyl starch, methylhydroxypropyl starch, etc.); cellulose polymers (methyl cellulose, ethyl cellulose, methylhydroxypropyl cellulose, hydroxyethyl cellulose, sodium cellulose sulfate, hydroxypropyl cellulose, carboxymethyl cellulose, sodium carboxymethyl cellulose, crystalline cellulose, cellulose powder, etc.); alginic acid polymers (e.g., sodium alginate, propylene glycol alginate, etc.); vinyl polymers (e.g., polyvinyl alcohol, polyvinyl methyl ether, polyvinyl pyrrolidone, carboxyvinyl polymer, etc.); polyoxyethylene polymers (e.g., polyoxyethylene-polyoxypropylene copolymers made from polyethylene glycol 20000, 40000 or 60000, etc.); acrylic polymers (e.g., sodium polyacrylate, polyethyl acrylate, polyacrylamide, etc.); polyethylene imine; cationic polymers, etc., and one or more of them can be used.

[0045] Examples of the metal ion blocking agent include 1-hydroxyethylidene-1,1-diphosphonic acid, 1-hydroxyethylidene-1,1-diphosphonic acid tetrasodium salt, disodium edetate, trisodium edetate, tetrasodium edetate, sodium citrate, sodium polyphosphate, sodium metaphosphate, gluconic acid, phosphoric acid, citric acid, ascorbic acid, succinic acid, edetic acid, trisodium hydroxyethylethylenediaminetriacetate, and the like. One or more of these can be used.

[0046] Examples of the lower alcohol include ethanol, propanol, isopropanol, isobutanol, and tert-butanol, and one or more of these can be used.

[0047] Examples of the polyol include diols (e.g., ethylene glycol, propylene glycol, 1,3-butanediol, 1,2-hexanediol, etc.); triols (e.g., glycerol, trimethylolpropane, etc.); tetraols (e.g., pentaerythritol such as 1,2,6-hexanetriol, etc.); pentaols (e.g., xylitol, etc.); hexaols (e.g., sorbitol, mannitol, etc.); polyol polymers (e.g., diethylene glycol, dipropylene glycol, triethylene glycol, polypropylene glycol, tetraethylene glycol, diglycerol, polyethylene glycol, triglycerol, tetraglycerol, polyglycerol, etc.); diols; ethylene glycol alkyl ethers (e.g., ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, ethylene glycol monophenyl ether, ethylene glycol monohexyl ether, ethylene glycol mono-2-methylhexyl ether, ethylene glycol isopentyl ether, ethylene glycol benzyl ether, ethylene glycol isopropyl ether, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethylene glycol dibutyl ether, etc.); glycol alkyl ethers (e.g., diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol butyl ether, diethylene glycol methyl ethyl ether, triethylene glycol monomethyl ether, triethylene glycol propylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, propylene glycol isopropyl ether, dipropylene glycol methyl ether, dipropylene glycol ethyl ether, dipropylene glycol butyl ether, etc.); glycol ether esters (for example, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, ethylene glycol monobutyl ether acetate, ethylene glycol monophenyl ether acetate, ethylene glycol adipate, ethylene glycol disuccinate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, Propylene glycol monophenyl ether acetate, etc.); sugar alcohols (for example, sorbitol, maltitol, maltotriose, mannitol, sucrose, erythritol, glucose, fructose, amylolytic sugar, maltose, xylitol, amylolytic sugar reducing alcohol, etc.); glycerides; tetrahydrofurfuryl alcohol; POE-tetrahydrofurfuryl alcohol; POP-butyl ether; POP·POE-butyl ether; tripolyoxypropylene glyceryl ether; POP-glycerol ether; POP-glycerol ether phosphoric acid; POP·POE-pentaerythritol ether; polyglycerol, etc., and one or more of them can be used.

[0048] Examples of monosaccharides include trisaccharides (e.g., D-glyceraldehyde, dihydroxyacetone, etc.); tetrasaccharides (e.g., D-erythrose, D-erythrulose, D-threose, erythritol, etc.); pentoses (e.g., L-arabinose, D-xylose, L-lyxose, D-arabinose, D-ribose, D-ribulose, D-xylulose, L-xylulose, etc.); hexoses (e.g., D-glucose, D-talose, D-psicose, D-galactose, D-fructose, L-galactose, L-mannose, D-tagatose, etc.); ); heptose (e.g., aldoheptose, heptulose, etc.); octose (e.g., octulose, etc.); deoxy sugar (e.g., 2-deoxy-D-ribose, 6-deoxy-L-galactose, 6-deoxy-L-mannose, etc.); amino sugar (e.g., D-glucosamine, D-galactosamine, sialic acid, aminouronic acid, muramic acid, etc.); uronic acid (e.g., D-glucuronic acid, D-mannuronic acid, L-guluronic acid, D-galacturonic acid, L-iduronic acid, etc.), etc., and one or more of them can be used.

[0049] Examples of the oligosaccharide include sucrose, umbelliferyl, lactose, psyllose, isolysaccharides, α,α-trehalose, raffinose, lysin, umbilicin, stachyose and verbascose, and one or more of them can be used.

[0050] Examples of the polysaccharide include cellulose, quince seeds, chondroitin sulfate, starch, galactan, dermatan sulfate, glycogen, gum arabic, heparan sulfate, hyaluronic acid, tragacanth gum, keratan sulfate, chondroitin, xanthan gum, mucin sulfate, guar gum, dextran, keratin sulfate, locust bean gum, succinylglucose, and caronnic acid. One or more of these can be used.

[0051] Examples of amino acids include neutral amino acids (e.g., threonine, cysteine, etc.), basic amino acids (e.g., hydroxylysine, etc.), etc. In addition, examples of amino acid derivatives include sodium acyl sarcosinate (sodium lauroyl sarcosinate), acyl glutamate, sodium acyl β-alanine, glutathione, pyrrolidone carboxylic acid, etc., and one or more of them can be used.

[0052] Examples of the organic amine include monoethanolamine, diethanolamine, triethanolamine, morpholine, triisopropanolamine, 2-amino-2-methyl-1,3-propanediol, and 2-amino-2-methyl-1-propanol. One or more of these may be used.

[0053] Examples of the pH adjuster include buffers such as lactic acid-sodium lactate, citric acid-sodium citrate, and succinic acid-sodium succinate, and one or more of these may be used.

[0054] Examples of the vitamins include vitamins A, B1, B2, B6, C, E and derivatives thereof, pantothenic acid and derivatives thereof, and biotin. One or more of these may be used.

[0055] As the UV protection component, inorganic UV protection components such as powder pigments and metal powder pigments and their surface-treated products, or organic UV protection components can be used, for example: metal oxides such as titanium oxide, zinc oxide, cerium oxide, low-order titanium oxide, iron-doped titanium oxide, metal hydroxides such as iron hydroxide, plate-like iron oxide, metal flakes such as aluminum flakes, ceramics such as silicon carbide and their fluorine compound-treated products, silicone-treated products, silicone resin-treated products, pendant-treated products, silane coupling agent-treated products, titanium coupling agent-treated products, silane-treated products, oil-treated products, N-acylated lysine-treated products, polyacrylic acid-treated products, metal soap-treated products, acrylic resin-treated products, metal oxides The present invention can be used for processing products of materials, or salicylic acid-based, p-aminobenzoic acid-based, benzophenone-based, cinnamic acid-based, benzoylmethane-based, 2-ethylhexyl 2-cyano-3,3-diphenylprop-2-enoate, 2-ethylhexyl dimethoxybenzylidene dioxoimidazolidinylpropionate, 1-(3,4-dimethoxyphenyl)-4,4-dimethyl-1,3-pentanedione, cinoxate, methyl O-aminobenzoate, 2-ethylhexyl 2-cyano-3,3-diphenylacrylate, 3-(4-methylbenzylidene) camphor, octyl triazone, 2-ethylhexyl 4-(3,4-dimethoxybenzylidene)-2,5-dioxo-1-imidazolidinylpropionate, and polymer derivatives thereof, and one or more of them can be used.

[0056] Examples of the antioxidant include tocopherols, butylated hydroxytoluene, butylated hydroxyanisole, and gallic acid esters, and one or more of these may be used.

[0057] Examples of the thickener include xanthan gum, carrageenan, high methoxy pectin, low methoxy pectin, guar gum, gum arabic, crystalline cellulose, arabinogalactan, gum karaya, gum tragacanth, alginic acid, albumin, casein, curdlan, β-glucan, β-glucan derivatives, gellan gum, dextran, α-glucose and α-glucose derivatives, cellulose or its derivatives, keratin and collagen or their derivatives, calcium alginate, pullulan, agar, gelatin, tamarind seed polysaccharides, carbomer, dimethyldiallylammonium chloride-acrylamide copolymer, dimethyldiallylammonium chloride-hectorite, acrylamide-acrylic acid-dimethyldiallylammonium chloride copolymer, and dibutylethylhexanoylglutamine. One or more of these may be used.

[0058] Examples of the surfactant include cationic surfactants (e.g., lauryl trimethyl ammonium chloride, hexadecyl trimethyl ammonium chloride, stearyl trimethyl ammonium chloride, alkyl trimethyl ammonium chloride, distearyl dimethyl ammonium chloride, stearyl trimethyl ammonium saccharin, hexadecyl trimethyl ammonium saccharin, behenyl trimethyl ammonium chloride, Trimethylammonium methyl sulfate, behenate Dimethylamine, behenyl Diethylaminoacetamide, behenyl alcohol Dimethylaminopropionamide, behenyl alcohol acid dimethylaminoacetamide, stearyl dimethylamine, palmitoyloxypropyl dimethylamine, stearyloxypropyl dimethylamine, etc.); anionic surfactants (for example, alkyl ether sulfates, alkyl sulfates, alkyl ether sulfate ester salts, alkenyl ether sulfates, alkenyl sulfates, olefin sulfonates, alkane sulfonates, saturated or unsaturated fatty acid salts, alkyl or alkenyl ether carboxylates, α-sulfo fatty acid salts, N-acyl amino acid type surfactants, phosphoric acid monoester or phosphoric acid diester type surfactants, sulfosuccinates, N-alkanoyl methyl taurates, and their derivatives, etc.); amphoteric surfactants (for example, coconut fatty acids betaine-type amphoteric surfactants such as amidopropyl dimethylacetic acid betaine, lauryl dimethyl amino acid betaine, 2-alkyl-N-carboxymethyl-N-hydroxymethylimidazoline betaine, lauryl hydroxysulfonyl betaine, lauryl amide ethyl hydroxyethyl carboxymethyl betaine, metal salts of hydroxypropyl phosphate, amino acid-type amphoteric surfactants such as metal salts of β-lauryl aminopropionic acid, sulfate-type amphoteric surfactants and sulfonic acid-type amphoteric surfactants, etc.); nonionic surfactants (for example, POE hexadecyl ether (hexadecyl polyoxyethylene ether), POE stearyl ether (stearyl polyoxyethylene ether), POE betaine-type amphoteric surfactants such as metal salts of hydroxypropyl phosphate, metal salts of β-lauryl aminopropionic acid, etc.); POE ether, POE oleyl ether (oleyl polyoxyethylene ether), POE lauryl ether (lauryl polyoxyethylene ether), POE octyl dodecyl ether, POE hexyl decyl ether, POE isostearyl ether, POE nonyl phenyl ether, POE octyl phenyl ether, POE polyoxypropylene hexadecyl ether, POE polyoxypropylene decyl tetradecyl ether, POE sorbitan monooleate, POE sorbitan monostearate, POE sorbitan monopalmitate, POE sorbitan monolaurate, POE sorbitan trioleate, POE glycerol monostearate, POE glycerol monomyristate, POE sorbitol tetraoleate, POE sorbitol hexastearate, POE sorbitan Sugar alcohol monolaurate, POE sorbitol beeswax, polyethylene glycol monooleate, polyethylene glycol monostearate, polyethylene glycol monolaurate, lipophilic glycerol monooleate, lipophilic glycerol monostearate, self-emulsifying monostearate glyceryl, sorbitan monooleate, sorbitan sesquioleate, sorbitan trioleate, sorbitan monostearate, sorbitan monopalmitate, sorbitan monolaurate, sucrose fatty acid ester, monolauric acid decaglyceryl, monostearic acid decaglyceryl, monooleic acid decaglyceryl, monomyristic acid decaglyceryl, alkyl glucoside, POE methyl glucoside, POE dioleic acid methyl glucoside, etc.), and one or more of them can be used.

[0059] Other ingredients that can be added include, for example, preservatives (methyl paraben, ethyl paraben, butyl paraben, phenoxyethanol, etc.); anti-inflammatory agents (for example, glycyrrhizic acid derivatives, glycyrrhetinic acid derivatives, salicylic acid derivatives, hibiscus alcohol, zinc oxide, allantoin, etc.); whitening agents (for example, saxifrage extract, arbutin, etc.); various extracts (such as phellodendron, coptis root, purple root, peony, Japanese angelica root, birch, sage, loquat, carrot, aloe, mallow, iris, grape, coix seed, loofah, lily, saffron, Chuanxiong, ginger, forsythia, red formonone, garlic , pepper, tangerine peel, angelica, seaweed, etc.); activators (for example, royal jelly, photosensitizers, cholesterol derivatives, etc.); blood circulation promoters (for example, benzyl nicotinate, β-butoxyethyl nicotinate, capsaicin, ginger ketone, cantharidin, ichthyol, tannic acid, α-borneol, nicotinic acid tocopherol, hexanicotinate inositol lipids, cyclomandelate, cinnarizine, tolazoline, acetylcholine, verapamil, cepharanthin, γ-oryzanol, etc.); anti-seborrheic agents (for example, sulfur, dimethylthiothrene, etc.); anti-inflammatory agents (for example, tranexamic acid, thiotaurine, hypotaurine, etc.), etc., and one or more of them can be used.

[0060] The respective contents of the higher alcohol, powder component, higher fatty acid, humectant, water-soluble polymer, metal ion blocking agent, lower alcohol, water, polyol, monosaccharide, oligosaccharide, polysaccharide, amino acid and its derivatives, organic amine, pH adjuster, vitamin, ultraviolet protection component, antioxidant, thickener, surfactant, and other optional ingredients (preservative, blood circulation promoter, anti-inflammatory agent, activator, whitening agent, anti-seborrheic agent, anti-inflammatory agent, various extracts and plant seaweed extracts, etc.) in the cosmetic composition or detergent composition of the present invention when added separately are not particularly limited and can be adjusted according to the embodiment and purpose. For example, 0.001 to 50.0% by mass can be added respectively relative to the total mass of the cosmetic composition or detergent composition. Example

[0061] The present invention is specifically described below by way of examples, but the present invention is not limited to these examples and may be varied without departing from the scope of the present invention. It should be noted that in the following examples, % is a mass basis unless otherwise specified.

[0062] <Example 1> After adding 3552g of bio-derived n-butanol, 424g of tripotassium phosphate, 448g of calcium oxide and 160g of copper catalyst into an autoclave, the reaction was carried out at 290°C for 5 hours, and further filtration and distillation were performed to obtain 1248g of bio-derived branched primary alcohol, i.e., bio-derived 2-ethylhexanol, which is a dimerized bio-derived n-butanol, and 1812g of unreacted bio-derived n-butanol.

[0063] Next, 1051 g of the obtained bio-derived 2-ethylhexanol and 3.5 g of anhydrous tin chloride as a catalyst were added to another reaction container, and 249 g of bio-derived epichlorohydrin (Epicerol (registered trademark) manufactured by Solvay) was added while the temperature was raised to 80°C, and the mixture was reacted at 80°C for 4 hours to obtain 570 g of an alcoholate. Then, the unreacted bio-derived 2-ethylhexanol was removed by reducing the pressure to 2.0 kPa at 150°C. Next, 234 g of a 48% sodium hydroxide aqueous solution was added at normal pressure, and the mixture was reacted at 60°C for 5 hours to close the alcoholate through a ring-closing reaction, thereby obtaining 429 g of a closed-ring compound. Next, the obtained closed-ring compound was reduced to 2.0 kPa at 130°C, and distilled. Next, 585 g of water and 1.3 g of 75% phosphoric acid aqueous solution were added under normal pressure, and the mixture was reacted at 170° C. and 0.8 kPa to open the closed ring to obtain 423 g of biologically derived 2-ethylhexylglyceryl ether. The mixture was then distilled at 160° C. to 210° C. and 1.0 kPa to obtain biologically derived 2-ethylhexylglyceryl ether A.

[0064] <Example 2> After adding 370.5 g of bio-derived n-butanol, 1.1 L of p-xylene, 39.8 g of dichloro(pentamethylcyclopentadienyl)iridium(III) dimer, 55.1 g of 1,7-octadiene, and 224.42 g of potassium tert-butoxide to an autoclave, the reaction was carried out at 120°C for 4 hours, and further filtered and distilled to obtain 260 g of bio-derived 2-ethylhexanol, which is a bio-derived branched primary alcohol dimerized with bio-derived n-butanol.

[0065] Next, 250 g of the obtained bio-derived 2-ethylhexanol and 0.8 g of anhydrous tin chloride as a catalyst were added to another reaction container, and 59.2 g of bio-derived epichlorohydrin (Epicerol (registered trademark) manufactured by Solvay) was added while the temperature was raised to 80°C, and the mixture was reacted at 80°C for 4 hours to obtain 135.6 g of an alcoholate. Then, the unreacted bio-derived 2-ethylhexanol was removed by reducing the pressure to 2.0 kPa at 150°C. Next, 55.7 g of a 48% sodium hydroxide aqueous solution was added at normal pressure, and the mixture was reacted at 60°C for 5 hours to close the alcoholate through a ring-closing reaction, thereby obtaining 102.1 g of a closed-ring compound. Next, the obtained closed-ring compound was reduced to 2.0 kPa at 130°C, and distilled. Next, 139.2 g of water and 0.3 g of 75% phosphoric acid aqueous solution were added under normal pressure, and the mixture was reacted at 170° C. and 0.8 kPa to open the closed ring to obtain 100.6 g of biologically derived 2-ethylhexylglyceryl ether. The mixture was then distilled at 160° C. to 210° C. and 1.0 kPa to obtain biologically derived 2-ethylhexylglyceryl ether B.

[0066] <Example 3> After adding 3100 g of n-butanol from biological sources, 398 g of copper (I) iodide, 327 g of TEMPO, 344 g of 1-methylimidazole, and 16 L of acetonitrile to a reaction vessel of an atmosphere-open system, the mixture was reacted at 25° C. for 24 hours, and then filtered and distilled to obtain 2100 g of n-butyraldehyde from biological sources. Next, 2000 g of n-butyraldehyde from biological sources was mixed with 2 L of a 2 wt % sodium hydroxide aqueous solution, reacted at 90° C. for 4 hours, and then separated into oil and water to obtain 1720 g of an oil phase. By distilling the obtained oil phase, 1400 g of 2-ethylhexenal from biological sources in which n-butyraldehyde from biological sources was dimerized was obtained. Furthermore, the obtained 2-ethylhexenal from biological sources was hydrogenated at a temperature of 120° C. and a pressure of 4.0 MPa for 2 hours in the presence of a nickel-based catalyst, and then distilled to obtain 1260 g of 2-ethylhexanol from biological sources, which is a branched primary alcohol from biological sources.

[0067] Next, 1051 g of the obtained bio-derived 2-ethylhexanol and 3.5 g of anhydrous tin chloride as a catalyst were added to another reaction container, and 249 g of bio-derived epichlorohydrin (Epicerol (registered trademark) manufactured by Solvay) was added while the temperature was raised to 80°C, and the mixture was reacted at 80°C for 4 hours to obtain an alcoholate. Then, the unreacted bio-derived 2-ethylhexanol was removed by reducing the pressure to 2.0 kPa at 150°C. Next, 234 g of a 48% sodium hydroxide aqueous solution was added at normal pressure, and the mixture was reacted at 60°C for 5 hours, thereby closing the alcoholate through a ring-closing reaction to obtain a closed-ring body. Next, the obtained closed-ring body was reduced to 2.0 kPa at 130°C, and distilled. Next, 585 g of water and 1.3 g of 75% phosphoric acid aqueous solution were added under normal pressure, and the mixture was reacted at 170° C. and 0.8 kPa to open the closed ring to obtain 423 g of biologically derived 2-ethylhexylglyceryl ether. The mixture was then distilled at 160° C. to 210° C. and 1.0 kPa to obtain biologically derived 2-ethylhexylglyceryl ether C.

[0068] <Comparative Example 1> In Example 1, 2-ethylhexyl glyceryl ether D derived from a petroleum raw material was obtained by the same method except that 1051 g of 2-ethylhexanol derived from a petroleum raw material was used, which was produced by producing n-butyraldehyde from propylene derived from a petroleum raw material by an oxo process and then subjecting n-butyraldehyde to aldol condensation and hydrogenation.

[0069] <Deodorization evaluation> The deodorizing properties of the 2-ethylhexylglyceryl ethers produced in Examples 1 to 3 and Comparative Example 1 were evaluated immediately after production. Specifically, the odor of the produced 2-ethylhexylglyceryl ether was confirmed by 7 testers, and 10 points were given to 2-ethylhexylglyceryl ether that was completely odorless (odor suppressed), and 1 point was given to 2-ethylhexylglyceryl ether that was strongly odorous. The scores were scored on a 10-point scale of 1 to 10 points, and the total score of the scoring results of each tester was calculated. When the total score was 60 points or more, it was evaluated as ◎, when the total score was 45 points or more and less than 60 points, it was evaluated as ○, and when the total score was less than 45 points, it was evaluated as ×, and the deodorizing properties were evaluated accordingly. The evaluation results are shown in Table 1.

[0070] [Table 1] Deodorization evaluation Example 1 Bio-derived 2-ethylhexylglycerol ether A ◎ Example 2 Bio-derived 2-ethylhexylglycerol ether B ◎ Example 3 Bio-derived 2-ethylhexylglycerol ether C ◎ Comparative Example 1 2-Ethylhexylglycerol ether D from petroleum raw materials ×

[0071] According to the present invention, it is possible to obtain a bio-derived branched alkyl glyceryl ether with suppressed odor by using a bio-derived raw material.

Claims

1. A method for producing a branched alkyl glyceryl ether from biological sources, comprising the following steps: A step of obtaining a bio-derived branched primary alcohol having a branched alkyl group with 6 to 12 carbon atoms, comprising dimerizing one or more selected from a bio-derived straight-chain primary alcohol having a straight-chain alkyl group with 3 to 6 carbon atoms, a bio-derived straight-chain primary alcohol having a straight-chain alkenyl group with 3 to 6 carbon atoms, a bio-derived straight-chain aldehyde having a straight-chain alkyl group with 3 to 6 carbon atoms, and a bio-derived straight-chain aldehyde having a straight-chain alkenyl group with 3 to 6 carbon atoms, and A step of producing a bio-derived branched-chain alkyl glyceryl ether using the obtained bio-derived branched-chain primary alcohol.

2. The method for producing a biologically derived branched alkyl glyceryl ether according to claim 1, wherein: The process of producing a bio-derived branched alkyl glyceryl ether using a bio-derived branched primary alcohol comprises an alcoholization step of reacting a bio-derived branched primary alcohol with bio-derived epichlorohydrin to obtain an alcoholation product, a ring-closing step of closing the obtained alcoholation product through a ring-closing reaction to obtain a closed ring product, and a ring-opening step of opening the obtained closed ring product through a ring-opening reaction to obtain a bio-derived branched alkyl glyceryl ether.

3. Branched alkyl glyceryl ether of biological origin, produced by the method according to claim 1 or 2.

4. A cosmetic composition or a detergent composition comprising the bio-derived branched alkyl glyceryl ether according to claim 3.