Method for producing a bio-derived branched alkyl glycerol ether and the bio-derived branched alkyl glycerol ether produced by the method

Abstract

The present invention provides a method for producing a bio-derived branched alkyl glycerol ether and a bio-derived branched alkyl glycerol ether obtained by the production method. The production method includes the following steps: a step of dimerizing one or more selected from bio-derived straight-chain primary alcohols having a straight-chain alkyl group with 3 to 6 carbon atoms, bio-derived straight-chain primary alcohols having a straight-chain alkenyl group with 3 to 6 carbon atoms, bio-derived straight-chain aldehydes having a straight-chain alkyl group with 3 to 6 carbon atoms, and bio-derived straight-chain aldehydes having a straight-chain alkenyl group with 3 to 6 carbon atoms to obtain a bio-derived branched primary alcohol having a branched alkyl group with 6 to 12 carbon atoms; and a step of producing a bio-derived branched alkyl glycerol ether using the obtained bio-derived branched primary alcohol.

Description

Technical Field

[0001] The present invention relates to a method for producing a branched alkyl glycerol ether of biological origin, which can obtain a branched alkyl glycerol ether of biological origin with suppressed odor using raw materials of biological origin. Background Art

[0002] In cosmetics, detergents, etc., antibacterial agents are generally used for preservation, etc. Among them, as compounds with high safety for the human body, the use of alkyl glycerol ethers is known (for example, Patent Documents 1 to 2).

[0003] However, among such alkyl glycerol ethers, it is known that depending on their structure and production method, oxidative deterioration during storage, decomposition over time, and unpleasant odors may occur. As a countermeasure, for example, Patent Document 3 describes a method for producing a composition containing glycerol ether that can maintain its quality for a long time.

[0004] In addition, in recent years, in all fields of chemicals including cosmetic ingredients, from the viewpoint of environmental protection, etc., it has been sought to make some or all of the raw materials used for production derived from living organisms. Influenced by this trend, the market demands the development of a method for producing a composition containing glycerol ether that can use raw materials of biological origin and maintain its quality for a long time by a simple method.

[0005] Prior Art Documents

[0006] Patent Documents

[0007] Patent Document 1: Japanese Unexamined Patent Publication No. 51-076424

[0008] Patent Document 2: Japanese Unexamined Patent Publication No. 08-310947

[0009] Patent Document 3: International Publication No. 2020 / 066893 Summary of the Invention

[0010] Problems to be Solved by the Invention

[0011] An object of the present invention is to provide a method for producing a branched alkyl glycerol ether of biological origin, which can obtain a branched alkyl glycerol ether of biological origin using raw materials of biological origin and suppressing odor.

[0012] Means for Solving the Problems

[0013] Therefore, the present inventors have conducted in-depth research and completed the present invention. That is, the present invention is a method for producing a bio-derived branched alkyl glycerol ether, which comprises the following steps: a step of dimerizing one or more selected from bio-derived straight-chain primary alcohols having a straight-chain alkyl group with 3 to 6 carbon atoms, bio-derived straight-chain primary alcohols having a straight-chain alkenyl group with 3 to 6 carbon atoms, bio-derived straight-chain aldehydes having a straight-chain alkyl group with 3 to 6 carbon atoms, and bio-derived straight-chain aldehydes having a straight-chain alkenyl group with 3 to 6 carbon atoms to obtain a bio-derived straight-chain primary alcohol having a branched alkyl group with 6 to 12 carbon atoms; and a step of producing a bio-derived branched alkyl glycerol ether using the obtained bio-derived straight-chain primary alcohol.

[0014] Advantages of the Invention

[0015] According to the present invention, there can be provided a method for producing a bio-derived branched alkyl glycerol ether, which can obtain a bio-derived branched alkyl glycerol ether with suppressed odor using bio-derived raw materials. Detailed Embodiments

[0016] The bio-derived straight-chain primary alcohols used in the present invention are one or more selected from bio-derived straight-chain primary alcohols having a straight-chain alkyl group with 3 to 6 carbon atoms and bio-derived straight-chain primary alcohols having a straight-chain alkenyl group with 3 to 6 carbon atoms obtained from plant resources, etc. For example, there can be mentioned: primary alcohols obtained by refining and / or separating vegetable 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 oil, camellia oil, and linseed oil; primary alcohols obtained by fermenting and / or metabolizing biomass from corn, sugarcane, beet, banana, wheat, barley, rye, potato, sweet potato, cassava, taro, broad bean, lentil, pea, etc. using microorganisms; and primary alcohols obtained by synthesizing using various bio-derived 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 oil, camellia oil, and linseed oil as raw materials, etc.

[0017] 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 refining and / or separating the above vegetable oils is not particularly limited, and known methods can be used, such as methods using fatty acids obtained by hydrolyzing fatty acid glycerides contained in vegetable oils for production, etc. At this time, the method for producing 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 from fatty acids can use known methods, for example, a method of methyl esterifying and then hydrogenating fatty acids, or a method of directly hydrogenating fatty acids, etc.

[0018] In addition, the method for obtaining a bio-derived linear primary alcohol having a linear alkyl group with 3 to 6 carbon atoms or a bio-derived linear primary alcohol having a linear alkenyl group with 3 to 6 carbon atoms by fermenting the above biomass using microorganisms is not particularly limited, and known methods can be used. For example, a method can be used in which sugars such as cellulose obtained from biomass are fermented and / or metabolized by fermentation and / or microorganisms such as fungi, enzymes, and yeasts having metabolic ability under appropriate temperature, humidity, atmosphere, and other environments.

[0019] In addition, the method for synthesizing a bio-derived linear primary alcohol having a linear alkyl group with 3 to 6 carbon atoms or a bio-derived linear primary alcohol having a linear alkenyl group with 3 to 6 carbon atoms using various bio-derived compounds obtained from the above plant resources and the like as raw materials is not particularly limited, and known methods can be used. At this time, a bio-derived linear primary alcohol having a hydrocarbon group with the same number of carbon atoms as the bio-derived compound used as a raw material can be produced, or a bio-derived linear primary alcohol having a hydrocarbon group with a different number of carbon atoms from the bio-derived compound used as a raw material can be produced. Examples of such methods include: a method of hydrogenating 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 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.

[0020] As the bio-derived linear primary alcohol having a linear alkyl group with 3 to 6 carbon atoms used in the present invention, as long as it is a bio-derived linear primary alcohol having a linear alkyl group and a hydroxyl group with 3 to 6 carbon atoms in the molecule, it is not particularly limited. Specifically, examples 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), and the like. As the bio-derived linear primary alcohol having a linear alkenyl group with 3 to 6 carbon atoms, as long as it is a bio-derived linear primary alcohol having a linear alkenyl group and a hydroxyl group with 3 to 6 carbon atoms in the molecule, it is not particularly limited. Specifically, examples include: bio-derived n-propenol (allyl alcohol), bio-derived n-butenol (butenol), bio-derived n-pentenol, bio-derived n-hexenol, and the like. Among them, from the viewpoint of obtaining a bio-derived branched alkyl glycerol ether with more suppressed odor, as the bio-derived linear primary alcohol, bio-derived n-butanol (1-butanol) is preferably used. These bio-derived linear primary alcohols are not particularly limited as long as they are obtained by known methods from plant resources and the like.

[0021] The straight-chain aldehydes of biological origin used in the present invention are one or more selected from straight-chain aldehydes of biological origin having a straight-chain alkyl group with 3 to 6 carbon atoms and straight-chain aldehydes of biological origin having a straight-chain alkenyl group with 3 to 6 carbon atoms obtained from plant resources or the like. For example, aldehydes obtained by fermenting and / or metabolizing biomass from corn, sugarcane, sugar beet, banana, wheat, barley, rye, potato, sweet potato, cassava, taro, broad bean, lentil, pea, etc. using microorganisms, aldehydes obtained by synthesizing various biologically derived compounds such as straight-chain primary alcohols of biological origin 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 oil, camellia oil, linseed oil, etc. as raw materials, and the like.

[0022] The method for obtaining a straight-chain aldehyde of biological origin having a straight-chain alkyl group with 3 to 6 carbon atoms or a straight-chain aldehyde of biological origin having a straight-chain alkenyl group with 3 to 6 carbon atoms by fermenting the above biomass using microorganisms is not particularly limited, and known methods can be used. For example, a method of fermenting and / or metabolizing sugars such as cellulose obtained from biomass by microorganisms such as fungi, enzymes, yeast, etc. having metabolic ability under appropriate temperature, humidity, atmosphere, etc. can be used.

[0023] In addition, the method for synthesizing a straight-chain aldehyde of biological origin having a straight-chain alkyl group with 3 to 6 carbon atoms or a straight-chain aldehyde of biological origin having a straight-chain alkenyl group with 3 to 6 carbon atoms using various biologically derived compounds such as straight-chain primary alcohols of biological origin obtained from the above plant resources or the like as raw materials is not particularly limited, and known methods can be used. At this time, a straight-chain aldehyde of biological origin having a hydrocarbon group with the same number of carbon atoms as the biologically derived compound used as the raw material can be produced, or a straight-chain aldehyde of biological origin having a hydrocarbon group with a different number of carbon atoms from the biologically derived compound used as the raw material can be produced for use in the present invention. As such methods, for example, a method of oxidizing or dehydrogenating a straight-chain primary alcohol of biological origin having a straight-chain alkyl group with 3 to 6 carbon atoms or a straight-chain primary alcohol of biological origin having a straight-chain alkenyl group with 3 to 6 carbon atoms by a known method; a method of producing an aldehyde with an increased number of carbon atoms by hydroformylation using an olefin having 2 to 5 carbon atoms, carbon monoxide, and hydrogen by the oxo process; a method of producing an aldehyde with an increased number of carbon atoms by condensing aldehydes having 2 to 4 carbon atoms obtained by oxidizing or dehydrogenating biologically derived alcohols such as ethanol and propanol by a known method, etc. In the present invention, as the straight-chain aldehyde of biological origin, from the viewpoint of obtaining a branched-chain alkyl glycerol ether of biological origin with further suppressed odor, a straight-chain aldehyde of biological origin obtained by oxidizing or dehydrogenating a straight-chain primary alcohol of biological origin having a straight-chain alkyl group with 3 to 6 carbon atoms or a straight-chain primary alcohol of biological origin having a straight-chain alkenyl group with 3 to 6 carbon atoms by a known method is preferably used.

[0024] The straight-chain aldehyde of biological origin having a straight-chain alkyl group with 3 to 6 carbon atoms used in the present invention is not particularly limited as long as it is a straight-chain aldehyde of biological origin having a straight-chain alkyl group and an aldehyde group with 3 to 6 carbon atoms in the molecule. Specific examples include: biologically-derived n-propionaldehyde (propionaldehyde), biologically-derived n-butyraldehyde (butyraldehyde), biologically-derived n-valeraldehyde (valeraldehyde), and biologically-derived n-hexanal (hexanal). The straight-chain aldehyde of biological origin having a straight-chain alkenyl group with 3 to 6 carbon atoms is not particularly limited as long as it is a straight-chain aldehyde of biological origin having a straight-chain alkenyl group and an aldehyde group with 3 to 6 carbon atoms in the molecule. Specific examples include: biologically-derived acrolein (acrolein, propenal), biologically-derived crotonaldehyde (crotonaldehyde, butenal), biologically-derived pentenal (pentenal), and biologically-derived hexenal (hexenal), etc. Among them, from the viewpoint of obtaining a branched-chain alkyl glycerol ether of biological origin with further suppressed odor, as the straight-chain aldehyde of biological origin, biologically-derived n-butyraldehyde (butyraldehyde) is preferably used. These straight-chain aldehydes of biological origin can be used without particular limitation as long as they are obtained by known methods such as plant resources. For example, in the case of using biologically-derived n-butyraldehyde as the straight-chain aldehyde of biological origin having a straight-chain alkyl group with 3 to 6 carbon atoms, biologically-derived n-butyraldehyde obtained by oxidizing or dehydrogenating biologically-derived butanol by a known method, biologically-derived n-butyraldehyde obtained by hydroformylating biologically-derived propylene by the oxo process, etc. can be used. In the present invention, from the viewpoint of obtaining a branched-chain alkyl glycerol ether of biological origin with particularly suppressed odor, as the straight-chain aldehyde of biological origin, biologically-derived n-butyraldehyde obtained by oxidizing or dehydrogenating biologically-derived n-butanol by a known method is particularly preferably used.

[0025] 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.

[0026] 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.

[0027] As the basic compound that can be used when dimerizing a straight-chain primary alcohol or a straight-chain aldehyde of biological origin, for example, the following can be cited: oxides, hydroxides, carbonates, carboxylates, phosphates, amine salts, and alkoxide compounds of alkali metals such as lithium, sodium, and potassium; oxides, hydroxides, carbonates, carboxylates, phosphates, amine salts, and alkoxide compounds of alkaline earth metals such as magnesium and calcium, etc. One or more of them can be used. In addition, these catalysts can be supported on zeolite, silica, alumina, zirconia, magnesia, activated carbon, graphite, carbon nanotubes, etc. and then used.

[0028] In addition, when dimerizing a straight-chain primary alcohol or a straight-chain aldehyde of biological origin, a solvent can be used as needed. As such a solvent, for example, the following can be cited: 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, dioxane, N-methyl-2-pyrrolidone, ethyl butyrate, butyl butyrate, ethyl acetate, butyl acetate, dimethylformamide, N,N-dimethylacetamide, acetonitrile, propionitrile, benzonitrile, etc. One or more of them can be used.

[0029] As the process for obtaining the branched-chain primary alcohol of biological origin having a branched-chain alkyl group with 6 to 12 carbon atoms of the present invention, when only using a straight-chain primary alcohol of biological origin as the raw material, as long as it includes a process of dimerizing the straight-chain primary alcohol of biological origin, it can either only include the process of dimerizing the straight-chain primary alcohol of biological origin or can include other processes as needed. For example, when dimerizing straight-chain primary alcohols of biological origin having a straight-chain alkenyl group with 3 to 6 carbon atoms to obtain a branched-chain primary alcohol of biological origin having a branched-chain alkyl group with 6 to 12 carbon atoms, a hydrogenation process is carried out before or after the dimerization process.

[0030] In addition, when using a raw material containing a straight-chain aldehyde of biological origin, as long as it includes a process of dimerizing the straight-chain aldehyde of biological origin and a process of hydrogenating the obtained compound, it can either only include the process of dimerizing the straight-chain aldehyde of biological origin and the process of hydrogenating the obtained compound or can include other processes as needed.

[0031] In the present invention, through the above-described steps, as a bio-derived straight-chain primary alcohol, when using bio-derived n-propanol or bio-derived allyl alcohol, bio-derived 2-methylpentanol (a bio-derived branched-chain primary alcohol having a branched alkyl group with 6 to 12 carbon atoms) can be produced. When using bio-derived n-butanol or bio-derived butenol, bio-derived 2-ethylhexanol (a bio-derived branched-chain primary alcohol having a branched alkyl group with 6 to 12 carbon atoms) can be produced. When using bio-derived n-pentanol or bio-derived pentenol, bio-derived 2-propylheptanol (a bio-derived branched-chain primary alcohol having a branched alkyl group with 6 to 12 carbon atoms) can be produced. When using bio-derived n-hexanol or bio-derived hexenol, bio-derived 2-butyloctanol (a bio-derived branched-chain primary alcohol having a branched alkyl group with 6 to 12 carbon atoms) can be produced. These bio-derived branched-chain primary alcohols having a branched alkyl group with 6 to 12 carbon atoms can be used to easily produce a bio-derived branched alkyl glycerol ether with suppressed odor.

[0032] Similarly, through the above-described steps, as a bio-derived straight-chain aldehyde, when using bio-derived n-propionaldehyde or bio-derived acrolein, bio-derived 2-methylpentanol (a bio-derived branched-chain primary alcohol having a branched alkyl group with 6 to 12 carbon atoms) can be produced. When using bio-derived n-butyraldehyde or bio-derived crotonaldehyde, bio-derived 2-ethylhexanol (a bio-derived branched-chain primary alcohol having a branched alkyl group with 6 to 12 carbon atoms) can be produced. When using bio-derived n-valeraldehyde or bio-derived pentenal, bio-derived 2-propylheptanol (a bio-derived branched-chain primary alcohol having a branched alkyl group with 6 to 12 carbon atoms) can be produced. When using bio-derived n-hexanal or bio-derived hexenal, bio-derived 2-butyloctanol (a bio-derived branched-chain primary alcohol having a branched alkyl group with 6 to 12 carbon atoms) can be produced. These bio-derived branched-chain primary alcohols having a branched alkyl group with 6 to 12 carbon atoms can be used to easily produce a bio-derived branched alkyl glycerol ether with suppressed odor.

[0033] In the present invention, from the viewpoints of suppressing the odor and various properties of the obtained bio-derived branched alkyl glycerol ether, as the step for obtaining a bio-derived branched-chain primary alcohol, the following steps are preferably carried 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 it to obtain bio-derived 2-ethylhexanol, or a step of dimerizing bio-derived n-butanol and bio-derived n-butyraldehyde separately and then hydrogenating the bio-derived 2-ethylhexenol contained in the product to obtain bio-derived 2-ethylhexanol.

[0034] The process for producing the bio-based branched alkyl glycerol ether of the present invention is a process for producing a bio-based branched alkyl glycerol ether using the bio-based branched primary alcohol obtained in the above process. As a method for producing a bio-based branched alkyl glycerol ether using a bio-based branched primary alcohol, for example, a method of subjecting a bio-based branched primary alcohol and glycerol to a dehydration condensation reaction, a method of subjecting a bio-based branched primary alcohol and 1-chloro-2,3-propanediol to a dehydrochlorination reaction, a method of reacting a bio-based branched primary alcohol with epichlorohydrin and then hydrolyzing the resulting glycidyl ether, a method of reacting a bio-based branched primary alcohol with glycidol, a method of subjecting a bio-based branched primary alcohol and allyl chloride to a dehydrochlorination reaction and then oxidizing with hydrogen peroxide or the like and hydrolyzing the resulting glycidyl ether, etc. Among these methods, the compound reacting with the bio-based branched primary alcohol may be a compound derived from a living organism such as a plant resource or a compound derived from a petroleum raw material, but from the viewpoint of environmental protection, a bio-based compound is preferably used. In the present invention, a method of reacting a bio-based branched primary alcohol with a bio-based epichlorohydrin and then hydrolyzing the resulting glycidyl ether is preferably used.

[0035] Herein, the bio-based epichlorohydrin preferably used in the present invention refers to epichlorohydrin produced from plant resources or the like. For example, bio-based epichlorohydrin produced using vegetable oils such as soybean oil, rapeseed oil or palm kernel oil, and biomass derived from corn, sugarcane, beet, wheat, barley, rye or the like as raw materials can be cited. The method for producing such bio-based epichlorohydrin is not particularly limited, and known methods can be used. For example, a method of producing bio-based dichloropropanol using glycerol fatty acid esters contained in vegetable oils such as soybean oil, rapeseed oil or palm kernel oil or glycerol fatty acid esters produced from biomass derived from corn, sugarcane, beet, wheat, barley, rye or the like and a chlorinating agent, and then obtaining bio-based epichlorohydrin by dehydrochlorination can be cited. In addition, in the present invention, commercially available bio-based epichlorohydrin such as Epicerol (registered trademark) manufactured by Solvay can also be used.

[0036] As a method preferably used for producing the bio-based branched alkyl glycerol ether of the present invention, a method of reacting a bio-based branched primary alcohol with a bio-based epichlorohydrin and then hydrolyzing the resulting glycidyl ether is more specifically a method including the following steps: an alcoholization step of reacting a bio-based branched primary alcohol with a bio-based epichlorohydrin to obtain an alcoholized product; a ring-closure step of subjecting the obtained alcoholized product to a ring-closure reaction to obtain a ring-closed product; and an opening step of subjecting the obtained ring-closed product to an opening reaction to obtain a bio-based branched alkyl glycerol ether. In the present invention, by using a method including such steps, a bio-based branched alkyl glycerol ether with suppressed odor can be produced by a simple method using bio-based raw materials.

[0037] In the alcoholization step of obtaining an alcoholized product by reacting a branched primary alcohol of biological origin with epichlorohydrin of biological origin, the ratio of the amounts used of the branched primary alcohol of biological origin to epichlorohydrin of biological origin is not particularly limited. From the viewpoint of the odor suppression effect of the branched alkyl glycerol ether of biological origin obtained, the ratio of the amounts used of the branched primary alcohol of biological origin to epichlorohydrin of biological origin is preferably 1.0:0.1 to 1.0:1.2, more preferably 1.0:0.2 to 1.0:1.0, and still more preferably 1:0.3 to 1:0.8 in terms of molar ratio. In addition, in the alcoholization step, the method of reacting the branched primary alcohol of biological origin with epichlorohydrin of biological origin is not particularly limited. For example, there may be mentioned a method of mixing the branched primary alcohol of biological origin with epichlorohydrin of biological origin and reacting at 20 to 150°C for 1 minute to 24 hours while heating and cooling as needed, etc. In addition, in the alcoholization step, a known catalyst can be used.

[0038] The ring-closure step of obtaining a ring-closed product by ring-closing the alcoholized product obtained in the alcoholization step is specifically a step of causing the chlorine group to be eliminated from the alcoholized product obtained in the alcoholization step to form an epoxy group. The method of ring-closing the alcoholized product by a ring-closing reaction in the ring-closure step is not particularly limited. For example, a method of adding a known alkali agent to the alcoholized product and causing it to condense can be used, etc. At this time, as the known alkali agent, for example, hydroxides of alkali metals such as sodium hydroxide, potassium hydroxide, calcium hydroxide, lithium hydroxide, and their aqueous solutions, etc. can be used. The ratio of the amounts used of the alcoholized product to the alkali agent when adding a known alkali agent to the alcoholized product for dehydration condensation is not particularly limited. From the viewpoint of the odor suppression effect of the branched alkyl glycerol ether of biological origin obtained, the ratio of the amounts used of the alcoholized product to the alkali agent is preferably 1:0.5 to 1:3, more preferably 1:1 to 1:2 in terms of molar ratio. In addition, the specific method when using the method of adding a known alkali agent to the alcoholized product for dehydration condensation is not particularly limited. For example, there may be mentioned a method of adding an aqueous solution of a known alkali agent to the alcoholized product and mixing, and reacting at 20 to 150°C for 1 minute to 24 hours while heating and cooling as needed, etc. In addition, in the ring-closing reaction, a known catalyst can be used.

[0039] The ring-opening process for obtaining a bio-derived branched alkyl glycerol ether by ring-opening a closed-loop body obtained in a closed-loop process is specifically a ring-opening process in which the epoxy group of the closed-loop body obtained in the closed-loop process is ring-opened by a ring-opening reaction to form two hydroxyl groups, thereby obtaining a bio-derived branched alkyl glycerol ether. In the ring-opening process, the method for ring-opening the closed-loop body by a ring-opening reaction is not particularly limited. For example, a method of hydrolyzing the closed-loop body to ring-open it can be used. The method for hydrolyzing the closed-loop body to ring-open it is not particularly limited. For example, examples include: adding water to the closed-loop body and reacting it at 20 to 200 °C for 1 minute to 24 hours while heating or cooling as needed under a reduced pressure or pressurized environment (0.01 kPa to 10 MPa). In addition, in the ring-opening reaction, known catalysts can be used. For example, acids such as sulfuric acid, hydrochloric acid, perchloric acid, phosphoric acid, acetic acid, and peracetic acid can be used.

[0040] In the method for producing a bio-derived branched alkyl glycerol ether of the present invention, it may include: a process for obtaining a bio-derived branched primary alcohol having a branched alkyl group with 6 to 12 carbon atoms (which includes dimerizing one or more selected from the above-mentioned bio-derived straight-chain primary alcohols having a straight-chain alkyl group with 3 to 6 carbon atoms, bio-derived straight-chain primary alcohols having a straight-chain alkenyl group with 3 to 6 carbon atoms, bio-derived straight-chain aldehydes having a straight-chain alkyl group with 3 to 6 carbon atoms, and bio-derived straight-chain aldehydes having a straight-chain alkenyl group with 3 to 6 carbon atoms), and a process for producing a bio-derived branched alkyl glycerol ether using the obtained bio-derived branched primary alcohol. In addition, it may further include a distillation process for distilling the product by a known method. In the present invention, as the distillation process, examples include: a process for distilling a product containing a closed-loop body after the closed-loop process (intermediate distillation process), a process for distilling a product containing a bio-derived branched alkyl glycerol ether after the ring-opening process (final distillation), etc. Any one of these processes can be carried out, or both of these processes can be carried out. In addition, the method for distilling the product is not particularly limited. For example, methods such as atmospheric distillation, vacuum distillation, molecular distillation, and steam distillation can be used. More specifically, methods such as simple distillation, fractional distillation, flash distillation, steam distillation, vacuum distillation, short-path distillation, thin-film distillation, reactive distillation, and extractive distillation can be used.

[0041] In the method for producing a bio-derived branched alkyl glycerol ether of the present invention, it may further include a deodorization process for deodorizing a product containing a bio-derived branched alkyl glycerol ether after the ring-opening process. The method for deodorizing a product containing a bio-derived branched alkyl glycerol ether is not particularly limited. For example, a method of contacting the product containing a bio-derived branched alkyl glycerol ether with water, steam, or an inert gas under normal pressure or reduced pressure can be used.

[0042] The branched-chain alkyl glycerol ether of biological origin according to the present invention is a branched-chain alkyl glycerol ether of biological origin that can be produced by a method for producing a branched-chain alkyl glycerol ether of biological origin, the production method including: a step of obtaining a branched-chain primary alcohol of biological origin having a branched-chain alkyl with 6 to 12 carbon atoms (which includes dimerizing one or more selected from the biological origin straight-chain primary alcohols having a straight-chain alkyl with 3 to 6 carbon atoms, the biological origin straight-chain primary alcohols having a straight-chain alkenyl with 3 to 6 carbon atoms, the biological origin straight-chain aldehydes having a straight-chain alkyl with 3 to 6 carbon atoms, and the biological origin straight-chain aldehydes having a straight-chain alkenyl with 3 to 6 carbon atoms), and a step of producing a branched-chain alkyl glycerol ether of biological origin using the obtained branched-chain primary alcohol of biological origin. Each step in the present invention can be carried out using the above-mentioned methods, and the branched-chain alkyl glycerol ether of biological origin according to the present invention can be a branched-chain alkyl glycerol ether of biological origin produced by a production method further including the above-mentioned distillation step and / or deodorization step.

[0043] Here, the branched-chain alkyl glycerol ether of biological origin according to the present invention contains trace amounts of inevitable impurities derived from the raw materials. By determining these inevitable impurities, the branched-chain alkyl glycerol ether of the present invention can be distinguished from branched-chain alkyl glycerol ethers produced from non-biological origin raw materials such as petroleum raw materials. However, since the impurities contained vary depending on the type of plant or the like used as the raw material, the inevitable impurities cannot be determined in the same way. Therefore, the branched-chain alkyl glycerol ether of biological origin according to the present invention is determined by a production method that defines the raw materials.

[0044] From the aspect of long-term quality stability, the branched-chain alkyl glycerol ether of biological origin according to the present invention can be made into a composition containing the branched-chain alkyl glycerol ether of biological origin, the composition containing the branched-chain alkyl glycerol ether of biological origin and an antioxidant such as tocopherols in an amount of 0.05 to 0.30 parts by mass relative to 100 parts by mass of the branched-chain alkyl glycerol ether of biological origin. As the antioxidant, for example, tocopherols such as d-α-tocopherol, dl-α-tocopherol, and d-α-tocopherol acetate or other known antioxidants can be used. However, from the viewpoint of further improving long-term quality stability, the tocopherols in the total amount of antioxidants in the composition containing the branched-chain alkyl glycerol ether of biological origin 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).

[0045] 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.

[0046] 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.

[0047] 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.

[0048] 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.

[0049] 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.

[0050] Examples of powder components 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 (plaster of Paris), calcium phosphate, fluorapatite, hydroxyapatite, ceramic powder, metal soaps (e.g., zinc myristate, calcium palmitate, aluminum stearate), boron nitride, etc.); organic powders (e.g., polyamide resin powder (nylon powder), polyethylene powder, polymethyl methacrylate powder, polystyrene powder, styrene-acrylic copolymer resin powder, benzoguanamine resin powder, polytetrafluoroethylene powder, cellulose powder, etc.); inorganic white pigments (e.g., titanium dioxide, zinc oxide, etc.); inorganic red pigments (e.g., bengala (iron oxide), iron titanate, etc.); inorganic brown pigments (e.g., γ-iron oxide, etc.); inorganic yellow pigments (e.g., yellow iron oxide, loess, etc.); inorganic black pigments (e.g., black iron oxide, lower-order titanium oxide, etc.); inorganic 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, dark blue, etc.); pearl pigments (e.g., mica coated with titanium dioxide, bismuth oxychloride coated with titanium dioxide, talc coated with titanium dioxide, mica coated with colored titanium dioxide, bismuth oxychloride, fish scale foil, etc.); metal powder pigments (e.g., aluminum powder, copper powder, etc.); organic pigments such as zircon, barium, or aluminum lakes (e.g., organic pigments such as Red No. 201, Red No. 202, Red No. 204, Red No. 205, Red No. 220, 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, 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); natural pigments (e.g., chlorophyll, β-carotene, etc.), etc. One or more of them can be used.

[0051] Examples of higher fatty acids include: lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, oleic acid, undecylenic acid, tall oil fatty acid, isostearic acid, linoleic acid, linolenic acid, eicosapentaenoic acid (EPA), docosahexaenoic acid (DHA), etc. One or more of them can be used. Examples of higher fatty acids include: lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, oleic acid, undecylenic acid, tall oil fatty acid, isostearic acid, linoleic acid, linolenic acid, eicosapentaenoic acid (EPA), docosahexaenoic acid (DHA), etc. One or more of them can be used.

[0052] Examples of humectants include polyethylene glycol, xylitol, sorbitol, maltitol, chondroitin sulfate, hyaluronic acid, mucoitin sulfate, caronin sulfate, telopeptide collagen, cholesteryl 12-hydroxystearate, sodium lactate, bile salts, dl-pyrrolidone carboxylate, short-chain soluble collagen, diglycerol (EO) PO adduct, Rosa multiflora Thunb. extract, Achillea millefolium L. extract, Melilotus extract, etc. One or more of them can be used.

[0053] Examples of natural water-soluble polymers include plant-based polymers (e.g., gum arabic, tragacanth, galactan, guar gum, carob gum, karaya gum, carrageenan, pectin, agar, quince seed (Cydonia oblonga Mill.), alginate (brown algae extract), starch (rice, corn, potato, wheat), glycyrrhizic acid); microorganism-based polymers (e.g., xanthan gum, dextran, succinoglycan, pullulan, gellan gum, etc.); animal-based polymers (e.g., collagen, casein, albumin, gelatin, etc.). One or more of them can be used.

[0054] Examples of water-soluble polymers include starch-based polymers (e.g., carboxymethyl starch, methylhydroxypropyl starch, etc.); cellulose-based polymers (methylcellulose, ethylcellulose, methylhydroxypropylcellulose, hydroxyethylcellulose, sodium cellulose sulfate, hydroxypropylcellulose, carboxymethylcellulose, sodium carboxymethylcellulose, crystalline cellulose, cellulose powder, etc.); alginic acid-based polymers (e.g., sodium alginate, propylene glycol alginate, etc.); vinyl-based polymers (e.g., polyvinyl alcohol, polyvinyl methyl ether, polyvinylpyrrolidone, carboxyvinyl polymer, etc.); polyoxyethylene-based polymers (e.g., polyoxyethylene-polyoxypropylene copolymer based on polyethylene glycol 20000, 40000 or 60000 as raw material, etc.); acrylic acid-based polymers (e.g., sodium polyacrylate, ethyl polyacrylate, polyacrylamide, etc.); polyethyleneimine; cationic polymers, etc. One or more of them can be used.

[0055] Examples of sequestering agents for metal ions include 1-hydroxyethylidene-1,1-diphosphonic acid, tetrasodium 1-hydroxyethylidene-1,1-diphosphonate, 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, etc. One or more of them can be used.

[0056] Examples of lower alcohols include ethanol, propanol, isopropanol, isobutanol, tert-butanol, etc. One or more of them can be used.

[0057] Examples of the polyol include: diols (e.g., ethylene glycol, propylene glycol, 1,3 - butanediol, 1,2 - hexanediol, etc.); triols (e.g., glycerin, trimethylolpropane, etc.); tetrols (e.g., pentaerythritol such as 1,2,6 - hexanetriol, etc.); pentols (e.g., xylitol, etc.); hexols (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.); dialkyl ether of diols (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 isoamyl ether, ethylene glycol benzyl ether, ethylene glycol isopropyl ether, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethylene glycol dibutyl ether, etc.); dialkyl ether of diols (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 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.); diol ether esters (e.g., 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 (e.g., sorbitol, maltitol, maltotriose, mannitol, sucrose, erythritol, glucose, fructose, starch hydrolysate sugar, maltose, xylitol, starch hydrolysate reducing alcohol, etc.); glycerol esters; tetrahydrofurfuryl alcohol; POE - tetrahydrofurfuryl alcohol; POP - butyl ether; POP·POE - butyl ether; tripropylene glycol glycerol ether; POP - glycerol ether; POP - glycerol ether phosphate; POP·POE - pentaerythritol ether; polyglycerol, etc. One or more of them can be used.

[0058] As monosaccharides, for example, the following can be cited: trioses (e.g., D-glyceraldehyde, dihydroxyacetone, etc.); tetroses (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.); heptoses (e.g., heptaldose, heptulose, etc.); octoses (e.g., octulose, etc.); deoxysugars (e.g., 2-deoxy-D-ribose, 6-deoxy-L-galactose, 6-deoxy-L-mannose, etc.); amino sugars (e.g., D-glucosamine, D-galactosamine, sialic acid, amino sugar aldehyde acid, muramic acid, etc.); uronic acids (e.g., D-glucuronic acid, D-mannuronic acid, L-guluronic acid, D-galacturonic acid, L-iduronic acid, etc.). One or more than two of them can be used.

[0059] As oligosaccharides, for example, the following can be cited: sucrose, umbelliferone, lactose, planteose, isocaryophyllose, α,α-trehalose, raffinose, caryophyllose, umbilicin, stachyose, verbascose, etc. One or more than two of them can be used.

[0060] As polysaccharides, for example, the following can be cited: cellulose, quince seed, 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, keratosulfate, locust bean gum, succinylglucose, caronin sulfate, etc. One or more than two of them can be used.

[0061] As amino acids, for example, the following can be cited: neutral amino acids (e.g., threonine, cysteine, etc.); basic amino acids (e.g., hydroxylysine, etc.). In addition, as amino acid derivatives, for example, the following can be cited: sodium acylsarcosine (sodium lauroylsarcosine), acylglutamates, sodium acyl-β-alanine, glutathione, pyrrolidonecarboxylic acid, etc. One or more than two of them can be used.

[0062] As organic amines, for example, the following can be cited: monoethanolamine, diethanolamine, triethanolamine, morpholine, triisopropanolamine, 2-amino-2-methyl-1,3-propanediol, 2-amino-2-methyl-1-propanol, etc. One or more than two of them can be used.

[0063] As pH regulators, for example, the following can be cited: buffers such as lactic acid-sodium lactate, citric acid-sodium citrate, succinic acid-sodium succinate, etc. One or more than two of them can be used.

[0064] As vitamins, for example, vitamin A, B1, B2, B6, C, E and their derivatives, pantothenic acid and its derivatives, biotin, etc. can be cited, and one or more of them can be used.

[0065] As ultraviolet ray defense components, inorganic ultraviolet ray defense components such as powder pigments and metal powder pigments and their surface-treated products, or organic ultraviolet ray defense components can be used. For example, metal oxides such as titanium oxide, zinc oxide, cerium oxide, lower-order titanium oxide, iron-doped titanium oxide, metal hydroxides such as iron hydroxide, metal flakes such as plate-shaped iron oxide and 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 oxide-treated products, etc., or salicylic acid-based, p-aminobenzoic acid-based, benzophenone-based, cinnamic acid-based, benzoylmethane-based, 2-cyano-3,3-diphenylprop-2-enoic acid 2-ethylhexyl ester, 2-ethylhexyl dimethoxybenzylidene dioxoimidazolidine propionate, 1-(3,4-dimethoxyphenyl)-4,4-dimethyl-1,3-pentanedione, cinoxate, methyl O-aminobenzoate, 2-cyano-3,3-diphenylacrylic acid 2-ethylhexyl ester, 3-(4-methylbenzylidene) camphor, octyl triazone, 4-(3,4-dimethoxybenzylidene)-2,5-dioxo-1-imidazolidine propionic acid 2-ethylhexyl ester, their polymer derivatives, etc. can be cited, and one or more of them can be used.

[0066] As antioxidants, for example, tocopherols, dibutylhydroxytoluene, butylhydroxyanisole, gallate esters, etc. can be cited, and one or more of them can be used.

[0067] As thickeners, for example, xanthan gum, carrageenan, high-methoxyl pectin, low-methoxyl pectin, guar gum, gum arabic, crystalline cellulose, arabinogalactan, karaya gum, tragacanth gum, alginic acid, albumin, casein, gellan gum, 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-lithium montmorillonite, acrylamide-acrylic acid-dimethyldiallylammonium chloride copolymer, dibutylethylhexanoylglutamine, etc. can be cited, and one or more of them can be used.

[0068] As surfactants, examples include: cationic surfactants (e.g., lauryl trimethyl ammonium chloride, cetyl trimethyl ammonium chloride, stearyl trimethyl ammonium chloride, alkyl trimethyl ammonium chloride, distearyl dimethyl ammonium chloride, stearyl trimethyl saccharin ammonium, cetyl trimethyl saccharin ammonium, alkyl trimethyl methyl sulfate ammonium, alkyl dimethyl amine, diethylaminoethyl acetate, dimethylaminopropyl acetate, dimethylaminoethyl acetate, stearyl dimethyl amine, palmityloxypropyl dimethyl amine, stearyloxypropyl dimethyl amine, etc.); anionic surfactants (e.g., alkyl ether sulfates, alkyl sulfates, alkyl ether sulfate 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 diester type surfactants, sulfosuccinates, N-alkanoyl methyl taurates, and their derivatives, etc.); amphoteric surfactants (e.g., coconut fatty acid amide propyl dimethyl acetic acid betaine, lauryl dimethyl amino acid betaine, 2-alkyl-N-carboxymethyl-N-hydroxymethyl imidazoline betaine, lauryl hydroxy sulfobetaine, lauramide ethyl hydroxyethyl carboxymethyl betaine, metal salts of hydroxypropyl phosphoric acid, etc. betaine type amphoteric surfactants, metal salts of β-lauryl aminopropionic acid, etc. amino acid type amphoteric surfactants, sulfate ester type amphoteric surfactants and sulfonic acid type amphoteric surfactants, etc.); nonionic surfactants (e.g., POE cetyl ether (cetyl polyoxyethylene ether), POE stearyl ether (stearyl polyoxyethylene ether), POE Base ethers, POE oil-based ethers (oil-based polyoxyethylene ethers), POE lauryl ethers (lauryl polyoxyethylene ethers), POE octyldodecyl ethers, POE hexyl decyl ethers, POE isostearyl ethers, POE nonylphenyl ethers, POE octylphenyl ethers, POE polyoxypropylene cetyl ethers, POE polyoxypropylene decyltetradecyl ethers, POE sorbitan monooleates, POE sorbitan monostearates, POE sorbitan monopalmitates, POE sorbitan monolaurates, POE sorbitan trioleates, POE glycerol monostearates, POE glycerol monomyristates, POE sorbitol tetraoleates, POE sorbitol hexastearates, POE sorbitol monolaurates, POE sorbitol beeswax, polyethylene glycol monooleates, polyethylene glycol monostearates, polyethylene glycol monolaurates, lipophilic glycerol monooleates, lipophilic glycerol monostearates, self-emulsifying glyceryl monostearates, sorbitan monooleates, sorbitan sesquioleates, sorbitan trioleates, sorbitan monostearates, sorbitan monopalmitates, sorbitan monolaurates, sucrose fatty acid esters, decaglycerol monolaurate, decaglycerol monostearate, decaglycerol monooleate, decaglycerol monomyristate, alkyl glucosides, POE methyl glucosides, POE dimethyloleate methyl glucosides, etc.), and one or more of them can be used.

[0069] As other ingredients that can be incorporated, for example, there may be mentioned: preservatives (methyl p-hydroxybenzoate, ethyl p-hydroxybenzoate, butyl p-hydroxybenzoate, phenoxyethanol, etc.); anti-inflammatory agents (for example, glycyrrhizin derivatives, glycyrrhetinic acid derivatives, salicylic acid derivatives, hinokitiol, zinc oxide, allantoin, etc.); whitening agents (for example, saxifrage extract, arbutin, etc.); various extracts (such as phellodendron bark, coptis root, purple root, peony root, swertia japonica, birch, sage, loquat, carrot, aloe, mallow, iris, grape, coix seed, loofah, lily, saffron, chuanxiong, ginger, forsythia, ononis spinosa, garlic, pepper, tangerine peel, angelica, seaweed, etc.); activators (for example, royal jelly, phytochrome, cholesterol derivatives, etc.); blood circulation promoters (for example, benzyl nicotinate, β-butoxyethyl nicotinate, capsaicin, gingerone, cantharidin, ichthammol, tannic acid, α-borneol, tocopherol nicotinate, inositol hexanicotinate, cyclandelate, cinnarizine, tolazoline, acetylcholine, verapamil, stepholidine, γ-oryzanol, etc.); anti-seborrheic agents (for example, sulfur, dimethylthianthrene, etc.); anti-inflammatory agents (for example, tranexamic acid, thiotaurine, hypotaurine, etc.), and one or more of them can be used.

[0070] The contents of the higher alcohols, powder components, higher fatty acids, humectants, water-soluble polymers, sequestering agents, lower alcohols, water, polyols, monosaccharides, oligosaccharides, polysaccharides, amino acids and their derivatives, organic amines, pH adjusters, vitamins, UV protection components, antioxidants, thickeners, surfactants, and other components that can be incorporated (preservatives, blood circulation promoters, anti-inflammatory agents, activators, whitening agents, anti-seborrheic agents, anti-inflammatory agents, various extracts, and plant and seaweed extracts, etc.) when added separately in the cosmetic composition or detergent composition of the present invention are not particularly limited and can be adjusted according to the embodiments and purposes. For example, relative to the total mass of the cosmetic composition or detergent composition, they can be added in amounts of 0.001 to 50.0% by mass, respectively.

[0071] Examples

[0072] The present invention will be specifically described below through examples. However, the present invention is not limited by any of these examples, and can also be varied without departing from the scope of the present invention. It should be noted that in the following examples, etc., unless otherwise specified, % is based on mass.

[0073] <Example 1>

[0074] After adding 3552 g of bio-derived n-butanol, 424 g of tripotassium phosphate, 448 g of calcium oxide, and 160 g of copper catalyst to an autoclave, the reaction was carried out at 290 °C for 5 hours. Further filtration and distillation were performed to obtain 1248 g of bio-derived 2-ethylhexanol, which is a bio-derived branched primary alcohol obtained by dimerization of bio-derived n-butanol, and 1812 g of unreacted bio-derived n-butanol.

[0075] Next, 1051 g of the obtained bio-derived 2-ethylhexanol and 3.5 g of anhydrous stannous chloride as a catalyst were added to another reaction vessel. While heating to 80 °C, 249 g of bio-derived epichlorohydrin (Epicerol (registered trademark) manufactured by Solvay) was added, and the reaction was carried out at 80 °C for 4 hours to obtain 570 g of an alcoholized product. Then, by reducing the pressure to 2.0 kPa at 150 °C, the unreacted bio-derived 2-ethylhexanol was removed. Next, 234 g of a 48% aqueous sodium hydroxide solution was added at normal pressure, and the reaction was carried out at 60 °C for 5 hours to close the ring of the alcoholized product by a ring-closing reaction to obtain 429 g of a ring-closed product. Next, the obtained ring-closed product was distilled under reduced pressure to 2.0 kPa at 130 °C. Then, 585 g of water and 1.3 g of a 75% aqueous phosphoric acid solution were added at normal pressure, and the reaction was carried out at 170 °C and 0.8 kPa to open the ring of the ring-closed product to obtain 423 g of bio-derived 2-ethylhexyl glycerol ether. Further distillation was carried out at 160 °C to 210 °C and 1.0 kPa to obtain bio-derived 2-ethylhexyl glycerol ether A.

[0076] <Example 2>

[0077] Add 370.5 g of bio-based 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, react at 120 °C for 4 hours, and further filter and distill to obtain 260 g of bio-based branched primary alcohol in which bio-based n-butanol is dimerized, namely bio-based 2-ethylhexanol.

[0078] Next, add 250 g of the obtained bio-based 2-ethylhexanol and 0.8 g of anhydrous stannous chloride as a catalyst to another reaction vessel, add 59.2 g of bio-based epichlorohydrin (Epicerol (registered trademark) manufactured by Solvay) while heating to 80 °C, and react at 80 °C for 4 hours to obtain 135.6 g of an alcoholized product. Then, remove the unreacted bio-based 2-ethylhexanol by reducing the pressure to 2.0 kPa at 150 °C. Next, add 55.7 g of 48% aqueous sodium hydroxide solution at atmospheric pressure and react at 60 °C for 5 hours to cyclize the alcoholized product by a ring-closure reaction to obtain 102.1 g of a cyclized product. Then, reduce the pressure of the obtained cyclized product to 2.0 kPa at 130 °C and distill it accordingly. Next, add 139.2 g of water and 0.3 g of 75% aqueous phosphoric acid solution at atmospheric pressure and react at 170 °C and 0.8 kPa to open the ring of the cyclized product to obtain 100.6 g of bio-based 2-ethylhexyl glycerol ether. Distill again at 160 °C to 210 °C and 1.0 kPa to obtain bio-based 2-ethylhexyl glycerol ether B.

[0079] <Example 3>

[0080] Add 3100 g of bio-based n-butanol, 398 g of copper(I) iodide, 327 g of TEMPO, 344 g of 1-methylimidazole, and 16 L of acetonitrile to a reaction vessel open to the atmosphere, react at 25 °C for 24 hours, and further filter and distill to obtain 2100 g of bio-based n-butanal. Next, mix 2000 g of the obtained bio-based n-butanal with 2 L of 2 wt% aqueous sodium hydroxide solution, react at 90 °C for 4 hours, and then perform oil-water separation to obtain 1720 g of an oil phase. Distill the obtained oil phase to obtain 1400 g of bio-based 2-ethylhexenal in which bio-based n-butanal is dimerized. Furthermore, hydrogenate the obtained bio-based 2-ethylhexenal in the presence of a nickel-based catalyst at a temperature of 120 °C and a pressure of 4.0 MPa for 2 hours and then distill to obtain 1260 g of bio-based branched primary alcohol, namely bio-based 2-ethylhexanol.

[0081] Next, 1051 g of biogenic 2-ethylhexanol obtained and 3.5 g of anhydrous stannous chloride as a catalyst were added to another reaction vessel. While heating up to 80°C, 249 g of biogenic epichlorohydrin (Epicerol (registered trademark) manufactured by Solvay) was added, and then the reaction was carried out at 80°C for 4 hours to obtain an alcoholized product. Then, unreacted biogenic 2-ethylhexanol was removed by reducing the pressure to 2.0 kPa at 150°C. Next, after adding 234 g of 48% aqueous sodium hydroxide solution under normal pressure, the reaction was carried out at 60°C for 5 hours, whereby the alcoholized product was cyclized by a ring-closure reaction to obtain a cyclized product. Next, the obtained cyclized product was distilled under reduced pressure to 2.0 kPa at 130°C. Next, after adding 585 g of water and 1.3 g of 75% aqueous phosphoric acid solution under normal pressure, the reaction was carried out at 170°C and 0.8 kPa to open the ring of the cyclized product, and 423 g of biogenic 2-ethylhexyl glycerol ether was obtained. Then, distillation was carried out at 160°C to 210°C and 1.0 kPa to obtain biogenic 2-ethylhexyl glycerol ether C.

[0082] <Comparative Example 1>

[0083] In Example 1, instead of biogenic 2-ethylhexanol, 1051 g of 2-ethylhexanol from petroleum raw material sources, which was manufactured by subjecting propylene from petroleum raw material sources to aldol condensation and hydrogenation after producing n-butyraldehyde by the oxo process, was used. Otherwise, 2-ethylhexyl glycerol ether D from petroleum raw material sources was obtained by the same method.

[0084] <Deodorizing property evaluation>

[0085] For the 2-ethylhexyl glycerol ethers produced in Examples 1 to 3 and Comparative Example 1, the deodorizing properties immediately after production were evaluated respectively. Specifically, seven testers confirmed the odor of the produced 2-ethylhexyl glycerol ether respectively. The 2-ethylhexyl glycerol ether that was felt to be completely odorless (odor suppressed) was rated 10 points, and the 2-ethylhexyl glycerol ether that was felt to have a strong odor was rated 1 point. The rating was carried out on a 10-point scale from 1 to 10, and the total score of the rating 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 ×, thereby evaluating the deodorizing property. The evaluation results are shown in Table 1.

[0086] [Table 1]

[0087] Deodorizing property evaluation Example 1 Biologically-derived 2-ethylhexyl glycerol ether A ◎ Example 2 Biologically-derived 2-ethylhexyl glycerol ether B ◎ Example 3 Biologically-derived 2-ethylhexyl glycerol ether C ◎ Comparative Example 1 Petroleum raw material-derived 2-ethylhexyl glycerol ether D ×

[0088] According to the present invention, a branched-chain alkyl glycerol ether of biogenic origin with suppressed odor can be obtained using biogenic raw materials.

Claims

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

2. The method for manufacturing the branched alkyl glycerol ether of biological origin according to claim 1, wherein, The step of producing a branched alkyl glycerol ether of biological origin using a biological origin branched primary alcohol includes: an alcoholization step of reacting the biological origin branched primary alcohol with biological origin epichlorohydrin to obtain an alcoholized product, a ring-closing step of ring-closing the obtained alcoholized product by a ring-closing reaction to obtain a ring-closed product, and an opening step of opening the obtained ring-closed product by an opening reaction to obtain a branched alkyl glycerol ether of biological origin.