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

Abstract

The present invention provides a method for producing a bio-derived branched alkyl glyceryl ether, the method comprising: a step for producing a bio-derived branched primary alcohol having a branched alkyl group having 6 to 12 carbon atoms, the step including dimerizing at least one component selected from the group consisting of 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; and a step for producing a bio-derived branched alkyl glyceryl ether using the bio-derived branched primary alcohol. The present invention also provides a bio-derived branched alkyl glyceryl ether produced by the method.

Description

Technical Field

[0001] The present invention relates to a method for producing a bio-derived branched alkyl glyceryl ether capable of obtaining a bio-derived branched alkyl glyceryl ether with suppressed odor using a bio-derived raw material.

Background Art

[0002] In cosmetics, detergents, etc., antibacterial agents are generally used for purposes such as antiseptic, and among these, alkyl glyceryl ethers are known to be used as compounds with high safety for the human body (for example, Patent Documents 1 to 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 structure and production method. As a countermeasure, for example, Patent Document 3 describes a method for producing a glyceryl ether-containing composition capable of maintaining quality over a long period.

[0004] In recent years, in the entire chemical field including cosmetic ingredients, from the viewpoint of environmental consideration, etc., it has been required to bio-source some or all of the raw materials used in production. In response to this trend, there is a demand in the market for the development of a method for producing a glyceryl ether-containing composition that can maintain quality over a long period by a simple method while using bio-derived raw materials.

Prior Art Documents

Patent Documents

[0005]

Patent Document 1

Patent Document 2

Patent Document 3

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 that can obtain a bio-derived branched alkyl glyceryl ether with suppressed odor while using bio-derived raw materials.

Means for Solving the Problems

[0007] Therefore, the present inventors have conducted intensive studies and arrived at the present invention. That is, the present invention includes a step of obtaining a bio-derived branched primary alcohol having a branched alkyl group having 6 to 12 carbon atoms, including dimerizing one or more selected from the group consisting of 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, and a step of producing a bio-derived branched alkyl glyceryl ether using the obtained bio-derived branched primary alcohol. It is a method for producing a bio-derived branched alkyl glyceryl ether.

Advantages of the Invention

[0008] According to the present invention, it is possible to provide a method for producing a bio-derived branched alkyl glyceryl ether that can obtain a bio-derived branched alkyl glyceryl ether with suppressed odor using bio-derived raw materials.

Embodiments for Carrying Out the Invention

[0009] The bio-derived linear primary alcohol used in the present invention is one or more selected from the group consisting of bio-derived linear primary alcohols having a linear alkyl group with 3 to 6 carbon atoms and bio-derived linear primary alcohols having a linear alkenyl group with 3 to 6 carbon atoms, which are obtained from plant resources and the like. For example, primary alcohols obtained by purifying 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, linseed oil, etc., primary alcohols obtained by fermenting and / or metabolizing biomass derived from corn, sugarcane, sugar beet, banana, wheat, barley, rye, potato, sweet potato, cassava, taro, broad bean, lentil, pea, etc. by 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, linseed oil, etc. as raw materials, etc. can be mentioned.

[0010] 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 purifying and / or separating the above vegetable oil is not particularly limited, and known methods can be used. For example, a method of producing from the fatty acid obtained by hydrolyzing the fatty acid glyceride contained in the vegetable oil can be used. At this time, as the method for producing 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 from the fatty acid, known methods can be used. For example, a method of hydrogenating after methyl esterifying the fatty acid, a method of directly hydrogenating the fatty acid, etc. can be used.

[0011] 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 with microorganisms is not particularly limited, and known methods can be used. For example, saccharides such as cellulose obtained from biomass can be fermented and / or metabolized by microorganisms such as fungi, enzymes, and yeasts having fermentation and / or metabolic capabilities under an environment of appropriate temperature, humidity, atmosphere, etc.

[0012] 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 synthesizing using various bio-derived compounds obtained from the above plant resources, etc. 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 the raw material may 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 the raw material may be produced. Examples of such methods include, for example, 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, or a method of obtaining an aldehyde compound by oxidizing or dehydrogenating a bio-derived alcohol such as ethanol or propanol by a known method and then condensing and hydrogenating the obtained aldehyde compound.

[0013] The bio-derived linear primary alcohols having a linear alkyl group with 3 to 6 carbon atoms used in the present invention are not particularly limited as long as they are bio-derived linear primary alcohols having a linear alkyl group and a hydroxyl group in the molecule. Specifically, 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. can be mentioned. The bio-derived linear primary alcohols having a linear alkenyl group with 3 to 6 carbon atoms are not particularly limited as long as they are bio-derived linear primary alcohols having a linear alkenyl group and a hydroxyl group in the molecule. Specifically, bio-derived n-propenyl alcohol (allyl alcohol), bio-derived n-butenyl alcohol (crotyl alcohol), bio-derived n-pentenyl alcohol, bio-derived n-hexenyl alcohol, etc. can be mentioned. Among these, from the viewpoint of obtaining a bio-derived branched alkyl glyceryl ether with more suppressed odor, it is preferable to use bio-derived n-butanol (1-butanol) as the bio-derived linear primary alcohol. These bio-derived linear primary alcohols can be used without particular limitation as long as they are obtained by a known method from plant resources or the like.

[0014] The bio-derived linear aldehyde used in the present invention is one or more selected from the group consisting of bio-derived linear aldehydes having a linear alkyl group with 3 to 6 carbon atoms and bio-derived linear aldehydes having a linear alkenyl group with 3 to 6 carbon atoms, which are obtained from plant resources or the like. For example, aldehydes obtained by fermenting and / or metabolizing biomass derived from corn, sugarcane, sugar beet, banana, wheat, barley, rye, potato, sweet potato, cassava, taro, broad bean, lentil, pea, etc. by microorganisms, and aldehydes obtained by synthesizing using various bio-derived compounds such as bio-derived linear 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 oil, camellia oil, linseed oil, etc. as raw materials can be mentioned.

[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 biomass with microorganisms is not particularly limited, and known methods can be used. For example, saccharides such as cellulose obtained from biomass can be fermented and / or metabolized by microorganisms such as fungi, enzymes, and yeasts having fermentation and / or metabolic ability under an environment of appropriate temperature, humidity, atmosphere, etc.

[0016] In addition, the method for synthesizing 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 using various bio-derived compounds such as bio-derived linear primary alcohols 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, even if a bio-derived linear aldehyde having a hydrocarbon group with the same number of carbon atoms as the bio-derived compound used as the raw material is produced, or a bio-derived linear aldehyde having a hydrocarbon group with a different number of carbon atoms from the bio-derived compound used as the raw material is produced and used in the present invention, it may be used. Examples of such methods include, for example, a method of oxidizing or dehydrogenating 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 a known method, a method of producing an aldehyde with an increased number of carbon atoms by hydroformylation by the oxo process using an olefin with 2 to 5 carbon atoms, carbon monoxide, and hydrogen, and a method of producing an aldehyde with an increased number of carbon atoms by condensing an aldehyde with 2 to 4 carbon atoms obtained by oxidizing or dehydrogenating a bio-derived alcohol such as ethanol or propanol by a known method. In the present invention, among these bio-derived linear aldehydes, from the viewpoint of obtaining a bio-derived branched alkyl glyceryl ether with more suppressed odor, it is preferable to use a bio-derived linear aldehyde obtained by oxidizing or dehydrogenating 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 a known method.

[0017] Examples of the bio-derived linear aldehyde having a linear alkyl group with 3 to 6 carbon atoms used in the present invention include bio-derived linear aldehydes having a linear alkyl group and an aldehyde group in the molecule, and are not particularly limited as long as they are bio-derived linear aldehydes having 3 to 6 carbon atoms. Specifically, bio-derived n-propionaldehyde (propanal), bio-derived n-butylaldehyde (butanal), bio-derived n-valeraldehyde (pentanal), and bio-derived n-hexylaldehyde (hexanal) can be mentioned. Examples of the bio-derived linear aldehyde having a linear alkenyl group with 3 to 6 carbon atoms include bio-derived linear aldehydes having a linear alkenyl group and an aldehyde group in the molecule, and are not particularly limited as long as they are bio-derived linear aldehydes having 3 to 6 carbon atoms. Specifically, bio-derived n-propenal (propenal, acrolein), bio-derived n-butenal (butenal, crotonaldehyde), bio-derived n-pentenal (pentenal), bio-derived n-hexenal (hexenal), etc. can be mentioned. Among these, from the viewpoint of obtaining a bio-derived branched alkyl glyceryl ether with more suppressed odor, it is preferable to use bio-derived n-butylaldehyde (butanal) as the bio-derived linear aldehyde. These bio-derived linear aldehydes can be used without particular limitation as long as they are obtained by a known method from plant resources or the like. For example, when using bio-derived n-butylaldehyde as the bio-derived linear aldehyde having a linear alkyl group with 3 to 6 carbon atoms, bio-derived n-butylaldehyde obtained by oxidizing or dehydrogenating biobutanol by a known method, or bio-derived n-butylaldehyde obtained by hydroformylating biopropylene by the oxo process can be used. In the present invention, from the viewpoint of obtaining a bio-derived branched alkyl glyceryl ether with particularly suppressed odor, it is particularly preferable to use bio-derived n-butylaldehyde obtained by oxidizing or dehydrogenating biobutanol by a known method as the bio-derived linear aldehyde.

[0018] As a method for dimerizing one or more selected from the group consisting of bio-derived linear primary alcohols having a linear alkyl group with 3 to 6 carbon atoms, bio-derived linear primary alcohols having a linear alkenyl group with 3 to 6 carbon atoms, bio-derived linear aldehydes having a linear alkyl group with 3 to 6 carbon atoms, and bio-derived linear aldehydes having a linear alkenyl group with 3 to 6 carbon atoms, known methods can be used. For example, the method for dimerizing alcohols described in Catal. Sci. Technol., 2015, vol. 5, p. 3876-3902, the method for dimerizing aldehydes described in JP-A-09-124536, etc. can be used. Specifically, in the presence of a catalyst or a basic compound as necessary, at 60 to 320 ° C., bio-derived linear primary alcohols having a linear alkyl group with 3 to 6 carbon atoms with each other, bio-derived linear primary alcohols having a linear alkenyl group with 3 to 6 carbon atoms with each other, bio-derived linear aldehydes having a linear alkyl group with 3 to 6 carbon atoms with each other, or bio-derived linear aldehydes having a linear alkenyl group with 3 to 6 carbon atoms with each other can be reacted to dimerize. In the present invention, in a system in which two or more selected from the group consisting of bio-derived linear primary alcohols having a linear alkyl group with 3 to 6 carbon atoms, bio-derived linear primary alcohols having a linear alkenyl group with 3 to 6 carbon atoms, bio-derived linear aldehydes having a linear alkyl group with 3 to 6 carbon atoms, and bio-derived linear aldehydes having a linear alkenyl group with 3 to 6 carbon atoms are mixed, under the above conditions, bio-derived linear primary alcohols having a linear alkyl group with 3 to 6 carbon atoms with each other, bio-derived linear primary alcohols having a linear alkenyl group with 3 to 6 carbon atoms with each other, bio-derived linear aldehydes having a linear alkyl group with 3 to 6 carbon atoms with each other, or bio-derived linear aldehydes having a linear alkenyl group with 3 to 6 carbon atoms with each other can be reacted to dimerize them respectively. At this time, the reaction may be carried out in a reduced pressure or pressurized state in the reaction vessel.

[0019] As catalysts that can be used when dimerizing bio-derived linear primary alcohols or bio-derived linear aldehydes, known catalysts can be used. For example, metal catalysts such as metal powders, metal oxides, metal complexes, metal salts, and metal alkoxides of copper, silver, zinc, nickel, palladium, platinum, cobalt, rhodium, iridium, iron, ruthenium, manganese, chromium, molybdenum, etc., and nitroxyl radical catalysts such as 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) can be mentioned, and one or more of these can be used. Also, when using a metal catalyst, 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, pentamethylcyclopentadienyl; phosphine ligands such as ethylenebis(diphenylphosphine), cyclohexyldiphenylphosphine, dicyclohexylphenylphosphine, tri-t-butylphosphine, triphenylphosphine; nitrogen-containing ligands such as triethylamine, benzylamine, bipyridyl, bisiminopyridine, imidazole, etc., and one or more of these can be used.

[0020] As basic compounds that can be used when dimerizing bio-derived linear primary alcohols or bio-derived linear aldehydes, for example, oxides, hydroxides, carbonates, carboxylates, phosphates, amine salts, alkoxide compounds of alkali metals such as lithium, sodium, potassium, etc., and oxides, hydroxides, carbonates, carboxylates, phosphates, amine salts, alkoxide compounds of alkaline earth metals such as magnesium, calcium, etc. can be mentioned, and one or more of these can be used. Also, these catalysts may be supported on zeolite, silica, alumina zirconia, magnesia, activated carbon, graphite, carbon nanotubes, etc. and used.

[0021] In addition, when dimerizing a bio-derived linear primary alcohol or a bio-derived linear aldehyde, a solvent can 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, 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 these can be used.

[0022] As a process for obtaining a bio-derived branched primary alcohol having a branched alkyl group with 6 to 12 carbon atoms in the present invention, when only a bio-derived linear primary alcohol is used as a raw material, it is sufficient to include a step of dimerizing the bio-derived linear primary alcohol, and it may consist only of the step of dimerizing the bio-derived linear primary alcohol, or may include other steps as necessary. For example, when dimerizing bio-derived linear primary alcohols having a linear 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, a hydrogenation step is performed before or after the dimerization step. In addition, when using a raw material containing a bio-derived linear aldehyde, it is sufficient to include a step of dimerizing the bio-derived linear aldehyde and a step of hydrogenating the obtained compound, and it may consist only of 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 performing the above steps, when using bio-derived n-propanol or bio-derived n-propenyl alcohol as the bio-derived linear primary alcohol, bio-derived 2-methylpentanol can be produced; when using bio-derived n-butanol or bio-derived n-butenyl alcohol, bio-derived 2-ethylhexanol can be produced; when using bio-derived n-pentanol or bio-derived n-pentenyl alcohol, bio-derived 2-propylheptanol can be produced; when using bio-derived n-hexanol or bio-derived n-hexenyl alcohol, bio-derived 2-butyl octanol can be produced, and each can be produced as a bio-derived branched primary alcohol having a branched alkyl group with 6 to 12 carbon atoms, from which a bio-derived branched alkyl glyceryl ether with suppressed odor can be easily produced. Similarly, by performing the above steps, when using bio-derived n-propionaldehyde or bio-derived n-propenal as the bio-derived linear aldehyde, bio-derived 2-methylpentanol can be produced; when using bio-derived n-butyl aldehyde or bio-derived n-butenal, bio-derived 2-ethylhexanol can be produced; when using bio-derived n-valeraldehyde or bio-derived n-pentenal, bio-derived 2-propylheptanol can be produced; when using bio-derived n-hexyl aldehyde or bio-derived n-hexenal, bio-derived 2-butyl octanol can be produced, and each can be produced as a bio-derived branched primary alcohol having a branched alkyl group with 6 to 12 carbon atoms, from which a bio-derived branched alkyl glyceryl ether with suppressed odor can be easily produced.

[0024] In the present invention, from the viewpoints of suppressing the odor of the bio-derived branched alkyl glyceryl ether obtained and various properties, as a step of obtaining a bio-derived branched primary alcohol, a step of obtaining bio-derived 2-ethylhexanol by dimerizing bio-derived n-butanol (1-butanol), a step of dimerizing bio-derived n-butylaldehyde and further hydrogenating it to obtain bio-derived 2-ethylhexanol, or a step of dimerizing bio-derived n-butanol and bio-derived n-butylaldehyde respectively, and further hydrogenating bio-derived 2-ethylhexenal contained in the product to obtain bio-derived 2-ethylhexanol is preferably carried out.

[0025] The step of producing the bio-derived branched alkyl glyceryl ether in the present invention is a step of producing a bio-derived branched alkyl glyceryl ether using the bio-derived branched primary alcohol obtained in the above-described step. Examples of the method for producing a bio-derived branched alkyl glyceryl ether using a bio-derived branched primary alcohol include a method of subjecting a bio-derived branched primary alcohol and glycerin to a dehydration condensation reaction, a method of subjecting a bio-derived branched primary alcohol and 1-chloro-2,3-propanediol to a dehydrochlorination reaction, a method of reacting a bio-derived branched primary alcohol and epichlorohydrin and then hydrolyzing the obtained glycidyl ether, a method of reacting a bio-derived branched primary alcohol and glycidol, a method of subjecting a bio-derived branched primary alcohol and allyl chloride to a dehydrochlorination reaction and then oxidizing it with hydrogen peroxide or the like and hydrolyzing the obtained glycidyl ether, and the like. In these methods, the compound to be reacted with the bio-derived branched primary alcohol may be a bio-derived compound such as a plant resource or a compound derived from a petroleum raw material, but from the viewpoint of environmental consideration, it is preferable to use a bio-derived compound. In the present invention, among these, it is preferable to use a method of reacting a bio-derived branched primary alcohol and bio-derived epichlorohydrin and then hydrolyzing the obtained glycidyl ether.

[0026] Here, the bio-derived epichlorohydrin that can be preferably used in the present invention is epichlorohydrin produced from plant resources or the like. Examples include bio-derived epichlorohydrin produced using biomass derived from vegetable oils such as soybean oil, rapeseed oil, or palm kernel oil, and corn, sugarcane, sugar beet, wheat, barley, rye, etc. The method for producing such bio-derived epichlorohydrin is not particularly limited, and known methods can be used. For example, glycerin fatty acid esters contained in vegetable oils such as soybean oil, rapeseed oil, or palm kernel oil, and glycerin fatty acid esters produced from biomass derived from corn, sugarcane, sugar beet, wheat, barley, rye, etc., and a chlorinating agent are used to produce bio-derived dichloropropanol, and then bio-derived epichlorohydrin is obtained by dehydrochlorination. In the present invention, commercially available bio-derived epichlorohydrin such as Epicerol (registered trademark) manufactured by Solvay may also be used.

[0027] As a method that can be preferably used for producing the bio-derived branched alkyl glyceryl ether of the present invention, a method of reacting a bio-derived branched primary alcohol with a bio-derived epichlorohydrin and then hydrolyzing the resulting glycidyl ether is, more specifically, a hydrinization step of reacting a bio-derived branched primary alcohol with a bio-derived epichlorohydrin to obtain a hydrinized product, a ring-closing step of ring-closing the obtained hydrinized product by a ring-closing reaction to obtain a ring-closed product, and a ring-opening step of ring-opening the obtained ring-closed product 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 bio-derived raw materials.

[0028] In the hydrinization step of reacting a bio-derived branched primary alcohol with a bio-derived epichlorohydrin to obtain a hydrinized product, the ratio of the amounts of the bio-derived branched primary alcohol and the bio-derived epichlorohydrin used is not particularly limited. However, from the perspective of the odor suppression effect of the resulting bio-derived branched alkyl glyceryl ether, the amounts of the bio-derived branched primary alcohol and the bio-derived epichlorohydrin used are preferably in a molar ratio of 1.0:0.1 to 1.0:1.2, more preferably 1.0:0.2 to 1.0:1.0, and even more preferably 1:0.3 to 1:0.8. Also, the method of reacting the bio-derived branched primary alcohol with the bio-derived epichlorohydrin in the hydrinization step is not particularly limited. For example, a method of mixing the bio-derived branched primary alcohol and the bio-derived epichlorohydrin and reacting them at 20 to 150°C for 1 minute to 24 hours while heating and cooling as necessary can be mentioned. Further, in the hydrinization step, a known catalyst may be used.

[0029] The ring-closing step of obtaining a ring-closed product by subjecting the hydrinated product obtained in the hydrination step to a ring-closing reaction is specifically a step of eliminating a chloro group from the hydrinated product obtained in the hydrination step to form an epoxy group. The method of subjecting the hydrinated product to 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 hydrinated product and condensing it can be used. 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 aqueous solutions thereof can be used. The ratio of the usage amounts of the hydrinated product and the alkali agent when adding a known alkali agent to the hydrinated product and performing dehydration condensation is not particularly limited, but from the viewpoint of the odor suppression effect of the obtained bio-derived branched alkyl glycerol ether, the usage amounts of the hydrinated product and the alkali agent are preferably 1:0.5 to 1:3 in molar ratio, and more preferably 1:1 to 1:2. In addition, the specific method when using a method of adding a known alkali agent to the hydrinated product and performing dehydration condensation is not particularly limited, and for example, a method of adding an aqueous solution of a known alkali agent to the hydrinated product and mixing it, and reacting it at 20 to 150 °C for 1 minute to 24 hours while performing heating and cooling as necessary can be mentioned. Further, in the ring-closing reaction, a known catalyst may be used.

[0030] The ring-opening step of obtaining bio-derived branched alkyl glyceryl ether by ring-opening the cyclized product obtained in the ring-closure step through a ring-opening reaction is specifically a ring-opening step of obtaining bio-derived branched alkyl glyceryl ether by ring-opening the epoxy group of the cyclized product obtained in the ring-closure step through a ring-opening reaction to form two hydroxyl groups. In the ring-opening step, the method for ring-opening the cyclized product through a ring-opening reaction is not particularly limited, and for example, a method of hydrolyzing the cyclized product to effect ring-opening can be used. The method for hydrolyzing the cyclized product to effect ring-opening is not particularly limited, and examples include a method of adding water to the cyclized product and reacting it at 20 to 200 °C for 1 minute to 24 hours while heating or cooling under a reduced pressure or increased pressure environment (0.01 kPa to 10 MPa) as necessary. Also, in the ring-opening reaction, a known catalyst may be used, and for example, acids such as sulfuric acid, hydrochloric acid, perchloric acid, phosphoric acid, acetic acid, and peracetic acid can be used.

[0031] In the method for producing a bio-derived branched alkyl glyceryl ether of the present invention, in addition to the step of obtaining a bio-derived branched primary alcohol having a branched alkyl group having 6 to 12 carbon atoms, which includes dimerizing one or more selected from the group consisting of a 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 the step of producing a bio-derived branched alkyl glyceryl ether using the obtained bio-derived branched primary alcohol, a distillation step of distilling the product by a known method may further be included. In the present invention, examples of the distillation step include a step of distilling a product containing a cyclized product after a ring-closing step (intermediate distillation step), a step of distilling a product containing a bio-derived branched alkyl glyceryl ether after a ring-opening step (final distillation), etc. Any of these steps may be performed, or both steps may be performed. Further, the method for distilling the product is not particularly limited, and for example, methods such as atmospheric distillation, vacuum distillation, molecular distillation, steam distillation, etc. 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, extractive distillation, etc. can be used.

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

[0033] The bio-derived branched alkyl glyceryl ether of the present invention is obtained by dimerizing one or more selected from the group consisting of 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 glyceryl ether using the obtained bio-derived branched primary alcohol. The bio-derived branched alkyl glyceryl ether is produced by a method for producing a bio-derived branched alkyl glyceryl ether including these steps. Each step in the present invention can use the methods described above, and further, it may be a bio-derived branched alkyl glyceryl ether produced by a production method including the distillation step and / or deodorization step described above.

[0034] Here, the bio-derived branched alkyl glyceryl ether of the present invention slightly contains inevitable impurities derived from raw materials. By identifying these inevitable impurities, it is possible to distinguish the branched alkyl glyceryl ether of the present invention from branched alkyl glyceryl ethers produced from non-bio-derived 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, it is impossible to uniformly identify the inevitable impurities. Therefore, the bio-derived branched alkyl glyceryl ether of the present invention is specified by a production method with limited raw materials.

[0035] From the perspective of long-term quality stability, the bio-derived branched alkyl glyceryl ether of the present invention may be a bio-derived branched alkyl glyceryl ether-containing composition containing 0.05 to 0.30 parts by mass of an antioxidant such as tocopherols with respect to 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, and other known antioxidants can be used. However, from the perspective of further enhancing long-term quality stability, it is preferable that tocopherols account for 50% by mass or more and 100% by mass or less of the total amount of antioxidants in the bio-derived branched alkyl glyceryl ether-containing composition, more preferably 75% by mass or more and 100% by mass or less, and particularly preferably 100% by mass (the antioxidant consists only of tocopherols).

[0036] The cosmetic composition or detergent composition of the present invention is a cosmetic composition or detergent composition containing the aforementioned bio-derived branched alkyl glyceryl ether. The blending amount of the bio-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 still more preferably 0.10 to 5.0% by mass, based on the total amount of the cosmetic composition or detergent composition. By incorporating the above-mentioned bio-derived branched alkyl glyceryl ether into the cosmetic composition or detergent composition, the bio-derived branched alkyl glyceryl ether functions as an antibacterial agent (preservative) for the composition. In addition, since the bio-derived branched alkyl glyceryl ether of the present invention has suppressed odor, it can prevent adverse effects on the fragrance of the composition even when contained in the cosmetic composition or detergent composition.

[0037] The specific usage forms of the cosmetic composition or detergent composition of the present invention are not particularly limited. For example, shampoo, rinse, conditioner, treatment, lotion, emulsion, milk, cream, facial wash foam, cleansing milk, cleansing lotion, cleansing oil, hair nourishing agent, hair liquid, setting lotion, hair bleach, color rinse, permanent wave liquid, lipstick, pack, foundation, cologne, sunscreen, deodorant, perfume, and cosmetic oil, etc. may be mentioned.

[0038] The cosmetic composition or detergent composition of the present invention can be formulated with additives generally used in cosmetics or detergents in order to improve and modify various properties (solubility, dispersibility, stability, feel in use, spreadability, penetrability, moisturizing property, safety, design property, optical property, aromatic property, whitening property, etc.) during storage, use, and after use according to the purpose of use. Examples of such additives include, for example, higher alcohols, powder components, higher fatty acids, moisturizing agents, water-soluble polymers, sequestering agents, lower alcohols, water, polyhydric alcohols, monosaccharides, oligosaccharides, polysaccharides, amino acids and their derivatives, organic amines, pH adjusters, vitamins, ultraviolet ray protecting components, antioxidants, thickeners, surfactants, other blendable components (preservatives, blood circulation promoters, anti-inflammatory agents, activators, whitening agents, anti-seborrheic agents, anti-inflammatory agents, various extracts, and plant and seaweed extracts, etc.). One or more of these can be arbitrarily formulated.

[0039] Examples of higher alcohols include linear higher alcohols such as lauryl alcohol, cetyl alcohol, stearyl alcohol, behenyl alcohol, myristyl alcohol, oleyl alcohol, and cetostearyl alcohol; branched-chain higher alcohols such as monostearyl glycerin ether (batyl alcohol), 2-decyltetradecynol, lanolin alcohol, cholesterol, phytosterol, hexyl dodecanol, isostearyl alcohol, and octyl dodecanol, etc. One or more of these can be used.

[0040] Examples of the powder components include inorganic powders (e.g., talc, kaolin, mica, sericite, muscovite, phlogopite, synthetic mica, biotite, vermiculite, magnesium carbonate, calcium carbonate, aluminum silicate, barium silicate, calcium silicate, magnesium silicate, strontium silicate, metal tungstate salts, magnesium, silica, zeolite, barium sulfate, calcined calcium sulfate (calcined gypsum), 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, copolymer resin powder of styrene and acrylic acid, benzoguanamine resin powder, polytetrafluoroethylene powder, cellulose powder, etc.); inorganic white pigments (e.g., titanium dioxide, zinc oxide, etc.); inorganic red pigments (e.g., iron oxide (red 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 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, navy blue, etc.); pearl pigments (e.g., titanium dioxide-coated mica, titanium dioxide-coated bismuth oxychloride, titanium dioxide-coated talc, colored titanium dioxide-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., 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, etc.);Examples include natural pigments (e.g., chlorophyll, β-carotene, etc.), and one or more of these can be used.

[0041] 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., and one or more of these can be used.

[0042] Examples of humectants include polyethylene glycol, xylitol, sorbitol, maltitol, chondroitin sulfate, hyaluronic acid, mucoitin sulfate, calonic acid, atelocollagen, cholesteryl-12-hydroxystearate, sodium lactate, bile salts, dl-pyrrolidone carboxylate, short-chain soluble collagen, diglycerin (EO)PO adduct, extract of Rosa multiflora var. cathayensis, extract of Galium aparine, extract of Prunus mume, etc., and one or more of these can be used.

[0043] Examples of natural water-soluble polymers include plant-based polymers (e.g., gum arabic, tragacanth gum, galactan, guar gum, carob gum, karaya gum, carrageenan, pectin, agar, quince seed (marmelo), algal colloid (cassou extract), starch (rice, corn, potato, wheat), glycyrrhizic acid); microbial-based polymers (e.g., xanthan gum, dextran, succinoglucan, pullulan, gellan gum, etc.); animal-based polymers (e.g., collagen, casein, albumin, gelatin, etc.), etc., and one or more of these can be used.

[0044] Examples of the water-soluble polymer include starch polymers (e.g., carboxymethyl starch, methyl hydroxypropyl starch, etc.); cellulose polymers (methyl cellulose, ethyl cellulose, methyl hydroxypropyl 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 ester, etc.); vinyl polymers (e.g., polyvinyl alcohol, polyvinyl methyl ether, polyvinyl pyrrolidone, carboxyvinyl polymer, etc.); polyoxyethylene polymers (e.g., polyoxyethylene-polyoxypropylene copolymer using polyethylene glycol 20,000, 40,000 or 60,000 as a raw material, etc.); acrylic polymers (e.g., sodium polyacrylate, polyethyl acrylate, polyacrylamide, etc.); polyethyleneimine; cationic polymers, etc. One or more of these can be used.

[0045] Examples of the sequestering agent for metal ions include 1-hydroxyethane-1,1-diphosphonic acid, tetrasodium 1-hydroxyethane-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 ethylenediamine hydroxyethyltriacetate, etc. One or more of these can be used.

[0046] Examples of the lower alcohol include ethanol, propanol, isopropanol, isobutyl alcohol, t-butyl alcohol, etc. One or more of these can be used.

[0047] Examples of the polyhydric alcohol include dihydric alcohols (e.g., ethylene glycol, propylene glycol, 1,3 - butylene glycol, 1,2 - hexanediol, etc.); trihydric alcohols (e.g., glycerin, trimethylolpropane, etc.); tetrahydric alcohols (e.g., pentaerythritol such as 1,2,6 - hexanetriol, etc.); pentahydric alcohols (e.g., xylitol, etc.); hexahydric alcohols (e.g., sorbitol, mannitol, etc.); polyhydric alcohol polymers (e.g., diethylene glycol, dipropylene glycol, triethylene glycol, polypropylene glycol, tetraethylene glycol, diglycerin, polyethylene glycol, triglycerin, tetraglycerin, polyglycerin, etc.); dialkyl ethers of dihydric alcohols (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 ethers of dihydric alcohols (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.);Divalent alcohol ethers (e.g., ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, ethylene glycol monobutyl ether acetate, ethylene glycol monophenyl ether acetate, ethylene glycol diacetate, 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 hydrolyzate, maltose, xylitol, starch hydrolyzate reduced alcohol, etc.); glycidol; tetrahydrofurfuryl alcohol; POE-tetrahydrofurfuryl alcohol; POP-butyl ether; POP·POE-butyl ether; tripolyoxypropylene glycerin ether; POP-glycerin ether; POP-glycerin ether phosphate; POP·POE-pentaerythritol ether; polyglycerin, etc. may be mentioned, and one or more of these can be used.;

[0048] Examples of monosaccharides include 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-bucicose, D-galactose, D-fructose, L-galactose, L-mannose, D-tagatose, etc.); heptoses (e.g., aldheptose, heptulose, etc.); octoses (e.g., octulose, etc.); deoxy sugars (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 uronic acid, muramic acid, etc.); uronic acids (e.g., D-glucuronic acid, D-mannuronic acid, L-glucuronic acid, D-galacturonic acid, L-iduronic acid, etc.), etc. One or more of these can be used.

[0049] Examples of oligosaccharides include sucrose, umbelliferose, lactose, planteose, isolicnoses, α,α-trehalose, raffinose, licnoses, umbellisin, stachyose, verbascoses, etc. One or more of these can be used.

[0050] Examples of polysaccharides include cellulose, quince seed, chondroitin sulfate, starch, galactan, dermatan sulfate, glycogen, gum arabic, heparan sulfate, hyaluronic acid, tragacanth gum, keratan sulfate, chondroitin, xanthan gum, mucoitin sulfate, guar gum, dextran, kerato sulfate, locust bean gum, succinoglucan, caronin acid, etc. One or more of these can be used.

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

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

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

[0054] Examples of the vitamins include vitamin A, B1, B2, B6, C, E and their derivatives, pantothenic acid and its derivatives, biotin, etc., and one or more of these can be used.

[0055] As the ultraviolet ray protecting component, inorganic ultraviolet ray protecting components such as powder pigments and metal powder pigments, surface-treated products thereof, and organic ultraviolet ray protecting components can be used. For example, metal oxides such as titanium oxide, zinc oxide, cerium oxide, lower 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, silicone-treated, silicone resin-treated, pendant-treated, silane coupling agent-treated, titanium coupling agent-treated, silane-treated, oil-treated, N-acylated lysine-treated, polyacrylic acid-treated, metal soap-treated, acrylic resin-treated, metal oxide-treated products, etc., and salicylic acid-based, para-aminobenzoic acid-based, benzophenone-based, cinnamic acid-based, benzoylmethane-based, 2-ethylhexyl 2-cyano-3,3-diphenylprop-2-enoate, 2-ethylhexyl dimethoxybenzylidene dioxoimidazolidine propionate, 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-dimethoxyphenylmethylene)-2,5-dioxo-1-imidazolidine propionate, their polymer derivatives, etc. may be mentioned, and one or more of these can be used.

[0056] As the antioxidant, for example, tocopherols, dibutylhydroxytoluene, butylhydroxyanisole, gallic acid esters, etc. may be mentioned, and one or more of these can be used.

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

[0058] Examples of surfactants 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 ammonium saccharin, cetyl trimethyl ammonium saccharin, behenyl trimethyl ammonium methyl sulfate, behenyl dimethyl amine, diethylaminoethyl amide of behenic acid, dimethylaminopropyl amide of behenic acid, dimethylaminoethyl amide of behenic acid, stearyl dimethyl amine, palmityloxypropyl dimethyl amine, stearyloxypropyl dimethyl amine, etc.); anionic surfactants (e.g., alkyl ether sulfates, alkyl sulfates, alkyl ether sulfate esters, alkenyl ether sulfates, alkenyl sulfates, olefin sulfonates, alkane sulfonates, saturated or unsaturated fatty acid salts, alkyl or alkenyl ether carboxylates, α-sulfonated fatty acid salts, N-acyl amino acid type surfactants, phosphoric acid mono- or diester type surfactants, sulfosuccinic acid esters, N-alkyloyl methyl taurine salts, and their derivatives, etc.); amphoteric surfactants (e.g., betaine type amphoteric surfactants such as coconut oil fatty acid amide propyl dimethyl acetic acid betaine, lauryl dimethyl amino acid betaine, 2-alkyl-N-carboxymethyl-N-hydroxymethyl imidazolinium betaine, lauryl hydroxy sulfobetaine, lauroyl amide ethyl hydroxyethyl carboxymethyl betaine, metal salts of hydroxypropyl phosphoric acid, etc., amino acid type amphoteric surfactants such as metal salts of β-lauryl aminopropionic acid, etc., sulfate ester type amphoteric surfactants, and sulfonate type amphoteric surfactants, etc.);Nonionic surfactants (e.g., POE cetyl ether (Cetes), POE stearyl ether (Steares), POE behenyl ether, POE oleyl ether (Ores), POE lauryl ether (Laures), POE octyldodecyl ether, POE hexyldecyl ether, POE isostearyl ether, POE nonylphenyl ether, POE octylphenyl ether, POE polyoxypropylene cetyl ether, POE polyoxypropylene decyltetradecyl ether, POE sorbitan monooleate, POE sorbitan monostearate, POE sorbitan monopalmitate, POE sorbitan monolaurate, POE sorbitan trioleate, POE glycerin monostearate, POE glycerin monomyristate, POE sorbitol tetraoleate, POE sorbitol hexastearate, POE sorbitan monolaurate, POE sorbitol beeswax, polyethylene glycol monooleate, polyethylene glycol monostearate, polyethylene glycol monolaurate, lipophilic glycerin monooleate, lipophilic glycerin monostearate, self-emulsifying glycerin monostearate, sorbitan monooleate, sorbitan sesquioleate, sorbitan trioleate, sorbitan monostearate, sorbitan monopalmitate, sorbitan monolaurate, sucrose fatty acid ester, decaglyceryl monolaurate, decaglyceryl monostearate, decaglyceryl monooleate, decaglyceryl monomyristate, alkyl glucoside, POE methyl glucoside, POE methyl glucoside dioleate, etc.) and the like can be mentioned, and one or more of these can be used.;

[0059] Other components that can be formulated include, for example, preservatives (such as methylparaben, ethylparaben, butylparaben, phenoxyethanol, etc.); anti-inflammatory agents (such as glycyrrhizic acid derivatives, glycyrrhetinic acid derivatives, salicylic acid derivatives, hinokitiol, zinc oxide, allantoin, etc.); whitening agents (such as extract of Saxifraga stolonifera, arbutin, etc.); various extracts (such as Acanthopanax senticosus, Cinnamomum cassia, Citrus unshiu, Paeonia lactiflora, Polygonatum odoratum, Betula platyphylla, Salvia officinalis, Eriobotrya japonica, Daucus carota, Aloe vera, Abelmoschus manihot, Iris tectorum, Vitis vinifera, Dioscorea opposita, Benincasa hispida, Lilium brownii, Crocus sativus, Curcuma longa, Zingiber officinale, Viola philippica, Ononis spinosa, Allium sativum, Capsicum annuum, Coptis chinensis, Atractylodes lancea, Ligustrum lucidum, seaweed, etc.); activating agents (such as royal jelly, photosensitizer, cholesterol derivatives, etc.); blood circulation promoters (such as benzyl nicotinate, β-butoxyethyl nicotinate, capsaicin, gingerol, cantharidin, ichthyol, tannic acid, α-borneol, tocopherol nicotinate, inositol hexanicotinate, cyclandelate, cinnarizine, tolazoline, acetylcholine, verapamil, cephalanthin, γ-oryzanol, etc.); anti-seborrheic agents (such as sulfur, thiolanthrene, etc.); anti-inflammatory agents (such as tranexamic acid, thiotaurine, hypotaurine, etc.), etc. One or more of these can be used.

[0060] In the cosmetic composition or detergent composition of the present invention, the respective contents when adding higher alcohols, powder components, higher fatty acids, humectants, water-soluble polymers, sequestering agents, lower alcohols, water, polyhydric alcohols, monosaccharides, oligosaccharides, polysaccharides, amino acids and their derivatives, organic amines, pH adjusters, vitamins, UV protection components, antioxidants, thickeners, surfactants, other components that can be formulated (preservatives, blood circulation promoters, anti-inflammatory agents, activating agents, whitening agents, anti-seborrheic agents, anti-inflammatory agents, various extracts, plant and seaweed extracts, etc.) are not particularly limited and may be adjusted according to the embodiment and purpose. For example, 0.001 to 50.0% by mass may be added respectively based on the total mass of the cosmetic composition or detergent composition.

Examples

[0061] The present invention will be specifically described below with reference to examples. However, the present invention is not limited to these examples and may be changed without departing from the scope of the present invention. In the following examples, etc., % is based on mass unless otherwise specified.

[0062] <Example 1> 3552 g of bio-derived n-butanol, 424 g of tripotassium phosphate, 448 g of calcium oxide, and 160 g of a copper catalyst were added to an autoclave, and then reacted at 290 °C for 5 hours. Further, by filtration and distillation, 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 were obtained.

[0063] Subsequently, 1051 g of the obtained bio-derived 2-ethylhexanol and 3.5 g of anhydrous stannic chloride as a catalyst were added to another reaction vessel. While raising the temperature to 80 °C, 249 g of bio-derived epichlorohydrin (Epicerol (registered trademark) manufactured by Solvay) was added, and then reacted at 80 °C for 4 hours to obtain 570 g of a hydrinated product. Then, by reducing the pressure to 2.0 kPa at 150 °C, unreacted bio-derived 2-ethylhexanol was removed. Subsequently, 234 g of a 48% aqueous sodium hydroxide solution was added at normal pressure, and then reacted at 60 °C for 5 hours to cyclize the hydrinated product by a ring-closing reaction to obtain 429 g of a cyclized product. Subsequently, the obtained cyclized product was distilled under reduced pressure at 130 °C and 2.0 kPa. Subsequently, 585 g of water and 1.3 g of a 75% phosphoric acid aqueous solution were added at normal pressure, and then reacted at 170 °C and 0.8 kPa to open the ring of the cyclized product to obtain 423 g of bio-derived 2-ethylhexyl glyceryl ether. Further, distillation was performed at 160 °C to 210 °C and 1.0 kPa to obtain bio-derived 2-ethylhexyl glyceryl ether A.

[0064] <Example 2> 370.5 g of bio-derived n-butanol, 1.1 L of p-xylene, 39.8 g of pentamethylcyclopentadienyliridium(III) dichloride dimer, 55.1 g of 1,7-octadiene, and 224.42 g of potassium tert-butoxide were added to an autoclave. After reacting at 120 °C for 4 hours and then filtering and distilling, 260 g of bio-derived 2-ethylhexanol, a bio-derived branched primary alcohol in which bio-derived n-butanol was dimerized, was obtained.

[0065] Subsequently, 250 g of the obtained bio-derived 2-ethylhexanol and 0.8 g of stannic chloride anhydrous as a catalyst were added to another reaction vessel. While raising the temperature to 80 °C, 59.2 g of bio-derived epichlorohydrin (Epicerol (registered trademark) manufactured by Solvay) was added, and then the mixture was reacted at 80 °C for 4 hours to obtain 135.6 g of a hydrinated product. Then, unreacted bio-derived 2-ethylhexanol was removed by reducing the pressure to 2.0 kPa at 150 °C. Subsequently, 55.7 g of a 48% aqueous sodium hydroxide solution was added at normal pressure, and then the mixture was reacted at 60 °C for 5 hours to cyclize the hydrinated product by a ring-closing reaction to obtain 102.1 g of a cyclized product. Subsequently, the obtained cyclized product was distilled under reduced pressure at 130 °C and 2.0 kPa. Subsequently, 139.2 g of water and 0.3 g of a 75% aqueous phosphoric acid solution were added at normal pressure, and then the cyclized product was ring-opened by reacting at 170 °C and 0.8 kPa to obtain 100.6 g of bio-derived 2-ethylhexyl glyceryl ether. Further, distillation was performed at 160 °C to 210 °C and 1.0 kPa to obtain bio-derived 2-ethylhexyl glyceryl ether B.

[0066] <Example 3> To a reaction vessel of an open system to the atmosphere, 3100 g of bio-derived n-butanol, 398 g of copper(I) iodide, 327 g of TEMPO, 344 g of 1-methylimidazole, and 16 L of acetonitrile were added. After reacting at 25 °C for 24 hours, and further filtering and distilling, 2100 g of bio-derived n-butyl aldehyde was obtained. Subsequently, 2000 g of the obtained bio-derived n-butyl aldehyde was mixed with 2 L of a 2 wt% aqueous sodium hydroxide solution and reacted at 90 °C for 4 hours. After liquid-liquid separation, a 1720 g oil phase was obtained. By distilling the obtained oil phase, 1400 g of bio-derived 2-ethylhexenal in which the bio-derived n-butyl aldehyde was dimerized was obtained. Furthermore, after hydrogenating the obtained bio-derived 2-ethylhexenal in the presence of a nickel-based catalyst at a temperature of 120 °C, a pressure of 4.0 MPa for 2 hours and then distilling, 1260 g of bio-derived 2-ethylhexanol, which is a bio-derived branched primary alcohol, was obtained.

[0067] Subsequently, 1051 g of the obtained bio-derived 2-ethylhexanol and 3.5 g of stannic chloride anhydride as a catalyst were added to another reaction vessel. While raising the temperature to 80 °C, 249 g of bio-derived epichlorohydrin (Epicerol (registered trademark) manufactured by Solvay) was added, and after reacting at 80 °C for 4 hours, a hydrinated product was obtained. Then, by reducing the pressure to 2.0 kPa at 150 °C, unreacted bio-derived 2-ethylhexanol was removed. Subsequently, after adding 234 g of a 48% aqueous sodium hydroxide solution at normal pressure and reacting at 60 °C for 5 hours, the hydrinated product was cyclized by a ring-closing reaction to obtain a cyclized product. Subsequently, the obtained cyclized product was distilled at 130 °C and 2.0 kPa. Subsequently, after adding 585 g of water and 1.3 g of a 75% phosphoric acid aqueous solution at normal pressure and reacting at 170 °C and 0.8 kPa, the cyclized product was ring-opened to obtain 423 g of bio-derived 2-ethylhexyl glyceryl ether. Furthermore, distillation was performed at 160 °C to 210 °C and 1.0 kPa to obtain bio-derived 2-ethylhexyl glyceryl ether C.

[0068] <Comparative Example 1> In Example 1, except that 1051 g of 2-ethylhexanol derived from petroleum raw materials, which was produced by aldol condensation and hydrogenation of n-butylaldehyde after producing n-butylaldehyde from propylene derived from petroleum raw materials using the oxo process instead of bio-derived 2-ethylhexanol, was used, 2-ethylhexyl glyceryl ether D derived from petroleum raw materials was obtained by the same method.

[0069] <Deodorizing property evaluation> Regarding the 2-ethylhexyl glyceryl ethers produced in Examples 1 to 3 and Comparative Example 1, the deodorizing properties immediately after production were evaluated. Specifically, seven testers confirmed the odor of the 2-ethylhexyl glyceryl ether produced respectively, and those who felt that it was completely odorless (the odor was suppressed) were scored 10 points, and those who felt that there was a strong odor were scored 1 point on a 10-point scale from 1 to 10. The total score of the scoring results of each tester was calculated. If the total score was 60 points or more, the evaluation was ◎, if it was 45 points or more and less than 60 points, the evaluation was ○, and if it was less than 45 points, the evaluation was ×, and the deodorizing property was evaluated. The evaluation results are shown in Table 1.

[0070]

Table 1

[0071] According to the present invention, a bio-derived branched alkyl glyceryl ether with suppressed odor can be obtained using bio-derived raw materials.

Claims

1. A step of obtaining a bio-derived branched primary alcohol having a branched alkyl group with 6 to 12 carbon atoms, including dimerizing one or more selected from the group consisting of 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; and a step of producing a bio-derived branched alkyl glyceryl ether using the obtained bio-derived branched primary alcohol. A method for producing a bio-derived branched alkyl glyceryl ether, comprising these steps.

2. The step of producing a bio-derived branched alkyl glyceryl ether using the bio-derived branched primary alcohol includes a hydrinization step of reacting the bio-derived branched primary alcohol with a bio-derived epichlorohydrin to obtain a hydrinized product, a ring-closing step of ring-closing the obtained hydrinized product by a ring-closing reaction to obtain a ring-closed product, and a ring-opening step of ring-opening the obtained ring-closed product by a ring-opening reaction to obtain a bio-derived branched alkyl glyceryl ether. The method for producing a bio-derived branched alkyl glyceryl ether according to Claim 1.

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