Classifications

• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q5/00—Preparations for care of the hair
  • A61Q5/02—Preparations for cleaning the hair
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
  • C07C41/01—Preparation of ethers
  • C07C41/09—Preparation of ethers by dehydration of compounds containing hydroxy groups
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
  • C07C41/01—Preparation of ethers
  • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
  • C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
  • A61K8/34—Alcohols
  • A61K8/345—Alcohols containing more than one hydroxy group
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q19/00—Preparations for care of the skin
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q19/00—Preparations for care of the skin
  • A61Q19/10—Washing or bathing preparations
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
  • C07C29/32—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions without formation of -OH groups
  • C07C29/34—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions without formation of -OH groups by condensation involving hydroxy groups or the mineral ester groups derived therefrom, e.g. Guerbet reaction
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
  • C07C41/01—Preparation of ethers
  • C07C41/02—Preparation of ethers from oxiranes
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
  • C07C41/01—Preparation of ethers
  • C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C43/00—Ethers; Compounds having groups, groups or groups
  • C07C43/02—Ethers
  • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
  • C07C43/04—Saturated ethers
  • C07C43/13—Saturated ethers containing hydroxy or O-metal groups
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
  • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
  • C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
  • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
  • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
  • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
  • C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
  • C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
  • A61K2800/10—General cosmetic use

Definitions

• the present invention relates to a method for producing a bio-derived branched alkyl glyceryl ether, which can obtain a bio-derived branched alkyl glyceryl ether with suppressed odor by using a bio-derived raw material.
• alkyl glyceryl ethers are known to be used as compounds that are highly safe for the human body (for example, Patent Documents 1 and 2).
• Patent Document 3 describes a method for manufacturing a glyceryl ether-containing composition that can maintain its quality over a long period of time.
• the present invention aims to provide a method for producing a bio-derived branched alkyl glyceryl ether that uses a bio-derived raw material and can produce a bio-derived branched alkyl glyceryl ether with a suppressed odor.
• the present invention is a method for producing a bio-derived branched alkyl glyceryl ether, comprising: a step of obtaining a bio-derived branched primary alcohol having a branched alkyl group having 6 to 12 carbon atoms, the step 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.
• the present invention provides a method for producing a bio-derived branched alkyl glyceryl ether that can obtain a bio-derived branched alkyl glyceryl ether with reduced odor using a bio-derived raw material.
• 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, etc.
• 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, etc.
• 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 examples include primary alcohols obtained by fermenting and/or metabolizing biomass derived from crops such as corn, sugarcane, sugar beet, banana, wheat, barley, rye, potato, sweet potato, cassava, taro, broad bean, lentil, and pea using microorganisms, and primary alcohols obtained by synthesis 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.
• crops such as corn, sugarcane, sugar beet, banana, wheat, barley, rye, potato, sweet potato, cassava, taro, broad bean, lentil, and pea using microorganisms
• primary alcohols obtained by synthesis using various bio-derived compounds obtained from plant resources such as palm oil, palm kernel oil, soybean oil, rapeseed oil, castor oil,
• 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 refining and/or separating the above-mentioned vegetable oil is not particularly limited, and any known method can be used, but a method for producing from fatty acids obtained by hydrolyzing fatty acid glycerides contained in the vegetable oil can be used.
• a known method can be used 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 fatty acids, and for example, a method of methyl esterifying fatty acids and then hydrogenating them, or a method of directly hydrogenating fatty acids can be used.
• the method of fermenting the above biomass with a microorganism to obtain 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 is not particularly limited, and any known method can be used.
• a method can be used in which sugars such as cellulose obtained from biomass are fermented and/or metabolized by microorganisms such as fungi, enzymes, and yeasts that have the ability to ferment and/or metabolize under an environment of appropriate temperature, humidity, atmosphere, etc.
• the method of synthesizing various bio-derived compounds obtained from the above-mentioned plant resources as raw materials to obtain 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 is not particularly limited, and a known method can be used.
• 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 a method 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, and 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.
• the bio-derived linear primary alcohol having a linear alkyl group with 3 to 6 carbon atoms used in the present invention is not particularly limited as long as it is a bio-derived linear primary alcohol having 3 to 6 carbon atoms and a linear alkyl group and a hydroxyl group in the molecule, and specific examples thereof include bio-derived n-propanol (1-propanol), bio-derived n-butanol (1-butanol), bio-derived n-pentanol (1-pentanol), and bio-derived n-hexanol (1-hexanol).
• the bio-derived linear primary alcohol having a linear alkenyl group with 3 to 6 carbon atoms is not particularly limited as long as it is a bio-derived linear primary alcohol having 3 to 6 carbon atoms and a linear alkenyl group and a hydroxyl group in the molecule, and specific examples thereof include bio-derived n-propenyl alcohol (allyl alcohol), bio-derived n-butenyl alcohol (crotyl alcohol), bio-derived n-pentenyl alcohol, and bio-derived n-hexenyl alcohol.
• bio-derived linear primary alcohol from the viewpoint of obtaining a bio-derived branched alkyl glyceryl ether with a more suppressed odor, it is preferable to use bio-derived n-butanol (1-butanol) as the bio-derived linear primary alcohol.
• bio-derived linear primary alcohols can be used without any particular limitations as long as they are obtained from plant resources or the like by a known method.
• 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, etc.
• linear aldehydes examples include aldehydes obtained by fermenting and/or metabolizing biomass derived from corn, sugar cane, sugar beet, banana, wheat, barley, rye, potato, sweet potato, cassava, taro, broad bean, lentil, pea, etc., using microorganisms, and aldehydes obtained by synthesis using various bio-derived compounds as raw materials, 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, and linseed oil.
• 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, and linseed
• the method of fermenting the above biomass with a microorganism to obtain 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 is not particularly limited, and any known method can be used, such as a method in which sugars such as cellulose obtained from biomass are fermented and/or metabolized by microorganisms such as fungi, enzymes, and yeasts that have the ability to ferment and/or metabolize under an appropriate environment such as temperature, humidity, and atmosphere.
• the method for obtaining a bio-derived linear aldehyde having a linear alkyl group having 3 to 6 carbon atoms or a bio-derived linear aldehyde having a linear alkenyl group having 3 to 6 carbon atoms by synthesis using various bio-derived compounds such as the above-mentioned bio-derived linear primary alcohols obtained from plant resources, etc. as raw materials is not particularly limited, and any known method can be used.
• 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 may be 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 may be produced and used in the present invention.
• Examples of such methods include a method of oxidizing or dehydrogenating a bio-derived linear primary alcohol having a linear alkyl group having 3 to 6 carbon atoms or a bio-derived linear primary alcohol having a linear alkenyl group having 3 to 6 carbon atoms by a known method, a method of producing an aldehyde having an increased number of carbon atoms by hydroformylating an olefin having 2 to 5 carbon atoms, carbon monoxide, and hydrogen by an oxo method, and a method of producing an aldehyde having an increased number of carbon atoms by condensing an aldehyde having 2 to 4 carbon atoms obtained by oxidizing or dehydrogenating a bio-derived alcohol such as ethanol or propanol by a known method.
• bio-derived linear aldehyde obtained by oxidizing or dehydrogenating a bio-derived linear primary alcohol having a linear alkyl group having 3 to 6 carbon atoms or a bio-derived linear primary alcohol having a linear alkenyl group having 3 to 6 carbon atoms by a known method.
• the bio-derived linear aldehyde having a linear alkyl group of 3 to 6 carbon atoms used in the present invention is not particularly limited as long as it is a bio-derived linear aldehyde having 3 to 6 carbon atoms and having a linear alkyl group and an aldehyde group in the molecule, and specific examples include bio-derived n-propionaldehyde (propanal), bio-derived n-butylaldehyde (butanal), bio-derived n-valeraldehyde (pentanal), and bio-derived n-hexylaldehyde (hexanal).
• the bio-derived linear aldehyde having a linear alkenyl group having 3 to 6 carbon atoms is not particularly limited as long as it is a bio-derived linear aldehyde having 3 to 6 carbon atoms and a linear alkenyl group and an aldehyde group in the molecule, and specific examples thereof include bio-derived n-propene aldehyde (propenal, acrolein), bio-derived n-butene aldehyde (butenal, crotonaldehyde), bio-derived n-pentene aldehyde (pentenal), bio-derived n-hexene aldehyde (hexenal), etc.
• bio-derived n-butyl aldehyde butanal
• bio-derived linear aldehydes can be used without any particular limitation as long as they are obtained from plant resources or the like by known methods.
• bio-derived n-butylaldehyde when using bio-derived n-butylaldehyde as a bio-derived linear aldehyde having a linear alkyl group having 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 method can be used.
• bio-derived n-butylaldehyde obtained by oxidizing or dehydrogenating bio-derived n-butanol by a known method as the bio-derived linear aldehyde.
• bio-derived linear primary alcohols having a linear alkyl group with 3 to 6 carbon atoms 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, such as the method for dimerizing alcohols described in Catal. Sci. Technol., 2015, vol. 5, pp. 3876-3902 and the method for dimerizing aldehydes described in JP-A-09-124536.
• a method can be used in which, in the presence of a catalyst or a basic compound as necessary, at 60 to 320° C., two bio-derived linear primary alcohols having a linear alkyl group with 3 to 6 carbon atoms, two bio-derived linear primary alcohols having a linear alkenyl group with 3 to 6 carbon atoms, two bio-derived linear aldehydes having a linear alkyl group with 3 to 6 carbon atoms, or two bio-derived linear aldehydes having a linear alkenyl group with 3 to 6 carbon atoms are reacted to dimerize the resulting mixture.
• a method of reacting bio-derived linear primary alcohols having linear alkyl groups with 3 to 6 carbon atoms, bio-derived linear primary alcohols having linear alkenyl groups with 3 to 6 carbon atoms, bio-derived linear aldehydes having linear alkyl groups with 3 to 6 carbon atoms, or bio-derived linear aldehydes having linear alkenyl groups with 3 to 6 carbon atoms may be used under the above conditions. At this time, the reaction may be carried out
• the catalyst that can be used when dimerizing the bio-derived linear primary alcohol or the bio-derived linear aldehyde can be a known catalyst, for example, a metal catalyst such as a metal powder, a metal oxide, a metal complex, a metal salt, or a metal alkoxide, such as copper, silver, zinc, nickel, palladium, platinum, cobalt, rhodium, iridium, iron, ruthenium, manganese, chromium, or molybdenum, or a nitroxyl radical catalyst such as 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO), and one or more of these can be used.
• a metal catalyst such as a metal powder, a metal oxide, a metal complex, a metal salt, or a metal alkoxide, such as copper, silver, zinc, nickel, palladium, platinum, cobalt, rhodium, iridium, iron, ruthenium, manganese, chromium, or
• a compound that serves as a ligand may be used in combination.
• 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-t-butylphosphine, and triphenylphosphine; and nitrogen-containing ligands such as triethylamine, benzylamine, bipyridyl, bisiminopyridine, and imidazole. One or more of these can be used.
• Basic compounds that can be used when dimerizing a bio-derived linear primary alcohol or a bio-derived linear aldehyde include, for example, oxides, hydroxides, carbonates, carboxylates, phosphates, amine salts, and alkoxide compounds of alkali metals such as lithium, sodium, and potassium, and oxides, hydroxides, carbonates, carboxylates, phosphates, amine salts, and alkoxide compounds of alkaline earth metals such as magnesium and calcium, and one or more of these can be used.
• These catalysts may also be supported on zeolite, silica, alumina zirconia, magnesia, activated carbon, graphite, carbon nanotubes, and the like.
• a solvent when dimerizing the bio-derived linear primary alcohol or the bio-derived linear aldehyde, a solvent can be used as necessary.
• 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, and the like. One or more of these can be used.
• the process for obtaining a bio-derived branched primary alcohol having a branched alkyl group having 6 to 12 carbon atoms may include a step of dimerizing the bio-derived linear primary alcohol, and may include only the step of dimerizing the bio-derived linear primary alcohol or may include other steps as necessary.
• a bio-derived linear primary alcohol having a branched alkyl group having 6 to 12 carbon atoms is obtained by dimerizing a bio-derived linear primary alcohol having a linear alkenyl group having 3 to 6 carbon atoms
• a hydrogenation step is performed before or after the dimerization step.
• the process includes a step of dimerizing the bio-derived linear aldehyde and a step of hydrogenating the obtained compound.
• the process may consist of only the step of dimerizing the bio-derived linear aldehyde and the step of hydrogenating the obtained compound, or may include other steps as necessary.
• bio-derived 2-methylpentanol can be produced; when bio-derived n-butanol or bio-derived n-butenyl alcohol is used, bio-derived 2-ethylhexanol can be produced; when bio-derived n-pentanol or bio-derived n-pentenyl alcohol is used, bio-derived 2-propylheptanol can be produced; and when bio-derived n-hexanol or bio-derived n-hexenyl alcohol is used, bio-derived 2-butyloctanol can be produced.
• bio-derived branched primary alcohols having branched alkyl groups having 6 to 12 carbon atoms that can easily produce odor-suppressed bio-derived branched alkyl glyceryl ethers.
• bio-derived 2-methylpentanol can be produced; when bio-derived n-butylaldehyde or bio-derived n-butenealdehyde is used, bio-derived 2-ethylhexanol can be produced; when bio-derived n-valeraldehyde or bio-derived n-pentenealdehyde is used, bio-derived 2-propylheptanol can be produced; and when bio-derived n-hexylaldehyde or bio-derived n-hexenealdehyde is used,
• bio-derived branched alkyl glyceryl ether from the viewpoint of odor suppression and various properties of the obtained bio-derived branched alkyl glyceryl ether, it is preferable to carry out the following process for obtaining a bio-derived branched primary alcohol: a process for obtaining bio-derived 2-ethylhexanol by dimerizing bio-derived n-butanol (1-butanol), a process for obtaining bio-derived 2-ethylhexanol by dimerizing bio-derived n-butylaldehyde and further hydrogenating the product, or a process for obtaining bio-derived 2-ethylhexanol by dimerizing bio-derived n-butanol and bio-derived n-butylaldehyde, respectively, and further hydrogenating the bio-derived 2-ethylhexenal contained in the product.
• the process for producing a bio-derived branched alkyl glyceryl ether in the present invention is a process for producing a bio-derived branched alkyl glyceryl ether using the bio-derived branched primary alcohol obtained in the process described above.
• Examples of the method for producing a bio-derived branched alkyl glyceryl ether using a bio-derived branched primary alcohol include a method for dehydration condensation reaction of a bio-derived branched primary alcohol with glycerin, a method for dehydrochlorinating a bio-derived branched primary alcohol with 1-chloro-2,3-propanediol, a method for reacting a bio-derived branched primary alcohol with epichlorohydrin and then hydrolyzing the resulting glycidyl ether, a method for reacting a bio-derived branched primary alcohol with glycidol, a method for dehydrochlorinating a bio-derived branched primary alcohol with allyl chloride and then oxidizing the resulting glycidyl ether with hydrogen peroxide or the like, and the like.
• the compound 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.
• a bio-derived compound such as a plant resource or a compound derived from a petroleum raw material
• it is preferable to use a bio-derived compound it is preferable to use a method in which a bio-derived branched primary alcohol is reacted with a bio-derived epichlorohydrin, and then the resulting glycidyl ether is hydrolyzed.
• the bio-derived epichlorohydrin that can be preferably used in the present invention is epichlorohydrin produced from plant resources, etc., and examples thereof include bio-derived epichlorohydrin produced using vegetable oils such as soybean oil, rapeseed oil, and palm kernel oil, and biomass derived from corn, sugarcane, sugar beet, wheat, barley, rye, etc. as raw materials.
• vegetable oils such as soybean oil, rapeseed oil, and palm kernel oil
• biomass derived from corn, sugarcane, sugar beet, wheat, barley, rye, etc. as raw materials there are no particular limitations on the method for producing such bio-derived epichlorohydrin, and any known method can be used.
• bio-derived dichloropropanol is produced using a glycerol fatty acid ester contained in vegetable oils such as soybean oil, rapeseed oil, and palm kernel oil, or a glycerol fatty acid ester produced from biomass derived from corn, sugarcane, sugar beet, wheat, barley, rye, etc., and a chlorinating agent, and then bio-derived epichlorohydrin is obtained by dehydrochlorination, etc.
• commercially available bio-derived epichlorohydrin such as Epicerol (registered trademark) manufactured by Solvay may also be used in 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 which can be preferably used as a method for producing the bio-derived branched alkyl glyceryl ether of the present invention, is more specifically a method including a hydrination step of reacting a bio-derived branched primary alcohol with a bio-derived epichlorohydrin to obtain a hydrinate, a ring-closing step of ring-closing the obtained hydrinate by a ring-closing reaction to obtain a closed-ring product, and a ring-opening step of opening the closed-ring product by a ring-opening reaction to obtain a bio-derived branched alkyl glyceryl ether.
• a bio-derived branched alkyl glyceryl ether with reduced odor can be produced by a simple method
• the ratio of the amounts of the bio-derived branched primary alcohol and the bio-derived epichlorohydrin used is not particularly limited, but from the viewpoint 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 1.0:0.1 to 1.0:1.2 in molar ratio, more preferably 1.0:0.2 to 1.0:1.0, and even more preferably 1:0.3 to 1:0.8.
• the method of reacting the bio-derived branched primary alcohol and the bio-derived epichlorohydrin in the hydrination process is not particularly limited, and examples of the method include 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.
• a known catalyst may be used in the hydrination process.
• the ring-closing step in which the hydrinate obtained in the hydrination step is subjected to a ring-closing reaction to obtain a ring-closed product is specifically a step in which a chloro group is eliminated from the hydrinate obtained in the hydrination step to form an epoxy group.
• the method for ring-closing the hydrinate in the ring-closing step is not particularly limited, and for example, a method of adding a known alkaline agent to the hydrinate and condensing the hydrinate can be used.
• examples of known alkaline agents that can be used include alkali metal hydroxides such as sodium hydroxide, potassium hydroxide, calcium hydroxide, and lithium hydroxide, and aqueous solutions thereof.
• the ratio of the amount of the hydrinate to the amount of the alkaline agent is not particularly limited, but from the viewpoint of the odor suppression effect of the resulting bio-derived branched alkyl glyceryl ether, the amount of the hydrinate to the amount of the alkaline agent is preferably 1:0.5 to 1:3 by molar ratio, and more preferably 1:1 to 1:2.
• the specific method for adding a known alkaline agent to the hydrinate and carrying out dehydration condensation is not particularly limited, but examples include a method in which a known aqueous alkaline agent solution is added to the hydrinate, mixed, and reacted at 20 to 150°C for 1 minute to 24 hours while heating and cooling as necessary.
• a known catalyst may be used in the ring-closing reaction.
• the ring-opening step in which the cyclized product obtained in the ring-closing step is opened by a ring-opening reaction to obtain a bio-derived branched alkyl glyceryl ether is specifically a ring-opening step in which the epoxy group of the cyclized product obtained in the ring-closing step is opened by a ring-opening reaction to form two hydroxyl groups to obtain a bio-derived branched alkyl glyceryl ether.
• the method for opening the cyclized product by a ring-opening reaction is not particularly limited, and for example, a method of hydrolyzing the cyclized product to open the ring can be used.
• the method for hydrolyzing the cyclized product to open the ring can be not particularly limited, and for example, a method of adding water to the cyclized product and reacting it at 20 to 200°C for 1 minute to 24 hours under reduced pressure or pressure (0.01 kPa to 10 MPa) while heating or cooling as necessary can be used.
• a known catalyst can be used in the ring-opening reaction, and for example, an acid such as sulfuric acid, hydrochloric acid, perchloric acid, phosphoric acid, acetic acid, or peracetic acid can be used.
• the method may further include a distillation step of distilling the product by a known method.
• examples of the distillation step include a step of distilling a product containing a closed ring product after the ring-closing step (intermediate distillation step), and a step of distilling a product containing a bio-derived branched alkyl glyceryl ether after the ring-opening step (final distillation), and the like, and either or both of these steps may be performed.
• the method for distilling the product is not particularly limited, and may be, for example, atmospheric distillation, reduced pressure distillation, molecular distillation, steam distillation, or the like. More specifically, methods such as single distillation, fractional distillation, flash distillation, steam distillation, vacuum distillation, short path distillation, thin film distillation, reactive distillation, and extractive distillation may be used.
• the method for producing a bio-derived branched alkyl glyceryl ether of the present invention may further include a deodorization step of deodorizing the product containing the bio-derived branched alkyl glyceryl ether after the ring-opening step.
• the method for deodorizing the product containing the bio-derived branched alkyl glyceryl ether is not particularly limited, but for example, a method of contacting the product containing the bio-derived branched alkyl glyceryl ether with water, water vapor, or an inert gas under normal or reduced pressure can be used.
• the bio-derived branched alkyl glyceryl ether of the present invention is a bio-derived branched alkyl glyceryl ether produced by a method for producing a bio-derived branched alkyl glyceryl ether, the method including: obtaining a bio-derived branched primary alcohol having a branched alkyl group having 6 to 12 carbon atoms, the method 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 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 producing a bio-derived branched alkyl glyceryl ether using the obtained bio-derived branched primary alcohol.
• Each step in the present invention can be performed by the method described above, and the bio-derived
• the bio-derived branched alkyl glyceryl ether of the present invention contains a small amount of unavoidable impurities derived from the raw materials. By identifying these unavoidable 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 other raw material, it is impossible to uniformly identify the unavoidable impurities. For this reason, the bio-derived branched alkyl glyceryl ether of the present invention is identified by a production method that limits the raw materials.
• the bio-derived branched alkyl glyceryl ether of the present invention may be a bio-derived branched alkyl glyceryl ether-containing composition containing the bio-derived branched alkyl glyceryl ether and 0.05 to 0.30 parts by mass of an antioxidant such as tocopherols per 100 parts by mass of the bio-derived branched alkyl glyceryl ether.
• tocopherols such as d- ⁇ -tocopherol, dl- ⁇ -tocopherol, d- ⁇ -tocopherol acetate, or other known antioxidants can be used, but from the viewpoint of further improving long-term quality stability, it is preferable that the 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).
• the cosmetic composition or cleanser composition of the present invention is a cosmetic composition or cleanser composition containing the above-mentioned bio-derived branched alkyl glyceryl ether.
• the amount of the bio-derived branched alkyl glyceryl ether in the cosmetic composition or cleanser composition of the present invention is not particularly limited, but is preferably 0.01 to 20.0 mass%, more preferably 0.05 to 10.0 mass%, and even more preferably 0.10 to 5.0 mass%, based on the total amount of the cosmetic composition or cleanser composition.
• the bio-derived branched alkyl glyceryl ether functions as an antibacterial agent (preservative) for the composition.
• the odor of the bio-derived branched alkyl glyceryl ether of the present invention is suppressed, even when it is incorporated in a cosmetic composition or a cleanser composition, it is possible to prevent the odor of the composition from being adversely affected.
• the specific form of use of the cosmetic composition or cleanser composition of the present invention is not particularly limited, and examples include shampoo, rinse, conditioner, treatment, lotion, lotion, milky lotion, cream, facial cleanser, cleansing milk, cleansing lotion, cleansing oil, hair tonic, hair liquid, setting lotion, hair bleach, color rinse, permanent wave solution, lipstick, pack, foundation, cologne, sunscreen, deodorant, perfume, and cosmetic oil.
• the cosmetic composition or detergent composition of the present invention can be blended with additives commonly used in cosmetics or detergents to improve or modify various properties (solubility, dispersibility, stability, usability, applicability, penetration, moisture retention, safety, design, optical properties, fragrance, whitening, etc.) during storage, during use, and after use depending on the purpose of use.
• additives commonly used in cosmetics or detergents to improve or modify various properties (solubility, dispersibility, stability, usability, applicability, penetration, moisture retention, safety, design, optical properties, fragrance, whitening, etc.) during storage, during use, and after use depending on the purpose of use.
• additives include 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, UV protection components, antioxidants, thickeners, surfactants, and other components that can be blended (preservatives, blood circulation promoters, anti-inflammatory agents, activators, whitening agents, antiseborrheic agents, anti-inflammatory agents, various extracts, and plant seaweed extracts, etc.), and one or more of these can be blended at will.
• higher alcohols include linear higher alcohols such as lauryl alcohol, cetyl alcohol, stearyl alcohol, behenyl alcohol, myristyl alcohol, oleyl alcohol, and cetostearyl alcohol; and branched higher alcohols such as monostearyl glycerin ether (batyl alcohol), 2-decyltetradecinol, lanolin alcohol, cholesterol, phytosterol, hexyldodecanol, isostearyl alcohol, and octyldodecanol. One or more of these can be used.
• linear higher alcohols such as lauryl alcohol, cetyl alcohol, stearyl alcohol, behenyl alcohol, myristyl alcohol, oleyl alcohol, and cetostearyl alcohol
• branched higher alcohols such as monostearyl glycerin ether (batyl alcohol), 2-decyltetradecinol, lanolin alcohol, cholesterol, phytosterol, hexyldodecanol,
• Powder components include, for example, inorganic powders (e.g., talc, kaolin, mica, sericite, muscovite, phlogopite, synthetic mica, red mica, black mica, permiculite, magnesium carbonate, calcium carbonate, aluminum silicate, barium silicate, calcium silicate, magnesium silicate, strontium silicate, tungstate metal salts, magnesium, silica, zeolite, barium sulfate, calcined calcium sulfate (calcined gypsum), calcium phosphate, fluorapatite, hydroxyapatite, ceramic powders, metal soaps (e.g., zinc myristate, palmitate, inorganic white pigments (for example, titanium dioxide, zinc oxide, etc.); inorganic red pigments (for example, iron oxide (red oxide), iron titanate, etc.); inorganic brown pigments (for example, ⁇ -iron oxide, etc.); inorganic yellow pigments (for example, yellow iron oxide, yellow
• Organic pigments 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.); natural dyes (e.g., chlorophyll, ⁇ -carotene, etc.), etc., and one or more of these can be used.
• natural dyes e.g., chlorophyll, ⁇ -carotene, etc.
• higher fatty acids examples include lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, oleic acid, undecylenic acid, tall oil fatty acid, isostearic acid, linoleic acid, linoleic acid, eicosapentaenoic acid (EPA), docosahexaenoic acid (DHA), etc., and one or more of these can be used.
• lauric acid myristic acid, palmitic acid, stearic acid, behenic acid, oleic acid, undecylenic acid, tall oil fatty acid, isostearic acid, linoleic acid, linoleic acid, eicosapentaenoic acid (EPA), docosahexaenoic acid (DHA), etc.
• Humectants include, for example, polyethylene glycol, xylitol, sorbitol, maltitol, chondroitin sulfate, hyaluronic acid, mucoitin sulfate, caronic acid, atelocollagen, cholesteryl-12-hydroxystearate, sodium lactate, bile salts, dl-pyrrolidone carboxylate, short-chain soluble collagen, diglycerin (EO) PO adduct, Rosa robur extract, Achillea millefolium extract, Melilot extract, etc., and one or more of these can be used.
• EO diglycerin
• Natural water-soluble polymers include, for example, plant-based polymers (e.g., gum arabic, tragacanth gum, galactan, guar gum, carob gum, karaya gum, carrageenan, pectin, agar, quince seed, algae colloid (cassow extract), starch (rice, corn, potato, wheat), glycyrrhizic acid); microbial-based polymers (e.g., xanthan gum, dextran, succinoglucan, pullulan, gellan gum, etc.); and animal-based polymers (e.g., collagen, casein, albumin, gelatin, etc.), and one or more of these can be used.
• plant-based polymers e.g., gum arabic, tragacanth gum, galactan, guar gum, carob gum, karaya gum, carrageenan, pectin, agar, quince seed, algae colloid (cassow extract), starch (rice, corn,
• water-soluble polymers examples include starch-based polymers (e.g., carboxymethyl starch, methylhydroxypropyl starch, etc.); cellulose-based polymers (methyl cellulose, ethyl cellulose, methylhydroxypropyl cellulose, hydroxyethyl cellulose, sodium cellulose sulfate, hydroxypropyl cellulose, carboxymethyl cellulose, sodium carboxymethyl cellulose, crystalline cellulose, cellulose powder, etc.); alginic acid-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 copolymers made from polyethylene glycol 20,000, 40,000, or 60,000); acrylic-based polymers (e.g., sodium polyacrylate, polye
• sequestering agents include 1-hydroxyethane-1,1-diphosphonic acid, 1-hydroxyethane-1,1-diphosphonic acid tetrasodium salt, disodium edetate, trisodium edetate, tetrasodium edetate, sodium citrate, sodium polyphosphate, sodium metaphosphate, gluconic acid, phosphoric acid, citric acid, ascorbic acid, succinic acid, edetic acid, trisodium ethylenediaminehydroxyethyltriacetate, etc., and one or more of these can be used.
• lower alcohols examples include ethanol, propanol, isopropanol, isobutyl alcohol, t-butyl alcohol, etc., and one or more of these can be used.
• polyhydric alcohols examples 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.); dihydric alcohol alky
• monosaccharides examples include trioses (e.g., D-glyceryl aldehyde, dihydroxyacetone, etc.); tetraoses (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-busicose, D-galactose, D-fructose, L-galactose, L-mannose, D-tag sugars (e.g., aldoheptose, heptose, etc.); octose (e.g., octos
• oligosaccharides include sucrose, umbelliferose, lactose, planteose, isolichinoses, ⁇ , ⁇ -trehalose, raffinose, lychinoses, umbilicin, stachyose, verbascoses, etc., and one or more of these can be used.
• polysaccharides examples 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, keratosulfate, locust bean gum, succinoglucan, and caronic acid, and one or more of these can be used.
• amino acids examples include neutral amino acids (e.g., threonine, cysteine, etc.); basic amino acids (e.g., hydroxylysine, etc.); and the like.
• amino acid derivatives include sodium acyl sarcosine (sodium lauroyl sarcosine), acyl glutamate, sodium acyl ⁇ -alanine, glutathione, pyrrolidone carboxylic acid, etc., and one or more of these can be used.
• organic amines examples 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.
• pH adjusters examples include buffers such as lactic acid-sodium lactate, citric acid-sodium citrate, and succinic acid-sodium succinate, and one or more of these can be used.
• vitamins examples include vitamins 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.
• inorganic UV protection components such as powder pigments and metal powder pigments and their surface-treated products, as well as organic UV protection components can be used, for example, metal oxides such as titanium oxide, zinc oxide, cerium oxide, low-order titanium oxide, and iron-doped titanium oxide, metal hydroxides such as iron hydroxide, metal flakes such as plate-like iron oxide and aluminum flakes, ceramics such as silicon carbide, and their fluorine compound treatments, silicone treatments, silicone resin treatments, pendant treatments, silane coupling agent treatments, titanium coupling agent treatments, silane treatments, oil treatments, N-acylated lysine treatments, polyacrylic acid treatments, metal soap treatments, acrylic resin treatments, metal oxide treatments, etc., as well as salicylic acid-based, para-aminobenzoic acid-based, Benzophenone-based, cinnamic acid-based, benzoylmethane-based, 2-cyano-3,3-diphenylprop-2-enoic acid 2-ethylhexyl este
• antioxidants examples include tocopherols, dibutylhydroxytoluene, butylhydroxyanisole, gallic acid esters, etc., and one or more of these can be used.
• Thickening agents include, 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, curdlan, ⁇ -glucan, ⁇ -glucan derivatives, gellan gum, dextran, ⁇ -glucose and ⁇ -glucose derivatives, cellulose or its derivatives, 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, dibutylethylhexanoyl glutamide, and the
• Surfactants include, for example, cationic surfactants (e.g., lauryltrimethylammonium chloride, cetyltrimethylammonium chloride, stearyltrimethylammonium chloride, alkyltrimethylammonium chloride, distearyldimethylammonium chloride, stearyltrimethylammonium saccharin, cetyltrimethylammonium saccharin, behenyltrimethylammonium methylsulfate, behenyldimethylamine, behenic acid diethylaminoethylamide, behenic acid dimethylaminopropylamide, behenic acid dimethylaminoethylamide, stearyldimethylamine, palmitoxypropyldimethylamine, stearoxypropyldimethylamine, etc.); anionic surfactants (e.g., alkyl ether sulfates, alkyl sulfates, alkyl ether sulfate ester salts,
• ingredients include, for example, preservatives (methylparaben, ethylparaben, butylparaben, phenoxyethanol, etc.); anti-inflammatory agents (for example, glycyrrhizic acid derivatives, glycyrrhetinic acid derivatives, salicylic acid derivatives, hinokitiol, zinc oxide, allantoin, etc.); skin whitening agents (for example, saxifrage extract, arbutin, etc.); various extracts (for example, Phellodendron bark, Coptis japonica, Lithospermum root, Peony root, Swertia japonica, Birch, Sage, Loquat, Carrot, Aloe, Mallow, Iris, Grape, Coix seed, Loofah, Lily, Saffron, Cnidium rhizome, Angelica acutiloba, Hypericum perforatum, Ononis, Garlic, chili pepper, Citrus chinensis, Angelica a
• the content of each is not particularly limited and may be adjusted according to the embodiment and purpose, but for example, 0.001 to 50.0% by mass of each may be added based on the total mass of the cosmetic composition or detergent composition.
• Example 1 3,552 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 the mixture was reacted at 290° C. for 5 hours. The mixture was then filtered and distilled to obtain 1,248 g of bio-derived 2-ethylhexanol, which is a bio-derived branched primary alcohol formed by dimerization of the bio-derived n-butanol, and 1,812 g of unreacted bio-derived n-butanol.
• Example 2 370.5 g of bio-derived n-butanol, 1.1 L of p-xylene, 39.8 g of pentamethylcyclopentadienyl iridium (III) dichloride dimer, 55.1 g of 1,7-octadiene, and 224.42 g of potassium tert-butoxide were added to an autoclave, and the mixture was reacted at 120°C for 4 hours, and then filtered and distilled to obtain 260 g of bio-derived 2-ethylhexanol, which is a bio-derived branched primary alcohol formed by dimerization of bio-derived n-butanol.
• III pentamethylcyclopentadienyl iridium
• Example 3 3100g of bio-derived n-butanol, 398g of copper (I) iodide, 327g of TEMPO, 344g of 1-methylimidazole, and 16L of acetonitrile were added to an open-air reaction vessel, and the mixture was reacted at 25°C for 24 hours, and then filtered and distilled to obtain 2100g of bio-derived n-butyraldehyde. Next, 2000g of the obtained bio-derived n-butyraldehyde was mixed with 2L of a 2wt% aqueous sodium hydroxide solution, and reacted at 90°C for 4 hours, followed by oil-water separation to obtain 1720g of an oil phase.
• the obtained oil phase was distilled to obtain 1400g of bio-derived 2-ethylhexenal, which was a dimerization of bio-derived n-butyraldehyde. Furthermore, the obtained bio-derived 2-ethylhexenal was hydrogenated 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 distilled to obtain 1,260 g of bio-derived 2-ethylhexanol, which is a bio-derived branched primary alcohol.
• Petroleum-derived 2-ethylhexyl glyceryl ether D was obtained by the same method as in Example 1, except that 1,051 g of petroleum-derived 2-ethylhexanol was used, which was produced by producing n-butylaldehyde from petroleum-derived propylene using the Oxo method, followed by aldol condensation of the n-butylaldehyde and hydrogenation, instead of the bio-derived 2-ethylhexanol.
• ⁇ Deodorizing property evaluation> The deodorizing property of each of the 2-ethylhexyl glyceryl ethers produced in Examples 1 to 3 and Comparative Example 1 immediately after production was evaluated. Specifically, seven examiners checked the odor of each of the 2-ethylhexyl glyceryl ethers produced, and scored them on a 10-point scale from 1 to 10, with 10 points being given for completely odorless (odor suppressed) and 1 point being given for a strong odor.
• the total score of each examiner's scores was calculated, and the deodorizing property was evaluated as follows: if the total score was 60 points or more, it was rated as ⁇ ; if the total score was 45 points or more but less than 60 points, it was rated as ⁇ ; and if the total score was less than 45 points, it was rated as x.
• the evaluation results are shown in Table 1.

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