Extractant

Abstract

To provide an extractant that reduces salt contained in treatment water without using a film.SOLUTION: An extractant contains a polymer having a constitutional unit derived from an amine containing a C4 to C30 hydrocarbon group and / or a constitutional unit derived from a hydroxy group-containing compound containing a C4 to C30 hydrocarbon group, and a constitutional unit derived from a C3 to C15 epoxy compound.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to an extractant. [Background technology]

[0002] Conventionally, separation techniques using membranes such as reverse osmosis and forward osmosis have been known as techniques for desalination of salt-containing water contained in seawater, industrial wastewater, and the like (Patent Document 1). [Prior art documents] [Patent documents]

[0003] [Patent Document 1] Patent No. 6172385 Summary of the Invention [Problem to be solved by the invention]

[0004] Desalination by membrane separation has problems such as membrane separation performance, as well as degradation and fouling. Therefore, an object of the present invention is to provide an extractant that can reduce solutes such as salts contained in treated water such as seawater without using a membrane. [Means for solving the problem]

[0005] The present inventors have conducted various studies to achieve the above object and have arrived at the present invention. Specifically, the present disclosure relates to an extractant characterized by comprising a polymer having structural units derived from an amine containing a hydrocarbon group having 4 to 30 carbon atoms and / or structural units derived from a hydroxyl group-containing compound containing a hydrocarbon group having 4 to 30 carbon atoms, and structural units derived from an epoxy compound having 3 to 15 carbon atoms. [Effects of the Invention]

[0006] The extractant disclosed herein has the function of reducing solutes such as salts contained in treated water without using a membrane, which not only facilitates energy conservation and ease of operation but also makes it possible to apply it to desalination technologies for seawater, industrial wastewater, etc. as an even cleaner process. DETAILED DESCRIPTION OF THE INVENTION

[0007] The present invention will be described in detail below. Note that a combination of two or more of the individual preferred embodiments of the present invention described below is also a preferred embodiment of the present invention. Extractants of the present disclosure In this disclosure, the term "extractant" refers to an agent that can be brought into contact with treated water to transfer water contained in the treated water to a liquid containing the extractant (hereinafter also referred to as "extraction liquid"). Therefore, contact with the extractant makes it possible to increase the concentration of solutes such as salts in the treated water.

[0008] The extractant of the present disclosure comprises a polymer having structural units derived from an amine containing a hydrocarbon group having 4 to 30 carbon atoms and / or structural units derived from a hydroxyl group-containing compound containing a hydrocarbon group having 4 to 30 carbon atoms, and structural units derived from an epoxy compound having 3 to 15 carbon atoms.

[0009] In the present disclosure, the term "structural unit derived from an amine" refers to a structural unit in which at least one hydrogen atom has been removed from at least one amino group contained in an amine.

[0010] In the present disclosure, the term "structural unit derived from a hydroxyl group-containing compound" refers to a structural unit obtained by removing at least one hydrogen atom from at least one hydroxyl group contained in a hydroxyl group-containing compound.

[0011] In the present disclosure, the term "structural unit derived from an epoxy compound" refers to a structural unit having the same structure as a structural unit formed by ring-opening of an epoxy compound. However, the structural unit derived from an epoxy compound is not limited to the structure actually formed by ring-opening of an epoxy compound, and even if formed by a different method, it is considered to be a structural unit derived from an epoxy compound as long as it has the same structure as a structural unit formed by ring-opening of an epoxy compound. For example, in the case of propylene oxide, the structural unit derived from propylene oxide can be represented by -CHCH(CH)-O- or -CH(CH)CH-O-.

[0012] In the present disclosure, the amine preferably has a structure in which a hydrocarbon group is bonded to an amino group.

[0013] In the present disclosure, the number of carbon atoms in the hydrocarbon group contained in the amine is preferably 4 or more, more preferably 6 or more, and even more preferably 8 or more. On the other hand, the number of carbon atoms is preferably 50 or less, more preferably 30 or less, and even more preferably 20 or less. This tends to facilitate the reduction of solutes such as salts contained in the treated water.

[0014] The hydrocarbon group contained in the amine may be any of a linear or branched aliphatic hydrocarbon group, a cyclic aliphatic hydrocarbon group, and an aromatic hydrocarbon group. The aliphatic hydrocarbon group may be any of a saturated aliphatic hydrocarbon group and an unsaturated aliphatic hydrocarbon group. The aromatic hydrocarbon group is a group having an aromatic ring and may have an aliphatic portion, and the alicyclic hydrocarbon group is a group having a cyclic aliphatic hydrocarbon portion and may have a linear or branched aliphatic hydrocarbon portion.

[0015] The linear aliphatic hydrocarbon group is not particularly limited, and examples thereof include an n-methyl group, an n-ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, an n-nonyl group, an n-decyl group, an n-undecyl group, an n-dodecyl group, an n-tridecyl group, an n-tetradecyl group, an n-pentadecyl group, an n-hexadecyl group, an n-heptadecyl group, an n-octadecyl group, an n-nonadecyl group, an n-icosyl group, an eicosyl group, a heneicosyl group, a triacontyl group, and a tetracontyl group.

[0016] The branched aliphatic hydrocarbon group is not particularly limited, and examples thereof include a sec-butyl group, an isobutyl group, a tert-butyl group, a 1-methylbutyl group, a 1-ethylpropyl group, a 2-methylbutyl group, an isoamyl group, a 1,2-dimethylpropyl group, a 1,1-dimethylpropyl group, a tert-amyl group, a 1,3-dimethylbutyl group, a 3,3-dimethylbutyl group, a 1-methylpentyl group, a 1-methylbutyl group, a 1-ethylbutyl group, a 2-ethylbutyl group, a 2-ethyl-2-methylpropyl group, a sec-heptyl group, a tert-heptyl group, an isoheptyl group, a sec-octyl group, a tert ... ethyl group, tert-octyl group, isooctyl group, 1-ethylhexyl group, 1-propylpentyl group, 2-ethylhexyl group, 2-propylpentyl group, sec-nonyl group, tert-nonyl group, neononyl group, 1-ethylheptyl group, 1-propylhexyl group, 1-butylpentyl group, 2-ethylheptyl group, 2-propylhexyl group, 2-butylpentyl group, isodecyl group, sec-decyl group, tert-decyl group, neodecyl group, 1-ethyloctyl group, 1-propylheptyl group, 1-butylhexyl group, 2-ethyloctyl group, 2-propylheptyl group butyl group, 2-butylhexyl group, isoundecyl group, sec-undecyl group, tert-undecyl group, neoundecyl group, 1-ethylnonyl group, 1-propyloctyl group, 1-butylheptyl group, 1-pentylhexyl group, 2-ethylnonyl group, 2-propyloctyl group, 2-butylheptyl group, 2-pentylhexyl group, isododecyl group, sec-dodecyl group, tert-dodecyl group, neododecyl group, 1-ethyldecyl group, 1-propylnonyl group, 1-butyloctyl group, 1-pentylheptyl group, 2-ethyldecyl group, 2-propylnonyl group , 2-butyloctyl group, 2-pentylheptyl group, isotridecyl group, sec-tridecyl group, tert-tridecyl group, neotridecyl group, 1-ethylundecyl group, 1-propyldecyl group, 1-butylnonyl group, 1-pentyloctyl group, 1-hexylheptyl group, 2-ethylundecyl group, 2-propyldecyl group, 2-butyloctyl group, 2-pentyloctyl group, 2-hexylheptyl group, isotetradecyl group, sec-tetradecyl group, tert-tetradecyl group, neotetradecyl group, 1-ethyldodecyl group, 1-propylundecyl group,1-butyldecyl group, 1-pentylnonyl group, 1-hexyloctyl group, 2-ethyldodecyl group, 2-propylundecyl group, 2-butyldecyl group, 2-pentylnonyl group, 2-hexyloctyl group, isopentadecyl group, sec-pentadecyl group, tert-pentadecyl group, neopentadecyl group, isohexadecyl group, sec-hexadecyl group, tert-hexadecyl group, neohexadecyl group, isoheptadecyl group, sec-heptadecyl group Decyl group, tert-heptadecyl group, neoheptadecyl group, isooctadecyl (isostearyl group), sec-octadecyl group, tert-octadecyl group, neooctadecyl group, isononadecyl group, sec-nonadecyl group, tert-nonadecyl group, neononadecyl group, isoicosyl group, sec-icosyl group, tert-icosyl group, neoicosyl group, isohenicosyl group, sec-henicosyl group, tert-henicosyl group, neohenicosyl group isocosyl, isodocosyl, sec-docosyl, tert-docosyl, neodocosyl, isotricosyl, sec-tricosyl, tert-tricosyl, neotricosyl, isotetracosyl, sec-tetracosyl, tert-tetracosyl, neotetracosyl, isopentacosyl, sec-pentacosyl, tert-pentacosyl, neopentacosyl, isohexacosyl, sec-hexacosyl, t Examples of such an alkyl group include an ert-hexacosyl group, a neohexacosyl group, an isoheptacosyl group, a sec-heptacosyl group, a tert-heptacosyl group, a neoheptacosyl group, an isooctacosyl group, a sec-octacosyl group, a tert-octacosyl group, a neooctacosyl group, an isononacosyl group, a sec-nonacosyl group, a tert-nonacosyl group, a neononacosyl group, an isotriacontyl group, a sec-triacontyl group, and a tert-triacontyl group.

[0017] The cyclic aliphatic hydrocarbon group is not particularly limited, but examples thereof include a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cyclooctyl group, a cyclodecyl group, a cyclododecyl group, a cyclohexadecyl group, and a cyclooctadecyl group.

[0018] The aromatic hydrocarbon group is not particularly limited, but examples thereof include a phenyl group, a naphthyl group, an anthryl group, a biphenyl group, a phenanthryl group, a fluorenyl group, a tolyl group, a xylyl group, a cumenyl group, a mesityl group, a biphenyl group, a phenanthryl group, a 2,6-diethylphenyl group, and a 2-methyl-6-ethylphenyl group.

[0019] The hydrocarbon group contained in the amine is preferably a linear or branched aliphatic hydrocarbon group, more preferably a linear aliphatic hydrocarbon group.

[0020] One or more hydrogen atoms of the hydrocarbon group may be replaced with other groups. Examples of other groups (sometimes referred to as substituents) include, but are not limited to, a hydroxyl group, an amino group, a hydrocarbon group, an alkoxy group, and a halogen atom.

[0021] The amine may be a primary amine in which only one type of hydrocarbon group is bonded to the amino group, or a secondary amine in which two types of hydrocarbon group are bonded.

[0022] The amine is not particularly limited in terms of the site where the amino group and the hydrocarbon group are bonded, but is preferably a primary amine having an aliphatic hydrocarbon group or a primary amine having an aromatic hydrocarbon group.

[0023] The number of amino groups contained in the amine is not limited.

[0024] The amine may be a single type or a mixture of two or more types.

[0025] The amine may be an aliphatic amine, an aromatic amine, or a heterocyclic amine.

[0026] Examples of aliphatic amines include aliphatic primary amines such as butylamine, 2-pentylamine, 3-pentylamine, neopentylamine, hexylamine, octylamine, 2-ethylhexylamine, nonylamine, decylamine, pentadecylamine, cetylamine, laurylamine, stearylamine, cyclopropylamine, cyclobutylamine, cyclopentylamine, cyclohexylamine, and 1-adamantanamine; butylmethylamine, methyl t-butylamine, dipropylamine, diisopropylamine, ethyl t-butylamine, and N-ethyl-1,2-dimethylamine. and aliphatic secondary amines such as dipropylamine, dibutylamine, diisobutylamine, di(t-butyl)amine, ethylhexylamine, dipentylamine, dihexylamine, di(2-ethylhexyl)amine, dioctylamine, didecylamine, dilaurylamine, dicetylamine, distearylamine, methylstearylamine, ethylstearylamine, butylstearylamine, methylcyclohexylamine, ethylcyclohexylamine, Nt-butylcyclohexylamine, dicyclohexylamine, and di(2-methylcyclohexyl)amine.

[0027] Examples of aromatic amines include aromatic primary amines such as benzylamine, phenylpropylamine, phenylbutylamine, 1,1-dimethyl-2-phenylethylamine, 3,4-dimethylbenzylamine, aniline, methylaniline, ethylaniline, propylaniline, isopropylaniline, butylaniline, laurylaniline, stearylaniline, dimethylaniline, diethylaniline, methylbenzylamine, 4,4'-methylenedianiline, naphthylamine, trimethylaniline, and 4-methylphenethylamine; and aromatic secondary amines such as methylbenzylamine, ethylbenzylamine, t-butylbenzylamine, diphenylamine, and dibenzylamine. Other aromatic amines include aromatic polyamines such as N-benzyl-1,3-propanediamine, 2,4,6-trimethyl-1,3-phenylenediamine, and 4-aminobenzylamine.

[0028] Examples of heterocyclic amines include pyrrolidine, 2-methylpyrrolidine, piperidine, 2-methylpiperidine, 3-methylpiperidine, 4-methylpiperidine, 2,4-dimethylpiperidine, 3,5-dimethylpiperidine, 2,6-dimethylpiperidine, 2,2,6,6-tetramethylpiperidine, N-cyclohexylpiperazine, N-cyclopentylpiperazine, N-phenylpiperazine, 1-(2-pyridyl)piperazine, 1-(4-pyridyl)piperazine, 1-(2-pyrimidyl)morpholine, pyrrole, 2-methylpyrrole, 2,4-dimethylpyrrole, 3,4-dimethylpyrrole, indole, 3-methylindole, and 2-phenylindole.

[0029] In the present disclosure, the hydroxyl group-containing compound preferably has a structure in which a hydrocarbon group is bonded to a hydroxyl group.

[0030] The number of carbon atoms in the hydrocarbon group contained in the hydroxyl group-containing compound is preferably 4 or more, more preferably 6 or more, and even more preferably 8 or more. On the other hand, it is preferably 30 or less, more preferably 20 or less, and even more preferably 18 or less. This tends to facilitate the reduction of solutes such as salts contained in the treated water.

[0031] The hydrocarbon group contained in the hydroxyl group-containing compound may be any of a linear or branched aliphatic hydrocarbon group, a cyclic aliphatic hydrocarbon group, and an aromatic hydrocarbon group. The aliphatic hydrocarbon group may be any of a saturated aliphatic hydrocarbon group and an unsaturated aliphatic hydrocarbon group. The aromatic hydrocarbon group is a group having an aromatic ring and may have an aliphatic portion, and the alicyclic hydrocarbon group is a group having a cyclic aliphatic hydrocarbon portion and may have a linear or branched aliphatic hydrocarbon portion.

[0032] The linear aliphatic hydrocarbon group is not particularly limited, and examples thereof include an n-methyl group, an n-ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, an n-nonyl group, an n-decyl group, an n-undecyl group, an n-dodecyl group, an n-tridecyl group, an n-tetradecyl group, an n-pentadecyl group, an n-hexadecyl group, an n-heptadecyl group, an n-octadecyl group, an n-nonadecyl group, an n-icosyl group, an eicosyl group, a heneicosyl group, a triacontyl group, and a tetracontyl group.

[0033] The branched aliphatic hydrocarbon group is not particularly limited, and examples thereof include a sec-butyl group, an isobutyl group, a tert-butyl group, a 1-methylbutyl group, a 1-ethylpropyl group, a 2-methylbutyl group, an isoamyl group, a 1,2-dimethylpropyl group, a 1,1-dimethylpropyl group, a tert-amyl group, a 1,3-dimethylbutyl group, a 3,3-dimethylbutyl group, a 1-methylpentyl group, a 1-methylbutyl group, a 1-ethylbutyl group, a 2-ethylbutyl group, a 2-ethyl-2-methylpropyl group, a sec-heptyl group, a tert-heptyl group, an isoheptyl group, a sec-octyl group, a tert ... ethyl group, tert-octyl group, isooctyl group, 1-ethylhexyl group, 1-propylpentyl group, 2-ethylhexyl group, 2-propylpentyl group, sec-nonyl group, tert-nonyl group, neononyl group, 1-ethylheptyl group, 1-propylhexyl group, 1-butylpentyl group, 2-ethylheptyl group, 2-propylhexyl group, 2-butylpentyl group, isodecyl group, sec-decyl group, tert-decyl group, neodecyl group, 1-ethyloctyl group, 1-propylheptyl group, 1-butylhexyl group, 2-ethyloctyl group, 2-propylheptyl group butyl group, 2-butylhexyl group, isoundecyl group, sec-undecyl group, tert-undecyl group, neoundecyl group, 1-ethylnonyl group, 1-propyloctyl group, 1-butylheptyl group, 1-pentylhexyl group, 2-ethylnonyl group, 2-propyloctyl group, 2-butylheptyl group, 2-pentylhexyl group, isododecyl group, sec-dodecyl group, tert-dodecyl group, neododecyl group, 1-ethyldecyl group, 1-propylnonyl group, 1-butyloctyl group, 1-pentylheptyl group, 2-ethyldecyl group, 2-propylnonyl group , 2-butyloctyl group, 2-pentylheptyl group, isotridecyl group, sec-tridecyl group, tert-tridecyl group, neotridecyl group, 1-ethylundecyl group, 1-propyldecyl group, 1-butylnonyl group, 1-pentyloctyl group, 1-hexylheptyl group, 2-ethylundecyl group, 2-propyldecyl group, 2-butyloctyl group, 2-pentyloctyl group, 2-hexylheptyl group, isotetradecyl group, sec-tetradecyl group, tert-tetradecyl group, neotetradecyl group, 1-ethyldodecyl group, 1-propylundecyl group,1-butyldecyl group, 1-pentylnonyl group, 1-hexyloctyl group, 2-ethyldodecyl group, 2-propylundecyl group, 2-butyldecyl group, 2-pentylnonyl group, 2-hexyloctyl group, isopentadecyl group, sec-pentadecyl group, tert-pentadecyl group, neopentadecyl group, isohexadecyl group, sec-hexadecyl group, tert-hexadecyl group, neohexadecyl group, isoheptadecyl group, sec-heptadecyl group Decyl group, tert-heptadecyl group, neoheptadecyl group, isooctadecyl (isostearyl group), sec-octadecyl group, tert-octadecyl group, neooctadecyl group, isononadecyl group, sec-nonadecyl group, tert-nonadecyl group, neononadecyl group, isoicosyl group, sec-icosyl group, tert-icosyl group, neoicosyl group, isohenicosyl group, sec-henicosyl group, tert-henicosyl group, neohenicosyl group isocosyl, isodocosyl, sec-docosyl, tert-docosyl, neodocosyl, isotricosyl, sec-tricosyl, tert-tricosyl, neotricosyl, isotetracosyl, sec-tetracosyl, tert-tetracosyl, neotetracosyl, isopentacosyl, sec-pentacosyl, tert-pentacosyl, neopentacosyl, isohexacosyl, sec-hexacosyl, t Examples of such an alkyl group include an ert-hexacosyl group, a neohexacosyl group, an isoheptacosyl group, a sec-heptacosyl group, a tert-heptacosyl group, a neoheptacosyl group, an isooctacosyl group, a sec-octacosyl group, a tert-octacosyl group, a neooctacosyl group, an isononacosyl group, a sec-nonacosyl group, a tert-nonacosyl group, a neononacosyl group, an isotriacontyl group, a sec-triacontyl group, and a tert-triacontyl group.

[0034] The cyclic aliphatic hydrocarbon group is not particularly limited, but examples thereof include a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cyclooctyl group, a cyclodecyl group, a cyclododecyl group, a cyclohexadecyl group, and a cyclooctadecyl group.

[0035] The aromatic hydrocarbon group is not particularly limited, but examples thereof include a phenyl group, a naphthyl group, an anthryl group, a biphenyl group, a phenanthryl group, a fluorenyl group, a tolyl group, a xylyl group, a cumenyl group, a mesityl group, a biphenyl group, a phenanthryl group, a 2,6-diethylphenyl group, and a 2-methyl-6-ethylphenyl group.

[0036] The hydrocarbon group contained in the hydroxyl group-containing compound is preferably a linear or branched aliphatic hydrocarbon group, more preferably a linear aliphatic hydrocarbon group.

[0037] One or more hydrogen atoms of the hydrocarbon group may be replaced with other groups. Examples of other groups (sometimes referred to as substituents) include, but are not limited to, a hydroxyl group, an amino group, a hydrocarbon group, an alkoxy group, and a halogen atom.

[0038] In the hydroxyl group-containing compound, the site where the hydroxyl group and the hydrocarbon group are bonded is not particularly limited.

[0039] The number of hydroxyl groups contained in the hydroxyl group-containing compound is not limited, but is preferably 2 or less, and more preferably 1.

[0040] The hydroxyl group-containing compound may be a single compound or a mixture of two or more compounds.

[0041] Examples of the hydroxyl group-containing compound include aliphatic alcohols and aromatic alcohols.

[0042] Examples of aliphatic alcohols include linear alkanols such as butanol, pentanol, hexanol, heptanol, octanol, nonaol, decanol, undecanol, dodecanol, tridecanol, tetradecanol, pentadecanol, hexadecanol, heptadecanol, octadecanol, nonadecanol, icosanol, eicosanol, henicosanol, heneicosanol, docosanol, tricosanol, tetracosanol, pentacosanol, hexacosanol, heptacosanol, octacosanol, nonacosanol, and triacosanol; 2-ethylhexanol, 2-propylheptanol, 2-butyloctanol, 1-methylheptadecanol, 2-hexyloctanol, 1-hexylheptanol, isodecanol, and isohexanol. Branched alkanols such as tridecanol and 3,5,5-trimethylhexanol; linear alkenols such as hexenol, heptenol, octenol, nonenol, decenol, undecenol, dodecenol, tridecenol, tetradecenol, pentadecenol, hexadecenol, pentadecenol, hexadecenol, heptadecenol, octadecenol, nonadecenol, eisenol, docosenol, tetracosenol, pentacosenol, hexacosenol, heptacosenol, heptacosenol, octacosenol, nonacosenol, and triaconsenol; branched alkenols such as isohexenol, 2-ethylhexenol, isotridecenol, 1-methylheptadecenol, 1-hexylheptenol, isotridecenol, and isooctadecenol;Examples of alkanediols include butyl ethyl propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,7-heptanediol, 1,6-octanediol, 1,9-nonanediol, 1,10-decanediol, 1,11-undecanediol, 1,12-dodecanediol, 1,13-tridecanediol, 1,14-tetradecanediol, 1,15-pentadecanediol, 1,16-hexadecanediol, 3-methyl-1,5-pentanediol, 2,4-diethyl-1,5-pentanediol, neopentyl glycol, 1,2-cyclohexanediol, 1,3-cyclohexanediol, 1,4-cyclohexanediol, tricyclodecane dimethanol, and cyclohexane dimethanol;

[0043] Aromatic alcohols include phenol, nonylphenol, octylphenol, tert-butylphenol, dinonylphenol, naphthol, hydroquinone, catechol, resorcinol, bisphenol A, hydrogenated bisphenol A, bisphenol F, bisphenol S, triphenol, tetraphenol, novolak, resol, and resorcinol. Other hydroxyl group-containing compounds include higher alcohols derived from natural fats and oils, such as coconut alcohol and palm alcohol, the Kalcol series (manufactured by Kao), the Conol series (manufactured by New Japan Chemical), the Oxocol series (manufactured by Kyowa Hakko Chemical), the Neodol series (manufactured by Shell Chemical), the ALFOL series (manufactured by Sasol), the EXXAL series (manufactured by Exxon Mobil), and the Softanol series (manufactured by Nippon Shokubai).

[0044] The epoxy compound in the polymer of the present disclosure is preferably an epoxy compound having 3 to 15 carbon atoms, more preferably an epoxy compound having 3 to 11 carbon atoms, even more preferably an epoxy compound having 3 to 7 carbon atoms, and most preferably propylene oxide (PO) or butylene oxide (BO).

[0045] The epoxy compound in the polymer of the present disclosure is not particularly limited, but examples thereof include propylene oxide, 1,2-butylene oxide, 2,3-butylene oxide, styrene oxide, epichlorohydrin, tetrahydrofuran, oxetane, dioxirane, trioxane, butyl glycidyl ether, phenyl glycidyl ether, 2-ethylhexyl glycidyl ether, bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, allyl glycidyl ether, etc. Ethylene oxide may be contained.

[0046] There is no limitation on the type of epoxy compound in the polymer of the present disclosure, and it may be one type, or more preferably two or more types.

[0047] Examples of the combination of two or more epoxy compounds in the polymer of the present disclosure include a combination of PO and EO, a combination of BO and EO, a combination of PO and BO, or a combination of EO, PO and BO, etc. More preferred are a combination of EO and PO, a combination of EO and BO, or a combination of PO and BO.

[0048] In the polymer of the present disclosure, for example, when the polymer has structural units derived from two types of epoxy compounds, the molar ratio of the epoxy compound having a smaller number of carbon atoms to the epoxy compound having a larger number of carbon atoms in the two types of epoxy compounds is, for example, preferably 1:1 to 20:1, more preferably 1:1 to 10:1, and even more preferably 1:1 to 4:1.

[0049] The polymers of the present disclosure may be block polymers, random polymers, or a combination thereof.

[0050] The number average molecular weight of the polymer of the present disclosure is preferably 300 to 10,000, more preferably 300 to 5,000, and even more preferably 300 to 2,000. The weight average molecular weight is preferably 300 to 10,000, more preferably 300 to 5,000, and even more preferably 300 to 2,000. The number average molecular weight and weight average molecular weight can be measured by gel permeation chromatography (GPC).

[0051] The polymer of the present disclosure preferably has a cloud point (lower critical solution temperature). The cloud point refers to the temperature at which a transparent or translucent liquid undergoes phase separation upon temperature change, resulting in the liquid becoming opaque.

[0052] By heating a liquid containing the polymer of the present disclosure, phase separation can be caused into a liquid mainly composed of the polymer of the present disclosure and a liquid mainly composed of water.

[0053] The cloud point of the polymer of the present disclosure can be adjusted appropriately by changing the structure of the polymer, for example, the structure of the amine, the structure of the hydroxyl group-containing compound, the type and number of moles of the epoxy compound, etc.

[0054] The cloud point of the polymer of the present disclosure is preferably 0 to 100°C, more preferably 10 to 50°C, and even more preferably 20 to 50°C.

[0055] The extractant of the present disclosure may contain one type of polymer alone or two or more types of polymers.

[0056] The polymer of the present disclosure can be obtained by addition polymerization of an epoxy compound with an amine and / or a hydroxyl group-containing compound. From the viewpoint of the amount of water recovered, the number of moles of epoxy compound per mole of amine and / or hydroxyl group-containing compound is preferably 4 moles or more, more preferably 6 moles or more, and even more preferably 8 moles or more. On the other hand, from the viewpoint of viscosity, it is preferably 100 moles or less, more preferably 50 moles or less, and even more preferably 25 moles or less.

[0057] The reaction conditions for addition polymerization (alkoxylation) of an epoxy compound are not particularly limited. For example, the amine and the epoxy compound can be reacted as is, or diluted with a solvent as necessary, at preferably 0 to 200°C, more preferably 120 to 180°C. In this case, an alkaline catalyst such as potassium hydroxide (KOH) or sodium hydroxide (NaOH) may be used as a catalyst. The reaction can be carried out, for example, by adding a catalyst to the amine and then feeding the epoxy compound into the reaction system. When two or more epoxy compounds are addition polymerized, they may be mixed and then fed, or they may be fed separately. When two or more epoxy compounds are fed separately, they may be fed simultaneously or sequentially. After feeding the epoxy compound, the reaction rate can be further increased by aging for 1 to 2 hours until the reaction is sufficient. After the reaction, it is preferable to neutralize the reaction mixture by adding an acid such as acetic acid, and then remove light impurities such as 2,3-butadione contained in the polymer under reduced pressure at 100 to 200°C, more preferably 120 to 180°C.

[0058] The reaction conditions for addition polymerization (alkoxylation) of an epoxy compound with a hydroxyl group-containing compound to produce a polymer of the present disclosure are not particularly limited. For example, the hydroxyl group-containing compound and the epoxy compound can be reacted as is, or diluted with a solvent as necessary, at preferably 0 to 200°C, more preferably 120 to 180°C. In this case, an alkaline catalyst such as potassium hydroxide (KOH) or sodium hydroxide (NaOH) may be used as a catalyst. The reaction can be carried out, for example, by adding a catalyst to the hydroxyl group-containing compound and then feeding the epoxy compound into the reaction system. When two or more epoxy compounds are addition polymerized, they may be mixed and then fed, or they may be fed separately. When two or more epoxy compounds are fed separately, they may be fed simultaneously or sequentially. After feeding the epoxy compounds, the reaction rate can be further increased by aging for 1 to 3 hours until they are fully reacted.

[0059] After the reaction, an acid such as acetic acid is added to neutralize the reaction mixture. Furthermore, it is preferable to carry out a step of removing impurities. The removal method is not particularly limited, but examples include centrifugation, filtration, evaporation, and distillation. Light impurities such as 2,3-butadione contained in the compound are preferably removed by heating the mixture under reduced pressure at 120 to 200°C, more preferably 120 to 180°C.

[0060] [Water treatment method of the present disclosure] <Process (I)> By contacting an extracting liquid containing the extractant of the present disclosure with treated water (hereinafter sometimes referred to as "water to be treated"), the extracting liquid acts as an attractant, and the water contained in the treated water migrates to a liquid containing the extractant (extracting liquid) to form a liquid (Ie), while the concentration of solutes such as salts contained in the treated water increases to form a concentrated liquid (Iw).

[0061] The contacting may be via a forward osmosis membrane or a reverse osmosis membrane, but is preferably carried out without the use of a membrane.

[0062] The contact time is preferably 5 minutes to 24 hours, more preferably 1 hour to 24 hours, and even more preferably 12 to 24 hours.

[0063] The temperature for contact is preferably 10 to 40° C., more preferably 25 to 30° C. The mixture may be heated or cooled.

[0064] Through contact, the treated water can be separated into a liquid (Ie) mainly composed of the extractant, in which the water contained in the treated water has moved to a liquid containing the extractant, and a liquid (Iw) mainly composed of water with an increased concentration of solutes such as salts contained in the treated water.

[0065] The separation method is not particularly limited, and may be, for example, static separation, centrifugation, or adsorption separation. From the viewpoint of energy saving, static separation is preferred. The standing time is preferably 5 minutes to 24 hours, more preferably 1 to 24 hours, and even more preferably 12 to 24 hours.

[0066] The temperature at which the mixture is left standing is preferably 10 to 40° C., more preferably 25 to 30° C. The mixture may be heated or cooled.

[0067] The phase-separated extractant-based liquid (Ie) and water-based liquid (Iw) can be obtained by separating the oil and water using a coalescer or separatory funnel, and by collecting them using a pump or dropper, respectively.

[0068] The ratio (mass %) of the amount of water contained in the water-based liquid (Iw) to the amount of water contained in the extractant-based liquid (Ie) (hereinafter sometimes referred to as the water partition coefficient (I-wp)) is preferably 100% or more, more preferably 200% or more, and even more preferably 300% or more.

[0069] The ratio (mass %) of the amount of salt contained in the water-based liquid (Iw) to the amount of salt contained in the extractant-based liquid (Ie) (hereinafter sometimes referred to as the salt distribution coefficient (I-sp)) is preferably 100% or more, more preferably 400% or more, and even more preferably 500% or more.

[0070] The ratio of the salt partition coefficient (I-sp) to the water partition coefficient (I-wp) is preferably 1.0 or more, more preferably 1.5 or more, and even more preferably 1.8 or more.

[0071] The hydrocarbon groups contained in the polymers of the present disclosure tend to efficiently reduce salts contained in the water being treated.

[0072] <Process (II)> By heating the liquid containing the extractant and water, it can be separated into a liquid mainly composed of the extractant and a liquid mainly composed of water.

[0073] By heating the liquid (Ie) mainly composed of the extractant obtained in the above step (I), it can be separated into a liquid (IIe) mainly composed of the extractant and a liquid (IIw) mainly composed of water.

[0074] The separation method is not particularly limited, but static separation is preferred.

[0075] The standing time is preferably 1 to 48 hours, more preferably 5 to 24 hours, and even more preferably 12 to 24 hours.

[0076] The temperature at which the mixture is allowed to stand is preferably 30 to 90°C, more preferably 40 to 70°C, and even more preferably 50 to 70°C.

[0077] By adjusting the temperature to the above range, the extractant acts as an attractant, and phase separation into a liquid (IIe) mainly composed of the extractant and a liquid (IIw) mainly composed of water can be achieved.

[0078] The phase-separated extractant-based liquid (IIe) and water-based liquid (IIw) can be obtained by known methods, such as oil-water separation using a coalescer or separatory funnel, or collection using a pump or dropper.

[0079] Step (I) may be carried out by mixing a liquid containing the extractant of the present disclosure with a liquid (IIe) mainly composed of the extractant.

[0080] The step (II) may be carried out by mixing the liquid (Ie) mainly containing the extractant with the liquid (IIw) mainly containing water.

[0081] Steps (I) and (II) can be repeated.

[0082] By performing water treatment including steps (I) and (II) using the extractant of the present disclosure, it is possible to reduce solutes such as salts contained in the treated water and desalinate it.

[0083] The amount of water recovered can be adjusted by the epoxy compound added to the polymer of the present disclosure and the number of moles added. [Example]

[0084] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples. Unless otherwise specified, "parts" means "parts by mass" and "%" means "% by mass."

[0085] <Salt concentration evaluation> The sodium ion concentration was measured by capillary electrophoresis and converted into sodium chloride concentration for calculation. System: Agilent 7100 capillary electrophoresis system Column: Agilent fused silica capillary column (inner diameter 75 μm × length 72 cm) Column temperature: 25℃ Voltage: 20kV Running solution: 10 mM imidazole, 5 mM 2-hydroxyisobutyric acid, 2 mM 18-crown-6-ether, 0.2 wt% acetic acid Detection: Indirect UV, UV detection wavelength 210nm <Moisture content evaluation> Approximately 0.2 to 1.0 g of the aqueous solution was collected and placed in an aluminum cup, which was then left to dry in an oven at 97°C for 2 hours, and the difference in weight before and after drying was calculated as the water content. [Polymer synthesis] <Production Example 1> An autoclave was charged with 404.0 g of laurylamine and 23.6 g of 48% KOH aqueous solution at room temperature. The gas phase was replaced with nitrogen gas, and the pressure was reduced to -0.1 MPa while bubbling nitrogen gas at 20 mL / min. The mixture was then heated to 125°C and stirred for 3 hours. After the pressure was increased to 0.20 MPa, the bubbling was stopped, and 576.1 g of ethylene oxide was injected over 3 hours. The mixture was then aged for 3 hours. 759.3 g of the intermediate thus obtained was charged into an autoclave at room temperature, and the gas phase was replaced with nitrogen gas to set the gauge pressure to 0.20 MPa. After heating to 125°C, 240.7 g of butylene oxide was added under pressure over 2 hours while stirring, and the mixture was aged for 5 hours. After cooling to 60°C, the pressure was released, and 27.8 g of 50% lactic acid was added. While bubbling nitrogen gas at 20 mL / min, the pressure was reduced to -0.1 MPa and the mixture was stirred at 125°C for 1 hour. This yielded polymer (i), a block polymer. <Production Example 2> An autoclave was charged with 300.0 g of aniline and 17.5 g of 48% KOH aqueous solution at room temperature. The gas phase was replaced with nitrogen gas, and the pressure was reduced to -0.1 MPa while bubbling nitrogen gas at 20 mL / min. The temperature was then raised to 125°C and the mixture was stirred for 3 hours. After the pressure was raised to 0.20 MPa, the bubbling was stopped, and 851.4 g of ethylene oxide was injected over 3 hours. The mixture was then aged for 3 hours. 714.01 g of the intermediate thus obtained was charged into an autoclave at room temperature, and the gas phase was replaced with nitrogen gas to set the gauge pressure to 0.20 MPa. After heating to 125°C, 286.0 g of butylene oxide was added under pressure over 2 hours while stirring, and the mixture was aged for 5 hours. After cooling to 60°C, the pressure was released, and 16.6 g of 50% lactic acid was added. While bubbling nitrogen gas at 20 mL / min, the pressure was reduced to -0.1 MPa and the mixture was stirred at 125°C for 1 hour. This yielded polymer (ii), a block polymer.

[0086] <Production Example 3> Softanol EP-7045 (manufactured by Nippon Shokubai) was used as polymer (iii).

[0087] <Production Example 4> An autoclave was charged with 150.0 g of 2-(N-methylanilino)ethanol and 8.75 g of 48% KOH aqueous solution at room temperature. The gas phase was replaced with nitrogen gas, and the pressure was reduced to -0.1 MPa while bubbling nitrogen gas at 20 mL / min. The temperature was then raised to 125°C and the mixture was stirred for 3 hours. After the pressure was raised to 0.20 MPa, the bubbling was stopped and 524.4 g of ethylene oxide was injected over 2 hours. The mixture was then aged for 3 hours. 452.4 g of the intermediate thus obtained was charged into an autoclave at room temperature, and the gas phase was replaced with nitrogen gas to set the gauge pressure to 0.20 MPa. 143.1 g of butylene oxide was added under pressure over 2 hours while stirring, and the mixture was aged for 3 hours. After the temperature was lowered to 60°C, the pressure was released, and 8.63 g of 50% lactic acid was added. While bubbling nitrogen gas at 20 mL / min, the pressure was reduced to -0.1 MPa, and the mixture was stirred at 125°C for 3 hours. This yielded polymer (iv), a block polymer.

[0088] <Production Example 5> An autoclave was charged with 150.0 g of 2-(dibutylamino)ethanol and 8.75 g of 48% KOH aqueous solution at room temperature. The gas phase was replaced with nitrogen gas, and the pressure was reduced to -0.1 MPa while bubbling nitrogen gas at 20 mL / min. The temperature was then raised to 125°C and the mixture was stirred for 3 hours. After the pressure was raised to 0.20 MPa, the bubbling was stopped and 419.4 g of ethylene oxide was injected over 2 hours. The mixture was then aged for 3 hours. 573.6 g of the intermediate thus obtained was charged into an autoclave at room temperature, and the gas phase was replaced with nitrogen gas to set the gauge pressure to 0.20 MPa. 187.2 g of butylene oxide was added under pressure over 2 hours while stirring, and the mixture was aged for 3 hours. After the temperature was lowered to 60°C, the pressure was released, and 13.0 g of 50% lactic acid was added. While bubbling nitrogen gas at 20 mL / min, the pressure was reduced to -0.1 MPa, and the mixture was stirred at 125°C for 3 hours. This yielded polymer (v), a block polymer.

[0089] <Production Example 6> An autoclave was charged with 150.0 g of 2-(dibutylamino)ethanol and 8.75 g of 48% KOH aqueous solution at room temperature. The gas phase was replaced with nitrogen gas, and the pressure was reduced to -0.1 MPa while bubbling nitrogen gas at 20 mL / min. The mixture was then heated to 125°C and stirred for 3 hours. After the pressure was increased to 0.20 MPa, the bubbling was stopped, and 316.5 g of ethylene oxide and 156.0 g of butylene oxide were added over 2 hours, followed by aging for 3 hours. The temperature was lowered to 60°C, the pressure was released, and 13.5 g of 50% lactic acid was added. The pressure was reduced to -0.1 MPa while bubbling nitrogen gas at 20 mL / min, and the mixture was stirred at 125°C for 3 hours. This yielded polymer (vi), a random polymer.

[0090] <Production Example 7> An autoclave was charged with 150.0 g of phenol and 8.75 g of 48% KOH aqueous solution at room temperature. The gas phase was replaced with nitrogen gas, and the pressure was reduced to -0.07 MPa while bubbling nitrogen gas at 20 mL / min. The mixture was then heated to 125°C and stirred for 3 hours. After the pressure was increased to 0.20 MPa, the bubbling was stopped, and 210.6 g of ethylene oxide was injected over 2 hours, followed by aging for 3 hours. The temperature was lowered to 60°C, the pressure was released, and 13.5 g of 50% lactic acid was added. The pressure was reduced to -0.1 MPa while bubbling nitrogen gas at 20 mL / min, and the mixture was stirred at 125°C for 3 hours. This yielded polymer (vii), a block polymer.

[0091] [Example 1] Polymer (i) was evaluated for its concentration rate, desalination performance, water recovery rate, and distribution property with respect to salts and water contained in the water to be treated from a liquid mainly composed of an extractant and a liquid mainly composed of water obtained by the following method.

[0092] <Process (I)> 8 g of a 2% sodium chloride aqueous solution (hereinafter referred to as the initial brine) was mixed with the same amount of polymer (i) as the initial brine and brought into contact. After standing at 30°C for 24 hours, phase separation into a lower phase (Ie-1) mainly composed of the extractant and an upper phase (Iw-1) mainly composed of water was confirmed, and the upper and lower phases were each collected with a dropper. The weight of the extractant-based liquid (Ie-1) was 10.6 g, and the weight of the water-based liquid (Iw-1) was 5.4 g.

[0093] <Process (II)> 10.6 g of the separated extractant-based liquid (Ie-1) was heated to 50°C and allowed to stand for 24 hours. Phase separation into a lower extractant-based liquid (IIe-1) and an upper water-based liquid (IIw-1) was confirmed, and the upper and lower phases were each collected with a dropper. The extractant-based liquid (IIe-1) weighed 9.1 g, and the water-based liquid (IIw-1) weighed 1.5 g.

[0094] <Evaluation> (Concentration rate evaluation) The concentration of salts contained in the water to be treated was evaluated using the following formula (1). TIFF0007752488000001.tif15150

[0095] (Desalination performance evaluation) The salt rejection rate was calculated for the salt removed from the salt contained in the water to be treated using the following formula (2). TIFF0007752488000002.tif17150

[0096] (Water recovery rate evaluation) The recovery rate (water recovery rate) of water contained in the water to be treated was calculated using the following formula (3). TIFF0007752488000003.tif19150

[0097] (Water partition coefficient (I-wp)) The distribution ratio of the water contained in the water treated in step (I) to the liquid mainly composed of the extractant (liquid Ie) and the liquid mainly composed of water (liquid Iw) was calculated using the following formula (4). TIFF0007752488000004.tif17150

[0098] (Salt distribution coefficient (I-sp)) The distribution ratio of salts contained in the water treated in step (I) to the liquid mainly composed of the extractant (liquid Ie) and the liquid mainly composed of water (liquid Iw) was calculated using the following equations (5) and (6). TIFF0007752488000005.tif17150

[0099] TIFF0007752488000006.tif36150

[0100] [Examples 2 to 9, Comparative Examples 1 and 2] The same procedure as in Example 1 was carried out except that the type of polymer to be blended, the concentration and mass of the initial salt water, and the temperature in step (II) were changed to those shown in Table 1.

[0101] [Table 1]

[0102] The results in Table 1 demonstrate that it is possible to efficiently extract water from treated water and increase the solute concentration in the treated water.

Claims

1. An extractant used to transfer water contained in the treated water to an extractant-containing extractant by contacting the treated water with the treated water without using a membrane, An extractant characterized by comprising a polymer having structural units derived from an amine containing a hydrocarbon group having 4 to 30 carbon atoms and / or structural units derived from a hydroxyl group-containing compound containing a hydrocarbon group having 4 to 30 carbon atoms, and structural units derived from an epoxy compound having 3 to 15 carbon atoms.

2. 2. The extractant according to claim 1, wherein the polymer has a cloud point of 10°C to 50°C.

3. 3. The extractant according to claim 1, wherein the number of moles of the epoxy compound added to the polymer is 4 to 100 per mole of the amine and / or hydroxyl group-containing compound.

4. The extractant according to any one of claims 1 to 3, wherein the epoxy compound is at least two or more epoxy compounds selected from the group consisting of ethylene oxide, propylene oxide, and butylene oxide.

5. The extractant according to any one of claims 1 to 4, wherein the number average molecular weight of the polymer is 300 to 10,000.

6. The extractant according to any one of claims 1 to 5, wherein the polymer has structural units derived from two types of epoxy compounds, and the molar ratio of the structural units derived from the epoxy compound having a smaller carbon number to the structural units derived from the epoxy compound having a larger carbon number is 1:1 to 20:

1.

7. A step (I) of contacting treated water with an extract containing the extractant according to any one of claims 1 to 6 without using a membrane, thereby transferring water contained in the treated water to the extract, thereby concentrating the treated water; and (II) heating the extract containing the extractant and water to separate it into a liquid mainly composed of the extractant and a liquid mainly composed of water.

8. The water treatment method according to claim 7, which is used for concentrating wastewater.

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