JP2017043556A - Compound, ionic liquid, platinum group element extraction agent, and platinum group element extraction method - Google Patents
Compound, ionic liquid, platinum group element extraction agent, and platinum group element extraction method Download PDFInfo
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 title claims abstract description 128
- 238000000605 extraction Methods 0.000 title claims abstract description 114
- 150000001875 compounds Chemical class 0.000 title claims abstract description 101
- 239000002608 ionic liquid Substances 0.000 title claims abstract description 86
- 239000003795 chemical substances by application Substances 0.000 title abstract 2
- 239000010948 rhodium Substances 0.000 claims description 42
- 239000007864 aqueous solution Substances 0.000 claims description 34
- 229910052751 metal Inorganic materials 0.000 claims description 27
- 229910052703 rhodium Inorganic materials 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 18
- 239000002184 metal Substances 0.000 claims description 16
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical group [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 16
- 230000002378 acidificating effect Effects 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- -1 cyclic amine Chemical class 0.000 claims description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 150000001450 anions Chemical class 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 78
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 62
- 239000000243 solution Substances 0.000 description 51
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 43
- 239000012071 phase Substances 0.000 description 32
- 238000006243 chemical reaction Methods 0.000 description 29
- 239000007788 liquid Substances 0.000 description 23
- 229910001361 White metal Inorganic materials 0.000 description 22
- 239000010969 white metal Substances 0.000 description 22
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- 229910052697 platinum Inorganic materials 0.000 description 18
- 238000000926 separation method Methods 0.000 description 18
- 238000005160 1H NMR spectroscopy Methods 0.000 description 17
- 150000002430 hydrocarbons Chemical group 0.000 description 16
- 229910052763 palladium Inorganic materials 0.000 description 16
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 14
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- 239000008346 aqueous phase Substances 0.000 description 13
- 230000001965 increasing effect Effects 0.000 description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 11
- 235000011114 ammonium hydroxide Nutrition 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- 238000001914 filtration Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 229940125782 compound 2 Drugs 0.000 description 8
- ZXMGHDIOOHOAAE-UHFFFAOYSA-N 1,1,1-trifluoro-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F ZXMGHDIOOHOAAE-UHFFFAOYSA-N 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 229910052786 argon Inorganic materials 0.000 description 7
- 230000018044 dehydration Effects 0.000 description 7
- 238000006297 dehydration reaction Methods 0.000 description 7
- 238000007738 vacuum evaporation Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 5
- 230000003247 decreasing effect Effects 0.000 description 4
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 238000009616 inductively coupled plasma Methods 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 229910021645 metal ion Inorganic materials 0.000 description 4
- MCTWTZJPVLRJOU-UHFFFAOYSA-O 1-methylimidazole Chemical class CN1C=C[NH+]=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-O 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 230000002708 enhancing effect Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 229910052741 iridium Inorganic materials 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- 238000005191 phase separation Methods 0.000 description 3
- 229910052707 ruthenium Inorganic materials 0.000 description 3
- VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 238000010908 decantation Methods 0.000 description 2
- LAWOZCWGWDVVSG-UHFFFAOYSA-N dioctylamine Chemical compound CCCCCCCCNCCCCCCCC LAWOZCWGWDVVSG-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- PXSXRABJBXYMFT-UHFFFAOYSA-N n-hexylhexan-1-amine Chemical compound CCCCCCNCCCCCC PXSXRABJBXYMFT-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
- NJBCRXCAPCODGX-UHFFFAOYSA-N 2-methyl-n-(2-methylpropyl)propan-1-amine Chemical compound CC(C)CNCC(C)C NJBCRXCAPCODGX-UHFFFAOYSA-N 0.000 description 1
- WHLZPGRDRYCVRQ-UHFFFAOYSA-O 3-butyl-2-methyl-1h-imidazol-3-ium Chemical compound CCCCN1C=C[NH+]=C1C WHLZPGRDRYCVRQ-UHFFFAOYSA-O 0.000 description 1
- 241001061225 Arcos Species 0.000 description 1
- SAIKULLUBZKPDA-UHFFFAOYSA-N Bis(2-ethylhexyl) amine Chemical compound CCCCC(CC)CNCC(CC)CCCC SAIKULLUBZKPDA-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 235000002597 Solanum melongena Nutrition 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- QZPSXPBJTPJTSZ-UHFFFAOYSA-N aqua regia Chemical compound Cl.O[N+]([O-])=O QZPSXPBJTPJTSZ-UHFFFAOYSA-N 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- INDFXCHYORWHLQ-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)azanide;1-butyl-3-methylimidazol-3-ium Chemical compound CCCCN1C=C[N+](C)=C1.FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F INDFXCHYORWHLQ-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical group CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000004693 imidazolium salts Chemical class 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P10/00—Technologies related to metal processing
- Y02P10/20—Recycling
Abstract
Description
本発明は、化合物、イオン液体、白金族元素の抽出剤、白金族元素の抽出方法に関する。 The present invention relates to a compound, an ionic liquid, a platinum group element extractant, and a platinum group element extraction method.
白金をはじめとする白金族元素（ＰＧＭｓ）は、現在、枯渇問題に直面しており、その高効率且つ高選択な抽出方法の開発が、広く工業分野において急務となっている。 Platinum group elements (PGMs), including platinum, are currently facing a depletion problem, and the development of a highly efficient and highly selective extraction method is widely urgent in the industrial field.
一方で、イオン液体は、低融点の溶融塩であり、難燃性、不揮発性、低毒性等を備えるため、環境に調和した溶媒となり得る、次世代の媒体として知られている。イオン液体は、構成分子の分子構造を調節することによって、有機溶媒及び水系溶媒の双方に対して二相分離する性質を付与することが可能であるため、排出物・廃棄物から有用金属塩を抽出・回収するために用いられる新たな媒体として注目を集めている。 On the other hand, an ionic liquid is a low-melting-point molten salt and is known as a next-generation medium that can be a solvent in harmony with the environment because it has flame retardancy, non-volatility, low toxicity, and the like. By adjusting the molecular structure of the constituent molecules, ionic liquids can be given the property of two-phase separation for both organic and aqueous solvents. It attracts attention as a new medium used for extraction and recovery.
イオン液体を用いた白金族元素の抽出の例としては、例えば、（Ｃ8Ｈ17）（ＣＨ3）Ｎ（ＣＯ）−ＣＨ2−Ｎ（Ｃ6Ｈ13）−ＣＨ2−（ＣＯ）Ｎ（ＣＨ3）（Ｃ8Ｈ17）で表される化合物からなるイオン性液体を用いた例が知られている（例えば、非特許文献１参照）。この手法によれば、パラジウム（２価）、白金（４価）、ロジウム（３価）をある程度の抽出率で抽出することが可能である。 Examples of extraction of platinum group elements using an ionic liquid include, for example, (C 8 H 17 ) (CH 3 ) N (CO) —CH 2 —N (C 6 H 13 ) —CH 2 — (CO) N An example using an ionic liquid composed of a compound represented by (CH 3 ) (C 8 H 17 ) is known (for example, see Non-Patent Document 1). According to this method, palladium (divalent), platinum (tetravalent), and rhodium (trivalent) can be extracted at a certain extraction rate.
しかしながら、上記従来の白金族元素の抽出方法には改善の余地も存在しており、白金族元素を十分に高い効率で抽出することを実現する新たな抽出手法の開発が望まれている。 However, there is room for improvement in the conventional platinum group element extraction method, and it is desired to develop a new extraction method that realizes extraction of the platinum group element with sufficiently high efficiency.
そこで、本発明は、白金族元素を高い抽出率で抽出することを目的とする。 Accordingly, an object of the present invention is to extract platinum group elements at a high extraction rate.
本発明の要旨は以下の通りである。
本発明の化合物は、下記式（１）
で表されることを特徴とする。
The gist of the present invention is as follows.
The compound of the present invention has the following formula (1)
It is represented by.
本発明のイオン液体は、本発明の化合物を含むことを特徴とする。ここで、本発明のイオン液体では、上記式（１）において、Ｒ1及びＲ2は、ブチル基、ヘキシル基、オクチル基からなる群から選択される少なくとも１種であり、ここで、Ｒ1とＲ2とは、同じであり、Ｒ3は、メチル基であり、Ａ-は、Ｎ-（ＣＦ3ＳＯ2）2であり、ｎは、３である、ことが好ましい。 The ionic liquid of the present invention contains the compound of the present invention. Here, in the ionic liquid of the present invention, in the above formula (1), R 1 and R 2 are at least one selected from the group consisting of a butyl group, a hexyl group, and an octyl group, where R 1 And R 2 are the same, R 3 is a methyl group, A − is N − (CF 3 SO 2 ) 2 , and n is preferably 3.
本発明の白金族元素の抽出剤は、本発明のイオン液体を含むことを特徴とする。ここで、前記白金族元素がロジウムであることが好ましい。 The platinum group element extractant of the present invention includes the ionic liquid of the present invention. Here, the platinum group element is preferably rhodium.
本発明の白金族元素の抽出方法は、本発明のイオン液体を用いて、白金族元素の金属塩の水溶液から、白金族元素の金属塩を抽出する、抽出工程を含むことを特徴とする。 The platinum group element extraction method of the present invention includes an extraction step of extracting a platinum group element metal salt from an aqueous solution of the platinum group element metal salt using the ionic liquid of the present invention.
本発明によれば、白金族元素を高い抽出率で抽出することができる。 According to the present invention, platinum group elements can be extracted at a high extraction rate.
以下、図面を参照して、本発明の、化合物、イオン液体、白金族元素の抽出剤、白金族元素の抽出方法の実施形態について、詳細に例示説明する。 Hereinafter, embodiments of the compound, ionic liquid, platinum group element extractant, and platinum group element extraction method of the present invention will be described in detail with reference to the drawings.
（化合物）
本発明を実施するための形態（以下、「本実施形態」ともいう）の化合物は、下記式（１）
で表される。
(Compound)
The compound of the form for carrying out the present invention (hereinafter also referred to as “this embodiment”) is represented by the following formula (1):
It is represented by
上記式（１）において、Ｒ1及びＲ2の炭素数としては、それぞれ、１〜１２としてよく、水相と二相分離する特性を高める観点から、２〜１２が好ましく、３〜８が更に好ましく、４〜８が特に好ましい。Ｒ1及びＲ2の炭化水素基としては、それぞれ、飽和であっても不飽和であってもよく、芳香族基、環状炭化水素基、直鎖炭化水素基、分岐鎖炭化水素基等が挙げられる。 In the above formula (1), the carbon numbers of R 1 and R 2 may be 1 to 12, respectively, preferably 2 to 12, more preferably 3 to 8 from the viewpoint of improving the property of two-phase separation from the aqueous phase. 4 to 8 are particularly preferable. The hydrocarbon group for R 1 and R 2 may be saturated or unsaturated, and includes an aromatic group, a cyclic hydrocarbon group, a straight chain hydrocarbon group, a branched chain hydrocarbon group, and the like. It is done.
上記式（１）において、Ｒ3の炭素数としては、１〜４としてよい。Ｒ3の炭化水素基としては、直鎖炭化水素基、分岐鎖炭化水素基等が挙げられ、具体的には、メチル基、エチル基、プロピル基、ブチル基が挙げられる。 In the above formula (1), R 3 may have 1 to 4 carbon atoms. Examples of the hydrocarbon group for R 3 include a straight chain hydrocarbon group and a branched chain hydrocarbon group, and specific examples include a methyl group, an ethyl group, a propyl group, and a butyl group.
Ｒ1及びＲ2の置換炭化水素基における置換基としては、炭化水素基（飽和であっても不飽和であってもよく、芳香族基、環状炭化水素基、直鎖炭化水素基、分岐鎖炭化水素基等）、ヒドロキシル基、エーテル基、モルホリノ基、エステル基、アミド基、パーフルオロアルキル基、ニトリル基（シアノ基）、アミノ基、イミノ基、ウレア基、カルボキシル基、カルボニル基（アルデヒド基、ケトン基）、スルホン酸基（スルホ基）、ニトロ基、ハロゲン、等が挙げられる。これらの中でも、水相と二相分離する特性を高める観点から、直鎖炭化水素基、分岐鎖炭化水素基が好ましい。
これらの詳細は、１種単独で用いてもよく、２種以上を組み合わせて用いてもよい。
As the substituent in the substituted hydrocarbon group of R 1 and R 2 , a hydrocarbon group (which may be saturated or unsaturated, an aromatic group, a cyclic hydrocarbon group, a linear hydrocarbon group, a branched chain) Hydrocarbon group, etc.), hydroxyl group, ether group, morpholino group, ester group, amide group, perfluoroalkyl group, nitrile group (cyano group), amino group, imino group, urea group, carboxyl group, carbonyl group (aldehyde group) , Ketone group), sulfonic acid group (sulfo group), nitro group, halogen, and the like. Among these, a straight chain hydrocarbon group and a branched chain hydrocarbon group are preferable from the viewpoint of enhancing the property of separating into two phases from the aqueous phase.
These details may be used individually by 1 type, and may be used in combination of 2 or more type.
上記式（１）において、Ｒ1及びＲ2の組み合わせの具体例としては、合成を容易にする観点、及び水相と二相分離する特性を高める観点から、ジブチル基、ジヘキシル基、ジオクチル基が好ましい。 In the above formula (1), specific examples of the combination of R 1 and R 2 include dibutyl group, dihexyl group and dioctyl group from the viewpoint of facilitating the synthesis and enhancing the property of two-phase separation from the aqueous phase. preferable.
また、上記具体例として、Ｒ1とＲ2とを同じとして、−Ｃ2Ｈ5ＯＨ、−Ｃ2Ｈ5ＯＣＨ3、−ＣＨ2ＣＯＯＣ2Ｈ5であってもよい。
更に、上記式（１）において、−ＮＲ1Ｒ2として、下記式（２）
Further, in the above formula (1), as —NR 1 R 2 , the following formula (2)
上記式（１）において、ｎは、２〜８としてよく、化合物の粘度及び疎水性を抽出剤として好適なものとする観点から、２〜６が好ましく、３が更に好ましい。 In the above formula (1), n may be 2 to 8, preferably 2 to 6, and more preferably 3 from the viewpoint of making the viscosity and hydrophobicity of the compound suitable as an extractant.
上記式（１）において、Ａ-は、Ｎ-（ＣＦ3ＳＯ2）2（以下、「ＮＴｆ2 -」とも称する）、Ｐ-Ｆ6、Ｂ-Ｆ4、Ｃｌ-、ＣＦ3ＳＯ3 -等が挙げられる。これらの中でも、Ａ-は、化合物の疎水性を高める観点から、Ｎ-（ＣＦ3ＳＯ2）2が好ましい。また、イオン液体の製造コストを低減する観点から、Ｃｌ-も好ましい。
これらは、１種単独で用いてもよく、２種以上を組み合わせて用いてもよい。
In the above formula (1), A − is N − (CF 3 SO 2 ) 2 (hereinafter also referred to as “NTf 2 − ”), P − F 6 , B − F 4 , Cl − , CF 3 SO 3 −. Etc. Among these, A − is preferably N − (CF 3 SO 2 ) 2 from the viewpoint of increasing the hydrophobicity of the compound. From the viewpoint of reducing the production cost of the ionic liquid, Cl - is also preferable.
These may be used alone or in combination of two or more.
これら化合物は、１種単独で用いてもよく、２種以上を組み合わせて用いてもよい。 These compounds may be used individually by 1 type, and may be used in combination of 2 or more type.
（イオン液体）
本実施形態のイオン液体は、前述の本実施形態の化合物からなる。
本実施形態のイオン液体は、水溶液（例えば、０〜１０ＭのＨＣｌ水溶液、０〜５ＭのＨＮＯ3等の酸性水溶液、０〜５Ｍのアンモニア水等の塩基性水溶液等）と混合したときに二相系を形成する（相分離する）ことが、白金族元素の抽出剤としての使用を可能にする観点から、望まれる。
(Ionic liquid)
The ionic liquid of this embodiment consists of the compound of this embodiment mentioned above.
When the ionic liquid of this embodiment is mixed with an aqueous solution (for example, a 0-10 M HCl aqueous solution, an acidic aqueous solution such as 0-5 M HNO 3 , a basic aqueous solution such as 0-5 M ammonia water, etc.), it is two-phase. Forming the system (phase-separating) is desirable from the viewpoint of enabling the use of platinum group elements as extractants.
（白金族元素の抽出剤）
本実施形態の白金族元素の抽出剤は、前述の本実施形態のイオン液体を含み、必要に応じて、その他の成分を含んでもよい。
(Platinum group element extractant)
The platinum group element extractant of the present embodiment includes the above-described ionic liquid of the present embodiment, and may include other components as necessary.
抽出される白金族元素としては、ルテニウム（Ｒｕ）、ロジウム（Ｒｈ）、パラジウム（Ｐｄ）、オスミウム（Ｏｓ）、イリジウム（Ｉｒ）、白金（Ｐｔ）であり、特に、価格が高く、回収の必要性が高い、ロジウムが、抽出対象として好ましい。
これら白金族元素は、１種単独でもよく、２種以上の組み合わせでもよい。
The platinum group elements to be extracted are ruthenium (Ru), rhodium (Rh), palladium (Pd), osmium (Os), iridium (Ir), and platinum (Pt), which are particularly expensive and need to be recovered. Rhodium, which has high properties, is preferable as an extraction target.
These platinum group elements may be used alone or in combination of two or more.
抽出率を高める観点からは、上記式（１）におけるイミダゾリウム骨格を含むカチオンとして、アルキルイミダゾリウム塩（特に、メチルイミダゾリウム塩）を、対アニオンとして、Ｎ-（ＣＦ3ＳＯ2）2、Ｐ-Ｆ6を、組み合わせて用いることが好ましい。 From the viewpoint of increasing the extraction rate, an alkyl imidazolium salt (particularly, a methyl imidazolium salt) is used as a cation containing the imidazolium skeleton in the above formula (1), and N − (CF 3 SO 2 ) 2 is used as a counter anion. P − F 6 is preferably used in combination.
本実施形態の白金族元素の抽出剤に含まれるカチオン種を複数種とした混合系を用いる場合には、上記式（１）で表されるアミノ基を有するイミダゾリウム塩と、メチルブチルイミダゾリウム塩とを、１：１０〜１０：１で混合して用いることが、白金族元素の抽出率を高める観点から、好ましい。上記混合比を、１：１〜１０：１とすれば、白金及びパラジウムを選択性に抽出する効果を高めることができる。また、１：１０〜１：１とすれば、ロジウムの抽出率を向上させることができる。 In the case of using a mixed system in which a plurality of cationic species contained in the platinum group element extractant of the present embodiment is used, an imidazolium salt having an amino group represented by the above formula (1) and methylbutylimidazolium are used. It is preferable to use the salt in a mixture of 1:10 to 10: 1 from the viewpoint of increasing the extraction rate of the platinum group element. When the mixing ratio is 1: 1 to 10: 1, the effect of extracting platinum and palladium selectively can be enhanced. Moreover, if it is set to 1: 10-1: 1, the extraction rate of rhodium can be improved.
抽出剤に含まれ得るその他の成分は、特に限定されることなく、目的に応じて適宜定められてよい。 Other components that can be contained in the extractant are not particularly limited and may be appropriately determined according to the purpose.
本実施形態の白金族元素の抽出剤中における、本実施形態のイオン液体の含有量は、抽出能を高める観点から、抽出剤を１００質量％として、１０〜１００質量％であることが好ましく、５０〜１００質量％であることが更に好ましく、１００質量％である（すなわち、本実施形態の白金族元素の抽出剤は、本実施形態のイオン液体からなる）ことが特に好ましい。 In the platinum group element extractant of the present embodiment, the content of the ionic liquid of the present embodiment is preferably 10 to 100% by mass, with the extractant being 100% by mass, from the viewpoint of enhancing the extractability. More preferably, it is 50-100 mass%, and it is especially preferable that it is 100 mass% (that is, the platinum group element extractant of this embodiment consists of the ionic liquid of this embodiment).
（白金族元素の抽出方法）
本実施形態の白金族元素の抽出方法は、前述の本実施形態のイオン液体を用いて、白金族元素の金属塩の酸性水溶液から、白金族元素の金属塩を抽出する、抽出工程を含む。かかる抽出により、白金族元素の金属塩のイオン液体溶液が得られる。
(Platinum group element extraction method)
The platinum group element extraction method of the present embodiment includes an extraction step of extracting the platinum group element metal salt from the acidic aqueous solution of the platinum group element metal salt using the ionic liquid of the present embodiment described above. By such extraction, an ionic liquid solution of a platinum group metal salt is obtained.
本実施形態では、例えば、排出・廃棄された白金族元素（例えば、プリント基板に含まれる白金等）を、王水等の極めて酸性度の高い（ｐＨ＝１程度）酸性溶液を用いて、溶解させることによって、上記抽出工程に供される白金族元素の金属塩の水溶液を調製してよい。 In the present embodiment, for example, discharged and discarded platinum group elements (for example, platinum contained in a printed circuit board) are dissolved using an acidic solution such as aqua regia having a very high acidity (pH = 1). By carrying out, you may prepare the aqueous solution of the metal salt of the platinum group element used for the said extraction process.
上記抽出工程では、白金族元素の金属塩の酸性水溶液とイオン液体とについて、通常の分液操作を行ってよく、必要に応じて、二相系を形成させるために、遠心分離を行ってもよい。 In the extraction step, a normal separation operation may be performed for the acidic aqueous solution of the platinum group metal salt and the ionic liquid, and if necessary, centrifugation may be performed to form a two-phase system. Good.
抽出される白金族元素の金属塩の水溶液における白金族元素の金属塩の濃度としては、抽出率を高める観点から、白金族元素の金属塩の水溶液を１００質量％として、１０-1〜１０6質量ｐｐｍであることが好ましく、５〜１０4質量ｐｐｍであることが更に好ましい。
なお、上記濃度は、１０-1ｐｐｍ未満の場合であっても、１０6ｐｐｍ超の場合であっても、本実施形態のイオン液体による抽出は可能である。
The concentration of the platinum group element metal salt in the aqueous solution of the platinum group element metal salt is 10 −1 to 10 6 from the viewpoint of increasing the extraction rate, with the platinum group element metal salt aqueous solution being 100% by mass. it is preferably mass ppm, and more preferably 5 to 10 4 mass ppm.
In addition, even if the said density | concentration is a case where it is less than 10 < -1 > ppm or a case where it exceeds 10 < 6 > ppm, extraction with the ionic liquid of this embodiment is possible.
白金族元素の金属塩の酸性水溶液に使用し得る酸としては、塩酸（ＨＣｌ）、硫酸（Ｈ2ＳＯ4）、硝酸（ＨＮＯ3）等が挙げられ、特に、塩酸が好ましい。
酸として塩酸を使用する場合、この水溶液における塩酸濃度としては、０．１〜１０Ｍとすることが好ましい。また、硝酸を使用する場合、水溶液における硝酸濃度としては、０〜５Ｍとすることが好ましい。
Examples of the acid that can be used for the acidic aqueous solution of the platinum group metal salt include hydrochloric acid (HCl), sulfuric acid (H 2 SO 4 ), nitric acid (HNO 3 ), and hydrochloric acid is particularly preferable.
When hydrochloric acid is used as the acid, the hydrochloric acid concentration in this aqueous solution is preferably 0.1 to 10M. When nitric acid is used, the nitric acid concentration in the aqueous solution is preferably 0 to 5M.
本実施形態の白金族元素の抽出方法では、前述の抽出工程を複数回行ってもよい。 In the platinum group element extraction method of the present embodiment, the above-described extraction step may be performed a plurality of times.
本実施形態では、前述の抽出工程を、用いるイオン液体を１種としつつ、酸濃度（塩酸濃度）の条件を変えて、複数回行うことが好ましい。これにより、他の白金族元素を含む他の金属元素の中から特定の白金族元素を選択的に抽出することが可能となる。
より具体的には、所望の白金族元素の抽出率が低く、他の金属元素の抽出率が高い、第１の酸濃度の条件で１回目の抽出工程を行い、続いて、所望の白金族元素の抽出率が高く、他の金属元素の抽出率が低い、第２の酸濃度の条件で２回目の抽出工程を行うことによって、抽出時の所望の白金族元素の選択性を高めることができる。
例えば、上記式（１）においてＲ1及びＲ2がヘキシル又はオクチル基である化合物（例えば、後述の化合物Ｃ６（実施例２）又は化合物Ｃ８（実施例３））からなるイオン液体を用いて、パラジウム、白金、ロジウムを含む酸性水溶液からロジウムを抽出する場合、第１の塩酸濃度（０．１〜０．５Ｍ、例えば、０．３Ｍ）で、パラジウム、白金を抽出し、その後、第２の塩酸濃度（２．０〜５．０Ｍ、例えば、４Ｍ）で、ロジウムを抽出することによって、他の白金族元素を含む他の金属元素の中からロジウムを選択的に抽出することが可能となる（図３、図４参照）。
In the present embodiment, it is preferable to perform the above-described extraction process a plurality of times while changing the conditions of the acid concentration (hydrochloric acid concentration) while using one type of ionic liquid. This makes it possible to selectively extract a specific platinum group element from other metal elements including other platinum group elements.
More specifically, the extraction step of the desired platinum group element is low, the extraction rate of other metal elements is high, and the first extraction step is performed under the condition of the first acid concentration, and then the desired platinum group element is obtained. By performing the second extraction step under the condition of the second acid concentration with a high extraction rate of elements and a low extraction rate of other metal elements, the selectivity of a desired platinum group element during extraction can be improved. it can.
For example, by using an ionic liquid composed of a compound in which R 1 and R 2 in formula (1) are hexyl or octyl groups (for example, compound C6 (Example 2) or compound C8 (Example 3) described later), When rhodium is extracted from an acidic aqueous solution containing palladium, platinum, and rhodium, palladium and platinum are extracted at a first hydrochloric acid concentration (0.1 to 0.5 M, for example, 0.3 M), and then the second By extracting rhodium at a hydrochloric acid concentration (2.0 to 5.0M, for example, 4M), rhodium can be selectively extracted from other metal elements including other platinum group elements. (See FIGS. 3 and 4).
また、本実施形態では、特定の白金族元素を選択的に抽出する観点から、前述の抽出工程を、酸濃度（塩酸濃度）の条件を一定としつつ、用いるイオン液体を変えて、複数回行うことも好ましい。
より具体的には、所望の白金族元素の抽出率が低く、他の金属元素の抽出率が高い、第１のイオン液体を用いて１回目の抽出工程を行い、続いて、所望の白金族元素の抽出率が高く、他の金属元素の抽出率が低い、第２のイオン液体を用いて２回目の抽出工程を行うことによって、抽出時の所望の白金族元素の選択性を高めることができる。
例えば、塩酸濃度２．０Ｍ〜４．０Ｍ、例えば、２．５Ｍの条件で、パラジウム、白金、ロジウムを含む酸性水溶液からロジウムを抽出する場合、上記式（１）においてＲ1及びＲ2がブチル基である化合物（例えば、後述の化合物Ｃ４（実施例１））からなるイオン液体を用いて、パラジウム、白金を抽出し、その後、上記式（１）においてＲ1及びＲ2がヘキシル又はオクチル基である化合物（例えば、後述の化合物Ｃ６（実施例２）又は化合物Ｃ８（実施例３））からなるイオン液体を用いて、ロジウムを抽出することによって、他の白金族元素を含む他の金属元素の中からロジウムを選択的に抽出することが可能となる（図２〜図４参照）。
Moreover, in this embodiment, from the viewpoint of selectively extracting a specific platinum group element, the above-described extraction process is performed a plurality of times while changing the ionic liquid to be used while keeping the condition of the acid concentration (hydrochloric acid concentration) constant. It is also preferable.
More specifically, the first extraction step is performed using the first ionic liquid having a low extraction rate of the desired platinum group element and a high extraction rate of the other metal elements, and then the desired platinum group element. By performing the second extraction step using the second ionic liquid that has a high extraction rate of elements and a low extraction rate of other metal elements, the selectivity of a desired platinum group element during extraction can be increased. it can.
For example, in the case where rhodium is extracted from an acidic aqueous solution containing palladium, platinum, and rhodium under a hydrochloric acid concentration of 2.0 M to 4.0 M, for example, 2.5 M, R 1 and R 2 are butyl in the above formula (1). Palladium and platinum are extracted using an ionic liquid composed of a group compound (for example, compound C4 (Example 1) described later), and then R 1 and R 2 in the above formula (1) are hexyl or octyl groups Other metal elements including other platinum group elements by extracting rhodium using an ionic liquid comprising a compound (for example, Compound C6 (Example 2) or Compound C8 (Example 3) described later) Rhodium can be selectively extracted from the inside (see FIGS. 2 to 4).
更に、本実施形態では、前述の抽出工程を、用いるイオン液体、及び、酸濃度（塩酸濃度）の条件を変えて、複数回行うことが好ましい。これにより、他の白金族元素を含む他の金属元素の中から特定の白金族元素をより選択的に抽出することが可能となる。
より具体的には、所望の白金族元素の抽出率が低く、他の金属元素の抽出率が高い、第１のイオン液体を用いた第１の酸濃度の条件で、１回目の抽出工程を行い、続いて、所望の白金族元素の抽出率が高く、他の金属元素の抽出率が低い、第２のイオン液体を用いた第２の酸濃度の条件で、２回目の抽出工程を行うことによって、抽出時の所望の白金族元素の選択性を高めることができる。
例えば、上記式（１）においてＲ1及びＲ2がブチル基である化合物（例えば、後述の化合物Ｃ４（実施例１））からなるイオン液体を用いて、塩酸濃度０．１〜１．０Ｍの条件で、パラジウム、白金を抽出し、その後、上記式（１）においてＲ1及びＲ2がヘキシル又はオクチル基である化合物（例えば、後述の化合物Ｃ６（実施例２）又は化合物Ｃ８（実施例３））からなるイオン液体を用いて、塩酸濃度３．０〜４．０Ｍの条件で、ロジウムを抽出することによって、他の白金族元素を含む他の金属元素の中からロジウムを選択的に抽出することが可能となる（図２〜図４参照）。
Furthermore, in this embodiment, it is preferable to perform the above-described extraction step a plurality of times while changing the conditions of the ionic liquid to be used and the acid concentration (hydrochloric acid concentration). Thereby, a specific platinum group element can be more selectively extracted from other metal elements including other platinum group elements.
More specifically, the first extraction step is performed under the condition of the first acid concentration using the first ionic liquid in which the extraction rate of the desired platinum group element is low and the extraction rate of the other metal elements is high. Subsequently, the second extraction step is performed under the condition of the second acid concentration using the second ionic liquid in which the extraction rate of the desired platinum group element is high and the extraction rate of the other metal elements is low. Thereby, the selectivity of a desired platinum group element at the time of extraction can be improved.
For example, using an ionic liquid composed of a compound in which R 1 and R 2 are butyl groups in the above formula (1) (for example, Compound C4 (Example 1) described later), the hydrochloric acid concentration is 0.1 to 1.0 M. Under conditions, palladium and platinum are extracted, and then a compound in which R 1 and R 2 are hexyl or octyl groups in the above formula (1) (for example, Compound C6 (Example 2) or Compound C8 (Example 3) described later) The rhodium is selectively extracted from other metal elements including other platinum group elements by extracting rhodium under the conditions of hydrochloric acid concentration of 3.0 to 4.0 M using the ionic liquid comprising (See FIGS. 2 to 4).
本実施形態の白金族元素の抽出方法は、前記抽出工程後、塩基性水溶液を用いて、白金族元素の金属塩のイオン液体溶液から、白金族元素の金属塩を逆抽出する、逆抽出工程を更に含んでもよい。かかる逆抽出により、白金族元素の金属塩の塩基性水溶液が得られる。 The platinum group element extraction method of the present embodiment is a back extraction step in which the metal salt of the platinum group element is back extracted from the ionic liquid solution of the metal salt of the platinum group element using a basic aqueous solution after the extraction step. May further be included. By such back extraction, a basic aqueous solution of a metal salt of a platinum group element is obtained.
塩基性水溶液に使用し得る塩基としては、アンモニア、第１〜第３級アミン等が挙げられ、特に、アンモニアが好ましい。 Examples of the base that can be used in the basic aqueous solution include ammonia and primary to tertiary amines, and ammonia is particularly preferable.
以上、図面を参照して、本発明の化合物、イオン液体、白金族元素の抽出剤、白金族元素の抽出方法の実施形態について例示説明したが、上記実施形態には、適宜変更を加えることができ、本発明の化合物、イオン液体、白金族元素の抽出剤、白金族元素の抽出方法は、上記例示の実施形態に限定されることはない。 The embodiments of the compound, the ionic liquid, the platinum group element extractant, and the platinum group element extraction method of the present invention have been illustrated and described above with reference to the drawings. However, the above embodiments may be appropriately modified. The compound of the present invention, the ionic liquid, the platinum group element extractant, and the platinum group element extraction method are not limited to the above-described exemplary embodiments.
以下、実施例により本発明を更に詳細に説明するが、本発明は下記の実施例に何ら限定されるものではない。 EXAMPLES Hereinafter, although an Example demonstrates this invention further in detail, this invention is not limited to the following Example at all.
（原材料）
・１，３−ジブロモプロパン（和光純薬社製）
・１−メチルイミダゾール（東京化成社製）
・ビス（トリフルオロメタンスルホニル）イミドリチウム（アルドリッチ社製）
・ジブチルアミン（和光純薬社製）
・ジヘキシルアミン（東京化成社製）
・ジオクチルアミン（和光純薬社製）
これらは、特に断りのない限り、更なる精製を行うことなく、使用した。
(raw materials)
・ 1,3-Dibromopropane (Wako Pure Chemical Industries, Ltd.)
・ 1-Methylimidazole (manufactured by Tokyo Chemical Industry Co., Ltd.)
・ Bis (trifluoromethanesulfonyl) imidolithium (Aldrich)
・ Dibutylamine (Wako Pure Chemical Industries, Ltd.)
・ Dihexylamine (manufactured by Tokyo Chemical Industry Co., Ltd.)
・ Dioctylamine (Wako Pure Chemical Industries)
These were used without further purification unless otherwise noted.
（解析機器）
・1Ｈ−ＮＭＲ：Ｂｒｕｋｅｒ Ｄａｌｔｏｎｉｃｓ社製、商品名：ＡＶ４００Ｍ ｄｉｇｉｔａｌ ＮＭＲ
・ＩＣＰ−ＡＥＳ：日立ハイテクサイエンス社製、商品名：ＳＰＥＣＴＲＯ ＡＲＣＯＳ
(Analysis equipment)
· 1 H-NMR: Bruker Daltonics Inc., trade name: AV400M digital NMR
ICP-AES: manufactured by Hitachi High-Tech Science Co., Ltd., trade name: SPECTRO ARCOS
（試験Ａ）化合物の合成、イオン液体の調製、白金族元素の抽出剤の調製
下記式（３）に示す合成スキームにより、化合物Ｃ４、化合物Ｃ６、化合物Ｃ８、化合物ｉｓｏＣ４、化合物Ｃｙ、化合物Ｃ２−６を合成した。
−［１−（３−ブロモプロピル）−３−メチルイミダゾリウムブロミド］（「化合物１」）の合成−
四口丸底フラスコ（１０００ｍＬ）に、１、３−ジブロモプロパン２００ｇ（１．０８ｍｏｌ）のアセトン溶液２５０ｍＬを加え、フラスコ内をアルゴン置換した。アセトン５０ｍＬに１−メチルイミダゾール８．２１ｇ（１００ｍｍｏｌ）を溶解させ、この溶液を３０分間かけて滴下した。その後、反応溶液を、４５℃に設定したオイルバスで２０時間、加熱環流させ、反応を行った。反応の際に生じた白色固体と反応溶液とを、デカンテーションにより分離した。また、白色固体を少量のエタノールで溶解させた後、アセトンを多量に加えることによって、白色固体を再沈殿させ、白色固体中の生成物をアセトンに溶解させた。残った固体と溶液とを、再びデカンテーションにより分離した。反応溶液とこの溶液とを合わせた後、ロータリーエバポレーター及び真空乾燥機を用いて減圧濃縮した。この後、反応溶液／水で分液操作を行い、上相の水相を取り出した。次いで、水（Ｈ2Ｏ）／ヘキサンで分液操作を行い、下相の水相を取り出した。得られた水溶液を、ロータリーエバポレーター及び真空乾燥機を用いて減圧濃縮した。こうして、無色液体の化合物１（Ｃ7Ｈ12Ｂｒ2Ｎ2）を収率８１％で得た（２３．２ｇ、８１．７ｍｍｏｌ）。
得られた化合物の1Ｈ−ＮＭＲの結果は下記の通りであった。
1Ｈ−ＮＭＲ（４００ＭＨｚ，ＣＤＣｌ3） δ ２．５８（ｑｕｉｎ，Ｊ＝６．６Ｈｚ，２Ｈ），３．５０（ｔ，Ｊ＝６．２Ｈｚ，２Ｈ），４．１３（ｓ，３Ｈ），４．６１（ｔ，Ｊ＝６．８Ｈｚ，２Ｈ），７．５８（ｔ，Ｊ＝１．８Ｈｚ，１Ｈ），７．６４（ｔ，Ｊ＝１．８Ｈｚ，１Ｈ），１０．３５（ｓ，１Ｈ）
-Synthesis of [1- (3-bromopropyl) -3-methylimidazolium bromide] ("Compound 1")-
To a four-necked round bottom flask (1000 mL), 250 mL of an acetone solution of 200 g (1.08 mol) of 1,3-dibromopropane was added, and the inside of the flask was purged with argon. 8.21 g (100 mmol) of 1-methylimidazole was dissolved in 50 mL of acetone, and this solution was added dropwise over 30 minutes. Thereafter, the reaction solution was heated to reflux in an oil bath set at 45 ° C. for 20 hours to carry out the reaction. The white solid produced during the reaction and the reaction solution were separated by decantation. Further, the white solid was dissolved in a small amount of ethanol, and then a large amount of acetone was added to reprecipitate the white solid, and the product in the white solid was dissolved in acetone. The remaining solid and solution were separated again by decantation. The reaction solution and this solution were combined and then concentrated under reduced pressure using a rotary evaporator and a vacuum dryer. Thereafter, a liquid separation operation was performed with the reaction solution / water, and the upper aqueous phase was taken out. Subsequently, liquid separation operation was performed with water (H 2 O) / hexane, and the lower aqueous phase was taken out. The obtained aqueous solution was concentrated under reduced pressure using a rotary evaporator and a vacuum dryer. Thus, a colorless liquid compound 1 (C 7 H 12 Br 2 N 2 ) was obtained with a yield of 81% (23.2 g, 81.7 mmol).
The results of 1 H-NMR of the obtained compound were as follows.
1 H-NMR (400 MHz, CDCl 3 ) δ 2.58 (quin, J = 6.6 Hz, 2H), 3.50 (t, J = 6.2 Hz, 2H), 4.13 (s, 3H), 4.61 (t, J = 6.8 Hz, 2H), 7.58 (t, J = 1.8 Hz, 1H), 7.64 (t, J = 1.8 Hz, 1H), 10.35 (s) , 1H)
−［１−（３−ブロモプロピル）−３−メチルイミダゾリウムビス（トリフルオロメタンスルホニル）イミド）］（「化合物２」）の合成−
ナスフラスコ（３００ｍＬ）に、水（Ｈ2Ｏ）１５０ｍＬを加え、化合物１ ２３．２０ｇ（８１．７ｍｍｏｌ）、ビス（トリフルオロメタンスルホニル）イミドリチウム２５．８ｇ（８９．９ｍｍｏｌ）を、水に溶解させた。その後、室温で１時間撹拌しながら反応を行い、反応溶液をクロロホルム（ＣＨＣｌ3）で抽出した。抽出溶液について、無水硫酸マグネシウム（ＭｇＳＯ4）を用いた脱水操作、セライト濾過、ロータリーエバポレーター及び真空乾燥機を用いた減圧濃縮を行った。こうして、無色液体の化合物２（Ｃ9Ｈ12ＢｒＦ6Ｎ3Ｏ4Ｓ2）を収率９１％で得た（３５．９１ｇ、７４．２ｍｍｏｌ）。
得られた化合物の1Ｈ−ＮＭＲの結果は下記の通りであった。
1Ｈ−ＮＭＲ（４００ＭＨｚ，ＣＤＣｌ3） δ ２．４４（ｑｕｉｎ，Ｊ＝６．５Ｈｚ，２Ｈ），３．５０（ｔ，Ｊ＝６．０Ｈｚ，２Ｈ），３．９７（ｓ，３Ｈ），４．４２（ｔ，Ｊ＝７．０Ｈｚ，２Ｈ），７．２９（ｔ，Ｊ＝１．８Ｈｚ，１Ｈ），７．３５（ｔ，Ｊ＝１．８Ｈｚ，１Ｈ），８．８５（ｓ，１Ｈ）
-Synthesis of [1- (3-bromopropyl) -3-methylimidazolium bis (trifluoromethanesulfonyl) imide)] ("Compound 2")-
To an eggplant flask (300 mL), 150 mL of water (H 2 O) was added, and 23.20 g (81.7 mmol) of Compound 1 and 25.8 g (89.9 mmol) of bis (trifluoromethanesulfonyl) imidolithium were dissolved in water. It was. Thereafter, the reaction was carried out with stirring at room temperature for 1 hour, and the reaction solution was extracted with chloroform (CHCl 3 ). The extracted solution was subjected to dehydration using anhydrous magnesium sulfate (MgSO 4 ), Celite filtration, vacuum evaporation using a rotary evaporator and a vacuum dryer. Thus, a colorless liquid compound 2 (C 9 H 12 BrF 6 N 3 O 4 S 2 ) was obtained in a yield of 91% (35.91 g, 74.2 mmol).
The results of 1 H-NMR of the obtained compound were as follows.
1 H-NMR (400 MHz, CDCl 3 ) δ 2.44 (quin, J = 6.5 Hz, 2H), 3.50 (t, J = 6.0 Hz, 2H), 3.97 (s, 3H), 4.42 (t, J = 7.0 Hz, 2H), 7.29 (t, J = 1.8 Hz, 1H), 7.35 (t, J = 1.8 Hz, 1H), 8.85 (s , 1H)
−［１−３−（ジブチルアミノプロピル）−３−メチルイミダゾリウムビス（トリフルオロメタンスルホニル）イミド］（「化合物Ｃ４」）の合成−
三口丸底フラスコ（３００ｍＬ）に、化合物２；１４．５ｇ（３０ｍｍｏｌ）、ジブチルアミン１１．６ｇ（９０ｍｍｏｌ）、アセトニトリル（ＣＨ3ＣＮ）（１５０ｍＬ）を加え、フラスコ内をアルゴン置換した。その後、反応溶液を８５℃に設定したオイルバスで３時間、加熱環流させ、反応を行った。反応溶液を、固体が析出するまで、ロータリーエバポレーターを用いて減圧濃縮した。その後、濾過により、反応溶液から固体を除去し、濾液を再びロータリーエバポレーターを用いて減圧濃縮した。その後、クロロホルム（ＣＨＣｌ3）／５ｗｔ％アンモニア水（ＮＨ3ａｑ．）で、分液操作を行い、上相の５ｗｔ％アンモニア水相を除去し、下相のクロロホルム相を取り出した。次いで、クロロホルム（ＣＨＣｌ3）／水（Ｈ2Ｏ）で、分液操作を行い、下相のクロロホルム相を洗浄した。クロロホルム溶液について、無水硫酸マグネシウム（ＭｇＳＯ4）を用いた脱水操作、セライト濾過、ロータリーエバポレーター及び真空乾燥機を用いた減圧濃縮を行った。こうして、化合物Ｃ４（Ｃ17Ｈ30Ｆ6Ｎ4Ｏ4Ｓ2）を収率８９％で得た（１４．３１ｇ、２６．９ｍｍｏｌ）。
得られた化合物の1Ｈ−ＮＭＲの結果は下記の通りであった。
1Ｈ−ＮＭＲ（４００ＭＨｚ，ＣＤＣｌ3） δ ０．９１（ｔ，Ｊ＝７．２Ｈｚ，６Ｈ），１．２３−１．４０（ｍ，８Ｈ），１．９９（ｑｕｉｎ，Ｊ＝６．８Ｈｚ，２Ｈ），２．３７（ｔ，Ｊ＝７．４Ｈｚ，４Ｈ），２．４２（ｔ，Ｊ＝６．４Ｈｚ，２Ｈ），３．９５（ｓ，３Ｈ），４．２４（ｔ，Ｊ＝７．２Ｈｚ，２Ｈ），７．２９（ｑｕｉｎ，Ｊ＝１．６Ｈｚ，２Ｈ），８．７６（ｓ，１Ｈ）
化合物Ｃ４を、実施例１の化合物、イオン液体、抽出剤として用いた。
-Synthesis of [1-3- (dibutylaminopropyl) -3-methylimidazolium bis (trifluoromethanesulfonyl) imide] ("Compound C4")-
Compound 2; 14.5 g (30 mmol), dibutylamine 11.6 g (90 mmol), and acetonitrile (CH 3 CN) (150 mL) were added to a three-necked round bottom flask (300 mL), and the atmosphere in the flask was replaced with argon. Thereafter, the reaction solution was heated and refluxed in an oil bath set at 85 ° C. for 3 hours to carry out the reaction. The reaction solution was concentrated under reduced pressure using a rotary evaporator until a solid precipitated. Thereafter, the solid was removed from the reaction solution by filtration, and the filtrate was again concentrated under reduced pressure using a rotary evaporator. Thereafter, a liquid separation operation was performed with chloroform (CHCl 3 ) / 5 wt% aqueous ammonia (NH 3 aq.), The upper 5 wt% aqueous ammonia phase was removed, and the lower chloroform phase was taken out. Subsequently, a liquid separation operation was performed with chloroform (CHCl 3 ) / water (H 2 O) to wash the lower chloroform phase. The chloroform solution was subjected to dehydration using anhydrous magnesium sulfate (MgSO 4 ), Celite filtration, vacuum evaporation using a rotary evaporator and a vacuum dryer. Thus, compound C4 (C 17 H 30 F 6 N 4 O 4 S 2 ) was obtained in 89% yield (14.31 g, 26.9 mmol).
The results of 1 H-NMR of the obtained compound were as follows.
1 H-NMR (400 MHz, CDCl 3 ) δ 0.91 (t, J = 7.2 Hz, 6H), 1.23-1.40 (m, 8H), 1.99 (quin, J = 6.8 Hz) , 2H), 2.37 (t, J = 7.4 Hz, 4H), 2.42 (t, J = 6.4 Hz, 2H), 3.95 (s, 3H), 4.24 (t, J = 7.2 Hz, 2H), 7.29 (quin, J = 1.6 Hz, 2H), 8.76 (s, 1H)
Compound C4 was used as the compound, ionic liquid, and extractant of Example 1.
−［１−３−（ジヘキシルアミノプロピル）−３−メチルイミダゾリウムビス（トリフルオロメタンスルホニル）イミド］（「化合物Ｃ６」）の合成−
三口丸底フラスコ（５００ｍＬ）に、化合物２；１９．３７ｇ（４０ｍｍｏｌ）、ジヘキシルアミン２２．２４ｇ（１２０ｍｍｏｌ）、アセトニトリル（ＣＨ3ＣＮ）（２００ｍＬ）を加え、フラスコ内をアルゴン置換した。その後、反応溶液を８５℃に設定したオイルバスで３時間、加熱環流させ、反応を行った。反応溶液を、固体が析出するまで、ロータリーエバポレーターを用いて減圧濃縮した。その後、濾過により、反応溶液から固体を除去し、濾液を再びロータリーエバポレーターを用いて減圧濃縮した。その後、クロロホルム（ＣＨＣｌ3）／５ｗｔ％アンモニア水（ＮＨ3ａｑ．）で、分液操作を行い、上相の５ｗｔ％アンモニア水相を除去し、下相のクロロホルム相を残した。次いで、クロロホルム（ＣＨＣｌ3）／水（Ｈ2Ｏ）で、分液操作を行い、下相のクロロホルム相を洗浄した。クロロホルム溶液について、無水硫酸マグネシウム（ＭｇＳＯ4）を用いた脱水操作、セライト濾過、ロータリーエバポレーター及び真空乾燥機を用いた減圧濃縮を行った。こうして、化合物Ｃ６（Ｃ21Ｈ38Ｆ6Ｎ4Ｏ4Ｓ2）を収率９１％で得た（２１．４ｇ、３６．３ｍｍｏｌ）。
得られた化合物の1Ｈ−ＮＭＲの結果は下記の通りであった。
1Ｈ−ＮＭＲ（４００ＭＨｚ，ＣＤＣｌ3） δ ０．８９（ｔ，Ｊ＝６．８Ｈｚ，６Ｈ），１．２６−１．３９（ｍ，１６Ｈ），１．９９（ｑｕｉｎ，Ｊ＝６．８Ｈｚ，２Ｈ），２．３７（ｔ，Ｊ＝７．６Ｈｚ，４Ｈ），２．４３（ｔ，Ｊ＝６．６Ｈｚ，２Ｈ），３．９５（ｓ，３Ｈ），４．２４（ｔ，Ｊ＝７．２Ｈｚ，２Ｈ），７．３０（ｑｕｉｎ，Ｊ＝１．６Ｈｚ，２Ｈ），８．７６（ｓ，１Ｈ）
化合物Ｃ６を、実施例２の化合物、イオン液体、抽出剤として用いた。
-Synthesis of [1-3- (dihexylaminopropyl) -3-methylimidazolium bis (trifluoromethanesulfonyl) imide] ("Compound C6")-
Compound 2; 19.37 g (40 mmol), dihexylamine 22.24 g (120 mmol), and acetonitrile (CH 3 CN) (200 mL) were added to a three-neck round bottom flask (500 mL), and the atmosphere in the flask was replaced with argon. Thereafter, the reaction solution was heated and refluxed in an oil bath set at 85 ° C. for 3 hours to carry out the reaction. The reaction solution was concentrated under reduced pressure using a rotary evaporator until a solid precipitated. Thereafter, the solid was removed from the reaction solution by filtration, and the filtrate was again concentrated under reduced pressure using a rotary evaporator. Thereafter, a liquid separation operation was performed with chloroform (CHCl 3 ) / 5 wt% aqueous ammonia (NH 3 aq.), The upper 5 wt% aqueous ammonia phase was removed, and the lower chloroform phase was left. Subsequently, a liquid separation operation was performed with chloroform (CHCl 3 ) / water (H 2 O) to wash the lower chloroform phase. The chloroform solution was subjected to dehydration using anhydrous magnesium sulfate (MgSO 4 ), Celite filtration, vacuum evaporation using a rotary evaporator and a vacuum dryer. Thus, compound C6 (C 21 H 38 F 6 N 4 O 4 S 2 ) was obtained with a yield of 91% (21.4 g, 36.3 mmol).
The results of 1 H-NMR of the obtained compound were as follows.
1 H-NMR (400 MHz, CDCl 3 ) δ 0.89 (t, J = 6.8 Hz, 6H), 1.26 to 1.39 (m, 16H), 1.99 (quin, J = 6.8 Hz) , 2H), 2.37 (t, J = 7.6 Hz, 4H), 2.43 (t, J = 6.6 Hz, 2H), 3.95 (s, 3H), 4.24 (t, J = 7.2 Hz, 2H), 7.30 (quin, J = 1.6 Hz, 2H), 8.76 (s, 1H)
Compound C6 was used as the compound of Example 2, ionic liquid, and extractant.
−［１−３−（ジオクチルアミノプロピル）−３−メチルイミダゾリウムビス（トリフルオロメタンスルホニル）イミド］（「化合物Ｃ８」）の合成−
三口丸底フラスコ（３００ｍＬ）に、化合物２；１４．５ｇ（３０ｍｍｏｌ）、ジオクチルアミン２１．７ｇ（９０ｍｍｏｌ）、アセトニトリル（ＣＨ3ＣＮ）（１５０ｍＬ）を加え、フラスコ内をアルゴン置換した。その後、反応溶液を８５℃に設定したオイルバスで３時間、加熱環流させ、反応を行った。反応溶液を、固体が析出するまで、ロータリーエバポレーターを用いて減圧濃縮した。その後、濾過により、反応溶液から固体を除去し、濾液を再びロータリーエバポレーターを用いて減圧濃縮した。その後、クロロホルム（ＣＨＣｌ3）／５ｗｔ％アンモニア水（ＮＨ3ａｑ．）で、分液操作を行い、上相の５ｗｔ％アンモニア水相を除去し、下相のクロロホルム相を残した。次いで、クロロホルム（ＣＨＣｌ3）／水（Ｈ2Ｏ）で、分液操作を行い、下相のクロロホルム相を洗浄した。クロロホルム溶液について、無水硫酸マグネシウム（ＭｇＳＯ4）を用いた脱水操作、セライト濾過、ロータリーエバポレーター及び真空乾燥機を用いた減圧濃縮を行った。こうして、化合物Ｃ８（Ｃ25Ｈ46Ｆ6Ｎ4Ｏ4Ｓ2）を収率８９％で得た（１７．３ｇ、２６．８ｍｍｏｌ）。
得られた化合物の1Ｈ−ＮＭＲの結果は下記の通りであった。
1Ｈ−ＮＭＲ（４００ＭＨｚ，ＣＤＣｌ3） δ ０．８８（ｔ，Ｊ＝６．８Ｈｚ，６Ｈ），１．２３−１．３８（ｍ，２４Ｈ），１．９９（ｑｕｉｎ，Ｊ＝６．７Ｈｚ，２Ｈ），２．３６（ｔ，Ｊ＝７．４Ｈｚ，４Ｈ），２．４２（ｔ，Ｊ＝６．４Ｈｚ，２Ｈ），３．９６（ｓ，３Ｈ），４．２５（ｔ，Ｊ＝７．０Ｈｚ，２Ｈ），７．２８（ｄ，Ｊ＝１．２Ｈｚ，２Ｈ），８．７６（ｓ，１Ｈ）
化合物Ｃ８を、実施例３の化合物、イオン液体、抽出剤として用いた。
-Synthesis of [1-3- (dioctylaminopropyl) -3-methylimidazolium bis (trifluoromethanesulfonyl) imide] ("Compound C8")-
Compound 2; 14.5 g (30 mmol), dioctylamine 21.7 g (90 mmol), and acetonitrile (CH 3 CN) (150 mL) were added to a three-necked round bottom flask (300 mL), and the atmosphere in the flask was replaced with argon. Thereafter, the reaction solution was heated and refluxed in an oil bath set at 85 ° C. for 3 hours to carry out the reaction. The reaction solution was concentrated under reduced pressure using a rotary evaporator until a solid precipitated. Thereafter, the solid was removed from the reaction solution by filtration, and the filtrate was again concentrated under reduced pressure using a rotary evaporator. Thereafter, a liquid separation operation was performed with chloroform (CHCl 3 ) / 5 wt% aqueous ammonia (NH 3 aq.), The upper 5 wt% aqueous ammonia phase was removed, and the lower chloroform phase was left. Subsequently, a liquid separation operation was performed with chloroform (CHCl 3 ) / water (H 2 O) to wash the lower chloroform phase. The chloroform solution was subjected to dehydration using anhydrous magnesium sulfate (MgSO 4 ), Celite filtration, vacuum evaporation using a rotary evaporator and a vacuum dryer. Thus, compound C8 the (C 25 H 46 F 6 N 4 O 4 S 2) was obtained in 89% yield (17.3 g, 26.8 mmol).
The results of 1 H-NMR of the obtained compound were as follows.
1 H-NMR (400 MHz, CDCl 3 ) δ 0.88 (t, J = 6.8 Hz, 6H), 1.23-1.38 (m, 24H), 1.99 (quin, J = 6.7 Hz) , 2H), 2.36 (t, J = 7.4 Hz, 4H), 2.42 (t, J = 6.4 Hz, 2H), 3.96 (s, 3H), 4.25 (t, J = 7.0 Hz, 2H), 7.28 (d, J = 1.2 Hz, 2H), 8.76 (s, 1H)
Compound C8 was used as the compound of Example 3, ionic liquid, and extractant.
−［１，３−（ジイソブチルアミノプロピル）−３−メチルイミダゾリウムビス（トリフルオロメタンスルホニル）イミド］（「化合物ｉｓｏＣ４」）の合成−
三口丸底フラスコ（１００ｍＬ）に、化合物２；４．８４ｇ（１０ｍｍｏｌ）、ジイソブチルアミン３．８８ｇ（３０ｍｍｏｌ）、アセトニトリル（ＣＨ3ＣＮ）（５０ｍＬ）を加え、フラスコ内をアルゴン置換した。その後、反応溶液を８５℃に設定したオイルバスで１８時間、加熱環流させ、反応を行った。反応溶液を、固体が析出するまで、ロータリーエバポレーターを用いて減圧濃縮した。その後、クロロホルム（ＣＨＣｌ3）／５ｗｔ％アンモニア水溶液（ＮＨ3ａｑ．）で、分液操作を２回行い、上相の５ｗｔ％アンモニア水相を除去し、下相のクロロホルム相を取り出した。次いで、クロロホルム（ＣＨＣｌ3）／水（Ｈ2Ｏ）で、分液操作を行い、下相のクロロホルム相を洗浄した。クロロホルム溶液について、無水硫酸マグネシウム（ＭｇＳＯ4）を用いた脱水操作、セライト濾過、ロータリーエバポレーター及び真空乾燥機を用いた減圧濃縮を行った。得られた液体／ヘキサンで、更に分液操作を行い、イオン液体相を洗浄した。イオン液体について、ロータリーエバポレーター及び真空乾燥機を用いた減圧濃縮を行った。こうして、化合物（Ｃ17Ｈ30Ｆ6Ｎ4Ｏ4Ｓ2）を収率８６％で得た（４．６０ｇ、８．６４ｍｍｏｌ）。
得られた化合物の1Ｈ−ＮＭＲの結果は下記の通りであった。
1Ｈ−ＮＭＲ（４００ＭＨｚ，ＣＤＣｌ3） δ ０．８０（ｄ，Ｊ＝６．４Ｈｚ，１２Ｈ），１．６２−１．７２（ｍ，２Ｈ），１．９８−２．０７（ｍ，２Ｈ），２．１１（ｄ，Ｊ＝７．２Ｈｚ，４Ｈ），２．４４（ｔ，Ｊ＝６．６Ｈｚ，２Ｈ），３．９７（ｓ，３Ｈ），４．２６（ｔ，Ｊ＝７．６Ｈｚ，２Ｈ），７．２４（ｔ，Ｊ＝１．６Ｈｚ，１Ｈ），７．２７（ｔ，Ｊ＝１．８Ｈｚ，１Ｈ），８．８２（ｓ，１Ｈ）
化合物ｉｓｏＣ４を、実施例４の化合物、イオン液体、抽出剤として用いた。
-Synthesis of [1,3- (diisobutylaminopropyl) -3-methylimidazolium bis (trifluoromethanesulfonyl) imide] ("Compound isoC4")-
Compound 2; 4.84 g (10 mmol), diisobutylamine 3.88 g (30 mmol) and acetonitrile (CH 3 CN) (50 mL) were added to a three-neck round bottom flask (100 mL), and the atmosphere in the flask was replaced with argon. Thereafter, the reaction solution was heated to reflux in an oil bath set at 85 ° C. for 18 hours to carry out the reaction. The reaction solution was concentrated under reduced pressure using a rotary evaporator until a solid precipitated. Thereafter, the liquid separation operation was performed twice with chloroform (CHCl 3 ) / 5 wt% aqueous ammonia (NH 3 aq.), The upper 5 wt% aqueous ammonia phase was removed, and the lower chloroform phase was taken out. Subsequently, a liquid separation operation was performed with chloroform (CHCl 3 ) / water (H 2 O) to wash the lower chloroform phase. The chloroform solution was subjected to dehydration using anhydrous magnesium sulfate (MgSO 4 ), Celite filtration, vacuum evaporation using a rotary evaporator and a vacuum dryer. Separation operation was further performed with the obtained liquid / hexane to wash the ionic liquid phase. The ionic liquid was concentrated under reduced pressure using a rotary evaporator and a vacuum dryer. Thus, the compound (C 17 H 30 F 6 N 4 O 4 S 2 ) was obtained with a yield of 86% (4.60 g, 8.64 mmol).
The results of 1 H-NMR of the obtained compound were as follows.
1 H-NMR (400 MHz, CDCl 3 ) δ 0.80 (d, J = 6.4 Hz, 12H), 1.62-1.72 (m, 2H), 1.98-2.07 (m, 2H) ), 2.11 (d, J = 7.2 Hz, 4H), 2.44 (t, J = 6.6 Hz, 2H), 3.97 (s, 3H), 4.26 (t, J = 7) .6 Hz, 2H), 7.24 (t, J = 1.6 Hz, 1H), 7.27 (t, J = 1.8 Hz, 1H), 8.82 (s, 1H)
Compound isoC4 was used as the compound of Example 4, ionic liquid, and extractant.
−［１，３−（ジシクロヘキシルアミノプロピル）−３−メチルイミダゾリウムビス（トリフルオロメタンスルホニル）イミド］（「化合物Ｃｙ」）の合成−
三口丸底フラスコ（１００ｍＬ）に、化合物２；４．８４ｇ（１０ｍｍｏｌ）、ジシクロヘキシルアミン５．４４ｇ（３０ｍｍｏｌ）、アセトニトリル（ＣＨ3ＣＮ）（５０ｍＬ）を加え、フラスコ内をアルゴン置換した。その後、反応溶液を８５℃に設定したオイルバスで６１時間、加熱環流させ、反応を行った。反応溶液を、固体が析出するまで、ロータリーエバポレーターを用いて減圧濃縮した。その後、クロロホルム（ＣＨＣｌ3）／５ｗｔ％アンモニア水溶液（ＮＨ3ａｑ．）で、分液操作を３回行い、上相の５ｗｔ％アンモニア水相を除去し、下相のクロロホルム相を取り出した。次いで、クロロホルム（ＣＨＣｌ3）／水（Ｈ2Ｏ）で、分液操作を行い、下相のクロロホルム相を洗浄した。クロロホルム溶液について、無水硫酸マグネシウム（ＭｇＳＯ4）を用いた脱水操作、セライト濾過、ロータリーエバポレーター及び真空乾燥機を用いた減圧濃縮を行った。得られた液体／ヘキサンで、更に分液操作を行い、イオン液体相を洗浄した。イオン液体について、ロータリーエバポレーター及び真空乾燥機を用いた減圧濃縮を行った。こうして、化合物（Ｃ21Ｈ34Ｆ6Ｎ4Ｏ4Ｓ2）を収率５９％で得た（３．４９ｇ、５．９７ｍｍｏｌ）。
得られた化合物の1Ｈ−ＮＭＲの結果は下記の通りであった。
1Ｈ−ＮＭＲ（４００ＭＨｚ，ＣＤＣｌ3） δ １．１４−１．３０（ｍ，８Ｈ），１．５８−１．７６（ｍ，１２Ｈ），１．９１−１．９８（ｍ，２Ｈ），２．４４−２．５０（ｍ，２Ｈ），２．６３（ｔ，Ｊ＝６．４Ｈｚ，２Ｈ），３．９４（ｓ，３Ｈ），４．２１（ｔ，Ｊ＝７．６Ｈｚ，２Ｈ），７．２７（ｔ，Ｊ＝１．８Ｈｚ，１Ｈ），７．３１（ｔ，Ｊ＝１．８Ｈｚ，１Ｈ），８．７４（ｔ，Ｊ＝１．７Ｈｚ，１Ｈ）
化合物Ｃｙを、実施例５の化合物、イオン液体、抽出剤として用いた。
-Synthesis of [1,3- (dicyclohexylaminopropyl) -3-methylimidazolium bis (trifluoromethanesulfonyl) imide] ("Compound Cy")-
Compound 2; 4.84 g (10 mmol), dicyclohexylamine 5.44 g (30 mmol), and acetonitrile (CH 3 CN) (50 mL) were added to a three-necked round bottom flask (100 mL), and the atmosphere in the flask was replaced with argon. Thereafter, the reaction solution was heated and refluxed in an oil bath set at 85 ° C. for 61 hours to carry out the reaction. The reaction solution was concentrated under reduced pressure using a rotary evaporator until a solid precipitated. Thereafter, the liquid separation operation was performed three times with chloroform (CHCl 3 ) / 5 wt% aqueous ammonia (NH 3 aq.), The upper 5 wt% aqueous ammonia phase was removed, and the lower chloroform phase was taken out. Subsequently, a liquid separation operation was performed with chloroform (CHCl 3 ) / water (H 2 O) to wash the lower chloroform phase. The chloroform solution was subjected to dehydration using anhydrous magnesium sulfate (MgSO 4 ), Celite filtration, vacuum evaporation using a rotary evaporator and a vacuum dryer. Separation operation was further performed with the obtained liquid / hexane to wash the ionic liquid phase. The ionic liquid was concentrated under reduced pressure using a rotary evaporator and a vacuum dryer. Thus, the compound (C 21 H 34 F 6 N 4 O 4 S 2 ) was obtained with a yield of 59% (3.49 g, 5.97 mmol).
The results of 1 H-NMR of the obtained compound were as follows.
1 H-NMR (400 MHz, CDCl 3 ) δ 1.14-1.30 (m, 8H), 1.58-1.76 (m, 12H), 1.91-1.98 (m, 2H), 2.44-2.50 (m, 2H), 2.63 (t, J = 6.4 Hz, 2H), 3.94 (s, 3H), 4.21 (t, J = 7.6 Hz, 2H) ), 7.27 (t, J = 1.8 Hz, 1H), 7.31 (t, J = 1.8 Hz, 1H), 8.74 (t, J = 1.7 Hz, 1H)
Compound Cy was used as the compound of Example 5, ionic liquid, and extractant.
−［１，３−（ジ（２−エチルヘキシル）アミノプロピル）−３−メチルイミダゾリウムビス（トリフルオロメタンスルホニル）イミド］（「化合物Ｃ２−６」）の合成−
三口丸底フラスコ（１００ｍＬ）に、化合物２；４．８４ｇ（１０ｍｍｏｌ）、ジ（２−エチルヘキシル）アミン７．２４ｇ（３０ｍｍｏｌ）、アセトニトリル（ＣＨ3ＣＮ）（５０ｍＬ）を加え、フラスコ内をアルゴン置換した。その後、反応溶液を８５℃に設定したオイルバスで３０時間、加熱環流させ、反応を行った。反応溶液を、固体が析出するまで、ロータリーエバポレーターを用いて減圧濃縮した。その後、クロロホルム（ＣＨＣｌ3）／飽和炭酸水素ナトリウム水溶液（ｓａｔ． ＮａＨＣＯ3 ａｑ．）で、分液操作を６回行い、上相の飽和炭酸水素ナトリウム水溶液相を除去し、下相のクロロホルム相を取り出した。次いで、クロロホルム（ＣＨＣｌ3）／水（Ｈ2Ｏ）で、分液操作を行い、下相のクロロホルム相を洗浄した。クロロホルム溶液について、無水硫酸マグネシウム（ＭｇＳＯ4）を用いた脱水操作、セライト濾過、ロータリーエバポレーター及び真空乾燥機を用いた減圧濃縮を行った。得られた液体／ヘキサンで、更に分液操作を行い、イオン液体相を洗浄した。イオン液体について、ロータリーエバポレーター及び真空乾燥機を用いた減圧濃縮を行った。こうして、化合物Ｃ２−６（Ｃ25Ｈ46Ｆ6Ｎ4Ｏ4Ｓ2）を収率８０％で得た（５．１６ｇ、８．０ｍｍｏｌ）。
得られた化合物の1Ｈ−ＮＭＲの結果は下記の通りであった。
1Ｈ−ＮＭＲ（４００ＭＨｚ，ＣＤＣｌ3） δ ０．７７−０．９７（ｍ，１２Ｈ），１．１５−１．５０（ｍ，１８Ｈ），２．００（ｑｕｉｎ，Ｊ＝７．３Ｈｚ，２Ｈ），２．１６（ｂｒ，４Ｈ），２．４２（ｂｒ，２Ｈ），３．９５（ｓ，３Ｈ），４．２４（ｔ，Ｊ＝７．３Ｈｚ，２Ｈ），７．２４（ｔ，Ｊ＝１．７Ｈｚ，１Ｈ），７．３３（ｔ，Ｊ＝１．７Ｈｚ，１Ｈ），８．７６（ｔ，Ｊ＝１．７Ｈｚ，１Ｈ）
化合物Ｃ２−６を、実施例６の化合物、イオン液体、抽出剤として用いた。
-Synthesis of [1,3- (di (2-ethylhexyl) aminopropyl) -3-methylimidazolium bis (trifluoromethanesulfonyl) imide] ("Compound C2-6")-
Compound 2; 4.84 g (10 mmol), di (2-ethylhexyl) amine 7.24 g (30 mmol) and acetonitrile (CH 3 CN) (50 mL) were added to a three-necked round bottom flask (100 mL), and the atmosphere in the flask was replaced with argon. did. Thereafter, the reaction solution was heated and refluxed in an oil bath set at 85 ° C. for 30 hours to carry out the reaction. The reaction solution was concentrated under reduced pressure using a rotary evaporator until a solid precipitated. Thereafter, liquid separation operation was performed 6 times with chloroform (CHCl 3 ) / saturated sodium hydrogen carbonate aqueous solution (sat. NaHCO 3 aq.), The upper saturated sodium hydrogen carbonate aqueous solution phase was removed, and the lower chloroform phase was I took it out. Subsequently, a liquid separation operation was performed with chloroform (CHCl 3 ) / water (H 2 O) to wash the lower chloroform phase. The chloroform solution was subjected to dehydration using anhydrous magnesium sulfate (MgSO 4 ), Celite filtration, vacuum evaporation using a rotary evaporator and a vacuum dryer. Separation operation was further performed with the obtained liquid / hexane to wash the ionic liquid phase. The ionic liquid was concentrated under reduced pressure using a rotary evaporator and a vacuum dryer. Thus, compound C2-6 a (C 25 H 46 F 6 N 4 O 4 S 2) was obtained in 80% yield (5.16 g, 8.0 mmol).
The results of 1 H-NMR of the obtained compound were as follows.
1 H-NMR (400 MHz, CDCl 3 ) δ 0.77-0.97 (m, 12H), 1.15-1.50 (m, 18H), 2.00 (quin, J = 7.3 Hz, 2H ), 2.16 (br, 4H), 2.42 (br, 2H), 3.95 (s, 3H), 4.24 (t, J = 7.3 Hz, 2H), 7.24 (t, J = 1.7 Hz, 1H), 7.33 (t, J = 1.7 Hz, 1H), 8.76 (t, J = 1.7 Hz, 1H)
Compound C2-6 was used as the compound, ionic liquid, and extractant of Example 6.
（試験Ｂ）白金族元素の抽出
（試験Ｂ−１）Ｐｄ、Ｐｔ、Ｒｈの抽出（白金族元素濃度１００質量ｐｐｍの場合）
５．０ｍＬバイアルチューブに、前述の（試験Ａ）で調製したイオン液体それぞれ０．４０ｇに、Ｐｄ（ＩＶ）、Ｐｔ（ＩＩ）、Ｒｈ（ＩＩＩ）をそれぞれ１００質量ｐｐｍずつ溶解させた、０．３〜４．０Ｍの塩酸（ＨＣｌ）溶液２．０ｍＬを加えた。
この二相系溶液を、１５００ｒｐｍで１５分間振とうさせた後、二相系を安定に形成させるため、６０００ｒｐｍ、５分間の遠心分離を行った。
チューブから水相１．０ｍＬを取り出し、２５ｍＬメスフラスコを用いて、１．０Ｍ塩酸溶液で希釈した。
希釈溶液について誘導結合プラズマ発光分光分析装置（ＩＣＰ−ＡＥＳ）を用いて分析することによって、抽出前後における水相中の各白金属元素の金属イオン濃度を測定し、（試験Ａ）で調製したイオン液体による白金属元素の抽出率Ｅ（％）を算出した。
実施例（実施例１〜６）の結果の詳細を、表１及び図２〜図７に示す。
(Test B) Extraction of platinum group element (Test B-1) Extraction of Pd, Pt, Rh (in the case of platinum group element concentration of 100 mass ppm)
100 mass ppm each of Pd (IV), Pt (II), and Rh (III) was dissolved in 0.40 g of the ionic liquid prepared in the above (Test A) in a 5.0 mL vial tube, respectively. 2.0 mL of 3-4.0 M hydrochloric acid (HCl) solution was added.
The two-phase solution was shaken at 1500 rpm for 15 minutes, and then centrifuged at 6000 rpm for 5 minutes in order to stably form the two-phase system.
1.0 mL of the aqueous phase was removed from the tube and diluted with 1.0 M hydrochloric acid solution using a 25 mL volumetric flask.
By analyzing the diluted solution using an inductively coupled plasma emission spectrometer (ICP-AES), the metal ion concentration of each white metal element in the aqueous phase before and after extraction was measured, and the ions prepared in (Test A) The extraction ratio E (%) of the white metal element with the liquid was calculated.
Details of the results of the examples (Examples 1 to 6) are shown in Table 1 and FIGS.
（試験Ｂ−２）Ｐｄ、Ｐｔ、Ｒｈの抽出（白金族元素濃度５０質量ｐｐｍの場合）
５．０ｍＬバイアルチューブに、前述の（試験Ａ）で調製したイオン液体のうちの化合物Ｃ４からなるイオン液体及び化合物Ｃ６からなるイオン液体それぞれ０．４０ｇに、Ｐｄ（ＩＶ）、Ｐｔ（ＩＩ）、Ｒｈ（ＩＩＩ）をそれぞれ５０質量ｐｐｍずつ溶解させた、１．０〜４．０Ｍの塩酸（ＨＣｌ）溶液２．０ｍＬを加えた。
この二相系溶液を、１５００ｒｐｍで１５分間振とうさせた後、二相系を安定に形成させるため、６０００ｒｐｍ、５分間の遠心分離を行った。
チューブから水相０．８ｍＬを取り出し、１０ｍＬメスフラスコを用いて、１．０Ｍ塩酸溶液で希釈した。
希釈溶液について誘導結合プラズマ発光分光分析装置（ＩＣＰ−ＡＥＳ）を用いて分析することによって、抽出前後における水相中の各白金属元素の金属イオン濃度を測定し、（試験Ａ）で調製したイオン液体による白金属元素の抽出率Ｅ（％）を算出した。
実施例（実施例７、８）の結果の詳細を、表２及び図８、図９に示す。
(Test B-2) Extraction of Pd, Pt, Rh (when platinum group element concentration is 50 mass ppm)
In a 5.0 mL vial tube, 0.40 g each of the ionic liquid composed of Compound C4 and the ionic liquid composed of Compound C6 among the ionic liquids prepared in the above (Test A), Pd (IV), Pt (II), 2.0 mL of a 1.0 to 4.0 M hydrochloric acid (HCl) solution in which 50 ppm by mass of Rh (III) was dissolved was added.
The two-phase solution was shaken at 1500 rpm for 15 minutes, and then centrifuged at 6000 rpm for 5 minutes in order to stably form the two-phase system.
0.8 mL of the aqueous phase was taken out from the tube, and diluted with 1.0 M hydrochloric acid solution using a 10 mL volumetric flask.
By analyzing the diluted solution using an inductively coupled plasma emission spectrometer (ICP-AES), the metal ion concentration of each white metal element in the aqueous phase before and after extraction was measured, and the ions prepared in (Test A) The extraction ratio E (%) of the white metal element with the liquid was calculated.
Details of the results of Examples (Examples 7 and 8) are shown in Table 2 and FIGS. 8 and 9.
（試験Ｂ−３）Ｐｄ、Ｐｔ、Ｒｈの抽出（白金族元素濃度１０質量ｐｐｍの場合）
５．０ｍＬバイアルチューブに、前述の（試験Ａ）で調製したイオン液体のうちの化合物Ｃ４からなるイオン液体及び化合物Ｃ６からなるイオン液体それぞれ０．４０ｇに、Ｐｄ（ＩＶ）、Ｐｔ（ＩＩ）、Ｒｈ（ＩＩＩ）をそれぞれ１０質量ｐｐｍずつ溶解させた、１．０〜４．０Ｍの塩酸（ＨＣｌ）溶液２．０ｍＬを加えた。
この二相系溶液を、１５００ｒｐｍで１５分間振とうさせた後、二相系を安定に形成させるため、６０００ｒｐｍ、５分間の遠心分離を行った。
チューブから水相１．５ｍＬを取り出し、１０ｍＬメスフラスコを用いて、１．０Ｍ塩酸溶液で希釈した。
希釈溶液について誘導結合プラズマ発光分光分析装置（ＩＣＰ−ＡＥＳ）を用いて分析することによって、抽出前後における水相中の各白金属元素の金属イオン濃度を測定し、（試験Ａ）で調製したイオン液体による白金属元素の抽出率Ｅ（％）を算出した。
実施例（実施例９、１０）の結果の詳細を、表３及び図１０、図１１に示す。
(Test B-3) Extraction of Pd, Pt, Rh (when platinum group element concentration is 10 mass ppm)
In a 5.0 mL vial tube, 0.40 g each of the ionic liquid composed of Compound C4 and the ionic liquid composed of Compound C6 among the ionic liquids prepared in the above (Test A), Pd (IV), Pt (II), 2.0 mL of a 1.0 to 4.0 M hydrochloric acid (HCl) solution in which 10 ppm by mass of Rh (III) was dissolved was added.
The two-phase solution was shaken at 1500 rpm for 15 minutes, and then centrifuged at 6000 rpm for 5 minutes in order to stably form the two-phase system.
1.5 mL of the aqueous phase was taken out from the tube, and diluted with 1.0 M hydrochloric acid solution using a 10 mL volumetric flask.
By analyzing the diluted solution using an inductively coupled plasma emission spectrometer (ICP-AES), the metal ion concentration of each white metal element in the aqueous phase before and after extraction was measured, and the ions prepared in (Test A) The extraction ratio E (%) of the white metal element with the liquid was calculated.
Details of the results of the examples (Examples 9 and 10) are shown in Table 3 and FIGS. 10 and 11.
（試験Ｂ−４）Ｒｕ、Ｉｒの抽出（白金族元素濃度１００質量ｐｐｍの場合）
５．０ｍＬバイアルチューブに、前述の（試験Ａ）で調製したイオン液体のうちの化合物Ｃ４からなるイオン液体、化合物Ｃ６からなるイオン液体、及び化合物Ｃ８からなるイオン液体それぞれ０．４０ｇに、Ｒｕ（ＩＩＩ）、Ｉｒ（ＩＩＩ）をそれぞれ１００質量ｐｐｍずつ溶解させた、１．０〜４．０Ｍの塩酸（ＨＣｌ）溶液２．０ｍＬを加えた。
この二相系溶液を、１５００ｒｐｍで１５分間振とうさせた後、二相系を安定に形成させるため、６０００ｒｐｍ、５分間の遠心分離を行った。
チューブから水相１．０ｍＬを取り出し、２５ｍＬメスフラスコを用いて、１．０Ｍ塩酸溶液で希釈した。
希釈溶液について誘導結合プラズマ発光分光分析装置（ＩＣＰ−ＡＥＳ）を用いて分析することによって、抽出前後における水相中の各白金属元素の金属イオン濃度を測定し、（試験Ａ）で調製したイオン液体による白金属元素の抽出率Ｅ（％）を算出した。
実施例（実施例１１、１２、１３）の結果の詳細を、表４及び図１２〜図１４に示す。
なお、Ｒｈ（ＩＩＩ）についても同様に抽出実験を行ったところ、４．０Ｍ ＨＣｌの条件で、化合物Ｃ４、化合物Ｃ６、化合物Ｃ８からなるイオン液体を用いた場合、抽出率は、それぞれ、３．９％、４３．５％、６７．８％となり、（試験Ｂ−１）において得られた結果と同様の結果が得られた。
(Test B-4) Extraction of Ru and Ir (in the case of platinum group element concentration of 100 mass ppm)
In a 5.0 mL vial tube, 0.40 g each of the ionic liquid composed of the compound C4, the ionic liquid composed of the compound C6, and the ionic liquid composed of the compound C8 among the ionic liquids prepared in the above (Test A) were added to Ru ( III) and Ir (III) were dissolved in an amount of 100 ppm by mass, respectively, and 2.0 mL of a 1.0 to 4.0 M hydrochloric acid (HCl) solution was added.
The two-phase solution was shaken at 1500 rpm for 15 minutes, and then centrifuged at 6000 rpm for 5 minutes in order to stably form the two-phase system.
1.0 mL of the aqueous phase was removed from the tube and diluted with 1.0 M hydrochloric acid solution using a 25 mL volumetric flask.
By analyzing the diluted solution using an inductively coupled plasma emission spectrometer (ICP-AES), the metal ion concentration of each white metal element in the aqueous phase before and after extraction was measured, and the ions prepared in (Test A) The extraction ratio E (%) of the white metal element with the liquid was calculated.
Details of the results of Examples (Examples 11, 12, and 13) are shown in Table 4 and FIGS.
The same extraction experiment was conducted for Rh (III). When an ionic liquid composed of Compound C4, Compound C6, and Compound C8 was used under the condition of 4.0 M HCl, the extraction rate was 3. The results were 9%, 43.5%, and 67.8%, and the same results as those obtained in (Test B-1) were obtained.
比較例の化合物として、１−ブチル−３−メチルイミダゾリウムビス（トリフルオロメタンスルホニル）イミドを準備した。そして、この化合物についても、上記（試験Ｂ−１）と同様に、抽出実験を行った。
比較例（比較例１）の結果の詳細を、表１に示す。
As a compound of a comparative example, 1-butyl-3-methylimidazolium bis (trifluoromethanesulfonyl) imide was prepared. And about this compound, extraction experiment was done similarly to the said (test B-1).
Details of the results of the comparative example (Comparative Example 1) are shown in Table 1.
実施例１では、図２に示す通り、Ｐｄ及びＰｔについては、０．３Ｍにおいて、それぞれ、Ｅ（Ｐｄ）＝９６．０％、Ｅ（Ｐｔ）＝９０．７％となり、いずれも高効率での抽出が可能であった。ＨＣｌ濃度が増加するに従って抽出率は減少した。Ｒｈについては、実施例１のイオン液体は、０．３〜４．０Ｍでは抽出能を示さなかった。 In Example 1, as shown in FIG. 2, for Pd and Pt, at 0.3 M, E (Pd) = 96.0% and E (Pt) = 90.7%, respectively, which are both highly efficient. Could be extracted. The extraction rate decreased as the HCl concentration increased. Regarding Rh, the ionic liquid of Example 1 did not exhibit extraction ability at 0.3 to 4.0 M.
実施例２では、図３に示す通り、Ｐｄについては、０．３Ｍにおいて、Ｅ（Ｐｄ）＝９６．８％となり、ＨＣｌ濃度が増加するに従って抽出率は減少したが、４．０Ｍにおいて、Ｅ（Ｐｄ）＝８８．１％と高い抽出率を維持していた。Ｐｔについては、０．３〜４．０Ｍにおいて、ほぼ１００％の抽出率での抽出が可能であった。Ｒｈについては、ＨＣｌ濃度が上昇するに従って抽出率が上昇し、３．０Ｍにおいて、Ｅ（Ｒｈ）＝５１．０％となった。 In Example 2, as shown in FIG. 3, for Pd, E (Pd) = 96.8% at 0.3M, and the extraction rate decreased as the HCl concentration increased, but at 4.0M, A high extraction rate of (Pd) = 88.1% was maintained. For Pt, extraction at an extraction rate of almost 100% was possible at 0.3 to 4.0 M. As for Rh, the extraction rate increased as the HCl concentration increased, and E (Rh) = 51.0% at 3.0M.
実施例３では、図４に示す通り、Ｐｄ、Ｐｔ、Ｒｈの全てについて、ＨＣｌ濃度が上昇するに従って抽出率が上昇した。Ｐｄ及びＰｔについては、３．０Ｍ、４．０Ｍにおいて、いずれも極めて高い効率での抽出が可能であった。特に、Ｒｈについては、３．０Ｍ、４．０Ｍにおいて、それぞれ、Ｅ（Ｒｈ）＝７３．１％、７１．８％を示した。 In Example 3, as shown in FIG. 4, for all of Pd, Pt, and Rh, the extraction rate increased as the HCl concentration increased. As for Pd and Pt, extraction at extremely high efficiency was possible at 3.0M and 4.0M. In particular, for Rh, E (Rh) = 73.1% and 71.8% were shown at 3.0M and 4.0M, respectively.
実施例４では、図５に示す通り、特に、Ｐｔについては、０．３Ｍにおいて、Ｅ（Ｐｔ）＝８１．３％となり、ＨＣｌ濃度が増加するに従って抽出率は減少した。 In Example 4, as shown in FIG. 5, in particular, for Pt, E (Pt) = 81.3% at 0.3 M, and the extraction rate decreased as the HCl concentration increased.
実施例５では、図６に示す通り、特に、Ｐｔについては、０．３Ｍにおいて、Ｅ（Ｐｔ）＝８６．４％となり、ＨＣｌ濃度が増加するに従って抽出率は減少した。 In Example 5, as shown in FIG. 6, particularly for Pt, E (Pt) = 86.4% at 0.3 M, and the extraction rate decreased as the HCl concentration increased.
実施例６では、図７に示す通り、特に、Ｐｄ及びＰｔについて、０．３〜４．０Ｍにおいて、極めて高い効率での抽出が可能であった。 In Example 6, as shown in FIG. 7, it was possible to extract Pd and Pt with extremely high efficiency at 0.3 to 4.0 M.
図８〜図１１に示すように、実施例７、８の結果と実施例１、２の結果との比較、及び実施例９、１０の結果と実施例１、２の結果との比較により、Ｐｄ、Ｐｔ、Ｒｈの濃度が５０質量ｐｐｍ、１０質量ｐｐｍの場合であっても、１００質量ｐｐｍの場合と同様に、抽出が可能であることが示された。 As shown in FIGS. 8 to 11, by comparing the results of Examples 7 and 8 with the results of Examples 1 and 2, and comparing the results of Examples 9 and 10 with the results of Examples 1 and 2, Even when the concentrations of Pd, Pt, and Rh were 50 ppm by mass and 10 ppm by mass, extraction was possible as in the case of 100 ppm by mass.
図１２〜図１４に示す通り、本実施形態の化合物からなるイオン液体は、Ｒｕ、Ｉｒも抽出可能であることが示された。図１４に示す通り、特に、化合物Ｃ８からなるイオン液体を用いた場合、Ｒｕについては、４．０Ｍにおいて、Ｅ（Ｒｕ）＝８６．３％と高い抽出率が得られた。 As shown in FIGS. 12-14, it was shown that Ru and Ir can also be extracted from the ionic liquid which consists of the compound of this embodiment. As shown in FIG. 14, in particular, when an ionic liquid composed of the compound C8 was used, a high extraction rate of E (Ru) = 86.3% was obtained for Ru at 4.0 M.
本発明によれば、白金族元素を高い抽出率で抽出することができる。 According to the present invention, platinum group elements can be extracted at a high extraction rate.
Claims (6)
で表されることを特徴とする、化合物。 Following formula (1)
A compound represented by the formula:
Ｒ1及びＲ2は、ブチル基、ヘキシル基、オクチル基からなる群から選択される少なくとも１種であり、ここで、Ｒ1とＲ2とは、同じであり、
Ｒ3は、メチル基であり、
Ａ-は、Ｎ-（ＣＦ3ＳＯ2）2であり、
ｎは、３である、
請求項２に記載のイオン液体。 In the above formula (1),
R 1 and R 2 are at least one selected from the group consisting of a butyl group, a hexyl group, and an octyl group, where R 1 and R 2 are the same;
R 3 is a methyl group,
A − is N − (CF 3 SO 2 ) 2 ,
n is 3.
The ionic liquid according to claim 2.
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