TWI501948B - Onium salt composition - Google Patents

Onium salt composition Download PDF

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TWI501948B
TWI501948B TW098124200A TW98124200A TWI501948B TW I501948 B TWI501948 B TW I501948B TW 098124200 A TW098124200 A TW 098124200A TW 98124200 A TW98124200 A TW 98124200A TW I501948 B TWI501948 B TW I501948B
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cation
ethyl
diethyl
methylpyridinium
salt composition
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TW098124200A
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TW201103890A (en
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Masatoshi Usui
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Koei Chemical Co
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Description

鎓鹽組成物Bismuth salt composition

本發明是有關鎓鹽組成物。The present invention relates to an onium salt composition.

具有六氟化磷(PF6 - )陰離子之鎓鹽廣泛地使用在電雙層電容器等電化學元件用電解質、界面活性劑、相轉移觸媒、抗靜電劑、殺菌劑等方面。然而,該鎓鹽因為很容易吸濕,同時,也容易引起水解,故在保存上及處理上,會因無法避免混入的微量水引起水解,而會有產生毒性及對金屬或樹脂有腐蝕性之氟化氫的問題。An onium salt having a phosphorus hexafluoride (PF 6 - ) anion is widely used in an electrolyte for an electrochemical element such as an electric double layer capacitor, a surfactant, a phase transfer catalyst, an antistatic agent, a bactericide, and the like. However, since the cerium salt is easily hygroscopic and is also liable to cause hydrolysis, it may be hydrolyzed due to the inability to avoid the incorporation of trace amounts of water during storage and treatment, and may cause toxicity and corrosiveness to metals or resins. The problem of hydrogen fluoride.

作為有良好保存安定性之PF6- 鎓鹽者,在日本特開2001-48846號公報中,雖然是揭示以特定之溶劑被覆具有PF6 - 之鎓鹽,但以該特定溶劑被覆具有PF6 - 之鎓鹽,在60℃以上時,亦會因微量之水分而引起水解,故也不能說有充分之安定性。As a good storage stability of PF6 - salts are, in Japanese Laid-Open Patent Publication No. 2001-48846, although PF 6 is disclosed having a particular non-solvent to the coating - the onium salts, but with the particular coating solvent PF 6 - When the salt is at 60 ° C or higher, it is also hydrolyzed by a trace amount of water, so it cannot be said that it has sufficient stability.

本發明提供以下<1>至<8>:The present invention provides the following <1> to <8>:

<1>一種鎓鹽組成物,其係含有式(1)所示鎓鹽,與有機鹼之組成物,<1> an onium salt composition containing a phosphonium salt represented by the formula (1) and a composition of an organic base,

式(1):Formula 1):

Q+ ‧A-  (1)Q + ‧A - (1)

(式中,Q+ 表示鎓離子,A- 表示PF6 - );(wherein Q + represents a cesium ion and A - represents PF 6 - );

<2>如<1>之鎓鹽組成物,其復含有溶劑;<2> a salt composition of <1>, which further comprises a solvent;

<3>如<1>或<2>之鎓鹽組成物,其中,鎓離子為四級銨陽離子或四級鏻陽離子;<3> a salt composition of <1> or <2>, wherein the cerium ion is a quaternary ammonium cation or a quaternary phosphonium cation;

<4>如<1>至<3>中任一項之鎓鹽組成物,其中,有機鹼為三級胺或三級膦(phosphine);<4> The bismuth salt composition according to any one of <1> to <3> wherein the organic base is a tertiary amine or a phosphine;

<5>如<4>之鎓鹽組成物,其中,三級胺為選自由脂肪族三級胺、芳香族三級胺、吡啶(pyridin)類及咪唑(imidazol)類所成群組中之至少一種;<5> The salt composition of <4>, wherein the tertiary amine is selected from the group consisting of aliphatic tertiary amines, aromatic tertiary amines, pyridin and imidazol. At least one

<6>如<1>至<5>中任一項之鎓鹽組成物,其中,有機鹼之含量,相對於式(1)所示之鎓鹽,為10至5000ppm;The salt composition of any one of <1> to <5>, wherein the content of the organic base is 10 to 5000 ppm with respect to the onium salt represented by the formula (1);

<7>一種鎓鹽之安定化方法,其特徵為混合式(1)所示之鎓鹽與有機鹼者;<7> A method for stabilization of a cerium salt, which is characterized by mixing a cerium salt and an organic base represented by the formula (1);

<8>一種鎓鹽之保存方法,其特徵為使式(1)所示之鎓鹽在有機鹼之存在下保存者。<8> A method for preserving a cerium salt, which is characterized in that the cerium salt represented by the formula (1) is preserved in the presence of an organic base.

實施發明之最佳形態Best form for implementing the invention

式(1)所示鎓鹽(以下,簡稱鎓鹽(1))之式中,作為Q+ 所示鎓離子者,可列舉如:四級銨陽離子、四級鏻陽離子等。In the formula of the onium salt (hereinafter referred to as the onium salt (1)) represented by the formula (1), examples of the onium ion represented by Q + include a quaternary ammonium cation and a quaternary phosphonium cation.

作為四級銨陽離子者,可列舉如:四烷基銨陽離子、吡咯烷鎓(pyrrolidinium)陽離子、嗎啉鎓(morpholinium)陽離子、咪唑啉鎓(imidazolium)陽離子、四氫嘧啶鎓(Tetrahydropyrimidinium)陽離子、哌嗪鎓(piperazinium)陽離子、哌啶鎓(piperidinium)陽離子、吡啶鎓(Pyridinium)陽離子等。作為四級鏻陽離子者,可列舉如:四烷基鏻陽離子。Examples of the quaternary ammonium cation include a tetraalkylammonium cation, a pyrrolidinium cation, a morpholinium cation, an imidazolium cation, a tetrahydropyrimidinium cation, Piperazinium cation, piperidinium cation, pyridinium cation, and the like. Examples of the fourth-order phosphonium cation include a tetraalkyl phosphonium cation.

作為四烷基銨陽離子者,可列舉如:四甲基銨陽離子、四乙基銨陽離子、四丙基銨陽離子、四丁基銨陽離子、四戊基銨陽離子、四己基銨陽離子、四庚基銨陽離子、四辛基銨陽離子、四壬基銨陽離子、四癸基銨陽離子、四(十二烷基)銨陽離子、乙基三甲基銨陽離子、二乙基二甲基銨陽離子、三乙基甲基銨陽離子、四乙基銨陽離子、三甲基丙基銨陽離子、三甲基異丙基銨陽離子、乙基二甲基丙基銨陽離子、乙基二甲基異丙基銨陽離子、二乙基甲基丙基銨陽離子、二乙基甲基異丙基銨陽離子、二甲基二丙基銨陽離子、二甲基丙基異丙基銨陽離子、二甲基二異丙基銨陽離子、三乙基丙基銨陽離子、丁基三甲基銨陽離子、異丁基三甲基銨陽離子、三級丁基三甲基銨陽離子、三乙基異丙基銨陽離子、乙基甲基二丙基銨陽離子、乙基甲基二異丙基銨陽離子、丁基乙基二甲基銨陽離子、異丁基乙基二甲基銨陽離子、三級丁基乙基二甲基銨陽離子、二乙基二丙基銨陽離子、二乙基丙基異丙基銨陽離子、二乙基二異丙基銨陽離子、甲基三丙基銨陽離子、甲基二丙基異丙基銨陽離子、甲基丙基二異丙基銨陽離子、丁基三乙基銨陽離子、異丁基三乙基銨陽離子、三級丁基三乙基銨陽離子、二丁基二甲基銨陽離子、二異丁基二甲基銨陽離子、二-三級丁基二甲基銨陽離子、丁基異丁基二甲基銨陽離子、丁基三級丁基二甲基銨陽離子、異丁基三級丁基二甲基銨陽離子、三辛基甲基銨陽離子等。Examples of the tetraalkylammonium cation include tetramethylammonium cation, tetraethylammonium cation, tetrapropylammonium cation, tetrabutylammonium cation, tetraamylammonium cation, tetrahexylammonium cation, and tetraheptyl group. Ammonium cation, tetraoctyl ammonium cation, tetradecylammonium cation, tetradecylammonium cation, tetrakis(dodecyl)ammonium cation, ethyltrimethylammonium cation, diethyldimethylammonium cation, triethyl Methyl ammonium cation, tetraethyl ammonium cation, trimethyl propyl ammonium cation, trimethyl isopropyl ammonium cation, ethyl dimethyl propyl ammonium cation, ethyl dimethyl isopropyl ammonium cation, Diethylmethylpropylammonium cation, diethylmethylisopropylammonium cation, dimethyldipropylammonium cation, dimethylpropylisopropylammonium cation, dimethyldiisopropylammonium cation , triethyl propyl ammonium cation, butyl trimethyl ammonium cation, isobutyl trimethyl ammonium cation, tertiary butyl trimethyl ammonium cation, triethyl isopropyl ammonium cation, ethyl methyl two Propyl ammonium cation, ethyl methyl diisopropyl ammonium cation, butyl Ethyl dimethyl ammonium cation, isobutyl ethyl dimethyl ammonium cation, tertiary butyl ethyl dimethyl ammonium cation, diethyl dipropyl ammonium cation, diethyl propyl isopropyl ammonium cation , diethyldiisopropylammonium cation, methyltripropylammonium cation, methyldipropylisopropylammonium cation, methylpropyldiisopropylammonium cation, butyltriethylammonium cation, different Butyl triethylammonium cation, tertiary butyl triethylammonium cation, dibutyldimethylammonium cation, diisobutyldimethylammonium cation, di-tertiary butyldimethylammonium cation, butyl Isobutyl dimethyl ammonium cation, butyl tertiary butyl dimethyl ammonium cation, isobutyl tertiary butyl dimethyl ammonium cation, trioctylmethyl ammonium cation, and the like.

作為吡咯烷鎓陽離子者,可列舉如:1,1-二甲基吡咯烷鎓陽離子、1-乙基-1-甲基吡咯烷鎓陽離子、1,1-二乙基吡咯烷鎓陽離子、1,1,2-三甲基吡咯烷鎓陽離子、1,1,3-三甲基吡咯烷鎓陽離子、1-乙基-1,2-二甲基吡咯烷鎓陽離子、1-乙基-1,3-二甲基吡咯烷鎓陽離子、2-乙基-1,1-二甲基吡咯烷鎓陽離子、3-乙基-1,1-二甲基吡咯烷鎓陽離子、1,1-二乙基-2-甲基吡咯烷鎓陽離子、1,1-二乙基-3-甲基吡咯烷鎓陽離子、1,2-二乙基-1-甲基吡咯烷鎓陽離子、1,3-二乙基-1-甲基吡咯烷鎓陽離子、1,1,2-三乙基吡咯烷鎓陽離子、1,1,3-三乙基吡咯烷鎓陽離子、1,1,2,2-四甲基吡咯烷鎓陽離子、1,1,2,3-四甲基吡咯烷鎓陽離子、1,1,2,4-四甲基吡咯烷鎓陽離子、1,1,2,5-四甲基吡咯烷鎓陽離子、1,1,3,4-四甲基吡咯烷鎓陽離子、1,1,3,3-四甲基吡咯烷鎓陽離子、1,1-二甲基吡咯烷鎓陽離子、1-乙基-1-甲基吡咯烷鎓陽離子、1,1-二乙基吡咯烷鎓陽離子、1,1,2-三甲基吡咯烷鎓陽離子、1,1,3-三甲基吡咯烷鎓陽離子、1-乙基-1,2-二甲基吡咯烷鎓陽離子、1-乙基-1,3-二甲基吡咯烷鎓陽離子、2-乙基-1,1-二甲基吡咯烷鎓陽離子、3-乙基-1,1-二甲基吡咯烷鎓陽離子、1,1-二乙基-2-甲基吡咯烷鎓陽離子、1,1-二乙基-3-甲基吡咯烷鎓陽離子、1,2-二乙基-1-甲基吡咯烷鎓陽離子、1,3-二乙基-1-甲基吡咯烷鎓陽離子、1,1,2-三乙基吡咯烷鎓陽離子、1,1,3-三乙基吡咯烷鎓陽離子、1,1,2,2-四甲基吡咯烷鎓陽離子、1,1,2,3-四甲基吡咯烷鎓陽離子、1,1,2,4-四甲基吡咯烷鎓陽離子、1,1,2,5-四甲基吡咯烷鎓陽離子、1,1,3,4-四甲基吡咯烷鎓陽離子、1,1,3,3-四甲基吡咯烷鎓陽離子、2-乙基-1,1,2-三甲基吡咯烷鎓陽離子、2-乙基-1,1,3-三甲基吡咯烷鎓陽離子、3-乙基-1,1,2-三甲基吡咯烷鎓陽離子、3-乙基-1,1,3-三甲基吡咯烷鎓陽離子、2-乙基-1,1,4-三甲基吡咯烷鎓陽離子、4-乙基-1,1,2-三甲基吡咯烷鎓陽離子、2-乙基-1,1,5-三甲基吡咯烷鎓陽離子、5-乙基-1,1,2-三甲基吡咯烷鎓陽離子、3-乙基-1,1,4-三甲基吡咯烷鎓陽離子、4-乙基-1,1,3-三甲基吡咯烷鎓陽離子、1-乙基-1,2,2-三甲基吡咯烷鎓陽離子、1-乙基-1,2,3-三甲基吡咯烷鎓陽離子、1-乙基-1,3,3-三甲基吡咯烷鎓陽離子、1-乙基-1,2,4-三甲基吡咯烷鎓陽離子、1-乙基-1,2,5-三甲基吡咯烷鎓陽離子、1-乙基-1,3,4-三甲基吡咯烷鎓陽離子、2,2-二乙基-1,1-二甲基吡咯烷鎓陽離子、2,3-二乙基-1,1-二甲基吡咯烷鎓陽離子、3,3-二乙基-1,1-二甲基吡咯烷鎓陽離子、2,4-二乙基-1,1-二甲基吡咯烷鎓陽離子、2,5-二乙基-1,1-二甲基吡咯烷鎓陽離子、3,4-二乙基-1,1-二甲基吡咯烷鎓陽離子、1,2-二乙基-1,2-二甲基吡咯烷鎓陽離子、1,2-二乙基-1,3-二甲基吡咯烷鎓陽離子、1,3-二乙基-1,2-二甲基吡咯烷鎓陽離子、1,3-二乙基-1,3-二甲基吡咯烷鎓陽離子、1,2-二乙基-1,4-二甲基吡咯烷鎓陽離子、1,4-二乙基-1,2-二甲基吡咯烷鎓陽離子、1,2-二乙基-1,5-二甲基吡咯烷鎓陽離子、1,5-二乙基-1,2-二甲基吡咯烷鎓陽離子、1,3-二乙基-1,4-二甲基吡咯烷鎓陽離子、1,1,2,2,3-五甲基吡咯烷鎓陽離子、1,1,2,2,4-五甲基吡咯烷鎓陽離子、1,1,2,2,5-五甲基吡咯烷鎓陽離子、1,1,2,3,4-五甲基吡咯烷鎓陽離子、1,1,2,3,5-五甲基吡咯烷鎓陽離子、1,1,3,3,4-五甲基吡咯烷鎓陽離子、1,1,3,3,5-五甲基吡咯烷鎓陽離子、1-乙基-1,2,2,3-四甲基吡咯烷鎓陽離子、1-乙基-1,2,2,4-四甲基吡咯烷鎓陽離子、1-乙基-1,2,2,5-四甲基吡咯烷鎓陽離子、1-乙基-1,2,3,4-四甲基吡咯烷鎓陽離子、1-乙基-1,2,3,5-四甲基吡咯烷鎓陽離子、1-乙基-1,2,4,5-四甲基吡咯烷鎓陽離子、1-乙基-1,3,3,4-四甲基吡咯烷鎓陽離子、1-乙基-1,3,3,5-四甲基吡咯烷鎓陽離子、1-乙基-1,3,4,5-四甲基吡咯烷鎓陽離子、2-乙基-1,1,2,3-四甲基吡咯烷鎓陽離子、2-乙基-1,1,2,4-四甲基吡咯烷鎓陽離子、2-乙基-1,1,2,5-四甲基吡咯烷鎓陽離子、2-乙基-1,1,3,3-四甲基吡咯烷鎓陽離子、2-乙基-1,1,3,4-四甲基吡咯烷鎓陽離子、2-乙基-1,1,3,5-四甲基吡咯烷鎓陽離子、2-乙基-1,1,4,4-四甲基吡咯烷鎓陽離子、2-乙基-1,1,4,5-四甲基吡咯烷鎓陽離子、2-乙基-1,1,5,5-四甲基吡咯烷鎓陽離子、3-乙基-1,1,2,2-四甲基吡咯烷鎓陽離子、3-乙基-1,1,2,3-四甲基吡咯烷鎓陽離子、3-乙基-1,1,2,4-四甲基吡咯烷鎓陽離子、3-乙基-1,1,2,5-四甲基吡咯烷鎓陽離子、3-乙基-1,1,3,4-四甲基吡咯烷鎓陽離子、3-乙基-1,1,4,4-四甲基吡咯烷鎓陽離子、3-乙基-1,1,4,5-四甲基吡咯烷鎓陽離子、1,1,2,2,3,3-六甲基吡咯烷鎓陽離子、1,1,2,2,3,4-六甲基吡咯烷鎓陽離子、1,1,2,2,3,5-六甲基吡咯烷鎓陽離子、1,1,2,2,4,4-六甲基吡咯烷鎓陽離子、1,1,2,2,4,5-六甲基吡咯烷鎓陽離子、1,1,2,2,5,5-六甲基吡咯烷鎓陽離子、1,1,2,3,3,4-六甲基吡咯烷鎓陽離子、1,1,2,3,3,5-六甲基吡咯烷鎓陽離子、1,1,2,3,4,4-六甲基吡咯烷鎓陽離子、1,1,2,3,5,5-六甲基吡咯烷鎓陽離子、1,1,2,3,4,5-六甲基吡咯烷鎓陽離子等在吡咯烷環之碳原子上有烷基之1,1-二烷基吡咯烷鎓陽離子。Examples of the pyrrolidinium cation include a 1,1-dimethylpyrrolidinium cation, a 1-ethyl-1-methylpyrrolidinium cation, a 1,1-diethylpyrrolidinium cation, and 1 1,1,3-trimethylpyrrolidinium cation, 1,1,3-trimethylpyrrolidinium cation, 1-ethyl-1,2-dimethylpyrrolidinium cation, 1-ethyl-1 , 3-dimethylpyrrolidinium cation, 2-ethyl-1,1-dimethylpyrrolidinium cation, 3-ethyl-1,1-dimethylpyrrolidinium cation, 1,1-di Ethyl-2-methylpyrrolidinium cation, 1,1-diethyl-3-methylpyrrolidinium cation, 1,2-diethyl-1-methylpyrrolidinium cation, 1,3- Diethyl-1-methylpyrrolidinium cation, 1,1,2-triethylpyrrolidinium cation, 1,1,3-triethylpyrrolidinium cation, 1,1,2,2-tetra Methyl pyrrolidinium cation, 1,1,2,3-tetramethylpyrrolidinium cation, 1,1,2,4-tetramethylpyrrolidinium cation, 1,1,2,5-tetramethyl Pyrrolidinium cation, 1,1,3,4-tetramethylpyrrolidinium cation, 1,1,3,3-tetramethylpyrrolidinium cation, 1,1-dimethylpyrrolidinium cation, 1 -ethyl-1-methylpyrrolidinium Ionic, 1,1-diethylpyrrolidinium cation, 1,1,2-trimethylpyrrolidinium cation, 1,1,3-trimethylpyrrolidinium cation, 1-ethyl-1,2 - dimethylpyrrolidinium cation, 1-ethyl-1,3-dimethylpyrrolidinium cation, 2-ethyl-1,1-dimethylpyrrolidinium cation, 3-ethyl-1, 1-dimethylpyrrolidinium cation, 1,1-diethyl-2-methylpyrrolidinium cation, 1,1-diethyl-3-methylpyrrolidinium cation, 1,2-diethyl 1,1-methylpyrrolidinium cation, 1,3-diethyl-1-methylpyrrolidinium cation, 1,1,2-triethylpyrrolidinium cation, 1,1,3-triethyl Pyrrolidinium cation, 1,1,2,2-tetramethylpyrrolidinium cation, 1,1,2,3-tetramethylpyrrolidinium cation, 1,1,2,4-tetramethylpyrrole Alkane cation, 1,1,2,5-tetramethylpyrrolidinium cation, 1,1,3,4-tetramethylpyrrolidinium cation, 1,1,3,3-tetramethylpyrrolidinium Cation, 2-ethyl-1,1,2-trimethylpyrrolidinium cation, 2-ethyl-1,1,3-trimethylpyrrolidinium cation, 3-ethyl-1,1,2 -trimethylpyrrolidinium cation, 3-ethyl-1,1,3-trimethylpyrrolidinium Ionic, 2-ethyl-1,1,4-trimethylpyrrolidinium cation, 4-ethyl-1,1,2-trimethylpyrrolidinium cation, 2-ethyl-1,1,5 - trimethylpyrrolidinium cation, 5-ethyl-1,1,2-trimethylpyrrolidinium cation, 3-ethyl-1,1,4-trimethylpyrrolidinium cation, 4-B 1,1-trimethylpyrrolidinium cation, 1-ethyl-1,2,2-trimethylpyrrolidinium cation, 1-ethyl-1,2,3-trimethylpyrrole Alkane cation, 1-ethyl-1,3,3-trimethylpyrrolidinium cation, 1-ethyl-1,2,4-trimethylpyrrolidinium cation, 1-ethyl-1,2 , 5-trimethylpyrrolidinium cation, 1-ethyl-1,3,4-trimethylpyrrolidinium cation, 2,2-diethyl-1,1-dimethylpyrrolidinium cation, 2,3-diethyl-1,1-dimethylpyrrolidinium cation, 3,3-diethyl-1,1-dimethylpyrrolidinium cation, 2,4-diethyl-1, a 1-dimethylpyrrolidinium cation, a 2,5-diethyl-1,1-dimethylpyrrolidinium cation, a 3,4-diethyl-1,1-dimethylpyrrolidinium cation, 1,2-diethyl-1,2-dimethylpyrrolidinium cation, 1,2-diethyl-1,3-dimethylpyrrolidinium cation, 1,3- Ethyl-1,2-dimethylpyrrolidinium cation, 1,3-diethyl-1,3-dimethylpyrrolidinium cation, 1,2-diethyl-1,4-dimethyl Pyrrolidinium cation, 1,4-diethyl-1,2-dimethylpyrrolidinium cation, 1,2-diethyl-1,5-dimethylpyrrolidinium cation, 1,5-di Ethyl-1,2-dimethylpyrrolidinium cation, 1,3-diethyl-1,4-dimethylpyrrolidinium cation, 1,1,2,2,3-pentamethylpyrrolidine Ruthenium cation, 1,1,2,2,4-pentamethylpyrrolidinium cation, 1,1,2,2,5-pentamethylpyrrolidinium cation, 1,1,2,3,4-five Methyl pyrrolidinium cation, 1,1,2,3,5-pentamethylpyrrolidinium cation, 1,1,3,3,4-pentamethylpyrrolidinium cation, 1,1,3,3 , 5-pentamethylpyrrolidinium cation, 1-ethyl-1,2,2,3-tetramethylpyrrolidinium cation, 1-ethyl-1,2,2,4-tetramethylpyrrolidine Ruthenium cation, 1-ethyl-1,2,2,5-tetramethylpyrrolidinium cation, 1-ethyl-1,2,3,4-tetramethylpyrrolidinium cation, 1-ethyl- 1,2,3,5-tetramethylpyrrolidinium cation, 1-ethyl-1,2,4,5-tetramethylpyrrolidinium cation, 1-ethyl-1,3,3,4- Tetramethylpyrrolidine cation 1-ethyl-1,3,3,5-tetramethylpyrrolidinium cation, 1-ethyl-1,3,4,5-tetramethylpyrrolidinium cation, 2-ethyl-1,1 , 2,3-tetramethylpyrrolidinium cation, 2-ethyl-1,1,2,4-tetramethylpyrrolidinium cation, 2-ethyl-1,1,2,5-tetramethyl Pyrrolidinium cation, 2-ethyl-1,1,3,3-tetramethylpyrrolidinium cation, 2-ethyl-1,1,3,4-tetramethylpyrrolidinium cation, 2-B 1,2-,3,5-tetramethylpyrrolidinium cation, 2-ethyl-1,1,4,4-tetramethylpyrrolidinium cation, 2-ethyl-1,1,4, 5-tetramethylpyrrolidinium cation, 2-ethyl-1,1,5,5-tetramethylpyrrolidinium cation, 3-ethyl-1,1,2,2-tetramethylpyrrolidinium Cation, 3-ethyl-1,1,2,3-tetramethylpyrrolidinium cation, 3-ethyl-1,1,2,4-tetramethylpyrrolidinium cation, 3-ethyl-1 , 1,2,5-tetramethylpyrrolidinium cation, 3-ethyl-1,1,3,4-tetramethylpyrrolidinium cation, 3-ethyl-1,1,4,4-tetra a methylpyrrolidine cation, a 3-ethyl-1,1,4,5-tetramethylpyrrolidinium cation, a 1,1,2,2,3,3-hexamethylpyrrolidinium cation, 1, 1,2,2,3,4-hexamethylpyrrolidinium cation, 1,1,2,2, 3,5-hexamethylpyrrolidinium cation, 1,1,2,2,4,4-hexamethylpyrrolidinium cation, 1,1,2,2,4,5-hexamethylpyrrolidinium a cation, a 1,1,2,2,5,5-hexamethylpyrrolidinium cation, a 1,1,2,3,3,4-hexamethylpyrrolidinium cation, 1,1,2,3, 3,5-hexamethylpyrrolidinium cation, 1,1,2,3,4,4-hexamethylpyrrolidinium cation, 1,1,2,3,5,5-hexamethylpyrrolidinium a 1,1-dialkylpyrrolidinium cation having an alkyl group at a carbon atom of the pyrrolidine ring, such as a cation, a 1,1,2,3,4,5-hexamethylpyrrolidinium cation.

作為嗎啉鎓陽離子者,可列舉如:4,4-二甲基嗎啉鎓陽離子、4-乙基-4-甲基嗎啉鎓陽離子、4,4-二乙基嗎啉鎓陽離子、3,4,4-三甲基嗎啉鎓陽離子、2,4,4-三甲基嗎啉鎓陽離子、3-乙基-4,4-二甲基嗎啉鎓陽離子、3,4-二甲基-4-乙基嗎啉鎓陽離子、2,4-二甲基-4-乙基嗎啉鎓陽離子、3-甲基-4,4-二乙基嗎啉鎓陽離子、2,4-二甲基-4-乙基嗎啉鎓陽離子、2-甲基-4,4-二乙基嗎啉鎓陽離子、3,4-二乙基-4-甲基嗎啉鎓陽離子、2,4-二乙基-4-甲基嗎啉鎓陽離子、3,4,4-三乙基嗎啉鎓陽離子、2,4,4-三乙基嗎啉鎓陽離子、3,3,4,4-四甲基嗎啉鎓陽離子、2,3,4,4-四甲基嗎啉鎓陽離子、2,4,4,5-四甲基嗎啉鎓陽離子、3,4,4,5-四甲基嗎啉鎓陽離子、2,2,4,4-四甲基嗎啉鎓陽離子、2,4,4,6-四甲基嗎啉鎓陽離子、2,4,4-三甲基-3-乙基嗎啉鎓陽離子、2-乙基-3,4,4-三甲基嗎啉鎓陽離子、2,4,4-三甲基-5-乙基嗎啉鎓陽離子、2-乙基-4,4,5-三甲基嗎啉鎓陽離子、3-乙基-4,4,6-三甲基嗎啉鎓陽離子、2-乙基-4,4,5-三甲基嗎啉鎓陽離子、2-乙基-4,4,6-三甲基嗎啉鎓陽離子、2,3-二甲基-4,4-二乙基嗎啉鎓陽離子、2,5-二甲基-4,4-二乙基嗎啉鎓陽離子、3,5-二甲基-4,4-二乙基嗎啉鎓陽離子、2,6-二甲基-4,4-二乙基嗎啉鎓陽離子、2,4-二甲基-3,4-二乙基嗎啉鎓陽離子、2,4-二乙基-3,4-二甲基嗎啉鎓陽離子、2,4-二甲基-4,5-二乙基嗎啉鎓陽離子、2,4-二乙基-4,5-二甲基嗎啉鎓陽離子、3,4-二乙基-4,5-二甲基嗎啉鎓陽離子、2,4-二乙基-4,6-二甲基嗎啉鎓陽離子、2,3-二乙基-4,4-二甲基嗎啉鎓陽離子、2,5-二乙基-4,4-二甲基嗎啉鎓陽離子、3,5-二乙基-4,4-二甲基嗎啉鎓陽離子、2,6-二乙基-4,4-二甲基嗎啉鎓陽離子、2,3,4,4,6-五甲基嗎啉鎓陽離子、2,3,4,4,5-五甲基嗎啉鎓陽離子、2,6,4,4-四甲基-3-乙基嗎啉鎓陽離子、2,4,4,5-四甲基-3-乙基嗎啉鎓陽離子、2-乙基-3,4,4,6-四甲基嗎啉鎓陽離子、2-乙基-3,4,4,5-四甲基嗎啉鎓陽離子、2,3,4,4,5,6-六甲基嗎啉鎓陽離子等在嗎啉環的碳原子上有烷基之4-烷基嗎啉鎓陽離子。Examples of the morpholinium cation include a 4,4-dimethylmorpholinium cation, a 4-ethyl-4-methylmorpholinium cation, a 4,4-diethylmorpholinium cation, and 3 , 4,4-trimethylmorpholinium cation, 2,4,4-trimethylmorpholinium cation, 3-ethyl-4,4-dimethylmorpholinium cation, 3,4-dimethyl 4-ethylmorpholinium cation, 2,4-dimethyl-4-ethylmorpholinium cation, 3-methyl-4,4-diethylmorpholinium cation, 2,4-di Methyl-4-ethylmorpholinium cation, 2-methyl-4,4-diethylmorpholinium cation, 3,4-diethyl-4-methylmorpholinium cation, 2,4- Diethyl-4-methylmorpholinium cation, 3,4,4-triethylmorpholinium cation, 2,4,4-triethylmorpholinium cation, 3,3,4,4-tetra Methylmorpholinium cation, 2,3,4,4-tetramethylmorpholinium cation, 2,4,4,5-tetramethylmorpholinium cation, 3,4,4,5-tetramethyl Morpholinium cation, 2,2,4,4-tetramethylmorpholinium cation, 2,4,4,6-tetramethylmorpholinium cation, 2,4,4-trimethyl-3-B Pyrazoline cation, 2-ethyl-3,4,4-trimethylmorpholinium cation, 2,4,4-trimethyl-5-ethylmorpholinium cation 2-ethyl-4,4,5-trimethylmorpholinium cation, 3-ethyl-4,4,6-trimethylmorpholinium cation, 2-ethyl-4,4,5-three Methylmorpholinium cation, 2-ethyl-4,4,6-trimethylmorpholinium cation, 2,3-dimethyl-4,4-diethylmorpholinium cation, 2,5- Dimethyl-4,4-diethylmorpholinium cation, 3,5-dimethyl-4,4-diethylmorpholinium cation, 2,6-dimethyl-4,4-di Pyrazoline cation, 2,4-dimethyl-3,4-diethylmorpholinium cation, 2,4-diethyl-3,4-dimethylmorpholinium cation, 2,4- Dimethyl-4,5-diethylmorpholinium cation, 2,4-diethyl-4,5-dimethylmorpholinium cation, 3,4-diethyl-4,5-dimethyl Pyrazoline cation, 2,4-diethyl-4,6-dimethylmorpholinium cation, 2,3-diethyl-4,4-dimethylmorpholinium cation, 2,5- Diethyl-4,4-dimethylmorpholinium cation, 3,5-diethyl-4,4-dimethylmorpholinium cation, 2,6-diethyl-4,4-dimethyl Pyrazoline cation, 2,3,4,4,6-pentamethylmorpholinium cation, 2,3,4,4,5-pentamethylmorpholinium cation, 2,6,4,4- Tetramethyl-3-ethylmorpholinium cation, 2,4,4,5-tetramethyl-3 -ethylmorpholinium cation, 2-ethyl-3,4,4,6-tetramethylmorpholinium cation, 2-ethyl-3,4,4,5-tetramethylmorpholinium cation, A 2,3,4,4,5,6-hexamethylmorpholinium cation or the like having an alkyl 4-alkylmorpholinium cation on the carbon atom of the morpholine ring.

作為咪唑啉鎓陽離子者,可列舉如:1,3-二甲基咪唑啉鎓陽離子、1-乙基-3-甲基咪唑啉鎓陽離子、1,3-二乙基咪唑啉鎓陽離子、1,2,3-三甲基咪唑啉鎓陽離子、1,3,4-三甲基咪唑啉鎓陽離子、1-乙基-2,3-二甲基咪唑啉鎓陽離子、1-乙基-3,4-二甲基咪唑啉鎓陽離子、1-乙基-3,5-二甲基咪唑啉鎓陽離子、2-乙基-1,3-二甲基咪唑啉鎓陽離子、4-乙基-1,3-二甲基咪唑啉鎓陽離子、1,2-二乙基-3-甲基咪唑啉鎓陽離子、1,4-二乙基-3-甲基咪唑啉鎓陽離子、1,5-二乙基-3-甲基咪唑啉鎓陽離子、1,3-二乙基-2-甲基咪唑啉鎓陽離子、1,3-二乙基-4-甲基咪唑啉鎓陽離子、1,2,3-三乙基咪唑啉鎓陽離子、1,3,4-三乙基咪唑啉鎓陽離子、1,2,3,4-四甲基咪唑啉鎓陽離子、1-乙基-2,3,4-三甲基咪唑啉鎓陽離子、1-乙基-2,3,5-三甲基咪唑啉鎓陽離子、1-乙基-3,4,5-三甲基咪唑啉鎓陽離子、2-乙基-1,3,4-三甲基咪唑啉鎓陽離子、4-乙基-1,2,3-三甲基咪唑啉鎓陽離子、1,2-二乙基-3,4-二甲基咪唑啉鎓陽離子、1,3-二乙基-2,4-二甲基咪唑啉鎓陽離子、1,4-二乙基-2,3-二甲基咪唑啉鎓陽離子、2,4-二乙基-1,3-二甲基咪唑啉鎓陽離子、4,5-二乙基-1,3-二甲基咪唑啉鎓陽離子、1,2,3-三乙基-4-甲基咪唑啉鎓陽離子、1,2,4-三乙基-3-甲基咪唑啉鎓陽離子、1,2,5-三乙基-3-甲基咪唑啉鎓陽離子、1,3,4-三乙基-2-甲基咪唑啉鎓陽離子、1,3,4-三乙基-5-甲基咪唑啉鎓陽離子、1,4,5-三乙基-3-甲基咪唑啉鎓陽離子、1,2,3,4,5-五甲基咪唑啉鎓陽離子、1-甲基-3-丙基咪唑啉鎓陽離子等在咪唑環的碳原子上有烷基之1,3-二烷基咪唑啉鎓陽離子。Examples of the imidazolinium cation include 1,3-dimethylimidazolium cation, 1-ethyl-3-methylimidazolium cation, 1,3-diethylimidazolium cation, and 1 , 2,3-trimethylimidazolinium cation, 1,3,4-trimethylimidazolinium cation, 1-ethyl-2,3-dimethylimidazolium cation, 1-ethyl-3 , 4-dimethylimidazolinium cation, 1-ethyl-3,5-dimethylimidazolium cation, 2-ethyl-1,3-dimethylimidazolium cation, 4-ethyl- 1,3-Dimethylimidazolinium cation, 1,2-diethyl-3-methylimidazolinium cation, 1,4-diethyl-3-methylimidazolium cation, 1,5- Diethyl-3-methylimidazolinium cation, 1,3-diethyl-2-methylimidazolinium cation, 1,3-diethyl-4-methylimidazolinium cation, 1,2 , 3-triethylimidazolium cation, 1,3,4-triethylimidazolium cation, 1,2,3,4-tetramethylimidazolium cation, 1-ethyl-2,3, 4-trimethylimidazolinium cation, 1-ethyl-2,3,5-trimethylimidazolinium cation, 1-ethyl-3,4,5-trimethylimidazolium cation, 2- Ethyl-1,3,4-trimethylimidazolinium Cation, 4-ethyl-1,2,3-trimethylimidazolinium cation, 1,2-diethyl-3,4-dimethylimidazolium cation, 1,3-diethyl-2 , 4-dimethylimidazolium cation, 1,4-diethyl-2,3-dimethylimidazolium cation, 2,4-diethyl-1,3-dimethylimidazolium cation , 4,5-diethyl-1,3-dimethylimidazolium cation, 1,2,3-triethyl-4-methylimidazolinium cation, 1,2,4-triethyl- 3-methylimidazolinium cation, 1,2,5-triethyl-3-methylimidazolinium cation, 1,3,4-triethyl-2-methylimidazolinium cation, 1,3 , 4-triethyl-5-methylimidazolinium cation, 1,4,5-triethyl-3-methylimidazolinium cation, 1,2,3,4,5-pentamethylimidazoline An anthracene cation, a 1-methyl-3-propylimidazolium cation or the like has an alkyl group of a 1,3-dialkylimidazolinium cation on the carbon atom of the imidazole ring.

作為四氫嘧啶鎓陽離子者,可列舉如:1,3-二甲基四氫嘧啶鎓陽離子、1-乙基-3-甲基四氫嘧啶鎓陽離子、1,3-二乙基四氫嘧啶鎓陽離子、1,2,3-三甲基四氫嘧啶鎓陽離子、1,3,4-三甲基四氫嘧啶鎓陽離子、1,3,5-三甲基四氫嘧啶鎓陽離子、1-乙基-2,3-二甲基四氫嘧啶鎓陽離子、1-乙基-3,4-二甲基四氫嘧啶鎓陽離子、1-乙基-3,5-二甲基四氫嘧啶鎓陽離子、1-乙基-3,6-二甲基四氫嘧啶鎓陽離子、2-乙基-1,3-二甲基四氫嘧啶鎓陽離子、4-乙基-1,3-二甲基四氫嘧啶鎓陽離子、5-乙基-1,3-二甲基四氫嘧啶鎓陽離子、1,2,3,4-四甲基四氫嘧啶鎓陽離子、1,2,3,5-四甲基四氫嘧啶鎓陽離子、1-乙基-2,3,4-三甲基四氫嘧啶鎓陽離子、1-乙基-2,3,5-三甲基四氫嘧啶鎓陽離子、1-乙基-2,3,6-三甲基四氫嘧啶鎓陽離子、2-乙基-1,3,4-三甲基四氫嘧啶鎓陽離子、2-乙基-1,3,5-三甲基四氫嘧啶鎓陽離子、4-乙基-1,2,3-三甲基四氫嘧啶鎓陽離子、4-乙基-1,3,5-三甲基四氫嘧啶鎓陽離子、4-乙基-1,3,6-三甲基四氫嘧啶鎓陽離子、5-乙基-1,2,3-三甲基四氫嘧啶鎓陽離子、5-乙基-1,3,4-三甲基四氫嘧啶鎓陽離子、1,2-二乙基-3,4-二甲基四氫嘧啶鎓陽離子、1,2-二乙基-3,5-二甲基四氫嘧啶鎓陽離子、1,2-二乙基-3,6-二甲基四氫嘧啶鎓陽離子、1,3-二乙基-2,4-二甲基四氫嘧啶鎓陽離子、1,3-二乙基-2,5-二甲基四氫嘧啶鎓陽離子、1,4-二乙基-2,3-二甲基四氫嘧啶鎓陽離子、1,4-二乙基-3,5-二甲基四氫嘧啶鎓陽離子、1,4-二乙基-3,6-二甲基四氫嘧啶鎓陽離子、1,5-二乙基-2,3-二甲基四氫嘧啶鎓陽離子、1,5-二乙基-3,4-二甲基四氫嘧啶鎓陽離子、1,5-二乙基-3,6-二甲基四氫嘧啶鎓陽離子、2,4-二乙基-1,3-二甲基四氫嘧啶鎓陽離子、2,5-二乙基-1,3-二甲基四氫嘧啶鎓陽離子、4,5-二乙基-1,3-二甲基四氫嘧啶鎓陽離子、4,6-二乙基-1,3-二甲基四氫嘧啶鎓陽離子、1,2,3,4,5-五甲基四氫嘧啶鎓陽離子、1,2,3,4,6-五甲基四氫嘧啶鎓陽離子、1,2,3,4,5,6-六甲基四氫嘧啶鎓陽離子等在四氫嘧啶環之碳原子上有烷基之1,3-二烷基四氫嘧啶鎓陽離子。Examples of the tetrahydropyrimidinium cation include 1,3-dimethyltetrahydropyrimidinium cation, 1-ethyl-3-methyltetrahydropyrimidinium cation, and 1,3-diethyltetrahydropyrimidine. Ruthenium cation, 1,2,3-trimethyltetrahydropyrimidinium cation, 1,3,4-trimethyltetrahydropyrimidinium cation, 1,3,5-trimethyltetrahydropyrimidinium cation, 1- Ethyl-2,3-dimethyltetrahydropyrimidinium cation, 1-ethyl-3,4-dimethyltetrahydropyrimidinium cation, 1-ethyl-3,5-dimethyltetrahydropyrimidine Cation, 1-ethyl-3,6-dimethyltetrahydropyrimidinium cation, 2-ethyl-1,3-dimethyltetrahydropyrimidinium cation, 4-ethyl-1,3-dimethyl Tetrahydropyrimidinium cation, 5-ethyl-1,3-dimethyltetrahydropyrimidinium cation, 1,2,3,4-tetramethyltetrahydropyrimidinium cation, 1,2,3,5-tetra Methyltetrahydropyrimidine cation, 1-ethyl-2,3,4-trimethyltetrahydropyrimidinium cation, 1-ethyl-2,3,5-trimethyltetrahydropyrimidinium cation, 1- Ethyl-2,3,6-trimethyltetrahydropyrimidinium cation, 2-ethyl-1,3,4-trimethyltetrahydropyrimidinium cation, 2-ethyl-1,3,5-three Methyltetrahydropyrimidine cation, 4-ethyl-1,2, 3-trimethyltetrahydropyrimidinium cation, 4-ethyl-1,3,5-trimethyltetrahydropyrimidinium cation, 4-ethyl-1,3,6-trimethyltetrahydropyrimidinium cation , 5-ethyl-1,2,3-trimethyltetrahydropyrimidinium cation, 5-ethyl-1,3,4-trimethyltetrahydropyrimidinium cation, 1,2-diethyl-3 , 4-dimethyltetrahydropyrimidinium cation, 1,2-diethyl-3,5-dimethyltetrahydropyrimidinium cation, 1,2-diethyl-3,6-dimethyltetrahydro Pyrimidine cation, 1,3-diethyl-2,4-dimethyltetrahydropyrimidinium cation, 1,3-diethyl-2,5-dimethyltetrahydropyrimidinium cation, 1,4- Diethyl-2,3-dimethyltetrahydropyrimidinium cation, 1,4-diethyl-3,5-dimethyltetrahydropyrimidinium cation, 1,4-diethyl-3,6- Dimethyltetrahydropyrimidine cation, 1,5-diethyl-2,3-dimethyltetrahydropyrimidinium cation, 1,5-diethyl-3,4-dimethyltetrahydropyrimidinium cation 1,5-diethyl-3,6-dimethyltetrahydropyrimidinium cation, 2,4-diethyl-1,3-dimethyltetrahydropyrimidinium cation, 2,5-diethyl -1,3-dimethyltetrahydropyrimidinium cation, 4,5-diethyl-1,3-dimethyltetrahydropyrimidinium cation, 4, 6-Diethyl-1,3-dimethyltetrahydropyrimidinium cation, 1,2,3,4,5-pentamethyltetrahydropyrimidinium cation, 1,2,3,4,6-penta a tetrahydrotetrapyrimidine cation, an 1,2,3,4,5,6-hexamethyltetrahydropyrimidinium cation or the like having an alkyl group of 1,3-dialkyltetrahydrogen at a carbon atom of a tetrahydropyrimidine ring Pyrimidine cation.

作為哌嗪鎓(piperazinium)陽離子者,可列舉如:1,1,4,4-四甲基哌嗪鎓陽離子、1-乙基-1,4,4-三甲基哌嗪鎓陽離子、1,1-二乙基-4,4-二甲基哌嗪鎓陽離子、1,1,4-三乙基-4-甲基哌嗪鎓陽離子、1,1,4,4-四乙基哌嗪鎓陽離子、1,1,2,4,4-五甲基哌嗪鎓陽離子、1,1,3,4,4-五甲基哌嗪鎓陽離子、1,1,2,3,4,4-六甲基哌嗪鎓陽離子、1,1,2,4,4,5-六甲基哌嗪鎓陽離子、1,1,2,4,4,6-六甲基哌嗪鎓陽離子、1,1,3,4,4,5-六甲基哌嗪鎓陽離子、1-乙基-1,2,4,4-四甲基哌嗪鎓陽離子、1-乙基-1,3,4,4-四甲基哌嗪鎓陽離子、2-乙基-1,1,4,4-四甲基哌嗪鎓陽離子、1-乙基-1,2,4,4-四甲基哌嗪鎓陽離子、1-乙基-1,3,4,4-四甲基哌嗪鎓陽離子、1,1-二乙基-2,4,4-三甲基哌嗪鎓陽離子、1,4-二乙基-1,2,4-三甲基哌嗪鎓陽離子、1,2-二乙基-1,4,4-三甲基哌嗪鎓陽離子、1,3-二乙基-1,4,4-三甲基哌嗪鎓陽離子等在哌嗪環之碳原子上有烷基之1,1,4,4-四烷基哌嗪鎓陽離子。Examples of the piperazinium cation include 1,1,4,4-tetramethylpiperazinium cation, 1-ethyl-1,4,4-trimethylpiperazinium cation, and 1 , 1-diethyl-4,4-dimethylpiperazinium cation, 1,1,4-triethyl-4-methylpiperazinium cation, 1,1,4,4-tetraethylper Pyridinium cation, 1,1,2,4,4-pentamethylpiperazinium cation, 1,1,3,4,4-pentamethylpiperazinium cation, 1,1,2,3,4, 4-hexamethylpiperazinium cation, 1,1,2,4,4,5-hexamethylpiperazinium cation, 1,1,2,4,4,6-hexamethylpiperazinium cation, 1,1,3,4,4,5-hexamethylpiperazinium cation, 1-ethyl-1,2,4,4-tetramethylpiperazinium cation, 1-ethyl-1,3, 4,4-tetramethylpiperazinium cation, 2-ethyl-1,1,4,4-tetramethylpiperazinium cation, 1-ethyl-1,2,4,4-tetramethylper Pyridinium cation, 1-ethyl-1,3,4,4-tetramethylpiperazinium cation, 1,1-diethyl-2,4,4-trimethylpiperazinium cation, 1,4 -diethyl-1,2,4-trimethylpiperazinium cation, 1,2-diethyl-1,4,4-trimethylpiperazinium cation, 1,3-diethyl-1 , 4,4-trimethylpiperazinium cation, etc., having an alkyl group 1,1,4 on the carbon atom of the piperazine ring , 4-tetraalkyl piperazine cation.

作為哌啶鎓(piperidinium)陽離子者,可列舉如:1,1-二甲基哌啶鎓陽離子、1-乙基-1-甲基哌啶鎓陽離子、1,1-二乙基哌啶鎓陽離子、1,1,2-三甲基哌啶鎓陽離子、1,1,3-三甲基哌啶鎓陽離子、1,1,4-三甲基哌啶鎓陽離子、1,1,2,2-四甲基哌啶鎓陽離子、1,1,2,3-四甲基哌啶鎓陽離子、1,1,2,4-四甲基哌啶鎓陽離子、1,1,2,5-四甲基哌啶鎓陽離子、1,1,2,6-四甲基哌啶鎓陽離子、1,1,3,3-四甲基哌啶鎓陽離子、1,1,3,4-四甲基哌啶鎓陽離子、1,1,3,5-四甲基哌啶鎓陽離子、1-乙基-1,2-二甲基哌啶鎓陽離子、1-乙基-1,3-二甲基哌啶鎓陽離子、1-乙基-1,4-二甲基哌啶鎓陽離子、1-乙基-1,2,3-三甲基哌啶鎓陽離子、1-乙基-1,2,4-三甲基哌啶鎓陽離子、1-乙基-1,2,5-三甲基哌啶鎓陽離子、1-乙基-1,2,6-三甲基哌啶鎓陽離子、1-乙基-1,3,4-三甲基哌啶鎓陽離子、1-乙基-1,3,5-三甲基哌啶鎓陽離子、1,1-二乙基-2-甲基哌啶鎓陽離子、1,1-二乙基-3-甲基哌啶鎓陽離子、1,1-二乙基-4-甲基哌啶鎓陽離子、1,1-二乙基-2,3-二甲基哌啶鎓陽離子、1,1-二乙基-2,4-二甲基哌啶鎓陽離子、1,1-二乙基-2,5-二甲基哌啶鎓陽離子、1,1-二乙基-2,6-二甲基哌啶鎓陽離子、1,1-二乙基-3,4-二甲基哌啶鎓陽離子、1,1-二乙基-3,5-二甲基哌啶鎓陽離子、2-乙基-1,1,3-三甲基哌啶鎓陽離子、2-乙基-1,1,4-三甲基哌啶鎓陽離子、2-乙基-1,1,5-三甲基哌啶鎓陽離子、2-乙基-1,1,6-三甲基哌啶鎓陽離子、3-乙基-1,1,2-三甲基哌啶鎓陽離子、3-乙基-1,1,4-三甲基哌啶鎓陽離子、3-乙基-1,1,5-三甲基哌啶鎓陽離子、3-乙基-1,1,6-三甲基哌啶鎓陽離子、4-乙基-1,1,2-三甲基哌啶鎓陽離子、4-乙基-1,1,3-三甲基哌啶鎓陽離子、1,2-二乙基-1,3-二甲基哌啶鎓陽離子、1-乙基-1,2,4-三甲基哌啶鎓陽離子、1,2-二乙基-1,5-二甲基哌啶鎓陽離子、1,2-二乙基-1,6-二甲基哌啶鎓陽離子、1,3-二乙基-1,5-二甲基哌啶鎓陽離子、1,3-二乙基-1,4-二甲基哌啶鎓陽離子、1,3-二乙基-1,5-二甲基哌啶鎓陽離子、1,3-二乙基-1,6-二甲基哌啶鎓陽離子、1,4-二乙基-1,2-二甲基哌啶鎓陽離子、1,4-二乙基-1,3-二甲基哌啶鎓陽離子、1,1,2-三乙基-3-甲基哌啶鎓陽離子、1,1,2-三乙基-4-甲基哌啶鎓陽離子、1,1,2-三乙基-5-甲基哌啶鎓陽離子、1,1,2-三乙基-6-甲基哌啶鎓陽離子、1,1,3-三乙基-2-甲基哌啶鎓陽離子、1,1,3-三乙基-4-甲基哌啶鎓陽離子、1,1,3-二乙基-5-甲基哌啶鎓陽離子、1,1,3-三乙基-6-甲基哌啶鎓陽離子、1,1,4-三乙基-2-甲基哌啶鎓陽離子、1,1,4-二乙基-3-甲基哌啶鎓陽離子、2-乙基-1,1-二甲基哌啶鎓陽離子、3-乙基-1,1-二甲基哌啶鎓陽離子、4-乙基-1,1-二甲基哌啶鎓陽離子、2,3-二乙基-1,1-二甲基哌啶鎓陽離子、2,4-二乙基-1,1-二甲基哌啶鎓陽離子、2,5-二乙基-1,1-二甲基哌啶鎓陽離子、2,6-二乙基-1,1-二甲基哌啶鎓陽離子、3,4-二乙基-1,1-二甲基哌啶鎓陽離子、3,5-二乙基-1,1-二甲基哌啶鎓陽離子、1,2-二乙基-1-甲基哌啶鎓陽離子、1,3-二乙基-1-甲基哌啶鎓陽離子、1,4-二乙基-1-甲基哌啶鎓陽離子、1,2,3-三乙基-1-甲基哌啶鎓陽離子、1,2,4-三乙基-1-甲基哌啶鎓陽離子、1,2,5-三乙基-1-甲基哌啶鎓陽離子、1,2,6-三乙基-1-甲基哌啶鎓陽離子、1,3,4-三乙基-1-甲基哌啶鎓陽離子、1,3,5-三乙基-1-甲基哌啶鎓陽離子、1,1,2-三乙基哌啶鎓陽離子、1,1,2-三乙基哌啶鎓陽離子、1,1,4-三乙基哌啶鎓陽離子、1,1,2,3-四乙基哌啶鎓陽離子、1,1,2,4-四乙基哌啶鎓陽離子、1,1,2,5-四乙基哌啶鎓陽離子、1,1,2,6-四乙基哌啶鎓陽離子、1,1,3,4-四乙基哌啶鎓陽離子、1,1,3,5-四乙基哌啶鎓陽離子等在哌啶環之碳原子上有烷基之1,1-二烷基哌啶鎓陽離子。Examples of the piperidinium cation include 1,1-dimethylpiperidinium cation, 1-ethyl-1-methylpiperidinium cation, and 1,1-diethylpiperidinium. a cation, a 1,1,2-trimethylpiperidinium cation, a 1,1,3-trimethylpiperidinium cation, a 1,1,4-trimethylpiperidinium cation, 1,1,2, 2-tetramethylpiperidinium cation, 1,1,2,3-tetramethylpiperidinium cation, 1,1,2,4-tetramethylpiperidinium cation, 1,1,2,5- Tetramethylpiperidinium cation, 1,1,2,6-tetramethylpiperidinium cation, 1,1,3,3-tetramethylpiperidinium cation, 1,1,3,4-tetra Keipridinium cation, 1,1,3,5-tetramethylpiperidinium cation, 1-ethyl-1,2-dimethylpiperidinium cation, 1-ethyl-1,3-dimethyl Isopiperidinium cation, 1-ethyl-1,4-dimethylpiperidinium cation, 1-ethyl-1,2,3-trimethylpiperidinium cation, 1-ethyl-1,2 , 4-trimethylpiperidinium cation, 1-ethyl-1,2,5-trimethylpiperidinium cation, 1-ethyl-1,2,6-trimethylpiperidinium cation, 1 -ethyl-1,3,4-trimethylpiperidinium cation, 1-ethyl-1,3,5-trimethylpiperidinium cation, 1,1-diethyl-2-methyl Pyridinium cation, 1,1-diethyl-3-methylpiperidinium cation, 1,1-diethyl-4-methylpiperidinium cation, 1,1-diethyl-2,3- Dimethylpiperidinium cation, 1,1-diethyl-2,4-dimethylpiperidinium cation, 1,1-diethyl-2,5-dimethylpiperidinium cation, 1, 1-diethyl-2,6-dimethylpiperidinium cation, 1,1-diethyl-3,4-dimethylpiperidinium cation, 1,1-diethyl-3,5- Dimethylpiperidinium cation, 2-ethyl-1,1,3-trimethylpiperidinium cation, 2-ethyl-1, 1,4-trimethylpiperidinium cation, 2-ethyl -1,1,5-trimethylpiperidinium cation, 2-ethyl-1,1,6-trimethylpiperidinium cation, 3-ethyl-1,1,2-trimethylpiperidine Ruthenium cation, 3-ethyl-1,1,4-trimethylpiperidinium cation, 3-ethyl-1,1,5-trimethylpiperidinium cation, 3-ethyl-1,1, 6-trimethylpiperidinium cation, 4-ethyl-1,1,2-trimethylpiperidinium cation, 4-ethyl-1,1,3-trimethylpiperidinium cation, 1, 2-Diethyl-1,3-dimethylpiperidinium cation, 1-ethyl-1,2,4-trimethylpiperidinium cation, 1,2-diethyl-1,5-di Methylpiperidinium cation, 1,2-diethyl-1, 6-dimethylpiperidinium cation, 1,3-diethyl-1,5-dimethylpiperidinium cation, 1,3-diethyl-1,4-dimethylpiperidinium cation, 1,3-Diethyl-1,5-dimethylpiperidinium cation, 1,3-diethyl-1,6-dimethylpiperidinium cation, 1,4-diethyl-1, 2-dimethylpiperidinium cation, 1,4-diethyl-1,3-dimethylpiperidinium cation, 1,1,2-triethyl-3-methylpiperidinium cation, 1 1,2-triethyl-4-methylpiperidinium cation, 1,1,2-triethyl-5-methylpiperidinium cation, 1,1,2-triethyl-6- Isopiperidinium cation, 1,1,3-triethyl-2-methylpiperidinium cation, 1,1,3-triethyl-4-methylpiperidinium cation, 1,1,3- Diethyl-5-methylpiperidinium cation, 1,1,3-triethyl-6-methylpiperidinium cation, 1,1,4-triethyl-2-methylpiperidinium cation 1,1,4-diethyl-3-methylpiperidinium cation, 2-ethyl-1,1-dimethylpiperidinium cation, 3-ethyl-1,1-dimethylper Pyridinium cation, 4-ethyl-1,1-dimethylpiperidinium cation, 2,3-diethyl-1,1-dimethylpiperidinium cation, 2,4-diethyl-1 , 1-dimethylpiperidinium cation, 2,5- Ethyl-1,1-dimethylpiperidinium cation, 2,6-diethyl-1,1-dimethylpiperidinium cation, 3,4-diethyl-1,1-dimethyl Piperidinium cation, 3,5-diethyl-1,1-dimethylpiperidinium cation, 1,2-diethyl-1-methylpiperidinium cation, 1,3-diethyl- 1-methylpiperidinium cation, 1,4-diethyl-1-methylpiperidinium cation, 1,2,3-triethyl-1-methylpiperidinium cation, 1,2,4 -Triethyl-1-methylpiperidinium cation, 1,2,5-triethyl-1-methylpiperidinium cation, 1,2,6-triethyl-1-methylpiperidinium Cation, 1,3,4-triethyl-1-methylpiperidinium cation, 1,3,5-triethyl-1-methylpiperidinium cation, 1,1,2-triethylper a pyridine cation, a 1,1,2-triethylpiperidinium cation, a 1,1,4-triethylpiperidinium cation, a 1,1,2,3-tetraethylpiperidinium cation, 1, 1,2,4-tetraethylpiperidinium cation, 1,1,2,5-tetraethylpiperidinium cation, 1,1,2,6-tetraethylpiperidinium cation, 1,1, a 1,1-dialkylpiperidinium having an alkyl group at a carbon atom of a piperidine ring, such as a 3,4-tetraethylpiperidinium cation, a 1,1,3,5-tetraethylpiperidinium cation or the like. cation.

作為吡啶鎓(Pyridinium)陽離子者,可列舉如:1-甲基吡啶鎓陽離子、1-乙基吡啶鎓陽離子、1-丙基吡啶鎓陽離子、1-丁基吡啶鎓陽離子、1-戊基吡啶鎓陽離子、1-己基吡啶鎓陽離子、1-庚基吡啶鎓陽離子、1-辛基吡啶鎓陽離子、1-壬基吡啶鎓陽離子、1-癸基吡啶鎓陽離子、1,2-二甲基吡啶鎓陽離子、1,3-二甲基吡啶鎓陽離子、1,4-二甲基吡啶鎓陽離子、1-乙基-2-甲基吡啶鎓陽離子、2-乙基-1-甲基吡啶鎓陽離子、1-乙基-3-甲基吡啶鎓陽離子、3-乙基-1-甲基吡啶鎓陽離子、1-乙基-4-甲基吡啶鎓陽離子、4-乙基-1-甲基吡啶鎓陽離子、1,2-二乙基吡啶鎓陽離子、1,3-二乙基吡啶鎓陽離子、1,4-二乙基吡啶鎓陽離子、1,2,3-三甲基吡啶鎓陽離子、1,2,4-三甲基吡啶鎓陽離子、1,3,4-三甲基吡啶鎓陽離子、1,3,5-三甲基吡啶鎓陽離子、1,2,5-三甲基吡啶鎓陽離子、1,2,6-三甲基吡啶鎓陽離子、1-乙基-2,3-二甲基吡啶鎓陽離子、1-乙基-2,4-二甲基吡啶鎓陽離子、1-乙基-2,5-二甲基吡啶鎓陽離子、1-乙基-2,6-二甲基吡啶鎓陽離子、1-乙基-3,4-二甲基吡啶鎓陽離子、1-乙基-3,5-二甲基吡啶鎓陽離子、2-乙基-1,3-二甲基吡啶鎓陽離子、2-乙基-1,4-二甲基吡啶鎓陽離子、2-乙基-1,5-二甲基吡啶鎓陽離子、2-乙基-1,6-二甲基吡啶鎓陽離子、3-乙基-1,2-二甲基吡啶鎓陽離子、3-乙基-1,4-二甲基吡啶鎓陽離子、3-乙基-1,5-二甲基吡啶鎓陽離子、3-乙基-1,6-二甲基吡啶鎓陽離子、4-乙基-1,2-二甲基吡啶鎓陽離子、4-乙基-1,3-二甲基吡啶鎓陽離子、1,2-二乙基-3-甲基吡啶鎓陽離子、1,2-二乙基-4-甲基吡啶鎓陽離子、1,2-二乙基-5-甲基吡啶鎓陽離子、1,2-二乙基-6-甲基吡啶鎓陽離子、1,3-二乙基-2-甲基吡啶鎓陽離子、1,3-二乙基-4-甲基吡啶鎓陽離子、1,3-二乙基-5-甲基吡啶鎓陽離子、1,3-二乙基-6-甲基吡啶鎓陽離子、1,4-二乙基-2-甲基吡啶鎓陽離子、1,4-二乙基-3-甲基吡啶鎓陽離子、2,3-二乙基-1-甲基吡啶鎓陽離子、2,4-二乙基-1-甲基吡啶鎓陽離子、2,5-二乙基-1-甲基吡啶鎓陽離子、2,6-二乙基-1-甲基吡啶鎓陽離子、3,4-二乙基-1-甲基吡啶鎓陽離子、3,5-二乙基-1-甲基吡啶鎓陽離子、1,2,3,4,5-五甲基吡啶鎓陽離子、1,2,3,4,6-五甲基吡啶鎓陽離子、1,2,3,5,6-五甲基吡啶鎓陽離子、1,2,3,4,5,6-六甲基吡啶鎓陽離子、1-甲基-4-甲基吡啶鎓陽離子、1-乙基-4-甲基吡啶鎓陽離子、1-丙基-4-甲基吡啶鎓陽離子、1-丁基-4-甲基吡啶鎓陽離子、1-戊基-4-甲基吡啶鎓陽離子、1-己基-4-甲基吡啶鎓陽離子、1-庚基-4-甲基吡啶鎓陽離子、1-辛基-4-甲基吡啶鎓陽離子、1-壬基-4-甲基吡啶鎓陽離子、1-癸基-4-甲基吡啶鎓陽離子等在吡啶環之碳原子上有烷基之1-烷基吡啶鎓陽離子。Examples of the pyridinium cation include 1-methylpyridinium cation, 1-ethylpyridinium cation, 1-propylpyridinium cation, 1-butylpyridinium cation, and 1-pentylpyridine. Ruthenium cation, 1-hexylpyridinium cation, 1-heptylpyridinium cation, 1-octylpyridinium cation, 1-mercaptopyridinium cation, 1-mercaptopyridinium cation, 1,2-dimethylpyridine Ruthenium cation, 1,3-dimethylpyridinium cation, 1,4-dimethylpyridinium cation, 1-ethyl-2-methylpyridinium cation, 2-ethyl-1-methylpyridinium cation , 1-ethyl-3-methylpyridinium cation, 3-ethyl-1-methylpyridinium cation, 1-ethyl-4-methylpyridinium cation, 4-ethyl-1-methylpyridine Ruthenium cation, 1,2-diethylpyridinium cation, 1,3-diethylpyridinium cation, 1,4-diethylpyridinium cation, 1,2,3-trimethylpyridinium cation, 1 , 2,4-trimethylpyridinium cation, 1,3,4-trimethylpyridinium cation, 1,3,5-trimethylpyridinium cation, 1,2,5-trimethylpyridinium cation 1,2,6-trimethylpyridinium cation, 1-B Benzyl-2,3-dimethylpyridinium cation, 1-ethyl-2,4-dimethylpyridinium cation, 1-ethyl-2,5-dimethylpyridinium cation, 1-ethyl- 2,6-lutidine cation, 1-ethyl-3,4-dimethylpyridinium cation, 1-ethyl-3,5-dimethylpyridinium cation, 2-ethyl-1, 3-dimethylpyridinium cation, 2-ethyl-1,4-dimethylpyridinium cation, 2-ethyl-1,5-dimethylpyridinium cation, 2-ethyl-1,6- Dimethylpyridinium cation, 3-ethyl-1,2-dimethylpyridinium cation, 3-ethyl-1,4-dimethylpyridinium cation, 3-ethyl-1,5-dimethyl Pyridinium cation, 3-ethyl-1,6-dimethylpyridinium cation, 4-ethyl-1,2-dimethylpyridinium cation, 4-ethyl-1,3-dimethylpyridine Ruthenium cation, 1,2-diethyl-3-methylpyridinium cation, 1,2-diethyl-4-methylpyridinium cation, 1,2-diethyl-5-methylpyridinium cation 1,2-diethyl-6-methylpyridinium cation, 1,3-diethyl-2-methylpyridinium cation, 1,3-diethyl-4-methylpyridinium cation, 1 , 3-diethyl-5-methylpyridinium cation, 1,3-diethyl-6- Methylpyridinium cation, 1,4-diethyl-2-methylpyridinium cation, 1,4-diethyl-3-methylpyridinium cation, 2,3-diethyl-1-methyl Pyridinium cation, 2,4-diethyl-1-methylpyridinium cation, 2,5-diethyl-1-methylpyridinium cation, 2,6-diethyl-1-methylpyridinium Cation, 3,4-diethyl-1-methylpyridinium cation, 3,5-diethyl-1-methylpyridinium cation, 1,2,3,4,5-pentamethylpyridinium cation 1,2,3,4,6-pentamethylpyridinium cation, 1,2,3,5,6-pentamethylpyridinium cation, 1,2,3,4,5,6-hexamethyl Pyridinium cation, 1-methyl-4-methylpyridinium cation, 1-ethyl-4-methylpyridinium cation, 1-propyl-4-methylpyridinium cation, 1-butyl-4- Methylpyridinium cation, 1-pentyl-4-methylpyridinium cation, 1-hexyl-4-methylpyridinium cation, 1-heptyl-4-methylpyridinium cation, 1-octyl-4 a 1-alkylpyridinium group having an alkyl group at a carbon atom of the pyridine ring, such as a methylpyridinium cation, a 1-mercapto-4-methylpyridinium cation, a 1-mercapto-4-methylpyridinium cation or the like cation.

作為四烷基鏻陽離子者,可列舉如:四甲基鏻陽離子、四乙基鏻陽離子、四丙基鏻陽離子、四丁基鏻陽離子、四戊基鏻陽離子、四己基鏻陽離子、四庚基鏻陽離子、四辛基鏻陽離子、四壬基鏻陽離子、四癸甲基鏻陽離子、四苯基鏻陽離子、1,1,1-三丁基-1-辛基鏻陽離子、1,1,1-三丁基-1-壬基鏻陽離子、1,1,1-三丁基-1-癸基鏻陽離子、1,1,1-三丁基-1-十一烷基鏻陽離子、1,1,1-三丁基-1-十二烷基鏻陽離子、1,1,1-三丁基-1-十三烷基鏻陽離子、1,1,1-三丁基-1-十四烷基鏻陽離子、1,1,1-三丁基-1-十五烷基鏻陽離子、1,1,1-三丁基-1-十六烷基鏻陽離子、1,1,1-三丁基-1-十七烷基鏻陽離子、1,1,1-三丁基-1-十八烷基鏻陽離子、1,1,1-三丁基-1-十九烷基鏻陽離子、1,1,1-三丁基-1-二十烷基鏻陽離子、1,1,1-三戊基-1-辛基鏻陽離子、1,1,1-三戊基-1-壬基鏻陽離子、1,1,1-三戊基-1-癸基鏻陽離子、1,1,1-三戊基-1-十一烷基鏻陽離子、1,1,1-三戊基-1-十二烷基鏻陽離子、1,1,1-三戊基-1-十三烷基鏻陽離子、1,1,1-三戊基-1-十四烷基鏻陽離子、1,1,1-三戊基-1-十五烷基鏻陽離子、1,1,1-三戊基-1-十六烷基鏻陽離子、1,1,1-三戊基-1-十七烷基鏻陽離子、1,1,1-三戊基-1-十八烷基鏻陽離子、1,1,1-三戊基-1-十九烷基鏻陽離子、1,1,1-三戊基-1-二十烷基鏻陽離子、1,1,1-三己基-1-辛基鏻陽離子、1,1,1-三己基-1-壬基鏻陽離子、1,1,1-三己基-1-癸基鏻陽離子、1,1,1-三己基-1-十一烷基鏻陽離子、1,1,1-三己基-1-十二烷基鏻陽離子、1,1,1-三己基-1-十三烷基鏻陽離子、1,1,1-三己基-1-十五烷基鏻陽離子、1,1,1-三己基-1-十六烷基鏻陽離子、1,1,1-三己基-1-十七烷基鏻陽離子、1,1,1-三己基-1-十八烷基鏻陽離子、1,1,1-三己基-1-十九烷基鏻陽離子、1,1,1-三己基-1-二十烷基鏻陽離子、1,1,1-三庚基-1-辛基鏻陽離子、1,1,1-三庚基-1-壬基鏻陽離子、1,1,1-三庚基-1-癸基鏻陽離子、1,1,1-三庚基-1-十一烷基鏻陽離子、1,1,1-三庚基-1-十二烷基鏻陽離子、1,1,1-三庚基-1-十三烷基鏻陽離子、1,1,1-三庚基-1-十四烷基鏻陽離子、1,1,1-三庚基-1-十五烷基鏻陽離子、1,1,1-三庚基-1-十六烷基鏻陽離子、1,1,1-三庚基-1-十七烷基鏻陽離子、1,1,1-三庚基-1-十八烷基鏻陽離子、1,1,1-三庚基-1-十九烷基鏻陽離子、1,1,1-三庚基-1-二十烷基鏻陽離子、1,1,1,1-四辛基鏻陽離子、1,1,1-三辛基-1-壬基鏻陽離子、1,1,1-三辛基-1-癸基鏻陽離子、1,1,1-三辛基-1-十一烷基鏻陽離子、1,1,1-三辛基-1-十二烷基鏻陽離子、1,1,1-三辛基-1-十三烷基鏻陽離子、1,1,1-三辛基-1-十四烷基鏻陽離子、1,1,1-三辛基-1-十五烷基鏻陽離子、1,1,1-三辛基-1-十六烷基鏻陽離子、1,1,1-三辛基-1-十七烷基鏻陽離子、1,1,1-三辛基-1-十八烷基鏻陽離子、1,1,1-三辛基-1-十九烷基鏻陽離子、1,1,1-三辛基-1-二十烷基鏻陽離子等。Examples of the tetraalkyl phosphonium cation include a tetramethyl phosphonium cation, a tetraethyl phosphonium cation, a tetrapropyl phosphonium cation, a tetrabutyl phosphonium cation, a tetrapentyl phosphonium cation, a tetrahexyl phosphonium cation, and a tetraheptyl group. Ruthenium cation, tetraoctylphosphonium cation, tetradecylphosphonium cation, tetramethylhydrazine cation, tetraphenylphosphonium cation, 1,1,1-tributyl-1-octylphosphonium cation, 1,1,1 a tributyl-1-indenyl cation, a 1,1,1-tributyl-1-indenyl cation, a 1,1,1-tributyl-1-undecylphosphonium cation, 1, 1,1-tributyl-1-dodecylphosphonium cation, 1,1,1-tributyl-1-tridecylphosphonium cation, 1,1,1-tributyl-1-tetradecyl Alkyl phosphonium cation, 1,1,1-tributyl-1-pentadecyl phosphonium cation, 1,1,1-tributyl-1-hexadecyl sulfonium cation, 1,1,1-three a butyl-1-heptadecylphosphonium cation, a 1,1,1-tributyl-1-octadecylphosphonium cation, a 1,1,1-tributyl-1-nonylalkylphosphonium cation, 1,1,1-tributyl-1-eicosylphosphonium cation, 1,1,1-tripentyl-1-octylphosphonium cation, 1,1,1-tripentyl-1-fluorenyl Ruthenium cation, 1,1,1-tripentyl-1-indenyl cation, 1 1,1,1-tripentyl-1-undecylphosphonium cation, 1,1,1-tripentyl-1-dodecylphosphonium cation, 1,1,1-tripentyl-1-deca Trialkylsulfonium cation, 1,1,1-tripentyl-1-tetradecylphosphonium cation, 1,1,1-tripentyl-1-pentadecylsulfonium cation, 1,1,1- Triamyl-1-hexadecylphosphonium cation, 1,1,1-tripentyl-1-heptadecylphosphonium cation, 1,1,1-tripentyl-1-octadecylphosphonium cation 1,1,1-Tripentyl-1-nonadecylphosphonium cation, 1,1,1-tripentyl-1-eicosylphosphonium cation, 1,1,1-trihexyl-1- Octyl cation, 1,1,1-trihexyl-1-indenyl cation, 1,1,1-trihexyl-1-indenyl cation, 1,1,1-trihexyl-1-111 Alkyl phosphonium cation, 1,1,1-trihexyl-1-dodecylphosphonium cation, 1,1,1-trihexyl-1-tridecylphosphonium cation, 1,1,1-trihexyl- 1-pentadecylphosphonium cation, 1,1,1-trihexyl-1-hexadecylphosphonium cation, 1,1,1-trihexyl-1-heptadecylphosphonium cation, 1,1,1 - trihexyl-1-octadecylphosphonium cation, 1,1,1-trihexyl-1-nonylalkylphosphonium cation, 1,1,1-trihexyl-1-eicosylphosphonium cation, 1 1,1-triheptyl-1-octylhydrazine Ionic, 1,1,1-triheptyl-1-indenyl cation, 1,1,1-triheptyl-1-indenyl cation, 1,1,1-triheptyl-1-111 Alkyl phosphonium cation, 1,1,1-triheptyl-1-dodecyl sulfonium cation, 1,1,1-triheptyl-1-tridecyl sulfonium cation, 1,1,1-three a heptyl-1-tetradecylphosphonium cation, a 1,1,1-triheptyl-1-pentadecylsulfonium cation, a 1,1,1-triheptyl-1-hexadecylphosphonium cation, 1,1,1-triheptyl-1-heptadecylphosphonium cation, 1,1,1-triheptyl-1-octadecylphosphonium cation, 1,1,1-triheptyl-1- Pentadecylphosphonium cation, 1,1,1-triheptyl-1-eicosylphosphonium cation, 1,1,1,1-tetraoctylphosphonium cation, 1,1,1-trioctyl- 1-indenyl cation, 1,1,1-trioctyl-1-indenyl cation, 1,1,1-trioctyl-1-undecylphosphonium cation, 1,1,1-three An octyl-1-dodecylphosphonium cation, a 1,1,1-trioctyl-1-tridecylsulfonium cation, a 1,1,1-trioctyl-1-tetradecylphosphonium cation, 1,1,1-trioctyl-1-pentadecylsulfonium cation, 1,1,1-trioctyl-1-hexadecylphosphonium cation, 1,1,1-trioctyl-1- Heptadecylphosphonium cation, 1,1,1-trioctyl-1-octadecyl cation Child, 1,1,1-octyl-1-phosphonium cations, nonadecyl, eicosyl 1,1,1-octyl-1-phosphonium cation.

在此等鎓離子中,以三辛基甲基銨陽離子、1-甲基-3-丙基咪唑啉鎓陽離子、1-己基-4-甲基吡啶鎓陽離子、1-辛基-4-甲基吡啶鎓陽離子、及1-辛基吡啶鎓陽離子為佳。Among these cesium ions, trioctylmethylammonium cation, 1-methyl-3-propylimidazolium cation, 1-hexyl-4-methylpyridinium cation, 1-octyl-4-methyl The pyridinium cation and the 1-octylpyridinium cation are preferred.

A- 所示陰離子,係六氟化磷陰離子(PF6 - ;hexafluoro phosphate anion),作為鎓鹽(1)者,以三辛基甲基銨=六氟磷酸、1-甲基-3-丙基咪唑啉鎓=六氟磷酸、1-己基-4-甲基吡啶鎓=六氟磷酸、1-辛基-4-甲基吡啶鎓=六氟磷、及1-辛基吡啶鎓=六氟磷酸為佳。A - shown anion, hexafluorophosphate anion (PF 6 - ; hexafluoro phosphate anion), as a sulfonium salt (1), trioctylmethylammonium = hexafluorophosphoric acid, 1-methyl-3-propanol Imidazolinium hydrazine=hexafluorophosphoric acid, 1-hexyl-4-methylpyridinium=hexafluorophosphoric acid, 1-octyl-4-methylpyridinium=hexafluorophosphorus, and 1-octylpyridinium=hexafluoro Phosphoric acid is preferred.

鎓鹽(1),例如,可以藉由式(2):The bismuth salt (1), for example, can be obtained by the formula (2):

Q+ ‧X-  (2)Q + ‧X - (2)

(式中,Q+ 表示與前述相同意義,X- 表示鹵素離子。)(wherein, Q + represents the same meaning as described above, and X - represents a halogen ion.)

所示鎓=鹵化物,與式(3):Show 鎓 = halide, and formula (3):

M+ ‧A-  (3)M + ‧A - (3)

(式中,M+ 表示氫離子或鹼金屬離子,A- 表示與前述相同意義。)(wherein M + represents a hydrogen ion or an alkali metal ion, and A - represents the same meaning as described above.)

所示酸或其之鹼金屬鹽的離子交換反應而製造。該離子交換反應,可以根據習知之方法來進行。It is produced by an ion exchange reaction of an acid or an alkali metal salt thereof. This ion exchange reaction can be carried out according to a conventional method.

有機鹼,可以列舉一級胺、二級胺、三級胺等有機氮化合物、三級膦等有機磷化合物等。其中以三級胺及三級膦為佳。三級胺可以列舉:三甲基胺、三乙基胺、三丙基胺、三丁基胺、三戊基胺、三己基胺、三庚基胺、三辛基胺、三壬基胺、三癸基胺等脂肪族三級胺、N,N-二甲基苯胺、N,N-二乙基苯胺、N-苄基-N-乙基苯胺等芳香族三級胺、吡啶、2-甲基吡啶、3-甲基吡啶、4-甲基吡啶、2,6-二甲基吡啶(lutidine)、3,5-二甲基吡啶、2,3,5-可力丁(即,2,3,5-三甲基吡啶;2,3,5-Collidine)、3,5-二乙基吡啶、2,2’-聯吡啶、2,4’-聯吡啶、4,4’-聯吡啶等吡啶類、1-甲基咪唑等咪唑類。三級膦可以列舉:三辛基膦、三苯基膦等。其中,以三丁基胺、三辛基胺、N-苄基-N-乙基苯胺、吡啶、2-甲基吡啶、3-甲基吡啶、4-甲基吡啶、3,5-二乙基吡啶、2,2’-聯吡啶、1-甲基咪唑、三辛基膦、及三苯基膦為佳。Examples of the organic base include organic nitrogen compounds such as primary amines, secondary amines, and tertiary amines, and organic phosphorus compounds such as tertiary phosphines. Among them, tertiary amines and tertiary phosphines are preferred. The tertiary amine may, for example, be trimethylamine, triethylamine, tripropylamine, tributylamine, tripentylamine, trihexylamine, triheptylamine, trioctylamine, tridecylamine, An aliphatic tertiary amine such as tridecylamine, an aromatic tertiary amine such as N,N-dimethylaniline, N,N-diethylaniline or N-benzyl-N-ethylaniline, pyridine, 2- Methylpyridine, 3-methylpyridine, 4-methylpyridine, 2,6-lutidine, 3,5-lutidine, 2,3,5-collidine (ie, 2 , 3,5-trimethylpyridine; 2,3,5-Collidine), 3,5-diethylpyridine, 2,2'-bipyridine, 2,4'-bipyridine, 4,4'-linked Pyridines such as pyridine and imidazoles such as 1-methylimidazole. The tertiary phosphine may, for example, be trioctylphosphine or triphenylphosphine. Among them, tributylamine, trioctylamine, N-benzyl-N-ethylaniline, pyridine, 2-methylpyridine, 3-methylpyridine, 4-methylpyridine, 3,5-diethyl Pyridine, 2,2'-bipyridine, 1-methylimidazole, trioctylphosphine, and triphenylphosphine are preferred.

本發明之鎓鹽組成物係含有鎓鹽(1)與有機鹼。有機鹼之含量,相對於鎓鹽(1),通常是1ppm以上,較佳是10至5000ppm,更佳是10至1000ppm。The onium salt composition of the present invention contains a phosphonium salt (1) and an organic base. The content of the organic base is usually 1 ppm or more, preferably 10 to 5,000 ppm, more preferably 10 to 1,000 ppm based on the cerium salt (1).

本發明之鎓鹽組成物,例如在鎓鹽(1)中添加有機鹼,藉由混合方法等即可製造。添加有機鹼時之溫度,只要可以均勻地混合兩者之溫度就可以而無限制,通常是在10℃以上,而以15℃至100℃為佳,以在20℃至50℃為特佳。The onium salt composition of the present invention can be produced, for example, by adding an organic base to the onium salt (1), by a mixing method or the like. The temperature at which the organic base is added is not particularly limited as long as the temperature of both of them can be uniformly mixed, and is usually 10 ° C or more, preferably 15 ° C to 100 ° C, and particularly preferably 20 ° C to 50 ° C.

本發明之鎓鹽組成物,也可以含有溶劑。溶劑只要對鎓鹽(1)及有機鹼為失活者就可以,而無特別限制,具體上,可以列舉:戊烷、己烷、庚烷、辛烷、癸烷等脂肪族烴溶劑;甲醇、乙醇、丁醇、戊醇、己醇等醇類溶劑、乙酸甲酯、乙酸乙酯等酯溶劑;丙酮、甲基乙基酮、甲基異丁酮等酮溶劑;苯、甲苯、二甲苯等芳香族烴溶劑等,以酯溶劑為佳,乙酸乙酯更佳。此等溶劑可以單獨使用,也可以混合2種以上使用。本發明之鎓鹽組成物在含有溶劑時,此溶劑之含量,相對於鎓鹽(1),通常為1至100重量%,較佳是1至50重量%。The onium salt composition of the present invention may contain a solvent. The solvent may be any one of the sulfonium salt (1) and the organic base, and is not particularly limited. Specific examples thereof include aliphatic hydrocarbon solvents such as pentane, hexane, heptane, octane, and decane; and methanol. Alcohol solvent such as ethanol, butanol, pentanol or hexanol; ester solvent such as methyl acetate or ethyl acetate; ketone solvent such as acetone, methyl ethyl ketone or methyl isobutyl ketone; benzene, toluene and xylene The aromatic hydrocarbon solvent or the like is preferably an ester solvent, and ethyl acetate is more preferable. These solvents may be used singly or in combination of two or more. When the cerium salt composition of the present invention contains a solvent, the content of the solvent is usually from 1 to 100% by weight, preferably from 1 to 50% by weight based on the cerium salt (1).

實施例Example

以下,藉由實施例更具體說明本發明,但本發明不侷限於此等實施例。同時,在以下之實施例中,水分是使用日本京都電子工業公司製Karl-Fisher水分測定裝置(MKA-520)測定,氟離子(F- )是使用Dionex公司製離子層析分析儀(DX-100)測定(測定界限是10ppm)。Hereinafter, the present invention will be specifically described by way of examples, but the invention is not limited to the examples. Meanwhile, in the following examples, the moisture was measured using a Karl-Fisher moisture measuring device (MKA-520) manufactured by Kyoto Electronics Manufacturing Co., Ltd., and the fluoride ion (F - ) was an ion chromatography analyzer (DX-made by Dionex). 100) Measurement (measurement limit is 10 ppm).

製造例1Manufacturing example 1

混合三辛基甲基銨=氯化物39.6g、水51.3g、鉀=六氟磷酸18.0g及甲基乙基酮51.3g。將所得混合物在25℃中攪拌1小時並使之反應。反應終了後,自所得反應混合物,藉由分液操作分離出有機層。將所得之有機層以32.2g水洗淨2次。濃縮所得之有機層。減壓下乾燥所得濃縮殘渣,得到三辛基甲基銨=六氟磷酸(以下簡稱TOMA-PF6)49.3g(收率98%,水分400ppm)。Trioctylmethylammonium chloride = 39.6 g of chloride, 51.3 g of water, 18.0 g of potassium = hexafluorophosphate, and 51.3 g of methyl ethyl ketone. The resulting mixture was stirred at 25 ° C for 1 hour and allowed to react. After the end of the reaction, the organic layer was separated from the obtained reaction mixture by a liquid separation operation. The resulting organic layer was washed twice with 32.2 g of water. The resulting organic layer was concentrated. The obtained concentrated residue was dried under reduced pressure to give 40.3 g of trioctylmethylammonium (hereinafter referred to as TOMA-PF6) (yield 98%, moisture: 400 ppm).

製造例2Manufacturing Example 2

在製造例1中,除了使用1-甲基-3-丙基咪唑啉鎓=溴化物取代三辛基甲基銨=氯化物,以二氯甲烷取代甲基乙基酮之外,其餘與製造例1同樣實施,製得1-甲基-3-丙基咪唑啉鎓=六氟磷酸(以下簡稱MPIM-PF6)24.2g(收率91%,水分900ppm)。In Production Example 1, except that 1-methyl-3-propylimidazolinium oxime = bromide was substituted for trioctylmethylammonium = chloride, and methyl ethyl ketone was replaced with dichloromethane. In the same manner as in Example 1, 24.2 g of 1-methyl-3-propylimidazolinium = hexafluorophosphoric acid (hereinafter abbreviated as MPIM-PF6) (yield 91%, moisture: 900 ppm) was obtained.

製造例3Manufacturing Example 3

在製造例2中,除了使用1-己基-4-甲基吡啶鎓=溴化物取代1-甲基-3-丙基咪唑啉鎓=溴化物之外,其餘與製造例2同樣實施,製得1-己基-4-甲基吡啶鎓=六氟磷酸(以下簡稱HMPy-PF6)30.6g(收率96%,水分600ppm)。In Production Example 2, the same procedure as in Production Example 2 was carried out except that 1-hexyl-4-methylpyridinium bromide was used instead of 1-methyl-3-propylimidazolinium oxime bromide. 1-hexyl-4-methylpyridinium=hexafluorophosphoric acid (hereinafter abbreviated as HMPy-PF6) 30.6 g (yield 96%, moisture 600 ppm).

製造例4Manufacturing Example 4

在製造例2中,除了使用1-辛基-4-甲基吡啶鎓=溴化物取代1-甲基-3-丙基咪唑啉鎓=溴化物之外,其餘與製造例2同樣實施,製得1-辛基-4-甲基吡啶鎓=六氟磷酸(以下簡稱OMPy-PF6)33.5g(收率97%,水分600ppm)。In Production Example 2, the same procedure as in Production Example 2 was carried out except that 1-octyl-4-methylpyridinium bromide was used instead of 1-methyl-3-propylimidazolinium oxime bromide. 1-octyl-4-methylpyridinium=hexafluorophosphoric acid (hereinafter abbreviated as OMPy-PF6) 33.5 g (yield 97%, moisture 600 ppm) was obtained.

製造例5Manufacturing Example 5

在製造例2中,除了使用1-辛基吡啶鎓=溴化物取代1-甲基-3-丙基咪唑啉鎓=溴化物之外,其餘與製造例2同樣實施,製得1-辛基吡啶鎓=六氟磷酸(以下簡稱OPy-PF6)32.1g(收率97%,水分200ppm)。In Production Example 2, 1-octyl was obtained in the same manner as in Production Example 2 except that 1-octylpyridinium bromide was used instead of 1-methyl-3-propylimidazolinium oxime bromide. Pyridinium = hexafluorophosphoric acid (hereinafter abbreviated as OPy-PF6) 32.1 g (yield 97%, moisture 200 ppm).

實施例1Example 1

將TOMA-PF6 100g及三辛基胺0.05g秤量到玻璃容器內之後,在大氣中密封,藉由回旋式旋轉攪拌機,在室溫中混合1小時,調製含有TOMA-PF6與三辛基胺之鎓鹽組成物。將含有所得鎓鹽組成物之玻璃容器保存在80℃之恆溫槽中。每天採取預定量之試料,測定試料中氟離子(F- )之濃度。結果在表1中表示。After weighing 100 g of TOMA-PF6 and 0.05 g of trioctylamine into a glass container, it was sealed in the atmosphere, and mixed at room temperature for 1 hour by a rotary rotary mixer to prepare a product containing TOMA-PF6 and trioctylamine. Barium salt composition. The glass container containing the obtained cerium salt composition was stored in a thermostat at 80 °C. A predetermined amount of sample is taken every day to measure the concentration of fluoride ion (F - ) in the sample. The results are shown in Table 1.

實施例2Example 2

在實施例1中,除了使用4-甲基吡啶取代三辛基胺之外,其餘與實施例1同樣實施,調製含有TOMA-PF6與4-甲基吡啶之鎓鹽組成物。與實施例1同樣,將含有所得鎓鹽組成物之玻璃容器保存在80℃之恆溫槽中。每天採取預定量之試料,測定試料中氟離子(F- )之濃度。結果在表1中表示。In the same manner as in Example 1, except that 4-methylpyridine was used instead of trioctylamine, a hydrazine salt composition containing TOMA-PF6 and 4-methylpyridine was prepared. In the same manner as in Example 1, the glass container containing the obtained cerium salt composition was stored in a thermostatic chamber at 80 °C. A predetermined amount of sample is taken every day to measure the concentration of fluoride ion (F - ) in the sample. The results are shown in Table 1.

實施例3Example 3

在實施例1中,除了使用MPIM-PF6取代TOMA-PF6,以1-甲基咪唑取代三辛基胺之外,其餘與實施例1同樣實施,調製含有MPIM-PF6與1-甲基咪唑之鎓鹽組成物。與實施例1同樣,將含有所得鎓鹽組成物之玻璃容器保存在80℃之恆溫槽中。每天採取預定量之試料,測定試料中F- 之濃度。結果在表1中表示。In Example 1, except that MPIM-PF6 was used instead of TOMA-PF6, and 1-methylimidazole was substituted for trioctylamine, the same procedure as in Example 1 was carried out to prepare a solution containing MPIM-PF6 and 1-methylimidazole. Barium salt composition. In the same manner as in Example 1, the glass container containing the obtained cerium salt composition was stored in a thermostatic chamber at 80 °C. A predetermined amount of the sample is taken every day, and the concentration of F - in the sample is measured. The results are shown in Table 1.

實施例4Example 4

在實施例3中,除了使用4-甲基吡啶取代1-甲基咪唑之外,其餘與實施例3同樣實施,調製含有MPIM-PF6與4-甲基吡啶之鎓鹽組成物。與實施例3同樣,將含有所得鎓鹽組成物之玻璃容器保存在80℃之恆溫槽中。每天採取預定量之試料,測定試料中F- 濃度。結果在表1中表示。In Example 3, a ruthenium salt composition containing MPIM-PF6 and 4-methylpyridine was prepared in the same manner as in Example 3 except that 4-methylpyridine was used instead of 1-methylimidazole. In the same manner as in Example 3, the glass container containing the obtained cerium salt composition was stored in a thermostatic chamber at 80 °C. A predetermined amount of sample is taken every day to determine the F - concentration in the sample. The results are shown in Table 1.

實施例5Example 5

在實施例4中,除了使用HMPy-PF6取代MPIM-PF6之外,其餘與實施例4同樣實施,調製含有HMPy-PF6與4-甲基吡啶之鎓鹽組成物。與實施例4同樣,將含有所得鎓鹽組成物之玻璃容器保存在80℃之恆溫槽中。每天採取預定量之試料,測定試料中F- 之濃度。結果在表1中表示。In Example 4, a ruthenium salt composition containing HMPy-PF6 and 4-methylpyridine was prepared in the same manner as in Example 4 except that HMPy-PF6 was used instead of MPIM-PF6. In the same manner as in Example 4, the glass container containing the obtained cerium salt composition was stored in a thermostatic chamber at 80 °C. A predetermined amount of the sample is taken every day, and the concentration of F - in the sample is measured. The results are shown in Table 1.

實施例6Example 6

在實施例4中,除了使用OMPy-PF6取代MPIM-PF6之外,其餘與實施例4同樣實施,調製含有OMPy-PF6與4-甲基吡啶之鎓鹽組成物。與實施例4同樣,將含有所得鎓鹽組成物之玻璃容器保存在80℃之恆溫槽中。每天採取預定量之試料,測定試料中F- 之濃度。結果在表1中表示。In the same manner as in Example 4 except that OMPy-PF6 was used instead of MPIM-PF6, a sulfonium salt composition containing OMPy-PF6 and 4-methylpyridine was prepared. In the same manner as in Example 4, the glass container containing the obtained cerium salt composition was stored in a thermostatic chamber at 80 °C. A predetermined amount of the sample is taken every day, and the concentration of F - in the sample is measured. The results are shown in Table 1.

實施例7Example 7

在實施例1中,除了使用OPy-PF6取代TOMA-PF6,以3,5-二乙基吡啶取代三辛基胺之外,其餘與實施例1同樣實施,調製含有OPy-PF6與3,5-二甲基吡啶之鎓鹽組成物。與實施例1同樣,將含有所得鎓鹽組成物之玻璃容器保存在80℃之恆溫槽中。每天採取所預定量之試料,測定試料中F- 之濃度。結果在表1中表示。同時,在表1中,分別以「F- 檢測日數」表示檢測出在1000ppm以上之F- 的試料保存日數,「F- 濃度」是表示當時之F- 濃度測定值。In Example 1, except that OPY-PF6 was used instead of TOMA-PF6, and 3,5-diethylpyridine was substituted for trioctylamine, the same procedure as in Example 1 was carried out, and the preparation contained OPy-PF6 and 3,5. - a quinone salt composition of lutidine. In the same manner as in Example 1, the glass container containing the obtained cerium salt composition was stored in a thermostatic chamber at 80 °C. A predetermined amount of the sample is taken every day, and the concentration of F - in the sample is measured. The results are shown in Table 1. Meanwhile, in Table 1, respectively, "F - detect the number of days" means that F is detected in more than 1000ppm - A sample stored for several days, "F - concentration" is a time of F - concentration measurement.

由表1可知,本發明之鎓鹽組成物,即使有微量水分的存在,在80℃下30天內仍為穩定。As is clear from Table 1, the onium salt composition of the present invention was stable at 80 ° C for 30 days even in the presence of a trace amount of water.

比較例1Comparative example 1

在實施例1中,除了不使用三辛基胺之外,其餘與實施例1同樣實施,每天採取預定量之試料,測定試料中F- 之濃度。結果在表2中表示。同時,在表2中,分別以「F- 檢測日數」表示檢測出在1000ppm以上之F- 濃度的試料保存日數,「(F- 濃度)」是表示當時之F- 濃度測定值。In Example 1, except that trioctylamine was not used, the same procedure as in Example 1 was carried out, and a predetermined amount of the sample was taken every day to measure the concentration of F - in the sample. The results are shown in Table 2. Meanwhile, in Table 2, the number of sample storage days at which the F - concentration of 1000 ppm or more was detected is indicated by "F - detection day number", and "(F - concentration)" is the measured value of the F - concentration at that time.

比較例2Comparative example 2

在實施例3中,除了不使用1-甲基咪唑之外,其餘與實施例3同樣實施,每天採取預定量之試料,測定試料中F- 之濃度。結果在表2中表示。In Example 3, except that 1-methylimidazole was not used, the same procedure as in Example 3 was carried out, and a predetermined amount of the sample was taken every day to measure the concentration of F - in the sample. The results are shown in Table 2.

比較例3Comparative example 3

在實施例5中,除了不使用4-甲基吡啶之外,其餘與實施例5同樣實施,每天採取預定量之試料,測定試料中F- 之濃度。結果在表2中表示。In Example 5, except that 4-methylpyridine was not used, the same procedure as in Example 5 was carried out, and a predetermined amount of the sample was taken every day to measure the concentration of F - in the sample. The results are shown in Table 2.

比較例4Comparative example 4

在實施例6中,除了不使用4-甲基吡啶之外,其餘與實施例6同樣實施,每天採取預定量之試料,測定試料中F- 之濃度。結果在表2中表示。In Example 6, except that 4-methylpyridine was not used, the same procedure as in Example 6 was carried out, and a predetermined amount of the sample was taken every day to measure the concentration of F - in the sample. The results are shown in Table 2.

比較例5Comparative Example 5

在實施例7中,除了不使用3,5-二乙基吡啶之外,其餘與實施例7同樣實施,每天採取預定量之試料,測定試料中F- 之濃度。結果在表2中表示。In Example 7, except that 3,5-diethylpyridine was not used, the same procedure as in Example 7 was carried out, and a predetermined amount of the sample was taken every day to measure the concentration of F - in the sample. The results are shown in Table 2.

實施例8至18Examples 8 to 18

在實施例5中,除了使用表3所記載之有機鹼以取代4-甲基吡啶之外,其餘與實施例5同樣實施,調製鎓鹽組成物。將含有所得鎓鹽組成物之玻璃容器在80℃之恆溫槽中保存。每天採取預定量之試料,測定試料中F- 之濃度。結果,即使經過30天後,F- 濃度仍在檢測界限以下。由此結果可知,本發明之鎓鹽組成物,即使有微量之水分存在,在80℃下30天之內仍為穩定。In the same manner as in Example 5 except that the organic base described in Table 3 was used instead of 4-methylpyridine, the sulfonium salt composition was prepared. The glass vessel containing the obtained cerium salt composition was stored in a thermostat at 80 °C. A predetermined amount of the sample is taken every day, and the concentration of F - in the sample is measured. As a result, even after 30 days, the F - concentration was below the detection limit. From this result, it is understood that the onium salt composition of the present invention is stable even within 30 days at 80 ° C even if a trace amount of water is present.

比較例6至12Comparative Examples 6 to 12

在實施例5中,除了表4所記載之化合物以取代4-甲基吡啶之外,其餘與實施例5同樣實施,調製比較用之鎓鹽組成物。將含有所得比較用之鎓鹽組成物的玻璃容器在80℃之恆溫槽中保存。每天採取預定量之試料,測定試料中之F- 濃度。結果在表4中表示。同時,在表4中,分別以「F- 檢測日數」表示檢測出1000ppm以上之F- 濃度的試料保存日數,「(F- 濃度)」是表示當時F- 濃度之測定值。In Example 5, except that the compound described in Table 4 was substituted for 4-methylpyridine, the same procedure as in Example 5 was carried out to prepare a cerium salt composition for comparison. The glass container containing the obtained cerium salt composition for comparison was stored in a thermostat at 80 °C. A predetermined amount of the sample is taken every day to determine the F - concentration in the sample. The results are shown in Table 4. At the same time, in Table 4, the number of sample storage days at which F - concentration of 1000 ppm or more is detected is indicated by "F - number of detection days", and "(F - concentration)" is a measured value indicating the F - concentration at that time.

實施例19Example 19

將HMPy-PF6 100g、4-甲基吡啶0.05g及乙酸乙酯50g秤量到玻璃容器內之後,在大氣中密封,藉由回旋式旋轉攪拌機,在室溫中混合1小時,調製含有HMPy-PF6與4-甲基吡啶之鎓鹽組成物。將含有所得鎓鹽組成物之玻璃容器保存在60℃之恆溫槽中。每天採取預定量之試料,測定試料中氟離子(F- )之濃度。結果在表5中表示。同時,在表5中,分別以「F- 檢測日數」表示檢測出1000ppm以上之F- 濃度的試料保存日數,「(F- 濃度)」是表示當時F- 濃度之測定值。100 g of HMPy-PF6, 0.05 g of 4-methylpyridine and 50 g of ethyl acetate were weighed into a glass container, sealed in the air, and mixed at room temperature for 1 hour by a rotary rotary mixer to prepare HMPy-PF6. A salt composition with 4-methylpyridine. The glass container containing the obtained cerium salt composition was stored in a thermostat at 60 °C. A predetermined amount of sample is taken every day to measure the concentration of fluoride ion (F - ) in the sample. The results are shown in Table 5. At the same time, in Table 5, the number of sample storage days at which F - concentration of 1000 ppm or more is detected is indicated by "F - number of detection days", and "(F - concentration)" is a measured value indicating the F - concentration at that time.

實施例20Example 20

在實施例19中,除了4-甲基吡啶之使用量改成0.01g之外,其餘與實施例19同樣實施,結果在表5中表示。In Example 19, the same procedure as in Example 19 was carried out except that the amount of 4-methylpyridine used was changed to 0.01 g, and the results are shown in Table 5.

比較例13Comparative Example 13

在實施例19中,除了不使用4-甲基吡啶之外,其餘與實施例19同樣實施,結果在表5中表示。In Example 19, the same procedure as in Example 19 was carried out except that 4-methylpyridine was not used, and the results are shown in Table 5.

比較例14Comparative Example 14

在實施例19中,除了不使用4-甲基吡啶,且乙酸乙酯之使用量改成25g之外,其餘與實施例19同樣實施,結果在表5中表示。In Example 19, the same procedure as in Example 19 was carried out except that 4-methylpyridine was not used, and the amount of ethyl acetate used was changed to 25 g, and the results are shown in Table 5.

比較例15Comparative Example 15

在比較例14中,除了使用異丙醇取代乙酸乙酯之外,其餘與比較例14同樣實施,結果在表5中表示。In Comparative Example 14, the same procedure as in Comparative Example 14 was carried out except that isopropyl alcohol was used instead of ethyl acetate, and the results are shown in Table 5.

實施例21至24Examples 21 to 24

在實施例5中,除了4-甲基吡啶之使用量改由表6所示之量以外,其餘與實施例5同樣實施,調製含有HMPy-PF6與4-甲基吡啶之鎓鹽組成物。與實施例5同樣,將含有所得鎓鹽組成物之玻璃容器在80℃之恆溫槽中保存。每天採取預定量之試料,測定試料中F- 之濃度。結果在表6所示,同時,在表6中,分別以「F- 檢測日數」表示檢測出1000ppm以上之F- 濃度的試料保存日數,「(F- 濃度)」是表示當時F- 濃度之測定值。In the same manner as in Example 5 except that the amount of the 4-methylpyridine used was changed from the amount shown in Table 6, the composition containing the sulfonium salt of HMPy-PF6 and 4-methylpyridine was prepared. In the same manner as in Example 5, the glass container containing the obtained cerium salt composition was stored in a thermostat at 80 °C. A predetermined amount of the sample is taken every day, and the concentration of F - in the sample is measured. The results are shown in Table 6. At the same time, in Table 6, the "F - test days" indicates the number of sample storage days at which F - concentration of 1000 ppm or more was detected, and "(F - concentration)" indicates that F- at that time . The measured value of the concentration.

產業上之可利用性Industrial availability

本發明之鎓鹽組成物,由於很難由微量水分與加熱而起水解,故在處理與長期保存方面,可以維持穩定性。又,如依據本發明之方法,藉由含有有機鹼,就可以抑制因鎓鹽(1)之微量水分與加熱所引起之水解,可以使鎓鹽(1)穩定地保存。Since the onium salt composition of the present invention is difficult to be hydrolyzed by a trace amount of water and heating, stability can be maintained in terms of handling and long-term storage. Further, according to the method of the present invention, by containing an organic base, hydrolysis due to a trace amount of moisture and heating of the cerium salt (1) can be suppressed, and the cerium salt (1) can be stably stored.

Claims (4)

一種鎓鹽組成物,其係含有式(1)所示鎓鹽,與有機氮化合物或有機磷化合物之組成物,其中,相對於式(1)所示鎓鹽,有機氮化合物或有機磷化合物之含量為10至5000ppm,有機氮化合物為選自由脂肪族三級胺、芳香族三級胺及吡啶類所成群組中之至少一種,有機磷化合物為三級膦,式(1):Q+ ‧A- (1)(式中,Q+ 表示四級銨陽離子或四級鏻陽離子,A- 表示PF6 - )。An onium salt composition containing a phosphonium salt represented by the formula (1), and a composition of an organic nitrogen compound or an organophosphorus compound, wherein an organic nitrogen compound or an organic phosphorus compound is represented with respect to the onium salt represented by the formula (1). The content of the organic nitrogen compound is at least one selected from the group consisting of aliphatic tertiary amines, aromatic tertiary amines, and pyridines, and the organophosphorus compound is a tertiary phosphine, and the formula (1): Q + ‧A - (1) (wherein Q + represents a quaternary ammonium cation or a quaternary phosphonium cation, and A - represents PF 6 - ). 如申請專利範圍第1項之鎓鹽組成物,其復含有溶劑。 For example, the bismuth salt composition of claim 1 of the patent scope contains a solvent. 一種鎓鹽之安定化方法,其特徵為混合申請專利範圍第1項之式(1)所示之鎓鹽與有機氮化合物或有機磷化合物者。 A method for the stabilization of a cerium salt, which is characterized by mixing an onium salt and an organic nitrogen compound or an organic phosphorus compound represented by the formula (1) of claim 1 of the patent application. 一種鎓鹽之保存方法,其特徵為使申請專利範圍第1項之式(1)所示之鎓鹽在有機氮化合物或有機磷化合物之存在下保存者。A method for preserving a cerium salt, which is characterized in that the cerium salt represented by the formula (1) of the first aspect of the patent application is preserved in the presence of an organic nitrogen compound or an organic phosphorus compound.
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Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
Dummling S. et al., Current Separations, 1996, 15(2): 53-56 *
Fraser K. J. and MacFarlane D. R., Aust. J. Chem., 2009, 62: 309-321 *
Hernandez-Fernandes F. J. et al., J. Chem. Technol. Biotech., 2007, 82: 882-887 *
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