TW200710070A - Solvent for reaction and production method using the same - Google Patents

Description

200710070 IX. Description of the invention: • Technical field to which the invention pertains - The present invention relates to a solvent for reaction and a method for producing the same. More specifically, it is a solvent for the reaction using a liquid compound (ionic liquid) composed of a cation and an anion, and a production method using the solvent. [Prior Art] The ionic liquid system is a liquid compound composed of a cation and an anion, and has ion conductivity, and is widely used, for example, in a primary battery, a clock (ion) secondary battery, or a fuel cell. And electrochemical devices such as batteries for discharge mechanisms, electrolytic capacitors, electric double layer capacitors, solar cells, electrochromic display elements, and the like. Further, in addition to the use of the temple, the use of various properties of the ionic liquid itself has been discussed for various applications. For example, those having a property of being less reactive with a raw material or a product during the reaction and having stability properties have been discussed as a solvent for various reactions. Regarding ionic liquids, it has been revealed that an alcohol or a hydrocarbon is subjected to acetylation in an ionic liquid (see, for example, 'Stewart A.

Forsyth) ’ "chemical communication", (UK) 'Royal Society of Chemistry, 2002' p. 714-715. ). This document describes that the acetylation reaction can be carried out rapidly and in high yield under mild conditions by using a dicyandiamide-based ionic liquid which is an effective solvent and is an active alkali catalyst. However, there is still room for review in order to obtain an ionic liquid which can be effectively used in reactions other than the acetylation reaction and which can further increase the reaction rate. 5 200710070 Further, the practice of using a specific ionic compound as a solvent for chemical, photochemical, and electrochemical reactions has also been disclosed (refer to, for example, Japanese Patent Laid-Open Publication No. 2000-508677 (Application No. In the examples, 74, and the following examples, etc.)), in the examples, the form in which a salt is used as a catalyst is described. However, there is still room for review as a solvent that is sufficient for stability and can improve the efficiency of the reaction and can also be applied to various reactions. SUMMARY OF THE INVENTION The present invention has been made in view of the above circumstances, and an object of the present invention is to provide a reaction agent which does not volatilize in various processes, does not react with a raw material or a product, is stable over time, and can sufficiently improve reaction efficiency. A method of producing the solvent. The inventors of the present invention have conducted various investigations on the reaction solvent, and have focused on the ionic liquid, and have not reacted with the raw material or the product during the reaction, and have chemical stability and thermal stability characteristics, and found that: When the ionic liquid containing a specific anion is used, the solvent for the reaction exhibits such characteristics because it has such an anion, and does not volatilize to the outside during various reaction processes, and does not react with the raw material or the product. It has been used for a long period of time, and it has been found that it can significantly improve the reaction rate and greatly improve the reaction efficiency, and it can perfectly solve the above problems. Further, it has been found that the effects of the present invention can be more fully exerted by using the solvent for the reaction as a solvent for polymerization. The present invention has been achieved. In other words, the present invention is a solvent for the reaction, which is characterized in that it contains an ionic liquid having an anion represented by the following formula (1). 6 200710070

(where x represents at least one of the groups consisting of B, C, N, 〇, A1, Si, p, and Se). The symplectic symplectic · τη ^ is 1, 1 and 3 are the same or different. The organic linking group; Q represents an organic beauty, and is an integer of i or more, and b, 〇, 3, and 6 are integers of 0 or more. Hereinafter, the present invention will be described in detail.

The solvent (reaction solvent) for the reaction of the present invention contains an ionic liquid having a specific anion, and the "ionic liquid" means a liquid which is composed of a compound composed of a cation and an anion. In the present invention, two or more kinds of the ionic liquids may be contained, and two or more kinds of compounds composed of a cation and an anion may be contained in a mixture of two or more kinds of ionic liquid hydrazine, and the cation or anion may also be used. Can be the same species. The ionic liquid is preferably a liquid having a predetermined volume and fluidity at 40 ° C, and specifically, preferably 4 (200 mPa· under TC, liquid underneath, more preferably The liquid below ^ 〇〇mpa · s is more preferably a liquid of less than $50mPa.s at 40C. Further, the method of measuring the viscosity can be used as a TV_2G (four) meter taper plate type (specially made by the company) The ionic liquid system has an anion represented by the above formula (1). These anions may be an anion of the ionic liquid contained in the solvent for the reaction of the present invention, or may constitute other compounds. By having such an anion, the solvent for the reaction can be sufficiently suppressed from volatilizing to the outside during each reaction, or reacted with a raw material or a product, and the stability of the long period of 2007 200770 can be fully exerted, and the stability can be remarkably improved. The reaction rate greatly increases the reaction efficiency.

In the anion represented by the above formula (1), X represents at least one element selected from the group consisting of B, C, N, 0, Al, Si, p, s, As, and Se, preferably c, N or S. 'It is better to use c or S. Thereby, the heat resistance of the solvent for the reaction can be sufficiently improved, and C is particularly preferable. A and B represent the same or different organic linking groups, and are preferably independently selected from at least one of -S-, -0-, -S02-, and -CO-, and -S〇2_, _c〇• is better. q represents a branch base 'preferably: hydrogen atom, halogen atom, CpFpp+yHq, 0CpF(2P+iq)Hq . S〇2CpF(2p+1.q)Hq ^ C02CpF(2p+1.q)Hq ^ S03C6F5_rHr, N02 (where i 6 , 0 < q$ 13 , 〇 < r$ 5), etc.; ^ ^ ^ ^ ^ ^ ^ ^ ^ . CpF(2p+1.q)Hq > S02CpF(2p+, q) Hq 〇a is an integer of 1 or more, and b, c, d, and e are integers above 〇, and a, ^, and ^ are determined by the valence of the element X, for example, when X is a sulfur (s) atom The occasion is: a = hd = 〇, e = 0; where X is a nitrogen atom: (l) a = 2, (four), e = 0, (2) a = 1, deduction 1, or (7) Π, Any one of deductions and e=1. Also, b&c is better. The anion represented by the above formula (1) is preferably a dicyanamide anion (DCA), a thiocyanate anion, an I cyanomethionate anion (曰T=M), a tetracyanoborate anion, or a cyanide anion ( By cy〇), the physical properties such as heat resistance can be improved, and the reaction efficiency can be further improved by fully exhibiting electrical, chemical, and safety properties. Among them, a tricyanomethylate anion is more preferable. The solvent for the above reaction may suitably be used as a solvent, and may also contain other anions. Other anions may contain, for example, a monocarboxylic acid such as bistrifluoromethanesulfonimide anion (TFSI), tetrafluoroborate anion, acetic acid or benzoic acid; benzoic acid, maleic acid, succinic anion, etc. An acid-reducing anion; a sulfate anion such as methyl sulfate or ethyl sulfate. Further, an oxygen-containing inorganic ion such as a hexafluorophosphate ion, a hexafluoroarsenic acid ion, a hexafluoroantimonic acid ion, a hexafluoroacyl acid ion or a hexa-acid acid ion; a hydrogen phthalate hydrogen ion and a hydrogen maleate can be used. Carboxylic acid ions such as ions, salicylic acid ions, benzoic acid ions, adipic acid ions, etc.; stupid sulfonic acid ions, sulfonium benzene sulfonate ions, dodecane benzene sulfonate ions, trifluoromethanesulfonate ions, perfluoro Acidic ions such as acid ions; inorganic acid ions such as boric acid ions and acid ions; bis(trifluoromethanesulfonate) imine ions, bis(pentafluoroethanesulfonyl)imide ions, three (Trifluoromethanesulfonate) methide ion, perfluoroalkyl fluoroborate ion, perfluoroalkyl fluorophosphate ion, boronic borodicatecholate, boron Borodi glycol at e, borodi salicylate, borotetrakis (trinuoroacetate), bis(oxalato)borate Four-coordinate boron 1 of the foregoing ions or two or. The amount of the anion in the solvent for the reaction (the amount of all the anions present) is 1% by mass of the solvent for the reaction, and the lower limit of the content of the compound derived from the anion is preferably 1% by mass, more preferably It is 5% by weight, and more preferably 10% by mass. Further, the upper limit is preferably 99.5% by mass, more preferably 95% by mass, still more preferably 90% by mass. 9 200710070 Further, in the total anion contained in the reaction, the mass ratio of the anion of the above formula (1) is not more than 1% by mass of the anion, and the lower limit is preferably 8〇. / 1 I ^ 0 in WO g /. . Thereby, the stability of the long period can be more fully exerted, and the reaction rate can be sufficiently increased. The lower limit is more preferably 90% by mass. Further, the solvent for the reaction may contain a cation which constitutes an ionic liquid, and may contain other cations. The cation contained in the solvent for the reaction of the present invention can be suitably used as long as it is a solvent.

Preferably, for example, 'the rust cation represented by the following general formula (7) is used as a necessary component. L——Rs (2) (wherein L represents C, Si, N, P, S or 〇. R is the same or different organic groups, and may also be bonded to each other. 3 is 3, 4 or 5, The cation of the ionic liquid contained in the solvent for the reaction of the present invention is preferably such a cation. Preferably, the ionic liquid is composed of an anion represented by the above formula (1) and a cation represented by the above formula (2). In this case, the ionic liquid composed of the anion represented by the above formula (1) and the cation represented by the above formula (2) is a room temperature molten salt which can be stably maintained in a molten state at normal temperature, and contains such a molten salt. The molten salt of the reaction system of the present invention can exert a more sufficient stability for a long period of time, and can further increase the reaction rate in various reaction processes. Further, the molten salt refers to a liquid which is stable in a temperature range from room temperature to 8 (TC). The phosphonium cation represented by the above formula (2), more preferably represented by the following formula 200710070

Rl~frR R

R R-

R

R

R~〇e-R r\^r

RR is the same as (wherein R is the same as the above formula (2), and the cation of the following (1) to (IV) is particularly preferable. Further, the following (ΐΜΐπ) represents a cation. In the formula, r1 to ru are the same or different organic groups, and may also be a bond to each other, preferably a dimethane atom, a fluorine atom, an amine group, an imine group, an amine group, a (10) group, an ester group, : a base, a slow base, an amine methyl group, a cyano group, a continuation base, a sulfonyl group (tetra) cytidine, or a linear, branched or cyclic carbon and may contain a nitrogen atom, an oxygen atom, a sulfur atom or the like. More preferably, it is a hydrocarbon group, a carbonized fluorine group or the like; more preferably: a hydrogen atom, a fluorine atom, a cyano group, a mercapto group, a carbon group of a carbon number 8, and a carbonized a group. (1) Ten kinds of heterocyclic rust cations represented by the following formula. 11 200710070

12 200710070 (II) Five kinds of unsaturated rust cations represented by the following formula.

(III) Nine kinds of saturated ring-recording cations represented by the following formula.

13 200710070 (IV) R is a chain rust cation of an alkyl group of Cl~C8. Among these rust cations, the most preferable one is the neutron of the general formula (2); the best one is · the following general formula L is the scorpion

(wherein R1 to R12 are the same as those of Ri to R12 in the above formula (I) to (III)), or triethylmethylammonium or dimethylethlyl. A chain ruthenium cation such as money, diethylmethylmethoxyethylammonium, trimethylpropylammonium, trimethylbutylammonium or trimethylhexylammonium. In the solvent for the above reaction, the amount of the cation (the presence of all cations 1) is the lower limit, and the anion of the anion present in the solvent for the reaction is 1 mol, and 200710070 is preferably 〇·5 mol, more preferably 〇· 8 moles. Further, the upper limit is preferably 2. 莫 Moule, more preferably 1.2 Mo. Further, the mass ratio of the rust cations represented by the above formula (2) in the total cations contained in the solvent for the reaction is 100% by mass based on the total amount of the cations, and the lower limit is preferably 80% by mass. Thereby, the stability in the long period can be more fully exhibited' and the reaction rate can be sufficiently increased. A lower limit is preferably 9 〇 mass%. The solvent for the above reaction may further contain water or an organic solvent. The organic > solvent may, for example, be 1,2-dimethoxyethane, tetrahydrofuran, 2-methyltetrahydrofuran, crown test, triethylene glycol methyl ether, tetraethylene glycol dimethyl scale, and second odor burn Scales; carbonates such as ethylene carbonate, propylene carbonate, diethyl carbonate, mercaptoethyl carbonate; dimethyl carbonate, ethyl methyl carbonate, diethyl carbonate, carbonic acid a chain carbonate such as phenyl ester or methyl phenyl carbonate; ethylene carbonate, propylene carbonate, 2,3-dimethylethylene carbonate, butylene carbonate, vinylene carbonate, 2-Asia a cyclic carbonate such as ethylene vinyl carbonate; an aliphatic carboxylic acid ester such as methyl formate, methyl acetate, propionic acid, methyl propionate, ethyl acetate, propyl acetate, butyl acetate or amyl acetate; An aromatic carboxylic acid ester such as methyl benzoate or ethyl benzoate; a carboxylic acid ester such as Τ-butyrolactone, 7-valerolactone or 6-valerolactone; trimethyl phosphate, phosphoric acid Phosphate esters such as ethyl dimethyl ester, diethyl phosphate, and triethyl phosphate; acetonitrile, propionitrile, methoxypropionitrile, glutaronitrile a nitrile such as adiponitrile or 2-methylglutaronitrile; Ν-methylformamide, Ν-ethyl decylamine, hydrazine, hydrazine-dimethylformamide, hydrazine, hydrazine-dimethyl Ethyl amide, Ν-曱 卩 洛 洛 _ ( (pyrrolidinon), Ν-methyl itt σ each ketone, Ν-ethylene group 15 200710070 pyrrolidone and other guanamines; Sulfur compounds such as methylmethyl maple, diethylene maple, cyclobutyl milling, 3_fluorene ring milling, 2,4-dimethylcyclobutyl maple; ethylene glycol, propylene glycol, ethylene glycol monomethyl ether, Alcohols such as ethylene glycol monoethyl ether; ethylene glycol dimethyl ether, ethylene glycol diethyl ether, 14-dioxane, iota, 2-dioxolane, tetrahydrofuran, 2-methyltetrahydrofuran, 2,6 An ether of dimethyltetrahydrofuran or tetrahydropyran; a sub-mill of dimethyl arylene, methyl ethyl yam, diethyl yam, etc.; an aromatic nitrile of benzonitrile, tolyl nitrile, etc. Class; nitropyrrolidine, 1,3-dimethyl-2-mercaptopurine (imidazolidinone), 1,3·dimethyl-3,4,5,6-tetrahydro-2(1H)- One or two or more of these may be used, such as pyrimidinone and 3-methyl-2-oxazolidine. Among them, carbonates, aliphatic esters, and sulphones are preferred, and carbonates are more preferred, and cyclic esters such as 7-butyrolactone and 7-valerolactone are preferred. When the solvent for the above reaction contains water or an organic solvent, the upper limit of the content ratio of the water to the organic solvent is preferably 99% by mass. Thereby, the volatile matter can be sufficiently reduced, and for example, at a low temperature of -55 ° C. It is not; East knot, which is excellent in chemical and thermal stability. It is preferably 85 mass%./◦, more preferably 75 mass%, especially preferably 65 mass%. The lower limit is i mass%. Preferably, the ratio is 1.5% by mass, more preferably 20% by mass, and particularly preferably 5% by mass. Further, when the solvent for the reaction contains a nonaqueous solvent, it is preferred to control the moisture content, whereby the influence of water can be sufficiently reduced, and the reaction efficiency can be improved. Specifically, when a nonaqueous solvent is contained, the upper limit of the concentration of the water in the solvent for the reaction is 1 詈. Only set / 〇 Feng Jia, to 〇. 1 夤 % % is better. Further, the lower limit is preferably 0.01% by mass. 200710070 The solvent for the above reaction is preferably a viscosity of 300 mPa·s or less at 25 ° C, whereby the reaction efficiency can be sufficiently improved. It is preferably 200 mPa·s or less, and more preferably 100 mPa·s or less. The method for measuring the viscosity is not particularly limited, and is preferably, for example, a method of measuring at a temperature of 25 ° C using a TV-20 type viscometer cone-and-plate type (manufactured by Hitachi, Ltd.). The solvent for the above reaction is preferably composed of a nitrogen heterocyclic cation having a conjugated double bond as an essential component, whereby electrochemical stability can be improved, and the reaction can be applied to more reactions. The nitrogen heterocyclic cation having a conjugated double bond, the heterocyclic rust cation of the oxime type of the above (1) or the unsaturated rust cation of the above five types (11) preferably have a common double bond. Further, in the above formula (2), L is a nitrogen atom. The solvent for the above reaction may preferably be one which contains an alkali metal salt and/or an alkaline earth metal salt. The solvent for the reaction of the present invention containing an alkali metal salt and/or an alkaline earth metal salt is electrolyte-containing, and may be suitable for use in an electric reaction. The alkali metal salt is preferably a lithium salt, a sodium salt or a potassium salt, and the alkaline earth metal salt is preferably a calcium salt or a magnesium salt. Especially lithium salt is better. Further, the alkali metal salt and/or the alkaline earth metal salt may be a compound which is formed by the above anion, or may be another compound. In the case of a compound having an anion as an essential component, it is preferably an alkali metal salt and/or an alkaline earth metal salt of an anion represented by the above formula (1), more preferably a clock salt. ^ Hold this lithium salt, in addition to the above preferred anion 1 , with LiC(CN)3, LiSi(CN)3, LiB(CN)4, UA1(CN)4, 17 200710070

LiP(CN)2, LiP(CN)6, LiAs(CN)6, LiOCN, LiSCN, etc. are preferred. In the case of other compounds, an electrolyte salt having a large dissociation constant in the solvent for the reaction is preferred, and for example, an alkali metal salt or an alkaline earth metal salt of methanesulfonic acid is preferably referred to as LiCF3S03, NaCF3S03, KCFsSO3 or the like;

Perfluoroalkane (alkane) sulfonate such as LiN(CF3S03)3 and LiN(CF3CF3S02)2

A metal salt or an alkaline earth metal salt of an acid imine; an alkali metal salt or an alkaline earth metal salt of a hexafluorophosphoric acid such as LipF6, NaPF6 or KPF6; a peroxyacid alkali metal salt or an alkaline earth metal salt such as LiCl〇4 or NaC1〇4; ; LiBF4, NaBF4, etc., tetracycline, LiAsF6, Lil, Nal, NaAsF6, KI, etc. alkali metal salts. Among these, in view of solubility or ionic conductivity, it is preferred to use an alkali metal salt or an alkaline earth metal salt of UBF4, LiAsF6 or perfluoroalkanesulfinate. The solvent for the reaction may also contain other electrolyte salts, preferably: a tetrabasic salt of a peroxyacid such as a peroxyacid tetraethyl group; a fourth-grade tetrahydrotetrafluoroborate of AH Shanqing 4 or the like; Γ Γ ( (c2h5) 4npf6 4 quaternary salt; (CH3) 4P · BF4, (C2H5) 4p · z 丄, 2 bf4 4 quaternary salt, etc., in terms of solubility or ionic conductivity, quaternary ammonium Salt is better. In the above reaction, the solvent is used in the presence of a Thunder and a sputum, and the presence of a scorpion, a scorpion, and a lower limit of 0.1% by mass. The upper limit of the electrolyte salt is 50% by mass. If you come to the market, you can't get it. The right is less than 0.1%, and the ion is not enough. You can't fully improve it. χ ^ ^ 疋 虞 虞 若 若 若 若 若 若 若 若 若 若 若 若 若 若 若 若 若 若 若 若 若 若 若 若The ion movement is made smoother. The upper limit of the yttrium is 30 masses. The electrophoresis can be made into a solvent more suitable for electrochemical reaction by containing the substance. These are more suitable for the reaction of protons. 2007 2007070 Solvent is also one of the preferred forms of the invention. Further, in the present invention, protons are present in the solvent by containing a compound which can dissociate and generate protons. The amount of proton present in the solvent for the above reaction is preferably 0. 01 mol/L for the anti-application solvent, and preferably 1 〇 mol/L. If it is less than 0.01 m/L, the absolute amount of protons is insufficient, and there is no possibility of improving the proton conductivity; if it exceeds 10 m/L, the movement of protons cannot be smoother. A preferred upper limit is 5 moles/L. In the above-mentioned reaction, the granules may contain one or more of the above-mentioned constituent elements, and may contain various inorganic oxide fine particles, as long as the effects of the present invention are exerted. The inorganic oxide fine particles are preferably those which have stable non-electron conduction and electrochemical properties. Such fine particles are preferably ion conductivity of α, cold, 7-alumina, cerium oxide, titania, cerium oxide, magnesium oxide, barium titanate, titanium oxide, hydrotalcite, and the like.戋非

Conductive ceramic microparticles. The specific surface area of the inorganic oxide fine particles is preferably as large as possible. Specifically, the 卩BET method is preferably 5 m 2 /g or more, more preferably 5 〇 m 2 /g or more. The crystal grain size of the inorganic oxide fine particles may be mixed with other components in the solvent for reaction, and the size (average crucible, particle diameter) is preferably 〇. 20"m below is better than ol/zm and below 2/zm. As the shape of the inorganic oxide fine particles, various shapes such as a spherical shape, an oval shape, a cubic shape, a rectangular parallelepiped shape, a cylindrical shape, and a rod shape can be used. 200710070 The amount of the inorganic oxide fine particles added is preferably 100 parts by weight based on the weight of the solvent loo for the reaction. If it exceeds 1 part by weight, the movement of the ions may not be smoother; more preferably, the lower limit is the weight, and the upper limit is 20 parts by weight. Further, an acid anhydride such as acetic anhydride, phthalic anhydride, maleic anhydride, succinic anhydride or pyromellitic anhydride or an acid compound thereof, or a basic compound such as trimethylimidazole may be added. The solvent for the reaction is 1% by mass, and the amount added is preferably 50% by mass or less. 〇〇 1% by mass or more, 2 〇 2: The following is more preferable. In the solvent for the above reaction, various additives may be contained in addition to the above salts or solvents. The addition of the additive has various purposes, such as: introduction of rare, heat sensitivity of the heat, suppression of electrode deterioration due to hydration or dissolution, suppression of gas generation, improvement of withstand voltage, improvement of affinity, and the like. These additives may be used alone or in combination of two or more of the following: nitro compounds such as p-nitrophenol, J-nitroethyl phenol, p-nitrobenzoic acid, etc.; Phosphate compounds such as monobutyl ester, dioctyl phosphate, octylphosphonic acid monooctyl ester, phosphoric acid, etc.; boric acid or boric acid and polyhydric alcohol (ethylene glycol, glycerin, glycerol + = sugar alcohol, polyvinyl alcohol, etc.) or more Boron-like compound of saccharide, such as nitroso compound; urea compound; arsenic compound; bismuth compound, phthalic acid compound; aluminate compound; nitric acid and nitrous acid compound; 2-hydroxyl N-methyl Benzoic acid, di(tri)hydroxybenzoic acid, etc.; benzoic acid; digluconate, dichromic acid, sorbic acid, dicarboxylic acid, EDTA, fluorocarboxylic acid, picric acid, hexa-S, s-acid, miscellaneous Polyacids (haric acid, | acid), gentisic acid uronic acid, salicylic acid, N-aminosalicylic acid, boron di-catechin acid 200710070 boron di pyrocatechol (borodiprotocatechuic acid) ( Borodipyrocatechol), carbamic acid, rotten acid, phthalic acid, meta-hydroxybenzoic acid, pentane Acids such as acid, dithiocarbamic acid, etc.; such esters, such guanamines and salts thereof; decane coupling agents;

Anthraquinone compounds such as Shixi, amino phthalate, etc.; amine compounds such as triethylamine and hexamethylenetetramine; L-amino acids; benzol; polyphenylene; oxyquinoline; N-fluorenyl pyrocatechol; quinoline; thioanisole, thio-methyl, thiobenzoic acid and the like sulfur compounds; sorbitol; histidine and the like. The content of the above-mentioned additive is not particularly limited, and is, for example, 100% by mass of the solvent for the reaction, preferably 〇·1% by mass or more and 2% by mass or less, more preferably 0.5% by mass or more and 1% by mass or less. The solvent for the reaction of the present invention has stability over time in various reaction processes and can sufficiently increase the efficiency of the reaction, so that it can be used in various reactions. It is preferably suitable for the following reactions, and is preferably, for example, radical polymerization, anionic polymerization, cationic polymerization, coordination polymerization, photopolymerization, radiation polymerization, ring-opening polymerization, addition polymerization, polycondensation, addition condensation Polymerization of electrolytic polymerization, oxidative polymerization, polymer reaction, depolymerization, etc.; telomerization of conjugated diene; quantification of olefins, oligomerization of olefins, polymerization of smoky tobacco, alkylation of olefins , hydrogenation of olefins, metathesis of olefins, hydroformylation of olefins, ring closure metathesis of olefins, ring-opening metathesis of olefins, symmetry or asymmetric epoxidation of olefins (hetero-substituted olefins), maternity The reaction of dilute smoke, such as condensation, hydrogenation, isomerization, Suzuki cross-linking, amination, partial oxidation of alkanes, dynamic partitioning of racemic mixtures, imine Hydrogenation and ketone 21 200710070 Hydrogenation moves 5L hydrogenation, reaction of alkaloids such as aromatic organic compounds. As described above, the present invention is also a method of using the solvent for the above reaction. Among the above reactions, preferred is a polymerization reaction, and the solvent for the above reaction is a solvent for polymerization. When the solvent for the above reaction is used in the polymerization reaction, the reaction between the above-mentioned counter solvent and the raw material monomer and the produced polymer can be sufficiently suppressed, and the polymerization reaction rate can be greatly improved, and the polymerization efficiency can be greatly improved.

The present invention is also a process for producing a compound obtained by using the above solvent for reaction. Further, the obtained compound also contains a polymer, and the compound obtained by such a production method is also one of the inventions. In the above production method, the amount of the solvent for the reaction can be appropriately selected depending on the reaction to be carried out, and is not particularly limited. For example, when a polymerization reaction is carried out using a solvent for a reaction to obtain a polymer, 100 parts by weight of the total amount of monomers of the raw material is preferably limited to 5 parts by weight, and upper limit is 10,000 parts by weight. More preferably, the lower limit is 1 part by weight and the upper limit is 5000 parts by weight. Further, the reaction conditions such as the reaction temperature, the reaction time, and the amount of the raw materials in the above production method can be appropriately set depending on the reaction to be carried out. Since the solvent for the reaction of the present invention has the above-described constitution, it does not volatilize during various reaction processes, does not react with raw materials and products, and has stability over time and can sufficiently improve reaction efficiency. Suitable for various reactions. [Embodiment] Hereinafter, the present invention will be described in more detail by way of examples, however, the present invention 22 "%" is in the following examples and the like.

200710070 is not limited to only these embodiments. In addition, as long as the description of the hunting is not made, it means "% by mass". ^ ^ ^ _ ▼ The degree of dispersion is measured by GPC (gel permeation chromatography) based on stupid ethylene conversion. Model: HTC-8020 manufactured by Tosoh Corporation

Column: TSKgel GMHxl-L (2) Solvent: THF Flow rate: 1 mL/min Standard: Use standard polystyrene <Use as polymerization solvent for ionic liquid> (Example 1) In test tube 2 mL of EMlmDCA as a solvent, dimethyl methacrylate (MMA) as a monomer, azobisisobutyronitrile as a starter and 5 mmol of monomer 1 molar, under a nitrogen atmosphere The polymerization was carried out at 7 ° C for 20 hours. The recovery of the polymer is carried out by reprecipitation in methanol. The yield of the obtained polymer was 63.1 ° /. The number average molecular weight was 166,000' and the polydispersity was 4.3. (Examples 2 to 3 and Comparative Example 1) The same conditions as in Example 1 were carried out except that the solvent was changed to EMImTCM (Example 2), EMImTFSI (Real Example 3) or toluene (Comparative Example). The polymerization of MMA was carried out, and the physical properties of the obtained polymer were determined in the same manner as in Example 1. The results are shown in Table i. 23 200710070 [Table i] Solvent yield number average molecular weight polydispersity Example 1 EMImDCA 63.1 16.6 million 4.3 Example 2 EMImTCM 26.9 89,000 2.4 Example 3 EMImTFSI 40.6 11.5 million 2.6 Comparative Example 1 Toluene 33.1 4.3 million 1.8 Table 1 The description is as follows: EMImDCA: 1-ethyl-3-mercaptoimidazole rust dicyanamide EMImTCM: 1-ethyl-3-methylimidazole rust tricyanomethylated product EMImTFSI : 1-ethyl- 3-methylimidazole rust bis(trifluoromethanesulfonimide) <Use as solvent for reaction of ionic solution (organic synthesis example in ionic liquid)> (Example 4) In ionic liquid The following organic synthesis reaction was carried out. 0.86 mL of triethylamine and 0.36 mL of ethanol were added to 5 mL of EMImDCA. 0.5 mL of propionate chloride was added thereto. Ethyl acrylate was obtained from the solution after the reaction. The structure of the synthesized compound was confirmed by iH-NMR to obtain a chemical shift of l-3 ppm (t), 4_2 ppm (q), 5.8 ppm (d), 6.1 ppm (q), and 6.4 ppm (d) 〇 ( Examples 5 to 6) Ethyl acrylate was obtained in the same manner as in Example 4 except that EMImTCM (Example 5) or EMImTFSI (Example 6) was used instead of EMImDCA. The structure of the synthesized compound was confirmed by 1H-NMR, and the chemical shift was obtained. In Example 5 and Example 6, 1.3 ppm (t), 4.2 ppm (q), 5.8 ppm (d), and 6.1 ppm (q) were obtained. 6.4 ppm (d) 〇24 200710070 Since the solvent for the reaction of the present invention is as described above, it does not volatilize during various reaction processes, does not react with raw materials or products, and is stable over time and can be sufficiently improved. The reaction efficiency is preferably applied to various reactions. The present application is based on Japanese Patent Application No. 2005-217419, the entire disclosure of which is incorporated herein by reference. right. The contents of this application are all used in this application. [Simple description of the diagram] None [Key component symbol description] None 25

Claims (1)

200710070 C. Patent application: A solvent for the reaction, which is characterized in that it contains an ionic liquid having an anion represented by the following formula (1). (1) (wherein 'X represents at least one element selected from the group consisting of B, C, N, 〇, AhSi, P, S, As, and Se. 丨8 and ^ denote the same or different organic linking group ;Q represents an organic group; a is an integer of 1 or more, b, 0, (1 and 6 are integers of 〇 or more.) 2. The solvent for the reaction of the ninth aspect of the patent application, the solvent for the reaction is a solvent for polymerization 3. A manufacturing method characterized in that a compound is produced by using a solvent for the reaction of the first or second aspect of the patent application. XI. 囷: Yi η, 26 200710070 VII. Designated representative map: (1) The representative representative picture of this case is: the (none) picture. (2) The simple description of the symbol of the representative figure: No. 8. If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention: 4