Catalyst for organic synthesis and method for producing organic compound

Abstract

Provided are: a catalyst for organic synthesis, which has high catalytic activity, can be easily solid-liquid separated from a reaction system, and can synthesize an organic compound at high efficiency; and a method for producing an organic compound using the catalyst. A catalyst for organic synthesis, which is an anion exchange resin having a halogen acid salt having a tertiary amino group as an ion exchange group. Also provided is a method for producing an organic compound using, as a catalyst, an anion exchange resin in which a haloid salt having a tertiary amino group is used as an ion exchange group.

Description

Technical Field

[0001] The present invention relates to a catalyst for organic synthesis used for synthesizing an organic compound, and a method for producing an organic compound using the catalyst. Background Art

[0002] For example, a cyclic carbonate synthesis catalyst for synthesizing a cyclic carbonate from an alkylene oxide and carbon dioxide and a method for producing a cyclic carbonate have long been known in the art.

[0003] As heterogeneous catalysts for synthesizing cyclic carbonates, for example, there can be mentioned: a strong anion exchange resin having a quaternary ammonium group with a halogen ion as a counter ion as an ion exchange group (see Patent Document 1), a strong anion exchange resin having a water content of 0.5% by weight or less (see Patent Document 2), and an anion exchange resin having a tertiary amino group or a quaternary ammonium group as an ion exchange group with a silicate as a counter anion (see Patent Document 3), etc.

[0004] In addition, as a method for synthesizing cyclic carbonates from alkylene oxides and carbon dioxide, there are known methods of using a strong anion exchange resin having a quaternary ammonium group with an iodide ion as a counter ion as a heterogeneous catalyst in the presence of water (see Non-Patent Document 1), and a method of using a hydroiodide of a tertiary amine as a homogeneous catalyst (see Non-Patent Document 2).

[0005] However, the method using a strong anion exchange resin having a quaternary ammonium group as an ion exchange group has a problem of insufficient catalytic activity. In addition, the method using a homogeneous catalyst has a problem of difficulty in removing the catalyst from the reaction system.

[0006] For example, as a homogeneous catalyst for synthesizing oxazolidinone, a quaternary ammonium salt having a halogen ion as a counter ion is known (see Non-Patent Document 3).

[0007] However, in the method using a homogeneous catalyst, there is a problem that it is difficult to remove the catalyst from the reaction system.

[0008] Prior art literature Patent Literature Patent Document 1: U.S. Patent No. 2773070 Patent Document 2: Japanese Patent Application Laid-Open No. 3-120270 Patent Document 3: Japanese Patent No. 3568226 Non-patent literature Non-patent literature 1: ACS Sustainable Chem. Eng. 2020, 8, 7993?8003 Non-patent literature 2: ACS Sustainable Chem. Eng. 2017, 5, 7295?7301 Non-patent document 3: Green Chem. 2011, 13, 2351-2353 Summary of the invention Technical problem to be solved by the invention An object of the present invention is to provide a catalyst for organic synthesis which has high catalytic activity, can be easily separated from a reaction system into solid and liquid, and can synthesize an organic compound with high efficiency, and a method for producing an organic compound using the catalyst.

[0009] Technical solutions for solving technical problems The present invention is a catalyst for organic synthesis, which is an anion exchange resin having a hydrohalide salt of a tertiary amino group as an ion exchange group.

[0010] In the above-mentioned catalyst for organic synthesis, the above-mentioned hydrohalide salt is preferably a hydrobromide or a hydroiodide.

[0011] The above-mentioned catalyst for organic synthesis is preferably used for the synthesis of cyclic carbonates.

[0012] The present invention is a method for producing an organic compound using an anion exchange resin having a hydrohalide salt of a tertiary amino group as an ion exchange group as a catalyst.

[0013] In the above method for producing an organic compound, the above hydrohalide salt is preferably a hydrobromide salt or a hydroiodide salt.

[0014] In the method for producing an organic compound, the organic compound is preferably a cyclic carbonate.

[0015] Effects of the Invention According to the present invention, there can be provided a catalyst for organic synthesis which has high catalytic activity, can be easily separated into solid and liquid from a reaction system, and can synthesize an organic compound with high efficiency, and a method for producing an organic compound using the catalyst. DETAILED DESCRIPTION

[0016] Hereinafter, an embodiment of the present invention will be described. This embodiment is an example for carrying out the present invention, and the present invention is not limited to this embodiment.

[0017] <Catalysts for organic synthesis> The catalyst for organic synthesis provided by the embodiment of the present invention is a catalyst for synthesizing organic compounds, for example, a catalyst for synthesizing cyclic carbonates from alkylene oxide and carbon dioxide, and in addition, for example, a catalyst for synthesizing organic compounds such as oxazolidinones from aziridine and carbon dioxide. The catalyst is an anion exchange resin having a hydrohalide salt of a tertiary amino group as an ion exchange group, and can be used as a heterogeneous catalyst.

[0018] The inventors etc. have found that the hydrohalide with tertiary amino group functions as a catalyst as a weak anion exchange resin of an ion exchange group, and the catalyst has a high catalytic activity in the reaction of synthesizing organic compounds, can easily separate solid from liquid from the reaction system, can synthesize cyclic carbonates with high efficiency. The catalyst for organic synthesis provided by the present embodiment is, for example, in the reaction of the alkylene oxide and carbon dioxide synthesizing cyclic carbonates shown in the following reaction formula, high as a catalytic activity, can easily separate solid from liquid from the reaction system, can synthesize cyclic carbonates with high efficiency.

[0019] For example, when being synthesized cyclic carbonate by alkylene oxide and carbon dioxide, by using the salt with tertiary amino group as the weak anion exchange resin of functional group and hydrogen halide as catalyzer, cyclic carbonate can be obtained with high conversion rate, and then the heterogeneous catalyst that can easily separate solid and liquid from reaction system is provided.By using this catalyzer, cyclic carbonate can be synthesized with the conversion rate higher than the catalyzer of known document record.

[0020] [Chemistry 1] In the above reaction formula, R in the alkylene oxide is not particularly limited as long as it does not hinder the reaction, and each independently represents, for example, a hydrogen atom; a straight-chain, branched, or cyclic alkyl group having 1 to 20 carbon atoms which may be substituted by a halogen atom, an aryl group having 6 to 15 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an oxo group, a nitro group, a cyano group, or the like; an alkenyl group having 2 to 12 carbon atoms; an alkynyl group having 2 to 12 carbon atoms; an aryl group having 6 to 18 carbon atoms; an alkoxy group having 1 to 8 carbon atoms; an acyl group having 1 to 8 carbon atoms; a halogen atom; a nitro group; a cyano group, etc., preferably an alkyl group having 1 to 8 carbon atoms or an aryl group having 6 to 10 carbon atoms, and more preferably a methyl group or a phenyl group.

[0021] The alkylene oxide is not particularly limited as long as it does not inhibit the reaction, and examples thereof include propylene oxide, ethylene oxide, 1,2-butylene oxide, propylethylene oxide, epichlorohydrin, styrene oxide, styrene oxide, 4-chlorostyrene oxide, 1,2-epoxy-5-hexene, allyl glycidyl ether, benzyl glycidyl ether, and the like. Preferred are propylene oxide, epichlorohydrin, and styrene oxide.

[0022] Examples of the tertiary amino group in the catalyst for organic synthesis provided in this embodiment include dimethylamino, diethylamino, dipropylamino, dibutylamino, methylhydroxyethylamino, methylhydroxypropylamino, dicyclohexylamino, pyrrolidinyl, piperidinyl, 2,2,6,6-tetramethylpiperidinyl, morpholinyl and the like.

[0023] The halogen ions used as counter ions are F, Cl, Br, I, etc. From the perspective of safety in catalyst preparation, Cl, Br, and I are preferred. From the perspective of high reaction conversion rate, Br and I are more preferred. From the perspective of less by-products, I is further preferred.

[0024] There is no particular restriction on the type of polymer material constituting the skeleton of the anion exchange resin, and examples thereof include: aromatic vinyl polymers such as polystyrene, poly(α-methylstyrene), polyvinyltoluene, polyvinylbenzyl chloride, polyvinylbiphenyl, and polyvinylnaphthalene; polyolefins such as polyethylene and polypropylene; poly(halogenated polyolefins) such as polyvinyl chloride and polytetrafluoroethylene; nitrile polymers such as polyacrylonitrile; crosslinked polymers such as (meth)acrylic polymers such as polymethyl methacrylate, polyglycidyl methacrylate, and polyethyl acrylate. The above polymers may be polymers obtained by copolymerizing a single vinyl monomer with a crosslinking agent, or may be polymers obtained by polymerizing a plurality of vinyl monomers with a crosslinking agent, or may be polymers blended from two or more polymers. As a polymer material constituting the skeleton of the anion exchange resin, styrene-divinylbenzene copolymer resin is preferred from the aspects of heat resistance and the like.

[0025] The weak anion exchange resin having a hydrohalide salt of a tertiary amino group as an ion exchange group can be used as a granular resin of 300 to 1000 μm, for example.

[0026] <Method for producing organic compound> The manufacture method of the organic compound that the present embodiment provides is to use the hydrohalide with tertiary amino group as the method for the anion exchange resin of ion exchange group as catalyst.The manufacture method of the organic compound that the present embodiment provides is, for example, to use the hydrohalide with tertiary amino group as the method for the anion exchange resin of ion exchange group as catalyst, by the method for synthesizing cyclic carbonate of alkylene oxide and carbon dioxide.In addition, the manufacture method of the organic compound that the present embodiment provides is, for example, to use the hydrohalide with tertiary amino group as the method for the anion exchange resin of ion exchange group as catalyst, by the method for synthesizing oxazolidinone of aziridine and carbon dioxide.

[0027] In the reaction of the catalyst for organic synthesis provided by the present embodiment, the reaction conditions are not particularly limited as long as they can obtain the condition of the target organic compound. In the reaction of the catalyst for organic synthesis provided by the present embodiment, the reaction conditions are not particularly limited as long as they can obtain the condition of the target cyclic carbonate. In addition, in the reaction of the catalyst for organic synthesis provided by the present embodiment, the reaction conditions are not particularly limited as long as they can obtain the condition of the target cyclic carbonate.

[0028] As the reaction conditions in the reaction of synthesizing cyclic carbonates from alkylene oxide and carbon dioxide using the catalyst for organic synthesis provided by the present embodiment, the reaction temperature is, for example, 0 to 120° C., preferably 10 to 100° C. The reaction time is, for example, 1 to 96 hours, preferably 3 to 48 hours. The reaction pressure is, for example, atmospheric pressure to 5.0 MPa, preferably atmospheric pressure to 1.0 MPa. The reaction of synthesizing cyclic carbonates using the catalyst for organic synthesis provided by the present embodiment is a heterogeneous system, and can also be carried out at room temperature (15 to 30° C.) and atmospheric pressure.

[0029] As the solvent used in the reaction of synthesizing cyclic carbonate from alkylene oxide and carbon dioxide, there is no particular limitation as long as the reaction is not hindered, and examples thereof include water, alcohol solvents such as methanol, ethanol, propanol, butanol, benzyl alcohol, ketone solvents such as acetone, methyl ethyl ketone, nitrile solvents such as acetonitrile, amide solvents such as dimethylformamide, dimethylacetamide, N-methylpyrrolidone, ether solvents such as dimethyl ether, tetrahydrofuran, etc., which can be used alone or in combination of two or more. In the case where the alkylene oxide is in a liquid state under the reaction conditions, no solvent may be used.

[0030] The reaction of synthesizing cyclic carbonate by alkylene oxide and carbon dioxide can be carried out as follows: in a pressure-resistant reaction vessel, alkylene oxides such as propylene oxide and hydrohalide salts with tertiary amino groups are added to a weak anion exchange resin as an ion exchange group in a solvent such as water, carbon dioxide is enclosed in the reaction vessel, and a predetermined time is reacted at a predetermined temperature and a predetermined pressure in a heterogeneous system. After the reaction, the weak anion exchange resin is removed by solid-liquid separations such as filtration, and the solvent is removed by distillation, so that the target cyclic carbonate can be obtained. In the case where alkylene oxide is in a liquid state under reaction conditions, the reaction can be carried out as follows: in a pressure-resistant reaction vessel, a weak anion exchange resin as an ion exchange group is added to alkylene oxides such as propylene oxide, carbon dioxide is enclosed in the reaction vessel, and a predetermined time is reacted at a predetermined temperature and a predetermined pressure in a heterogeneous system. After the reaction, the weak anion exchange resin is removed by solid-liquid separations such as filtration, so that the target cyclic carbonate can be obtained. The completion of the reaction can be confirmed by, for example, thin layer chromatography (TLC), liquid chromatography (LC), gas chromatography (GC), nuclear magnetic resonance (NMR), Fourier transform infrared spectroscopy (FT-IR), etc. The obtained cyclic carbonate can be purified by a known method.

[0031] By such a reaction, a cyclic carbonate can be obtained at a reaction conversion rate of, for example, 8% or more, preferably 80% or more.

[0032] <Method for producing catalyst for organic synthesis> The catalyst for organic synthesis provided in this embodiment is produced from, for example, an anion exchange resin having a tertiary amino group and hydrogen halide.

[0033] In the reaction for synthesizing the catalyst for organic synthesis provided by the present embodiment, the reaction conditions are not particularly limited as long as an anion exchange resin having a hydrohalide salt of a tertiary amino group as an ion exchange group can be obtained.

[0034] The reaction can be carried out, for example, by mixing an anion exchange resin having a tertiary amino group with a hydrogen halide such as hydrogen chloride, hydrogen bromide, or hydrogen iodide, and reacting at a predetermined temperature (e.g., 10 to 30° C.) for a predetermined time (e.g., 0.5 to 24 hours). The obtained resin can be washed with water, an alcohol solvent, or the like.

[0035] Compared with the manufacturing process of a strong anion exchange resin having a quaternary ammonium group with a halogen ion as a counter ion, the manufacturing process of a weak anion exchange resin having a hydrohalide salt of a tertiary amino group as an ion exchange group has fewer reaction steps such as the counter ion conversion step, and the weak anion exchange resin having a tertiary amino group as an ion exchange group can be easily made into a hydrohalide salt.

[0036] Example Hereinafter, the present invention will be described in more detail with reference to Examples and Comparative Examples, but the present invention is not limited to the following Examples.

[0037] <Examples 1-1 to 1-3> Using an anion exchange resin (salt of Amberlyst A21 (manufactured by ORGANO Co., Ltd.) and a hydrohalic acid) having a tertiary amino group having the following structure as an ion exchange group as a catalyst, a synthesis reaction of 4-methyl-1,3-dioxirane-2-one shown below was carried out.

[0038] (Reaction implemented) [Chemistry 2] (Chemical structure of the catalyst used) Resin-N(CH3)2·HX X=I (Examples 1-1, 1-2), Br (Example 1-3) Resin = Styrene-divinylbenzene copolymer resin The synthesis reaction of the catalyst for organic synthesis (cyclic carbonate synthesis catalyst) was carried out according to the following steps.

[0039] [Preparation of A21·HI] In a reaction vessel, 2.17 g of a dried product of an anion exchange resin having a tertiary amino group (Amberlyst A21 (manufactured by ORGANO Co., Ltd.), resin-N(CH3)2), 30 mL of water, and 2.24 g of 55% to 58% hydroiodic acid were mixed and stirred at room temperature (25°C) for 1 hour to react. Next, the product was filtered, and the filtrate was washed with water and then dried under reduced pressure to obtain A21·HI, which was the target catalyst for organic synthesis.

[0040] [Preparation of A21·HBr] In a reaction vessel, 1.08 g of a dried product of an anion exchange resin having a tertiary amino group (Amberlyst A21 (manufactured by ORGANO Co., Ltd.)), 15 mL of water, and 0.827 g of 49% hydrobromic acid were mixed and stirred at room temperature for 1 hour to react. Next, the product was filtered, and the filtrate was washed with water and then dried under reduced pressure to obtain A21·HBr, which was the target catalyst for organic synthesis.

[0041] [Preparation of IRA98·HI] In a reaction vessel, 2.21 g of a dried product of an anion exchange resin having a tertiary amino group (Amberlite IRA98 (manufactured by ORGANO Co., Ltd.), resin-N(CH3)2), 30 mL of water, and 2.28 g of 55% to 58% hydroiodic acid were mixed and stirred at room temperature for 1 hour to react. Next, the product was filtered, and the filtrate was washed with water and then dried under reduced pressure to obtain IRA98·HI, which is a catalyst for organic synthesis as the target.

[0042] The synthesis reaction of 4-methyl-1,3-dioxirane-2-one in Examples 1-1 to 1-3 was carried out according to the following steps.

[0043] In a reaction vessel, 2.5 g of water and a predetermined amount of the obtained catalyst for organic synthesis were added to 0.290 g of propylene oxide and mixed. A balloon filled with carbon dioxide was installed, and the mixture was stirred at atmospheric pressure and room temperature for 24 hours to react. After the reaction, the catalyst for organic synthesis was removed by filtration to obtain crude 4-methyl-1,3-dioxirane-2-one. A nuclear magnetic resonance device (Bruker Ascend 400 MHz) was used to measure 1 The reaction conversion rate (%) of 4-methyl-1,3-dioxirane-2-one was determined from the integrated value of each spectrum by H-NMR. The results are shown in Table 1.

[0044] <Comparative Example 1-1> As Comparative Example 1-1, a synthesis reaction of 4-methyl-1,3-dioxirane-2-one was carried out in the same manner as in Example without using a catalyst.

[0045] <Comparative Example 1-2> As Comparative Example 1-2, a synthesis reaction of 4-methyl-1,3-dioxirane-2-one was carried out in the same manner as in Example using a type I catalyst (a strong anion exchange resin having a quaternary ammonium group as an ion exchange group with an iodine ion as a counter ion) in which Amberlite IRA900J CL (manufactured by ORGANO Co., Ltd.) as a strong anion exchange resin was converted to an iodine type. The results are shown in Table 1.

[0046] (Chemical structure of the catalyst used) Resin-N(CH3)3·HX X=I(Comparative Example 1-2) Resin = Styrene-divinylbenzene copolymer resin The synthesis reaction of the catalyst used for organic synthesis is carried out according to the following steps.

[0047] [Preparation of IRA900J·I] An anion exchange resin having a quaternary amino group (Amberlite IRA900J CL (manufactured by ORGANO Co., Ltd.), resin-N (CH3) 3·HCl) and an excess of 1 equivalent of NaOH aqueous solution were added to the reaction container and stirred at room temperature for 4 hours. Next, the product was filtered and the filtrate was washed with water. Then, 10 mL of the obtained product and 1.90 g of 55-58% hydroiodic acid were mixed in the reaction container and stirred at room temperature for 3 hours to react. Next, the product was filtered, the filtrate was washed with water, and then dried under reduced pressure to obtain IRA900J·I.

[0048] <Comparative Examples 1-3> As Comparative Example 1-3, a synthesis reaction of 4-methyl-1,3-dioxirane-2-one was carried out in the same manner as in Example using a dry product of Amberlyst A21 (manufactured by ORGANO CORPORATION) as a weak anion exchange resin.

[0049] <Comparative Examples 1-4> As Comparative Example 1-4, a synthesis reaction of 4-methyl-1,3-dioxirane-2-one was carried out in the same manner as in Example using a dry product of Amberlite IRA98 (manufactured by ORGANO CORPORATION) as a strong anion exchange resin.

[0050] [Table 1] The experimental results show that the weak anion exchange resin having a hydrohalide salt of a tertiary amino group as an ion exchange group in the examples has a higher reaction conversion rate to 4-methyl-1,3-dioxirane-2-one than the strong anion exchange resin having a quaternary ammonium group and a halogen ion and the weak anion exchange resin having a tertiary amino group as an ion exchange group. In addition, the case of using a salt of hydrogen iodide (Examples 1-1 and 1-2) has less by-products than the case of using a salt of hydrogen bromide (Example 1-3).

[0051] <Examples 2-1, 2-2> In the synthesis reaction of 4-methyl-1,3-dioxirane-2-one, the synthesis reaction is carried out by changing the solvent, temperature and pressure conditions.

[0052] The synthesis reaction of 4-methyl-1,3-dioxirane-2-one in Example 2-1 was carried out according to the following steps.

[0053] In a reaction vessel, a predetermined amount of the obtained catalyst A21·HI for organic synthesis was added to 0.145 g of propylene oxide and mixed. A balloon filled with carbon dioxide was installed, and the mixture was stirred at atmospheric pressure and room temperature for 24 hours to allow the reaction to proceed. After the reaction, the catalyst for organic synthesis was removed by filtration to obtain crude 4-methyl-1,3-dioxirane-2-one. The results were measured using a nuclear magnetic resonance device. 1 The reaction conversion rate (%) of 4-methyl-1,3-dioxirane-2-one was determined from the integrated value of each spectrum by H-NMR. The results are shown in Table 2.

[0054] The synthesis reaction of 4-methyl-1,3-dioxirane-2-one in Example 2-2 was carried out according to the following steps.

[0055] In a pressurized reaction vessel, a predetermined amount of the obtained catalyst A21·HI for organic synthesis was added to 0.145 g of propylene oxide and mixed. 0.3 MPa of carbon dioxide was introduced and stirred at 40°C for 24 hours to allow the reaction to proceed. After the reaction, the catalyst for organic synthesis was removed by filtration to obtain crude 4-methyl-1,3-dioxirane-2-one. The results were measured using a nuclear magnetic resonance device. 1 The reaction conversion rate (%) of 4-methyl-1,3-dioxirane-2-one was determined from the integrated value of each spectrum by H-NMR. The results are shown in Table 2.

[0056] [Table 2] The experimental results show that the reaction proceeds even in the absence of a solvent, and the reaction conversion rate is increased by applying temperature and pressure.

[0057] <Examples 3-1 to 3-5> In order to examine substrate suitability, the synthesis reactions of 4-(chloromethyl)-1,3-dioxirane-2-one and 4-phenyl-1,3-dioxirane-2-one shown below were carried out.

[0058] (Reaction implemented) [Chemistry 3] [Chemistry 4] (Chemical structure of the catalyst used) Resin-N(CH3)2·HX X=I (Examples 3-2, 3-3, 3-5), Br (Example 3-1), Cl (Example 3-4) Resin = Styrene-divinylbenzene copolymer resin The synthesis reaction of the catalyst used for organic synthesis is carried out according to the following steps.

[0059] [Preparation of IRA98·HCl] In a reaction container, 2.21 g of a dried product of an anion exchange resin having a tertiary amino group (Amberlite IRA98 (manufactured by ORGANO Co., Ltd.)), 30 mL of water, and 1.04 g of 35% hydrochloric acid were mixed and stirred at room temperature for 1 hour to react. Next, the product was filtered, and the filtrate was washed with water and then dried under reduced pressure to obtain IRA98·HCl, which was the target catalyst for organic synthesis.

[0060] The synthesis reaction of 4-(chloromethyl)-1,3-dioxirane-2-one in Examples 3-1 and 3-2 was carried out according to the following steps.

[0061] In a reaction vessel, 2.5 g of water and a predetermined amount of the obtained catalyst for organic synthesis were added to 0.463 g of epichlorohydrin and mixed. A balloon filled with carbon dioxide was installed, and the mixture was stirred at atmospheric pressure and room temperature for 24 hours to react. After the reaction, the catalyst for organic synthesis was removed by filtration to obtain crude 4-methyl-1,3-dioxirane-2-one. The results were measured using a nuclear magnetic resonance device. 1 The reaction conversion rate (%) of 4-methyl-1,3-dioxirane-2-one was determined from the integrated value of each spectrum by H-NMR. The results are shown in Table 3.

[0062] The synthesis reaction of 4-(chloromethyl)-1,3-dioxirane-2-one in Examples 3-3 and 3-4 was carried out according to the following steps.

[0063] In a pressurized reaction vessel, a predetermined amount of the obtained catalyst for organic synthesis was added to 1.85 g of epichlorohydrin and mixed. 0.3 MPa of carbon dioxide was introduced and stirred at 50°C for 24 hours to allow the reaction to proceed. After the reaction, the catalyst for organic synthesis was removed by filtration to obtain crude epichlorohydrin carbonate. The carbon dioxide was measured using a nuclear magnetic resonance device. 1 The reaction conversion rate (%) of 4-(chloromethyl)-1,3-dioxirane-2-one was determined from the integrated value of each spectrum by H-NMR. The results are shown in Table 3.

[0064] The synthesis reaction of 4-phenyl-1,3-dioxirane-2-one in Example 3-5 was carried out according to the following steps.

[0065] In a pressurized reaction vessel, a predetermined amount of the obtained catalyst for organic synthesis was added to 2.40 g of styrene oxide and mixed. 0.3 MPa of carbon dioxide was introduced and stirred at 50°C for 24 hours to allow the reaction to proceed. After the reaction, the catalyst for organic synthesis was removed by filtration to obtain crude styrene oxide carbonate. The results were measured using a nuclear magnetic resonance device. 1 The reaction conversion rate (%) of 4-phenyl-1,3-dioxirane-2-one was determined from the integrated value of each spectrum by H-NMR. The results are shown in Table 3.

[0066] [Table 3] According to the experimental results, cyclic carbonates can also be synthesized in substrates having halogenated alkyl or aromatic substituents.

[0067] Thus, by using the catalyst of the example, the catalyst activity is high, and solid-liquid separation from the reaction system can be easily achieved, so that an organic compound such as a cyclic carbonate can be synthesized with high efficiency.

Claims

1. A catalyst for organic synthesis, characterized in that It is an anion exchange resin having a hydrohalide salt of a tertiary amino group as an ion exchange group.

2. The catalyst for organic synthesis according to claim 1, wherein The hydrohalide salt is hydrobromide or hydroiodide.

3. The catalyst for organic synthesis according to claim 1 or 2, wherein The catalyst for organic synthesis is used for the synthesis of cyclic carbonate.

4. A method for producing an organic compound, characterized in that: An anion exchange resin having a hydrohalide salt of a tertiary amino group as an ion exchange group is used as a catalyst.

5. The method for producing an organic compound according to claim 4, wherein: The hydrohalide salt is hydrobromide or hydroiodide.

6. The method for producing an organic compound according to claim 4 or 5, wherein: The organic compound is a cyclic carbonate.

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