JP2010013426A - Method for producing epoxy ketones - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a method which can be used for producing epoxy ketones having a target structure with good selectivity, while inhibiting the formation of by-products. <P>SOLUTION: The method for producing epoxy ketones comprises reacting conjugated enones with the use of an anion exchangeable compound as a catalyst in the presence of an oxidizing agent, and as the anion exchangeable compound, at least any one of a compound having a botallackite structure, a hydrotalcite-like compound and an anion-exchange resin is used. <P>COPYRIGHT: (C)2010,JPO&INPIT

Description

  The present invention relates to a method for producing epoxy ketones, and more particularly to a method for producing epoxy ketones using hydrogen peroxide and conjugated enones.

  Epoxy ketones are compounds having an epoxide and a carbonyl moiety in the molecule, and are used in various applications. Epoxy ketones are important as flavoring agents and intermediates for medicines and agricultural chemicals. In particular, the material conversion by regioselective epoxide ring opening has high utility value industrially.

  In general, the synthesis of epoxy ketones has a very slow reaction rate and many side reactions without catalyst. For this reason, epoxy ketones are generally produced using a catalyst.

  For example, as an example of epoxy ketones, a method of synthesizing 2,3-poxy-1-cyclohexanone using an alkali metal salt and a large amount of hydrogen peroxide has been conventionally known.

  By the way, if the catalyst remains in the epoxy ketones which are reaction products, the product (epoxy ketones) may be adversely affected. Therefore, it is preferable to remove the catalyst after the production of epoxy ketones.

  In addition, in a reaction using hydrogen peroxide that is greater than the stoichiometric amount of the reaction substrate, it is necessary to remove the hydrogen peroxide after completion of the reaction, and thus a catalytic reaction system with high hydrogen peroxide utilization efficiency is desired.

  Then, this invention is made | formed in view of the said situation, and it is providing the method which can manufacture the epoxy ketone which has the target structure with sufficient selectivity, suppressing the production | generation of a by-product.

  That is, the method for producing epoxy ketones according to one means of the present invention for solving the above-mentioned problems is to produce an epoxy ketone by reacting a conjugated enone in the presence of an oxidizing agent using an anion exchange compound as a catalyst. And a compound having a botalakite structure is used as the anion exchange compound.

  Moreover, the method for producing an epoxy ketone according to another means of the present invention is a method for producing an epoxy ketone by reacting a conjugated enone in the presence of an oxidizing agent using an anion exchange compound as a catalyst. Thus, a hydrotalcite-like compound is used as the anion exchange compound.

  Moreover, the method for producing an epoxy ketone according to another means of the present invention is a method for producing an epoxy ketone by reacting a conjugated enone in the presence of an oxidizing agent using an anion exchange compound as a catalyst. An anion exchange resin is used as the anion exchange compound.

  As described above, according to the present invention, in producing a corresponding epoxy ketone by reacting hydrogen peroxide with enones, an anion-exchange layered compound is used as a catalyst, thereby increasing the reaction activity and generating by-products. Thus, epoxy ketones having the target structure can be produced with good yield.

  In the present invention, by using an anion-exchange layered compound as a catalyst, the above-mentioned epoxy ketones can be produced with a high yield by increasing the reaction activity.

  Moreover, the target compound (epoxy ketones) and the catalyst can be easily separated and can be used repeatedly. Since the catalyst can be easily separated, a neutralization step of the catalyst after the reaction is not required. In addition, since it is not necessary to add an excess of hydrogen peroxide, the production of by-products is small, and the production selectivity of epoxy ketones having the target structure is good.

(Embodiment)
Hereinafter, the method for producing the epoxy ketones according to the present embodiment will be described in detail.

  The method for producing epoxy ketones according to this embodiment uses an anion exchange compound as a catalyst and reacts enones in the presence of an oxidizing agent.

  The raw material enones used in the present embodiment mean α, β-unsaturated ketones. Examples of α, β-unsaturated ketones include, but are not limited to, acyl styrene derivatives and 2-cycloalkene 1-ones. More specific examples include 2-cyclopentene- 1-one, 3-methyl-2-cyclopenten-1-one, 2-cyclohexen-1-one, 3-methyl-2-cyclohexen-1-one, naphthoquinone, 4-hexen-3-one, chalcone, 2- Examples include, but are not limited to, methyl-2-penten-4-one, 3-nonen-2-one, benzalacetone, isophorone, 2-methyl-5-isopropenyl-2-cyclohexenone, and the like. . In the present embodiment, the raw material enones may be either solid or liquid, and there is no particular limitation on the form (packaging) and purity.

  The anion exchange compound used as a catalyst in the present embodiment is a compound having anion exchange ability, and includes (A) a compound having a bottalakite structure, (B) a hydrotalcite-like compound, and (C) an anion exchange resin. At least one is used.

  In this embodiment, (A) a compound having a bottalachite structure is a compound having a bottalakite structure that has a plurality of layers and contains anions between these layers, and can perform anion exchange by entering and exiting these anions. Say.

As an example of a compound having a botalakite structure, there can be mentioned Hydroxy Double Salts (hereinafter “HDSs”), and the general formula thereof is M _I ²⁺ _1-x M _II ²⁺ _{1 + x} (OH) _{3 (1-y) / z} Y ^z− _{(1 + 3y)} · nH ₂ O HDSs is deficient part _M ^{I 2+} to form a _M ^I 2+ _{(OH) 2} vulcite layer, _M ^{II 2+} to form a hydroxide layer and tetrahedral above and below, to compensate for the charge ^Therefore , Y ^z− is forcibly present in the vicinity of M _II ²⁺ .

Here, M _I ²⁺ is Ni, Co or Zn, and M _II ²⁺ is Cu or Zn. Y is a unitary or polyvalent anion, and examples include Cl ⁻ , Br ⁻ , I ⁻ , NO ³⁻ , OAc ⁻ , HOCO ⁻ , SO ₄ ²⁻ , CO ₃ ²⁻ , PO ₄ ^{3−, and the} like. be able to.

In particular, among the compounds represented by the above general formula, Ni—Zn dibasic salt (hereinafter referred to as “NiZn—OAc”) is M _I ²⁺ = Ni, M _II ²⁺ = Zn ²⁺ , Y = AcO ⁻ . The composition formula is preferably Ni _1-x Zn ^2x (OH) ₂ (OAc) _2x · nH ₂ O (0.15 <x <0.25).

  The anion exchange type Ni—Zn dibasic salt is prepared by an intercalation method in order to insert various anions between layers. The intercalation method is a very simple method that does not require consideration of the order of ion selectivity, and can be applied to many anions, and highly converts the acetate anion of the above-mentioned acetate anion-type Ni-Zn dibasic salt. It can be replaced with other anions at a rate. Here, the intercalation means a reaction in which various atoms, molecules or ions break into the weak bond between the layers of the layered crystal and are inserted between the layers in the layered compound.

  Examples of “anions other than carbonate ions” include various inorganic anions and organic anions. As inorganic anions, halogen anions such as fluorine ion, chlorine ion, bromine ion and iodine ion: sulfate anion, thiosulfate anion, nitrate anion, phosphate anion, chlorate anion, perchlorate anion, silicate anion, chromic acid Examples include anions of inorganic acids such as anions and tungstate anions; and complex anions such as ferricyan anions and ferrocyan anions. Organic anions include acetic acid anion, propionate anion, succinate anion, glutarate anion, adipate anion, benzoate anion, terephthalate anion, etc. Sulfonic acid anions such as p-toluenesulfonic acid anion; phenoxy anion and the like. Among these, a chloride ion, a sulfate anion, an acetate anion, a succinate anion, a glutarate anion, an adipate anion, a terephthalate anion, and a phenoxy anion are preferable, and a phenoxy anion is particularly preferable. Most preferably, it is a phenoxy anion derived from the same type of phenol as that used in the synthesis of the aromatic ether.

  Examples of the layered anion-exchange clay include natural botalacite type compounds.

An anion-exchange layered compound having a bottalackite structure means a copper-based chloride and its ion-exchange derivative. On page 82 of “Encyclopedia of Minerals (VAN NOS TRAND REINHOLD COMPANY)”, the basic structure “Cu ₂ Cl (OH) ₃ ” is classified as “Bbottalackite”. ₂ Cl (OH) ₃ ”and its ion exchange derivative, which means“ A ₂ (OH) ₃ (X) · nH ₂ O ”. Here, A is a divalent metal ion such as Cu ion, and may be the same type of divalent metal ion or a different type of divalent metal ion. Examples of the divalent metal ion include each ion such as Mg, Mn, Fe, Co, Ni, Cu, Zn, and Ca, but are not limited to these divalent metal ions. In addition, monovalent and trivalent metal ions can be substituted with A as long as they can retain the boratecite structure. Botarakkaito type compounds, nH in a plurality of layers indicated by _{"A 2 (OH) 3 (X} ) ", the water between the layers (the _{"A 2 (OH) 3 (X} ) · nH 2 O " ₂ O).

X is a site that directly coordinates to the metal and corresponds to Cl in the basic structure. This X can be exchanged for various anions. The initial anion species of the compound having the botarakite structure according to this embodiment is not particularly limited. Examples thereof include hydroxide ions, halide ions (fluorine ions, chlorine ions, bromine ions, iodine ions, etc.), organic acid anions (carboxylate anions, phenoxy anions, etc.), or non-conformal anions. Examples of inorganic acid anions include sulfate anion, sulfite anion, bisulfite anion, phosphate anion, borate anion, cyanide anion, carbonate anion, thiocyanate anion, nitrate anion, phosphate anion, hydrogen phosphate anion, polyanion. Oxymetalate anions (for example, molybdate anions, tungstate anions, phosphotungstate anions, metavanadate anions, pyrovanadate anions, hydrogen pyrovanadate anions, niobate anions, tantalate anions, etc.) are included. Among the anionic species exemplified above, anions of various organic acids, hydroxide ions, and halide ions are preferable. In addition to these, oxyanions such as perchlorate ion (Cl ⁴⁻ ), Mn ⁴⁻ , isopolyion, and heteropolyion (AF Wells, Structural Inorganic Chemistry, 5th Ed, Clarendon Press, Oxford, 1984, pp. 196 510-530), SCN ⁻ , acetate anion, RCOO ⁻ , [R: CH ₃ (CH ₂ ) n, n = 0 to 22], a monocarboxylic acid anion, R (COO ⁻ ) ₂ , R (COO ⁻ ) ₂ , [R: (CH ₂ ) n, n = 0 to 22], dicarboxylic acid anions, and silicate anions such as Si ₈ O ₂₀ ^8- .

Further, Cu ²⁺ shown in the basic structure can be exchanged for a divalent metal ion, and a synthesis example of 10 such as Zn ²⁺ / Ni ²⁺ has been reported (Material Research Society of Symposium Processings, Vol. 371, 131-). 142, 1994), and these are included in the botalakite type compound according to this embodiment.

  The anion species in the botalakite-type compound is directly coordinated to metal ions such as copper and has exchangeability, so it can be exchanged with various anions while maintaining the structure, but it is reported to show catalytic ability Never before.

  The botalakite type compound can be a highly selective catalyst because it can exchange ions while maintaining the crystal structure (that is, maintaining the uniformity of the structure). In addition, since metal acetate (botarakite type compound whose anion is acetate ion) can be used in the synthesis, there is an advantage that the synthesis conditions are flexible. When metal acetate is used for synthesis, there is little risk of corrosion of the reaction vessel. Further, since the acetic acid anion easily forms a layered structure as an interlayer anion, a botalakite type compound can be obtained in a high yield. Furthermore, the acetate anion is also characterized in that it can be easily exchanged with other anions.

  In the present embodiment, the (B) hydrotalcite-like compound refers to a compound having a plurality of brucite layers, containing an anion between these layers, and capable of anion exchange by entering and exiting the anion. Examples of hydrotalcite-like compounds include, for example, specific techniques for natural or synthesized hydrotalcite and natural or synthesized hydrotalcite-like compounds (hydrotalcite-like compounds having a carbonate anion). A compound in which a carbonate anion is exchanged with another anion using can be mentioned.

The brucite layer of the hydrotalcite-like compound is a layer composed of a double hydroxide, and specifically, a divalent metal ion is the center as in the case of brucite [Mg (OH) ₂ ]. Octahedrons are two-dimensionally connected to form a layer, and some of the divalent metal ions are replaced by trivalent metal ions. Exists for.

The hydrotalcite-like compound is represented by the following general formula (1).

In the general formula (1), [M ^II _1-a M ^III _a (OH) ₂ ] constitutes the brucite layer, and anion (and water molecules) [X ^m− _{a / m} · nH ₂ O] exists. These anions are exchangeable.

Of the compounds represented by the general formula (1), hydrotalys have M ^I = Mg, M ^III = Al, X = CO ₃ , a = 1/4, m = 2, and n = 1/2. It is a site, and the others are hydrotalcite-like compounds. As natural products, in addition to this hydrotalcite, pyroaurite (Pyroaurite, M ^II = Mg, M ^III = Fe, X = CO ₃ , a = 1/4, m = 2, n = 1/2), etc. It has been known.

  Details of such layered compounds are disclosed in "Anion Clays: Trends in Pillaring Chemistry" ("Expanded Clays and Other Microporous Solids", Vol. 2, New York, 1992, p. 108-169).

  In the present embodiment, (C) anion exchange resin means an ion exchange resin having a cation in a functional group and capable of interacting with an anion by electrostatic attraction and exchanging the anion by entering and exiting the anion.

  The chemical structure of the ion exchange resin is a polymer electrolyte in which an ion exchange exchange group is chemically bonded to a polymer matrix that is three-dimensionally polycondensed. When the exchange group is quaternary ammonium, it is called a strongly basic anion exchange resin, and when it is a primary amine, secondary amine or tertiary amine, it is called a weakly basic anion exchange resin.

  In this embodiment, when hydrogen peroxide and enones are reacted, it is not necessary to use a solvent. In the case of using a solvent, an aqueous solvent, an organic solvent, or a mixed solvent thereof can be used.

  Specific examples of solvents other than water that can be used in the present embodiment include alcohols having 1 to 6 carbon atoms such as methanol, ethanol, n-propanol, 2-propanol, n-butanol, hexanol, and cyclohexanol, and ethylene glycol. Examples thereof include glycol ethers having 3 to 6 carbon atoms such as monomethyl ether, ethylene glycol monoethyl ether and ethylene glycol monobutyl ether, and ethers having 2 to 6 carbon atoms such as tetrahydrofuran and dioxane. In addition, aliphatic hydrocarbons such as pentane, hexane and heptane, aromatic hydrocarbons such as benzene, toluene and xylene, alicyclic hydrocarbons such as cyclohexane, acetone, methyl ethyl ketone, methyl isobutyl ketone, methyl isopropyl ketone, Ketones such as cyclohexanone, esters such as ethyl acetate and butyl acetate, halogenated hydrocarbons such as dichloromethane and 1,2-dichloroethane, glycols such as ethylene glycol, pyridine, acetonitrile, dimethyl sulfoxide, dimethylformamide, ethylene carbonate Etc. can also be used.

  The reaction form in this embodiment is not specifically limited, For example, the said reaction may be implemented by a batch system and may be implemented by a continuous system. In the case of a continuous system, the catalyst can be suspended in the anti-response, and the reaction can be advanced by passing the reaction raw material through the catalyst as a fixed bed. In the method according to this embodiment, the raw materials are preferably mixed uniformly during the reaction, but may be separated into two phases as long as they can be reacted.

  In carrying out the above reaction, the amount of raw material charged, the amount of catalyst, the amount of solvent, the reaction time and the reaction temperature are not particularly limited, and these conditions may be appropriately selected according to the structure of the target epoxy ketone.

  For example, when producing a corresponding epoxy ketone using 2-cycloalkene-1-one as an enone, it is desirable to employ the following conditions. The amount of raw material charged is preferably 0.1 to 5.0 in terms of molar ratio of hydrogen peroxide with respect to the amount of enones to be reacted. More preferably, it is 2.0 or less. More preferably, it is 1.0 or more and 1.2 or less.

  The catalyst amount, solvent amount, reaction time, and reaction temperature are recommended to be selected from the following ranges regardless of the structure of the target epoxy ketones.

  The amount of the catalyst is preferably 1% by volume or more and 70% by volume or less, more preferably 5% by volume or more and 30% by volume or less with respect to the total volume of the reaction liquid containing the catalyst.

  The amount of the solvent is preferably 0 or more and 50 or less, and more preferably 0 or more and 25 or less, by mass ratio with respect to the enones that are raw materials.

  The reaction temperature is preferably 30 ° C. or higher and 80 ° C. or lower, and more preferably 30 ° C. or higher and 60 ° C. or lower. In view of productivity, the reaction time is preferably 1 hour or more and 24 hours or less, and more preferably 1 hour or more and 12 hours or less.

  The epoxy ketones obtained by this embodiment have a structure having a carbonyl group at the α-position of the epoxide. In addition, since the epoxy ketones produced by the method according to the present embodiment have high purity, it can be used as a product after the reaction, but if necessary, only the epoxy ketones are distilled, extracted and crystallized after the reaction. It is also preferable to separate the product by a general method such as analysis. Moreover, you may isolate | separate only enone which is a raw material by methods, such as distillation, extraction, and crystallization. In addition, the enones, which are raw materials, are converted using a catalyst so that the enones are substantially absent in the system, and the products after the conversion of the enones are separated by a general method as described above. It doesn't matter.

  Examples of the distillation method include, but are not limited to, vacuum distillation, steam distillation, molecular distillation, and extractive distillation. The crystallization method includes (1) cooling the reaction solution after completion of the reaction, (2) adding a poor solvent for the target product to the reaction solution, (3) distilling off the solvent during the reaction journey, 4) There is a method of gradually pressurizing the reaction solution, and these can be carried out alone or in combination.

  Among these, it is preferable that a solvent is used in the reaction step of hydrogen peroxide and enones, and the solvent used in the crystallization step after the reaction step is the same as the solvent used in the reaction step. In this case, the cost for solvent loss and solvent recovery is low, and the target compound can be obtained economically advantageously. Here, “common” means that different types of solvents are not added to the reaction solution obtained in the reaction step. For example, the reaction solution obtained in the reaction step is substantially subjected to the crystallization step as it is, or the same type of solvent as that used in the reaction step is added to the reaction solution, and this is subjected to the crystallization step. This is true. In this case, all or part of the solvent used in the reaction step may be contained in the crystallization solution in the crystallization step.

  Furthermore, the crystallization process can consist of one or more crystallization stages. During the crystallization process, it is preferable not to be in an open atmosphere but to be sealed with an inert gas. In the open state, oxygen is absorbed in the crystallization mother liquor, the hue is deteriorated, and it is difficult to obtain a high-quality product. The crystallization mother liquor from which the crystallization product has been separated is circulated to the reaction step as necessary from the viewpoint of efficient use of the raw material enones. In this case, at least a part of the crystallization mother liquor obtained in the crystallization step can be used as the raw material mother liquor. Usually, a multi-stage crystallization step and a solid-liquid separation step of the crystallization product are employed, and according to this, a plurality of types of mother liquors (enone-type solutions) are obtained. The mother liquor at the stage can be used as a raw material mother liquor for the reaction step or the crystallization step. In these steps, as described above, it is more efficient to use a common solvent for the reaction step and the crystallization step.

  As described above, if the produced epoxy ketones have no problem in use depending on the application, after the completion of the reaction, the product remains in the state containing unreacted raw materials and other impurities. Can be used.

  In the method according to this embodiment, since an anion-exchange layered compound is used as a catalyst, the crude product and the purified product after the completion of the reaction have a low content of impurities such as metals and halogens and are substantially reduced. Products that do not contain metals or halogens can also be manufactured. Specifically, a metal and / or halogen content of 50 ppm or less (mass basis, the same shall apply hereinafter), more preferably 10 ppm or less is obtained.

  Moreover, in this embodiment, since an anion exchange layered compound is used for the catalyst, the content of impurities is small and the target compound can be produced efficiently. Furthermore, since the catalyst can be easily separated, the product can be purified efficiently. The amount of unreacted enones can be 500 ppm or less (mass basis, the same applies hereinafter), preferably 100 ppm or less, more preferably 30 ppm or less, based on epoxy ketones. Moreover, in the said epoxy ketone, the ratio of an impurity can be 10 mass% or less, Preferably it is 5 mass% or less, More preferably, it is 2 mass% or less.

  The epoxy ketones thus obtained can be used alone or mixed with other components depending on the application. There is no particular limitation on the shape and state, and it can be handled in the form of a solid (eg, powder, flakes, grains, etc.), slurry, solution (eg, organic solvent solution).

  Hereinafter, the compound was actually created and the effect of the present invention was confirmed. However, it goes without saying that the present invention is not limited to the description of the following examples.

Example 1
First, a reaction between 2-cyclohexen-1-one, which is an α, β-unsaturated ketone, and hydrogen peroxide was performed. 0.048 g of 2-cyclohexen-1-one, 0.224 mL of 30% hydrogen peroxide, 2 mL of dimethylformamide as a solvent, and 0.05 g of NiZn-OAc as a catalyst are put into a 50 mL heat-resistant glass Schlenk tube. did. Subsequently, a 20 cm ball-containing cooling tube was installed and heated in an oil bath at 60 ° C. while shaking. And after making it react for 3 hours, the reaction liquid and the catalyst were isolate | separated by filtration, manganese dioxide was added to the reaction liquid, and the unreacted hydrogen peroxide was processed.

The reaction solution was analyzed by gas chromatography analysis (hereinafter referred to as “GC analysis”). In the GC analysis in this example, “GC-8A” manufactured by Shimadzu Corporation was used as the apparatus, “Thermon 3000 (φ5 mm × 3 m)” manufactured by GL Science Co., Ltd., and nitrogen as the carrier. The temperature condition was a pattern in which the temperature was raised from 100 ° C. to 240 ° C. at a rate of 10 ° C. per minute after sample injection, and then maintained at 240 ° C. The conversion rate and reaction selectivity of the measurement sample were calculated according to the following formula from the area ratio of the corresponding peak shown in the obtained GC chart.

  As a result of the GC analysis, the raw material 2-cyclohexen-1-one was 98% converted, and the reaction selectivity was 99.9% for the corresponding epoxy ketone. As a result, it was confirmed that it was a method capable of producing epoxy ketones having the target structure with high selectivity while suppressing the formation of by-products.

(Example 2)
Using NiZn—PO ₄ intercalated with a phosphate anion (PO ₄ ³⁻ ) as a catalyst, 2-cyclohexen-1-one and hydrogen peroxide were reacted in the same manner as in Example 1 to obtain a reaction solution. Got. As a result of performing GC analysis with respect to the obtained reaction liquid, the raw material 2-cyclohexen-1-one was 45% converted, and the reaction selectivity was 98% of the corresponding epoxy ketone. Also in this example, it was confirmed that it was a method capable of producing epoxy ketones having the target structure with high selectivity while suppressing the formation of by-products.

(Comparative Example 1)
A reaction solution was obtained by reacting 2-cyclohexen-1-one with hydrogen peroxide in the same manner as in Example 1 except that no catalyst was used. When GC analysis was performed on the obtained reaction solution, the conversion rate of the raw material 2-cyclohexen-1-one was only less than 1%.

<Synthesis example of catalysts A and B>
Nickel acetate tetrahydrate 32.8 g and zinc acetate dihydrate 14.5 g were placed in a 200 mL volumetric flask, and deionized water was added up to the marked line. This solution was hydrothermally synthesized at 200 ° C. for 24 hours in an autoclave. Thereafter, the solution was filtered, washed with deionized water, and then vacuum dried to obtain Catalyst A. The catalyst A is represented by [Ni _4/3 Zn _2/3 (OH) ₃ (CH ₃ COO) · nH ₂ O], and is an anion in which acetate ion (CH ₃ COO) ⁻ in the formula can be exchanged. .

To a 100 mL Erlenmeyer two-necked flask, 50 mL of 0.2 M aqueous K ₃ PO ₄ solution was added, and Catalyst A (2.0 g) was added. The resulting reaction mixture was stirred at 35 ° C. for 24 hours. Thereafter, it was washed and filtered using degassed water, and vacuum dried to obtain catalyst B.

  INDUSTRIAL APPLICABILITY The present invention has industrial applicability as a method for producing epoxy ketones, and the resulting epoxy ketones are useful as a perfume compounding agent and a pharmaceutical / agrochemical intermediate.

Claims (3)

  A method for producing an epoxy ketone by reacting a conjugated enone in the presence of an oxidizing agent using an anion exchange compound as a catalyst, wherein the epoxy ketone uses a compound having a botalakite structure as the anion exchange compound How to manufacture.   A method for producing an epoxyketone by reacting a conjugated enone in the presence of an oxidizing agent using an anion exchangeable compound as a catalyst, and using the hydrotalcite-like compound as the anion exchangeable compound How to manufacture. A method for producing an epoxy ketone by reacting a conjugated enone in the presence of an oxidizing agent using an anion exchange compound as a catalyst, and producing an epoxy ketone using an anion exchange resin as the anion exchange compound how to.