TW200837063A - Process for preparation of an oxirane - Google Patents

Abstract

The present invention relates to a process for preparing an oxirane compound, in particular to a solvent extraction process for a reaction mixture prepared by the reaction of an olefin and a peroxide in presence of a catalyst and an alcohol, to obtain an extract containing an oxirane and an olefin, and a raffinate containing an alcohol and water, by solvent extraction using water employed as an additional extraction solvent together with an organic extraction solvent. An example of the said oxirane compound is epichlorohydrine which can be obtained by epoxidation reaction of allyl chloride with hydrogen peroxide in presence of a catalyst and an alcohol as diluent.

Description

200837063 IX. DESCRIPTION OF THE INVENTION: TECHNICAL FIELD OF THE INVENTION The present invention relates to a method for producing an epoxy compound, and more particularly to a solvent extraction method, which uses a solvent as a solvent The water and an organic extraction solvent are used for solvent extraction, and the reaction mixture prepared by reacting the hydrocarbon with a peroxide in the presence of a catalyst and an alcohol is separated to obtain an extract containing ethylene bromide and anthracene (plus coffee). With raffinate containing alcohol and water (his). The

An example of a compound of the epoxy compound is epichlorohydrin which can be obtained by epoxidation of chloropropene with hydrogen peroxide in the presence of a catalyst and as a dilute alcohol. [Prior Art] The miscibility of olefins with hydrogen peroxide which is usually supplied as an aqueous solution for economic reasons is usually extremely poor. Therefore, the olefin and the aqueous hydrogen peroxide solution are mixed and diluted with an organic solvent which is preferably miscible with the rare candle and water. Examples of such organic solvents are methanol, ethanol, propanol and butanol. Methanol is especially preferred. The reaction of the dilute hydrocarbon which produces the epoxy ethene compound via the ring emulsification reaction with hydrogen peroxide is usually represented by the following reaction formula:

+ ΗεΟ, catalyst

0

For example, chloropropene undergoes an epoxidation reaction with hydrogen peroxide to produce epichlorohydrin. The reaction is an exothermic reaction represented by the following reaction formula:

Η2〇2 _catalyst

Η2ο Therefore, epoxidation occurs in the presence of chloropropene and hydrogen peroxide in the presence of methanol as a catalyst and as a diluent. The main components of the resulting reaction product are epichlorohydrin, water, chloropropene and methanol. The epichlorohydrin and chloropropene in the reaction product can be extracted into the extract' while methanol and water can be separated into the raffinate by solvent extraction using an organic compound or a toothed organic compound as an extraction solvent. The solvent extraction method comprises contacting the reaction product with an extraction solvent in an extraction apparatus, when using the solvent extraction method, by methanol, and the like, for example (USP 6, 288, 248, USP 6,350, 888, Korean Patent Publication No. 1999-45646) Epoxy chlorination, chloropropene

The main component of the extract such as an alkene and an extraction solvent has a chemical affinity, so at least a part of methanol is extracted into the extract. Further, since methanol and water have an affinity with each other, the read extract is accompanied by water. The methanol in the extract forms a mixture which is not easily separated from the epichlorohydrin by fractional distillation. The methanol in the extract makes it difficult to separate the high-purity epichlorohydrin from the extract by a conventional distillation method, and the water in the extract is difficult to design and operate steam due to the separation of water from the organic liquid in the distillation column. The remaining method. In addition, when the extract is heated to carry out steaming, at least a portion of the epichlorohydrin can be reacted with methanol and/or water via a reaction, and the epichlorohydrin can be converted into an undesired chlorinated impurity. For example, 1 - gas winter methoxy 1 propanol, 1 - chloromethyl 3-propanol di-propyl, propane. SUMMARY OF THE INVENTION The object of the present invention is to provide an effective solvent extraction method for separating a reaction mixture prepared by reacting an alkene with a peroxide in the presence of a catalyst and an alcohol to obtain an epoxy resin. And olefin extracts and raffinates containing alcohol and water 7 200837063 liquid. The present invention relates to a process for producing an oxirane compound, and more particularly to a solvent extraction process for separating solvent from olefins and peroxidation by using water as an additional extraction solvent and an organic extraction solvent for solvent extraction. The reaction mixture produced by reacting in the presence of a catalyst and an alcohol to obtain an extract containing ethylene oxide and an olefin and a raffinate containing an alcohol and water. The olefin is represented by an air propylene; the oxirane compound produced by reacting chloropropene with a peroxide is epichlorohydrin; from an economic point of view, the peroxide is an aqueous hydrogen peroxide solution; The alcohol may be a lower alcohol such as methanol, ethanol, n-propanol, isopropanol or butanol, with decyl alcohol being preferred. As the catalyst for producing ethylene oxide, a titanium silicalite catalyst having a structure similar to zeolite ZSM-5, which is generally called TS-1, can be used. The dilute hydrocarbon and the peroxygen peroxide are the main substances used for the reaction of the ethylene oxide compound by the epoxidation reaction, and the olefin and the hydrogen peroxide are mixed in various molar ratios to carry out the epoxidation reaction. The molar ratio of olefin to hydrogen peroxide is at least 0.1 to not more than 10. φ Since it is difficult to carry out the method for recovering unreacted hydrogen peroxide from the reaction product, it is preferred to deplete the hydrogen peroxide as much as possible. Therefore, in view of the operating cost of olefin recovery, the molar ratio of olefin to hydrogen peroxide is preferably not less than 1.0 but not more than 5,000. When a dilute hydrocarbon and an aqueous hydrogen peroxide solution which are used as an epoxidation reaction material for producing an oxirane compound are diluted with an alcohol such as methanol, the amount of the alcohol is selected in a wide range, but the amount of the alcohol used is at least a single liquid. The phase is mixed with a dilute hydrocarbon and an aqueous hydrogen peroxide solution. In view of the equipment cost and operating cost for recovering the alcohol, the amount of the alcohol is preferably not more than five times, more preferably not more than two times, the minimum amount required for mixing in a single liquid phase. In the range of 1 8 200837063 to 5 olefin/hydrogen peroxide molar ratio, to! Mohr peroxygen gas is an increase in the molar amount of alcohol required to mix an olefin and an aqueous hydrogen peroxide solution in a single liquid phase with an increase in the olefin/hydrogen peroxide molar ratio and water/excession. The molar ratio of 11 is preferably such that the aqueous hydrogen peroxide solution contains at least 2% by weight of the solution of Μ I - - 铁 铁 铁 铁 , , , , , , , , , , , , , , , , , , , , , , , , , Chlorine reading is used for the amount of methanol required for the reaction material in the thin-single-liquid phase. Therefore, it is better to use a plant containing at least 35% by weight of bismuth peroxide for cost and safety. The water-free or nearly anhydrous over-emulsified wind is less safe to stay in. Anti-= mixed and diluted in the liquid phase as an epoxidized product for producing epichlorohydrin;: and an aqueous solution of perchloric acid, such as methanol The alcohol is determined as the amount of dilute _ required methanol, the molar ratio of Wei _ / hydrogen peroxide = the molar ratio of water / peremulsified hydrogen. For example, when chloropropene / chlorine peroxide, ear, When the temperature is from 1 to 5, the aqueous solution of 35% by weight of hydrogen peroxide and the fine powder of propylene are mixed in a single-liquid phase. Then, the number of 4 ears is about 6 to 1 of the molar number of hydrogen peroxide. Epoxidation of ruthenium/olefin with hydrogen peroxide, (4) source ruthenium oxide in the reaction product by epoxidation The water contained in the water, and the alcohol in the hydrogen peroxide solution, such as methanol, are derived from the desired amount or more mixed with the reaction material to recognize the mouth; Materials such as methanol, etc. 9 200837063 Water as an additional extraction solvent of the present invention refers to water which is additionally included in the organic solvent extraction stage, and does not contain water present in the olefin and hydrogen peroxide reactant or present in the reaction product. Meanwhile, in the epoxidation reaction of chloropropene, the amount of methanol is determined by the liquid-liquid phase equilibrium, and the minimum amount of methanol is determined by the ratio of the propylene/hydrogen peroxide ratio and the ratio of water/hydrogen peroxide. The amount of sterol in the reaction product also reflects the amount of water. Therefore, the amount of water as an additional extraction solvent can be determined according to the amount of methanol in the reaction product, as an additional extraction solvent relative to the alcohol present in the reaction product. The amount of water used is preferably from 0.05 to 50 molar ratio, more preferably from 0.1 to 10 mole percent. The extraction solvent used in the method of the present invention is preferably selected from organic compounds or functionalized organication. The compounds have excellent compatibility with epoxy propane and chloropropene, but have low compatibility with water, and the difference in boiling point between the compounds and epichlorohydrin is at least 5 ° C to effectively The extract of the reaction product separates the final product. To achieve effective phase separation of the reaction product, the organic solvent is selected to produce a density difference of at least 0.01 g/cm 3 (g/cc) between the extract and the raffinate. And particularly a compound having a density difference of at least 0.1 φ g/cm 3 . The amount of the organic extraction solvent fed to the organic solvent extraction stage is preferably proportional to the amount of sterol in the reaction product. The organic extraction solvent is relative to 1 The amount of methanol in the ear is at least 0.05 to about 50 moles, preferably about 0.1 moles to 10 moles. The organic solvent as the extraction solvent is selected from the group consisting of (C1-C5)alkylbenzenes, halogenated benzenes, and nitrobenzenes. Halogenated (C3-C9) alkanes, (C7-C15) alkanes, halogenated (C3-C9) alkenes, (C7-C15) alkenes, and mixtures thereof. Examples of the organic solvent include o-xylene, m-xylene, p-xylene, ethylbenzene, 1,3,5-triphenylbenzene, o-dichlorobenzene, meta-200837063 chlorobenzene, p-dichlorobenzene, 1, 3,5-trichlorobenzene, o-chlorophenylbenzene, m-chlorophenylbenzene, p-chlorotoluene, 1,2,3-trichloropropane, nitrobenzene, n-decane, n-decane, chloropropene and mixtures thereof. The solvent extraction method of the present invention can be carried out in an extraction apparatus consisting of at least one extraction stage, and the organic solvent and water as an additional extraction solvent are fed to each other in opposite directions to the extraction apparatus to which the reaction product is supplied. . In particular, it is preferred that the water system as an additional extraction solvent is fed in a countercurrent to the extract, and the extraction solvent is fed in a countercurrent to the raffinate. The operating temperature of the extraction apparatus is preferably a temperature at which water which is an additional extraction solvent does not evaporate even in a small amount, and is usually lower than 10 °C. The operating temperature of the extraction apparatus is preferably such that the temperature of the water as an additional extraction solvent, even if it is small, is not frozen, and is usually higher than o °c. In order to suppress the decomposition of the reaction product, especially to inhibit the ring opening of epichlorohydrin, the extraction device is preferably operated at a temperature not exceeding 8 (TC). The operating pressure of the solvent extraction device is preferably higher than atmospheric pressure, but Not more than 10 bar, although it can be operated at atmospheric pressure, or greater than atmospheric pressure or less than atmospheric pressure. As a separation method suitable for separating extracts and extracting residues, distillation, azeotropic distillation, extraction can be used. Distillation or the like. After the extract is obtained from the reaction product by the extraction method of the present invention, the raffinate is separated into an alcohol mixture containing an alcohol as a main component and contains water as a main component by fractionation or the like. An aqueous mixture. The alcohol mixture is a reaction step of recycling recycled propylene with a peroxide, and a portion of the mixture comprising water as a main component is recycled back to the extraction device as an additional extraction solvent. The extract is extracted from the reaction product. After separating the epoxy propane and the chloropropene, the chloropropene is recycled back to the reaction step, and 11 20083706 3 from the epoxy chloride, but the extraction solvent is recovered and returned to the extraction step, while purifying the propane to provide high purity epichlorohydrin. Now refer to Figure 3 for the separation of extract and raffinate The detailed invention is not limited thereto. ^ The extract obtained by the dissolution method of the present invention is fractionated in a propylene-removing device 20 to be firstly extracted from the top of the column, a mixture of monoolefins as a main component. Contains chlorine recovery package

The mixture of 12 is recycled to the reaction stage. If the amount of chloroform as the main component. The amount of impurities in the lanthanum exceeds the desired amount, it is “minimum (4) to be purified to remove light and heavy impurities before recycling to the reaction stage. In the apparatus for recovering chloropropene 20 In the bottom effluent, τ 筏 contains a mixture of epichlorohydrin and an extraction solvent as a main component. The bottom substance is fractionated in a unit 3 for recovering the extraction solvent, and is supplied as a a mixture comprising epichlorohydrin as a main component 14, : L product, .u and a mixture of bottoms as a bottoms comprising a stroke solvent as a main component. In this case, it is preferred to maintain the operating force. Below atmospheric pressure, so that the operating temperature of the lower portion of the column does not rise excessively. The mixture 14 recovered from the apparatus 30 for recovering the extraction solvent has a predominantly 8% oxychloropropane, and the mixture 14 may comprise an epoxy. The volatiles of chloropropanone and the water. In order to remove these light impurities and water, in the device 40 for removing light impurities, the light impurities 16 and water are removed from the upper part of the tower, and in the lower part of the tower. Recycling Oxychloropropane 17. The mixture 17 obtained from the apparatus 40 for removing light impurities has the main component epichlorohydrin, and the mixture 17 is used for removing heavy impurities (having lower than 戸-, ^ gas 12 200837063 propane) Distillation is carried out in apparatus 50 to obtain an epichlorohydrin product 18 having an epichlorohydrin purity of at least 99% by weight as an overhead effluent. Heavy impurities 19 are used as by-products in the form of a bottoms effluent. (by-products) is discharged. The extraction solvent 15 recovered as the bottoms effluent of the apparatus 30 for recovering the extraction solvent is recycled to the solvent extraction apparatus. At this time, in order to prevent accumulation of impurities in the extraction solvent, A portion of the extraction solvent is discharged outwardly. The raffinate 21 is fractionated in a unit 60 for recovering methanol to recover a mixture 22 containing methanol as a main component as an overhead effluent, and as a bottoms effluent. a mixture of component water and an organic compound or a vaporized organic compound as a by-product. 23. The methanol recovered from the apparatus 60 for recovering methanol is returned to the reverse Step: cooling the mixture 23 containing water as a main component recovered from the apparatus 60 for recovering methanol, and subjecting the mixture 23 to liquid-liquid phase separation in a decanter to separate into an organic compound or a chlorinated organic compound An organic layer as a main component and an aqueous layer containing water as a main component. The organic substances are discharged as a by-product and supplied to a device 30 for recovering an extraction solvent to recover a trace amount of epichlorohydrin or an extract thereof. The solvent is supplied to the apparatus 10 for solvent extraction. The aqueous layer containing water as a main component can be separated into water and organic by-products by means of extractive distillation, solvent extraction or azeotropic distillation. A part of the water can be returned to the solvent extraction. The step is provided to the solvent extraction unit as an additional extraction solvent. BRIEF DESCRIPTION OF THE DRAWINGS Other and further objects, features and advantages of the present invention will become more fully apparent from the description. EXAMPLES 13 200837063 The examples are described to more specifically illustrate the invention, but the invention is not limited to the following examples. [Examples 1 to 5] An extraction solvent composed of an organic compound or a functional organic compound was added to a reaction product containing epichlorohydrin, chloropropene, water and methanol as main components. Then, liquid-liquid phase separation occurs, and is separated into an extract containing an extraction solvent, epichlorohydrin, and chloropropene as main components, and a raffinate containing methanol and water as main components. Due to the chemical affinity between the sterol and the main component of the extract, the extract contains a certain proportion of methanol, and the chemical affinity between the main component of the raffinate and the extraction solvent causes the raffinate to contain a certain proportion of the extraction solvent. In order to confirm the phenomenon in which sterol is extracted into the extract, a solvent extraction method is carried out in an extraction apparatus consisting of one extraction stage. Five extraction solvents were added to the product, and the main components of the extract and the raffinate were analyzed to calculate the extraction rate. The results are shown in Table 1, wherein the extraction ratio is defined as the ratio of the weight of a component in the extract to the weight of the same component in the reaction product. The reaction product is obtained by epoxidation reaction by diluting the gas propylene and hydrogen peroxide with methanol and mixing with a TS-1 catalyst (titanium-containing silicalite compound), and the exemplary components of the reaction product are by weight. Methanol: Epoxy chlorinated: 75% water: 13%: 12%. To the reaction product, a double amount (by volume) of the extraction solvent was added at room temperature. The resulting mixture was vigorously stirred to achieve thorough mixing. After the mixture was sufficiently left for a while, the contents of the main components of the extract and the raffinate thus obtained were analyzed to calculate the extraction ratio. The extraction solvent used 14 200837063 The knife is o-dichlorobenzene, o-xylene, and 1 calcination. The results are summarized in the table! in. ,,-------------------------------------------------------------------------------------------------------------- 3-trichloropropane

—————————-°-01 1.00 It can be seen from Table 1 that in the examples., 3 and 4 in which the extraction ratio of epichlorohydrin is not lower than 〇5, the extraction rate of methanol is not low. At 0.07. The reason why this occurs is that methanol is accompanied by the chemical affinity of methanol as the main extract of the extract. The yield of methanol in real _ 5 is lower than that in the examples 2, 3 or 4. However, since the epichlorohydrin in Example 5 has a low extraction ratio, the positive Wei system has a low practical extraction solvent. In Examples 1 to 5, it can be seen that 'there is a higher chemical affinity with Epoxy Chloride and is therefore suitable for extracting an epoxy-like organic compound or an organic compound, and also having a disc affinity. Therefore, at least at least one of the extracted products. - Part of the methanol is extracted as an extract. [Examples 6 and 7] / The reaction product was obtained by diluting with a methanol: a reagent containing a molar ratio of chloropropene and hydrogen peroxide, and reacting with a TS] catalyst, and the reaction product was obtained: 15 200837063 The composition consists of epichlorohydrin oxime, water 2 68 mol and methanol 8 i6 mol. To the reaction product, ortho-dichlorobenzene or U,3-trichloropropanone is added to the reaction product at room temperature. The mixture was vigorously transferred and thoroughly placed for a period of time, and the contents of the main components of the extract and the raffinate thus obtained were analyzed according to the same method as that of Examples 1 to 5, To calculate the extraction rate. The molar ratio of the amount of water added as an additional extraction enthalpy to the amount of methanol in the reaction product is adjusted. The experimental results are summarized in Tables 2 and 3.

16 200837063 From the results of Examples # and 7 not shown in Tables 2 and 3, it can be seen that when the ratio of methanol in the water and the reaction product as an additional granule is increased, the extraction rate of methanol accompanying the extract is remarkable. Increasing, and thus the extraction rate of epichlorohydrin and the extraction solvent is increased by 0. These results confirm that o-dichlorobenzene or 1,2,3-trichloropropane is used as an extraction solvent and water is added as an additional extraction solvent.玎 inhibits the accompanying extraction of methanol. [Example 8] 10 Countercurrent multistage extraction using an extraction apparatus consisting of three extraction stages Although in Examples 1 to 7, solvent extraction was performed on the reaction product in an extraction apparatus consisting of one extraction stage, However, a solvent extraction device consisting of multiple extraction stages should be used to increase the extraction rate of epichlorohydrin and chlorpromazine into the extract. As a method for suppressing the phenomenon of methanol and water in the extract in a solvent extraction apparatus composed of a plurality of stages, by using an extraction apparatus consisting of three extraction stages according to a countercurrent multi-stage extraction method, Use water as an additional solvent • Solvent extraction method and compare extraction rates. The chemical method used in the simulation experiment simulates the soft system Aspen Plus 2004 of Aspen Tech (U.S.A.), and uses the UNIQUAC model on the physical properties of the phase balance as a model for explaining the liquid/liquid phase equilibrium behavior. The parameters of the UNIQUAC phase equilibrium model were obtained by self-optimization techniques (〇ptimizati〇ntechnique) using the results of various liquid/liquid phase separation experiments performed by the Applicant. The main component of the reaction product obtained by diluting with 2:1 molar ratio of a reactant containing chloropropene and hydrogen peroxide, and mixing and reacting with the TS-1 catalyst is chloropropene ι·οο莫Ear, epichlorohydrin 1 〇〇 Mo Er, water 2. 89 Mo and A 17 200837063 Alcohol 5.91 Mo. As the extraction solvent, the molar amount of 1,2,3-trichloropropane is the same as that of the methanol in the reaction product. The methods and results of the simulation experiments are shown in Table 4. In the extraction apparatus, the relatively light raffinate is discharged in the first of the three stages, while the relatively heavy extract is discharged in the third stage. The operating temperature is 25 °C. The extraction solvent is supplied in a countercurrent to the raffinate, and the water as an additional extraction solvent is supplied in a countercurrent to the extract. [Table 4] Example 8: Results of countercurrent multistage extraction using an extraction apparatus consisting of three extraction stages The presence of water as an additional solvent does not provide a means of providing water to the extraction apparatus reaction product: reaction product: The third stage extraction solvent is provided: the first stage is supplied to the second stage extraction solvent: supplied to the first stage water: the third stage is provided as the additional extraction solvent and the molar ratio of the sterol in the reaction product is 1 : 1. Extraction rate Extraction rate Extraction rate (1) Chlorpromium (1) 0.998 (1) 0.990 (2) Epichlorohydrin (2) 0.999 (2) 0.990 (3) Water (3) 0.169 (3) 0.046 (4) Methanol (4) 0.503 (4) 0.039 18 200837063 (5) Extraction solvent (5) 0.971 (5) 0.986 [Example 9] Bayesan Example 9 was carried out according to the method described in Example 8, but in a countercurrent flow An extraction apparatus having seven extraction stages is used in the stage extraction method. The relatively light raffinate is discharged from the first stage, and the relatively heavy extract is discharged from the white ##. The operating temperature is 25 〇c. The extraction solvent is supplied in a countercurrent to the raffinate as an additional extraction solvent to provide a countercurrent to the extract. [Table 51: Example 9: Countercurrent flow using an extraction device consisting of seven extraction stages] White result as water for additional solvent No provision for providing water to the extraction device Reaction product: supplied to the seventh stage Extraction solvent: supplied to the first stage reaction product: supplied to the fourth stage extraction solvent: supplied to the first stage water: supplied to the seventh stage as an additional extraction solvent and the molar ratio of sterol in the reaction product ^ ^ --- ---------- is 1:1. % take rate (1) chlorine dilute extraction rate (1) 0.999 extraction rate (1) 0.999 (2) epichlorohydrin (3) water (2) 0.999 (2) 0.999 --_ one (3) 0.170 (3 0.040 19 200837063 (4) Methanol (4) 0.505 (5) Extraction solvent (5) 0.971 (4) 0.003 (5) 0.984 In Example 8, when the solvent extraction device consisting of three extraction stages was not added as In the case of additional solvent water, the extraction rate of methanol is 〇·5〇3, and when water is supplied as an additional solvent, the extraction rate of methanol is lowered to 0.039. When water was added as an additional solvent, the extraction rate of water contained in the reaction product was also lowered from 0.169 to 〇46. As a secondary effect of adding water as an additional solvent, the extraction rate of the extraction solvent was found to increase from 0,971 to 0.986. In the solvent extraction apparatus consisting of seven extraction layers of Example 9, when the water as an additional extraction solvent was not added, the extraction ratio of methanol was 0 505. When water is added as an additional extraction solvent in a countercurrent to the extract, the extraction rate of methanol is lowered to 〇3. When water is supplied as an additional extraction solvent, the extraction rate of water in the reaction product is lowered from 0.170 to 〇.〇40. From the results of Examples 8 and 9, it can be confirmed that the phenomenon that methanol and water are taken out from the reaction product with the extract can be provided by supplying the extraction solvent in a countercurrent to the raffinate and by countercurrent to the extract. It is suppressed as an additional solvent water. When water is not supplied as an additional solvent, the extraction ratio of m >, methanol and water does not decrease even if the number of extraction stages is increased from 3 stages to 7. However, when water is supplied as an additional solvent, the number of extraction stages from left to right is increased from 3 to 7. The extraction rate of methanol is also reduced from 0.039 to 0.003. It can be confirmed from Examples 6 and 7, that the extraction rate of methanol can be controlled by adjusting the molar ratio of methanol in the hydrazine & 〃 product as an additional extraction solvent to reduce the single rate of methanol's stroke. . It can be confirmed from Examples 8 and 9 that the extraction of methanol can be controlled according to the same method in a solvent extraction apparatus consisting of a plurality of extracted Mi 20 200837063. As described above, the solvent extraction method of the present invention using water as an additional solvent can significantly reduce the extraction rate of alcohol into the extract as compared with the solvent extraction method using only the extraction solvent. Therefore, it is advantageous to overcome the design and operation difficulties due to the alcohol and water contained in the extract during the separation of the olefin, ethylene oxide and the extraction solvent in the extract. According to the present invention, a high-purity oxirane compound can be obtained by a series of separations of an extract containing a small amount of alcohol and water recovered from a solvent extraction method and a raffinate containing an alcohol and water as a main component. Advantageously, at least a portion of the olefin, extraction solvent, alcohol, and water can be reused during the process of making the oxirane compound. BRIEF DESCRIPTION OF THE DRAWINGS Fig. 1 is a structural view of a single stage extraction apparatus of the present invention; Fig. 2 is a structural view of the multistage extraction apparatus of the present invention; and Fig. 3 is an illustration of the present invention. A block diagram of the process of inventing the extraction process. [Main component symbol description] 1 : Initial solution or mixture of reaction products 2 : Extraction solvent ^ 3: Water as an additional extraction solvent 4 : Extract 5 : Raffinate 6 : Single stage extraction device 7 : Multistage extraction device 10 Organic solvent extraction apparatus 11 : Extract 12: Mixture containing chloropropene as a main component 21 200837063 13: Mixture containing epichlorohydrin and an extraction solvent as a main component 14: Mixture 15 containing epichlorohydrin as a main component: a mixture comprising an extraction solvent as a main component 16: a light impurity in epichlorohydrin 17 : a mixture containing epoxidized gas as a main component from which light impurities have been removed 18: an epichlorohydrin product having removed heavy impurities 19 : Heavy impurities in epichlorohydrin 20 : Device for recovering chloropropene ® 21 : Raffinate 22 : Mixture containing methanol as a main component 23 : Mixture containing water as a main component 30 : For recovery of extraction solvent Apparatus 40: Apparatus for removing light impurities 50: Apparatus for removing heavy impurities 60: Apparatus for recovering sterols 22

Claims (1)

200837063 X. Patent application scope: 1. A solvent extraction method for performing solvent extraction by using water as an additional extraction solvent and an organic extraction solvent, and separating by dilute hydrocarbon and peroxide in the presence of a catalyst and an alcohol The reaction mixture is prepared to obtain an extract comprising ethylene oxide and an olefin and a raffinate comprising an alcohol and water. 2. The method of claim 1, wherein the olefin is chloropropene and the corresponding epoxidized compound is epichlorohydrin. 3. The method of claim 2, wherein the molar ratio of water to the alcohol present in the reaction mixture as the additional extraction solvent is between 0.05:1 and 50:1. 4. The method of claim 3, wherein the molar ratio of water to the alcohol present in the reaction mixture as the additional extraction solvent is between 0.1 and 1 :1. 5. The method of claim 2, wherein the molar ratio of the extraction solvent to the alcohol present in the reaction mixture is between 0.1:1 and 10:1. The method of claim 2, wherein the temperature difference between the boiling point of the organic solvent and the boiling point of the epichlorohydrin is at least 5 °C. 7. The method of claim 2, wherein the organic solvent is selected such that the difference between the density of the extract and the density of the raffinate is at least 0.1 grams per cubic centimeter (g/cc). 8. The method of claim 6, wherein the organic solvent is selected from the group consisting of (C1-C5)alkylbenzenes, halogenated benzenes, nitrobenzenes, halogenated (C3-C9) alkanes, (C7) - C15) alkanes, halogenated (C3-C9) olefins, (C7-C15) olefins, and mixtures thereof. The method of claim 8, wherein the organic solvent is selected from the group consisting of o-xylene, m-xylene, p-xylene, ethylbenzene, 1,3,5-trimethylbenzene, O-dichlorobenzene, m-dichlorobenzene, p-dichlorobenzene, 1,3,5-trichlorobenzene, o-chlorophenylbenzene, m-chlorotoluene, p-chlorotoluene, 1,2,3-trichloropropane, nitro Benzene, n-decane, n-ray, chloropropene and mixtures thereof. 10. The method of claim 1 , characterized in that it consists of at least one extraction stage, and the organic solvent and water as an additional solvent are fed to the extraction apparatus in opposite directions to each other, wherein the reaction product is Provided to the extraction device. 11. The method of claim 10, wherein the aqueous system as an additional extraction solvent is provided in a countercurrent to the extract, and the extraction solvent is provided in a countercurrent to the raffinate. 12. The method of claim 2, wherein the peroxide is hydrogen peroxide and the alcohol is methanol. 13. The method of claim 10, wherein the temperature of the extraction device is in the range of 0 °C to 100 °C. 14. The method according to any one of claims 1 to 6, 10 and 11, wherein the raffinate is separated into an alcohol mixture containing an alcohol as a main component and an aqueous mixture containing water as a main component; and the alcohol The mixture is recycled back to the reaction step for the reaction of the chloropropene with the peroxide, and a portion of the aqueous mixture comprising water as the main component is recycled back to the extraction unit. twenty four