Method for producing aliphatic nitrile compounds

Abstract

A method for producing an aliphatic nitrile compound is disclosed, which involves directly substituting an aliphatic compound having two or more carboxyl groups with a nitrile compound.

Description

Detailed Description of the Invention

[0001] [Technical Field] The present invention relates to a method for producing an aliphatic nitrile compound, and more particularly to an environmentally friendly method for producing an aliphatic nitrile compound.

[0002] [Background Art] Due to the rapid development of information and communication technologies in recent years, the market for portable electronic devices such as mobile phones, notebook computers, and tablet computers has been growing. As a result, the demand for secondary batteries used as power sources for these electronic devices has also been increasing. Such an increase in demand has led to the development of secondary battery technology, and its application fields have been expanding to electric vehicles, energy storage devices, and the like.

[0003] The usage time of portable electronic devices, the driving distance of electric vehicles, and the capacity of energy storage devices are mainly determined by the performance of secondary batteries. Lithium secondary batteries have higher discharge voltages and energy densities compared to conventional alkaline secondary batteries, and the most research and development have been conducted on them. In particular, the demand for lithium secondary batteries with high output, large capacity, and long life has been increasing.

[0004] A lithium secondary battery is manufactured by injecting an organic electrolyte into a battery cell including a positive electrode containing a positive electrode active material capable of intercalating and deintercalating lithium, a negative electrode containing a negative electrode active material capable of intercalating and deintercalating lithium, and a separator insulating these. Here, copper used as a current collector of the negative electrode is easily oxidized during over-discharge of the secondary battery. As a result, there is a problem that the life and capacity of the lithium secondary battery are reduced.

[0005] To address these issues, aliphatic nitrile compounds such as adiponitrile are used as additives to the electrolyte. These aliphatic nitrile compounds do not hinder the formation of the solid electrolyte interface (SEI) layer and can suppress copper oxidation without impairing other properties of the secondary battery.

[0006] Conventional aliphatic nitrile compounds were produced by chlorinating olefins and then reacting them with cyanide, or by hydrocyanizing olefins in the presence of a nickel catalyst. These production methods are economically disadvantageous due to the use of catalysts, and even after purification processes, it is difficult to produce high-purity products due to the generation of impurities. Furthermore, when aliphatic nitrile compounds are produced in organic solvents to suppress the generation of impurities, there is a problem of wastewater generation during the washing process.

[0007] Therefore, there is a growing demand for processes that produce high-purity aliphatic nitrile compounds in an economical and environmentally friendly manner.

[0008] [Overview of the prefecture] [Problems the invention aims to solve] The provisions described herein were devised in consideration of the problems of the prior art described above, and their main objective is to provide high-purity aliphatic nitrile compounds in an environmentally friendly manner without using the water washing step that was essential in conventional manufacturing methods due to catalysts and other organic reactions.

[0009] Furthermore, according to the provisions of this specification, high-purity aliphatic nitrile compounds can be produced by a simple method, while the reaction products can be easily reused.

[0010] [Means for solving the problem] In one aspect, a method for producing an aliphatic nitrile compound is provided, comprising the steps of (a) producing a mixture containing a nitrile compound and a carbonyl compound; and (b) reacting the mixture, wherein the carbonyl compound is an aliphatic compound containing two or more carboxyl groups, and the reaction in step (b) is a reaction in which two or more carboxyl groups are directly substituted for nitrile groups.

[0011] In one embodiment, the nitrile compound is one or more selected from the group consisting of hydrogen cyanide, acetonitrile, acrylonitrile, butyronitrile, isobutyronitrile, pivalonitrile, succinonitrile, fumaronitrile, crotonitrile, and benzonitrile.

[0012] In one embodiment, the carbonyl compound is one or more selected from the group consisting of adipic acid, pimlic acid, suberic acid, azelaic acid, sebacic acid, undecanedicarboxylic acid, and dodecanedicarboxylic acid.

[0013] In one embodiment, the mixture in step (a) may consist of the nitrile compound and the carbonyl compound.

[0014] In one embodiment, in step (a), the content of the nitrile compound may be 1 to 500 parts by weight based on 1 part by weight of the carbonyl compound.

[0015] In one embodiment, the water content of the mixture in step (a) may be 6,000 ppm or less.

[0016] In one embodiment, the reaction in step (b) may be carried out under conditions of 260-500°C and 40-200 bar.

[0017] In one embodiment, step (b) may be performed for 1 to 500 minutes.

[0018] In one embodiment, the method may further include step (c) after step (b) above, in which the product of step (b) is separated to obtain an aliphatic nitrile compound.

[0019] In one embodiment, the purity of the obtained aliphatic nitrile compound may be further characterized by being 60% by weight or more.

[0020] [Effects of the invention] From one perspective, aliphatic nitrile compounds can be produced by a simple method.

[0021] From another perspective, it is possible to reuse raw materials and obtain products without a separate washing process, and to produce aliphatic nitrile compounds in an environmentally friendly manner.

[0022] Furthermore, from another perspective, it is possible to produce high-purity aliphatic nitrile compounds.

[0023] The effects of one aspect of this specification should be understood to include all effects that can be inferred from the detailed description or claims herein, and not limited to those described herein.

[0024] [Modes for carrying out the invention] The following describes one aspect of this specification. However, the provisions described herein can be implemented in various different forms and are therefore not limited to the embodiments described herein.

[0025] Wherever a specification states that a part is “connected” to another part, this includes not only cases where they are “directly connected” but also cases where they are “indirectly connected” through other components. Furthermore, wherever a part is said to “include” a component, unless otherwise stated, this does not exclude other components, but rather means that it may further include other components.

[0026] When a numerical value range is described in this specification, unless the specific range is separately described, the value has the accuracy of significant figures given according to the standard rules of chemistry regarding significant figures. For example, 10 includes the range from 5.0 to 14.9, and the numerical value 10.0 includes the range from 9.50 to 10.49. Also, when multiple examples of numerical values are described in this specification, unless explicitly stated to exclude intermediate values, these examples may include intermediate values. For example, "x1, x2, x3 or x4" may include the ranges of "x1~x2", "x1~x3", "x1~x4", "x2~x3", "x2~x4", "x3~x4".

[0027] In this specification, "supercritical condition" means a state that satisfies conditions above the critical point which is the endpoint of the phase equilibrium curve. For example, when the critical temperature of compound A is Tc and the critical pressure is Pc, the supercritical condition of compound A means a state where the temperature is above Tc and the pressure is above Pc.

[0028] Hereinafter, one embodiment of this specification will be described in detail.

[0029] Method for producing aliphatic nitrile compounds According to one aspect, the method for producing an aliphatic nitrile compound includes: (a) a step of producing a mixture containing a nitrile compound and a carbonyl compound; and (b) a step of reacting the mixture, wherein the carbonyl compound is an aliphatic compound containing two or more carboxy groups, and the reaction in step (b) may be a reaction in which two or more carboxy groups are directly substituted by nitrile groups respectively.

[0030] The nitrile compound may be one or more selected from the group consisting of hydrogen cyanide, acetonitrile, acrylonitrile, butyronitrile, isobutyronitrile, pivalonitrile, succinonitrile, fumaronitrile, crotonitrile and benzonitrile, but is not limited thereto.

[0031] The carbonyl compound may be a compound having two or more carboxyl groups. Furthermore, the carbonyl compound may have at least one carboxyl group at the end of its main chain. For example, the carbonyl compound may have one or more carboxyl groups at each end of its main chain, one or more carboxyl groups at one end of its main chain and one or more carboxyl groups on its side chain, or one or more carboxyl groups at each end of its main chain and one or more carboxyl groups on its side chain.

[0032] As an example, the carbonyl compound may be, but is not limited to, the compound represented by the following chemical formula 1.

[0033] [ka]

[0034] In the above chemical formula, n is an integer greater than or equal to 3, m is an integer from 0 to 2 determined for each of the n carbon chains, k and k' are integers from 0 to 3, and k+k'+m may be greater than or equal to 2.

[0035] In the above chemical formula, n is an integer greater than or equal to 3, and may be, but is not limited to, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15. If the value of n deviates from the above range, only a portion of the carboxyl groups of the compound may be replaced with nitrile groups, or mixing of nitrile compounds and carbonyl compounds may become difficult.

[0036] In the above chemical formula, m is the number of carboxyl groups in the side chain, and can be an integer from 0 to 2 for each of the n carbon atoms constituting the main chain. For example, m can be 0 or 1.

[0037] In the above chemical formula, k and k' are the number of carboxyl groups at the ends of the main chain, and can be integers from 0 to 3. For example, a main chain end with k or k' being 1 has one carboxyl group. As an example, k and k' can be 0 or 1, while satisfying k+k'>0. If the density of carboxyl groups is excessively high in a certain region of the carbonyl compound, only some of the carboxyl groups may be substituted with nitrile groups.

[0038] For example, the carbonyl compound may be, but is not limited to, at least one selected from the group consisting of adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, undecanedioic acid, and dodecanedioic acid.

[0039] As an example, the carbonyl compounds may have a total number of carbon-carbon bonds associated with each carbon located between each carboxyl group of 7 or more, or 8 or more. For example, adipic acid contains four alkylene carbons between two carboxyl groups. Since an alkylene carbon contains two carbon-carbon bonds and two carbon-hydrogen bonds, the total number of carbon-carbon bonds associated with each carbon located between each carboxyl group of adipic acid is 8. Although the provisions of this specification are not limited to the above scope, nitrile substitution reactions using carbonyl compounds that satisfy the above conditions may yield products with excellent purity and yield in which all carboxyl groups are substituted with nitrile groups. On the other hand, carbonyl compounds that do not satisfy the above conditions may result in only some of the carboxyl groups being substituted with nitrile groups, or the formation of compounds different from the target compound.

[0040] In step (b), the mixture can be reacted without the addition of ammonia, high-concentration oxygen, or catalysts. Because the reaction in step (b) can be carried out without the addition of other additives, the mixture in step (a) may, but is not limited to, consist of the nitrile compound and the carbonyl compound. For example, the mixture may, but is not limited to, a solution of the carbonyl compound in a nitrile compound solvent.

[0041] In step (a) above, the content of the nitrile compound may be 1 to 500 parts by weight based on 1 part by weight of the carbonyl compound. For example, the content of the nitrile compound may be 1 part by weight, 5 parts by weight, 10 parts by weight, 15 parts by weight, 20 parts by weight, 25 parts by weight, 30 parts by weight, 35 parts by weight, 40 parts by weight, 45 parts by weight, 50 parts by weight, 55 parts by weight, 60 parts by weight, 65 parts by weight, 70 parts by weight, 75 parts by weight, 80 parts by weight, 85 parts by weight, 90 parts by weight, 95 parts by weight, 100 parts by weight, 105 parts by weight, 110 parts by weight, 115 parts by weight, based on 1 part by weight of the carbonyl compound. Parts by weight, 120 parts by weight, 125 parts by weight, 130 parts by weight, 135 parts by weight, 145 parts by weight, 150 parts by weight, 155 parts by weight, 160 parts by weight, 165 parts by weight, 170 parts by weight, 175 parts by weight, 180 parts by weight, 185 parts by weight parts, 190 parts by weight, 195 parts by weight, 200 parts by weight, 205 parts by weight, 210 parts by weight, 215 parts by weight, 220 parts by weight, 225 parts by weight, 230 parts by weight, 235 parts by weight, 240 parts by weight, 245 parts by weight, 250 parts by weight, 255 parts by weight, 260 parts by weight, 265 parts by weight, 270 parts by weight, 275 parts by weight, 280 parts by weight, 285 parts by weight, 290 parts by weight, 295 parts by weight, 300 parts by weight, 305 parts by weight, 310 parts by weight, 315 parts by weight, 3 20 parts by weight, 325 parts by weight, 330 parts by weight, 335 parts by weight, 340 parts by weight, 345 parts by weight, 350 parts by weight, 355 parts by weight, 360 parts by weight, 365 parts by weight, 370 parts by weight, 375 parts by weight, 380 parts by weight, 385 The amount may be parts by weight, 390 parts by weight, 395 parts by weight, 400 parts by weight, 405 parts by weight, 410 parts by weight, 415 parts by weight, 420 parts by weight, 425 parts by weight, 430 parts by weight, 435 parts by weight, 440 parts by weight, 445 parts by weight, 450 parts by weight, 455 parts by weight, 460 parts by weight, 465 parts by weight, 470 parts by weight, 475 parts by weight, 480 parts by weight, 485 parts by weight, 490 parts by weight, 495 parts by weight, 500 parts by weight, or a range between these two values. The higher the content of the nitrile compound relative to the carbonyl compound, the higher the purity of the product may be, but if the nitrile compound is excessively high, it may be disadvantageous from an economic standpoint.

[0042] In step (a) above, the water content of the mixture may be 6,000 ppm or less. For example, the water content of the mixture may be less than 6,000 ppm, less than 5,000 ppm, less than 4,000 ppm, less than 3,000 ppm, less than 2,000 ppm, less than 1,000 ppm, less than 750 ppm, less than 500 ppm, or less than 250 ppm. The lower the water content of the mixture, the higher the purity of the product may be.

[0043] The reaction can be carried out if the temperature and pressure conditions in step (b) are above the critical point of the nitrile compound. Step (b) can be carried out under conditions of 260-500°C and 40-200 bar. For example, step (b) can be carried out at reaction temperatures of 260°C, 265°C, 270°C, 275°C, 280°C, 285°C, 290°C, 295°C, 300°C, 305°C, 310°C, 315°C, 320°C, 325°C, 330°C, 335°C, 340°C, 345°C, 350°C, 355°C, 360°C, 365°C, 370°C, 375°C, 380°C, It can be done at 385°C, 390°C, 395°C, 400°C, 405°C, 410°C, 415°C, 420°C, 425°C, 430°C, 435°C, 440°C, 445°C, 450°C, 455°C, 460°C, 465°C, 470°C, 475°C, 480°C, 485°C, 490°C, 495°C, 500°C, or within a range between these two values. For example, step (b) may be carried out at reaction pressures of 40 bar, 45 bar, 50 bar, 55 bar, 60 bar, 65 bar, 70 bar, 75 bar, 80 bar, 85 bar, 90 bar, 95 bar, 100 bar, 105 bar, 110 bar, 115 bar, 120 bar, 125 bar, 130 bar, 135 bar, 140 bar, 145 bar, 150 bar, 155 bar, 160 bar, 165 bar, 170 bar, 175 bar, 180 bar, 185 bar, 190 bar, 195 bar, 200 bar, or in the range between these two values. If the reaction temperature in step (b) is too low, the purity of the product may decrease or the reaction may not occur at all, and if the reaction temperature is too high, the formation of by-products may increase and the purity may decrease. If the reaction pressure in step (b) is excessively low, the reaction may not occur, and if the reaction pressure is excessively high, safety may be compromised.

[0044] As an example, if the nitrile compound is hydrogen cyanide, step (b) may be carried out at a temperature of 183.5°C or higher and a pressure of 50 bar or higher. If the nitrile compound is acetonitrile, step (b) may be carried out at a temperature of 272°C or higher and a pressure of 48.7 bar or higher. If the nitrile compound is acrylonitrile, step (b) may be carried out at a temperature of 267°C or higher and a pressure of 46 bar or higher. If the nitrile compound is butyronitrile, step (b) may be carried out at a temperature of 309°C or higher and a pressure of 37.8 bar or higher. If the nitrile compound is isobutyronitrile, step (b) may be carried out at a temperature of 336°C or higher and a pressure of 40 bar or higher. If the nitrile compound is pivalonitrile, step (b) may be carried out at a temperature of 343°C or higher and a pressure of 34.4 bar or higher. In addition, the conditions for step (b) may vary depending on the type of nitrile compound. Therefore, all of the above conditions are exemplary and do not limit the scope of this specification. The nitrile compound may be a solvent and a reactant.

[0045] The aforementioned step (b) may be performed for 1 to 500 minutes. For example, the aforementioned step (b) may be 1 minute, 5 minutes, 10 minutes, 15 minutes, 20 minutes, 25 minutes, 30 minutes, 35 minutes, 40 minutes, 45 minutes, 50 minutes, 55 minutes, 60 minutes, 65 minutes, 70 minutes, 75 minutes, 80 minutes, 85 minutes, 90 minutes, 95 minutes, 100 minutes, 105 minutes, 110 minutes, 115 minutes, 120 minutes, 125 minutes, 130 minutes, 135 minutes minutes, 145 minutes, 150 minutes, 155 minutes, 160 minutes, 165 minutes, 170 minutes, 175 minutes, 180 minutes, 185 minutes, 190 minutes, 195 minutes, 200 minutes, 205 minutes, 210 minutes, 215 minutes, 220 minutes, 225 minutes, 230 minutes, 235 minutes, 240 minutes, 245 minutes, 250 minutes, 255 minutes, 260 minutes, 265 minutes, 2 It can be done in the range of 70 minutes, 275 minutes, 280 minutes, 285 minutes, 290 minutes, 295 minutes, 300 minutes, 305 minutes, 310 minutes, 315 minutes, 320 minutes, 325 minutes, 330 minutes, 335 minutes, 340 minutes, 345 minutes, 350 minutes, 355 minutes, 360 minutes, 365 minutes, 370 minutes, 375 minutes, 380 minutes, 385 minutes, 390 minutes, 395 minutes, 400 minutes, 405 minutes, 410 minutes, 415 minutes, 420 minutes, 425 minutes, 430 minutes, 435 minutes, 440 minutes, 445 minutes, 450 minutes, 455 minutes, 460 minutes, 465 minutes, 470 minutes, 475 minutes, 480 minutes, 485 minutes, 490 minutes, 495 minutes, 500 minutes, or a range between these two values. While a longer reaction time in step (b) may improve the purity of the product, excessively long reaction times may reduce productivity.

[0046] The procedure may further include (c) separating the product of step (b) to obtain an aliphatic nitrile compound. The separation in step (c) may be carried out by separating the generated aliphatic nitrile compound from the remainder compound, and may be carried out by various known methods such as distillation separation. The remainder compound may include, but is not limited to, one or more compounds selected from the group consisting of, for example, an unreacted carbonyl compound, an unreacted nitrile compound, and a compound in which only a portion of the carboxyl group of the carbonyl compound has reacted.

[0047] The remaining compound separated in step (c) can be reused in step (a). Since the method for producing the aliphatic nitrile compound can be carried out without the use of additional additives such as catalysts, the remaining compound can be reused without further purification.

[0048] The purity of the obtained aliphatic nitrile compound may be 60% by weight or more, 65% by weight or more, 70% by weight or more, 75% by weight or more, 80% by weight or more, 85% by weight or more, or 90% by weight or more.

[0049] As an example, the aliphatic nitrile compound can be represented by the following chemical formula 2, but is not limited to this.

[0050] [ka]

[0051] In the above chemical formula, n is an integer greater than or equal to 3, m is an integer from 0 to 2 determined for each of the n carbon chains, k and k' are integers from 0 to 3, and k+k'+m may be greater than or equal to 2.

[0052] The aliphatic nitrile compound represented by chemical formula 2 may be a compound represented by chemical formula 1 described above, in which all carboxyl groups are replaced with nitrile groups.

[0053] The moisture content of the product obtained by the above manufacturing method may be 500 ppm or less. For example, the moisture content of the product may be less than 500 ppm, less than 400 ppm, less than 300 ppm, less than 200 ppm, less than 100 ppm, less than 75 ppm, or less than 50 ppm. The lower the moisture content of the product, the less likely it is that side reactions of the aliphatic nitrile compound will occur during storage, resulting in better storage stability.

[0054] The embodiments of this specification will be described in more detail below. However, the following experimental results represent only representative results from the embodiments described above, and the scope and content of this specification should not be narrowed or limited by the embodiments. The effects of any of the embodiments of this specification that are not explicitly presented below will be described in detail in the relevant sections.

[0055] Example 1 A reaction system was formed by adding 10 parts by weight of adipic acid and 100 parts by weight of acetonitrile to a 1,000 mL autoclave equipped with a stirrer. The inside of the autoclave was purged with nitrogen three times at a pressure of 2-3 bar. The internal temperature of the autoclave was raised to 280°C while stirring at 300 rpm at atmospheric pressure. The reaction was carried out for 4 hours while maintaining the reaction temperature, and the reaction pressure was 90 bar. After the reaction was complete, the reaction system was cooled to room temperature. Subsequently, the reaction system was separated under reduced pressure to separate acetonitrile and adiponitrile (ADN). The acetonitrile was reused, and the purity of the adiponitrile was confirmed by gas chromatography (GC). The water content of the obtained product was also measured.

[0056] Example 2 A reaction system was formed by adding 10 parts by weight of adipic acid and 100 parts by weight of acetonitrile to a 1,000 mL reactor equipped with a stirrer. The reactor was purged with nitrogen three times at a pressure of 2-3 bar. The reactor was heated to 350°C while being stirred at 300 rpm under atmospheric pressure. The reaction was carried out for 4 hours while maintaining the reaction temperature, and the reaction pressure was 90 bar. After the reaction was complete, the reaction system was cooled to room temperature. Subsequently, the reaction system was separated under reduced pressure to separate acetonitrile and adiponitrile. The acetonitrile was reused, and the purity of the product was confirmed by gas chromatography analysis of the adiponitrile. The water content of the obtained product was also measured.

[0057] Example 3 A reaction system was formed by adding 10 parts by weight of sebacic acid and 100 parts by weight of acetonitrile to a 1,000 mL reactor equipped with a stirrer. The reactor was purged with nitrogen three times at a pressure of 2-3 bar. The reactor was heated to 280°C while being stirred at 300 rpm under atmospheric pressure. The reaction was carried out for 4 hours while maintaining the reaction temperature, and the reaction pressure was 90 bar. After the reaction was complete, the reaction system was cooled to room temperature. Subsequently, the reaction system was separated under reduced pressure to separate acetonitrile and adiponitrile. The acetonitrile was reused, and the purity of the product was confirmed by gas chromatography analysis of the adiponitrile. The water content of the obtained product was also measured.

[0058] Example 4 A reaction system was formed by adding 10 parts by weight of sebacic acid and 100 parts by weight of acetonitrile to a 1,000 mL reactor equipped with a stirrer. The reactor was purged with nitrogen three times at a pressure of 2-3 bar. The reactor was heated to 350°C while being stirred at 300 rpm under atmospheric pressure. The reaction was carried out for 4 hours while maintaining the reaction temperature, and the reaction pressure was 90 bar. After the reaction was complete, the reaction system was cooled to room temperature. Subsequently, the reaction system was separated under reduced pressure to separate acetonitrile and adiponitrile. The acetonitrile was reused, and the purity of the product was confirmed by gas chromatography analysis of the adiponitrile. The water content of the obtained product was also measured.

[0059] Example 5 A reaction system was formed by adding 10 parts by weight of suberic acid and 100 parts by weight of acetonitrile to a 1,000 mL reactor equipped with a stirrer. The reactor was purged with nitrogen three times at a pressure of 2-3 bar. The reactor was heated to 280°C while being stirred at 300 rpm at atmospheric pressure. The reaction was carried out for 4 hours while maintaining the reaction temperature, and the reaction pressure was 90 bar. After the reaction was complete, the reaction system was cooled to room temperature. Subsequently, the reaction system was separated under reduced pressure to separate acetonitrile and adiponitrile. The acetonitrile was reused, and the purity of the product was confirmed by gas chromatography analysis of the adiponitrile. The water content of the obtained product was also measured.

[0060] Comparative Example 1 A reaction system was formed by adding 10 parts by weight of maleic acid and 100 parts by weight of acetonitrile to a 1,000 mL reactor equipped with a stirrer. The reactor was purged with nitrogen three times at a pressure of 2-3 bar. The reactor was heated to 280°C while being stirred at 300 rpm at atmospheric pressure. The reaction was carried out for 4 hours while maintaining the reaction temperature, and the reaction pressure was 90 bar. After the reaction was completed, the reaction system was cooled to room temperature. Subsequently, the reaction system was separated under reduced pressure to separate the product from the acetonitrile. The acetonitrile was reused, and the purity of the product was confirmed by gas chromatography, but the target product, an aliphatic nitrile compound, was not sufficiently produced.

[0061] Comparative Example 2 A reaction system was formed by adding 10 parts by weight of succinic acid and 100 parts by weight of acetonitrile to a 1,000 mL reactor equipped with a stirrer. The reactor was purged with nitrogen three times at a pressure of 2-3 bar. The reactor was heated to 280°C while being stirred at 300 rpm under atmospheric pressure. The reaction was carried out for 4 hours while maintaining the reaction temperature, and the reaction pressure was 90 bar. After the reaction was completed, the reaction system was cooled to room temperature. Subsequently, the reaction system was separated under reduced pressure to separate the product from the acetonitrile. The acetonitrile was reused, and the purity of the product was confirmed by gas chromatography, but the target product, an aliphatic nitrile compound, was not sufficiently produced.

[0062] Comparative Example 3 A reaction system was formed by adding 10 parts by weight of glutaric acid and 100 parts by weight of acetonitrile to a 1,000 mL reactor equipped with a stirrer. The reactor was purged with nitrogen three times at a pressure of 2-3 bar. The reactor was heated to 280°C while being stirred at 300 rpm under atmospheric pressure. The reaction was carried out for 4 hours while maintaining the reaction temperature, and the reaction pressure was 90 bar. After the reaction was completed, the reaction system was cooled to room temperature. Subsequently, the reaction system was separated under reduced pressure to separate the product from the acetonitrile. The acetonitrile was reused, and the purity of the product was confirmed by gas chromatography, but the target product, an aliphatic nitrile compound, was not sufficiently produced.

[0063] The reaction conditions and product purity for the examples and comparative examples are summarized in Table 1 below.

[0064] [Table 1]

[0065] Referring to the table above, among aliphatic acid compounds having two or more carboxyl groups, maleic acid, succinic acid, glutaric acid, etc., were difficult to obtain aliphatic nitrile compound products when reacting with nitrile compounds, but adipic acid, sebacic acid, suberic acid, etc., were able to produce aliphatic nitrile compounds in high purity.

[0066] The descriptions herein provided herein are illustrative, and a person with ordinary skill in the art to which any aspect of this specification belongs will understand that the technical ideas and essential features described herein can be readily adapted to other specific forms without alteration. Therefore, the embodiments described herein should be understood to be illustrative and not limiting in all respects. For example, each component described in a single form may be implemented in a distributed manner, and similarly, components described as distributed may be implemented in a combined manner.

[0067] The scope of this specification is defined by the claims, and all modifications or variations derived from the meaning and scope of the claims and the concept of equivalents thereof should be construed as being included within the scope of this specification.

Claims

1. (a) the step of producing a mixture containing a nitrile compound and a carbonyl compound; and (b) a step of reacting the mixture; The carbonyl compound is an aliphatic compound containing two or more carboxyl groups, A method for producing an aliphatic nitrile compound, wherein the reaction in step (b) is a reaction in which two or more carboxyl groups are directly substituted for nitrile groups.

2. The method for producing an aliphatic nitrile compound according to claim 1, characterized in that the nitrile compound is one or more selected from the group consisting of hydrogen cyanide, acetonitrile, acrylonitrile, butyronitrile, isobutyronitrile, pivalonitrile, succinonitrile, fumaronitrile, crotonitrile, and benzonitrile.

3. The method for producing an aliphatic nitrile compound according to claim 1, characterized in that the carbonyl compound is one or more selected from the group consisting of adipic acid, pimlic acid, suberic acid, azelaic acid, sebacic acid, undecanedicarboxylic acid, and dodecanedicarboxylic acid.

4. The method for producing an aliphatic nitrile compound according to claim 1, wherein the mixture in step (a) is composed of the nitrile compound and the carbonyl compound.

5. The method for producing an aliphatic nitrile compound according to claim 1, characterized in that, in step (a) above, the content of the nitrile compound is 1 to 500 parts by weight based on 1 part by weight of the carbonyl compound.

6. The method for producing an aliphatic nitrile compound according to claim 1, characterized in that, in step (a), the water content of the mixture is 6,000 ppm or less.

7. The method for producing an aliphatic nitrile compound according to claim 1, characterized in that the reaction in step (b) is carried out under conditions of 260 to 500°C and 40 to 200 bar.

8. The method for producing an aliphatic nitrile compound according to claim 1, characterized in that step (b) is carried out for 1 to 500 minutes.

9. The method for producing an aliphatic nitrile compound according to claim 1, further comprising the step of (c) separating the product of step (b) to obtain an aliphatic nitrile compound.

10. The method for producing an aliphatic nitrile compound according to claim 9, characterized in that the purity of the obtained aliphatic nitrile compound is 60% by weight or more.

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